# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_btmres10 #TrackingRef '- BTMRES10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H28 B N6 O3 Re S3' _chemical_formula_weight 849.80 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' B B 0.0013 0.0007 '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' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 16.147(3) _cell_length_b 10.510(2) _cell_length_c 19.719(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.087(3) _cell_angle_gamma 90.00 _cell_volume 3341.5(12) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 9828 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 32.11 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.689 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 3.868 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5592 _exptl_absorpt_correction_T_max 0.8301 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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_reflns_number 49786 _diffrn_reflns_av_R_equivalents 0.0517 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 29.57 _reflns_number_total 9381 _reflns_number_gt 7614 _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^)+(0.0270P)^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 9381 _refine_ls_number_parameters 431 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0581 _refine_ls_wR_factor_gt 0.0538 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.003 _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 Re Re 0.289166(6) 0.547887(9) 0.425307(5) 0.01759(3) Uani 1 1 d . . . B B 0.24479(18) 0.9353(3) 0.40390(15) 0.0162(6) Uani 1 1 d . . . H1 H 0.2346(17) 1.038(2) 0.3966(14) 0.017(7) Uiso 1 1 d . . . S1 S 0.40097(4) 0.71092(6) 0.40572(3) 0.01803(13) Uani 1 1 d . . . S2 S 0.22802(4) 0.68678(6) 0.51521(3) 0.02022(14) Uani 1 1 d . . . S3 S 0.19159(4) 0.64417(6) 0.33410(3) 0.02068(13) Uani 1 1 d . . . N11 N 0.31987(13) 0.92061(19) 0.45554(11) 0.0158(4) Uani 1 1 d . . . N12 N 0.43262(13) 0.8595(2) 0.51597(11) 0.0178(4) Uani 1 1 d . . . N21 N 0.16455(12) 0.8792(2) 0.43123(11) 0.0162(4) Uani 1 1 d . . . N22 N 0.07187(13) 0.7676(2) 0.48365(11) 0.0186(4) Uani 1 1 d . . . N31 N 0.26699(13) 0.8800(2) 0.33419(11) 0.0164(4) Uani 1 1 d . . . N32 N 0.29000(15) 0.7601(2) 0.24535(11) 0.0234(5) Uani 1 1 d . . . O1 O 0.16207(13) 0.3383(2) 0.44783(13) 0.0430(6) Uani 1 1 d . . . O2 O 0.37244(14) 0.3761(2) 0.32388(12) 0.0369(5) Uani 1 1 d . . . O3 O 0.40524(14) 0.4465(2) 0.54069(11) 0.0368(5) Uani 1 1 d . . . C1 C 0.20879(19) 0.4181(3) 0.43922(16) 0.0280(6) Uani 1 1 d . . . C2 C 0.34094(17) 0.4412(3) 0.36115(15) 0.0239(6) Uani 1 1 d . . . C3 C 0.36086(18) 0.4823(3) 0.49766(15) 0.0235(6) Uani 1 1 d . . . C4 C 0.1006(3) 0.2081(4) 0.7446(2) 0.0538(10) Uani 1 1 d . . . H4A H 0.0949 0.1320 0.7699 0.065 Uiso 1 1 calc R . . C5 C 0.0313(2) 0.2689(4) 0.7163(2) 0.0505(10) Uani 1 1 d . . . H5A H -0.0223 0.2343 0.7216 0.061 Uiso 1 1 calc R . . C6 C 0.0401(2) 0.3785(4) 0.6809(2) 0.0516(10) Uani 1 1 d . . . H6A H -0.0077 0.4214 0.6622 0.062 Uiso 1 1 calc R . . C7 C 0.1175(2) 0.4276(4) 0.67180(19) 0.0489(10) Uani 1 1 