# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_publication_text _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef 'All Cif.cif' _publ_contact_author_name 'Dr. Gopal Das' _publ_contact_author_address ;Department of Chemistry Indian Institute of Technology Guwahati Assam 781039 India ; _publ_contact_author_email gdas@iitg.ernet.in _publ_contact_author_phone 00913612582313 _publ_contact_author_fax 00913612582349 loop_ _publ_author_address ;Department of Chemistry Indian Institute of Technology Guwahati Assam 781039 India ; loop_ _publ_author_name A.Basu G.Das data_L2 _database_code_depnum_ccdc_archive 'CCDC 777755' #TrackingRef 'All Cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H13 N3 S' _chemical_formula_weight 255.34 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.2254(3) _cell_length_b 8.4194(4) _cell_length_c 21.4719(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1306.21(10) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 7344 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 26.40 _exptl_crystal_description square _exptl_crystal_colour red _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.235 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.928 _exptl_absorpt_correction_T_max 0.955 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17862 _diffrn_reflns_av_R_equivalents 0.0874 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.31 _reflns_number_total 1854 _reflns_number_gt 1645 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0577P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_number_reflns 3253 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0557 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1053 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 S1 S -0.25099(6) 0.54962(6) 0.13174(2) 0.05917(17) Uani 1 1 d . . . N1 N 0.09534(18) 0.45401(17) 0.15894(6) 0.0418(3) Uani 1 1 d . . . C1 C 0.1922(2) 0.5503(2) 0.11344(7) 0.0416(4) Uani 1 1 d . . . C2 C 0.2617(3) 0.6941(2) 0.13107(8) 0.0536(4) Uani 1 1 d . . . H2 H 0.2482 0.7290 0.1719 0.064 Uiso 1 1 calc R . . C8 C 0.1279(3) 0.3487(2) 0.03082(8) 0.0492(4) Uani 1 1 d . . . H8 H 0.0653 0.2840 0.0589 0.059 Uiso 1 1 calc R . . C9 C 0.2070(2) 0.49343(18) 0.05165(7) 0.0410(4) Uani 1 1 d . . . C10 C 0.3029(2) 0.5900(2) 0.00788(8) 0.0469(4) Uani 1 1 d . . . C4 C 0.3736(3) 0.7383(3) 0.02756(10) 0.0615(6) Uani 1 1 d . . . H4 H 0.4350 0.8025 -0.0010 0.074 Uiso 1 1 calc R . . C5 C 0.3175(3) 0.5365(3) -0.05492(8) 0.0621(5) Uani 1 1 d . . . H5 H 0.3819 0.5975 -0.0838 0.075 Uiso 1 1 calc R . . C7 C 0.1427(3) 0.3032(3) -0.03029(9) 0.0599(5) Uani 1 1 d . . . H7 H 0.0884 0.2088 -0.0434 0.072 Uiso 1 1 calc R . . C6 C 0.2387(3) 0.3976(3) -0.07305(8) 0.0656(6) Uani 1 1 d . . . H6 H 0.2487 0.3650 -0.1143 0.079 Uiso 1 1 calc R . . C3 C 0.3539(3) 0.7891(3) 0.08715(11) 0.0631(5) Uani 1 1 d . . . H3 H 0.4016 0.8872 0.0990 0.076 Uiso 1 1 calc R . . N3 N 0.0224(3) 0.2880(2) 0.23831(8) 0.0690(5) Uani 1 1 d . . . N2 N -0.1235(3) 0.3467(2) 0.21909(8) 0.0641(5) Uani 1 1 d . . . C11 C -0.0861(2) 0.4560(2) 0.16737(7) 