data_dym _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 Cl Dy N4 O2' _chemical_formula_weight 650.49 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' 'Cl' 'Cl' 0.1484 0.1585 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M C222(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.7031(5) _cell_length_b 17.1806(9) _cell_length_c 16.9926(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2540.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6202 _cell_measurement_theta_min 3.375 _cell_measurement_theta_max 27.515 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.701 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1292 _exptl_absorpt_coefficient_mu 3.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7482 _exptl_absorpt_correction_T_max 0.8867 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7078 _diffrn_reflns_av_R_equivalents 0.0612 _diffrn_reflns_av_sigmaI/netI 0.0756 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2805 _reflns_number_gt 2465 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0102P)^2^+1.6667P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00 _refine_ls_number_reflns 2805 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.0686 _refine_ls_wR_factor_gt 0.0653 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Dy1 Dy 0.5000 0.007389(16) 0.2500 0.01543(9) Uani 1 2 d S . . Cl1 Cl 0.5000 -0.14871(9) 0.2500 0.0325(4) Uani 1 2 d S . . O1 O 0.5971(4) 0.0355(2) 0.1361(2) 0.0211(9) Uani 1 1 d . . . N1 N 0.6622(5) 0.1309(3) 0.2763(3) 0.0180(11) Uani 1 1 d . . . N2 N 0.7549(5) -0.0186(3) 0.3229(3) 0.0216(11) Uani 1 1 d . . . C1 C 0.8280(7) -0.0869(4) 0.3284(4) 0.0283(15) Uani 1 1 d . . . H1 H 0.7820 -0.1311 0.3045 0.034 Uiso 1 1 calc R . . C2 C 0.9663(7) -0.0970(4) 0.3669(4) 0.0302(18) Uani 1 1 d . . . H2 H 1.0159 -0.1463 0.3676 0.036 Uiso 1 1 calc R . . C3 C 1.0307(7) -0.0332(4) 0.4043(4) 0.0315(18) Uani 1 1 d . . . H3 H 1.1245 -0.0380 0.4325 0.038 Uiso 1 1 calc R . . C4 C 0.9564(6) 0.0364(4) 0.3998(4) 0.0261(15) Uani 1 1 d . . . H4 H 0.9999 0.0810 0.4244 0.031 Uiso 1 1 calc R . . C5 C 0.8176(6) 0.0432(3) 0.3598(3) 0.0186(12) Uani 1 1 d . . . C6 C 0.7344(8) 0.1198(4) 0.3562(5) 0.0194(17) Uani 1 1 d . . . H6A H 0.8075 0.1627 0.3666 0.023 Uiso 1 1 calc R . . H6B H 0.6537 0.1212 0.3972 0.023 Uiso 1 1 calc R . . C7 C 0.5657(6) 0.2026(3) 0.2806(3) 0.0194(13) Uani 1 1 d . . . H7A H 0.6317 0.2488 0.2718 0.023 Uiso 1 1 calc R . . H7B H 0.5211 0.2069 0.3341 0.023 Uiso 1 1 calc R . . C8 C 0.7896(6) 0.1398(4) 0.2189(3) 0.0200(13) Uani 1 1 d . . . H8A H 0.8540 0.0923 0.2212 0.024 Uiso 1 1 calc R . . H8B H 0.8545 0.1840 0.2359 0.024 Uiso 1 1 calc R . . C9 C 0.7436(8) 0.1530(4) 0.1351(5) 0.0204(16) Uani 1 1 d . . . C10 C 0.7987(7) 0.2163(4) 0.0918(4) 0.0246(14) Uani 1 1 d . . . H10 H 0.8607 0.2543 0.1173 0.030 Uiso 1 1 calc R . . C11 C 0.7652(7) 0.2248(4) 0.0132(4) 0.0296(15) Uani 1 1 d . . . H11 H 0.8052 0.2678 -0.0153 0.036 Uiso 1 1 calc R . . C12 C 0.6740(7) 0.1712(4) -0.0240(4) 0.0273(15) Uani 1 1 d . . . H12 H 0.6491 0.1779 -0.0780 0.033 Uiso 1 1 calc R . . C13 C 0.6177(6) 0.1073(3) 0.0166(3) 0.0216(14) Uani 1 1 d . . . H13 H 0.5556 0.0704 -0.0103 0.026 Uiso 1 1 calc R . . C14 C 0.6506(6) 0.0961(3) 0.0958(4) 0.0214(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Dy1 0.01899(14) 0.00980(15) 0.01750(15) 0.000 -0.0004(3) 0.000 Cl1 0.0383(10) 0.0154(8) 0.0437(12) 0.000 -0.016(2) 0.000 O1 0.024(2) 0.019(2) 0.021(2) 0.0004(17) -0.0003(18) -0.0047(16) N1 0.024(2) 0.013(2) 0.017(3) 0.0040(16) 0.0062(19) 0.000(2) N2 0.024(2) 0.025(3) 0.016(2) -0.002(2) -0.002(2) -0.002(2) C1 0.033(4) 0.021(4) 0.031(4) -0.004(3) -0.001(3) 0.003(3) C2 0.027(5) 0.026(3) 0.038(4) 0.001(2) -0.003(3) 0.009(3) C3 0.024(5) 0.038(4) 0.033(3) 0.007(3) -0.006(3) 0.002(3) C4 0.026(4) 0.025(3) 0.027(3) 0.004(2) 0.001(2) -0.008(2) C5 0.022(3) 0.020(3) 0.014(3) 0.003(2) 0.004(3) -0.005(2) C6 0.021(3) 0.014(4) 0.023(4) 0.000(3) -0.005(3) 0.001(3) C7 0.022(3) 0.009(3) 0.027(3) -0.004(2) -0.002(2) -0.002(2) C8 0.015(3) 0.021(3) 0.023(3) 0.000(2) 0.001(2) 0.002(2) C9 0.018(3) 0.018(4) 0.025(4) -0.003(3) 0.004(3) 0.007(3) C10 0.028(3) 0.021(3) 0.025(4) -0.003(3) 0.004(3) -0.002(3) C11 0.033(3) 0.027(4) 0.028(4) 0.003(3) 0.010(3) -0.001(3) C12 0.030(3) 0.031(4) 0.020(3) 0.002(3) 0.001(3) 0.011(3) C13 0.023(3) 0.020(3) 0.022(4) -0.002(2) -0.002(3) 0.004(2) C14 0.018(3) 0.022(3) 0.024(3) -0.003(2) 0.005(3) 0.001(2) _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 2.166(4) . ? Dy1 O1 2.166(4) 3_655 ? Dy1 N2 2.579(4) 3_655 ? Dy1 N2 2.579(4) . ? Dy1 N1 2.587(5) . ? Dy1 N1 2.587(5) 3_655 ? Dy1 Cl1 2.6818(16) . ? O1 C14 1.331(7) . ? N1 C8 1.484(6) . ? N1 C7 1.493(7) . ? N1 C6 1.508(8) . ? N2 C1 1.338(7) . ? N2 C5 1.349(7) . ? C1 C2 1.381(8) . ? C1 H1 0.9500 . ? C2 C3 1.386(8) . ? C2 H2 0.9500 . ? C3 C4 1.362(8) . ? C3 H3 0.9500 . ? C4 C5 1.391(7) . ? C4 H4 0.9500 . ? C5 C6 1.503(9) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C7 1.547(10) 3_655 ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.497(9) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.398(10) . ? C9 C14 1.435(9) . ? C10 C11 1.375(9) . ? C10 H10 0.9500 . ? C11 C12 1.371(9) . ? C11 H11 0.9500 . ? C12 C13 1.386(9) . ? C12 H12 0.9500 . ? C13 C14 1.390(8) . ? C13 H13 0.9500 . ? 