# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_sh32 #TrackingRef '1-Co.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 Co N4 S2' _chemical_formula_sum 'C14 H14 Co N4 S2' _chemical_formula_weight 361.34 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' S S 0.1246 0.1234 '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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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 8.6910(4) _cell_length_b 12.9024(7) _cell_length_c 14.6057(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1637.81(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10794 _cell_measurement_theta_min 3.15 _cell_measurement_theta_max 28.00 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.2581 _exptl_crystal_size_mid 0.1563 _exptl_crystal_size_min 0.0858 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 1.300 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6532 _exptl_absorpt_correction_T_max 0.8603 _exptl_absorpt_process_details 'X-Shape and X-Red32 (Stoe, 2008)' _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 'STOE IPDS-2' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10794 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 28.00 _reflns_number_total 3937 _reflns_number_gt 3138 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area (Stoe, 2008)' _computing_cell_refinement 'X-Area (Stoe, 2008)' _computing_data_reduction 'X-Area (Stoe, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; XP in SHELXTL (Sheldrick, 2008) and Diamond (Brandenburg, 2011) ; _computing_publication_material 'XCIF in 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^)+(0.0474P)^2^+0.0698P] 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 0.0105(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(8) _refine_ls_number_reflns 3937 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0875 _refine_ls_wR_factor_gt 0.0798 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 0.50238(5) 0.24036(2) 0.73326(2) 0.04359(11) Uani 1 1 d . . . N1 N 0.7075(3) 0.2225(2) 0.68087(19) 0.0595(6) Uani 1 1 d . . . C1 C 0.8387(4) 0.2241(2) 0.66845(18) 0.0471(6) Uani 1 1 d . . . S1 S 1.02089(10) 0.22752(8) 0.65223(6) 0.0720(3) Uani 1 1 d . . . N2 N 0.5172(3) 0.25361(19) 0.86521(17) 0.0600(6) Uani 1 1 d . . . C2 C 0.5209(4) 0.2639(2) 0.94389(18) 0.0500(6) Uani 1 1 d . . . S2 S 0.52736(14) 0.27849(8) 1.05325(5) 0.0739(3) Uani 1 1 d . . . N10 N 0.4130(3) 0.36833(18) 0.66956(14) 0.0428(5) Uani 1 1 d . . . C10 C 0.3084(3) 0.4340(2) 0.70399(19) 0.0437(6) Uani 1 1 d . . . C11 C 0.2527(4) 0.5163(2) 0.6516(2) 0.0533(7) Uani 1 1 d . . . H11 H 0.1801 0.5613 0.6763 0.064 Uiso 1 1 calc R . . C12 C 0.3044(4) 0.5311(3) 0.5639(2) 0.0584(8) Uani 1 1 d . . . H12 H 0.2670 0.5855 0.5286 0.070 Uiso 1 1 calc R . . C13 C 0.4127(5) 0.4637(3) 0.5291(2) 0.0612(9) Uani 1 1 d . . . H13 H 0.4498 0.4719 0.4698 0.073 Uiso 1 1 calc R . . C14 C 0.4648(4) 0.3846(2) 0.58349(19) 0.0567(8) Uani 1 1 d . . . H14 H 0.5391 0.3400 0.5601 0.068 Uiso 1 1 calc R . . C15 C 0.2545(4) 0.4176(3) 0.7998(2) 0.0627(9) Uani 1 1 d . . . H15A H 0.3053 0.3582 0.8253 0.094 Uiso 1 1 calc R . . H15B H 0.1453 0.4064 0.7999 0.094 Uiso 1 1 calc R . . H15C H 0.2783 0.4777 0.8359 0.094 Uiso 1 1 calc R . . N20 N 0.3692(3) 0.11209(18) 0.71239(15) 0.0439(5) Uani 1 1 d . . . C20 C 0.3526(4) 0.0616(2) 0.6331(2) 0.0506(7) Uani 1 1 d . . . C21 C 0.2601(4) -0.0272(2) 0.6261(3) 0.0610(9) Uani 1 1 d . . . H21 H 0.2516 -0.0627 0.5709 0.073 Uiso 1 1 calc R . . C22 C 0.1838(5) -0.0602(3) 0.7010(3) 0.0678(9) Uani 1 1 d . . . H22 H 0.1209 -0.1184 0.6970 0.081 Uiso 1 1 calc R . . C23 C 0.1978(5) -0.0086(3) 0.7835(3) 0.0727(10) Uani 1 1 d . . . H23 H 0.1452 -0.0312 0.8353 0.087 Uiso 1 1 calc R . . C24 C 0.2907(4) 0.0761(2) 0.7869(2) 0.0554(8) Uani 1 1 d . . . H24 H 0.3012 0.1111 0.8423 0.066 Uiso 1 1 calc R . . C25 C 0.4346(6) 0.1032(4) 0.5524(2) 0.0798(12) Uani 1 1 d . . . H25A H 0.4917 0.1637 0.5698 0.120 Uiso 1 1 calc R . . H25B H 0.3614 0.1213 0.5058 0.120 Uiso 1 1 calc R . . H25C H 0.5039 0.0516 0.5291 0.120 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 0.04748(18) 0.04346(17) 0.03984(16) 0.00088(12) -0.00108(16) 0.0003(2) N1 0.0507(15) 0.0601(16) 0.0676(16) -0.0005(13) 0.0022(12) 0.0024(13) C1 0.0550(17) 0.0433(14) 0.0430(13) -0.0037(11) -0.0057(11) 0.0100(13) S1 0.0447(4) 0.0960(6) 0.0755(5) -0.0204(4) -0.0045(4) 0.0135(5) N2 0.0744(17) 0.0595(13) 0.0461(11) 0.0020(10) -0.0125(12) 0.0010(18) C2 0.0567(18) 0.0457(12) 0.0475(13) 0.0029(10) -0.0079(12) 0.0051(16) S2 0.0957(8) 0.0835(5) 0.0426(3) -0.0047(3) -0.0102(4) 0.0193(6) N10 0.0469(13) 0.0430(11) 0.0384(11) 0.0015(9) -0.0003(9) -0.0039(10) C10 0.0449(15) 0.0399(13) 0.0462(14) -0.0033(10) 0.0016(12) -0.0051(12) C11 0.0564(18) 0.0458(15) 0.0578(19) -0.0001(13) -0.0006(15) 0.0042(14) C12 0.071(2) 0.0472(15) 0.0569(18) 0.0078(13) -0.0115(16) -0.0022(15) C13 0.076(2) 0.062(2) 0.0450(16) 0.0107(14) 0.0020(15) 0.0001(17) C14 0.070(2) 0.0568(15) 0.0437(14) 0.0036(11) 0.0071(14) 0.0085(15) C15 0.066(2) 0.067(2) 0.0554(18) 0.0034(15) 0.0128(17) 0.0094(17) N20 0.0423(12) 0.0431(12) 0.0462(12) 0.0023(9) -0.0027(10) 0.0028(10) C20 0.0528(17) 0.0499(15) 0.0491(15) -0.0034(13) -0.0035(13) 0.0048(13) C21 0.061(2) 0.0468(16) 0.075(2) -0.0068(15) -0.0178(18) 0.0065(15) C22 0.072(2) 0.0477(17) 0.084(2) 0.0055(17) -0.016(2) -0.0072(17) C23 0.073(2) 0.067(2) 0.077(2) 0.0205(18) 0.004(2) -0.013(2) C24 0.063(2) 0.0508(16) 0.0524(17) 0.0086(12) 0.0005(14) -0.0053(15) C25 0.095(3) 0.091(3) 0.0527(18) -0.0124(18) 0.0129(18) -0.019(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 Co1 N2 1.939(2) . ? Co1 N1 1.954(3) . ? Co1 N20 2.042(2) . ? Co1 N10 2.048(2) . ? N1 C1 1.154(4) . ? C1 S1 1.602(3) . ? N2 C2 1.157(4) . ? C2 S2 1.609(3) . ? N10 C10 1.341(4) . ? N10 C14 1.351(4) . ? C10 C11 1.395(4) . ? C10 C15 1.491(4) . ? C11 C12 1.371(5) . ? C12 C13 1.378(5) . ? C13 C14 1.370(4) . ? N20 C20 1.337(4) . ? N20 C24 1.366(4) . ? C20 C21 1.404(5) . ? C20 C25 1.478(5) . ? C21 C22 1.348(6) . ? C22 C23 1.383(6) . ? C23 C24 1.360(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 N2 Co1 N1 109.81(12) . . ? N2 Co1 N20 104.92(10) . . ? N1 Co1 N20 111.27(11) . . ? N2 Co1 N10 113.94(9) . . ? N1 Co1 N10 105.26(11) . . ? N20 Co1 N10 111.76(9) . . ? C1 N1 Co1 163.8(3) . . ? N1 C1 S1 179.2(3) . . ? C2 N2 Co1 177.3(3) . . ? N2 C2 S2 179.5(3) . . ? C10 N10 C14 118.5(2) . . ? C10 N10 Co1 126.61(18) . . ? C14 N10 Co1 114.9(2) . . ? N10 C10 C11 120.7(3) . . ? N10 C10 C15 118.4(3) . . ? C11 C10 C15 120.9(3) . . ? C12 C11 C10 120.3(3) . . ? C11 C12 C13 118.7(3) . . ? C14 C13 C12 118.8(3) . . ? N10 C14 C13 123.0(3) . . ? C20 N20 C24 118.1(3) . . ? C20 N20 Co1 125.8(2) . . ? C24 N20 Co1 116.1(2) . . ? N20 C20 C21 121.5(3) . . ? N20 C20 C25 117.5(3) . . ? C21 C20 C25 121.0(3) . . ? C22 C21 C20 118.8(3) . . ? C21 C22 C23 120.8(3) . . ? C24 C23 C22 118.1(4) . . ? C23 C24 N20 122.7(3) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.227 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 910141' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment '1-Zn.CIF' data_woe1911 #TrackingRef '1-Zn.