# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name C.Murdock Z.Lu D.Jenkins _publ_contact_author_name 'David Jenkins' _publ_contact_author_email jenkins@ion.chem.utk.edu data_3 _database_code_depnum_ccdc_archive 'CCDC 862714' #TrackingRef '- 3_02_01_2012.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H28 Cu2 N6 O17 S2' _chemical_formula_weight 671.56 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 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.9676(3) _cell_length_b 17.4113(8) _cell_length_c 18.6278(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2259.83(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9890 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 28.23 _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.974 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 2.160 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7665 _exptl_absorpt_correction_T_max 0.9380 _exptl_absorpt_process_details SADABS _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 graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15324 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0427 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 28.32 _reflns_number_total 4532 _reflns_number_gt 4295 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0378P)^2^+0.2782P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.157(9) _refine_ls_number_reflns 4532 _refine_ls_number_parameters 371 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0269 _refine_ls_wR_factor_ref 0.0692 _refine_ls_wR_factor_gt 0.0674 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.044 _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 C1 C 0.4120(5) 0.89533(14) 0.41012(14) 0.0120(7) Uani 1 1 d . . . H1 H 0.2855 0.9109 0.3978 0.014 Uiso 1 1 calc R . . C2 C 0.7187(5) 0.89274(14) 0.42064(14) 0.0119(7) Uani 1 1 d . . . H2 H 0.8505 0.9062 0.4170 0.014 Uiso 1 1 calc R . . C3 C 0.4108(5) 0.61150(15) 0.40535(14) 0.0123(7) Uani 1 1 d . . . H3 H 0.2863 0.5988 0.3883 0.015 Uiso 1 1 calc R . . C4 C 0.7165(5) 0.60883(14) 0.42435(14) 0.0118(7) Uani 1 1 d . . . H4 H 0.8477 0.5940 0.4230 0.014 Uiso 1 1 calc R . . C5 C 0.5946(5) 0.50638(14) 0.34150(14) 0.0127(7) Uani 1 1 d . . . H5A H 0.5032 0.4657 0.3558 0.015 Uiso 1 1 calc R . . H5B H 0.7262 0.4855 0.3461 0.015 Uiso 1 1 calc R . . C6 C 0.5586(5) 0.52822(14) 0.26488(14) 0.0139(7) Uani 1 1 d . . . H6 H 0.6256 0.5708 0.2451 0.017 Uiso 1 1 calc R . . C7 C 0.4373(5) 0.49037(14) 0.22430(15) 0.0123(7) Uani 1 1 d . . . H7 H 0.3627 0.4507 0.2454 0.015 Uiso 1 1 calc R . . C8 C 0.5882(6) 1.00704(14) 0.35344(14) 0.0148(8) Uani 1 1 d . . . H8A H 0.7155 1.0307 0.3617 0.018 Uiso 1 1 calc R . . H8B H 0.4885 1.0436 0.3697 0.018 Uiso 1 1 calc R . . N1 N 0.4566(4) 0.83204(12) 0.44482(11) 0.0096(6) Uani 1 1 d . . . N2 N 0.5728(4) 0.93445(12) 0.39482(11) 0.0108(6) Uani 1 1 d . . . N3 N 0.4524(4) 0.66964(12) 0.44788(12) 0.0109(6) Uani 1 1 d . . . N4 N 0.5728(4) 0.57304(12) 0.38995(11) 0.0109(6) Uani 1 1 d . . . N5 N 0.1523(4) 0.66991(12) 0.54815(12) 0.0094(6) Uani 1 1 d . . . N6 N 0.1470(4) 0.83250(12) 0.53985(12) 0.0117(6) Uani 1 1 d . . . O1 O -0.1812(3) 0.73524(11) 0.31252(9) 0.0163(5) Uani 1 1 d . . . O2 O 0.0349(3) 0.73186(10) 0.41383(9) 0.0141(4) Uani 1 1 d . . . O3 O 0.1047(3) 0.81462(11) 0.31373(10) 0.0159(5) Uani 1 1 d . . . O4 O 0.1304(3) 0.67703(11) 0.30011(10) 0.0153(5) Uani 1 1 d . . . O5 O 0.7607(3) 0.58800(10) 0.00887(10) 0.0150(5) Uani 1 1 d . . . O6 O 1.0978(3) 0.56192(11) -0.00353(10) 0.0172(5) Uani 1 1 d . . . O7 O 0.9301(4) 0.51972(10) 0.10274(10) 0.0162(5) Uani 1 1 d . . . O8 O 0.9877(3) 0.65567(10) 0.08265(9) 0.0147(5) Uani 1 1 d . . . O9 O 0.6749(4) 0.84269(14) 0.11597(12) 0.0227(6) Uani 1 1 d . . . H25 H 0.767(6) 0.847(2) 0.135(2) 0.027 Uiso 1 1 d . . . H21 H 0.663(6) 0.866(2) 0.081(2) 0.027 Uiso 1 1 d . . . O10 O 0.3054(4) 0.68136(11) 0.16829(11) 0.0143(5) Uani 1 1 d . . . H22 H 0.232(6) 0.6785(18) 0.1368(19) 0.017 Uiso 1 1 d . . . H28 H 0.256(5) 0.6791(18) 0.2128(17) 0.017 Uiso 1 1 d . . . O11 O 0.7072(4) 0.69579(11) 0.17627(11) 0.0151(5) Uani 1 1 d . . . H23 H 0.796(6) 0.6800(18) 0.1498(19) 0.018 Uiso 1 1 d . . . H26 H 0.750(5) 0.7058(18) 0.2169(17) 0.018 Uiso 1 1 d . . . O12 O 0.2728(4) 0.82759(11) 0.11187(10) 0.0169(5) Uani 1 1 d D . . H27 