# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'J. Dilworth' 'Andrew R. Cowley' 'Jason Davis' 'Rachel Dobson' 'Paul S. Donnelly' 'David Kerr' 'Adrian Nightingale' J.M.Peach 'Len Seymour' 'Ben Shore' _publ_contact_author_name 'J. Dilworth' _publ_contact_author_address ; Department of Inorganic Chemistry University of Oxford Chemistry Research Laboratory 12 Mansfield Rd Oxford Oxon. OX1 3TA UNITED KINGDOM ; _publ_contact_author_email JON.DILWORTH@CHEMISTRY.OXFORD.AC.UK _publ_section_title ; Fluorescence studies of the intra-cellular distribution of zinc bis(thiosemicarbazone) complexes in human cancer cells ; data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 256169' #=========================================================================== #=============================================== # Diffractometer details #=========================================================================== #=============================================== _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #=========================================================================== #=============================================== # General computing #=========================================================================== #=============================================== _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed #=========================================================================== #=============================================== _cell_length_a 17.1632(5) _cell_angle_alpha 90 _cell_length_b 8.1574(3) _cell_angle_beta 120.6784(13) _cell_length_c 17.4311(6) _cell_angle_gamma 90 _cell_volume 2098.9 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B 'S ' 0.1100 0.1240 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 International_Tables_Vol_IV_Table_2.2B 'Zn ' 0.2220 1.4310 14.0743 3.2655 7.0318 0.2333 5.1652 10.3163 2.4100 58.7097 1.3041 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C12 H26 N6 O2 S4 Zn1 ' _chemical_formula_moiety ' C12 H26 N6 O2 S4 Zn1 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 480.00 _cell_measurement_reflns_used 19382 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _cell_formula_units_Z 4 _exptl_crystal_description ' block ' _exptl_crystal_colour ' yellow ' _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_meas ? _exptl_crystal_F_000 1002.696 _exptl_absorpt_coefficient_mu 1.586 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.73 _exptl_absorpt_correction_T_max 0.88 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 19382 _reflns_number_total 4765 #5095 unique reflections including absences _diffrn_reflns_av_R_equivalents 0.057 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_gt 3307 _diffrn_reflns_theta_min 5.18 _diffrn_reflns_theta_max 27.43 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min -22 _reflns_limit_h_max 19 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _refine_diff_density_min -0.64 _refine_diff_density_max 0.74 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 3307 _refine_ls_number_parameters 262 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0407 _refine_ls_goodness_of_fit_ref 1.0822 _refine_ls_shift/su_max 0.022508 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters, Carruthers & Watkin , 1979, 0.620 0.287 0.325 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv == arithmetic mean of Ui # i.e. Ueqiv == (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type Zn1 0.19574(2) 0.38580(4) 0.17669(2) 0.0227 1.0000 Uani S1 0.30791(5) 0.30631(9) 0.14563(5) 0.0288 1.0000 Uani C1 0.30343(18) 0.4872(4) 0.08893(18) 0.0263 1.0000 Uani N1 0.24586(16) 0.6111(3) 0.06690(15) 0.0266 1.0000 Uani N2 0.18187(15) 0.5814(3) 0.09051(15) 0.0239 1.0000 Uani C2 0.11656(18) 0.6844(3) 0.06899(17) 0.0235 1.0000 Uani C3 0.04859(17) 0.6304(3) 0.09345(17) 0.0220 1.0000 Uani N3 0.06815(15) 0.4926(3) 0.13645(15) 0.0225 1.0000 Uani N4 0.00988(15) 0.4270(3) 0.16064(15) 0.0226 1.0000 Uani C4 0.03415(18) 0.2768(3) 0.19360(17) 0.0225 1.0000 Uani S2 0.12904(5) 0.16501(9) 0.20981(5) 0.0276 1.0000 Uani N5 0.36565(18) 0.4987(3) 0.06396(18) 0.0325 1.0000 Uani C5 0.3686(2) 0.6333(5) 0.0111(2) 0.0432 1.0000 Uani C6 0.1058(2) 0.8445(4) 0.02369(19) 0.0280 1.0000 Uani C7 -0.0352(2) 0.7278(4) 0.0655(2) 0.0300 1.0000 Uani N6 -0.02208(17) 0.1982(3) 0.21338(17) 0.0259 1.0000 Uani C8 -0.1087(2) 0.2664(4) 0.1936(2) 0.0306 1.0000 Uani O1 0.26944(14) 0.5027(3) 0.29980(13) 0.0347 1.0000 Uani S3 0.31599(11) 0.3598(2) 0.3752(1) 0.0322 0.495(4) Uani C9 0.2496(9) 0.3778(16) 0.4256(7) 0.0419 0.495(4) Uani C10 0.4237(5) 0.4448(9) 0.4506(5) 0.0477 0.495(4) Uani S103 0.32695(11) 0.4727(2) 0.3967(1) 0.0343 0.505(4) Uani C109 0.2651(9) 0.4097(18) 0.4447(8) 0.0454 0.505(4) Uani C110 0.3803(5) 0.2836(9) 0.4003(4) 0.0458 0.505(4) Uani O2 0.52308(15) 0.2969(3) 0.12219(16) 0.0458 1.0000 Uani S4 0.58928(6) 0.2730(1) 0.21997(6) 0.0381 1.0000 Uani C11 0.5571(3) 0.4145(6) 0.2771(3) 0.0539 1.0000 Uani C12 0.6907(2) 0.3769(5) 0.2421(3) 0.0467 1.0000 Uani H1 0.407(2) 0.433(4) 0.085(2) 0.04(1) 1.0000 Uiso H2 -0.004(2) 0.114(4) 0.242(2) 0.027(8) 1.0000 Uiso H51 0.4201 0.6166 0.0006 0.0582 1.0000 Uiso H52 0.3773 0.7388 0.0438 0.0582 1.0000 Uiso H53 0.3104 0.6375 -0.0474 0.0582 1.0000 Uiso H61 0.1569 0.8604 0.0125 0.0334 1.0000 Uiso H62 0.1062 0.9351 0.0625 0.0334 1.0000 Uiso H63 0.0470 0.8456 -0.0344 0.0334 1.0000 Uiso H71 -0.0722 0.6734 0.0877 0.0364 1.0000 Uiso H72 -0.0183 0.8408 0.0911 0.0364 1.0000 Uiso H73 -0.0713 0.7347 -0.0011 0.0364 1.0000 Uiso H81 -0.1395 0.1882 0.2138 0.0389 1.0000 Uiso H82 -0.0984 0.3731 0.2256 0.0389 1.0000 Uiso H83 -0.1476 0.2847 0.1279 0.0389 1.0000 Uiso H91 0.2705 0.2957 0.4749 0.0521 0.4954 Uiso H92 0.2563 0.4908 0.4505 0.0521 0.4954 Uiso H93 0.1846 0.3571 0.3801 0.0521 0.4954 Uiso H101 0.4589 0.3662 0.5006 0.0472 0.4954 Uiso H102 0.4156 0.5502 0.4750 0.0472 0.4954 Uiso H103 0.4572 0.4659 0.4185 0.0472 0.4954 Uiso H1091 0.3070 0.3912 0.5100 0.0567 0.5046 Uiso H1092 0.2199 0.4963 0.4358 0.0567 0.5046 Uiso H1093 0.2327 0.3054 0.4161 0.0567 0.5046 Uiso H1101 0.4216 0.2507 0.4638 0.0512 0.5046 Uiso H1102 0.4162 0.2967 0.3700 0.0512 0.5046 Uiso H1103 0.3331 0.1972 0.3691 0.0512 0.5046 Uiso H111 0.5993 0.4036 