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 N4 S2 Zn' _chemical_formula_sum 'C14 H14 N4 S2 Zn' _chemical_formula_weight 367.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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 8.7299(5) _cell_length_b 12.9000(6) _cell_length_c 14.6546(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1650.34(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 14644 _cell_measurement_theta_min 2.10 _cell_measurement_theta_max 29.00 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.1250 _exptl_crystal_size_mid 0.0973 _exptl_crystal_size_min 0.0467 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 1.738 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6539 _exptl_absorpt_correction_T_max 0.8518 _exptl_absorpt_process_details 'X-Shape and X-Red32 (Stoe, 2008)' _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 'STOE IPDS-2' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14644 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 29.00 _reflns_number_total 4368 _reflns_number_gt 3419 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area (Stoe, 2008)' _computing_cell_refinement 'X-Area (Stoe, 2008)' _computing_data_reduction 'X-Area (Stoe, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; XP in SHELXTL (Sheldrick, 2008) and Diamond (Brandenburg, 2011) ; _computing_publication_material 'XCIF in 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^)+(0.0385P)^2^+0.1494P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(13) _refine_ls_number_reflns 4368 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.0847 _refine_ls_wR_factor_gt 0.0790 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 0.50226(4) 0.24080(2) 0.73334(2) 0.05326(9) Uani 1 1 d . . . N1 N 0.7050(3) 0.2222(2) 0.6780(2) 0.0700(7) Uani 1 1 d . . . C1 C 0.8347(4) 0.2241(2) 0.6677(2) 0.0567(7) Uani 1 1 d . . . S1 S 1.01748(10) 0.22674(9) 0.65329(7) 0.0852(3) Uani 1 1 d . . . N2 N 0.5179(4) 0.2532(2) 0.86456(19) 0.0729(7) Uani 1 1 d . . . C2 C 0.5216(3) 0.2633(2) 0.9433(2) 0.0580(7) Uani 1 1 d . . . S2 S 0.52710(13) 0.27782(9) 1.05209(6) 0.0853(3) Uani 1 1 d . . . N10 N 0.4123(3) 0.36850(19) 0.66947(17) 0.0501(6) Uani 1 1 d . . . C10 C 0.3065(3) 0.4333(2) 0.7043(2) 0.0521(7) Uani 1 1 d . . . C11 C 0.2514(4) 0.5157(2) 0.6517(3) 0.0624(8) Uani 1 1 d . . . H11 H 0.1790 0.5606 0.6762 0.075 Uiso 1 1 calc R . . C12 C 0.3025(4) 0.5309(3) 0.5651(3) 0.0680(9) Uani 1 1 d . . . H12 H 0.2654 0.5857 0.5303 0.082 Uiso 1 1 calc R . . C13 C 0.4099(4) 0.4641(3) 0.5295(2) 0.0712(10) Uani 1 1 d . . . H13 H 0.4460 0.4724 0.4702 0.085 Uiso 1 1 calc R . . C14 C 0.4624(4) 0.3846(3) 0.5837(2) 0.0662(9) Uani 1 1 d . . . H14 H 0.5360 0.3400 0.5601 0.079 Uiso 1 1 calc R . . C15 C 0.2551(4) 0.4161(3) 0.7992(3) 0.0740(10) Uani 1 1 d . . . H15A H 0.3060 0.3563 0.8238 0.111 Uiso 1 1 calc R . . H15B H 0.1464 0.4049 0.7999 0.111 Uiso 1 1 calc R . . H15C H 0.2794 0.4758 0.8355 0.111 Uiso 1 1 calc R . . N20 N 0.3687(3) 0.11315(19) 0.71162(17) 0.0529(6) Uani 1 1 d . . . C20 C 0.3504(4) 0.0628(3) 0.6329(3) 0.0634(8) Uani 1 1 d . . . C21 C 0.2596(4) -0.0261(3) 0.6267(3) 0.0727(10) Uani 1 1 d . . . H21 H 0.2514 -0.0618 0.5718 0.087 Uiso 1 1 calc R . . C22 C 0.1848(5) -0.0590(3) 0.7009(3) 0.0790(11) Uani 1 1 d . . . H22 H 0.1217 -0.1170 0.6968 0.095 Uiso 1 1 calc R . . C23 C 0.1999(5) -0.0078(3) 0.7840(4) 0.0858(13) Uani 1 1 d . . . H23 H 0.1496 -0.0310 0.8361 0.103 Uiso 1 1 calc R . . C24 C 0.2903(4) 0.0768(3) 0.7859(3) 0.0678(9) Uani 1 1 d . . . H24 H 0.3001 0.1125 0.8408 0.081 Uiso 1 1 calc R . . C25 C 0.4308(6) 0.1037(4) 0.5527(3) 0.0924(13) Uani 1 1 d . . . H25A H 0.4873 0.1646 0.5695 0.139 Uiso 1 1 calc R . . H25B H 0.3576 0.1211 0.5063 0.139 Uiso 1 1 calc R . . H25C H 0.5001 0.0521 0.5297 0.139 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 0.05808(15) 0.05265(16) 0.04904(15) 0.00094(13) -0.00190(16) -0.0006(2) N1 0.0583(14) 0.0715(18) 0.080(2) -0.0011(15) 0.0021(12) 0.0019(13) C1 0.0680(18) 0.0524(17) 0.0496(16) -0.0045(13) -0.0076(13) 0.0086(14) S1 0.0536(4) 0.1116(7) 0.0904(7) -0.0237(5) -0.0061(4) 0.0163(6) N2 0.0918(18) 0.0719(16) 0.0549(13) -0.0001(13) -0.0160(15) 0.000(2) C2 0.0628(17) 0.0505(14) 0.0608(16) 0.0018(12) -0.0110(13) 0.0042(16) S2 0.1063(8) 0.0982(7) 0.0515(4) -0.0056(4) -0.0111(5) 0.0225(6) N10 0.0541(13) 0.0504(13) 0.0459(13) 0.0008(11) -0.0019(10) -0.0048(10) C10 0.0540(15) 0.0487(15) 0.0535(17) -0.0047(13) 0.0008(13) -0.0064(12) C11 0.0685(18) 0.0502(18) 0.069(2) -0.0005(16) 0.0026(17) 0.0061(14) C12 0.079(2) 0.0542(18) 0.071(2) 0.0079(17) -0.0140(19) 0.0040(16) C13 0.084(2) 0.078(2) 0.052(2) 0.0141(18) -0.0012(16) -0.0024(19) C14 0.078(2) 0.0679(19) 0.0523(17) 0.0017(15) 0.0054(16) 0.0096(16) C15 0.078(2) 0.080(3) 0.063(2) 0.0007(19) 0.014(2) 0.0113(19) N20 0.0542(12) 0.0516(14) 0.0528(15) 0.0030(11) -0.0030(11) 0.0056(10) C20 0.0620(18) 0.066(2) 0.062(2) -0.0021(17) -0.0070(16) 0.0111(15) C21 0.073(2) 0.0533(19) 0.092(3) -0.0039(19) -0.024(2) 0.0053(16) C22 0.085(3) 0.059(2) 0.092(3) 0.004(2) -0.017(2) -0.0059(19) C23 0.083(2) 0.082(3) 0.093(3) 0.026(2) 0.011(2) -0.011(2) C24 0.075(2) 0.066(2) 0.063(2) 0.0095(16) -0.0022(17) -0.0035(16) C25 0.109(3) 0.105(3) 0.063(2) -0.014(2) 0.009(2) -0.021(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 Zn1 N2 1.934(3) . ? Zn1 N1 1.962(3) . ? Zn1 N20 2.042(3) . ? Zn1 N10 2.051(2) . ? N1 C1 1.143(4) . ? C1 S1 1.610(3) . ? N2 C2 1.162(4) . ? C2 S2 1.606(3) . ? N10 C10 1.346(4) . ? N10 C14 1.347(4) . ? C10 C11 1.398(4) . ? C10 C15 1.478(5) . ? C11 C12 1.360(5) . ? C12 C13 1.376(5) . ? C13 C14 1.376(5) . ? N20 C20 1.333(4) . ? N20 C24 1.369(4) . ? C20 C21 1.397(5) . ? C20 C25 