# Electronic Supplementary Material (ESI) for RSC Advances # 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_1 _database_code_depnum_ccdc_archive 'CCDC 888570' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H3 Cl N4 S4' _chemical_formula_sum 'C8 H3 Cl N4 S4' _chemical_formula_weight 318.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Monoclinic _symmetry_space_group_name_H-M P121/c1 _symmetry_space_group_name_Hall -P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.4751(11) _cell_length_b 22.522(2) _cell_length_c 7.5169(9) _cell_angle_alpha 90.000(11) _cell_angle_beta 109.736(9) _cell_angle_gamma 90.000(12) _cell_volume 1191.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 14171 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 28.98 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.778 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 1.000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7621 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14171 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0553 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 28.98 _reflns_number_total 3099 _reflns_number_gt 1835 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'Denzo and Scalepak' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0278P)^2^+1.1242P] 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 3099 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1116 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1026 _refine_ls_wR_factor_gt 0.0852 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 S1 S -0.07231(13) 0.30865(4) 0.29740(13) 0.0522(2) Uani 1 1 d . . . S2 S -0.11449(14) 0.40656(4) 0.02477(13) 0.0606(3) Uani 1 1 d . . . S3 S 0.20335(12) 0.39097(4) 0.63335(12) 0.0495(2) Uani 1 1 d . . . S4 S 0.16320(11) 0.48939(3) 0.35906(11) 0.0433(2) Uani 1 1 d . . . N1 N 0.5048(4) 0.56693(12) 0.8293(4) 0.0489(7) Uani 1 1 d . . . N2 N 0.3670(4) 0.59894(11) 0.5089(4) 0.0438(6) Uani 1 1 d . . . N3 N 0.5827(4) 0.61975(12) 0.8770(4) 0.0509(7) Uani 1 1 d . . . N4 N 0.4460(4) 0.65236(11) 0.5578(4) 0.0476(7) Uani 1 1 d . . . Cl1 Cl 0.64029(14) 0.72912(4) 0.80447(14) 0.0662(3) Uani 1 1 d . . . C1 C -0.2168(5) 0.29743(17) 0.0655(5) 0.0619(10) Uani 1 1 d . . . H1 H -0.2796 0.2615 0.0278 0.074 Uiso 1 1 calc R . . C2 C -0.2352(6) 0.34057(18) -0.0550(5) 0.0666(11) Uani 1 1 d . . . H2 H -0.3113 0.3361 -0.1808 0.080 Uiso 1 1 calc R . . C3 C -0.0109(4) 0.38192(13) 0.2587(4) 0.0421(7) Uani 1 1 d . . . C4 C 0.1031(4) 0.41594(13) 0.3977(4) 0.0407(7) Uani 1 1 d . . . C5 C 0.3231(5) 0.45572(14) 0.7157(5) 0.0474(8) Uani 1 1 d . . . H5 H 0.3982 0.4595 0.8421 0.057 Uiso 1 1 calc R . . C6 C 0.3068(4) 0.50085(13) 0.5948(4) 0.0400(7) Uani 1 1 d . . . C7 C 0.3959(4) 0.55877(13) 0.6465(5) 0.0412(7) Uani 1 1 d . . . C8 C 0.5473(4) 0.65995(14) 0.7383(5) 0.0455(8) 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 S1 0.0569(5) 0.0420(4) 0.0586(6) 0.0006(4) 0.0207(4) -0.0030(4) S2 0.0706(6) 0.0634(6) 0.0417(5) 0.0070(4) 0.0108(5) -0.0044(5) S3 0.0571(5) 0.0407(4) 0.0438(5) 0.0093(4) 0.0079(4) 0.0009(4) S4 0.0463(5) 0.0405(4) 0.0399(4) 0.0062(4) 0.0103(4) -0.0009(4) N1 0.0526(17) 0.0433(15) 0.0436(16) 0.0006(13) 0.0066(14) 0.0031(13) N2 0.0484(16) 0.0396(14) 0.0423(15) 0.0023(12) 0.0136(12) 0.0025(12) N3 0.0518(17) 0.0460(16) 0.0492(17) -0.0040(14) 0.0095(14) 0.0022(13) N4 0.0522(17) 0.0409(15) 0.0503(17) 0.0009(13) 0.0183(14) 0.0009(13) Cl1 0.0735(6) 0.0505(5) 0.0744(7) -0.0111(5) 0.0249(5) -0.0157(5) C1 0.073(3) 0.051(2) 0.064(3) -0.022(2) 0.026(2) -0.0058(19) C2 0.076(3) 0.071(3) 0.048(2) -0.018(2) 0.014(2) -0.003(2) C3 0.0414(17) 0.0423(17) 0.0425(18) 0.0025(14) 0.0142(14) 0.0027(14) C4 0.0436(18) 0.0379(16) 0.0408(18) 0.0063(14) 0.0144(15) 0.0059(14) C5 0.051(2) 0.0450(18) 0.0394(18) 0.0050(15) 0.0061(15) 0.0047(15) C6 0.0391(17) 0.0400(17) 0.0396(17) 0.0020(14) 0.0117(14) 0.0055(13) C7 0.0358(17) 0.0403(17) 0.0463(19) 0.0012(15) 0.0124(15) 0.0086(14) C8 0.0419(18) 0.0423(18) 0.055(2) -0.0080(16) 0.0201(16) 0.0001(14) _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 S1 C1 1.731(4) . ? S1 C3 1.763(3) . ? S2 C2 1.737(4) . ? S2 C3 1.755(3) . ? S3 C5 1.714(3) . ? S3 C4 1.766(3) . ? S4 C6 1.753(3) . ? S4 C4 1.764(3) . ? N1 N3 1.320(4) . ? N1 C7 1.352(4) . ? N2 N4 1.336(3) . ? N2 C7 1.335(4) . ? N3 C8 1.338(4) . ? N4 C8 1.323(4) . ? Cl1 C8 1.710(3) . ? C1 C2 1.303(5) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.343(4) . ? C5 C6 1.341(4) . ? C5 H5 0.9300 . ? C6 C7 1.457(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 C1 S1 C3 94.54(17) . . ? C2 S2 C3 94.43(18) . . ? C5 S3 C4 94.84(15) . . ? C6 S4 C4 94.27(15) . . ? N3 N1 C7 117.2(3) . . ? N4 N2 C7 117.2(3) . . ? N1 N3 C8 116.4(3) . . ? C8 N4 N2 116.4(3) . . ? C2 C1 S1 118.3(3) . . ? C2 C1 H1 120.8 . . ? S1 C1 H1 120.8 . . ? C1 C2 S2 118.5(3) . . ? C1 C2 H2 120.7 . . ? S2 C2 H2 120.7 . . ? C4 C3 S2 123.3(2) . . ? C4 C3 S1 122.5(2) . . ? S2 C3 S1 114.18(18) . . ? C3 C4 S4 122.5(2) . . ? C3 C4 S3 122.8(2) . . ? S4 C4 S3 114.74(18) . . ? C6 C5 S3 118.9(3) . . ? C6 C5 H5 120.6 . . ? S3 C5 H5 120.6 . . ? C5 C6 C7 124.7(3) . . ? C5 C6 S4 117.3(2) . . ? C7 C6 S4 118.0(2) . . ? N2 C7 N1 125.4(3) . . ? N2 C7 C6 117.4(3) . . ? N1 C7 