# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Hongwei Hou' _publ_contact_author_email houhongw@zzu.edu.cn _publ_author_name 'Hongwei Hou' data_complex-1 _database_code_depnum_ccdc_archive 'CCDC 869685' #TrackingRef '- Revised CIF for 1 and 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H49 Cu4 N17 O19 S2' _chemical_formula_sum 'C28 H49 Cu4 N17 O19 S2' _chemical_formula_weight 1246.12 _symmetry_space_group_name_Hall '-R 3' 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 trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 41.3528(18) _cell_length_b 41.3528(18) _cell_length_c 18.2765(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 27067(3) _cell_formula_units_Z 18 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.25 _cell_measurement_theta_max 28.25 _exptl_crystal_description rhombus _exptl_crystal_colour green _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 11448 _exptl_absorpt_coefficient_mu 1.535 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.590 _exptl_absorpt_correction_T_max 0.661 _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 SMART APEX CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 58156 _diffrn_reflns_av_R_equivalents 0.0619 _diffrn_reflns_av_sigmaI/netI 0.0817 _diffrn_reflns_limit_h_min -52 _diffrn_reflns_limit_h_max 54 _diffrn_reflns_limit_k_min -54 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 28.25 _reflns_number_total 14834 _reflns_number_gt 7871 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0733P)^2^+61.0308P] 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 14834 _refine_ls_number_parameters 564 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.1004 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1649 _refine_ls_wR_factor_gt 0.1523 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 1.001 _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 0.422512(14) 0.127703(14) 0.42765(3) 0.03565(14) Uani 1 1 d . . . Cu2 Cu 0.408526(15) 0.028816(15) 0.49975(3) 0.03887(15) Uani 1 1 d . . . Cu3 Cu 0.413739(16) 0.226419(15) 0.39486(3) 0.04015(15) Uani 1 1 d . . . Cu4 Cu 0.408245(16) -0.074350(15) 0.52230(3) 0.04179(15) Uani 1 1 d . . . N1 N 0.45036(11) -0.08155(11) 0.4794(2) 0.0457(9) Uani 1 1 d . . . N2 N 0.43882(10) -0.02562(10) 0.4746(2) 0.0406(9) Uani 1 1 d . . . N3 N 0.43618(10) 0.00508(10) 0.46152(19) 0.0392(8) Uani 1 1 d . . . N4 N 0.48336(10) 0.00913(10) 0.3924(2) 0.0421(9) Uani 1 1 d . . . N5 N 0.44373(9) 0.06901(9) 0.42756(18) 0.0334(8) Uani 1 1 d . . . N6 N 0.45073(9) 0.10263(9) 0.39928(18) 0.0336(8) Uani 1 1 d . . . N8 N 0.38306(13) 0.24014(12) 0.4644(2) 0.0586(12) Uani 1 1 d . . . N9 N 0.39657(11) 0.18545(10) 0.4651(2) 0.0454(9) Uani 1 1 d . . . N10 N 0.39834(11) 0.15376(10) 0.47479(19) 0.0400(9) Uani 1 1 d . . . N11 N 0.36188(15) 0.15547(13) 0.5641(2) 0.0694(14) Uani 1 1 d . . . N12 N 0.39496(11) 0.09204(10) 0.5111(2) 0.0438(9) Uani 1 1 d . . . N13 N 0.38862(12) 0.05881(11) 0.5380(2) 0.0499(10) Uani 1 1 d . . . N14 N 0.35573(16) 0.07774(14) 0.6052(3) 0.0835(18) Uani 1 1 d . . . N15 N 0.5251(2) 0.2901(3) 0.4913(6) 0.170(4) Uani 1 1 d D . . N16 N 0.3213(4) -0.1410(5) 0.3610(7) 0.318(9) Uani 1 1 d DU . . O1 O 0.42660(9) 0.20013(9) 0.32078(16) 0.0464(8) Uani 1 1 d . . . O2 O 0.49369(9) 0.22954(9) 0.31060(19) 0.0582(9) Uani 1 1 d . . . O3 O 0.46095(8) 0.17358(8) 0.37815(16) 0.0436(7) Uani 1 1 d . . . O5 O 0.33700(9) -0.04276(10) 0.63298(18) 0.0557(9) Uani 1 1 d . . . O6 O 0.37018(8) -0.06225(8) 0.55402(17) 0.0463(8) Uani 1 1 d . . . O7 O 0.39917(9) 0.00220(8) 0.59299(16) 0.0457(8) Uani 1 1 d . . . O9 O 0.36222(11) 0.00066(12) 0.4161(2) 0.0632(11) Uani 1 1 d . . . O10 O 0.46760(13) 0.26689(12) 0.4446(2) 0.0808(13) Uani 1 1 d . . . O11 O 0.37410(14) -0.10413(13) 0.4216(2) 0.0844(13) Uani 1 1 d . . . O12 O 0.5453(5) 0.3131(4) 0.2447(9) 0.417(11) Uani 1 1 d . . . O13 O 0.4201(5) 0.0464(4) 0.7768(8) 0.399(10) Uani 1 1 d . . . O14 O 0.4313(6) 0.9299(6) 0.2461(11) 0.490(13) Uani 1 1 d . . . O15 O 0.5288(4) 0.8258(4) 0.3898(11) 0.411(11) Uani 1 1 d . . . S2 S 0.37402(3) -0.03716(3) 0.61581(6) 0.0381(3) Uani 1 1 d . . . S1 S 0.45917(3) 0.19469(3) 0.31442(6) 0.0381(3) Uani 1 1 d . . . C1 C 0.45462(16) -0.11113(14) 0.4857(3) 0.0560(13) Uani 1 1 