# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Matti Haukka' _publ_contact_author_email matti.haukka@uef.fi loop_ _publ_author_name 'Maximilian N. Kopylovich' 'Andreia C. C. Nunes' 'Kamran T. Mahmudov' 'Matti Haukka' 'Tatiana C. O. Mac Leod' ; L.M.D.R.S.Martins ; 'Maxim L. Kuznetsova' 'Armando J. L. Pombeiro' data_9 _database_code_depnum_ccdc_archive 'CCDC 798948' #TrackingRef 'Kopylovich.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H26 As2 Cu2 N4 O12' _chemical_formula_sum 'C22 H26 As2 Cu2 N4 O12' _chemical_formula_weight 815.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' As As 0.0499 2.0058 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9753(4) _cell_length_b 9.0989(4) _cell_length_c 10.3280(6) _cell_angle_alpha 112.022(4) _cell_angle_beta 94.776(6) _cell_angle_gamma 98.031(4) _cell_volume 680.42(6) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3525 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 30.03 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.990 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 406 _exptl_absorpt_coefficient_mu 4.047 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4836 _exptl_absorpt_correction_T_max 0.6402 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _publ_section_exptl_refinement ; The OH and H~2~O hydrogen atoms were located from the difference Fourier map but constrained to ride on their parent atom, with U~iso~ = 1.5 U~eq~(parent atom). Other hydrogen atoms were positioned geometrically and constrained to ride on their parent atoms, with C---H = 0.95-0.98 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 0.74\%A from atom O5 and the deepest hole is located 0.61 \%A from atom Cu1. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Bruker KAPPA APEX II CCD' _diffrn_measurement_device '62mm x 62mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 16 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11269 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3962 _reflns_number_gt 3400 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2008)' _computing_cell_refinement 'EvalCCD (Duisenberg, 2003)' _computing_data_reduction 'EvalCCD (Duisenberg, 2003)' _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond v.3.2c (Brandenburg, 2009)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0178P)^2^+1.4905P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3962 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0749 _refine_ls_wR_factor_gt 0.0680 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 As1 As 0.84511(3) 0.09757(3) 0.65516(3) 0.00897(7) Uani 1 1 d . . . Cu1 Cu 0.47771(4) 0.17127(4) 0.59888(3) 0.01122(8) Uani 1 1 d . . . O1 O 0.6385(2) 0.0195(2) 0.5750(2) 0.0130(4) Uani 1 1 d . . . O2 O 0.9681(2) -0.0353(2) 0.6534(2) 0.0130(4) Uani 1 1 d . . . O3 O 0.9336(3) 0.2244(2) 0.5794(2) 0.0153(4) Uani 1 1 d . . . H3O H 0.9727 0.1696 0.5071 0.023 Uiso 1 1 d R . . O4 O 0.4010(3) 0.8000(3) 0.7110(3) 0.0306(6) Uani 1 1 d . . . O5 O 0.3400(3) 0.3014(2) 0.5485(2) 0.0165(4) Uani 1 1 d . . . O6 O 0.3235(2) 0.0950(2) 0.7442(2) 0.0153(4) Uani 1 1 d . . . H6O H 0.2179 0.0609 0.7118 0.023 Uiso 1 1 d R . . H6P H 0.3597 0.0115 0.7419 0.023 Uiso 1 1 d R . . N1 N 0.6154(3) 0.3658(3) 0.7552(2) 0.0101(4) Uani 1 1 d . . . N2 N 0.5979(3) 0.5134(3) 0.7821(2) 0.0119(4) Uani 1 1 d . . . C1 C 0.8276(3) 0.2367(3) 0.8418(3) 0.0112(5) Uani 1 1 d . . . C2 C 0.9316(3) 0.2247(3) 0.9521(3) 0.0137(5) Uani 1 1 d . . . H2 H 0.9982 0.1422 0.9330 0.016 Uiso 1 1 calc R . . C3 C 0.9371(4) 0.3343(4) 1.0901(3) 0.0170(6) Uani 1 1 d . . . H3 H 1.0062 0.3261 1.1658 0.020 Uiso 1 1 calc R . . C4 C 0.8405(4) 0.4559(3) 1.1163(3) 0.0151(5) Uani 1 1 d . . . H4 H 0.8480 0.5335 1.2098 0.018 Uiso 1 1 calc R . . C5 C 0.7335(3) 0.4653(3) 1.0078(3) 0.0128(5) Uani 1 1 d . . . H5 H 0.6653 0.5466 1.0282 0.015 Uiso 1 1 calc R . . C6 C 0.7255(3) 0.3559(3) 0.8686(3) 0.0101(5) Uani 1 1 d . . . C7 C 0.4869(3) 0.5596(3) 0.7058(3) 0.0125(5) Uani 1 1 d . . . C8 C 0.5005(4) 0.7374(3) 0.7610(3) 0.0160(6) Uani 1 1 d . . . C9 C 0.6391(4) 0.8415(4) 0.8797(4) 0.0262(7) Uani 1 1 d . . . H9A H 0.6220 0.9536 0.9129 0.039 Uiso 1 1 calc R . . H9B H 0.7506 0.8347 0.8466 0.039 Uiso 1 1 calc R . . H9C H 0.6356 0.8045 0.9573 0.039 Uiso 1 1 calc R . . C10 C 0.3559(4) 0.4518(3) 0.5915(3) 0.0139(5) Uani 1 1 d . . . C11 C 0.2232(4) 0.5103(4) 0.5204(3) 0.0182(6) Uani 1 1 d . . . H11A H 0.1524 0.4183 0.4418 0.027 Uiso 1 1 calc R . . H11B H 0.2801 0.5866 0.4844 0.027 Uiso 1 1 calc R . . H11C H 0.1506 0.5641 0.5887 0.027 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 As1 0.00749(12) 0.00932(12) 0.00902(12) 0.00218(10) -0.00035(9) 0.00305(9) Cu1 0.00969(16) 0.00946(15) 0.01229(16) 0.00216(12) -0.00123(12) 0.00243(12) O1 0.0091(8) 0.0115(9) 0.0136(9) -0.0002(7) -0.0028(7) 0.0042(7) O2 0.0110(9) 0.0136(9) 0.0144(9) 0.0045(8) 0.0013(7) 0.0056(7) O3 0.0187(10) 0.0138(9) 0.0151(10) 0.0061(8) 0.0057(8) 0.0055(8) O4 0.0292(13) 0.0153(11) 0.0464(16) 0.0127(11) -0.0060(11) 0.0064(10) O5 0.0164(10) 0.0137(9) 0.0179(10) 0.0045(8) -0.0014(8) 0.0049(8) O6 0.0120(9) 0.0145(9) 0.0202(10) 0.0078(8) 0.0011(8) 0.0027(8) N1 0.0093(10) 0.0107(10) 0.0110(10) 0.0040(8) 0.0026(8) 0.0039(8) N2 0.0106(10) 0.0129(10) 0.0138(11) 0.0053(9) 0.0050(8) 0.0048(8) C1 0.0104(12) 0.0119(12) 0.0099(11) 0.0034(10) 0.0009(9) 0.0007(9) C2 0.0092(12) 0.0170(13) 0.0140(12) 0.0058(11) -0.0012(10) 0.0019(10) C3 0.0133(13) 0.0232(14) 0.0135(13) 0.0074(11) -0.0019(10) 0.0016(11) C4 0.0131(12) 0.0164(13) 0.0121(12) 0.0031(10) 0.0017(10) -0.0022(10) C5 0.0133(12) 0.0125(12) 0.0109(12) 0.0024(10) 0.0038(10) 0.0019(10) C6 0.0093(11) 0.0098(11) 0.0103(11) 0.0039(9) 0.0015(9) -0.0009(9) C7 0.0120(12) 0.0115(12) 0.0150(12) 0.0056(10) 0.0040(10) 0.0030(10) C8 0.0137(13) 0.0132(13) 0.0237(14) 0.0092(11) 0.0043(11) 0.0043(10) C9 0.0317(18) 0.0111(13) 0.0319(18) 0.0055(13) -0.0011(14) 0.0036(12) C10 0.0127(12) 0.0159(13) 0.0150(12) 0.0070(10) 0.0046(10) 0.0042(10) C11 0.0158(13) 0.0219(14) 0.0188(14) 0.0096(12) 0.0012(11) 0.0061(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 As1 O2 1.6558(19) . ? As1 O1 1.7056(19) . ? As1 O3 1.728(2) . ? As1 C1 1.898(3) . ? Cu1 O5 1.900(2) . yes Cu1 O1 1.9760(19) . yes Cu1 N1 1.991(2) . yes Cu1 O1 2.0082(19) 2_656 ? Cu1 O6 2.257(2) . yes O1 Cu1 2.0082(19) 2_656 ? O3 H3O 0.8398 . ? O4 C8 1.225(4) . ? O5 C10 1.255(3) . ? O6 H6O 0.8489 . ? O6 H6P 0.8422 . ? N1 N2 1.295(3) . ? N1 C6 1.442(3) . ? N2 C7 1.349(4) . ? C1 C2 1.400(4) . ? C1 C6 1.406(4) . ? C2 C3 1.392(4) . ? C2 H2 0.9500 . ? C3 C4 1.393(4) . ? C3 H3 0.9500 . ? C4 C5 1.388(4) . ? C4 H4 0.9500 . ? C5 C6 1.398(3) . ? C5 H5 0.9500 . ? C7 C10 1.444(4) . ? C7 C8 1.484(4) . ? C8 C9 1.494(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.505(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 As1 O1 116.00(9) . . ? O2 As1 O3 110.68(10) . . ? O1 As1 O3 107.93(10) . . ? O2 As1 C1 111.96(11) . . ? O1 As1 C1 104.80(10) . . ? O3 As1 C1 104.71(11) . . ? O5 Cu1 O1 157.40(9) . . yes O5 Cu1 N1 90.56(9) . . yes O1 Cu1 N1 100.10(8) . . yes O5 Cu1 O1 89.42(8) . 2_656 ? O1 Cu1 O1 77.40(8) . 2_656 ? N1 Cu1 O1 172.37(9) . 2_656 ? O5 Cu1 O6 101.75(8) . . yes O1 Cu1 O6 97.41(8) . . yes N1 Cu1 O6 93.73(8) . . yes O1 Cu1 O6 93.75(8) 2_656 . ? As1 O1 Cu1 117.55(10) . . ? As1 O1 Cu1 135.15(10) . 2_656 ? Cu1 O1 Cu1 102.60(8) . 2_656 ? As1 O3 H3O 108.8 . . ? C10 O5 Cu1 130.73(19) . . ? Cu1 O6 H6O 113.8 . . ? Cu1 O6 H6P 102.7 . . ? H6O O6 H6P 103.6 . . ? N2 N1 C6 111.0(2) . . ? N2 N1 Cu1 125.49(18) . . ? C6 N1 Cu1 122.53(17) . . ? N1 N2 C7 125.2(2) . . ? C2 C1 C6 120.9(2) . . ? C2 C1 As1 117.1(2) . . ? C6 C1 As1 121.8(2) . . ? C3 C2 C1 119.7(3) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 119.4(3) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 121.0(3) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 120.4(3) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C1 118.5(2) . . ? C5 C6 N1 120.7(2) . . ? C1 C6 N1 120.8(2) . . ? N2 C7 C10 125.2(2) . . ? N2 C7 C8 112.5(2) . . ? C10 C7 C8 122.0(3) . . ? O4 C8 C7 121.4(3) . . ? O4 C8 C9 119.6(3) . . ? C7 C8 C9 119.1(3) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C10 C7 122.1(3) . . ? O5 C10 C11 114.9(3) . . ? C7 C10 C11 122.9(3) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 _geom_hbond_publ_flag O3 H3O O2 0.84 1.80 2.635(3) 173.0 2_756 yes O6 H6O O2 0.85 2.00 2.847(3) 172.2 1_455 yes O6 H6P O4 0.84 1.91 2.741(3) 168.6 1_545 yes _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.659 _refine_diff_density_min -0.890 _refine_diff_density_rms 0.118 #===END======================================================================== data_10 _database_code_depnum_ccdc_archive 'CCDC 798949' #TrackingRef 'Kopylovich.