# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4(ruben09-culsh)-1 _audit_creation_date 2013-03-22T17:49:51-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C14 H16 Cu2 N8 S4' _chemical_formula_sum 'C14 H16 Cu2 N8 S4' _chemical_formula_weight 551.66 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.668(5) _cell_length_b 8.251(5) _cell_length_c 8.861(5) _cell_angle_alpha 111.221(7) _cell_angle_beta 93.978(8) _cell_angle_gamma 108.043(7) _cell_volume 486.4(5) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _exptl_crystal_colour green _exptl_crystal_description prismatic _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.884 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 278 _exptl_absorpt_coefficient_mu 2.635 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7092 _exptl_absorpt_correction_T_max 0.9492 #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_measurement_device_type 'Bruker Smart with Apex detector' _diffrn_measurement_method 'Phi and omega scans' _diffrn_ambient_temperature 100(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_reflns_number 2307 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_unetI/netI 0.0733 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 21.64 _diffrn_reflns_theta_full 21.64 _diffrn_measured_fraction_theta_max 0.976 _diffrn_measured_fraction_theta_full 0.976 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 #============================================================================== # STRUCTURE SOLUTION _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #============================================================================== # REFINEMENT DATA _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. ; _reflns_number_total 1114 _reflns_number_gt 827 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0818 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1347 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_number_reflns 1114 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0611P)^2^+1.7436P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.855 _refine_diff_density_min -0.547 _refine_diff_density_rms 0.119 _refine_ls_extinction_method none 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 0 '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' _computing_data_collection 'Bruker SMART (Bruker, 2007)' _computing_cell_refinement 'Bruker SMART (Bruker, 2007)' _computing_data_reduction 'Bruker SAINT (Bruker, 2007)' _computing_molecular_graphics 'CrystalMaker 4.1 (Palmer, D.C., 1994-2001)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cu1 0.97365(17) 0.16235(15) 0.42881(14) 0.0297(5) Uani d . 1 . . Cu S1 0.8040(4) 0.0401(3) 0.5896(3) 0.0302(7) Uani d . 1 . . S S2 0.7598(4) -0.0087(3) 0.1895(3) 0.0406(8) Uani d . 1 . . S H2A 0.6178 0.0223 0.2056 0.061 Uiso calc R 1 . . H N1 1.1559(11) 0.3326(10) 0.3482(9) 0.028(2) Uani d . 1 . . N N2 1.0877(10) 0.3803(10) 0.6422(9) 0.026(2) Uani d . 1 . . N N3 1.0391(11) 0.3929(10) 0.7894(9) 0.029(2) Uani d . 1 . . N N4 0.8395(11) 0.2364(11) 0.9094(9) 0.035(2) Uani d . 1 . . N H4A 0.8851 0.3358 1.0031 0.042 Uiso calc R 1 . . H H4B 0.7505 0.1361 0.9047 0.042 Uiso calc R 1 . . H C1 1.1947(14) 0.2996(13) 0.1966(12) 0.035(3) Uani d . 1 . . C H1 1.1278 0.1811 0.1096 0.042 Uiso calc R 1 . . H C2 1.3286(13) 0.4320(13) 0.1620(12) 0.034(3) Uani d . 1 . . C H2 1.3523 0.4034 0.0533 0.04 Uiso calc R 1 . . H C3 1.4258(13) 0.6030(13) 0.2849(12) 0.032(3) Uani d . 1 . . C H3 1.5158 0.6955 0.2624 0.038 Uiso calc R 1 . . H C4 1.3912(13) 0.6406(13) 0.4447(12) 0.032(3) Uani d . 1 . . C H4 1.4577 0.7585 0.5327 0.039 Uiso calc R 1 . . H C5 1.2594(13) 0.5035(12) 0.4714(11) 0.025(2) Uani d . 1 . . C C6 1.2156(13) 0.5244(13) 0.6349(11) 0.025(2) Uani d . 1 . . C H6 1.2768 0.6367 0.7304 0.03 Uiso calc R 1 . . H C7 0.9051(14) 0.2377(13) 0.7744(12) 0.029(2) Uani d . 1 . . C loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu1 0.0360(8) 0.0190(7) 0.0252(7) -0.0005(6) 0.0098(6) 0.0074(6) S1 0.0384(17) 0.0179(13) 0.0283(14) 0.0018(12) 0.0137(12) 0.0084(12) S2 0.0482(19) 0.0254(15) 0.0242(15) -0.0128(14) 0.0060(13) 0.0059(12) N1 0.040(5) 0.020(5) 0.023(5) 0.006(4) 0.010(4) 0.012(4) N2 0.023(5) 0.024(5) 0.027(5) 0.007(4) 0.007(4) 0.007(4) N3 0.034(5) 0.021(5) 0.029(5) 0.004(4) 0.014(4) 0.011(4) N4 0.044(6) 0.024(5) 0.030(5) -0.002(4) 0.019(4) 0.012(4) C1 0.037(7) 0.022(6) 0.036(7) -0.002(5) 0.005(5) 0.013(5) C2 0.028(6) 0.032(6) 0.034(6) 0.000(5) 0.007(5) 0.016(5) C3 0.028(6) 0.019(6) 0.045(7) 0.002(5) 0.011(5) 0.014(5) C4 0.029(6) 0.018(5) 0.044(7) 0.004(5) 0.012(5) 0.010(5) C5 0.023(6) 0.023(6) 0.029(6) 0.007(5) 0.004(5) 0.009(5) C6 0.016(6) 0.021(6) 0.025(5) -0.001(5) 0.004(4) 0.001(5) C7 0.027(6) 0.030(6) 0.035(6) 0.008(5) 0.015(5) 0.020(5) #============================================================================== # MOLECULAR GEOMETRY _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 N2 . 1.977(7) ? Cu1 N1 . 2.021(8) ? Cu1 S2 . 2.257(3) ? Cu1 S1 . 2.285(3) ? Cu1 S1 2_756 2.708(3) ? S1 C7 . 1.746(10) ? S1 Cu1 2_756 2.708(3) ? N3 C7 . 1.325(12) ? N3 N2 . 1.358(10) ? N4 C7 . 1.332(11) ? N4 H4A . 0.88 ? N4 H4B . 0.88 ? C6 N2 . 1.312(11) ? C6 C5 . 1.471(12) ? C6 H6 . 0.95 ? N1 C1 . 1.345(12) ? N1 C5 . 1.372(11) ? C4 C5 . 1.370(13) ? C4 C3 . 1.399(13) ? C4 H4 . 0.95 ? C1 C2 . 1.390(13) ? C1 H1 . 0.95 ? C2 C3 . 1.362(12) ? C2 H2 . 0.95 ? C3 H3 . 0.95 ? S2 H2A . 1.2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N1 81.3(3) . . ? N2 Cu1 S2 153.6(2) . . ? N1 Cu1 S2 97.5(2) . . ? N2 Cu1 S1 82.5(2) . . ? N1 Cu1 S1 163.9(2) . . ? S2 Cu1 S1 96.90(11) . . ? N2 Cu1 S1 103.9(2) . 2_756 ? N1 Cu1 S1 91.2(2) . 2_756 ? S2 Cu1 S1 102.56(10) . 2_756 ? S1 Cu1 S1 92.67(10) . 2_756 ? C7 S1 Cu1 95.9(3) . . ? C7 S1 Cu1 105.0(3) . 2_756 ? Cu1 S1 Cu1 87.33(10) . 2_756 ? C7 N3 N2 111.5(7) . . ? C7 N4 H4A 120 . . ? C7 N4 H4B 120 . . ? H4A N4 H4B 120 . . ? N2 C6 C5 116.7(8) . . ? N2 C6 H6 121.7 . . ? C5 C6 H6 121.7 . . ? C1 N1 C5 116.8(8) . . ? C1 N1 Cu1 129.8(6) . . ? C5 N1 Cu1 113.3(6) . . ? C5 C4 C3 118.5(9) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? C4 C5 N1 123.2(8) . . ? C4 C5 C6 123.4(8) . . ? N1 C5 C6 113.3(8) . . ? N3 C7 N4 117.1(8) . . ? N3 C7 S1 124.6(7) . . ? N4 C7 S1 118.2(7) . . ? N1 C1 C2 122.7(9) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C6 N2 N3 119.2(7) . . ? C6 N2 Cu1 115.3(6) . . ? N3 N2 Cu1 125.4(6) . . ? C3 C2 C1 119.6(9) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 119.2(9) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? Cu1 S2 H2A 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 N2 Cu1 S1 C7 1.2(4) . . . . ? N1 Cu1 S1 C7 1.1(9) . . . . ? S2 Cu1 S1 C7 -152.2(3) . . . . ? S1 Cu1 S1 C7 104.8(3) 2_756 . . . ? N2 Cu1 S1 Cu1 -103.6(2) . . . 2_756 ? N1 Cu1 S1 Cu1 -103.7(8) . . . 2_756 ? S2 Cu1 S1 Cu1 103.00(11) . . . 2_756 ? S1 Cu1 S1 Cu1 0 2_756 . . 