d . . . H1 H 0.4374 -0.1313 0.5135 0.067 Uiso 1 1 calc R . . C2 C 0.48362(17) -0.11335(16) 0.4525(3) 0.0618(15) Uani 1 1 d . . . H2 H 0.4862 -0.1343 0.4586 0.074 Uiso 1 1 calc R . . C3 C 0.50851(16) -0.08356(17) 0.4101(3) 0.0663(15) Uani 1 1 d . . . H3 H 0.5281 -0.0845 0.3870 0.080 Uiso 1 1 calc R . . C4 C 0.50476(14) -0.05271(15) 0.4019(3) 0.0531(12) Uani 1 1 d . . . H4 H 0.5215 -0.0324 0.3738 0.064 Uiso 1 1 calc R . . C5 C 0.47505(13) -0.05294(13) 0.4368(2) 0.0433(11) Uani 1 1 d . . . C6 C 0.46661(12) -0.02237(12) 0.4331(2) 0.0397(10) Uani 1 1 d . . . C7 C 0.46352(12) 0.02492(12) 0.4127(2) 0.0370(10) Uani 1 1 d . . . C8 C 0.46632(11) 0.06032(11) 0.3930(2) 0.0336(9) Uani 1 1 d . . . C10 C 0.3780(2) 0.27004(16) 0.4602(3) 0.080(2) Uani 1 1 d . . . H10 H 0.3881 0.2862 0.4206 0.096 Uiso 1 1 calc R . . C11 C 0.3586(3) 0.2773(2) 0.5121(4) 0.119(3) Uani 1 1 d . . . H11 H 0.3562 0.2985 0.5086 0.143 Uiso 1 1 calc R . . C12 C 0.3428(3) 0.2532(2) 0.5687(4) 0.138(4) Uani 1 1 d . . . H12 H 0.3288 0.2572 0.6035 0.165 Uiso 1 1 calc R . . C13 C 0.3478(2) 0.2224(2) 0.5745(4) 0.106(3) Uani 1 1 d . . . H13 H 0.3376 0.2058 0.6133 0.127 Uiso 1 1 calc R . . C14 C 0.36834(18) 0.21721(16) 0.5210(3) 0.0672(17) Uani 1 1 d . . . C15 C 0.37472(16) 0.18498(14) 0.5191(3) 0.0548(13) Uani 1 1 d . . . C16 C 0.37718(15) 0.13715(13) 0.5331(3) 0.0509(13) Uani 1 1 d . . . C17 C 0.37496(15) 0.10214(14) 0.5530(3) 0.0543(13) Uani 1 1 d . . . C18 C 0.36525(19) 0.05142(17) 0.5938(3) 0.079(2) Uani 1 1 d . . . H18 H 0.3563 0.0300 0.6223 0.095 Uiso 1 1 calc R . . C20 C 0.4907(3) 0.2630(3) 0.4676(5) 0.128(3) Uani 1 1 d . . . H20 H 0.4859 0.2386 0.4709 0.153 Uiso 1 1 calc R . . C21 C 0.5365(4) 0.3289(3) 0.4880(10) 0.258(9) Uani 1 1 d D . . H21A H 0.5209 0.3311 0.4519 0.387 Uiso 1 1 d R . . H21B H 0.5621 0.3425 0.4723 0.387 Uiso 1 1 d R . . H21C H 0.5340 0.3388 0.5337 0.387 Uiso 1 1 d R . . C22 C 0.5525(5) 0.2808(5) 0.5253(13) 0.375(16) Uani 1 1 d D . . H22A H 0.5492 0.2809 0.5773 0.562 Uiso 1 1 d R . . H22B H 0.5774 0.2999 0.5126 0.562 Uiso 1 1 d R . . H22C H 0.5488 0.2569 0.5105 0.562 Uiso 1 1 d R . . C23 C 0.3401(4) -0.1242(4) 0.4193(6) 0.169(5) Uani 1 1 d U . . H23 H 0.3268 -0.1276 0.4625 0.203 Uiso 1 1 calc R . . C24 C 0.2795(5) -0.1675(8) 0.3669(13) 0.50(2) Uani 1 1 d DU . . H24A H 0.2767 -0.1891 0.3417 0.745 Uiso 1 1 d R . . H24B H 0.2636 -0.1596 0.3448 0.745 Uiso 1 1 d R . . H24C H 0.2727 -0.1736 0.4174 0.745 Uiso 1 1 d R . . C25 C 0.3412(7) -0.1226(9) 0.2879(9) 0.58(3) Uani 1 1 d DU . . H25A H 0.3427 -0.1404 0.2565 0.871 Uiso 1 1 d R . . H25B H 0.3659 -0.1036 0.3016 0.871 Uiso 1 1 d R . . H25C H 0.3290 -0.1113 0.2625 0.871 Uiso 1 1 d R . . O4 O 0.45362(8) 0.17252(9) 0.24696(17) 0.0478(8) Uani 1 1 d . . . O8 O 0.39168(9) -0.04405(9) 0.67808(17) 0.0506(8) Uani 1 1 d . . . N7 N 0.48782(9) 0.08605(10) 0.34356(18) 0.0354(8) Uani 1 1 d . . . C9 C 0.47695(12) 0.11174(12) 0.3495(2) 0.0380(10) Uani 1 1 d . . . H9 H 0.4868 0.1334 0.3216 0.046 Uiso 1 1 calc R . . C19 C 0.3588(2) -0.0300(2) 0.3738(4) 0.105(3) Uani 1 1 d . . . H19A H 0.3799 -0.0214 0.3416 0.157 Uiso 1 1 calc R . . H19B H 0.3363 -0.0405 0.3454 0.157 Uiso 1 1 calc R . . H19C H 0.3580 -0.0488 0.4059 0.157 Uiso 1 1 calc R . . H9A H 0.3675(19) 0.0163(19) 0.392(4) 0.08(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 0.0381(3) 0.0341(3) 0.0376(3) 0.0047(2) 0.0053(2) 0.0202(2) Cu2 0.0426(3) 0.0360(3) 0.0427(3) 0.0091(2) 0.0109(2) 0.0231(3) Cu3 0.0516(3) 0.0369(3) 0.0376(3) 0.0023(2) 0.0012(2) 0.0263(3) Cu4 0.0476(3) 0.0372(3) 0.0444(3) 0.0025(2) 0.0032(3) 0.0240(3) N1 0.058(3) 0.043(2) 0.044(2) 0.0005(18) -0.0022(19) 0.032(2) N2 0.042(2) 0.038(2) 0.048(2) 0.0074(17) 0.0050(17) 0.0248(18) N3 0.045(2) 0.037(2) 0.044(2) 0.0083(16) 0.0081(17) 0.0268(18) N4 0.040(2) 0.044(2) 0.051(2) 0.0023(18) 0.0068(17) 0.0273(18) N5 0.0362(19) 0.0340(19) 0.0335(18) 0.0061(15) 0.0049(15) 0.0201(16) N6 0.0317(18) 0.0301(18) 0.0372(19) 0.0036(15) 0.0032(15) 0.0140(15) N8 0.093(3) 0.048(2) 0.052(3) 0.009(2) 0.019(2) 0.048(3) N9 0.064(3) 0.043(2) 0.040(2) 0.0033(17) 0.0056(19) 0.035(2) N10 0.057(2) 0.034(2) 0.037(2) 0.0035(16) 0.0080(17) 0.0290(19) N11 0.112(4) 0.067(3) 0.059(3) 0.025(2) 0.043(3) 0.067(3) N12 0.052(2) 0.041(2) 0.046(2) 0.0126(17) 