d . . . H7A H 0.1230 0.5035 0.6463 0.059 Uiso 1 1 calc R . . C8 C 0.1869(2) 0.3679(4) 0.69932(18) 0.0442(9) Uani 1 1 d . . . H8A H 0.2403 0.4024 0.6929 0.053 Uiso 1 1 calc R . . C9 C 0.1793(2) 0.2591(4) 0.73588(19) 0.0492(10) Uani 1 1 d . . . H9A H 0.2272 0.2180 0.7554 0.059 Uiso 1 1 calc R . . C11 C 0.50487(16) 0.7851(3) 0.53939(14) 0.0239(6) Uani 1 1 d . . . H11B H 0.5139 0.7946 0.5887 0.036 Uiso 1 1 calc R . . H11C H 0.5538 0.8154 0.5169 0.036 Uiso 1 1 calc R . . H11A H 0.4954 0.6952 0.5283 0.036 Uiso 1 1 calc R . . C12 C 0.38214(15) 0.8340(2) 0.46025(13) 0.0166(5) Uani 1 1 d . . . C13 C 0.40222(16) 0.9657(2) 0.54882(13) 0.0190(5) Uani 1 1 d . . . C14 C 0.33084(16) 1.0032(2) 0.51104(13) 0.0173(5) Uani 1 1 d . . . C15 C 0.28499(17) 1.1079(3) 0.53000(14) 0.0216(6) Uani 1 1 d . . . H15A H 0.2362 1.1338 0.5047 0.026 Uiso 1 1 calc R . . C16 C 0.31375(18) 1.1725(3) 0.58745(15) 0.0267(6) Uani 1 1 d . . . H16A H 0.2838 1.2445 0.6018 0.032 Uiso 1 1 calc R . . C17 C 0.38541(19) 1.1356(3) 0.62516(15) 0.0301(7) Uani 1 1 d . . . H17A H 0.4029 1.1827 0.6645 0.036 Uiso 1 1 calc R . . C18 C 0.43157(18) 1.0312(3) 0.60625(14) 0.0242(6) Uani 1 1 d . . . H18A H 0.4807 1.0059 0.6314 0.029 Uiso 1 1 calc R . . C21 C 0.03374(18) 0.6701(3) 0.52477(16) 0.0272(6) Uani 1 1 d . . . H21A H 0.0738 0.6018 0.5349 0.041 Uiso 1 1 calc R . . H21B H -0.0151 0.6352 0.4996 0.041 Uiso 1 1 calc R . . H21C H 0.0170 0.7080 0.5673 0.041 Uiso 1 1 calc R . . C22 C 0.15369(16) 0.7815(2) 0.47412(13) 0.0172(5) Uani 1 1 d . . . C23 C 0.02747(15) 0.8594(2) 0.44635(13) 0.0182(5) Uani 1 1 d . . . C24 C 0.08565(15) 0.9290(2) 0.41231(13) 0.0167(5) Uani 1 1 d . . . C25 C 0.06086(17) 1.0278(2) 0.36881(14) 0.0211(6) Uani 1 1 d . . . H25A H 0.0997 1.0755 0.3447 0.025 Uiso 1 1 calc R . . C26 C -0.02393(17) 1.0533(3) 0.36246(15) 0.0251(6) Uani 1 1 d . . . H26A H -0.0433 1.1196 0.3330 0.030 Uiso 1 1 calc R . . C27 C -0.08135(17) 0.9838(3) 0.39833(15) 0.0249(6) Uani 1 1 d . . . H27A H -0.1385 1.0055 0.3933 0.030 Uiso 1 1 calc R . . C28 C -0.05711(16) 0.8853(3) 0.44049(14) 0.0226(6) Uani 1 1 d . . . H28A H -0.0960 0.8373 0.4644 0.027 Uiso 1 1 calc R . . C31 C 0.2897(2) 0.6523(3) 0.19867(16) 0.0385(8) Uani 1 1 d . . . H31A H 0.2504 0.5879 0.2131 0.058 Uiso 1 1 calc R . . H31B H 0.3454 0.6153 0.1988 0.058 Uiso 1 1 calc R . . H31C H 0.2730 0.6813 0.1527 0.058 Uiso 1 1 calc R . . C32 C 0.25024(16) 0.7668(2) 0.30400(13) 0.0193(5) Uani 1 1 d . . . C33 C 0.33721(17) 0.8698(3) 0.23879(14) 0.0223(6) Uani 1 1 d . . . C34 C 0.32309(15) 0.9449(2) 0.29469(13) 0.0180(5) Uani 1 1 d . . . C35 C 0.36252(16) 1.0616(2) 0.30463(14) 0.0198(5) Uani 1 1 d . . . H35A H 0.3529 1.1136 0.3428 0.024 Uiso 1 1 calc R . . C36 C 0.41677(17) 1.0982(3) 0.25583(14) 0.0241(6) Uani 1 1 d . . . H36A H 0.4451 1.1771 0.2610 0.029 Uiso 1 1 calc R . . C37 C 0.43074(19) 1.0229(3) 0.19957(16) 0.0303(7) Uani 1 1 d . . . H37A H 0.4685 1.0512 0.1674 0.036 Uiso 1 1 calc R . . C38 C 0.3905(2) 0.9068(3) 0.18945(16) 0.0320(7) Uani 1 1 d . . . H38A H 0.3991 0.8555 0.1508 0.038 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 Re 0.01645(5) 0.01446(5) 0.02202(6) 