H 0.282(6) 0.8577(15) 0.0737(13) 0.020 Uiso 1 1 d D . . H29 H 0.188(6) 0.8443(18) 0.1425(19) 0.020 Uiso 1 1 d . . . O13 O 0.4819(4) 0.80487(12) 0.26057(11) 0.0176(5) Uani 1 1 d . . . H30 H 0.555(6) 0.785(2) 0.2824(19) 0.021 Uiso 1 1 d . . . H31 H 0.371(6) 0.8047(19) 0.2799(19) 0.021 Uiso 1 1 d . . . O14 O 0.4985(4) 0.71510(12) 0.02855(11) 0.0206(5) Uani 1 1 d . . . H20 H 0.503(6) 0.741(2) -0.0019(18) 0.025 Uiso 1 1 d . . . H37 H 0.596(6) 0.6926(19) 0.0210(19) 0.025 Uiso 1 1 d . . . O15 O 0.9838(4) 0.88465(11) 0.19413(10) 0.0175(5) Uani 1 1 d . . . H34 H 0.965(6) 0.9237(18) 0.2071(17) 0.021 Uiso 1 1 d D . . H35 H 1.014(5) 0.8609(17) 0.2283(17) 0.021 Uiso 1 1 d D . . O16 O 0.5013(4) 0.96825(11) 0.74622(11) 0.0198(5) Uani 1 1 d . . . H24 H 0.484(6) 0.9674(18) 0.7899(19) 0.024 Uiso 1 1 d . . . H36 H 0.539(6) 0.9311(19) 0.7323(17) 0.024 Uiso 1 1 d . . . O17 O 0.9495(4) 0.99787(12) 0.04990(12) 0.0189(5) Uani 1 1 d . . . H32 H 1.044(6) 0.979(2) 0.0300(19) 0.023 Uiso 1 1 d . . . H33 H 0.852(6) 0.978(2) 0.035(2) 0.023 Uiso 1 1 d . . . S3 S 0.02080(12) 0.73975(3) 0.33465(3) 0.01125(16) Uani 1 1 d . . . S4 S 0.94561(12) 0.58019(3) 0.04797(3) 0.01166(17) Uani 1 1 d . . . Cu1 Cu 0.49135(6) 0.762735(16) 0.143387(15) 0.01150(10) Uani 1 1 d . . . Cu2 Cu 0.29221(5) 0.750637(18) 0.491778(15) 0.00991(9) 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 C1 0.016(2) 0.0084(11) 0.0115(13) -0.0002(10) -0.0008(13) 0.0007(13) C2 0.014(2) 0.0096(11) 0.0121(12) -0.0007(9) -0.0013(14) -0.0006(13) C3 0.013(2) 0.0107(11) 0.0126(13) -0.0002(10) -0.0005(14) -0.0011(13) C4 0.0113(19) 0.0100(11) 0.0141(12) -0.0016(10) 0.0014(14) 0.0016(14) C5 0.015(2) 0.0060(11) 0.0167(13) -0.0047(9) -0.0003(14) 0.0006(12) C6 0.020(2) 0.0069(10) 0.0151(13) 0.0000(10) 0.0015(14) 0.0027(13) C7 0.012(2) 0.0095(11) 0.0157(13) -0.0033(10) 0.0027(14) 0.0034(13) C8 0.022(2) 0.0060(11) 0.0161(13) 0.0040(10) 0.0001(14) -0.0014(12) N1 0.0089(17) 0.0086(9) 0.0114(10) -0.0004(8) 0.0006(11) 0.0006(11) N2 0.0124(17) 0.0096(10) 0.0105(11) -0.0001(8) -0.0008(11) -0.0006(11) N3 0.0095(17) 0.0077(9) 0.0153(11) 0.0012(8) 0.0000(11) -0.0007(11) N4 0.0128(17) 0.0067(9) 0.0132(11) -0.0013(8) 0.0000(11) 0.0013(11) N5 0.0063(17) 0.0091(9) 0.0127(11) -0.0005(8) 0.0011(11) 0.0027(11) N6 0.0134(18) 0.0090(10) 0.0128(10) 0.0019(8) -0.0011(11) -0.0026(11) O1 0.0130(13) 0.0223(10) 0.0138(8) 0.0017(8) -0.0028(8) -0.0002(10) O2 0.0152(12) 0.0159(9) 0.0111(8) 0.0000(6) -0.0010(8) -0.0031(10) O3 0.0207(15) 0.0110(9) 0.0158(9) 0.0036(7) -0.0015(10) -0.0038(9) O4 0.0203(15) 0.0112(9) 0.0146(9) -0.0005(7) 0.0007(10) 0.0028(10) O5 0.0177(13) 0.0116(8) 0.0158(9) 0.0018(7) -0.0030(10) -0.0018(9) O6 0.0197(14) 0.0143(9) 0.0176(10) 0.0000(7) 0.0037(10) 0.0016(9) O7 0.0208(15) 0.0117(8) 0.0161(9) 0.0037(7) -0.0004(10) -0.0004(10) O8 0.0183(14) 0.0097(8) 0.0160(9) -0.0035(6) -0.0004(10) -0.0020(10) O9 0.0191(16) 0.0265(11) 0.0224(12) 0.0118(9) -0.0067(11) -0.0079(12) O10 0.0170(15) 0.0128(9) 0.0132(9) 0.0009(8) -0.0017(10) -0.0018(10) O11 0.0155(14) 0.0158(9) 0.0139(9) -0.0029(8) 0.0010(10) 0.0017(10) O12 0.0221(15) 0.0127(9) 0.0158(10) 0.0035(8) 0.0051(11) 0.0032(10) O13 0.0172(15) 0.0175(9) 0.0180(10) -0.0010(7) -0.0001(11) 0.0020(12) O14 0.0245(15) 0.0205(10) 0.0168(10) -0.0003(8) 0.0018(12) 0.0048(11) O15 0.0250(16) 0.0111(8) 0.0163(9) 0.0026(7) -0.0027(11) 0.0015(11) O16 0.0264(16) 0.0135(8) 0.0195(10) 0.0006(8) 0.0013(12) 0.0036(12) O17 0.0154(16) 0.0161(9) 0.0253(11) -0.0044(8) -0.0006(12) -0.0008(10) S3 0.0139(5) 0.0099(3) 0.0099(3) 0.0006(2) -0.0004(3) 0.0002(3) S4 0.0145(5) 0.0090(3) 0.0115(3) -0.0001(2) 0.0000(3) -0.0001(3) Cu1 0.0134(2) 0.00790(14) 0.01323(14) 0.00072(10) 0.00021(15) -0.00019(15) Cu2 0.0124(2) 0.00520(12) 0.01209(14) -0.00009(12) 0.00161(13) 0.00012(16) _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 C1 N1 1.315(3) . ? C1 N2 1.342(4) . ? C1 H1 0.9500 . ? C2 N5 1.320(3) 4_566 ? C2 N2 1.339(4) . ? C2 H2 0.9500 . ? C3 N3 1.318(3) . ? C3 N4 1.343(4) . ? C3 H3 0.9500 . ? C4 N6 1.313(3) 4_566 ? C4 N4 1.343(4) . ? C4 H4 0.9500 . ? C5 N4 1.478(3) . ? C5 C6 1.498(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.311(4) . ? C6 H6 0.9500 . ? C7 C8 1.488(4) 3_645 ? C7 H7 0.9500 . ? C8 N2 1.484(3) . ? C8 C7 1.488(4) 3_655 ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? N1 