0.0144(18) 0.0280(19) N13 0.066(3) 0.047(2) 0.053(2) 0.0198(19) 0.023(2) 0.040(2) N14 0.138(5) 0.077(3) 0.075(3) 0.046(3) 0.065(3) 0.082(4) N15 0.108(6) 0.185(10) 0.220(10) -0.048(8) -0.080(7) 0.075(7) N16 0.227(12) 0.378(18) 0.153(8) -0.038(11) -0.046(9) 0.004(13) O1 0.057(2) 0.055(2) 0.0390(17) -0.0038(15) -0.0018(15) 0.0367(17) O2 0.051(2) 0.0360(18) 0.063(2) 0.0059(16) -0.0042(17) 0.0027(16) O3 0.0348(16) 0.0409(17) 0.0521(19) 0.0110(14) 0.0031(14) 0.0167(14) O5 0.0439(19) 0.066(2) 0.060(2) -0.0043(18) 0.0055(16) 0.0293(18) O6 0.0405(18) 0.0418(18) 0.057(2) -0.0042(15) 0.0020(15) 0.0207(15) O7 0.060(2) 0.0334(16) 0.0425(18) 0.0093(13) 0.0085(15) 0.0230(16) O9 0.060(2) 0.051(2) 0.073(3) 0.007(2) -0.008(2) 0.022(2) O10 0.080(3) 0.072(3) 0.088(3) -0.011(2) -0.043(2) 0.036(2) O11 0.091(3) 0.082(3) 0.076(3) -0.020(2) -0.030(3) 0.040(3) O12 0.358(19) 0.275(15) 0.39(2) 0.051(15) 0.046(16) -0.012(14) O13 0.54(3) 0.326(18) 0.245(13) 0.055(12) -0.011(15) 0.151(18) O14 0.48(3) 0.53(3) 0.35(2) -0.06(2) -0.16(2) 0.17(3) O15 0.223(13) 0.331(17) 0.64(3) 0.072(18) -0.144(16) 0.109(13) S2 0.0388(6) 0.0354(6) 0.0416(6) 0.0070(5) 0.0070(5) 0.0197(5) S1 0.0370(6) 0.0323(6) 0.0422(6) 0.0004(5) -0.0008(5) 0.0151(5) C1 0.077(4) 0.045(3) 0.058(3) 0.003(2) 0.004(3) 0.039(3) C2 0.080(4) 0.058(3) 0.070(4) -0.004(3) -0.002(3) 0.051(3) C3 0.063(4) 0.080(4) 0.076(4) -0.005(3) 0.004(3) 0.051(3) C4 0.053(3) 0.059(3) 0.058(3) 0.004(2) 0.005(2) 0.036(3) C5 0.052(3) 0.051(3) 0.036(2) -0.001(2) -0.001(2) 0.032(2) C6 0.038(2) 0.043(3) 0.042(2) -0.001(2) -0.002(2) 0.022(2) C7 0.034(2) 0.042(2) 0.037(2) 0.0026(19) 0.0041(18) 0.020(2) C8 0.028(2) 0.039(2) 0.035(2) 0.0032(18) -0.0009(17) 0.0168(19) C10 0.140(6) 0.061(4) 0.069(4) 0.019(3) 0.042(4) 0.072(4) C11 0.230(10) 0.115(6) 0.082(5) 0.039(4) 0.076(6) 0.139(7) C12 0.263(12) 0.130(7) 0.102(6) 0.049(5) 0.097(7) 0.159(8) C13 0.187(8) 0.111(6) 0.073(4) 0.031(4) 0.066(5) 0.114(6) C14 0.110(5) 0.065(4) 0.053(3) 0.015(3) 0.033(3) 0.064(4) C15 0.080(4) 0.055(3) 0.049(3) 0.005(2) 0.021(3) 0.048(3) C16 0.076(4) 0.047(3) 0.044(3) 0.014(2) 0.024(3) 0.041(3) C17 0.073(4) 0.053(3) 0.052(3) 0.016(2) 0.025(3) 0.043(3) C18 0.111(5) 0.078(4) 0.078(4) 0.045(3) 0.063(4) 0.068(4) C20 0.139(9) 0.124(8) 0.128(8) -0.049(6) -0.055(7) 0.072(7) C21 0.256(18) 0.082(8) 0.39(2) 0.007(11) -0.103(16) 0.046(10) C22 0.25(2) 0.27(2) 0.64(4) -0.09(2) -0.25(3) 0.162(18) C23 0.187(11) 0.187(12) 0.108(7) -0.040(7) -0.046(8) 0.075(10) C24 0.193(15) 0.65(5) 0.36(3) -0.07(3) -0.088(15) -0.01(2) C25 0.50(3) 0.84(5) 0.110(9) -0.06(2) 0.077(16) 0.11(3) O4 0.0347(17) 0.0514(19) 0.056(2) -0.0135(16) -0.0029(14) 0.0201(15) O8 0.055(2) 0.0436(19) 0.0498(19) 0.0127(15) -0.0017(16) 0.0224(17) N7 0.0354(19) 0.037(2) 0.0353(19) 0.0058(15) 0.0051(15) 0.0193(17) C9 0.035(2) 0.039(2) 0.041(2) 0.0077(19) 0.0076(19) 0.019(2) C19 0.108(6) 0.077(5) 0.117(6) -0.003(5) -0.035(5) 0.037(5) _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 N6 1.979(3) . ? Cu1 O3 1.982(3) . ? Cu1 N10 1.995(3) . ? Cu1 N12 2.029(3) . ? Cu1 O8 2.218(3) 8_544 ? Cu2 N13 1.930(4) . ? Cu2 O7 1.959(3) . ? Cu2 N3 1.970(3) . ? Cu2 N5 2.050(3) . ? Cu2 O9 2.265(4) . ? Cu3 N9 1.955(4) . ? Cu3 O1 1.969(3) . ? Cu3 N7 1.983(3) 17 ? Cu3 N8 2.065(4) . ? Cu3 O10 2.204(4) . ? Cu4 O4 1.957(3) 6 ? Cu4 O6 1.963(3) . ? Cu4 N2 1.968(4) . ? Cu4 N1 2.063(4) . ? Cu4 O11 2.271(4) . ? N1 C1 1.325(6) . ? N1 C5 1.356(6) . ? N2 C6 1.327(5) . ? N2 N3 1.349(5) . ? N3 C7 1.350(5) . ? N4 C7 1.331(5) . ? N4 C6 1.351(6) . ? N5 C8 1.317(5) . ? N5 N6 1.371(4) . ? N6 C9 1.318(5) . ? N8 C14 1.327(6) . ? N8 C10 1.356(6) . ? N9 C15 1.332(6) . ? N9 N10 1.360(5) . ? N10 C16 1.332(5) . ? N11 C16 1.332(6) . ? N11 C15 1.341(6) . ? N12 C17 1.338(6) . ? N12 N13 1.355(5) . ? N13 C18 1.331(6) . ? N14 C17 1.326(6) . ? N14 C18 1.346(7) . ? N15 C20 1.367(11) . ? N15 C21 1.427(11) . ? N15 C22 1.504(12) . ? N16 C23 1.298(14) . ? N16 C24 1.519(15) . ? N16 C25 1.553(15) . ? O1 S1 1.477(3) . ? O2 S1 1.436(3) . ? O3 S1 1.479(3) . ? O5 S2 1.463(3) . ? O6 S2 1.487(3) . ? O7 S2 1.487(3) . ? O9 C19 1.431(8) . ? O9 H9A 0.72(6) . ? O10 C20 1.127(10) . ? O11 C23 1.225(13) . ? S2 O8 1.455(3) . ? S1 O4 1.484(3) . ? C1 C2 1.387(7) . ? C1 H1 0.9300 . ? C2 C3 