# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cutda-11 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H20 Cu N2 O4 S, 0.5(C6 H18 N2), N O3, H2 O' _chemical_formula_sum 'C13 H31 Cu N4 O8 S' _chemical_formula_weight 467.01 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall -P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6003(4) _cell_length_b 31.6173(18) _cell_length_c 7.5682(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.671(4) _cell_angle_gamma 90.00 _cell_volume 2028.69(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4075 _cell_measurement_theta_min 3.0078 _cell_measurement_theta_max 29.2343 _exptl_crystal_description rectangular _exptl_crystal_colour blue _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.526 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984.0 _exptl_absorpt_coefficient_mu 1.226 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.87636 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'CrysAlisPro, Agilent Technologies' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0938 _diffrn_reflns_number 17609 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 29.15 _reflns_number_total 4848 _reflns_number_gt 3956 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlisPro, Agilent Technologies' _computing_cell_refinement 'CrysAlisPro, Agilent Technologies' _computing_data_reduction 'CrysAlisPro, Agilent Technologies' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 ver2.02' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0288P)^2^+1.5719P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4848 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.0912 _refine_ls_wR_factor_gt 0.0846 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _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 0.67585(3) 0.140251(9) 0.85338(4) 0.02582(9) Uani 1 1 d . . . S1 S 0.76768(7) 0.18939(2) 0.60386(8) 0.03195(15) Uani 1 1 d . . . O3 O 0.8348(2) 0.10336(6) 0.7802(2) 0.0354(4) Uani 1 1 d . . . O1 O 0.8409(2) 0.17189(6) 1.0113(2) 0.0377(4) Uani 1 1 d . . . N4 N 0.0404(2) 0.04125(7) 0.1845(3) 0.0287(4) Uani 1 1 d . . . O4 O 1.0107(2) 0.08326(6) 0.6170(3) 0.0442(5) Uani 1 1 d . . . O2 O 1.0620(2) 0.20906(7) 1.0567(3) 0.0458(5) Uani 1 1 d . . . O8 O 0.1902(3) 0.21021(10) 0.4392(4) 0.0616(7) Uani 1 1 d . . . N1 N 0.5025(2) 0.17468(7) 0.9441(3) 0.0329(5) Uani 1 1 d . . . O5 O 0.7125(3) 0.08221(8) 0.1487(4) 0.0702(7) Uani 1 1 d . . . N3 N 0.6514(3) 0.05153(8) 0.2143(3) 0.0391(5) Uani 1 1 d . . . C13 C 0.1376(3) 0.01805(9) 0.3338(3) 0.0381(6) Uani 1 1 d . . . H13A H 0.2453 0.0173 0.3150 0.057 Uiso 1 1 calc