C6 117.2(3) . . ? N4 C8 N3 127.3(3) . . ? N4 C8 Cl1 116.9(3) . . ? N3 C8 Cl1 115.8(3) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 28.98 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.415 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.068 data_(3)ZnCl2 _database_code_depnum_ccdc_archive 'CCDC 888571' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H15 Cl2 N7 S4 Zn' _chemical_formula_sum 'C20 H15 Cl2 N7 S4 Zn' _chemical_formula_weight 617.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7852(17) _cell_length_b 9.2555(14) _cell_length_c 16.386(4) _cell_angle_alpha 74.976(17) _cell_angle_beta 88.387(14) _cell_angle_gamma 72.238(14) _cell_volume 1223.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3978 _cell_measurement_theta_min 3.9 _cell_measurement_theta_max 26.00 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.677 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 1.589 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6109 _exptl_absorpt_correction_T_max 0.7459 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16903 _diffrn_reflns_av_R_equivalents 0.0708 _diffrn_reflns_av_sigmaI/netI 0.0737 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.91 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4739 _reflns_number_gt 3153 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'Denzo and Scalepak' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0388P)^2^+0.1470P] 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 4739 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0952 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.0923 _refine_ls_wR_factor_gt 0.0817 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.002 _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 0.62714(5) 0.80246(4) 0.11550(2) 0.03846(14) Uani 1 1 d . . . S1 S 0.67140(12) -0.13845(11) 0.55869(6) 0.0439(2) Uani 1 1 d . . . S2 S 0.96325(12) -0.22620(11) 0.66877(6) 0.0478(3) Uani 1 1 d . . . S3 S 0.68122(12) 0.21067(10) 0.48898(6) 0.0447(3) Uani 1 1 d . . . S4 S 0.97715(12) 0.14017(11) 0.59530(6) 0.0437(2) Uani 1 1 d . . . N1 N 0.5415(4) 0.5198(3) 0.38754(18) 0.0416(7) Uani 1 1 d . . . N2 N 0.7421(4) 0.6332(3) 0.40919(17) 0.0458(8) Uani 1 1 d . . . N3 N 0.4638(4) 0.6492(3) 0.33021(17) 0.0440(8) Uani 1 1 d . . . N4 N 0.6667(4) 0.7626(3) 0.35164(18) 0.0481(8) Uani 1 1 d . . . N5 N 0.4622(4) 0.8924(3) 0.24518(17) 0.0418(8) Uani 1 1 d . . . N6 N 0.4194(3) 0.7427(3) 0.12066(18) 0.0402(7) Uani 1 1 d . . . N7 N 0.6924(4) 0.9853(3) 0.13614(18) 0.0406(7) Uani 1 1 d . . . Cl1 Cl 0.69146(14) 0.81047(12) -0.02143(6) 0.0612(3) Uani 1 1 d . . . Cl2 Cl 0.79223(12) 0.58023(11) 0.20198(7) 0.0550(3) Uani 1 1 d . . . C1 C 0.7454(5) -0.3305(4) 0.6194(3) 0.0556(11) Uani 1 1 d . . . H1 H 0.6937 -0.4039 0.6181 0.067 Uiso 1 1 calc R . . C2 C 0.8753(6) -0.3697(5) 0.6670(3) 0.0621(12) Uani 1 1 d . . . H2 H 0.9201 -0.4725 0.6995 0.074 Uiso 1 1 calc R . . C3 C 0.8217(4) -0.0762(4) 0.5946(2) 0.0347(8) Uani 1 1 d . . . C4 C 0.8264(4) 0.0708(4) 0.5651(2) 0.0360(8) Uani 1 1 d . . . C5 C 0.7641(4) 0.3638(4) 0.4832(2) 0.0362(8) Uani 1 1 d . . . C6 C 0.8953(5) 0.3293(4) 0.5322(2) 0.0414(9) Uani 1 1 d . . . H6 H 0.9427 0.4064 0.5325 0.050 Uiso 1 1 calc R . . C7 C 0.6800(5) 0.5119(4) 0.4232(2) 0.0395(9) Uani 1 1 d . . . C8 C 0.5335(5) 0.7643(4) 0.3113(2) 0.0400(9) Uani 1 1 d . . . C9 C 0.3011(5) 0.9062(4) 0.2142(2) 0.0476(10) Uani 1 1 d . . . H9A H 0.2553 1.0103 0.1765 0.057 Uiso 1 1 calc R . . H9B H 0.2338 0.8963 0.2620 0.057 Uiso 1 1 calc R . . C10 C 0.4955(5) 1.0399(4) 0.2424(2) 0.0535(11) Uani 1 1 d . . . H10A H 0.5155 1.0416 0.3000 0.064 Uiso 1 1 calc R . . H10B H 0.4001 1.1267 0.2193 0.064 Uiso 1 1 calc R . . C11 C 0.2982(4) 0.7864(4) 0.1683(2) 0.0386(9) Uani 1 1 d . . . C12 C 0.1701(5) 0.7281(5) 0.1731(2) 0.0553(11) Uani 1 1 d . . . H12 H 0.0851 0.7614 0.2059 0.066 Uiso 1 1 calc R . . C13 C 0.1688(6) 0.6202(5) 0.1289(3) 0.0670(13) Uani 1 1 d . . . H13 H 0.0821 0.5821 0.1305 0.080 Uiso 1 1 calc R . . C14 C 0.2966(6) 0.5705(5) 0.0831(3) 0.0667(13) Uani 1 1 d . . . H14 H 0.3009 0.4947 0.0547 0.080 Uiso 1 1 calc R . . C15 C 0.4181(5) 0.6344(5) 0.0799(3) 0.0576(11) Uani 1 1 d . . . H15 H 0.5046 0.6013 0.0479 0.069 Uiso 1 1 calc R . . C16 C 0.6340(5) 1.0680(4) 0.1917(2) 0.0424(9) Uani 1 1 d . . . C17 C 0.6934(6) 1.1848(4) 0.2017(3) 0.0621(12) Uani 1 1 d . . . H17 H 0.6513 1.2408 0.2411 0.075 Uiso 1 1 calc R . . C18 C 0.8149(6) 1.2180(5) 0.1534(3) 0.0669(13) Uani 1 1 d . . . H18 H 0.8537 1.2982 0.1588 0.080 Uiso 1 1 calc R . . C19 C 0.8780(5) 1.1324(5) 0.0974(3) 0.0636(12) Uani 1 1 d . . . H19 H 0.9626 1.1504 0.0652 0.076 Uiso 1 1 calc R . . C20 C 0.8130(5) 1.0189(4) 0.0898(2) 0.0524(10) Uani 1 1 d . . . H20 H 0.8542 0.9619 0.0507 0.063 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 0.0374(3) 0.0414(2) 0.0410(3) -0.01254(18) 0.00537(19) -0.0174(2) S1 0.0420(6) 0.0456(5) 0.0471(6) -0.0095(4) -0.0097(4) -0.0190(5) S2 0.0410(6) 0.0500(5) 0.0498(6) -0.0063(4) -0.0115(5) -0.0145(5) S3 0.0442(6) 0.0434(5) 0.0499(6) -0.0044(4) -0.0116(5) -0.0236(5) S4 0.0376(6) 0.0537(6) 0.0447(6) -0.0109(4) -0.0045(4) -0.0223(5) N1 0.046(2) 0.0445(17) 0.0381(17) -0.0032(14) -0.0048(15) -0.0244(16) N2 0.062(2) 0.0497(18) 