0.0446(4) Uani 1 1 d . . . C12 C 0.1854(3) 0.3486(2) 0.20435(8) 0.0523(5) Uani 1 1 d . . . C13 C 0.2822(4) 0.2072(3) 0.17365(11) 0.0785(7) Uani 1 1 d . . . H13A H 0.1962 0.1521 0.1473 0.118 Uiso 1 1 calc R . . H13C H 0.3268 0.1361 0.2053 0.118 Uiso 1 1 calc R . . H13B H 0.3845 0.2445 0.1491 0.118 Uiso 1 1 calc R . . C14 C 0.3136(4) 0.4345(3) 0.24907(10) 0.0763(6) Uani 1 1 d . . . H14A H 0.4148 0.4803 0.2263 0.114 Uiso 1 1 calc R . . H14B H 0.3608 0.3606 0.2792 0.114 Uiso 1 1 calc R . . H14C H 0.2465 0.5171 0.2700 0.114 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 S1 0.0442(3) 0.0662(3) 0.0671(3) 0.0050(2) 0.0014(2) 0.0035(3) N1 0.0390(8) 0.0459(7) 0.0407(7) 0.0076(7) 0.0068(5) 0.0028(7) C1 0.0342(8) 0.0442(9) 0.0465(8) 0.0071(8) 0.0053(6) 0.0026(7) C2 0.0519(11) 0.0505(10) 0.0586(10) -0.0023(8) 0.0060(10) -0.0018(9) C8 0.0468(10) 0.0526(10) 0.0481(9) 0.0010(8) 0.0021(8) -0.0013(9) C9 0.0324(9) 0.0446(9) 0.0461(8) 0.0092(7) 0.0034(6) 0.0052(6) C10 0.0338(8) 0.0543(11) 0.0527(9) 0.0170(8) 0.0067(7) 0.0069(7) C4 0.0438(11) 0.0596(12) 0.0812(14) 0.0255(11) 0.0118(10) -0.0064(9) C5 0.0544(11) 0.0805(14) 0.0514(10) 0.0219(11) 0.0161(9) 0.0199(12) C7 0.0589(13) 0.0640(12) 0.0568(11) -0.0067(10) -0.0040(9) 0.0068(10) C6 0.0679(13) 0.0844(15) 0.0446(9) 0.0019(10) 0.0049(10) 0.0207(13) C3 0.0514(12) 0.0469(10) 0.0910(15) 0.0040(11) 0.0072(11) -0.0128(9) N3 0.0637(12) 0.0839(13) 0.0594(11) 0.0289(10) 0.0092(9) 0.0023(10) N2 0.0538(10) 0.0788(11) 0.0595(9) 0.0217(9) 0.0140(8) -0.0032(9) C11 0.0441(9) 0.0467(9) 0.0429(8) 0.0002(8) 0.0071(7) -0.0030(8) C12 0.0500(10) 0.0609(11) 0.0459(9) 0.0149(8) 0.0057(8) 0.0062(9) C13 0.0894(17) 0.0719(13) 0.0741(13) 0.0166(12) 0.0072(13) 0.0360(14) C14 0.0750(15) 0.0917(17) 0.0621(12) 0.0075(13) -0.0148(11) 0.0083(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 C11 1.6203(18) . ? N1 C11 1.324(2) . ? N1 C1 1.450(2) . ? N1 C12 1.470(2) . ? C1 C2 1.365(3) . ? C1 C9 1.415(2) . ? C2 C3 1.405(3) . ? C8 C7 1.371(3) . ? C8 C9 1.419(2) . ? C9 C10 1.423(2) . ? C10 C4 1.414(3) . ? C10 C5 1.426(3) . ? C4 C3 1.357(3) . ? C5 C6 1.357(3) . ? C7 C6 1.399(3) . ? N3 N2 1.235(3) . ? N3 C12 1.476(3) . ? N2 C11 1.467(2) . ? C12 C14 1.518(3) . ? C12 C13 1.530(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 C11 N1 C1 124.27(14) . . ? C11 N1 C12 110.83(14) . . ? C1 N1 C12 124.81(13) . . ? C2 C1 C9 122.18(16) . . ? C2 C1 N1 119.15(15) . . ? C9 C1 N1 118.65(16) . . ? C1 C2 C3 119.58(17) . . ? C7 C8 C9 120.66(18) . . ? C1 C9 C8 123.77(15) . . ? C1 C9 C10 117.59(15) . . ? C8 C9 C10 118.62(16) . . ? C4 C10 C9 118.90(17) . . ? C4 C10 C5 122.34(18) . . ? C9 C10 C5 118.71(18) . . ? C3 C4 C10 121.49(18) . . ? C6 C5 C10 120.82(18) . . ? C8 C7 C6 120.6(2) . . ? C5 C6 C7 120.62(17) . . ? C4 C3 C2 120.23(19) . . ? N2 N3 C12 112.17(15) . . ? N3 N2 C11 110.31(15) . . ? N1 C11 N2 106.11(15) . . ? N1 C11 S1 132.05(14) . . ? N2 C11 S1 121.83(13) . . ? N1 C12 N3 100.55(15) . . ? N1 C12 C14 113.71(16) . . ? N3 C12 C14 109.84(17) . . ? N1 C12 C13 112.73(15) . . ? N3 C12 C13 107.95(17) . . ? C14 C12 C13 111.38(18) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.218 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.032 data_L1 _database_code_depnum_ccdc_archive 'CCDC 777756' #TrackingRef 'All Cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H15 N3 S' _chemical_formula_weight 257.