1.468(6) . ? C21 C22 1.337(6) . ? C22 C23 1.392(7) . ? C23 C24 1.347(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 N2 Zn1 N1 110.96(13) . . ? N2 Zn1 N20 105.16(11) . . ? N1 Zn1 N20 110.61(11) . . ? N2 Zn1 N10 114.49(11) . . ? N1 Zn1 N10 104.78(11) . . ? N20 Zn1 N10 110.96(9) . . ? C1 N1 Zn1 161.1(3) . . ? N1 C1 S1 180.0(4) . . ? C2 N2 Zn1 177.0(3) . . ? N2 C2 S2 179.7(3) . . ? C10 N10 C14 118.7(3) . . ? C10 N10 Zn1 126.1(2) . . ? C14 N10 Zn1 115.2(2) . . ? N10 C10 C11 119.9(3) . . ? N10 C10 C15 118.1(3) . . ? C11 C10 C15 121.9(3) . . ? C12 C11 C10 120.8(3) . . ? C11 C12 C13 119.2(3) . . ? C12 C13 C14 118.3(3) . . ? N10 C14 C13 123.1(3) . . ? C20 N20 C24 117.5(3) . . ? C20 N20 Zn1 126.6(2) . . ? C24 N20 Zn1 115.9(2) . . ? N20 C20 C21 121.6(4) . . ? N20 C20 C25 117.5(3) . . ? C21 C20 C25 120.9(4) . . ? C22 C21 C20 119.0(4) . . ? C21 C22 C23 120.9(4) . . ? C24 C23 C22 117.3(4) . . ? C23 C24 N20 123.6(4) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.204 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 910142' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_woe1814 #TrackingRef 'CCDC 910143_2-Co.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 Br2 Co N4 S2' _chemical_formula_sum 'C12 H8 Br2 Co N4 S2' _chemical_formula_weight 491.09 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' Br Br -0.2901 2.4595 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P bcn' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 11.3517(7) _cell_length_b 9.6554(5) _cell_length_c 15.5866(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1708.37(16) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 8998 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 28.08 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.2095 _exptl_crystal_size_mid 0.0920 _exptl_crystal_size_min 0.0512 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.909 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 948 _exptl_absorpt_coefficient_mu 5.923 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.1973 _exptl_absorpt_correction_T_max 0.6312 _exptl_absorpt_process_details 'X-Shape and X-Red32 (Stoe, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'STOE IPDS-1' _diffrn_measurement_method 'phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8998 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 28.08 _reflns_number_total 2060 _reflns_number_gt 1636 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area (Stoe, 2008)' _computing_cell_refinement 'X-Area (Stoe, 2008)' _computing_data_reduction 'X-Area (Stoe, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; XP in SHELXTL (Sheldrick, 2008) and Diamond (Brandenburg, 2011) ; _computing_publication_material 'XCIF in 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^)+(0.0515P)^2^+4.9681P] 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 0.0082(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2060 _refine_ls_number_parameters 97 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0650 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1265 _refine_ls_wR_factor_gt 0.1182 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.5000 0.15797(9) 0.2500 0.0383(3) Uani 1 2 d S . . N10 N 0.3661(3) 0.2614(4) 0.3094(2) 0.0371(7) Uani 1 1 d . . . C10 C 0.3852(4) 0.3580(5) 0.3687(3) 0.0429(9) Uani 1 1 d . . . C11 C 0.2978(4) 0.4230(5) 0.4148(3) 0.0504(11) Uani 1 1 d . . . H11 H 0.3159 0.4927 0.4557 0.060 Uiso 1 1 calc R . . C12 C 0.1835(5) 0.3835(6) 0.3997(3) 0.0543(13) Uani 1 1 d . . . H12 H 0.1209 0.4238 0.4315 0.065 Uiso 1 1 calc R . . C13 C 0.1603(4) 0.2853(6) 0.3382(3) 0.0555(12) Uani 1 1 d . . . H13 H 0.0815 0.2585 0.3262 0.067 Uiso 1 1 calc R . . C14 C 0.2529(4) 0.2262(5) 0.2941(3) 0.0455(10) Uani 1 1 d . . . H14 H 0.2365 0.1584 0.2516 0.055 Uiso 1 1 calc R . . Br1 Br 0.54567(5) 0.39807(8) 0.38824(4) 0.0771(3) Uani 1 1 d . . . N1 N 0.4193(4) 0.0384(5) 0.1690(3) 0.0518(10) Uani 1 1 d . . . C1 C 0.3857(4) -0.0512(5) 0.1256(3) 0.0393(9) Uani 1 1 d . . . S1 S 0.34117(12) -0.17640(15) 0.06568(9) 0.0566(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0305(4) 0.0436(5) 0.0409(4) 0.000 0.0020(3) 0.000 N10 0.0324(16) 0.0427(18) 0.0361(16) 0.0031(14) -0.0007(14) 0.0000(14) C10 0.038(2) 0.053(3) 0.037(2) -0.0026(18) 0.0000(17) 0.0017(19) C11 0.049(2) 0.062(3) 0.040(2) -0.005(2) 0.000(2) 0.011(2) C12 0.048(3) 0.069(3) 0.046(2) 0.001(2) 0.001(2) 0.022(2) C13 0.032(2) 0.071(3) 0.064(3) -0.001(3) -0.004(2) 0.009(2) C14 0.0335(19) 0.053(3) 0.050(2) -0.001(2) -0.0013(18) 0.0045(19) Br1 0.0459(3) 0.1187(6) 0.0667(4) -0.0446(4) 0.0083(3) -0.0213(3) N1 0.043(2) 0.055(2) 0.058(2) -0.0106(19) -0.0027(18) 0.0019(18) C1 0.0288(17) 0.048(2) 0.041(2) 0.0027(18) 0.0005(16) 0.0042(17) S1 0.0511(7) 0.0605(8) 0.0582(7) -0.0136(6) -0.0121(6) 0.0002(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 Co1 N1 1.941(4) . ? Co1 N1 1.941(4) 4_655 ? Co1 N10 2.041(3) 4_655 ? Co1 N10 2.041(3) . ? N10 C10 1.332(6) . ? N10 C14 1.351(6) . ? C10 C11 1.377(6) . ? C10 Br1 1.886(5) . ? C11 C12 1.373(7) . ? C12 C13 1.374(8) . ? C13 C14 1.380(6) . ? N1 C1 1.162(6) . ? C1 S1 1.609(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 N1 Co1 N1 107.0(3) . 4_655 ? N1 Co1 N10 110.36(16) . 4_655 ? N1 Co1 N10 103.57(15) 4_655 4_655 ? N1 Co1 N10 103.57(15) . . ? N1 Co1 N10 110.36(16) 4_655 . ? N10 Co1 N10 121.4(2) 4_655 . ? C10 N10 C14 117.0(4) . . ? C10 N10 Co1 122.4(3) . . ? C14 N10 Co1 120.3(3) . . ? N10 C10 C11 124.3(4) . . ? N10 C10 Br1 114.4(3) . . ? C11 C10 Br1 121.3(4) . . ? C12 C11 C10 117.7(5) . . ? C11 C12 C13 119.5(5) . . ? C12 C13 C14 119.1(5) . . ? N10 C14 C13 122.2(4) . . ? C1 N1 Co1 167.5(4) . . ? N1 C1 S1 179.1(4) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.08 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.345 _refine_diff_density_min -1.674 _refine_diff_density_rms 0.096 _database_code_depnum_ccdc_archive 'CCDC 910143' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment '2-Zn.CIF' data_woe1900 #TrackingRef '2-Zn.