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H28 Cu2 N4 O14 S2, 2(H2 O)' _chemical_formula_sum 'C22 H32 Cu2 N4 O16 S2' _chemical_formula_weight 799.72 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 '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 11.3561(3) _cell_length_b 9.1757(3) _cell_length_c 15.5166(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.876(2) _cell_angle_gamma 90.00 _cell_volume 1510.69(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7287 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 36.15 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.758 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 820 _exptl_absorpt_coefficient_mu 1.628 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6108 _exptl_absorpt_correction_T_max 0.8138 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _publ_section_exptl_refinement ; The H~2~O hydrogen atoms were located from the difference Fourier map but constrained to ride on their parent atom, with U~iso~ = 1.5 U~eq~(parent atom). Other hydrogen atoms were positioned geometrically and were also constrained to ride on their parent atoms, with C---H = 0.95-0.98 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 0.70 \%A from atom C1 and the deepest hole is located 0.61 \%A from atom Cu1. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'flat graphite crystal' _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_device '62mm x 62mm CCD camera on three-circle goniostat' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_measurement_method '\f scans and \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23254 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 36.31 _reflns_number_total 7238 _reflns_number_gt 5948 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2009)' _computing_cell_refinement 'SAINT (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond v.3.2c (Brandenburg, 2009)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0405P)^2^+0.3262P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7238 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0809 _refine_ls_wR_factor_gt 0.0765 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.340426(12) 0.068631(16) 0.475937(10) 0.00937(4) Uani 1 1 d . . . S1 S 0.43464(2) 0.19208(3) 0.667617(19) 0.00994(5) Uani 1 1 d . . . O1 O 0.42426(8) 0.21345(10) 0.57040(6) 0.01256(15) Uani 1 1 d . . . O2 O 0.48014(8) 0.32417(10) 0.71994(6) 0.01463(16) Uani 1 1 d . . . O3 O 0.50564(8) 0.06254(10) 0.70834(6) 0.01446(16) Uani 1 1 d . . . O4 O 0.25334(10) -0.50338(11) 0.44512(7) 0.02058(19) Uani 1 1 d . . . O5 O 0.28139(8) -0.07474(9) 0.38194(6) 0.01245(15) Uani 1 1 d . . . O6 O 0.17566(9) 0.21545(10) 0.40605(6) 0.01631(17) Uani 1 1 d . . . H6O H 0.1212 0.1991 0.3572 0.024 Uiso 1 1 d R . . H6P H 0.1957 0.3003 0.4168 0.024 Uiso 1 1 d R . . O7 O 0.46397(8) 0.12812(10) 0.41823(6) 0.01259(15) Uani 1 1 d . . . H7O H 0.4673 0.2215 0.4124 0.019 Uiso 1 1 d R . . H7P H 0.4526 0.0888 0.3657 0.019 Uiso 1 1 d R . . O8 O 0.46720(11) 0.41948(11) 0.39358(8) 0.0244(2) Uani 1 1 d . . . H8O H 0.4189 0.4573 0.4170 0.037 Uiso 1 1 d R . . H8P H 0.5019 0.4841 0.3727 0.037 Uiso 1 1 d R . . N1 N 0.25290(9) -0.03151(11) 0.54742(7) 0.00992(16) Uani 1 1 d . . . N2 N 0.22276(9) -0.16735(11) 0.54018(7) 0.01108(17) Uani 1 1 d . . . C1 C 0.27925(10) 0.16109(13) 0.66303(8) 0.01031(18) Uani 1 1 d . . . C2 C 0.23245(11) 0.24384(14) 0.71843(8) 0.0136(2) Uani 1 1 d . . . H2 H 0.2810 0.3219 0.7539 0.016 Uiso 1 1 calc R . . C3 C 0.11433(11) 0.21256(15) 0.72212(9) 0.0154(2) Uani 1 1 d . . . H3 H 0.0811 0.2705 0.7588 0.018 Uiso 1 1 calc R . . C4 C 0.04557(11) 0.09615(14) 0.67183(9) 0.0141(2) Uani 1 1 d . . . H4 H -0.0335 0.0722 0.6763 0.017 Uiso 1 1 calc R . . C5 C 0.09107(10) 0.01408(13) 0.61497(8) 0.01205(19) Uani 1 1 d . . . H5 H 0.0424 -0.0642 0.5799 0.014 Uiso 1 1 calc R . . C6 C 0.20804(10) 0.04655(12) 0.60936(8) 0.00979(18) Uani 1 1 d . . . C7 C 0.23976(11) -0.25508(13) 0.47543(8) 0.01205(19) Uani 1 1 d . . . C8 C 0.22174(12) -0.40982(14) 0.48982(9) 0.0158(2) Uani 1 1 d . . . C9 C 0.16911(16) -0.45459(16) 0.56175(11) 0.0249(3) Uani 1 1 d . . . H9A H 0.1402 -0.5559 0.5511 0.037 Uiso 1 1 calc R . . H9B H 0.0980 -0.3912 0.5581 0.037 Uiso 1 1 calc R . . H9C H 0.2347 -0.4459 0.6230 0.037 Uiso 1 1 calc R . . C10 C 0.25520(10) -0.20475(13) 0.39229(8) 0.01162(19) Uani 1 1 d . . . C11 C 0.22671(12) -0.29845(14) 0.30800(9) 0.0163(2) Uani 1 1 d . . . H11A H 0.1968 -0.2371 0.2527 0.024 Uiso 1 1 calc R . . H11B H 0.1614 -0.3695 0.3061 0.024 Uiso 1 1 calc R . . H11C H 0.3033 -0.3499 0.3102 0.024 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01005(6) 0.00875(7) 0.00895(7) -0.00119(4) 0.00293(5) -0.00127(4) S1 0.00894(10) 0.01036(12) 0.00955(11) -0.00234(9) 0.00212(8) -0.00055(8) O1 0.0140(3) 0.0132(4) 0.0103(4) -0.0021(3) 0.0041(3) -0.0038(3) O2 0.0133(3) 0.0140(4) 0.0151(4) -0.0069(3) 0.0033(3) -0.0031(3) O3 0.0128(3) 0.0152(4) 0.0133(4) 0.0002(3) 0.0022(3) 0.0044(3) O4 0.0242(4) 0.0105(4) 0.0248(5) -0.0033(3) 0.0059(4) 0.0002(3) O5 0.0135(3) 0.0110(4) 0.0120(4) -0.0023(3) 0.0035(3) -0.0012(3) O6 0.0167(4) 0.0106(4) 0.0161(4) 0.0009(3) -0.0010(3) 0.0010(3) O7 0.0146(3) 0.0116(4) 0.0124(4) -0.0011(3) 0.0058(3) -0.0009(3) O8 0.0273(5) 0.0141(5) 0.0354(6) 0.0029(4) 0.0157(5) 0.0021(4) N1 0.0102(3) 0.0085(4) 0.0101(4) -0.0006(3) 0.0025(3) -0.0007(3) N2 0.0111(4) 0.0082(4) 0.0115(4) 0.0005(3) 0.0011(3) -0.0002(3) C1 0.0097(4) 0.0108(5) 0.0099(4) -0.0004(3) 0.0027(3) -0.0001(3) C2 0.0137(4) 0.0146(5) 0.0127(5) -0.0020(4) 0.0051(4) 0.0008(4) C3 0.0144(5) 0.0184(6) 0.0148(5) -0.0003(4) 0.0069(4) 0.0034(4) C4 0.0114(4) 0.0173(6) 0.0140(5) 0.0033(4) 0.0049(4) 0.0023(4) C5 0.0104(4) 0.0128(5) 0.0121(5) 0.0023(4) 0.0030(4) 0.0000(4) C6 0.0109(4) 0.0091(5) 0.0085(4) 0.0014(3) 0.0024(3) 0.0009(3) C7 0.0124(4) 0.0089(5) 0.0124(5) -0.0016(3) 0.0015(4) -0.0005(3) C8 0.0167(5) 0.0104(5) 0.0155(5) -0.0002(4) -0.0002(4) -0.0017(4) C9 0.0388(8) 0.0149(6) 0.0210(7) 0.0002(5) 0.0109(6) -0.0087(6) C10 0.0078(4) 0.0118(5) 0.0130(5) -0.0022(4) 0.0009(3) 0.0007(3) C11 0.0177(5) 0.0147(5) 0.0146(5) -0.0052(4) 0.0034(4) -0.0007(4) _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 O5 1.9001(9) . yes Cu1 O1 1.9560(9) . yes Cu1 N1 1.9616(10) . yes Cu1 O7 1.9908(9) . yes Cu1 O6 2.2462(9) . yes S1 O2 1.4478(9) . ? S1 O3 1.4489(9) . ? S1 O1 1.4837(9) . ? S1 C1 1.7636(11) . ? O4 C8 1.2346(17) . ? O5 C10 1.2536(15) . ? O6 H6O 0.8040 . ? O6 H6P 0.8118 . ? O7 H7O 0.8640 . ? O7 H7P 0.8577 . ? O8 H8O 0.8345 . ? O8 H8P 0.8381 . ? N1 N2 1.2868(14) . ? N1 C6 1.4301(15) . ? N2 C7 1.3539(15) . ? C1 C2 1.3869(16) . ? C1 C6 1.4043(16) . ? C2 C3 1.3927(17) . ? C2 H2 0.9500 . ? C3 C4 1.3875(18) . ? C3 H3 0.9500 . ? C4 C5 1.3920(17) . ? C4 H4 0.9500 . ? C5 C6 1.3939(15) . ? C5 H5 0.9500 . ? C7 C10 1.4385(17) . ? C7 C8 1.4630(17) . ? C8 C9 1.499(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.5010(17) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Cu1 O1 171.85(4) . . yes O5 Cu1 N1 89.91(4) . . yes O1 Cu1 N1 95.96(4) . . yes O5 Cu1 O7 87.54(4) . . yes O1 Cu1 O7 85.29(4) . . yes N1 Cu1 O7 164.37(4) . . yes O5 Cu1 O6 92.25(4) . . yes O1 Cu1 O6 93.07(4) . . yes N1 Cu1 O6 92.93(4) . . yes O7 Cu1 O6 102.57(4) . . yes O2 S1 O3 114.22(5) . . ? O2 S1 O1 110.04(5) . . ? O3 S1 O1 112.46(5) . . ? O2 S1 C1 108.04(5) . . ? O3 S1 C1 106.18(6) . . ? O1 S1 C1 105.34(5) . . ? S1 O1 Cu1 120.88(5) . . ? C10 O5 Cu1 126.54(8) . . ? Cu1 O6 H6O 124.9 . . ? Cu1 O6 H6P 110.6 . . ? H6O O6 H6P 116.0 . . ? Cu1 O7 H7O 112.5 . . ? Cu1 O7 H7P 114.9 . . ? H7O O7 H7P 108.4 . . ? H8O O8 H8P 110.3 . . ? N2 N1 C6 113.35(9) . . ? N2 N1 Cu1 125.24(8) . . ? C6 N1 Cu1 121.27(8) . . ? N1 N2 C7 122.46(10) . . ? C2 C1 C6 120.69(10) . . ? C2 C1 S1 119.05(9) . . ? C6 C1 S1 120.07(9) . . ? C1 C2 C3 120.00(11) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 119.53(11) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 120.75(11) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C6 120.08(11) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 118.89(11) . . ? C5 C6 N1 120.70(10) . . ? C1 C6 N1 120.37(10) . . ? N2 C7 C10 124.74(11) . . ? N2 C7 C8 113.52(11) . . ? C10 C7 C8 121.12(11) . . ? O4 C8 C7 120.31(13) . . ? O4 C8 C9 120.03(12) . . ? C7 C8 C9 119.62(12) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C10 C7 122.06(11) . . ? O5 C10 C11 114.88(11) . . ? C7 C10 C11 122.70(11) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 _geom_hbond_publ_flag O6 H6O O2 0.80 2.17 2.9718(13) 174.0 4_565 yes O6 H6P O4 0.81 1.91 2.7241(14) 176.5 1_565 yes O7 H7O O8 0.86 1.84 2.7027(14) 176.8 . yes O7 H7P O3 0.86 1.97 2.7422(13) 150.1 3_656 yes O7 H7P S1 0.86 3.00 3.5813(9) 126.6 3_656 yes O8 H8O O4 0.83 2.11 2.9022(15) 159.3 1_565 yes O8 H8P O2 0.84 2.33 3.1215(14) 158.5 3_666 yes _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 36.31 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.693 _refine_diff_density_min -0.554 _refine_diff_density_rms 0.093 #===END======================================================================== data_11 _database_code_depnum_ccdc_archive 'CCDC 798950' #TrackingRef 'Kopylovich.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H14 Cu N2 O7 S' _chemical_formula_sum 'C11 H14 Cu N2 O7 S' _chemical_formula_weight 381.84 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 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 15.222(7) _cell_length_b 7.432(2) _cell_length_c 26.225(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2966.9(19) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1385 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 24.04 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.710 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1560 _exptl_absorpt_coefficient_mu 1.649 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6833 _exptl_absorpt_correction_T_max 0.8794 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _publ_section_exptl_refinement ; The H~2~O hydrogen atoms were located from the difference Fourier map but constrained to ride on their parent atom, with U~iso~ = 1.5 U~eq~(parent atom). Other hydrogen atoms were positioned geometrically and were also constrained to ride on their parent atoms, with C---H = 0.95-0.98 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 1.04 \%A from atom O6 and the deepest hole is located 0.87 \%A from atom S1. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'flat graphite crystal' _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_device '62mm x 62mm CCD camera on three-circle goniostat' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_measurement_method '\f scans and \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11212 _diffrn_reflns_av_R_equivalents 0.0916 _diffrn_reflns_av_sigmaI/netI 0.0847 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2603 _reflns_number_gt 1785 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2009)' _computing_cell_refinement 'SAINT (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond v.3.2d (Brandenburg, 2010)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0740P)^2^+0.1732P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2603 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1480 _refine_ls_wR_factor_gt 0.1294 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 Cu1 Cu 0.09698(5) 0.45149(8) 0.36069(2) 0.0157(2) Uani 1 1 d . . . S1 S 0.07935(10) 0.06021(16) 0.31043(5) 0.0145(3) Uani 1 1 d . . . O1 O 0.1136(3) 0.2396(4) 0.29707(14) 0.0167(9) Uani 1 1 d . . . O2 O 0.0765(3) -0.0636(5) 0.26744(15) 0.0206(9) Uani 1 1 d . . . O3 O 0.1245(3) -0.0145(5) 0.35417(14) 0.0169(9) Uani 1 1 d . . . O4 O 0.1048(3) 0.3565(5) 0.56807(15) 0.0261(11) Uani 1 1 d . . . O5 O 0.1820(3) 0.4082(5) 0.41542(15) 0.0213(10) Uani 1 1 d . . . O6 O -0.0046(3) 0.5832(5) 0.32872(17) 0.0375(12) Uani 1 1 d . . . H6O H -0.0394 0.6146 0.3537 0.056 Uiso 1 1 d R . . H6P H -0.0386 0.5343 0.3060 0.056 Uiso 1 1 d R . . O7 O 0.1859(3) 0.6137(5) 0.32969(18) 0.0402(13) Uani 1 1 d . . . H7O H 0.2396 0.5898 0.3381 0.060 Uiso 1 1 d R . . H7P H 0.1751 0.7224 0.3390 0.060 Uiso 1 1 d R . . N1 N 0.0206(3) 0.2856(5) 0.39838(17) 0.0141(11) Uani 1 1 d . . . N2 N 0.0161(3) 0.2647(5) 0.44708(17) 0.0150(11) Uani 1 1 d . . . C1 C -0.0310(4) 0.0946(6) 0.3291(2) 0.0130(12) Uani 1 1 d . . . C2 C -0.0988(4) 0.0131(7) 0.3029(2) 0.0165(13) Uani 1 1 d . . . H2 H -0.0862 -0.0584 0.2738 0.020 Uiso 1 1 calc R . . C3 C -0.1846(4) 0.0345(7) 0.3185(2) 0.0183(13) Uani 1 1 d . . . H3 H -0.2307 -0.0228 0.3003 0.022 Uiso 1 1 calc R . . C4 C -0.2037(4) 0.1391(7) 0.3606(2) 0.0226(14) Uani 1 1 d . . . H4 H -0.2630 0.1542 0.3711 0.027 Uiso 1 1 calc R . . C5 C -0.1363(4) 0.2224(7) 0.3876(2) 0.0188(13) Uani 1 1 d . . . H5 H -0.1492 0.2945 0.4165 0.023 Uiso 1 1 calc R . . C6 C -0.0506(4) 0.1993(6) 0.37195(19) 0.0118(12) Uani 1 1 d . . . C7 C 0.0801(4) 0.3244(7) 0.4789(2) 0.0170(13) Uani 1 1 d . . . C8 C 0.0565(5) 0.3001(7) 0.5333(2) 0.0217(14) Uani 1 1 d . . . C9 C -0.0272(4) 0.2094(7) 0.5460(2) 0.0234(15) Uani 1 1 d . . . H9A H -0.0313 0.1930 0.5830 0.035 Uiso 1 1 calc R . . H9B H -0.0293 0.0918 0.5291 0.035 Uiso 1 1 calc R . . H9C H -0.0765 0.2834 0.5342 0.035 Uiso 1 1 calc R . . C10 C 0.1640(4) 0.3821(7) 0.4616(2) 0.0180(13) Uani 1 1 d . . . C11 C 0.2404(5) 0.4075(8) 0.4973(2) 0.0289(16) Uani 1 1 d . . . H11A H 0.2929 0.4397 0.4777 0.043 Uiso 1 1 calc R . . H11B H 0.2512 0.2953 0.5159 0.043 Uiso 1 1 calc R . . H11C H 0.2269 0.5039 0.5216 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0214(5) 0.0105(4) 0.0153(4) 0.0030(3) -0.0005(3) -0.0015(3) S1 0.0209(9) 0.0090(6) 0.0137(7) 0.0003(5) 0.0001(6) 0.0006(6) O1 0.026(3) 0.0098(17) 0.014(2) 0.0039(15) 0.0017(17) -0.0010(16) O2 0.026(3) 0.0157(19) 0.020(2) -0.0056(17) 0.0003(18) 0.0022(18) O3 0.019(2) 0.0120(18) 0.019(2) 0.0045(16) -0.0029(17) 0.0030(16) O4 0.033(3) 0.026(2) 0.019(2) -0.0044(19) -0.009(2) -0.003(2) O5 0.019(3) 0.026(2) 0.019(2) 0.0056(18) -0.0053(17) -0.0010(17) O6 0.045(3) 0.037(3) 0.030(3) -0.003(2) -0.003(2) 0.000(2) O7 0.034(3) 0.029(2) 0.058(3) 0.005(2) 0.000(3) 0.003(2) N1 0.020(3) 0.010(2) 0.012(3) 0.0001(19) -0.007(2) -0.003(2) N2 0.026(3) 0.008(2) 0.011(3) -0.0006(18) 0.001(2) 0.001(2) C1 0.022(4) 0.005(2) 0.012(3) 0.004(2) 0.002(2) -0.001(2) C2 0.029(4) 0.008(2) 0.012(3) 0.000(2) 0.000(3) 0.000(2) C3 0.016(4) 0.017(3) 0.023(3) -0.003(2) -0.008(2) -0.006(2) C4 0.016(4) 0.024(3) 0.028(4) 0.004(3) -0.002(3) -0.008(3) C5 0.026(4) 0.013(3) 0.017(3) 0.001(2) 0.005(3) 0.001(3) C6 0.019(3) 0.007(2) 0.010(3) 0.005(2) 0.000(2) 0.001(2) C7 0.031(4) 0.007(2) 0.013(3) 0.001(2) -0.002(3) -0.002(2) C8 0.040(4) 0.005(2) 0.020(3) -0.002(2) -0.005(3) 0.004(3) C9 0.045(5) 0.011(3) 0.014(3) 0.001(2) 0.001(3) -0.006(3) C10 0.027(4) 0.008(2) 0.020(3) 0.000(2) -0.006(3) 0.005(2) C11 0.031(4) 0.026(3) 0.030(4) -0.002(3) -0.009(3) 0.001(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 Cu1 O5 1.959(4) . yes Cu1 N1 1.962(5) . yes Cu1 O7 1.987(5) . yes Cu1 O6 2.013(5) . yes Cu1 O1 2.308(4) . yes S1 O3 1.448(4) . ? S1 O2 1.456(4) . ? S1 O1 1.474(4) . ? S1 C1 1.769(6) . ? O4 C8 1.244(7) . ? O5 C10 1.256(7) . ? O6 H6O 0.8741 . ? O6 H6P 0.8688 . ? O7 H7O 0.8644 . ? O7 H7P 0.8600 . ? N1 N2 1.288(6) . ? N1 C6 1.438(7) . ? N2 C7 1.358(7) . ? C1 C2 1.380(8) . ? C1 C6 1.398(7) . ? C2 C3 1.378(8) . ? C2 H2 0.9500 . ? C3 C4 1.380(8) . ? C3 H3 0.9500 . ? C4 C5 1.393(8) . ? C4 H4 0.9500 . ? C5 C6 1.377(8) . ? C5 H5 0.9500 . ? C7 C10 1.423(9) . ? C7 C8 1.482(8) . ? C8 C9 1.480(9) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.505(8) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Cu1 N1 85.36(18) . . yes O5 Cu1 O7 87.11(18) . . yes N1 Cu1 O7 172.5(2) . . yes O5 Cu1 O6 153.18(17) . . yes