N5 1.370(4) 4_566 ? N1 Cu2 2.021(2) . ? N3 N6 1.376(4) 4_566 ? N3 Cu2 1.976(2) . ? N5 C2 1.320(3) 4_466 ? N5 N1 1.370(4) 4_466 ? N5 Cu2 2.007(2) . ? N6 C4 1.313(3) 4_466 ? N6 N3 1.376(4) 4_466 ? N6 Cu2 1.964(2) . ? O1 S3 1.469(2) . ? O2 S3 1.4845(17) . ? O2 Cu2 2.330(2) . ? O3 S3 1.4809(19) . ? O4 S3 1.480(2) . ? O5 S4 1.486(2) . ? O6 S4 1.465(2) . ? O7 S4 1.4702(19) . ? O8 S4 1.4934(18) . ? O9 Cu1 1.958(2) . ? O9 H25 0.74(4) . ? O9 H21 0.77(4) . ? O10 Cu1 1.975(2) . ? O10 H22 0.78(4) . ? O10 H28 0.90(3) . ? O11 Cu1 1.999(2) . ? O11 H23 0.84(4) . ? O11 H26 0.83(3) . ? O12 Cu1 1.985(2) . ? O12 H27 0.885(18) . ? O12 H29 0.87(4) . ? O13 Cu1 2.304(2) . ? O13 H30 0.73(4) . ? O13 H31 0.85(4) . ? O14 Cu1 2.295(2) . ? O14 H20 0.73(4) . ? O14 H37 0.80(4) . ? O15 H34 0.73(3) . ? O15 H35 0.79(3) . ? O16 H24 0.82(3) . ? O16 H36 0.74(3) . ? O17 H32 0.82(4) . ? O17 H33 0.81(4) . ? 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 N1 C1 N2 109.4(3) . . ? N1 C1 H1 125.3 . . ? N2 C1 H1 125.3 . . ? N5 C2 N2 109.9(3) 4_566 . ? N5 C2 H2 125.1 4_566 . ? N2 C2 H2 125.1 . . ? N3 C3 N4 109.1(3) . . ? N3 C3 H3 125.5 . . ? N4 C3 H3 125.5 . . ? N6 C4 N4 109.2(3) 4_566 . ? N6 C4 H4 125.4 4_566 . ? N4 C4 H4 125.4 . . ? N4 C5 C6 111.4(2) . . ? N4 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? N4 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? C7 C6 C5 122.0(3) . . ? C7 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? C6 C7 C8 122.7(3) . 3_645 ? C6 C7 H7 118.7 . . ? C8 C7 H7 118.7 3_645 . ? N2 C8 C7 109.3(2) . 3_655 ? N2 C8 H8A 109.8 . . ? C7 C8 H8A 109.8 3_655 . ? N2 C8 H8B 109.8 . . ? C7 C8 H8B 109.8 3_655 . ? H8A C8 H8B 108.3 . . ? C1 N1 N5 107.7(3) . 4_566 ? C1 N1 Cu2 131.8(2) . . ? N5 N1 Cu2 120.35(17) 4_566 . ? C2 N2 C1 106.4(2) . . ? C2 N2 C8 126.4(3) . . ? C1 N2 C8 127.1(3) . . ? C3 N3 N6 107.2(2) . 4_566 ? C3 N3 Cu2 132.3(2) . . ? N6 N3 Cu2 120.50(17) 4_566 . ? C4 N4 C3 107.1(2) . . ? C4 N4 C5 125.4(3) . . ? C3 N4 C5 127.5(3) . . ? C2 N5 N1 106.7(2) 4_466 4_466 ? C2 N5 Cu2 129.7(2) 4_466 . ? N1 N5 Cu2 123.42(18) 4_466 . ? C4 N6 N3 107.5(3) 4_466 4_466 ? C4 N6 Cu2 127.3(2) 4_466 . ? N3 N6 Cu2 124.32(18) 4_466 . ? S3 O2 Cu2 131.07(13) . . ? Cu1 O9 H25 121(3) . . ? Cu1 O9 H21 122(3) . . ? H25 O9 H21 116(4) . . ? Cu1 O10 H22 107(3) . . ? Cu1 O10 H28 120(2) . . ? H22 O10 H28 116(4) . . ? Cu1 O11 H23 124(2) . . ? Cu1 O11 H26 115(2) . . ? H23 O11 H26 110(3) . . ? Cu1 O12 H27 121(3) . . ? Cu1 O12 H29 121(2) . . ? H27 O12 H29 112(3) . . ? Cu1 O13 H30 111(3) . . ? Cu1 O13 H31 115(2) . . ? H30 O13 H31 113(4) . . ? Cu1 O14 H20 120(3) . . ? Cu1 O14 H37 111(3) . . ? H20 O14 H37 98(4) . . ? H34 O15 H35 105(3) . . ? H24 O16 H36 112(3) . . ? H32 O17 H33 110(3) . . ? O1 S3 O4 109.46(12) . . ? O1 S3 O3 110.58(12) . . ? O4 S3 O3 109.36(12) . . ? O1 S3 O2 109.71(12) . . ? O4 S3 O2 109.25(11) . . ? O3 S3 O2 108.47(11) . . ? O6 S4 O7 110.61(12) . . ? O6 S4 O5 109.05(12) . . ? O7 S4 O5 110.00(13) . . ? O6 S4 O8 109.40(13) . . ? O7 S4 O8 110.15(11) . . ? O5 S4 O8 107.56(12) . . ? O9 Cu1 O10 178.46(9) . . ? O9 Cu1 O12 91.13(10) . . ? O10 Cu1 O12 88.52(9) . . ? O9 Cu1 O11 90.17(10) . . ? O10 Cu1 O11 90.19(9) . . ? O12 Cu1 O11 178.67(10) . . ? O9 Cu1 O14 89.99(9) . . ? O10 Cu1 O14 88.50(9) . . ? O12 Cu1 O14 86.93(9) . . ? O11 Cu1 O14 93.36(9) . . ? O9 Cu1 O13 92.26(9) . . ? O10 Cu1 O13 89.26(9) . . ? O12 Cu1 O13 94.43(9) . . ? O11 Cu1 O13 85.23(9) . . ? O14 Cu1 O13 177.35(8) . . ? N6 Cu2 N3 176.19(12) . . ? N6 Cu2 N5 91.12(9) . . ? N3 Cu2 N5 89.49(10) . . ? N6 Cu2 N1 88.87(10) . . ? N3 Cu2 N1 90.07(9) . . ? N5 Cu2 N1 173.04(11) . . ? N6 Cu2 O2 89.41(9) . . ? N3 Cu2 O2 94.40(9) . . ? N5 Cu2 O2 81.61(8) . . ? N1 Cu2 O2 105.35(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C5 C6 C7 -128.1(3) . . . . ? C5 C6 C7 C8 -174.7(3) . . . 3_645 ? N2 C1 N1 N5 -0.3(3) . . . 4_566 ? N2 C1 N1 Cu2 174.10(18) . . . . ? N5 C2 N2 C1 -0.7(3) 4_566 . . . ? N5 C2 N2 C8 -177.2(2) 4_566 . . . ? N1 C1 N2 C2 0.6(3) . . . . ? N1 C1 N2 C8 177.1(2) . . . . ? C7 C8 N2 C2 100.5(3) 3_655 . . . ? C7 C8 N2 C1 -75.3(4) 3_655 . . . ? N4 C3 N3 N6 -0.4(3) . . . 