Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Hongwei Hou' _publ_contact_author_address ; Department of Chemistry Zhengzhou University Zhengzhou Henan 450052 CHINA ; _publ_contact_author_email HOUHONGW@ZZU.EDU.CN _publ_section_title ; Coordination Frameworks Constructed from Bipyridyl Piperazine and MCl2 (M = Co, Ni, Zn): Structural Characterization and Optical Properties ; loop_ _publ_author_name 'Hongwei Hou' 'Yaoting Fan' 'Liwei Mi' 'Yan Pan' 'Yali Sang' ; Yinglin Song ; 'Mingsheng Tang' 'Hong Xu' data_Complex_1 _database_code_depnum_ccdc_archive 'CCDC 254993' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 Cl2 Co N4 O2' _chemical_formula_weight 426.16 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' Co Co 0.3494 0.9721 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.537(3) _cell_length_b 9.7307(19) _cell_length_c 13.620(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1661.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 320 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25.1 _exptl_crystal_description Prismatic _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.704 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 1.373 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7708 _exptl_absorpt_correction_T_max 0.8001 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 R-AXIS-IV _diffrn_measurement_method 'Oscillation frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3867 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1282 _reflns_number_gt 1135 _reflns_threshold_expression >2sigma(I) _computing_data_collection raxis _computing_cell_refinement raxis _computing_data_reduction raxis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics texsan _computing_publication_material texsan _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^)+(0.0000P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.00136(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1282 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0408 _refine_ls_wR_factor_gt 0.0398 _refine_ls_goodness_of_fit_ref 1.660 _refine_ls_restrained_S_all 1.660 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.0000 0.0000 0.5000 0.01656(15) Uani 1 2 d S . . Cl1 Cl -0.17471(6) 0.06447(7) 0.56677(5) 0.02489(19) Uani 1 1 d . . . O1 O -0.00367(17) 0.32974(16) 0.89958(12) 0.0226(4) Uani 1 1 d . . . N1 N 0.07946(18) 0.1197(2) 0.61103(15) 0.0187(6) Uani 1 1 d . . . N2 N -0.00065(19) 0.09937(19) 0.92346(14) 0.0182(5) Uani 1 1 d . . . C1 C 0.1662(2) 0.1965(2) 0.59350(19) 0.0227(7) Uani 1 1 d . . . H1A H 0.1946 0.1957 0.5304 0.027 Uiso 1 1 calc R . . C2 C 0.2160(2) 0.2770(3) 0.6641(2) 0.0267(7) Uani 1 1 d . . . H2A H 0.2767 0.3276 0.6487 0.032 Uiso 1 1 calc R . . C3 C 0.1733(2) 0.2802(3) 0.7576(2) 0.0242(7) Uani 1 1 d . . . H3A H 0.2037 0.3348 0.8061 0.029 Uiso 1 1 calc R . . C4 C 0.0836(2) 0.2001(3) 0.77781(19) 0.0172(6) Uani 1 1 d . . . C5 C 0.0406(2) 0.1222(3) 0.70313(18) 0.0190(7) Uani 1 1 d . . . H5A H -0.0186 0.0681 0.7172 0.023 Uiso 1 1 calc R . . C6 C 0.0248(2) 0.2130(3) 0.87364(18) 0.0158(7) Uani 1 1 d . . . C7 C 0.0427(3) -0.0387(3) 0.9042(2) 0.0220(7) Uani 1 1 d . . . C8 C -0.0816(2) 0.1016(3) 1.0005(2) 0.0217(6) Uani 1 1 d . . . H8B H -0.107(2) 0.194(2) 1.010(2) 0.026 Uiso 1 1 d . . . H7B H 0.099(2) -0.035(3) 0.8600(18) 0.026 Uiso 