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 Br2 N4 S2 Zn' _chemical_formula_sum 'C12 H8 Br2 N4 S2 Zn' _chemical_formula_weight 497.53 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' S S 0.1246 0.1234 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P bcn' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.3675(3) _cell_length_b 9.7875(3) _cell_length_c 15.6246(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1738.38(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 28167 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 27.99 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.1071 _exptl_crystal_size_mid 0.0621 _exptl_crystal_size_min 0.0413 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.901 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 6.246 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.3747 _exptl_absorpt_correction_T_max 0.6457 _exptl_absorpt_process_details 'X-Shape and X-Red32 (Stoe, 2008)' _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 'STOE IPDS-2' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 28167 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0129 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 27.99 _reflns_number_total 2096 _reflns_number_gt 1855 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area (Stoe, 2008)' _computing_cell_refinement 'X-Area (Stoe, 2008)' _computing_data_reduction 'X-Area (Stoe, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; XP in SHELXTL (Sheldrick, 2008) and Diamond (Brandenburg, 2011) ; _computing_publication_material 'XCIF in 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^)+(0.0281P)^2^+0.9669P] 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 2096 _refine_ls_number_parameters 105 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.0917 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.327 _refine_ls_restrained_S_all 1.327 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.5000 0.65455(6) 0.2500 0.06040(18) Uani 1 2 d S . . N1 N 0.4173(3) 0.5389(4) 0.3307(2) 0.0797(9) Uani 1 1 d . . . C1 C 0.3864(3) 0.4514(4) 0.3743(2) 0.0613(8) Uani 1 1 d . . . S1 S 0.34432(11) 0.32823(13) 0.43438(8) 0.0876(3) Uani 1 1 d . . . N10 N 0.3687(2) 0.7596(3) 0.18998(17) 0.0561(6) Uani 1 1 d . A . C10 C 0.3875(3) 0.8560(4) 0.1316(2) 0.0663(9) Uani 1 1 d . . . C11 C 0.3004(4) 0.9194(4) 0.0861(3) 0.0752(10) Uani 1 1 d . A . H11 H 0.3178 0.9876 0.0467 0.090 Uiso 1 1 calc R . . C12 C 0.1865(4) 0.8794(5) 0.1005(3) 0.0822(12) Uani 1 1 d . . . H12 H 0.1253 0.9175 0.0691 0.099 Uiso 1 1 calc R A . C13 C 0.1642(3) 0.7829(5) 0.1616(3) 0.0833(12) Uani 1 1 d . A . H13 H 0.0873 0.7565 0.1736 0.100 Uiso 1 1 calc R . . C14 C 0.2565(3) 0.7256(4) 0.2049(3) 0.0692(9) Uani 1 1 d . . . H14 H 0.2406 0.6602 0.2465 0.083 Uiso 1 1 calc R A . Br1 Br 0.5517(4) 0.8794(4) 0.1050(3) 0.0805(6) Uani 0.50 1 d P A 1 Br1' Br 0.5386(4) 0.9237(4) 0.1207(3) 0.1027(10) Uani 0.50 1 d P A 2 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 0.0480(3) 0.0650(3) 0.0682(3) 0.000 -0.0036(2) 0.000 N1 0.0668(19) 0.083(2) 0.089(2) 0.019(2) 0.0007(18) -0.0013(17) C1 0.0442(16) 0.074(2) 0.065(2) -0.0002(18) 0.0003(15) 0.0069(15) S1 0.0759(6) 0.0917(7) 0.0952(8) 0.0239(6) 0.0177(6) -0.0006(6) N10 0.0477(14) 0.0637(17) 0.0570(15) -0.0056(13) -0.0010(12) 0.0004(12) C10 0.0573(19) 0.081(3) 0.0602(19) 0.0015(18) -0.0033(16) 0.0004(18) C11 0.074(2) 0.086(3) 0.065(2) 0.008(2) 0.0000(19) 0.016(2) C12 0.069(3) 0.103(3) 0.074(2) -0.003(2) -0.005(2) 0.032(2) C13 0.0457(18) 0.106(3) 0.098(3) 0.001(3) 0.003(2) 0.013(2) C14 0.0528(18) 0.076(2) 0.079(2) 0.003(2) 0.0027(18) 0.0023(17) Br1 0.0599(8) 0.1049(16) 0.0767(10) 0.0274(10) 0.0028(6) -0.0089(10) Br1' 0.0672(13) 0.137(3) 0.104(2) 0.0493(17) -0.0083(12) -0.0203(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 N1 1.938(4) 3_655 ? Zn1 N1 1.938(4) . ? Zn1 N10 2.041(3) 3_655 ? Zn1 N10 2.041(3) . ? N1 C1 1.148(5) . ? C1 S1 1.601(4) . ? N10 C10 1.329(5) . ? N10 C14 1.338(4) . ? C10 C11 1.368(5) . ? C10 Br1' 1.849(6) . ? C10 Br1 1.927(6) . ? C11 C12 1.370(6) . ? C12 C13 1.367(6) . ? C13 C14 1.369(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 N1 Zn1 N1 108.5(2) 3_655 . ? N1 Zn1 N10 103.80(13) 3_655 3_655 ? N1 Zn1 N10 110.49(13) . 3_655 ? N1 Zn1 N10 110.49(13) 3_655 . ? N1 Zn1 N10 103.80(13) . . ? N10 Zn1 N10 119.49(16) 3_655 . ? C1 N1 Zn1 165.8(3) . . ? N1 C1 S1 179.3(4) . . ? C10 N10 C14 116.7(3) . . ? C10 N10 Zn1 123.7(2) . . ? C14 N10 Zn1 119.5(2) . . ? N10 C10 C11 124.2(4) . . ? N10 C10 Br1' 117.9(3) . . ? C11 C10 Br1' 117.5(4) . . ? N10 C10 Br1 112.9(3) . . ? C11 C10 Br1 122.4(3) . . ? Br1' C10 Br1 15.66(17) . . ? C10 C11 C12 118.0(4) . . ? C13 C12 C11 119.2(4) . . ? C12 C13 C14 119.0(4) . . ? N10 C14 C13 122.9(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.218 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 910144' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment '3-Co_Modi_I.CIF' data_br17 #TrackingRef '3-Co_Modi_I.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 Cl2 Co N4 S2' _chemical_formula_sum 'C12 H8 Cl2 Co N4 S2' _chemical_formula_weight 402.17 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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 8.6064(2) _cell_length_b 12.7726(3) _cell_length_c 14.6199(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1607.11(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 28595 _cell_measurement_theta_min 2.12 _cell_measurement_theta_max 28.99 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.2906 _exptl_crystal_size_mid 0.1822 _exptl_crystal_size_min 0.1230 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 1.655 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.4860 _exptl_absorpt_correction_T_max 0.7014 _exptl_absorpt_process_details 'X-Shape and X-Red32 (Stoe, 2008)' _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 'STOE IPDS-2' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 28595 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0153 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 28.99 _reflns_number_total 4250 _reflns_number_gt 4013 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area (Stoe, 2008)' _computing_cell_refinement 'X-Area (Stoe, 2008)' _computing_data_reduction 'X-Area (Stoe, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; XP in SHELXTL (Sheldrick, 2008) and Diamond (Brandenburg, 2011) ; _computing_publication_material 'XCIF in 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^)+(0.0318P)^2^+0.1937P] 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 0.027(13) _refine_ls_number_reflns 4250 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0640 _refine_ls_wR_factor_gt 0.0629 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _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 0.50739(3) 