data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Chris Adams' 'Mukhtar Kurawa' A.Orpen _publ_contact_author_name 'Chris Adams' _publ_contact_author_email chcja@bris.ac.uk _publ_section_title ; Coordination chemistry in the solid state: synthesis and interconversion of pyrazolium salts, pyrazole complexes, and pyrazolate MOFs ; # Attachment '- Combined CIFs.cif' data_1LT _database_code_depnum_ccdc_archive 'CCDC 771207' #TrackingRef '- Combined CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H10 Cl4 Co N4' _chemical_formula_weight 338.91 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.5428(16) _cell_length_b 12.724(3) _cell_length_c 13.045(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.600(9) _cell_angle_gamma 90.00 _cell_volume 1250.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10250 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 27.46 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.800 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 2.199 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.350 _exptl_absorpt_correction_T_max 0.686 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _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_% 0 _diffrn_reflns_number 12687 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0180 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2854 _reflns_number_gt 2787 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0170P)^2^+1.2946P] 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_number_reflns 2854 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0235 _refine_ls_R_factor_gt 0.0226 _refine_ls_wR_factor_ref 0.0590 _refine_ls_wR_factor_gt 0.0581 _refine_ls_goodness_of_fit_ref 1.244 _refine_ls_restrained_S_all 1.244 _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 0.23196(3) 0.789993(18) 0.246235(18) 0.01006(7) Uani 1 1 d . . . Cl1 Cl 0.22560(6) 0.97157(3) 0.23981(3) 0.01267(10) Uani 1 1 d . . . Cl2 Cl 0.25717(6) 0.74202(3) 0.41409(3) 0.01323(10) Uani 1 1 d . . . Cl3 Cl -0.02315(6) 0.72688(4) 0.17512(3) 0.01511(10) Uani 1 1 d . . . Cl4 Cl 0.46958(6) 0.73936(3) 0.15718(4) 0.01578(10) Uani 1 1 d . . . N1 N 0.2809(2) 0.02525(14) 0.47510(13) 0.0197(3) Uani 1 1 d . . . H1A H 0.3036 0.0159 0.4102 0.024 Uiso 1 1 calc R . . N2 N 0.2110(2) -0.04699(13) 0.53628(13) 0.0191(3) Uani 1 1 d . . . H2A H 0.1784 -0.1109 0.5178 0.023 Uiso 1 1 calc R . . N3 N 0.1518(2) 0.54714(13) 0.61640(13) 0.0204(4) Uani 1 1 d . . . H3A H 0.1128 0.6108 0.6289 0.024 Uiso 1 1 calc R . . N4 N 0.0541(2) 0.45918(14) 0.61675(13) 0.0195(4) Uani 1 1 d . . . H4A H -0.0596 0.4559 0.6289 0.023 Uiso 1 1 calc R . . C1 C 0.1991(3) -0.00627(15) 0.62934(15) 0.0183(4) Uani 1 1 d . . . H1B H 0.1560 -0.0414 0.6875 0.022 Uiso 1 1 calc R . . C2 C 0.2605(3) 0.09649(15) 0.62712(15) 0.0185(4) Uani 1 1 d . . . H2B H 0.2667 0.1451 0.6824 0.022 Uiso 1 1 calc R . . C3 C 0.3105(3) 0.11338(16) 0.52821(16) 0.0198(4) Uani 1 1 d . . . H3B H 0.3578 0.1768 0.5024 0.024 Uiso 1 1 calc R . . C4 C 0.3166(3) 0.52273(16) 0.59422(16) 0.0198(4) Uani 1 1 d . . . H4B H 0.4121 0.5707 0.5884 0.024 Uiso 1 1 calc R . . C5 C 0.3248(3) 0.41484(16) 0.58107(16) 0.0191(4) Uani 1 1 d . . . H5A H 0.4261 0.3747 0.5651 0.023 Uiso 1 1 calc R . . C6 C 0.1568(3) 0.37760(15) 0.59572(16) 0.0185(4) Uani 1 1 d . . . H6A H 0.1204 0.3062 0.5916 0.022 Uiso 1 1 calc R . . 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 0.00932(12) 0.01082(12) 0.01008(13) -0.00077(8) 0.00094(9) -0.00085(8) Cl1 0.0142(2) 0.01070(19) 0.0133(2) -0.00009(14) 0.00281(16) -0.00016(14) Cl2 0.0166(2) 0.01214(19) 0.0108(2) 0.00029(14) -0.00023(15) 0.00026(15) Cl3 0.0127(2) 0.0177(2) 0.0147(2) -0.00157(16) -0.00148(16) -0.00334(15) Cl4 0.0141(2) 0.01115(19) 0.0227(2) -0.00193(16) 0.00768(17) -0.00016(15) N1 0.0221(9) 0.0260(9) 0.0109(8) -0.0031(6) 0.0014(6) 0.0054(7) N2 0.0221(9) 0.0131(8) 0.0217(9) -0.0031(6) -0.0044(7) 0.0010(6) N3 0.0310(10) 0.0149(8) 0.0150(8) -0.0024(6) -0.0013(7) 0.0084(7) N4 0.0134(8) 0.0262(9) 0.0193(9) 0.0030(7) 0.0053(6) 0.0043(6) C1 0.0225(10) 0.0150(9) 0.0176(9) 0.0021(7) 0.0016(8) 0.0009(7) C2 0.0283(11) 0.0135(9) 0.0137(9) -0.0015(7) 0.0000(8) 0.0003(8) C3 0.0234(10) 0.0179(9) 0.0182(10) 0.0033(7) -0.0004(8) -0.0014(7) C4 0.0216(10) 0.0191(9) 0.0184(10) 0.0010(7) -0.0020(8) -0.0041(8) C5 0.0152(9) 0.0189(9) 0.0235(10) 0.0003(8) 0.0055(7) 0.0035(7) C6 0.0194(10) 0.0147(9) 0.0216(10) 0.0006(7) 0.0042(8) -0.0005(7) _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 Cl3 2.2464(6) . ? Co1 Cl2 2.2728(7) . ? Co1 Cl4 2.2728(6) . ? Co1 Cl1 2.3124(7) . ? N1 C3 1.332(3) . ? N1 N2 1.341(2) . ? N1 H1A 0.8800 . ? N2 C1 1.327(3) . ? N2 H2A 0.8800 . ? N3 C4 1.327(3) . ? N3 N4 1.340(2) . ? N3 H3A 0.8800 . ? N4 C6 1.331(3) . ? N4 H4A 0.8800 . ? C1 C2 1.388(3) . ? C1 H1B 0.9500 . ? C2 C3 1.378(3) . ? C2 H2B 0.9500 . ? C3 H3B 0.9500 . ? C4 C5 1.385(3) . ? C4 H4B 0.9500 . ? C5 C6 1.374(3) . ? C5 H5A 0.9500 . ? C6 H6A 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 Cl3 Co1 Cl2 109.54(2) . . ? Cl3 Co1 Cl4 111.60(2) . . ? Cl2 Co1 Cl4 112.51(2) . . ? Cl3 Co1 Cl1 109.039(19) . . ? Cl2 Co1 Cl1 107.697(18) . . ? Cl4 Co1 Cl1 106.276(18) . . ? C3 N1 N2 109.19(16) . . ? C3 N1 H1A 125.4 . . ? N2 N1 H1A 125.4 . . ? C1 N2 N1 108.77(16) . . ? C1 N2 H2A 125.6 . . ? N1 N2 H2A 125.6 . . ? C4 N3 N4 109.03(16) . . ? C4 N3 H3A 125.5 . . ? N4 N3 H3A 125.5 . . ? C6 N4 N3 109.00(16) . . ? C6 N4 H4A 125.5 . . ? N3 N4 H4A 125.5 . . ? N2 C1 C2 108.20(18) . . ? N2 C1 H1B 125.9 . . ? C2 C1 H1B 125.9 . . ? C3 C2 C1 105.80(17) . . ? C3 C2 H2B 127.1 . . ? C1 C2 H2B 127.1 . . ? N1 C3 C2 108.02(18) . . ? N1 C3 H3B 126.0 . . ? C2 C3 H3B 126.0 . . ? N3 C4 C5 107.85(18) . . ? N3 C4 H4B 126.1 . . ? C5 C4 H4B 126.1 . . ? C6 C5 C4 106.14(18) . . ? C6 C5 H5A 126.9 . . ? C4 C5 H5A 126.9 . . ? N4 C6 C5 107.98(17) . . ? N4 C6 H6A 126.0 . . ? C5 C6 H6A 126.0 . . ? 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 C3 N1 N2 C1 -1.3(2) . . . . ? C4 N3 N4 C6 0.6(2) . . . . ? N1 N2 C1 C2 1.2(2) . . . . ? N2 C1 C2 C3 -0.6(2) . . . . ? N2 N1 C3 C2 1.0(2) . . . . ? C1 C2 C3 N1 -0.2(2) . . . . ? N4 N3 C4 C5 -0.7(2) . . . . ? N3 C4 C5 C6 0.5(2) . . . . ? N3 N4 C6 C5 -0.3(2) . . . . ? C4 C5 C6 N4 -0.1(2) . . . . ? 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 N1 H1A Cl1 0.88 2.34 3.1537(18) 153.5 1_545 N2 H2A Cl2 0.88 2.40 3.1497(18) 143.3 1_545 N3 H3A Cl4 0.88 2.23 3.1012(17) 170.6 4_576 N4 H4A Cl1 0.88 2.40 3.1391(18) 141.1 4_576 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.385 _refine_diff_density_min -0.579 _refine_diff_density_rms 0.090 # = = = END data_1RT _database_code_depnum_ccdc_archive 'CCDC 771208' #TrackingRef '- Combined CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H10 Cl4 Co N4' _chemical_formula_weight 338.91 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.6306(7) _cell_length_b 12.8943(13) _cell_length_c 13.3727(14) _cell_angle_alpha 90.00 _cell_angle_beta 92.822(4) _cell_angle_gamma 90.00 _cell_volume 1314.