1 1 d . . . H7A H -0.015(2) -0.092(2) 0.8778(18) 0.026 Uiso 1 1 d . . . H8A H -0.142(2) 0.045(3) 0.9781(19) 0.026 Uiso 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 Co1 0.0224(3) 0.0163(3) 0.0110(2) -0.0001(2) 0.0013(3) -0.0008(2) Cl1 0.0240(4) 0.0264(4) 0.0243(4) -0.0005(3) 0.0023(4) 0.0005(3) O1 0.0361(12) 0.0126(9) 0.0193(9) -0.0040(8) 0.0047(11) -0.0004(9) N1 0.0234(16) 0.0201(13) 0.0125(12) -0.0014(10) 0.0010(12) -0.0020(10) N2 0.0222(13) 0.0163(12) 0.0162(12) 0.0024(9) 0.0060(13) 0.0016(10) C1 0.0237(17) 0.0269(16) 0.0177(16) -0.0011(12) 0.0073(15) 0.0000(14) C2 0.0218(17) 0.0332(18) 0.0249(17) -0.0041(15) 0.0087(14) -0.0055(14) C3 0.0273(17) 0.0249(16) 0.0204(16) -0.0048(12) -0.0013(15) -0.0049(14) C4 0.0217(16) 0.0164(14) 0.0134(15) -0.0005(11) 0.0012(13) 0.0022(13) C5 0.0229(18) 0.0164(15) 0.0177(17) 0.0007(12) 0.0026(13) -0.0036(12) C6 0.0137(18) 0.0233(16) 0.0105(14) -0.0031(11) -0.0028(11) -0.0040(11) C7 0.0296(19) 0.0182(16) 0.0182(16) -0.0009(13) 0.0042(14) 0.0011(12) C8 0.0227(16) 0.0178(16) 0.0245(15) 0.0020(14) 0.0101(17) 0.0036(12) _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 Co1 O1 2.1488(16) 7_565 ? Co1 O1 2.1488(16) 3_546 ? Co1 N1 2.153(2) 5_556 ? Co1 N1 2.153(2) . ? Co1 Cl1 2.4531(8) . ? Co1 Cl1 2.4532(8) 5_556 ? O1 C6 1.242(3) . ? O1 Co1 2.1488(16) 3_556 ? N1 C1 1.340(3) . ? N1 C5 1.346(3) . ? N2 C6 1.336(3) . ? N2 C8 1.460(3) . ? N2 C7 1.472(3) . ? C1 C2 1.388(4) . ? C1 H1A 0.9300 . ? C2 C3 1.382(4) . ? C2 H2A 0.9300 . ? C3 C4 1.396(4) . ? C3 H3A 0.9300 . ? C4 C5 1.378(3) . ? C4 C6 1.504(4) . ? C5 H5A 0.9300 . ? C7 C8 1.516(4) 5_557 ? C7 H7B 0.93(3) . ? C7 H7A 0.96(3) . ? C8 C7 1.516(4) 5_557 ? C8 H8B 0.96(2) . ? C8 H8A 0.98(3) . ? 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 Co1 O1 180.0 7_565 3_546 ? O1 Co1 N1 87.72(7) 7_565 5_556 ? O1 Co1 N1 92.28(7) 3_546 5_556 ? O1 Co1 N1 92.28(7) 7_565 . ? O1 Co1 N1 87.72(7) 3_546 . ? N1 Co1 N1 180.0 5_556 . ? O1 Co1 Cl1 91.13(6) 7_565 . ? O1 Co1 Cl1 88.88(6) 3_546 . ? N1 Co1 Cl1 89.18(6) 5_556 . ? N1 Co1 Cl1 90.82(6) . . ? O1 Co1 Cl1 88.87(6) 7_565 5_556 ? O1 Co1 Cl1 91.12(6) 3_546 5_556 ? N1 Co1 Cl1 90.82(6) 5_556 5_556 ? N1 Co1 Cl1 89.18(6) . 5_556 ? Cl1 Co1 Cl1 180.0 . 5_556 ? C6 O1 Co1 151.65(18) . 3_556 ? C1 N1 C5 116.7(2) . . ? C1 N1 Co1 123.47(18) . . ? C5 N1 Co1 119.79(18) . . ? C6 N2 C8 121.2(2) . . ? C6 N2 C7 125.2(2) . . ? C8 N2 C7 113.4(2) . . ? N1 C1 C2 123.8(3) . . ? N1 C1 H1A 118.1 . . ? C2 C1 H1A 118.1 . . ? C3 C2 C1 118.4(3) . . ? C3 C2 H2A 120.8 . . ? C1 C2 H2A 120.8 . . ? C2 C3 C4 118.8(3) . . ? C2 C3 H3A 120.6 . . ? C4 C3 H3A 120.6 . . ? C5 C4 C3 118.4(2) . . ? C5 C4 C6 119.7(3) . . ? C3 C4 C6 121.3(2) . . ? N1 C5 C4 123.8(3) . . ? N1 C5 H5A 118.1 . . ? C4 C5 H5A 118.1 . . ? O1 C6 N2 122.9(2) . . ? O1 C6 C4 117.7(2) . . ? N2 C6 C4 119.2(2) . . ? N2 C7 C8 109.6(2) . 5_557 ? N2 C7 H7B 110.9(16) . . ? C8 C7 H7B 108.9(16) 5_557 . ? N2 C7 H7A 106.4(15) . . ? C8 C7 H7A 110.1(15) 5_557 . ? H7B C7 H7A 111(2) . . ? N2 C8 C7 112.7(2) . 