N1 Cu1 O6 93.44(19) . . yes O7 Cu1 O6 93.3(2) . . yes O5 Cu1 O1 110.18(15) . . yes N1 Cu1 O1 90.04(16) . . yes O7 Cu1 O1 92.48(17) . . yes O6 Cu1 O1 96.61(16) . . yes O3 S1 O2 112.7(2) . . ? O3 S1 O1 111.5(2) . . ? O2 S1 O1 113.4(2) . . ? O3 S1 C1 106.7(2) . . ? O2 S1 C1 106.1(2) . . ? O1 S1 C1 105.8(2) . . ? S1 O1 Cu1 114.0(2) . . ? C10 O5 Cu1 126.0(4) . . ? Cu1 O6 H6O 106.4 . . ? Cu1 O6 H6P 122.7 . . ? H6O O6 H6P 105.4 . . ? Cu1 O7 H7O 114.6 . . ? Cu1 O7 H7P 108.9 . . ? H7O O7 H7P 107.6 . . ? N2 N1 C6 112.6(4) . . ? N2 N1 Cu1 127.3(3) . . ? C6 N1 Cu1 119.0(3) . . ? N1 N2 C7 122.2(5) . . ? C2 C1 C6 119.0(5) . . ? C2 C1 S1 120.5(4) . . ? C6 C1 S1 120.4(4) . . ? C3 C2 C1 120.6(5) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 C4 120.2(5) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C5 120.0(6) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 119.5(5) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C1 120.7(5) . . ? C5 C6 N1 121.0(5) . . ? C1 C6 N1 118.3(5) . . ? N2 C7 C10 123.1(5) . . ? N2 C7 C8 112.3(5) . . ? C10 C7 C8 124.2(5) . . ? O4 C8 C9 119.9(5) . . ? O4 C8 C7 121.4(6) . . ? C9 C8 C7 118.7(5) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C10 C7 123.4(5) . . ? O5 C10 C11 114.4(6) . . ? C7 C10 C11 122.2(5) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 _geom_hbond_publ_flag O6 H6O O4 0.87 2.29 3.139(6) 163.7 5_566 yes O6 H6P O2 0.87 2.14 2.957(6) 157.0 4 yes O7 H7O O3 0.86 2.25 3.106(6) 171.0 7_665 yes O7 H7O S1 0.86 2.86 3.630(5) 149.6 7_665 yes O7 H7P O3 0.86 2.14 2.987(6) 168.7 1_565 yes O7 H7P S1 0.86 3.00 3.728(5) 144.0 1_565 yes _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.673 _refine_diff_density_min -0.680 _refine_diff_density_rms 0.133 #===END======================================================================== data_12 _database_code_depnum_ccdc_archive 'CCDC 798951' #TrackingRef 'Kopylovich.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H30 Cu N4 O14 S2' _chemical_formula_sum 'C22 H30 Cu N4 O14 S2' _chemical_formula_weight 702.16 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 '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 9.6052(2) _cell_length_b 13.5156(2) _cell_length_c 11.6369(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.9336(8) _cell_angle_gamma 90.00 _cell_volume 1428.97(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7963 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 38.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.632 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 726 _exptl_absorpt_coefficient_mu 0.987 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8825 _exptl_absorpt_correction_T_max 0.9252 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _publ_section_exptl_refinement ; The H~2~O and NH hydrogen atoms were located from the difference Fourier map but constrained to ride on their parent atom, with U~iso~ = 1.5 U~eq~(parent atom). Other hydrogen atoms were positioned geometrically and were also constrained to ride on their parent atoms, with C---H = 0.95-0.98 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 1.30 \%A from atom H7O and the deepest hole is located 0.48 \%A from atom Cu1. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'curved graphite crystal' _diffrn_measurement_device_type 'Bruker KAPPA APEX II DUO CCD' _diffrn_measurement_device '62mm x 62mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20758 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 29.00 _reflns_number_total 3795 _reflns_number_gt 3301 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2009)' _computing_cell_refinement 'SAINT (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond v.3.2c (Brandenburg, 2009)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0392P)^2^+1.1792P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3795 _refine_ls_number_parameters 198 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0806 _refine_ls_wR_factor_gt 0.0774 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 Cu1 Cu 0.5000 0.0000 0.5000 0.01008(8) Uani 1 2 d S . . S1 S 0.66736(4) 0.18316(3) 0.85483(4) 0.01180(9) Uani 1 1 d . . . O1 O 0.55001(14) 0.21587(9) 0.74634(11) 0.0165(2) Uani 1 1 d . . . O2 O 0.79356(15) 0.24787(11) 0.88952(12) 0.0241(3) Uani 1 1 d . . . O3 O 0.70506(14) 0.07963(9) 0.84456(11) 0.0166(2) Uani 1 1 d . . . O4 O -0.05406(13) -0.06070(9) 0.64867(11) 0.0152(2) Uani 1 1 d . . . O5 O 0.35647(13) 0.00965(9) 0.63934(11) 0.0150(2) Uani 1 1 d . . . O6 O 0.47863(13) -0.14358(9) 0.47410(10) 0.0130(2) Uani 1 1 d . . . H6O H 0.4653 -0.1663 0.4016 0.019 Uiso 1 1 d R . . H6P H 0.5510 -0.1712 0.5190 0.019 Uiso 1 1 d R . . O7 O 0.66496(13) -0.02771(9) 0.64551(11) 0.0134(2) Uani 1 1 d . . . H7O H 0.6646 0.0092 0.7006 0.020 Uiso 1 1 d . . . H7P H 0.7477 -0.0468 0.6481 0.020 Uiso 1 1 d . . . N1 N 0.38906(15) 0.07982(10) 0.85672(12) 0.0121(3) Uani 1 1 d . . . H1N H 0.4235 0.0770 0.8012 0.018 Uiso 1 1 d R . . N2 N 0.26317(15) 0.03709(10) 0.84547(13) 0.0121(3) Uani 1 1 d . . . C1 C 0.59060(18) 0.18537(12) 0.97432(14) 0.0116(3) Uani 1 1 d . . . C2 C 0.65942(19) 0.23965(12) 1.07893(15) 0.0145(3) Uani 1 1 d . . . H2 H 0.7467 0.2757 1.0857 0.017 Uiso 1 1 calc R . . C3 C 0.6009(2) 0.24135(13) 1.17357(15) 0.0167(3) Uani 1 1 d . . . H3 H 0.6476 0.2788 1.2447 0.020 Uiso 1 1 calc R . . C4 C 0.4735(2) 0.18791(14) 1.16385(16) 0.0181(3) Uani 1 1 d . . . H4 H 0.4340 0.1889 1.2289 0.022 Uiso 1 1 calc R . . C5 C 0.40395(19) 0.13341(13) 1.06031(15) 0.0157(3) Uani 1 1 d . . . H5 H 0.3176 0.0967 1.0547 0.019 Uiso 1 1 calc R . . C6 C 0.46111(18) 0.13251(12) 0.96404(15) 0.0121(3) Uani 1 1 d . . . C7 C 0.19097(17) -0.01309(11) 0.74733(15) 0.0109(3) Uani 1 1 d . . . C8 C 0.04213(17) -0.04421(12) 0.74561(15) 0.0119(3) Uani 1 1 d . . . C9 C 0.01046(19) -0.04924(14) 0.86360(16) 0.0178(3) Uani 1 1 d . . . H9A H -0.0239 0.0155 0.8813 0.027 Uiso 1 1 calc R . . H9B H 0.1004 -0.0675 0.9291 0.027 Uiso 1 1 calc R . . H9C H -0.0658 -0.0990 0.8575 0.027 Uiso 1 1 calc R . . C10 C 0.24624(17) -0.03488(12) 0.64516(15) 0.0118(3) Uani 1 1 d . . . C11 C 0.17422(19) -0.11339(13) 0.55484(16) 0.0162(3) Uani 1 1 d . . . H11A H 0.0918 -0.0846 0.4899 0.024 Uiso 1 1 calc R . . H11B H 0.1376 -0.1661 0.5954 0.024 Uiso 1 1 calc R . . H11C H 0.2460 -0.1410 0.5200 0.024 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.00787(13) 0.01136(14) 0.00943(13) -0.00073(10) 0.00063(10) 0.00084(10) S1 0.01176(18) 0.01278(19) 0.00964(18) -0.00208(14) 0.00180(14) -0.00274(14) O1 0.0196(6) 0.0168(6) 0.0110(6) 0.0007(5) 0.0020(5) 0.0015(5) O2 0.0220(7) 0.0328(8) 0.0182(6) -0.0088(6) 0.0075(5) -0.0171(6) O3 0.0183(6) 0.0163(6) 0.0146(6) -0.0018(5) 0.0045(5) 0.0040(5) O4 0.0105(5) 0.0203(6) 0.0139(6) -0.0002(5) 0.0027(5) -0.0009(5) O5 0.0127(6) 0.0185(6) 0.0148(6) -0.0024(5) 0.0061(5) -0.0050(4) O6 0.0122(5) 0.0133(6) 0.0111(5) -0.0003(4) 0.0006(4) 0.0019(4) O7 0.0089(5) 0.0183(6) 0.0113(5) -0.0029(5) 0.0008(4) 0.0029(4) N1 0.0121(6) 0.0129(7) 0.0112(6) -0.0021(5) 0.0035(5) -0.0023(5) N2 0.0107(6) 0.0106(6) 0.0137(7) 0.0009(5) 0.0020(5) 0.0008(5) C1 0.0132(7) 0.0104(7) 0.0098(7) 0.0006(6) 0.0018(6) 0.0011(6) C2 0.0151(7) 0.0124(8) 0.0130(8) -0.0011(6) 0.0006(6) -0.0003(6) C3 0.0225(9) 0.0148(8) 0.0102(7) -0.0027(6) 0.0016(6) 0.0000(6) C4 0.0237(9) 0.0191(8) 0.0125(8) -0.0004(6) 0.0071(7) 0.0011(7) C5 0.0174(8) 0.0152(8) 0.0148(8) 0.0008(6) 0.0057(7) -0.0016(6) C6 0.0132(7) 0.0096(7) 0.0117(7) 0.0000(6) 0.0016(6) 0.0015(6) C7 0.0100(7) 0.0109(7) 0.0114(7) 0.0008(6) 0.0028(6) -0.0004(5) C8 0.0102(7) 0.0112(7) 0.0141(8) 0.0000(6) 0.0038(6) 0.0008(5) C9 0.0124(7) 0.0279(10) 0.0139(8) -0.0008(7) 0.0055(6) -0.0014(7) C10 0.0111(7) 0.0116(7) 0.0118(7) 0.0012(6) 0.0025(6) 0.0008(6) C11 0.0149(8) 0.0176(8) 0.0170(8) -0.0049(7) 0.0065(7) -0.0042(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 O7 1.9434(12) 3_656 ? Cu1 O7 1.9434(12) . yes Cu1 O6 1.9644(12) . yes Cu1 O6 1.9644(12) 3_656 ? Cu1 O5 2.4489(11) . yes S1 O2 1.4422(13) . ? S1 O3 1.4599(13) . ? S1 O1 1.4617(13) . ? S1 C1 1.7729(16) . ? O4 C8 1.225(2) . ? O5 C10 1.2388(19) . ? O6 H6O 0.8670 . ? O6 H6P 0.8121 . ? O7 H7O 0.8128 . ? O7 H7P 0.8265 . ? N1 N2 1.3077(19) . yes N1 C6 1.409(2) . yes N1 H1N 0.8170 . ? N2 C7 1.316(2) . yes C1 C2 1.391(2) . ? C1 C6 1.405(2) . ? C2 C3 1.390(2) . ? C2 H2 0.9500 . ? C3 C4 1.393(3) . ? C3 H3 0.9500 . ? C4 C5 1.385(2) . ? C4 H4 0.9500 . ? C5 C6 1.399(2) . ? C5 H5 0.9500 . ? C7 C10 1.480(2) . ? C7 C8 1.484(2) . ? C8 C9 1.501(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.496(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 Cu1 O7 180.0 3_656 . ? O7 Cu1 O6 92.39(5) 3_656 . ? O7 Cu1 O6 87.61(5) . . yes O7 Cu1 O6 87.61(5) 3_656 3_656 ? O7 Cu1 O6 92.39(5) . 