0.238551(18) 0.731058(17) 0.04354(7) Uani 1 1 d . . . N1 N 0.7102(2) 0.22005(16) 0.67587(14) 0.0573(4) Uani 1 1 d . . . C1 C 0.8433(3) 0.22267(15) 0.66286(13) 0.0461(4) Uani 1 1 d . . . S1 S 1.02734(7) 0.22870(6) 0.64536(5) 0.06620(16) Uani 1 1 d . . . N2 N 0.5316(2) 0.25113(15) 0.86199(13) 0.0598(5) Uani 1 1 d . . . C2 C 0.5343(3) 0.26081(16) 0.94076(14) 0.0506(5) Uani 1 1 d . . . S2 S 0.53954(10) 0.27367(6) 1.05009(4) 0.07323(19) Uani 1 1 d . . . N10 N 0.4129(2) 0.36635(12) 0.66701(11) 0.0424(3) Uani 1 1 d . . . C10 C 0.3068(2) 0.43032(16) 0.70174(14) 0.0449(4) Uani 1 1 d . . . C11 C 0.2411(3) 0.51302(16) 0.65528(17) 0.0534(5) Uani 1 1 d . . . H11 H 0.1686 0.5566 0.6832 0.064 Uiso 1 1 calc R . . C12 C 0.2864(3) 0.52894(18) 0.56579(17) 0.0589(6) Uani 1 1 d . . . H12 H 0.2430 0.5828 0.5315 0.071 Uiso 1 1 calc R . . C13 C 0.3961(3) 0.46440(19) 0.52816(16) 0.0614(6) Uani 1 1 d . . . H13 H 0.4290 0.4745 0.4682 0.074 Uiso 1 1 calc R . . C14 C 0.4568(3) 0.38485(18) 0.57966(14) 0.0534(5) Uani 1 1 d . . . H14 H 0.5315 0.3416 0.5535 0.064 Uiso 1 1 calc R . . Cl1 Cl 0.24979(9) 0.40522(7) 0.81179(4) 0.0751(2) Uani 1 1 d . . . N20 N 0.3665(2) 0.11073(13) 0.71691(11) 0.0426(3) Uani 1 1 d . . . C20 C 0.3415(3) 0.06003(16) 0.63884(15) 0.0475(4) Uani 1 1 d . . . C21 C 0.2494(3) -0.02723(17) 0.62991(18) 0.0558(5) Uani 1 1 d . . . H21 H 0.2379 -0.0606 0.5738 0.067 Uiso 1 1 calc R . . C22 C 0.1754(3) -0.0634(2) 0.70636(19) 0.0634(6) Uani 1 1 d . . . H22 H 0.1115 -0.1219 0.7031 0.076 Uiso 1 1 calc R . . C23 C 0.1967(3) -0.0121(2) 0.78857(19) 0.0636(6) Uani 1 1 d . . . H23 H 0.1466 -0.0352 0.8412 0.076 Uiso 1 1 calc R . . C24 C 0.2929(3) 0.07357(18) 0.79119(15) 0.0527(5) Uani 1 1 d . . . H24 H 0.3077 0.1074 0.8468 0.063 Uiso 1 1 calc R . . Cl2 Cl 0.43005(10) 0.11229(6) 0.54344(4) 0.07211(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.04741(13) 0.04313(12) 0.04006(11) 0.00227(9) -0.00073(11) -0.00129(12) N1 0.0511(11) 0.0580(11) 0.0627(11) -0.0023(9) 0.0032(8) 0.0025(8) C1 0.0559(12) 0.0420(10) 0.0404(9) -0.0031(7) -0.0049(8) 0.0101(9) S1 0.0441(3) 0.0814(4) 0.0731(4) -0.0168(3) -0.0061(3) 0.0130(3) N2 0.0722(12) 0.0618(10) 0.0452(8) 0.0016(7) -0.0107(8) -0.0011(10) C2 0.0563(12) 0.0447(9) 0.0508(10) 0.0047(8) -0.0109(8) 0.0019(9) S2 0.0946(5) 0.0820(4) 0.0431(3) -0.0036(3) -0.0104(3) 0.0160(4) N10 0.0465(9) 0.0398(8) 0.0410(8) -0.0004(6) 0.0005(7) -0.0021(6) C10 0.0460(11) 0.0448(10) 0.0440(9) -0.0039(8) 0.0013(8) -0.0053(8) C11 0.0575(13) 0.0430(10) 0.0598(13) -0.0022(9) 0.0006(12) 0.0061(10) C12 0.0661(16) 0.0456(11) 0.0651(14) 0.0106(10) -0.0079(12) 0.0009(10) C13 0.0778(18) 0.0615(14) 0.0450(11) 0.0129(10) 0.0039(11) 0.0036(12) C14 0.0649(15) 0.0524(10) 0.0428(9) 0.0027(8) 0.0083(9) 0.0034(10) Cl1 0.0779(4) 0.1002(5) 0.0472(3) 0.0065(3) 0.0173(3) 0.0239(4) N20 0.0419(8) 0.0427(8) 0.0433(8) 0.0043(6) 0.0009(7) 0.0034(6) C20 0.0482(11) 0.0454(10) 0.0490(11) 0.0019(9) 0.0012(9) 0.0045(9) C21 0.0594(13) 0.0429(10) 0.0651(13) -0.0051(9) -0.0121(12) 0.0027(10) C22 0.0615(14) 0.0483(11) 0.0804(17) 0.0157(11) -0.0107(13) -0.0086(10) C23 0.0622(14) 0.0622(14) 0.0665(15) 0.0190(11) 0.0053(12) -0.0066(11) C24 0.0589(13) 0.0535(11) 0.0459(10) 0.0082(9) 0.0039(9) 0.0006(10) Cl2 0.0897(5) 0.0814(4) 0.0452(3) -0.0078(3) 0.0118(3) -0.0222(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 Co1 N2 1.9322(19) . ? Co1 N1 1.9375(19) . ? Co1 N20 2.0441(17) . ? Co1 N10 2.0499(16) . ? N1 C1 1.162(3) . ? C1 S1 1.606(2) . ? N2 C2 1.159(3) . ? C2 S2 1.607(2) . ? N10 C10 1.326(3) . ? N10 C14 1.353(3) . ? C10 C11 1.378(3) . ? C10 Cl1 1.712(2) . ? C11 C12 1.380(4) . ? C12 C13 1.368(4) . ? C13 C14 1.368(3) . ? N20 C20 1.330(3) . ? N20 C24 1.344(3) . ? C20 C21 1.374(3) . ? C20 Cl2 1.724(2) . ? C21 C22 1.367(4) . ? C22 C23 1.381(4) . ? C23 C24 1.372(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Co1 N1 109.01(9) . . ? N2 Co1 N20 103.32(8) . . ? N1 Co1 N20 113.26(8) . . ? N2 Co1 N10 115.41(8) . . ? N1 Co1 N10 105.32(8) . . ? N20 Co1 N10 110.77(6) . . ? C1 N1 Co1 162.38(19) . . ? N1 C1 S1 178.9(2) . . ? C2 N2 Co1 174.8(2) . . ? N2 C2 S2 179.5(2) . . ? C10 N10 C14 116.49(18) . . ? C10 N10 Co1 126.07(14) . . ? C14 N10 Co1 117.37(14) . . ? N10 C10 C11 124.51(19) . . ? N10 C10 Cl1 116.21(16) . . ? C11 C10 Cl1 119.27(17) . . ? C10 C11 C12 117.6(2) . . ? C13 C12 C11 119.2(2) . . ? C12 C13 C14 119.3(2) . . ? N10 C14 C13 122.9(2) . . ? C20 N20 C24 116.43(19) . . ? C20 N20 Co1 124.88(14) . . ? C24 N20 Co1 118.69(15) . . ? N20 C20 C21 124.8(2) . . ? N20 C20 Cl2 115.74(16) . . ? C21 C20 Cl2 119.49(18) . . ? C20 C21 C22 117.7(2) . . ? C21 C22 C23 119.3(2) . . ? C24 C23 C22 118.8(2) . . ? N20 C24 C23 122.9(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.258 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 910145' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment '3-Co_Modi_II.CIF' data_woe1754 #TrackingRef '3-Co_Modi_II.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 Cl2 Co N4 S2' _chemical_formula_sum 'C12 H8 Cl2 Co N4 S2' _chemical_formula_weight 402.17 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' S S 0.1246 0.1234 '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 orthorhombic _symmetry_space_group_name_H-M 'P bcn' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.2928(7) _cell_length_b 9.7123(5) _cell_length_c 15.1913(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1666.17(16) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 11189 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 28.03 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.1845 _exptl_crystal_size_mid 0.1414 _exptl_crystal_size_min 0.1037 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.603 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 1.597 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6702 _exptl_absorpt_correction_T_max 0.7569 _exptl_absorpt_process_details 'X-Shape and X-Red32 (Stoe, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'STOE IPDS-1' _diffrn_measurement_method 'phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11189 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 28.03 _reflns_number_total 2005 _reflns_number_gt 1671 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area (Stoe, 2008)' _computing_cell_refinement 'X-Area (Stoe, 2008)' _computing_data_reduction 'X-Area (Stoe, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; XP in SHELXTL (Sheldrick, 2008) and Diamond (Brandenburg, 2011) ; _computing_publication_material 'XCIF in 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^)+(0.0461P)^2^+0.5308P] 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 0.0128(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2005 _refine_ls_number_parameters 97 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0799 _refine_ls_wR_factor_gt 0.0754 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.16042(3) 0.2500 0.03125(13) Uani 1 2 d S . . N1 N 0.08218(15) 0.04185(18) 0.33302(11) 0.0423(4) Uani 1 1 d . . . C1 C 0.11605(15) -0.05129(19) 0.37391(11) 0.0331(4) Uani 1 1 d . . . S1 S 0.16078(5) -0.18185(6) 0.43040(4) 0.04749(17) Uani 1 1 d . . . N10 N 0.13270(13) 0.26656(15) 0.18920(10) 0.0318(3) Uani 1 1 d . . . C10 C 0.11120(17) 0.3650(2) 0.13024(12) 0.0372(4) Uani 1 1 d . . . C11 C 0.19866(19) 0.4319(2) 0.08301(13) 0.0433(5) Uani 1 1 d . . . H11 H 0.1797 0.5029 0.0423 0.052 Uiso 1 1 calc R . . C12 C 0.31441(19) 0.3921(2) 0.09698(13) 0.0467(5) Uani 1 1 d . . . H12 H 0.3768 0.4338 0.0646 0.056 Uiso 1 1 calc R . . C13 C 0.33885(18) 0.2910(2) 0.15856(15) 0.0473(5) Uani 1 1 d . . . H13 H 0.4181 0.2633 0.1696 0.057 Uiso 1 1 calc R . . C14 C 0.24644(16) 0.2313(2) 0.20351(13) 0.0375(4) Uani 1 1 d . . . H14 H 0.2635 0.1627 0.2462 0.045 Uiso 1 1 calc R . . Cl1 Cl -0.03567(5) 0.40413(9) 0.11485(5) 0.0707(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.02462(19) 0.0339(2) 0.0352(2) 0.000 0.00292(12) 0.000 N1 0.0350(8) 0.0440(9) 0.0480(9) 0.0062(8) -0.0003(7) -0.0017(7) C1 0.0255(8) 0.0405(9) 0.0334(8) -0.0007(7) -0.0009(7) -0.0044(7) S1 0.0467(3) 0.0464(3) 0.0493(3) 0.0094(2) -0.0127(2) 0.0013(2) N10 0.0277(7) 0.0354(7) 0.0323(7) -0.0025(6) 0.0019(6) -0.0024(6) C10 0.0351(9) 0.0434(10) 0.0331(9) 0.0027(8) 0.0016(7) -0.0013(8) C11 0.0466(11) 0.0474(11) 0.0359(9) 0.0056(8) -0.0014(8) -0.0118(9) C12 0.0409(11) 0.0595(12) 0.0396(10) 0.0013(9) 0.0017(8) -0.0224(9) C13 0.0273(9) 0.0606(12) 0.0539(12) 0.0032(10) -0.0007(8) -0.0096(8) C14 0.0286(8) 0.0418(10) 0.0422(9) 0.0006(8) 0.0002(7) -0.0027(7) Cl1 0.0400(3) 0.1034(5) 0.0687(4) 0.0432(4) 0.0060(3) 0.0177(3) _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 1.9438(17) 3 ? Co1 N1 1.9438(17) . ? Co1 N10 2.0400(14) 3 ? Co1 N10 2.0400(14) . ? N1 C1 1.162(2) . ? C1 S1 1.6124(19) . ? N10 C10 1.332(2) . ? N10 C14 1.347(2) . ? C10 C11 1.383(3) . ? C10 Cl1 1.718(2) . ? C11 C12 1.379(3) . ? C12 C13 1.384(3) . ? C13 C14 1.375(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Co1 N1 107.34(10) 3 . ? N1 Co1 N10 104.03(6) 3 3 ? N1 Co1 N10 110.87(6) . 3 ? N1 Co1 N10 110.87(6) 3 . ? N1 Co1 N10 104.03(6) . . ? N10 Co1 N10 119.30(8) 3 . ? C1 N1 Co1 164.83(16) . . ? N1 C1 S1 178.98(17) . . ? C10 N10 C14 117.69(16) . . ? C10 N10 Co1 122.21(12) . . ? C14 N10 Co1 119.93(12) . . ? N10 C10 C11 123.78(19) . . ? N10 C10 Cl1 115.24(14) . . ? C11 C10 Cl1 120.97(16) . . ? C12 C11 C10 117.72(19) . . ? C11 C12 C13 119.44(18) . . ? C14 C13 C12 118.91(19) . . ? N10 C14 C13 122.43(18) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.03 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.377 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 910146' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment 'CCDC 910147_3-Zn_alpha.CIF' data_woe2128a #TrackingRef 'CCDC 910147_3-Zn_alpha.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 Cl2 N4 S2 Zn' _chemical_formula_sum 'C12 H8 Cl2 N4 S2 Zn' _chemical_formula_weight 408.61 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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 8.6264(4) _cell_length_b 12.7738(4) _cell_length_c 14.6614(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1615.57(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 21176 _cell_measurement_theta_min 2.11 _cell_measurement_theta_max 29.00 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.1803 _exptl_crystal_size_mid 0.1450 _exptl_crystal_size_min 0.0782 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.680 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 2.105 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6238 _exptl_absorpt_correction_T_max 0.7572 _exptl_absorpt_process_details 'X-Shape and X-Red32 (Stoe, 2008)' _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 'STOE IPDS-2' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 21176 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 29.00 _reflns_number_total 4288 _reflns_number_gt 3915 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'X-Area (Stoe, 2008)' _computing_data_reduction 'X-Area (Stoe, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; XP in SHELXTL (Sheldrick, 2008) and Diamond (Brandenburg, 2011) ; _computing_publication_material 'XCIF in 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^)+(0.0316P)^2^+0.1914P] 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 0.000(17) _refine_ls_number_reflns 4288 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0637 _refine_ls_wR_factor_gt 0.0618 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.49061(3) 0.261357(18) 0.268217(16) 0.04895(7) Uani 1 1 d . . . N2 N 0.4672(3) 0.25017(18) 0.13752(14) 0.0663(5) Uani 1 1 d . . . C2 C 0.4654(3) 0.23996(18) 0.05941(16) 0.0552(5) Uani 1 1 d . . . S2 S 0.46155(10) 0.22677(7) -0.04965(4) 0.0791(2) Uani 1 1 d . . . N1 N 0.2907(2) 0.27995(18) 0.32656(15) 0.0636(5) Uani 1 1 d . . . C1 C 0.1581(3) 0.27701(17) 0.33792(14) 0.0507(5) Uani 1 1 d . . . S1 S -0.02602(7) 0.27094(6) 0.35396(5) 0.07161(18) Uani 1 1 d . . . N10 N 0.5876(2) 0.13413(14) 0.33217(12) 0.0463(4) Uani 1 1 d . . . C10 C 0.6927(2) 0.06996(18) 0.29746(15) 0.0492(5) Uani 1 1 d . . . C11 C 0.7594(3) -0.01251(19) 0.34438(19) 0.0582(6) Uani 1 1 d . . . H11 H 0.8316 -0.0562 0.3167 0.070 Uiso 1 1 calc R . . C12 C 0.7147(3) -0.0275(2) 0.43361(19) 0.0637(6) Uani 1 1 d . . . H12 H 0.7582 -0.0812 0.4680 0.076 Uiso 1 1 calc R . . C13 C 0.6055(3) 0.0373(2) 0.47126(17) 0.0650(7) Uani 1 1 d . . . H13 H 0.5734 0.0277 0.5312 0.078 Uiso 1 1 calc R . . C14 C 0.5443(3) 0.11627(19) 0.41976(16) 0.0575(6) Uani 1 1 d . . . H14 H 0.4699 0.1596 0.4458 0.069 Uiso 1 1 calc R . . Cl1 Cl 0.74910(10) 0.09413(7) 0.18739(4) 0.0797(2) Uani 1 1 d . . . N20 N 0.6334(2) 0.38921(14) 0.28406(12) 0.0472(4) Uani 1 1 d . . . C20 C 0.6587(3) 0.43984(18) 0.36156(16) 0.0514(5) Uani 1 1 d . . . C21 C 0.7517(3) 0.52737(19) 0.36998(19) 0.0600(6) Uani 