# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound1 #TrackingRef 'structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H10 Cu2 N2 O8 S2' _chemical_formula_weight 537.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' '-x-1/2, y, z-1/2' 'x, -y-1/2, z-1/2' _cell_length_a 9.225(4) _cell_length_b 30.478(13) _cell_length_c 8.366(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2352.2(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 2.024 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.737 _exptl_absorpt_correction_T_max 0.784 _exptl_absorpt_process_details ; Data were corrected for absorption effects using the program SADABS (Sheldrick, G.M.; 1996). ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13566 _diffrn_reflns_av_R_equivalents 0.1293 _diffrn_reflns_av_sigmaI/netI 0.1402 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 28.07 _reflns_number_total 2803 _reflns_number_gt 1459 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1209P)^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 2803 _refine_ls_number_parameters 132 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1473 _refine_ls_R_factor_gt 0.0922 _refine_ls_wR_factor_ref 0.2392 _refine_ls_wR_factor_gt 0.2165 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _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 Cu1 Cu 0.76299(8) 0.53306(3) 0.11499(9) 0.0258(3) Uani 1 1 d . . . C8 C 0.9707(7) 0.4774(3) 0.0105(8) 0.0266(17) Uani 1 1 d . . . C7 C 0.5129(7) 0.5060(3) -0.0869(8) 0.0239(16) Uani 1 1 d . . . O4 O 0.9511(5) 0.55530(18) 0.0294(6) 0.0286(12) Uani 1 1 d . . . O2 O 0.5797(5) 0.50592(19) 0.1894(5) 0.0297(13) Uani 1 1 d . . . O3 O 0.8425(4) 0.47418(17) 0.0631(5) 0.0247(11) Uani 1 1 d . . . C3 C 0.6478(13) 0.6772(3) 0.2985(11) 0.056(3) Uani 1 1 d . . . C4 C 0.5384(11) 0.6503(3) 0.2285(16) 0.067(3) Uani 1 1 d . . . H4 H 0.4439 0.6605 0.2175 0.080 Uiso 1 1 calc R . . C2 C 0.7841(13) 0.6599(3) 0.3106(13) 0.058(3) Uani 1 1 d . . . H2 H 0.8579 0.6759 0.3589 0.070 Uiso 1 1 calc R . . C1 C 0.8113(10) 0.6186(3) 0.2505(11) 0.047(2) Uani 1 1 d . . . H1 H 0.9051 0.6075 0.2569 0.057 Uiso 1 1 calc R . . C5 C 0.5756(8) 0.6099(3) 0.1790(11) 0.044(2) Uani 1 1 d . . . H5 H 0.5027 0.5920 0.1385 0.052 Uiso 1 1 calc R . . N1 N 0.7091(7) 0.5938(2) 0.1839(7) 0.0286(14) Uani 1 1 d . . . O1 O 0.6270(5) 0.52635(17) -0.1202(6) 0.0314(12) Uani 1 1 d . . . S1 S 0.5936(5) 0.72999(11) 0.3642(5) 0.0925(13) Uani 1 1 d . . . C6 C 0.7500 0.7500 0.472(2) 0.165(15) Uani 1 2 d S . . H6A H 0.7171 0.7735 0.5411 0.198 Uiso 0.50 1 calc PR . . H6B H 0.7829 0.7265 0.5411 0.198 Uiso 0.50 1 calc PR . . 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 0.0161(4) 0.0393(6) 0.0221(5) -0.0014(4) 0.0036(3) -0.0008(4) C8 0.017(3) 0.043(5) 0.020(4) 0.004(3) 0.001(3) 0.000(3) C7 0.011(3) 0.042(5) 0.019(4) 0.000(3) -0.002(2) -0.002(3) O4 0.023(3) 0.038(3) 0.024(3) -0.003(2) 0.008(2) 0.002(2) O2 0.016(2) 0.060(4) 0.013(2) -0.002(2) -0.0009(18) -0.003(2) O3 0.009(2) 0.038(3) 0.027(3) 0.003(2) 0.0034(17) -0.0031(19) C3 0.085(8) 0.041(6) 0.042(6) 0.002(4) 0.016(5) 0.020(5) C4 0.037(5) 0.046(7) 0.117(10) -0.005(6) -0.006(6) 0.012(5) C2 0.070(7) 0.044(7) 0.061(7) -0.005(5) -0.011(5) 0.009(5) C1 0.044(5) 0.037(6) 0.062(6) -0.012(5) -0.020(4) 0.014(4) C5 0.022(4) 0.055(6) 0.054(6) -0.007(5) 0.000(3) 0.003(4) N1 0.023(3) 0.037(4) 0.027(3) 0.003(3) 0.002(2) 0.001(3) O1 0.026(2) 0.045(4) 0.023(3) 0.002(2) -0.003(2) -0.007(2) S1 0.123(3) 0.0422(19) 0.112(3) -0.0109(19) 0.054(2) 0.0111(18) C6 0.42(5) 0.038(11) 0.035(9) 0.000 0.000 -0.014(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 Cu1 O2 1.983(5) . ? Cu1 O3 1.987(5) . ? Cu1 O4 1.996(5) . ? Cu1 N1 2.001(7) . ? Cu1 O1 2.342(5) . ? C8 O3 1.266(7) . ? C8 O4 1.275(9) 5_765 ? C8 C8 1.491(15) 5_765 ? C7 O1 1.252(8) . ? C7 O2 1.264(8) 5_665 ? C7 C7 1.519(13) 5_665 ? O4 C8 1.275(9) 5_765 ? O2 C7 1.264(8) 5_665 ? C3 C2 1.367(14) . ? C3 C4 1.425(15) . ? C3 S1 1.773(10) . ? C4 C5 1.345(13) . ? C2 C1 1.380(13) . ? C1 N1 1.330(11) . ? C5 N1 1.326(10) . ? S1 C6 1.808(10) . ? C6 S1 1.808(10) 2_665 ? 