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 O1 154.3(2) . 3_655 ? O1 Dy1 N2 86.85(14) . 3_655 ? O1 Dy1 N2 97.59(14) 3_655 3_655 ? O1 Dy1 N2 97.59(14) . . ? O1 Dy1 N2 86.85(14) 3_655 . ? N2 Dy1 N2 160.0(2) 3_655 . ? O1 Dy1 N1 76.05(14) . . ? O1 Dy1 N1 82.87(14) 3_655 . ? N2 Dy1 N1 133.96(15) 3_655 . ? N2 Dy1 N1 65.80(15) . . ? O1 Dy1 N1 82.87(14) . 3_655 ? O1 Dy1 N1 76.05(14) 3_655 3_655 ? N2 Dy1 N1 65.80(15) 3_655 3_655 ? N2 Dy1 N1 133.96(15) . 3_655 ? N1 Dy1 N1 69.8(2) . 3_655 ? O1 Dy1 Cl1 102.86(11) . . ? O1 Dy1 Cl1 102.86(11) 3_655 . ? N2 Dy1 Cl1 80.02(11) 3_655 . ? N2 Dy1 Cl1 80.02(11) . . ? N1 Dy1 Cl1 145.10(10) . . ? N1 Dy1 Cl1 145.10(10) 3_655 . ? C14 O1 Dy1 140.4(4) . . ? C8 N1 C7 111.6(4) . . ? C8 N1 C6 107.0(4) . . ? C7 N1 C6 107.1(4) . . ? C8 N1 Dy1 112.2(3) . . ? C7 N1 Dy1 112.3(3) . . ? C6 N1 Dy1 106.2(4) . . ? C1 N2 C5 117.7(5) . . ? C1 N2 Dy1 126.5(4) . . ? C5 N2 Dy1 115.8(4) . . ? N2 C1 C2 123.9(6) . . ? N2 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C1 C2 C3 118.1(6) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C4 C3 C2 118.5(5) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C3 C4 C5 120.9(6) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? N2 C5 C4 120.8(6) . . ? N2 C5 C6 118.4(5) . . ? C4 C5 C6 120.8(5) . . ? C5 C6 N1 110.4(5) . . ? C5 C6 H6A 109.6 . . ? N1 C6 H6A 109.6 . . ? C5 C6 H6B 109.6 . . ? N1 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? N1 C7 C7 112.5(3) . 3_655 ? N1 C7 H7A 109.1 . . ? C7 C7 H7A 109.1 3_655 . ? N1 C7 H7B 109.1 . . ? C7 C7 H7B 109.1 3_655 . ? H7A C7 H7B 107.8 . . ? N1 C8 C9 116.1(5) . . ? N1 C8 H8A 108.3 . . ? C9 C8 H8A 108.3 . . ? N1 C8 H8B 108.3 . . ? C9 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? C10 C9 C14 118.6(7) . . ? C10 C9 C8 121.8(6) . . ? C14 C9 C8 119.4(6) . . ? C11 C10 C9 121.4(6) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C12 C11 C10 120.0(6) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 120.5(6) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C14 121.3(6) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? O1 C14 C13 122.3(5) . . ? O1 C14 C9 119.4(6) . . ? C13 C14 C9 118.2(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 O1 Dy1 O1 C14 10.4(5) 3_655 . . . ? N2 Dy1 O1 C14 111.4(6) 3_655 . . . ? N2 Dy1 O1 C14 -88.2(6) . . . . ? N1 Dy1 O1 C14 -25.5(6) . . . . ? N1 Dy1 O1 C14 45.4(6) 3_655 . . . ? Cl1 Dy1 O1 C14 -169.6(5) . . . . ? O1 Dy1 N1 C8 -25.7(3) . . . . ? O1 Dy1 N1 C8 169.2(3) 3_655 . . . ? N2 Dy1 N1 C8 -97.1(4) 3_655 . . . ? N2 Dy1 N1 C8 79.4(3) . . . . ? N1 Dy1 N1 C8 -113.1(4) 3_655 . . . ? Cl1 Dy1 N1 C8 66.9(4) . . . . ? O1 Dy1 N1 C7 101.0(3) . . . . ? O1 Dy1 N1 C7 -64.2(3) 3_655 . . . ? N2 Dy1 N1 C7 29.5(4) 3_655 . . . ? N2 Dy1 N1 C7 -153.9(4) . . . . ? N1 Dy1 N1 C7 13.5(2) 3_655 . . . ? Cl1 Dy1 N1 C7 -166.5(2) . . . . ? O1 Dy1 N1 C6 -142.3(4) . . . . ? O1 Dy1 N1 C6 52.6(4) 3_655 . . . ? N2 Dy1 N1 C6 146.3(3) 3_655 . . . ? N2 Dy1 N1 C6 -37.2(3) . . . . ? N1 Dy1 N1 C6 130.3(4) 3_655 . . . ? Cl1 Dy1 N1 C6 -49.7(4) . . . . ? O1 Dy1 N2 C1 -89.6(5) . . . . ? O1 Dy1 N2 C1 115.9(5) 3_655 . . . ? N2 Dy1 N2 C1 12.2(5) 3_655 . . . ? N1 Dy1 N2 C1 -160.5(5) . . . . ? N1 Dy1 N2 C1 -177.0(5) 3_655 . . . ? Cl1 Dy1 N2 C1 12.2(5) . . . . ? O1 Dy1 N2 C5 91.6(4) . . . . ? O1 Dy1 N2 C5 -63.0(4) 3_655 . . . ? N2 Dy1 N2 C5 -166.6(4) 3_655 . . . ? N1 Dy1 N2 C5 20.6(4) . . . . ? N1 Dy1 N2 C5 4.2(5) 3_655 . . . ? Cl1 Dy1 N2 C5 -166.6(4) . . . . ? C5 N2 C1 C2 -2.7(10) . . . . ? Dy1 N2 C1 C2 178.5(5) . . . . ? N2 C1 C2 C3 2.4(10) . . . . ? C1 C2 C3 C4 -1.5(10) . . . . ? C2 C3 C4 C5 1.1(9) . . . . ? C1 N2 C5 C4 2.1(8) . . . . ? Dy1 N2 C5 C4 -178.9(4) . . . . ? C1 N2 C5 C6 -178.2(6) . . . . ? Dy1 N2 C5 C6 0.8(7) . . . . ? C3 C4 C5 N2 -1.5(9) . . . . ? C3 C4 C5 C6 178.8(6) . . . . ? N2 C5 C6 N1 -37.7(8) . . . . ? C4 C5 C6 N1 142.0(5) . . . . ? C8 N1 C6 C5 -67.3(6) . . . . ? C7 N1 C6 C5 172.9(5) . . . . ? Dy1 N1 C6 C5 52.7(5) . . . . ? C8 N1 C7 C7 88.0(6) . . . 3_655 ? C6 N1 C7 C7 -155.2(5) . . . 3_655 ? Dy1 N1 C7 C7 -39.0(6) . . . 3_655 ? C7 N1 C8 C9 -62.1(7) . . . . ? C6 N1 C8 C9 -178.9(6) . . . . ? Dy1 N1 C8 C9 64.9(6) . . . . ? N1 C8 C9 C10 126.1(6) . . . . ? N1 C8 C9 C14 -59.1(8) . . . . ? C14 C9 C10 C11 0.2(9) . . . . ? C8 C9 C10 C11 175.0(6) . . . . ? C9 C10 C11 C12 1.0(10) . . . . ? C10 C11 C12 C13 -1.5(9) . . . . ? C11 C12 C13 C14 0.7(9) . . . . ? Dy1 O1 C14 C13 -138.6(5) . . . . ? Dy1 O1 C14 C9 40.4(8) . . . . ? C12 C13 C14 O1 179.6(6) . . . . ? C12 C13 C14 C9 0.6(9) . . . . ? C10 C9 C14 O1 180.0(5) . . . . ? C8 C9 C14 O1 5.1(9) . . . . ? C10 C9 C14 C13 -1.0(9) . . . . ? C8 C9 C14 C13 -175.