R . . H13B H 0.0987 -0.0103 0.3381 0.057 Uiso 1 1 calc R . . H13C H 0.1319 0.0321 0.4449 0.057 Uiso 1 1 calc R . . N2 N 0.4981(2) 0.10328(7) 0.7286(3) 0.0327(5) Uani 1 1 d . . . O7 O 0.5079(2) 0.05022(8) 0.2153(3) 0.0615(6) Uani 1 1 d . . . O6 O 0.7385(3) 0.02240(8) 0.2752(4) 0.0733(8) Uani 1 1 d . . . C1 C 0.9403(3) 0.19627(9) 0.9607(3) 0.0321(6) Uani 1 1 d . . . C11 C 0.0406(3) 0.02127(9) 0.0065(3) 0.0388(6) Uani 1 1 d . . . H11A H 0.1486 0.0177 -0.0126 0.047 Uiso 1 1 calc R . . H11B H -0.0127 0.0397 -0.0867 0.047 Uiso 1 1 calc R . . C3 C 0.8829(3) 0.14722(8) 0.5321(3) 0.0354(6) Uani 1 1 d . . . H3A H 0.8310 0.1380 0.4147 0.042 Uiso 1 1 calc R . . H3B H 0.9846 0.1587 0.5178 0.042 Uiso 1 1 calc R . . C12 C 0.0914(3) 0.08600(8) 0.1819(4) 0.0381(6) Uani 1 1 d . . . H12A H 0.0858 0.0989 0.2955 0.057 Uiso 1 1 calc R . . H12B H 0.0234 0.1009 0.0888 0.057 Uiso 1 1 calc R . . H12C H 0.1979 0.0872 0.1596 0.057 Uiso 1 1 calc R . . C5 C 0.3479(3) 0.15590(11) 0.8587(4) 0.0504(8) Uani 1 1 d . . . H5A H 0.2697 0.1604 0.9354 0.060 Uiso 1 1 calc R . . H5B H 0.3113 0.1697 0.7447 0.060 Uiso 1 1 calc R . . C2 C 0.9118(3) 0.21444(9) 0.7713(4) 0.0399(6) Uani 1 1 d . . . H2A H 1.0118 0.2142 0.7280 0.048 Uiso 1 1 calc R . . H2B H 0.8812 0.2438 0.7794 0.048 Uiso 1 1 calc R . . C6 C 0.3677(3) 0.10980(11) 0.8301(4) 0.0520(8) Uani 1 1 d . . . H6A H 0.3910 0.0954 0.9447 0.062 Uiso 1 1 calc R . . H6B H 0.2709 0.0981 0.7639 0.062 Uiso 1 1 calc R . . C4 C 0.9120(3) 0.10838(8) 0.6523(3) 0.0287(5) Uani 1 1 d . . . C7 C 0.5052(4) 0.21947(10) 0.8942(5) 0.0571(9) Uani 1 1 d . . . H7A H 0.4203 0.2341 0.9359 0.086 Uiso 1 1 calc R . . H7B H 0.4931 0.2219 0.7662 0.086 Uiso 1 1 calc R . . H7C H 0.6039 0.2318 0.9479 0.086 Uiso 1 1 calc R . . C9 C 0.4536(4) 0.11632(12) 0.5401(4) 0.0560(9) Uani 1 1 d . . . H9A H 0.3603 0.1014 0.4866 0.084 Uiso 1 1 calc R . . H9B H 0.5381 0.1099 0.4761 0.084 Uiso 1 1 calc R . . H9C H 0.4334 0.1462 0.5345 0.084 Uiso 1 1 calc R . . C8 C 0.5197(4) 0.17134(12) 1.1408(4) 0.0566(9) Uani 1 1 d . . . H8A H 0.6191 0.1832 1.1948 0.085 Uiso 1 1 calc R . . H8B H 0.5158 0.1421 1.1743 0.085 Uiso 1 1 calc R . . H8C H 0.4356 0.1865 1.1813 0.085 Uiso 1 1 calc R . . C10 C 0.5336(4) 0.05726(10) 0.7302(5) 0.0601(9) Uani 1 1 d . . . H10A H 0.4393 0.0419 0.6840 0.090 Uiso 1 1 calc R . . H10B H 0.5722 0.0483 0.8509 0.090 Uiso 1 1 calc R . . H10C H 0.6123 0.0518 0.6569 0.090 Uiso 1 1 calc R . . H8WB H 0.149(5) 0.2050(16) 0.334(6) 0.103(18) Uiso 1 1 d . . . H8WA H 0.152(6) 0.2362(19) 0.468(7) 0.14(2) Uiso 1 1 d . . . H01 H -0.050(4) 0.0409(10) 0.200(4) 0.042(9) Uiso 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 