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9203 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 27.33 _exptl_crystal_description Block _exptl_crystal_colour Blue _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.713 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 2.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.376 _exptl_absorpt_correction_T_max 0.6561 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _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 13390 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 27.38 _reflns_number_total 2964 _reflns_number_gt 2619 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0400P)^2^+0.5628P] 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 SHELXL _refine_ls_extinction_coef 0.110(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2964 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0827 _refine_ls_wR_factor_gt 0.0786 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _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 0.23929(3) 0.78961(2) 0.248982(18) 0.03709(13) Uani 1 1 d . . . Cl1 Cl 0.23505(7) 0.96813(4) 0.24371(4) 0.04759(16) Uani 1 1 d . . . Cl2 Cl 0.25728(8) 0.74149(4) 0.41259(4) 0.05273(17) Uani 1 1 d . . . Cl3 Cl -0.01111(7) 0.73057(5) 0.17299(4) 0.05473(18) Uani 1 1 d . . . Cl4 Cl 0.47837(8) 0.74064(4) 0.16585(5) 0.0605(2) Uani 1 1 d . . . N1 N 0.2756(4) 0.0252(2) 0.47342(17) 0.0764(7) Uani 1 1 d . . . H1A H 0.2943 0.0179 0.4109 0.092 Uiso 1 1 calc R . . N2 N 0.2183(4) -0.04738(19) 0.5319(2) 0.0783(8) Uani 1 1 d . . . H2A H 0.1947 -0.1102 0.5141 0.094 Uiso 1 1 calc R . . N3 N 0.1555(5) 0.5490(2) 0.61894(18) 0.0786(8) Uani 1 1 d . . . H3A H 0.1131 0.6098 0.6283 0.094 Uiso 1 1 calc R . . N4 N 0.0685(4) 0.4633(3) 0.6214(2) 0.0904(9) Uani 1 1 d . . . H4A H -0.0405 0.4580 0.6343 0.108 Uiso 1 1 calc R . . C1 C 0.2023(5) -0.0093(3) 0.6217(2) 0.0764(8) Uani 1 1 d . . . H1B H 0.1638 -0.0451 0.6769 0.092 Uiso 1 1 calc R . . C2 C 0.2522(5) 0.0917(2) 0.6199(2) 0.0777(9) Uani 1 1 d . . . H2B H 0.2533 0.1385 0.6729 0.093 Uiso 1 1 calc R . . C3 C 0.3002(5) 0.1109(2) 0.5250(2) 0.0773(9) Uani 1 1 d . . . H3B H 0.3427 0.1733 0.5012 0.093 Uiso 1 1 calc R . . C4 C 0.3190(5) 0.5287(3) 0.5999(3) 0.0845(10) Uani 1 1 d . . . H4B H 0.4102 0.5761 0.5955 0.101 Uiso 1 1 calc R . . C5 C 0.3277(5) 0.4233(3) 0.5880(3) 0.0958(12) Uani 1 1 d . . . H5A H 0.4258 0.3845 0.5730 0.115 Uiso 1 1 calc R . . C6 C 0.1689(6) 0.3881(3) 0.6019(3) 0.0911(11) Uani 1 1 d . . . H6A H 0.1352 0.3188 0.5981 0.109 Uiso 1 1 calc R . . 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 0.03618(17) 0.03702(18) 0.03821(18) -0.00300(10) 0.00312(11) -0.00208(10) Cl1 0.0570(3) 0.0367(3) 0.0499(3) -0.0009(2) 0.0102(2) 0.0002(2) Cl2 0.0725(4) 0.0432(3) 0.0420(3) 0.0018(2) -0.0027(2) -0.0016(2) Cl3 0.0456(3) 0.0589(4) 0.0586(4) -0.0075(3) -0.0084(2) -0.0067(2) Cl4 0.0524(3) 0.0405(3) 0.0911(5) -0.0086(3) 0.0296(3) -0.0002(2) N1 0.0839(17) 0.099(2) 0.0461(12) -0.0128(13) 0.0039(11) 0.0244(15) N2 0.0889(18) 0.0507(13) 0.0925(19) -0.0224(13) -0.0220(15) 0.0021(12) N3 0.120(2) 0.0583(15) 0.0565(13) -0.0079(11) -0.0011(14) 0.0381(15) N4 0.0662(16) 0.113(3) 0.094(2) 0.0095(17) 0.0179(15) 0.0138(16) C1 0.104(2) 0.0617(17) 0.0639(17) 0.0130(14) 0.0046(16) -0.0043(17) C2 0.136(3) 0.0483(15) 0.0481(14) -0.0084(12) -0.0066(16) 0.0070(16) C3 0.109(3) 0.0565(16) 0.0661(18) 0.0113(14) 0.0032(16) -0.0067(15) C4 0.083(2) 0.082(2) 0.088(2) 0.0199(17) 0.0023(17) -0.0333(18) C5 0.087(2) 0.091(3) 0.113(3) 0.021(2) 0.043(2) 0.046(2) C6 0.104(3) 0.0591(18) 0.113(3) -0.0001(17) 0.028(2) -0.0040(18) _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 Cl3 2.2521(6) . ? Co1 Cl2 2.2718(6) . ? Co1 Cl4 2.2721(6) . ? Co1 Cl1 2.3032(6) . ? N1 N2 1.309(4) . ? N1 C3 1.311(4) . ? N1 H1A 0.8600 . ? N2 C1 1.309(4) . ? N2 H2A 0.8600 . ? N3 N4 1.290(4) . ? N3 C4 1.311(5) . ? N3 H3A 0.8600 . ? N4 C6 1.272(4) . ? N4 H4A 0.8600 . ? C1 C2 1.358(4) . ? C1 H1B 0.9300 . ? C2 C3 1.361(4) . ? C2 H2B 0.9300 . ? C3 H3B 0.9300 . ? C4 C5 1.371(5) . ? C4 H4B 0.9300 . ? C5 C6 1.316(5) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? 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 Cl3 Co1 Cl2 110.61(3) . . ? Cl3 Co1 Cl4 111.66(3) . . ? Cl2 Co1 Cl4 112.54(3) . . ? Cl3 Co1 Cl1 108.28(2) . . ? Cl2 Co1 Cl1 107.61(2) . . ? Cl4 Co1 Cl1 105.85(2) . . ? N2 N1 C3 109.4(2) . . ? N2 N1 H1A 125.3 . . ? C3 N1 H1A 125.3 . . ? C1 N2 N1 109.2(2) . . ? C1 N2 H2A 125.4 . . ? N1 N2 H2A 125.4 . . ? N4 N3 C4 109.3(3) . . ? N4 N3 H3A 125.4 . . ? C4 N3 H3A 125.4 . . ? C6 N4 N3 109.4(3) . . ? C6 N4 H4A 125.3 . . ? N3 N4 H4A 125.3 . . ? N2 C1 C2 107.8(3) . . ? N2 C1 H1B 126.1 . . ? C2 C1 H1B 126.1 . . ? C1 C2 C3 106.2(3) . . ? C1 C2 H2B 126.9 . . ? C3 C2 H2B 126.9 . . ? N1 C3 C2 107.5(3) . . ? N1 C3 H3B 126.3 . . ? C2 C3 H3B 126.3 . . ? N3 C4 C5 105.8(3) . . ? N3 C4 H4B 127.1 . . ? C5 C4 H4B 127.1 . . ? C6 C5 C4 106.0(3) . . ? C6 C5 H5A 127.0 . . ? C4 C5 H5A 127.0 . . ? N4 C6 C5 109.5(3) . . ? N4 C6 H6A 125.2 . . ? C5 C6 H6A 125.2 . . ? 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 C3 N1 N2 C1 1.0(4) . . . . ? C4 N3 N4 C6 -1.8(4) . . . . ? N1 N2 C1 C2 -0.1(4) . . . . ? N2 C1 C2 C3 -0.7(4) . . . . ? N2 N1 C3 C2 -1.4(4) . . . . ? C1 C2 C3 N1 1.3(4) . . . . ? N4 N3 C4 C5 1.5(4) . . . . ? N3 C4 C5 C6 -0.7(4) . . . . ? N3 N4 C6 C5 1.3(5) . . . . ? C4 C5 C6 N4 -0.3(5) . . . . ? 