5_557 ? N2 C8 H8B 109.5(16) . . ? C7 C8 H8B 111.9(17) 5_557 . ? N2 C8 H8A 107.7(16) . . ? C7 C8 H8A 106.8(16) 5_557 . ? H8B C8 H8A 108(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 O1 Co1 N1 C1 -48.9(2) 7_565 . . . ? O1 Co1 N1 C1 131.1(2) 3_546 . . . ? N1 Co1 N1 C1 54(12) 5_556 . . . ? Cl1 Co1 N1 C1 -140.1(2) . . . . ? Cl1 Co1 N1 C1 39.9(2) 5_556 . . . ? O1 Co1 N1 C5 129.6(2) 7_565 . . . ? O1 Co1 N1 C5 -50.4(2) 3_546 . . . ? N1 Co1 N1 C5 -128(12) 5_556 . . . ? Cl1 Co1 N1 C5 38.4(2) . . . . ? Cl1 Co1 N1 C5 -141.6(2) 5_556 . . . ? C5 N1 C1 C2 -0.5(4) . . . . ? Co1 N1 C1 C2 178.1(2) . . . . ? N1 C1 C2 C3 -1.0(4) . . . . ? C1 C2 C3 C4 1.5(4) . . . . ? C2 C3 C4 C5 -0.7(4) . . . . ? C2 C3 C4 C6 -171.8(3) . . . . ? C1 N1 C5 C4 1.3(4) . . . . ? Co1 N1 C5 C4 -177.3(2) . . . . ? C3 C4 C5 N1 -0.7(4) . . . . ? C6 C4 C5 N1 170.5(3) . . . . ? Co1 O1 C6 N2 66.6(5) 3_556 . . . ? Co1 O1 C6 C4 -118.0(3) 3_556 . . . ? C8 N2 C6 O1 12.7(4) . . . . ? C7 N2 C6 O1 -171.1(3) . . . . ? C8 N2 C6 C4 -162.6(2) . . . . ? C7 N2 C6 C4 13.5(4) . . . . ? C5 C4 C6 O1 -118.8(3) . . . . ? C3 C4 C6 O1 52.2(4) . . . . ? C5 C4 C6 N2 56.8(4) . . . . ? C3 C4 C6 N2 -132.3(3) . . . . ? C6 N2 C7 C8 130.4(3) . . . 5_557 ? C8 N2 C7 C8 -53.1(3) . . . 5_557 ? C6 N2 C8 C7 -128.6(3) . . . 5_557 ? C7 N2 C8 C7 54.8(3) . . . 5_557 ? _diffrn_measured_fraction_theta_max 0.880 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.880 _refine_diff_density_max 0.262 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.065 data_Complex2 _database_code_depnum_ccdc_archive 'CCDC 254994' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H38 Cl2 N8 Ni O7' _chemical_formula_weight 776.31 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' Ni Ni 0.3393 1.1124 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6448(19) _cell_length_b 11.203(2) _cell_length_c 8.7152(17) _cell_angle_alpha 104.11(3) _cell_angle_beta 91.67(3) _cell_angle_gamma 72.79(3) _cell_volume 871.5(3) _cell_formula_units_Z 1 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 250 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25.1 _exptl_crystal_description Prismatic _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.769 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8614 _exptl_absorpt_correction_T_max 0.8868 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 R-AXIS-IV _diffrn_measurement_method 'Oscillation frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2433 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2433 _reflns_number_gt 2223 _reflns_threshold_expression >2sigma(I) _computing_data_collection raxis _computing_cell_refinement raxis _computing_data_reduction raxis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics texsan _computing_publication_material texsan _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^)+(0.0998P)^2^+3.5222P] 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 SHELXL _refine_ls_extinction_coef 0.012(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2433 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1517 _refine_ls_wR_factor_gt 0.1464 _refine_ls_goodness_of_fit_ref 0.862 _refine_ls_restrained_S_all 0.862 _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 Ni1 Ni 1.0000 0.5000 0.5000 0.0280(3) Uani 1 2 d S . . Cl1 Cl 1.06859(14) 0.27748(11) 0.34783(14) 0.0363(4) Uani 1 1 d . . . N1 N 1.0581(4) 0.5570(4) 0.2966(4) 0.0314(9) Uani 1 1 d . . . N2 N 0.9545(5) 0.9140(5) 0.0625(8) 0.0654(18) Uani 1 1 d . . . N3 N 0.7758(5) 0.5227(4) 0.4285(5) 0.0334(9) Uani 1 1 d . . . N4 N 0.4695(5) 0.8894(5) 0.4070(5) 0.0467(12) Uani 1 1 d . . . C1 C 1.1616(5) 0.4754(5) 0.1890(6) 