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8572(9) _cell_length_b 8.9640(9) _cell_length_c 9.6791(10) _cell_angle_alpha 98.898(7) _cell_angle_beta 99.319(7) _cell_angle_gamma 113.365(5) _cell_volume 675.52(12) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2899 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 30.26 _exptl_crystal_description rectangle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272.0 _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.952 _exptl_absorpt_correction_T_max 0.968 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10475 _diffrn_reflns_av_R_equivalents 0.0795 _diffrn_reflns_av_sigmaI/netI 0.0691 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 34.40 _reflns_number_total 5694 _reflns_number_gt 5284 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1421P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_number_reflns 4855 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1368 _refine_ls_R_factor_gt 0.0828 _refine_ls_wR_factor_ref 0.2043 _refine_ls_wR_factor_gt 0.1915 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 S1 S -0.16157(8) 0.07203(10) 0.36004(8) 0.0573(3) Uani 1 1 d . . . C1 C -0.1212(3) 0.2320(3) 0.0951(3) 0.0479(6) Uani 1 1 d . . . C8 C -0.0198(4) 0.5326(4) 0.2169(3) 0.0598(7) Uani 1 1 d . . . H8 H 0.0673 0.5296 0.2827 0.072 Uiso 1 1 calc R . . C4 C -0.3846(4) 0.2467(5) -0.0907(3) 0.0680(9) Uani 1 1 d . . . H4 H -0.4741 0.2500 -0.1533 0.082 Uiso 1 1 calc R . . C5 C -0.2761(5) 0.5496(5) 0.0226(4) 0.0720(10) Uani 1 1 d . . . H5 H -0.3602 0.5575 -0.0429 0.086 Uiso 1 1 calc R . . C2 C -0.2363(5) 0.0947(4) -0.0072(4) 0.0684(8) Uani 1 1 d . . . H2 H -0.2258 -0.0053 -0.0161 0.082 Uiso 1 1 calc R . . C3 C -0.3708(4) 0.1022(5) -0.0996(4) 0.0772(10) Uani 1 1 d . . . H3 H -0.4510 0.0063 -0.1674 0.093 Uiso 1 1 calc R . . C6 C -0.1678(6) 0.6833(5) 0.1245(5) 0.0870(12) Uani 1 1 d . . . H6 H -0.1776 0.7835 0.1299 0.104 Uiso 1 1 calc R . . C7 C -0.0381(6) 0.6770(5) 0.2248(5) 0.0836(11) Uani 1 1 d . . . H7 H 0.0355 0.7720 0.2969 0.100 Uiso 1 1 calc R . . C9 C -0.1326(3) 0.3870(3) 0.1090(3) 0.0459(6) Uani 1 1 d . . . C10 C -0.2664(3) 0.3930(4) 0.0112(3) 0.0537(7) Uani 1 1 d . . . N2 N 0.1660(3) 0.1795(3) 0.3770(3) 0.0500(5) Uani 1 1 d . . . N1 N 0.0190(3) 0.2271(3) 0.1871(3) 0.0582(6) Uani 1 1 d . . . N3 N 0.3091(3) 0.2630(3) 0.3295(2) 0.0515(5) Uani 1 1 d . . . C11 C 0.0144(3) 0.1636(3) 0.3036(3) 0.0444(5) Uani 1 1 d . . . C14 C 0.6055(4) 0.3775(5) 0.3487(4) 0.0696(9) Uani 1 1 d . . . H14B H 0.5718 0.4129 0.2651 0.104 Uiso 1 1 calc R . . H14A H 0.6580 0.3051 0.3239 0.104 Uiso 1 1 calc R . . H14C H 0.6848 0.4737 0.4233 0.104 Uiso 1 1 calc R . . C12 C 0.4533(3) 0.2854(3) 0.4010(3) 0.0500(6) Uani 1 1 d . . . C13 C 0.4843(4) 0.2307(6) 0.5345(5) 0.0969(15) Uani 1 1 d . . . H13A