Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Phil Blower' 'Thomas C. Castle' 'Andrew R. Cowley' 'J. Dilworth' 'Paul S. Donnelly' 'Elena Labisbal' 'Frank E. Sowrey' 'Simon J. Teat' 'M. Went' _publ_contact_author_name 'Dr Phil Blower' _publ_contact_author_address ; School of Physical Sciences & Dept of Biosciences University of Kent Canterbury Kent CT2 7NJ UNITED KINGDOM ; _publ_contact_author_email P.J.BLOWER@KENT.AC.UK _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Structural trends in copper(II) bis(thiosemicarbazone) radiopharmaceuticals ; data_NiASTM _database_code_CSD 213898 #============================================================= # 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_hydrogens geom _refine_ls_hydrogen_treatment mixed #============================================================= _cell_length_a 7.2586(2) _cell_angle_alpha 90 _cell_length_b 16.9149(4) _cell_angle_beta 105.8679(9) _cell_length_c 12.8679(3) _cell_angle_gamma 90 _cell_volume 1519.7 _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 'Ni ' 0.2850 1.1130 12.8376 3.8785 7.2920 0.2565 4.4438 12.1763 2.3800 66.3421 1.0341 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 _chemical_formula_sum ' C10 H17 N7 Ni1 S2 ' _chemical_formula_moiety ' C10 H17 N7 Ni1 S2 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 358.12 _cell_measurement_reflns_used 11398 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _cell_formula_units_Z 4 _exptl_crystal_description ' fragment ' _exptl_crystal_colour ' dark brown ' _exptl_crystal_size_min 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_meas ? _exptl_crystal_F_000 745.995 _exptl_absorpt_coefficient_mu 1.552 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.63 _exptl_absorpt_correction_T_max 0.63 _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 11398 _reflns_number_total 3567 _diffrn_reflns_av_R_equivalents 0.027 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_gt 2698 _diffrn_reflns_theta_min 5.15 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 21 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _refine_diff_density_min -0.60 _refine_diff_density_max 0.60 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 2698 _refine_ls_number_parameters 189 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0376 _refine_ls_goodness_of_fit_ref 1.3644 _refine_ls_shift/su_max 0.011029 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979) 0.377 0.105 0.136 ; _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 Ni1 0.20688(4) 0.101474(18) 0.05761(2) 0.0177 1.0000 Uani C11 0.3054(3) -0.05040(15) 0.0397(2) 0.0207 1.0000 Uani N11 0.2351(3) 0.01102(12) -0.01894(16) 0.0193 1.0000 Uani N12 0.1886(3) 0.00600(12) -0.13000(16) 0.0210 1.0000 Uani C12 0.1170(3) 0.07381(15) -0.17263(19) 0.0209 1.0000 Uani S1 0.08521(9) 0.15715(4) -0.09652(5) 0.0214 1.0000 Uani C1 0.3388(4) -0.12820(16) -0.0061(2) 0.0254 1.0000 Uani N13 0.0614(3) 0.08100(14) -0.28033(18) 0.0264 1.0000 Uani C13 0.0692(5) 0.01562(17) -0.3517(2) 0.0333 1.0000 Uani C22 0.2937(3) 0.13816(16) 0.2849(2) 0.0235 1.0000 Uani N21 0.3119(3) 0.03859(12) 0.17729(16) 0.0202 1.0000 Uani N22 0.3445(3) 0.06346(13) 0.28251(16) 0.0235 1.0000 Uani C21 0.3494(3) -0.03415(15) 0.15616(19) 0.0212 1.0000 Uani S2 0.19951(9) 0.19654(4) 0.16846(5) 0.0234 1.0000 Uani C2 0.4272(4) -0.09489(16) 0.2408(2) 0.0280 1.0000 Uani N23 0.3136(4) 0.17358(16) 0.38012(18) 0.0308 1.0000 Uani C23 0.3798(4) 0.13332(19) 0.4832(2) 0.0346 1.0000 Uani N31 -0.1249(4) 0.33162(16) -0.0016(2) 0.0436 1.0000 Uani C31 -0.1757(4) 0.32565(17) -0.0934(3) 0.0338 1.0000 Uani C32 -0.2387(4) 0.31857(18) -0.2109(2) 0.0349 1.0000 Uani H1 0.023(4) 0.1211(19) -0.308(3) 0.023(8) 1.0000 Uiso H2 0.270(5) 0.216(2) 0.379(3) 0.028(8) 1.0000 Uiso H11 0.2952 -0.1257 -0.0867 0.0306 1.0000 Uiso H12 0.4786 -0.1411 0.0177 0.0306 1.0000 Uiso H13 0.2653 -0.1701 0.0201 0.0306 1.0000 Uiso H131 0.0215 0.0335 -0.4285 0.0399 1.0000 Uiso H132 0.2045 -0.0031 -0.3375 0.0399 1.0000 Uiso H133 -0.0130 -0.0286 -0.3384 0.0399 1.0000 Uiso H21 0.4461 -0.0708 0.3139 0.0328 1.0000 Uiso H22 0.5527 -0.1147 0.2332 0.0328 1.0000 Uiso H23 0.3349 -0.1399 0.2319 0.0328 1.0000 Uiso H231 0.3833 0.1715 0.5430 0.0408 1.0000 Uiso H232 0.5112 0.1118 0.4912 0.0408 1.0000 Uiso H233 0.2904 0.0890 0.4864 0.0408 1.0000 Uiso H321 -0.3276 0.3631 -0.2417 0.0406 1.0000 Uiso H322 -0.1249 0.3207 -0.2405 0.0406 1.0000 Uiso H323 -0.3069 0.2671 -0.2311 0.0406 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 Ni1 0.01847(15) 0.02022(16) 0.01396(15) 0.00185(11) 0.00367(11) 0.00087(12) C11 0.016(1) 0.0224(12) 0.0232(11) 0.0016(9) 0.0055(9) -0.0025(9) N11 0.0185(9) 0.022(1) 0.017(1) 0.0012(8) 0.0050(7) -0.0003(8) N12 0.024(1) 0.0243(11) 0.0157(9) 0.0005(8) 0.0062(8) 0.0002(8) C12 0.0197(11) 0.0254(12) 0.0184(11) 0.0000(9) 0.0067(9) -0.0020(9) S1 0.0254(3) 0.0225(3) 0.0155(3) 0.0018(2) 0.0043(2) 0.0030(2) C1 0.0262(12) 0.0229(12) 0.0275(12) 0.001(1) 0.008(1) 0.003(1) N13 0.0336(12) 0.0271(12) 0.017(1) 0.0015(9) 0.0044(9) 0.005(1) C13 0.0482(17) 0.0309(15) 0.0208(12) -0.0043(11) 0.0095(11) 0.0006(13) C21 0.0176(11) 0.0241(12) 0.0216(11) 0.0048(9) 0.0050(9) -0.0015(9) N21 0.0180(9) 0.025(1) 0.0177(9) 0.0027(8) 0.0048(7) -0.0009(8) N22 0.026(1) 0.0281(11) 0.0152(9) 0.0019(8) 0.0039(8) -0.0002(9) C22 0.0201(11) 0.0312(13) 0.0191(11) 0.002(1) 0.0052(9) -0.000(1) S2 0.0283(3) 0.0247(3) 0.0163(3) 0.0009(2) 0.0044(2) 0.0038(2) C2 0.0293(13) 0.0282(13) 0.0246(13) 0.006(1) 0.004(1) 0.0025(11) N23 0.0372(13) 0.0354(14) 0.0180(11) -0.0002(9) 0.0047(9) 0.0087(11) C23 0.0389(15) 0.0468(17) 0.0163(12) 0.0024(12) 0.0047(11) 0.0036(13) N31 0.0526(17) 0.0359(14) 0.0398(15) -0.0003(12) 0.0086(12) 0.0006(13) C31 0.0306(14) 0.0262(14) 0.0440(17) 0.0005(12) 0.0092(12) 0.0015(11) C32 0.0335(14) 0.0324(15) 0.0356(15) 0.0027(12) 0.0038(12) 0.0036(12) _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 Ni1 . N11 . 1.861(2) yes Ni1 . S1 . 2.1546(6) yes Ni1 . N21 . 1.855(2) yes Ni1 . S2 . 2.1598(7) yes C11 . N11 . 1.303(3) yes C11 . C1 . 1.489(4) yes C11 . C21 . 1.470(3) yes N11 . N12 . 1.378(3) yes N12 . C12 . 1.315(3) yes C12 . S1 . 1.767(3) yes C12 . N13 . 1.339(3) yes C1 . H11 . 1.000 no C1 . H12 . 1.000 no C1 . H13 . 1.000 no N13 . C13 . 1.449(3) yes N13 . H1 . 0.78(3) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C13 . H133 . 1.000 no C22 . N22 . 1.319(4) yes C22 . S2 . 1.768(3) yes C22 . N23 . 1.336(3) yes N21 . N22 . 1.375(3) yes N21 . C21 . 1.305(3) yes C21 . C2 . 1.491(3) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C2 . H23 . 1.000 no N23 . C23 . 1.451(3) yes N23 . H2 . 0.79(3) yes C23 . H231 . 1.000 no C23 . H232 . 1.000 no C23 . H233 . 1.000 no N31 . C31 . 1.142(4) yes C31 . C32 . 1.460(4) yes C32 . H321 . 1.000 no C32 . H322 . 1.000 no C32 . H323 . 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 N11 . Ni1 . S1 . 87.07(6) yes N11 . Ni1 . N21 . 83.59(9) yes S1 . Ni1 . N21 . 170.61(7) yes N11 . Ni1 . S2 . 171.04(6) yes S1 . Ni1 . S2 . 101.81(3) yes N21 . Ni1 . S2 . 87.56(7) yes N11 . C11 . C1 . 123.7(2) yes N11 . C11 . C21 . 112.5(2) yes C1 . C11 . C21 . 123.7(2) yes Ni1 . N11 . C11 . 115.52(17) yes Ni1 . N11 . N12 . 124.62(16) yes C11 . N11 . N12 . 119.9(2) yes N11 . N12 . C12 . 109.6(2) yes N12 . C12 . S1 . 124.12(18) yes N12 . C12 . N13 . 118.9(2) yes S1 . C12 . N13 . 116.9(2) yes Ni1 . S1 . C12 . 94.51(8) yes C11 . C1 . H11 . 109.5 no C11 . C1 . H12 . 109.5 no H11 . C1 . H12 . 109.5 no C11 . C1 . H13 . 109.5 no H11 . C1 . H13 . 109.5 no H12 . C1 . H13 . 109.5 no C12 . N13 . C13 . 122.3(2) yes C12 . N13 . H1 . 122.(3) yes C13 . N13 . H1 . 116.(3) yes N13 . C13 . H131 . 109.5 no N13 . C13 . H132 . 109.5 no H131 . C13 . H132 . 109.5 no N13 . C13 . H133 . 109.5 no H131 . C13 . H133 . 109.5 no H132 . C13 . H133 . 109.5 no N22 . C22 . S2 . 124.13(19) yes N22 . C22 . N23 . 119.4(2) yes S2 . C22 . N23 . 116.5(2) yes Ni1 . N21 . N22 . 124.25(16) yes Ni1 . N21 . C21 . 115.43(17) yes N22 . N21 . C21 . 120.3(2) yes C22 . N22 . N21 . 110.0(2) yes C11 . C21 . N21 . 112.9(2) yes C11 . C21 . C2 . 123.3(2) yes N21 . C21 . C2 . 123.8(2) yes Ni1 . S2 . C22 . 94.02(9) yes C21 . C2 . H21 . 109.5 no C21 . C2 . H22 . 109.5 no H21 . C2 . H22 . 109.5 no C21 . C2 . H23 . 109.5 no H21 . C2 . H23 . 109.5 no H22 . C2 . H23 . 109.5 no C22 . N23 . C23 . 123.6(3) yes C22 . N23 . H2 . 117.(3) yes C23 . N23 . H2 . 118.(3) yes N23 . C23 . H231 . 109.5 no N23 . C23 . H232 . 109.5 no H231 . C23 . H232 . 109.5 no N23 . C23 . H233 . 109.5 no H231 . C23 . H233 . 109.5 no H232 . C23 . H233 . 109.5 no N31 . C31 . C32 . 179.3(3) yes C31 . C32 . H321 . 109.5 no C31 . C32 . H322 . 109.5 no H321 . C32 . H322 . 109.5 no C31 . C32 . H323 . 109.5 no H321 . C32 . H323 . 109.5 no H322 . C32 . H323 . 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 N23 H2 S1 4_555 0.79(3) 2.59(3) 3.363(3) 167.(3) yes data_kent7 _database_code_CSD 213899 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H20 Cu N6 O S3' _chemical_formula_weight 400.04 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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 8.0485(13) _cell_length_b 14.086(2) _cell_length_c 15.071(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.864(3) _cell_angle_gamma 90.00 _cell_volume 1692.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8401 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 29.29 _exptl_crystal_description needle _exptl_crystal_colour orange/red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.570 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 828 _exptl_absorpt_coefficient_mu 1.667 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.62 _exptl_absorpt_correction_T_max 0.96 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6872 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART 1K CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 15 _diffrn_reflns_number 16313 _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 29.38 _reflns_number_total 4753 _reflns_number_gt 3976 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0403P)^2^+0.3936P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4753 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0899 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 Cu Cu 0.33333(3) 0.432877(16) 0.095127(14) 0.02354(8) Uani 1 1 d . . . S1 S 0.30389(6) 0.47253(4) 0.23658(3) 0.02923(11) Uani 1 1 d . . . C1 C 0.0721(3) 0.64900(15) -0.06121(13) 0.0329(4) Uani 1 1 d . . . H1A H 0.0033 0.6730 -0.0173 0.049 Uiso 1 1 calc R . . H1B H -0.0007 0.6300 -0.1158 0.049 Uiso 1 1 calc R . . H1C H 0.1488 0.6990 -0.0756 0.049 Uiso 1 1 calc R . . S2 S 0.47972(6) 0.29695(3) 0.09602(3) 0.02968(11) Uani 1 1 d . . . C2 C 0.2363(3) 0.50950(15) -0.17905(12) 0.0311(4) Uani 1 1 d . . . H2A H 0.3065 0.4619 -0.2034 0.047 Uiso 1 1 calc R . . H2B H 0.2747 0.5732 -0.1927 0.047 Uiso 1 1 calc R . . H2C H 0.1194 0.5013 -0.2062 0.047 Uiso 1 1 calc R . . C11 C 0.1709(2) 0.56547(13) -0.02319(12) 0.0254(4) Uani 1 1 d . . . N11 N 0.1968(2) 0.54576(11) 0.06170(10) 0.0244(3) Uani 1 1 d . . . C12 C 0.1767(2) 0.57222(13) 0.20525(12) 0.0252(4) Uani 1 1 d . . . N12 N 0.1315(2) 0.60261(11) 0.12238(10) 0.0258(3) Uani 1 1 d . . . N13 N 0.1164(2) 0.61953(12) 0.27144(10) 0.0301(3) Uani 1 1 d . . . H13 H 0.1460 0.6012 0.3272 0.036 Uiso 1 1 calc R . . C13 C 0.0031(3) 0.70044(14) 0.25362(14) 0.0365(5) Uani 1 1 d . . . H13A H 0.0671 0.7565 0.2400 0.055 Uiso 1 1 calc R . . H13B H -0.0520 0.7132 0.3065 0.055 Uiso 1 1 calc R . . H13C H -0.0820 0.6860 0.2025 0.055 Uiso 1 1 calc R . . N21 N 0.3285(2) 0.42806(11) -0.03553(10) 0.0254(3) Uani 1 1 d . . . C21 C 0.2488(2) 0.49746(14) -0.07986(11) 0.0259(4) Uani 1 1 d . . . N22 N 0.4060(2) 0.35892(12) -0.07886(11) 0.0287(3) Uani 1 1 d . . . C22 C 0.4816(2) 0.29615(13) -0.02109(13) 0.0276(4) Uani 1 1 d . . . N23 N 0.5662(2) 0.22512(13) -0.05369(12) 0.0343(4) Uani 1 1 d . . . H23 H 0.6176 0.1832 -0.0162 0.041 Uiso 1 1 calc R . . C23 C 0.5758(3) 0.21500(16) -0.14919(15) 0.0418(5) Uani 1 1 d . . . H23A H 0.4662 0.1954 -0.1803 0.063 Uiso 1 1 calc R . . H23B H 0.6599 0.1669 -0.1581 0.063 Uiso 1 1 calc R . . H23C H 0.6078 0.2759 -0.1734 0.063 Uiso 1 1 calc R . . O1S O 0.21992(19) 0.56442(9) 0.45938(9) 0.0305(3) Uani 1 1 d . . . S1S S 0.29323(6) 0.46578(3) 0.47768(3) 0.02683(11) Uani 1 1 d . . . C1S C 0.2928(3) 0.44673(16) 0.59481(14) 0.0387(5) Uani 1 1 d . . . H1S1 H 0.3730 0.4900 0.6288 0.058 Uiso 1 1 calc R . . H1S2 H 0.3249 0.3809 0.6098 0.058 Uiso 1 1 calc R . . H1S3 H 0.1802 0.4588 0.6101 