0.3429 0.0647 1.0000 Uiso H112 0.5602 0.5288 0.2581 0.0647 1.0000 Uiso H113 0.4938 0.3903 0.2624 0.0647 1.0000 Uiso H121 0.7376 0.3651 0.3067 0.0533 1.0000 Uiso H122 0.7138 0.3277 0.2050 0.0533 1.0000 Uiso H123 0.6773 0.4957 0.2271 0.0533 1.0000 Uiso 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 0.02464(16) 0.02172(16) 0.02345(16) 0.00392(13) 0.01359(12) 0.00324(12) S1 0.0320(4) 0.0275(4) 0.0337(4) 0.0064(3) 0.0217(3) 0.0073(3) C1 0.0263(13) 0.0299(14) 0.0233(13) 0.0004(11) 0.0130(11) 0.0015(11) N1 0.0282(11) 0.0296(12) 0.0276(11) 0.006(1) 0.018(1) 0.002(1) N2 0.0246(11) 0.0250(12) 0.0244(11) 0.0026(9) 0.0142(9) 0.0022(9) C2 0.0274(13) 0.0218(13) 0.0212(12) 0.001(1) 0.0123(11) 0.0001(11) C3 0.0240(12) 0.0217(13) 0.0194(11) 0.000(1) 0.011(1) 0.002(1) N3 0.025(1) 0.0220(11) 0.0229(11) 0.0003(9) 0.0136(9) -0.0000(9) N4 0.0252(11) 0.0226(11) 0.0228(11) 0.0013(9) 0.0143(9) -0.0007(9) C4 0.0267(13) 0.0217(12) 0.0198(12) -0.000(1) 0.012(1) -0.002(1) S2 0.0290(3) 0.0208(3) 0.0365(4) 0.0058(3) 0.0192(3) 0.0040(3) N5 0.0316(13) 0.0376(14) 0.0360(14) 0.0092(12) 0.0228(11) 0.0071(11) C5 0.0456(18) 0.051(2) 0.0487(19) 0.0126(17) 0.0356(17) 0.0058(16) C6 0.0321(14) 0.0242(14) 0.0272(13) 0.0049(11) 0.0147(12) 0.0020(11) C7 0.0334(15) 0.0255(14) 0.0320(15) 0.0055(12) 0.0173(13) 0.0075(12) N6 0.0294(12) 0.0206(11) 0.0322(12) 0.004(1) 0.019(1) 0.0010(9) C8 0.0309(15) 0.0303(15) 0.0359(16) 0.0025(12) 0.0209(13) 0.0018(12) O1 0.034(1) 0.0455(13) 0.023(1) 0.0017(9) 0.0133(8) 0.000(1) S3 0.0379(9) 0.0281(11) 0.0239(7) 0.0039(6) 0.0109(6) 0.0045(6) C9 0.077(6) 0.035(5) 0.019(4) -0.004(4) 0.028(4) -0.013(4) C10 0.045(4) 0.036(3) 0.037(3) 0.002(3) 0.003(3) 0.003(3) S103 0.0454(9) 0.0298(11) 0.0209(7) -0.0042(6) 0.0120(6) 0.0017(7) C109 0.065(5) 0.044(6) 0.033(5) -0.018(4) 0.029(4) -0.011(4) C110 0.048(4) 0.047(4) 0.033(3) 0.007(3) 0.014(3) 0.014(3) O2 0.0320(12) 0.0641(17) 0.0364(12) -0.0117(12) 0.014(1) 0.0059(11) S4 0.0350(4) 0.0343(4) 0.0417(4) 0.0003(3) 0.0171(3) -0.0008(3) C11 0.046(2) 0.074(3) 0.0422(19) -0.0220(19) 0.0225(17) -0.0113(19) C12 0.0318(16) 0.049(2) 0.053(2) 0.0037(17) 0.0168(15) -0.0006(15) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Zn1 . S1 . 2.3418(7) yes Zn1 . N2 . 2.120(2) yes Zn1 . N3 . 2.116(2) yes Zn1 . S2 . 2.3585(7) yes Zn1 . O1 . 2.084(2) yes S1 . C1 . 1.756(3) yes C1 . N1 . 1.326(4) yes C1 . N5 . 1.346(4) yes N1 . N2 . 1.377(3) yes N2 . C2 . 1.294(4) yes C2 . C3 . 1.498(4) yes C2 . C6 . 1.488(4) yes C3 . N3 . 1.297(3) yes C3 . C7 . 1.491(4) yes N3 . N4 . 1.376(3) yes N4 . C4 . 1.327(3) yes C4 . S2 . 1.759(3) yes C4 . N6 . 1.342(4) yes N5 . C5 . 1.450(4) yes N5 . H1 . 0.82(3) yes C5 . H51 . 1.000 no C5 . H52 . 1.000 no C5 . H53 . 1.000 no C6 . H61 . 1.000 no C6 . H62 . 1.000 no C6 . H63 . 1.000 no C7 . H71 . 1.000 no C7 . H72 . 1.000 no C7 . H73 . 1.000 no N6 . C8 . 1.454(4) yes N6 . H2 . 0.82(3) yes C8 . H81 . 1.000 no C8 . H82 . 1.000 no C8 . H83 . 1.000 no O1 . S3 . 1.629(3) yes O1 . S103 . 1.478(2) yes S3 . C9 . 1.764(12) yes S3 . C10 . 1.774(7) yes C9 . H91 . 1.000 no C9 . H92 . 1.000 no C9 . H93 . 1.000 no C10 . H101 . 