# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_mm421
_database_code_depnum_ccdc_archive 'CCDC 1426599'
_audit_update_record             
;
2015-09-22 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        1
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H60 Gd2 N6 O14'
_chemical_formula_weight         1139.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.3263(3)
_cell_length_b                   8.3727(2)
_cell_length_c                   20.7908(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.8720(11)
_cell_angle_gamma                90
_cell_volume                     2261.48(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9832
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.31

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_F_000             1140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.976
_shelx_estimated_absorpt_T_min   0.647
_shelx_estimated_absorpt_T_max   0.755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5149
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'

_exptl_special_details           
; 
 Data collection is performed with three batch runs at phi = 0.00 deg 
 (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg 
 (650 frames). 
 Frame width = 0.30 deg in omega. 
 Data is merged, corrected for decay (if any), and treated with multi-scan 
 absorption corrections (if required). All symmetry-equivalent reflections 
 are merged for centrosymmetric data. 
 Friedel pairs are not merged for noncentrosymmetric data. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29945
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.257
_diffrn_reflns_theta_max         28.312
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             5567
_reflns_number_gt                5333
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0239P)²+3.1676P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5567
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0200
_refine_ls_wR_factor_ref         0.0510
_refine_ls_wR_factor_gt          0.0503
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Gd1 Gd 0.36428(2) 0.97262(2) 0.52477(2) 0.01453(4) Uani 1 1 d . . . . .
O1 O 0.29553(12) 0.97438(18) 0.61706(8) 0.0205(3) Uani 1 1 d . . . . .
O2 O 0.14453(14) 1.0779(2) 0.66750(9) 0.0310(4) Uani 1 1 d . . . . .
O3 O 0.53240(11) 0.87113(17) 0.53510(7) 0.0163(3) Uani 1 1 d . . . . .
O4 O 0.19487(12) 0.8863(2) 0.48856(8) 0.0271(4) Uani 1 1 d . . . . .
O5 O 0.34984(12) 0.8238(2) 0.42427(7) 0.0225(3) Uani 1 1 d . . . . .
O6 O 0.45700(13) 1.1690(2) 0.59674(8) 0.0248(3) Uani 1 1 d . . . . .
H6A H 0.4429 1.2118 0.6364 0.037 Uiso 1 1 d R U . . .
H6B H 0.5314 1.1850 0.5960 0.037 Uiso 1 1 d R U . . .
N4 N 0.40141(14) 0.7116(2) 0.58180(9) 0.0184(3) Uani 1 1 d . . . . .
N5 N 0.49056(14) 0.6273(2) 0.57511(9) 0.0213(4) Uani 1 1 d . . . . .
N6 N 0.72319(14) 0.7685(2) 0.53227(9) 0.0228(4) Uani 1 1 d . . . . .
C1 C 0.23678(16) 0.8653(3) 0.63475(10) 0.0191(4) Uani 1 1 d . . . . .
C2 C 0.15162(17) 0.9152(3) 0.66167(10) 0.0232(4) Uani 1 1 d . . . . .
C3 C 0.08531(19) 0.8061(3) 0.67967(13) 0.0318(5) Uani 1 1 d . . . . .
H3A H 0.0276 0.8424 0.6954 0.038 Uiso 1 1 calc R U . . .
C4 C 0.1026(2) 0.6427(4) 0.67489(15) 0.0385(6) Uani 1 1 d . . . . .
H4A H 0.0564 0.5678 0.6869 0.046 Uiso 1 1 calc R U . . .
C5 C 0.1866(2) 0.5904(3) 0.65278(13) 0.0319(5) Uani 1 1 d . . . . .
H5A H 0.1997 0.4790 0.6513 0.038 Uiso 1 1 calc R U . . .
C6 C 0.25388(17) 0.6997(3) 0.63212(11) 0.0221(4) Uani 1 1 d . . . . .
C7 C 0.0752(2) 1.1361(4) 0.70515(15) 0.0400(6) Uani 1 1 d . . . . .
H7A H 0.0765 1.2531 0.7055 0.060 Uiso 1 1 calc R U . . .
H7B H 0.0960 1.0962 0.7505 0.060 Uiso 1 1 calc R U . . .
H7C H 0.0054 1.0990 0.6854 0.060 Uiso 1 1 calc R U . . .
C8 C 0.34468(17) 0.6337(3) 0.61373(11) 0.0224(4) Uani 1 1 d . . . . .
H8A H 0.3632 0.5266 0.6260 0.027 Uiso 1 1 calc R U . . .
C9 C 0.54906(16) 0.7201(3) 0.54928(10) 0.0180(4) Uani 1 1 d . . . . .
C10 C 0.64280(17) 0.6479(3) 0.53130(12) 0.0232(4) Uani 1 1 d . . . . .
H10A H 0.6702 0.5616 0.5629 0.028 Uiso 1 1 calc R U . . .
H10B H 0.6230 0.6001 0.4867 0.028 Uiso 1 1 calc R U . . .
C11 C 0.7745(2) 0.8064(4) 0.60093(13) 0.0370(6) Uani 1 1 d . . . . .
H11A H 0.7236 0.8474 0.6243 0.055 Uiso 1 1 calc R U . . .
H11B H 0.8276 0.8874 0.6012 0.055 Uiso 1 1 calc R U . . .
H11C H 0.8063 0.7095 0.6229 0.055 Uiso 1 1 calc R U . . .
C12 C 0.7991(2) 0.7084(4) 0.49646(16) 0.0410(7) Uani 1 1 d . . . . .
H12A H 0.7645 0.6837 0.4508 0.062 Uiso 1 1 calc R U . . .
H12B H 0.8315 0.6115 0.5181 0.062 Uiso 1 1 calc R U . . .
H12C H 0.8519 0.7900 0.4966 0.062 Uiso 1 1 calc R U . . .
C13 C 0.14611(17) 0.7835(3) 0.44940(12) 0.0258(5) Uani 1 1 d . . . . .
C14 C 0.18285(18) 0.7135(3) 0.39795(12) 0.0278(5) Uani 1 1 d . . . . .
H14A H 0.1383 0.6437 0.3687 0.033 Uiso 1 1 calc R U . . .
C15 C 0.28107(17) 0.7402(3) 0.38705(10) 0.0214(4) Uani 1 1 d . . . . .
C16 C 0.0417(2) 0.7387(4) 0.45990(15) 0.0433(7) Uani 1 1 d . . . . .
H16A H 0.0474 0.7100 0.5063 0.065 Uiso 1 1 calc R U . . .
H16B H 0.0150 0.6473 0.4318 0.065 Uiso 1 1 calc R U . . .
H16C H -0.0053 0.8295 0.4485 0.065 Uiso 1 1 calc R U . . .
C17 C 0.3109(2) 0.6630(3) 0.32829(12) 0.0330(5) Uani 1 1 d . . . . .