4_566 ? N4 C3 N3 Cu2 179.60(18) . . . . ? N6 C4 N4 C3 0.1(3) 4_566 . . . ? N6 C4 N4 C5 177.2(2) 4_566 . . . ? N3 C3 N4 C4 0.2(3) . . . . ? N3 C3 N4 C5 -176.8(2) . . . . ? C6 C5 N4 C4 -109.3(3) . . . . ? C6 C5 N4 C3 67.2(4) . . . . ? Cu2 O2 S3 O1 -169.64(12) . . . . ? Cu2 O2 S3 O4 70.37(17) . . . . ? Cu2 O2 S3 O3 -48.76(18) . . . . ? C4 N6 Cu2 N3 25.0(16) 4_466 . . . ? N3 N6 Cu2 N3 -143.0(14) 4_466 . . . ? C4 N6 Cu2 N5 124.2(2) 4_466 . . . ? N3 N6 Cu2 N5 -43.8(2) 4_466 . . . ? C4 N6 Cu2 N1 -48.9(2) 4_466 . . . ? N3 N6 Cu2 N1 143.1(2) 4_466 . . . ? C4 N6 Cu2 O2 -154.2(2) 4_466 . . . ? N3 N6 Cu2 O2 37.8(2) 4_466 . . . ? C3 N3 Cu2 N6 163.3(14) . . . . ? N6 N3 Cu2 N6 -16.7(17) 4_566 . . . ? C3 N3 Cu2 N5 64.0(2) . . . . ? N6 N3 Cu2 N5 -116.0(2) 4_566 . . . ? C3 N3 Cu2 N1 -122.9(3) . . . . ? N6 N3 Cu2 N1 57.07(19) 4_566 . . . ? C3 N3 Cu2 O2 -17.5(2) . . . . ? N6 N3 Cu2 O2 162.48(19) 4_566 . . . ? C2 N5 Cu2 N6 -137.5(2) 4_466 . . . ? N1 N5 Cu2 N6 48.9(2) 4_466 . . . ? C2 N5 Cu2 N3 38.7(2) 4_466 . . . ? N1 N5 Cu2 N3 -134.9(2) 4_466 . . . ? C2 N5 Cu2 N1 -47.6(9) 4_466 . . . ? N1 N5 Cu2 N1 138.7(7) 4_466 . . . ? C2 N5 Cu2 O2 133.3(2) 4_466 . . . ? N1 N5 Cu2 O2 -40.4(2) 4_466 . . . ? C1 N1 Cu2 N6 -48.6(2) . . . . ? N5 N1 Cu2 N6 125.2(2) 4_566 . . . ? C1 N1 Cu2 N3 135.0(2) . . . . ? N5 N1 Cu2 N3 -51.18(19) 4_566 . . . ? C1 N1 Cu2 N5 -138.6(7) . . . . ? N5 N1 Cu2 N5 35.2(9) 4_566 . . . ? C1 N1 Cu2 O2 40.5(2) . . . . ? N5 N1 Cu2 O2 -145.77(18) 4_566 . . . ? S3 O2 Cu2 N6 118.41(15) . . . . ? S3 O2 Cu2 N3 -61.54(15) . . . . ? S3 O2 Cu2 N5 -150.37(16) . . . . ? S3 O2 Cu2 N1 29.74(16) . . . . ? _diffrn_measured_fraction_theta_max 0.835 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.499 _refine_diff_density_min -0.926 _refine_diff_density_rms 0.088 data_4 _database_code_depnum_ccdc_archive 'CCDC 862715' #TrackingRef '- 4_02_27_2012.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H30 Cu6 N18 O28 S5' _chemical_formula_weight 1560.20 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 n n a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x+1/2, y+1/2, -z+1/2' 'x, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x-1/2, -y-1/2, z-1/2' '-x, y-1/2, z-1/2' _cell_length_a 24.569(4) _cell_length_b 14.682(2) _cell_length_c 22.399(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8080(2) _cell_formula_units_Z 4 _cell_measurement_temperature 278(2) _cell_measurement_reflns_used 9954 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 23.29 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3112 _exptl_absorpt_coefficient_mu 1.747 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4753 _exptl_absorpt_correction_T_max 0.7213 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 278(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II CCD' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 64167 _diffrn_reflns_av_R_equivalents 0.0647 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 23.39 _reflns_number_total 5881 _reflns_number_gt 3909 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The crystal loses solvent very quickly, even at -173.15 degree celsius. Therefore, the crystal was mounted in a capillary and flame sealed to prevent the loss of solvent during the collection. The data was collected at 5 degree celsius. Orientation disorder of the third sulphate anion (SO4) was present. In the final least- squares refinement this disorder was taken into account by two SO4 anions, Part 1 with S2', O33',O30', O31', and O32' and Part 2 with S2", O33", O30", O31", and O32". Disordered water molecules were also present in the structure. SQUEEZE routine was used to simplify and improve the refinement. Relative poor data quality prevents the anisotropic refinement for all non-hydrogen atoms. Atoms O31, O32 and O33 as well as O30', O31', O32' and O33' were refined iostropically. ; _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^)+(0.2000P)^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 5881 _refine_ls_number_parameters 364 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.1204 _refine_ls_R_factor_gt 0.0997 _refine_ls_wR_factor_ref 0.3151 _refine_ls_wR_factor_gt 0.2924 _refine_ls_goodness_of_fit_ref 1.232 _refine_ls_restrained_S_all 1.250 _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 S2 S 0.3776(6) 0.1821(7) 0.1511(4) 0.180(4) Uani 0.652(6) 1 d P A 1 O32 O 0.3835(7) 0.1968(11) 0.0769(8) 0.133(6) Uiso 0.652(6) 1 d PD A 1 O30 O 0.4026(8) 