1.000 no C10 . H102 . 1.000 no C10 . H103 . 1.000 no S103 . C109 . 1.732(13) yes S103 . C110 . 1.779(7) yes C109 . H1091 . 1.000 no C109 . H1092 . 1.000 no C109 . H1093 . 1.000 no C110 . H1101 . 1.000 no C110 . H1102 . 1.000 no C110 . H1103 . 1.000 no O2 . S4 . 1.503(2) yes S4 . C11 . 1.786(4) yes S4 . C12 . 1.792(4) yes C11 . H111 . 1.000 no C11 . H112 . 1.000 no C11 . H113 . 1.000 no C12 . H121 . 1.000 no C12 . H122 . 1.000 no C12 . H123 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag S1 . Zn1 . N2 . 81.54(6) yes S1 . Zn1 . N3 . 150.59(6) yes N2 . Zn1 . N3 . 74.47(9) yes S1 . Zn1 . S2 . 113.84(3) yes N2 . Zn1 . S2 . 148.78(7) yes N3 . Zn1 . S2 . 81.14(6) yes S1 . Zn1 . O1 . 103.06(6) yes N2 . Zn1 . O1 . 100.08(9) yes N3 . Zn1 . O1 . 97.75(9) yes S2 . Zn1 . O1 . 102.28(6) yes Zn1 . S1 . C1 . 95.30(9) yes S1 . C1 . N1 . 128.0(2) yes S1 . C1 . N5 . 115.2(2) yes N1 . C1 . N5 . 116.7(3) yes C1 . N1 . N2 . 111.7(2) yes Zn1 . N2 . N1 . 121.75(17) yes Zn1 . N2 . C2 . 117.49(18) yes N1 . N2 . C2 . 120.3(2) yes N2 . C2 . C3 . 114.3(2) yes N2 . C2 . C6 . 125.3(2) yes C3 . C2 . C6 . 120.3(2) yes C2 . C3 . N3 . 114.2(2) yes C2 . C3 . C7 . 120.8(2) yes N3 . C3 . C7 . 125.0(2) yes Zn1 . N3 . C3 . 117.86(18) yes Zn1 . N3 . N4 . 121.95(16) yes C3 . N3 . N4 . 120.0(2) yes N3 . N4 . C4 . 112.0(2) yes N4 . C4 . S2 . 127.5(2) yes N4 . C4 . N6 . 116.4(2) yes S2 . C4 . N6 . 116.1(2) yes Zn1 . S2 . C4 . 95.16(9) yes C1 . N5 . C5 . 123.2(3) yes C1 . N5 . H1 . 118.(3) yes C5 . N5 . H1 . 118.(3) yes N5 . C5 . H51 . 109.5 no N5 . C5 . H52 . 109.5 no H51 . C5 . H52 . 109.5 no N5 . C5 . H53 . 109.5 no H51 . C5 . H53 . 109.5 no H52 . C5 . H53 . 109.5 no C2 . C6 . H61 . 109.5 no C2 . C6 . H62 . 109.5 no H61 . C6 . H62 . 109.5 no C2 . C6 . H63 . 109.5 no H61 . C6 . H63 . 109.5 no H62 . C6 . H63 . 109.5 no C3 . C7 . H71 . 109.5 no C3 . C7 . H72 . 109.5 no H71 . C7 . H72 . 109.5 no C3 . C7 . H73 . 109.5 no H71 . C7 . H73 . 109.5 no H72 . C7 . H73 . 109.5 no C4 . N6 . C8 . 122.6(2) yes C4 . N6 . H2 . 118.(3) yes C8 . N6 . H2 . 119.(3) yes N6 . C8 . H81 . 109.5 no N6 . C8 . H82 . 109.5 no H81 . C8 . H82 . 109.5 no N6 . C8 . H83 . 109.5 no H81 . C8 . H83 . 109.5 no H82 . C8 . H83 . 109.5 no Zn1 . O1 . S3 . 107.08(14) yes Zn1 . O1 . S103 . 143.25(17) yes O1 . S3 . C9 . 99.6(5) yes O1 . S3 . C10 . 102.4(3) yes C9 . S3 . C10 . 107.0(5) yes S3 . C9 . H91 . 109.4 no S3 . C9 . H92 . 109.5 no H91 . C9 . H92 . 109.5 no S3 . C9 . H93 . 109.5 no H91 . C9 . H93 . 109.5 no H92 . C9 . H93 . 109.5 no S3 . C10 . H101 . 109.5 no S3 . C10 . H102 . 109.5 no H101 . C10 . H102 . 109.5 no S3 . C10 . H103 . 109.5 no H101 . C10 . H103 . 109.5 no H102 . C10 . H103 . 109.5 no O1 . S103 . C109 . 112.6(5) yes O1 . S103 . C110 . 102.4(3) yes C109 . S103 . C110 . 99.0(6) yes S103 . C109 . H1091 . 109.5 no S103 . C109 . H1092 . 109.4 no S103 . C109 . H1093 . 109.5 no H1091 . C109 . H1092 . 109.5 no H1091 . C109 . H1093 . 109.5 no H1092 . C109 . H1093 . 109.5 no S103 . C110 . H1101 . 109.5 no S103 . C110 . H1102 . 109.5 no H1101 . C110 . H1102 . 109.5 no S103 . C110 . H1103 . 109.5 no H1101 . C110 . H1103 . 