0.00103(4) 0.00267(4) 0.00169(4) B 0.0146(13) 0.0163(14) 0.0179(14) -0.0011(11) 0.0024(11) 0.0009(11) S1 0.0156(3) 0.0171(3) 0.0216(3) -0.0039(2) 0.0029(2) 0.0015(2) S2 0.0201(3) 0.0209(3) 0.0200(3) 0.0040(3) 0.0044(3) 0.0060(3) S3 0.0192(3) 0.0189(3) 0.0236(3) 0.0005(3) -0.0020(3) -0.0032(3) N11 0.0150(10) 0.0155(10) 0.0169(11) -0.0017(8) 0.0014(8) -0.0003(8) N12 0.0149(10) 0.0196(11) 0.0186(11) -0.0004(9) -0.0005(8) -0.0001(9) N21 0.0130(10) 0.0164(11) 0.0192(11) 0.0010(8) 0.0021(8) 0.0021(8) N22 0.0170(11) 0.0169(11) 0.0223(12) 0.0008(9) 0.0041(9) 0.0019(8) N31 0.0157(10) 0.0165(11) 0.0169(11) 0.0018(8) 0.0005(8) -0.0006(8) N32 0.0307(13) 0.0209(11) 0.0191(12) -0.0014(9) 0.0054(10) -0.0011(10) O1 0.0284(12) 0.0310(12) 0.0702(18) 0.0141(12) 0.0092(12) -0.0036(10) O2 0.0379(13) 0.0292(12) 0.0444(14) -0.0130(10) 0.0104(11) -0.0003(10) O3 0.0411(13) 0.0361(12) 0.0326(12) 0.0024(10) -0.0028(10) 0.0168(10) C1 0.0267(15) 0.0221(14) 0.0357(17) 0.0065(12) 0.0054(13) 0.0072(12) C2 0.0211(13) 0.0179(13) 0.0325(16) 0.0001(12) -0.0014(11) -0.0031(11) C3 0.0244(14) 0.0189(14) 0.0275(15) 0.0002(11) 0.0045(12) 0.0062(11) C4 0.075(3) 0.045(2) 0.042(2) -0.0164(18) 0.006(2) -0.001(2) C5 0.037(2) 0.068(3) 0.047(2) -0.032(2) 0.0061(17) -0.0079(19) C6 0.032(2) 0.068(3) 0.053(2) -0.023(2) -0.0108(17) 0.0124(19) C7 0.051(2) 0.057(2) 0.038(2) -0.0103(18) -0.0085(18) 0.0021(19) C8 0.0308(18) 0.060(2) 0.042(2) -0.0243(19) -0.0010(15) -0.0021(17) C9 0.042(2) 0.059(2) 0.045(2) -0.0251(19) -0.0145(17) 0.0197(19) C11 0.0159(13) 0.0281(15) 0.0272(15) 0.0016(12) -0.0036(11) 0.0028(11) C12 0.0155(12) 0.0159(12) 0.0186(13) 0.0004(10) 0.0036(10) 0.0002(9) C13 0.0197(13) 0.0197(13) 0.0183(13) -0.0012(10) 0.0057(10) -0.0041(10) C14 0.0190(13) 0.0165(11) 0.0168(13) -0.0002(10) 0.0050(10) -0.0025(10) C15 0.0190(13) 0.0196(13) 0.0267(15) -0.0030(11) 0.0056(11) 0.0000(10) C16 0.0313(16) 0.0226(14) 0.0272(15) -0.0077(12) 0.0108(12) -0.0017(12) C17 0.0380(17) 0.0301(16) 0.0223(15) -0.0091(12) 0.0031(13) -0.0086(13) C18 0.0249(14) 0.0272(15) 0.0205(14) -0.0024(11) 0.0006(11) -0.0066(11) C21 0.0239(14) 0.0225(14) 0.0361(17) 0.0075(12) 0.0085(12) -0.0023(11) C22 0.0186(13) 0.0157(12) 0.0175(13) -0.0032(10) 0.0031(10) 0.0008(10) C23 0.0157(12) 0.0183(12) 0.0208(13) -0.0022(10) 0.0015(10) -0.0001(10) C24 0.0140(12) 0.0175(13) 0.0185(13) -0.0044(10) 0.0012(10) 0.0005(9) C25 0.0215(13) 0.0218(14) 0.0202(13) 0.0043(10) 0.0020(11) 0.0022(10) C26 0.0233(14) 0.0261(14) 0.0257(14) 0.0035(12) -0.0016(11) 0.0066(12) C27 0.0154(13) 0.0287(15) 0.0304(16) -0.0034(12) 0.0002(11) 0.0036(11) C28 0.0153(13) 0.0275(15) 0.0252(14) -0.0038(12) 0.0036(11) 0.0003(11) C31 0.064(2) 0.0263(16) 0.0258(16) -0.0091(13) 0.0090(16) -0.0036(16) C32 0.0182(13) 0.0216(13) 0.0178(13) 0.0020(10) -0.0024(10) 0.0019(10) C33 0.0264(14) 0.0209(13) 0.0197(13) 0.0026(11) 0.0034(11) 0.0038(11) C34 0.0143(12) 0.0225(13) 0.0173(12) 0.0045(11) 0.0023(9) 0.0021(10) C35 0.0193(13) 0.0192(13) 0.0210(13) 0.0030(10) 0.0004(10) 0.0008(10) C36 0.0196(13) 0.0259(14) 0.0266(15) 0.0090(12) 0.0008(11) -0.0021(11) C37 0.0294(16) 0.0349(17) 0.0280(16) 0.0085(13) 