2_756 ? N2 Cu1 N1 C1 175.9(9) . . . . ? S2 Cu1 N1 C1 -30.7(8) . . . . ? S1 Cu1 N1 C1 176.0(7) . . . . ? S1 Cu1 N1 C1 72.1(8) 2_756 . . . ? N2 Cu1 N1 C5 -0.8(6) . . . . ? S2 Cu1 N1 C5 152.6(6) . . . . ? S1 Cu1 N1 C5 -0.7(13) . . . . ? S1 Cu1 N1 C5 -104.6(6) 2_756 . . . ? C3 C4 C5 N1 -1.8(14) . . . . ? C3 C4 C5 C6 177.9(9) . . . . ? C1 N1 C5 C4 2.9(13) . . . . ? Cu1 N1 C5 C4 -180.0(7) . . . . ? C1 N1 C5 C6 -176.8(8) . . . . ? Cu1 N1 C5 C6 0.3(9) . . . . ? N2 C6 C5 C4 -179.1(9) . . . . ? N2 C6 C5 N1 0.6(11) . . . . ? N2 N3 C7 N4 -177.0(8) . . . . ? N2 N3 C7 S1 0.5(11) . . . . ? Cu1 S1 C7 N3 -1.3(9) . . . . ? Cu1 S1 C7 N3 87.5(8) 2_756 . . . ? Cu1 S1 C7 N4 176.1(7) . . . . ? Cu1 S1 C7 N4 -95.1(7) 2_756 . . . ? C5 N1 C1 C2 -1.9(14) . . . . ? Cu1 N1 C1 C2 -178.5(7) . . . . ? C5 C6 N2 N3 -178.8(7) . . . . ? C5 C6 N2 Cu1 -1.2(10) . . . . ? C7 N3 N2 C6 178.3(8) . . . . ? C7 N3 N2 Cu1 1.0(10) . . . . ? N1 Cu1 N2 C6 1.1(6) . . . . ? S2 Cu1 N2 C6 -88.3(8) . . . . ? S1 Cu1 N2 C6 -178.9(6) . . . . ? S1 Cu1 N2 C6 90.2(6) 2_756 . . . ? N1 Cu1 N2 N3 178.5(7) . . . . ? S2 Cu1 N2 N3 89.0(8) . . . . ? S1 Cu1 N2 N3 -1.5(6) . . . . ? S1 Cu1 N2 N3 -92.4(7) 2_756 . . . ? N1 C1 C2 C3 -0.1(15) . . . . ? C1 C2 C3 C4 1.3(14) . . . . ? C5 C4 C3 C2 -0.4(14) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 930871' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_clgua-abs-std _audit_creation_date 2010-11-29T13:14:03-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_formula_sum 'C26 H22 Cl2 Cu3 N10 O4 S2' _chemical_formula_moiety 'C14 H14 Cl2 Cu2 N8 S2, C12 H8 Cu N2 O4' _chemical_formula_weight 864.18 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.968(4) _cell_length_b 16.018(6) _cell_length_c 9.462(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.91(3) _cell_angle_gamma 90.00 _cell_volume 1552.9(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.16 _cell_measurement_theta_min 2.36 _cell_measurement_reflns_used 1238 _exptl_crystal_density_diffrn 1.848 _exptl_crystal_density_method 'not measured' _exptl_crystal_colour geen _exptl_crystal_description prismatic _exptl_crystal_size_max 0.0107 _exptl_crystal_size_mid 0.0077 _exptl_crystal_size_min 0.0048 _exptl_crystal_F_000 866 _exptl_absorpt_coefficient_mu 2.395 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; a grid of 8 x 8 x 8 = 512 sampling points was used ; _exptl_absorpt_correction_T_min 0.8362 _exptl_absorpt_correction_T_max 0.9289 #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_measurement_device_type 'Stoe IPDS I' _diffrn_measurement_method 'Phi scans' _diffrn_ambient_temperature 293(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_reflns_number 11981 _diffrn_reflns_av_R_equivalents 0.2374 _diffrn_reflns_av_unetI/netI 0.3158 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 26.16 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_max 0.955 _diffrn_measured_fraction_theta_full 0.974 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 #============================================================================== # STRUCTURE SOLUTION _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #============================================================================== # REFINEMENT DATA _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^ > 2\s(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. ; _reflns_number_total 2961 _reflns_number_gt 796 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.2246 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1087 _refine_ls_goodness_of_fit_ref 0.669 _refine_ls_restrained_S_all 0.669 _refine_ls_number_reflns 2961 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0058P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.339 _refine_diff_density_min -0.58 _refine_diff_density_rms 0.091 _refine_ls_extinction_method none 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Stoe IPDS Software (Stoe, 1998)' _computing_cell_refinement 'Stoe IPDS Software (Stoe, 1998)' _computing_data_reduction 'Stoe IPDS Software (Stoe, 1998)' _computing_molecular_graphics 'CrystalMaker 4.1 (Palmer, D.C., 1994-2001)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cu1 0.66023(14) -0.03654(8) 0.53027(17) 0.0508(4) Uani d . 1 . . Cu Cl1 0.5260(3) 0.00887(16) 0.3056(3) 0.0608(9) Uani d . 1 . . Cl S1 0.7795(3) 0.08172(16) 0.6019(4) 0.0571(10) Uani d . 1 . . S N1 0.6073(8) -0.1571(5) 0.5047(11) 0.047(2) Uani d . 1 . . N N2 0.7820(8) -0.0801(5) 0.7195(10) 0.045(3) Uani d . 1 . . N N3 0.8724(8) -0.0320(6) 0.8279(10) 0.051(3) Uani d . 1 . . N N4 0.9641(9) 0.0959(5) 0.8725(11) 0.066(3) Uani d . 1 . . N H4A 1.0147 0.0775 0.9589 0.098 Uiso calc R 1 . . H H4B 0.9708 0.1467 0.847 0.098 Uiso calc R 1 . . H C1 0.5219(11) -0.1970(6) 0.3866(14) 0.061(4) Uani d . 1 . . C H1 0.4738 -0.1657 0.3025 0.091 Uiso calc R 1 . . H C2 0.5010(11) -0.2824(7) 0.3822(15) 0.065(4) Uani d . 1 . . C H2 0.4395 -0.3077 0.2985 0.098 Uiso calc R 1 . . H C3 0.5738(12) -0.3282(7) 0.5049(16) 0.068(4) Uani d . 1 . . C H3 0.5626 -0.3858 0.5041 0.102 Uiso calc R 1 . . H C4 0.6644(11) -0.2903(6) 0.6311(15) 0.065(4) Uani d . 1 . . C H4 0.714 -0.3213 0.715 0.098 Uiso calc R 1 . . H C5 0.6774(11) -0.2061(6) 0.6267(14) 0.049(3) Uani d . 1 . . C C6 0.7719(11) -0.1589(7) 0.7451(14) 0.054(3) Uani d . 1 . . C H6 0.8233 -0.1837 0.8356 0.081 Uiso calc R 1 . . H C7 0.8755(10) 0.0457(6) 0.7785(12) 0.041(3) Uani d . 1 . . C Cu2 1 0 0.5 0.0630(7) Uani d S 1 . . Cu O1 0.9174(7) -0.1088(4) 0.4559(9) 0.056(2) Uani d . 1 . . O O2 0.9384(8) -0.2380(4) 0.5475(10) 0.069(3) Uani d . 1 . . O N5 1.1047(9) -0.0522(5) 0.6900(11) 0.049(3) Uani d . 1 . . N C8 1.1963(10) -0.0162(7) 0.8153(14) 0.057(3) Uani d . 1 . . C H8 1.2151 0.0403 0.8131 0.085 Uiso calc R 1 . . H C9 1.2601(11) -0.0613(7) 0.9425(14) 0.058(4) Uani d . 1 . . C H9 1.325 -0.0369 1.0242 0.088 Uiso calc R 1 . . H C10 1.2263(12) -0.1436(8) 0.9472(15) 0.075(4) Uani d . 1 . . C H10 1.2655 -0.1745 1.035 0.112 Uiso calc R 1 . . H C11 1.1333(12) -0.1815(7) 0.8211(15) 0.064(4) Uani d . 1 . . C H11 1.1128 -0.2379 0.821 0.096 Uiso calc R 1 . . H C12 1.0749(11) -0.1324(7) 0.6996(15) 0.053(3) Uani d . 1 . . C C13 0.9686(11) -0.1634(8) 0.5583(15) 0.059(4) Uani d . 1 . . C loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu1 0.0490(8) 0.0406(7) 0.0482(11) 0.0001(7) -0.0004(7) 0.0008(7) Cl1 0.0590(18) 0.0633(18) 0.045(2) 0.0023(15) 0.0007(15) 0.0090(14) S1 0.054(2) 0.0481(16) 0.053(2) -0.0060(14) 0.0003(16) 0.0024(15) N1 0.044(5) 0.057(6) 0.035(7) 0.006(4) 0.007(5) -0.007(5) N2 0.042(5) 0.046(5) 0.045(7) 0.001(4) 0.012(5) -0.004(4) N3 0.050(5) 0.052(5) 0.041(7) -0.005(5) 0.004(4) -0.011(5) N4 0.076(7) 0.041(5) 0.054(7) -0.012(5) -0.008(5) -0.011(5) C1 0.077(9) 0.045(7) 0.047(9) -0.003(6) 0.007(7) -0.012(6) C2 0.061(8) 0.049(7) 0.070(11) -0.014(6) 0.006(7) -0.001(7) C3 0.074(9) 0.050(7) 0.074(12) -0.006(6) 0.020(8) -0.013(7) C4 0.077(9) 0.040(6) 0.071(10) 0.009(6) 0.018(8) 0.003(6) C5 0.061(8) 0.033(6) 0.049(9) 0.004(5) 0.014(6) -0.002(5) C6 0.049(7) 0.048(7) 0.063(10) 0.005(6) 0.019(6) 0.006(6) C7 0.058(7) 0.026(5) 0.042(8) -0.006(5) 0.022(5) -0.005(5) Cu2 0.0670(14) 0.0561(12) 0.0490(16) -0.0165(11) 0.0002(11) 0.0024(11) O1 0.058(5) 0.050(5) 0.045(6) -0.010(4) 0.002(4) 0.008(4) O2 0.077(6) 0.036(4) 0.075(7) -0.002(4) 0.005(5) 0.000(4) N5 0.053(6) 0.044(6) 0.051(7) -0.003(4) 0.018(5) -0.010(5) C8 0.053(7) 0.053(8) 0.058(9) -0.003(6) 0.013(6) 0.000(6) C9 0.052(7) 0.062(8) 0.050(10) -0.004(6) 0.003(6) -0.006(6) C10 0.075(10) 0.073(9) 0.054(11) 0.010(7) -0.004(7) 0.002(7) C11 0.062(8) 0.048(7) 0.063(10) 0.001(6) -0.001(7) 0.007(6) C12 0.056(8) 0.040(6) 0.059(10) -0.005(6) 0.016(6) -0.007(6) C13 0.058(8) 0.058(8) 0.057(10) 0.017(6) 0.016(7) 0.005(7) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 N2 . 1.942(9) ? Cu1 N1 . 2.005(8) ? Cu1 Cl1 . 2.232(3) ? Cu1 S1 . 2.264(3) ? S1 C7 . 1.725(11) ? N1 C1 . 1.337(12) ? N1 C5 . 1.381(13) ? N2 C6 . 1.296(11) ? N2 N3 . 1.379(10) ? N3 C7 . 1.335(11) ? N4 C7 . 1.328(11) ? N4 H4A . 0.86 ? N4 H4B . 0.86 ? C1 C2 . 1.385(13) ? C1 H1 . 0.93 ? C2 C3 . 1.364(15) ? C2 H2 . 0.93 ? C3 C4 . 1.392(15) ? C3 H3 . 0.93 ? C4 C5 . 1.358(13) ? C4 H4 . 0.93 ? C5 C6 . 1.440(14) ? C6 H6 . 0.93 ? Cu2 O1 3_756 1.940(7) ? Cu2 O1 . 1.940(7) ? Cu2 N5 3_756 1.943(9) ? Cu2 N5 . 1.943(9) ? O1 C13 . 1.277(13) ? O2 C13 . 1.233(12) ? N5 C12 . 1.337(12) ? N5 C8 . 1.377(13) ? C8 C9 . 1.364(14) ? C8 H8 . 0.93 ? C9 C10 . 1.375(14) ? C9 H9 . 0.93 ? C10 C11 . 1.401(15) ? C10 H10 . 0.93 ? C11 C12 . 1.351(15) ? C11 H11 . 0.93 ? C12 C13 . 