109.5 no H1102 . C110 . H1103 . 109.5 no O2 . S4 . C11 . 106.22(17) yes O2 . S4 . C12 . 105.83(17) yes C11 . S4 . C12 . 96.72(19) yes S4 . C11 . H111 . 109.5 no S4 . C11 . H112 . 109.5 no H111 . C11 . H112 . 109.5 no S4 . C11 . H113 . 109.5 no H111 . C11 . H113 . 109.5 no H112 . C11 . H113 . 109.5 no S4 . C12 . H121 . 109.5 no S4 . C12 . H122 . 109.5 no H121 . C12 . H122 . 109.5 no S4 . C12 . H123 . 109.5 no H121 . C12 . H123 . 109.5 no H122 . C12 . H123 . 109.5 no loop_ _geom_hbond_atom_site_label_d _geom_hbond_atom_site_label_h _geom_hbond_atom_site_label_a _geom_hbond_site_symmetry_a _geom_hbond_distance_dh _geom_hbond_distance_ha _geom_hbond_distance_da _geom_hbond_angle_dha _geom_hbond_publ_flag N5 H1 O2 . 0.82(3) 2.07(3) 2.871(4) 168.(4) yes N6 H2 N4 3_545 0.82(3) 2.32(3) 3.048(3) 150.(3) yes data_ARC647 _database_code_depnum_ccdc_archive 'CCDC 256170' #=========================================================================== #=============================================== # Diffractometer details #=========================================================================== #=============================================== _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'EvalCCD' (Bruker-Nonius, 2002) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #=========================================================================== #=============================================== # General computing #=========================================================================== #=============================================== _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_special_details ; The NH hydrogen atom was located in a difference Fourier map and its coordinates and isotropic thermal parameters subsequently refined. Other hydrogen atoms were positioned geometrically. The orientations of the two methyl groups were determined by examination of a difference Fourier map ; #=========================================================================== #=============================================== _cell_length_a 7.8934(3) _cell_angle_alpha 74.5790(15) _cell_length_b 8.5558(3) _cell_angle_beta 87.2903(16) _cell_length_c 14.1976(5) _cell_angle_gamma 85.2071(19) _cell_volume 920.76(6) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'Cl ' 0.1320 0.1590 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'S ' 0.1100 0.1240 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 International_Tables_Vol_IV_Table_2.2B 'Zn ' 0.2220 1.4310 14.0743 3.2655 7.0318 0.2333 5.1652 10.3163 2.4100 58.7097 1.3041 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C14 H23 Cl1 N6 S2 Zn1 ' _chemical_formula_moiety ' C14 H23 Cl1 N6 S2 Zn1 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 440.33 _cell_measurement_reflns_used 16265 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _cell_formula_units_Z 2 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' yellow ' _exptl_crystal_size_min 0.06 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_max 0.44 _exptl_crystal_density_diffrn 1.588 _exptl_crystal_density_meas ? _exptl_crystal_F_000 