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 1.058 _refine_diff_density_min -1.421 _refine_diff_density_rms 0.144 data_dym _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 Br Dy N4 O2' _chemical_formula_weight 694.95 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' 'Br' 'Br' -0.2901 2.4595 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M C222(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.7136(6) _cell_length_b 17.3862(13) _cell_length_c 17.0830(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2588.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5049 _cell_measurement_theta_min 3.345 _cell_measurement_theta_max 27.53 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.784 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1364 _exptl_absorpt_coefficient_mu 4.464 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4319 _exptl_absorpt_correction_T_max 0.5882 _exptl_absorpt_process_details '(ABSCOR; Higashi, 1995)' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS SPIDE IP' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5202 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2480 _reflns_number_gt 2358 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'PROCESS-AUTO (Rigaku, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0261P)^2^+5.8657P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00 _refine_ls_number_reflns 2480 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0289 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_ref 0.0675 _refine_ls_wR_factor_gt 0.0617 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Dy1 Dy 0.5000 0.009766(14) 0.2500 0.01481(9) Uani 1 2 d S . . Br1 Br 0.5000 -0.15424(3) 0.2500 0.02811(15) Uani 1 2 d S . . O1 O 0.5954(4) 0.03586(19) 0.13615(18) 0.0196(7) Uani 1 1 d . . . N1 N 0.6610(4) 0.1315(3) 0.2761(2) 0.0161(8) Uani 1 1 d . . . N2 N 0.7577(4) -0.0155(3) 0.3216(2) 0.0214(8) Uani 1 1 d . . . C1 C 0.8323(6) -0.0834(3) 0.3268(3) 0.0296(12) Uani 1 1 d . . . H1 H 0.7880 -0.1272 0.3024 0.036 Uiso 1 1 calc R . . C2 C 0.9706(5) -0.0922(3) 0.3661(3) 0.0302(14) Uani 1 1 d . . . H2 H 1.0212 -0.1406 0.3668 0.036 Uiso 1 1 calc R . . C3 C 1.0334(5) -0.0297(3) 0.4039(3) 0.0283(13) Uani 1 1 d . . . H3 H 1.1275 -0.0344 0.4316 0.034 Uiso 1 1 calc R . . C4 C 0.9571(5) 0.0398(3) 0.4007(3) 0.0233(11) Uani 1 1 d . . . H4 H 0.9974 0.0835 0.4270 0.028 Uiso 1 1 calc R . . C5 C 0.8200(5) 0.0452(3) 0.3586(2) 0.0180(9) Uani 1 1 d . . . C6 C 0.7337(6) 0.1204(4) 0.3542(3) 0.0202(12) Uani 1 1 d . . . H6A H 0.6534 0.1212 0.3952 0.024 Uiso 1 1 calc R . . H6B H 0.8054 0.1634 0.3646 0.024 Uiso 1 1 calc R . . C7 C 0.5650(5) 0.2026(3) 0.2795(3) 0.0191(9) Uani 1 1 d . . . H7A H 0.6312 0.2479 0.2699 0.023 Uiso 1 1 calc R . . H7B H 0.5214 0.2077 0.3328 0.023 Uiso 1 1 calc R . . C8 C 0.7887(5) 0.1404(3) 0.2177(3) 0.0199(10) Uani 1 1 d . . . H8A H 0.8524 0.1849 0.2336 0.024 Uiso 1 1 calc R . . H8B H 0.8545 0.0940 0.2204 0.024 Uiso 1 1 calc R . . C9 C 0.7409(6) 0.1518(3) 0.1347(3) 0.0178(11) Uani 1 1 d . . . C10 C 0.7938(6) 0.2150(3) 0.0920(3) 0.0244(10) Uani 1 1 d . . . H10 H 0.8532 0.2532 0.1178 0.029 Uiso 1 1 calc R . . C11 C 0.7617(6) 0.2236(4) 0.0126(3) 0.0312(12) Uani 1 1 d . . . H11 H 0.8022 0.2660 -0.0156 0.037 Uiso 1 1 calc R . . C12 C 0.6709(6) 0.1700(3) -0.0247(3) 0.0286(11) Uani 1 1 d . . . H12 H 0.6464 0.1765 -0.0785 0.034 Uiso 1 1 calc R . . C13 C 0.6144(6) 0.1061(3) 0.0162(3) 0.0241(11) Uani 1 1 d . . . H13 H 0.5530 0.0693 -0.0103 0.029 Uiso 1 1 calc R . . C14 C 0.6478(5) 0.0960(3) 0.0959(3) 0.0198(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Dy1 0.01735(12) 0.01214(14) 0.01495(12) 0.000 -0.00008(18) 0.000 Br1 0.0336(3) 0.0147(3) 0.0361(3) 0.000 -0.0136(6) 0.000 O1 0.0262(16) 0.0141(18) 0.0184(14) -0.0003(13) 0.0044(13) -0.0002(14) N1 0.0163(16) 0.016(2) 0.0162(15) 0.0012(14) 0.0009(13) 0.0023(15) N2 0.0210(17) 0.023(2) 0.0199(18) 0.0017(17) -0.0028(16) -0.0003(17) C1 0.029(3) 0.024(3) 0.037(3) -0.007(2) -0.011(2) 0.003(2) C2 0.024(4) 0.028(3) 0.039(3) 0.006(2) -0.003(2) 0.0072(19) C3 0.021(3) 0.040(3) 0.024(2) 0.005(2) -0.0043(18) 0.0026(19) C4 0.024(2) 0.027(3) 0.0195(19) 0.0025(19) -0.0014(17) -0.0030(17) C5 0.018(2) 0.021(3) 0.0149(19) 0.0067(19) 0.0007(17) -0.0004(19) C6 0.022(2) 0.014(3) 0.024(3) -0.002(2) -0.002(2) -0.006(2) C7 0.0227(18) 0.010(2) 0.0244(18) 0.0003(16) 0.0032(18) -0.0013(18) C8 0.019(2) 0.024(3) 0.0169(18) -0.003(2) 0.0005(17) -0.0015(19) C9 0.023(2) 0.014(3) 0.017(2) -0.005(2) 0.0044(19) -0.002(2) C10 0.026(2) 0.022(3) 0.026(2) 0.000(2) 0.003(2) 0.000(2) C11 0.037(3) 0.026(3) 0.031(3) 0.008(2) 0.001(2) -0.004(2) C12 0.033(3) 0.031(3) 0.021(2) 0.008(2) 0.000(2) 0.006(2) C13 0.025(2) 0.027(3) 0.020(2) -0.001(2) -0.0005(19) 0.001(2) C14 0.019(2) 0.022(3) 0.018(2) -0.0053(19) 0.0050(19) -0.0007(19) _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 2.163(3) 3_655 ? Dy1 O1 2.163(3) . ? Dy1 N1 2.578(4) . ? Dy1 N1 2.578(4) 3_655 ? Dy1 N2 2.594(4) . ? Dy1 N2 2.594(4) 3_655 ? Dy1 Br1 2.8515(6) . ? O1 C14 1.332(6) . ? N1 C6 1.491(6) . ? N1 C7 1.495(6) . ? N1 C8 1.501(5) . ? N2 C5 1.345(7) . ? N2 C1 1.351(7) . ? C1 C2 1.388(7) . ? C1 H1 0.9500 . ? C2 C3 1.377(8) . ? C2 H2 0.9500 . ? C3 C4 1.380(8) . ? C3 H3 0.9500 . ? C4 C5 1.398(6) . ? C4 H4 0.9500 . ? C5 C6 1.509(8) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C7 1.516(9) 3_655 ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.491(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.398(8) . ? C9 C14 1.427(7) . ? C10 C11 1.391(7) . ? C10 H10 0.9500 . ? C11 C12 1.378(8) . ? C11 H11 0.9500 . ? C12 C13 1.402(7) . ? C12 H12 0.9500 . ? C13 C14 1.404(6) . ? C13 H13 0.9500 . ? 