1.510(15) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N1 80.8(4) . . ? N2 Cu1 Cl1 176.6(3) . . ? N1 Cu1 Cl1 97.7(3) . . ? N2 Cu1 S1 83.7(3) . . ? N1 Cu1 S1 162.4(2) . . ? Cl1 Cu1 S1 97.28(12) . . ? C7 S1 Cu1 95.6(4) . . ? C1 N1 C5 116.1(9) . . ? C1 N1 Cu1 130.4(8) . . ? C5 N1 Cu1 113.3(6) . . ? C6 N2 N3 119.4(9) . . ? C6 N2 Cu1 116.5(7) . . ? N3 N2 Cu1 124.1(7) . . ? C7 N3 N2 111.3(8) . . ? C7 N4 H4A 120 . . ? C7 N4 H4B 120 . . ? H4A N4 H4B 120 . . ? N1 C1 C2 123.8(11) . . ? N1 C1 H1 118.1 . . ? C2 C1 H1 118.1 . . ? C3 C2 C1 117.7(11) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C2 C3 C4 121.1(11) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 117.3(11) . . ? C5 C4 H4 121.4 . . ? C3 C4 H4 121.4 . . ? C4 C5 N1 123.9(10) . . ? C4 C5 C6 123.5(10) . . ? N1 C5 C6 112.5(9) . . ? N2 C6 C5 116.9(10) . . ? N2 C6 H6 121.6 . . ? C5 C6 H6 121.6 . . ? N4 C7 N3 115.7(9) . . ? N4 C7 S1 119.7(8) . . ? N3 C7 S1 124.6(8) . . ? O1 Cu2 O1 180.0000(10) 3_756 . ? O1 Cu2 N5 83.6(3) 3_756 3_756 ? O1 Cu2 N5 96.4(3) . 3_756 ? O1 Cu2 N5 96.4(3) 3_756 . ? O1 Cu2 N5 83.6(3) . . ? N5 Cu2 N5 180.0000(10) 3_756 . ? C13 O1 Cu2 114.0(7) . . ? C12 N5 C8 117.7(10) . . ? C12 N5 Cu2 113.5(7) . . ? C8 N5 Cu2 128.6(7) . . ? C9 C8 N5 121.6(10) . . ? C9 C8 H8 119.2 . . ? N5 C8 H8 119.2 . . ? C8 C9 C10 118.5(10) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? C9 C10 C11 120.7(11) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C10 116.9(11) . . ? C12 C11 H11 121.5 . . ? C10 C11 H11 121.5 . . ? N5 C12 C11 124.3(11) . . ? N5 C12 C13 112.7(11) . . ? C11 C12 C13 122.9(11) . . ? O2 C13 O1 124.6(11) . . ? O2 C13 C12 119.4(11) . . ? O1 C13 C12 115.9(11) . . ? 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 #Cl1 Cu1 N2 C6 -66(5) . . . . ? #Cl1 Cu1 N2 N3 117(5) . . . . ? #O1 Cu2 O1 C13 -0E1(10) 3_756 . . . ? #N5 Cu2 N5 C12 -2E1(10) 3_756 . . . ? #N5 Cu2 N5 C8 17E1(10) 3_756 . . . ? N2 Cu1 S1 C7 -6.1(5) . . . . ? N1 Cu1 S1 C7 -34.7(11) . . . . ? Cl1 Cu1 S1 C7 177.1(4) . . . . ? N2 Cu1 N1 C1 -174.5(11) . . . . ? Cl1 Cu1 N1 C1 2.4(11) . . . . ? S1 Cu1 N1 C1 -145.7(9) . . . . ? N2 Cu1 N1 C5 1.0(8) . . . . ? Cl1 Cu1 N1 C5 178.0(8) . . . . ? S1 Cu1 N1 C5 29.8(16) . . . . ? N1 Cu1 N2 C6 -2.6(9) . . . . ? S1 Cu1 N2 C6 -174.2(9) . . . . ? N1 Cu1 N2 N3 -179.8(9) . . . . ? S1 Cu1 N2 N3 8.7(8) . . . . ? C6 N2 N3 C7 175.7(11) . . . . ? Cu1 N2 N3 C7 -7.2(12) . . . . ? C5 N1 C1 C2 0.5(18) . . . . ? Cu1 N1 C1 C2 175.9(9) . . . . ? N1 C1 C2 C3 -1(2) . . . . ? C1 C2 C3 C4 1(2) . . . . ? C2 C3 C4 C5 0(2) . . . . ? C3 C4 C5 N1 -0.7(19) . . . . ? C3 C4 C5 C6 -176.5(13) . . . . ? C1 N1 C5 C4 0.5(18) . . . . ? Cu1 N1 C5 C4 -175.7(10) . . . . ? C1 N1 C5 C6 176.7(11) . . . . ? Cu1 N1 C5 C6 0.5(13) . . . . ? N3 N2 C6 C5 -179.0(10) . . . . ? Cu1 N2 C6 C5 3.7(14) . . . . ? C4 C5 C6 N2 173.5(12) . . . . ? N1 C5 C6 N2 -2.7(16) . . . . ? N2 N3 C7 N4 -177.0(10) . . . . ? N2 N3 C7 S1 -0.2(13) . . . . ? Cu1 S1 C7 N4 -177.9(9) . . . . ? Cu1 S1 C7 N3 5.4(10) . . . . ? N5 Cu2 O1 C13 176.5(9) 3_756 . . . ? N5 Cu2 O1 C13 -3.5(9) . . . . ? O1 Cu2 N5 C12 -179.0(8) 3_756 . . . ? O1 Cu2 N5 C12 1.0(8) . . . . ? O1 Cu2 N5 C8 5.8(11) 3_756 . . . ? O1 Cu2 N5 C8 -174.2(11) . . . . ? C12 N5 C8 C9 3.5(17) . . . . ? Cu2 N5 C8 C9 178.5(9) . . . . ? N5 C8 C9 C10 -3.5(19) . . . . ? C8 C9 C10 C11 3(2) . . . . ? C9 C10 C11 C12 -3(2) . . . . ? C8 N5 C12 C11 -3.6(19) . . . . ? Cu2 N5 C12 C11 -179.3(11) . . . . ? C8 N5 C12 C13 177.0(11) . . . . ? Cu2 N5 C12 C13 1.3(13) . . . . ? C10 C11 C12 N5 3(2) . . . . ? C10 C11 C12 C13 -177.2(13) . . . . ? Cu2 O1 C13 O2 -173.7(10) . . . . ? Cu2 O1 C13 C12 5.1(14) . . . . ? N5 C12 C13 O2 174.6(11) . . . . ? C11 C12 C13 O2 -5(2) . . . . ? N5 C12 C13 O1 -4.3(16) . . . . ? C11 C12 C13 O1 176.3(13) . . . . ? 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 N4 H4A N3 0.86 2.09 2.945(12) 177 3_757 N4 H4B O2 0.86 2.17 2.868(10) 139 2_756 # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 930872' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_culpic _audit_creation_date 2013-03-17T10:36:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H11 Cu N5 O2 S, 3(H2 O)' _chemical_formula_sum 'C13 H17 Cu N5 O5 S' _chemical_formula_weight 418.92 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 11.663(3) _cell_length_b 28.967(9) _cell_length_c 11.259(4) _cell_angle_alpha 90 _cell_angle_beta 109.92(2) _cell_angle_gamma 90 _cell_volume 3576.3(19) _cell_formula_units_Z 8 _cell_measurement_reflns_used 2711 _cell_measurement_theta_min 3.55 _cell_measurement_theta_max 46.44 _cell_measurement_temperature 293(2) _exptl_crystal_description prismatic _exptl_crystal_colour orange _exptl_crystal_size_max 0.056 _exptl_crystal_size_mid 0.025 _exptl_crystal_size_min 0.021 _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1720 _exptl_absorpt_coefficient_mu 1.372 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_measurement_device_type 'Stoe StadiVari Dectris detector' _diffrn_measurement_method 'Phi and omega scans' _diffrn_ambient_temperature 293(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_monochromator graphite _diffrn_reflns_number 14985 _diffrn_reflns_av_R_equivalents 0.4924 _diffrn_reflns_av_unetI/netI 0.9528 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 5 #============================================================================== # STRUCTURE SOLUTION _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #============================================================================== # REFINEMENT DATA _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^ > 2\s(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. O-H bond lengths and H-H distances corresponding to water molecules (O1W, O2W and O3W) were tightly restrained to be 0.850(5) angstrom and 1.37(1) angstrom respectively. Anti-bumping restraints were applied to atoms H1, H4B, H1W1, H2W1 and H1W2. Also the sets of adjacent atoms (C5, C6, N2) and (S1, C7, N3) were restrained to have similar Uij components. In addition rigid bond restraints were used for the pairs of atoms (S1, C7), (N5, C8) and the triplet (C6, C5, C4). ; _reflns_number_total 3136 _reflns_number_gt 613 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.3381 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.1494 _refine_ls_goodness_of_fit_ref 0.572 _refine_ls_restrained_S_all 0.575 _refine_ls_number_reflns 3136 _refine_ls_number_parameters 244 _refine_ls_number_restraints 37 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.355 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.093 _refine_ls_extinction_method none 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'X-AREA (Stoe, 2002)' _computing_cell_refinement 'X-AREA (Stoe, 2002)' _computing_data_reduction 'X-AREA (Stoe, 2002)' _computing_molecular_graphics 'CrystalMaker 4.1 (Palmer, D.C., 1994-2001)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cu1 0.30532(14) 0.11319(6) 0.15574(19) 0.0362(5) Uani d . 1 . . Cu S1 0.4433(3) 0.12913(12) 0.0586(4) 0.0408(11) Uani d U 1 . . S N1 0.2278(9) 0.0817(4) 0.2722(12) 0.038(4) Uani d . 1 . . N N2 0.3491(8) 0.0499(4) 0.1413(10) 0.027(3) Uani d U 1 . . N N3 0.4194(9) 0.0364(4) 0.0745(11) 0.033(3) Uani d U 1 . . N N4 0.5316(9) 0.0619(3) -0.0409(10) 0.037(3) Uani d . 1 . . N H4A 0.545 0.0337 -0.0553 0.056 Uiso calc R 1 . . H H4B 0.5622 0.0839 -0.0721 0.056 Uiso calc R 1 . . H C1 0.1680(11) 0.1002(6) 0.3449(14) 0.045(5) Uani d . 1 . . C H1 0.1638 0.1321 0.3503 0.068 Uiso calc RD 1 . . H C2 0.1135(13) 0.0735(6) 0.4109(16) 0.054(5) Uani d . 1 . . C H2 0.0728 0.0876 0.4593 0.081 Uiso calc R 1 . . H C3 0.1181(11) 0.0259(6) 0.4065(15) 0.050(5) Uani d . 1 . . C H3 0.081 0.0074 0.4505 0.075 Uiso calc R 1 . . H C4 0.1827(12) 0.0065(5) 0.3312(15) 0.039(4) Uani d U 1 . . C H4 0.1894 -0.0253 0.3242 0.059 Uiso calc R 1 . . H C5 0.2347(11) 0.0364(5) 0.2695(14) 0.032(3) Uani d U 1 . . C C6 0.3076(11) 0.0181(5) 0.1945(13) 0.030(3) Uani d U 1 . . C H6 0.3215 -0.0132 0.187 0.046 Uiso calc R 1 . . H C7 0.4647(11) 0.0716(5) 0.0285(13) 0.032(3) Uani d U 1 . . C O1 0.1261(6) 0.1175(3) -0.0050(8) 0.038(3) Uani d . 1 . . O O2 -0.0325(8) 0.1657(4) -0.0705(10) 0.061(3) Uani d . 