0.2595(8) 0.1936(8) 0.078(5) Uani 0.652(6) 1 d PD A 1 O33 O 0.3131(9) 0.1655(16) 0.1630(10) 0.188(9) Uiso 0.652(6) 1 d PD A 1 O31 O 0.3986(9) 0.0907(14) 0.1648(11) 0.171(9) Uiso 0.652(6) 1 d PD A 1 S2' S 0.4449(9) 0.1757(11) 0.1507(8) 0.180(4) Uani 0.348(6) 1 d PD A 2 O33' O 0.5062(10) 0.176(2) 0.1487(16) 0.176(12) Uiso 0.348(6) 1 d PD A 2 O31' O 0.4330(16) 0.0872(16) 0.1740(17) 0.176(12) Uiso 0.348(6) 1 d PD A 2 O32' O 0.4255(14) 0.187(2) 0.0872(10) 0.147(13) Uiso 0.348(6) 1 d PD A 2 O30' O 0.4153(12) 0.2498(11) 0.1819(11) 0.050(9) Uiso 0.348(6) 1 d PD A 2 O20 O 0.3131(6) 0.2433(7) 0.0070(5) 0.144(3) Uani 1 1 d D . . Cu1 Cu 0.40876(4) 0.40762(8) 0.14797(5) 0.0393(4) Uani 1 1 d D . . Cu2 Cu 0.47794(4) 0.39480(7) 0.01801(4) 0.0383(4) Uani 1 1 d D . . Cu3 Cu 0.34072(4) 0.40700(8) 0.01680(5) 0.0425(4) Uani 1 1 d D . . S4 S 0.40910(8) 0.59314(15) 0.05561(11) 0.0388(6) Uani 1 1 d . . . N5 N 0.4378(3) 0.3881(4) -0.0576(3) 0.0363(16) Uani 1 1 d . A . N2 N 0.3007(3) 0.3993(4) 0.0934(3) 0.0393(17) Uani 1 1 d . A . N8 N 0.5174(3) 0.3968(5) 0.0950(3) 0.0415(18) Uani 1 1 d . A . N4 N 0.3826(3) 0.3904(5) -0.0592(3) 0.0472(19) Uani 1 1 d . A . N1 N 0.3275(3) 0.3986(5) 0.1468(3) 0.0399(18) Uani 1 1 d . A . N3 N 0.2426(3) 0.3749(5) 0.1646(3) 0.0415(17) Uani 1 1 d . A . N7 N 0.4895(3) 0.3974(4) 0.1479(3) 0.0382(17) Uani 1 1 d . A . N9 N 0.5755(3) 0.3774(6) 0.1678(4) 0.051(2) Uani 1 1 d . A . N6 N 0.4091(3) 0.3765(6) -0.1498(4) 0.062(3) Uani 1 1 d . A . C2 C 0.2485(3) 0.3856(6) 0.1063(4) 0.043(2) Uani 1 1 d . . . H2 H 0.2203 0.3838 0.0785 0.052 Uiso 1 1 calc R A . C6 C 0.5251(3) 0.3857(6) 0.1904(4) 0.047(2) Uani 1 1 d . . . H6 H 0.5167 0.3833 0.2308 0.057 Uiso 1 1 calc R A . C4 C 0.4526(4) 0.3838(6) -0.1133(4) 0.047(2) Uani 1 1 d . . . H4 H 0.4886 0.3854 -0.1263 0.057 Uiso 1 1 calc R A . C1 C 0.2938(3) 0.3848(7) 0.1885(4) 0.054(3) Uani 1 1 d . . . H1 H 0.3024 0.3818 0.2289 0.065 Uiso 1 1 calc R A . C3 C 0.3662(4) 0.3854(6) -0.1133(4) 0.054(3) Uani 1 1 d . . . H3 H 0.3300 0.3876 -0.1255 0.065 Uiso 1 1 calc R A . C5 C 0.5702(4) 0.3846(5) 0.1084(4) 0.039(2) Uani 1 1 d . . . H5 H 0.5985 0.3815 0.0809 0.047 Uiso 1 1 calc R A . O2 O 0.4571(2) 0.5578(4) 0.0235(2) 0.0418(14) Uani 1 1 d . . . O1 O 0.3603(2) 0.5565(4) 0.0263(3) 0.0515(16) Uani 1 1 d . A . O3 O 0.4127(2) 0.5603(5) 0.1164(3) 0.0544(17) Uani 1 1 d . A . O4 O 0.4094(2) 0.6911(4) 0.0522(3) 0.063(2) Uani 1 1 d . A . C9 C 0.6262(3) 0.3585(7) 0.2018(4) 0.054(3) Uani 1 1 d . . . H9A H 0.6284 0.3984 0.2363 0.065 Uiso 1 1 calc R A . H9B H 0.6578 0.3694 0.1768 0.065 Uiso 1 1 calc R . . C10 C 0.6254(3) 0.2627(7) 0.2214(4) 0.049(2) Uani 1 1 d . . . H10 H 0.6248 0.2175 0.1923 0.059 Uiso 1 1 calc R . . C14 C 0.4103(4) 0.3681(9) -0.2156(4) 0.068(3) Uani 1 1 d . . . H14A H 0.3779 0.3960 -0.2324 0.082 Uiso 1 1 calc R A . H14B H 0.4418 0.3998 -0.2312 0.082 Uiso 1 1 calc R . . O7 O 0.40870(18) 0.3695(4) 0.0620(2) 0.0341(13) Uani 1 1 d . A . C12 C 0.4125(6) 0.2733(8) -0.2326(5) 0.133(8) Uani 1 1 d . . . H12 H 0.4150 0.2399 -0.1975 0.159 Uiso 1 1 calc R . . S1 S 0.2500 0.5000 -0.06351(15) 0.0678(11) Uani 1 2 d S . . O8 O 0.2727(2) 0.4288(5) -0.0247(3) 0.0626(19) Uani 1 1 d . A . O9 O 0.2065(3) 0.4585(6) -0.0993(3) 0.097(3) Uani 1 1 d . A . O10 O 0.4986(6) 0.2360(7) 0.0102(5) 0.144(3) Uani 1 1 d D A . O5 O 0.4077(2) 0.4586(5) 0.2291(3) 0.063(2) Uani 1 1 d . A . C8 C 0.1925(3) 0.2610(6) 0.2220(4) 0.049(2) Uani 1 1 d . . . H8 H 0.1931 0.2140 0.1941 0.059 Uiso 1 1 calc R . . C7 C 0.1916(3) 0.3557(7) 0.1991(4) 0.053(3) Uani 1 1 d . . . H7A H 0.1886 0.3980 0.2322 0.064 Uiso 1 1 calc R A . H7B H 0.1602 0.3642 0.1734 0.064 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 S2 0.253(12) 0.135(7) 0.151(7) 0.022(5) 0.035(8) -0.016(7) O30 0.083(12) 0.056(8) 0.095(12) 0.012(7) 0.033(9) 0.000(6) S2' 0.253(12) 0.135(7) 0.151(7) 0.022(5) 0.035(8) -0.016(7) O20 0.192(10) 0.104(6) 0.136(7) 0.000(5) 0.015(5) 0.003(5) Cu1 0.0293(7) 0.0620(8) 0.0266(7) 0.0013(5) 0.0020(4) -0.0005(4) Cu2 0.0295(7) 0.0594(8) 0.0261(7) 0.0019(4) 0.0017(4) 0.0012(4) Cu3 0.0284(7) 0.0681(8) 0.0311(7) 0.0054(5) 0.0010(4) -0.0022(5) S4 0.0350(13) 0.0445(13) 0.0367(13) 0.0006(9) 0.0066(9) 0.0062(9) N5 0.029(4) 0.045(4) 0.035(4) -0.001(3) 0.009(3) -0.006(3) N2 0.027(4) 0.054(4) 0.037(4) 0.007(3) 0.003(3) -0.004(3) N8 