0.058 Uiso 1 1 calc R . . C2S C 0.1321(3) 0.38276(15) 0.43752(14) 0.0342(4) Uani 1 1 d . . . H2S1 H 0.0314 0.3961 0.4654 0.051 Uiso 1 1 calc R . . H2S2 H 0.1710 0.3181 0.4529 0.051 Uiso 1 1 calc R . . H2S3 H 0.1054 0.3886 0.3723 0.051 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 Cu 0.02544(12) 0.02646(13) 0.01784(12) 0.00066(8) -0.00015(8) -0.00219(8) S1 0.0321(2) 0.0365(3) 0.0179(2) 0.00249(17) -0.00068(17) 0.00606(19) C1 0.0371(10) 0.0339(11) 0.0257(9) 0.0065(7) -0.0029(8) 0.0003(8) S2 0.0353(3) 0.0270(2) 0.0260(2) 0.00003(17) 0.00164(18) -0.00029(18) C2 0.0366(10) 0.0372(11) 0.0186(8) 0.0017(7) 0.0007(7) -0.0083(8) C11 0.0251(8) 0.0295(9) 0.0201(8) 0.0032(7) -0.0026(6) -0.0056(7) N11 0.0272(7) 0.0250(8) 0.0201(7) 0.0006(5) -0.0001(6) -0.0046(6) C12 0.0277(9) 0.0240(9) 0.0225(8) -0.0008(6) -0.0007(7) -0.0037(7) N12 0.0303(8) 0.0251(8) 0.0208(7) -0.0011(6) -0.0007(6) -0.0014(6) N13 0.0379(9) 0.0303(9) 0.0206(7) -0.0037(6) -0.0015(6) 0.0012(7) C13 0.0529(13) 0.0260(10) 0.0300(10) -0.0048(8) 0.0029(9) 0.0052(9) N21 0.0276(8) 0.0271(8) 0.0209(7) -0.0012(6) 0.0014(6) -0.0051(6) C21 0.0273(9) 0.0311(9) 0.0184(8) 0.0000(7) -0.0006(6) -0.0085(7) N22 0.0321(8) 0.0297(8) 0.0241(7) -0.0055(6) 0.0036(6) -0.0047(6) C22 0.0279(9) 0.0270(9) 0.0277(9) -0.0050(7) 0.0026(7) -0.0081(7) N23 0.0403(10) 0.0296(9) 0.0335(9) -0.0061(7) 0.0065(7) -0.0018(7) C23 0.0549(14) 0.0330(11) 0.0398(12) -0.0124(9) 0.0150(10) -0.0064(10) O1S 0.0398(8) 0.0276(7) 0.0240(7) 0.0018(5) 0.0037(6) 0.0033(6) S1S 0.0265(2) 0.0287(2) 0.0254(2) -0.00146(17) 0.00422(17) 0.00199(17) C1S 0.0524(13) 0.0362(12) 0.0268(10) 0.0053(8) 0.0032(9) 0.0092(9) C2S 0.0327(10) 0.0307(10) 0.0389(11) -0.0031(8) 0.0041(8) -0.0022(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu S1 2.2474(6) . ? Cu S2 2.2473(6) . ? Cu N11 1.9592(16) . ? Cu N21 1.9654(16) . ? S1 C12 1.7636(19) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C1 C11 1.490(3) . ? S2 C22 1.7671(19) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C2 C21 1.494(2) . ? C11 N11 1.298(2) . ? C11 C21 1.479(3) . ? N11 N12 1.373(2) . ? C12 N12 1.323(2) . ? C12 N13 1.344(2) . ? N13 H13 0.8800 . ? N13 C13 1.462(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? N21 C21 1.303(2) . ? N21 N22 1.369(2) . ? N22 C22 1.329(3) . ? C22 N23 1.341(2) . ? N23 H23 0.8800 . ? N23 C23 1.459(3) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? O1S S1S 1.5200(14) . ? S1S C1S 1.786(2) . ? S1S C2S 1.789(2) . ? C1S H1S1 0.9800 . ? C1S H1S2 0.9800 . ? C1S H1S3 0.9800 . ? C2S H2S1 0.9800 . ? C2S H2S2 0.9800 . ? C2S H2S3 0.9800 . ? 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 S1 Cu S2 109.23(2) . . ? S1 Cu N11 85.07(5) . . ? S1 Cu N21 165.65(5) . . ? S2 Cu N11 165.52(5) . . ? S2 Cu N21 85.12(5) . . ? N11 Cu N21 80.62(6) . . ? Cu S1 C12 94.39(6) . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1A C1 C11 109.5 . . ? H1B C1 H1C 109.5 . . ? H1B C1 C11 109.5 . . ? H1C C1 C11 109.5 . . ? Cu S2 C22 94.34(7) . . ? H2A C2 H2B 109.5 . . ? H2A C2 H2C 109.5 . . ? H2A C2 C21 109.5 . . ? H2B C2 H2C 109.5 . . ? H2B C2 C21 109.5 . . ? H2C C2 C21 109.5 . . ? C1 C11 N11 123.58(18) . . ? C1 C11 C21 122.38(16) . . ? N11 C11 C21 114.04(16) . . ? Cu N11 C11 115.83(13) . . ? Cu N11 N12 123.67(11) . . ? C11 N11 N12 120.49(16) . . ? S1 C12 N12 125.79(14) . . ? S1 C12 N13 116.83(14) . . ? N12 C12 N13 117.34(17) . . ? N11 N12 C12 111.04(15) . . ? C12 N13 H13 119.0 . . ? C12 N13 C13 122.00(16) . . ? H13 N13 C13 119.0 . . ? N13 C13 H13A 109.5 . . ? N13 C13 H13B 109.5 . . ? N13 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? Cu N21 C21 115.38(13) . . ? Cu N21 N22 123.68(12) . . ? C21 N21 N22 120.91(16) . . ? C2 C21 C11 121.90(17) . . ? C2 C21 N21 124.02(18) . . ? C11 C21 N21 114.08(15) . . ? N21 N22 C22 111.01(15) . . ? S2 C22 N22 125.77(15) . . ? S2 C22 N23 116.42(15) . . ? N22 C22 N23 117.81(17) . . ? C22 N23 H23 118.9 . . ? C22 N23 C23 122.18(18) . . ? H23 N23 C23 118.9 . . ? N23 C23 H23A 109.5 . . ? N23 C23 H23B 109.5 . . ? N23 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O1S S1S C1S 105.27(9) . . ? O1S S1S C2S 106.90(9) . . ? C1S S1S C2S 97.86(11) . . ? S1S C1S H1S1 109.5 . . ? S1S C1S H1S2 109.5 . . ? S1S C1S H1S3 109.5 . . ? H1S1 C1S H1S2 109.5 . . ? H1S1 C1S H1S3 109.5 . . ? H1S2 C1S H1S3 109.5 . . ? S1S C2S H2S1 109.5 . . ? S1S C2S H2S2 109.5 . . ? S1S C2S H2S3 109.5 . . ? H2S1 C2S H2S2 109.5 . . ? H2S1 C2S H2S3 109.5 . . ? H2S2 C2S H2S3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S2 Cu S1 C12 -176.22(6) . . . . ? N11 Cu S1 C12 1.39(7) . . . . ? N21 Cu S1 C12 5.6(2) . . . . ? S1 Cu S2 C22 -177.34(6) . . . . ? N11 Cu S2 C22 12.2(2) . . . . ? N21 Cu S2 C22 2.21(7) . . . . ? C1 C11 N11 Cu -179.22(14) . . . . ? C1 C11 N11 N12 0.3(3) . . . . ? C21 C11 N11 Cu 0.7(2) . . . . ? C21 C11 N11 N12 -179.78(14) . . . . ? S1 Cu N11 C11 177.53(13) . . . . ? S1 Cu N11 N12 -1.98(13) . . . . ? S2 Cu N11 C11 -11.5(3) . . . . ? S2 Cu N11 N12 168.96(12) . . . . ? N21 Cu N11 C11 -1.41(13) . . . . ? N21 Cu N11 N12 179.07(14) . . . . ? Cu S1 C12 N12 -1.27(17) . . . . ? Cu S1 C12 N13 176.52(13) . . . . ? S1 C12 N12 N11 0.1(2) . . . . ? N13 C12 N12 N11 -177.69(15) . . . . ? Cu N11 N12 C12 1.6(2) . . . . ? C11 N11 N12 C12 -177.90(16) . . . . ? S1 C12 N13 C13 -176.98(15) . . . . ? N12 C12 N13 C13 1.0(3) . . . . ? S1 Cu N21 C21 -2.3(3) . . . . ? S1 Cu N21 N22 176.11(12) . . . . ? S2 Cu N21 C21 179.44(13) . . . . ? S2 Cu N21 N22 -2.17(13) . . . . ? N11 Cu N21 C21 1.96(13) . . . . ? N11 Cu N21 N22 -179.64(14) . . . . ? Cu N21 C21 C2 177.36(14) . . . . ? Cu N21 C21 C11 -2.1(2) . . . . ? N22 N21 C21 C2 -1.1(3) . . . . ? N22 N21 C21 C11 179.43(15) . . . . ? C1 C11 C21 C2 1.4(3) . . . . ? C1 C11 C21 N21 -179.14(17) . . . . ? N11 C11 C21 C2 -178.55(16) . . . . ? N11 C11 C21 N21 1.0(2) . . . . ? Cu N21 N22 C22 0.7(2) . . . . ? C21 N21 N22 C22 179.06(16) . . . . ? N21 N22 C22 S2 2.0(2) . . . . ? N21 N22 C22 N23 -178.58(15) . . . . ? Cu S2 C22 N22 -3.08(17) . . . . ? Cu S2 C22 N23 177.47(13) . . . . ? S2 C22 N23 C23 179.04(15) . . . . ? N22 C22 N23 C23 -0.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N13 H13 O1S 0.88 2.07 2.945(2) 177.4 . N23 H23 O1S 0.88 2.22 3.072(2) 162.3 2_645 _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.461 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.090 data_CRYSTALS_cif_2 _database_code_CSD 213900 _audit_creation_date 01-13-06 _audit_creation_method CRYSTALS_ver_12-03-99 # arc103 # Check this file using the IUCr facility at: # http://www/iucr.ac.uk/iucr-top/journals/acta/c/services/checkcif.html #========================================================================== # 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 'not measured' _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens difmap # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment refall #**************************************************************************** _cell_length_a 8.3300(2) _cell_angle_alpha 90 _cell_length_b 13.0822(3) _cell_angle_beta 101.3738(9) _cell_length_c 16.2402(5) _cell_angle_gamma 90 _cell_volume 1735.0 _symmetry_cell_setting 'Monoclinic ' _symmetry_space_group_name_H-M 'P 1 21/n 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-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 'Cu ' 0.2630 1.2660 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 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 _chemical_formula_sum ' C11 H21 Cu1 N7 O1 S2 ' _chemical_formula_moiety ' C11 H21 Cu1 N7 O1 S2 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 395.00 _cell_measurement_reflns_used 45757 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _cell_formula_units_Z 4 _exptl_crystal_description ' fragment ' _exptl_crystal_colour ' orange-brown ' _exptl_crystal_size_min 0.14 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_max 0.35 _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 821.937 _exptl_absorpt_coefficient_mu 1.511 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.72 _exptl_absorpt_correction_T_max 0.81 _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 12576 _reflns_number_total 4137 _diffrn_reflns_av_R_equivalents 0.02 _diffrn_measured_fraction_theta_max 0.99 _reflns_number_gt 3321 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 27.87 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _refine_diff_density_min -0.32 _refine_diff_density_max 0.70 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 3321 _refine_ls_number_parameters 200 _refine_ls_R_factor_gt 0.0256 _refine_ls_wR_factor_ref 0.0285 _refine_ls_goodness_of_fit_ref 1.0364 _refine_ls_shift/su_max 0.001251 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters, Carruthers & Watkin , 1979, 3.21 -1.49 2.08 ; _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 Cu1 0.32182(2) 0.416924(14) 0.560618(11) 0.0170 1.0000 Uani S1 0.29681(5) 0.41984(3) 0.69522(2) 0.0236 1.0000 Uani S2 0.45118(5) 0.27285(3) 0.53590(3) 0.0244 1.0000 Uani O1 0.19170(18) 0.46790(11) 0.92266(8) 0.0356 1.0000 Uani N1 0.13340(16) 0.5861(1) 0.61464(8) 0.0205 1.0000 Uani N2 0.19466(16) 0.5439(1) 0.55027(8) 0.0184 1.0000 Uani N3 0.12622(18) 0.56440(11) 0.75335(9) 0.0252 1.0000 Uani N4 0.39029(16) 0.38758(11) 0.39093(8) 0.0210 1.0000 Uani N5 0.32056(16) 0.4489(1) 0.44248(8) 0.0182 1.0000 Uani N6 0.52673(18) 0.23746(12) 0.3871(1) 0.0277 1.0000 Uani N7 0.30005(19) 0.53545(12) 1.05123(9) 0.0284 1.0000 Uani C1 0.17685(19) 0.53172(12) 0.6842(1) 0.0201 1.0000 Uani C2 0.17483(18) 0.58883(12) 0.4776(1) 0.0190 1.0000 Uani C3 0.0242(2) 0.65510(14) 0.75211(11) 0.0300 1.0000 Uani C4 0.0884(2) 0.68855(14) 0.45894(11) 0.0269 1.0000 Uani C5 0.45397(19) 0.30439(13) 0.4310(1) 0.0213 1.0000 Uani C6 0.24756(18) 0.53314(12) 0.41473(9) 0.0187 1.0000 Uani C7 0.5373(2) 0.25673(15) 0.30029(12) 0.0308 1.0000 Uani C8 0.2364(2) 0.57139(13) 0.3273(1) 0.0237 1.0000 Uani C9 0.2710(2) 0.53344(15) 0.96815(12) 0.0311 1.0000 Uani C10 0.2294(3) 0.46049(17) 1.09920(14) 0.0463 1.0000 Uani C11 0.3879(3) 0.61995(18) 1.09912(13) 0.0423 1.0000 Uani H3 0.1549(3) 0.5252(3) 0.8011(3) 0.0495(3) 1.0000 Uiso H6 0.5799(3) 0.1782(3) 0.4157(3) 0.0495(3) 1.0000 Uiso H31 0.0056(3) 0.6677(3) 0.8022(3) 0.0495(3) 1.0000 Uiso H32 0.0881(3) 0.7143(3) 0.7345(3) 0.0495(3) 1.0000 Uiso H33 -0.0865(3) 0.6457(3) 0.7140(3) 0.0495(3) 1.0000 Uiso H41 0.0067(3) 0.6830(3) 0.4082(3) 0.0495(3) 1.0000 Uiso H42 0.1442(3) 0.7386(3) 0.4951(3) 0.0495(3) 1.0000 Uiso H43 0.0038(3) 0.6930(3) 0.4832(3) 0.0495(3) 1.0000 Uiso H71 0.5924(3) 0.1966(3) 0.2830(3) 0.0495(3) 1.0000 Uiso H72 0.5935(3) 0.3175(3) 0.2945(3) 0.0495(3) 1.0000 Uiso H73 0.4245(3) 0.2582(3) 0.2628(3) 0.0495(3) 1.0000 Uiso H81 0.3103(3) 0.5393(3) 0.3017(3) 0.0495(3) 1.0000 Uiso H82 0.2649(3) 0.6443(3) 0.3278(3) 0.0495(3) 1.0000 Uiso H83 0.1299(3) 0.5661(3) 0.2917(3) 0.0495(3) 1.0000 Uiso H91 0.3320(3) 0.5918(3) 0.9445(3) 0.0495(3) 1.0000 Uiso H101 0.1406(3) 0.4973(3) 1.1284(3) 0.0495(3) 1.0000 Uiso H102 0.1970(3) 0.4011(3) 1.0730(3) 0.0495(3) 1.0000 Uiso H103 0.3113(3) 0.4280(3) 1.1449(3) 0.0495(3) 1.0000 Uiso H111 0.4049(3) 0.6784(3) 1.0611(3) 0.0495(3) 1.0000 Uiso H112 0.4803(3) 0.6045(3) 1.1409(3) 0.0495(3) 1.0000 Uiso H113 0.3081(3) 0.6532(3) 1.1338(3) 0.0495(3) 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 Cu1 0.0186(1) 0.0186(1) 0.0140(1) 0.00184(7) 0.00363(6) -0.00032(7) S1 0.0290(2) 0.0266(2) 0.01591(18) 0.00469(15) 0.00624(15) 0.00154(16) S2 0.0309(2) 0.02043(19) 0.0222(2) 0.00257(15) 0.00601(16) 0.00416(15) O1 0.0525(9) 0.0331(7) 0.0213(6) -0.0025(5) 0.0073(6) -0.0020(6) N1 0.0224(6) 0.0229(7) 0.0167(6) -0.0036(5) 0.0050(5) -0.0012(5) N2 0.0191(6) 0.0206(6) 0.0152(6) -0.0009(5) 0.0027(5) -0.0018(5) N3 0.0320(7) 0.0286(7) 0.0163(7) -0.0028(5) 0.0076(5) -0.0038(6) N4 0.0223(6) 0.0239(7) 0.0178(6) -0.0023(5) 0.0061(5) 0.0007(5) N5 0.0182(6) 0.0219(6) 0.0142(6) -0.0000(5) 0.0022(5) -0.0008(5) N6 0.0292(7) 0.0270(7) 0.0279(8) -0.0058(6) 0.0082(6) 0.0027(6) N7 0.0320(8) 0.0267(8) 0.0254(7) 0.0021(6) 0.0032(6) -0.0018(6) C1 0.0199(7) 0.0233(8) 0.0173(7) -0.0028(6) 0.0039(6) -0.0072(6) C2 0.0172(7) 0.0213(8) 0.0172(7) -0.0001(6) 0.0005(5) -0.0007(6) C3 0.040(1) 0.0285(9) 0.0246(9) -0.0086(7) 0.0128(7) -0.0019(7) C4 0.0302(9) 0.0268(9) 0.0225(8) 0.0023(6) 0.0024(7) 0.0075(7) C5 0.0190(7) 0.0226(8) 0.0223(7) -0.0036(6) 0.0044(6) -0.0031(6) C6 0.0180(7) 0.0224(8) 0.0147(7) -0.0001(6) 0.0006(5) -0.0030(6) C7 0.0321(9) 0.035(1) 0.0272(9) -0.0130(7) 0.0106(7) -0.0050(7) C8 0.0275(8) 0.0280(8) 0.0146(7) 0.0025(6) 0.0018(6) 0.0016(7) C9 0.0347(9) 0.033(1) 0.0257(9) 0.0042(7) 0.0074(7) -0.0007(8) C10 0.0752(16) 0.0360(11) 0.029(1) -0.0013(8) 0.013(1) -0.0163(11) C11 0.0451(12) 0.0447(12) 0.032(1) -0.0006(9) -0.0062(9) -0.0145(9) _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 Cu1 . S1 . 