H 0.4280 0.2654 0.6008 0.145 Uiso 1 1 calc R . . H13B H 0.6040 0.2802 0.5775 0.145 Uiso 1 1 calc R . . H13C H 0.4410 0.1109 0.5121 0.145 Uiso 1 1 calc R . . H1N H 0.112(4) 0.274(4) 0.179(3) 0.054(8) Uiso 1 1 d . . . H2N H 0.158(4) 0.120(4) 0.438(4) 0.063(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0431(4) 0.0810(5) 0.0590(5) 0.0372(4) 0.0170(3) 0.0289(3) C1 0.0404(11) 0.0670(15) 0.0429(12) 0.0257(11) 0.0120(10) 0.0246(12) C8 0.0519(14) 0.0718(18) 0.0476(14) 0.0165(13) 0.0126(12) 0.0179(14) C4 0.0463(14) 0.112(3) 0.0429(14) 0.0327(16) 0.0033(11) 0.0287(17) C5 0.074(2) 0.106(3) 0.078(2) 0.054(2) 0.0404(18) 0.061(2) C2 0.0725(19) 0.0635(17) 0.0648(19) 0.0205(15) 0.0147(16) 0.0241(16) C3 0.0599(18) 0.087(2) 0.0556(18) 0.0123(17) -0.0045(14) 0.0119(18) C6 0.113(3) 0.091(3) 0.101(3) 0.049(2) 0.058(3) 0.066(3) C7 0.100(3) 0.0643(19) 0.081(2) 0.0121(17) 0.037(2) 0.0263(19) C9 0.0365(10) 0.0677(15) 0.0393(12) 0.0239(11) 0.0132(9) 0.0230(11) C10 0.0450(12) 0.0869(19) 0.0461(14) 0.0366(13) 0.0193(11) 0.0351(14) N2 0.0430(10) 0.0684(13) 0.0508(12) 0.0325(11) 0.0148(9) 0.0287(10) N1 0.0438(11) 0.0867(17) 0.0586(15) 0.0423(13) 0.0171(10) 0.0321(13) N3 0.0439(11) 0.0721(14) 0.0515(12) 0.0291(11) 0.0171(9) 0.0309(11) C11 0.0430(11) 0.0517(12) 0.0452(13) 0.0166(10) 0.0100(10) 0.0258(10) C14 0.0507(15) 0.097(2) 0.079(2) 0.0419(18) 0.0302(15) 0.0366(16) C12 0.0435(12) 0.0626(15) 0.0530(14) 0.0226(12) 0.0161(11) 0.0273(12) C13 0.0525(17) 0.157(4) 0.101(3) 0.088(3) 0.0198(18) 0.044(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 S1 C11 1.674(3) . ? C1 C2 1.354(4) . ? C1 C9 1.420(4) . ? C1 N1 1.427(3) . ? C8 C7 1.359(5) . ? C8 C9 1.414(4) . ? C4 C3 1.339(5) . ? C4 C10 1.401(5) . ? C5 C6 1.321(6) . ? C5 C10 1.429(5) . ? C2 C3 1.400(5) . ? C6 C7 1.405(6) . ? C9 C10 1.417(4) . ? N2 C11 1.356(3) . ? N2 N3 1.386(3) . ? N1 C11 1.338(3) . ? N3 C12 1.272(3) . ? C14 C12 1.491(4) . ? C12 C13 1.474(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 C2 C1 C9 120.8(3) . . ? C2 C1 N1 121.0(3) . . ? C9 C1 N1 118.2(2) . . ? C7 C8 C9 120.3(3) . . ? C3 C4 C10 121.2(3) . . ? C6 C5 C10 121.2(3) . . ? C1 C2 C3 120.5(3) . . ? C4 C3 C2 120.4(3) . . ? C5 C6 C7 121.2(3) . . ? C8 C7 C6 120.2(4) . . ? C8 C9 C10 119.1(3) . . ? C8 C9 C1 123.2(2) . . ? C10 C9 C1 117.7(2) . . ? C4 C10 C9 119.4(3) . . ? C4 C10 C5 122.7(3) . . ? C9 C10 C5 117.9(3) . . ? C11 N2 N3 118.4(2) . . ? C11 N1 C1 126.0(2) . . ? C12 N3 N2 119.1(2) . . ? N1 C11 N2 115.1(2) . . ? N1 C11 S1 124.3(2) . . ? N2 C11 S1 120.65(19) . . ? N3 C12 C13 125.4(2) . . ? N3 C12 C14 118.1(2) . . ? C13 C12 C14 116.5(2) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 34.40 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.585 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.080 data_Ni_L1 _database_code_depnum_ccdc_archive 'CCDC 777757' #TrackingRef 'All Cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 N6 Ni S2' _chemical_formula_weight 571.39 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.9620(10) _cell_length_b 7.7407(3) _cell_length_c 