0.02177(14) 0.02755(17) 0.02788(15) -0.00127(12) 0.00339(10) 0.00157(12) S1 0.0362(3) 0.0271(3) 0.0315(3) 0.0033(3) 0.0027(2) 0.0041(3) O3 0.0344(9) 0.0345(11) 0.0401(10) 0.0096(8) 0.0144(8) 0.0107(8) O1 0.0344(10) 0.0429(12) 0.0336(9) 0.0012(8) -0.0002(7) -0.0083(8) N4 0.0249(11) 0.0285(12) 0.0324(11) -0.0020(9) 0.0035(8) 0.0003(9) O4 0.0411(11) 0.0399(12) 0.0554(12) -0.0014(9) 0.0188(9) 0.0127(9) O2 0.0309(10) 0.0567(14) 0.0472(11) -0.0117(10) -0.0007(8) -0.0085(9) O8 0.0559(15) 0.0648(19) 0.0623(17) 0.0194(14) 0.0042(12) 0.0116(13) N1 0.0342(11) 0.0330(13) 0.0323(11) -0.0014(9) 0.0076(9) 0.0077(9) O5 0.0514(14) 0.0599(17) 0.0969(19) 0.0250(14) 0.0059(13) -0.0093(12) N3 0.0343(12) 0.0441(15) 0.0394(12) -0.0037(11) 0.0074(9) 0.0009(11) C13 0.0467(16) 0.0357(16) 0.0303(13) 0.0025(11) 0.0022(11) 0.0029(12) N2 0.0298(11) 0.0316(13) 0.0355(11) -0.0037(9) 0.0017(8) -0.0029(9) O7 0.0346(11) 0.0733(18) 0.0803(16) 0.0049(13) 0.0205(11) 0.0069(11) O6 0.0420(13) 0.0638(17) 0.113(2) 0.0351(15) 0.0102(13) 0.0090(12) C1 0.0291(12) 0.0317(15) 0.0355(13) -0.0082(11) 0.0054(10) 0.0029(10) C11 0.0547(17) 0.0343(16) 0.0263(13) 0.0010(11) 0.0035(11) -0.0076(13) C3 0.0425(15) 0.0320(15) 0.0339(13) -0.0014(11) 0.0130(11) 0.0021(11) C12 0.0419(15) 0.0290(15) 0.0410(15) -0.0015(12) 0.0001(11) -0.0014(12) C5 0.0272(14) 0.065(2) 0.0596(19) -0.0036(16) 0.0087(12) 0.0111(14) C2 0.0443(16) 0.0320(16) 0.0428(15) -0.0011(12) 0.0053(12) -0.0083(12) C6 0.0294(14) 0.063(2) 0.065(2) -0.0073(17) 0.0121(13) -0.0108(14) C4 0.0248(12) 0.0268(13) 0.0337(13) -0.0029(10) 0.0031(9) 0.0002(10) C7 0.068(2) 0.0361(19) 0.072(2) 0.0002(16) 0.0233(17) 0.0172(16) C9 0.060(2) 0.065(2) 0.0363(16) -0.0039(15) -0.0103(14) -0.0113(17) C8 0.064(2) 0.072(3) 0.0359(16) -0.0028(16) 0.0152(14) 0.0211(18) C10 0.066(2) 0.0354(19) 0.075(2) -0.0070(16) 0.0008(17) -0.0086(16) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O3 1.9470(17) . ? Cu1 O1 1.9680(17) . ? Cu1 N2 2.027(2) . ? Cu1 N1 2.055(2) . ? Cu1 S1 2.6655(7) . ? S1 C3 1.799(3) . ? S1 C2 1.801(3) . ? O3 C4 1.272(3) . ? O1 C1 1.258(3) . ? N4 C13 1.482(3) . ? N4 C12 1.482(3) . ? N4 C11 1.488(3) . ? N4 H01 0.80(3) . ? O4 C4 1.224(3) . ? O2 C1 1.238(3) . ? O8 H8WB 0.83(5) . ? O8 H8WA 0.93(6) . ? N1 C7 1.467(4) . ? N1 C8 1.474(3) . ? N1 C5 1.500(4) . ? O5 N3 1.245(3) . ? N3 O6 1.227(3) . ? N3 O7 1.236(3) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? N2 C9 1.473(3) . ? N2 C6 1.477(3) . ? N2 C10 1.486(4) . ? C1 C2 1.525(4) . ? C11 C11 1.511(5) 3 ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C3 C4 1.524(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C5 C6 1.488(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? 