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 N1 H1A Cl1 0.86 2.35 3.159(2) 157.2 1_545 N2 H2A Cl2 0.86 2.41 3.177(2) 149.3 1_545 N3 H3A Cl4 0.86 2.25 3.109(2) 172.7 4_576 N4 H4A Cl1 0.86 2.50 3.215(3) 141.7 4_576 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.38 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.325 _refine_diff_density_min -0.634 _refine_diff_density_rms 0.096 # = = = END data_2 _database_code_depnum_ccdc_archive 'CCDC 771209' #TrackingRef '- Combined CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H16 Cl2 Co1 N4' _chemical_formula_weight 274.06 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' Cl Cl 0.1484 0.1585 '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' N N 0.0061 0.0033 '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/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 17.896(4) _cell_length_b 3.6423(7) _cell_length_c 6.8331(14) _cell_angle_alpha 90.00 _cell_angle_beta 93.99(3) _cell_angle_gamma 90.00 _cell_volume 444.32(16) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 964 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.44 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.048 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 282 _exptl_absorpt_coefficient_mu 2.486 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.557 _exptl_absorpt_correction_T_max 0.781 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _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 1559 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 27.44 _reflns_number_total 587 _reflns_number_gt 506 _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^)+(0.0341P)^2^+1.0663P] 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_number_reflns 587 _refine_ls_number_parameters 53 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0312 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0771 _refine_ls_wR_factor_gt 0.0756 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_restrained_S_all 1.166 _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 Co1 Co 0.0000 0.5000 1.0000 0.0093(2) Uani 1 4 d S . . Cl2 Cl -0.05188(4) 1.0000 0.77580(11) 0.0105(2) Uani 1 2 d S . . N1 N 0.09690(16) 0.5000 0.8492(4) 0.0106(6) Uani 1 2 d S . . N2 N 0.0986(2) 0.6179(11) 0.6615(6) 0.0119(9) Uani 0.50 1 d P . . H4 H 0.0609 0.7134 0.5952 0.014 Uiso 1 1 calc R . . C1 C 0.1648(2) 0.3754(13) 0.8943(7) 0.0121(10) Uani 0.50 1 d P . . H1 H 0.1806 0.2769 1.0158 0.014 Uiso 1 1 calc R . . C2 C 0.2102(3) 0.4093(11) 0.7376(7) 0.0136(12) Uani 0.50 1 d P . . H2 H 0.2601 0.3390 0.7332 0.016 Uiso 1 1 calc R . . C3 C 0.1653(2) 0.5686(14) 0.5921(7) 0.0127(18) Uani 0.50 1 d P . . H3 H 0.1789 0.6311 0.4674 0.015 Uiso 1 1 calc R . . 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 0.0095(3) 0.0087(3) 0.0098(4) 0.000 0.0014(2) 0.000 Cl2 0.0118(4) 0.0090(4) 0.0107(4) 0.000 0.0001(3) 0.000 N1 0.0115(13) 0.0107(14) 0.0095(14) 0.000 0.0003(10) 0.000 N2 0.0103(18) 0.012(2) 0.013(2) 0.0023(14) -0.0012(14) 0.0016(13) C1 0.015(2) 0.012(2) 0.009(2) 0.0002(16) -0.0016(17) 0.0003(17) C2 0.0088(18) 0.011(3) 0.022(2) -0.0020(16) 0.0051(17) 0.0004(15) C3 0.018(2) 0.010(5) 0.011(2) 0.0017(17) 0.0066(15) -0.0018(17) _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 N1 2.078(3) 5_567 ? Co1 N1 2.078(3) . ? Co1 Cl2 2.5155(7) 5_577 ? Co1 Cl2 2.5155(7) 5_567 ? Co1 Cl2 2.5155(7) 1_545 ? Co1 Cl2 2.5155(7) . ? Co1 Cl2 2.5155(7) 1 ? Cl2 Cl2 0.0000(15) 1 ? Cl2 Co1 2.5155(7) 1_565 ? N1 C1 1.314(5) . ? N1 N2 1.355(5) . ? N2 C3 1.327(6) . ? N2 H4 0.8600 . ? C1 C2 1.394(6) . ? C1 H1 0.9300 . ? C2 C3 1.365(6) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? 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 Co1 N1 180.0 5_567 . ? N1 Co1 Cl2 89.04(6) 5_567 5_577 ? N1 Co1 Cl2 90.96(6) . 5_577 ? N1 Co1 Cl2 89.04(6) 5_567 5_567 ? N1 Co1 Cl2 90.96(6) . 5_567 ? Cl2 Co1 Cl2 92.77(3) 5_577 5_567 ? N1 Co1 Cl2 90.96(6) 5_567 1_545 ? N1 Co1 Cl2 89.04(6) . 1_545 ? Cl2 Co1 Cl2 179.999(1) 5_577 1_545 ? Cl2 Co1 Cl2 87.23(3) 5_567 1_545 ? N1 Co1 Cl2 90.96(6) 5_567 . ? N1 Co1 Cl2 89.04(6) . . ? Cl2 Co1 Cl2 87.23(3) 5_577 . ? Cl2 Co1 Cl2 180.0 5_567 . ? Cl2 Co1 Cl2 92.77(3) 1_545 . ? N1 Co1 Cl2 90.96(6) 5_567 1 ? N1 Co1 Cl2 89.04(6) . 1 ? Cl2 Co1 Cl2 87.23(3) 5_577 1 ? Cl2 Co1 Cl2 180.0 5_567 1 ? Cl2 Co1 Cl2 92.77(3) 1_545 1 ? Cl2 Co1 Cl2 0.00(4) . 1 ? Cl2 Cl2 Co1 0.00(11) 1 1_565 ? Cl2 Cl2 Co1 0.00(4) 1 . ? Co1 Cl2 Co1 92.77(3) 1_565 . ? C1 N1 N2 104.5(3) . . ? C1 N1 Co1 132.4(3) . . ? N2 N1 Co1 122.9(2) . . ? C3 N2 N1 112.1(4) . . ? C3 N2 H4 124.0 . . ? N1 N2 H4 124.0 . . ? N1 C1 C2 111.6(4) . . ? N1 C1 H1 124.2 . . ? C2 C1 H1 124.2 . . ? C3 C2 C1 104.6(4) . . ? C3 C2 H2 127.7 . . ? C1 C2 H2 127.7 . . ? N2 C3 C2 107.2(4) . . ? N2 C3 H3 126.4 . . ? C2 C3 H3 126.4 . . ? 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 N1 Co1 Cl2 Cl2 0.00(18) 5_567 . . 1 ? N1 Co1 Cl2 Cl2 0.00(18) . . . 1 ? Cl2 Co1 Cl2 Cl2 0.00(18) 5_577 . . 1 ? Cl2 Co1 Cl2 Cl2 0(37) 5_567 . . 1 ? Cl2 Co1 Cl2 Cl2 0.00(18) 1_545 . . 1 ? N1 Co1 Cl2 Co1 88.99(6) 5_567 . . 1_565 ? N1 Co1 Cl2 Co1 -91.01(6) . . . 1_565 ? Cl2 Co1 Cl2 Co1 0.0 5_577 . . 1_565 ? Cl2 Co1 Cl2 Co1 141(16) 5_567 . . 1_565 ? Cl2 Co1 Cl2 Co1 180.0 1_545 . . 1_565 ? Cl2 Co1 Cl2 Co1 0.00(17) 1 . . 1_565 ? N1 Co1 N1 C1 6(3) 5_567 . . . ? Cl2 Co1 N1 C1 74.2(3) 5_577 . . . ? Cl2 Co1 N1 C1 -18.5(3) 5_567 . . . ? Cl2 Co1 N1 C1 -105.8(3) 1_545 . . . ? Cl2 Co1 N1 C1 161.5(3) . . . . ? Cl2 Co1 N1 C1 161.5(3) 1 . . . ? N1 Co1 N1 N2 -180(3) 5_567 . . . ? Cl2 Co1 N1 N2 -111.4(2) 5_577 . . . ? Cl2 Co1 N1 N2 155.8(2) 5_567 . . . ? Cl2 Co1 N1 N2 68.6(2) 1_545 . . . ? Cl2 Co1 N1 N2 -24.2(2) . . . . ? Cl2 Co1 N1 N2 -24.2(2) 1 . . . ? C1 N1 N2 C3 0.0(4) . . . . ? Co1 N1 N2 C3 -175.7(3) . . . . ? N2 N1 C1 C2 -0.4(4) . . . . ? Co1 N1 C1 C2 174.7(2) . . . . ? N1 C1 C2 C3 0.6(5) . . . . ? N1 N2 C3 C2 0.4(5) . . . . ? C1 C2 C3 N2 -0.6(5) . . . . ? 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 N2 H4 Cl2 0.86 2.65 3.176(4) 120.6 1 N2 H4 Cl2 0.86 2.74 3.349(4) 129.5 5_576 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.374 _refine_diff_density_min -0.515 _refine_diff_density_rms 0.094 # = = = END data_3LT _database_code_depnum_ccdc_archive 'CCDC 771210' #TrackingRef '- Combined CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H10 Cl4 N4 Zn' _chemical_formula_weight 345.35 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.5495(15) _cell_length_b 12.693(3) _cell_length_c 13.068(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.66(3) _cell_angle_gamma 90.00 _cell_volume 1250.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7604 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.834 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 2.790 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.377 _exptl_absorpt_correction_T_max 0.572 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _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_% 0 _diffrn_reflns_number 14060 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2866 _reflns_number_gt 2730 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0184P)^2^+0.5497P] 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_number_reflns 2866 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0180 _refine_ls_R_factor_gt 0.0167 _refine_ls_wR_factor_ref 0.0417 _refine_ls_wR_factor_gt 0.0412 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.23099(2) 0.789492(12) 0.246082(11) 0.01086(5) Uani 1 1 d . . . Cl1 Cl 0.22462(4) 0.97125(2) 0.23981(2) 0.01289(7) Uani 1 1 d . . . Cl2 Cl 0.25802(4) 0.74206(2) 