1 . . O N5 0.2587(9) 0.1778(4) 0.1672(11) 0.031(3) Uani d U 1 . . N C8 0.3287(11) 0.2108(6) 0.2384(14) 0.043(4) Uani d U 1 . . C H8 0.4029 0.2016 0.297 0.064 Uiso calc R 1 . . H C9 0.3023(15) 0.2559(6) 0.2336(17) 0.069(6) Uani d . 1 . . C H9 0.3561 0.2768 0.2871 0.103 Uiso calc R 1 . . H C10 0.1899(15) 0.2711(6) 0.1447(14) 0.053(5) Uani d . 1 . . C H10 0.1683 0.3021 0.1352 0.079 Uiso calc R 1 . . H C11 0.1166(12) 0.2382(5) 0.0752(15) 0.052(5) Uani d . 1 . . C H11 0.0398 0.2463 0.02 0.078 Uiso calc R 1 . . H C12 0.1514(11) 0.1939(5) 0.0836(14) 0.036(4) Uani d . 1 . . C C13 0.0767(12) 0.1545(5) 0.0005(15) 0.042(5) Uani d . 1 . . C O1W 0.3743(8) 0.1367(4) 0.6663(10) 0.073(4) Uani d D 1 . . O H1W1 0.326(9) 0.153(3) 0.692(4) 0.11 Uiso d D 1 . . H H2W1 0.4008(3) 0.1179(5) 0.7292(10) 0.11 Uiso d D 1 . . H O2W 0.2295(10) 0.2019(4) 0.4940(12) 0.075(4) Uani d D 1 . . O H1W2 0.278(11) 0.179(3) 0.499(4) 0.112 Uiso d D 1 . . H H2W2 0.193(12) 0.197(4) 0.546(12) 0.112 Uiso d D 1 . . H O3W 0.1872(8) 0.1085(5) 0.7537(11) 0.073(4) Uani d D 1 . . O H1W3 0.200(5) 0.116(5) 0.830(4) 0.11 Uiso d D 1 . . H H2W3 0.127(10) 0.124(5) 0.708(10) 0.11 Uiso d D 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu1 0.0319(8) 0.0317(10) 0.0435(14) 0.0069(10) 0.0110(9) -0.0037(12) S1 0.043(2) 0.027(2) 0.057(3) 0.0040(17) 0.022(2) 0.001(2) N1 0.020(6) 0.019(7) 0.072(12) 0.006(5) 0.013(7) -0.012(7) N2 0.032(6) 0.029(7) 0.024(8) 0.007(5) 0.016(5) 0.000(6) N3 0.031(6) 0.048(8) 0.021(8) 0.002(5) 0.010(5) -0.004(6) N4 0.060(8) 0.014(6) 0.044(10) -0.003(6) 0.027(7) -0.003(7) C1 0.026(8) 0.059(12) 0.042(13) 0.012(7) 0.000(9) 0.012(10) C2 0.054(11) 0.060(14) 0.052(16) -0.001(9) 0.024(11) -0.018(11) C3 0.012(7) 0.079(14) 0.054(15) 0.005(8) 0.005(8) 0.011(11) C4 0.032(8) 0.038(9) 0.043(12) 0.007(7) 0.005(8) 0.010(9) C5 0.026(6) 0.032(7) 0.032(9) -0.005(6) 0.003(6) -0.004(7) C6 0.033(6) 0.028(7) 0.029(8) 0.005(5) 0.008(5) -0.006(6) C7 0.029(7) 0.048(7) 0.018(9) -0.003(6) 0.009(6) -0.014(7) O1 0.034(5) 0.031(6) 0.040(8) 0.008(5) 0.000(5) -0.005(6) O2 0.039(6) 0.074(9) 0.050(9) 0.017(6) -0.009(6) -0.005(7) N5 0.027(6) 0.034(8) 0.034(10) -0.002(5) 0.014(6) 0.002(7) C8 0.023(8) 0.056(12) 0.045(13) -0.001(7) 0.008(8) 0.006(9) C9 0.066(12) 0.037(11) 0.089(19) -0.013(9) 0.007(12) -0.012(12) C10 0.089(13) 0.040(11) 0.015(12) 0.016(10) -0.001(10) -0.002(9) C11 0.036(8) 0.041(11) 0.062(15) 0.015(8) -0.007(9) 0.005(11) C12 0.030(8) 0.029(9) 0.034(12) 0.014(7) -0.009(8) -0.004(8) C13 0.035(9) 0.040(10) 0.051(14) 0.007(8) 0.014(9) 0.013(9) O1W 0.059(7) 0.095(11) 0.071(10) 0.030(6) 0.027(7) 0.002(8) O2W 0.067(8) 0.093(10) 0.065(11) 0.006(7) 0.023(7) -0.005(8) O3W 0.064(7) 0.094(10) 0.064(9) 0.017(7) 0.025(7) 0.012(9) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 N2 . 1.926(11) ? Cu1 N5 . 1.965(11) ? Cu1 N1 . 2.043(12) ? Cu1 O1 . 2.255(8) ? Cu1 S1 . 2.280(4) ? S1 C7 . 1.734(14) ? N1 C5 . 1.315(15) ? N1 C1 . 1.354(16) ? N2 C6 . 1.280(15) ? N2 N3 . 1.346(12) ? N3 C7 . 1.333(16) ? N4 C7 . 1.309(14) ? N4 H4A . 0.86 ? N4 H4B . 0.86 ? C1 C2 . 1.369(19) ? C1 H1 . 0.93 ? C2 C3 . 1.38(2) ? C2 H2 . 0.93 ? C3 C4 . 1.427(18) ? C3 H3 . 0.93 ? C4 C5 . 1.374(18) ? C4 H4 . 0.93 ? C5 C6 . 1.486(17) ? C6 H6 . 0.93 ? O1 C13 . 1.229(15) ? O2 C13 . 1.293(14) ? N5 C8 . 1.332(16) ? N5 C12 . 1.366(14) ? C8 C9 . 1.34(2) ? C8 H8 . 0.93 ? C9 C10 . 1.421(18) ? C9 H9 . 0.93 ? C10 C11 . 1.339(18) ? C10 H10 . 0.93 ? C11 C12 . 1.339(18) ? C11 H11 . 0.93 ? C12 C13 . 1.543(18) ? O1W H1W1 . 0.862(5) ? O1W H2W1 . 0.862(5) ? O2W H1W2 . 0.854(5) ? O2W H2W2 . 0.849(5) ? O3W H1W3 . 0.850(5) ? O3W H2W3 . 0.850(5) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N5 179.0(5) . . ? N2 Cu1 N1 79.5(5) . . ? N5 Cu1 N1 101.0(4) . . ? N2 Cu1 O1 100.6(4) . . ? N5 Cu1 O1 78.4(4) . . ? N1 Cu1 O1 92.7(4) . . ? N2 Cu1 S1 84.4(3) . . ? N5 Cu1 S1 95.4(3) . . ? N1 Cu1 S1 159.6(3) . . ? O1 Cu1 S1 102.5(2) . . ? C7 S1 Cu1 94.1(5) . . ? C5 N1 C1 117.1(13) . . ? C5 N1 Cu1 112.8(10) . . ? C1 N1 Cu1 130.1(10) . . ? C6 N2 N3 116.9(12) . . ? C6 N2 Cu1 119.5(9) . . ? N3 N2 Cu1 123.6(9) . . ? C7 N3 N2 113.1(12) . . ? C7 N4 H4A 120 . . ? C7 N4 H4B 120 . . ? H4A N4 H4B 120 . . ? N1 C1 C2 122.4(16) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C1 C2 C3 120.8(16) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C2 C3 C4 116.7(15) . . ? C2 C3 H3 121.6 . . ? C4 C3 H3 121.6 . . ? C5 C4 C3 117.7(14) . . ? C5 C4 H4 121.2 . . ? C3 C4 H4 121.2 . . ? N1 C5 C4 125.2(14) . . ? N1 C5 C6 114.9(12) . . ? C4 C5 C6 119.9(14) . . ? N2 C6 C5 112.9(13) . . ? N2 C6 H6 123.5 . . ? C5 C6 H6 123.5 . . ? N4 C7 N3 117.6(13) . . ? N4 C7 S1 118.5(11) . . ? N3 C7 S1 123.9(11) . . ? C13 O1 Cu1 109.2(10) . . ? C8 N5 C12 113.6(12) . . ? C8 N5 Cu1 126.5(9) . . ? C12 N5 Cu1 119.2(9) . . ? N5 C8 C9 126.1(15) . . ? N5 C8 H8 116.9 . . ? C9 C8 H8 116.9 . . ? C8 C9 C10 118.3(15) . . ? C8 C9 H9 120.9 . . ? C10 C9 H9 120.9 . . ? C11 C10 C9 116.4(15) . . ? C11 C10 H10 121.8 . . ? C9 C10 H10 121.8 . . ? C10 C11 C12 121.5(14) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C11 C12 N5 124.0(14) . . ? C11 C12 C13 124.8(13) . . ? N5 C12 C13 111.2(12) . . ? O1 C13 O2 124.5(15) . . ? O1 C13 C12 119.9(12) . . ? O2 C13 C12 115.1(13) . . ? H1W1 O1W H2W1 99.3(11) . . ? H1W2 O2W H2W2 107.4(14) . . ? H1W3 O3W H2W3 107.4(14) . . ? 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 #N5 Cu1 N2 C6 -110(3) . . . . ? #N5 Cu1 N2 N3 70(3) . . . . ? #N2 Cu1 N5 C8 -150(3) . . . . ? #N2 Cu1 N5 C12 20(3) . . . . ? N2 Cu1 S1 C7 7.5(6) . . . . ? N5 Cu1 S1 C7 -171.4(6) . . . . ? N1 Cu1 S1 C7 45.2(12) . . . . ? O1 Cu1 S1 C7 -92.1(5) . . . . ? N2 Cu1 N1 C5 -6.3(10) . . . . ? N5 Cu1 N1 C5 172.8(10) . . . . ? O1 Cu1 N1 C5 94.0(10) . . . . ? S1 Cu1 N1 C5 -44.5(17) . . . . ? N2 Cu1 N1 C1 176.8(12) . . . . ? N5 Cu1 N1 C1 -4.2(13) . . . . ? O1 Cu1 N1 C1 -82.9(12) . . . . ? S1 Cu1 N1 C1 138.6(9) . . . . ? N1 Cu1 N2 C6 5.6(11) . . . . ? O1 Cu1 N2 C6 -85.3(11) . . . . ? S1 Cu1 N2 C6 173.0(11) . . . . ? N1 Cu1 N2 N3 -176.3(10) . . . . ? O1 Cu1 N2 N3 92.8(9) . . . . ? S1 Cu1 N2 N3 -8.9(9) . . . . ? C6 N2 N3 C7 -176.3(13) . . . . ? Cu1 N2 N3 C7 5.6(14) . . . . ? C5 N1 C1 C2 -2(2) . . . . ? Cu1 N1 C1 C2 175.1(11) . . . . ? N1 C1 C2 C3 0(2) . . . . ? C1 C2 C3 C4 0(2) . . . . ? C2 C3 C4 C5 0(2) . . . . ? C1 N1 C5 C4 2(2) . . . . ? Cu1 N1 C5 C4 -175.1(12) . . . . ? C1 N1 C5 C6 -176.5(12) . . . . ? Cu1 N1 C5 C6 6.2(15) . . . . ? C3 C4 C5 N1 -1(2) . . . . ? C3 C4 C5 C6 177.3(13) . . . . ? N3 N2 C6 C5 178.0(10) . . . . ? Cu1 N2 C6 C5 -3.8(16) . . . . ? N1 C5 C6 N2 -1.9(18) . . . . ? C4 C5 C6 N2 179.3(13) . . . . ? N2 N3 C7 N4 -178.1(11) . . . . ? N2 N3 C7 S1 3.6(17) . . . . ? Cu1 S1 C7 N4 173.3(11) . . . . ? Cu1 S1 C7 N3 -8.5(12) . . . . ? N2 Cu1 O1 C13 171.2(10) . . . . ? N5 Cu1 O1 C13 -9.2(10) . . . . ? N1 Cu1 O1 C13 91.4(10) . . . . ? S1 Cu1 O1 C13 -102.3(10) . . . . ? N1 Cu1 N5 C8 99.8(12) . . . . ? O1 Cu1 N5 C8 -169.6(13) . . . . ? S1 Cu1 N5 C8 -67.9(12) . . . . ? N1 Cu1 N5 C12 -90.0(11) . . . . ? O1 Cu1 N5 C12 0.6(10) . . . . ? S1 Cu1 N5 C12 102.3(10) . . . . ? C12 N5 C8 C9 0(2) . . . . ? Cu1 N5 C8 C9 170.7(13) . . . . ? N5 C8 C9 C10 0(3) . . . . ? C8 C9 C10 C11 2(3) . . . . ? C9 C10 C11 C12 -4(3) . . . . ? C10 C11 C12 N5 4(3) . . . . ? C10 C11 C12 C13 -175.4(15) . . . . ? C8 N5 C12 C11 -2(2) . . . . ? Cu1 N5 C12 C11 -173.4(12) . . . . ? C8 N5 C12 C13 177.8(12) . . . . ? Cu1 N5 C12 C13 6.4(16) . . . . ? Cu1 O1 C13 O2 -172.9(12) . . . . ? Cu1 O1 C13 C12 15.7(17) . . . . ? C11 C12 C13 O1 163.9(16) . . . . ? N5 C12 C13 O1 -16(2) . . . . ? C11 C12 C13 O2 -8(2) . . . . ? N5 C12 C13 O2 171.9(13) . . . . ? 