1 1 d . . . H21 H 0.7638 0.5611 0.4257 0.072 Uiso 1 1 calc R . . C22 C 0.8249(3) 0.5624(2) 0.2934(2) 0.0693(7) Uani 1 1 d . . . H22 H 0.8893 0.6206 0.2964 0.083 Uiso 1 1 calc R . . C23 C 0.8031(3) 0.5112(2) 0.2114(2) 0.0674(7) Uani 1 1 d . . . H23 H 0.8525 0.5342 0.1587 0.081 Uiso 1 1 calc R . . C24 C 0.7069(3) 0.4253(2) 0.20944(16) 0.0562(5) Uani 1 1 d . . . H24 H 0.6920 0.3909 0.1543 0.067 Uiso 1 1 calc R . . Cl2 Cl 0.57071(10) 0.38894(7) 0.45754(4) 0.0775(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.05306(12) 0.04839(12) 0.04539(11) 0.00225(9) -0.00097(10) -0.00142(11) N2 0.0812(13) 0.0698(12) 0.0480(9) 0.0012(9) -0.0114(9) 0.0001(12) C2 0.0596(12) 0.0481(11) 0.0581(12) 0.0051(9) -0.0107(9) 0.0026(10) S2 0.1012(5) 0.0881(5) 0.0481(3) -0.0038(3) -0.0107(3) 0.0168(4) N1 0.0545(10) 0.0660(13) 0.0704(12) -0.0034(11) 0.0042(9) 0.0014(9) C1 0.0617(12) 0.0462(11) 0.0443(10) -0.0025(9) -0.0051(9) 0.0090(10) S1 0.0491(3) 0.0864(4) 0.0793(4) -0.0176(4) -0.0069(3) 0.0127(3) N10 0.0517(9) 0.0436(9) 0.0435(8) 0.0002(7) 0.0000(7) -0.0015(7) C10 0.0497(11) 0.0468(11) 0.0512(11) -0.0043(9) 0.0017(9) -0.0042(9) C11 0.0627(13) 0.0477(12) 0.0643(14) -0.0022(11) -0.0002(12) 0.0052(11) C12 0.0723(17) 0.0501(13) 0.0686(15) 0.0102(12) -0.0097(12) 0.0018(11) C13 0.0838(18) 0.0631(15) 0.0480(12) 0.0114(11) 0.0033(12) 0.0030(13) C14 0.0708(15) 0.0567(12) 0.0451(10) 0.0031(9) 0.0076(10) 0.0044(11) Cl1 0.0840(4) 0.1035(6) 0.0515(3) 0.0055(3) 0.0183(3) 0.0235(4) N20 0.0470(9) 0.0462(9) 0.0484(9) 0.0042(7) 0.0016(7) 0.0028(7) C20 0.0542(12) 0.0471(11) 0.0527(12) 0.0002(10) -0.0002(10) 0.0037(9) C21 0.0636(13) 0.0478(12) 0.0687(14) -0.0040(11) -0.0103(12) 0.0013(11) C22 0.0670(15) 0.0539(13) 0.0870(19) 0.0163(13) -0.0113(14) -0.0094(12) C23 0.0661(15) 0.0673(15) 0.0687(17) 0.0186(13) 0.0074(13) -0.0068(12) C24 0.0618(13) 0.0573(13) 0.0496(12) 0.0075(10) 0.0061(10) 0.0004(10) Cl2 0.0962(5) 0.0869(5) 0.0496(3) -0.0085(3) 0.0121(3) -0.0231(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 N2 1.932(2) . ? Zn1 N1 1.939(2) . ? Zn1 N10 2.0545(17) . ? Zn1 N20 2.0589(18) . ? N2 C2 1.153(3) . ? C2 S2 1.608(2) . ? N1 C1 1.157(3) . ? C1 S1 1.608(2) . ? N10 C10 1.324(3) . ? N10 C14 1.357(3) . ? C10 C11 1.383(3) . ? C10 Cl1 1.714(2) . ? C11 C12 1.377(4) . ? C12 C13 1.370(4) . ? C13 C14 1.366(3) . ? N20 C20 1.326(3) . ? N20 C24 1.346(3) . ? C20 C21 1.381(3) . ? C20 Cl2 1.726(2) . ? C21 C22 1.363(4) . ? C22 C23 1.382(4) . ? C23 C24 1.376(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 N2 Zn1 N1 110.72(9) . . ? N2 Zn1 N10 115.89(8) . . ? N1 Zn1 N10 104.94(9) . . ? N2 Zn1 N20 103.47(8) . . ? N1 Zn1 N20 112.65(9) . . ? N10 Zn1 N20 109.40(7) . . ? C2 N2 Zn1 174.3(2) . . ? N2 C2 S2 179.4(2) . . ? C1 N1 Zn1 159.9(2) . . ? N1 C1 S1 179.1(2) . . ? C10 N10 C14 116.6(2) . . ? C10 N10 Zn1 126.40(15) . . ? C14 N10 Zn1 116.92(15) . . ? N10 C10 C11 124.4(2) . . ? N10 C10 Cl1 116.41(17) . . ? C11 C10 Cl1 119.18(18) . . ? C12 C11 C10 117.5(2) . . ? C13 C12 C11 119.4(2) . . ? C14 C13 C12 119.3(2) . . ? N10 C14 C13 122.7(2) . . ? C20 N20 C24 116.9(2) . . ? C20 N20 Zn1 125.61(15) . . ? C24 N20 Zn1 117.52(16) . . ? N20 C20 C21 124.6(2) . . ? N20 C20 Cl2 116.27(18) . . ? C21 C20 Cl2 119.2(2) . . ? C22 C21 C20 117.4(3) . . ? C21 C22 C23 119.9(2) . . ? C24 C23 C22 118.5(2) . . ? N20 C24 C23 122.7(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.249 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 910147' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment '3-Zn_Modi_II.CIF' data_woe1906 #TrackingRef '3-Zn_Modi_II.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 Cl2 N4 S2 Zn' _chemical_formula_sum 'C12 H8 Cl2 N4 S2 Zn' _chemical_formula_weight 408.61 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 'P bcn' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.3237(4) _cell_length_b 9.7997(3) _cell_length_c 15.2661(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1694.06(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 27065 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 28.00 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.2469 _exptl_crystal_size_mid 0.1855 _exptl_crystal_size_min 0.0917 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.602 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 2.007 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.4631 _exptl_absorpt_correction_T_max 0.7013 _exptl_absorpt_process_details 'X-Shape and X-Red32 (Stoe, 2008)' _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 'STOE IPDS-2' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 27065 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0106 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 28.00 _reflns_number_total 2024 _reflns_number_gt 1842 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'X-Area (Stoe, 2008)' _computing_data_reduction 'X-Area (Stoe, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; XP in SHELXTL (Sheldrick, 2008) and Diamond (Brandenburg, 2011) ; _computing_publication_material 'XCIF in 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^)+(0.0366P)^2^+0.5409P] 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 2024 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0891 _refine_ls_wR_factor_gt 0.0867 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_restrained_S_all 1.166 _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 0.5000 0.65876(4) 0.7500 0.05960(14) Uani 1 2 d S . . N1 N 0.58317(19) 0.5438(2) 0.66731(15) 0.0767(6) Uani 1 1 d . . . C1 C 0.61480(19) 0.4518(3) 0.62662(14) 0.0604(5) Uani 1 1 d . . . S1 S 0.65786(7) 0.32338(8) 0.57027(5) 0.0863(2) Uani 1 1 d . . . N10 N 0.63065(15) 0.76538(19) 0.81114(12) 0.0575(4) Uani 1 1 d . . . C10 C 0.6104(2) 0.8621(3) 0.87021(15) 0.0676(6) Uani 1 1 d . . . C11 C 0.6974(3) 0.9268(3) 0.91685(17) 0.0775(7) Uani 1 1 d . . . H11 H 0.6793 0.9956 0.9566 0.093 Uiso 1 1 calc R . . C12 C 0.8118(3) 0.8871(3) 0.90310(18) 0.0816(8) Uani 1 1 d . . . H12 H 0.8729 0.9262 0.9352 0.098 Uiso 1 1 calc R . . C13 C 0.8353(2) 0.7893(3) 0.8417(2) 0.0832(8) Uani 1 1 d . . . H13 H 0.9127 0.7630 0.8303 0.100 Uiso 1 1 calc R . . C14 C 0.7434(2) 0.7305(3) 0.79695(17) 0.0684(6) Uani 1 1 d . . . H14 H 0.7599 0.6640 0.7553 0.082 Uiso 1 1 calc R . . Cl1 Cl 0.46484(8) 0.90329(12) 0.88566(7) 0.1182(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0500(2) 0.0619(2) 0.0669(2) 0.000 -0.00524(15) 0.000 N1 