H17A H 0.3735 0.5996 0.3433 0.050 Uiso 1 1 calc R U . . .
H17B H 0.3235 0.7460 0.2978 0.050 Uiso 1 1 calc R U . . .
H17C H 0.2549 0.5934 0.3057 0.050 Uiso 1 1 calc R U . . .
O7 O 0.35148(15) 1.2514(2) 0.68483(9) 0.0335(4) Uani 1 1 d . . . . .
H7D H 0.3224 1.1647 0.6717 0.049(10) Uiso 1 1 calc R . . . .
C18 C 0.3685(3) 1.2600(4) 0.75446(14) 0.0471(8) Uani 1 1 d . . . . .
H18A H 0.4029 1.1613 0.7742 0.057 Uiso 1 1 calc R U . . .
H18B H 0.3016 1.2689 0.7675 0.057 Uiso 1 1 calc R U . . .
C19 C 0.4330(3) 1.3993(4) 0.77918(16) 0.0553(9) Uani 1 1 d . . . . .
H19A H 0.4447 1.4034 0.8274 0.083 Uiso 1 1 calc R U . . .
H19B H 0.3980 1.4971 0.7603 0.083 Uiso 1 1 calc R U . . .
H19C H 0.4991 1.3900 0.7663 0.083 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Gd1 O1 2.3032(14) . ?
Gd1 O4 2.3300(16) . ?
Gd1 O3 2.3608(14) . ?
Gd1 O6 2.3758(16) . ?
Gd1 O5 2.4035(15) . ?
Gd1 O3 2.4333(14) 3_676 ?
Gd1 N4 2.4831(18) . ?
Gd1 N6 2.6166(19) 3_676 ?
Gd1 Gd1 4.0021(2) 3_676 ?
O1 C1 1.308(3) . ?
O2 C2 1.373(3) . ?
O2 C7 1.423(3) . ?
O3 C9 1.306(3) . ?
O3 Gd1 2.4333(13) 3_676 ?
O4 C13 1.261(3) . ?
O5 C15 1.270(3) . ?
N4 C8 1.289(3) . ?
N4 N5 1.415(2) . ?
N5 C9 1.299(3) . ?
N6 C10 1.469(3) . ?
N6 C12 1.472(3) . ?
N6 C11 1.473(3) . ?
N6 Gd1 2.6166(19) 3_676 ?
C1 C6 1.408(3) . ?
C1 C2 1.435(3) . ?
C2 C3 1.379(3) . ?
C3 C4 1.395(4) . ?
C4 C5 1.373(3) . ?
C5 C6 1.414(3) . ?
C6 C8 1.457(3) . ?
C9 C10 1.508(3) . ?
C13 C14 1.400(3) . ?
C13 C16 1.503(3) . ?
C14 C15 1.395(3) . ?
C15 C17 1.511(3) . ?
O7 C18 1.416(3) . ?
C18 C19 1.471(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Gd1 O4 74.61(6) . . ?
O1 Gd1 O3 118.17(5) . . ?
O4 Gd1 O3 138.53(6) . . ?
O1 Gd1 O6 73.65(5) . . ?
O4 Gd1 O6 138.48(6) . . ?
O3 Gd1 O6 80.90(5) . . ?
O1 Gd1 O5 139.28(5) . . ?
O4 Gd1 O5 70.98(5) . . ?
O3 Gd1 O5 77.47(5) . . ?
O6 Gd1 O5 146.72(5) . . ?
O1 Gd1 O3 142.96(5) . 3_676 ?
O4 Gd1 O3 128.28(5) . 3_676 ?
O3 Gd1 O3 66.82(6) . 3_676 ?
O6 Gd1 O3 71.10(5) . 3_676 ?
O5 Gd1 O3 77.22(5) . 3_676 ?
O1 Gd1 N4 71.45(6) . . ?
O4 Gd1 N4 87.53(6) . . ?
O3 Gd1 N4 63.61(5) . . ?
O6 Gd1 N4 106.74(6) . . ?
O5 Gd1 N4 85.84(6) . . ?
O3 Gd1 N4 129.96(5) 3_676 . ?
O1 Gd1 N6 98.78(6) . 3_676 ?
O4 Gd1 N6 78.97(6) . 3_676 ?
O3 Gd1 N6 131.09(5) . 3_676 ?
O6 Gd1 N6 80.15(6) . 3_676 ?
O5 Gd1 N6 95.40(6) . 3_676 ?
O3 Gd1 N6 64.44(5) 3_676 3_676 ?
N4 Gd1 N6 165.18(6) . 3_676 ?
O1 Gd1 Gd1 139.80(4) . 3_676 ?
O4 Gd1 Gd1 144.95(4) . 3_676 ?
O3 Gd1 Gd1 33.98(3) . 3_676 ?
O6 Gd1 Gd1 73.13(4) . 3_676 ?
O5 Gd1 Gd1 74.78(4) . 3_676 ?
O3 Gd1 Gd1 32.84(3) 3_676 3_676 ?
N4 Gd1 Gd1 97.37(4) . 3_676 ?
N6 Gd1 Gd1 97.20(4) 3_676 3_676 ?
C1 O1 Gd1 127.15(13) . . ?
C2 O2 C7 117.0(2) . . ?
C9 O3 Gd1 118.64(12) . . ?
C9 O3 Gd1 123.29(12) . 3_676 ?
Gd1 O3 Gd1 113.18(6) . 3_676 ?
C13 O4 Gd1 138.00(15) . . ?
C15 O5 Gd1 136.27(14) . . ?
C8 N4 N5 113.56(18) . . ?
C8 N4 Gd1 127.88(15) . . ?
N5 N4 Gd1 118.32(12) . . ?
C9 N5 N4 109.66(17) . . ?
C10 N6 C12 109.8(2) . . ?
C10 N6 C11 109.90(18) . . ?
C12 N6 C11 109.9(2) . . ?
C10 N6 Gd1 108.27(13) . 3_676 ?
C12 N6 Gd1 109.93(15) . 3_676 ?
C11 N6 Gd1 108.94(16) . 3_676 ?
O1 C1 C6 124.38(19) . . ?
O1 C1 C2 118.8(2) . . ?
C6 C1 C2 116.79(19) . . ?
O2 C2 C3 124.9(2) . . ?
O2 C2 C1 113.55(19) . . ?
C3 C2 C1 121.5(2) . . ?
C2 C3 C4 120.3(2) . . ?
C5 C4 C3 119.8(2) . . ?
C4 C5 C6 121.0(2) . . ?
C1 C6 C5 120.4(2) . . ?
C1 C6 C8 122.34(19) . . ?
C5 C6 C8 117.0(2) . . ?
N4 C8 C6 124.0(2) . . ?
N5 C9 O3 125.82(19) . . ?
N5 C9 C10 117.96(19) . . ?
O3 C9 C10 116.18(18) . . ?
N6 C10 C9 111.25(18) . . ?
O4 C13 C14 124.1(2) . . ?
O4 C13 C16 115.9(2) . . ?
C14 C13 C16 119.9(2) . . ?
C15 C14 C13 123.9(2) . . ?
O5 C15 C14 124.4(2) . . ?
O5 C15 C17 116.4(2) . . ?
C14 C15 C17 119.2(2) . . ?
O7 C18 C19 110.2(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N4 N5 C9 -172.7(2) . . . . ?
Gd1 N4 N5 C9 12.4(2) . . . . ?
Gd1 O1 C1 C6 43.5(3) . . . . ?
Gd1 O1 C1 C2 -139.61(16) . . . . ?
C7 O2 C2 C3 11.5(4) . . . . ?
C7 O2 C2 C1 -168.2(2) . . . . ?
O1 C1 C2 O2 -2.0(3) . . . . ?
C6 C1 C2 O2 175.14(19) . . . . ?
O1 C1 C2 C3 178.3(2) . . . . ?
C6 C1 C2 C3 -4.5(3) . . . . ?
O2 C2 C3 C4 -176.6(2) . . . . ?
C1 C2 C3 C4 3.0(4) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -2.6(4) . . . . ?
O1 C1 C6 C5 179.5(2) . . . . ?
C2 C1 C6 C5 2.6(3) . . . . ?
O1 C1 C6 C8 4.8(3) . . . . ?
C2 C1 C6 C8 -172.2(2) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C4 C5 C6 C8 175.9(3) . . . . ?
N5 N4 C8 C6 174.4(2) . . . . ?
Gd1 N4 C8 C6 -11.3(3) . . . . ?
C1 C6 C8 N4 -19.7(4) . . . . ?
C5 C6 C8 N4 165.4(2) . . . . ?
N4 N5 C9 O3 3.9(3) . . . . ?
N4 N5 C9 C10 -173.61(18) . . . . ?
Gd1 O3 C9 N5 -19.2(3) . . . . ?
Gd1 O3 C9 N5 -172.67(17) 3_676 . . . ?
Gd1 O3 C9 C10 158.36(14) . . . . ?
Gd1 O3 C9 C10 4.9(2) 3_676 . . . ?
C12 N6 C10 C9 -163.4(2) . . . . ?
C11 N6 C10 C9 75.5(2) . . . . ?
Gd1 N6 C10 C9 -43.4(2) 3_676 . . . ?
N5 C9 C10 N6 -153.8(2) . . . . ?
O3 C9 C10 N6 28.4(3) . . . . ?
Gd1 O4 C13 C14 -20.4(4) . . . . ?
Gd1 O4 C13 C16 160.5(2) . . . . ?
O4 C13 C14 C15 5.1(4) . . . . ?
C16 C13 C14 C15 -175.9(2) . . . . ?
Gd1 O5 C15 C14 0.6(4) . . . . ?
Gd1 O5 C15 C17 -177.88(16) . . . . ?
C13 C14 C15 O5 3.9(4) . . . . ?
C13 C14 C15 C17 -177.7(2) . . . . ?