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 O1W H2W1 O1W 0.862(5) 2.541(9) 2.895(19) 105.7(11) 2_656 O1W H1W1 O3W 0.862(5) 2.35(10) 2.803(15) 113(9) . O2W H2W2 O2 0.849(5) 2.18(11) 2.910(14) 145(17) 2 O2W H1W2 O1W 0.854(5) 2.212(5) 2.821(15) 128.2(18) . O3W H1W3 O1 0.850(5) 2.300(5) 3.045(14) 147(3) 1_556 O3W H2W3 O2 0.850(5) 1.97(5) 2.778(17) 158(15) 2 N4 H4A N3 0.86 2.1 2.955(15) 175 5_655 N4 H4B O1W 0.86 2.13 2.990(15) 175 2_655 # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 930873' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_culatp-1 _audit_creation_date 2013-05-06T13:20:40-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_formula_sum 'C16 H16 Cu2 N12 O6 S4' _chemical_formula_moiety 'C8 H8 Cu N6 O3 S2, C8 H8 Cu N5 S2, N O3' _chemical_formula_weight 727.73 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 10.133(9) _cell_length_b 20.184(7) _cell_length_c 13.385(6) _cell_angle_alpha 90 _cell_angle_beta 105.16(8) _cell_angle_gamma 90 _cell_volume 2642(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.829 _exptl_crystal_density_method 'not measured' _exptl_crystal_colour_modifier bluish _exptl_crystal_colour_primary green _exptl_crystal_description prismatic _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 1.985 #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_measurement_device_type 'Stoe IPDS I' _diffrn_measurement_method 'Phi scans' _diffrn_ambient_temperature 293(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_monochromator graphite _diffrn_reflns_number 12505 _diffrn_reflns_av_R_equivalents 0.3645 _diffrn_reflns_av_unetI/netI 0.5721 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 25.85 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_max 0.951 _diffrn_measured_fraction_theta_full 0.964 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 #============================================================================== # STRUCTURE SOLUTION _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #============================================================================== # REFINEMENT DATA _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^ > 2\s(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. ; _reflns_number_total 4863 _reflns_number_gt 897 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.3127 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1184 _refine_ls_goodness_of_fit_ref 0.581 _refine_ls_restrained_S_all 0.581 _refine_ls_number_reflns 4863 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.351 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.082 _refine_ls_extinction_method none 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' _computing_data_collection 'Stoe IPDS Software (Stoe, 1998)' _computing_cell_refinement 'Stoe IPDS Software (Stoe, 1998)' _computing_data_reduction 'Stoe IPDS Software (Stoe, 1998)' _computing_molecular_graphics 'CrystalMaker 4.1 (Palmer, D.C., 1994-2001)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cu1 0.88116(19) 0.41299(9) 0.10874(17) 0.0489(6) Uani d . 1 . . Cu Cu2 1.1460(2) 0.35398(9) 0.35966(19) 0.0516(7) Uani d . 1 . . Cu S3 1.0794(4) 0.3559(2) 0.1199(4) 0.0512(13) Uani d . 1 . . S S4 1.1752(4) 0.5881(2) 0.1256(4) 0.0600(14) Uani d . 1 . . S S5 0.9478(4) 0.40771(19) 0.3594(4) 0.0539(13) Uani d . 1 . . S S6 0.8594(5) 0.1794(2) 0.3316(5) 0.0875(18) Uani d . 1 . . S C7 0.6696(17) 0.3232(8) 0.0979(13) 0.053(5) Uani d . 1 . . C H7 0.6231 0.2831 0.0897 0.08 Uiso calc R 1 . . H O8 1.5031(10) 0.4059(5) 0.6138(10) 0.074(4) Uani d . 1 . . O N9 1.2257(13) 0.4444(5) 0.3611(9) 0.044(4) Uani d . 1 . . N O10 1.2930(10) 0.3695(4) 0.5723(8) 0.057(3) Uani d . 1 . . O N11 0.9370(13) 0.5393(6) 0.3714(11) 0.067(5) Uani d . 1 . . N H11A 0.9717 0.5782 0.3713 0.1 Uiso calc R 1 . . H H11B 0.8531 0.535 0.3727 0.1 Uiso calc R 1 . . H N12 0.8743(14) 0.2691(6) 0.1018(11) 0.052(4) Uani d . 1 . . N H12 0.8395 0.23 0.0974 0.078 Uiso calc R 1 . . H C13 1.0108(16) 0.4876(8) 0.3695(12) 0.040(5) Uani d . 1 . . C C14 0.5990(15) 0.3855(6) 0.1059(12) 0.041(5) Uani d . 1 . . C N15 1.3359(13) 0.3288(7) 0.3534(10) 0.054(4) Uani d . 1 . . N N16 1.1414(13) 0.4976(5) 0.3675(10) 0.043(4) Uani d . 1 . . N H16 1.173 0.5373 0.3701 0.064 Uiso calc R 1 . . H N17 0.7939(13) 0.3257(5) 0.1026(10) 0.049(4) Uani d . 1 . . N N18 0.1015(16) 0.6850(7) 0.3925(12) 0.066(4) Uani d . 1 . . N C19 1.6109(18) 0.3138(9) 0.3609(13) 0.062(5) Uani d . 1 . . C H19 1.7025 0.3081 0.3627 0.092 Uiso calc R 1 . . H C20 0.9838(15) 0.2305(6) 0.3542(13) 0.042(5) Uani d . 1 . . C N21 0.9607(13) 0.4990(6) 0.1170(10) 0.046(4) Uani d . 1 . . N N22 1.3808(16) 0.4166(6) 0.5995(10) 0.052(3) Uani d . 1 . . N O23 1.3360(11) 0.4722(5) 0.6058(10) 0.069(4) Uani d . 1 . . O O24 -0.0204(12) 0.6744(5) 0.3831(11) 0.090(5) Uani d . 1 . . O O25 0.1848(10) 0.6363(5) 0.3993(9) 0.071(4) Uani d . 1 . . O C26 0.4191(16) 0.4535(8) 0.1156(13) 0.049(5) Uani d . 1 . . C H26 0.3273 0.46 0.1126 0.073 Uiso calc R 1 . . H C27 0.5084(16) 0.5063(8) 0.1318(14) 0.054(5) Uani d . 1 . . C H27 0.478 0.548 0.1452 0.081 Uiso calc R 1 . . H C28 0.4672(14) 0.3921(8) 0.1042(13) 0.051(5) Uani d . 1 . . C H28 0.4098 0.3554 0.0954 0.077 Uiso calc R 1 . . H N29 1.0810(12) 0.2258(5) 0.1134(11) 0.051(4) Uani d . 1 . . N H29A 1.0432 0.1876 0.1126 0.076 Uiso calc R 1 . . H H29B 1.167 0.2286 0.1176 0.076 Uiso calc R 1 . . H O30 0.1493(12) 0.7433(5) 0.4015(11) 0.085(5) Uani d . 1 . . O C31 1.4187(15) 0.3860(8) 0.3616(13) 0.046(5) Uani d . 1 . . C C32 1.0094(16) 0.2784(7) 0.1083(13) 0.040(4) Uani d . 1 . . C N33 0.6880(11) 0.4394(6) 0.1183(10) 0.041(3) Uani d . 1 . . N C34 1.526(2) 0.2612(9) 0.3529(15) 0.067(6) Uani d . 1 . . C H34 1.5609 0.2191 0.3472 0.1 Uiso calc R 1 . . H N35 1.0774(13) 0.2662(6) 0.3682(11) 0.056(4) Uani d . 1 . . N C37 1.0479(15) 0.5347(7) 0.1210(13) 0.043(5) Uani d . 1 . . C C38 1.3889(18) 0.2677(7) 0.3528(14) 0.059(5) Uani d . 1 . . C H38 1.3349 0.2304 0.3523 0.089 Uiso calc R 1 . . H C39 0.6390(15) 0.4983(7) 0.1284(13) 0.046(5) Uani d . 1 . . C H39 0.6953 0.5352 0.1333 0.069 Uiso calc R 1 . . H C41 1.5578(16) 0.3769(9) 0.3666(13) 0.058(5) Uani d . 1 . . C H41 1.6152 0.4135 0.3738 0.087 Uiso calc R 1 . . H C47 1.3552(17) 0.4491(8) 0.3641(13) 0.054(5) Uani d . 1 . . C H47 1.4012 0.4892 0.3676 0.082 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu1 0.0431(12) 0.0351(11) 0.0671(18) -0.0046(10) 0.0118(12) 0.0004(12) Cu2 0.0475(13) 0.0369(11) 0.0689(18) -0.0058(10) 0.0126(12) 0.0002(12) S3 0.048(3) 0.044(2) 0.060(4) -0.003(2) 0.010(3) -0.001(2) S4 0.046(3) 0.050(3) 0.081(4) -0.008(2) 0.012(2) 0.000(3) S5 0.050(3) 0.043(2) 0.067(4) -0.002(2) 0.014(2) -0.007(2) S6 0.079(3) 0.068(3) 0.117(5) -0.018(3) 0.029(3) -0.002(3) C7 0.050(11) 0.061(11) 0.044(13) -0.039(9) 0.005(9) 0.004(9) O8 0.021(6) 0.069(8) 0.127(11) 0.003(6) 0.011(6) -0.004(7) N9 0.052(9) 0.032(7) 0.036(10) -0.002(6) -0.008(7) 0.001(6) O10 0.067(7) 0.037(6) 0.061(9) 0.000(5) 0.004(6) 0.000(5) N11 0.068(10) 0.050(8) 0.081(13) 0.020(8) 0.018(9) -0.011(8) N12 0.056(9) 0.042(8) 0.066(12) 0.001(7) 0.028(8) -0.008(7) C13 0.026(9) 0.053(10) 0.033(11) 0.002(7) -0.007(8) 0.001(8) C14 0.059(11) 0.010(7) 0.049(13) -0.012(8) 0.006(9) 0.002(7) N15 0.057(9) 0.070(10) 0.033(10) 0.010(8) 0.011(7) -0.002(7) N16 0.045(8) 0.020(6) 0.059(11) -0.001(6) 0.006(7) 0.004(7) N17 0.049(9) 0.042(8) 0.057(11) -0.004(7) 0.016(8) -0.021(7) N18 0.061(11) 0.062(10) 0.081(13) -0.011(9) 0.031(9) -0.005(9) C19 0.066(12) 0.066(12) 0.044(14) 0.006(11) -0.003(10) -0.005(10) C20 0.052(10) 0.019(7) 0.062(13) -0.010(7) 0.027(9) 0.007(8) N21 0.045(8) 0.041(8) 0.056(11) -0.022(7) 0.019(7) 0.001(7) N22 0.069(9) 0.034(7) 0.048(9) 0.016(8) 0.008(7) -0.014(7) O23 0.068(8) 0.035(6) 0.108(12) 0.009(6) 0.028(8) -0.022(6) O24 0.049(8) 0.068(8) 0.160(15) -0.007(6) 0.042(8) 0.010(8) O25 0.055(7) 0.053(7) 0.111(11) 0.006(6) 0.034(7) -0.019(7) C26 0.043(11) 0.057(11) 0.045(13) 0.008(9) 0.009(9) 0.000(9) C27 0.053(12) 0.048(10) 0.065(14) 0.008(10) 0.021(10) -0.001(9) C28 0.023(9) 0.073(12) 0.059(14) -0.007(8) 0.012(8) 0.014(9) N29 0.032(8) 0.033(7) 0.078(12) 0.004(6) -0.001(7) -0.015(7) O30 0.080(9) 0.050(7) 0.127(14) 0.004(7) 0.028(9) 0.005(8) C31 0.033(9) 0.071(12) 0.037(12) -0.014(9) 0.012(8) 0.013(9) C32 0.035(10) 0.035(8) 0.051(13) 0.007(8) 0.010(8) -0.001(8) N33 0.043(7) 0.049(7) 0.037(9) 0.014(6) 0.017(6) 0.016(6) C34 0.073(14) 0.044(11) 0.084(17) 0.014(10) 0.023(12) -0.022(10) N35 0.061(10) 0.037(8) 0.078(13) 0.010(7) 0.034(9) 0.015(7) C37 0.030(10) 0.038(9) 0.055(13) 0.008(7) 0.000(8) 0.006(8) C38 0.070(13) 0.032(9) 0.078(16) 0.002(9) 0.022(11) 0.000(9) C39 0.037(10) 0.032(8) 0.064(14) 0.002(8) 0.005(9) -0.010(9) C41 0.050(11) 0.072(12) 0.059(15) -0.004(10) 0.028(10) 0.013(10) C47 0.047(11) 0.054(11) 0.051(14) 0.015(9) -0.008(9) 0.005(9) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 N21 . 