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 O1 155.79(18) 3_655 . ? O1 Dy1 N1 83.20(12) 3_655 . ? O1 Dy1 N1 76.94(11) . . ? O1 Dy1 N1 76.94(11) 3_655 3_655 ? O1 Dy1 N1 83.20(12) . 3_655 ? N1 Dy1 N1 69.65(16) . 3_655 ? O1 Dy1 N2 86.82(13) 3_655 . ? O1 Dy1 N2 97.27(13) . . ? N1 Dy1 N2 65.57(13) . . ? N1 Dy1 N2 133.75(13) 3_655 . ? O1 Dy1 N2 97.27(13) 3_655 3_655 ? O1 Dy1 N2 86.82(13) . 3_655 ? N1 Dy1 N2 133.75(13) . 3_655 ? N1 Dy1 N2 65.57(13) 3_655 3_655 ? N2 Dy1 N2 160.5(2) . 3_655 ? O1 Dy1 Br1 102.11(9) 3_655 . ? O1 Dy1 Br1 102.11(9) . . ? N1 Dy1 Br1 145.18(8) . . ? N1 Dy1 Br1 145.18(8) 3_655 . ? N2 Dy1 Br1 80.26(10) . . ? N2 Dy1 Br1 80.26(10) 3_655 . ? C14 O1 Dy1 139.5(3) . . ? C6 N1 C7 108.1(4) . . ? C6 N1 C8 107.0(3) . . ? C7 N1 C8 110.8(4) . . ? C6 N1 Dy1 106.2(3) . . ? C7 N1 Dy1 112.4(2) . . ? C8 N1 Dy1 111.9(3) . . ? C5 N2 C1 117.4(4) . . ? C5 N2 Dy1 116.0(3) . . ? C1 N2 Dy1 126.6(3) . . ? N2 C1 C2 123.1(5) . . ? N2 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C3 C2 C1 119.0(5) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 118.7(4) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C3 C4 C5 119.4(5) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N2 C5 C4 122.2(5) . . ? N2 C5 C6 117.1(4) . . ? C4 C5 C6 120.7(5) . . ? N1 C6 C5 111.6(4) . . ? N1 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? N1 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? N1 C7 C7 113.1(3) . 3_655 ? N1 C7 H7A 109.0 . . ? C7 C7 H7A 109.0 3_655 . ? N1 C7 H7B 109.0 . . ? C7 C7 H7B 109.0 3_655 . ? H7A C7 H7B 107.8 . . ? C9 C8 N1 116.0(4) . . ? C9 C8 H8A 108.3 . . ? N1 C8 H8A 108.3 . . ? C9 C8 H8B 108.3 . . ? N1 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? C10 C9 C14 118.6(5) . . ? C10 C9 C8 120.6(5) . . ? C14 C9 C8 120.7(5) . . ? C11 C10 C9 121.8(5) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? C12 C11 C10 119.6(5) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 120.4(5) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C14 120.7(5) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? O1 C14 C13 121.8(5) . . ? O1 C14 C9 119.2(4) . . ? C13 C14 C9 118.9(5) . . ? 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 O1 Dy1 O1 C14 10.0(4) 3_655 . . . ? N1 Dy1 O1 C14 -25.7(4) . . . . ? N1 Dy1 O1 C14 44.9(4) 3_655 . . . ? N2 Dy1 O1 C14 -88.5(5) . . . . ? N2 Dy1 O1 C14 110.6(5) 3_655 . . . ? Br1 Dy1 O1 C14 -170.0(4) . . . . ? O1 Dy1 N1 C6 52.4(3) 3_655 . . . ? O1 Dy1 N1 C6 -141.6(3) . . . . ? N1 Dy1 N1 C6 130.9(3) 3_655 . . . ? N2 Dy1 N1 C6 -37.2(3) . . . . ? N2 Dy1 N1 C6 146.0(3) 3_655 . . . ? Br1 Dy1 N1 C6 -49.1(3) . . . . ? O1 Dy1 N1 C7 -65.6(3) 3_655 . . . ? O1 Dy1 N1 C7 100.4(3) . . . . ? N1 Dy1 N1 C7 12.9(2) 3_655 . . . ? N2 Dy1 N1 C7 -155.2(3) . . . . ? N2 Dy1 N1 C7 28.0(3) 3_655 . . . ? Br1 Dy1 N1 C7 -167.1(2) . . . . ? O1 Dy1 N1 C8 168.9(3) 3_655 . . . ? O1 Dy1 N1 C8 -25.1(3) . . . . ? N1 Dy1 N1 C8 -112.6(3) 3_655 . . . ? N2 Dy1 N1 C8 79.3(3) . . . . ? N2 Dy1 N1 C8 -97.5(3) 3_655 . . . ? Br1 Dy1 N1 C8 67.4(3) . . . . ? O1 Dy1 N2 C5 -63.0(3) 3_655 . . . ? O1 Dy1 N2 C5 93.1(3) . . . . ? N1 Dy1 N2 C5 21.0(3) . . . . ? N1 Dy1 N2 C5 5.5(4) 3_655 . . . ? N2 Dy1 N2 C5 -165.8(3) 3_655 . . . ? Br1 Dy1 N2 C5 -165.8(3) . . . . ? O1 Dy1 N2 C1 115.2(4) 3_655 . . . ? O1 Dy1 N2 C1 -88.7(4) . . . . ? N1 Dy1 N2 C1 -160.8(5) . . . . ? N1 Dy1 N2 C1 -176.3(4) 3_655 . . . ? N2 Dy1 N2 C1 12.4(4) 3_655 . . . ? Br1 Dy1 N2 C1 12.4(4) . . . . ? C5 N2 C1 C2 -2.1(8) . . . . ? Dy1 N2 C1 C2 179.8(4) . . . . ? N2 C1 C2 C3 2.2(8) . . . . ? C1 C2 C3 C4 -0.6(7) . . . . ? C2 C3 C4 C5 -0.9(7) . . . . ? C1 N2 C5 C4 0.4(7) . . . . ? Dy1 N2 C5 C4 178.8(3) . . . . ? C1 N2 C5 C6 -178.4(5) . . . . ? Dy1 N2 C5 C6 0.0(5) . . . . ? C3 C4 C5 N2 1.0(7) . . . . ? C3 C4 C5 C6 179.8(4) . . . . ? C7 N1 C6 C5 174.1(4) . . . . ? C8 N1 C6 C5 -66.5(5) . . . . ? Dy1 N1 C6 C5 53.3(4) . . . . ? N2 C5 C6 N1 -37.3(6) . . . . ? C4 C5 C6 N1 143.8(4) . . . . ? C6 N1 C7 C7 -154.8(4) . . . 3_655 ? C8 N1 C7 C7 88.2(5) . . . 3_655 ? Dy1 N1 C7 C7 -37.9(5) . . . 3_655 ? C6 N1 C8 C9 179.6(5) . . . . ? C7 N1 C8 C9 -62.8(6) . . . . ? Dy1 N1 C8 C9 63.6(5) . . . . ? N1 C8 C9 C10 125.5(5) . . . . ? N1 C8 C9 C14 -58.3(7) . . . . ? C14 C9 C10 C11 -1.9(8) . . . . ? C8 C9 C10 C11 174.4(5) . . . . ? C9 C10 C11 C12 2.4(8) . . . . ? C10 C11 C12 C13 -1.8(8) . . . . ? C11 C12 C13 C14 0.8(8) . . . . ? Dy1 O1 C14 C13 -139.2(4) . . . . ? Dy1 O1 C14 C9 41.0(7) . . . . ? C12 C13 C14 O1 179.9(4) . . . . ? C12 C13 C14 C9 -0.3(7) . . . . ? C10 C9 C14 O1 -179.4(4) . . . . ? C8 C9 C14 O1 4.3(7) . . . . ? C10 C9 C14 C13 0.8(7) . . . . ? C8 C9 C14 C13 -175.