0.41382(2) 0.01356(7) Uani 1 1 d . . . Cl3 Cl -0.02349(4) 0.72680(3) 0.17522(2) 0.01530(7) Uani 1 1 d . . . Cl4 Cl 0.46946(4) 0.73925(3) 0.15788(3) 0.01594(7) Uani 1 1 d . . . N1 N 0.28088(17) 0.02523(10) 0.47502(9) 0.0201(3) Uani 1 1 d . . . H1A H 0.3034 0.0158 0.4102 0.024 Uiso 1 1 calc R . . N2 N 0.21093(17) -0.04700(9) 0.53629(10) 0.0199(3) Uani 1 1 d . . . H2A H 0.1783 -0.1110 0.5178 0.024 Uiso 1 1 calc R . . N3 N 0.14977(18) 0.54672(9) 0.61686(9) 0.0208(3) Uani 1 1 d . . . H3A H 0.1104 0.6104 0.6299 0.025 Uiso 1 1 calc R . . N4 N 0.05301(16) 0.45848(10) 0.61648(9) 0.0199(3) Uani 1 1 d . . . H4A H -0.0605 0.4547 0.6286 0.024 Uiso 1 1 calc R . . C1 C 0.1989(2) -0.00624(12) 0.62928(11) 0.0187(3) Uani 1 1 d . . . H1B H 0.1558 -0.0415 0.6872 0.022 Uiso 1 1 calc R . . C2 C 0.2601(2) 0.09625(11) 0.62709(11) 0.0189(3) Uani 1 1 d . . . H2B H 0.2661 0.1450 0.6823 0.023 Uiso 1 1 calc R . . C3 C 0.3108(2) 0.11336(12) 0.52795(11) 0.0200(3) Uani 1 1 d . . . H3B H 0.3585 0.1769 0.5023 0.024 Uiso 1 1 calc R . . C4 C 0.3153(2) 0.52293(12) 0.59439(11) 0.0203(3) Uani 1 1 d . . . H4B H 0.4103 0.5714 0.5889 0.024 Uiso 1 1 calc R . . C5 C 0.32442(19) 0.41508(12) 0.58045(11) 0.0196(3) Uani 1 1 d . . . H5A H 0.4258 0.3752 0.5643 0.023 Uiso 1 1 calc R . . C6 C 0.1560(2) 0.37740(11) 0.59484(11) 0.0191(3) Uani 1 1 d . . . H6A H 0.1198 0.3058 0.5901 0.023 Uiso 1 1 calc R . . 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 0.01065(8) 0.01145(8) 0.01052(8) -0.00080(5) 0.00081(5) -0.00084(5) Cl1 0.01496(15) 0.01078(14) 0.01311(15) -0.00016(11) 0.00260(11) -0.00012(11) Cl2 0.01697(16) 0.01270(15) 0.01088(15) 0.00016(11) -0.00066(11) 0.00043(12) Cl3 0.01329(15) 0.01810(16) 0.01430(15) -0.00148(12) -0.00171(11) -0.00322(12) Cl4 0.01494(16) 0.01167(15) 0.02179(17) -0.00185(12) 0.00709(12) 0.00005(12) N1 0.0235(6) 0.0263(7) 0.0104(5) -0.0027(5) 0.0006(5) 0.0062(5) N2 0.0234(6) 0.0132(6) 0.0226(6) -0.0039(5) -0.0046(5) 0.0005(5) N3 0.0325(7) 0.0146(6) 0.0151(6) -0.0026(4) -0.0007(5) 0.0086(5) N4 0.0147(6) 0.0267(7) 0.0186(6) 0.0036(5) 0.0045(5) 0.0038(5) C1 0.0225(7) 0.0165(7) 0.0171(7) 0.0025(5) 0.0023(5) 0.0011(6) C2 0.0300(8) 0.0129(6) 0.0136(6) -0.0012(5) -0.0014(6) 0.0003(6) C3 0.0242(8) 0.0181(7) 0.0176(7) 0.0025(5) -0.0006(6) -0.0016(6) C4 0.0228(8) 0.0195(7) 0.0184(7) 0.0016(5) -0.0028(6) -0.0045(6) C5 0.0163(7) 0.0182(7) 0.0246(7) 0.0012(6) 0.0055(6) 0.0035(6) C6 0.0204(7) 0.0157(7) 0.0213(7) 0.0008(5) 0.0034(6) -0.0005(6) _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 Cl3 2.2397(6) . ? Zn1 Cl2 2.2732(5) . ? Zn1 Cl4 2.2736(7) . ? Zn1 Cl1 2.3089(6) . ? N1 C3 1.3290(19) . ? N1 N2 1.3415(18) . ? N1 H1A 0.8800 . ? N2 C1 1.3277(19) . ? N2 H2A 0.8800 . ? N3 C4 1.332(2) . ? N3 N4 1.3371(18) . ? N3 H3A 0.8800 . ? N4 C6 1.3279(19) . ? N4 H4A 0.8800 . ? C1 C2 1.381(2) . ? C1 H1B 0.9500 . ? C2 C3 1.385(2) . ? C2 H2B 0.9500 . ? C3 H3B 0.9500 . ? C4 C5 1.383(2) . ? C4 H4B 0.9500 . ? C5 C6 1.380(2) . ? C5 H5A 0.9500 . ? C6 H6A 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 Cl3 Zn1 Cl2 109.97(3) . . ? Cl3 Zn1 Cl4 112.022(19) . . ? Cl2 Zn1 Cl4 112.14(3) . . ? Cl3 Zn1 Cl1 108.919(15) . . ? Cl2 Zn1 Cl1 107.44(3) . . ? Cl4 Zn1 Cl1 106.14(3) . . ? C3 N1 N2 109.06(12) . . ? C3 N1 H1A 125.5 . . ? N2 N1 H1A 125.5 . . ? C1 N2 N1 109.00(12) . . ? C1 N2 H2A 125.5 . . ? N1 N2 H2A 125.5 . . ? C4 N3 N4 109.11(12) . . ? C4 N3 H3A 125.4 . . ? N4 N3 H3A 125.4 . . ? C6 N4 N3 108.96(12) . . ? C6 N4 H4A 125.5 . . ? N3 N4 H4A 125.5 . . ? N2 C1 C2 108.12(13) . . ? N2 C1 H1B 125.9 . . ? C2 C1 H1B 125.9 . . ? C1 C2 C3 105.92(13) . . ? C1 C2 H2B 127.0 . . ? C3 C2 H2B 127.0 . . ? N1 C3 C2 107.89(13) . . ? N1 C3 H3B 126.1 . . ? C2 C3 H3B 126.1 . . ? N3 C4 C5 107.84(13) . . ? N3 C4 H4B 126.1 . . ? C5 C4 H4B 126.1 . . ? C6 C5 C4 105.87(13) . . ? C6 C5 H5A 127.1 . . ? C4 C5 H5A 127.1 . . ? N4 C6 C5 108.22(13) . . ? N4 C6 H6A 125.9 . . ? C5 C6 H6A 125.9 . . ? 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 C3 N1 N2 C1 -1.23(17) . . . . ? C4 N3 N4 C6 0.63(16) . . . . ? N1 N2 C1 C2 1.18(17) . . . . ? N2 C1 C2 C3 -0.68(17) . . . . ? N2 N1 C3 C2 0.78(17) . . . . ? C1 C2 C3 N1 -0.06(17) . . . . ? N4 N3 C4 C5 -0.77(16) . . . . ? N3 C4 C5 C6 0.60(16) . . . . ? N3 N4 C6 C5 -0.24(17) . . . . ? C4 C5 C6 N4 -0.22(17) . . . . ? 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 N1 H1A Cl1 0.88 2.35 3.1586(14) 153.5 1_545 N2 H2A Cl2 0.88 2.40 3.1478(13) 143.0 1_545 N3 H3A Cl4 0.88 2.22 3.0964(13) 171.2 4_576 N4 H4A Cl1 0.88 2.42 3.1481(15) 140.7 4_576 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.294 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.061 # = = = END data_3RT _database_code_depnum_ccdc_archive 'CCDC 771211' #TrackingRef '- Combined CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H10 Cl4 N4 Zn' _chemical_formula_weight 345.35 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.5750(18) _cell_length_b 12.858(3) _cell_length_c 13.302(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.822(11) _cell_angle_gamma 90.00 _cell_volume 1294.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20364 _cell_measurement_theta_min 3.03 _cell_measurement_theta_max 30.02 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.773 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 2.697 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2533 _exptl_absorpt_correction_T_max 0.3887 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _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_% 0 _diffrn_reflns_number 34843 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0164 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 30.14 _reflns_number_total 3755 _reflns_number_gt 3135 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0887P)^2^+2.7119P] 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 SHELXL _refine_ls_extinction_coef 0.045(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3755 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0654 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.2005 _refine_ls_wR_factor_gt 0.1404 _refine_ls_goodness_of_fit_ref 1.235 _refine_ls_restrained_S_all 1.235 _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 0.23868(6) 0.78964(4) 0.24857(3) 0.0402(2) Uani 1 1 d . . . Cl1 Cl 0.23377(16) 0.96788(10) 0.24340(8) 0.0489(3) Uani 1 1 d . . . Cl2 Cl 0.25831(19) 0.74174(10) 0.41218(9) 0.0530(3) Uani 1 1 d . . . Cl3 Cl -0.01100(16) 0.73050(11) 0.17260(10) 0.0546(3) Uani 1 1 d . . . Cl4 Cl 0.47823(17) 0.74089(10) 0.16589(12) 0.0604(4) Uani 1 1 d . . . N1 N 0.2758(8) 0.0249(5) 0.4733(4) 0.0772(17) Uani 1 1 d . . . H1A H 0.2953 0.0172 0.4106 0.093 Uiso 1 1 calc R . . N2 N 