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 O2 Cu1 O3 90.4(2) . . ? O2 Cu1 O4 174.8(2) . . ? O3 Cu1 O4 84.7(2) . . ? O2 Cu1 N1 94.8(2) . . ? O3 Cu1 N1 171.9(2) . . ? O4 Cu1 N1 90.3(2) . . ? O2 Cu1 O1 76.73(18) . . ? O3 Cu1 O1 86.30(19) . . ? O4 Cu1 O1 101.19(19) . . ? N1 Cu1 O1 100.9(2) . . ? O3 C8 O4 124.0(7) . 5_765 ? O3 C8 C8 116.9(8) . 5_765 ? O4 C8 C8 119.1(8) 5_765 5_765 ? O1 C7 O2 124.0(6) . 5_665 ? O1 C7 C7 117.7(7) . 5_665 ? O2 C7 C7 118.3(7) 5_665 5_665 ? C8 O4 Cu1 108.7(5) 5_765 . ? C7 O2 Cu1 118.9(4) 5_665 . ? C8 O3 Cu1 110.5(5) . . ? C2 C3 C4 117.5(9) . . ? C2 C3 S1 125.9(9) . . ? C4 C3 S1 116.7(8) . . ? C5 C4 C3 118.2(9) . . ? C3 C2 C1 119.4(10) . . ? N1 C1 C2 122.8(9) . . ? N1 C5 C4 124.5(9) . . ? C5 N1 C1 117.4(8) . . ? C5 N1 Cu1 124.3(6) . . ? C1 N1 Cu1 118.0(6) . . ? C7 O1 Cu1 107.9(4) . . ? C3 S1 C6 103.6(5) . . ? S1 C6 S1 120.1(10) 2_665 . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 28.07 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 1.197 _refine_diff_density_min -1.681 _refine_diff_density_rms 0.172 _database_code_depnum_ccdc_archive 'CCDC 919612' ####################################################################### # # 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_compound2 #TrackingRef 'structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 Cu N2 O7 S2' _chemical_formula_weight 446.91 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P21/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 9.7573(10) _cell_length_b 16.7259(17) _cell_length_c 10.2055(10) _cell_angle_alpha 90.00 _cell_angle_beta 95.508(2) _cell_angle_gamma 90.00 _cell_volume 1657.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.791 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 1.611 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.697 _exptl_absorpt_correction_T_max 0.824 _exptl_absorpt_process_details ; Data were corrected for absorption effects using the program SADABS (Sheldrick, G.M.; 1996). ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10738 _diffrn_reflns_av_R_equivalents 0.0979 _diffrn_reflns_av_sigmaI/netI 0.1672 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 28.07 _reflns_number_total 3956 _reflns_number_gt 1753 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0106P)^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 3956 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1270 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.0685 _refine_ls_wR_factor_gt 0.0568 _refine_ls_goodness_of_fit_ref 0.754 _refine_ls_restrained_S_all 0.754 _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 Cu1 Cu 0.74731(5) 0.44479(3) 0.61295(4) 0.03390(14) Uani 1 1 d . . . O6 O 0.6585(3) 0.54545(15) 0.5541(2) 0.0352(7) Uani 1 1 d . . . N1 N 0.8625(3) 0.43643(18) 0.4620(3) 0.0280(8) Uani 1 1 d . . . C12 C 0.7928(4) 0.3347(3) 0.8071(4) 0.0364(11) Uani 1 1 d . . . O2 O 0.6921(3) 0.46360(16) 0.7891(2) 0.0421(7) Uani 1 1 d . . . O3 O 0.8140(3) 0.27348(17) 0.8706(2) 0.0545(9) Uani 1 1 d . . . N2 N 1.2311(4) 0.2241(2) -0.3493(3) 0.0452(10) Uani 1 1 d . . . O1 O 0.8242(3) 