1.381(8) . ? C2 H2 0.9300 . ? C3 C4 1.368(7) . ? C3 H3 0.9300 . ? C4 C5 1.381(6) . ? C4 H4 0.9300 . ? C5 C6 1.472(6) . ? C7 C8 1.454(6) . ? C8 N7 1.339(5) . ? C10 C11 1.371(8) . ? C10 H10 0.9300 . ? C11 C12 1.356(9) . ? C11 H11 0.9300 . ? C12 C13 1.393(9) . ? C12 H12 0.9300 . ? C13 C14 1.379(7) . ? C13 H13 0.9300 . ? C14 C15 1.482(7) . ? C16 C17 1.450(6) . ? C18 H18 0.9300 . ? C20 H20 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? O4 Cu4 1.957(3) 8_544 ? O8 Cu1 2.218(3) 6 ? N7 C9 1.349(5) . ? N7 Cu3 1.984(3) 18_545 ? C9 H9 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 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 N6 Cu1 O3 88.92(13) . . ? N6 Cu1 N10 169.18(15) . . ? O3 Cu1 N10 93.37(14) . . ? N6 Cu1 N12 94.58(14) . . ? O3 Cu1 N12 158.24(15) . . ? N10 Cu1 N12 79.46(14) . . ? N6 Cu1 O8 98.69(13) . 8_544 ? O3 Cu1 O8 102.86(12) . 8_544 ? N10 Cu1 O8 91.11(14) . 8_544 ? N12 Cu1 O8 97.83(14) . 8_544 ? N13 Cu2 O7 91.06(14) . . ? N13 Cu2 N3 171.42(17) . . ? O7 Cu2 N3 91.69(14) . . ? N13 Cu2 N5 94.01(14) . . ? O7 Cu2 N5 151.14(14) . . ? N3 Cu2 N5 79.73(14) . . ? N13 Cu2 O9 92.98(17) . . ? O7 Cu2 O9 114.80(15) . . ? N3 Cu2 O9 93.25(16) . . ? N5 Cu2 O9 93.30(15) . . ? N9 Cu3 O1 93.13(14) . . ? N9 Cu3 N7 167.35(16) . 17 ? O1 Cu3 N7 91.84(13) . 17 ? N9 Cu3 N8 80.05(15) . . ? O1 Cu3 N8 161.34(16) . . ? N7 Cu3 N8 91.64(15) 17 . ? N9 Cu3 O10 100.28(17) . . ? O1 Cu3 O10 104.68(16) . . ? N7 Cu3 O10 89.69(15) 17 . ? N8 Cu3 O10 93.66(19) . . ? O4 Cu4 O6 91.79(13) 6 . ? O4 Cu4 N2 169.99(14) 6 . ? O6 Cu4 N2 93.23(14) . . ? O4 Cu4 N1 95.47(14) 6 . ? O6 Cu4 N1 172.63(14) . . ? N2 Cu4 N1 79.80(15) . . ? O4 Cu4 O11 92.65(16) 6 . ? O6 Cu4 O11 90.98(16) . . ? N2 Cu4 O11 95.92(17) . . ? N1 Cu4 O11 87.39(17) . . ? C1 N1 C5 117.7(4) . . ? C1 N1 Cu4 127.7(4) . . ? C5 N1 Cu4 114.4(3) . . ? C6 N2 N3 106.1(3) . . ? C6 N2 Cu4 116.0(3) . . ? N3 N2 Cu4 136.9(3) . . ? C7 N3 N2 104.6(3) . . ? C7 N3 Cu2 116.8(3) . . ? N2 N3 Cu2 138.3(3) . . ? C7 N4 C6 100.1(3) . . ? C8 N5 N6 106.1(3) . . ? C8 N5 Cu2 113.6(3) . . ? N6 N5 Cu2 140.2(3) . . ? C9 N6 N5 106.0(3) . . ? C9 N6 Cu1 130.3(3) . . ? N5 N6 Cu1 123.5(2) . . ? C14 N8 C10 118.1(4) . . ? C14 N8 Cu3 114.1(3) . . ? C10 N8 Cu3 127.7(4) . . ? C15 N9 N10 104.7(4) . . ? C15 N9 Cu3 116.7(3) . . ? N10 N9 Cu3 138.5(3) . . ? C16 N10 N9 105.2(3) . . ? C16 N10 Cu1 116.4(3) . . ? N9 N10 Cu1 138.4(3) . . ? C16 N11 C15 100.0(4) . . ? C17 N12 N13 105.8(3) . . ? C17 N12 Cu1 114.4(3) . . ? N13 N12 Cu1 139.7(3) . . ? C18 N13 N12 105.1(4) . . ? C18 N13 Cu2 128.6(3) . . ? N12 N13 Cu2 126.3(3) . . ? C17 N14 C18 101.4(4) . . ? C20 N15 C21 122.1(10) . . ? C20 N15 C22 122.0(11) . . ? C21 N15 C22 115.8(11) . . ? C23 N16 C24 119.2(16) . . ? C23 N16 C25 114.5(15) . . ? C24 N16 C25 123.3(16) . . ? S1 O1 Cu3 131.06(19) . . ? S1 O3 Cu1 132.18(18) . . ? S2 O6 Cu4 125.63(19) . . ? S2 O7 Cu2 133.8(2) . . ? C19 O9 Cu2 120.2(4) . . ? C19 O9 H9A 109(6) . . ? Cu2 O9 H9A 98(6) . . ? C20 O10 Cu3 130.8(6) . . ? C23 O11 Cu4 125.9(7) . . ? O5 S2 O8 112.9(2) . . ? O5 S2 O7 109.7(2) . . ? O8 S2 O7 106.79(19) . . ? O5 S2 O6 108.30(19) . . ? O8 S2 O6 110.25(19) . . ? O7 S2 O6 108.83(18) . . ? O2 S1 O3 108.22(19) . . ? O2 S1 O4 110.4(2) . . ? O3 S1 O4 109.10(19) . . ? O2 S1 O1 112.1(2) . . ? O3 S1 O1 110.26(18) . . ? O4 S1 O1 106.76(18) . . ? N1 C1 C2 122.8(5) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C3 C2 C1 118.0(5) . . ? C3 C2 H2 121.0 . . ? C1 C2 H2 121.0 . . ? C2 C3 C4 120.8(5) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 117.2(5) . . ? C5 C4 H4 121.4 . . ? C3 C4 H4 121.4 . . ? N1 C5 C4 123.4(4) . . ? N1 C5 C6 112.2(4) . . ? C4 C5 C6 124.4(4) . . ? N2 C6 N4 114.4(4) . . ? N2 C6 C5 116.8(4) . . ? N4 C6 C5 128.8(4) . . ? N4 C7 N3 114.8(4) . . ? N4 C7 C8 131.8(4) . . ? N3 C7 C8 113.3(4) . . ? N5 C8 N7 112.7(4) . . ? N5 C8 C7 116.5(4) . . ? N7 C8 C7 130.8(4) . . ? N8 C10 C11 122.4(5) . . ? N8 C10 H10 118.8 . . ? C11 C10 H10 118.8 . . ? C12 C11 C10 119.0(6) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C11 C12 C13 119.6(6) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 118.2(6) . . ? C14 C13 H13 120.9 . . ? C12 C13 H13 120.9 . . ? N8 C14 C13 122.6(5) . . ? N8 C14 C15 113.6(4) . . ? C13 C14 C15 123.7(5) . . ? N9 C15 N11 115.1(4) . . ? N9 C15 C14 115.4(4) . . ? N11 C15 C14 129.6(4) . . ? N10 C16 N11 115.0(4) . . ? N10 C16 C17 114.4(4) . . ? N11 C16 C17 130.6(4) . . ? N14 C17 N12 113.8(4) . . ? N14 C17 C16 130.9(4) . . ? N12 C17 C16 115.3(4) . . ? N13 C18 N14 113.9(5) . . ? N13 C18 H18 123.1 . . ? N14 C18 H18 123.1 . . ? O10 C20 N15 127.6(10) . . ? O10 C20 H20 116.2 . . ? N15 C20 H20 116.2 . . ? N15 C21 H21A 106.1 . . ? N15 C21 H21B 108.8 . . ? H21A C21 H21B 109.5 . . ? N15 C21 H21C 113.