0.0133(13) 0.0013(13) C38 0.0392(18) 0.0336(16) 0.0244(16) 0.0000(13) 0.0132(13) 0.0030(14) _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 Re C1 1.913(3) . ? Re C2 1.916(3) . ? Re C3 1.917(3) . ? Re S1 2.5337(7) . ? Re S3 2.5369(8) . ? Re S2 2.5372(7) . ? B H1 1.10(3) . ? B N21 1.547(3) . ? B N11 1.548(4) . ? B N31 1.552(4) . ? S1 C12 1.720(3) . ? S2 C22 1.727(3) . ? S3 C32 1.724(3) . ? N11 C12 1.356(3) . ? N11 C14 1.401(3) . ? N12 C12 1.359(3) . ? N12 C13 1.394(3) . ? N12 C11 1.458(3) . ? N21 C22 1.348(3) . ? N21 C24 1.409(3) . ? N22 C22 1.352(3) . ? N22 C23 1.389(3) . ? N22 C21 1.463(3) . ? N31 C32 1.351(3) . ? N31 C34 1.403(3) . ? N32 C32 1.354(3) . ? N32 C33 1.392(3) . ? N32 C31 1.460(4) . ? O1 C1 1.147(3) . ? O2 C2 1.144(3) . ? O3 C3 1.144(3) . ? C4 C5 1.381(6) . ? C4 C9 1.398(6) . ? C5 C6 1.358(6) . ? C6 C7 1.373(5) . ? C7 C8 1.371(5) . ? C8 C9 1.361(5) . ? C13 C18 1.387(4) . ? C13 C14 1.395(4) . ? C14 C15 1.389(4) . ? C15 C16 1.380(4) . ? C16 C17 1.396(4) . ? C17 C18 1.388(4) . ? C23 C28 1.391(3) . ? C23 C24 1.392(3) . ? C24 C25 1.392(4) . ? C25 C26 1.394(4) . ? C26 C27 1.401(4) . ? C27 C28 1.372(4) . ? C33 C34 1.384(4) . ? C33 C38 1.389(4) . ? C34 C35 1.391(4) . ? C35 C36 1.390(4) . ? C36 C37 1.391(4) . ? C37 C38 1.391(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 C1 Re C2 90.06(12) . . ? C1 Re C3 91.37(13) . . ? C2 Re C3 90.77(12) . . ? C1 Re S1 177.06(9) . . ? C2 Re S1 87.43(8) . . ? C3 Re S1 87.13(9) . . ? C1 Re S3 89.19(9) . . ? C2 Re S3 92.39(9) . . ? C3 Re S3 176.79(8) . . ? S1 Re S3 92.44(2) . . ? C1 Re S2 91.00(9) . . ? C2 Re S2 176.56(9) . . ? C3 Re S2 85.93(8) . . ? S1 Re S2 91.42(2) . . ? S3 Re S2 90.90(3) . . ? H1 B N21 107.3(15) . . ? H1 B N11 106.9(15) . . ? N21 B N11 111.9(2) . . ? H1 B N31 106.9(15) . . ? N21 B N31 113.8(2) . . ? N11 B N31 109.6(2) . . ? C12 S1 Re 105.19(9) . . ? C22 S2 Re 106.89(9) . . ? C32 S3 Re 102.16(9) . . ? C12 N11 C14 107.5(2) . . ? C12 N11 B 131.6(2) . . ? C14 N11 B 120.9(2) . . ? C12 N12 C13 108.8(2) . . ? C12 N12 C11 125.8(2) . . ? C13 N12 C11 125.3(2) . . ? C22 N21 C24 107.6(2) . . ? C22 N21 B 130.5(2) . . ? C24 N21 B 121.9(2) . . ? C22 N22 C23 109.4(2) . . ? C22 N22 C21 126.6(2) . . ? C23 N22 C21 124.0(2) . . ? C32 N31 C34 107.6(2) . . ? C32 N31 B 132.0(2) . . ? C34 N31 B 119.8(2) . . ? C32 N32 C33 108.9(2) . . ? C32 N32 C31 126.4(2) . . ? C33 N32 C31 124.6(2) . . ? O1 C1 Re 178.4(3) . . ? O2 C2 Re 178.7(3) . . ? O3 C3 Re 177.8(3) . . ? C5 C4 C9 119.7(4) . . ? C6 C5 C4 119.7(4) . . ? C5 C6 C7 120.4(4) . . ? C8 C7 C6 120.5(4) . . ? C9 C8 C7 119.9(4) . . ? C8 C9 C4 119.8(4) . . ? N11 C12 N12 109.5(2) . . ? N11 C12 S1 128.1(2) . . ? N12 C12 S1 122.33(19) . . ? C18 C13 N12 131.6(3) . . ? C18 C13 C14 122.2(2) . . ? N12 C13 C14 106.3(2) . . ? C15 C14 C13 121.1(2) . . ? C15 C14 N11 130.9(2) . . ? C13 C14 N11 107.9(2) . . ? C16 C15 C14 116.8(3) . . ? C15 C16 C17 122.2(3) . . ? C18 C17 C16 121.2(3) . . ? C13 C18 C17 116.5(3) . . ? N21 C22 N22 109.3(2) . . ? N21 C22 S2 128.5(2) . . ? N22 C22 S2 122.13(19) . . ? N22 C23 C28 131.0(2) . . ? N22 C23 C24 106.1(2) . . ? C28 C23 C24 122.8(2) . . ? C23 