0.34679(15) 0.6901(2) 0.0450(8) Uani 1 1 d . . . C4 C 0.9979(4) 0.4131(2) 0.2373(3) 0.0340(10) Uani 1 1 d . . . C2 C 0.9629(4) 0.3832(2) 0.4585(3) 0.0349(10) Uani 1 1 d . . . H2 H 0.9869 0.3534 0.5341 0.042 Uiso 1 1 calc R . . C13 C 0.7172(4) 0.4047(3) 0.8656(4) 0.0374(11) Uani 1 1 d . . . C3 C 1.0345(4) 0.3692(2) 0.3500(3) 0.0382(11) Uani 1 1 d . . . H3 H 1.1048 0.3315 0.3528 0.046 Uiso 1 1 calc R . . C6 C 0.8340(4) 0.4796(2) 0.3547(4) 0.0402(11) Uani 1 1 d . . . H6 H 0.7672 0.5192 0.3558 0.048 Uiso 1 1 calc R . . C10 C 1.1889(4) 0.2536(2) -0.1315(4) 0.0409(11) Uani 1 1 d . . . H10 H 1.1396 0.2440 -0.0595 0.049 Uiso 1 1 calc R . . C8 C 1.3548(4) 0.3265(2) -0.2377(3) 0.0365(10) Uani 1 1 d . . . H8 H 1.4202 0.3670 -0.2372 0.044 Uiso 1 1 calc R . . C7 C 1.3248(4) 0.2821(2) -0.3478(4) 0.0422(11) Uani 1 1 d . . . H7 H 1.3698 0.2921 -0.4225 0.051 Uiso 1 1 calc R . . C5 C 0.8979(4) 0.4693(2) 0.2405(3) 0.0445(12) Uani 1 1 d . . . H5 H 0.8727 0.5006 0.1668 0.053 Uiso 1 1 calc R . . C9 C 1.2881(4) 0.3119(2) -0.1252(3) 0.0313(10) Uani 1 1 d . . . C11 C 1.1629(4) 0.2097(2) -0.2435(4) 0.0497(12) Uani 1 1 d . . . H11 H 1.0971 0.1694 -0.2469 0.060 Uiso 1 1 calc R . . C1 C 1.2280(4) 0.3489(2) 0.1308(3) 0.0448(12) Uani 1 1 d . . . H1A H 1.2670 0.3668 0.2167 0.054 Uiso 1 1 calc R . . H1B H 1.2123 0.2917 0.1350 0.054 Uiso 1 1 calc R . . O5 O 0.5415(3) 0.39933(14) 0.5249(2) 0.0350(7) Uani 1 1 d . . . O4 O 0.6823(3) 0.39967(17) 0.9794(2) 0.0518(8) Uani 1 1 d . . . C14 C 0.5317(4) 0.5425(2) 0.5082(3) 0.0300(10) Uani 1 1 d . . . O1W O 0.5621(3) 0.47406(18) 1.1960(3) 0.0662(9) Uani 1 1 d . . . H1 H 1.219(4) 0.187(3) -0.429(4) 0.094(17) Uiso 1 1 d . . . S1 S 1.06754(12) 0.39963(8) 0.08628(10) 0.0496(3) Uani 1 1 d . . . S2 S 1.34433(11) 0.36999(7) 0.01080(9) 0.0461(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0396(3) 0.0345(3) 0.0290(3) 0.0033(3) 0.0104(2) 0.0054(3) O6 0.0344(17) 0.0331(18) 0.0387(15) 0.0035(13) 0.0067(13) -0.0037(14) N1 0.031(2) 0.029(2) 0.0244(17) 0.0006(16) 0.0036(14) 0.0023(16) C12 0.042(3) 0.037(3) 0.029(2) 0.003(2) 0.002(2) 0.005(2) O2 0.059(2) 0.0408(19) 0.0283(15) 0.0053(14) 0.0115(14) 0.0122(15) O3 0.093(3) 0.040(2) 0.0315(17) 0.0090(15) 0.0134(16) 0.0102(18) N2 0.057(3) 0.042(3) 0.038(2) -0.0110(19) 0.006(2) -0.006(2) O1 0.063(2) 0.0453(19) 0.0300(16) 0.0061(14) 0.0196(14) 0.0161(16) C4 0.035(3) 0.040(3) 0.027(2) -0.002(2) 0.0044(19) -0.002(2) C2 0.039(3) 0.041(3) 0.025(2) 0.006(2) 0.0045(19) 0.004(2) C13 0.031(3) 0.047(3) 0.035(3) -0.002(2) 0.006(2) -0.001(2) C3 0.040(3) 0.045(3) 0.030(2) 0.005(2) 0.007(2) 0.007(2) C6 0.041(3) 0.045(3) 0.036(2) 0.006(2) 0.008(2) 0.009(2) C10 0.048(3) 0.041(3) 0.037(3) -0.002(2) 0.017(2) -0.009(2) C8 0.043(3) 0.034(3) 0.034(2) 0.000(2) 0.012(2) -0.003(2) C7 0.057(3) 0.041(3) 0.031(3) -0.005(2) 0.015(2) 0.001(2) C5 0.056(3) 0.056(3) 0.023(2) 0.012(2) 0.008(2) 0.013(3) C9 0.035(3) 0.028(2) 0.032(2) -0.003(2) 0.009(2) 0.004(2) C11 0.048(3) 0.044(3) 0.060(3) -0.007(3) 0.015(3) -0.013(2) C1 0.048(3) 0.059(3) 0.030(2) -0.001(2) 0.015(2) 0.004(2) O5 0.0359(17) 0.0224(16) 0.0473(17) 0.0060(14) 0.0065(13) 0.0064(13) O4 0.069(2) 0.058(2) 0.0315(16) 0.0116(15) 0.0218(15) 0.0228(17) C14 0.040(3) 0.031(3) 0.021(2) 0.001(2) 0.0142(19) -0.004(2) O1W 0.074(2) 0.067(2) 0.058(2) -0.0080(17) 0.0079(17) 0.0050(18) S1 0.0509(8) 0.0729(9) 0.0266(6) 0.0033(6) 0.0120(5) 0.0161(7) S2 0.0455(7) 0.0621(9) 0.0328(6) -0.0132(6) 0.0145(5) -0.0111(6) _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 Cu1 O1 1.938(2) . ? Cu1 O2 1.951(2) . ? Cu1 O6 1.961(2) . ? Cu1 N1 1.997(3) . ? Cu1 O5 2.252(3) . ? O6 C14 1.281(4) . ? N1 C6 1.319(4) . ? N1 C2 1.327(4) . ? C12 O3 1.218(4) . ? C12 O1 1.277(4) . ? C12 C13 1.535(5) . ? O2 C13 1.267(4) . ? N2 C7 1.332(5) . ? N2 C11 1.343(5) . ? C4 C5 1.358(5) . ? C4 C3 1.382(4) . ? C4 S1 1.758(4) . ? C2 C3 1.385(5) . ? C13 O4 1.244(4) . ? C6 C5 1.384(5) . ? C10 C11 1.362(5) . ? C10 C9 1.371(5) . ? C8 C7 1.356(5) . ? C8 C9 1.395(4) . ? C9 S2 1.739(4) . ? C1 S2 1.783(3) . ? C1 S1 1.800(4) . ? O5 C14 1.235(4) 3_666 ? C14 O5 1.235(4) 3_666 ? C14 C14 1.553(7) 3_666 ? 