0.0365(17) -0.0067(14) -0.0036(15) -0.0351(18) N3 0.048(2) 0.0489(18) 0.0371(17) -0.0030(14) -0.0017(15) -0.0243(17) N4 0.062(2) 0.0525(19) 0.0397(18) -0.0100(15) -0.0005(17) -0.0337(19) N5 0.048(2) 0.0400(17) 0.0399(18) -0.0114(14) 0.0071(15) -0.0173(16) N6 0.0346(19) 0.0451(16) 0.0429(17) -0.0126(14) 0.0054(15) -0.0145(15) N7 0.042(2) 0.0378(16) 0.0443(18) -0.0091(13) 0.0006(15) -0.0175(15) Cl1 0.0786(9) 0.0788(7) 0.0445(6) -0.0242(5) 0.0187(5) -0.0450(7) Cl2 0.0426(6) 0.0455(5) 0.0678(7) -0.0081(5) -0.0028(5) -0.0056(5) C1 0.056(3) 0.045(2) 0.069(3) -0.006(2) -0.007(2) -0.027(2) C2 0.064(3) 0.045(2) 0.071(3) 0.007(2) -0.017(2) -0.024(2) C3 0.029(2) 0.0430(19) 0.0349(19) -0.0128(15) -0.0016(16) -0.0128(17) C4 0.032(2) 0.043(2) 0.0355(19) -0.0107(15) -0.0034(16) -0.0151(17) C5 0.041(2) 0.0421(19) 0.0327(19) -0.0085(15) 0.0037(17) -0.0242(18) C6 0.046(3) 0.052(2) 0.037(2) -0.0130(17) 0.0037(18) -0.030(2) C7 0.045(2) 0.049(2) 0.034(2) -0.0117(16) 0.0039(17) -0.026(2) C8 0.049(3) 0.040(2) 0.032(2) -0.0084(16) 0.0038(18) -0.0170(19) C9 0.047(3) 0.043(2) 0.040(2) -0.0023(17) 0.0072(19) -0.0019(19) C10 0.075(3) 0.038(2) 0.050(2) -0.0142(17) 0.014(2) -0.018(2) C11 0.037(2) 0.0396(19) 0.032(2) -0.0012(15) 0.0021(17) -0.0085(18) C12 0.039(3) 0.071(3) 0.051(2) -0.005(2) 0.007(2) -0.019(2) C13 0.056(3) 0.092(3) 0.067(3) -0.017(3) 0.001(2) -0.047(3) C14 0.066(3) 0.086(3) 0.075(3) -0.040(3) 0.017(3) -0.047(3) C15 0.048(3) 0.075(3) 0.071(3) -0.040(2) 0.020(2) -0.032(2) C16 0.058(3) 0.0325(18) 0.035(2) -0.0036(15) -0.0061(18) -0.0148(19) C17 0.083(4) 0.054(2) 0.061(3) -0.025(2) -0.004(2) -0.029(3) C18 0.077(4) 0.067(3) 0.070(3) -0.015(2) -0.009(3) -0.044(3) C19 0.066(3) 0.073(3) 0.068(3) -0.020(2) 0.006(2) -0.042(3) C20 0.051(3) 0.053(2) 0.060(3) -0.0155(19) 0.003(2) -0.026(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 N7 2.051(3) . ? Zn1 N6 2.056(3) . ? Zn1 Cl2 2.2643(12) . ? Zn1 Cl1 2.2862(11) . ? S1 C1 1.728(4) . ? S1 C3 1.762(3) . ? S2 C2 1.734(4) . ? S2 C3 1.763(4) . ? S3 C5 1.761(3) . ? S3 C4 1.762(4) . ? S4 C6 1.728(4) . ? S4 C4 1.769(3) . ? N1 N3 1.318(4) . ? N1 C7 1.339(4) . ? N2 N4 1.315(4) . ? N2 C7 1.357(4) . ? N3 C8 1.350(4) . ? N4 C8 1.354(5) . ? N5 C8 1.375(4) . ? N5 C10 1.470(4) . ? N5 C9 1.474(5) . ? N6 C11 1.327(4) . ? N6 C15 1.344(4) . ? N7 C16 1.332(4) . ? N7 C20 1.352(4) . ? C1 C2 1.302(5) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.333(4) . ? C5 C6 1.331(5) . ? C5 C7 1.455(5) . ? C6 H6 0.9300 . ? C9 C11 1.499(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C16 1.504(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.381(5) . ? C12 C13 