13.1235(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.079(4) _cell_angle_gamma 90.00 _cell_volume 2622.52(17) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 8090 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description square _exptl_crystal_colour green _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.929 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.736 _exptl_absorpt_correction_T_max 0.770 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24283 _diffrn_reflns_av_R_equivalents 0.0993 _diffrn_reflns_av_sigmaI/netI 0.0457 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 28.38 _reflns_number_total 3275 _reflns_number_gt 2473 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_number_reflns 3275 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0923 _refine_ls_wR_factor_gt 0.0879 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.007 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.0000 0.10888(4) 0.7500 0.03592(13) Uani 1 2 d S . . S1 S 0.053795(18) 0.30515(6) 0.71259(4) 0.04869(16) Uani 1 1 d . . . C1 C 0.18284(7) 0.1411(2) 0.59796(14) 0.0366(4) Uani 1 1 d . . . C10 C 0.27263(7) 0.0578(2) 0.58393(13) 0.0371(4) Uani 1 1 d . . . C9 C 0.23588(6) 0.1457(2) 0.63905(13) 0.0336(4) Uani 1 1 d . . . C4 C 0.25570(8) -0.0279(2) 0.49194(15) 0.0479(5) Uani 1 1 d . . . H4 H 0.2796 -0.0856 0.4563 0.057 Uiso 1 1 calc R . . C8 C 0.25395(7) 0.2320(2) 0.73075(13) 0.0397(4) Uani 1 1 d . . . H8 H 0.2304 0.2903 0.7670 0.048 Uiso 1 1 calc R . . C7 C 0.30516(7) 0.2317(3) 0.76729(15) 0.0457(5) Uani 1 1 d . . . H7 H 0.3162 0.2912 0.8272 0.055 Uiso 1 1 calc R . . C5 C 0.32564(7) 0.0583(3) 0.62588(16) 0.0475(5) Uani 1 1 d . . . H5 H 0.3500 0.0002 0.5916 0.057 Uiso 1 1 calc R . . C2 C 0.16814(8) 0.0571(2) 0.50763(15) 0.0442(4) Uani 1 1 d . . . H2 H 0.1334 0.0560 0.4813 0.053 Uiso 1 1 calc R . . C6 C 0.34119(7) 0.1417(3) 0.71457(16) 0.0486(5) Uani 1 1 d . . . H6 H 0.3759 0.1395 0.7407 0.058 Uiso 1 1 calc R . . C3 C 0.20488(8) -0.0273(3) 0.45450(15) 0.0500(5) Uani 1 1 d . . . H3 H 0.1944 -0.0834 0.3931 0.060 Uiso 1 1 calc R . . N1 N 0.14543(6) 0.2283(2) 0.65093(14) 0.0466(4) Uani 1 1 d . . . C11 C 0.09830(7) 0.1607(2) 0.66878(14) 0.0378(4) Uani 1 1 d . . . N2 N 0.08892(5) -0.0001(2) 0.65059(12) 0.0417(4) Uani 1 1 d . . . N3 N -0.03745(5) -0.04471(19) 0.83330(11) 0.0371(3) Uani 1 1 d . . . C12 C -0.01982(7) -0.1769(2) 0.88770(14) 0.0401(4) Uani 1 1 d . . . C13 C 0.03406(8) -0.2401(3) 0.88203(17) 0.0559(5) Uani 1 1 d . . . H13A H 0.0330 -0.3502 0.8482 0.084 Uiso 1 1 calc R . . H13B H 0.0513 -0.2518 0.9500 0.084 Uiso 1 1 calc R . . H13C H 0.0525 -0.1589 0.8442 0.084 Uiso 1 1 calc R . . C14 C -0.05122(8) -0.2711(3) 0.95920(16) 0.0544(5) Uani 1 1 d . . . H14A H -0.0397 -0.2390 1.0286 0.082 Uiso 1 1 calc R . . H14B H -0.0470 -0.3933 0.9510 0.082 Uiso 1 1 calc R . . H14C H -0.0871 -0.2413 0.9439 0.082 Uiso 1 1 calc R . . H1N H 0.1519(7) 0.327(3) 0.6824(14) 0.038(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.02687(18) 0.03420(19) 0.0467(2) 0.000 0.00393(13) 0.000 S1 0.0357(3) 0.0344(3) 0.0784(4) -0.0055(2) 