0.0670(12) 0.0775(13) 0.0856(14) -0.0154(11) 0.0009(11) 0.0004(11) C1 0.0473(10) 0.0716(14) 0.0621(12) 0.0023(11) 0.0010(9) -0.0073(10) S1 0.0851(5) 0.0849(5) 0.0890(5) -0.0174(4) 0.0204(4) 0.0033(4) N10 0.0521(9) 0.0607(10) 0.0598(10) 0.0028(8) -0.0023(8) -0.0029(8) C10 0.0640(13) 0.0760(15) 0.0627(12) -0.0042(11) -0.0012(10) -0.0033(11) C11 0.0831(17) 0.0846(17) 0.0649(13) -0.0092(12) -0.0012(12) -0.0195(14) C12 0.0726(17) 0.101(2) 0.0713(15) 0.0016(14) -0.0022(12) -0.0343(15) C13 0.0518(12) 0.103(2) 0.0945(19) -0.0037(16) 0.0020(12) -0.0146(13) C14 0.0560(12) 0.0742(15) 0.0751(14) -0.0022(12) -0.0010(11) -0.0057(11) Cl1 0.0745(5) 0.1617(9) 0.1183(7) -0.0672(6) -0.0090(4) 0.0268(5) _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 1.936(2) . ? Zn1 N1 1.936(2) 3_656 ? Zn1 N10 2.0375(18) . ? Zn1 N10 2.0375(18) 3_656 ? N1 C1 1.152(3) . ? C1 S1 1.601(3) . ? N10 C10 1.328(3) . ? N10 C14 1.339(3) . ? C10 C11 1.371(3) . ? C10 Cl1 1.714(3) . ? C11 C12 1.369(4) . ? C12 C13 1.367(4) . ? C13 C14 1.372(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 N1 108.86(14) . 3_656 ? N1 Zn1 N10 104.11(8) . . ? N1 Zn1 N10 110.66(8) 3_656 . ? N1 Zn1 N10 110.66(8) . 3_656 ? N1 Zn1 N10 104.11(8) 3_656 3_656 ? N10 Zn1 N10 118.30(10) . 3_656 ? C1 N1 Zn1 163.3(2) . . ? N1 C1 S1 179.6(2) . . ? C10 N10 C14 117.2(2) . . ? C10 N10 Zn1 123.49(16) . . ? C14 N10 Zn1 119.15(16) . . ? N10 C10 C11 124.0(2) . . ? N10 C10 Cl1 115.31(18) . . ? C11 C10 Cl1 120.7(2) . . ? C12 C11 C10 117.9(3) . . ? C13 C12 C11 119.2(2) . . ? C12 C13 C14 119.2(3) . . ? N10 C14 C13 122.4(3) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.289 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 910148' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_woe1754 #TrackingRef 'WOE1754.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 Cl2 Co N4 S2' _chemical_formula_sum 'C12 H8 Cl2 Co N4 S2' _chemical_formula_weight 402.17 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' S S 0.1246 0.1234 '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 orthorhombic _symmetry_space_group_name_H-M 'P bcn' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.3570(8) _cell_length_b 9.7125(5) _cell_length_c 15.3910(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1697.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 177770 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 29.01 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.0800 _exptl_crystal_size_mid 0.0656 _exptl_crystal_size_min 0.0407 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 1.567 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7759 _exptl_absorpt_correction_T_max 0.9346 _exptl_absorpt_process_details 'X-Shape and X-Red32 (Stoe, 2008)' _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 'STOE IPDS-2' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17770 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.0164 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 29.01 _reflns_number_total 2257 _reflns_number_gt 1759 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area (Stoe, 2008)' _computing_cell_refinement 'X-Area (Stoe, 2008)' _computing_data_reduction 'X-Area (Stoe, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; XP in SHELXTL (Sheldrick, 2008) and Diamond (Brandenburg, 2011) ; _computing_publication_material 'XCIF in 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^)+(0.0283P)^2^+0.6678P] 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 2257 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0685 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.0986 _refine_ls_wR_factor_gt 0.0921 _refine_ls_goodness_of_fit_ref 1.186 _refine_ls_restrained_S_all 1.186 _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 0.16027(6) 0.2500 0.06590(17) Uani 1 2 d S . . N1 N 0.0806(2) 0.0425(3) 0.33180(17) 0.0808(7) Uani 1 1 d . . . C1 C 0.1143(2) -0.0494(3) 0.37321(18) 0.0679(7) Uani 1 1 d . . . S1 S 0.15922(8) -0.17761(10) 0.42968(6) 0.0944(3) Uani 1 1 d . . . N10 N 0.13142(18) 0.2660(2) 0.18972(14) 0.0643(5) Uani 1 1 d . . . C10 C 0.1108(2) 0.3621(3) 0.13021(19) 0.0747(7) Uani 1 1 d . . . C11 C 0.1969(3) 0.4275(3) 0.0832(2) 0.0843(8) Uani 1 1 d . . . H11 H 0.1782 0.4959 0.0432 0.101 Uiso 1 1 calc R . . C12 C 0.3115(3) 0.3886(4) 0.0973(2) 0.0898(10) Uani 1 1 d . . . H12 H 0.3722 0.4280 0.0652 0.108 Uiso 1 1 calc R . . C13 C 0.3355(3) 0.2914(4) 0.1589(2) 0.0905(10) Uani 1 1 d . . . H13 H 0.4129 0.2655 0.1702 0.109 Uiso 1 1 calc R . . C14 C 0.2445(2) 0.2324(3) 0.20395(19) 0.0761(7) Uani 1 1 d . . . H14 H 0.2617 0.1665 0.2459 0.091 Uiso 1 1 calc R . . Cl1 Cl -0.03500(8) 0.40131(13) 0.11456(7) 0.1230(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0511(2) 0.0696(3) 0.0770(3) 0.000 0.0042(2) 0.000 N1 0.0670(13) 0.0822(16) 0.0933(17) 0.0098(14) 0.0002(13) -0.0016(12) C1 0.0505(13) 0.0796(18) 0.0735(16) -0.0049(15) -0.0015(12) -0.0075(12) S1 0.0882(6) 0.0950(6) 0.1001(6) 0.0174(5) -0.0207(5) 0.0035(5) N10 0.0555(11) 0.0672(13) 0.0701(13) -0.0027(11) 0.0006(10) -0.0036(10) C10 0.0665(16) 0.083(2) 0.0747(17) 0.0021(15) 0.0009(13) -0.0056(14) C11 0.086(2) 0.089(2) 0.0772(18) 0.0079(17) -0.0007(16) -0.0198(17) C12 0.077(2) 0.110(3) 0.083(2) -0.002(2) 0.0032(16) -0.0343(18) C13 0.0541(15) 0.111(3) 0.106(2) 0.005(2) -0.0027(16) -0.0152(16) C14 0.0580(14) 0.0832(19) 0.0872(18) 0.0027(16) 0.0011(14) -0.0065(13) Cl1 0.0762(5) 0.1652(10) 0.1275(8) 0.0612(7) 0.0071(5) 0.0243(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 Co1 N1 1.932(3) 3 ? Co1 N1 1.932(3) . ? Co1 N10 2.036(2) . ? Co1 N10 2.036(2) 3 ? N1 C1 1.162(3) . ? C1 S1 1.602(3) . ? N10 C10 1.329(3) . ? N10 C14 1.344(3) . ? C10 C11 1.371(4) . ? C10 Cl1 1.716(3) . ? C11 C12 1.373(5) . ? C12 C13 1.366(5) . ? C13 C14 1.370(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 Co1 N1 107.40(15) 3 . ? N1 Co1 N10 110.45(10) 3 . ? N1 Co1 N10 104.37(9) . . ? N1 Co1 N10 104.37(9) 3 3 ? N1 Co1 N10 110.45(10) . 3 ? N10 Co1 N10 119.39(12) . 3 ? C1 N1 Co1 165.6(2) . . ? N1 C1 S1 179.1(3) . . ? C10 N10 C14 116.8(2) . . ? C10 N10 Co1 122.68(18) . . ? C14 N10 Co1 120.26(19) . . ? N10 C10 C11 124.3(3) . . ? N10 C10 Cl1 115.0(2) . . ? C11 C10 Cl1 120.7(3) . . ? C10 C11 C12 117.7(3) . . ? C13 C12 C11 119.3(3) . . ? C12 C13 C14 119.4(3) . . ? N10 C14 C13 122.5(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.220 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 934076'