457.149 _exptl_absorpt_coefficient_mu 1.715 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SORTAV (Blessing, 1997) ; _exptl_absorpt_correction_T_min 0.50 _exptl_absorpt_correction_T_max 0.90 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 16265 _reflns_number_total 4209 _diffrn_reflns_av_R_equivalents 0.074 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measured_fraction_theta_full 0.994 _reflns_number_gt 2527 _diffrn_reflns_theta_min 5.05 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 27.49 _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 -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min -10 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _refine_diff_density_min -0.76 _refine_diff_density_max 0.75 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 2527 _refine_ls_number_parameters 221 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0396 _refine_ls_goodness_of_fit_ref 1.0511 _refine_ls_shift/su_max 0.015915 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979) 0.802 0.371 0.541 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv == arithmetic mean of Ui # i.e. Ueqiv == (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type Zn1 0.17212(5) 0.09955(5) 0.13839(3) 0.0171 1.0000 Uani Cl1 0.40960(11) 0.13654(11) 0.21435(6) 0.0226 1.0000 Uani S1 0.16163(12) 0.3217(1) -0.00747(6) 0.0208 1.0000 Uani C1 0.2678(4) 0.2299(4) -0.0884(2) 0.0175 1.0000 Uani N1 0.3044(4) 0.0652(4) -0.0658(2) 0.0198 1.0000 Uani N2 0.2523(4) -0.0235(3) 0.0247(2) 0.0194 1.0000 Uani C2 0.2631(4) -0.1802(4) 0.0491(2) 0.0172 1.0000 Uani C3 0.1925(4) -0.2550(4) 0.1482(2) 0.0174 1.0000 Uani N3 0.1381(4) -0.1497(3) 0.1962(2) 0.0180 1.0000 Uani N4 0.0632(4) -0.2027(3) 0.2868(2) 0.0198 1.0000 Uani C4 -0.0253(4) -0.0810(4) 0.3138(2) 0.0185 1.0000 Uani S2 -0.06603(11) 0.11815(11) 0.24222(6) 0.0224 1.0000 Uani N5 0.3195(4) 0.3170(3) -0.1752(2) 0.0200 1.0000 Uani C5 0.2972(5) 0.4958(4) -0.2061(3) 0.0231 1.0000 Uani C6 0.3269(6) 0.5366(5) -0.3167(3) 0.0338 1.0000 Uani C7 0.4498(5) 0.3968(5) -0.3318(3) 0.0284 1.0000 Uani C8 0.3981(5) 0.2491(4) -0.2539(2) 0.0221 1.0000 Uani C9 0.3308(5) -0.2853(4) -0.0151(3) 0.0218 1.0000 Uani C10 0.1819(5) -0.4340(4) 0.1841(2) 0.0211 1.0000 Uani N6 -0.0965(4) -0.1212(3) 0.4041(2) 0.0203 1.0000 Uani C11 -0.0712(5) -0.2860(5) 0.4689(3) 0.0278 1.0000 Uani C12 -0.1737(6) -0.2766(5) 0.5613(3) 0.0350 1.0000 Uani C13 -0.3130(6) -0.1419(6) 0.5243(3) 0.0348 1.0000 Uani C14 -0.2240(5) -0.0184(5) 0.4435(3) 0.0259 1.0000 Uani H1 0.347(5) 0.020(5) -0.101(3) 0.02(1) 1.0000 Uiso H51 0.3823 0.5450 -0.1749 0.0273 1.0000 Uiso H52 0.1798 0.5351 -0.1892 0.0273 1.0000 Uiso H61 0.3789 0.6431 -0.3412 0.0394 1.0000 Uiso H62 0.2179 0.5407 -0.3507 0.0394 1.0000 Uiso H71 0.5699 0.4185 -0.3233 0.0350 1.0000 Uiso H72 0.4380 0.3811 -0.3985 0.0350 1.0000 Uiso H81 0.4997 0.1734 -0.2298 0.0273 1.0000 Uiso H82 0.3144 0.1901 -0.2796 0.0273 1.0000 Uiso H91 0.3253 -0.4023 0.0212 0.0276 1.0000 Uiso H92 0.4516 -0.2628 -0.0347 0.0276 1.0000 Uiso H93 0.2608 -0.2611 -0.0749 0.0276 1.0000 Uiso H101 0.1312 -0.4612 0.2518 0.0255 1.0000 