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N15 C22 H22A 106.3 . . ? N15 C22 H22B 108.9 . . ? H22A C22 H22B 109.5 . . ? N15 C22 H22C 113.1 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O11 C23 N16 124.6(13) . . ? O11 C23 H23 117.7 . . ? N16 C23 H23 117.7 . . ? N16 C24 H24A 101.6 . . ? N16 C24 H24B 116.7 . . ? H24A C24 H24B 109.5 . . ? N16 C24 H24C 109.7 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N16 C25 H25A 110.9 . . ? N16 C25 H25B 105.3 . . ? H25A C25 H25B 109.5 . . ? N16 C25 H25C 112.0 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? S1 O4 Cu4 124.45(18) . 8_544 ? S2 O8 Cu1 133.5(2) . 6 ? C8 N7 C9 102.8(3) . . ? C8 N7 Cu3 125.1(3) . 18_545 ? C9 N7 Cu3 131.5(3) . 18_545 ? N6 C9 N7 112.4(4) . . ? N6 C9 H9 123.8 . . ? N7 C9 H9 123.8 . . ? O9 C19 H19A 109.5 . . ? O9 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O9 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.754 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.106 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material 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 _platon_squeeze_void_content 1 0.000 0.000 -0.006 3035 701 ' ' 2 0.333 0.667 0.187 3035 701 ' ' 3 0.667 0.333 0.853 3035 701 ' ' _platon_squeeze_details ; ; #===END data_complex-2 _database_code_depnum_ccdc_archive 'CCDC 869686' #TrackingRef '- Revised CIF for 1 and 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H33 Cu2 N7 O13 S2' _chemical_formula_sum 'C14 H33 Cu2 N7 O13 S2' _chemical_formula_weight 698.67 _symmetry_space_group_name_Hall '-R 3' 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 trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 34.4325(12) _cell_length_b 34.4325(12) _cell_length_c 13.0911(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 13441.4(11) _cell_formula_units_Z 18 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.18 _cell_measurement_theta_max 25.49 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 6480 _exptl_absorpt_coefficient_mu 1.629 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.562 _exptl_absorpt_correction_T_max 0.613 _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 SMART APEX CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24617 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.18 _diffrn_reflns_theta_max 25.49 _reflns_number_total 5559 _reflns_number_gt 4233 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1284P)^2^+30.5603P] 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 5559 _refine_ls_number_parameters 338 _refine_ls_number_restraints 183 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1985 _refine_ls_wR_factor_gt 0.1873 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.105 _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 0.620552(17) 0.068099(19) 0.68097(4) 0.0392(2) Uani 1 1 d . . . Cu2 Cu 0.47778(2) 0.04396(2) 0.97582(5) 0.0567(3) Uani 1 1 d . . . N1 N 0.64813(14) -0.09711(15) 0.9098(3) 0.0478(10) Uani 1 1 d . . . N2 N 0.59090(14) -0.07012(14) 0.9327(3) 0.0449(10) Uani 1 1 d . . . N3 N 0.56743(13) -0.04854(14) 0.9360(3) 0.0436(10) Uani 1 1 d . . . N4 N 0.61486(14) -0.02100(15) 0.8032(3) 0.0470(10) Uani 1 1 d . . . N5 N 0.53377(14) 0.00365(14) 0.9194(3) 0.0455(10) Uani 1 1 d . . . N6 N 0.52051(14) 0.03415(14) 0.8966(3) 0.0455(10) Uani 1 1 d . . . N7 N 0.57108(12) 0.04111(13) 0.7818(3) 0.0388(9) Uani 1 1 d . . . S1 S 0.68868(11) 0.13068(12) 0.8367(2) 0.0588(8) Uani 0.781(8) 1 d PDU . 1 O1 O 0.65269(16) 0.12195(19) 0.7639(4) 0.0565(17) Uani 0.781(8) 1 d PDU . 1 O2 O 0.6852(3) 0.0886(2) 0.8646(5) 0.110(3) Uani 0.781(8) 1 d PDU . 1 O3 O 0.6884(3) 0.1558(3) 0.9232(5) 0.093(3) Uani 0.781(8) 1 d PDU . 1 O4 O 0.73139(17) 0.1589(2) 0.7807(5) 0.076(2) Uani 0.781(8) 1 d PDU . 