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.561 _refine_diff_density_min -1.012 _refine_diff_density_rms 0.133 data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 Cl N4 O2 Y' _chemical_formula_weight 576.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Y' 'Y' -0.2670 2.0244 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M C222(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.6871(4) _cell_length_b 17.1521(6) _cell_length_c 17.0046(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2533.72(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1925 _cell_measurement_theta_min 5.6800 _cell_measurement_theta_max 60.9670 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 4.480 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.90306 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2839 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 5.16 _diffrn_reflns_theta_max 60.99 _reflns_number_total 1697 _reflns_number_gt 1638 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _chemical_absolute_configuration R _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0392P)^2^+1.8784P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00 _refine_ls_number_reflns 1697 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0319 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0765 _refine_ls_wR_factor_gt 0.0754 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Y1 Y 0.5000 0.00801(2) 0.2500 0.01982(16) Uani 1 2 d S . . Cl1 Cl 0.5000 -0.14699(7) 0.2500 0.0383(3) Uani 1 2 d S . . O1 O 0.5970(3) 0.03578(16) 0.13661(16) 0.0257(6) Uani 1 1 d . . . N1 N 0.6615(4) 0.13123(18) 0.27697(19) 0.0221(8) Uani 1 1 d . . . N2 N 0.7534(4) -0.0177(2) 0.3225(2) 0.0269(8) Uani 1 1 d . . . C1 C 0.8275(6) -0.0866(3) 0.3272(3) 0.0352(11) Uani 1 1 d . . . H1 H 0.7825 -0.1307 0.3023 0.042 Uiso 1 1 calc R . . C2 C 0.9651(5) -0.0966(3) 0.3664(3) 0.0382(13) Uani 1 1 d . . . H2 H 1.0141 -0.1461 0.3676 0.046 Uiso 1 1 calc R . . C3 C 1.0301(5) -0.0336(3) 0.4037(3) 0.0338(13) Uani 1 1 d . . . H3 H 1.1246 -0.0388 0.4313 0.041 Uiso 1 1 calc R . . C4 C 0.9559(5) 0.0373(3) 0.4003(2) 0.0282(12) Uani 1 1 d . . . H4 H 0.9989 0.0817 0.4256 0.034 Uiso 1 1 calc R . . C5 C 0.8177(5) 0.0435(2) 0.3596(2) 0.0226(9) Uani 1 1 d . . . C6 C 0.7327(5) 0.1199(3) 0.3552(3) 0.0237(10) Uani 1 1 d . . . H6A H 0.6516 0.1210 0.3961 0.028 Uiso 1 1 calc R . . H6B H 0.8051 0.1632 0.3658 0.028 Uiso 1 1 calc R . . C7 C 0.5650(5) 0.2030(2) 0.2803(2) 0.0239(9) Uani 1 1 d . . . H7A H 0.6314 0.2490 0.2711 0.029 Uiso 1 1 calc R . . H7B H 0.5201 0.2079 0.3335 0.029 Uiso 1 1 calc R . . C8 C 0.7900(5) 0.1405(3) 0.2187(3) 0.0264(9) Uani 1 1 d . . . H8A H 0.8540 0.1853 0.2353 0.032 Uiso 1 1 calc R . . H8B H 0.8556 0.0934 0.2214 0.032 Uiso 1 1 calc R . . C9 C 0.7443(5) 0.1528(3) 0.1350(3) 0.0238(10) Uani 1 1 d . . . C10 C 0.8006(5) 0.2164(3) 0.0929(3) 0.0301(10) Uani 1 1 d . . . H10 H 0.8628 0.2541 0.1187 0.036 Uiso 1 1 calc R . . C11 C 0.7668(6) 0.2252(3) 0.0140(3) 0.0371(12) Uani 1 1 d . . . H11 H 0.8062 0.2687 -0.0141 0.045 Uiso 1 1 calc R . . C12 C 0.6761(6) 0.1712(3) -0.0241(3) 0.0350(11) Uani 1 1 d . . . H12 H 0.6526 0.1779 -0.0782 0.042 Uiso 1 1 calc R . . C13 C 0.6189(5) 0.1073(3) 0.0161(2) 0.0286(10) Uani 1 1 d . . . H13 H 0.5571 0.0703 -0.0109 0.034 Uiso 1 1 calc R . . C14 C 0.6510(5) 0.0964(2) 0.0966(3) 0.0241(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Y1 0.0257(2) 0.0127(2) 0.0211(2) 0.000 -0.0002(2) 0.000 Cl1 0.0475(8) 0.0151(6) 0.0522(8) 0.000 -0.0175(11) 0.000 O1 0.0328(16) 0.0189(14) 0.0253(14) -0.0006(12) 0.0036(12) -0.0031(12) N1 0.0281(19) 0.0140(15) 0.0241(17) -0.0017(13) 0.0002(13) -0.0013(15) N2 0.0302(19) 0.0207(17) 0.0298(19) -0.0020(17) 0.0001(16) 0.0020(16) C1 0.040(3) 0.022(2) 0.044(3) -0.007(2) -0.006(2) 0.005(2) C2 0.043(4) 0.027(2) 0.045(2) -0.002(2) -0.004(2) 0.011(2) C3 0.028(3) 0.040(3) 0.033(2) 0.008(2) -0.0054(19) 0.001(2) C4 0.030(3) 0.030(2) 0.024(2) 0.0016(19) -0.0049(16) -0.0047(17) C5 0.027(2) 0.021(2) 0.0197(18) 0.0006(18) 0.0027(17) -0.0032(18) C6 0.027(2) 0.020(2) 0.024(2) -0.001(2) -0.0023(18) -0.002(2) C7 0.029(2) 0.0118(18) 0.0312(19) -0.0036(16) 0.0046(17) -0.0015(16) C8 0.025(2) 0.025(2) 0.030(2) -0.0016(19) 0.0013(17) -0.0036(18) C9 0.027(2) 0.017(2) 0.027(2) -0.001(2) 0.0034(18) 0.003(2) C10 0.035(3) 0.021(2) 0.035(3) -0.001(2) 0.004(2) -0.0009(19) C11 0.050(3) 0.027(3) 0.035(3) 0.008(2) 0.005(2) -0.004(2) C12 0.048(3) 0.033(3) 0.024(2) 0.008(2) 0.004(2) 0.010(2) C13 0.035(2) 0.026(2) 0.025(2) -0.003(2) 0.0025(18) 0.004(2) C14 0.025(2) 0.021(2) 0.026(2) 0.0006(19) 0.0072(18) 0.0047(19) _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 Y1 O1 2.158(3) . ? Y1 O1 2.158(3) 3_655 ? Y1 N2 2.561(3) 3_655 ? Y1 N2 2.561(3) . ? Y1 N1 2.578(3) . ? Y1 N1 2.578(3) 3_655 ? Y1 Cl1 2.6586(12) . ? O1 C14 1.328(5) . ? N1 C6 1.480(6) . ? N1 C7 1.490(5) . ? N1 C8 1.501(5) . ? N2 C5 1.345(5) . ? N2 C1 1.349(6) . ? C1 C2 1.380(7) . ? C1 H1 0.9500 . ? C2 C3 1.374(7) . ? C2 H2 0.9500 . ? C3 C4 1.378(7) . ? C3 H3 0.9500 . ? C4 C5 1.390(6) . ? C4 H4 0.9500 . ? C5 C6 1.506(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C7 1.528(8) 3_655 ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.492(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.394(7) . ? C9 C14 1.421(7) . ? C10 C11 1.382(7) . ? C10 H10 0.9500 . ? C11 C12 1.377(7) . ? C11 H11 0.9500 . ? C12 C13 1.384(6) . ? C12 H12 0.9500 . ? C13 C14 1.408(6) . ? C13 H13 0.9500 . ? 