0.030(4) 0.061(5) 0.034(4) 0.003(3) 0.003(3) 0.005(3) N4 0.029(4) 0.074(5) 0.038(5) -0.018(4) 0.000(3) 0.002(3) N1 0.033(4) 0.060(5) 0.026(4) 0.010(3) 0.002(3) -0.002(3) N3 0.032(4) 0.063(5) 0.030(4) 0.017(3) 0.001(3) -0.002(3) N7 0.042(4) 0.052(4) 0.020(4) 0.007(3) 0.004(3) 0.010(3) N9 0.040(4) 0.070(5) 0.044(5) 0.023(4) -0.010(4) 0.000(4) N6 0.081(7) 0.054(5) 0.050(6) -0.004(4) -0.007(5) -0.006(4) C2 0.020(4) 0.059(6) 0.050(6) 0.007(4) -0.004(4) -0.006(4) C6 0.033(5) 0.076(6) 0.032(5) 0.018(4) 0.008(4) -0.003(4) C4 0.055(6) 0.051(5) 0.037(5) -0.008(4) -0.001(5) 0.002(4) C1 0.035(5) 0.090(7) 0.037(5) 0.020(5) -0.003(4) 0.013(5) C3 0.055(6) 0.067(6) 0.039(6) -0.016(5) 0.014(5) -0.002(5) C5 0.037(5) 0.045(5) 0.036(5) 0.006(4) 0.004(4) 0.001(4) O2 0.040(3) 0.050(3) 0.036(3) 0.003(3) 0.013(3) -0.001(3) O1 0.032(3) 0.056(4) 0.066(4) 0.000(3) -0.005(3) 0.003(3) O3 0.067(5) 0.057(4) 0.039(4) -0.006(3) 0.012(3) 0.003(3) O4 0.071(5) 0.045(4) 0.073(5) 0.001(3) 0.020(3) 0.003(3) C9 0.023(4) 0.090(7) 0.050(5) 0.027(5) -0.002(4) 0.002(4) C10 0.032(5) 0.071(6) 0.044(5) 0.014(5) 0.006(4) 0.007(4) C14 0.076(8) 0.108(9) 0.021(5) -0.021(6) -0.003(4) 0.004(6) O7 0.032(3) 0.048(3) 0.023(3) 0.001(3) 0.000(2) -0.002(2) C12 0.33(3) 0.052(8) 0.020(6) -0.014(5) -0.006(8) -0.013(9) S1 0.050(2) 0.117(3) 0.0367(19) 0.000 0.000 0.018(2) O8 0.035(3) 0.104(5) 0.048(4) 0.026(4) -0.011(3) -0.005(3) O9 0.105(6) 0.118(7) 0.067(5) -0.040(5) -0.049(5) 0.036(5) O10 0.192(10) 0.104(6) 0.136(7) 0.000(5) 0.015(5) 0.003(5) O5 0.065(4) 0.094(6) 0.030(4) -0.014(4) 0.006(3) -0.004(3) C8 0.036(5) 0.062(6) 0.048(5) 0.016(5) 0.000(4) 0.004(4) C7 0.022(4) 0.087(7) 0.051(5) 0.032(5) -0.002(4) 0.008(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 S2 O31 1.47(2) . ? S2 O33 1.62(2) . ? S2 O32 1.683(19) . ? S2 O30 1.60(2) . ? O30 Cu1 2.407(10) . ? S2' O31' 1.430(17) . ? S2' O33' 1.507(17) . ? S2' O30' 1.484(16) . ? S2' O32' 1.510(17) . ? O30' Cu1 2.443(15) . ? Cu1 O5 1.966(6) . ? Cu1 N7 1.989(7) . ? Cu1 N1 2.001(7) . ? Cu1 O7 2.004(5) . ? Cu1 O3 2.352(7) . ? Cu2 N5 1.962(7) . ? Cu2 O2 1.974(5) 5_665 ? Cu2 N8 1.978(7) . ? Cu2 O7 2.001(5) . ? Cu2 O10 2.393(10) . ? Cu3 O8 1.938(6) . ? Cu3 N2 1.981(7) . ? Cu3 N4 2.003(7) . ? Cu3 O7 2.029(5) . ? Cu3 O1 2.257(6) . ? S4 O4 1.441(7) . ? S4 O3 1.447(7) . ? S4 O1 1.469(6) . ? S4 O2 1.475(6) . ? N5 C4 1.301(11) . ? N5 N4 1.358(11) . ? N2 C2 1.331(10) . ? N2 N1 1.364(10) . ? N8 C5 1.344(11) . ? N8 N7 1.369(9) . ? N4 C3 1.280(12) . ? N1 C1 1.264(11) . ? N3 C2 1.324(11) . ? N3 C1 1.376(11) . ? N3 C7 1.497(10) . ? N7 C6 1.304(10) . ? N9 C5 1.341(11) . ? N9 C6 1.345(11) . ? N9 C9 1.486(11) . ? N6 C4 1.350(12) . ? N6 C3 1.340(12) . ? N6 C14 1.479(13) . ? C2 H2 0.9300 . ? C6 H6 0.9300 . ? C4 H4 0.9300 . ? C1 H1 0.9300 . ? C3 H3 0.9300 . ? C5 H5 0.9300 . ? O2 Cu2 1.974(5) 5_665 ? C9 C10 1.474(13) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C10 1.334(17) 4 ? C10 H10 0.9300 . ? C14 C12 1.444(16) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C12 C12 1.04(2) 4_554 ? C12 H12 0.9300 . ? S1 O9 1.469(7) . ? S1 O9 1.469(8) 2_565 ? S1 O8 1.470(7) 2_565 ? S1 O8 1.470(7) . ? C8 C8 1.297(17) 4 ? C8 C7 1.483(12) . ? C8 H8 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? 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 O31 S2 O33 99.9(12) . . ? O31 S2 O32 107.0(12) . . ? O33 S2 O32 105.4(13) . . ? O31 S2 O30 112.8(13) . . ? O33 S2 O30 112.6(12) . . ? O32 S2 O30 117.5(10) . . ? S2 O30 Cu1 114.3(10) . . ? O31' S2' O33' 102(2) . . ? O31' S2' O30' 113.3(18) . . ? O33' S2' O30' 120(2) . . ? O31' S2' O32' 113(2) . . ? O33' S2' O32' 106.7(18) . . ? O30' S2' O32' 101.9(18) . . ? S2' O30' Cu1 125.5(13) . . ? O5 Cu1 N7 92.5(2) . . ? O5 Cu1 N1 91.4(2) . . ? N7 Cu1 N1 171.8(3) . . ? O5 Cu1 O7 173.7(3) . . ? N7 Cu1 O7 88.8(2) . . ? N1 Cu1 O7 88.2(2) . . ? O5 Cu1 O3 85.1(3) . . ? N7 Cu1 O3 91.7(2) . . ? N1 Cu1 O3 95.8(2) . . ? O7 Cu1 O3 88.7(2) . . ? O5 Cu1 O30 87.2(5) . . ? N7 Cu1 O30 89.7(5) . . ? N1 Cu1 O30 83.3(5) . . ? O7 Cu1 O30 99.0(5) . . ? O3 Cu1 O30 172.3(5) . . ? O5 Cu1 O30' 94.3(6) . . ? N7 Cu1 O30' 82.2(7) . . ? N1 Cu1 O30' 90.4(7) . . ? O7 Cu1 O30' 92.0(6) . . ? O3 Cu1 O30' 173.8(7) . . ? O30 Cu1 O30' 10.1(7) . . ? N5 Cu2 O2 91.0(2) . 