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 O3 Cu1 O1 90.47(8) . . ? O3 Cu1 N2 91.86(8) . . ? O1 Cu1 N2 170.52(8) . . ? O3 Cu1 N1 174.80(8) . . ? O1 Cu1 N1 91.01(8) . . ? N2 Cu1 N1 85.90(9) . . ? O3 Cu1 S1 80.90(5) . . ? O1 Cu1 S1 82.23(5) . . ? N2 Cu1 S1 107.21(6) . . ? N1 Cu1 S1 104.24(6) . . ? C3 S1 C2 100.92(13) . . ? C3 S1 Cu1 91.47(9) . . ? C2 S1 Cu1 90.50(9) . . ? C4 O3 Cu1 128.53(16) . . ? C1 O1 Cu1 125.75(16) . . ? C13 N4 C12 110.6(2) . . ? C13 N4 C11 113.2(2) . . ? C12 N4 C11 110.3(2) . . ? C13 N4 H01 109(2) . . ? C12 N4 H01 108(2) . . ? C11 N4 H01 106(2) . . ? H8WB O8 H8WA 107(4) . . ? C7 N1 C8 109.0(2) . . ? C7 N1 C5 108.8(2) . . ? C8 N1 C5 109.8(2) . . ? C7 N1 Cu1 112.42(17) . . ? C8 N1 Cu1 110.10(17) . . ? C5 N1 Cu1 106.66(16) . . ? O6 N3 O7 121.3(3) . . ? O6 N3 O5 117.6(2) . . ? O7 N3 O5 121.1(3) . . ? N4 C13 H13A 109.5 . . ? N4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C9 N2 C6 111.6(2) . . ? C9 N2 C10 107.6(2) . . ? C6 N2 C10 107.8(2) . . ? C9 N2 Cu1 110.06(18) . . ? C6 N2 Cu1 104.86(17) . . ? C10 N2 Cu1 115.01(17) . . ? O2 C1 O1 124.9(2) . . ? O2 C1 C2 114.5(2) . . ? O1 C1 C2 120.5(2) . . ? N4 C11 C11 111.5(3) . 3 ? N4 C11 H11A 109.3 . . ? C11 C11 H11A 109.3 3 . ? N4 C11 H11B 109.3 . . ? C11 C11 H11B 109.3 3 . ? H11A C11 H11B 108.0 . . ? C4 C3 S1 117.43(17) . . ? C4 C3 H3A 107.9 . . ? S1 C3 H3A 107.9 . . ? C4 C3 H3B 107.9 . . ? S1 C3 H3B 107.9 . . ? H3A C3 H3B 107.2 . . ? N4 C12 H12A 109.5 . . ? N4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C6 C5 N1 109.6(2) . . ? C6 C5 H5A 109.7 . . ? N1 C5 H5A 109.7 . . ? C6 C5 H5B 109.7 . . ? N1 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? C1 C2 S1 118.58(19) . . ? C1 C2 H2A 107.7 . . ? S1 C2 H2A 107.7 . . ? C1 C2 H2B 107.7 . . ? S1 C2 H2B 107.7 . . ? H2A C2 H2B 107.1 . . ? N2 C6 C5 109.1(2) . . ? N2 C6 H6A 109.9 . . ? C5 C6 H6A 109.9 . . ? N2 C6 H6B 109.9 . . ? C5 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? O4 C4 O3 123.7(2) . . ? O4 C4 C3 116.3(2) . . ? O3 C4 C3 120.0(2) . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.886 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.329 _refine_diff_density_min -0.550 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 951794' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_nsrep _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H36 Cu2 N4 O6, 2(N O3), 2(C2 H3 N)' _chemical_formula_sum 'C18 H42 Cu2 N8 O12' _chemical_formula_weight 689.70 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.9414(6) _cell_length_b 