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 Y1 O1 154.49(15) . 3_655 ? O1 Y1 N2 86.76(11) . 3_655 ? O1 Y1 N2 97.61(11) 3_655 3_655 ? O1 Y1 N2 97.61(11) . . ? O1 Y1 N2 86.76(11) 3_655 . ? N2 Y1 N2 160.21(15) 3_655 . ? O1 Y1 N1 76.43(10) . . ? O1 Y1 N1 82.68(11) 3_655 . ? N2 Y1 N1 133.97(11) 3_655 . ? N2 Y1 N1 65.64(11) . . ? O1 Y1 N1 82.68(11) . 3_655 ? O1 Y1 N1 76.43(10) 3_655 3_655 ? N2 Y1 N1 65.64(11) 3_655 3_655 ? N2 Y1 N1 133.97(11) . 3_655 ? N1 Y1 N1 69.85(15) . 3_655 ? O1 Y1 Cl1 102.76(7) . . ? O1 Y1 Cl1 102.76(7) 3_655 . ? N2 Y1 Cl1 80.10(8) 3_655 . ? N2 Y1 Cl1 80.10(8) . . ? N1 Y1 Cl1 145.07(7) . . ? N1 Y1 Cl1 145.07(7) 3_655 . ? C14 O1 Y1 140.3(2) . . ? C6 N1 C7 108.1(3) . . ? C6 N1 C8 107.2(3) . . ? C7 N1 C8 110.8(3) . . ? C6 N1 Y1 106.2(2) . . ? C7 N1 Y1 112.2(2) . . ? C8 N1 Y1 112.0(2) . . ? C5 N2 C1 117.2(4) . . ? C5 N2 Y1 116.7(3) . . ? C1 N2 Y1 126.1(3) . . ? N2 C1 C2 123.4(4) . . ? N2 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 118.8(4) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 118.9(4) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C3 C4 C5 119.5(4) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N2 C5 C4 122.2(4) . . ? N2 C5 C6 116.8(4) . . ? C4 C5 C6 121.0(4) . . ? N1 C6 C5 111.4(4) . . ? N1 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? N1 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? N1 C7 C7 113.0(3) . 3_655 ? N1 C7 H7A 109.0 . . ? C7 C7 H7A 109.0 3_655 . ? N1 C7 H7B 109.0 . . ? C7 C7 H7B 109.0 3_655 . ? H7A C7 H7B 107.8 . . ? C9 C8 N1 116.5(4) . . ? C9 C8 H8A 108.2 . . ? N1 C8 H8A 108.2 . . ? C9 C8 H8B 108.2 . . ? N1 C8 H8B 108.2 . . ? H8A C8 H8B 107.3 . . ? C10 C9 C14 119.7(4) . . ? C10 C9 C8 120.5(4) . . ? C14 C9 C8 119.6(4) . . ? C11 C10 C9 120.7(5) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C10 120.3(4) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 120.3(4) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C14 121.0(4) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? O1 C14 C13 122.1(4) . . ? O1 C14 C9 119.9(4) . . ? C13 C14 C9 118.0(4) . . ? 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 O1 Y1 O1 C14 10.7(4) 3_655 . . . ? N2 Y1 O1 C14 111.6(4) 3_655 . . . ? N2 Y1 O1 C14 -87.8(4) . . . . ? N1 Y1 O1 C14 -25.2(4) . . . . ? N1 Y1 O1 C14 45.7(4) 3_655 . . . ? Cl1 Y1 O1 C14 -169.3(4) . . . . ? O1 Y1 N1 C6 -141.9(3) . . . . ? O1 Y1 N1 C6 52.8(3) 3_655 . . . ? N2 Y1 N1 C6 146.4(2) 3_655 . . . ? N2 Y1 N1 C6 -36.9(2) . . . . ? N1 Y1 N1 C6 131.0(3) 3_655 . . . ? Cl1 Y1 N1 C6 -49.0(3) . . . . ? O1 Y1 N1 C7 100.2(3) . . . . ? O1 Y1 N1 C7 -65.1(3) 3_655 . . . ? N2 Y1 N1 C7 28.5(3) 3_655 . . . ? N2 Y1 N1 C7 -154.8(3) . . . . ? N1 Y1 N1 C7 13.13(19) 3_655 . . . ? Cl1 Y1 N1 C7 -166.87(19) . . . . ? O1 Y1 N1 C8 -25.2(2) . . . . ? O1 Y1 N1 C8 169.6(3) 3_655 . . . ? N2 Y1 N1 C8 -96.9(3) 3_655 . . . ? N2 Y1 N1 C8 79.8(3) . . . . ? N1 Y1 N1 C8 -112.2(3) 3_655 . . . ? Cl1 Y1 N1 C8 67.8(3) . . . . ? O1 Y1 N2 C5 91.6(3) . . . . ? O1 Y1 N2 C5 -63.1(3) 3_655 . . . ? N2 Y1 N2 C5 -166.7(3) 3_655 . . . ? N1 Y1 N2 C5 20.3(3) . . . . ? N1 Y1 N2 C5 4.5(4) 3_655 . . . ? Cl1 Y1 N2 C5 -166.7(3) . . . . ? O1 Y1 N2 C1 -88.8(4) . . . . ? O1 Y1 N2 C1 116.5(4) 3_655 . . . ? N2 Y1 N2 C1 12.9(4) 3_655 . . . ? N1 Y1 N2 C1 -160.1(4) . . . . ? N1 Y1 N2 C1 -175.9(3) 3_655 . . . ? Cl1 Y1 N2 C1 12.9(4) . . . . ? C5 N2 C1 C2 -1.3(7) . . . . ? Y1 N2 C1 C2 179.1(4) . . . . ? N2 C1 C2 C3 0.9(8) . . . . ? C1 C2 C3 C4 -0.3(7) . . . . ? C2 C3 C4 C5 0.1(6) . . . . ? C1 N2 C5 C4 1.1(6) . . . . ? Y1 N2 C5 C4 -179.3(3) . . . . ? C1 N2 C5 C6 -178.9(4) . . . . ? Y1 N2 C5 C6 0.7(5) . . . . ? C3 C4 C5 N2 -0.5(6) . . . . ? C3 C4 C5 C6 179.5(4) . . . . ? C7 N1 C6 C5 173.5(3) . . . . ? C8 N1 C6 C5 -67.0(4) . . . . ? Y1 N1 C6 C5 52.9(4) . . . . ? N2 C5 C6 N1 -37.8(5) . . . . ? C4 C5 C6 N1 142.2(4) . . . . ? C6 N1 C7 C7 -155.0(4) . . . 3_655 ? C8 N1 C7 C7 87.8(4) . . . 3_655 ? Y1 N1 C7 C7 -38.2(5) . . . 3_655 ? C6 N1 C8 C9 180.0(4) . . . . ? C7 N1 C8 C9 -62.3(5) . . . . ? Y1 N1 C8 C9 63.8(4) . . . . ? N1 C8 C9 C10 126.3(4) . . . . ? N1 C8 C9 C14 -57.9(6) . . . . ? C14 C9 C10 C11 -0.1(7) . . . . ? C8 C9 C10 C11 175.7(4) . . . . ? C9 C10 C11 C12 0.3(7) . . . . ? C10 C11 C12 C13 -0.5(7) . . . . ? C11 C12 C13 C14 0.4(7) . . . . ? Y1 O1 C14 C13 -139.4(4) . . . . ? Y1 O1 C14 C9 40.5(6) . . . . ? C12 C13 C14 O1 179.7(4) . . . . ? C12 C13 C14 C9 -0.2(6) . . . . ? C10 C9 C14 O1 -179.9(4) . . . . ? C8 C9 C14 O1 4.3(6) . . . . ? C10 C9 C14 C13 0.0(6) . . . . ? C8 C9 C14 C13 -175.