5_665 ? N5 Cu2 N8 177.8(3) . . ? O2 Cu2 N8 90.5(3) 5_665 . ? N5 Cu2 O7 89.4(2) . . ? O2 Cu2 O7 170.0(2) 5_665 . ? N8 Cu2 O7 89.4(2) . . ? N5 Cu2 O10 89.7(4) . . ? O2 Cu2 O10 97.9(4) 5_665 . ? N8 Cu2 O10 88.6(4) . . ? O7 Cu2 O10 92.0(4) . . ? O8 Cu3 N2 89.8(3) . . ? O8 Cu3 N4 93.2(3) . . ? N2 Cu3 N4 169.7(3) . . ? O8 Cu3 O7 173.4(3) . . ? N2 Cu3 O7 87.7(2) . . ? N4 Cu3 O7 88.2(3) . . ? O8 Cu3 O1 93.9(3) . . ? N2 Cu3 O1 94.6(3) . . ? N4 Cu3 O1 95.1(3) . . ? O7 Cu3 O1 92.3(2) . . ? O4 S4 O3 112.5(4) . . ? O4 S4 O1 110.2(4) . . ? O3 S4 O1 110.4(4) . . ? O4 S4 O2 108.7(3) . . ? O3 S4 O2 107.0(3) . . ? O1 S4 O2 107.8(4) . . ? C4 N5 N4 104.8(7) . . ? C4 N5 Cu2 133.6(6) . . ? N4 N5 Cu2 121.6(5) . . ? C2 N2 N1 105.9(7) . . ? C2 N2 Cu3 132.4(6) . . ? N1 N2 Cu3 121.3(5) . . ? C5 N8 N7 106.9(7) . . ? C5 N8 Cu2 131.8(6) . . ? N7 N8 Cu2 120.6(5) . . ? C3 N4 N5 109.7(7) . . ? C3 N4 Cu3 130.5(7) . . ? N5 N4 Cu3 119.6(5) . . ? C1 N1 N2 109.5(7) . . ? C1 N1 Cu1 130.8(6) . . ? N2 N1 Cu1 119.5(5) . . ? C2 N3 C1 105.7(7) . . ? C2 N3 C7 128.5(7) . . ? C1 N3 C7 125.8(7) . . ? C6 N7 N8 107.2(7) . . ? C6 N7 Cu1 132.6(5) . . ? N8 N7 Cu1 120.0(5) . . ? C5 N9 C6 106.0(7) . . ? C5 N9 C9 127.3(8) . . ? C6 N9 C9 126.6(8) . . ? C4 N6 C3 104.3(9) . . ? C4 N6 C14 126.5(9) . . ? C3 N6 C14 129.1(9) . . ? N2 C2 N3 109.7(7) . . ? N2 C2 H2 125.1 . . ? N3 C2 H2 125.1 . . ? N7 C6 N9 110.8(7) . . ? N7 C6 H6 124.6 . . ? N9 C6 H6 124.6 . . ? N5 C4 N6 111.3(9) . . ? N5 C4 H4 124.4 . . ? N6 C4 H4 124.4 . . ? N1 C1 N3 109.2(8) . . ? N1 C1 H1 125.4 . . ? N3 C1 H1 125.4 . . ? N4 C3 N6 109.6(9) . . ? N4 C3 H3 125.2 . . ? N6 C3 H3 125.2 . . ? N9 C5 N8 109.1(8) . . ? N9 C5 H5 125.4 . . ? N8 C5 H5 125.4 . . ? S4 O2 Cu2 138.7(4) . 5_665 ? S4 O1 Cu3 124.9(4) . . ? S4 O3 Cu1 126.7(4) . . ? N9 C9 C10 108.6(7) . . ? N9 C9 H9A 110.0 . . ? C10 C9 H9A 110.0 . . ? N9 C9 H9B 110.0 . . ? C10 C9 H9B 110.0 . . ? H9A C9 H9B 108.3 . . ? C10 C10 C9 123.5(12) 4 . ? C10 C10 H10 118.3 4 . ? C9 C10 H10 118.3 . . ? C12 C14 N6 110.2(10) . . ? C12 C14 H14A 109.6 . . ? N6 C14 H14A 109.6 . . ? C12 C14 H14B 109.6 . . ? N6 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? Cu2 O7 Cu1 114.9(2) . . ? Cu2 O7 Cu3 113.8(3) . . ? Cu1 O7 Cu3 113.9(2) . . ? C12 C12 C14 146.7(18) 4_554 . ? C12 C12 H12 106.7 4_554 . ? C14 C12 H12 106.7 . . ? O9 S1 O9 113.8(7) . 2_565 ? O9 S1 O8 109.9(4) . 2_565 ? O9 S1 O8 107.8(5) 2_565 2_565 ? O9 S1 O8 107.8(5) . . ? O9 S1 O8 109.9(4) 2_565 . ? O8 S1 O8 107.5(6) 2_565 . ? S1 O8 Cu3 136.7(4) . . ? C8 C8 C7 124.7(12) 4 . ? C8 C8 H8 117.7 4 . ? C7 C8 H8 117.7 . . ? C8 C7 N3 110.0(7) . . ? C8 C7 H7A 109.7 . . ? N3 C7 H7A 109.7 . . ? C8 C7 H7B 109.7 . . ? N3 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O31 S2 O30 Cu1 150.5(12) . . . . ? O33 S2 O30 Cu1 -97.4(12) . . . . ? O32 S2 O30 Cu1 25.4(16) . . . . ? O31' S2' O30' Cu1 -168(2) . . . . ? O33' S2' O30' Cu1 70(3) . . . . ? O32' S2' O30' Cu1 -47(3) . . . . ? S2 O30 Cu1 O5 156.2(11) . . . . ? S2 O30 Cu1 N7 -111.3(10) . . . . ? S2 O30 Cu1 N1 64.5(10) . . . . ? S2 O30 Cu1 O7 -22.6(11) . . . . ? S2 O30 Cu1 O3 148(3) . . . . ? S2 O30 Cu1 O30' -70(6) . . . . ? S2' O30' Cu1 O5 -147(2) . . . . ? S2' O30' Cu1 N7 -55(2) . . . . ? S2' O30' Cu1 N1 122(2) . . . . ? S2' O30' Cu1 O7 34(2) . . . . ? S2' O30' Cu1 O3 -63(7) . . . . ? S2' O30' Cu1 O30 167(9) . . . . ? O2 Cu2 N5 C4 21.7(8) 5_665 . . . ? N8 Cu2 N5 C4 -112(7) . . . . ? O7 Cu2 N5 C4 -168.2(8) . . . . ? O10 Cu2 N5 C4 -76.2(8) . . . . ? O2 Cu2 N5 N4 -155.9(6) 5_665 . . . ? N8 Cu2 N5 N4 70(7) . . . . ? O7 Cu2 N5 N4 14.2(5) . . . . ? O10 Cu2 N5 N4 106.2(6) . . . . ? O8 Cu3 N2 C2 18.3(8) . . . . ? N4 Cu3 N2 C2 -88.7(17) . . . . ? O7 Cu3 N2 C2 -155.5(8) . . . . ? O1 Cu3 N2 C2 112.3(8) . . . . ? O8 Cu3 N2 N1 -169.0(6) . . . . ? N4 Cu3 N2 N1 83.9(17) . . . . ? O7 Cu3 N2 N1 17.1(6) . . . . ? O1 Cu3 N2 N1 -75.1(6) . . . . ? N5 Cu2 N8 C5 102(7) . . . . ? O2 Cu2 N8 C5 -31.8(8) 5_665 . . . ? O7 Cu2 N8 C5 158.2(7) . . . . ? O10 Cu2 N8 C5 66.1(8) . . . . ? N5 Cu2 N8 N7 -67(8) . . . . ? O2 Cu2 N8 N7 159.4(6) 5_665 . . . ? O7 Cu2 N8 N7 -10.6(6) . . . . ? O10 Cu2 N8 N7 -102.7(6) . . . . ? C4 N5 N4 C3 1.5(9) . . . . ? Cu2 N5 N4 C3 179.7(6) . . . . ? C4 N5 N4 Cu3 -175.3(6) . . . . ? Cu2 N5 N4 Cu3 2.9(8) . . . . ? O8 Cu3 N4 C3 -7.5(9) . . . . ? N2 Cu3 N4 C3 99.2(18) . . . . ? O7 Cu3 N4 C3 166.0(8) . . . . ? O1 Cu3 N4 C3 -101.8(8) . . . . ? O8 