0.0177(2) -0.00199(18) C1 0.0360(9) 0.0309(9) 0.0444(10) 0.0029(7) 0.0109(8) -0.0026(7) C10 0.0428(10) 0.0302(9) 0.0402(10) 0.0051(7) 0.0137(8) 0.0009(7) C9 0.0364(9) 0.0279(8) 0.0378(9) 0.0050(7) 0.0109(7) -0.0020(7) C4 0.0595(12) 0.0405(10) 0.0475(11) -0.0014(9) 0.0235(10) 0.0015(9) C8 0.0411(10) 0.0369(10) 0.0425(10) -0.0011(8) 0.0110(8) -0.0047(8) C7 0.0453(11) 0.0461(11) 0.0451(11) 0.0036(9) 0.0020(9) -0.0081(9) C5 0.0397(10) 0.0439(11) 0.0619(13) 0.0090(9) 0.0197(9) 0.0072(8) C2 0.0444(10) 0.0416(10) 0.0459(11) 0.0023(8) 0.0014(9) -0.0052(8) C6 0.0341(10) 0.0507(12) 0.0606(13) 0.0150(10) 0.0025(9) -0.0019(8) C3 0.0685(14) 0.0447(11) 0.0377(11) -0.0053(8) 0.0100(10) -0.0099(10) N1 0.0339(8) 0.0379(9) 0.0694(11) -0.0131(8) 0.0122(8) -0.0061(7) C11 0.0287(9) 0.0386(10) 0.0458(10) -0.0007(8) 0.0028(8) -0.0019(7) N2 0.0307(8) 0.0373(9) 0.0578(10) -0.0023(7) 0.0084(7) -0.0009(6) N3 0.0281(7) 0.0366(8) 0.0459(9) -0.0014(7) 0.0008(6) 0.0031(6) C12 0.0400(10) 0.0357(10) 0.0434(10) -0.0020(8) -0.0014(8) 0.0029(8) C13 0.0464(12) 0.0612(14) 0.0588(13) 0.0094(11) -0.0002(10) 0.0151(10) C14 0.0551(13) 0.0487(12) 0.0589(13) 0.0122(10) 0.0041(10) 0.0044(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N3 1.9440(15) . ? Ni1 N3 1.9440(15) 2_556 ? Ni1 S1 2.1552(5) 2_556 ? Ni1 S1 2.1552(5) . ? S1 C11 1.7484(18) . ? C1 C2 1.371(3) . ? C1 N1 1.423(2) . ? C1 C9 1.425(2) . ? C10 C4 1.407(3) . ? C10 C5 1.427(3) . ? C10 C9 1.429(2) . ? C9 C8 1.412(3) . ? C4 C3 1.358(3) . ? C8 C7 1.365(2) . ? C7 C6 1.405(3) . ? C5 C6 1.355(3) . ? C2 C3 1.401(3) . ? N1 C11 1.374(2) . ? C11 N2 1.285(2) . ? N2 N3 1.4174(19) 2_556 ? N3 C12 1.302(2) . ? N3 N2 1.4174(19) 2_556 ? C12 C13 1.491(2) . ? C12 C14 1.496(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 N3 Ni1 N3 104.60(8) . 2_556 ? N3 Ni1 S1 85.88(4) . 2_556 ? N3 Ni1 S1 159.07(5) 2_556 2_556 ? N3 Ni1 S1 159.07(5) . . ? N3 Ni1 S1 85.88(4) 2_556 . ? S1 Ni1 S1 90.35(3) 2_556 . ? C11 S1 Ni1 95.21(6) . . ? C2 C1 N1 120.39(17) . . ? C2 C1 C9 120.56(16) . . ? N1 C1 C9 119.04(16) . . ? C4 C10 C5 122.23(17) . . ? C4 C10 C9 119.61(17) . . ? C5 C10 C9 118.15(17) . . ? C8 C9 C1 123.70(16) . . ? C8 C9 C10 118.48(16) . . ? C1 C9 C10 117.82(16) . . ? C3 C4 C10 120.82(17) . . ? C7 C8 C9 121.47(17) . . ? C8 C7 C6 120.14(18) . . ? C6 C5 C10 121.34(17) . . ? C1 C2 C3 120.66(18) . . ? C5 C6 C7 120.39(18) . . ? C4 C3 C2 120.52(18) . . ? C11 N1 C1 124.66(16) . . ? N2 C11 N1 119.48(16) . . ? N2 C11 S1 124.14(13) . . ? N1 C11 S1 116.35(14) . . ? C11 N2 N3 111.81(14) . 2_556 ? C12 N3 N2 113.08(15) . 2_556 ? C12 N3 Ni1 128.38(12) . . ? N2 N3 Ni1 118.05(11) 2_556 . ? N3 C12 C13 120.49(17) . . ? N3 C12 C14 122.90(17) . . ? C13 C12 C14 116.60(17) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.38 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.344 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.053 data_Zn_L1 _database_code_depnum_ccdc_archive 'CCDC 777758' #TrackingRef 'All Cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 N6 S2 Zn' _chemical_formula_weight 578.09 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' 