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 O1 Cu1 O2 83.83(10) . . ? O1 Cu1 O6 173.17(10) . . ? O2 Cu1 O6 89.47(10) . . ? O1 Cu1 N1 91.70(12) . . ? O2 Cu1 N1 161.39(11) . . ? O6 Cu1 N1 95.08(11) . . ? O1 Cu1 O5 99.91(11) . . ? O2 Cu1 O5 96.16(10) . . ? O6 Cu1 O5 79.44(9) . . ? N1 Cu1 O5 102.41(10) . . ? C14 O6 Cu1 117.5(3) . . ? C6 N1 C2 116.3(3) . . ? C6 N1 Cu1 120.8(3) . . ? C2 N1 Cu1 122.7(2) . . ? O3 C12 O1 125.9(4) . . ? O3 C12 C13 119.8(4) . . ? O1 C12 C13 114.2(4) . . ? C13 O2 Cu1 112.8(2) . . ? C7 N2 C11 120.9(4) . . ? C12 O1 Cu1 113.3(3) . . ? C5 C4 C3 118.5(3) . . ? C5 C4 S1 116.7(3) . . ? C3 C4 S1 124.8(3) . . ? N1 C2 C3 124.5(3) . . ? O4 C13 O2 125.0(4) . . ? O4 C13 C12 119.8(4) . . ? O2 C13 C12 115.2(3) . . ? C4 C3 C2 117.7(4) . . ? N1 C6 C5 123.7(4) . . ? C11 C10 C9 119.8(3) . . ? C7 C8 C9 120.4(4) . . ? N2 C7 C8 120.1(4) . . ? C4 C5 C6 119.3(4) . . ? C10 C9 C8 118.0(4) . . ? C10 C9 S2 127.0(3) . . ? C8 C9 S2 115.0(3) . . ? N2 C11 C10 120.7(4) . . ? S2 C1 S1 109.2(2) . . ? C14 O5 Cu1 108.3(2) 3_666 . ? O5 C14 O6 125.6(4) 3_666 . ? O5 C14 C14 118.6(5) 3_666 3_666 ? O6 C14 C14 115.8(5) . 3_666 ? C4 S1 C1 103.84(18) . . ? C9 S2 C1 105.33(18) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 28.07 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.393 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.085 _database_code_depnum_ccdc_archive 'CCDC 919613' ####################################################################### # # 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_compound3 #TrackingRef 'structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 Cu N4 O7 S4' _chemical_formula_weight 640.17 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' 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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 14.860(3) _cell_length_b 30.778(5) _cell_length_c 11.919(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.102(3) _cell_angle_gamma 90.00 _cell_volume 5429.7(17) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prims _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2600 _exptl_absorpt_coefficient_mu 1.161 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.733 _exptl_absorpt_correction_T_max 0.890 _exptl_absorpt_process_details ; Data were corrected for absorption effects using the program SADABS (Sheldrick, G.M.; 1996). ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16432 _diffrn_reflns_av_R_equivalents 0.0765 _diffrn_reflns_av_sigmaI/netI 0.0827 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 25.71 _reflns_number_total 4585 _reflns_number_gt 3078 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1190P)^2^+19.0853P] 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 4585 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0983 _refine_ls_R_factor_gt 0.0610 _refine_ls_wR_factor_ref 0.1782 _refine_ls_wR_factor_gt 0.1538 _refine_ls_goodness_of_fit_ref 0.846 _refine_ls_restrained_S_all 0.846 _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 -0.09050(4) 0.20590(2) 0.53925(5) 0.0397(2) Uani 1 1 