_refine_diff_density_max         1.141
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.076

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mm300
_database_code_depnum_ccdc_archive 'CCDC 1426600'
_audit_update_record             
;
2015-09-22 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        2
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H60 Dy2 N6 O14'
_chemical_formula_weight         1149.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.3404(5)
_cell_length_b                   8.3937(3)
_cell_length_c                   20.8588(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.218(2)
_cell_angle_gamma                90
_cell_volume                     2282.77(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9982
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      28.22

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_F_000             1148
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    3.316
_shelx_estimated_absorpt_T_min   0.692
_shelx_estimated_absorpt_T_max   0.826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6100
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'

_exptl_special_details           
; 
 Data collection is performed with three batch runs at phi = 0.00 deg 
 (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg 
 (650 frames). 
 Frame width = 0.30 deg in omega. 
 Data is merged, corrected for decay (if any), and treated with multi-scan 
 absorption corrections (if required). All symmetry-equivalent reflections 
 are merged for centrosymmetric data. 
 Friedel pairs are not merged for noncentrosymmetric data. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35453
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.562
_diffrn_reflns_theta_max         28.407
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             5642
_reflns_number_gt                4290
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+6.8197P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5642
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Dy1 Dy 0.36511(2) 0.97254(3) 0.52486(2) 0.02302(9) Uani 1 1 d . . . . .
O1 O 0.2954(3) 0.9770(5) 0.6152(2) 0.0309(10) Uani 1 1 d . . . . .
O2 O 0.1453(4) 1.0824(6) 0.6668(3) 0.0481(13) Uani 1 1 d . . . . .
O3 O 0.5317(3) 0.8731(4) 0.5341(2) 0.0233(9) Uani 1 1 d . . . . .
O4 O 0.1984(3) 0.8881(6) 0.4902(2) 0.0383(11) Uani 1 1 d . . . . .
O5 O 0.3512(3) 0.8262(6) 0.4254(2) 0.0336(10) Uani 1 1 d . . . . .
O6 O 0.4557(3) 1.1633(5) 0.5966(2) 0.0358(11) Uani 1 1 d . . . . .
H6A H 0.5253 1.1733 0.5921 0.054 Uiso 1 1 d R U . . .
H6B H 0.4489 1.1979 0.6415 0.054 Uiso 1 1 d R U . . .
O7 O 0.3516(4) 1.2532(6) 0.6849(3) 0.0535(15) Uani 1 1 d . . . . .
H7D H 0.3175 1.1706 0.6722 0.064 Uiso 1 1 calc R U . . .
N1 N 0.4001(4) 0.7155(6) 0.5804(3) 0.0267(11) Uani 1 1 d . . . . .
N2 N 0.4893(4) 0.6303(6) 0.5734(3) 0.0313(12) Uani 1 1 d . . . . .
N3 N 0.7217(4) 0.7709(6) 0.5305(3) 0.0319(13) Uani 1 1 d . . . . .
C1 C 0.2369(4) 0.8690(7) 0.6341(3) 0.0272(13) Uani 1 1 d . . . . .
C2 C 0.1518(5) 0.9190(9) 0.6614(4) 0.0354(15) Uani 1 1 d . . . . .
C3 C 0.0866(5) 0.8111(10) 0.6794(4) 0.050(2) Uani 1 1 d . . . . .
H3A H 0.0295 0.8475 0.6959 0.060 Uiso 1 1 calc R U . . .
C4 C 0.1023(6) 0.6498(10) 0.6742(4) 0.055(2) Uani 1 1 d . . . . .
H4A H 0.0550 0.5761 0.6857 0.066 Uiso 1 1 calc R U . . .
C5 C 0.1856(6) 0.5960(9) 0.6524(4) 0.048(2) Uani 1 1 d . . . . .
H5A H 0.1985 0.4848 0.6515 0.058 Uiso 1 1 calc R U . . .
C6 C 0.2532(5) 0.7056(8) 0.6312(3) 0.0316(15) Uani 1 1 d . . . . .
C7 C 0.0772(7) 1.1413(11) 0.7056(5) 0.062(2) Uani 1 1 d . . . . .
H7A H 0.0785 1.2581 0.7056 0.093 Uiso 1 1 calc R U . . .
H7B H 0.0988 1.1022 0.7506 0.093 Uiso 1 1 calc R U . . .
H7C H 0.0074 1.1043 0.6871 0.093 Uiso 1 1 calc R U . . .
C8 C 0.3434(5) 0.6376(8) 0.6122(3) 0.0325(14) Uani 1 1 d . . . . .
H8A H 0.3610 0.5303 0.6240 0.039 Uiso 1 1 calc R U . . .
C9 C 0.5480(4) 0.7220(7) 0.5479(3) 0.0250(12) Uani 1 1 d . . . . .
C10 C 0.6416(5) 0.6509(7) 0.5301(4) 0.0327(15) Uani 1 1 d . . . . .
H10A H 0.6688 0.5655 0.5617 0.039 Uiso 1 1 calc R U . . .
H10B H 0.6226 0.6025 0.4859 0.039 Uiso 1 1 calc R U . . .
C11 C 0.7977(6) 0.7139(10) 0.4944(5) 0.058(2) Uani 1 1 d . . . . .
H11A H 0.7635 0.6886 0.4492 0.087 Uiso 1 1 calc R U . . .
H11B H 0.8312 0.6181 0.5157 0.087 Uiso 1 1 calc R U . . .
H11C H 0.8492 0.7970 0.4941 0.087 Uiso 1 1 calc R U . . .
C12 C 0.7728(6) 0.8084(10) 0.5991(4) 0.051(2) Uani 1 1 d . . . . .
H12A H 0.7216 0.8462 0.6231 0.077 Uiso 1 1 calc R U . . .
H12B H 0.8244 0.8916 0.5993 0.077 Uiso 1 1 calc R U . . .
H12C H 0.8061 0.7124 0.6204 0.077 Uiso 1 1 calc R U . . .
C13 C 0.1497(5) 0.7870(9) 0.4515(4) 0.0370(16) Uani 1 1 d . . . . .
C14 C 0.1856(5) 0.7167(9) 0.4008(4) 0.0396(17) Uani 1 1 d . . . . .
H14A H 0.1411 0.6467 0.3722 0.048 Uiso 1 1 calc R U . . .
C15 C 0.2837(5) 0.7428(8) 0.3892(3) 0.0317(14) Uani 1 1 d . . . . .
C16 C 0.0448(6) 0.7434(12) 0.4628(5) 0.062(2) Uani 1 1 d . . . . .
H16A H 0.0313 0.8029 0.5005 0.093 Uiso 1 1 calc R U . . .
H16B H 0.0424 0.6289 0.4714 0.093 Uiso 1 1 calc R U . . .