2.2367(4) yes Cu1 . S2 . 2.2462(4) yes Cu1 . N2 . 1.9590(14) yes Cu1 . N5 . 1.9616(13) yes S1 . C1 . 1.7613(17) yes S2 . C5 . 1.7580(17) yes O1 . C9 . 1.235(2) yes N1 . N2 . 1.3673(18) yes N1 . C1 . 1.324(2) yes N2 . C2 . 1.299(2) yes N3 . C1 . 1.344(2) yes N3 . C3 . 1.457(2) yes N3 . H3 . 0.921(2) no N4 . N5 . 1.3687(19) yes N4 . C5 . 1.324(2) yes N5 . C6 . 1.296(2) yes N6 . C5 . 1.346(2) yes N6 . C7 . 1.451(2) yes N6 . H6 . 0.9658(16) no N7 . C9 . 1.323(2) yes N7 . C10 . 1.448(3) yes N7 . C11 . 1.462(3) yes C2 . C4 . 1.492(2) yes C2 . C6 . 1.478(2) yes C3 . H31 . 0.874(5) no C3 . H32 . 1.012(3) no C3 . H33 . 1.012(5) no C4 . H41 . 0.963(5) no C4 . H42 . 0.940(6) no C4 . H43 . 0.874(2) no C6 . C8 . 1.490(2) yes C7 . H71 . 0.979(4) no C7 . H72 . 0.936(4) no C7 . H73 . 1.014(4) no C8 . H81 . 0.911(3) no C8 . H82 . 0.983(4) no C8 . H83 . 0.962(4) no C9 . H91 . 1.032(3) no C10 . H101 . 1.069(4) no C10 . H102 . 0.901(6) no C10 . H103 . 0.999(4) no C11 . H111 . 1.011(2) no C11 . H112 . 0.942(4) no C11 . H113 . 1.046(4) 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 . Cu1 . S2 . 109.234(17) yes S1 . Cu1 . N2 . 85.20(4) yes S2 . Cu1 . N2 . 165.08(4) yes S1 . Cu1 . N5 . 165.62(4) yes S2 . Cu1 . N5 . 85.08(4) yes N2 . Cu1 . N5 . 80.62(5) yes Cu1 . S1 . C1 . 94.33(5) yes Cu1 . S2 . C5 . 94.30(6) yes N2 . N1 . C1 . 110.76(13) yes Cu1 . N2 . N1 . 123.7(1) yes Cu1 . N2 . C2 . 115.56(11) yes N1 . N2 . C2 . 120.74(14) yes C1 . N3 . C3 . 121.70(14) yes C1 . N3 . H3 . 117.0(3) no C3 . N3 . H3 . 121.2(3) no N5 . N4 . C5 . 111.02(13) yes Cu1 . N5 . N4 . 123.5(1) yes Cu1 . N5 . C6 . 115.66(11) yes N4 . N5 . C6 . 120.81(13) yes C5 . N6 . C7 . 121.41(15) yes C5 . N6 . H6 . 118.6(3) no C7 . N6 . H6 . 119.8(3) no C9 . N7 . C10 . 121.57(16) yes C9 . N7 . C11 . 121.94(16) yes C10 . N7 . C11 . 116.08(16) yes S1 . C1 . N1 . 125.97(12) yes S1 . C1 . N3 . 116.41(12) yes N1 . C1 . N3 . 117.62(15) yes N2 . C2 . C4 . 123.40(15) yes N2 . C2 . C6 . 114.09(14) yes C4 . C2 . C6 . 122.50(14) yes N3 . C3 . H31 . 110.55(19) no N3 . C3 . H32 . 106.83(18) no H31 . C3 . H32 . 108.5(6) no N3 . C3 . H33 . 111.6(3) no H31 . C3 . H33 . 106.58(19) no H32 . C3 . H33 . 112.8(2) no C2 . C4 . H41 . 109.8(3) no C2 . C4 . H42 . 108.85(15) no H41 . C4 . H42 . 140.1(3) no C2 . C4 . H43 . 111.43(19) no H41 . C4 . H43 . 83.9(3) no H42 . C4 . H43 . 90.9(5) no S2 . C5 . N4 . 126.04(12) yes S2 . C5 . N6 . 117.02(13) yes N4 . C5 . N6 . 116.94(15) yes N5 . C6 . C2 . 114.01(13) yes N5 . C6 . C8 . 123.61(14) yes C2 . C6 . C8 . 122.38(14) yes N6 . C7 . H71 . 105.1(2) no N6 . C7 . H72 . 111.8(3) no H71 . C7 . H72 . 112.45(18) no N6 . C7 . H73 . 111.1(2) no H71 . C7 . H73 . 105.9(6) no H72 . C7 . H73 . 110.3(2) no C6 . C8 . H81 . 111.1(2) no C6 . C8 . H82 . 110.4(3) no H81 . C8 . H82 . 105.5(2) no C6 . C8 . H83 . 115.26(17) no H81 . C8 . H83 . 108.5(6) no H82 . C8 . H83 . 105.47(16) no O1 . C9 . N7 . 126.32(17) yes O1 . C9 . H91 . 122.4(4) no N7 . C9 . H91 . 111.1(4) no N7 . C10 . H101 . 108.9(2) no N7 . C10 . H102 . 116.4(2) no H101 . C10 . H102 . 115.4(4) no N7 . C10 . H103 . 113.5(2) no H101 . C10 . H103 . 107.0(4) no H102 . C10 . H103 . 94.6(3) no N7 . C11 . H111 . 111.3(4) no N7 . C11 . H112 . 118.3(4) no H111 . C11 . H112 . 114.1(4) no N7 . C11 . H113 . 107.2(3) no H111 . C11 . H113 . 101.2(3) no H112 . C11 . H113 . 102.5(5) no data_kent4 _database_code_CSD 213901 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H18 Cu N6 S2' _chemical_formula_weight 349.96 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' Cu Cu 0.3201 1.2651 '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 7.3791(3) _cell_length_b 8.5020(4) _cell_length_c 11.9417(5) _cell_angle_alpha 104.281(2) _cell_angle_beta 97.775(2) _cell_angle_gamma 90.630(2) _cell_volume 718.59(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3649 _cell_measurement_theta_min 5.42 _cell_measurement_theta_max 58.27 _exptl_crystal_description block _exptl_crystal_colour red/orange _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.617 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 362 _exptl_absorpt_coefficient_mu 1.806 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.83 _exptl_absorpt_correction_T_max 0.95 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6904 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS Station 9.8' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_measurement_device_type 'Bruker AXS SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 15 _diffrn_reflns_number 4988 _diffrn_reflns_av_R_equivalents 0.0068 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 29.13 _reflns_number_total 3625 _reflns_number_gt 3055 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS SMART' _computing_cell_refinement 'Bruker AXS SAINT v6.02a' _computing_data_reduction 'Bruker AXS SAINT' _computing_structure_solution 'Bruker AXS SHELXTL' _computing_structure_refinement 'Bruker AXS SHELXTL' _computing_molecular_graphics 'Bruker AXS SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0800P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3625 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0451 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1061 _refine_ls_wR_factor_gt 0.1048 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 Cu Cu 0.28916(3) 0.57615(3) 0.88512(2) 0.02044(10) Uani 1 1 d . . . S1 S 0.29036(8) 0.60422(7) 0.70351(5) 0.02683(14) Uani 1 1 d . . . S2 S 0.39089(8) 0.81228(7) 1.01289(5) 0.02415(14) Uani 1 1 d . . . C1 C 0.0671(3) 0.0998(3) 0.8404(2) 0.0284(5) Uani 1 1 d . . . H1A H 0.0361 0.0692 0.7552 0.034 Uiso 1 1 calc R . . H1B H -0.0438 0.0928 0.8761 0.034 Uiso 1 1 calc R . . H1C H 0.1565 0.0259 0.8646 0.034 Uiso 1 1 calc R . . C2 C 0.1676(4) 0.2709(3) 1.0984(2) 0.0290(5) Uani 1 1 d . . . H2A H 0.2459 0.3267 1.1706 0.035 Uiso 1 1 calc R . . H2B H 0.2017 0.1576 1.0747 0.035 Uiso 1 1 calc R . . H2C H 0.0393 0.2739 1.1116 0.035 Uiso 1 1 calc R . . C11 C 0.1467(3) 0.2691(3) 0.87890(19) 0.0216(4) Uani 1 1 d . . . N11 N 0.1838(3) 0.3564(2) 0.80891(17) 0.0221(4) Uani 1 1 d . . . N12 N 0.1514(3) 0.2961(2) 0.69024(17) 0.0235(4) Uani 1 1 d . . . C12 C 0.1994(3) 0.4046(3) 0.6350(2) 0.0229(4) Uani 1 1 d . . . N13 N 0.1743(3) 0.3575(3) 0.51757(18) 0.0287(4) Uani 1 1 d . . . C13 C 0.0972(4) 0.1950(3) 0.4588(2) 0.0357(6) Uani 1 1 d . . . H13A H 0.1843 0.1144 0.4748 0.043 Uiso 1 1 calc R . . H13B H 0.0730 0.1845 0.3745 0.043 Uiso 1 1 calc R . . H13C H -0.0174 0.1769 0.4876 0.043 Uiso 1 1 calc R . . C14 C 0.2345(4) 0.4533(3) 0.4427(2) 0.0316(5) Uani 1 1 d . . . H14A H 0.2593 0.5665 0.4874 0.038 Uiso 1 1 calc R . . H14B H 0.1383 0.4486 0.3766 0.038 Uiso 1 1 calc R . . H14C H 0.3463 0.4095 0.4136 0.038 Uiso 1 1 calc R . . C21 C 0.1917(3) 0.3537(3) 1.0043(2) 0.0216(4) Uani 1 1 d . . . N21 N 0.2546(3) 0.5020(2) 1.02386(17) 0.0220(4) Uani 1 1 d . . . C22 C 0.3670(3) 0.7417(3) 1.1372(2) 0.0215(4) Uani 1 1 d . . . N22 N 0.3037(3) 0.5945(2) 1.13556(17) 0.0235(4) Uani 1 1 d . . . N23 N 0.4151(3) 0.8435(2) 1.24444(18) 0.0264(4) Uani 1 1 d . . . C23 C 0.3834(4) 0.7878(3) 1.3469(2) 0.0310(5) Uani 1 1 d . . . H23A H 0.2515 0.7755 1.3477 0.037 Uiso 1 1 calc R . . H23B H 0.4386 0.8676 1.4178 0.037 Uiso 1 1 calc R . . H23C H 0.4391 0.6830 1.3439 0.037 Uiso 1 1 calc R . . C24 C 0.4970(4) 1.0055(3) 1.2645(2) 0.0335(6) Uani 1 1 d . . . H24A H 0.5147 1.0268 1.1896 0.040 Uiso 1 1 calc R . . H24B H 0.6156 1.0140 1.3142 0.040 Uiso 1 1 calc R . . H24C H 0.4160 1.0853 1.3032 0.040 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 Cu 0.02286(15) 0.01986(16) 0.02046(16) 0.00873(11) 0.00282(10) -0.00040(10) S1 0.0337(3) 0.0258(3) 0.0226(3) 0.0095(2) 0.0035(2) -0.0028(2) S2 0.0294(3) 0.0199(3) 0.0255(3) 0.0090(2) 0.0061(2) -0.0008(2) C1 0.0343(12) 0.0220(11) 0.0294(12) 0.0074(9) 0.0042(9) -0.0034(9) C2 0.0372(12) 0.0281(12) 0.0254(11) 0.0120(9) 0.0083(9) -0.0036(10) C11 0.0202(9) 0.0217(10) 0.0238(11) 0.0075(8) 0.0030(8) 0.0003(8) N11 0.0228(8) 0.0223(9) 0.0218(9) 0.0076(7) 0.0019(7) 0.0001(7) N12 0.0270(9) 0.0240(10) 0.0189(9) 0.0050(7) 0.0022(7) -0.0003(7) C12 0.0229(10) 0.0229(11) 0.0234(11) 0.0066(9) 0.0037(8) 0.0016(8) N13 0.0360(11) 0.0287(11) 0.0213(9) 0.0062(8) 0.0046(8) -0.0017(9) C13 0.0468(15) 0.0299(13) 0.0266(12) 0.0009(10) 0.0035(10) -0.0019(11) C14 0.0355(13) 0.0376(15) 0.0243(12) 0.0121(10) 0.0051(10) 0.0010(11) C21 0.0221(10) 0.0207(11) 0.0241(10) 0.0086(8) 0.0053(8) 0.0011(8) N21 0.0233(9) 0.0211(9) 0.0227(9) 0.0086(7) 0.0013(7) -0.0014(7) C22 0.0206(9) 0.0214(11) 0.0244(11) 0.0089(8) 0.0039(8) 0.0018(8) N22 0.0296(9) 0.0199(9) 0.0217(9) 0.0072(7) 0.0026(7) -0.0015(8) N23 0.0320(10) 0.0215(10) 0.0254(10) 0.0061(8) 0.0031(8) -0.0025(8) C23 0.0404(13) 0.0312(13) 0.0211(11) 0.0062(9) 0.0043(9) -0.0017(11) C24 0.0417(14) 0.0249(12) 0.0323(13) 0.0019(10) 0.0098(11) -0.0044(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N21 1.9580(19) . ? Cu N11 1.965(2) . ? Cu S1 2.2408(6) . ? Cu S2 2.2511(7) . ? S1 C12 1.772(2) . ? S2 C22 1.762(2) . ? C1 C11 1.487(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C21 1.494(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C11 N11 1.299(3) . ? C11 C21 1.483(3) . ? N11 N12 1.369(3) . ? N12 C12 1.330(3) . ? C12 N13 1.347(3) . ? N13 C14 1.456(3) . ? N13 C13 1.456(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C21 N21 1.293(3) . ? N21 N22 1.369(3) . ? C22 N22 1.325(3) . ? C22 N23 1.356(3) . ? N23 C24 1.449(3) . ? N23 C23 1.462(3) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 N21 Cu N11 80.68(8) . . ? N21 Cu S1 165.99(6) . . ? N11 Cu S1 85.44(6) . . ? N21 Cu S2 85.02(6) . . ? N11 Cu S2 165.55(6) . . ? S1 Cu S2 108.77(2) . . ? C12 S1 Cu 94.46(8) . . ? C22 S2 Cu 94.53(8) . . ? C11 C1 H1A 109.5 . . ? C11 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C11 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C21 C2 H2A 109.5 . . ? C21 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C21 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N11 C11 C21 113.7(2) . . ? N11 C11 C1 124.6(2) . . ? C21 C11 C1 121.6(2) . . ? C11 N11 N12 121.2(2) . . ? C11 N11 Cu 115.51(16) . . ? N12 N11 Cu 123.30(15) . . ? C12 N12 N11 111.48(19) . . ? N12 C12 N13 116.5(2) . . ? N12 C12 S1 125.31(18) . . ? N13 C12 S1 118.23(18) . . ? C12 N13 C14 124.3(2) . . ? C12 N13 C13 119.5(2) . . ? C14 N13 C13 116.0(2) . . ? N13 C13 H13A 109.5 . . ? N13 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N13 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N13 C14 H14A 109.5 . . ? N13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N21 C21 C11 114.4(2) . . ? N21 C21 C2 123.8(2) . . ? C11 C21 C2 121.8(2) . . ? C21 N21 N22 120.8(2) . . ? C21 N21 Cu 115.61(16) . . ? N22 N21 Cu 123.45(15) . . ? N22 C22 N23 115.9(2) . . ? N22 C22 S2 125.23(18) . . ? N23 C22 S2 118.88(18) . . ? C22 N22 N21 111.67(19) . . ? C22 N23 C24 124.1(2) . . ? C22 N23 C23 118.5(2) . . ? C24 N23 C23 117.4(2) . . ? N23 C23 H23A 109.5 . . ? N23 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N23 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N23 C24 H24A 109.5 . . ? N23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N21 Cu S1 C12 -9.0(3) . . . . ? N11 Cu S1 C12 -1.04(9) . . . . ? S2 Cu S1 C12 -178.37(7) . . . . ? N21 Cu S2 C22 2.00(9) . . . . ? N11 Cu S2 C22 10.2(2) . . . . ? S1 Cu S2 C22 179.43(7) . . . . ? C21 C11 N11 N12 179.63(18) . . . . ? C1 C11 N11 N12 -0.3(3) . . . . ? C21 C11 N11 Cu 0.1(2) . . . . ? C1 C11 N11 Cu -179.82(17) . . . . ? N21 Cu N11 C11 -1.40(16) . . . . ? S1 Cu N11 C11 -179.46(16) . . . . ? S2 Cu N11 C11 -9.6(3) . . . . ? N21 Cu N11 N12 179.03(18) . . . . ? S1 Cu N11 N12 0.98(16) . . . . ? S2 Cu N11 N12 170.79(15) . . . . ? C11 N11 N12 C12 -179.81(19) . . . . ? Cu N11 N12 C12 -0.3(3) . . . . ? N11 N12 C12 N13 179.64(19) . . . . ? N11 N12 C12 S1 -1.0(3) . . . . ? Cu S1 C12 N12 1.5(2) . . . . ? Cu S1 C12 N13 -179.16(18) . . . . ? N12 C12 N13 C14 -173.9(2) . . . . ? S1 C12 N13 C14 6.7(3) . . . . ? N12 C12 N13 C13 0.3(3) . . . . ? S1 C12 N13 C13 -179.11(18) . . . . ? N11 C11 C21 N21 2.2(3) . . . . ? C1 C11 C21 N21 -177.92(19) . . . . ? N11 C11 C21 C2 -177.0(2) . . . . ? C1 C11 C21 C2 2.9(3) . . . . ? C11 C21 N21 N22 -179.35(18) . . . . ? C2 C21 N21 N22 -0.2(3) . . . . ? C11 C21 N21 Cu -3.4(2) . . . . ? C2 