20.8386(13) _cell_length_c 9.5765(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.996(6) _cell_angle_gamma 90.00 _cell_volume 1560.73(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1466 _cell_measurement_theta_min 3.0800 _cell_measurement_theta_max 28.9918 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 1.428 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.36294 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. _exptl_special_details ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0938 _diffrn_standards_number 12476 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10992 _diffrn_reflns_av_R_equivalents 0.1110 _diffrn_reflns_av_avetI/netI 0.1585 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 29.00 _reflns_number_total 3593 _reflns_number_gt 1779 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlisPro, Agilent Technologies' _computing_cell_refinement 'CrysAlisPro, Agilent Technologies' _computing_data_reduction 'CrysAlisPro, Agilent Technologies' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 ver2.02' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0278P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3593 _refine_ls_number_parameters 216 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1418 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1225 _refine_ls_wR_factor_gt 0.0964 _refine_ls_goodness_of_fit_ref 0.927 _refine_ls_restrained_S_all 0.927 _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 0.31277(7) -0.07866(2) 0.82911(5) 0.0395(2) Uani 1 1 d . . . O2 O 0.4479(4) 0.07308(13) 1.0681(3) 0.0467(8) Uani 1 1 d . . . O1 O 0.2869(4) 0.00576(13) 0.9180(3) 0.0457(8) Uani 1 1 d . . . C8 C -0.1942(8) -0.1916(3) 0.3527(7) 0.076(2) Uani 1 1 d . . . OW O 0.3676(7) -0.0302(2) 0.6345(4) 0.0864(16) Uani 1 1 d . . . N1 N 0.0585(5) -0.09261(18) 0.7724(4) 0.0523(11) Uani 1 1 d . . . N2 N 0.3437(5) -0.17091(17) 0.7757(4) 0.0453(10) Uani 1 1 d . . . C9 C 0.4247(6) 0.02260(19) 0.9963(4) 0.0361(10) Uani 1 1 d . . . N3 N 0.3046(9) -0.1001(3) 0.2798(8) 0.0749(16) Uani 1 1 d . . . C4 C 0.1794(7) -0.1902(2) 0.6899(5) 0.0588(15) Uani 1 1 d . . . H4A H 0.1708 -0.2366 0.6874 0.071 Uiso 1 1 calc R . . H4B H 0.1730 -0.1749 0.5934 0.071 Uiso 1 1 calc R . . C6 C 0.4836(7) -0.1794(2) 0.6920(5) 0.0709(17) Uani 1 1 d . . . H6A H 0.5895 -0.1647 0.7466 0.106 Uiso 1 1 calc R . . H6B H 0.4580 -0.1551 0.6059 0.106 Uiso 1 1 calc R . . H6C H 0.4936 -0.2240 0.6697 0.106 Uiso 1 1 calc R . . N4 N -0.1841(9) -0.2256(3) 0.4429(6) 0.117(3) Uani 1 1 d . . . C5 C 0.3846(8) -0.2089(2) 0.9079(5) 0.077(2) Uani 1 1 d . . . H5A H 