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 Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.8575(10) _cell_length_b 7.4489(3) _cell_length_c 13.6206(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.572(4) _cell_angle_gamma 90.00 _cell_volume 2694.48(17) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3594 _cell_measurement_theta_min 2.84 _cell_measurement_theta_max 26.51 _exptl_crystal_description Square _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 1.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.696 _exptl_absorpt_correction_T_max 0.760 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15664 _diffrn_reflns_av_R_equivalents 0.0789 _diffrn_reflns_av_sigmaI/netI 0.0683 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 28.37 _reflns_number_total 3321 _reflns_number_gt 2079 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0546P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_number_reflns 3321 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1073 _refine_ls_wR_factor_gt 0.0997 _refine_ls_goodness_of_fit_ref 0.890 _refine_ls_restrained_S_all 0.890 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.008 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 0.11093(5) 0.2500 0.04344(17) Uani 1 2 d S . . S1 S 0.42578(3) 0.26164(10) 0.22257(6) 0.0616(3) Uani 1 1 d . . . C1 C 0.32150(9) 0.1301(3) 0.39165(19) 0.0373(6) Uani 1 1 d . . . C9 C 0.26834(8) 0.1377(3) 0.35594(19) 0.0353(6) Uani 1 1 d . . . C2 C 0.33848(9) 0.0527(3) 0.4815(2) 0.0450(6) Uani 1 1 d . . . H2 H 0.3729 0.0482 0.5039 0.054 Uiso 1 1 calc R . . C10 C 0.23516(9) 0.0618(3) 0.4165(2) 0.0385(6) Uani 1 1 d . . . C8 C 0.24782(9) 0.2119(3) 0.2639(2) 0.0420(6) Uani 1 1 d . . . H8 H 0.2693 0.2611 0.2234 0.050 Uiso 1 1 calc R . . C4 C 0.25443(10) -0.0152(3) 0.5086(2) 0.0468(7) Uani 1 1 d . . . H4 H 0.2325 -0.0634 0.5483 0.056 Uiso 1 1 calc R . . C5 C 0.18264(9) 0.0641(3) 0.3811(2) 0.0477(7) Uani 1 1 d . . . H5 H 0.1605 0.0136 0.4196 0.057 Uiso 1 1 calc R . . C7 C 0.19695(10) 0.2134(3) 0.2326(2) 0.0492(7) Uani 1 1 d . . . H7 H 0.1841 0.2643 0.1717 0.059 Uiso 1 1 calc R . . C3 C 0.30487(10) -0.0198(3) 0.5401(2) 0.0484(7) Uani 1 1 d . . . H3 H 0.3171 -0.0716 0.6011 0.058 Uiso 1 1 calc R . . C6 C 0.16429(10) 0.1382(3) 0.2922(2) 0.0509(7) Uani 1 1 d . . . H6 H 0.1298 0.1392 0.2708 0.061 Uiso 1 1 calc R . . N1 N 0.35447(8) 0.2047(3) 0.33072(18) 0.0461(6) Uani 1 1 d . . . C11 C 0.40096(9) 0.1460(3) 0.31621(19) 0.0380(6) Uani 1 1 d . . . C12 C 0.51423(9) -0.1848(4) 0.1040(2) 0.0453(6) Uani 1 1 d . . . C13 C 0.46317(10) -0.2502(4) 0.1181(2) 0.0600(8) Uani 1 1 d . . . H13A H 0.4664 -0.3595 0.1559 0.090 Uiso 1 1 calc R . . H13B H 0.4434 -0.2720 0.0545 0.090 Uiso 1 1 calc R . . H13C H 0.4469 -0.1610 0.1531 0.090 Uiso 1 1 calc R . . C14 C 0.54367(11) -0.2914(4) 0.0406(2) 0.0729(10) Uani 1 1 d . . . H14A H 0.5711 -0.2203 0.0242 0.109 Uiso 1 1 calc R . . H14B H 0.5222 -0.3261 -0.0192 0.109 Uiso 1 1 calc R . . H14C H 0.5567 -0.3969 0.0759 0.109 Uiso 1 1 calc R . . N3 N 0.53129(7) -0.0388(3) 0.14918(16) 