C21 N21 Cu 175.77(17) . . . . ? N11 Cu N21 C21 2.70(16) . . . . ? S1 Cu N21 C21 10.7(4) . . . . ? S2 Cu N21 C21 -179.36(16) . . . . ? N11 Cu N21 N22 178.55(18) . . . . ? S1 Cu N21 N22 -173.42(15) . . . . ? S2 Cu N21 N22 -3.51(17) . . . . ? Cu S2 C22 N22 -1.1(2) . . . . ? Cu S2 C22 N23 179.27(17) . . . . ? N23 C22 N22 N21 178.52(18) . . . . ? S2 C22 N22 N21 -1.1(3) . . . . ? C21 N21 N22 C22 179.14(19) . . . . ? Cu N21 N22 C22 3.5(3) . . . . ? N22 C22 N23 C24 176.2(2) . . . . ? S2 C22 N23 C24 -4.1(3) . . . . ? N22 C22 N23 C23 -3.7(3) . . . . ? S2 C22 N23 C23 175.96(17) . . . . ? _diffrn_measured_fraction_theta_max 0.859 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.629 _refine_diff_density_min -0.492 _refine_diff_density_rms 0.161 data_kent6 _database_code_CSD 213902 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H12 Cu N6 S2' _chemical_formula_weight 307.89 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' Cu Cu 0.3201 1.2651 '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 17.878(7) _cell_length_b 16.856(6) _cell_length_c 7.978(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.930(6) _cell_angle_gamma 90.00 _cell_volume 2343.2(15) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5783 _cell_measurement_theta_min 4.54 _cell_measurement_theta_max 58.28 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.745 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 2.202 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.76 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6904 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS Station 9.8' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_measurement_device_type 'Bruker AXS SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 10 _diffrn_reflns_number 9121 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2248 _reflns_number_gt 1694 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS SMART' _computing_cell_refinement 'Bruker AXS SAINT v6.02a' _computing_data_reduction 'Bruker AXS SAINT' _computing_structure_solution 'Bruker AXS SHELXTL' _computing_structure_refinement 'Bruker AXS SHELXTL' _computing_molecular_graphics 'Bruker AXS SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0712P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2248 _refine_ls_number_parameters 147 _refine_ls_number_restraints 93 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.960 _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 Cu Cu 0.27233(3) 0.16903(3) 0.83771(6) 0.02548(19) Uani 1 1 d U . . S1 S 0.19093(7) 0.21245(8) 0.60078(14) 0.0331(3) Uani 1 1 d U . . S2 S 0.39171(6) 0.16964(8) 0.79150(14) 0.0317(3) Uani 1 1 d U . . C1 C 0.1290(3) 0.0983(3) 1.1690(6) 0.0395(13) Uani 1 1 d . . . H1A H 0.1485 0.0996 1.2953 0.047 Uiso 1 1 calc R . . H1B H 0.0867 0.1373 1.1386 0.047 Uiso 1 1 calc R . . C1A C 0.0993(4) 0.0171(5) 1.1153(9) 0.073(2) Uani 1 1 d . . . H1A1 H 0.0814 0.0154 0.9899 0.110 Uiso 1 1 calc R . . H1A2 H 0.0565 0.0046 1.1692 0.110 Uiso 1 1 calc R . . H1A3 H 0.1404 -0.0218 1.1515 0.110 Uiso 1 1 calc R . . C2 C 0.2988(3) 0.0593(4) 1.3286(7) 0.0527(16) Uani 1 1 d . . . H2A H 0.3447 0.0278 1.3278 0.079 Uiso 1 1 calc R . . H2B H 0.2575 0.0243 1.3463 0.079 Uiso 1 1 calc R . . H2C H 0.3104 0.0983 1.4220 0.079 Uiso 1 1 calc R . . C11 C 0.1920(3) 0.1203(3) 1.0821(6) 0.0300(10) Uani 1 1 d U . . N11 N 0.1797(2) 0.1516(2) 0.9278(5) 0.0281(8) Uani 1 1 d U . . N12 N 0.1069(2) 0.1665(2) 0.8333(5) 0.0276(8) Uani 1 1 d U . . C12 C 0.1082(3) 0.1924(3) 0.6767(6) 0.0270(10) Uani 1 1 d U . . N13 N 0.0414(2) 0.2026(3) 0.5658(5) 0.0357(10) Uani 1 1 d U . . H13A H -0.0018 0.1922 0.5971 0.043 Uiso 1 1 calc R . . H13B H 0.0403 0.2197 0.4611 0.043 Uiso 1 1 calc R . . C21 C 0.2735(3) 0.1021(3) 1.1580(6) 0.0347(11) Uani 1 1 d U . . N21 N 0.3203(2) 0.1212(2) 1.0620(5) 0.0292(8) Uani 1 1 d U . . N22 N 0.3974(2) 0.1046(2) 1.1115(5) 0.0320(9) Uani 1 1 d U . . C22 C 0.4337(3) 0.1235(3) 0.9885(5) 0.0283(10) Uani 1 1 d U . . N23 N 0.5082(2) 0.1069(2) 1.0177(5) 0.0349(10) Uani 1 1 d U . . H23A H 0.5313 0.0843 1.1151 0.042 Uiso 1 1 calc R . . H23B H 0.5344 0.1184 0.9398 0.042 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.0213(3) 0.0478(4) 0.0083(3) 0.0016(2) 0.00538(19) -0.0013(3) S1 0.0232(6) 0.0638(8) 0.0131(5) 0.0102(5) 0.0059(4) -0.0024(6) S2 0.0227(6) 0.0618(8) 0.0115(5) 0.0044(5) 0.0057(4) -0.0005(6) C1 0.028(3) 0.072(4) 0.021(2) 0.011(2) 0.012(2) 0.001(2) C1A 0.073(5) 0.111(6) 0.041(4) 0.003(4) 0.025(4) -0.028(4) C2 0.033(3) 0.102(5) 0.024(3) 0.022(3) 0.007(2) 0.001(3) C11 0.027(2) 0.051(3) 0.014(2) 0.0048(19) 0.0078(18) 0.001(2) N11 0.0226(18) 0.046(2) 0.0168(18) 0.0028(15) 0.0073(15) 0.0016(16) N12 0.0240(18) 0.043(2) 0.0166(18) 0.0031(16) 0.0068(14) 0.0030(17) C12 0.024(2) 0.040(3) 0.019(2) 0.0023(18) 0.0098(18) 0.0002(18) N13 0.022(2) 0.068(3) 0.017(2) 0.0122(19) 0.0059(16) 0.0003(19) C21 0.028(2) 0.060(3) 0.018(2) 0.006(2) 0.0068(18) 0.002(2) N21 0.027(2) 0.049(2) 0.0130(17) 0.0016(16) 0.0068(15) -0.0026(17) N22 0.023(2) 0.056(2) 0.0159(18) 0.0049(17) 0.0040(15) 0.0003(17) C22 0.023(2) 0.049(3) 0.012(2) -0.0022(19) 0.0020(17) -0.003(2) N23 0.026(2) 0.067(3) 0.0134(19) 0.0064(18) 0.0068(16) -0.0017(19) _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 Cu N11 1.969(4) . ? Cu N21 1.975(4) . ? Cu S1 2.2350(14) . ? Cu S2 2.2458(15) . ? S1 C12 1.753(5) . ? S2 C22 1.764(5) . ? C1 C1A 1.495(9) . ? C1 C11 1.496(6) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? C2 C21 1.517(7) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C11 N11 1.312(6) . ? C11 C21 1.480(7) . ? N11 N12 1.374(5) . ? N12 C12 1.329(6) . ? C12 N13 1.329(6) . ? N13 H13A 0.8800 . ? N13 H13B 0.8800 . ? C21 N21 1.295(6) . ? N21 N22 1.373(5) . ? N22 C22 1.331(6) . ? C22 N23 1.329(6) . ? N23 H23A 0.8800 . ? N23 H23B 0.8800 . ? 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 N11 Cu N21 80.72(15) . . ? N11 Cu S1 85.20(12) . . ? N21 Cu S1 165.60(12) . . ? N11 Cu S2 165.52(11) . . ? N21 Cu S2 85.08(11) . . ? S1 Cu S2 108.81(5) . . ? C12 S1 Cu 94.87(16) . . ? C22 S2 Cu 94.74(15) . . ? C1A C1 C11 110.5(5) . . ? C1A C1 H1A 109.5 . . ? C11 C1 H1A 109.5 . . ? C1A C1 H1B 109.5 . . ? C11 C1 H1B 109.5 . . ? H1A C1 H1B 108.1 . . ? C1 C1A H1A1 109.5 . . ? C1 C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? C1 C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? C21 C2 H2A 109.5 . . ? C21 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C21 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N11 C11 C21 114.2(4) . . ? N11 C11 C1 123.3(4) . . ? C21 C11 C1 122.3(4) . . ? C11 N11 N12 121.8(4) . . ? C11 N11 Cu 115.2(3) . . ? N12 N11 Cu 122.9(3) . . ? C12 N12 N11 111.3(4) . . ? N13 C12 N12 117.8(4) . . ? N13 C12 S1 116.6(3) . . ? N12 C12 S1 125.6(4) . . ? C12 N13 H13A 120.0 . . ? C12 N13 H13B 120.0 . . ? H13A N13 H13B 120.0 . . ? N21 C21 C11 114.5(4) . . ? N21 C21 C2 123.1(5) . . ? C11 C21 C2 122.2(4) . . ? C21 N21 N22 121.2(4) . . ? C21 N21 Cu 115.4(3) . . ? N22 N21 Cu 123.2(3) . . ? C22 N22 N21 111.3(4) . . ? N23 C22 N22 117.1(4) . . ? N23 C22 S2 117.4(3) . . ? N22 C22 S2 125.5(4) . . ? C22 N23 H23A 120.0 . . ? C22 N23 H23B 120.0 . . ? H23A N23 H23B 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N11 Cu S1 C12 -2.70(19) . . . . ? N21 Cu S1 C12 9.2(5) . . . . ? S2 Cu S1 C12 173.54(16) . . . . ? N11 Cu S2 C22 -9.2(5) . . . . ? N21 Cu S2 C22 2.09(19) . . . . ? S1 Cu S2 C22 -174.04(16) . . . . ? C1A C1 C11 N11 85.0(6) . . . . ? C1A C1 C11 C21 -89.6(6) . . . . ? C21 C11 N11 N12 174.9(4) . . . . ? C1 C11 N11 N12 0.0(7) . . . . ? C21 C11 N11 Cu -1.5(5) . . . . ? C1 C11 N11 Cu -176.5(4) . . . . ? N21 Cu N11 C11 1.0(3) . . . . ? S1 Cu N11 C11 178.0(3) . . . . ? S2 Cu N11 C11 12.4(7) . . . . ? N21 Cu N11 N12 -175.4(4) . . . . ? S1 Cu N11 N12 1.6(3) . . . . ? S2 Cu N11 N12 -164.0(3) . . . . ? C11 N11 N12 C12 -175.3(4) . . . . ? Cu N11 N12 C12 0.9(5) . . . . ? N11 N12 C12 N13 174.2(4) . . . . ? N11 N12 C12 S1 -4.2(6) . . . . ? Cu S1 C12 N13 -173.6(4) . . . . ? Cu S1 C12 N12 4.8(4) . . . . ? N11 C11 C21 N21 1.3(7) . . . . ? C1 C11 C21 N21 176.3(5) . . . . ? N11 C11 C21 C2 -174.7(5) . . . . ? C1 C11 C21 C2 0.4(8) . . . . ? C11 C21 N21 N22 -177.0(4) . . . . ? C2 C21 N21 N22 -1.0(8) . . . . ? C11 C21 N21 Cu -0.5(6) . . . . ? C2 C21 N21 Cu 175.4(4) . . . . ? N11 Cu N21 C21 -0.2(4) . . . . ? S1 Cu N21 C21 -12.3(8) . . . . ? S2 Cu N21 C21 -177.4(4) . . . . ? N11 Cu N21 N22 176.2(4) . . . . ? S1 Cu N21 N22 164.1(3) . . . . ? S2 Cu N21 N22 -1.0(3) . . . . ? C21 N21 N22 C22 175.0(5) . . . . ? Cu N21 N22 C22 -1.2(6) . . . . ? N21 N22 C22 N23 -177.0(4) . . . . ? N21 N22 C22 S2 3.8(6) . . . . ? Cu S2 C22 N23 176.8(4) . . . . ? Cu S2 C22 N22 -4.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.989 _refine_diff_density_min -0.970 _refine_diff_density_rms 0.126 data_kent8 _database_code_CSD 213903 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 Cu N6 S2' _chemical_formula_weight 321.91 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 7.884(2) _cell_length_b 9.188(2) _cell_length_c 17.962(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.585(4) _cell_angle_gamma 90.00 _cell_volume 1274.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2297 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 25.33 _exptl_crystal_description lath _exptl_crystal_colour yellow _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.005 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.677 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 2.028 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 0.96 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6872 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART 1K CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6984 _diffrn_reflns_av_R_equivalents 0.0530 _diffrn_reflns_av_sigmaI/netI 0.0644 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.43 _reflns_number_total 2566 _reflns_number_gt 1817 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0688P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2566 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1222 _refine_ls_wR_factor_gt 0.1070 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 Cu Cu 0.16211(6) 0.35100(6) 0.47931(3) 0.02158(18) Uani 1 1 d . . . S1 S 0.39946(14) 0.42426(13) 0.55987(7) 0.0268(3) Uani 1 1 d . . . C1 C -0.1763(6) 0.2167(5) 0.6225(3) 0.0273(10) Uani 1 1 d . . . H1A H -0.3034 0.2212 0.6043 0.033 Uiso 1 1 calc R . . H1B H -0.1447 0.2880 0.6644 0.033 Uiso 1 1 calc R . . C1A C -0.1263(9) 0.0657(7) 0.6523(4) 0.062(2) Uani 1 1 d . . . H1A1 H -0.1511 -0.0043 0.6104 0.093 Uiso 1 1 calc R . . H1A2 H -0.1929 0.0400 0.6910 0.093 Uiso 1 1 calc R . . H1A3 H -0.0024 0.0635 0.6749 0.093 Uiso 1 1 calc R . . S2 S 0.20952(13) 0.36603(14) 0.36057(7) 0.0269(3) Uani 1 1 d . . . C2 C -0.3423(5) 0.1713(5) 0.4503(3) 0.0288(11) Uani 1 1 d . . . H2A H -0.4047 0.2276 0.4062 0.035 Uiso 1 1 calc R . . H2B H -0.4090 0.1791 0.4913 0.035 Uiso 1 1 calc R . . C2A C -0.3353(8) 0.0135(6) 0.4276(4) 0.0535(17) Uani 1 1 d . . . H2A1 H -0.2648 0.0042 0.3886 0.080 Uiso 1 1 calc R . . H2A2 H -0.4528 -0.0216 0.4072 0.080 Uiso 1 1 calc R . . H2A3 H -0.2836 -0.0445 0.4721 0.080 Uiso 1 1 calc R . . N11 N 0.0689(5) 0.3089(4) 0.5707(2) 0.0245(8) Uani 1 1 d . . . C11 C -0.0880(5) 0.2575(5) 0.5586(3) 0.0234(10) Uani 1 1 d . . . N12 N 0.1646(5) 0.3259(4) 0.6428(2) 0.0258(9) Uani 1 1 d . . . C12 C 0.3238(6) 0.3748(5) 0.6413(3) 0.0273(10) Uani 1 1 d . . . N13 N 0.4360(5) 0.3855(5) 0.7072(2) 0.0355(10) Uani 1 1 d . . . H13A H 0.4043 0.3609 0.7497 0.043 Uiso 1 1 calc R . . H13B H 0.5417 0.4173 0.7082 0.043 Uiso 1 1 calc R . . C21 C -0.1666(5) 0.2375(5) 0.4772(3) 0.0224(9) Uani 1 1 d . . . N21 N -0.0653(4) 0.2746(4) 0.4315(2) 0.0222(8) Uani 1 1 d . . . N22 N -0.1174(4) 0.2569(4) 0.3542(2) 0.0245(8) Uani 1 1 d . . . C22 C 0.0077(5) 0.2920(5) 0.3182(3) 0.0253(10) Uani 1 1 d . . . N23 N -0.0209(5) 0.2698(5) 0.2432(2) 0.0336(10) Uani 1 1 d . . . H23A H -0.1202 0.2329 0.2195 0.040 Uiso 1 1 calc R . . H23B H 0.0595 0.2919 0.2175 0.040 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 Cu 0.0145(3) 0.0359(3) 0.0153(3) 0.0007(2) 0.0054(2) -0.0008(2) S1 0.0185(6) 0.0428(7) 0.0197(6) 0.0009(5) 0.0053(5) -0.0052(5) C1 0.016(2) 0.046(3) 0.020(3) 0.000(2) 0.007(2) -0.001(2) C1A 0.073(5) 0.061(4) 0.064(5) 0.025(3) 0.042(4) 0.013(3) S2 0.0160(5) 0.0496(7) 0.0162(6) -0.0002(5) 0.0061(5) -0.0049(5) C2 0.015(2) 0.050(3) 0.022(3) 0.000(2) 0.005(2) -0.0027(19) C2A 0.044(3) 0.048(3) 0.073(5) -0.015(3) 0.023(3) -0.017(3) N11 0.0154(18) 0.040(2) 0.018(2) -0.0006(16) 0.0044(16) 0.0014(15) C11 0.019(2) 0.029(2) 0.023(3) 0.0024(18) 0.007(2) 0.0039(17) N12 0.0193(19) 0.045(2) 0.012(2) -0.0024(16) 0.0021(16) -0.0002(16) C12 0.023(2) 0.038(3) 0.021(3) -0.0013(19) 0.005(2) -0.0002(19) N13 0.021(2) 0.070(3) 0.015(2) 0.0006(19) 0.0023(18) -0.0087(19) C21 0.019(2) 0.032(2) 0.018(2) 0.0027(18) 0.0074(19) 0.0033(18) N21 0.0168(17) 0.034(2) 0.017(2) -0.0010(16) 0.0060(16) -0.0014(15) N22 0.0182(18) 0.043(2) 0.013(2) -0.0012(16) 0.0040(16) -0.0016(16) C22 0.016(2) 0.037(3) 0.023(3) 0.006(2) 0.0053(19) 0.0022(18) N23 0.019(2) 0.068(3) 0.014(2) -0.0025(19) 0.0049(17) -0.0095(19) _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 Cu S1 2.2274(14) . ? Cu S2 2.2424(13) . ? Cu N11 1.967(4) . ? Cu N21 1.956(4) . ? S1 C12 1.746(5) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C1 C1A 1.511(8) . ? C1 C11 1.505(6) . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? S2 C22 1.757(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C2A 1.510(7) . ? C2 C21 1.501(6) . ? C2A H2A1 0.9800 . ? C2A H2A2 0.9800 . ? C2A H2A3 0.9800 . ? N11 C11 1.301(5) . ? N11 N12 1.370(5) . ? C11 C21 1.480(6) . ? N12 C12 1.339(5) . ? C12 N13 1.332(6) . ? N13 H13A 0.8800 . ? N13 H13B 0.8800 . ? C21 N21 1.301(5) . ? N21 N22 1.377(5) . ? N22 C22 1.324(5) . ? C22 N23 1.335(6) . ? N23 H23A 0.8800 . ? N23 H23B 0.8800 . ? 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 S1 Cu S2 108.69(5) . . ? S1 Cu N11 85.59(12) . . ? S1 Cu N21 165.94(11) . . ? S2 Cu N11 165.36(12) . . ? S2 Cu N21 85.28(11) . . ? N11 Cu N21 80.37(15) . . ? Cu S1 C12 94.68(16) . . ? H1A C1 H1B 107.9 . . ? H1A C1 C1A 109.3 . . ? H1A C1 C11 109.3 . . ? H1B C1 C1A 109.3 . . ? H1B C1 C11 109.3 . . ? C1A C1 C11 111.8(4) . . ? C1 C1A H1A1 109.5 . . ? C1 C1A H1A2 109.5 . . ? C1 C1A H1A3 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? Cu S2 C22 94.53(16) . . ? H2A C2 H2B 107.8 . . ? H2A C2 C2A 108.9 . . ? H2A C2 C21 108.9 . . ? H2B C2 C2A 108.9 . . ? H2B C2 C21 108.9 . . ? C2A C2 C21 113.2(4) . . ? C2 C2A H2A1 109.5 . . ? C2 C2A H2A2 109.5 . . ? C2 C2A H2A3 109.5 . . ? H2A1 C2A H2A2 109.5 . . ? H2A1 C2A H2A3 109.5 . . ? H2A2 C2A H2A3 109.5 . . ? Cu N11 C11 115.7(3) . . ? Cu N11 N12 122.6(3) . . ? C11 N11 N12 121.6(4) . . ? C1 C11 N11 122.2(4) . . ? C1 C11 C21 123.8(4) . . ? N11 C11 C21 114.0(4) . . ? N11 N12 C12 111.0(4) . . ? S1 C12 N12 125.7(4) . . ? S1 C12 N13 116.6(3) . . ? N12 C12 N13 117.7(4) . . ? C12 N13 H13A 120.0 . . ? C12 N13 H13B 120.0 . . ? H13A N13 H13B 120.0 . . ? C2 C21 C11 123.0(4) . . ? C2 C21 N21 123.2(4) . . ? C11 C21 N21 113.7(4) . . ? Cu N21 C21 116.2(3) . . ? Cu N21 N22 123.2(3) . . ? C21 N21 N22 120.6(4) . . ? N21 N22 C22 111.3(4) . . ? S2 C22 N22 125.5(4) . . ? S2 C22 N23 116.8(3) . . ? N22 C22 N23 117.6(4) . . ? C22 N23 H23A 120.0 . . ? C22 N23 H23B 120.0 . . ? H23A N23 H23B 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S2 Cu S1 C12 -172.66(16) . . . . ? N11 Cu S1 C12 4.08(19) . . . . ? N21 Cu S1 C12 0.9(5) . . . . ? S1 Cu S2 C22 176.71(16) . . . . ? N11 Cu S2 C22 9.7(5) . . . . ? N21 Cu S2 C22 -1.73(19) . . . . ? S1 Cu N11 C11 179.4(3) . . . . ? S1 Cu N11 N12 -3.5(3) . . . . ? S2 Cu N11 C11 -12.9(7) . . . . ? S2 Cu N11 N12 164.2(3) . . . . ? N21 Cu N11 C11 -1.4(3) . . . . ? N21 Cu N11 N12 175.7(4) . . . . ? Cu N11 C11 C1 178.6(3) . . . . ? Cu N11 C11 C21 1.1(5) . . . . ? N12 N11 C11 C1 1.5(7) . . . . ? N12 N11 C11 C21 -176.0(4) . . . . ? C1A C1 C11 N11 -83.0(6) . . . . ? C1A C1 C11 C21 94.2(6) . . . . ? Cu N11 N12 C12 0.5(5) . . . . ? C11 N11 N12 C12 177.5(4) . . . . ? N11 N12 C12 S1 4.4(6) . . . . ? N11 N12 C12 N13 -174.8(4) . . . . ? Cu S1 C12 N12 -6.1(4) . . . . ? Cu S1 C12 N13 173.1(4) . . . . ? C1 C11 C21 C2 -1.2(7) . . . . ? C1 C11 C21 N21 -177.4(4) . . . . ? N11 C11 C21 C2 176.3(4) . . . . ? N11 C11 C21 N21 0.0(6) . . . . ? C2A C2 C21 C11 -100.5(5) . . . . ? C2A C2 C21 N21 75.3(6) . . . . ? C2 C21 N21 Cu -177.4(3) . . . . ? C2 C21 N21 N22 1.2(7) . . . . ? C11 C21 N21 Cu -1.2(5) . . . . ? C11 C21 N21 N22 177.4(4) . . . . ? S1 Cu N21 C21 4.6(7) . . . . ? S1 Cu N21 N22 -174.0(3) . . . . ? S2 Cu N21 C21 178.5(3) . . . . ? S2 Cu N21 N22 -0.1(3) . . . . ? N11 Cu N21 C21 1.4(3) . . . . ? N11 Cu N21 N22 -177.2(4) . . . . ? Cu N21 N22 C22 2.7(5) . . . . ? C21 N21 N22 C22 -175.9(4) . . . . ? N21 N22 C22 S2 -4.9(6) . . . . ? N21 N22 C22 N23 175.2(4) . . . . ? Cu S2 C22 N22 4.3(4) . . . . ? Cu S2 C22 N23 -175.7(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N13 H13A N12 0.88 2.13 3.007(6) 173.4 2_556 N23 H23A N22 0.88 2.23 3.034(5) 151.3 2_455 N23 H23B S2 0.88 2.60 3.482(4) 177.8 2 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.43 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.352 _refine_diff_density_min -0.767 _refine_diff_density_rms 0.130 data_kent3 _database_code_CSD 213904 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H6 Cu N6 S2' _chemical_formula_weight 265.81 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 6.7026(6) _cell_length_b 3.9436(3) _cell_length_c 32.307(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.919(2) _cell_angle_gamma 90.00 _cell_volume 852.84(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6415 _cell_measurement_theta_min 4.91 _cell_measurement_theta_max 58.11 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.070 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 3.007 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.34 _exptl_absorpt_correction_T_max 0.95 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6904 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS Station 9.8' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_measurement_device_type 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 15 _diffrn_reflns_number 7780 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 29.05 _reflns_number_total 2328 _reflns_number_gt 1946 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Buker AXS SAINT v6.02a' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0431P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2328 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0751 _refine_ls_wR_factor_gt 0.0739 _refine_ls_goodness_of_fit_ref 0.976 _refine_ls_restrained_S_all 0.976 _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 Cu Cu 0.25275(4) 0.02613(7) 0.124059(8) 0.01639(10) Uani 1 1 d . . . S1 S 0.42502(8) -0.04217(16) 0.066638(18) 0.01831(13) Uani 1 1 d . . . S2 S 0.41091(8) 0.40446(15) 0.167381(18) 0.01830(14) Uani 1 1 d . . . N11 N 0.0403(3) -0.2275(5) 0.09250(6) 0.0166(4) Uani 1 1 d . . . C11 C -0.1195(3) -0.2783(6) 0.11279(7) 0.0188(5) Uani 1 1 d . . . H11A H -0.2291 -0.4084 0.1018 0.023 Uiso 1 1 calc R . . N12 N 0.0576(3) -0.3409(6) 0.05333(6) 0.0186(4) Uani 1 1 d . . . C12 C 0.2324(3) -0.2530(6) 0.03847(7) 0.0174(4) Uani 1 1 d . . . N13 N 0.2618(3) -0.3368(6) -0.00068(6) 0.0224(4) Uani 1 1 d . . . H13A H 0.1682 -0.4451 -0.0155 0.027 Uiso 1 1 calc R . . H13B H 0.3750 -0.2839 -0.0118 0.027 Uiso 1 1 calc R . . N21 N 0.0415(3) 0.0470(5) 0.16433(6) 0.0167(4) Uani 1 1 d . . . C21 C -0.1187(3) -0.1219(6) 0.15351(7) 0.0189(5) Uani 1 1 d . . . H21A H -0.2278 -0.1420 0.1710 0.023 Uiso 1 1 calc R . . N22 N 0.0601(3) 0.2149(5) 0.20144(6) 0.0180(4) Uani 1 1 d . . . C22 C 0.2317(3) 0.3822(6) 0.20519(7) 0.0167(4) Uani 1 1 d . . . N23 N 0.2732(3) 0.5487(5) 0.24103(6) 0.0223(4) Uani 1 1 d . . . H23A H 0.1878 0.5436 0.2608 0.027 Uiso 1 1 calc R . . H23B H 0.3857 0.6625 0.2446 0.027 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 Cu 0.01476(15) 0.01980(16) 0.01490(15) -0.00203(10) 0.00347(10) -0.00309(11) S1 0.0162(3) 0.0239(3) 0.0150(3) -0.0011(2) 0.0032(2) -0.0044(2) S2 0.0177(3) 0.0194(3) 0.0181(3) -0.0031(2) 0.0041(2) -0.0029(2) N11 0.0154(9) 0.0202(10) 0.0141(9) 0.0015(7) 0.0004(7) -0.0012(7) C11 0.0144(10) 0.0222(12) 0.0198(11) 0.0013(9) 0.0017(8) -0.0016(9) N12 0.0165(9) 0.0247(10) 0.0146(9) -0.0025(8) 0.0019(7) -0.0032(8) C12 0.0178(10) 0.0188(11) 0.0156(10) 0.0010(8) 0.0010(8) -0.0009(8) N13 0.0189(10) 0.0328(12) 0.0157(9) -0.0028(8) 0.0028(7) -0.0080(9) N21 0.0182(9) 0.0167(9) 0.0156(9) 0.0026(7) 0.0043(7) 0.0003(7) C21 0.0141(10) 0.0231(12) 0.0201(11) 0.0029(9) 0.0053(8) -0.0002(9) N22 0.0211(9) 0.0183(10) 0.0149(9) 0.0017(7) 0.0052(7) 0.0012(8) C22 0.0198(11) 0.0143(11) 0.0161(10) 0.0036(8) 0.0035(8) 0.0033(8) N23 0.0272(11) 0.0245(11) 0.0152(10) -0.0019(8) 0.0030(8) -0.0024(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N21 1.9727(19) . ? Cu N11 1.9797(19) . ? Cu S1 2.2506(6) . ? Cu S2 2.2710(6) . ? S1 C12 1.751(2) . ? S2 C22 1.759(2) . ? N11 C11 1.300(3) . ? N11 N12 1.353(3) . ? C11 C21 1.453(3) . ? C11 H11A 0.9500 . ? N12 C12 1.335(3) . ? C12 N13 1.332(3) . ? N13 H13A 0.8800 . ? N13 H13B 0.8800 . ? N21 C21 1.296(3) . ? N21 N22 1.370(3) . ? C21 H21A 0.9500 . ? N22 C22 1.326(3) . ? C22 N23 1.348(3) . ? N23 H23A 0.8800 . ? N23 H23B 0.8800 . ? 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 N21 Cu N11 80.75(8) . . ? N21 Cu S1 164.61(6) . . ? N11 Cu S1 84.30(6) . . ? N21 Cu S2 83.93(6) . . ? N11 Cu S2 161.84(6) . . ? S1 Cu S2 110.10(2) . . ? C12 S1 Cu 95.14(8) . . ? C22 S2 Cu 94.67(8) . . ? C11 N11 N12 122.19(19) . . ? C11 N11 Cu 114.08(16) . . ? N12 N11 Cu 123.73(14) . . ? N11 C11 C21 115.2(2) . . ? N11 C11 H11A 122.4 . . ? C21 C11 H11A 122.4 . . ? C12 N12 N11 111.68(18) . . ? N13 C12 N12 116.9(2) . . ? N13 C12 S1 118.07(17) . . ? N12 C12 S1 125.01(17) . . ? C12 N13 H13A 120.0 . . ? C12 N13 H13B 120.0 . . ? H13A N13 H13B 120.0 . . ? C21 N21 N22 121.43(19) . . ? C21 N21 Cu 114.40(16) . . ? N22 N21 Cu 124.14(15) . . ? N21 C21 C11 115.3(2) . . ? N21 C21 H21A 122.3 . . ? C11 C21 H21A 122.3 . . ? C22 N22 N21 111.12(18) . . ? N22 C22 N23 117.5(2) . . ? N22 C22 S2 125.53(17) . . ? N23 C22 S2 117.00(18) . . ? C22 N23 H23A 120.0 . . ? C22 N23 H23B 120.0 . . ? H23A N23 H23B 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N21 Cu S1 C12 -11.8(2) . . . . ? N11 Cu S1 C12 1.97(10) . . . . ? S2 Cu S1 C12 -166.65(8) . . . . ? N21 Cu S2 C22 5.79(9) . . . . ? N11 Cu S2 C22 38.3(2) . . . . ? S1 Cu S2 C22 179.29(7) . . . . ? N21 Cu N11 C11 -4.53(17) . . . . ? S1 Cu N11 C11 179.13(17) . . . . ? S2 Cu N11 C11 -37.4(3) . . . . ? N21 Cu N11 N12 175.7(2) . . . . ? S1 Cu N11 N12 -0.66(18) . . . . ? S2 Cu N11 N12 142.86(16) . . . . ? N12 N11 C11 C21 -176.3(2) . . . . ? Cu N11 C11 C21 3.9(3) . . . . ? C11 N11 N12 C12 178.6(2) . . . . ? Cu N11 N12 C12 -1.6(3) . . . . ? N11 N12 C12 N13 -176.8(2) . . . . ? N11 N12 C12 S1 4.0(3) . . . . ? Cu S1 C12 N13 176.78(19) . . . . ? Cu S1 C12 N12 -4.0(2) . . . . ? N11 Cu N21 C21 4.45(17) . . . . ? S1 Cu N21 C21 18.3(3) . . . . ? S2 Cu N21 C21 174.67(17) . . . . ? N11 Cu N21 N22 -177.50(18) . . . . ? S1 Cu N21 N22 -163.64(15) . . . . ? S2 Cu N21 N22 -7.28(16) . . . . ? N22 N21 C21 C11 178.2(2) . . . . ? Cu N21 C21 C11 -3.7(3) . . . . ? N11 C11 C21 N21 -0.2(3) . . . . ? C21 N21 N22 C22 -177.2(2) . . . . ? Cu N21 N22 C22 4.9(3) . . . . ? N21 N22 C22 N23 -177.49(19) . . . . ? N21 N22 C22 S2 2.2(3) . . . . ? Cu S2 C22 N22 -6.4(2) . . . . ? Cu S2 C22 N23 173.34(17) . . . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.736 _refine_diff_density_min -0.648 _refine_diff_density_rms 0.155 data_CRYSTALS_cif_3 _database_code_CSD 213905 #============================================================= # 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_hydrogens geom _refine_ls_hydrogen_treatment mixed #============================================================= _cell_length_a 8.8447(3) _cell_angle_alpha 106.010(2) _cell_length_b 9.1298(3) _cell_angle_beta 100.630(2) _cell_length_c 9.5442(4) _cell_angle_gamma 115.952(2) _cell_volume 623.2 _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 'Cu ' 0.2630 1.2660 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 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 _chemical_formula_sum ' C8 H14 Cu1 N6 S2 ' _chemical_formula_moiety ' C8 H14 Cu1 N6 S2 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 321.90 _cell_measurement_reflns_used 9774 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _cell_formula_units_Z 2 _exptl_crystal_description ' block ' _exptl_crystal_colour ' black ' _exptl_crystal_size_min 0.06 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_max 0.10 _exptl_crystal_density_diffrn 1.715 _exptl_crystal_density_meas ? _exptl_crystal_F_000 330.952 _exptl_absorpt_coefficient_mu 2.074 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 0.88 _diffrn_ambient_temperature 150 _diffrn_reflns_number 9774 _reflns_number_total 2802 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_measured_fraction_theta_max 0.986 _reflns_number_gt 1835 _diffrn_reflns_theta_min 5.15 _diffrn_reflns_theta_max 27.43 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min -11 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 12 _refine_diff_density_min -0.35 _refine_diff_density_max 0.37 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 1835 _refine_ls_number_parameters 162 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0325 _refine_ls_goodness_of_fit_ref 1.0656 _refine_ls_shift/su_max 0.009144 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979) 1.36 0.0827 0.786 ; _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 Cu1 0.99902(5) 0.03547(5) 0.69214(4) 0.0207 1.0000 Uani C11 0.7680(4) -0.3024(4) 0.6720(4) 0.0260 1.0000 Uani N11 0.7709(3) -0.1931(4) 0.6071(3) 0.0239 1.0000 Uani N12 0.6229(3) -0.2414(4) 0.4878(3) 0.0263 1.0000 Uani C12 0.6549(4) -0.1094(4) 0.4427(4) 0.0218 1.0000 Uani C13 0.3470(4) -0.2982(5) 0.2462(4) 0.0300 1.0000 Uani S1 0.8568(1) 0.0964(1) 0.51272(9) 0.0231 1.0000 Uani N13 0.5203(4) -0.1351(4) 0.3271(3) 0.0284 1.0000 Uani C14 0.2316(5) -0.2753(5) 0.1273(4) 0.0375 1.0000 Uani C21 0.9331(4) -0.2310(4) 0.8005(4) 0.0235 1.0000 Uani N21 1.0584(3) -0.0700(3) 0.8330(3) 0.0215 1.0000 Uani N22 1.2183(3) 0.0160(3) 0.9528(3) 0.0231 1.0000 Uani C22 1.3127(4) 0.1869(4) 0.9772(3) 0.0211 1.0000 Uani S2 1.2415(1) 0.2913(1) 0.87326(9) 0.0238 1.0000 Uani N23 1.4726(4) 0.2908(4) 1.0911(3) 0.0248 1.0000 Uani C23 1.5550(4) 0.2299(4) 1.1917(4) 0.0267 1.0000 Uani C24 1.7359(5) 0.3849(5) 1.3075(4) 0.0393 1.0000 Uani H1 0.530(5) -0.059(5) 0.306(4) 0.02(1) 1.0000 Uiso H2 1.538(5) 0.404(6) 1.111(5) 0.03(1) 1.0000 Uiso H111 0.6616 -0.4246 0.6367 0.0295 1.0000 Uiso H131 0.3636 -0.3980 0.1928 0.0344 1.0000 Uiso H132 0.2876 -0.3259 0.3227 0.0344 1.0000 Uiso H141 0.1117 -0.3878 0.0712 0.0420 1.0000 Uiso H142 0.2911 -0.2476 0.0509 0.0420 1.0000 Uiso H143 0.2152 -0.1754 0.1809 0.0420 1.0000 Uiso H211 0.9486 -0.3015 0.8595 0.0275 1.0000 Uiso H231 1.5713 0.1353 1.1264 0.0324 1.0000 Uiso H232 1.4752 0.1804 1.2490 0.0324 1.0000 Uiso H241 1.7919 0.3433 1.3760 0.0428 1.0000 Uiso H242 1.8157 0.4344 1.2503 0.0428 1.0000 Uiso H243 1.7196 0.4795 1.3728 0.0428 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 Cu1 0.01821(19) 0.0207(2) 0.02008(19) 0.00949(15) 0.00331(15) 0.00817(16) C11 0.0265(16) 0.0218(16) 0.0254(16) 0.0101(13) 0.0078(13) 0.0094(13) N11 0.0190(12) 0.0264(14) 0.0220(13) 0.0083(11) 0.006(1) 0.0096(11) N12 0.0220(14) 0.0319(15) 0.0240(14) 0.0132(12) 0.0077(11) 0.0122(12) C12 0.0200(14) 0.0238(16) 0.0225(15) 0.0087(13) 0.0088(12) 0.0120(13) C13 0.0225(16) 0.0312(18) 0.0322(17) 0.0130(15) 0.0066(14) 0.0118(14) S1 0.0208(4) 0.0232(4) 0.0233(4) 0.0103(3) 0.0045(3) 0.0105(3) N13 0.0251(14) 0.0263(15) 0.0300(15) 0.0118(13) 0.0050(12) 0.0119(13) C14 0.0282(18) 0.044(2) 0.0329(19) 0.0157(17) 0.0044(15) 0.0152(17) C21 0.0213(15) 0.0238(16) 0.0238(15) 0.0117(13) 0.0070(13) 0.0095(13) N21 0.0214(13) 0.0249(14) 0.0180(12) 0.0088(11) 0.006(1) 0.0119(12) N22 0.0218(13) 0.0255(14) 0.0216(13) 0.0101(11) 0.0070(11) 0.0117(11) C22 0.0204(15) 0.0250(16) 0.0192(14) 0.0081(12) 0.0081(12) 0.0128(13) S2 0.0223(4) 0.0197(4) 0.0230(4) 0.0074(3) 0.0004(3) 0.0095(3) N23 0.0224(14) 0.0230(15) 0.0238(13) 0.0098(12) 0.0014(11) 0.0100(12) C23 0.0295(17) 0.0306(18) 0.0209(15) 0.0100(14) 0.0040(13) 0.0183(15) C24 0.041(2) 0.037(2) 0.0289(18) 0.0092(16) -0.0056(16) 0.0208(18) _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 Cu1 . N11 . 1.965(3) yes Cu1 . S1 . 2.2735(8) yes Cu1 . S1 2_756 2.8045(9) yes Cu1 . N21 . 1.977(3) yes Cu1 . S2 . 2.2505(8) yes C11 . N11 . 1.306(4) yes C11 . C21 . 1.458(4) yes C11 . H111 . 1.000 no N11 . N12 . 1.369(4) yes N12 . C12 . 1.322(4) yes C12 . S1 . 1.760(3) yes C12 . N13 . 1.348(4) yes C13 . N13 . 1.447(4) yes C13 . C14 . 1.504(5) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no N13 . H1 . 0.74(4) yes C14 . H141 . 1.000 no C14 . H142 . 1.000 no C14 . H143 . 1.000 no C21 . N21 . 1.296(4) yes C21 . H211 . 1.000 no N21 . N22 . 1.363(3) yes N22 . C22 . 1.331(4) yes C22 . S2 . 1.763(3) yes C22 . N23 . 1.331(4) yes N23 . C23 . 1.468(4) yes N23 . H2 . 0.88(4) yes C23 . C24 . 1.512(5) yes C23 . H231 . 1.000 no C23 . H232 . 1.000 no C24 . H241 . 1.000 no C24 . H242 . 1.000 no C24 . H243 . 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 N11 . Cu1 . S1 . 84.57(8) yes N11 . Cu1 . S1 2_756 93.14(8) yes S1 . Cu1 . S1 2_756 91.97(3) yes N11 . Cu1 . N21 . 80.74(11) yes S1 . Cu1 . N21 . 164.98(8) yes S1 2_756 Cu1 . N21 . 91.92(8) yes N11 . Cu1 . S2 . 158.07(8) yes S1 . Cu1 . S2 . 109.15(3) yes S1 2_756 Cu1 . S2 . 103.09(3) yes N21 . Cu1 . S2 . 84.04(8) yes N11 . C11 . C21 . 114.2(3) yes N11 . C11 . H111 . 122.9 no C21 . C11 . H111 . 122.9 no Cu1 . N11 . C11 . 115.1(2) yes Cu1 . N11 . N12 . 124.6(2) yes C11 . N11 . N12 . 120.3(3) yes N11 . N12 . C12 . 109.9(3) yes N12 . C12 . S1 . 127.5(2) yes N12 . C12 . N13 . 117.1(3) yes S1 . C12 . N13 . 115.4(2) yes N13 . C13 . C14 . 109.3(3) yes N13 . C13 . H131 . 109.5 no C14 . C13 . H131 . 109.5 no N13 . C13 . H132 . 109.5 no C14 . C13 . H132 . 109.5 no H131 . C13 . H132 . 109.5 no Cu1 . S1 . Cu1 2_756 88.03(3) yes Cu1 . S1 . C12 . 93.44(11) yes Cu1 2_756 S1 . C12 . 93.7(1) yes C12 . N13 . C13 . 124.7(3) yes C12 . N13 . H1 . 119.(3) yes C13 . N13 . H1 . 116.(3) yes C13 . C14 . H141 . 109.5 no C13 . C14 . H142 . 109.5 no H141 . C14 . H142 . 109.5 no C13 . C14 . H143 . 109.5 no H141 . C14 . H143 . 109.5 no H142 . C14 . H143 . 109.5 no C11 . C21 . N21 . 115.6(3) yes C11 . C21 . H211 . 122.2 no N21 . C21 . H211 . 122.2 no Cu1 . N21 . C21 . 114.3(2) yes Cu1 . N21 . N22 . 123.53(19) yes C21 . N21 . N22 . 122.2(3) yes N21 . N22 . C22 . 110.7(2) yes N22 . C22 . S2 . 125.3(2) yes N22 . C22 . N23 . 118.5(3) yes S2 . C22 . N23 . 116.1(2) yes Cu1 . S2 . C22 . 94.5(1) yes C22 . N23 . C23 . 124.5(3) yes C22 . N23 . H2 . 121.(3) yes C23 . N23 . H2 . 114.(3) yes N23 . C23 . C24 . 109.5(3) yes N23 . C23 . H231 . 109.5 no C24 . C23 . H231 . 109.5 no N23 . C23 . H232 . 109.5 no C24 . C23 . H232 . 109.5 no H231 . C23 . H232 . 109.5 no C23 . C24 . H241 . 109.5 no C23 . C24 . H242 . 109.5 no H241 . C24 . H242 . 109.5 no C23 . C24 . H243 . 109.5 no H241 . C24 . H243 . 109.5 no H242 . C24 . H243 . 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 N23 H2 S2 2_867 0.88(4) 2.55(4) 3.404(3) 167.(3) yes data_kent1 _database_code_CSD 213906 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H10 Cu N6 S2' _chemical_formula_weight 293.86 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.0832(4) _cell_length_b 19.9969(19) _cell_length_c 12.7651(12) _cell_angle_alpha 90.00 _cell_angle_beta 98.607(2) _cell_angle_gamma 90.00 _cell_volume 1030.55(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4722 _cell_measurement_theta_min 5.05 _cell_measurement_theta_max 58.38 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.894 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 2.498 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.61 _exptl_absorpt_correction_T_max 0.94 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6904 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS Station 9.8' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_measurement_device_type 'Bruker AXS SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 15 _diffrn_reflns_number 7252 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 29.23 _reflns_number_total 2811 _reflns_number_gt 2229 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS SMART' _computing_cell_refinement 'Bruker AXS SAINT v6.02a' _computing_data_reduction 'Bruker AXS SAINT' _computing_structure_solution 'Bruker AXS SHELXTL' _computing_structure_refinement 'Bruker AXS SHELXTL' _computing_molecular_graphics 'Bruker AXS SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0368P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2811 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0383 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0662 _refine_ls_wR_factor_gt 0.0649 _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_restrained_S_all 0.937 _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 Cu Cu 0.69692(7) 0.128468(12) 0.19661(2) 0.01775(8) Uani 1 1 d . . . S1 S 0.56966(15) 0.21427(2) 0.08466(4) 0.02234(12) Uani 1 1 d . . . S2 S 1.12915(13) 0.15648(2) 0.32370(4) 0.01848(11) Uani 1 1 d . . . N11 N 0.3890(5) 0.07707(9) 0.09237(14) 0.0193(4) Uani 1 1 d . . . C11 C 0.3493(6) 0.01487(10) 0.11916(17) 0.0210(4) Uani 1 1 d . . . H11 H 0.2081 -0.0152 0.0759 0.025 Uiso 1 1 calc R . . C12 C 0.3084(5) 0.16692(10) -0.00912(17) 0.0203(4) Uani 1 1 d . . . N12 N 0.2315(5) 0.10232(9) -0.00092(15) 0.0219(4) Uani 1 1 d . . . N13 N 0.1793(5) 0.19889(9) -0.09864(15) 0.0247(4) Uani 1 1 d . . . H13N H 0.2362 0.2408 -0.1066 0.030 Uiso 1 1 calc R . . C13 C -0.0490(6) 0.16788(12) -0.18282(18) 0.0283(5) Uani 1 1 d . . . H13A H 0.0565 0.1287 -0.2097 0.042 Uiso 1 1 calc R . . H13B H -0.1081 0.2001 -0.2404 0.042 Uiso 1 1 calc R . . H13C H -0.2495 0.1539 -0.1551 0.042 Uiso 1 1 calc R . . C21 C 0.5374(6) -0.00485(10) 0.22006(17) 0.0203(4) Uani 1 1 d . . . H21 H 0.5215 -0.0484 0.2488 0.024 Uiso 1 1 calc R . . N21 N 0.7293(4) 0.04104(8) 0.26855(14) 0.0173(3) Uani 1 1 d . . . N22 N 0.9196(5) 0.02907(8) 0.36392(14) 0.0187(4) Uani 1 1 d . . . C22 C 1.1102(5) 0.08242(10) 0.39637(16) 0.0169(4) Uani 1 1 d . . . C23 C 1.5158(6) 0.12623(11) 0.54523(18) 0.0243(4) Uani 1 1 d . . . H23A H 1.6132 0.1525 0.4928 0.037 Uiso 1 1 calc R . . H23B H 1.6926 0.1045 0.5938 0.037 Uiso 1 1 calc R . . H23C H 1.3891 0.1559 0.5854 0.037 Uiso 1 1 calc R . . N23 N 1.2966(5) 0.07552(9) 0.49124(15) 0.0209(4) Uani 1 1 d . . . H23N H 1.2859 0.0370 0.5238 0.025 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 Cu 0.02129(14) 0.01504(12) 0.01629(13) 0.00178(10) 0.00077(9) -0.00095(10) S1 0.0278(3) 0.0178(2) 0.0203(3) 0.0029(2) -0.0004(2) -0.0032(2) S2 0.0198(3) 0.0172(2) 0.0181(2) 0.00287(19) 0.00151(19) -0.00139(19) N11 0.0210(9) 0.0214(8) 0.0157(8) 0.0003(7) 0.0036(7) 0.0016(7) C11 0.0235(11) 0.0205(10) 0.0191(10) -0.0029(8) 0.0031(8) -0.0015(8) C12 0.0217(11) 0.0215(10) 0.0187(10) -0.0014(8) 0.0061(8) 0.0013(8) N12 0.0260(10) 0.0215(8) 0.0175(9) 0.0001(7) 0.0012(7) 0.0010(7) N13 0.0318(11) 0.0209(9) 0.0207(9) 0.0035(7) 0.0021(8) 0.0000(8) C13 0.0357(14) 0.0295(12) 0.0181(11) -0.0003(9) -0.0016(10) 0.0040(10) C21 0.0260(11) 0.0153(9) 0.0201(10) 0.0022(8) 0.0053(9) 0.0017(8) N21 0.0177(8) 0.0186(8) 0.0160(8) -0.0001(7) 0.0038(7) 0.0003(7) N22 0.0213(9) 0.0182(8) 0.0163(8) 0.0032(7) 0.0016(7) -0.0010(7) C22 0.0168(10) 0.0177(9) 0.0171(10) 0.0019(8) 0.0057(8) 0.0025(7) C23 0.0240(11) 0.0251(10) 0.0226(11) 0.0002(9) -0.0007(9) -0.0010(9) N23 0.0219(10) 0.0190(8) 0.0214(9) 0.0038(7) 0.0016(7) -0.0011(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N21 1.9701(17) . ? Cu N11 1.9767(19) . ? Cu S1 2.2435(6) . ? Cu S2 2.2812(6) . ? S1 C12 1.756(2) . ? S2 C22 1.755(2) . ? N11 C11 1.307(3) . ? N11 N12 1.363(2) . ? C11 C21 1.452(3) . ? C11 H11 0.9500 . ? C12 N12 1.337(3) . ? C12 N13 1.346(3) . ? N13 C13 1.452(3) . ? N13 H13N 0.8800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C21 N21 1.301(3) . ? C21 H21 0.9500 . ? N21 N22 1.364(2) . ? N22 C22 1.349(3) . ? C22 N23 1.337(3) . ? C23 N23 1.456(3) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? N23 H23N 0.8800 . ? 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 N21 Cu N11 81.02(7) . . ? N21 Cu S1 165.59(5) . . ? N11 Cu S1 84.58(5) . . ? N21 Cu S2 84.01(5) . . ? N11 Cu S2 162.35(5) . . ? S1 Cu S2 110.24(2) . . ? C12 S1 Cu 94.65(7) . . ? C22 S2 Cu 94.48(7) . . ? C11 N11 N12 121.38(19) . . ? C11 N11 Cu 114.22(15) . . ? N12 N11 Cu 124.40(13) . . ? N11 C11 C21 114.89(19) . . ? N11 C11 H11 122.6 . . ? C21 C11 H11 122.6 . . ? N12 C12 N13 117.29(19) . . ? N12 C12 S1 126.37(17) . . ? N13 C12 S1 116.32(16) . . ? C12 N12 N11 109.93(17) . . ? C12 N13 C13 123.50(19) . . ? C12 N13 H13N 118.3 . . ? C13 N13 H13N 118.3 . . ? N13 C13 H13A 109.5 . . ? N13 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N13 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N21 C21 C11 115.55(18) . . ? N21 C21 H21 122.2 . . ? C11 C21 H21 122.2 . . ? C21 N21 N22 121.52(17) . . ? C21 N21 Cu 114.24(14) . . ? N22 N21 Cu 124.14(13) . . ? C22 N22 N21 111.16(16) . . ? N23 C22 N22 114.87(18) . . ? N23 C22 S2 120.10(15) . . ? N22 C22 S2 125.03(16) . . ? N23 C23 H23A 109.5 . . ? N23 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N23 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 N23 C23 125.65(18) . . ? C22 N23 H23N 117.2 . . ? C23 N23 H23N 117.