C24 C25 120.7(2) . . ? C23 C24 N21 107.5(2) . . ? C25 C24 N21 131.8(2) . . ? C24 C25 C26 116.5(2) . . ? C25 C26 C27 121.9(3) . . ? C28 C27 C26 121.6(3) . . ? C27 C28 C23 116.4(3) . . ? N31 C32 N32 109.2(2) . . ? N31 C32 S3 127.4(2) . . ? N32 C32 S3 123.3(2) . . ? C34 C33 C38 122.2(3) . . ? C34 C33 N32 106.5(2) . . ? C38 C33 N32 131.3(3) . . ? C33 C34 C35 121.4(2) . . ? C33 C34 N31 107.7(2) . . ? C35 C34 N31 130.9(2) . . ? C36 C35 C34 116.6(3) . . ? C35 C36 C37 122.0(3) . . ? C38 C37 C36 121.3(3) . . ? C33 C38 C37 116.6(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.57 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.337 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.109 _database_code_depnum_ccdc_archive 'CCDC 794058' ####################################################################### # # 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_tmbs10 #TrackingRef '- tmbs10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C60 H68 B2 N12 Na2 O3 S6' _chemical_formula_weight 1265.22 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' B B 0.0013 0.0007 '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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 34.381(13) _cell_length_b 16.553(6) _cell_length_c 11.073(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.783(6) _cell_angle_gamma 90.00 _cell_volume 6257(4) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 8221 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 30.37 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2656 _exptl_absorpt_coefficient_mu 0.288 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.9527 _exptl_absorpt_correction_T_max 0.9829 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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_reflns_number 37010 _diffrn_reflns_av_R_equivalents 0.0796 _diffrn_reflns_av_sigmaI/netI 0.0812 _diffrn_reflns_limit_h_min -49 _diffrn_reflns_limit_h_max 48 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.19 _diffrn_reflns_theta_max 30.55 _reflns_number_total 9564 _reflns_number_gt 5774 _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^)+(0.0464P)^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 9564 _refine_ls_number_parameters 391 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1018 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1176 _refine_ls_wR_factor_gt 0.0990 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 Na Na 0.04658(2) 0.25726(5) 0.22753(7) 0.02121(18) Uani 1 1 d . . . B B 0.16642(7) 0.24115(14) 0.1922(2) 0.0198(5) Uani 1 1 d . . . H1 H 0.1990(5) 0.2359(10) 0.1845(16) 0.010(5) Uiso 1 1 d . . . N12 N 0.13569(5) 0.44406(10) 0.29488(15) 0.0235(4) Uani 1 1 d . . . N11 N 0.15930(5) 0.32674(9) 0.24084(14) 0.0190(3) Uani 1 1 d . . . N22 N 0.13484(5) 0.09667(10) 0.42361(14) 0.0199(4) Uani 1 1 d . . . N21 N 0.15636(5) 0.17355(9) 0.28149(14) 0.0176(3) Uani 1 1 d . . . N32 N 0.10632(5) 0.19797(10) -0.10581(14) 0.0206(4) Uani 1 1 d . . . N31 N 0.14594(5) 0.22663(9) 0.06138(14) 0.0167(3) Uani 1 1 d . . . S1 S 0.089996(15) 0.37472(3) 0.10715(5) 0.02212(12) Uani 1 1 d . . . S2 S 