d . . . S1 S 0.30784(11) 0.22425(5) 0.33215(14) 0.0561(4) Uani 1 1 d . . . S2 S 0.38364(11) 0.17260(6) 0.39016(14) 0.0616(5) Uani 1 1 d . . . S3 S -0.16673(14) 0.02347(5) 0.24849(14) 0.0659(5) Uani 1 1 d . . . S4 S -0.08117(13) 0.02396(6) 0.12530(16) 0.0731(6) Uani 1 1 d . . . O1 O -0.0395(3) 0.16004(13) 0.6670(3) 0.0508(10) Uani 1 1 d . . . O2 O -0.0415(3) 0.24673(14) 0.6667(3) 0.0581(11) Uani 1 1 d . . . O3 O -0.2190(3) 0.20770(13) 0.5913(3) 0.0580(11) Uani 1 1 d . . . O4 O -0.1514(3) 0.25550(15) 0.4333(3) 0.0591(11) Uani 1 1 d . . . N1 N 0.0319(3) 0.21162(14) 0.4689(4) 0.0426(11) Uani 1 1 d . . . N2 N 0.3900(4) 0.0774(2) 0.0982(6) 0.0719(16) Uani 1 1 d . . . N11 N -0.1256(3) 0.15102(14) 0.4371(4) 0.0436(11) Uani 1 1 d . . . N12 N -0.2262(6) 0.0857(2) -0.1869(5) 0.086(2) Uani 1 1 d . . . C1 C 0.0952(4) 0.18122(19) 0.4905(5) 0.0481(14) Uani 1 1 d . . . H1 H 0.0808 0.1576 0.5341 0.060(18) Uiso 1 1 d R . . C2 C 0.1804(4) 0.18274(19) 0.4534(5) 0.0505(14) Uani 1 1 d . . . H2 H 0.2218 0.1607 0.4724 0.030(13) Uiso 1 1 d R . . C3 C 0.2030(4) 0.21710(18) 0.3867(4) 0.0430(13) Uani 1 1 d . . . C4 C 0.1387(4) 0.24927(19) 0.3642(5) 0.0478(14) Uani 1 1 d . . . H4 H 0.1517 0.2735 0.3217 0.041(14) Uiso 1 1 d R . . C5 C 0.0551(4) 0.24515(18) 0.4053(4) 0.0456(13) Uani 1 1 d . . . H5 H 0.0124 0.2668 0.3878 0.049(16) Uiso 1 1 d R . . C6 C 0.3797(4) 0.1365(2) 0.2727(5) 0.0507(15) Uani 1 1 d . . . C7 C 0.3855(4) 0.0929(2) 0.2938(6) 0.0619(17) Uani 1 1 d . . . H7 H 0.3861 0.0825 0.3671 0.10(3) Uiso 1 1 d R . . C8 C 0.3906(5) 0.0643(2) 0.2051(8) 0.072(2) Uani 1 1 d . . . H8 H 0.3953 0.0348 0.2210 0.13(3) Uiso 1 1 d R . . C9 C 0.3844(4) 0.1200(2) 0.0807(6) 0.0652(18) Uani 1 1 d . . . H9 H 0.3829 0.1297 0.0066 0.037(14) Uiso 1 1 d R . . C10 C 0.3800(4) 0.1507(2) 0.1638(5) 0.0561(16) Uani 1 1 d . . . H10 H 0.3774 0.1802 0.1471 0.055(17) Uiso 1 1 d R . . C11 C -0.1079(4) 0.14847(19) 0.3298(5) 0.0490(14) Uani 1 1 d . . . H11 H -0.0898 0.1735 0.2945 0.066(19) Uiso 1 1 d R . . C12 C -0.1176(4) 0.1110(2) 0.2681(5) 0.0536(15) Uani 1 1 d . . . H12 H -0.1027 0.1102 0.1940 0.054(17) Uiso 1 1 d R . . C13 C -0.1486(4) 0.07401(18) 0.3174(5) 0.0500(14) Uani 1 1 d . . . C14 C -0.1696(4) 0.07682(18) 0.4271(5) 0.0479(14) Uani 1 1 d . . . H14 H -0.1910 0.0526 0.4633 0.057(17) Uiso 1 1 d R . . C15 C -0.1581(4) 0.1159(2) 0.4822(5) 0.0519(15) Uani 1 1 d . . . H15 H -0.1745 0.1178 0.5556 0.07(2) Uiso 1 1 d R . . C16 C -0.1424(4) 0.0477(2) 0.0072(5) 0.0565(16) Uani 1 1 d . . . C17 C -0.0926(5) 0.0673(2) -0.0710(6) 0.0667(19) Uani 1 1 d . . . H17 H -0.0298 0.0677 -0.0607 0.09(3) Uiso 1 1 d R . . C18 C -0.1374(7) 0.0855(2) -0.1640(7) 0.078(2) Uani 1 1 d . . . H18 H -0.1028 0.0990 -0.2150 0.14(4) Uiso 1 1 d R . . C19 C -0.2728(6) 0.0658(3) -0.1116(6) 0.078(2) Uani 1 1 d . . . H19 H -0.3353 0.0651 -0.1268 0.08(2) Uiso 1 1 d R . . C20 C -0.2358(4) 0.0465(2) -0.0145(6) 0.0588(16) Uani 1 1 d . . . H20 H -0.2720 0.0334 0.0355 0.07(2) Uiso 1 1 d R . . C21 C 0.0000 0.1786(3) 0.7500 0.0417(18) Uani 1 2 d S . . C22 C 0.0000 0.2285(3) 0.7500 0.0429(18) Uani 1 2 d S . . C23 C -0.2703(4) 0.23611(18) 0.5458(4) 0.0438(13) Uani 1 1 d . . . O1W O 0.1649(5) 0.3454(2) 0.2140(5) 0.117(2) Uani 1 1 d . . . O2W O 0.5000 0.0471(3) 0.7500 0.126(3) Uani 1 2 d S . . O3W O 0.5811(5) 0.0132(2) 0.5662(6) 0.130(3) Uani 1 1 d . . . O4W O 0.4866(12) 0.1334(5) 0.6824(13) 0.148(6) Uani 0.50 1 d P . . 