0.2997 -0.2011 0.9660 0.116 Uiso 1 1 calc R . . H5B H 0.4950 -0.1966 0.9584 0.116 Uiso 1 1 calc R . . H5C H 0.3857 -0.2538 0.8848 0.116 Uiso 1 1 calc R . . C7 C -0.2025(9) -0.1485(3) 0.2334(7) 0.118(3) Uani 1 1 d . . . H7A H -0.2047 -0.1730 0.1482 0.177 Uiso 1 1 calc R . . H7B H -0.1040 -0.1210 0.2478 0.177 Uiso 1 1 calc R . . H7C H -0.3042 -0.1229 0.2250 0.177 Uiso 1 1 calc R . . C3 C 0.0369(7) -0.1630(2) 0.7512(5) 0.0684(17) Uani 1 1 d . . . H3A H 0.0327 -0.1835 0.8415 0.082 Uiso 1 1 calc R . . H3B H -0.0703 -0.1716 0.6884 0.082 Uiso 1 1 calc R . . O02 O 0.2037(19) -0.1313(7) 0.3296(18) 0.108(5) Uani 0.50 1 d P A 1 C1 C -0.0095(8) -0.0593(3) 0.6386(6) 0.095(2) Uani 1 1 d . . . H1A H -0.1308 -0.0658 0.6157 0.142 Uiso 1 1 calc R . . H1B H 0.0439 -0.0761 0.5638 0.142 Uiso 1 1 calc R . . H1C H 0.0141 -0.0142 0.6493 0.142 Uiso 1 1 calc R . . C2 C -0.0366(8) -0.0732(3) 0.8834(6) 0.104(3) Uani 1 1 d . . . H2A H -0.0355 -0.0273 0.8913 0.156 Uiso 1 1 calc R . . H2B H 0.0159 -0.0917 0.9722 0.156 Uiso 1 1 calc R . . H2C H -0.1525 -0.0880 0.8596 0.156 Uiso 1 1 calc R . . O03 O 0.336(2) -0.1008(10) 0.1653(15) 0.149(6) Uani 0.50 1 d P A 1 O01 O 0.417(2) -0.0700(6) 0.3699(14) 0.153(6) Uani 0.50 1 d P A 1 003A O 0.400(2) -0.0630(9) 0.257(3) 0.172(7) Uiso 0.50 1 d P A 2 O02A O 0.250(2) -0.1363(6) 0.1809(15) 0.128(5) Uani 0.50 1 d P A 2 O01A O 0.257(3) -0.0952(11) 0.3788(17) 0.163(9) Uani 0.50 1 d P A 2 HW1 H 0.441(7) 0.003(2) 0.640(5) 0.162(6) Uiso 1 1 d . . . HW2 H 0.381(9) -0.054(3) 0.567(6) 0.11(3) Uiso 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 0.0366(4) 0.0387(3) 0.0425(3) -0.0070(3) 0.0051(2) -0.0041(3) O2 0.036(2) 0.0421(17) 0.060(2) -0.0182(16) 0.0023(15) -0.0001(15) O1 0.029(2) 0.0451(17) 0.060(2) -0.0164(15) -0.0003(14) 0.0009(15) C8 0.076(5) 0.068(4) 0.075(5) -0.010(3) -0.010(4) -0.002(3) OW 0.132(5) 0.077(3) 0.057(3) -0.004(2) 0.034(3) -0.047(3) N1 0.037(3) 0.057(3) 0.063(3) -0.023(2) 0.011(2) -0.006(2) N2 0.046(3) 0.044(2) 0.043(2) -0.0045(19) 0.0001(18) -0.004(2) C9 0.032(3) 0.037(2) 0.041(3) -0.002(2) 0.010(2) 0.004(2) N3 0.086(5) 0.058(3) 0.082(5) -0.006(4) 0.015(4) -0.021(4) C4 0.057(4) 0.047(3) 0.069(4) -0.017(3) 0.000(3) -0.007(3) C6 0.063(5) 0.069(4) 0.079(4) -0.022(3) 0.009(3) 0.007(3) N4 0.148(7) 0.101(5) 0.088(5) 0.001(4) -0.018(4) -0.022(4) C5 0.109(6) 0.051(3) 0.064(4) 0.006(3) -0.004(3) 0.008(3) C7 0.114(8) 0.119(6) 0.110(6) 0.022(5) -0.010(5) 0.005(5) C3 0.057(4) 0.076(4) 0.072(4) -0.015(3) 0.009(3) -0.028(3) O02 0.083(9) 0.116(11) 0.131(15) 0.038(9) 0.036(9) -0.035(8) C1 0.064(5) 0.101(4) 0.104(5) 0.011(4) -0.027(4) 0.006(4) C2 0.050(5) 