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 60.99 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.245 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.061 data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 Br N4 O2 Y' _chemical_formula_weight 621.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Y' 'Y' -0.2670 2.0244 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M C222(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.6882(4) _cell_length_b 17.3517(9) _cell_length_c 17.0584(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2571.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1904 _cell_measurement_theta_min 2.5710 _cell_measurement_theta_max 60.7160 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 5.278 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.90669 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2879 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 5.19 _diffrn_reflns_theta_max 60.90 _reflns_number_total 1749 _reflns_number_gt 1664 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _chemical_absolute_configuration R _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+5.2160P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00 _refine_ls_number_reflns 1749 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0340 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0802 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Y1 Y 0.5000 0.01055(3) 0.2500 0.01877(17) Uani 1 2 d S . . Br1 Br 0.5000 -0.15252(3) 0.2500 0.0346(2) Uani 1 2 d S . . O1 O 0.5955(4) 0.03660(19) 0.13665(19) 0.0255(7) Uani 1 1 d . . . N1 N 0.6604(4) 0.1317(2) 0.2764(2) 0.0211(9) Uani 1 1 d . . . N2 N 0.7568(5) -0.0151(2) 0.3213(2) 0.0256(9) Uani 1 1 d . . . C1 C 0.8328(6) -0.0831(3) 0.3261(3) 0.0351(13) Uani 1 1 d . . . H1 H 0.7892 -0.1268 0.3009 0.042 Uiso 1 1 calc R . . C2 C 0.9691(6) -0.0921(3) 0.3653(4) 0.0365(14) Uani 1 1 d . . . H2 H 1.0192 -0.1408 0.3662 0.044 Uiso 1 1 calc R . . C3 C 1.0324(6) -0.0300(3) 0.4032(3) 0.0344(14) Uani 1 1 d . . . H3 H 1.1269 -0.0348 0.4308 0.041 Uiso 1 1 calc R . . C4 C 0.9562(5) 0.0396(3) 0.4004(3) 0.0291(13) Uani 1 1 d . . . H4 H 0.9969 0.0834 0.4268 0.035 Uiso 1 1 calc R . . C5 C 0.8194(5) 0.0452(3) 0.3588(3) 0.0219(10) Uani 1 1 d . . . C6 C 0.7341(6) 0.1204(3) 0.3545(3) 0.0245(12) Uani 1 1 d . . . H6A H 0.6540 0.1216 0.3957 0.029 Uiso 1 1 calc R . . H6B H 0.8067 0.1632 0.3646 0.029 Uiso 1 1 calc R . . C7 C 0.5655(6) 0.2024(3) 0.2799(3) 0.0248(10) Uani 1 1 d . . . H7A H 0.6322 0.2478 0.2705 0.030 Uiso 1 1 calc R . . H7B H 0.5215 0.2075 0.3332 0.030 Uiso 1 1 calc R . . C8 C 0.7889(5) 0.1403(3) 0.2178(3) 0.0230(10) Uani 1 1 d . . . H8A H 0.8542 0.0937 0.2206 0.028 Uiso 1 1 calc R . . H8B H 0.8533 0.1846 0.2340 0.028 Uiso 1 1 calc R . . C9 C 0.7418(6) 0.1522(3) 0.1338(3) 0.0235(11) Uani 1 1 d . . . C10 C 0.7953(6) 0.2155(3) 0.0924(3) 0.0291(12) Uani 1 1 d . . . H10 H 0.8550 0.2534 0.1186 0.035 Uiso 1 1 calc R . . C11 C 0.7633(7) 0.2243(3) 0.0133(3) 0.0354(13) Uani 1 1 d . . . H11 H 0.8032 0.2671 -0.0149 0.043 Uiso 1 1 calc R . . C12 C 0.6725(7) 0.1701(3) -0.0239(3) 0.0347(12) Uani 1 1 d . . . H12 H 0.6483 0.1760 -0.0778 0.042 Uiso 1 1 calc R . . C13 C 0.6167(6) 0.1072(3) 0.0170(3) 0.0281(11) Uani 1 1 d . . . H13 H 0.5548 0.0703 -0.0095 0.034 Uiso 1 1 calc R . . C14 C 0.6493(5) 0.0967(3) 0.0962(3) 0.0231(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Y1 0.0231(3) 0.0141(3) 0.0191(3) 0.000 -0.0003(3) 0.000 Br1 0.0428(4) 0.0164(3) 0.0446(4) 0.000 -0.0145(5) 0.000 O1 0.0306(18) 0.0225(17) 0.0232(16) -0.0010(15) 0.0019(15) -0.0035(15) N1 0.028(2) 0.0176(19) 0.0179(19) -0.0023(16) -0.0001(15) -0.0016(17) N2 0.027(2) 0.020(2) 0.030(2) -0.0030(18) -0.0014(19) 0.0009(19) C1 0.035(3) 0.027(3) 0.043(3) -0.006(3) -0.006(3) 0.006(2) C2 0.033(4) 0.033(3) 0.044(3) 0.001(2) -0.005(3) 0.007(2) C3 0.029(3) 0.043(3) 0.031(3) 0.006(2) -0.008(2) 0.001(2) C4 0.032(3) 0.034(3) 0.022(2) 0.005(2) -0.0001(19) -0.007(2) C5 0.024(2) 0.024(3) 0.018(2) 0.004(2) 0.002(2) -0.002(2) C6 0.029(3) 0.024(3) 0.020(3) -0.003(2) -0.001(2) -0.005(2) C7 0.029(2) 0.015(2) 0.031(2) -0.001(2) -0.001(2) 0.000(2) C8 0.021(2) 0.021(2) 0.027(2) 0.001(2) 0.0015(18) -0.004(2) C9 0.022(2) 0.025(3) 0.023(2) 0.001(2) 0.003(2) 0.002(2) C10 0.035(3) 0.020(3) 0.032(3) 0.000(2) 0.002(2) -0.004(2) C11 0.048(3) 0.027(3) 0.031(3) 0.008(2) 0.003(3) -0.003(3) C12 0.047(3) 0.033(3) 0.024(3) 0.005(2) -0.001(2) 0.007(3) C13 0.035(3) 0.026(3) 0.023(3) -0.004(2) 0.000(2) 0.003(2) C14 0.023(3) 0.020(3) 0.026(3) -0.004(2) 0.007(2) 0.004(2) _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 Y1 O1 2.152(3) 3_655 ? Y1 O1 2.152(3) . ? Y1 N1 2.562(4) . ? Y1 N1 2.562(4) 3_655 ? Y1 N2 2.580(4) 3_655 ? Y1 N2 2.580(4) . ? Y1 Br1 2.8296(7) . ? O1 C14 1.335(6) . ? N1 C7 1.481(6) . ? N1 C6 1.491(7) . ? N1 C8 1.505(6) . ? N2 C5 1.342(7) . ? N2 C1 1.354(7) . ? C1 C2 1.369(8) . ? C1 H1 0.9500 . ? C2 C3 1.373(8) . ? C2 H2 0.9500 . ? C3 C4 1.378(8) . ? C3 H3 0.9500 . ? C4 C5 1.387(7) . ? C4 H4 0.9500 . ? C5 C6 1.501(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C7 1.529(10) 3_655 ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.505(8) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.386(8) . ? C9 C14 1.409(7) . ? C10 C11 1.385(8) . ? C10 H10 0.9500 . ? C11 C12 1.382(8) . ? C11 H11 0.9500 . ? C12 C13 1.383(8) . ? C12 H12 0.9500 . ? C13 C14 1.391(7) . ? C13 H13 0.9500 . ? 