1.906(12) ? Cu1 N17 . 1.964(11) ? Cu1 N33 . 2.065(11) ? Cu1 S3 . 2.286(5) ? Cu2 N35 . 1.918(13) ? Cu2 N9 . 1.993(11) ? Cu2 N15 . 2.013(13) ? Cu2 S5 . 2.282(5) ? S3 C32 . 1.707(14) ? S4 C37 . 1.669(16) ? S5 C13 . 1.727(15) ? S6 C20 . 1.595(14) ? C7 N17 . 1.245(17) ? C7 C14 . 1.463(19) ? C7 H7 . 0.93 ? O8 N22 . 1.223(14) ? N9 C47 . 1.305(17) ? N9 N16 . 1.389(15) ? O10 N22 . 1.289(14) ? N11 C13 . 1.288(16) ? N11 H11A . 0.86 ? N11 H11B . 0.86 ? N12 C32 . 1.362(17) ? N12 N17 . 1.405(14) ? N12 H12 . 0.86 ? C13 N16 . 1.346(18) ? C14 C28 . 1.337(18) ? C14 N33 . 1.395(15) ? N15 C38 . 1.346(17) ? N15 C31 . 1.414(16) ? N16 H16 . 0.86 ? N18 O24 . 1.227(15) ? N18 O30 . 1.266(15) ? N18 O25 . 1.283(15) ? C19 C34 . 1.35(2) ? C19 C41 . 1.39(2) ? C19 H19 . 0.93 ? C20 N35 . 1.165(15) ? N21 C37 . 1.130(14) ? N22 O23 . 1.222(13) ? C26 C28 . 1.356(19) ? C26 C27 . 1.38(2) ? C26 H26 . 0.93 ? C27 C39 . 1.345(19) ? C27 H27 . 0.93 ? C28 H28 . 0.93 ? N29 C32 . 1.279(15) ? N29 H29A . 0.86 ? N29 H29B . 0.86 ? C31 C41 . 1.405(19) ? C31 C47 . 1.43(2) ? N33 C39 . 1.309(16) ? C34 C38 . 1.40(2) ? C34 H34 . 0.93 ? C38 H38 . 0.93 ? C39 H39 . 0.93 ? C41 H41 . 0.93 ? C47 H47 . 0.93 ? 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 Cu1 N17 177.8(5) . . ? N21 Cu1 N33 98.9(5) . . ? N17 Cu1 N33 79.1(5) . . ? N21 Cu1 S3 96.0(4) . . ? N17 Cu1 S3 85.9(4) . . ? N33 Cu1 S3 163.1(3) . . ? N35 Cu2 N9 175.9(5) . . ? N35 Cu2 N15 97.8(5) . . ? N9 Cu2 N15 80.9(5) . . ? N35 Cu2 S5 96.1(4) . . ? N9 Cu2 S5 85.4(4) . . ? N15 Cu2 S5 166.0(4) . . ? C32 S3 Cu1 96.8(5) . . ? C13 S5 Cu2 97.8(6) . . ? N17 C7 C14 118.0(13) . . ? N17 C7 H7 121 . . ? C14 C7 H7 121 . . ? C47 N9 N16 124.8(13) . . ? C47 N9 Cu2 117.9(11) . . ? N16 N9 Cu2 117.1(9) . . ? C13 N11 H11A 120 . . ? C13 N11 H11B 120 . . ? H11A N11 H11B 120 . . ? C32 N12 N17 117.5(12) . . ? C32 N12 H12 121.3 . . ? N17 N12 H12 121.3 . . ? N11 C13 N16 117.3(14) . . ? N11 C13 S5 123.6(12) . . ? N16 C13 S5 118.9(12) . . ? C28 C14 N33 122.4(13) . . ? C28 C14 C7 126.1(13) . . ? N33 C14 C7 111.4(12) . . ? C38 N15 C31 121.2(14) . . ? C38 N15 Cu2 128.2(12) . . ? C31 N15 Cu2 110.2(9) . . ? C13 N16 N9 120.6(11) . . ? C13 N16 H16 119.7 . . ? N9 N16 H16 119.7 . . ? C7 N17 N12 123.2(13) . . ? C7 N17 Cu1 118.4(11) . . ? N12 N17 Cu1 118.3(9) . . ? O24 N18 O30 121.4(15) . . ? O24 N18 O25 120.0(14) . . ? O30 N18 O25 118.4(14) . . ? C34 C19 C41 118.5(17) . . ? C34 C19 H19 120.7 . . ? C41 C19 H19 120.7 . . ? N35 C20 S6 177.1(14) . . ? C37 N21 Cu1 153.8(13) . . ? O23 N22 O8 122.1(14) . . ? O23 N22 O10 117.2(13) . . ? O8 N22 O10 120.6(12) . . ? C28 C26 C27 119.0(15) . . ? C28 C26 H26 120.5 . . ? C27 C26 H26 120.5 . . ? C39 C27 C26 120.9(15) . . ? C39 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? C14 C28 C26 118.4(14) . . ? C14 C28 H28 120.8 . . ? C26 C28 H28 120.8 . . ? C32 N29 H29A 120 . . ? C32 N29 H29B 120 . . ? H29A N29 H29B 120 . . ? C41 C31 N15 117.7(14) . . ? C41 C31 C47 124.6(15) . . ? N15 C31 C47 117.8(13) . . ? N29 C32 N12 115.8(13) . . ? N29 C32 S3 122.7(12) . . ? N12 C32 S3 121.3(11) . . ? C39 N33 C14 118.0(12) . . ? C39 N33 Cu1 129.2(10) . . ? C14 N33 Cu1 112.6(9) . . ? C19 C34 C38 122.4(16) . . ? C19 C34 H34 118.8 . . ? C38 C34 H34 118.8 . . ? C20 N35 Cu2 148.6(11) . . ? N21 C37 S4 179.2(16) . . ? N15 C38 C34 119.0(15) . . ? N15 C38 H38 120.5 . . ? C34 C38 H38 120.5 . . ? N33 C39 C27 121.1(15) . . ? N33 C39 H39 119.5 . . ? C27 C39 H39 119.5 . . ? C19 C41 C31 120.9(15) . . ? C19 C41 H41 119.5 . . ? C31 C41 H41 119.5 . . ? N9 C47 C31 112.9(15) . . ? N9 C47 H47 123.6 . . ? C31 C47 H47 123.6 . . ? 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 #N35 Cu2 N9 C47 67(8) . . . . ? #N35 Cu2 N9 N16 -108(8) . . . . ? #N21 Cu1 N17 C7 26(15) . . . . ? #N21 Cu1 N17 N12 -155(14) . . . . ? #N17 Cu1 N21 C37 157(13) . . . . ? #S6 C20 N35 Cu2 13E1(3) . . . . ? #N9 Cu2 N35 C20 134(7) . . . . ? #Cu1 N21 C37 S4 13E1(10) . . . . ? N21 Cu1 S3 C32 -178.1(7) . . . . ? N17 Cu1 S3 C32 2.9(7) . . . . ? N33 Cu1 S3 C32 30.0(16) . . . . ? N35 Cu2 S5 C13 172.3(7) . . . . ? N9 Cu2 S5 C13 -3.8(7) . . . . ? N15 Cu2 S5 C13 -14(2) . . . . ? N15 Cu2 N9 C47 -4.1(12) . . . . ? S5 Cu2 N9 C47 178.5(12) . . . . ? N15 Cu2 N9 N16 -178.9(11) . . . . ? S5 Cu2 N9 N16 3.7(9) . . . . ? Cu2 S5 C13 N11 179.1(13) . . . . ? Cu2 S5 C13 N16 4.4(14) . . . . ? N17 C7 C14 C28 -178.8(18) . . . . ? N17 C7 C14 N33 0(2) . . . . ? N35 Cu2 N15 C38 1.7(15) . . . . ? N9 Cu2 N15 C38 177.7(15) . . . . ? S5 Cu2 N15 C38 -171.7(14) . . . . ? N35 Cu2 N15 C31 -171.5(11) . . . . ? N9 Cu2 N15 C31 4.5(10) . . . . ? S5 Cu2 N15 C31 15(3) . . . . ? N11 C13 N16 N9 -177.4(13) . . . . ? S5 C13 N16 N9 -2(2) . . . . ? C47 N9 N16 C13 -176.2(16) . . . . ? Cu2 N9 N16 C13 -1.8(18) . . . . ? C14 C7 N17 N12 176.3(14) . . . . ? C14 C7 N17 Cu1 -5(2) . . . . ? C32 N12 N17 C7 -179.3(17) . . . . ? C32 N12 N17 Cu1 1.8(18) . . . . ? N33 Cu1 N17 C7 5.8(13) . . . . ? S3 Cu1 N17 C7 178.1(13) . . . . ? N33 Cu1 N17 N12 -175.2(11) . . . . ? S3 Cu1 N17 N12 -3.0(10) . . . . ? N33 Cu1 N21 C37 177(3) . . . . ? S3 Cu1 N21 C37 5(3) . . . . ? C28 C26 C27 C39 5(3) . . . . ? N33 C14 C28 C26 0(3) . . . . ? C7 C14 C28 C26 178.0(17) . . . . ? C27 C26 C28 C14 -2(3) . . . . ? C38 N15 C31 C41 1(2) . . . . ? Cu2 N15 C31 C41 175.2(13) . . . . ? C38 N15 C31 C47 -178.6(16) . . . . ? Cu2 N15 C31 C47 -4.8(18) . . . . ? N17 N12 C32 N29 176.2(14) . . . . ? N17 N12 C32 S3 1(2) . . . . ? Cu1 S3 C32 N29 -177.5(13) . . . . ? Cu1 S3 C32 N12 -3.2(15) . . . . ? C28 C14 N33 C39 0(2) . . . . ? C7 C14 N33 C39 -178.8(14) . . . . ? C28 C14 N33 Cu1 -176.6(14) . . . . ? C7 C14 N33 Cu1 4.8(15) . . . . ? N21 Cu1 N33 C39 -0.8(14) . . . . ? N17 Cu1 N33 C39 178.5(14) . . . . ? S3 Cu1 N33 C39 150.9(12) . . . . ? N21 Cu1 N33 C14 175.2(10) . . . . ? N17 Cu1 N33 C14 -5.6(10) . . . . ? S3 Cu1 N33 C14 -33(2) . . . . ? C41 C19 C34 C38 -2(3) . . . . ? N15 Cu2 N35 C20 -155(3) . . . . ? S5 Cu2 N35 C20 23(3) . . . . ? C31 N15 C38 C34 -5(3) . . . . ? Cu2 N15 C38 C34 -177.1(13) . . . . ? C19 C34 C38 N15 5(3) . . . . ? C14 N33 C39 C27 3(2) . . . . ? Cu1 N33 C39 C27 178.9(13) . . . . ? C26 C27 C39 N33 -6(3) . . . . ? C34 C19 C41 C31 -1(3) . . . . ? N15 C31 C41 C19 2(2) . . . . ? C47 C31 C41 C19 -178.3(17) . . . . ? N16 N9 C47 C31 176.8(14) . . . . ? Cu2 N9 C47 C31 2.5(19) . . . . ? C41 C31 C47 N9 -178.3(16) . . . . ? N15 C31 C47 N9 2(2) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 930874' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_culatp _audit_creation_date 2012-01-25T12:59:34-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_formula_sum 'C15.72 H16 Cu2 N12 O6.83 S3.72' _chemical_formula_moiety 'C7.72 H8 Cu N6 O3.83 S1.72, C8 H8 Cu N5 S2, N O3' _chemical_formula_weight 728.82 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 10.164(2) _cell_length_b 20.143(8) _cell_length_c 13.375(4) _cell_angle_alpha 90 _cell_angle_beta 105.39(3) _cell_angle_gamma 90 _cell_volume 2640.3(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 986 _cell_measurement_theta_max 25.94 _cell_measurement_theta_min 2.02 _exptl_crystal_density_diffrn 1.833 _exptl_crystal_density_method 'not measured' #_exptl_crystal_F_000 1466 _exptl_crystal_F_000 1466.2 _exptl_crystal_colour_modifier bluish _exptl_crystal_colour_primary