1 S1B S 0.6990(4) 0.1419(5) 0.8120(12) 0.090(4) Uani 0.219(8) 1 d PDU . 2 O1B O 0.6527(4) 0.1069(7) 0.796(2) 0.078(7) Uani 0.219(8) 1 d PDU . 2 O2B O 0.7272(6) 0.1214(8) 0.8189(15) 0.078(5) Uani 0.219(8) 1 d PDU . 2 O3B O 0.7016(9) 0.1743(8) 0.886(2) 0.119(11) Uani 0.219(8) 1 d PDU . 2 O4B O 0.7270(10) 0.1707(10) 0.7297(19) 0.101(9) Uani 0.219(8) 1 d PDU . 2 O5 O 0.58871(16) 0.10359(15) 0.5982(4) 0.0825(14) Uani 1 1 d . . . O6 O 0.4180(3) -0.0071(3) 0.8634(7) 0.157(3) Uani 1 1 d . . . H6A H 0.4231 -0.0055 0.7934 0.189 Uiso 1 1 calc R . . O7 O 0.5408(4) 0.0974(4) 1.0890(10) 0.226(5) Uani 1 1 d . . . H7A H 0.5384 0.1008 1.1588 0.271 Uiso 1 1 calc R A 1 S2 S 0.60534(14) 0.15184(11) 0.5932(4) 0.193(2) Uani 1 1 d D . . C1 C 0.6755(2) -0.1144(2) 0.9008(5) 0.0624(15) Uani 1 1 d . . . H1 H 0.6745 -0.1341 0.9509 0.075 Uiso 1 1 calc R . . C2 C 0.7044(3) -0.1043(3) 0.8220(6) 0.088(2) Uani 1 1 d . . . H2 H 0.7233 -0.1163 0.8196 0.106 Uiso 1 1 calc R . . C3 C 0.7058(3) -0.0769(3) 0.7470(7) 0.108(3) Uani 1 1 d . . . H3 H 0.7245 -0.0708 0.6907 0.130 Uiso 1 1 calc R . . C4 C 0.6780(3) -0.0576(3) 0.7562(5) 0.087(2) Uani 1 1 d . . . H4 H 0.6791 -0.0374 0.7076 0.105 Uiso 1 1 calc R . . C5 C 0.65002(19) -0.0691(2) 0.8369(4) 0.0533(13) Uani 1 1 d . . . C6 C 0.61862(17) -0.05295(17) 0.8549(4) 0.0444(11) Uani 1 1 d . . . C7 C 0.58314(16) -0.01973(16) 0.8580(4) 0.0422(11) Uani 1 1 d . . . C8 C 0.56351(15) 0.00904(16) 0.8496(3) 0.0412(11) Uani 1 1 d . . . C9 C 0.54418(16) 0.05629(16) 0.8151(4) 0.0444(11) Uani 1 1 d . . . H9 H 0.5423 0.0797 0.7844 0.053 Uiso 1 1 calc R . . C10 C 0.5997(10) 0.1787(7) 0.6996(15) 0.266(14) Uani 0.779(14) 1 d PD . 1 H10A H 0.5685 0.1671 0.7136 0.400 Uiso 0.779(14) 1 calc PR . 1 H10B H 0.6139 0.2103 0.6866 0.400 Uiso 0.779(14) 1 calc PR . 1 H10C H 0.6136 0.1734 0.7574 0.400 Uiso 0.779(14) 1 calc PR . 1 C11 C 0.5653(6) 0.1621(7) 0.543(2) 0.221(12) Uani 0.779(14) 1 d PD . 1 H11A H 0.5546 0.1464 0.4799 0.331 Uiso 0.779(14) 1 calc PR . 1 H11B H 0.5781 0.1937 0.5320 0.331 Uiso 0.779(14) 1 calc PR . 1 H11C H 0.5408 0.1520 0.5906 0.331 Uiso 0.779(14) 1 calc PR . 1 C10B C 0.6612(7) 0.1885(16) 0.571(5) 0.266(14) Uani 0.221(14) 1 d PD . 2 H10D H 0.6790 0.1806 0.6136 0.400 Uiso 0.221(14) 1 calc PR . 2 H10E H 0.6679 0.2184 0.5871 0.400 Uiso 0.221(14) 1 calc PR . 2 H10F H 0.6679 0.1869 0.5007 0.400 Uiso 0.221(14) 1 calc PR . 2 C11B C 0.599(2) 0.169(2) 0.474(3) 0.221(12) Uani 0.221(14) 1 d PD . 2 H11D H 0.5678 0.1604 0.4643 0.331 Uiso 0.221(14) 1 calc PR . 2 H11E H 0.6071 0.1542 0.4228 0.331 Uiso 0.221(14) 1 calc PR . 2 H11F H 0.6172 0.2005 0.4679 0.331 Uiso 0.221(14) 1 calc PR . 2 C12 C 0.3774(6) -0.0380(9) 0.900(2) 0.43(2) Uani 1 1 d . . . H12A H 0.3792 -0.0623 0.9313 0.646 Uiso 1 1 d R . . H12B H 0.3547 -0.0496 0.8481 0.646 Uiso 1 1 d R . . H12C H 0.3700 -0.0227 0.9510 0.646 Uiso 1 1 d R . . C13 C 0.5882(5) 0.1263(6) 1.0197(12) 0.166(9) Uani 0.673(14) 1 d P B 1 H13A H 0.5903 0.1085 0.9659 0.249 Uiso 0.673(14) 1 d PR B 1 H13B H 0.6131 0.1356 1.0655 0.249 Uiso 0.673(14) 1 d PR B 1 H13C H 0.5887 0.1522 0.9911 0.249 Uiso 0.673(14) 1 d PR B 1 C13B C 0.5715(11) 0.1470(13) 1.070(3) 0.166(9) Uani 0.327(14) 1 d P B 2 H13D H 0.5704 0.1637 1.1278 0.249 Uiso 0.327(14) 1 calc PR B 2 H13E H 0.5619 0.1558 1.0100 0.249 Uiso 0.327(14) 1 calc PR B 2 H13F H 0.6016 0.1529 1.0608 0.249 Uiso 0.327(14) 1 calc PR B 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 0.0278(3) 0.0481(4) 0.0357(3) -0.0010(2) 0.0042(2) 0.0144(2) Cu2 0.0712(5) 0.0732(5) 0.0575(4) 0.0368(3) 0.0360(3) 0.0600(4) N1 0.058(3) 0.062(3) 0.046(2) 0.005(2) 0.0033(19) 0.047(2) N2 0.054(2) 0.058(2) 0.041(2) 0.0152(19) 0.0127(18) 0.042(2) N3 0.052(2) 0.059(2) 0.041(2) 0.0181(18) 0.0165(18) 0.043(2) N4 0.055(2) 0.060(3) 0.045(2) 0.0172(19) 0.0157(19) 0.043(2) N5 0.052(2) 0.059(2) 0.046(2) 0.0228(19) 0.0209(19) 0.044(2) N6 0.053(2) 0.051(2) 0.050(2) 0.0250(19) 0.0220(19) 0.039(2) N7 0.0365(19) 0.047(2) 0.040(2) 0.0143(17) 0.0112(16) 0.0267(17) S1 0.0318(13) 0.0886(18) 0.0442(14) -0.0251(12) 0.0006(10) 0.0212(13) O1 0.040(3) 0.065(3) 0.060(4) -0.022(3) -0.009(2) 0.023(2) O2 0.127(7) 0.103(6) 0.097(5) -0.002(4) -0.027(5) 0.055(5) O3 0.085(5) 0.126(6) 0.062(5) -0.040(4) -0.002(4) 0.048(5) O4 0.041(3) 0.080(4) 0.093(5) -0.038(4) 