H16C H -0.0074 0.7702 0.4236 0.093 Uiso 1 1 calc R U . . .
C17 C 0.3133(6) 0.6679(10) 0.3301(4) 0.049(2) Uani 1 1 d . . . . .
H17A H 0.3840 0.6972 0.3291 0.073 Uiso 1 1 calc R U . . .
H17B H 0.2671 0.7062 0.2901 0.073 Uiso 1 1 calc R U . . .
H17C H 0.3078 0.5518 0.3328 0.073 Uiso 1 1 calc R U . . .
C18 C 0.3699(9) 1.2627(12) 0.7538(5) 0.075(3) Uani 1 1 d . . . . .
H18A H 0.4028 1.1629 0.7730 0.090 Uiso 1 1 calc R U . . .
H18B H 0.3037 1.2741 0.7677 0.090 Uiso 1 1 calc R U . . .
C19 C 0.4349(10) 1.3956(13) 0.7779(6) 0.093(4) Uani 1 1 d . . . . .
H19A H 0.4476 1.3978 0.8259 0.140 Uiso 1 1 calc R U . . .
H19B H 0.4012 1.4948 0.7603 0.140 Uiso 1 1 calc R U . . .
H19C H 0.5002 1.3849 0.7639 0.140 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Dy1 O1 2.271(4) . ?
Dy1 O4 2.301(4) . ?
Dy1 O3 2.344(4) . ?
Dy1 O6 2.345(4) . ?
Dy1 O3 2.408(4) 3_676 ?
Dy1 O5 2.385(4) . ?
Dy1 N1 2.446(5) . ?
Dy1 N3 2.597(5) 3_676 ?
Dy1 Dy1 3.9775(5) 3_676 ?
O1 C1 1.311(7) . ?
O2 C2 1.380(9) . ?
O2 C7 1.427(8) . ?
O3 C9 1.308(7) . ?
O3 Dy1 2.408(4) 3_676 ?
O4 C13 1.253(9) . ?
O5 C15 1.258(7) . ?
O7 C18 1.408(10) . ?
N1 C8 1.286(7) . ?
N1 N2 1.422(7) . ?
N2 C9 1.290(7) . ?
N3 C10 1.467(8) . ?
N3 C11 1.465(8) . ?
N3 C12 1.484(9) . ?
N3 Dy1 2.597(5) 3_676 ?
C1 C6 1.392(9) . ?
C1 C2 1.437(8) . ?
C2 C3 1.363(9) . ?
C3 C4 1.377(11) . ?
C4 C5 1.363(10) . ?
C5 C6 1.423(9) . ?
C6 C8 1.460(8) . ?
C9 C10 1.501(8) . ?
C13 C14 1.384(10) . ?
C13 C16 1.512(9) . ?
C14 C15 1.397(9) . ?
C15 C17 1.508(9) . ?
C18 C19 1.437(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Dy1 O4 74.18(16) . . ?
O1 Dy1 O3 119.03(15) . . ?
O4 Dy1 O3 138.87(16) . . ?
O1 Dy1 O6 72.90(15) . . ?
O4 Dy1 O6 138.13(16) . . ?
O3 Dy1 O6 80.72(15) . . ?
O1 Dy1 O3 142.50(15) . 3_676 ?
O4 Dy1 O3 128.62(16) . 3_676 ?
O3 Dy1 O3 66.37(16) . 3_676 ?
O6 Dy1 O3 71.66(15) . 3_676 ?
O1 Dy1 O5 139.48(15) . . ?
O4 Dy1 O5 71.07(15) . . ?
O3 Dy1 O5 77.66(14) . . ?
O6 Dy1 O5 147.32(14) . . ?
O3 Dy1 O5 77.32(14) 3_676 . ?
O1 Dy1 N1 72.09(16) . . ?
O4 Dy1 N1 87.23(17) . . ?
O3 Dy1 N1 64.19(14) . . ?
O6 Dy1 N1 106.24(17) . . ?
O3 Dy1 N1 130.07(14) 3_676 . ?
O5 Dy1 N1 85.95(17) . . ?
O1 Dy1 N3 97.63(16) . 3_676 ?
O4 Dy1 N3 78.77(17) . 3_676 ?
O3 Dy1 N3 131.12(14) . 3_676 ?
O6 Dy1 N3 80.70(18) . 3_676 ?
O3 Dy1 N3 64.93(14) 3_676 3_676 ?
O5 Dy1 N3 95.45(17) . 3_676 ?
N1 Dy1 N3 164.59(16) . 3_676 ?
O1 Dy1 Dy1 140.03(11) . 3_676 ?
O4 Dy1 Dy1 145.27(12) . 3_676 ?
O3 Dy1 Dy1 33.69(9) . 3_676 ?
O6 Dy1 Dy1 73.41(10) . 3_676 ?
O3 Dy1 Dy1 32.68(9) 3_676 3_676 ?
O5 Dy1 Dy1 75.00(10) . 3_676 ?
N1 Dy1 Dy1 97.66(11) . 3_676 ?
N3 Dy1 Dy1 97.53(11) 3_676 3_676 ?
C1 O1 Dy1 127.8(4) . . ?
C2 O2 C7 116.7(6) . . ?
C9 O3 Dy1 118.2(3) . . ?
C9 O3 Dy1 123.2(3) . 3_676 ?
Dy1 O3 Dy1 113.63(15) . 3_676 ?
C13 O4 Dy1 138.3(4) . . ?
C15 O5 Dy1 136.3(4) . . ?
C8 N1 N2 113.2(5) . . ?
C8 N1 Dy1 128.2(4) . . ?
N2 N1 Dy1 118.3(3) . . ?
C9 N2 N1 109.6(5) . . ?
C10 N3 C11 110.8(6) . . ?
C10 N3 C12 109.7(5) . . ?
C11 N3 C12 109.8(6) . . ?
C10 N3 Dy1 108.1(4) . 3_676 ?
C11 N3 Dy1 109.5(4) . 3_676 ?
C12 N3 Dy1 108.9(4) . 3_676 ?
O1 C1 C6 124.1(5) . . ?
O1 C1 C2 119.2(6) . . ?
C6 C1 C2 116.7(5) . . ?
C3 C2 O2 125.7(6) . . ?
C3 C2 C1 121.2(6) . . ?
O2 C2 C1 113.0(5) . . ?
C2 C3 C4 121.0(6) . . ?
C5 C4 C3 120.1(7) . . ?
C4 C5 C6 120.3(7) . . ?
C1 C6 C5 120.5(6) . . ?
C1 C6 C8 122.9(5) . . ?
C5 C6 C8 116.4(6) . . ?
N1 C8 C6 123.4(6) . . ?
N2 C9 O3 125.6(5) . . ?
N2 C9 C10 118.3(5) . . ?
O3 C9 C10 116.0(5) . . ?
N3 C10 C9 111.7(5) . . ?
O4 C13 C14 124.4(6) . . ?
O4 C13 C16 115.8(7) . . ?
C14 C13 C16 119.8(7) . . ?
C13 C14 C15 123.6(6) . . ?
O5 C15 C14 124.1(6) . . ?
O5 C15 C17 116.4(6) . . ?
C14 C15 C17 119.5(6) . . ?
O7 C18 C19 111.2(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 N2 C9 -172.6(6) . . . . ?
Dy1 N1 N2 C9 12.4(7) . . . . ?
Dy1 O1 C1 C6 41.3(9) . . . . ?
Dy1 O1 C1 C2 -140.4(5) . . . . ?
C7 O2 C2 C3 12.5(11) . . . . ?
C7 O2 C2 C1 -167.3(7) . . . . ?
O1 C1 C2 C3 177.5(7) . . . . ?
C6 C1 C2 C3 -4.1(11) . . . . ?
O1 C1 C2 O2 -2.7(9) . . . . ?
C6 C1 C2 O2 175.7(6) . . . . ?
O2 C2 C3 C4 -177.6(8) . . . . ?
C1 C2 C3 C4 2.2(13) . . . . ?
C2 C3 C4 C5 1.9(14) . . . . ?
C3 C4 C5 C6 -4.0(14) . . . . ?
O1 C1 C6 C5 -179.6(7) . . . . ?
C2 C1 C6 C5 2.0(10) . . . . ?
O1 C1 C6 C8 5.9(11) . . . . ?
C2 C1 C6 C8 -172.4(6) . . . . ?
C4 C5 C6 C1 1.9(12) . . . . ?
C4 C5 C6 C8 176.7(8) . . . . ?
N2 N1 C8 C6 173.9(6) . . . . ?
Dy1 N1 C8 C6 -11.8(10) . . . . ?
C1 C6 C8 N1 -19.4(11) . . . . ?
C5 C6 C8 N1 166.0(7) . . . . ?
N1 N2 C9 O3 3.9(9) . . . . ?
N1 N2 C9 C10 -174.1(6) . . . . ?
Dy1 O3 C9 N2 -19.1(8) . . . . ?
Dy1 O3 C9 N2 -172.6(5) 3_676 . . . ?
Dy1 O3 C9 C10 158.9(4) . . . . ?
Dy1 O3 C9 C10 5.4(7) 3_676 . . . ?
C11 N3 C10 C9 -162.6(6) . . . . ?
C12 N3 C10 C9 76.1(7) . . . . ?
Dy1 N3 C10 C9 -42.5(6) 3_676 . . . ?
N2 C9 C10 N3 -154.2(6) . . . . ?
O3 C9 C10 N3 27.6(8) . . . . ?
Dy1 O4 C13 C14 -19.5(12) . . . . ?
Dy1 O4 C13 C16 160.9(6) . . . . ?
O4 C13 C14 C15 4.3(12) . . . . ?
C16 C13 C14 C15 -176.1(7) . . . . ?
Dy1 O5 C15 C14 1.7(11) . . . . ?
Dy1 O5 C15 C17 -178.2(5) . . . . ?
C13 C14 C15 O5 3.7(12) . . . . ?
C13 C14 C15 C17 -176.4(7) . . . . ?