green _exptl_crystal_description prismatic _exptl_crystal_size_max 0.273 _exptl_crystal_size_mid 0.211 _exptl_crystal_size_min 0.095 _exptl_absorpt_coefficient_mu 1.968 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; a grid of 16 x 16 x 16 = 4096 sampling points was used ; _exptl_absorpt_correction_T_min 0.7753 _exptl_absorpt_correction_T_max 0.9117 #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_measurement_device_type 'Stoe IPDS I' _diffrn_measurement_method 'Phi scans' _diffrn_ambient_temperature 293(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_monochromator graphite _diffrn_reflns_number 20296 _diffrn_reflns_av_R_equivalents 0.1193 _diffrn_reflns_av_unetI/netI 0.1418 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.94 _diffrn_reflns_theta_full 25.94 _diffrn_measured_fraction_theta_max 0.974 _diffrn_measured_fraction_theta_full 0.974 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 #============================================================================== # STRUCTURE SOLUTION _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #============================================================================== # REFINEMENT DATA _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^ > 2\s(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. ; _reflns_number_total 5020 _reflns_number_gt 2202 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.123 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0715 _refine_ls_goodness_of_fit_ref 0.745 _refine_ls_restrained_S_all 0.745 _refine_ls_number_reflns 5020 _refine_ls_number_parameters 380 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0221P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.328 _refine_diff_density_min -0.563 _refine_diff_density_rms 0.075 _refine_ls_extinction_method none 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Stoe IPDS Software (Stoe, 1998)' _computing_cell_refinement 'Stoe IPDS Software (Stoe, 1998)' _computing_data_reduction 'Stoe IPDS Software (Stoe, 1998)' _computing_molecular_graphics 'CrystalMaker 4.1 (Palmer, D.C., 1994-2001)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cu1 0.88058(6) 0.08619(3) 0.10884(4) 0.04071(18) Uani d . 1 . . Cu Cu2 0.14396(7) 0.14578(3) 0.35837(5) 0.04202(19) Uani d . 1 . . Cu S1 1.07832(14) 0.14307(6) 0.12016(10) 0.0441(3) Uani d . 1 . . S S2 -0.05210(14) 0.09250(6) 0.35914(10) 0.0452(3) Uani d . 1 . . S S3 1.17649(16) -0.08813(7) 0.12551(11) 0.0580(4) Uani d . 1 . . S S4 -0.1442(3) 0.31998(10) 0.32924(18) 0.0682(10) Uani d P 0.722(5) . . S O11 0.3498(4) 0.25732(17) 0.0968(3) 0.0765(13) Uani d . 1 . . O O12 0.2936(4) 0.13190(15) 0.5731(3) 0.0520(9) Uani d . 1 . . O O13 0.0890(6) 0.2351(2) 0.3741(4) 0.0702(15) Uani d P 0.278(5) . . O O21 0.3145(4) 0.36233(16) 0.1007(3) 0.0667(11) Uani d . 1 . . O O22 0.3332(4) 0.02792(17) 0.6075(3) 0.0652(12) Uani d . 1 . . O O23 -0.1033(15) 0.2361(7) 0.3123(10) 0.059(4) Uani d P 0.278(5) . . O O31 0.5184(5) 0.32435(18) 0.1179(4) 0.0830(14) Uani d . 1 . . O O32 0.5001(5) 0.09371(17) 0.6134(3) 0.0705(12) Uani d . 1 . . O O33 -0.0068(18) 0.3263(6) 0.3896(12) 0.080(5) Uani d P 0.278(5) . . O N1 0.3942(6) 0.3150(2) 0.1047(3) 0.0518(12) Uani d . 1 . . N N2 0.3758(6) 0.0849(2) 0.5991(3) 0.0478(11) Uani d . 1 . . N N3 -0.0110(7) 0.2684(2) 0.3554(4) 0.0462(14) Uani d P 0.278(5) . . N N11 0.6913(4) 0.06152(17) 0.1172(3) 0.0368(10) Uani d . 1 . . N N12 0.3345(4) 0.16941(18) 0.3538(3) 0.0404(10) Uani d . 1 . . N N21 0.7969(5) 0.17501(16) 0.1017(3) 0.0359(10) Uani d . 1 . . N N22 0.2223(5) 0.05602(17) 0.3619(3) 0.0348(10) Uani d . 1 . . N N31 0.8729(5) 0.22983(17) 0.0987(3) 0.0393(10) Uani d . 1 . . N H31A 0.8365 0.2687 0.0901 0.059 Uiso calc R 1 . . H N32 0.1428(5) 0.00271(17) 0.3673(3) 0.0403(10) Uani d . 1 . . N H32A 0.1752 -0.0369 0.3712 0.06 Uiso calc R 1 . . H N41 1.0832(5) 0.27349(18) 0.1130(3) 0.0505(12) Uani d . 1 . . N H41A 1.0478 0.3125 0.1081 0.076 Uiso calc R 1 . . H H41B 1.1693 0.2689 0.12 0.076 Uiso calc R 1 . . H N42 -0.0640(5) -0.03778(19) 0.3725(3) 0.0531(12) Uani d . 1 . . N H42A -0.0303 -0.0772 0.377 0.08 Uiso calc R 1 . . H H42B -0.148 -0.0321 0.3721 0.08 Uiso calc R 1 . . H N51 0.9602(5) -0.00074(19) 0.1182(3) 0.0451(11) Uani d . 1 . . N N52 0.0890(6) 0.2351(2) 0.3741(4) 0.0702(15) Uani d P 0.722(5) . . N C11 0.6424(6) 0.0017(2) 0.1310(3) 0.0432(13) Uani d . 1 . . C H11 0.7009 -0.0346 0.1393 0.065 Uiso calc R 1 . . H C12 0.3853(6) 0.2299(2) 0.3484(4) 0.0474(14) Uani d . 1 . . C H12 0.3282 0.2666 0.3423 0.071 Uiso calc R 1 . . H C21 0.5109(6) -0.0087(2) 0.1337(4) 0.0481(15) Uani d . 1 . . C H21 0.4814 -0.0508 0.1463 0.072 Uiso calc R 1 . . H C22 0.5225(7) 0.2393(3) 0.3518(4) 0.0564(16) Uani d . 1 . . C H22 0.5567 0.2818 0.348 0.085 Uiso calc R 1 . . H C31 0.4222(6) 0.0446(3) 0.1172(4) 0.0527(15) Uani d . 1 . . C H31 0.3308 0.0385 0.115 0.079 Uiso calc R 1 . . H C32 0.6063(6) 0.1848(3) 0.3608(4) 0.0567(16) Uani d . 1 . . C H32 0.6982 0.1901 0.3638 0.085 Uiso calc R 1 . . H C41 0.4708(6) 0.1074(2) 0.1040(4) 0.0488(14) Uani d . 1 . . C H41 0.4131 0.144 0.0941 0.073 Uiso calc R 1 . . H C42 0.5528(6) 0.1220(3) 0.3652(4) 0.0522(15) Uani d . 1 . . C H42 0.6079 0.0845 0.3711 0.078 Uiso calc R 1 . . H C51 0.6062(6) 0.1146(2) 0.1056(3) 0.0361(12) Uani d . 1 . . C C52 0.4169(6) 0.1162(2) 0.3607(3) 0.0382(12) Uani d . 1 . . C C61 0.6705(6) 0.1780(2) 0.0987(3) 0.0385(13) Uani d . 1 . . C H61 0.6231 0.2179 0.0926 0.058 Uiso calc R 1 . . H C62 0.3481(6) 0.0520(2) 0.3640(3) 0.0424(13) Uani d . 1 . . C H62 0.3933 0.0116 0.3673 0.064 Uiso calc R 1 . . H C71 1.0065(6) 0.2214(2) 0.1097(3) 0.0382(13) Uani d . 1 . . C C72 0.0127(6) 0.0135(2) 0.3664(4) 0.0418(14) Uani d . 1 . . C C81 1.0509(6) -0.0367(2) 0.1215(3) 0.0403(13) Uani d . 1 . . C C82 -0.0110(7) 0.2684(2) 0.3554(4) 0.0462(14) Uani d P 0.722(5) . . C loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu1 0.0420(5) 0.0243(3) 0.0539(4) 0.0035(3) 0.0093(3) 0.0000(3) Cu2 0.0448(5) 0.0268(3) 0.0536(4) 0.0032(3) 0.0116(3) -0.0011(3) S1 0.0448(10) 0.0314(7) 0.0554(8) 0.0023(6) 0.0120(7) 0.0012(6) S2 0.0452(10) 0.0341(7) 0.0571(8) 0.0039(6) 0.0147(7) 0.0025(6) S3 0.0514(11) 0.0429(8) 0.0773(10) 0.0108(7) 0.0127(8) 0.0027(7) S4 0.070(2) 0.0488(13) 0.0873(18) 0.0152(11) 0.0237(15) 0.0002(11) O11 0.063(3) 0.036(2) 0.129(4) -0.005(2) 0.023(3) -0.006(2) O12 0.049(3) 0.035(2) 0.073(2) 0.0064(17) 0.0170(19) -0.0017(17) O13 0.095(5) 0.034(3) 0.093(4) 0.012(3) 0.045(3) -0.004(2) O21 0.053(3) 0.035(2) 0.114(3) 0.0032(18) 0.025(2) -0.0129(19) O22 0.071(3) 0.037(2) 0.088(3) -0.0046(19) 0.021(2) 0.0133(18) O23 0.041(10) 0.068(9) 0.067(9) 0.014(7) 0.012(8) -0.002(7) O31 0.055(4) 0.054(3) 0.141(4) 0.003(2) 0.028(3) 0.015(2) O32 0.048(3) 0.044(2) 0.121(3) 0.000(2) 0.024(3) 0.010(2) O33 0.083(15) 0.043(8) 0.102(12) 0.020(8) 0.006(10) -0.019(8) N1 0.049(4) 0.045(3) 0.060(3) -0.007(3) 0.013(2) 0.001(2) N2 0.062(4) 0.035(2) 0.048(2) -0.002(3) 0.017(2) 0.000(2) N3 0.056(5) 0.036(3) 0.049(3) -0.002(3) 0.018(3) -0.008(3) N11 0.040(3) 0.030(2) 0.037(2) -0.0040(19) 0.0062(19) 0.0016(17) N12 0.041(3) 0.037(2) 0.042(2) -0.002(2) 0.008(2) 0.0005(18) N21 0.040(3) 0.026(2) 0.038(2) -0.004(2) 0.006(2) 0.0030(16) N22 0.040(3) 0.028(2) 0.034(2) 0.0004(19) 0.006(2) 0.0014(16) N31 0.039(3) 0.025(2) 0.054(3) 0.003(2) 0.013(2) 0.0063(18) N32 0.046(3) 0.027(2) 0.047(3) 0.003(2) 0.010(2) 0.0010(18) N41 0.051(3) 0.032(2) 0.067(3) -0.004(2) 0.013(2) 0.005(2) N42 0.061(3) 0.039(2) 0.061(3) -0.004(2) 0.018(2) 0.007(2) N51 0.064(4) 0.027(2) 0.044(2) 0.008(2) 0.014(2) 0.0013(19) N52 0.095(5) 0.034(3) 0.093(4) 0.012(3) 0.045(3) -0.004(2) C11 0.043(4) 0.040(3) 0.043(3) -0.001(3) 0.004(3) 0.001(2) C12 0.054(4) 0.036(3) 0.050(3) -0.007(3) 0.009(3) -0.001(2) C21 0.056(5) 0.040(3) 0.047(3) -0.012(3) 0.011(3) -0.003(2) C22 0.068(5) 0.047(3) 0.057(4) -0.018(3) 0.022(3) 0.000(3) C31 0.046(4) 0.058(4) 0.056(3) -0.009(3) 0.016(3) -0.013(3) C32 0.055(5) 0.061(4) 0.052(4) -0.007(3) 0.012(3) -0.007(3) C41 0.053(5) 0.043(3) 0.052(3) 0.004(3) 0.018(3) -0.002(2) C42 0.045(5) 0.054(4) 0.056(3) 0.004(3) 0.011(3) -0.001(3) C51 0.038(4) 0.036(3) 0.034(3) 0.007(3) 0.009(2) -0.001(2) C52 0.036(4) 0.039(3) 0.037(3) 0.001(3) 0.005(2) -0.002(2) C61 0.045(4) 0.027(3) 0.042(3) 0.006(2) 0.010(3) 0.001(2) C62 0.047(4) 0.034(3) 0.042(3) 0.007(3) 0.005(3) -0.001(2) C71 0.048(4) 0.031(3) 0.034(3) -0.006(3) 0.008(3) 0.002(2) C72 0.051(4) 0.036(3) 0.038(3) -0.006(3) 0.011(3) 0.000(2) C81 0.051(4) 0.026(3) 0.040(3) 0.001(3) 0.007(3) 0.003(2) C82 0.056(5) 0.036(3) 0.049(3) -0.002(3) 0.018(3) -0.008(3) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 N51 . 