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 0.0327(4) 0.0453(4) 0.0413(4) -0.0015(3) 0.0047(3) 0.0042(3) S1 0.0516(9) 0.0513(9) 0.0690(10) -0.0035(8) 0.0260(8) -0.0049(7) S2 0.0464(9) 0.0774(12) 0.0614(10) -0.0060(8) 0.0076(8) 0.0100(8) S3 0.0921(14) 0.0402(9) 0.0634(10) -0.0055(7) -0.0033(9) -0.0058(8) S4 0.0683(12) 0.0702(12) 0.0779(12) -0.0254(10) -0.0091(9) 0.0210(9) O1 0.049(2) 0.061(3) 0.042(2) -0.010(2) 0.0043(18) -0.0073(19) O2 0.055(3) 0.058(3) 0.063(3) 0.017(2) 0.017(2) 0.014(2) O3 0.064(3) 0.055(3) 0.053(2) 0.007(2) -0.002(2) 0.011(2) O4 0.039(2) 0.076(3) 0.063(3) 0.001(2) 0.0117(19) 0.004(2) N1 0.049(3) 0.040(3) 0.039(2) 0.001(2) 0.007(2) -0.004(2) N2 0.057(4) 0.060(4) 0.098(5) -0.023(3) 0.007(3) 0.006(3) N11 0.041(3) 0.042(3) 0.048(3) 0.004(2) 0.003(2) -0.002(2) N12 0.124(7) 0.068(4) 0.068(4) 0.008(3) 0.008(4) -0.012(4) C1 0.048(3) 0.044(3) 0.054(3) 0.005(3) 0.017(3) -0.001(3) C2 0.049(3) 0.047(3) 0.057(4) 0.004(3) 0.011(3) 0.011(3) C3 0.049(3) 0.044(3) 0.038(3) -0.004(2) 0.016(3) -0.004(3) C4 0.052(3) 0.040(3) 0.052(3) 0.003(3) 0.013(3) 0.001(3) C5 0.045(3) 0.045(3) 0.046(3) 0.006(3) 0.005(3) 0.007(3) C6 0.033(3) 0.056(4) 0.064(4) 0.002(3) 0.009(3) -0.005(3) C7 0.051(4) 0.061(4) 0.075(5) 0.010(4) 0.008(3) -0.002(3) C8 0.054(4) 0.052(4) 0.111(7) -0.003(4) 0.012(4) -0.001(3) C9 0.063(4) 0.078(5) 0.055(4) -0.002(4) 0.005(3) 0.001(4) C10 0.062(4) 0.045(4) 0.062(4) -0.002(3) 0.010(3) -0.002(3) C11 0.065(4) 0.041(3) 0.041(3) 0.005(3) 0.002(3) -0.006(3) C12 0.068(4) 0.056(4) 0.037(3) 0.003(3) 0.006(3) -0.010(3) C13 0.054(4) 0.038(3) 0.056(4) 0.000(3) -0.006(3) 0.001(3) C14 0.057(4) 0.038(3) 0.047(3) 0.006(3) -0.002(3) -0.010(3) C15 0.047(3) 0.059(4) 0.051(4) 0.000(3) 0.007(3) -0.007(3) C16 0.071(4) 0.041(3) 0.058(4) -0.017(3) 0.009(3) -0.006(3) C17 0.067(5) 0.055(4) 0.080(5) -0.024(4) 0.018(4) -0.010(3) C18 0.098(7) 0.055(4) 0.084(6) -0.013(4) 0.016(5) -0.030(4) C19 0.074(5) 0.076(5) 0.081(5) -0.002(4) -0.008(4) 0.008(4) C20 0.052(4) 0.062(4) 0.063(4) -0.007(3) 0.008(3) 0.003(3) C21 0.036(4) 0.055(5) 0.037(4) 0.000 0.014(3) 0.000 C22 0.034(4) 0.049(5) 0.048(5) 0.000 0.019(4) 0.000 C23 0.039(3) 0.047(3) 0.044(3) -0.002(3) -0.001(2) 0.009(3) O1W 0.143(6) 0.090(5) 0.126(5) -0.032(4) 0.054(4) -0.008(4) O2W 0.133(8) 0.111(7) 0.132(8) 0.000 0.009(6) 0.000 O3W 0.162(6) 0.097(5) 0.139(6) 0.044(4) 0.055(5) 0.020(4) O4W 0.161(14) 0.123(12) 0.167(14) 0.011(10) 0.056(14) 0.034(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 O2 2.054(5) . ? Cu O3 2.060(5) . ? Cu N1 2.078(5) . ? Cu N11 2.120(5) . ? Cu O4 2.131(4) . ? Cu O1 2.163(4) . ? S1 C3 1.755(5) . ? S1 S2 2.034(2) . ? S2 C6 1.785(6) . ? S3 C13 1.769(6) . ? S3 S4 2.026(3) . ? S4 C16 1.765(7) . ? O1 C21 1.244(5) . ? O2 C22 1.254(5) . ? O3 C23 1.251(6) . ? O4 C23 1.239(6) 7_456 ? N1 C1 1.335(7) . ? N1 C5 1.343(7) . ? N2 C9 1.331(9) . ? N2 C8 1.334(9) . ? N11 C15 1.319(7) . ? N11 C11 1.330(7) . ? N12 C18 1.325(11) . ? N12 C19 1.329(10) . ? C1 C2 1.379(8) . ? C2 C3 1.382(8) . ? C3 C4 1.385(8) . ? C4 C5 1.381(7) . ? C6 C7 1.367(9) . ? C6 C10 1.369(8) . ? C7 C8 1.382(10) . ? C9 C10 1.374(9) . ? C11 C12 1.369(8) . ? C12 C13 1.378(8) . ? C13 C14 1.373(8) . ? C14 C15 1.373(8) . ? C16 C17 1.379(9) . ? C16 C20 1.390(9) . ? C17 C18 1.361(10) . ? C19 C20 1.372(10) . ? C21 O1 1.244(5) 2_556 ? C21 C22 1.535(11) . ? C22 O2 1.254(5) 2_556 ? C23 O4 1.239(6) 7_456 ? C23 C23 1.551(11) 7_456 ? O4W O4W 1.62(3) 2_656 ? 