0.2172(9) -0.0473(4) 0.5323(5) 0.0783(17) Uani 1 1 d . . . H2A H 0.1925 -0.1102 0.5147 0.094 Uiso 1 1 calc R . . N3 N 0.1542(11) 0.5484(5) 0.6189(4) 0.0776(18) Uani 1 1 d . . . H3A H 0.1116 0.6093 0.6289 0.093 Uiso 1 1 calc R . . N4 N 0.0671(9) 0.4631(6) 0.6215(5) 0.089(2) Uani 1 1 d . . . H4A H -0.0426 0.4581 0.6348 0.107 Uiso 1 1 calc R . . C1 C 0.2021(11) -0.0084(6) 0.6222(5) 0.0771(18) Uani 1 1 d . . . H1B H 0.1637 -0.0440 0.6779 0.093 Uiso 1 1 calc R . . C2 C 0.2518(12) 0.0917(5) 0.6202(5) 0.080(2) Uani 1 1 d . . . H2B H 0.2530 0.1386 0.6734 0.096 Uiso 1 1 calc R . . C3 C 0.3001(12) 0.1111(6) 0.5250(5) 0.0773(19) Uani 1 1 d . . . H3B H 0.3425 0.1737 0.5009 0.093 Uiso 1 1 calc R . . C4 C 0.3170(12) 0.5286(7) 0.5988(6) 0.086(2) Uani 1 1 d . . . H4B H 0.4081 0.5765 0.5935 0.103 Uiso 1 1 calc R . . C5 C 0.3272(12) 0.4236(7) 0.5871(7) 0.095(3) Uani 1 1 d . . . H5A H 0.4266 0.3853 0.5721 0.114 Uiso 1 1 calc R . . C6 C 0.1667(13) 0.3869(6) 0.6015(7) 0.088(2) Uani 1 1 d . . . H6A H 0.1328 0.3175 0.5976 0.106 Uiso 1 1 calc R . . 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 0.0359(3) 0.0463(4) 0.0387(3) -0.00319(18) 0.00352(19) -0.00228(19) Cl1 0.0526(6) 0.0484(6) 0.0463(6) -0.0012(4) 0.0109(5) 0.0004(5) Cl2 0.0681(8) 0.0506(7) 0.0397(5) 0.0019(5) -0.0026(5) -0.0013(5) Cl3 0.0434(6) 0.0631(8) 0.0562(7) -0.0076(5) -0.0075(5) -0.0069(5) Cl4 0.0486(7) 0.0483(7) 0.0866(10) -0.0078(6) 0.0283(6) 0.0001(5) N1 0.083(4) 0.102(5) 0.047(2) -0.016(3) 0.003(2) 0.027(3) N2 0.087(4) 0.054(3) 0.091(4) -0.018(3) -0.023(3) -0.002(3) N3 0.114(5) 0.062(3) 0.056(3) -0.007(2) -0.001(3) 0.036(3) N4 0.062(3) 0.116(6) 0.090(4) 0.010(4) 0.017(3) 0.014(4) C1 0.099(5) 0.070(4) 0.063(4) 0.012(3) 0.002(3) -0.006(4) C2 0.140(7) 0.053(3) 0.046(3) -0.007(2) -0.005(3) 0.010(4) C3 0.103(6) 0.063(4) 0.065(4) 0.012(3) 0.001(4) -0.008(4) C4 0.086(5) 0.083(5) 0.089(5) 0.020(4) 0.002(4) -0.032(4) C5 0.082(5) 0.094(6) 0.112(6) 0.019(5) 0.042(5) 0.041(4) C6 0.096(6) 0.064(4) 0.106(6) 0.001(4) 0.024(5) -0.005(4) _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 Cl3 2.2335(13) . ? Zn1 Cl4 2.2565(13) . ? Zn1 Cl2 2.2597(13) . ? Zn1 Cl1 2.2931(16) . ? N1 N2 1.307(9) . ? N1 C3 1.311(9) . ? N1 H1A 0.8600 . ? N2 C1 1.306(9) . ? N2 H2A 0.8600 . ? N3 N4 1.281(9) . ? N3 C4 1.299(11) . ? N3 H3A 0.8600 . ? N4 C6 1.273(10) . ? N4 H4A 0.8600 . ? C1 C2 1.342(11) . ? C1 H1B 0.9300 . ? C2 C3 1.358(10) . ? C2 H2B 0.9300 . ? C3 H3B 0.9300 . ? C4 C5 1.362(12) . ? C4 H4B 0.9300 . ? C5 C6 1.326(12) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? 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 Cl3 Zn1 Cl4 111.61(6) . . ? Cl3 Zn1 Cl2 110.92(6) . . ? Cl4 Zn1 Cl2 112.17(6) . . ? Cl3 Zn1 Cl1 108.34(5) . . ? Cl4 Zn1 Cl1 105.98(5) . . ? Cl2 Zn1 Cl1 107.55(5) . . ? N2 N1 C3 109.2(5) . . ? N2 N1 H1A 125.4 . . ? C3 N1 H1A 125.4 . . ? C1 N2 N1 108.9(6) . . ? C1 N2 H2A 125.5 . . ? N1 N2 H2A 125.5 . . ? N4 N3 C4 109.5(6) . . ? N4 N3 H3A 125.2 . . ? C4 N3 H3A 125.2 . . ? C6 N4 N3 110.0(7) . . ? C6 N4 H4A 125.0 . . ? N3 N4 H4A 125.0 . . ? N2 C1 C2 108.2(6) . . ? N2 C1 H1B 125.9 . . ? C2 C1 H1B 125.9 . . ? C1 C2 C3 106.4(6) . . ? C1 C2 H2B 126.8 . . ? C3 C2 H2B 126.8 . . ? N1 C3 C2 107.2(6) . . ? N1 C3 H3B 126.4 . . ? C2 C3 H3B 126.4 . . ? N3 C4 C5 106.1(7) . . ? N3 C4 H4B 127.0 . . ? C5 C4 H4B 127.0 . . ? C6 C5 C4 106.2(7) . . ? C6 C5 H5A 126.9 . . ? C4 C5 H5A 126.9 . . ? N4 C6 C5 108.3(8) . . ? N4 C6 H6A 125.9 . . ? C5 C6 H6A 125.9 . . ? 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 C3 N1 N2 C1 0.4(9) . . . . ? C4 N3 N4 C6 -1.4(10) . . . . ? N1 N2 C1 C2 0.3(9) . . . . ? N2 C1 C2 C3 -0.8(10) . . . . ? N2 N1 C3 C2 -0.9(9) . . . . ? C1 C2 C3 N1 1.1(10) . . . . ? N4 N3 C4 C5 0.9(9) . . . . ? N3 C4 C5 C6 -0.1(11) . . . . ? N3 N4 C6 C5 1.3(11) . . . . ? C4 C5 C6 N4 -0.7(12) . . . . ? 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 N1 H1A Cl1 0.86 2.34 3.146(5) 156.7 1_545 N2 H2A Cl2 0.86 2.41 3.171(6) 148.1 1_545 N3 H3A Cl4 0.86 2.24 3.097(5) 173.5 4_576 N4 H4A Cl1 0.86 2.47 3.193(6) 142.0 4_576 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.687 _refine_diff_density_min -2.719 _refine_diff_density_rms 0.166 # = = = END data_4LT _database_code_depnum_ccdc_archive 'CCDC 771212' #TrackingRef '- Combined CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H8 Cl2 N4 Zn' _chemical_formula_weight 272.43 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 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' _cell_length_a 7.94360(10) _cell_length_b 11.3609(2) _cell_length_c 11.9034(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1074.24(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 34672 _cell_measurement_theta_min 2.4684 _cell_measurement_theta_max 32.8624 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.684 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 2.744 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5147 _exptl_absorpt_correction_T_max 0.95 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Oxford Diffraction Gemini-R Ultra' _diffrn_measurement_method 'Omega scans, 1 degree width' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 98981 _diffrn_reflns_av_R_equivalents 0.0793 _diffrn_reflns_av_sigmaI/netI 0.0624 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 32.94 _reflns_number_total 3924 _reflns_number_gt 2917 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material 'SHELXTL (Bruker, 2001)' _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^)+(0.0510P)^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 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 0.025(13) _refine_ls_number_reflns 3924 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0889 _refine_ls_wR_factor_gt 0.0831 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 Zn1 Zn 0.09510(4) 0.47466(3) 0.69529(2) 0.02024(9) Uani 1 1 d . . . Cl1 Cl 0.12249(9) 0.39664(6) 0.86626(5) 0.02366(15) Uani 1 1 d . . . Cl2 Cl -0.15598(9) 0.55866(6) 0.66088(6) 0.02387(15) Uani 1 1 d . . . N1 N 0.2528(3) 0.6101(2) 0.6648(2) 0.0218(5) Uani 1 1 d . . . N2 N 0.1979(3) 0.7166(2) 0.6311(2) 0.0230(5) Uani 1 1 d . . . H2A H 0.0938 0.7347 0.6215 0.028 Uiso 1 1 calc R . . N3 N 0.1447(3) 0.3433(2) 0.5885(2) 0.0231(5) Uani 1 1 d . . . N4 N 0.1485(3) 0.2281(2) 0.6191(2) 0.0261(6) Uani 1 1 d . . . H4A H 0.1418 0.2034 0.6873 0.031 Uiso 1 1 calc R . . C1 C 0.4197(4) 0.6188(3) 0.6680(2) 0.0239(6) Uani 1 1 d . . . H1A H 0.4919 0.5578 0.6879 0.029 Uiso 1 1 calc R . . C2 C 0.4721(4) 0.7312(3) 0.6378(2) 0.0264(6) Uani 1 1 d . . . H2B H 0.5816 0.7599 0.6341 0.032 Uiso 1 1 calc R . . C3 C 0.3258(4) 0.7899(3) 0.6146(2) 0.0288(7) Uani 1 1 d . . . H3A H 0.3173 0.8678 0.5913 0.035 Uiso 1 1 calc R . . C4 C 0.1599(5) 0.3425(3) 0.4763(2) 0.0304(7) Uani 1 1 d . . . H4B H 0.1626 0.4094 0.4313 0.037 Uiso 1 1 calc R . . C5 C 0.1713(5) 0.2268(3) 0.4363(3) 0.0382(8) Uani 1 1 d . . . H5A H 0.1816 0.2023 0.3621 0.046 Uiso 1 1 calc R . . C6 C 0.1641(5) 0.1584(3) 0.5297(3) 0.0346(8) Uani 1 1 d . . . H6B H 0.1692 0.0766 0.5310 0.042 Uiso 1 1 calc R . . 