0.0348(11) Uani 1 1 d . . . H1A H 1.2154 0.3975 0.2094 0.042 Uiso 1 1 calc R . . C2 C 1.1914(6) 0.5026(5) 0.0493(6) 0.0397(12) Uani 1 1 d . . . H2A H 1.2633 0.4435 -0.0228 0.048 Uiso 1 1 calc R . . C3 C 1.1140(6) 0.6176(6) 0.0179(6) 0.0418(13) Uani 1 1 d . . . H3A H 1.1317 0.6367 -0.0763 0.050 Uiso 1 1 calc R . . C4 C 1.0087(5) 0.7051(5) 0.1286(6) 0.0337(11) Uani 1 1 d . . . C5 C 0.9864(6) 0.6696(5) 0.2657(6) 0.0342(11) Uani 1 1 d . . . H5A H 0.9169 0.7281 0.3410 0.041 Uiso 1 1 calc R . . C6 C 0.9041(6) 0.8274(5) 0.1040(6) 0.0407(13) Uani 1 1 d . . . C7 C 0.8518(7) 1.0285(10) 0.0245(16) 0.130(5) Uani 1 1 d . . . H7A H 0.7736 1.0014 -0.0315 0.157 Uiso 1 1 calc R . . H7B H 0.8096 1.0883 0.1239 0.157 Uiso 1 1 calc R . . C8 C 1.1056(7) 0.9125(11) 0.052(2) 0.174(8) Uani 1 1 d . . . H8A H 1.1331 0.9403 0.1596 0.209 Uiso 1 1 calc R . . H8B H 1.1622 0.8229 0.0136 0.209 Uiso 1 1 calc R . . C9 C 0.7239(6) 0.4211(5) 0.3836(6) 0.0393(12) Uani 1 1 d . . . H9A H 0.7786 0.3423 0.4008 0.047 Uiso 1 1 calc R . . C10 C 0.5930(6) 0.4288(6) 0.3131(7) 0.0467(14) Uani 1 1 d . . . H10A H 0.5613 0.3562 0.2821 0.056 Uiso 1 1 calc R . . C11 C 0.5097(6) 0.5451(6) 0.2890(7) 0.0477(14) Uani 1 1 d . . . H11A H 0.4226 0.5516 0.2381 0.057 Uiso 1 1 calc R . . C12 C 0.5578(6) 0.6525(5) 0.3418(6) 0.0376(12) Uani 1 1 d . . . C13 C 0.6905(5) 0.6367(5) 0.4107(6) 0.0328(11) Uani 1 1 d . . . H13A H 0.7225 0.7089 0.4465 0.039 Uiso 1 1 calc R . . C14 C 0.4770(6) 0.7767(6) 0.3028(7) 0.0435(13) Uani 1 1 d . . . C15 C 0.4823(7) 0.9079(6) 0.5793(6) 0.0503(15) Uani 1 1 d . . . H15A H 0.5204 0.8247 0.6038 0.060 Uiso 1 1 calc R . . H15B H 0.3868 0.9497 0.6318 0.060 Uiso 1 1 calc R . . C16 C 0.4183(7) 1.0106(6) 0.3595(7) 0.0556(17) Uani 1 1 d . . . H16A H 0.3200 1.0565 0.4023 0.067 Uiso 1 1 calc R . . H16B H 0.4174 0.9936 0.2450 0.067 Uiso 1 1 calc R . . O1 O 0.7735(4) 0.8436(4) 0.1241(5) 0.0523(11) Uani 1 1 d . . . O2 O 0.4259(5) 0.7731(5) 0.1702(5) 0.0617(12) Uani 1 1 d . . . O3 O 0.5475(7) 0.8063(6) 0.8985(7) 0.0784(16) Uani 1 1 d . . . H3F H 0.623(11) 0.834(9) 0.943(12) 0.11(3) Uiso 1 1 d . . . H3E H 0.509(10) 0.792(9) 0.972(11) 0.09(3) Uiso 1 1 d . . . O4 O 0.0580(14) 0.959(2) 0.507(2) 0.155(10) Uani 0.50 1 d P . . 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 Ni1 0.0351(5) 0.0233(5) 0.0259(5) 0.0089(4) -0.0036(4) -0.0067(4) Cl1 0.0437(8) 0.0285(7) 0.0344(7) 0.0077(5) -0.0037(5) -0.0077(5) N1 0.040(2) 0.029(2) 0.026(2) 0.0091(17) -0.0025(17) -0.0111(18) N2 0.030(3) 0.068(3) 0.127(5) 0.074(4) -0.020(3) -0.017(2) N3 0.040(2) 0.030(2) 0.031(2) 0.0084(18) -0.0035(18) -0.0106(18) N4 0.048(3) 0.047(3) 0.041(3) 0.020(2) -0.006(2) 0.000(2) C1 0.036(3) 0.034(3) 0.037(3) 0.012(2) -0.004(2) -0.011(2) C2 0.046(3) 0.042(3) 0.033(3) 0.008(2) 0.004(2) -0.017(3) C3 0.049(3) 0.058(3) 0.031(3) 0.023(3) -0.004(2) -0.027(3) C4 0.036(3) 0.039(3) 0.032(3) 0.015(2) -0.006(2) -0.017(2) C5 0.041(3) 0.035(3) 0.031(2) 0.011(2) -0.003(2) -0.013(2) C6 0.043(3) 0.047(3) 0.045(3) 0.028(3) -0.008(2) -0.021(3) C7 0.029(3) 0.135(8) 0.289(15) 0.184(10) -0.014(5) -0.010(4) C8 0.026(4) 0.170(10) 0.42(2) 0.244(14) -0.042(7) -0.026(5) C9 0.042(3) 0.036(3) 0.042(3) 0.008(2) 0.004(2) -0.016(2) C10 0.050(4) 0.046(3) 0.050(3) 0.006(3) 0.001(3) -0.027(3) C11 0.037(3) 0.063(4) 0.047(3) 0.015(3) -0.012(2) -0.021(3) C12 0.035(3) 0.047(3) 