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 O2 Cu O3 92.17(16) . . ? O2 Cu N1 88.93(16) . . ? O3 Cu N1 170.99(17) . . ? O2 Cu N11 164.81(17) . . ? O3 Cu N11 90.39(17) . . ? N1 Cu N11 90.88(17) . . ? O2 Cu O4 95.95(17) . . ? O3 Cu O4 78.64(15) . . ? N1 Cu O4 92.35(16) . . ? N11 Cu O4 99.23(17) . . ? O2 Cu O1 78.46(15) . . ? O3 Cu O1 94.70(15) . . ? N1 Cu O1 94.29(16) . . ? N11 Cu O1 86.40(16) . . ? O4 Cu O1 171.23(15) . . ? C3 S1 S2 105.0(2) . . ? C6 S2 S1 104.0(2) . . ? C13 S3 S4 104.5(2) . . ? C16 S4 S3 105.6(2) . . ? C21 O1 Cu 111.8(4) . . ? C22 O2 Cu 115.4(4) . . ? C23 O3 Cu 115.7(4) . . ? C23 O4 Cu 112.8(4) 7_456 . ? C1 N1 C5 115.9(5) . . ? C1 N1 Cu 119.3(4) . . ? C5 N1 Cu 124.8(4) . . ? C9 N2 C8 116.2(6) . . ? C15 N11 C11 117.0(5) . . ? C15 N11 Cu 120.0(4) . . ? C11 N11 Cu 122.6(4) . . ? C18 N12 C19 115.3(7) . . ? N1 C1 C2 124.4(5) . . ? C1 C2 C3 119.2(5) . . ? C2 C3 C4 117.4(5) . . ? C2 C3 S1 125.3(5) . . ? C4 C3 S1 117.3(4) . . ? C5 C4 C3 119.5(5) . . ? N1 C5 C4 123.6(5) . . ? C7 C6 C10 118.8(6) . . ? C7 C6 S2 118.0(5) . . ? C10 C6 S2 122.8(5) . . ? C6 C7 C8 119.4(7) . . ? N2 C8 C7 122.8(7) . . ? N2 C9 C10 124.8(7) . . ? C6 C10 C9 117.9(6) . . ? N11 C11 C12 123.1(5) . . ? C11 C12 C13 119.3(5) . . ? C14 C13 C12 117.8(5) . . ? C14 C13 S3 117.3(4) . . ? C12 C13 S3 124.8(5) . . ? C13 C14 C15 118.8(5) . . ? N11 C15 C14 123.8(6) . . ? C17 C16 C20 118.2(7) . . ? C17 C16 S4 116.8(6) . . ? C20 C16 S4 125.0(5) . . ? C18 C17 C16 118.5(7) . . ? N12 C18 C17 125.2(8) . . ? N12 C19 C20 125.1(8) . . ? C19 C20 C16 117.7(7) . . ? O1 C21 O1 125.3(8) 2_556 . ? O1 C21 C22 117.4(4) 2_556 . ? O1 C21 C22 117.4(4) . . ? O2 C22 O2 126.9(8) . 2_556 ? O2 C22 C21 116.6(4) . . ? O2 C22 C21 116.6(4) 2_556 . ? O4 C23 O3 127.3(6) 7_456 . ? O4 C23 C23 117.2(6) 7_456 7_456 ? O3 C23 C23 115.5(6) . 7_456 ? _diffrn_measured_fraction_theta_max 0.887 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.934 _refine_diff_density_max 0.667 _refine_diff_density_min -0.858 _refine_diff_density_rms 0.093 _database_code_depnum_ccdc_archive 'CCDC 919614' ####################################################################### # # 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_compound4 ############### # CCDC 919615 # ############### _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Cu N2 O10 S2' _chemical_formula_weight 467.86 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 10.010(4) _cell_length_b 24.790(9) _cell_length_c 9.343(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.657(7) _cell_angle_gamma 90.00 _cell_volume 2123.5(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 654 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 19.40 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 940 _exptl_absorpt_coefficient_mu 1.272 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.680 _exptl_absorpt_correction_T_max 0.776 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6934 _diffrn_reflns_av_R_equivalents 0.1317 _diffrn_reflns_av_sigmaI/netI 0.2276 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 28.36 _reflns_number_total 2574 _reflns_number_gt 974 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1253P)^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 2574 _refine_ls_number_parameters 123 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2339 _refine_ls_R_factor_gt 0.0768 _refine_ls_wR_factor_ref 0.2848 _refine_ls_wR_factor_gt 0.1930 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.0000 0.43985(5) 0.2500 0.0400(5) Uani 1 2 d S . . S1 S -0.4014(3) 0.26101(9) -0.2555(3) 0.0511(7) Uani 1 1 d . . . N1 N -0.1224(7) 0.3836(2) 0.0995(7) 0.0385(16) Uani 1 1 d . . . O1 O -0.1162(6) 0.4963(2) 0.0991(6) 0.0441(14) Uani 1 1 d . . . O2 O 0.1366(6) 0.4538(2) 0.1079(6) 0.0449(15) Uani 1 1 d . . . C1 C -0.0696(9) 0.3518(3) 0.0200(9) 0.043(2) Uani 1 1 d . . . H1 H 0.0286 0.3546 0.0385 0.052 Uiso 1 1 calc R . . C2 C -0.1550(10) 0.3146(3) -0.0895(10) 