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 0.02316(17) 0.01969(16) 0.01785(15) -0.00119(12) -0.00024(12) 0.00046(13) Cl1 0.0307(4) 0.0216(3) 0.0186(3) 0.0020(2) -0.0016(3) -0.0017(3) Cl2 0.0225(3) 0.0230(3) 0.0261(3) -0.0039(3) -0.0039(2) 0.0023(3) N1 0.0219(12) 0.0203(11) 0.0233(12) 0.0030(9) -0.0006(9) -0.0024(10) N2 0.0243(13) 0.0215(12) 0.0231(12) 0.0012(10) -0.0006(10) 0.0043(10) N3 0.0307(13) 0.0202(11) 0.0184(11) 0.0000(9) 0.0069(10) 0.0023(10) N4 0.0366(15) 0.0245(13) 0.0171(12) 0.0043(10) 0.0038(10) 0.0019(11) C1 0.0189(13) 0.0299(15) 0.0228(13) 0.0002(11) -0.0007(10) 0.0030(12) C2 0.0246(15) 0.0321(17) 0.0227(15) 0.0003(12) 0.0035(11) -0.0072(12) C3 0.0398(17) 0.0264(16) 0.0202(15) 0.0026(12) 0.0028(12) -0.0039(14) C4 0.0454(18) 0.0272(16) 0.0187(14) 0.0002(12) 0.0069(13) 0.0016(14) C5 0.067(2) 0.0308(17) 0.0170(15) -0.0059(13) 0.0079(15) 0.0028(17) C6 0.053(2) 0.0227(16) 0.0280(17) 0.0001(13) 0.0079(16) 0.0011(15) _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 N3 1.999(2) . ? Zn1 N1 2.017(2) . ? Zn1 Cl1 2.2303(7) . ? Zn1 Cl2 2.2486(7) . ? N1 C1 1.330(4) . ? N1 N2 1.347(3) . ? N2 C3 1.328(4) . ? N3 C4 1.341(4) . ? N3 N4 1.359(3) . ? N4 C6 1.333(4) . ? C1 C2 1.390(4) . ? C2 C3 1.368(5) . ? C4 C5 1.400(4) . ? C5 C6 1.357(5) . ? 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 N3 Zn1 N1 109.41(10) . . ? N3 Zn1 Cl1 105.32(7) . . ? N1 Zn1 Cl1 114.01(7) . . ? N3 Zn1 Cl2 112.06(8) . . ? N1 Zn1 Cl2 101.22(7) . . ? Cl1 Zn1 Cl2 114.92(3) . . ? C1 N1 N2 105.3(2) . . ? C1 N1 Zn1 132.1(2) . . ? N2 N1 Zn1 122.51(18) . . ? C3 N2 N1 111.1(2) . . ? C4 N3 N4 104.9(2) . . ? C4 N3 Zn1 131.0(2) . . ? N4 N3 Zn1 123.57(18) . . ? C6 N4 N3 111.1(2) . . ? N1 C1 C2 111.1(3) . . ? C3 C2 C1 104.2(3) . . ? N2 C3 C2 108.3(3) . . ? N3 C4 C5 110.6(3) . . ? C6 C5 C4 104.9(3) . . ? N4 C6 C5 108.5(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 N3 Zn1 N1 C1 -60.4(3) . . . . ? Cl1 Zn1 N1 C1 57.2(3) . . . . ? Cl2 Zn1 N1 C1 -178.8(3) . . . . ? N3 Zn1 N1 N2 117.4(2) . . . . ? Cl1 Zn1 N1 N2 -125.0(2) . . . . ? Cl2 Zn1 N1 N2 -1.0(2) . . . . ? C1 N1 N2 C3 -0.5(3) . . . . ? Zn1 N1 N2 C3 -178.83(19) . . . . ? N1 Zn1 N3 C4 -50.9(3) . . . . ? Cl1 Zn1 N3 C4 -173.9(3) . . . . ? Cl2 Zn1 N3 C4 60.5(3) . . . . ? N1 Zn1 N3 N4 138.1(2) . . . . ? Cl1 Zn1 N3 N4 15.2(3) . . . . ? Cl2 Zn1 N3 N4 -110.5(2) . . . . ? C4 N3 N4 C6 -0.5(4) . . . . ? Zn1 N3 N4 C6 172.4(2) . . . . ? N2 N1 C1 C2 0.7(3) . . . . ? Zn1 N1 C1 C2 178.84(19) . . . . ? N1 C1 C2 C3 -0.7(3) . . . . ? N1 N2 C3 C2 0.1(3) . . . . ? C1 C2 C3 N2 0.4(3) . . . . ? N4 N3 C4 C5 0.7(4) . . . . ? Zn1 N3 C4 C5 -171.5(3) . . . . ? N3 C4 C5 C6 -0.7(5) . . . . ? N3 N4 C6 C5 0.1(4) . . . . ? C4 C5 C6 N4 0.3(4) . . . . ? 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 N2 H2A Cl1 0.86 2.52 3.266(2) 145.3 3_556 N4 H4A Cl2 0.86 2.45 3.251(2) 156.0 3_546 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 32.94 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.801 _refine_diff_density_min -0.518 _refine_diff_density_rms 0.116 # = = = END data_4RT _database_code_depnum_ccdc_archive 'CCDC 771213' #TrackingRef '- Combined CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H8 Cl2 N4 Zn' _chemical_formula_weight 272.43 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 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' _cell_length_a 7.9779(12) _cell_length_b 11.3785(16) _cell_length_c 12.0866(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1097.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 12702 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 27.41 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 2.686 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3448 _exptl_absorpt_correction_T_max 0.5816 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _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_% 0 _diffrn_reflns_number 19078 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0182 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 27.63 _reflns_number_total 2514 _reflns_number_gt 2387 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0288P)^2^+0.1065P] 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 0.279(9) _refine_ls_number_reflns 2514 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0227 _refine_ls_R_factor_gt 0.0205 _refine_ls_wR_factor_ref 0.0498 _refine_ls_wR_factor_gt 0.0490 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 Zn1 Zn 0.09092(3) 0.975785(18) 0.306106(18) 0.03895(7) Uani 1 1 d . . . Cl1 Cl 0.13307(7) 0.89837(5) 0.13972(4) 0.05155(14) Uani 1 1 d . . . Cl2 Cl -0.16140(6) 1.05558(5) 0.33317(5) 0.05339(14) Uani 1 1 d . . . N1 N 0.1394(2) 0.84520(15) 0.41265(14) 0.0462(4) Uani 1 1 d . . . N2 N 0.1450(3) 0.73198(16) 0.38354(17) 0.0570(5) Uani 1 1 d . . . H2A H 0.1414 0.7069 0.3165 0.068 Uiso 1 1 calc R . . N3 N 0.2455(2) 1.11093(14) 0.33963(14) 0.0407(4) Uani 1 1 d . . . N4 N 0.1904(2) 1.21762(15) 0.36918(15) 0.0467(4) Uani 1 1 d . . . H4B H 0.0866 1.2361 0.3773 0.056 Uiso 1 1 calc R . . C1 C 0.1507(5) 0.8447(2) 0.5216(2) 0.0711(8) Uani 1 1 d . . . H1A H 0.1504 0.9117 0.5657 0.085 Uiso 1 1 calc R . . C2 C 0.1631(5) 0.7315(3) 0.5608(2) 0.0861(10) Uani 1 1 d . . . H2B H 0.1737 0.7080 0.6342 0.103 Uiso 1 1 calc R . . C3 C 0.1569(5) 0.6632(2) 0.4724(2) 0.0765(9) Uani 1 1 d . . . H3A H 0.1602 0.5815 0.4723 0.092 Uiso 1 1 calc R . . C4 C 0.4110(3) 1.1200(2) 0.33726(19) 0.0511(5) Uani 1 1 d . . . H4A H 0.4837 1.0591 0.3192 0.061 Uiso 1 1 calc R . . C5 C 0.3173(4) 1.2908(2) 0.3843(2) 0.0596(6) Uani 1 1 d . . . H5A H 0.3088 1.3694 0.4045 0.072 Uiso 1 1 calc R . . C6 C 0.4610(3) 1.2320(3) 0.3652(2) 0.0587(6) Uani 1 1 d . . . H6A H 0.5699 1.2606 0.3699 0.070 Uiso 1 1 calc R . . 