0.106150(16) 0.24873(3) 0.42298(4) 0.02258(12) Uani 1 1 d . . . S3 S 0.080400(15) 0.13606(3) 0.09516(5) 0.02187(12) Uani 1 1 d . . . O1 O 0.0000 0.14605(11) 0.2500 0.0219(4) Uani 1 2 d S . . O2 O 0.01058(4) 0.31677(8) 0.39194(12) 0.0240(3) Uani 1 1 d . . . C11 C 0.12933(6) 0.38043(12) 0.21587(17) 0.0202(4) Uani 1 1 d . . . C12 C 0.16983(6) 0.43084(12) 0.37241(19) 0.0256(5) Uani 1 1 d . . . C13 C 0.18796(7) 0.47655(14) 0.4686(2) 0.0340(6) Uani 1 1 d . . . H13A H 0.1772 0.5262 0.4920 0.041 Uiso 1 1 calc R . . C14 C 0.22253(7) 0.44601(15) 0.5287(2) 0.0387(6) Uani 1 1 d . . . H14A H 0.2357 0.4752 0.5953 0.046 Uiso 1 1 calc R . . C15 C 0.23823(7) 0.37393(15) 0.4938(2) 0.0361(6) Uani 1 1 d . . . H15A H 0.2623 0.3554 0.5358 0.043 Uiso 1 1 calc R . . C16 C 0.21970(6) 0.32769(14) 0.39860(19) 0.0281(5) Uani 1 1 d . . . H16A H 0.2304 0.2777 0.3761 0.034 Uiso 1 1 calc R . . C17 C 0.18490(6) 0.35787(12) 0.33788(18) 0.0225(4) Uani 1 1 d . . . C18 C 0.11210(7) 0.51713(13) 0.2955(2) 0.0343(5) Uani 1 1 d . . . H18A H 0.0875 0.5096 0.2423 0.051 Uiso 1 1 calc R . . H18B H 0.1265 0.5627 0.2660 0.051 Uiso 1 1 calc R . . H18C H 0.1064 0.5282 0.3785 0.051 Uiso 1 1 calc R . . C21 C 0.13330(6) 0.17273(12) 0.37337(17) 0.0196(4) Uani 1 1 d . . . C22 C 0.15874(6) 0.04792(11) 0.36215(17) 0.0185(4) Uani 1 1 d . . . C23 C 0.16945(6) -0.03291(12) 0.37761(19) 0.0245(5) Uani 1 1 d . . . H23A H 0.1600 -0.0654 0.4385 0.029 Uiso 1 1 calc R . . C24 C 0.19457(6) -0.06358(12) 0.2997(2) 0.0272(5) Uani 1 1 d . . . H24A H 0.2027 -0.1184 0.3077 0.033 Uiso 1 1 calc R . . C25 C 0.20809(6) -0.01572(13) 0.2101(2) 0.0266(5) Uani 1 1 d . . . H25A H 0.2252 -0.0387 0.1582 0.032 Uiso 1 1 calc R . . C26 C 0.19723(6) 0.06473(12) 0.19442(18) 0.0224(4) Uani 1 1 d . . . H26A H 0.2065 0.0970 0.1329 0.027 Uiso 1 1 calc R . . C27 C 0.17212(5) 0.09616(11) 0.27287(17) 0.0183(4) Uani 1 1 d . . . C28 C 0.11586(6) 0.07143(13) 0.52837(18) 0.0273(5) Uani 1 1 d . . . H28A H 0.0939 0.1077 0.5379 0.041 Uiso 1 1 calc R . . H28B H 0.1348 0.0735 0.6017 0.041 Uiso 1 1 calc R . . H28C H 0.1061 0.0161 0.5159 0.041 Uiso 1 1 calc R . . C31 C 0.11178(6) 0.18896(11) 0.01825(17) 0.0185(4) Uani 1 1 d . . . C32 C 0.13733(6) 0.24097(12) -0.14304(18) 0.0211(4) Uani 1 1 d . . . C33 C 0.14527(7) 0.26319(13) -0.25897(19) 0.0287(5) Uani 1 1 d . . . H33A H 0.1280 0.2501 -0.3296 0.034 Uiso 1 1 calc R . . C34 C 0.17960(7) 0.30520(14) -0.2657(2) 0.0335(5) Uani 1 1 d . . . H34A H 0.1861 0.3217 -0.3430 0.040 Uiso 1 1 calc R . . C35 C 0.20499(7) 0.32409(14) -0.1618(2) 0.0334(5) Uani 1 1 d . . . H35A H 0.2285 0.3526 -0.1702 0.040 Uiso 1 1 calc R . . C36 C 0.19671(6) 0.30210(13) -0.0454(2) 0.0275(5) Uani 1 1 d . . . H36A H 0.2139 0.3157 0.0253 0.033 Uiso 1 1 calc R . . C37 C 0.16224(6) 0.25935(11) -0.03800(18) 0.0187(4) Uani 1 1 d . . . C38 C 0.07467(6) 0.16258(14) -0.18694(19) 0.0313(5) Uani 1 1 d . . . H38A H 0.0505 0.1634 -0.1479 0.047 Uiso 1 1 calc R . . H38B H 0.0813 0.1066 -0.2051 0.047 Uiso 1 1 calc R . . H38C H 0.0708 0.1938 -0.2626 0.047 Uiso 1 1 calc R . . C41 C 0.01601(7) 0.09500(13) 0.3501(2) 0.0316(5) Uani 1 1 d . . . H41A H 0.0070 0.1134 0.4273 