0.009(3) 0.018(3) S1B 0.041(5) 0.118(7) 0.066(6) -0.045(5) 0.021(4) 0.007(5) O1B 0.045(9) 0.093(11) 0.063(10) -0.027(9) -0.002(8) 0.010(9) O2B 0.057(8) 0.111(10) 0.061(9) -0.028(8) -0.004(7) 0.038(8) O3B 0.087(15) 0.126(17) 0.059(14) -0.058(13) 0.026(11) -0.011(13) O4B 0.079(11) 0.096(12) 0.090(13) -0.025(11) 0.028(11) 0.014(10) O5 0.081(3) 0.063(3) 0.101(4) 0.014(2) -0.019(3) 0.034(2) O6 0.131(6) 0.183(8) 0.142(6) -0.007(6) -0.013(5) 0.067(6) O7 0.157(9) 0.226(12) 0.255(13) -0.052(10) 0.021(8) 0.065(8) S2 0.145(3) 0.094(2) 0.331(6) 0.070(3) -0.018(3) 0.051(2) C1 0.074(4) 0.078(4) 0.065(4) 0.009(3) 0.013(3) 0.060(3) C2 0.099(5) 0.124(6) 0.098(5) 0.029(5) 0.036(4) 0.097(5) C3 0.130(7) 0.152(8) 0.111(6) 0.058(6) 0.071(5) 0.122(7) C4 0.104(5) 0.128(6) 0.082(5) 0.049(4) 0.051(4) 0.097(5) C5 0.069(3) 0.073(4) 0.044(3) 0.013(3) 0.015(2) 0.055(3) C6 0.053(3) 0.059(3) 0.040(3) 0.012(2) 0.011(2) 0.042(3) C7 0.048(3) 0.054(3) 0.039(2) 0.011(2) 0.011(2) 0.037(2) C8 0.043(2) 0.054(3) 0.040(2) 0.015(2) 0.013(2) 0.033(2) C9 0.048(3) 0.050(3) 0.049(3) 0.017(2) 0.014(2) 0.035(2) C10 0.42(4) 0.159(17) 0.27(3) -0.060(18) 0.00(3) 0.19(2) C11 0.161(18) 0.176(16) 0.34(3) 0.093(19) -0.035(19) 0.095(16) C10B 0.42(4) 0.159(17) 0.27(3) -0.060(18) 0.00(3) 0.19(2) C11B 0.161(18) 0.176(16) 0.34(3) 0.093(19) -0.035(19) 0.095(16) C12 0.103(12) 0.35(3) 0.60(5) -0.17(4) 0.08(2) -0.070(16) C13 0.098(9) 0.167(14) 0.124(11) -0.074(10) 0.039(8) -0.016(9) C13B 0.098(9) 0.167(14) 0.124(11) -0.074(10) 0.039(8) -0.016(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.947(5) . ? Cu1 O1B 1.95(2) . ? Cu1 N2 1.979(4) 9_654 ? Cu1 N7 1.981(4) . ? Cu1 N1 2.032(4) 9_654 ? Cu1 O5 2.283(4) . ? Cu2 O4 1.940(6) 17_556 ? Cu2 N6 1.962(4) . ? Cu2 N3 2.007(4) 10_657 ? Cu2 N5 2.019(4) 10_657 ? Cu2 O4B 2.06(4) 17_556 ? Cu2 O2B 2.06(2) 17_556 ? Cu2 O6 2.423(8) . ? Cu2 O7 2.510(12) . ? Cu2 S1B 2.798(13) 17_556 ? N1 C5 1.335(6) . ? N1 C1 1.349(6) . ? N1 Cu1 2.032(4) 5_545 ? N2 C6 1.317(6) . ? N2 N3 1.345(5) . ? N2 Cu1 1.979(4) 5_545 ? N3 C7 1.335(6) . ? N3 Cu2 2.007(4) 10_657 ? N4 C7 1.326(6) . ? N4 C6 1.352(6) . ? N5 C8 1.314(6) . ? N5 N6 1.371(5) . ? N5 Cu2 2.019(4) 10_657 ? N6 C9 1.328(6) . ? N7 C8 1.337(6) . ? N7 C9 1.343(6) . ? S1 O3 1.427(5) . ? S1 O2 1.439(5) . ? S1 O1 1.470(5) . ? S1 O4 1.489(5) . ? O4 Cu2 1.940(6) 18_546 ? S1B O3B 1.447(8) . ? S1B O1B 1.453(8) . ? S1B O4B 1.456(8) . ? S1B O2B 1.462(8) . ? S1B Cu2 2.798(13) 18_546 ? O2B Cu2 2.06(2) 18_546 ? O4B Cu2 2.06(4) 18_546 ? O5 S2 1.463(5) . ? O6 C12 1.352(17) . ? O6 H6A 0.9300 . ? O7 C13B 1.51(4) . ? O7 C13 1.688(17) . ? O7 H7A 0.9300 . ? S2 C11 1.715(13) . ? S2 C10B 1.717(15) . ? S2 C11B 1.721(15) . ? S2 C10 1.735(14) . ? C1 C2 1.353(9) . ? C1 H1 0.9300 . ? C2 C3 1.348(10) . ? C2 H2 0.9300 . ? C3 C4 1.417(8) . ? C3 H3 0.9300 . ? C4 C5 1.350(7) . ? C4 H4 0.9300 . ? C5 C6 1.460(6) . ? C7 C8 1.456(6) . ? C9 H9 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C10B H10D 0.9600 . ? C10B H10E 0.9600 . ? C10B H10F 0.9600 . ? C11B H11D 0.9600 . ? C11B H11E 0.9600 . ? C11B H11F 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C13B H13C 1.1615 . ? C13B H13D 0.9600 . ? C13B H13E 0.9600 . ? C13B H13F 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 O1B 19.8(8) . . ? O1 Cu1 N2 97.4(2) . 9_654 ? O1B Cu1 N2 99.3(6) . 9_654 ? O1 Cu1 N7 91.2(2) . . ? O1B Cu1 N7 82.3(6) . . ? N2 Cu1 N7 158.13(17) 9_654 . ? O1 Cu1 N1 171.1(2) . 9_654 ? O1B Cu1 N1 168.9(8) . 9_654 ? N2 Cu1 N1 80.14(15) 9_654 9_654 ? N7 Cu1 N1 94.13(16) . 9_654 ? O1 Cu1 O5 87.2(2) . . ? O1B Cu1 O5 105.2(7) . . ? N2 Cu1 O5 108.28(19) 9_654 . ? N7 Cu1 O5 92.12(17) . . ? N1 Cu1 O5 85.41(18) 9_654 . ? O4 Cu2 N6 87.3(2) 17_556 . ? O4 Cu2 N3 98.2(2) 17_556 10_657 ? N6 Cu2 N3 174.50(15) . 10_657 ? O4 Cu2 N5 174.1(3) 17_556 10_657 ? N6 Cu2 N5 94.56(14) . 10_657 ? N3 Cu2 N5 80.05(14) 10_657 10_657 ? O4 Cu2 O4B 23.8(7) 17_556 17_556 ? N6 Cu2 O4B 96.3(9) . 17_556 ? N3 Cu2 O4B 89.0(9) 10_657 17_556 ? N5 Cu2 O4B 150.3(7) 10_657 17_556 ? O4 Cu2 O2B 38.5(6) 17_556 17_556 ? N6 Cu2 O2B 92.6(5) . 