0.034(3) 0.015(2) -0.003(2) -0.013(2) C13 0.034(3) 0.033(3) 0.034(3) 0.012(2) -0.006(2) -0.012(2) C14 0.032(3) 0.057(4) 0.048(3) 0.025(3) -0.009(2) -0.012(3) C15 0.056(4) 0.049(3) 0.038(3) 0.019(3) 0.006(3) 0.002(3) C16 0.064(4) 0.049(4) 0.045(3) 0.020(3) -0.016(3) 0.001(3) O1 0.039(2) 0.059(3) 0.072(3) 0.037(2) -0.0018(19) -0.0168(19) O2 0.065(3) 0.076(3) 0.055(3) 0.032(2) -0.031(2) -0.026(2) O3 0.084(4) 0.107(5) 0.055(3) 0.027(3) -0.020(3) -0.041(4) O4 0.119(14) 0.27(3) 0.086(9) -0.034(13) 0.019(13) -0.14(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 Ni1 N1 2.164(4) . ? Ni1 N1 2.164(4) 2_766 ? Ni1 N3 2.191(4) 2_766 ? Ni1 N3 2.191(4) . ? Ni1 Cl1 2.4237(14) 2_766 ? Ni1 Cl1 2.4237(14) . ? N1 C5 1.334(6) . ? N1 C1 1.345(6) . ? N2 C6 1.330(7) . ? N2 C8 1.458(8) . ? N2 C7 1.474(7) . ? N3 C13 1.342(6) . ? N3 C9 1.345(6) . ? N4 C14 1.347(8) . ? N4 C16 1.458(7) . ? N4 C15 1.471(7) . ? C1 C2 1.382(7) . ? C1 H1A 0.9300 . ? C2 C3 1.372(8) . ? C2 H2A 0.9300 . ? C3 C4 1.389(8) . ? C3 H3A 0.9300 . ? C4 C5 1.390(7) . ? C4 C6 1.501(7) . ? C5 H5A 0.9300 . ? C6 O1 1.230(6) . ? C7 C8 1.199(11) 2_775 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C7 1.199(11) 2_775 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.376(8) . ? C9 H9A 0.9300 . ? C10 C11 1.375(8) . ? C10 H10A 0.9300 . ? C11 C12 1.387(8) . ? C11 H11A 0.9300 . ? C12 C13 1.379(7) . ? C12 C14 1.494(7) . ? C13 H13A 0.9300 . ? C14 O2 1.239(7) . ? C15 C16 1.512(9) 2_676 ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C15 1.512(9) 2_676 ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? O3 H3F 0.91(10) . ? O3 H3E 0.82(9) . ? O4 O4 1.24(4) 2_576 ? 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 N1 Ni1 N1 180.00(19) . 2_766 ? N1 Ni1 N3 87.51(15) . 2_766 ? N1 Ni1 N3 92.49(15) 2_766 2_766 ? N1 Ni1 N3 92.49(15) . . ? N1 Ni1 N3 87.51(15) 2_766 . ? N3 Ni1 N3 180.0 2_766 . ? N1 Ni1 Cl1 90.30(11) . 2_766 ? N1 Ni1 Cl1 89.70(11) 2_766 2_766 ? N3 Ni1 Cl1 89.59(11) 2_766 2_766 ? N3 Ni1 Cl1 90.41(11) . 2_766 ? N1 Ni1 Cl1 89.70(11) . . ? N1 Ni1 Cl1 90.30(11) 2_766 . ? N3 Ni1 Cl1 90.41(11) 2_766 . ? N3 Ni1 Cl1 89.59(11) . . ? Cl1 Ni1 Cl1 180.000(1) 2_766 . ? C5 N1 C1 117.0(4) . . ? C5 N1 Ni1 122.0(3) . . ? C1 N1 Ni1 120.9(3) . . ? C6 N2 C8 127.4(5) . . ? C6 N2 C7 119.6(5) . . ? C8 N2 C7 112.9(5) . . ? C13 N3 C9 117.2(4) . . ? C13 N3 Ni1 120.7(3) . . ? C9 N3 Ni1 121.7(3) . . ? C14 N4 C16 120.6(5) . . ? C14 N4 C15 125.5(5) . . ? C16 N4 C15 112.9(5) . . ? N1 C1 C2 122.7(5) . . ? N1 C1 H1A 118.7 . . ? C2 C1 H1A 118.7 . . ? C3 C2 C1 119.4(5) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? C2 C3 C4 119.2(5) . . ? C2 C3 H3A 120.4 . . ? C4 C3 H3A 120.4 . . ? C3 C4 C5 117.4(5) . . ? C3 C4 C6 125.4(4) . . ? C5 C4 C6 116.8(5) . . ? N1 C5 C4 124.3(5) . . ? N1 C5 H5A 117.8 . . ? C4 C5 H5A 117.8 . . ? O1 C6 N2 122.4(5) . . ? O1 C6 C4 118.0(5) . . ? N2 C6 C4 119.7(5) . . ? C8 C7 N2 119.5(7) 2_775 . ? C8 C7 H7A 107.5 2_775 . ? N2 C7 H7A 107.5 . . ? C8 C7 H7B 107.5 2_775 . ? N2 C7 H7B 107.5 . . ? H7A C7 H7B 107.0 . . ? C7 C8 N2 123.8(7) 2_775 . ? C7 C8 H8A 106.4 2_775 . ? N2 C8 H8A 106.4 . . ? C7 C8 H8B 106.4 2_775 . ? N2 C8 H8B 106.4 . . ? H8A C8 H8B 106.5 . . ? N3 C9 C10 122.7(5) . . ? N3 C9 H9A 118.6 . . ? C10 C9 H9A 118.6 . . ? C11 C10 C9 119.3(5) . . ? C11 C10 H10A 120.3 . . ? C9 C10 H10A 120.3 . . ? C10 C11 C12 118.8(5) . . ? C10 C11 H11A 120.6 . . ? C12 C11 H11A 120.6 . . ? C13 C12 C11 118.3(5) . . ? C13 C12 C14 121.4(5) . . ? C11 C12 C14 119.7(5) . . ? N3 C13 C12 123.4(5) . . ? N3 C13 H13A 118.3 . . ? C12 C13 H13A 118.3 . . ? O2 C14 N4 121.5(5) . . ? O2 C14 C12 118.6(5) . . ? N4 C14 C12 119.8(5) . . ? N4 C15 C16 111.0(5) . 