0.0405(5) Uani 1 1 d . . . N2 N 0.42110(7) 0.0138(3) 0.37001(16) 0.0433(5) Uani 1 1 d . . . H1N H 0.3425(9) 0.283(4) 0.295(2) 0.049(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0349(3) 0.0398(2) 0.0588(3) 0.000 0.0175(2) 0.000 S1 0.0463(4) 0.0612(5) 0.0845(6) 0.0348(4) 0.0336(4) 0.0175(3) C1 0.0376(13) 0.0294(12) 0.0485(16) -0.0015(11) 0.0179(11) 0.0003(10) C9 0.0367(13) 0.0237(11) 0.0486(16) -0.0052(10) 0.0162(11) -0.0003(9) C2 0.0407(14) 0.0454(14) 0.0498(17) -0.0015(13) 0.0099(12) 0.0021(12) C10 0.0412(14) 0.0279(11) 0.0499(16) -0.0072(11) 0.0184(12) -0.0035(10) C8 0.0410(14) 0.0351(13) 0.0528(17) 0.0027(12) 0.0166(12) 0.0019(10) C4 0.0550(16) 0.0395(14) 0.0516(17) -0.0013(12) 0.0263(13) -0.0073(12) C5 0.0431(15) 0.0406(14) 0.064(2) -0.0057(13) 0.0229(14) -0.0086(11) C7 0.0470(16) 0.0422(15) 0.0581(18) -0.0013(13) 0.0067(13) 0.0047(12) C3 0.0574(17) 0.0474(15) 0.0424(16) 0.0052(12) 0.0140(13) 0.0029(13) C6 0.0348(14) 0.0447(15) 0.074(2) -0.0076(14) 0.0115(13) -0.0031(11) N1 0.0378(12) 0.0406(12) 0.0636(17) 0.0153(12) 0.0194(11) 0.0086(10) C11 0.0323(12) 0.0344(13) 0.0497(16) 0.0008(11) 0.0140(11) 0.0001(10) C12 0.0455(15) 0.0421(14) 0.0498(17) -0.0030(13) 0.0124(13) -0.0092(12) C13 0.0484(16) 0.0590(18) 0.073(2) -0.0111(15) 0.0113(15) -0.0193(14) C14 0.074(2) 0.0602(19) 0.091(3) -0.0347(19) 0.0336(19) -0.0224(17) N3 0.0332(11) 0.0385(11) 0.0519(14) -0.0029(10) 0.0132(9) -0.0049(9) N2 0.0372(11) 0.0417(12) 0.0551(14) 0.0076(10) 0.0199(10) 0.0081(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N3 2.044(2) . ? Zn1 N3 2.044(2) 2_655 ? Zn1 S1 2.2696(7) 2_655 ? Zn1 S1 2.2696(7) . ? S1 C11 1.751(2) . ? C1 C2 1.368(4) . ? C1 N1 1.414(3) . ? C1 C9 1.439(3) . ? C9 C8 1.405(3) . ? C9 C10 1.419(3) . ? C2 C3 1.400(3) . ? C10 C4 1.406(4) . ? C10 C5 1.421(3) . ? C8 C7 1.369(3) . ? C4 C3 1.359(4) . ? C5 C6 1.354(4) . ? C7 C6 1.398(4) . ? N1 C11 1.365(3) . ? C11 N2 1.296(3) . ? C12 N3 1.299(3) . ? C12 C14 1.485(4) . ? C12 C13 1.495(3) . ? N3 N2 1.399(2) 2_655 ? N2 N3 1.399(2) 2_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Zn1 N3 113.89(11) . 2_655 ? N3 Zn1 S1 86.64(5) . 2_655 ? N3 Zn1 S1 126.74(6) 2_655 2_655 ? N3 Zn1 S1 126.74(6) . . ? N3 Zn1 S1 86.64(5) 2_655 . ? S1 Zn1 S1 120.71(4) 2_655 . ? C11 S1 Zn1 93.27(8) . . ? C2 C1 N1 122.4(2) . . ? C2 C1 C9 120.0(2) . . ? N1 C1 C9 117.6(2) . . ? C8 C9 C10 118.6(2) . . ? C8 C9 C1 123.7(2) . . ? C10 C9 C1 117.7(2) . . ? C1 C2 C3 121.0(2) . . ? C4 C10 C9 120.1(2) . . ? C4 C10 C5 121.5(2) . . ? C9 C10 C5 118.4(2) . . ? C7 C8 C9 121.4(2) . . ? C3 C4 C10 120.6(2) . . ? C6 C5 C10 121.3(2) . . ? C8 C7 C6 120.0(3) . . ? C4 C3 C2 120.5(3) . . ? C5 C6 C7 120.4(2) . . ? C11 N1 C1 128.7(2) . . ? N2 C11 N1 118.4(2) . . ? N2 C11 S1 127.82(18) . . ? N1 C11 S1 113.79(18) . . ? N3 C12 C14 122.9(2) . . ? N3 C12 C13 118.5(2) . . ? C14 C12 C13 118.6(2) . . ? C12 N3 N2 114.4(2) . 2_655 ? C12 N3 Zn1 128.58(16) . . ? N2 N3 Zn1 116.84(15) 2_655 . ? C11 N2 N3 115.0(2) . 2_655 ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.466 _refine_diff_density_min -0.594 _refine_diff_density_rms 0.067