0.038 Uiso 1 1 calc R . . H41B H 0.0450 0.0961 0.3590 0.038 Uiso 1 1 calc R . . C51 C 0.01041(7) 0.29021(14) 0.51684(19) 0.0311(5) Uani 1 1 d . . . H51A H 0.0298 0.2465 0.5364 0.037 Uiso 1 1 calc R . . H51B H -0.0158 0.2699 0.5302 0.037 Uiso 1 1 calc R . . C52 C 0.02116(8) 0.36444(15) 0.5955(2) 0.0444(7) Uani 1 1 d . . . H52A H -0.0025 0.3948 0.6116 0.053 Uiso 1 1 calc R . . H52B H 0.0363 0.3492 0.6739 0.053 Uiso 1 1 calc R . . C53 C 0.04600(7) 0.41321(14) 0.5175(2) 0.0379(6) Uani 1 1 d . . . H53A H 0.0467 0.4711 0.5402 0.046 Uiso 1 1 calc R . . H53B H 0.0731 0.3922 0.5228 0.046 Uiso 1 1 calc R . . C54 C 0.02405(7) 0.39982(13) 0.3927(2) 0.0297(5) Uani 1 1 d . . . H54A H 0.0016 0.4374 0.3782 0.036 Uiso 1 1 calc R . . H54B H 0.0415 0.4084 0.3289 0.036 Uiso 1 1 calc R . . C55 C 0.00092(8) 0.01075(14) 0.3180(2) 0.0472(7) Uani 1 1 d . . . H55A H 0.0192 -0.0311 0.3550 0.057 Uiso 1 1 calc R . . H55B H -0.0253 0.0020 0.3444 0.057 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 Na 0.0205(4) 0.0223(4) 0.0207(4) 0.0003(3) 0.0021(3) 0.0002(3) B 0.0186(11) 0.0214(11) 0.0188(11) 0.0024(9) 0.0000(9) -0.0006(9) N12 0.0312(10) 0.0166(8) 0.0218(9) -0.0006(7) 0.0001(7) -0.0012(7) N11 0.0214(9) 0.0176(8) 0.0170(8) 0.0017(6) -0.0023(7) -0.0033(7) N22 0.0237(9) 0.0206(9) 0.0154(8) 0.0018(7) 0.0029(7) 0.0006(7) N21 0.0201(8) 0.0181(8) 0.0146(8) -0.0004(6) 0.0021(6) -0.0004(7) N32 0.0226(9) 0.0222(9) 0.0167(8) -0.0008(7) 0.0012(7) -0.0016(7) N31 0.0171(8) 0.0178(8) 0.0156(8) 0.0010(6) 0.0033(6) -0.0021(6) S1 0.0227(3) 0.0213(3) 0.0213(3) 0.0024(2) -0.0018(2) 0.0001(2) S2 0.0260(3) 0.0240(3) 0.0177(2) -0.0010(2) 0.0021(2) 0.0053(2) S3 0.0211(3) 0.0210(3) 0.0245(3) -0.0018(2) 0.0071(2) -0.0042(2) O1 0.0212(10) 0.0197(10) 0.0249(11) 0.000 0.0030(8) 0.000 O2 0.0244(8) 0.0248(8) 0.0227(8) -0.0046(6) 0.0026(6) -0.0021(6) C11 0.0245(10) 0.0178(9) 0.0179(10) 0.0017(8) 0.0014(8) -0.0036(8) C12 0.0330(12) 0.0232(11) 0.0199(10) 0.0032(8) 0.0007(9) -0.0089(9) C13 0.0514(15) 0.0267(12) 0.0229(11) -0.0004(9) -0.0005(11) -0.0158(11) C14 0.0515(16) 0.0402(14) 0.0218(12) 0.0016(10) -0.0063(11) -0.0276(12) C15 0.0336(13) 0.0432(15) 0.0280(12) 0.0120(11) -0.0112(10) -0.0188(11) C16 0.0286(12) 0.0296(12) 0.0246(11) 0.0079(9) -0.0031(9) -0.0088(10) C17 0.0265(11) 0.0209(10) 0.0194(10) 0.0033(8) -0.0007(8) -0.0087(8) C18 0.0427(14) 0.0208(11) 0.0392(14) -0.0053(10) 0.0044(11) 0.0028(10) C21 0.0195(10) 0.0239(10) 0.0142(9) -0.0004(8) -0.0035(8) 0.0011(8) C22 0.0191(10) 0.0200(10) 0.0154(9) -0.0009(8) -0.0019(8) -0.0005(8) C23 0.0266(11) 0.0198(10) 0.0255(11) 0.0029(8) -0.0043(9) -0.0017(9) C24 0.0292(12) 0.0184(10) 0.0318(12) -0.0058(9) -0.0057(9) 0.0028(9) C25 0.0218(11) 0.0290(12) 0.0282(12) -0.0079(9) 0.0005(9) 0.0019(9) C26 0.0214(10) 0.0261(11) 0.0193(10) -0.0021(8) 0.0008(8) -0.0025(8) C27 0.0171(9) 0.0182(9) 0.0183(10) -0.0006(8) -0.0030(8) -0.0005(8) C28 0.0296(12) 0.0312(12) 0.0218(11) 0.0074(9) 0.0061(9) -0.0003(9) C31 0.0193(10) 0.0168(9) 0.0196(10) -0.0013(8) 0.0035(8) 0.0026(8) C32 0.0268(11) 0.0194(10) 0.0181(10) 0.0000(8) 0.0073(8) 0.0035(8) C33 0.0398(13) 0.0291(12) 0.0180(10) 