Uiso H102 0.2985 -0.4897 0.1845 0.0255 1.0000 Uiso H103 0.1088 -0.4714 0.1399 0.0255 1.0000 Uiso H111 0.0519 -0.3152 0.4834 0.0327 1.0000 Uiso H112 -0.1153 -0.3675 0.4391 0.0327 1.0000 Uiso H121 -0.1011 -0.2476 0.6091 0.0413 1.0000 Uiso H122 -0.2239 -0.3821 0.5928 0.0413 1.0000 Uiso H131 -0.3570 -0.0921 0.5777 0.0419 1.0000 Uiso H132 -0.4090 -0.1849 0.4977 0.0419 1.0000 Uiso H141 -0.1686 0.0607 0.4705 0.0318 1.0000 Uiso H142 -0.3056 0.0420 0.3923 0.0318 1.0000 Uiso 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 0.0211(2) 0.0150(2) 0.0165(2) -0.00701(15) 0.00316(15) -0.00140(15) Cl1 0.0224(4) 0.0247(4) 0.0226(4) -0.0095(3) 0.0003(3) -0.0019(3) S1 0.0288(5) 0.0161(4) 0.0181(4) -0.0070(3) 0.0028(3) 0.0012(3) C1 0.0185(16) 0.0169(16) 0.0193(16) -0.0080(13) -0.0041(13) -0.0003(13) N1 0.0282(16) 0.0165(15) 0.0167(14) -0.0095(12) 0.0068(12) -0.0003(12) N2 0.0245(15) 0.0199(15) 0.0162(14) -0.0090(12) 0.0029(11) -0.0027(12) C2 0.0177(15) 0.0155(16) 0.0210(16) -0.0094(13) 0.0019(13) -0.0025(12) C3 0.0150(15) 0.0189(16) 0.0190(16) -0.0066(13) -0.0022(12) 0.0007(12) N3 0.0188(14) 0.0194(14) 0.0163(13) -0.0066(11) 0.0003(11) 0.0006(11) N4 0.0239(15) 0.0186(15) 0.0186(14) -0.0084(11) 0.0036(12) -0.0016(12) C4 0.0195(16) 0.0184(17) 0.0203(16) -0.0090(13) -0.0035(13) -0.0026(13) S2 0.0240(4) 0.0195(4) 0.0213(4) -0.0037(3) 0.0064(3) 0.0031(3) N5 0.0262(15) 0.0164(14) 0.0185(14) -0.0071(11) 0.0027(12) -0.0006(11) C5 0.034(2) 0.0139(16) 0.0200(17) -0.0034(13) 0.0011(15) 0.0001(14) C6 0.057(3) 0.022(2) 0.0192(18) -0.0016(15) 0.0032(18) -0.0009(18) C7 0.039(2) 0.029(2) 0.0197(18) -0.0105(15) 0.0089(16) -0.0066(17) C8 0.0261(18) 0.0252(18) 0.0171(16) -0.0094(14) 0.0034(14) -0.0032(14) C9 0.0271(18) 0.0187(17) 0.0231(17) -0.0127(14) 0.0072(14) -0.0024(14) C10 0.0327(19) 0.0127(16) 0.0185(16) -0.0049(13) 0.0001(14) -0.0023(14) N6 0.0271(15) 0.0184(15) 0.0150(13) -0.0053(11) 0.0034(12) 0.0004(12) C11 0.042(2) 0.0226(19) 0.0177(17) -0.0025(14) 0.0000(16) -0.0028(16) C12 0.050(3) 0.041(2) 0.0126(16) -0.0036(16) 0.0063(17) -0.008(2) C13 0.038(2) 0.047(3) 0.0206(19) -0.0104(18) 0.0146(17) -0.0090(19) C14 0.0269(19) 0.028(2) 0.0250(18) -0.0111(15) 0.0096(15) -0.0045(15) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Zn1 . Cl1 . 2.2910(9) yes Zn1 . S1 . 2.4092(9) yes Zn1 . N2 . 2.194(3) yes Zn1 . N3 . 2.107(3) yes Zn1 . S2 . 2.3548(9) yes S1 . C1 . 1.708(3) yes C1 . N1 . 1.369(4) yes C1 . N5 . 1.326(4) yes N1 . N2 . 1.370(4) yes N1 . H1 . 0.76(4) yes N2 . C2 . 1.289(4) yes C2 . C3 . 1.485(5) yes C2 . C9 . 1.496(4) yes C3 . N3 . 1.303(4) yes C3 . C10 . 1.488(5) yes N3 . N4 . 1.368(4) yes N4 . C4 . 1.335(4) yes C4 . S2 . 1.748(4) yes C4 . N6 . 1.344(4) yes N5 . C5 . 1.472(4) yes N5 . C8 . 1.481(4) yes C5 . C6 . 1.526(5) yes C5 . H51 . 1.000 no C5 . H52 . 1.000 no C6 . C7 . 1.530(6) yes C6 . H61 . 1.000 no C6 . H62 . 1.000 no C7 . C8 . 1.512(5) yes C7 . H71 . 1.000 no C7 . H72 . 1.000 no C8 . H81 . 1.000 no C8 . H82 . 1.000 no C9 . H91 . 1.000 no C9 . H92 . 1.000 no C9 . H93 . 1.000 no C10 . H101 . 1.000 no C10 . H102 . 1.000 no C10 . H103 . 1.000 no N6 . C11 . 