_refine_diff_density_max         2.207
_refine_diff_density_min         -1.308
_refine_diff_density_rms         0.151

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mm424
_database_code_depnum_ccdc_archive 'CCDC 1426601'
_audit_update_record             
;
2015-09-22 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        3
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H60 Ho2 N6 O14'
_chemical_formula_weight         1154.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ho Ho -0.2175 4.6783 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.2891(8)
_cell_length_b                   8.3607(6)
_cell_length_c                   20.7052(15)
_cell_angle_alpha                90
_cell_angle_beta                 102.908(4)
_cell_angle_gamma                90
_cell_volume                     2242.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    7947
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      28.38

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    3.572
_shelx_estimated_absorpt_T_min   0.695
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4817
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'

_exptl_special_details           
; 
 Data collection is performed with three batch runs at phi = 0.00 deg 
 (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg 
 (650 frames). 
 Frame width = 0.30 deg in omega. 
 Data is merged, corrected for decay (if any), and treated with multi-scan 
 absorption corrections (if required). All symmetry-equivalent reflections 
 are merged for centrosymmetric data. 
 Friedel pairs are not merged for noncentrosymmetric data. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29357
_diffrn_reflns_av_unetI/netI     0.0935
_diffrn_reflns_av_R_equivalents  0.1324
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.572
_diffrn_reflns_theta_max         28.389
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             5476
_reflns_number_gt                3951
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5476
_refine_ls_number_parameters     271
_refine_ls_number_restraints     408
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ho1 Ho 0.36536(2) 0.97187(3) 0.52461(2) 0.01608(9) Uani 1 1 d . U . . .
O1 O 0.2957(3) 0.9775(5) 0.6154(2) 0.0217(9) Uani 1 1 d . U . . .
O2 O 0.1457(4) 1.0823(6) 0.6667(2) 0.0321(11) Uani 1 1 d . U . . .
O3 O 0.5326(3) 0.8747(5) 0.5352(2) 0.0188(9) Uani 1 1 d . U . . .
O4 O 0.3515(3) 0.8259(5) 0.4253(2) 0.0239(10) Uani 1 1 d . U . . .
O5 O 0.1984(3) 0.8861(6) 0.4899(2) 0.0287(10) Uani 1 1 d . U . . .
O6 O 0.4559(3) 1.1650(5) 0.5957(2) 0.0249(10) Uani 1 1 d . U . . .
H6A H 0.4775 1.1772 0.6427 0.037 Uiso 1 1 d R U . . .
H6B H 0.5044 1.2232 0.5730 0.037 Uiso 1 1 d R U . . .
O7 O 0.3522(4) 1.2537(5) 0.6845(2) 0.0331(12) Uani 1 1 d . U . . .
H7D H 0.3112 1.1785 0.6704 0.040 Uiso 1 1 calc R U . . .
N1 N 0.4002(4) 0.7145(6) 0.5805(3) 0.0208(11) Uani 1 1 d . U . . .
N2 N 0.4898(4) 0.6294(6) 0.5734(3) 0.0222(11) Uani 1 1 d . U . . .
N3 N 0.7238(4) 0.7743(6) 0.5320(3) 0.0238(11) Uani 1 1 d . U . . .
C1 C 0.2366(4) 0.8687(7) 0.6339(3) 0.0194(12) Uani 1 1 d . U . . .
C2 C 0.1523(5) 0.9207(8) 0.6611(3) 0.0258(14) Uani 1 1 d . U . . .
C3 C 0.0860(5) 0.8125(9) 0.6793(4) 0.0339(17) Uani 1 1 d . U . . .
H3A H 0.0282 0.8498 0.6950 0.041 Uiso 1 1 calc R U . . .
C4 C 0.1026(6) 0.6481(9) 0.6750(4) 0.0415(19) Uani 1 1 d . U . . .
H4A H 0.0563 0.5743 0.6879 0.050 Uiso 1 1 calc R U . . .
C5 C 0.1850(5) 0.5937(9) 0.6524(4) 0.0333(17) Uani 1 1 d . U . . .
H5A H 0.1976 0.4820 0.6510 0.040 Uiso 1 1 calc R U . . .
C6 C 0.2521(5) 0.7037(7) 0.6307(3) 0.0208(13) Uani 1 1 d . U . . .
C7 C 0.0767(6) 1.1430(10) 0.7050(4) 0.043(2) Uani 1 1 d . U . . .
H7A H 0.0783 1.2601 0.7048 0.064 Uiso 1 1 calc R U . . .
H7B H 0.0982 1.1041 0.7507 0.064 Uiso 1 1 calc R U . . .
H7C H 0.0064 1.1060 0.6858 0.064 Uiso 1 1 calc R U . . .
C8 C 0.3442(5) 0.6366(8) 0.6129(3) 0.0224(13) Uani 1 1 d . U . . .
H8A H 0.3635 0.5300 0.6261 0.027 Uiso 1 1 calc R U . . .
C9 C 0.5493(4) 0.7229(7) 0.5490(3) 0.0185(12) Uani 1 1 d . U . . .
C10 C 0.6438(5) 0.6508(7) 0.5309(3) 0.0231(13) Uani 1 1 d . U . . .
H10A H 0.6719 0.5649 0.5628 0.028 Uiso 1 1 calc R U . . .
H10B H 0.6243 0.6026 0.4862 0.028 Uiso 1 1 calc R U . . .
C11 C 0.7753(5) 0.8103(9) 0.6012(4) 0.0367(16) Uani 1 1 d . U . . .
H11A H 0.7241 0.8494 0.6249 0.055 Uiso 1 1 calc R U . . .
H11B H 0.8281 0.8925 0.6019 0.055 Uiso 1 1 calc R U . . .
H11C H 0.8077 0.7130 0.6226 0.055 Uiso 1 1 calc R U . . .
C12 C 0.8002(5) 0.7152(9) 0.4960(4) 0.0371(18) Uani 1 1 d . U . . .
H12A H 0.7657 0.6917 0.4500 0.056 Uiso 1 1 calc R U . . .
H12B H 0.8325 0.6176 0.5173 0.056 Uiso 1 1 calc R U . . .
H12C H 0.8532 0.7970 0.4967 0.056 Uiso 1 1 calc R U . . .
C13 C 0.2835(5) 0.7411(7) 0.3880(3) 0.0241(13) Uani 1 1 d . U . . .
C14 C 0.1859(5) 0.7129(8) 0.3991(3) 0.0273(14) Uani 1 1 d . U . . .
H14A H 0.1417 0.6413 0.3702 0.033 Uiso 1 1 calc R U . . .
C15 C 0.1490(5) 0.7840(8) 0.4504(4) 0.0278(14) Uani 1 1 d . U . . .
C16 C 0.3141(6) 0.6622(9) 0.3295(3) 0.0340(16) Uani 1 1 d . U . . .
H16A H 0.3847 0.6935 0.3283 0.051 Uiso 1 1 calc R U . . .