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N21 Cu S1 C12 -3.1(2) . . . . ? N11 Cu S1 C12 -1.96(9) . . . . ? S2 Cu S1 C12 168.19(7) . . . . ? N21 Cu S2 C22 -8.04(9) . . . . ? N11 Cu S2 C22 -40.1(2) . . . . ? S1 Cu S2 C22 174.13(7) . . . . ? N21 Cu N11 C11 1.37(16) . . . . ? S1 Cu N11 C11 -178.34(16) . . . . ? S2 Cu N11 C11 33.7(3) . . . . ? N21 Cu N11 N12 -177.61(18) . . . . ? S1 Cu N11 N12 2.68(16) . . . . ? S2 Cu N11 N12 -145.33(15) . . . . ? N12 N11 C11 C21 179.08(19) . . . . ? Cu N11 C11 C21 0.1(3) . . . . ? Cu S1 C12 N12 2.0(2) . . . . ? Cu S1 C12 N13 -176.66(16) . . . . ? N13 C12 N12 N11 178.22(19) . . . . ? S1 C12 N12 N11 -0.4(3) . . . . ? C11 N11 N12 C12 179.1(2) . . . . ? Cu N11 N12 C12 -2.0(2) . . . . ? N12 C12 N13 C13 3.2(3) . . . . ? S1 C12 N13 C13 -178.05(18) . . . . ? N11 C11 C21 N21 -2.4(3) . . . . ? C11 C21 N21 N22 -179.95(18) . . . . ? C11 C21 N21 Cu 3.5(3) . . . . ? N11 Cu N21 C21 -2.72(16) . . . . ? S1 Cu N21 C21 -1.6(3) . . . . ? S2 Cu N21 C21 -173.35(16) . . . . ? N11 Cu N21 N22 -179.15(17) . . . . ? S1 Cu N21 N22 -178.00(14) . . . . ? S2 Cu N21 N22 10.22(15) . . . . ? C21 N21 N22 C22 176.8(2) . . . . ? Cu N21 N22 C22 -7.0(2) . . . . ? N21 N22 C22 N23 177.84(17) . . . . ? N21 N22 C22 S2 -2.8(3) . . . . ? Cu S2 C22 N23 -172.06(16) . . . . ? Cu S2 C22 N22 8.65(19) . . . . ? N22 C22 N23 C23 -178.2(2) . . . . ? S2 C22 N23 C23 2.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.524 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.082 data_kent2 _database_code_CSD 213907 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H7 Cu N6 S2' _chemical_formula_weight 278.83 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' 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 5.5081(4) _cell_length_b 15.4057(10) _cell_length_c 11.6504(8) _cell_angle_alpha 90.00 _cell_angle_beta 102.193(2) _cell_angle_gamma 90.00 _cell_volume 966.31(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5258 _cell_measurement_theta_min 5.14 _cell_measurement_theta_max 58.26 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.917 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 2.659 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.68 _exptl_absorpt_correction_T_max 0.93 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6904 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS Station 9.8' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_measurement_device_type 'Bruker AXS SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 10 _diffrn_reflns_number 6518 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 29.22 _reflns_number_total 2587 _reflns_number_gt 2165 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS SMART' _computing_cell_refinement 'Bruker AXS SAINT v6.02a' _computing_data_reduction 'Bruker AXS SAINT' _computing_structure_solution 'Bruker AXS SHELXTL' _computing_structure_refinement 'Bruker AXS SHELXTL' _computing_molecular_graphics 'Bruker AXS SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0512P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2587 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0941 _refine_ls_wR_factor_gt 0.0918 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 Cu Cu 0.28036(6) 0.60065(2) 0.72461(3) 0.02289(12) Uani 1 1 d . . . S1 S 0.03218(14) 0.67719(5) 0.58420(7) 0.03105(18) Uani 1 1 d . . . S2 S 0.59613(14) 0.68448(4) 0.81518(7) 0.03163(18) Uani 1 1 d . . . C1 C -0.0750(12) 0.3590(4) 0.7223(5) 0.0253(14) Uani 0.459(6) 1 d P . . H1A H -0.2290 0.3754 0.7463 0.038 Uiso 0.459(6) 1 calc PR . . H1B H 0.0056 0.3116 0.7723 0.038 Uiso 0.459(6) 1 calc PR . . H1C H -0.1135 0.3400 0.6402 0.038 Uiso 0.459(6) 1 calc PR . . C2 C 0.4491(11) 0.3529(3) 0.8737(5) 0.0310(14) Uani 0.541(6) 1 d P . . H2A H 0.6037 0.3397 0.8484 0.047 Uiso 0.541(6) 1 calc PR . . H2B H 0.3321 0.3047 0.8525 0.047 Uiso 0.541(6) 1 calc PR . . H2C H 0.4845 0.3612 0.9590 0.047 Uiso 0.541(6) 1 calc PR . . N11 N 0.0327(4) 0.50779(14) 0.68093(19) 0.0211(4) Uani 1 1 d . . . C11 C 0.0935(5) 0.43470(17) 0.7347(2) 0.0233(5) Uani 1 1 d . . . C12 C -0.2004(5) 0.59771(17) 0.5546(2) 0.0235(5) Uani 1 1 d . . . N12 N -0.1878(4) 0.51868(14) 0.60279(19) 0.0226(4) Uani 1 1 d . . . N13 N -0.4079(5) 0.61763(15) 0.4758(2) 0.0285(5) Uani 1 1 d . . . H13A H -0.5284 0.5793 0.4579 0.034 Uiso 1 1 calc R . . H13B H -0.4235 0.6690 0.4421 0.034 Uiso 1 1 calc R . . C21 C 0.3384(5) 0.43356(17) 0.8148(2) 0.0236(5) Uani 1 1 d . . . N21 N 0.4574(4) 0.50686(14) 0.82186(19) 0.0216(4) Uani 1 1 d . . . N22 N 0.6888(4) 0.51643(14) 0.8922(2) 0.0239(5) Uani 1 1 d . . . C22 C 0.7669(5) 0.59797(17) 0.8905(3) 0.0264(6) Uani 1 1 d . . . N23 N 0.9981(5) 0.61607(16) 0.9509(3) 0.0355(6) Uani 1 1 d . . . H23A H 1.0910 0.5746 0.9895 0.043 Uiso 1 1 calc R . . H23B H 1.0562 0.6693 0.9518 0.043 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 Cu 0.01759(18) 0.01826(17) 0.03095(19) -0.00040(12) 0.00085(12) -0.00075(12) S1 0.0225(4) 0.0230(3) 0.0440(4) 0.0087(3) -0.0012(3) -0.0007(3) S2 0.0255(4) 0.0206(3) 0.0440(4) -0.0026(3) -0.0036(3) -0.0037(3) C1 0.023(3) 0.019(3) 0.029(3) 0.004(2) -0.005(2) 0.003(2) C2 0.029(3) 0.025(3) 0.035(3) -0.002(2) -0.003(2) -0.007(2) N11 0.0168(11) 0.0212(10) 0.0242(11) -0.0003(8) 0.0017(8) 0.0002(8) C11 0.0211(13) 0.0225(13) 0.0245(12) 0.0000(10) 0.0004(10) -0.0023(10) C12 0.0177(12) 0.0247(13) 0.0277(13) 0.0005(10) 0.0039(10) 0.0019(10) N12 0.0179(11) 0.0232(11) 0.0245(11) 0.0021(9) -0.0001(9) -0.0002(9) N13 0.0225(12) 0.0268(12) 0.0333(12) 0.0051(9) -0.0007(10) 0.0008(9) C21 0.0203(13) 0.0225(12) 0.0256(13) -0.0007(10) -0.0008(10) -0.0005(10) N21 0.0160(11) 0.0209(10) 0.0266(11) -0.0028(8) 0.0016(8) 0.0002(8) N22 0.0168(11) 0.0237(11) 0.0282(11) -0.0059(9) -0.0022(9) -0.0004(9) C22 0.0198(13) 0.0258(13) 0.0319(13) -0.0064(11) 0.0017(11) -0.0001(11) N23 0.0239(13) 0.0230(12) 0.0523(16) -0.0044(11) -0.0083(11) -0.0034(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 Cu N21 1.963(2) . ? Cu N11 1.968(2) . ? Cu S1 2.2340(8) . ? Cu S2 2.2431(8) . ? S1 C12 1.753(3) . ? S2 C22 1.756(3) . ? C1 C11 1.478(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C21 1.486(6) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? N11 C11 1.298(3) . ? N11 N12 1.365(3) . ? C11 C21 1.470(4) . ? C12 N12 1.336(3) . ? C12 N13 1.341(4) . ? N13 H13A 0.8800 . ? N13 H13B 0.8800 . ? C21 N21 1.299(3) . ? N21 N22 1.370(3) . ? N22 C22 1.329(3) . ? C22 N23 1.348(4) . ? N23 H23A 0.8800 . ? N23 H23B 0.8800 . ? 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 N21 Cu N11 81.20(9) . . ? N21 Cu S1 164.46(7) . . ? N11 Cu S1 84.88(7) . . ? N21 Cu S2 84.89(7) . . ? N11 Cu S2 165.11(7) . . ? S1 Cu S2 109.53(3) . . ? C12 S1 Cu 94.83(9) . . ? C22 S2 Cu 94.49(10) . . ? C11 C1 H1A 109.5 . . ? C11 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C11 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C21 C2 H2A 109.5 . . ? C21 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C21 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C11 N11 N12 122.1(2) . . ? C11 N11 Cu 114.31(18) . . ? N12 N11 Cu 123.60(16) . . ? N11 C11 C21 115.2(2) . . ? N11 C11 C1 123.0(3) . . ? C21 C11 C1 121.7(3) . . ? N12 C12 N13 117.2(2) . . ? N12 C12 S1 125.6(2) . . ? N13 C12 S1 117.2(2) . . ? C12 N12 N11 110.6(2) . . ? C12 N13 H13A 120.0 . . ? C12 N13 H13B 120.0 . . ? H13A N13 H13B 120.0 . . ? N21 C21 C11 114.4(2) . . ? N21 C21 C2 123.0(3) . . ? C11 C21 C2 122.4(3) . . ? C21 N21 N22 121.6(2) . . ? C21 N21 Cu 114.89(18) . . ? N22 N21 Cu 123.49(17) . . ? C22 N22 N21 110.8(2) . . ? N22 C22 N23 117.4(3) . . ? N22 C22 S2 125.7(2) . . ? N23 C22 S2 116.8(2) . . ? C22 N23 H23A 120.0 . . ? C22 N23 H23B 120.0 . . ? H23A N23 H23B 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N21 Cu S1 C12 31.2(3) . . . . ? N11 Cu S1 C12 4.80(11) . . . . ? S2 Cu S1 C12 -171.37(9) . . . . ? N21 Cu S2 C22 5.53(11) . . . . ? N11 Cu S2 C22 26.5(3) . . . . ? S1 Cu S2 C22 -168.54(10) . . . . ? N21 Cu N11 C11 1.7(2) . . . . ? S1 Cu N11 C11 174.8(2) . . . . ? S2 Cu N11 C11 -19.4(4) . . . . ? N21 Cu N11 N12 -179.6(2) . . . . ? S1 Cu N11 N12 -6.56(18) . . . . ? S2 Cu N11 N12 159.26(18) . . . . ? N12 N11 C11 C21 179.3(2) . . . . ? Cu N11 C11 C21 -2.0(3) . . . . ? N12 N11 C11 C1 -4.0(5) . . . . ? Cu N11 C11 C1 174.6(3) . . . . ? Cu S1 C12 N12 -4.7(2) . . . . ? Cu S1 C12 N13 176.0(2) . . . . ? N13 C12 N12 N11 -179.9(2) . . . . ? S1 C12 N12 N11 0.8(3) . . . . ? C11 N11 N12 C12 -176.5(2) . . . . ? Cu N11 N12 C12 5.0(3) . . . . ? N11 C11 C21 N21 1.2(4) . . . . ? C1 C11 C21 N21 -175.5(4) . . . . ? N11 C11 C21 C2 -173.3(3) . . . . ? C1 C11 C21 C2 10.0(5) . . . . ? C11 C21 N21 N22 -179.6(2) . . . . ? C2 C21 N21 N22 -5.1(5) . . . . ? C11 C21 N21 Cu 0.3(3) . . . . ? C2 C21 N21 Cu 174.7(3) . . . . ? N11 Cu N21 C21 -1.0(2) . . . . ? S1 Cu N21 C21 -27.6(4) . . . . ? S2 Cu N21 C21 173.6(2) . . . . ? N11 Cu N21 N22 178.8(2) . . . . ? S1 Cu N21 N22 152.22(19) . . . . ? S2 Cu N21 N22 -6.50(19) . . . . ? C21 N21 N22 C22 -176.3(2) . . . . ? Cu N21 N22 C22 3.8(3) . . . . ? N21 N22 C22 N23 -176.5(2) . . . . ? N21 N22 C22 S2 2.9(3) . . . . ? Cu S2 C22 N22 -6.5(3) . . . . ? Cu S2 C22 N23 172.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.628 _refine_diff_density_min -0.653 _refine_diff_density_rms 0.112 data_ATSMH2 _database_code_CSD 213908 #============================================================= # 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_hydrogens geom _refine_ls_hydrogen_treatment mixed #============================================================= _cell_length_a 9.4874(1) _cell_angle_alpha 60.9079(3) _cell_length_b 11.2045(1) _cell_angle_beta 87.3227(6) _cell_length_c 11.2427(1) _cell_angle_gamma 81.8540(5) _cell_volume 1033.5 _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 '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 _chemical_formula_sum ' C12 H28 N6 O2 S4 ' _chemical_formula_moiety ' C12 H28 N6 O2 S4 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 416.64 _cell_measurement_reflns_used 45757 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _cell_formula_units_Z 2 _exptl_crystal_description ' block ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.16 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_max 0.26 _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_meas ? _exptl_crystal_F_000 444.919 _exptl_absorpt_coefficient_mu 0.477 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_T_max 0.93 _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 19519 _reflns_number_total 4700 _diffrn_reflns_av_R_equivalents 0.025 _diffrn_measured_fraction_theta_max 0.990 _reflns_number_gt 4097 _diffrn_reflns_theta_min 5.37 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min -12 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _refine_diff_density_min -0.79 _refine_diff_density_max 0.67 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 4097 _refine_ls_number_parameters 233 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.0437 _refine_ls_goodness_of_fit_ref 1.6605 _refine_ls_shift/su_max 0.016829 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979) 1.85 -.591 0.687 ; _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 C1 0.8836(2) 0.0545(2) -0.1640(2) 0.0206 1.0000 Uani C11 0.92487(18) 0.02569(19) -0.02444(18) 0.0150 1.0000 Uani N11 0.83964(16) 0.04529(17) 0.05958(16) 0.0164 1.0000 Uani N12 0.69847(17) 0.09009(18) 0.01917(17) 0.0178 1.0000 Uani C12 0.60410(19) 0.11063(19) 0.10544(19) 0.0169 1.0000 Uani S1 0.42764(5) 0.13617(5) 0.06954(5) 0.0222 1.0000 Uani N13 0.65749(18) 0.11113(18) 0.21169(17) 0.0195 1.0000 Uani C13 0.5693(2) 0.1217(3) 0.3164(2) 0.0297 1.0000 Uani C3 0.5923(2) 0.4760(2) 0.1653(2) 0.0230 1.0000 Uani C31 0.4792(2) 0.5001(2) 0.06416(19) 0.0172 1.0000 Uani N31 0.34393(17) 0.52759(17) 0.07418(16) 0.0186 1.0000 Uani N32 0.29505(18) 0.52852(19) 0.19105(18) 0.0206 1.0000 Uani C32 0.1530(2) 0.5679(2) 0.1955(2) 0.0188 1.0000 Uani S3 0.08482(5) 0.55374(6) 0.34222(5) 0.0240 1.0000 Uani N33 0.07845(18) 0.6163(2) 0.07999(19) 0.0251 1.0000 Uani C33 -0.0734(2) 0.6637(3) 0.0642(3) 0.0324 1.0000 Uani O41 0.9242(2) 0.1245(3) 0.3055(3) 0.0617 1.0000 Uani S41 0.97544(7) 0.24275(7) 0.31225(6) 0.0355 1.0000 Uani C41 1.1563(3) 0.1839(3) 0.3699(3) 0.0409 1.0000 Uani C42 0.9001(3) 0.2396(3) 0.4610(3) 0.0420 1.0000 Uani O51 0.42691(17) 0.33929(18) 