0.050(2) Uani 1 1 d . . . H2 H -0.1147 0.2931 -0.1436 0.060 Uiso 1 1 calc R . . C3 C -0.3004(9) 0.3099(3) -0.1167(8) 0.0369(19) Uani 1 1 d . . . C4 C -0.3555(9) 0.3425(4) -0.0374(10) 0.049(2) Uani 1 1 d . . . H4 H -0.4535 0.3406 -0.0546 0.059 Uiso 1 1 calc R . . C5 C -0.2633(10) 0.3786(4) 0.0696(10) 0.054(2) Uani 1 1 d . . . H5 H -0.3022 0.4006 0.1238 0.065 Uiso 1 1 calc R . . C6 C -0.0719(9) 0.5127(3) -0.0033(9) 0.0370(19) Uani 1 1 d . . . O1W O 0.359(3) 0.2850(8) 0.117(3) 0.329(12) Uani 1 1 d . . . O2W O 0.364(2) 0.3997(16) 0.063(4) 0.419(19) Uani 1 1 d . . . O3W O 0.388(3) 0.4659(13) -0.169(3) 0.49(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.0460(10) 0.0371(8) 0.0309(9) 0.000 0.0092(7) 0.000 S1 0.0520(15) 0.0459(13) 0.0403(13) -0.0078(10) 0.0028(11) 0.0027(11) N1 0.037(4) 0.037(4) 0.036(4) 0.000(3) 0.009(3) 0.003(3) O1 0.048(4) 0.044(3) 0.043(3) 0.007(3) 0.022(3) 0.007(3) O2 0.047(4) 0.044(3) 0.041(3) 0.013(3) 0.016(3) 0.013(3) C1 0.038(5) 0.042(5) 0.046(5) -0.006(4) 0.013(4) 0.005(4) C2 0.050(6) 0.050(5) 0.045(5) -0.014(4) 0.014(5) 0.009(4) C3 0.036(5) 0.040(5) 0.022(4) 0.002(3) -0.002(4) 0.008(4) C4 0.035(5) 0.056(6) 0.053(6) -0.008(5) 0.013(4) 0.000(4) C5 0.048(6) 0.059(6) 0.055(6) -0.025(5) 0.020(5) 0.001(5) C6 0.047(5) 0.036(4) 0.028(4) -0.002(4) 0.016(4) -0.003(4) O1W 0.48(3) 0.32(2) 0.38(2) -0.125(19) 0.38(3) -0.145(19) O2W 0.173(17) 0.65(5) 0.45(3) -0.19(4) 0.144(19) 0.11(2) O3W 0.40(4) 0.51(4) 0.35(3) -0.06(3) -0.05(3) 0.36(3) _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 O1 1.995(5) . ? Cu O1 1.995(5) 2 ? Cu N1 2.010(6) . ? Cu N1 2.010(6) 2 ? Cu O2 2.283(6) . ? Cu O2 2.283(6) 2 ? S1 C3 1.767(8) . ? S1 S1 2.018(5) 2_454 ? N1 C1 1.329(10) . ? N1 C5 1.329(10) . ? O1 C6 1.273(9) . ? O2 C6 1.247(9) 5_565 ? O2 O2W 2.815(17) . ? C1 C2 1.388(11) . ? C2 C3 1.378(11) . ? C3 C4 1.354(11) . ? C4 C5 1.382(12) . ? C6 O2 1.247(9) 5_565 ? C6 C6 1.549(16) 5_565 ? O1W O2W 2.89(4) . ? O1W O1W 2.92(5) 2_655 ? O1W O1W 2.95(4) 7 ? O1W S1 3.468(15) 8_556 ? O2W O3W 2.80(4) . ? O3W O3W 3.17(7) 2_654 ? O3W O1 3.18(3) 5_565 ? O3W O2 3.23(2) 6_565 ? 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 O1 Cu O1 91.0(3) . 2 ? O1 Cu N1 88.5(2) . . ? O1 Cu N1 178.2(2) 2 . ? O1 Cu N1 178.2(2) . 2 ? O1 Cu N1 88.5(2) 2 2 ? N1 Cu N1 92.1(4) . 2 ? O1 Cu O2 78.4(2) . . ? O1 Cu O2 89.4(2) 2 . ? N1 Cu O2 92.2(2) . . ? N1 Cu O2 99.9(2) 2 . ? O1 Cu O2 89.4(2) . 2 ? O1 Cu O2 78.4(2) 2 2 ? N1 Cu O2 99.9(2) . 2 ? N1 Cu O2 92.2(2) 2 2 ? O2 Cu O2 162.5(3) . 2 ? C3 S1 S1 104.2(3) . 2_454 ? C1 N1 C5 116.9(7) . . ? C1 N1 Cu 122.3(6) . . ? C5 N1 Cu 120.7(5) . . ? C6 O1 Cu 118.3(5) . . ? C6 O2 Cu 108.2(5) 5_565 . ? C6 O2 O2W 113.4(9) 5_565 . ? Cu O2 O2W 136.3(9) . . ? N1 C1 C2 122.7(8) . . ? C3 C2 C1 118.9(7) . . ? C4 C3 C2 118.7(8) . . ? C4 C3 S1 124.9(7) . . ? C2 C3 S1 116.4(6) . . ? C3 C4 C5 118.8(8) . . ? N1 C5 C4 123.9(8) . . ? O2 C6 O1 125.0(7) 5_565 . ? O2 C6 C6 118.9(8) 5_565 5_565 ? O1 C6 C6 116.0(9) . 5_565 ? O2W O1W O1W 94.0(7) . 2_655 ? O2W O1W O1W 120.6(15) . 7 ? O1W O1W O1W 143.6(10) 2_655 7 ? O2W O1W S1 116.8(8) . 8_556 ? O1W O1W S1 108.0(7) 2_655 8_556 ? O1W O1W S1 68.0(5) 7 8_556 ? O3W O2W O2 99.3(14) . . ? O3W O2W O1W 136.3(10) . . ? O2 O2W O1W 111.8(12) . . ? O2W O3W O3W 131.8(9) . 2_654 ? O2W O3W O1 70.7(11) . 5_565 ? O3W O3W O1 157.5(8) 2_654 5_565 ? O2W O3W O2 124.9(14) . 6_565 ? O3W O3W O2 102.0(9) 2_654 6_565 ? O1 O3W O2 56.1(4) 5_565 6_565 ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.652 _refine_diff_density_min -0.781 _refine_diff_density_rms 0.136 _database_code_depnum_ccdc_archive 'CCDC 919615'