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 0.03883(11) 0.03164(11) 0.04639(12) 0.00433(9) 0.00043(9) 0.00091(9) Cl1 0.0615(3) 0.0430(3) 0.0501(3) -0.0055(2) 0.0074(2) -0.0039(2) Cl2 0.0402(2) 0.0437(3) 0.0763(3) 0.0132(2) 0.0122(2) 0.0062(2) N1 0.0624(12) 0.0329(8) 0.0432(9) -0.0001(7) -0.0084(8) 0.0029(8) N2 0.0844(15) 0.0355(9) 0.0511(10) -0.0047(8) -0.0115(10) 0.0098(9) N3 0.0371(8) 0.0366(8) 0.0485(9) -0.0024(7) -0.0016(7) 0.0016(7) N4 0.0434(9) 0.0404(10) 0.0562(11) -0.0077(8) -0.0001(8) 0.0045(8) C1 0.122(3) 0.0468(13) 0.0446(13) -0.0074(11) -0.0207(14) 0.0095(15) C2 0.144(3) 0.0635(17) 0.0505(15) 0.0135(13) -0.0178(17) 0.0146(19) C3 0.119(3) 0.0396(12) 0.0710(17) 0.0118(12) -0.0123(17) 0.0103(15) C4 0.0373(10) 0.0542(12) 0.0618(13) -0.0011(10) -0.0026(9) 0.0025(10) C5 0.0760(17) 0.0416(12) 0.0612(14) -0.0097(11) -0.0037(12) -0.0112(12) C6 0.0455(12) 0.0694(16) 0.0613(14) -0.0015(12) -0.0046(10) -0.0186(11) _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 2.0039(17) . ? Zn1 N3 2.0123(17) . ? Zn1 Cl1 2.2211(6) . ? Zn1 Cl2 2.2323(6) . ? N1 C1 1.320(3) . ? N1 N2 1.336(2) . ? N2 C3 1.333(3) . ? N3 C4 1.325(3) . ? N3 N4 1.340(2) . ? N4 C5 1.324(3) . ? C1 C2 1.376(4) . ? C2 C3 1.322(4) . ? C4 C6 1.376(4) . ? C5 C6 1.347(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zn1 N3 108.60(7) . . ? N1 Zn1 Cl1 104.98(5) . . ? N3 Zn1 Cl1 113.11(5) . . ? N1 Zn1 Cl2 112.43(6) . . ? N3 Zn1 Cl2 102.25(5) . . ? Cl1 Zn1 Cl2 115.50(2) . . ? C1 N1 N2 104.86(19) . . ? C1 N1 Zn1 131.10(16) . . ? N2 N1 Zn1 123.51(14) . . ? C3 N2 N1 110.9(2) . . ? C4 N3 N4 105.19(18) . . ? C4 N3 Zn1 131.77(16) . . ? N4 N3 Zn1 123.03(13) . . ? C5 N4 N3 110.82(19) . . ? N1 C1 C2 110.6(2) . . ? C3 C2 C1 105.6(2) . . ? C2 C3 N2 108.0(2) . . ? N3 C4 C6 110.8(2) . . ? N4 C5 C6 108.4(2) . . ? C5 C6 C4 104.8(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 N3 Zn1 N1 C1 51.0(3) . . . . ? Cl1 Zn1 N1 C1 172.3(3) . . . . ? Cl2 Zn1 N1 C1 -61.4(3) . . . . ? N3 Zn1 N1 N2 -138.65(19) . . . . ? Cl1 Zn1 N1 N2 -17.4(2) . . . . ? Cl2 Zn1 N1 N2 108.94(19) . . . . ? C1 N1 N2 C3 0.9(3) . . . . ? Zn1 N1 N2 C3 -171.5(2) . . . . ? N1 Zn1 N3 C4 61.9(2) . . . . ? Cl1 Zn1 N3 C4 -54.2(2) . . . . ? Cl2 Zn1 N3 C4 -179.1(2) . . . . ? N1 Zn1 N3 N4 -119.41(16) . . . . ? Cl1 Zn1 N3 N4 124.48(15) . . . . ? Cl2 Zn1 N3 N4 -0.39(16) . . . . ? C4 N3 N4 C5 0.2(3) . . . . ? Zn1 N3 N4 C5 -178.76(15) . . . . ? N2 N1 C1 C2 -0.1(4) . . . . ? Zn1 N1 C1 C2 171.6(2) . . . . ? N1 C1 C2 C3 -0.8(5) . . . . ? C1 C2 C3 N2 1.3(5) . . . . ? N1 N2 C3 C2 -1.4(4) . . . . ? N4 N3 C4 C6 0.0(3) . . . . ? Zn1 N3 C4 C6 178.91(15) . . . . ? N3 N4 C5 C6 -0.4(3) . . . . ? N4 C5 C6 C4 0.4(3) . . . . ? N3 C4 C6 C5 -0.3(3) . . . . ? 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 N2 H2A Cl2 0.86 2.50 3.303(2) 155.2 3_545 N4 H4B Cl1 0.86 2.55 3.3015(19) 145.9 3 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.63 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.427 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.063 # = = = END data_6 _database_code_depnum_ccdc_archive 'CCDC 771214' #TrackingRef '- Combined CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H8 Cl2 Cu N4' _chemical_formula_weight 270.61 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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' _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 3.7606(8) _cell_length_b 8.8887(18) _cell_length_c 13.649(3) _cell_angle_alpha 86.21(3) _cell_angle_beta 86.88(4) _cell_angle_gamma 78.56(3) _cell_volume 445.80(16) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2130 _cell_measurement_theta_min 2.342 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.010 _exptl_crystal_size_min 0.010 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.016 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 270 _exptl_absorpt_coefficient_mu 3.001 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.767 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _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_% 0 _diffrn_reflns_number 4999 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2022 _reflns_number_gt 1828 _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^)+(0.0000P)^2^+8.6737P] 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_number_reflns 2022 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1499 _refine_ls_wR_factor_gt 0.1485 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 Cu1 Cu 0.5016(2) 0.49899(8) 0.25004(5) 0.0102(2) Uani 1 1 d . . . Cl1 Cl 1.1174(4) 0.39420(16) 0.36525(10) 0.0121(3) Uani 1 1 d . . . Cl2 Cl -0.1413(4) 0.61509(16) 0.13428(10) 0.0128(3) Uani 1 1 d . . . N1 N 0.4065(14) 0.6872(6) 0.3230(4) 0.0116(10) Uani 1 1 d . . . C1 C 0.2096(17) 0.8258(7) 0.3020(5) 0.0134(12) Uani 1 1 d . . . H2A H 0.0952 0.8566 0.2416 0.016 Uiso 1 1 calc R . . N2 N 0.5139(14) 0.6906(6) 0.4158(4) 0.0117(10) Uani 1 1 d . . . H1A H 0.6470 0.6122 0.4480 0.014 Uiso 1 1 calc R . . C2 C 0.3921(17) 0.8282(7) 0.4522(5) 0.0136(12) Uani 1 1 d . . . H2B H 0.4340 0.8575 0.5156 0.016 Uiso 1 1 calc R . . C3 C 0.1932(18) 0.9200(7) 0.3803(5) 0.0155(13) Uani 1 1 d . . . H3A H 0.0724 1.0242 0.3838 0.019 Uiso 1 1 calc R . . N3 N 0.5916(14) 0.3110(6) 0.1766(4) 0.0107(10) Uani 1 1 d . . . N4 N 0.7197(14) 0.3075(6) 0.0829(4) 0.0111(10) Uani 1 1 d . . . H4A H 0.7828 0.3866 0.0492 0.013 Uiso 1 1 calc R . . C4 C 0.5274(17) 0.1710(7) 0.2000(5) 0.0122(12) Uani 1 1 d . . . H4B H 0.4313 0.1397 0.2621 0.015 Uiso 1 1 calc R . . C5 C 0.6198(17) 0.0756(7) 0.1211(4) 0.0122(12) Uani 1 1 d . . . H5A H 0.6038 -0.0295 0.1191 0.015 Uiso 1 1 calc R . . C6 C 0.7402(17) 0.1696(7) 0.0466(5) 0.0125(12) Uani 1 1 d . . . H6A H 0.8217 0.1415 -0.0180 0.015 Uiso 1 1 calc R . . 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 Cu1 0.0128(4) 0.0082(4) 0.0097(4) -0.0016(3) 0.0017(3) -0.0028(3) Cl1 0.0119(7) 0.0134(7) 0.0109(7) -0.0001(5) 0.0012(5) -0.0026(5) Cl2 0.0142(7) 0.0144(7) 0.0108(7) 0.0000(5) 0.0010(5) -0.0057(5) N1 0.014(3) 0.013(2) 0.009(2) -0.0009(19) 0.0030(19) -0.006(2) C1 0.015(3) 0.015(3) 0.009(3) 0.003(2) -0.001(2) -0.003(2) N2 0.014(3) 0.013(2) 0.007(2) 0.0020(19) -0.0015(18) -0.0019(19) C2 0.014(3) 0.017(3) 0.010(3) -0.004(2) 0.003(2) -0.005(2) C3 0.014(3) 0.014(3) 0.018(3) -0.003(2) 0.001(2) -0.001(2) N3 0.010(2) 0.011(2) 0.012(3) -0.0022(19) 0.0009(19) -0.0033(19) N4 0.016(3) 0.011(2) 0.008(2) -0.0018(19) 0.0002(19) -0.0067(19) C4 0.015(3) 0.011(3) 0.010(3) 0.000(2) 0.001(2) -0.002(2) C5 0.014(3) 0.011(3) 0.012(3) -0.002(2) -0.002(2) -0.004(2) C6 0.013(3) 0.014(3) 0.011(3) -0.004(2) -0.002(2) -0.002(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 Cu1 N1 1.965(5) . ? Cu1 N3 1.968(5) . ? Cu1 Cl2 2.3384(17) 1_655 ? Cu1 Cl1 2.3495(17) 1_455 ? Cu1 Cl1 2.8375(19) . ? Cu1 Cl2 2.9354(19) . ? Cl1 Cu1 2.3495(17) 1_655 ? Cl2 Cu1 2.3384(17) 1_455 ? N1 C1 1.328(8) . ? N1 N2 1.354(7) . ? C1 C3 1.393(9) . ? C1 H2A 0.9500 . ? N2 C2 1.336(8) . ? N2 H1A 0.8800 . ? C2 C3 1.386(9) . ? C2 H2B 0.9500 . ? C3 H3A 0.9500 . ? N3 C4 1.329(8) . ? N3 N4 1.342(7) . ? N4 C6 1.338(8) . ? N4 H4A 0.8800 . ? C4 C5 1.400(9) . ? C4 H4B 0.9500 . ? C5 C6 1.388(9) . ? C5 H5A 0.9500 . ? C6 H6A 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 N1 Cu1 N3 179.4(2) . . ? N1 Cu1 Cl2 89.48(15) . 