2_676 ? N4 C15 H15A 109.4 . . ? C16 C15 H15A 109.4 2_676 . ? N4 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 2_676 . ? H15A C15 H15B 108.0 . . ? N4 C16 C15 109.4(5) . 2_676 ? N4 C16 H16A 109.8 . . ? C15 C16 H16A 109.8 2_676 . ? N4 C16 H16B 109.8 . . ? C15 C16 H16B 109.8 2_676 . ? H16A C16 H16B 108.2 . . ? H3F O3 H3E 104(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 N1 Ni1 N1 C5 88(100) 2_766 . . . ? N3 Ni1 N1 C5 -123.6(4) 2_766 . . . ? N3 Ni1 N1 C5 56.4(4) . . . . ? Cl1 Ni1 N1 C5 -34.0(4) 2_766 . . . ? Cl1 Ni1 N1 C5 146.0(4) . . . . ? N1 Ni1 N1 C1 -86(100) 2_766 . . . ? N3 Ni1 N1 C1 61.6(4) 2_766 . . . ? N3 Ni1 N1 C1 -118.4(4) . . . . ? Cl1 Ni1 N1 C1 151.1(4) 2_766 . . . ? Cl1 Ni1 N1 C1 -28.9(4) . . . . ? N1 Ni1 N3 C13 -58.9(4) . . . . ? N1 Ni1 N3 C13 121.1(4) 2_766 . . . ? N3 Ni1 N3 C13 167(100) 2_766 . . . ? Cl1 Ni1 N3 C13 31.4(4) 2_766 . . . ? Cl1 Ni1 N3 C13 -148.6(4) . . . . ? N1 Ni1 N3 C9 113.3(4) . . . . ? N1 Ni1 N3 C9 -66.7(4) 2_766 . . . ? N3 Ni1 N3 C9 -20(100) 2_766 . . . ? Cl1 Ni1 N3 C9 -156.4(4) 2_766 . . . ? Cl1 Ni1 N3 C9 23.6(4) . . . . ? C5 N1 C1 C2 -2.1(7) . . . . ? Ni1 N1 C1 C2 173.0(4) . . . . ? N1 C1 C2 C3 0.6(8) . . . . ? C1 C2 C3 C4 1.0(8) . . . . ? C2 C3 C4 C5 -0.9(7) . . . . ? C2 C3 C4 C6 -172.7(5) . . . . ? C1 N1 C5 C4 2.2(7) . . . . ? Ni1 N1 C5 C4 -172.8(4) . . . . ? C3 C4 C5 N1 -0.8(8) . . . . ? C6 C4 C5 N1 171.8(5) . . . . ? C8 N2 C6 O1 172.8(10) . . . . ? C7 N2 C6 O1 -5.8(11) . . . . ? C8 N2 C6 C4 -6.9(13) . . . . ? C7 N2 C6 C4 174.5(8) . . . . ? C3 C4 C6 O1 124.6(6) . . . . ? C5 C4 C6 O1 -47.3(7) . . . . ? C3 C4 C6 N2 -55.7(8) . . . . ? C5 C4 C6 N2 132.4(6) . . . . ? C6 N2 C7 C8 -160.2(13) . . . 2_775 ? C8 N2 C7 C8 21(2) . . . 2_775 ? C6 N2 C8 C7 159.2(14) . . . 2_775 ? C7 N2 C8 C7 -22(2) . . . 2_775 ? C13 N3 C9 C10 3.8(7) . . . . ? Ni1 N3 C9 C10 -168.7(4) . . . . ? N3 C9 C10 C11 -1.0(8) . . . . ? C9 C10 C11 C12 -2.3(8) . . . . ? C10 C11 C12 C13 2.6(8) . . . . ? C10 C11 C12 C14 173.9(5) . . . . ? C9 N3 C13 C12 -3.5(7) . . . . ? Ni1 N3 C13 C12 169.1(4) . . . . ? C11 C12 C13 N3 0.3(8) . . . . ? C14 C12 C13 N3 -170.8(5) . . . . ? C16 N4 C14 O2 -8.3(9) . . . . ? C15 N4 C14 O2 159.3(6) . . . . ? C16 N4 C14 C12 167.2(5) . . . . ? C15 N4 C14 C12 -25.3(8) . . . . ? C13 C12 C14 O2 132.9(6) . . . . ? C11 C12 C14 O2 -38.1(8) . . . . ? C13 C12 C14 N4 -42.7(7) . . . . ? C11 C12 C14 N4 146.3(6) . . . . ? C14 N4 C15 C16 134.8(6) . . . 2_676 ? C16 N4 C15 C16 -56.8(7) . . . 2_676 ? C14 N4 C16 C15 -135.1(6) . . . 2_676 ? C15 N4 C16 C15 55.9(7) . . . 2_676 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3F O1 0.91(10) 2.12(10) 2.946(7) 151(8) 1_556 O3 H3E O2 0.82(9) 2.01(10) 2.823(8) 173(9) 1_556 _diffrn_measured_fraction_theta_max 0.791 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.791 _refine_diff_density_max 0.869 _refine_diff_density_min -0.680 _refine_diff_density_rms 0.095 data_Complex_3_b _database_code_depnum_ccdc_archive 'CCDC 254995' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 Cl2 N4 O2 Zn' _chemical_formula_weight 432.60 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' Zn Zn 0.2839 1.4301 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.925(5) _cell_length_b 6.3403(13) _cell_length_c 12.061(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.62(3) _cell_angle_gamma 90.00 _cell_volume 1753.