1.468(5) yes N6 . C14 . 1.470(4) yes C11 . C12 . 1.526(5) yes C11 . H111 . 1.000 no C11 . H112 . 1.000 no C12 . C13 . 1.528(6) yes C12 . H121 . 1.000 no C12 . H122 . 1.000 no C13 . C14 . 1.526(5) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C14 . H141 . 1.000 no C14 . H142 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Cl1 . Zn1 . S1 . 103.71(3) yes Cl1 . Zn1 . N2 . 108.39(8) yes S1 . Zn1 . N2 . 77.92(8) yes Cl1 . Zn1 . N3 . 103.39(8) yes S1 . Zn1 . N3 . 144.79(8) yes N2 . Zn1 . N3 . 72.48(11) yes Cl1 . Zn1 . S2 . 108.41(3) yes S1 . Zn1 . S2 . 111.28(3) yes N2 . Zn1 . S2 . 138.29(8) yes N3 . Zn1 . S2 . 80.54(8) yes Zn1 . S1 . C1 . 100.21(12) yes S1 . C1 . N1 . 121.6(3) yes S1 . C1 . N5 . 120.7(3) yes N1 . C1 . N5 . 117.7(3) yes C1 . N1 . N2 . 117.2(3) yes C1 . N1 . H1 . 124.(3) yes N2 . N1 . H1 . 119.(3) yes Zn1 . N2 . N1 . 120.0(2) yes Zn1 . N2 . C2 . 117.6(2) yes N1 . N2 . C2 . 122.1(3) yes N2 . C2 . C3 . 114.5(3) yes N2 . C2 . C9 . 125.4(3) yes C3 . C2 . C9 . 120.1(3) yes C2 . C3 . N3 . 113.7(3) yes C2 . C3 . C10 . 121.1(3) yes N3 . C3 . C10 . 125.2(3) yes Zn1 . N3 . C3 . 120.8(2) yes Zn1 . N3 . N4 . 119.7(2) yes C3 . N3 . N4 . 119.4(3) yes N3 . N4 . C4 . 111.3(3) yes N4 . C4 . S2 . 126.9(3) yes N4 . C4 . N6 . 115.2(3) yes S2 . C4 . N6 . 117.8(3) yes Zn1 . S2 . C4 . 92.81(12) yes C1 . N5 . C5 . 123.0(3) yes C1 . N5 . C8 . 125.1(3) yes C5 . N5 . C8 . 111.8(3) yes N5 . C5 . C6 . 103.8(3) yes N5 . C5 . H51 . 110.9 no C6 . C5 . H51 . 110.9 no N5 . C5 . H52 . 110.9 no C6 . C5 . H52 . 110.9 no H51 . C5 . H52 . 109.5 no C5 . C6 . C7 . 103.8(3) yes C5 . C6 . H61 . 110.9 no C7 . C6 . H61 . 110.9 no C5 . C6 . H62 . 110.9 no C7 . C6 . H62 . 110.9 no H61 . C6 . H62 . 109.5 no C6 . C7 . C8 . 104.9(3) yes C6 . C7 . H71 . 110.6 no C8 . C7 . H71 . 110.6 no C6 . C7 . H72 . 110.6 no C8 . C7 . H72 . 110.6 no H71 . C7 . H72 . 109.5 no N5 . C8 . C7 . 104.0(3) yes N5 . C8 . H81 . 110.8 no C7 . C8 . H81 . 110.8 no N5 . C8 . H82 . 110.8 no C7 . C8 . H82 . 110.8 no H81 . C8 . H82 . 109.5 no C2 . C9 . H91 . 109.5 no C2 . C9 . H92 . 109.5 no H91 . C9 . H92 . 109.5 no C2 . C9 . H93 . 109.5 no H91 . C9 . H93 . 109.5 no H92 . C9 . H93 . 109.5 no C3 . C10 . H101 . 109.5 no C3 . C10 . H102 . 109.5 no H101 . C10 . H102 . 109.5 no C3 . C10 . H103 . 109.5 no H101 . C10 . H103 . 109.5 no H102 . C10 . H103 . 109.5 no C4 . N6 . C11 . 121.7(3) yes C4 . N6 . C14 . 125.3(3) yes C11 . N6 . C14 . 112.5(3) yes N6 . C11 . C12 . 103.8(3) yes N6 . C11 . H111 . 110.9 no C12 . C11 . H111 . 110.9 no N6 . C11 . H112 . 110.9 no C12 . C11 . H112 . 110.9 no H111 . C11 . H112 . 109.5 no C11 . C12 . C13 . 103.6(3) yes C11 . C12 . H121 . 110.9 no C13 . C12 . H121 . 110.9 no C11 . C12 . H122 . 110.9 no C13 . C12 . H122 . 110.9 no H121 . C12 . H122 . 109.5 no C12 . C13 . C14 . 104.0(3) yes C12 . C13 . H131 . 110.8 no C14 . C13 . H131 . 110.8 no C12 . C13 . H132 . 110.8 no C14 . C13 . H132 . 110.8 no H131 . C13 . H132 . 109.5 no N6 . C14 . C13 . 102.8(3) yes N6 . C14 . H141 . 111.1 no C13 . C14 . H141 . 111.1 no N6 . C14 . H142 . 111.1 no C13 . C14 . H142 . 111.1 no H141 . C14 . H142 . 109.5 no