17_556 ? N3 Cu2 O2B 91.3(5) 10_657 17_556 ? N5 Cu2 O2B 146.7(6) 10_657 17_556 ? O4B Cu2 O2B 60.1(7) 17_556 17_556 ? O4 Cu2 O6 91.5(3) 17_556 . ? N6 Cu2 O6 89.5(3) . . ? N3 Cu2 O6 89.8(3) 10_657 . ? N5 Cu2 O6 94.1(3) 10_657 . ? O4B Cu2 O6 113.5(6) 17_556 . ? O2B Cu2 O6 53.4(6) 17_556 . ? O4 Cu2 O7 87.8(4) 17_556 . ? N6 Cu2 O7 89.5(3) . . ? N3 Cu2 O7 91.3(3) 10_657 . ? N5 Cu2 O7 86.6(3) 10_657 . ? O4B Cu2 O7 66.0(7) 17_556 . ? O2B Cu2 O7 126.0(6) 17_556 . ? O6 Cu2 O7 178.8(3) . . ? O4 Cu2 S1B 14.9(3) 17_556 17_556 ? N6 Cu2 S1B 99.7(3) . 17_556 ? N3 Cu2 S1B 85.6(3) 10_657 17_556 ? N5 Cu2 S1B 165.5(3) 10_657 17_556 ? O4B Cu2 S1B 30.3(4) 17_556 17_556 ? O2B Cu2 S1B 30.5(4) 17_556 17_556 ? O6 Cu2 S1B 83.3(4) . 17_556 ? O7 Cu2 S1B 96.2(5) . 17_556 ? C5 N1 C1 117.7(4) . . ? C5 N1 Cu1 114.9(3) . 5_545 ? C1 N1 Cu1 127.0(4) . 5_545 ? C6 N2 N3 106.1(4) . . ? C6 N2 Cu1 114.7(3) . 5_545 ? N3 N2 Cu1 138.9(3) . 5_545 ? C7 N3 N2 104.7(3) . . ? C7 N3 Cu2 115.1(3) . 10_657 ? N2 N3 Cu2 140.0(3) . 10_657 ? C7 N4 C6 99.9(4) . . ? C8 N5 N6 106.0(3) . . ? C8 N5 Cu2 114.2(3) . 10_657 ? N6 N5 Cu2 139.8(3) . 10_657 ? C9 N6 N5 105.7(3) . . ? C9 N6 Cu2 128.6(3) . . ? N5 N6 Cu2 125.6(3) . . ? C8 N7 C9 102.6(4) . . ? C8 N7 Cu1 126.6(3) . . ? C9 N7 Cu1 129.2(3) . . ? O3 S1 O2 112.7(4) . . ? O3 S1 O1 112.2(4) . . ? O2 S1 O1 108.7(4) . . ? O3 S1 O4 107.4(4) . . ? O2 S1 O4 109.9(4) . . ? O1 S1 O4 105.7(4) . . ? S1 O1 Cu1 125.2(4) . . ? S1 O4 Cu2 132.6(4) . 18_546 ? O3B S1B O1B 110.7(8) . . ? O3B S1B O4B 102.0(18) . . ? O1B S1B O4B 123(2) . . ? O3B S1B O2B 122(2) . . ? O1B S1B O2B 109.0(8) . . ? O4B S1B O2B 89.9(19) . . ? O3B S1B Cu2 129.0(10) . 18_546 ? O1B S1B Cu2 120.0(10) . 18_546 ? O4B S1B Cu2 45.4(16) . 18_546 ? O2B S1B Cu2 45.5(9) . 18_546 ? S1B O1B Cu1 133.4(16) . . ? S1B O2B Cu2 104.0(12) . 18_546 ? S1B O4B Cu2 104(2) . 18_546 ? S2 O5 Cu1 127.5(3) . . ? C12 O6 Cu2 121.6(14) . . ? C12 O6 H6A 119.2 . . ? Cu2 O6 H6A 119.2 . . ? C13B O7 C13 47.4(15) . . ? C13B O7 Cu2 126.2(18) . . ? C13 O7 Cu2 109.9(8) . . ? C13B O7 H7A 94.2 . . ? C13 O7 H7A 125.0 . . ? Cu2 O7 H7A 125.0 . . ? O5 S2 C11 110.7(8) . . ? O5 S2 C10B 120(2) . . ? C11 S2 C10B 120(2) . . ? O5 S2 C11B 112(3) . . ? C11 S2 C11B 48(2) . . ? C10B S2 C11B 83.7(13) . . ? O5 S2 C10 119.0(9) . . ? C11 S2 C10 83.1(12) . . ? C10B S2 C10 97(2) . . ? C11B S2 C10 119(3) . . ? C2 C1 N1 122.7(5) . . ? C2 C1 H1 118.7 . . ? N1 C1 H1 118.7 . . ? C3 C2 C1 120.0(5) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 118.1(6) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C5 C4 C3 118.7(6) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? N1 C5 C4 122.7(5) . . ? N1 C5 C6 112.5(4) . . ? C4 C5 C6 124.8(5) . . ? N2 C6 N4 114.2(4) . . ? N2 C6 C5 117.5(4) . . ? N4 C6 C5 128.3(4) . . ? N4 C7 N3 115.1(4) . . ? N4 C7 C8 130.7(4) . . ? N3 C7 C8 114.2(4) . . ? N5 C8 N7 113.2(4) . . ? N5 C8 C7 116.4(4) . . ? N7 C8 C7 130.3(4) . . ? N6 C9 N7 112.4(4) . . ? N6 C9 H9 123.8 . . ? N7 C9 H9 123.8 . . ? S2 C10 H10A 109.5 . . ? S2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? S2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? S2 C11 H11A 109.5 . . ? S2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? S2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? S2 C10B H10D 109.5 . . ? S2 C10B H10E 109.5 . . ? H10D C10B H10E 109.5 . . ? S2 C10B H10F 109.5 . . ? H10D C10B H10F 109.5 . . ? H10E C10B H10F 109.5 . . ? S2 C11B H11D 109.5 . . ? S2 C11B H11E 109.5 . . ? H11D C11B H11E 109.5 . . ? S2 C11B H11F 109.5 . . ? H11D C11B H11F 109.5 . . ? H11E C11B H11F 109.5 . . ? O6 C12 H12A 110.2 . . ? O6 C12 H12B 112.5 . . ? H12A C12 H12B 109.5 . . ? O6 C12 H12C 105.6 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O7 C13 H13A 112.2 . . ? O7 C13 H13B 107.5 . . ? H13A C13 H13B 109.5 . . ? O7 C13 H13C 108.7 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O7 C13B H13C 109.5 . . ? O7 C13B H13D 109.5 . . ? O7 C13B H13E 109.5 . . ? H13D C13B H13E 109.5 . . ? O7 C13B H13F 109.5 . . ? H13D C13B H13F 109.5 . . ? H13E C13B H13F 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.884 _refine_diff_density_min -0.595 _refine_diff_density_rms 0.109 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material 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 _platon_squeeze_void_content 1 0.000 0.000 -0.002 1562 436 ' ' 2 0.333 0.667 0.680 1562 436 ' ' 3 0.667 0.333 0.347 1562 436 ' ' _platon_squeeze_details ; ; #===END