3_656 ? O6 Cu1 O6 179.999(1) . 3_656 ? O7 Cu1 O5 95.26(4) 3_656 . ? O7 Cu1 O5 84.74(4) . . yes O6 Cu1 O5 95.79(4) . . yes O6 Cu1 O5 84.21(4) 3_656 . ? O2 S1 O3 113.32(8) . . ? O2 S1 O1 113.63(8) . . ? O3 S1 O1 111.18(7) . . ? O2 S1 C1 107.21(8) . . ? O3 S1 C1 104.94(7) . . ? O1 S1 C1 105.78(7) . . ? C10 O5 Cu1 133.25(11) . . ? Cu1 O6 H6O 118.3 . . ? Cu1 O6 H6P 109.3 . . ? H6O O6 H6P 106.8 . . ? Cu1 O7 H7O 111.0 . . ? Cu1 O7 H7P 126.4 . . ? H7O O7 H7P 114.4 . . ? N2 N1 C6 118.97(13) . . yes N2 N1 H1N 119.9 . . ? C6 N1 H1N 121.1 . . ? N1 N2 C7 121.63(14) . . yes C2 C1 C6 119.92(15) . . ? C2 C1 S1 119.66(12) . . ? C6 C1 S1 120.43(12) . . ? C3 C2 C1 120.17(16) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 119.83(16) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 120.63(16) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 119.83(16) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 119.60(15) . . ? C5 C6 N1 120.46(15) . . ? C1 C6 N1 119.94(14) . . ? N2 C7 C10 125.05(14) . . ? N2 C7 C8 113.07(14) . . ? C10 C7 C8 121.85(14) . . ? O4 C8 C7 119.97(14) . . ? O4 C8 C9 121.21(14) . . ? C7 C8 C9 118.74(14) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C10 C7 118.87(15) . . ? O5 C10 C11 120.98(14) . . ? C7 C10 C11 120.06(14) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 _geom_hbond_publ_flag O6 H6O O1 0.87 1.81 2.6745(17) 176.3 3_656 yes O6 H6O S1 0.87 2.85 3.6635(12) 157.2 3_656 yes O6 H6P O2 0.81 1.88 2.6843(17) 171.6 2_646 yes O7 H7O O3 0.81 1.86 2.6531(17) 166.8 . yes O7 H7O S1 0.81 2.95 3.7443(12) 165.0 . yes O7 H7P O4 0.83 1.91 2.7240(16) 167.3 1_655 yes N1 H1N O5 0.82 2.00 2.6235(18) 132.6 . yes N1 H1N O1 0.82 2.43 2.9513(18) 122.5 . yes N1 H1N O3 0.82 2.59 3.0841(18) 120.7 . yes N1 H1N S1 0.82 2.64 3.0224(14) 110.0 . yes _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.211 _refine_diff_density_min -0.468 _refine_diff_density_rms 0.073 #===END======================================================================== data_13 _database_code_depnum_ccdc_archive 'CCDC 798952' #TrackingRef 'Kopylovich.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 Cu N2 O4' _chemical_formula_sum 'C12 H10 Cu N2 O4' _chemical_formula_weight 309.76 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' 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 '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 11.5658(13) _cell_length_b 5.2797(6) _cell_length_c 18.662(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.281(4) _cell_angle_gamma 90.00 _cell_volume 1139.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2335 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 25.60 _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.805 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 1.928 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3622 _exptl_absorpt_correction_T_max 0.8768 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _publ_section_exptl_refinement ; The hydrogen atoms were positioned geometrically and constrained to ride on their parent atoms, with C---H = 0.95-0.98 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 0.98 \%A from atom O6 and the deepest hole is located 0.90 \%A from atom Cu1. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'curved graphite crystal' _diffrn_measurement_device_type 'Bruker KAPPA APEX II DUO CCD' _diffrn_measurement_device '62mm x 62mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6932 _diffrn_reflns_av_R_equivalents 0.0624 _diffrn_reflns_av_sigmaI/netI 0.0582 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.85 _reflns_number_total 2149 _reflns_number_gt 1450 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2009)' _computing_cell_refinement 'SAINT (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SIR2008 (Burla et al., 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond v.3.2c (Brandenburg, 2009)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0888P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2149 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1378 _refine_ls_wR_factor_gt 0.1218 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _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 Cu1 Cu 0.36747(4) 0.25656(10) 0.24626(3) 0.0168(2) Uani 1 1 d . . . O4 O 0.0182(3) 0.9310(7) 0.18190(18) 0.0315(9) Uani 1 1 d . . . O5 O 0.2820(3) 0.5311(6) 0.28437(16) 0.0202(7) Uani 1 1 d . . . O6 O 0.4422(3) 0.2241(6) 0.34490(16) 0.0207(7) Uani 1 1 d . . . O7 O 0.4531(3) -0.0324(6) 0.22212(15) 0.0205(7) Uani 1 1 d . . . N1 N 0.2904(3) 0.2817(7) 0.15330(19) 0.0140(8) Uani 1 1 d . . . N2 N 0.2074(3) 0.4400(7) 0.13892(18) 0.0167(8) Uani 1 1 d . . . C1 C 0.3984(3) -0.0737(9) 0.0978(2) 0.0156(9) Uani 1 1 d . . . C2 C 0.4153(4) -0.2303(8) 0.0376(2) 0.0182(10) Uani 1 1 d . . . H2 H 0.4686 -0.3666 0.0412 0.022 Uiso 1 1 calc R . . C3 C 0.3583(4) -0.1938(9) -0.0254(2) 0.0198(10) Uani 1 1 d . . . H3 H 0.3707 -0.3043 -0.0648 0.024 Uiso 1 1 calc R . . C4 C 0.2814(4) 0.0077(9) -0.0313(2) 0.0208(10) Uani 1 1 d . . . H4 H 0.2428 0.0391 -0.0755 0.025 Uiso 1 1 calc R . . C5 C 0.2611(4) 0.1626(9) 0.0273(2) 0.0199(10) Uani 1 1 d . . . H5 H 0.2082 0.2994 0.0226 0.024 Uiso 1 1 calc R . . C6 C 0.3162(3) 0.1230(9) 0.0928(2) 0.0166(10) Uani 1 1 d . . . C7 C 0.1659(4) 0.6157(9) 0.1836(2) 0.0157(9) Uani 1 1 d . . . C8 C 0.0696(4) 0.7636(9) 0.1494(2) 0.0202(10) Uani 1 1 d . . . C9 C 0.0361(4) 0.6987(10) 0.0744(3) 0.0280(12) Uani 1 1 d . . . H9A H -0.0267 0.8104 0.0585 0.042 Uiso 1 1 calc R . . H9B H 0.0101 0.5222 0.0723 0.042 Uiso 1 1 calc R . . H9C H 0.1030 0.7208 0.0429 0.042 Uiso 1 1 calc R . . C10 C 0.2058(4) 0.6637(9) 0.2553(2) 0.0162(10) Uani 1 1 d . . . C11 C 0.1618(4) 0.8781(9) 0.2995(2) 0.0202(10) Uani 1 1 d . . . H11A H 0.0839 0.8380 0.3167 0.030 Uiso 1 1 calc R . . H11B H 0.1589 1.0323 0.2703 0.030 Uiso 1 1 calc R . . H11C H 0.2135 0.9050 0.3406 0.030 Uiso 1 1 calc R . . C12 C 0.4723(4) -0.1315(9) 0.1610(2) 0.0193(10) 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 0.0164(3) 0.0228(4) 0.0113(3) -0.0015(2) 0.0031(2) 0.0003(2) O4 0.0302(19) 0.033(2) 0.031(2) -0.0038(17) -0.0007(16) 0.0124(17) O5 0.0199(16) 0.0241(18) 0.0165(16) -0.0020(13) 0.0074(13) 0.0021(14) O6 0.0189(16) 0.030(2) 0.0129(15) -0.0015(14) 0.0003(13) -0.0053(14) O7 0.0265(18) 0.0241(19) 0.0111(16) -0.0009(13) 0.0054(13) 0.0030(14) N1 0.0108(17) 0.019(2) 0.0118(17) -0.0009(15) 0.0035(14) -0.0003(15) N2 0.0154(18) 0.019(2) 0.0156(19) 0.0000(16) 0.0066(15) -0.0045(16) C1 0.015(2) 0.022(3) 0.010(2) 0.0003(18) 0.0089(17) -0.0027(18) C2 0.020(2) 0.018(2) 0.017(2) 0.003(2) 0.0064(18) 0.0022(19) C3 0.020(2) 0.030(3) 0.010(2) -0.0050(19) 0.0047(18) -0.0008(19) C4 0.018(2) 0.033(3) 0.012(2) -0.0030(19) 0.0030(18) 0.003(2) C5 0.017(2) 0.026(3) 0.017(2) 0.0010(19) 0.0050(18) 0.0046(19) C6 0.018(2) 0.021(3) 0.011(2) -0.0012(19) 0.0077(17) -0.0039(19) C7 0.015(2) 0.019(3) 0.014(2) 0.0023(18) 0.0071(17) -0.0026(18) C8 0.017(2) 0.025(3) 0.018(2) 0.002(2) 0.0033(18) -0.002(2) C9 0.018(2) 0.043(3) 0.023(3) 0.002(2) 0.001(2) 0.004(2) C10 0.012(2) 0.019(2) 0.018(2) 0.0012(19) 0.0095(18) -0.0020(18) C11 0.022(3) 0.023(3) 0.016(2) -0.004(2) 0.0089(19) 0.000(2) C12 0.022(2) 0.023(3) 0.013(2) 0.004(2) 0.0065(18) -0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O7 1.875(3) . yes Cu1 O5 1.895(3) . yes Cu1 N1 1.951(4) . yes Cu1 O6 2.037(3) . yes Cu1 O7 2.426(3) 2_655 ? O4 C8 1.227(5) . yes O5 C10 1.248(5) . yes O6 C12 1.254(6) 2_655 ? O7 C12 1.275(5) . yes O7 Cu1 2.426(3) 2_645 ? N1 N2 1.300(5) . yes N1 C6 1.438(6) . yes N2 C7 1.338(6) . yes C1 C2 1.409(6) . ? C1 C6 1.411(6) . ? C1 C12 1.485(6) . ? C2 C3 1.359(7) . ? C2 H2 0.9500 . ? C3 C4 1.390(6) . ? C3 H3 0.9500 . ? C4 C5 1.387(6) . ? C4 H4 0.9500 . ? C5 C6 1.392(6) . ? C5 H5 0.9500 . ? C7 C10 1.435(6) . ? C7 C8 1.500(6) . ? C8 C9 1.491(7) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.492(6) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O6 1.254(6) 2_645 ? 