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 310 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25.1 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.639 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 1.723 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7244 _exptl_absorpt_correction_T_max 0.7467 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 R-AXIS-IV _diffrn_measurement_method 'Oscillation frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2392 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1384 _reflns_number_gt 1273 _reflns_threshold_expression >2sigma(I) _computing_data_collection raxis _computing_cell_refinement raxis _computing_data_reduction raxis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics texsan _computing_publication_material texsan _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^)+(0.0371P)^2^+0.1465P] 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 SHELXL _refine_ls_extinction_coef 0.0007(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1384 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0394 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0654 _refine_ls_wR_factor_gt 0.0634 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 Zn1 Zn 0.5000 0.62520(7) 0.7500 0.02770(18) Uani 1 2 d S . . Cl1 Cl 0.43799(3) 0.44504(12) 0.60792(6) 0.0370(2) Uani 1 1 d . . . O1 O 0.73732(8) 0.7918(3) 0.77767(14) 0.0364(5) Uani 1 1 d . . . N1 N 0.55316(9) 0.8263(3) 0.69129(17) 0.0265(5) Uani 1 1 d . . . N2 N 0.72929(9) 0.8417(4) 0.58741(17) 0.0271(5) Uani 1 1 d . . . C1 C 0.53353(12) 1.0128(5) 0.6442(2) 0.0303(6) Uani 1 1 d . . . H1A H 0.4952 1.0501 0.6384 0.036 Uiso 1 1 calc R . . C2 C 0.56726(12) 1.1521(4) 0.6041(2) 0.0317(7) Uani 1 1 d . . . H2A H 0.5522 1.2813 0.5729 0.038 Uiso 1 1 calc R . . C3 C 0.62389(12) 1.0965(4) 0.6110(2) 0.0292(6) Uani 1 1 d . . . H3A H 0.6475 1.1872 0.5838 0.035 Uiso 1 1 calc R . . C4 C 0.64519(11) 0.9029(4) 0.6594(2) 0.0251(6) Uani 1 1 d . . . C5 C 0.60878(11) 0.7752(5) 0.7000(2) 0.0278(6) Uani 1 1 d . . . H5A H 0.6233 0.6481 0.7351 0.033 Uiso 1 1 calc R . . C6 C 0.70819(11) 0.8374(4) 0.6796(2) 0.0248(6) Uani 1 1 d . . . C7 C 0.69579(12) 0.8662(5) 0.4659(2) 0.0309(6) Uani 1 1 d . . . C8 C 0.79185(12) 0.8178(5) 0.6039(2) 0.0328(7) Uani 1 1 d . . . H8B H 0.8096(12) 0.803(5) 0.682(2) 0.039 Uiso 1 1 d . . . H7B H 0.6544(14) 0.864(5) 0.459(2) 0.039 Uiso 1 1 d . . . H8A H 0.8058(13) 0.944(5) 0.582(2) 0.039 Uiso 1 1 d . . . H7 H 0.7065(13) 0.992(5) 0.439(2) 0.039 Uiso 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 Zn1 0.0200(3) 0.0280(3) 0.0387(3) 0.000 0.01410(19) 0.000 Cl1 0.0295(4) 0.0378(5) 0.0434(4) -0.0054(3) 0.0097(3) -0.0025(3) O1 0.0303(11) 0.0514(14) 0.0304(10) 0.0052(9) 0.0131(8) 0.0085(10) N1 0.0208(12) 0.0285(14) 0.0334(11) 0.0005(9) 0.0129(9) 0.0009(10) N2 0.0172(11) 0.0412(15) 0.0248(10) -0.0040(9) 0.0093(9) -0.0020(10) C1 0.0228(15) 0.0373(18) 0.0331(14) -0.0002(13) 0.0116(11) 0.0048(13) C2 0.0353(16) 