0.44839(15) 0.0300 1.0000 Uani S51 0.40242(5) 0.36264(5) 0.56935(5) 0.0204 1.0000 Uani C51 0.5570(2) 0.2727(2) 0.6771(2) 0.0293 1.0000 Uani C52 0.2802(2) 0.2493(2) 0.6735(2) 0.0315 1.0000 Uani H1 0.664(3) 0.075(3) -0.037(3) 0.031(7) 1.0000 Uiso H2 0.744(4) 0.106(3) 0.219(3) 0.045(9) 1.0000 Uiso H3 0.342(3) 0.483(3) 0.268(3) 0.035(7) 1.0000 Uiso H4 0.126(3) 0.619(3) 0.008(3) 0.037(7) 1.0000 Uiso H11 0.7792 0.0882 -0.1809 0.0245 1.0000 Uiso H12 0.9384 0.1265 -0.2335 0.0245 1.0000 Uiso H13 0.9055 -0.0320 -0.1706 0.0245 1.0000 Uiso H131 0.6314 0.1201 0.3867 0.0397 1.0000 Uiso H132 0.5025 0.2100 0.2742 0.0397 1.0000 Uiso H133 0.5134 0.0422 0.3602 0.0397 1.0000 Uiso H31 0.5466 0.4793 0.2457 0.0272 1.0000 Uiso H32 0.6561 0.5491 0.1219 0.0272 1.0000 Uiso H33 0.6495 0.3835 0.1955 0.0272 1.0000 Uiso H331 -0.1051 0.6952 -0.0313 0.0364 1.0000 Uiso H332 -0.0940 0.7422 0.0842 0.0364 1.0000 Uiso H333 -0.1257 0.5865 0.1289 0.0364 1.0000 Uiso H411 1.1974 0.2578 0.3769 0.0517 1.0000 Uiso H412 1.1612 0.0996 0.4614 0.0517 1.0000 Uiso H413 1.2118 0.1613 0.3040 0.0517 1.0000 Uiso H421 0.9301 0.3160 0.4716 0.0566 1.0000 Uiso H422 0.9339 0.1491 0.5423 0.0566 1.0000 Uiso H423 0.7939 0.2519 0.4528 0.0566 1.0000 Uiso H511 0.5481 0.2837 0.7603 0.0323 1.0000 Uiso H512 0.6435 0.3113 0.6269 0.0323 1.0000 Uiso H513 0.5658 0.1726 0.7044 0.0323 1.0000 Uiso H521 0.2603 0.2609 0.7557 0.0336 1.0000 Uiso H522 0.3224 0.1519 0.7026 0.0336 1.0000 Uiso H523 0.1894 0.2717 0.6207 0.0336 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 C1 0.0145(8) 0.0305(11) 0.0162(9) -0.0110(8) -0.0008(7) -0.0022(7) C11 0.0132(9) 0.0155(8) 0.0151(8) -0.0062(7) 0.0000(7) -0.0028(7) N11 0.0113(7) 0.0194(8) 0.0177(8) -0.0086(6) -0.0009(6) -0.0015(6) N12 0.0120(7) 0.0251(9) 0.0178(8) -0.0119(7) -0.0015(6) -0.0006(6) C12 0.0152(8) 0.0143(8) 0.0197(9) -0.0072(7) 0.0017(7) -0.0021(7) S1 0.0113(2) 0.0285(3) 0.0302(3) -0.0174(2) -0.00018(18) -0.00035(18) N13 0.0147(8) 0.0257(9) 0.0215(8) -0.0143(7) 0.0013(6) -0.0023(6) C13 0.0275(11) 0.0421(13) 0.0297(11) -0.0255(11) 0.0067(9) -0.0062(9) C3 0.0156(9) 0.0334(11) 0.0190(9) -0.0124(9) 0.0006(7) -0.0019(8) C31 0.0156(8) 0.0187(9) 0.0152(9) -0.0066(7) 0.0024(7) -0.0027(7) N31 0.0173(8) 0.0225(8) 0.0154(7) -0.0093(7) 0.0038(6) -0.0019(6) N32 0.0161(8) 0.0291(9) 0.0158(8) -0.0113(7) 0.0030(6) -0.0000(7) C32 0.0182(9) 0.0181(9) 0.0197(9) -0.0089(8) 0.0045(7) -0.0031(7) S3 0.0222(2) 0.0290(3) 0.0218(2) -0.0142(2) 0.00805(19) -0.00153(19) N33 0.0155(8) 0.035(1) 0.0209(9) -0.0116(8) 0.0029(7) 0.0012(7) C33 0.016(1) 0.0408(13) 0.0342(12) -0.0153(11) -0.0010(9) 0.0035(9) O41 0.0287(9) 0.114(2) 0.0956(18) -0.0926(17) -0.004(1) -0.0056(11) S41 0.0293(3) 0.0539(4) 0.0263(3) -0.0238(3) -0.0030(2) 0.0030(3) C41 0.0282(12) 0.0460(15) 0.0550(16) -0.0284(13) -0.0100(11) -0.0056(11) C42 0.0583(17) 0.0485(16) 0.0347(13) -0.0294(13) 0.0132(12) -0.0216(13) O51 0.0290(8) 0.0409(9) 0.0157(7) -0.0120(7) 0.0000(6) 0.0022(7) S51 0.0230(2) 0.0181(2) 0.0157(2) -0.00534(18) -0.00127(17) 0.00020(18) C51 0.0298(11) 0.0285(11) 0.023(1) -0.0075(9) -0.0085(9) 0.0009(9) C52 0.0252(11) 0.0300(12) 0.0288(11) -0.0074(9) 0.0080(9) -0.0017(9) _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 C1 . C11 . 1.499(3) yes C1 . H11 . 1.0000 no C1 . H12 . 1.000 no C1 . H13 . 1.000 no C11 . C11 2_755 1.483(3) yes C11 . N11 . 1.294(2) yes N11 . N12 . 1.377(2) yes N12 . C12 . 1.369(2) yes N12 . H1 . 0.83(3) yes C12 . S1 . 1.6919(19) yes C12 . N13 . 1.322(3) yes N13 . C13 . 1.454(3) yes N13 . H2 . 0.82(3) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C13 . H133 . 1.000 no C3 . C31 . 1.500(3) yes C3 . H31 . 1.000 no C3 . H32 . 1.000 no C3 . H33 . 1.000 no C31 . C31 2_665 1.479(4) yes C31 . N31 . 1.289(2) yes N31 . N32 . 1.377(2) yes N32 . C32 . 1.364(2) yes N32 . H3 . 0.87(3) yes C32 . S3 . 1.685(2) yes C32 . N33 . 1.331(3) yes N33 . C33 . 1.451(3) yes N33 . H4 . 0.89(3) yes C33 . H331 . 1.000 no C33 . H332 . 1.000 no C33 . H333 . 1.000 no O41 . S41 . 1.511(2) yes S41 . C41 . 1.779(3) yes S41 . C42 . 1.773(3) yes C41 . H411 . 1.000 no C41 . H412 . 1.000 no C41 . H413 . 1.000 no C42 . H421 . 1.000 no C42 . H422 . 1.000 no C42 . H423 . 1.000 no O51 . S51 . 1.5070(15) yes S51 . C51 . 1.787(2) yes S51 . C52 . 1.781(2) yes C51 . H511 . 1.000 no C51 . H512 . 1.000 no C51 . H513 . 1.000 no C52 . H521 . 1.000 no C52 . H522 . 1.000 no C52 . H523 . 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 C11 . C1 . H11 . 109.47 no C11 . C1 . H12 . 109.47 no H11 . C1 . H12 . 109.48 no C11 . C1 . H13 . 109.47 no H11 . C1 . H13 . 109.48 no H12 . C1 . H13 . 109.48 no C1 . C11 . C11 2_755 119.6(2) yes C1 . C11 . N11 . 125.28(16) yes C11 2_755 C11 . N11 . 115.1(2) yes C11 . N11 . N12 . 116.85(16) yes N11 . N12 . C12 . 118.90(16) yes N11 . N12 . H1 . 121.0(19) yes C12 . N12 . H1 . 115.5(19) yes N12 . C12 . S1 . 118.73(14) yes N12 . C12 . N13 . 117.36(17) yes S1 . C12 . N13 . 123.90(15) yes C12 . N13 . C13 . 122.89(17) yes C12 . N13 . H2 . 119.(2) yes C13 . N13 . H2 . 118.(2) yes N13 . C13 . H131 . 109.47 no N13 . C13 . H132 . 109.5 no H131 . C13 . H132 . 109.5 no N13 . C13 . H133 . 109.47 no H131 . C13 . H133 . 109.5 no H132 . C13 . H133 . 109.5 no C31 . C3 . H31 . 109.47 no C31 . C3 . H32 . 109.47 no H31 . C3 . H32 . 109.5 no C31 . C3 . H33 . 109.47 no H31 . C3 . H33 . 109.5 no H32 . C3 . H33 . 109.48 no C3 . C31 . C31 2_665 119.5(2) yes C3 . C31 . N31 . 126.24(17) yes C31 2_665 C31 . N31 . 114.2(2) yes C31 . N31 . N32 . 118.25(16) yes N31 . N32 . C32 . 117.33(17) yes N31 . N32 . H3 . 122.8(19) yes C32 . N32 . H3 . 117.0(19) yes N32 . C32 . S3 . 119.12(15) yes N32 . C32 . N33 . 115.95(17) yes S3 . C32 . N33 . 124.93(15) yes C32 . N33 . C33 . 124.15(18) yes C32 . N33 . H4 . 117.1(19) yes C33 . N33 . H4 . 118.7(19) yes N33 . C33 . H331 . 109.5 no N33 . C33 . H332 . 109.5 no H331 . C33 . H332 . 109.5 no N33 . C33 . H333 . 109.5 no H331 . C33 . H333 . 109.5 no H332 . C33 . H333 . 109.5 no O41 . S41 . C41 . 105.11(13) yes O41 . S41 . C42 . 105.30(13) yes C41 . S41 . C42 . 99.03(14) yes S41 . C41 . H411 . 109.5 no S41 . C41 . H412 . 109.5 no H411 . C41 . H412 . 109.5 no S41 . C41 . H413 . 109.5 no H411 . C41 . H413 . 109.5 no H412 . C41 . H413 . 109.5 no S41 . C42 . H421 . 109.5 no S41 . C42 . H422 . 109.5 no H421 . C42 . H422 . 109.5 no S41 . C42 . H423 . 109.5 no H421 . C42 . H423 . 109.5 no H422 . C42 . H423 . 109.5 no O51 . S51 . C51 . 105.0(1) yes O51 . S51 . C52 . 106.27(11) yes C51 . S51 . C52 . 97.35(11) yes S51 . C51 . H511 . 109.47 no S51 . C51 . H512 . 109.47 no H511 . C51 . H512 . 109.5 no S51 . C51 . H513 . 109.47 no H511 . C51 . H513 . 109.5 no H512 . C51 . H513 . 109.5 no S51 . C52 . H521 . 109.47 no S51 . C52 . H522 . 109.47 no H521 . C52 . H522 . 109.5 no S51 . C52 . H523 . 109.47 no H521 . C52 . H523 . 109.5 no H522 . C52 . H523 . 109.5 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N13 H2 O41 0.82(3) 2.09(3) 2.837(3) 152.(3) yes N32 H3 O51 0.87(3) 1.99(3) 2.838(2) 166.(3) yes data_CRYSTALS_cif_a _database_code_CSD 219684 #============================================================= # 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_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_special_details ; The NH hydrogen atom was located in a difference Fourier map. Other hydrogen atoms were positioned geometrically. The orientations of the methyl groups were found in a difference Fourier map and their hydrogen atoms subsequently placed geometrically in positions corresponding to the idealised geometries of the groups. ; #============================================================= _cell_length_a 12.3084(4) _cell_angle_alpha 90 _cell_length_b 12.9874(5) _cell_angle_beta 90.591(3) _cell_length_c 8.2414(3) _cell_angle_gamma 90 _cell_volume 1317.4 _symmetry_cell_setting 'Monoclinic ' _symmetry_space_group_name_H-M 'C 1 2/c 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-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 'Cu ' 0.2630 1.2660 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 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 _chemical_formula_sum ' C8 H14 Cu N6 S2 ' _chemical_formula_moiety ' C8 H14 Cu N6 S2 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 321.90 _cell_measurement_reflns_used 5344 _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 ' red ' _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.16 _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_meas ? _exptl_crystal_F_000 661.905 _exptl_absorpt_coefficient_mu 1.962 _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 0.85 _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 5344 _reflns_number_total 1513 #1576 unique reflections including absences _diffrn_reflns_av_R_equivalents 0.031 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_gt 1259 _diffrn_reflns_theta_min 5.18 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _reflns_limit_h_min -15 _reflns_limit_h_max 15 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 10 _refine_diff_density_min -0.44 _refine_diff_density_max 0.45 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 1259 _refine_ls_number_parameters 82 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0325 _refine_ls_goodness_of_fit_ref 1.0696 _refine_ls_shift/su_max 0.002989 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979) 1.74 0.0712 1.09 ; _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 Cu1 0.5000 0.56995(3) 0.2500 0.0179 1.0000 Uani C11 0.45127(16) 0.36371(16) 0.3018(2) 0.0206 1.0000 Uani N11 0.41729(14) 0.45490(13) 0.3400(2) 0.0192 1.0000 Uani N12 0.32806(15) 0.46741(14) 0.4358(2) 0.0224 1.0000 Uani C12 0.30448(17) 0.56613(16) 0.4555(3) 0.0215 1.0000 Uani S1 0.37759(4) 0.67009(4) 0.37421(6) 0.0227 1.0000 Uani C1 0.39676(19) 0.26668(16) 0.3560(3) 0.0285 1.0000 Uani N13 0.21661(17) 0.58928(15) 0.5430(3) 0.0281 1.0000 Uani C13 0.1470(2) 0.5120(2) 0.6131(3) 0.0339 1.0000 Uani H1 0.201(3) 0.655(3) 0.554(4) 0.036(8) 1.0000 Uiso H11 0.3329 0.2843 0.4247 0.0342 1.0000 Uiso H12 0.4494 0.2242 0.4207 0.0342 1.0000 Uiso H13 0.3717 0.2267 0.2589 0.0342 1.0000 Uiso H131 0.0868 0.5463 0.6729 0.0408 1.0000 Uiso H132 0.1903 0.4683 0.6899 0.0408 1.0000 Uiso H133 0.1158 0.4678 0.5248 0.0408 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 Cu1 0.02155(19) 0.01106(18) 0.02106(18) 0.0000 0.00090(12) 0.0000 C11 0.023(1) 0.0151(9) 0.0232(9) 0.0008(8) -0.0060(8) -0.0017(8) N11 0.0201(8) 0.0148(8) 0.0225(8) 0.0011(6) -0.0038(6) 0.0001(6) N12 0.0233(8) 0.0179(8) 0.0260(8) -0.0003(7) 0.0011(7) -0.0008(7) C12 0.021(1) 0.020(1) 0.0233(9) 0.0011(8) -0.0029(7) -0.0007(8) S1 0.0238(3) 0.0148(3) 0.0295(3) 0.00019(18) 0.0044(2) 0.00145(18) C1 0.0293(11) 0.015(1) 0.0414(13) 0.0019(9) -0.003(1) -0.0043(8) N13 0.0278(9) 0.0218(9) 0.035(1) -0.0007(8) 0.0080(8) -0.0008(8) C13 0.0274(11) 0.0363(13) 0.0383(12) 0.004(1) 0.0080(9) -0.005(1) _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 Cu1 . N11 . 1.9583(17) yes Cu1 . N11 5_655 1.9583(17) yes Cu1 . S1 . 2.2453(5) yes Cu1 . S1 5_655 2.2453(5) yes C11 . C11 5_655 1.480(4) yes C11 . N11 . 1.296(3) yes C11 . C1 . 1.498(3) yes N11 . N12 . 1.369(3) yes N12 . C12 . 1.325(3) yes C12 . S1 . 1.759(2) yes C12 . N13 . 1.340(3) yes C1 . H11 . 1.000 no C1 . H12 . 1.000 no C1 . H13 . 1.000 no N13 . C13 . 1.444(3) yes N13 . H1 . 0.88(3) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C13 . H133 . 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 N11 . Cu1 . N11 5_655 80.55(10) yes N11 . Cu1 . S1 . 85.14(5) yes N11 5_655 Cu1 . S1 . 165.61(5) yes N11 . Cu1 . S1 5_655 165.61(5) yes N11 5_655 Cu1 . S1 5_655 85.14(5) yes S1 . Cu1 . S1 5_655 109.21(3) yes C11 5_655 C11 . N11 . 113.94(12) yes C11 5_655 C11 . C1 . 122.71(12) yes N11 . C11 . C1 . 123.3(2) yes Cu1 . N11 . C11 . 115.78(15) yes Cu1 . N11 . N12 . 123.46(13) yes C11 . N11 . N12 . 120.76(17) yes N11 . N12 . C12 . 111.32(18) yes N12 . C12 . S1 . 125.63(17) yes N12 . C12 . N13 . 117.5(2) yes S1 . C12 . N13 . 116.85(16) yes Cu1 . S1 . C12 . 94.44(8) yes C11 . C1 . H11 . 109.47 no C11 . C1 . H12 . 109.47 no H11 . C1 . H12 . 109.5 no C11 . C1 . H13 . 109.5 no H11 . C1 . H13 . 109.5 no H12 . C1 . H13 . 109.5 no C12 . N13 . C13 . 123.0(2) yes C12 . N13 . H1 . 117.(2) yes C13 . N13 . H1 . 120.(2) yes N13 . C13 . H131 . 109.5 no N13 . C13 . H132 . 109.5 no H131 . C13 . H132 . 109.5 no N13 . C13 . H133 . 109.5 no H131 . C13 . H133 . 109.5 no H132 . C13 . H133 . 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 N13 H1 S1 4_566 0.88(3) 2.54(3) 3.405(2) 168.(3) yes