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 O7 Cu1 O5 171.76(13) . . yes O7 Cu1 N1 94.65(13) . . yes O5 Cu1 N1 92.57(14) . . yes O7 Cu1 O6 85.78(12) . . yes O5 Cu1 O6 86.85(13) . . yes N1 Cu1 O6 177.77(13) . . ? O7 Cu1 O7 88.86(6) . 2_655 ? O5 Cu1 O7 90.25(12) . 2_655 ? N1 Cu1 O7 124.85(13) . 2_655 ? O6 Cu1 O7 57.32(11) . 2_655 ? C10 O5 Cu1 129.4(3) . . ? C12 O6 Cu1 101.6(3) 2_655 . ? C12 O7 Cu1 130.0(3) . . ? C12 O7 Cu1 82.9(3) . 2_645 ? Cu1 O7 Cu1 140.12(15) . 2_645 ? N2 N1 C6 111.6(3) . . ? N2 N1 Cu1 124.1(3) . . ? C6 N1 Cu1 124.3(3) . . ? N1 N2 C7 125.7(4) . . ? C2 C1 C6 118.4(4) . . ? C2 C1 C12 115.6(4) . . ? C6 C1 C12 126.1(4) . . ? C3 C2 C1 122.6(4) . . ? C3 C2 H2 118.7 . . ? C1 C2 H2 118.7 . . ? C2 C3 C4 119.0(4) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 120.0(4) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 121.7(4) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C5 C6 C1 118.3(4) . . ? C5 C6 N1 120.5(4) . . ? C1 C6 N1 121.3(4) . . ? N2 C7 C10 126.1(4) . . ? N2 C7 C8 111.3(4) . . ? C10 C7 C8 122.6(4) . . ? O4 C8 C9 120.4(4) . . ? O4 C8 C7 121.7(4) . . ? C9 C8 C7 118.0(4) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C10 C7 122.0(4) . . ? O5 C10 C11 115.3(4) . . ? C7 C10 C11 122.7(4) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O6 C12 O7 118.0(4) 2_645 . ? O6 C12 C1 120.4(4) 2_645 . ? O7 C12 C1 121.6(4) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.85 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.909 _refine_diff_density_min -0.875 _refine_diff_density_rms 0.129 #===END======================================================================== data_14 _database_code_depnum_ccdc_archive 'CCDC 798953' #TrackingRef 'Kopylovich.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H16 Cu N8 O4, 2(C11 H11 N2 O5 S), 6(H2 O)' _chemical_formula_sum 'C26 H50 Cu N12 O20 S2' _chemical_formula_weight 978.44 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 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 6.9100(6) _cell_length_b 12.0491(13) _cell_length_c 14.337(2) _cell_angle_alpha 108.578(7) _cell_angle_beta 100.618(7) _cell_angle_gamma 104.892(5) _cell_volume 1046.3(2) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1556 _cell_measurement_theta_min 2.89 _cell_measurement_theta_max 27.36 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 511 _exptl_absorpt_coefficient_mu 0.713 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8226 _exptl_absorpt_correction_T_max 0.9465 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _publ_section_exptl_refinement ; The H~2~O, NH~2~, and NH hydrogen atoms were located from the difference Fourier map but constrained to ride on their parent atom, with U~iso~ = 1.5 U~eq~(parent atom). Other hydrogen atoms were positioned geometrically and were also constrained to ride on their parent atoms, with C---H = 0.95-0.98 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 0.95 \%A from atom O5 and the deepest hole is located 0.71 \%A from atom Cu1. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'flat graphite crystal' _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_device '62mm x 62mm CCD camera on three-circle goniostat' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_measurement_method '\f scans and \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8178 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.1218 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4674 _reflns_number_gt 2833 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2009)' _computing_cell_refinement 'SAINT (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond v.3.2d (Brandenburg, 2010)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0208P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4674 _refine_ls_number_parameters 279 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0878 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.0801 _refine_ls_wR_factor_gt 0.0705 _refine_ls_goodness_of_fit_ref 0.854 _refine_ls_restrained_S_all 0.854 _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 Cu1 Cu 0.0000 0.5000 0.5000 0.01162(14) Uani 1 2 d S . . S1 S 0.10174(10) 0.32918(7) 0.75791(6) 0.01337(18) Uani 1 1 d . . . O1 O -0.0926(3) 0.35538(19) 0.74612(16) 0.0204(5) Uani 1 1 d . . . O2 O 0.0817(3) 0.20365(18) 0.69674(16) 0.0227(5) Uani 1 1 d . . . O3 O 0.2674(3) 0.42175(18) 0.74452(16) 0.0173(5) Uani 1 1 d . . . O4 O 0.3050(3) 0.98815(19) 1.08449(17) 0.0243(6) Uani 1 1 d . . . O5 O 0.1190(3) 0.66738(19) 0.81701(16) 0.0195(5) Uani 1 1 d . . . O6 O 0.2512(2) 0.54582(17) 0.61580(15) 0.0172(5) Uani 1 1 d . . . H6O H 0.3122 0.6205 0.6601 0.026 Uiso 1 1 d R . . H6P H 0.2285 0.4968 0.6477 0.026 Uiso 1 1 d R . . O7 O -0.2884(3) 0.75289(17) 0.57523(15) 0.0175(5) Uani 1 1 d . . . H7O H -0.2857 0.6801 0.5621 0.026 Uiso 1 1 d R . . H7P H -0.3539 0.7516 0.5145 0.026 Uiso 1 1 d R . . O8 O -0.1759(3) 0.57407(17) 0.62321(15) 0.0171(5) Uani 1 1 d . . . H8O H -0.2764 0.5077 0.6061 0.026 Uiso 1 1 d R . . H8P H -0.0965 0.5953 0.6845 0.026 Uiso 1 1 d R . . O9 O 0.5181(3) 0.78118(19) 0.73064(18) 0.0356(7) Uani 1 1 d . . . H9O H 0.5941 0.7871 0.6913 0.053 Uiso 1 1 d R . . H9P H 0.5634 0.8474 0.7847 0.053 Uiso 1 1 d R . . O10 O -0.4510(3) 0.36591(17) 0.63445(15) 0.0181(5) Uani 1 1 d . . . H10O H -0.3576 0.3396 0.6550 0.027 Uiso 1 1 d R . . H10P H -0.5272 0.3781 0.6724 0.027 Uiso 1 1 d R . . N1 N 0.2135(3) 0.5662(2) 0.94346(19) 0.0157(6) Uani 1 1 d . . . H1N H 0.1675 0.5765 0.8855 0.023 Uiso 1 1 d R . . N2 N 0.2627(3) 0.6762(2) 1.01653(19) 0.0139(6) Uani 1 1 d . . . N3 N -0.1057(3) 0.3342(2) 0.50184(19) 0.0150(6) Uani 1 1 d . . . N4 N -0.3004(3) 0.1220(2) 0.48066(19) 0.0155(6) Uani 1 1 d . . . N5 N -0.0734(3) 0.0433(2) 0.39551(19) 0.0181(6) Uani 1 1 d . . . H5N H -0.0028 0.1108 0.3883 0.027 Uiso 1 1 d R . . H5M H -0.0466 -0.0249 0.3654 0.027 Uiso 1 1 d R . . N6 N -0.3472(3) -0.0853(2) 0.42167(19) 0.0163(6) Uani 1 1 d . . . H6M H -0.3225 -0.1495 0.3868 0.024 Uiso 1 1 d R . . H6N H -0.4567 -0.0987 0.4424 0.024 Uiso 1 1 d R . . C1 C 0.1843(4) 0.3488(3) 0.8885(2) 0.0128(7) Uani 1 1 d . . . C2 C 0.2017(4) 0.2491(3) 0.9131(2) 0.0156(7) Uani 1 1 d . . . H2 H 0.1718 0.1708 0.8595 0.019 Uiso 1 1 calc R . . C3 C 0.2615(4) 0.2610(3) 1.0139(2) 0.0177(7) Uani 1 1 d . . . H3 H 0.2733 0.1917 1.0294 0.021 Uiso 1 1 calc R . . C4 C 0.3046(4) 0.3751(3) 1.0927(2) 0.0181(8) Uani 1 1 d . . . H4 H 0.3458 0.3835 1.1623 0.022 Uiso 1 1 calc R . . C5 C 0.2878(4) 0.4757(3) 1.0705(2) 0.0166(7) Uani 1 1 d . . . H5 H 0.3163 0.5532 1.1249 0.020 Uiso 1 1 calc R . . C6 C 0.2291(4) 0.4651(3) 0.9686(2) 0.0133(7) Uani 1 1 d . . . C7 C 0.2457(4) 0.7732(3) 0.9957(2) 0.0135(7) Uani 1 1 d . . . C8 C 0.3125(4) 0.8895(3) 1.0894(2) 0.0166(7) Uani 1 1 d . . . C9 C 0.3913(4) 0.8825(3) 1.1910(2) 0.0200(8) Uani 1 1 d . . . H9A H 0.4179 0.9625 1.2463 0.030 Uiso 1 1 calc R . . H9B H 0.5214 0.8635 1.1942 0.030 Uiso 1 1 calc R . . H9C H 0.2861 0.8168 1.1991 0.030 Uiso 1 1 calc R . . C10 C 0.1665(4) 0.7679(3) 0.8912(2) 0.0162(7) Uani 1 1 d . . . C11 C 0.1376(4) 0.8771(3) 0.8701(3) 0.0243(8) Uani 1 1 d . . . H11A H 0.0795 0.8525 0.7960 0.036 Uiso 1 1 calc R . . H11B H 0.2730 0.9441 0.8948 0.036 Uiso 1 1 calc R . . H11C H 0.0413 0.9063 0.9058 0.036 Uiso 1 1 calc R . . C12 C -0.1938(4) 0.2336(3) 0.4901(2) 0.0124(7) Uani 1 1 d . . . C14 C -0.2363(4) 0.0281(3) 0.4327(2) 0.0137(7) 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 0.0123(3) 0.0072(3) 0.0138(3) 0.0037(3) 0.0037(2) 0.0013(2) S1 0.0140(4) 0.0127(4) 0.0139(5) 0.0044(4) 0.0049(3) 0.0057(3) O1 0.0157(10) 0.0291(14) 0.0205(14) 0.0093(11) 0.0062(9) 0.0137(9) O2 0.0371(12) 0.0142(12) 0.0157(13) 0.0017(10) 0.0088(10) 0.0114(9) O3 0.0168(10) 0.0194(12) 0.0157(13) 0.0079(10) 0.0056(9) 0.0039(9) O4 0.0333(13) 0.0130(12) 0.0189(14) 0.0007(11) 0.0016(10) 