H16B H 0.2667 0.6962 0.2884 0.051 Uiso 1 1 calc R U . . .
H16C H 0.3106 0.5457 0.3338 0.051 Uiso 1 1 calc R U . . .
C17 C 0.0448(6) 0.7381(10) 0.4615(4) 0.043(2) Uani 1 1 d . U . . .
H17A H 0.0305 0.7996 0.4987 0.064 Uiso 1 1 calc R U . . .
H17B H 0.0441 0.6236 0.4714 0.064 Uiso 1 1 calc R U . . .
H17C H -0.0082 0.7614 0.4214 0.064 Uiso 1 1 calc R U . . .
C18 C 0.3680(7) 1.2630(10) 0.7534(4) 0.047(2) Uani 1 1 d . U . . .
H18A H 0.4001 1.1628 0.7736 0.056 Uiso 1 1 calc R U . . .
H18B H 0.3007 1.2757 0.7659 0.056 Uiso 1 1 calc R U . . .
C19 C 0.4353(7) 1.3997(11) 0.7788(4) 0.056(2) Uani 1 1 d . U . . .
H19A H 0.4469 1.4033 0.8273 0.083 Uiso 1 1 calc R U . . .
H19B H 0.4022 1.4992 0.7601 0.083 Uiso 1 1 calc R U . . .
H19C H 0.5016 1.3874 0.7661 0.083 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ho1 O1 2.274(4) . ?
Ho1 O5 2.290(4) . ?
Ho1 O3 2.330(4) . ?
Ho1 O6 2.331(4) . ?
Ho1 O4 2.363(4) . ?
Ho1 O3 2.402(4) 3_676 ?
Ho1 N1 2.438(5) . ?
Ho1 N3 2.580(5) 3_676 ?
Ho1 Ho1 3.9618(5) 3_676 ?
O1 C1 1.313(7) . ?
O2 C2 1.360(9) . ?
O2 C7 1.434(7) . ?
O3 C9 1.308(7) . ?
O3 Ho1 2.402(4) 3_676 ?
O4 C13 1.266(8) . ?
O5 C15 1.261(8) . ?
O7 C18 1.397(9) . ?
N1 C8 1.286(7) . ?
N1 N2 1.422(6) . ?
N2 C9 1.294(7) . ?
N3 C12 1.472(7) . ?
N3 C11 1.474(9) . ?
N3 C10 1.479(7) . ?
N3 Ho1 2.580(5) 3_676 ?
C1 C6 1.398(8) . ?
C1 C2 1.430(8) . ?
C2 C3 1.373(9) . ?
C3 C4 1.398(10) . ?
C4 C5 1.362(9) . ?
C5 C6 1.422(8) . ?
C6 C8 1.466(8) . ?
C9 C10 1.513(8) . ?
C13 C14 1.387(8) . ?
C13 C16 1.514(9) . ?
C14 C15 1.399(9) . ?
C15 C17 1.503(9) . ?
C18 C19 1.474(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ho1 O5 73.79(15) . . ?
O1 Ho1 O3 119.04(15) . . ?
O5 Ho1 O3 139.24(16) . . ?
O1 Ho1 O6 73.22(14) . . ?
O5 Ho1 O6 137.95(15) . . ?
O3 Ho1 O6 80.53(14) . . ?
O1 Ho1 O4 139.75(14) . . ?
O5 Ho1 O4 71.55(14) . . ?
O3 Ho1 O4 77.82(14) . . ?
O6 Ho1 O4 146.78(13) . . ?
O1 Ho1 O3 142.76(14) . 3_676 ?
O5 Ho1 O3 128.67(16) . 3_676 ?
O3 Ho1 O3 66.31(17) . 3_676 ?
O6 Ho1 O3 71.59(14) . 3_676 ?
O4 Ho1 O3 76.73(14) . 3_676 ?
O1 Ho1 N1 72.26(15) . . ?
O5 Ho1 N1 86.60(17) . . ?
O3 Ho1 N1 64.62(14) . . ?
O6 Ho1 N1 107.17(17) . . ?
O4 Ho1 N1 85.81(16) . . ?
O3 Ho1 N1 130.29(14) 3_676 . ?
O1 Ho1 N3 97.33(15) . 3_676 ?
O5 Ho1 N3 78.48(16) . 3_676 ?
O3 Ho1 N3 131.39(14) . 3_676 ?
O6 Ho1 N3 80.61(17) . 3_676 ?
O4 Ho1 N3 95.22(17) . 3_676 ?
O3 Ho1 N3 65.28(14) 3_676 3_676 ?
N1 Ho1 N3 163.84(15) . 3_676 ?
O1 Ho1 Ho1 140.19(11) . 3_676 ?
O5 Ho1 Ho1 145.52(11) . 3_676 ?
O3 Ho1 Ho1 33.73(9) . 3_676 ?
O6 Ho1 Ho1 73.25(9) . 3_676 ?
O4 Ho1 Ho1 74.74(9) . 3_676 ?
O3 Ho1 Ho1 32.59(10) 3_676 3_676 ?
N1 Ho1 Ho1 98.05(11) . 3_676 ?
N3 Ho1 Ho1 97.77(10) 3_676 3_676 ?
C1 O1 Ho1 127.4(4) . . ?
C2 O2 C7 117.3(5) . . ?
C9 O3 Ho1 118.1(3) . . ?
C9 O3 Ho1 122.8(3) . 3_676 ?
Ho1 O3 Ho1 113.69(17) . 3_676 ?
C13 O4 Ho1 136.6(4) . . ?
C15 O5 Ho1 138.0(4) . . ?
C8 N1 N2 113.3(5) . . ?
C8 N1 Ho1 128.6(4) . . ?
N2 N1 Ho1 117.9(3) . . ?
C9 N2 N1 109.7(5) . . ?
C12 N3 C11 109.8(5) . . ?
C12 N3 C10 109.4(5) . . ?
C11 N3 C10 109.4(5) . . ?
C12 N3 Ho1 110.2(4) . 3_676 ?
C11 N3 Ho1 109.9(4) . 3_676 ?
C10 N3 Ho1 108.2(4) . 3_676 ?
O1 C1 C6 124.4(5) . . ?
O1 C1 C2 118.5(5) . . ?
C6 C1 C2 117.1(5) . . ?
O2 C2 C3 125.0(5) . . ?
O2 C2 C1 114.0(5) . . ?
C3 C2 C1 121.0(6) . . ?
C2 C3 C4 120.7(6) . . ?
C5 C4 C3 120.0(6) . . ?
C4 C5 C6 120.1(7) . . ?
C1 C6 C5 120.9(5) . . ?
C1 C6 C8 122.0(5) . . ?
C5 C6 C8 116.7(6) . . ?
N1 C8 C6 123.4(6) . . ?
N2 C9 O3 125.6(5) . . ?
N2 C9 C10 118.0(5) . . ?
O3 C9 C10 116.3(5) . . ?
N3 C10 C9 110.6(5) . . ?
O4 C13 C14 124.1(6) . . ?
O4 C13 C16 116.7(5) . . ?
C14 C13 C16 119.1(6) . . ?
C13 C14 C15 123.6(6) . . ?
O5 C15 C14 124.1(6) . . ?
O5 C15 C17 116.0(6) . . ?
C14 C15 C17 119.9(7) . . ?
O7 C18 C19 110.4(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 N2 C9 -170.9(6) . . . . ?
Ho1 N1 N2 C9 13.6(6) . . . . ?
Ho1 O1 C1 C6 41.0(8) . . . . ?
Ho1 O1 C1 C2 -140.9(5) . . . . ?
C7 O2 C2 C3 11.9(10) . . . . ?
C7 O2 C2 C1 -168.1(6) . . . . ?
O1 C1 C2 O2 -2.1(9) . . . . ?
C6 C1 C2 O2 176.0(6) . . . . ?
O1 C1 C2 C3 177.9(6) . . . . ?
C6 C1 C2 C3 -4.0(10) . . . . ?
O2 C2 C3 C4 -176.5(7) . . . . ?
C1 C2 C3 C4 3.5(11) . . . . ?
C2 C3 C4 C5 -0.2(12) . . . . ?
C3 C4 C5 C6 -2.3(12) . . . . ?
O1 C1 C6 C5 179.4(6) . . . . ?
C2 C1 C6 C5 1.4(10) . . . . ?
O1 C1 C6 C8 7.1(10) . . . . ?
C2 C1 C6 C8 -171.0(6) . . . . ?
C4 C5 C6 C1 1.7(11) . . . . ?
C4 C5 C6 C8 174.5(7) . . . . ?
N2 N1 C8 C6 175.5(6) . . . . ?
Ho1 N1 C8 C6 -9.6(10) . . . . ?
C1 C6 C8 N1 -21.7(10) . . . . ?
C5 C6 C8 N1 165.6(7) . . . . ?
N1 N2 C9 O3 2.6(9) . . . . ?
N1 N2 C9 C10 -173.9(5) . . . . ?
Ho1 O3 C9 N2 -18.4(8) . . . . ?
Ho1 O3 C9 N2 -170.8(5) 3_676 . . . ?
Ho1 O3 C9 C10 158.1(4) . . . . ?
Ho1 O3 C9 C10 5.7(7) 3_676 . . . ?
C12 N3 C10 C9 -163.3(6) . . . . ?
C11 N3 C10 C9 76.4(6) . . . . ?
Ho1 N3 C10 C9 -43.2(6) 3_676 . . . ?
N2 C9 C10 N3 -155.5(6) . . . . ?
O3 C9 C10 N3 27.7(8) . . . . ?
Ho1 O4 C13 C14 1.0(11) . . . . ?
Ho1 O4 C13 C16 -176.7(4) . . . . ?
O4 C13 C14 C15 4.5(11) . . . . ?
C16 C13 C14 C15 -177.8(7) . . . . ?
Ho1 O5 C15 C14 -18.5(12) . . . . ?
Ho1 O5 C15 C17 160.8(5) . . . . ?
C13 C14 C15 O5 3.4(11) . . . . ?
C13 C14 C15 C17 -176.0(7) . . . . ?