1_655 ? N3 Cu1 Cl2 90.72(16) . 1_655 ? N1 Cu1 Cl1 88.57(15) . 1_455 ? N3 Cu1 Cl1 91.21(16) . 1_455 ? Cl2 Cu1 Cl1 176.88(6) 1_655 1_455 ? N1 Cu1 Cl1 87.71(16) . . ? N3 Cu1 Cl1 92.83(16) . . ? Cl2 Cu1 Cl1 89.91(6) 1_655 . ? Cl1 Cu1 Cl1 92.45(6) 1_455 . ? N1 Cu1 Cl2 90.65(16) . . ? N3 Cu1 Cl2 88.80(16) . . ? Cl2 Cu1 Cl2 90.24(5) 1_655 . ? Cl1 Cu1 Cl2 87.35(5) 1_455 . ? Cl1 Cu1 Cl2 178.36(5) . . ? Cu1 Cl1 Cu1 92.45(6) 1_655 . ? Cu1 Cl2 Cu1 90.24(5) 1_455 . ? C1 N1 N2 105.7(5) . . ? C1 N1 Cu1 131.3(4) . . ? N2 N1 Cu1 122.7(4) . . ? N1 C1 C3 111.0(6) . . ? N1 C1 H2A 124.5 . . ? C3 C1 H2A 124.5 . . ? C2 N2 N1 111.4(5) . . ? C2 N2 H1A 124.3 . . ? N1 N2 H1A 124.3 . . ? N2 C2 C3 107.3(6) . . ? N2 C2 H2B 126.4 . . ? C3 C2 H2B 126.4 . . ? C2 C3 C1 104.7(6) . . ? C2 C3 H3A 127.6 . . ? C1 C3 H3A 127.6 . . ? C4 N3 N4 105.4(5) . . ? C4 N3 Cu1 131.7(4) . . ? N4 N3 Cu1 122.8(4) . . ? C6 N4 N3 112.2(5) . . ? C6 N4 H4A 123.9 . . ? N3 N4 H4A 123.9 . . ? N3 C4 C5 111.2(5) . . ? N3 C4 H4B 124.4 . . ? C5 C4 H4B 124.4 . . ? C6 C5 C4 104.2(5) . . ? C6 C5 H5A 127.9 . . ? C4 C5 H5A 127.9 . . ? N4 C6 C5 107.0(5) . . ? N4 C6 H6A 126.5 . . ? C5 C6 H6A 126.5 . . ? 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 N1 Cu1 Cl1 Cu1 -91.53(15) . . . 1_655 ? N3 Cu1 Cl1 Cu1 88.67(16) . . . 1_655 ? Cl2 Cu1 Cl1 Cu1 -2.05(6) 1_655 . . 1_655 ? Cl1 Cu1 Cl1 Cu1 180.0 1_455 . . 1_655 ? N1 Cu1 Cl2 Cu1 -90.52(15) . . . 1_455 ? N3 Cu1 Cl2 Cu1 89.29(16) . . . 1_455 ? Cl2 Cu1 Cl2 Cu1 180.0 1_655 . . 1_455 ? Cl1 Cu1 Cl2 Cu1 -1.98(6) 1_455 . . 1_455 ? Cl2 Cu1 N1 C1 70.4(6) 1_655 . . . ? Cl1 Cu1 N1 C1 -107.2(6) 1_455 . . . ? Cl1 Cu1 N1 C1 160.3(6) . . . . ? Cl2 Cu1 N1 C1 -19.8(6) . . . . ? Cl2 Cu1 N1 N2 -117.1(5) 1_655 . . . ? Cl1 Cu1 N1 N2 65.4(5) 1_455 . . . ? Cl1 Cu1 N1 N2 -27.1(4) . . . . ? Cl2 Cu1 N1 N2 152.7(4) . . . . ? N2 N1 C1 C3 0.9(7) . . . . ? Cu1 N1 C1 C3 174.4(4) . . . . ? C1 N1 N2 C2 -0.7(7) . . . . ? Cu1 N1 N2 C2 -174.9(4) . . . . ? N1 N2 C2 C3 0.3(7) . . . . ? N2 C2 C3 C1 0.2(7) . . . . ? N1 C1 C3 C2 -0.7(7) . . . . ? Cl2 Cu1 N3 C4 168.3(6) 1_655 . . . ? Cl1 Cu1 N3 C4 -14.2(6) 1_455 . . . ? Cl1 Cu1 N3 C4 78.3(6) . . . . ? Cl2 Cu1 N3 C4 -101.5(6) . . . . ? Cl2 Cu1 N3 N4 -16.7(5) 1_655 . . . ? Cl1 Cu1 N3 N4 160.9(4) 1_455 . . . ? Cl1 Cu1 N3 N4 -106.6(4) . . . . ? Cl2 Cu1 N3 N4 73.6(5) . . . . ? C4 N3 N4 C6 -0.3(7) . . . . ? Cu1 N3 N4 C6 -176.5(4) . . . . ? N4 N3 C4 C5 0.9(7) . . . . ? Cu1 N3 C4 C5 176.6(4) . . . . ? N3 C4 C5 C6 -1.1(7) . . . . ? N3 N4 C6 C5 -0.3(7) . . . . ? C4 C5 C6 N4 0.8(7) . . . . ? 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 N2 H1A Cl1 0.88 2.74 3.340(5) 126.9 2_766 N4 H4A Cl2 0.88 2.48 3.017(5) 120.3 1_655 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.813 _refine_diff_density_min -0.847 _refine_diff_density_rms 0.177 # = = = END data_[H2pz]Cl _database_code_depnum_ccdc_archive 'CCDC 771215' #TrackingRef '- Combined CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H5 Cl N2' _chemical_formula_weight 104.54 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' 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.3797(7) _cell_length_b 7.3935(8) _cell_length_c 8.7051(7) _cell_angle_alpha 90.00 _cell_angle_beta 114.398(5) _cell_angle_gamma 90.00 _cell_volume 491.16(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1459 _cell_measurement_theta_min 3.749 _cell_measurement_theta_max 27.46 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.136 _exptl_crystal_size_min 0.072 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 216 _exptl_absorpt_coefficient_mu 0.615 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.859776 _exptl_absorpt_correction_T_max 0.954368 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Smart APEX CCD area detector' _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 3637 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 27.65 _reflns_number_total 1136 _reflns_number_gt 947 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0692P)^2^+0.1137P] 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_number_reflns 1136 _refine_ls_number_parameters 55 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.1256 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 1.202 _refine_ls_restrained_S_all 1.202 _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 Cl1 Cl 0.68894(6) 0.23616(7) 0.36212(5) 0.0192(2) Uani 1 1 d . . . N1 N 0.1550(2) 0.2660(3) 0.5009(2) 0.0200(5) Uani 1 1 d . . . H1A H 0.1840 0.2907 0.6080 0.024 Uiso 1 1 calc R . . N2 N 0.1442(2) 0.1007(3) 0.4361(2) 0.0208(4) Uani 1 1 d . . . H2A H 0.1633 -0.0012 0.4932 0.025 Uiso 1 1 calc R . . C1 C 0.0996(2) 0.1149(3) 0.2708(2) 0.0209(5) Uani 1 1 d . . . H1B H 0.0838 0.0173 0.1950 0.025 Uiso 1 1 calc R . . C2 C 0.0803(3) 0.2951(3) 0.2293(3) 0.0192(5) Uani 1 1 d . . . H2B H 0.0494 0.3462 0.1207 0.023 Uiso 1 1 calc R . . C3 C 0.1152(3) 0.3873(3) 0.3783(3) 0.0199(5) Uani 1 1 d . . . H3A H 0.1113 0.5147 0.3906 0.024 Uiso 1 1 calc R . . 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 Cl1 0.0250(3) 0.0154(3) 0.0151(3) 0.00101(17) 0.0060(2) 0.00201(19) N1 0.0184(9) 0.0249(11) 0.0151(9) -0.0024(7) 0.0055(8) 0.0009(7) N2 0.0206(9) 0.0149(10) 0.0253(9) 0.0061(7) 0.0078(7) 0.0019(7) C1 0.0186(10) 0.0215(13) 0.0216(10) -0.0048(9) 0.0072(8) -0.0004(9) C2 0.0185(10) 0.0215(12) 0.0165(10) 0.0019(8) 0.0063(8) -0.0008(9) C3 0.0176(9) 0.0135(11) 0.0263(11) 0.0001(8) 0.0069(8) 0.0001(8) _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 N1 C3 1.327(3) . ? N1 N2 1.333(2) . ? N1 H1A 0.8800 . ? N2 C1 1.333(3) . ? N2 H2A 0.8800 . ? C1 C2 1.373(3) . ? C1 H1B 0.9500 . ? C2 C3 1.385(3) . ? C2 H2B 0.9500 . ? C3 H3A 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 C3 N1 N2 109.19(17) . . ? C3 N1 H1A 125.4 . . ? N2 N1 H1A 125.4 . . ? C1 N2 N1 108.92(18) . . ? C1 N2 H2A 125.5 . . ? N1 N2 H2A 125.5 . . ? N2 C1 C2 108.09(19) . . ? N2 C1 H1B 126.0 . . ? C2 C1 H1B 126.0 . . ? C1 C2 C3 105.96(18) . . ? C1 C2 H2B 127.0 . . ? C3 C2 H2B 127.0 . . ? N1 C3 C2 107.8(2) . . ? N1 C3 H3A 126.1 . . ? C2 C3 H3A 126.1 . . ? 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 C3 N1 N2 C1 0.9(2) . . . . ? N1 N2 C1 C2 -0.4(2) . . . . ? N2 C1 C2 C3 -0.2(2) . . . . ? N2 N1 C3 C2 -1.0(2) . . . . ? C1 C2 C3 N1 0.7(2) . . . . ? 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 N1 H1A Cl1 0.88 2.20 3.0378(18) 158.0 4_566 N2 H2A Cl1 0.88 2.20 3.0353(19) 157.9 3_656 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.65 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.418 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.107 #===END