1.919(4) ? Cu1 N21 . 1.972(4) ? Cu1 N11 . 2.019(4) ? Cu1 S1 . 2.2833(15) ? Cu2 O13 . 1.912(4) ? Cu2 N22 . 1.971(4) ? Cu2 N12 . 2.011(4) ? Cu2 S2 . 2.2658(16) ? S1 C71 . 1.729(5) ? S2 C72 . 1.715(5) ? S3 C81 . 1.634(6) ? S4 O33 . 1.421(16) ? S4 N3 . 1.669(7) ? S4 O23 . 1.769(13) ? O11 N1 . 1.240(5) ? O12 N2 . 1.250(5) ? O13 N3 . 1.187(6) ? O21 N1 . 1.244(5) ? O22 N2 . 1.242(5) ? O23 N3 . 1.161(14) ? O31 N1 . 1.242(6) ? O32 N2 . 1.240(5) ? O33 N3 . 1.250(12) ? N11 C11 . 1.335(5) ? N11 C51 . 1.358(5) ? N12 C12 . 1.333(6) ? N12 C52 . 1.349(6) ? N21 C61 . 1.277(6) ? N21 N31 . 1.354(5) ? N22 C62 . 1.274(6) ? N22 N32 . 1.357(5) ? N31 C71 . 1.337(6) ? N31 H31A . 0.86 ? N32 C72 . 1.338(7) ? N32 H32A . 0.86 ? N41 C71 . 1.301(5) ? N41 H41A . 0.86 ? N41 H41B . 0.86 ? N42 C72 . 1.310(6) ? N42 H42A . 0.86 ? N42 H42B . 0.86 ? N51 C81 . 1.164(6) ? C11 C21 . 1.363(7) ? C11 H11 . 0.93 ? C12 C22 . 1.396(7) ? C12 H12 . 0.93 ? C21 C31 . 1.382(7) ? C21 H21 . 0.93 ? C22 C32 . 1.375(7) ? C22 H22 . 0.93 ? C31 C41 . 1.385(6) ? C31 H31 . 0.93 ? C32 C42 . 1.385(7) ? C32 H32 . 0.93 ? C41 C51 . 1.378(7) ? C41 H41 . 0.93 ? C42 C52 . 1.371(7) ? C42 H42 . 0.93 ? C51 C61 . 1.448(6) ? C52 C62 . 1.475(7) ? C61 H61 . 0.93 ? C62 H62 . 0.93 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag #N3 S4 O23 39.3(5) . . ? N51 Cu1 N21 178.76(17) . . ? N51 Cu1 N11 99.42(17) . . ? N21 Cu1 N11 79.69(16) . . ? N51 Cu1 S1 96.02(15) . . ? N21 Cu1 S1 84.76(13) . . ? N11 Cu1 S1 162.73(11) . . ? O13 Cu2 N22 171.3(2) . . ? O13 Cu2 N12 95.30(19) . . ? N22 Cu2 N12 80.30(17) . . ? O13 Cu2 S2 99.34(17) . . ? N22 Cu2 S2 85.17(13) . . ? N12 Cu2 S2 165.36(11) . . ? C71 S1 Cu1 96.2(2) . . ? C72 S2 Cu2 96.6(2) . . ? O33 S4 N3 46.9(5) . . ? O33 S4 O23 85.9(7) . . ? N3 O13 Cu2 140.0(5) . . ? N3 O23 S4 65.7(8) . . ? N3 O33 S4 77.0(9) . . ? O11 N1 O31 119.2(5) . . ? O11 N1 O21 119.8(5) . . ? O31 N1 O21 121.0(5) . . ? O32 N2 O22 118.9(5) . . ? O32 N2 O12 120.9(4) . . ? O22 N2 O12 120.1(5) . . ? O23 N3 O13 108.8(8) . . ? O23 N3 O33 130.4(12) . . ? O13 N3 O33 120.4(10) . . ? O23 N3 S4 75.0(8) . . ? O13 N3 S4 175.8(5) . . ? O33 N3 S4 56.1(8) . . ? C11 N11 C51 118.5(5) . . ? C11 N11 Cu1 128.7(4) . . ? C51 N11 Cu1 112.8(3) . . ? C12 N12 C52 119.2(5) . . ? C12 N12 Cu2 127.5(4) . . ? C52 N12 Cu2 113.3(3) . . ? C61 N21 N31 122.6(4) . . ? C61 N21 Cu1 117.5(3) . . ? N31 N21 Cu1 120.0(4) . . ? C62 N22 N32 123.9(4) . . ? C62 N22 Cu2 117.1(3) . . ? N32 N22 Cu2 119.0(3) . . ? C71 N31 N21 117.6(4) . . ? C71 N31 H31A 121.2 . . ? N21 N31 H31A 121.2 . . ? C72 N32 N22 118.2(4) . . ? C72 N32 H32A 120.9 . . ? N22 N32 H32A 120.9 . . ? C71 N41 H41A 120 . . ? C71 N41 H41B 120 . . ? H41A N41 H41B 120 . . ? C72 N42 H42A 120 . . ? C72 N42 H42B 120 . . ? H42A N42 H42B 120 . . ? C81 N51 Cu1 152.5(4) . . ? N11 C11 C21 123.1(5) . . ? N11 C11 H11 118.5 . . ? C21 C11 H11 118.5 . . ? N12 C12 C22 121.3(5) . . ? N12 C12 H12 119.3 . . ? C22 C12 H12 119.3 . . ? C11 C21 C31 118.7(5) . . ? C11 C21 H21 120.7 . . ? C31 C21 H21 120.7 . . ? C32 C22 C12 119.0(5) . . ? C32 C22 H22 120.5 . . ? C12 C22 H22 120.5 . . ? C21 C31 C41 119.3(5) . . ? C21 C31 H31 120.3 . . ? C41 C31 H31 120.3 . . ? C22 C32 C42 119.5(6) . . ? C22 C32 H32 120.2 . . ? C42 C32 H32 120.2 . . ? C51 C41 C31 118.9(5) . . ? C51 C41 H41 120.6 . . ? C31 C41 H41 120.6 . . ? C52 C42 C32 118.6(5) . . ? C52 C42 H42 120.7 . . ? C32 C42 H42 120.7 . . ? N11 C51 C41 121.4(4) . . ? N11 C51 C61 114.6(5) . . ? C41 C51 C61 123.9(4) . . ? N12 C52 C42 122.3(5) . . ? N12 C52 C62 114.1(5) . . ? C42 C52 C62 123.6(5) . . ? N21 C61 C51 115.1(4) . . ? N21 C61 H61 122.4 . . ? C51 C61 H61 122.4 . . ? N22 C62 C52 115.1(5) . . ? N22 C62 H62 122.4 . . ? C52 C62 H62 122.4 . . ? N41 C71 N31 118.9(4) . . ? N41 C71 S1 119.8(5) . . ? N31 C71 S1 121.3(4) . . ? N42 C72 N32 118.3(5) . . ? N42 C72 S2 120.6(5) . . ? N32 C72 S2 121.0(4) . . ? N51 C81 S3 179.1(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 #N22 Cu2 O13 N3 -148.3(11) . . . . ? #Cu2 O13 N3 S4 -156(6) . . . . ? #O33 S4 N3 O13 -33(7) . . . . ? #O23 S4 N3 O13 155(7) . . . . ? #N51 Cu1 N21 C61 -48(9) . . . . ? #N51 Cu1 N21 N31 133(9) . . . . ? #O13 Cu2 N22 C62 -57.7(14) . . . . ? #O13 Cu2 N22 N32 119.1(12) . . . . ? #N21 Cu1 N51 C81 -135(8) . . . . ? N51 Cu1 S1 C71 179.11(19) . . . . ? N21 Cu1 S1 C71 -1.86(19) . . . . ? N11 Cu1 S1 C71 -27.6(4) . . . . ? O13 Cu2 S2 C72 -170.7(2) . . . . ? N22 Cu2 S2 C72 1.80(19) . . . . ? N12 Cu2 S2 C72 8.8(5) . . . . ? N12 Cu2 O13 N3 152.4(6) . . . . ? S2 Cu2 O13 N3 -27.7(7) . . . . ? O33 S4 O23 N3 -6.0(8) . . . . ? O23 S4 O33 N3 5.2(7) . . . . ? S4 O23 N3 O13 -178.1(5) . . . . ? S4 O23 N3 O33 8.9(12) . . . . ? Cu2 O13 N3 O23 -1.9(11) . . . . ? Cu2 O13 N3 O33 172.0(9) . . . . ? S4 O33 N3 O23 -10.4(15) . . . . ? S4 O33 N3 O13 177.3(6) . . . . ? O33 S4 N3 O23 171.8(12) . . . . ? O23 S4 N3 O33 -171.8(12) . . . . ? N51 Cu1 N11 C11 3.2(4) . . . . ? N21 Cu1 N11 C11 -175.9(4) . . . . ? S1 Cu1 N11 C11 -149.8(3) . . . . ? N51 Cu1 N11 C51 -176.0(3) . . . . ? N21 Cu1 N11 C51 4.9(3) . . . . ? S1 Cu1 N11 C51 30.9(6) . . . . ? O13 Cu2 N12 C12 -8.4(4) . . . . ? N22 Cu2 N12 C12 179.2(4) . . . . ? S2 Cu2 N12 C12 172.1(3) . . . . ? O13 Cu2 N12 C52 169.2(3) . . . . ? N22 Cu2 N12 C52 -3.2(3) . . . . ? S2 Cu2 N12 C52 -10.3(7) . . . . ? N11 Cu1 N21 C61 -4.1(3) . . . . ? S1 Cu1 N21 C61 -176.6(3) . . . . ? N11 Cu1 N21 N31 176.7(3) . . . . ? S1 Cu1 N21 N31 4.2(3) . . . . ? N12 Cu2 N22 C62 2.6(3) . . . . ? S2 Cu2 N22 C62 -179.2(3) . . . . ? N12 Cu2 N22 N32 179.3(3) . . . . ? S2 Cu2 N22 N32 -2.5(3) . . . . ? C61 N21 N31 C71 175.3(4) . . . . ? Cu1 N21 N31 C71 -5.5(5) . . . . ? C62 N22 N32 C72 178.7(4) . . . . ? Cu2 N22 N32 C72 2.2(5) . . . . ? N11 Cu1 N51 C81 -178.6(8) . . . . ? S1 Cu1 N51 C81 -6.3(8) . . . . ? C51 N11 C11 C21 0.3(6) . . . . ? Cu1 N11 C11 C21 -178.9(4) . . . . ? C52 N12 C12 C22 -1.2(7) . . . . ? Cu2 N12 C12 C22 176.2(3) . . . . ? N11 C11 C21 C31 2.6(7) . . . . ? N12 C12 C22 C32 0.0(7) . . . . ? C11 C21 C31 C41 -3.3(7) . . . . ? C12 C22 C32 C42 0.6(7) . . . . ? C21 C31 C41 C51 1.2(7) . . . . ? C22 C32 C42 C52 -0.1(7) . . . . ? C11 N11 C51 C41 -2.5(6) . . . . ? Cu1 N11 C51 C41 176.8(3) . . . . ? C11 N11 C51 C61 175.7(4) . . . . ? Cu1 N11 C51 C61 -5.0(5) . . . . ? C31 C41 C51 N11 1.7(7) . . . . ? C31 C41 C51 C61 -176.3(4) . . . . ? C12 N12 C52 C42 1.8(7) . . . . ? Cu2 N12 C52 C42 -176.0(4) . . . . ? C12 N12 C52 C62 -178.8(4) . . . . ? Cu2 N12 C52 C62 3.4(5) . . . . ? C32 C42 C52 N12 -1.1(7) . . . . ? C32 C42 C52 C62 179.6(4) . . . . ? N31 N21 C61 C51 -178.3(4) . . . . ? Cu1 N21 C61 C51 2.6(5) . . . . ? N11 C51 C61 N21 1.8(6) . . . . ? C41 C51 C61 N21 179.9(4) . . . . ? N32 N22 C62 C52 -178.1(4) . . . . ? Cu2 N22 C62 C52 -1.5(5) . . . . ? N12 C52 C62 N22 -1.3(6) . . . . ? C42 C52 C62 N22 178.1(5) . . . . ? N21 N31 C71 N41 -176.2(4) . . . . ? N21 N31 C71 S1 3.5(6) . . . . ? Cu1 S1 C71 N41 179.5(3) . . . . ? Cu1 S1 C71 N31 -0.2(4) . . . . ? N22 N32 C72 N42 -179.4(4) . . . . ? N22 N32 C72 S2 -0.2(6) . . . . ? Cu2 S2 C72 N42 177.7(4) . . . . ? Cu2 S2 C72 N32 -1.4(4) . . . . ? #Cu1 N51 C81 S3 -15E1(3) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 930875'