_refine_diff_density_max         3.222
_refine_diff_density_min         -1.352
_refine_diff_density_rms         0.219

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mm377_5
_database_code_depnum_ccdc_archive 'CCDC 1426602'
_audit_update_record             
;
2015-09-22 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        4
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H30 Er N3 O7'
_chemical_formula_weight         579.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5864(6)
_cell_length_b                   10.3618(8)
_cell_length_c                   13.2646(9)
_cell_angle_alpha                74.961(3)
_cell_angle_beta                 86.219(3)
_cell_angle_gamma                78.632(3)
_cell_volume                     1117.24(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9988
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      28.31

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_F_000             578
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.799
_shelx_estimated_absorpt_T_min   0.582
_shelx_estimated_absorpt_T_max   0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.495207
_exptl_absorpt_correction_T_max  0.745688
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'

_exptl_special_details           
; 
 Data collection is performed with four batch runs at phi = 0.00 deg 
 (600 frames), at phi = 90.00 deg (600 frames), at phi = 180.00 deg 
 (600 frames), and at phi = 270.00 deg (600 frames). 
 A fifth batch run is collected at phi = 0.00 deg (50 frames) to monitor 
 crystal and diffractometer stability. Frame width = 0.30 deg in omega. 
 Data is merged, corrected for decay (if any), and treated with multi-scan 
 absorption corrections (if required). All symmetry-equivalent reflections 
 are merged for centrosymmetric data. 
 Friedel pairs are not merged for noncentrosymmetric data. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8337
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.072
_diffrn_reflns_theta_max         28.307
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             5396
_reflns_number_gt                5125
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'