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 Y1 O1 155.75(18) 3_655 . ? O1 Y1 N1 83.09(12) 3_655 . ? O1 Y1 N1 77.04(12) . . ? O1 Y1 N1 77.04(12) 3_655 3_655 ? O1 Y1 N1 83.09(12) . 3_655 ? N1 Y1 N1 69.75(18) . 3_655 ? O1 Y1 N2 97.25(13) 3_655 3_655 ? O1 Y1 N2 86.92(13) . 3_655 ? N1 Y1 N2 134.02(13) . 3_655 ? N1 Y1 N2 65.67(12) 3_655 3_655 ? O1 Y1 N2 86.92(13) 3_655 . ? O1 Y1 N2 97.25(13) . . ? N1 Y1 N2 65.67(12) . . ? N1 Y1 N2 134.02(13) 3_655 . ? N2 Y1 N2 160.14(18) 3_655 . ? O1 Y1 Br1 102.13(9) 3_655 . ? O1 Y1 Br1 102.13(9) . . ? N1 Y1 Br1 145.12(9) . . ? N1 Y1 Br1 145.12(9) 3_655 . ? N2 Y1 Br1 80.07(9) 3_655 . ? N2 Y1 Br1 80.07(9) . . ? C14 O1 Y1 139.8(3) . . ? C7 N1 C6 108.2(4) . . ? C7 N1 C8 111.0(4) . . ? C6 N1 C8 106.7(4) . . ? C7 N1 Y1 112.6(3) . . ? C6 N1 Y1 106.4(3) . . ? C8 N1 Y1 111.6(3) . . ? C5 N2 C1 117.0(4) . . ? C5 N2 Y1 116.1(3) . . ? C1 N2 Y1 126.9(3) . . ? N2 C1 C2 123.4(5) . . ? N2 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C1 C2 C3 119.1(5) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C2 C3 C4 118.7(4) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C3 C4 C5 119.4(5) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N2 C5 C4 122.4(5) . . ? N2 C5 C6 117.0(4) . . ? C4 C5 C6 120.6(5) . . ? N1 C6 C5 111.8(4) . . ? N1 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? N1 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? N1 C7 C7 112.8(3) . 3_655 ? N1 C7 H7A 109.0 . . ? C7 C7 H7A 109.0 3_655 . ? N1 C7 H7B 109.0 . . ? C7 C7 H7B 109.0 3_655 . ? H7A C7 H7B 107.8 . . ? N1 C8 C9 116.4(4) . . ? N1 C8 H8A 108.2 . . ? C9 C8 H8A 108.2 . . ? N1 C8 H8B 108.2 . . ? C9 C8 H8B 108.2 . . ? H8A C8 H8B 107.3 . . ? C10 C9 C14 120.0(5) . . ? C10 C9 C8 120.2(5) . . ? C14 C9 C8 119.7(4) . . ? C11 C10 C9 121.1(5) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C12 C11 C10 119.1(5) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C11 C12 C13 120.4(5) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C14 121.4(5) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? O1 C14 C13 122.2(5) . . ? O1 C14 C9 119.9(5) . . ? C13 C14 C9 117.9(5) . . ? 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 O1 Y1 O1 C14 10.5(4) 3_655 . . . ? N1 Y1 O1 C14 -25.2(4) . . . . ? N1 Y1 O1 C14 45.5(5) 3_655 . . . ? N2 Y1 O1 C14 111.4(5) 3_655 . . . ? N2 Y1 O1 C14 -88.2(5) . . . . ? Br1 Y1 O1 C14 -169.5(4) . . . . ? O1 Y1 N1 C7 -65.5(3) 3_655 . . . ? O1 Y1 N1 C7 100.5(3) . . . . ? N1 Y1 N1 C7 13.2(2) 3_655 . . . ? N2 Y1 N1 C7 27.9(4) 3_655 . . . ? N2 Y1 N1 C7 -155.3(3) . . . . ? Br1 Y1 N1 C7 -166.8(2) . . . . ? O1 Y1 N1 C6 52.8(3) 3_655 . . . ? O1 Y1 N1 C6 -141.2(3) . . . . ? N1 Y1 N1 C6 131.5(3) 3_655 . . . ? N2 Y1 N1 C6 146.2(3) 3_655 . . . ? N2 Y1 N1 C6 -36.9(3) . . . . ? Br1 Y1 N1 C6 -48.5(3) . . . . ? O1 Y1 N1 C8 168.9(3) 3_655 . . . ? O1 Y1 N1 C8 -25.1(3) . . . . ? N1 Y1 N1 C8 -112.4(3) 3_655 . . . ? N2 Y1 N1 C8 -97.7(3) 3_655 . . . ? N2 Y1 N1 C8 79.2(3) . . . . ? Br1 Y1 N1 C8 67.6(3) . . . . ? O1 Y1 N2 C5 -62.6(3) 3_655 . . . ? O1 Y1 N2 C5 93.4(3) . . . . ? N1 Y1 N2 C5 21.2(3) . . . . ? N1 Y1 N2 C5 6.0(4) 3_655 . . . ? N2 Y1 N2 C5 -165.5(3) 3_655 . . . ? Br1 Y1 N2 C5 -165.5(3) . . . . ? O1 Y1 N2 C1 115.9(5) 3_655 . . . ? O1 Y1 N2 C1 -88.1(5) . . . . ? N1 Y1 N2 C1 -160.3(5) . . . . ? N1 Y1 N2 C1 -175.5(4) 3_655 . . . ? N2 Y1 N2 C1 13.0(4) 3_655 . . . ? Br1 Y1 N2 C1 13.0(4) . . . . ? C5 N2 C1 C2 -1.4(8) . . . . ? Y1 N2 C1 C2 -179.9(4) . . . . ? N2 C1 C2 C3 1.2(9) . . . . ? C1 C2 C3 C4 0.0(8) . . . . ? C2 C3 C4 C5 -0.8(8) . . . . ? C1 N2 C5 C4 0.5(7) . . . . ? Y1 N2 C5 C4 179.2(3) . . . . ? C1 N2 C5 C6 -179.2(5) . . . . ? Y1 N2 C5 C6 -0.5(5) . . . . ? C3 C4 C5 N2 0.6(7) . . . . ? C3 C4 C5 C6 -179.7(5) . . . . ? C7 N1 C6 C5 173.9(4) . . . . ? C8 N1 C6 C5 -66.6(5) . . . . ? Y1 N1 C6 C5 52.7(4) . . . . ? N2 C5 C6 N1 -36.5(6) . . . . ? C4 C5 C6 N1 143.8(4) . . . . ? C6 N1 C7 C7 -155.3(5) . . . 3_655 ? C8 N1 C7 C7 88.0(5) . . . 3_655 ? Y1 N1 C7 C7 -38.0(6) . . . 3_655 ? C7 N1 C8 C9 -62.6(5) . . . . ? C6 N1 C8 C9 179.8(4) . . . . ? Y1 N1 C8 C9 63.9(5) . . . . ? N1 C8 C9 C10 124.9(5) . . . . ? N1 C8 C9 C14 -58.3(6) . . . . ? C14 C9 C10 C11 -1.9(8) . . . . ? C8 C9 C10 C11 174.9(5) . . . . ? C9 C10 C11 C12 2.0(8) . . . . ? C10 C11 C12 C13 -1.1(8) . . . . ? C11 C12 C13 C14 0.2(8) . . . . ? Y1 O1 C14 C13 -139.3(4) . . . . ? Y1 O1 C14 C9 40.5(7) . . . . ? C12 C13 C14 O1 179.5(5) . . . . ? C12 C13 C14 C9 -0.2(7) . . . . ? C10 C9 C14 O1 -178.7(5) . . . . ? C8 C9 C14 O1 4.5(7) . . . . ? C10 C9 C14 C13 1.0(7) . . . . ? C8 C9 C14 C13 -175.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 60.90 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.813 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.069