0.0066(10) O5 0.0248(11) 0.0194(13) 0.0124(13) 0.0059(11) 0.0017(9) 0.0074(9) O6 0.0173(10) 0.0091(11) 0.0195(13) 0.0030(10) 0.0038(9) -0.0005(8) O7 0.0191(10) 0.0136(12) 0.0204(13) 0.0077(10) 0.0045(9) 0.0057(8) O8 0.0179(10) 0.0135(12) 0.0154(13) 0.0043(10) 0.0015(9) 0.0021(8) O9 0.0375(13) 0.0208(14) 0.0316(16) -0.0035(12) 0.0199(11) -0.0067(10) O10 0.0158(10) 0.0196(12) 0.0226(14) 0.0077(11) 0.0093(9) 0.0097(9) N1 0.0142(12) 0.0198(15) 0.0101(15) 0.0029(12) 0.0032(10) 0.0050(10) N2 0.0079(12) 0.0139(14) 0.0131(15) -0.0016(12) 0.0041(10) 0.0005(10) N3 0.0171(13) 0.0105(14) 0.0200(16) 0.0063(12) 0.0091(11) 0.0058(11) N4 0.0149(12) 0.0074(13) 0.0235(17) 0.0045(12) 0.0079(11) 0.0027(10) N5 0.0201(13) 0.0075(14) 0.0286(18) 0.0063(13) 0.0133(12) 0.0043(10) N6 0.0159(13) 0.0094(14) 0.0211(16) 0.0039(12) 0.0058(11) 0.0025(10) C1 0.0086(14) 0.0191(18) 0.0128(17) 0.0065(14) 0.0058(11) 0.0059(12) C2 0.0105(14) 0.0167(17) 0.022(2) 0.0101(15) 0.0057(12) 0.0046(12) C3 0.0105(15) 0.0235(19) 0.024(2) 0.0152(16) 0.0057(13) 0.0062(13) C4 0.0086(14) 0.029(2) 0.0151(19) 0.0103(16) 0.0016(12) 0.0026(13) C5 0.0090(14) 0.0230(19) 0.0150(18) 0.0050(15) 0.0033(12) 0.0038(12) C6 0.0077(13) 0.0146(17) 0.0187(19) 0.0068(15) 0.0061(12) 0.0035(11) C7 0.0102(14) 0.0158(17) 0.0128(18) 0.0032(14) 0.0033(12) 0.0047(12) C8 0.0102(14) 0.0186(18) 0.0176(19) 0.0042(15) 0.0055(12) 0.0016(12) C9 0.0216(16) 0.0151(18) 0.0160(19) 0.0001(15) 0.0014(13) 0.0046(13) C10 0.0086(14) 0.0175(18) 0.0200(19) 0.0052(15) 0.0058(12) 0.0018(12) C11 0.0279(18) 0.025(2) 0.020(2) 0.0091(16) 0.0033(14) 0.0091(14) C12 0.0131(14) 0.0180(18) 0.0111(17) 0.0068(14) 0.0069(12) 0.0093(12) C14 0.0145(15) 0.0107(16) 0.0103(17) 0.0032(14) -0.0014(12) -0.0002(12) _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 N3 1.953(2) 2_566 ? Cu1 N3 1.954(2) . yes Cu1 O6 1.9838(18) 2_566 ? Cu1 O6 1.9838(18) . yes Cu1 O8 2.3956(19) 2_566 ? Cu1 O8 2.3956(19) . yes S1 O2 1.442(2) . ? S1 O1 1.4492(18) . ? S1 O3 1.467(2) . ? S1 C1 1.773(3) . ? O4 C8 1.227(4) . ? O5 C10 1.246(3) . ? O6 H6O 0.8563 . ? O6 H6P 0.8566 . ? O7 H7O 0.8426 . ? O7 H7P 0.8974 . ? O8 H8O 0.8416 . ? O8 H8P 0.8638 . ? O9 H9O 0.8450 . ? O9 H9P 0.8508 . ? O10 H10O 0.8360 . ? O10 H10P 0.8308 . ? N1 N2 1.312(3) . ? N1 C6 1.400(4) . ? N1 H1N 0.8912 . ? N2 C7 1.323(4) . ? N3 C12 1.150(3) . ? N4 C12 1.306(4) . ? N4 C14 1.350(3) . ? N5 C14 1.328(3) . ? N5 H5N 0.8828 . ? N5 H5M 0.8812 . ? N6 C14 1.326(3) . ? N6 H6M 0.8541 . ? N6 H6N 0.8587 . ? C1 C2 1.382(4) . ? C1 C6 1.414(4) . ? C2 C3 1.376(4) . ? C2 H2 0.9500 . ? C3 C4 1.389(4) . ? C3 H3 0.9500 . ? C4 C5 1.375(4) . ? C4 H4 0.9500 . ? C5 C6 1.397(4) . ? C5 H5 0.9500 . ? C7 C10 1.473(4) . ? C7 C8 1.489(4) . ? C8 C9 1.495(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.492(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Cu1 N3 180.0 2_566 . ? N3 Cu1 O6 90.97(9) 2_566 2_566 ? N3 Cu1 O6 89.03(9) . 2_566 ? N3 Cu1 O6 89.04(9) 2_566 . ? N3 Cu1 O6 90.96(9) . . yes O6 Cu1 O6 180.00(12) 2_566 . ? N3 Cu1 O8 89.32(8) 2_566 2_566 ? N3 Cu1 O8 90.68(8) . 2_566 ? O6 Cu1 O8 88.63(7) 2_566 2_566 ? O6 Cu1 O8 91.37(7) . 2_566 ? N3 Cu1 O8 90.68(8) 2_566 . ? N3 Cu1 O8 89.32(8) . . yes O6 Cu1 O8 91.37(7) 2_566 . ? O6 Cu1 O8 88.63(7) . . yes O8 Cu1 O8 180.000(1) 2_566 . ? O2 S1 O1 114.56(12) . . ? O2 S1 O3 112.04(13) . . ? O1 S1 O3 111.90(13) . . ? O2 S1 C1 106.82(14) . . ? O1 S1 C1 105.06(13) . . ? O3 S1 C1 105.66(12) . . ? Cu1 O6 H6O 122.1 . . ? Cu1 O6 H6P 110.0 . . ? H6O O6 H6P 108.7 . . ? H7O O7 H7P 104.6 . . ? Cu1 O8 H8O 98.5 . . ? Cu1 O8 H8P 109.6 . . ? H8O O8 H8P 111.1 . . ? H9O O9 H9P 110.0 . . ? H10O O10 H10P 114.5 . . ? N2 N1 C6 120.0(3) . . ? N2 N1 H1N 104.5 . . ? C6 N1 H1N 135.3 . . ? N1 N2 C7 121.7(3) . . ? C12 N3 Cu1 169.1(2) . . ? C12 N4 C14 117.1(2) . . ? C14 N5 H5N 127.3 . . ? C14 N5 H5M 115.8 . . ? H5N N5 H5M 116.1 . . ? C14 N6 H6M 121.4 . . ? C14 N6 H6N 121.6 . . ? H6M N6 H6N 116.6 . . ? C2 C1 C6 119.2(3) . . ? C2 C1 S1 120.0(2) . . ? C6 C1 S1 120.8(2) . . ? C3 C2 C1 121.3(3) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 119.7(3) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.5(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 N1 121.9(3) . . ? C5 C6 C1 119.0(3) . . ? N1 C6 C1 119.0(3) . . ? N2 C7 C10 124.0(3) . . ? N2 C7 C8 113.1(3) . . ? C10 C7 C8 122.9(3) . . ? O4 C8 C7 121.9(3) . . ? O4 C8 C9 120.5(3) . . ? C7 C8 C9 117.6(3) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C10 C7 118.6(3) . . ? O5 C10 C11 118.5(3) . . ? C7 C10 C11 122.9(3) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 N4 176.5(3) . . ? N6 C14 N5 119.4(3) . . ? N6 C14 N4 116.8(3) . . ? N5 C14 N4 123.8(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O6 H6O O9 0.86 1.90 2.715(3) 159.2 . yes O6 H6P O3 0.86 1.90 2.724(3) 161.5 . yes O6 H6P S1 0.86 3.00 3.848(2) 173.5 . yes O7 H7O O8 0.84 1.98 2.707(3) 143.2 . yes O7 H7P O10 0.90 2.10 2.875(3) 143.9 2_466 yes O7 H7P N6 0.90 2.70 3.409(3) 137.0 1_565 yes O8 H8O O10 0.84 2.03 2.802(3) 152.9 . yes O8 H8P O5 0.86 1.95 2.808(3) 169.0 . yes O9 H9O O7 0.85 1.96 2.778(3) 163.4 1_655 yes O9 H9P O4 0.85 2.09 2.934(3) 176.0 2_677 yes O10 H10O O1 0.84 1.97 2.746(3) 154.4 . yes O10 H10P O3 0.83 1.98 2.803(3) 168.6 1_455 yes N1 H1N O5 0.89 1.74 2.565(3) 152.6 . yes N5 H5N O7 0.88 2.09 2.874(3) 146.8 2_566 yes N5 H5M O2 0.88 1.98 2.825(3) 160.2 2_556 yes N6 H6M O2 0.85 2.33 3.038(3) 140.7 2_556 yes N6 H6M O10 0.85 2.56 3.074(3) 119.6 2_456 yes N6 H6N N4 0.86 2.18 3.031(3) 170.8 2_456 yes _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.454 _refine_diff_density_min -0.578 _refine_diff_density_rms 0.085 #===END======================================================================== data_15 _database_code_depnum_ccdc_archive 'CCDC 798954' #TrackingRef 'Kopylovich.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 Cu N4 O5 S' _chemical_formula_sum 'C14 H14 Cu N4 O5 S' _chemical_formula_weight 413.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 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 4.9947(3) _cell_length_b 8.5337(5) _cell_length_c 19.0626(10) _cell_angle_alpha 87.866(3) _cell_angle_beta 82.974(3) _cell_angle_gamma 76.536(3) _cell_volume 784.21(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3855 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 30.37 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.753 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 422 _exptl_absorpt_coefficient_mu 1.561 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7772 _exptl_absorpt_correction_T_max 0.9274 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _publ_section_exptl_refinement ; The imidazole ring was disordered over two sites with occupancies 0.51 and 0.49. The nitrogen atoms N3 and N3B as well as N4 and N4B were constrained to have equal coordinates and anisotropic displacement parameters. Hdrogen atoms were positioned geometrically and constrained to ride on their parent atoms, with C---H = 0.95-0.99 \%A, N---H = 0.88 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 0.73 \%A from atom S1 and the deepest hole is located 0.52 \%A from atom Cu1. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'curved graphite crystal' _diffrn_measurement_device_type 'Bruker KAPPA APEX II DUO CCD' _diffrn_measurement_device '62mm x 62mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14341 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 30.61 _reflns_number_total 4783 _reflns_number_gt 3704 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2009)' _computing_cell_refinement 'SAINT (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Diamond v.3.2d (Brandenburg, 2010)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0370P)^2^+1.1027P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4783 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.0983 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 Cu1 Cu 0.50868(6) 0.16468(4) 0.320602(16) 0.01228(9) Uani 1 1 d . . . S1 S 1.02136(12) -0.06544(7) 0.31944(3) 0.01278(13) Uani 1 1 d . . . O1 O 0.7240(3) -0.0524(2) 0.34331(9) 0.0122(3) Uani 1 1 d . A . O2 O 1.0979(4) 0.0832(2) 0.33418(11) 0.0198(4) Uani 1 1 d . . . O3 O 1.1916(4) -0.2094(2) 0.34643(10) 0.0198(4) Uani 1 1 d . A . O4 O -0.1385(4) 0.4426(3) 0.11937(11) 0.0253(5) Uani 1 1 d . A . O5 O 0.2738(4) 0.3698(2) 0.30100(10) 0.0175(4) Uani 1 1 d . A . N1 N 0.6172(4) 0.1265(2) 0.21794(11) 0.0127(4) Uani 1 1 d . A . N2 N 0.4677(4) 0.1995(3) 0.17009(12) 0.0144(4) Uani 1 1 d . . . C1 C 1.0495(5) -0.0830(3) 0.22703(13) 0.0130(5) Uani 1 1 d . A . C2 C 1.2774(5) -0.1959(3) 0.19548(15) 0.0176(5) Uani 1 1 d . . . H2 H 1.4114 -0.2545 0.2238 0.021 Uiso 1 1 calc R A . C3 C 1.3109(6) -0.2235(4) 0.12387(15) 0.0229(6) Uani 1 1 d . A . H3 H 1.4672 -0.2997 0.1026 0.028 Uiso 1 1 calc R . . C4 C 1.1122(6) -0.1379(4) 0.08332(15) 0.0257(6) Uani 1 1 d . . . H4 H 1.1307 -0.1573 0.0340 0.031 Uiso 1 1 calc R A . C5 C 0.8860(6) -0.0238(3) 0.11418(15) 0.0214(6) Uani 1 1 d . A . H5 H 0.7530 0.0340 0.0854 0.026 Uiso 1 1 calc R . . C6 C 0.8504(5) 0.0075(3) 0.18625(13) 0.0138(5) Uani 1 1 d . . . C7 C 0.2371(5) 0.3162(3) 0.18277(13) 0.0141(5) Uani 1 1 d . A . C8 C 0.1008(6) 0.3651(3) 0.11725(14) 0.0195(5) Uani 1 1 d . . . C9 C 0.2722(6) 0.3152(4) 0.04778(15) 0.0285(7) Uani 1 1 d . A . H9A H 0.1745 0.3704 0.0091 0.043 Uiso 1 1 calc R . . H9B H 0.3025 0.1984 0.0424 0.043 Uiso 1 1 calc R . . H9C H 0.4513 0.3443 0.0466 0.043 Uiso 1 1 calc R . . C10 C 0.1413(5) 0.4005(3) 0.24804(13) 0.0136(5) Uani 1 1 d . . . C11 C -0.1148(5) 0.5332(3) 0.25693(15) 0.0187(5) Uani 1 1 d . A . H11A H -0.1186 0.5923 0.3003 0.028 Uiso 1 1 calc R . . H11B H -0.2786 0.4875 0.2601 0.028 Uiso 1 1 calc R . . H11C H -0.1151 0.6070 0.2163 0.028 Uiso 1 1 calc R . . N3 N 0.4675(4) 0.2292(3) 0.42075(12) 0.0153(4) Uani 0.486(5) 1 d P A 1 N4 N 0.5202(5) 0.2390(3) 0.53272(12) 0.0168(4) Uani 0.486(5) 1 d P A 1 H4A H 0.5628 0.2062 0.5751 0.020 Uiso 0.486(5) 1 calc PR A 1 C12 C 0.5779(15) 0.1466(9) 0.4737(4) 0.0154(14) Uani 0.486(5) 1 d P A 1 H12 H 0.6827 0.0383 0.4712 0.019 Uiso 0.486(5) 1 calc PR A 1 C13 C 0.3880(13) 0.3879(7) 0.5157(3) 0.0235(14) Uani 0.486(5) 1 d P A 1 H13 H 0.3279 0.4780 0.5462 0.028 Uiso 0.486(5) 1 calc PR A 1 C14 C 0.3572(13) 0.3846(7) 0.4464(3) 0.0231(14) Uani 0.486(5) 1 d P A 1 H14 H 0.2732 0.4743 0.4194 0.028 Uiso 0.486(5) 1 calc PR A 1 N3B N 0.4675(4) 0.2292(3) 0.42075(12) 0.0153(4) Uani 0.514(5) 1 d P A 2 N4B N 0.5202(5) 0.2390(3) 0.53272(12) 0.0168(4) Uani 0.514(5) 1 d P A 2 H4B H 0.6027 0.2296 0.5714 0.020 Uiso 0.514(5) 1 calc PR A 2 C12B C 0.6383(15) 0.1967(8) 0.4690(4) 0.0176(13) Uani 0.514(5) 1 d P A 2 H12B H 0.8296 0.1471 0.4587 0.021 Uiso 0.514(5) 1 calc PR A 2 C13B C 0.2361(11) 0.3024(6) 0.5278(3) 0.0196(12) Uani 0.514(5) 1 d P A 2 H13B H 0.0958 0.3440 0.5651 0.024 Uiso 0.514(5) 1 calc PR A 2 C14B C 0.2062(10) 0.2912(6) 0.4591(3) 0.0159(11) Uani 0.514(5) 1 d P A 2 H14B H 0.0354 0.3206 0.4394 0.019 Uiso 0.514(5) 1 calc PR A 2 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 0.01249(15) 0.01244(15) 0.01111(15) 0.00125(11) -0.00341(11) -0.00044(11) S1 0.0088(3) 0.0149(3) 0.0144(3) -0.0019(2) -0.0049(2) -0.0002(2) O1 0.0102(8) 0.0136(8) 0.0125(8) 0.0013(7) -0.0031(6) -0.0015(6) O2 0.0121(8) 0.0222(10) 0.0268(11) -0.0084(8) -0.0027(8) -0.0055(7) O3 0.0167(9) 0.0204(10) 0.0199(10) -0.0030(8) -0.0102(8) 0.0055(7) O4 0.0176(10) 0.0319(12) 0.0229(11) 0.0022(9) -0.0101(8) 0.0051(8) O5 0.0231(10) 0.0131(9) 0.0157(9) 0.0016(7) -0.0069(7) -0.0006(7) N1 0.0119(9) 0.0127(10) 0.0124(10) 0.0016(8) -0.0030(8) 0.0001(8) N2 0.0116(10) 0.0151(10) 0.0156(11) 0.0026(8) -0.0038(8) -0.0011(8) C1 0.0084(10) 0.0144(11) 0.0156(12) 0.0006(9) -0.0014(9) -0.0015(9) C2 0.0119(11) 0.0175(12) 0.0216(14) 0.0013(10) -0.0022(10) -0.0001(10) C3 0.0186(13) 0.0244(14) 0.0213(14) -0.0028(11) 0.0029(11) 0.0019(11) C4 0.0262(15) 0.0317(16) 0.0138(13) -0.0007(11) 0.0026(11) 0.0019(12) C5 0.0210(13) 0.0243(14) 0.0149(13) 0.0025(11) -0.0029(10) 0.0031(11) C6 0.0124(11) 0.0147(12) 0.0134(12) 0.0031(9) -0.0014(9) -0.0020(9) C7 0.0133(11) 0.0134(11) 0.0146(12) 0.0042(9) -0.0044(9) -0.0001(9) C8 0.0209(13) 0.0209(13) 0.0163(13) 0.0013(10) -0.0075(10) -0.0015(11) C9 0.0267(15) 0.0367(17) 0.0151(14) 0.0012(12) -0.0083(11) 0.0095(13) C10 0.0152(11) 0.0102(11) 0.0155(12) 0.0046(9) -0.0017(9) -0.0040(9) C11 0.0165(12) 0.0172(12) 0.0205(14) -0.0006(10) -0.0030(10) 0.0003(10) N3 0.0147(10) 0.0151(10) 0.0146(11) -0.0017(8) -0.0047(8) 0.0016(8) N4 0.0221(11) 0.0167(11) 0.0123(10) 0.0015(8) -0.0068(9) -0.0038(9) C12 0.020(3) 0.009(3) 0.018(3) -0.001(3) -0.003(2) -0.002(2) C13 0.037(4) 0.012(3) 0.018(3) -0.002(2) -0.007(2) 0.004(2) C14 0.035(3) 0.016(3) 0.016(3) -0.001(2) -0.009(2) 0.003(2) N3B 0.0147(10) 0.0151(10) 0.0146(11) -0.0017(8) -0.0047(8) 0.0016(8) N4B 0.0221(11) 0.0167(11) 0.0123(10) 0.0015(8) -0.0068(9) -0.0038(9) C12B 0.023(3) 0.012(3) 0.017(3) 0.001(3) -0.007(2) 0.000(2) C13B 0.024(3) 0.015(2) 0.017(3) 0.0011(19) -0.003(2) 0.001(2) C14B 0.014(2) 0.016(2) 0.016(2) 0.0004(19) -0.0054(19) 0.0006(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 O5 1.9192(18) . yes Cu1 O1 1.9754(17) . yes Cu1 N3 1.980(2) . yes Cu1 N1 1.984(2) . yes Cu1 O2 2.2981(18) 1_455 yes S1 O3 1.4391(19) . ? S1 O2 1.4536(19) . ? S1 O1 1.4788(17) . ? S1 C1 1.759(3) . ? O2 Cu1 2.2981(18) 1_655 ? O4 C8 1.220(3) . ? O5 C10 1.260(3) . ? N1 N2 1.298(3) . yes N1 C6 1.441(3) . ? N2 C7 1.339(3) . ? C1 C2 1.397(4) . ? C1 C6 1.406(3) . ? C2 C3 1.377(4) . ? C2 H2 0.9500 . ? C3 C4 1.387(4) . ? C3 H3 0.9500 . ? C4 C5 1.392(4) . ? C4 H4 0.9500 . ? C5 C6 1.391(4) . ? C5 H5 0.9500 . ? C7 C10 1.433(4) . ? C7 C8 1.495(4) . ? C8 C9 1.504(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.495(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? N3 C12 1.312(8) . ? N3 C14 1.395(6) . ? N4 C13 1.337(6) . ? N4 C12 1.360(8) . ? N4 H4A 0.8800 . ? C12 H12 0.9500 . ? C13 C14 1.349(8) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C12B H12B 0.9500 . ? C13B C14B 1.346(7) . ? C13B H13B 0.9500 . ? C14B H14B 0.9500 . ? 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 O5 Cu1 O1 175.54(8) . . ? O5 Cu1 N3 88.36(8) . . ? O1 Cu1 N3 91.03(8) . . yes O5 Cu1 N1 90.48(8) . . yes O1 Cu1 N1 91.10(8) . . ? N3 Cu1 N1 167.16(9) . . ? O5 Cu1 O2 83.10(8) . 1_455 ? O1 Cu1 O2 92.51(7) . 1_455 ? N3 Cu1 O2 92.85(8) . 1_455 ? N1 Cu1 O2 99.71(8) . 1_455 ? O3 S1 O2 114.95(11) . . ? O3 S1 O1 111.60(11) . . ? O2 S1 O1 109.98(11) . . ? O3 S1 C1 107.70(12) . . ? O2 S1 C1 107.42(12) . . ? O1 S1 C1 104.55(11) . . ? S1 O1 Cu1 109.73(10) . . ? S1 O2 Cu1 133.86(11) . 1_655 ? C10 O5 Cu1 124.67(17) . . ? N2 N1 C6 110.7(2) . . ? N2 N1 Cu1 122.84(17) . . ? C6 N1 Cu1 126.26(16) . . ? N1 N2 C7 125.0(2) . . ? C2 C1 C6 120.8(2) . . ? C2 C1 S1 116.68(19) . . ? C6 C1 S1 122.50(19) . . ? C3 C2 C1 121.0(2) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 118.8(3) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C3 C4 C5 120.6(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 121.5(3) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 117.3(2) . . ? C5 C6 N1 121.4(2) . . ? C1 C6 N1 121.3(2) . . ? N2 C7 C10 126.0(2) . . ? N2 C7 C8 111.7(2) . . ? C10 C7 C8 121.9(2) . . ? O4 C8 C7 122.0(3) . . ? O4 C8 C9 120.9(2) . . ? C7 C8 C9 117.1(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O5 C10 C7 121.6(2) . . ? O5 C10 C11 115.9(2) . . ? C7 C10 C11 122.4(2) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C12 N3 C14 105.2(4) . . ? C12 N3 Cu1 128.2(4) . . ? C14 N3 Cu1 125.6(3) . . ? C13 N4 C12 108.7(4) . . ? C13 N4 H4A 125.6 . . ? C12 N4 H4A 125.6 . . ? N3 C12 N4 110.0(5) . . ? N3 C12 H12 125.0 . . ? N4 C12 H12 125.0 . . ? N4 C13 C14 106.2(5) . . ? N4 C13 H13 126.9 . . ? C14 C13 H13 126.9 . . ? C13 C14 N3 109.5(5) . . ? C13 C14 H14 125.3 . . ? N3 C14 H14 125.3 . . ? C14B C13B H13B 127.4 . . ? C13B C14B H14B 125.2 . . ? 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 _geom_hbond_publ_flag N4 H4A O3 0.88 2.05 2.836(3) 147.8 2_756 yes N4 H4A O1 0.88 2.52 3.086(3) 122.4 2_656 yes N4B H4B O3 0.88 1.96 2.836(3) 176.3 2_756 yes _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 30.61 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.659 _refine_diff_density_min -0.583 _refine_diff_density_rms 0.107 #===END========================================================================