_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+4.5175P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5396
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Er1 Er 0.45118(3) 0.54272(2) 0.13576(2) 0.01733(8) Uani 1 1 d . . . . .
O1 O 0.4063(5) 0.7231(4) 0.2052(3) 0.0233(8) Uani 1 1 d . . . . .
O2 O 0.4769(6) 0.8259(5) 0.3512(4) 0.0361(11) Uani 1 1 d . . . . .
O3 O 0.3629(4) 0.5690(4) -0.0306(3) 0.0196(7) Uani 1 1 d . . . . .
O4 O 0.3816(5) 0.4622(4) 0.3063(3) 0.0286(9) Uani 1 1 d . . . . .
O5 O 0.3512(5) 0.3419(4) 0.1512(3) 0.0247(8) Uani 1 1 d . . . . .
O6 O 0.5954(5) 0.7011(4) 0.0386(3) 0.0299(9) Uani 1 1 d . . . . .
H6A H 0.6313 0.6874 -0.0282 0.045 Uiso 1 1 d R U . . .
H6B H 0.5615 0.8008 0.0342 0.045 Uiso 1 1 d R U . . .
O7 O 0.6671(6) 0.8517(6) 0.1566(5) 0.0461(13) Uani 1 1 d . . . . .
H7D H 0.7462 0.8181 0.1248 0.069 Uiso 1 1 calc R U . . .
N1 N 0.1740(5) 0.6480(5) 0.1062(4) 0.0229(9) Uani 1 1 d . . . . .
N2 N 0.1010(5) 0.6336(5) 0.0188(4) 0.0228(9) Uani 1 1 d . . . . .
N3 N 0.2805(6) 0.5705(5) -0.2221(4) 0.0257(10) Uani 1 1 d . . . . .
C1 C 0.2889(7) 0.7588(5) 0.2649(4) 0.0217(10) Uani 1 1 d . . . . .
C2 C 0.3191(7) 0.8154(6) 0.3472(5) 0.0261(11) Uani 1 1 d . . . . .
C3 C 0.2017(8) 0.8573(7) 0.4140(5) 0.0361(14) Uani 1 1 d . . . . .
H3A H 0.2272 0.8919 0.4693 0.043 Uiso 1 1 calc R U . . .
C4 C 0.0444(8) 0.8482(7) 0.3996(6) 0.0365(15) Uani 1 1 d . . . . .
H4A H -0.0373 0.8764 0.4455 0.044 Uiso 1 1 calc R U . . .
C5 C 0.0083(7) 0.7990(7) 0.3196(5) 0.0310(13) Uani 1 1 d . . . . .
H5A H -0.0991 0.7951 0.3097 0.037 Uiso 1 1 calc R U . . .
C6 C 0.1279(7) 0.7537(6) 0.2511(4) 0.0238(11) Uani 1 1 d . . . . .
C7 C 0.5134(9) 0.9019(9) 0.4191(7) 0.0449(18) Uani 1 1 d . . . . .
H7A H 0.6278 0.9015 0.4159 0.067 Uiso 1 1 calc R U . . .
H7B H 0.4820 0.8607 0.4908 0.067 Uiso 1 1 calc R U . . .
H7C H 0.4554 0.9958 0.3973 0.067 Uiso 1 1 calc R U . . .
C8 C 0.0783(7) 0.7125(6) 0.1633(5) 0.0244(11) Uani 1 1 d . . . . .
H8A H -0.0314 0.7346 0.1471 0.029 Uiso 1 1 calc R U . . .
C9 C 0.2090(6) 0.5908(5) -0.0445(4) 0.0196(10) Uani 1 1 d . . . . .
C10 C 0.1567(6) 0.5565(6) -0.1391(5) 0.0257(11) Uani 1 1 d . . . . .
H10A H 0.1372 0.4620 -0.1198 0.031 Uiso 1 1 calc R U . . .
H10B H 0.0562 0.6183 -0.1652 0.031 Uiso 1 1 calc R U . . .
C11 C 0.2812(9) 0.7157(7) -0.2687(6) 0.0369(14) Uani 1 1 d . . . . .
H11A H 0.3634 0.7250 -0.3235 0.055 Uiso 1 1 calc R U . . .
H11B H 0.3035 0.7582 -0.2146 0.055 Uiso 1 1 calc R U . . .
H11C H 0.1772 0.7604 -0.2988 0.055 Uiso 1 1 calc R U . . .
C12 C 0.2460(8) 0.5056(8) -0.3033(6) 0.0396(16) Uani 1 1 d . . . . .
H12A H 0.3283 0.5138 -0.3581 0.059 Uiso 1 1 calc R U . . .
H12B H 0.1422 0.5508 -0.3336 0.059 Uiso 1 1 calc R U . . .
H12C H 0.2445 0.4092 -0.2717 0.059 Uiso 1 1 calc R U . . .
C13 C 0.2836(7) 0.3909(6) 0.3550(5) 0.0263(11) Uani 1 1 d . . . . .
C14 C 0.2270(7) 0.2957(6) 0.3164(5) 0.0289(12) Uani 1 1 d . . . . .
H14A H 0.1578 0.2432 0.3600 0.035 Uiso 1 1 calc R U . . .
C15 C 0.2659(7) 0.2729(6) 0.2177(5) 0.0244(11) Uani 1 1 d . . . . .
C16 C 0.2285(10) 0.4127(8) 0.4599(6) 0.0437(17) Uani 1 1 d . . . . .
H16A H 0.2789 0.4827 0.4747 0.066 Uiso 1 1 calc R U . . .
H16B H 0.2577 0.3274 0.5136 0.066 Uiso 1 1 calc R U . . .
H16C H 0.1128 0.4422 0.4601 0.066 Uiso 1 1 calc R U . . .
C17 C 0.2042(8) 0.1641(6) 0.1851(5) 0.0320(13) Uani 1 1 d . . . . .
H17A H 0.2404 0.1632 0.1137 0.048 Uiso 1 1 calc R U . . .
H17B H 0.0878 0.1828 0.1881 0.048 Uiso 1 1 calc R U . . .
H17C H 0.2441 0.0755 0.2324 0.048 Uiso 1 1 calc R U . . .
C18 C 0.6533(12) 0.9928(8) 0.1321(8) 0.059(2) Uani 1 1 d . . . . .
H18A H 0.6610 1.0219 0.1967 0.071 Uiso 1 1 calc R U . . .
H18B H 0.5477 1.0363 0.1017 0.071 Uiso 1 1 calc R U . . .
C19 C 0.7777(13) 1.0384(9) 0.0576(9) 0.065(3) Uani 1 1 d . . . . .
H19A H 0.7656 1.1375 0.0428 0.097 Uiso 1 1 calc R U . . .
H19B H 0.7682 1.0123 -0.0073 0.097 Uiso 1 1 calc R U . . .
H19C H 0.8823 0.9957 0.0876 0.097 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Er1 O1 2.248(4) . ?
Er1 O4 2.282(4) . ?
Er1 O3 2.312(4) . ?
Er1 O6 2.319(4) . ?
Er1 O5 2.360(4) . ?
Er1 O3 2.376(4) 2_665 ?
Er1 N1 2.426(5) . ?
Er1 N3 2.566(5) 2_665 ?
Er1 Er1 3.9270(5) 2_665 ?
O1 C1 1.296(7) . ?
O2 C2 1.385(7) . ?
O2 C7 1.426(8) . ?
O3 C9 1.313(6) . ?
O3 Er1 2.376(4) 2_665 ?
O4 C13 1.264(7) . ?
O5 C15 1.272(7) . ?
O7 C18 1.396(9) . ?
N1 C8 1.289(7) . ?
N1 N2 1.407(6) . ?
N2 C9 1.300(7) . ?
N3 C11 1.472(8) . ?
N3 C10 1.479(7) . ?
N3 C12 1.481(8) . ?
N3 Er1 2.566(5) 2_665 ?
C1 C6 1.419(8) . ?
C1 C2 1.426(8) . ?
C2 C3 1.378(8) . ?
C3 C4 1.401(10) . ?
C4 C5 1.367(9) . ?
C5 C6 1.418(8) . ?
C6 C8 1.454(8) . ?
C9 C10 1.507(8) . ?
C13 C14 1.398(9) . ?
C13 C16 1.499(9) . ?
C14 C15 1.398(8) . ?
C15 C17 1.502(8) . ?
C18 C19 1.469(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Er1 O4 74.16(15) . . ?
O1 Er1 O3 119.09(14) . . ?
O4 Er1 O3 140.34(14) . . ?
O1 Er1 O6 72.01(15) . . ?
O4 Er1 O6 138.14(15) . . ?
O3 Er1 O6 78.97(15) . . ?
O1 Er1 O5 138.66(14) . . ?
O4 Er1 O5 71.62(15) . . ?
O3 Er1 O5 77.11(14) . . ?
O6 Er1 O5 148.27(14) . . ?
O1 Er1 O3 141.95(13) . 2_665 ?
O4 Er1 O3 128.18(15) . 2_665 ?
O3 Er1 O3 66.24(15) . 2_665 ?
O6 Er1 O3 72.56(14) . 2_665 ?
O5 Er1 O3 78.86(13) . 2_665 ?
O1 Er1 N1 73.26(15) . . ?
O4 Er1 N1 87.19(16) . . ?
O3 Er1 N1 64.79(15) . . ?
O6 Er1 N1 105.64(17) . . ?
O5 Er1 N1 82.52(15) . . ?
O3 Er1 N1 130.27(15) 2_665 . ?
O1 Er1 N3 96.97(15) . 2_665 ?
O4 Er1 N3 77.01(16) . 2_665 ?
O3 Er1 N3 131.55(14) . 2_665 ?
O6 Er1 N3 83.34(17) . 2_665 ?
O5 Er1 N3 97.26(16) . 2_665 ?
O3 Er1 N3 65.47(14) 2_665 2_665 ?
N1 Er1 N3 163.33(16) . 2_665 ?
O1 Er1 Er1 139.71(11) . 2_665 ?
O4 Er1 Er1 145.83(11) . 2_665 ?
O3 Er1 Er1 33.63(9) . 2_665 ?
O6 Er1 Er1 72.90(10) . 2_665 ?
O5 Er1 Er1 75.62(10) . 2_665 ?
O3 Er1 Er1 32.61(9) 2_665 2_665 ?
N1 Er1 Er1 98.07(12) . 2_665 ?
N3 Er1 Er1 98.01(11) 2_665 2_665 ?
C1 O1 Er1 128.1(3) . . ?
C2 O2 C7 116.9(5) . . ?
C9 O3 Er1 118.0(3) . . ?
C9 O3 Er1 122.3(3) . 2_665 ?
Er1 O3 Er1 113.76(15) . 2_665 ?
C13 O4 Er1 136.2(4) . . ?
C15 O5 Er1 135.6(4) . . ?
C8 N1 N2 113.4(5) . . ?
C8 N1 Er1 128.5(4) . . ?
N2 N1 Er1 118.0(3) . . ?
C9 N2 N1 109.7(4) . . ?
C11 N3 C10 109.4(5) . . ?
C11 N3 C12 109.8(6) . . ?
C10 N3 C12 109.2(5) . . ?
C11 N3 Er1 109.1(4) . 2_665 ?
C10 N3 Er1 107.3(3) . 2_665 ?
C12 N3 Er1 112.0(4) . 2_665 ?
O1 C1 C6 124.9(5) . . ?
O1 C1 C2 118.7(5) . . ?
C6 C1 C2 116.3(5) . . ?
C3 C2 O2 124.1(5) . . ?
C3 C2 C1 122.8(6) . . ?
O2 C2 C1 113.0(5) . . ?
C2 C3 C4 119.3(6) . . ?
C5 C4 C3 120.1(6) . . ?
C4 C5 C6 121.3(6) . . ?
C5 C6 C1 120.0(5) . . ?
C5 C6 C8 117.9(5) . . ?
C1 C6 C8 121.9(5) . . ?
N1 C8 C6 124.1(5) . . ?
N2 C9 O3 125.0(5) . . ?
N2 C9 C10 118.7(5) . . ?
O3 C9 C10 116.2(5) . . ?
N3 C10 C9 110.1(4) . . ?
O4 C13 C14 123.7(6) . . ?
O4 C13 C16 116.2(6) . . ?
C14 C13 C16 120.1(6) . . ?
C15 C14 C13 124.1(5) . . ?
O5 C15 C14 123.1(5) . . ?
O5 C15 C17 116.9(5) . . ?
C14 C15 C17 120.0(5) . . ?
O7 C18 C19 111.5(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 N2 C9 168.3(5) . . . . ?
Er1 N1 N2 C9 -14.7(6) . . . . ?
Er1 O1 C1 C6 -41.3(8) . . . . ?
Er1 O1 C1 C2 142.7(4) . . . . ?
C7 O2 C2 C3 -9.1(10) . . . . ?
C7 O2 C2 C1 169.7(6) . . . . ?
O1 C1 C2 C3 179.5(6) . . . . ?
C6 C1 C2 C3 3.1(9) . . . . ?
O1 C1 C2 O2 0.6(8) . . . . ?
C6 C1 C2 O2 -175.7(5) . . . . ?
O2 C2 C3 C4 176.8(7) . . . . ?
C1 C2 C3 C4 -1.9(11) . . . . ?
C2 C3 C4 C5 -0.3(11) . . . . ?
C3 C4 C5 C6 1.3(11) . . . . ?
C4 C5 C6 C1 0.0(10) . . . . ?
C4 C5 C6 C8 -175.4(6) . . . . ?
O1 C1 C6 C5 -178.2(6) . . . . ?
C2 C1 C6 C5 -2.1(8) . . . . ?
O1 C1 C6 C8 -3.0(9) . . . . ?
C2 C1 C6 C8 173.1(5) . . . . ?
N2 N1 C8 C6 -173.0(5) . . . . ?
Er1 N1 C8 C6 10.4(9) . . . . ?
C5 C6 C8 N1 -167.5(6) . . . . ?
C1 C6 C8 N1 17.1(9) . . . . ?
N1 N2 C9 O3 -2.1(8) . . . . ?
N1 N2 C9 C10 174.7(5) . . . . ?
Er1 O3 C9 N2 18.7(7) . . . . ?
Er1 O3 C9 N2 169.8(4) 2_665 . . . ?
Er1 O3 C9 C10 -158.1(4) . . . . ?
Er1 O3 C9 C10 -7.1(6) 2_665 . . . ?
C11 N3 C10 C9 -73.3(6) . . . . ?
C12 N3 C10 C9 166.5(5) . . . . ?
Er1 N3 C10 C9 44.9(5) 2_665 . . . ?
N2 C9 C10 N3 154.7(5) . . . . ?
O3 C9 C10 N3 -28.2(7) . . . . ?
Er1 O4 C13 C14 26.1(9) . . . . ?
Er1 O4 C13 C16 -154.0(5) . . . . ?
O4 C13 C14 C15 -3.2(10) . . . . ?
C16 C13 C14 C15 176.9(6) . . . . ?
Er1 O5 C15 C14 -10.7(9) . . . . ?
Er1 O5 C15 C17 168.3(4) . . . . ?
C13 C14 C15 O5 -3.5(10) . . . . ?
C13 C14 C15 C17 177.5(6) . . . . ?

_refine_diff_density_max         2.124
_refine_diff_density_min         -1.847
_refine_diff_density_rms         0.170

_shelxl_version_number           2013-4