1.379(6) . ? C12 H12 0.9300 . ? C13 C14 1.361(6) . ? C13 H13 0.9300 . ? C14 C15 1.363(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.381(5) . ? C17 C18 1.374(6) . ? C17 H17 0.9300 . ? C18 C19 1.363(6) . ? C18 H18 0.9300 . ? C19 C20 1.372(5) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N7 Zn1 N6 135.75(12) . . ? N7 Zn1 Cl2 106.30(9) . . ? N6 Zn1 Cl2 99.97(8) . . ? N7 Zn1 Cl1 102.48(8) . . ? N6 Zn1 Cl1 101.77(9) . . ? Cl2 Zn1 Cl1 108.94(5) . . ? C1 S1 C3 94.85(18) . . ? C2 S2 C3 94.43(19) . . ? C5 S3 C4 94.59(16) . . ? C6 S4 C4 94.34(17) . . ? N3 N1 C7 118.9(3) . . ? N4 N2 C7 117.2(3) . . ? N1 N3 C8 116.2(3) . . ? N2 N4 C8 117.4(3) . . ? C8 N5 C10 117.2(3) . . ? C8 N5 C9 116.8(3) . . ? C10 N5 C9 116.8(3) . . ? C11 N6 C15 118.2(3) . . ? C11 N6 Zn1 125.8(2) . . ? C15 N6 Zn1 115.4(2) . . ? C16 N7 C20 117.7(3) . . ? C16 N7 Zn1 127.3(2) . . ? C20 N7 Zn1 114.9(2) . . ? C2 C1 S1 118.3(3) . . ? C2 C1 H1 120.9 . . ? S1 C1 H1 120.9 . . ? C1 C2 S2 118.7(3) . . ? C1 C2 H2 120.7 . . ? S2 C2 H2 120.7 . . ? C4 C3 S1 121.5(3) . . ? C4 C3 S2 124.7(3) . . ? S1 C3 S2 113.76(17) . . ? C3 C4 S3 121.0(3) . . ? C3 C4 S4 124.1(3) . . ? S3 C4 S4 114.80(18) . . ? C6 C5 C7 128.5(3) . . ? C6 C5 S3 116.7(3) . . ? C7 C5 S3 114.7(3) . . ? C5 C6 S4 119.5(3) . . ? C5 C6 H6 120.3 . . ? S4 C6 H6 120.3 . . ? N1 C7 N2 124.5(3) . . ? N1 C7 C5 116.4(3) . . ? N2 C7 C5 119.1(3) . . ? N3 C8 N4 125.4(3) . . ? N3 C8 N5 116.4(3) . . ? N4 C8 N5 118.2(3) . . ? N5 C9 C11 114.2(3) . . ? N5 C9 H9A 108.7 . . ? C11 C9 H9A 108.7 . . ? N5 C9 H9B 108.7 . . ? C11 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? N5 C10 C16 116.2(3) . . ? N5 C10 H10A 108.2 . . ? C16 C10 H10A 108.2 . . ? N5 C10 H10B 108.2 . . ? C16 C10 H10B 108.2 . . ? H10A C10 H10B 107.4 . . ? N6 C11 C12 121.2(3) . . ? N6 C11 C9 117.9(3) . . ? C12 C11 C9 120.8(3) . . ? C13 C12 C11 119.6(4) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C14 C13 C12 118.9(4) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C13 C14 C15 118.5(4) . . ? C13 C14 H14 120.7 . . ? C15 C14 H14 120.7 . . ? N6 C15 C14 123.3(4) . . ? N6 C15 H15 118.3 . . ? C14 C15 H15 118.3 . . ? N7 C16 C17 121.4(3) . . ? N7 C16 C10 119.9(3) . . ? C17 C16 C10 118.6(3) . . ? C18 C17 C16 119.8(4) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C19 C18 C17 119.4(4) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C18 C19 C20 118.0(4) . . ? C18 C19 H19 121.0 . . ? C20 C19 H19 121.0 . . ? N7 C20 C19 123.6(4) . . ? N7 C20 H20 118.2 . . ? C19 C20 H20 118.2 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.364 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.080