0.0292(17) 0.0341(14) 0.0054(12) 0.0158(12) 0.0064(12) C3 0.0302(15) 0.0289(16) 0.0328(13) 0.0007(12) 0.0158(11) -0.0035(12) C4 0.0226(14) 0.0313(16) 0.0248(12) -0.0040(11) 0.0121(10) -0.0022(12) C5 0.0241(15) 0.0289(16) 0.0328(13) 0.0032(12) 0.0120(11) 0.0042(12) C6 0.0227(14) 0.0246(16) 0.0294(14) -0.0033(11) 0.0112(11) -0.0008(11) C7 0.0205(14) 0.0451(19) 0.0282(13) 0.0004(13) 0.0087(11) 0.0006(13) C8 0.0181(14) 0.052(2) 0.0292(14) -0.0058(14) 0.0081(11) -0.0036(13) _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 Zn1 N1 2.064(2) 2_656 ? Zn1 N1 2.064(2) . ? Zn1 Cl1 2.2334(10) . ? Zn1 Cl1 2.2335(10) 2_656 ? O1 C6 1.224(3) . ? N1 C1 1.338(4) . ? N1 C5 1.344(3) . ? N2 C6 1.346(3) . ? N2 C8 1.460(3) . ? N2 C7 1.463(3) . ? C1 C2 1.374(4) . ? C1 H1A 0.9300 . ? C2 C3 1.379(4) . ? C2 H2A 0.9300 . ? C3 C4 1.391(4) . ? C3 H3A 0.9300 . ? C4 C5 1.379(4) . ? C4 C6 1.514(3) . ? C5 H5A 0.9300 . ? C7 C8 1.517(4) 7_666 ? C7 H7B 0.97(3) . ? C7 H7 0.93(3) . ? C8 C7 1.517(4) 7_666 ? C8 H8B 0.92(3) . ? C8 H8A 0.94(3) . ? 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 N1 Zn1 N1 103.70(12) 2_656 . ? N1 Zn1 Cl1 103.88(6) 2_656 . ? N1 Zn1 Cl1 113.08(6) . . ? N1 Zn1 Cl1 113.08(6) 2_656 2_656 ? N1 Zn1 Cl1 103.88(6) . 2_656 ? Cl1 Zn1 Cl1 118.48(5) . 2_656 ? C1 N1 C5 117.8(2) . . ? C1 N1 Zn1 121.04(17) . . ? C5 N1 Zn1 121.17(18) . . ? C6 N2 C8 119.8(2) . . ? C6 N2 C7 127.0(2) . . ? C8 N2 C7 113.20(19) . . ? N1 C1 C2 123.2(2) . . ? N1 C1 H1A 118.4 . . ? C2 C1 H1A 118.4 . . ? C1 C2 C3 118.7(3) . . ? C1 C2 H2A 120.7 . . ? C3 C2 H2A 120.7 . . ? C2 C3 C4 119.1(2) . . ? C2 C3 H3A 120.4 . . ? C4 C3 H3A 120.4 . . ? C5 C4 C3 118.3(2) . . ? C5 C4 C6 118.8(2) . . ? C3 C4 C6 122.6(2) . . ? N1 C5 C4 122.9(3) . . ? N1 C5 H5A 118.6 . . ? C4 C5 H5A 118.6 . . ? O1 C6 N2 124.0(2) . . ? O1 C6 C4 119.1(2) . . ? N2 C6 C4 116.9(2) . . ? N2 C7 C8 109.6(2) . 7_666 ? N2 C7 H7B 110.1(16) . . ? C8 C7 H7B 107.2(17) 7_666 . ? N2 C7 H7 108.6(18) . . ? C8 C7 H7 110.4(18) 7_666 . ? H7B C7 H7 111(3) . . ? N2 C8 C7 111.0(2) . 7_666 ? N2 C8 H8B 107.9(17) . . ? C7 C8 H8B 112.3(19) 7_666 . ? N2 C8 H8A 107.9(19) . . ? C7 C8 H8A 110.9(18) 7_666 . ? H8B C8 H8A 107(3) . . ? 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 N1 Zn1 N1 C1 -32.90(17) 2_656 . . . ? Cl1 Zn1 N1 C1 79.0(2) . . . . ? Cl1 Zn1 N1 C1 -151.32(18) 2_656 . . . ? N1 Zn1 N1 C5 146.4(2) 2_656 . . . ? Cl1 Zn1 N1 C5 -101.7(2) . . . . ? Cl1 Zn1 N1 C5 28.0(2) 2_656 . . . ? C5 N1 C1 C2 0.5(4) . . . . ? Zn1 N1 C1 C2 179.89(19) . . . . ? N1 C1 C2 C3 0.9(4) . . . . ? C1 C2 C3 C4 -0.7(4) . . . . ? C2 C3 C4 C5 -0.9(4) . . . . ? C2 C3 C4 C6 -174.7(2) . . . . ? C1 N1 C5 C4 -2.2(4) . . . . ? Zn1 N1 C5 C4 178.40(18) . . . . ? C3 C4 C5 N1 2.4(4) . . . . ? C6 C4 C5 N1 176.5(2) . . . . ? C8 N2 C6 O1 -8.2(4) . . . . ? C7 N2 C6 O1 171.1(3) . . . . ? C8 N2 C6 C4 169.0(2) . . . . ? C7 N2 C6 C4 -11.8(4) . . . . ? C5 C4 C6 O1 -51.7(3) . . . . ? C3 C4 C6 O1 122.0(3) . . . . ? C5 C4 C6 N2 131.0(3) . . . . ? C3 C4 C6 N2 -55.3(3) . . . . ? C6 N2 C7 C8 -123.9(3) . . . 7_666 ? C8 N2 C7 C8 55.4(3) . . . 7_666 ? C6 N2 C8 C7 123.2(3) . . . 7_666 ? C7 N2 C8 C7 -56.2(4) . . . 7_666 ? _diffrn_measured_fraction_theta_max 0.893 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.893 _refine_diff_density_max 0.370 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.061