Cu3 N4 N5 168.5(6) . . . . ? N2 Cu3 N4 N5 -84.7(17) . . . . ? O7 Cu3 N4 N5 -17.9(6) . . . . ? O1 Cu3 N4 N5 74.3(6) . . . . ? C2 N2 N1 C1 0.4(9) . . . . ? Cu3 N2 N1 C1 -173.9(6) . . . . ? C2 N2 N1 Cu1 175.4(5) . . . . ? Cu3 N2 N1 Cu1 1.1(8) . . . . ? O5 Cu1 N1 C1 -31.3(9) . . . . ? N7 Cu1 N1 C1 87(2) . . . . ? O7 Cu1 N1 C1 155.0(9) . . . . ? O3 Cu1 N1 C1 -116.5(8) . . . . ? O30 Cu1 N1 C1 55.7(9) . . . . ? O30' Cu1 N1 C1 63.0(10) . . . . ? O5 Cu1 N1 N2 155.0(6) . . . . ? N7 Cu1 N1 N2 -87(2) . . . . ? O7 Cu1 N1 N2 -18.8(6) . . . . ? O3 Cu1 N1 N2 69.7(6) . . . . ? O30 Cu1 N1 N2 -118.0(7) . . . . ? O30' Cu1 N1 N2 -110.8(8) . . . . ? C5 N8 N7 C6 -0.1(9) . . . . ? Cu2 N8 N7 C6 171.1(6) . . . . ? C5 N8 N7 Cu1 -176.9(5) . . . . ? Cu2 N8 N7 Cu1 -5.6(8) . . . . ? O5 Cu1 N7 C6 28.6(8) . . . . ? N1 Cu1 N7 C6 -90(2) . . . . ? O7 Cu1 N7 C6 -157.5(8) . . . . ? O3 Cu1 N7 C6 113.9(8) . . . . ? O30 Cu1 N7 C6 -58.5(9) . . . . ? O30' Cu1 N7 C6 -65.3(10) . . . . ? O5 Cu1 N7 N8 -155.6(6) . . . . ? N1 Cu1 N7 N8 86(2) . . . . ? O7 Cu1 N7 N8 18.2(6) . . . . ? O3 Cu1 N7 N8 -70.4(6) . . . . ? O30 Cu1 N7 N8 117.2(7) . . . . ? O30' Cu1 N7 N8 110.4(8) . . . . ? N1 N2 C2 N3 -1.2(9) . . . . ? Cu3 N2 C2 N3 172.3(6) . . . . ? C1 N3 C2 N2 1.4(10) . . . . ? C7 N3 C2 N2 -178.4(8) . . . . ? N8 N7 C6 N9 0.1(10) . . . . ? Cu1 N7 C6 N9 176.2(6) . . . . ? C5 N9 C6 N7 0.0(10) . . . . ? C9 N9 C6 N7 -176.6(8) . . . . ? N4 N5 C4 N6 -4.5(9) . . . . ? Cu2 N5 C4 N6 177.6(6) . . . . ? C3 N6 C4 N5 5.7(11) . . . . ? C14 N6 C4 N5 -178.6(9) . . . . ? N2 N1 C1 N3 0.4(10) . . . . ? Cu1 N1 C1 N3 -173.8(6) . . . . ? C2 N3 C1 N1 -1.2(11) . . . . ? C7 N3 C1 N1 178.7(8) . . . . ? N5 N4 C3 N6 2.0(10) . . . . ? Cu3 N4 C3 N6 178.4(7) . . . . ? C4 N6 C3 N4 -4.6(11) . . . . ? C14 N6 C3 N4 179.8(10) . . . . ? C6 N9 C5 N8 -0.1(10) . . . . ? C9 N9 C5 N8 176.4(8) . . . . ? N7 N8 C5 N9 0.1(9) . . . . ? Cu2 N8 C5 N9 -169.8(6) . . . . ? O4 S4 O2 Cu2 4.3(7) . . . 5_665 ? O3 S4 O2 Cu2 -117.5(5) . . . 5_665 ? O1 S4 O2 Cu2 123.8(5) . . . 5_665 ? O4 S4 O1 Cu3 178.4(4) . . . . ? O3 S4 O1 Cu3 -56.8(5) . . . . ? O2 S4 O1 Cu3 59.8(5) . . . . ? O8 Cu3 O1 S4 179.7(4) . . . . ? N2 Cu3 O1 S4 89.5(5) . . . . ? N4 Cu3 O1 S4 -86.8(5) . . . . ? O7 Cu3 O1 S4 1.6(4) . . . . ? O4 S4 O3 Cu1 176.2(4) . . . . ? O1 S4 O3 Cu1 52.6(5) . . . . ? O2 S4 O3 Cu1 -64.5(5) . . . . ? O5 Cu1 O3 S4 -172.9(4) . . . . ? N7 Cu1 O3 S4 94.8(4) . . . . ? N1 Cu1 O3 S4 -82.0(4) . . . . ? O7 Cu1 O3 S4 6.1(4) . . . . ? O30 Cu1 O3 S4 -165(3) . . . . ? O30' Cu1 O3 S4 102(6) . . . . ? C5 N9 C9 C10 -103.4(10) . . . . ? C6 N9 C9 C10 72.4(12) . . . . ? N9 C9 C10 C10 -117.8(6) . . . 4 ? C4 N6 C14 C12 90.1(13) . . . . ? C3 N6 C14 C12 -95.3(13) . . . . ? N5 Cu2 O7 Cu1 -159.2(3) . . . . ? O2 Cu2 O7 Cu1 -67.0(13) 5_665 . . . ? N8 Cu2 O7 Cu1 22.6(3) . . . . ? O10 Cu2 O7 Cu1 111.2(4) . . . . ? N5 Cu2 O7 Cu3 -25.4(3) . . . . ? O2 Cu2 O7 Cu3 66.7(13) 5_665 . . . ? N8 Cu2 O7 Cu3 156.4(3) . . . . ? O10 Cu2 O7 Cu3 -115.1(4) . . . . ? O5 Cu1 O7 Cu2 77(2) . . . . ? N7 Cu1 O7 Cu2 -24.5(3) . . . . ? N1 Cu1 O7 Cu2 163.1(3) . . . . ? O3 Cu1 O7 Cu2 67.3(3) . . . . ? O30 Cu1 O7 Cu2 -114.0(5) . . . . ? O30' Cu1 O7 Cu2 -106.6(7) . . . . ? O5 Cu1 O7 Cu3 -57(2) . . . . ? N7 Cu1 O7 Cu3 -158.2(3) . . . . ? N1 Cu1 O7 Cu3 29.3(3) . . . . ? O3 Cu1 O7 Cu3 -66.5(3) . . . . ? O30 Cu1 O7 Cu3 112.3(5) . . . . ? O30' Cu1 O7 Cu3 119.7(7) . . . . ? O8 Cu3 O7 Cu2 129(2) . . . . ? N2 Cu3 O7 Cu2 -163.2(3) . . . . ? N4 Cu3 O7 Cu2 26.3(3) . . . . ? O1 Cu3 O7 Cu2 -68.7(3) . . . . ? O8 Cu3 O7 Cu1 -97(2) . . . . ? N2 Cu3 O7 Cu1 -28.9(3) . . . . ? N4 Cu3 O7 Cu1 160.6(3) . . . . ? O1 Cu3 O7 Cu1 65.5(3) . . . . ? N6 C14 C12 C12 176.3(8) . . . 4_554 ? O9 S1 O8 Cu3 156.6(6) . . . . ? O9 S1 O8 Cu3 32.0(8) 2_565 . . . ? O8 S1 O8 Cu3 -85.0(7) 2_565 . . . ? N2 Cu3 O8 S1 122.4(7) . . . . ? N4 Cu3 O8 S1 -67.5(7) . . . . ? O7 Cu3 O8 S1 -169.5(18) . . . . ? O1 Cu3 O8 S1 27.8(7) . . . . ? C8 C8 C7 N3 117.0(6) 4 . . . ? C2 N3 C7 C8 108.9(10) . . . . ? C1 N3 C7 C8 -70.9(12) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 23.39 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 3.748 _refine_diff_density_min -0.984 _refine_diff_density_rms 0.198 # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 -0.001 -0.019 -0.009 3409.0 1037.5 _platon_squeeze_details ; ? ;