0.156(6) 0.116(5) -0.077(5) 0.042(4) -0.027(4) O03 0.198(18) 0.192(17) 0.073(8) -0.013(10) 0.066(9) -0.048(12) O01 0.175(15) 0.187(11) 0.103(9) -0.030(8) 0.038(8) -0.149(11) O02A 0.195(18) 0.102(9) 0.088(10) -0.040(8) 0.028(9) -0.038(8) O01A 0.20(2) 0.23(2) 0.065(8) -0.047(11) 0.044(10) -0.015(16) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.980(3) . ? Cu1 O2 1.986(3) 3_657 ? Cu1 N2 2.015(4) . ? Cu1 N1 2.019(4) . ? Cu1 OW 2.228(4) . ? O2 C9 1.253(4) . ? O2 Cu1 1.986(3) 3_657 ? O1 C9 1.264(5) . ? C8 N4 1.110(7) . ? C8 C7 1.445(8) . ? OW HW1 0.91(5) . ? OW HW2 0.83(6) . ? N1 C2 1.464(6) . ? N1 C1 1.475(6) . ? N1 C3 1.487(6) . ? N2 C4 1.473(6) . ? N2 C5 1.480(5) . ? N2 C6 1.489(6) . ? C9 C9 1.515(8) 3_657 ? N3 O01A 1.087(19) . ? N3 003A 1.131(18) . ? N3 O03 1.166(14) . ? N3 O02 1.195(16) . ? N3 O02A 1.230(13) . ? N3 O01 1.290(12) . ? C4 C3 1.475(7) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O2 84.08(11) . 3_657 ? O1 Cu1 N2 169.33(14) . . ? O2 Cu1 N2 91.90(13) 3_657 . ? O1 Cu1 N1 94.01(14) . . ? O2 Cu1 N1 165.47(15) 3_657 . ? N2 Cu1 N1 87.41(16) . . ? O1 Cu1 OW 90.38(17) . . ? O2 Cu1 OW 94.54(16) 3_657 . ? N2 Cu1 OW 99.80(18) . . ? N1 Cu1 OW 99.89(18) . . ? C9 O2 Cu1 111.0(3) . 3_657 ? C9 O1 Cu1 111.0(3) . . ? N4 C8 C7 177.9(8) . . ? Cu1 OW HW1 121(3) . . ? Cu1 OW HW2 117(4) . . ? HW1 OW HW2 109(5) . . ? C2 N1 C1 110.1(5) . . ? C2 N1 C3 108.0(5) . . ? C1 N1 C3 109.3(4) . . ? C2 N1 Cu1 112.5(3) . . ? C1 N1 Cu1 111.3(3) . . ? C3 N1 Cu1 105.4(3) . . ? C4 N2 C5 111.9(4) . . ? C4 N2 C6 109.8(4) . . ? C5 N2 C6 108.8(4) . . ? C4 N2 Cu1 105.4(3) . . ? C5 N2 Cu1 108.2(3) . . ? C6 N2 Cu1 112.7(3) . . ? O2 C9 O1 126.1(4) . . ? O2 C9 C9 117.1(5) . 3_657 ? O1 C9 C9 116.8(5) . 3_657 ? O01A N3 003A 117.1(18) . . ? O01A N3 O03 170.7(16) . . ? 003A N3 O03 64.2(12) . . ? O01A N3 O02 48.8(11) . . ? 003A N3 O02 165.8(17) . . ? O03 N3 O02 129.6(14) . . ? O01A N3 O02A 126.7(17) . . ? 003A N3 O02A 115.5(16) . . ? O03 N3 O02A 51.2(9) . . ? O02 N3 O02A 78.5(11) . . ? O01A N3 O01 71.2(13) . . ? 003A N3 O01 52.4(10) . . ? O03 N3 O01 113.5(13) . . ? O02 N3 O01 115.5(12) . . ? O02A N3 O01 157.5(14) . . ? N2 C4 C3 109.9(4) . . ? N2 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? N2 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C5 H5A 109.5 . . ? N2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C3 N1 110.8(4) . . ? C4 C3 H3A 109.5 . . ? N1 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.866 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.572 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.101 _database_code_depnum_ccdc_archive 'CCDC 951795'