0.0016(9) 0.0066(9) 0.0021(10) C34 0.0454(15) 0.0336(13) 0.0246(12) 0.0066(10) 0.0170(11) 0.0024(11) C35 0.0331(13) 0.0327(13) 0.0370(13) 0.0080(10) 0.0149(11) -0.0066(10) C36 0.0255(11) 0.0276(11) 0.0297(12) 0.0029(9) 0.0050(9) -0.0031(9) C37 0.0216(10) 0.0158(9) 0.0198(10) 0.0029(8) 0.0066(8) 0.0016(8) C38 0.0308(12) 0.0392(13) 0.0223(11) -0.0052(10) -0.0040(9) -0.0071(10) C41 0.0264(12) 0.0310(12) 0.0370(13) 0.0116(10) 0.0019(10) 0.0047(10) C51 0.0338(13) 0.0371(13) 0.0233(11) 0.0004(10) 0.0067(9) -0.0010(10) C52 0.0623(18) 0.0454(16) 0.0256(12) -0.0100(11) 0.0060(12) 0.0036(14) C53 0.0408(14) 0.0300(13) 0.0413(14) -0.0144(11) -0.0025(12) -0.0022(11) C54 0.0339(13) 0.0224(11) 0.0334(12) -0.0051(9) 0.0073(10) -0.0042(9) C55 0.0537(17) 0.0244(12) 0.0689(19) 0.0094(12) 0.0298(16) 0.0090(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Na O2 2.4430(17) 2 ? Na O1 2.4715(17) . ? Na O2 2.5195(17) . ? Na S2 2.8021(12) . ? Na S3 2.8157(11) . ? Na S1 2.8734(11) . ? Na Na 3.2987(19) 2 ? B H1 1.138(18) . ? B N11 1.545(3) . ? B N31 1.553(3) . ? B N21 1.559(3) . ? N12 C11 1.370(2) . ? N12 C12 1.387(3) . ? N12 C18 1.457(3) . ? N11 C11 1.364(3) . ? N11 C17 1.404(2) . ? N22 C21 1.375(2) . ? N22 C22 1.386(2) . ? N22 C28 1.458(3) . ? N21 C21 1.362(2) . ? N21 C27 1.399(2) . ? N32 C31 1.373(2) . ? N32 C32 1.385(3) . ? N32 C38 1.450(2) . ? N31 C31 1.365(2) . ? N31 C37 1.401(2) . ? S1 C11 1.704(2) . ? S2 C21 1.696(2) . ? S3 C31 1.695(2) . ? O1 C41 1.450(2) 2 ? O1 C41 1.450(2) . ? O1 Na 2.4716(17) 2 ? O2 C54 1.450(2) . ? O2 C51 1.452(3) . ? O2 Na 2.4431(17) 2 ? C12 C17 1.386(3) . ? C12 C13 1.393(3) . ? C13 C14 1.387(3) . ? C14 C15 1.383(4) . ? C15 C16 1.395(3) . ? C16 C17 1.394(3) . ? C22 C27 1.391(3) . ? C22 C23 1.393(3) . ? C23 C24 1.387(3) . ? C24 C25 1.392(3) . ? C25 C26 1.388(3) . ? C26 C27 1.396(3) . ? C32 C33 1.393(3) . ? C32 C37 1.394(3) . ? C33 C34 1.379(3) . ? C34 C35 1.395(3) . ? C35 C36 1.400(3) . ? C36 C37 1.391(3) . ? C41 C55 1.515(3) . ? C51 C52 1.526(3) . ? C52 C53 1.517(4) . ? C53 C54 1.510(3) . ? C55 C55 1.501(5) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Na O1 82.27(5) 2 . ? O2 Na O2 78.54(6) 2 . ? O1 Na O2 80.74(5) . . ? O2 Na S2 155.01(5) 2 . ? O1 Na S2 107.93(4) . . ? O2 Na S2 80.69(5) . . ? O2 Na S3 111.14(5) 2 . ? O1 Na S3 80.45(4) . . ? O2 Na S3 157.37(5) . . ? S2 Na S3 93.27(3) . . ? O2 Na S1 84.53(5) 2 . ? O1 Na S1 158.28(3) . . ? O2 Na S1 113.39(5) . . ? S2 Na S1 91.14(3) . . ? S3 Na S1 88.37(4) . . ? O2 Na Na 49.34(4) 2 2 ? O1 Na Na 48.14(4) . 2 ? O2 Na Na 47.36(4) . 2 ? S2 Na Na 121.18(4) . 2 ? S3 Na Na 123.13(3) . 2 ? S1 Na Na 129.56(3) . 2 ? H1 B N11 107.1(9) . . ? H1 B N31 105.1(9) . . ? N11 B N31 113.18(16) . . ? H1 B N21 106.7(9) . . ? N11 B N21 112.41(17) . . ? N31 B N21 111.73(16) . . ? C11 N12 C12 109.47(17) . . ? C11 N12 C18 126.46(17) . . ? C12 N12 C18 123.99(17) . . ? C11 N11 C17 107.84(16) . . ? C11 N11 B 132.36(16) . . ? C17 N11 B 119.47(16) . . ? C21 N22 C22 109.34(16) . . ? C21 N22 C28 125.80(17) . . ? C22 N22 C28 124.81(17) . . ? C21 N21 C27 107.84(16) . . ? C21 N21 B 132.32(17) . . ? C27 N21 B 119.83(16) . . ? C31 N32 C32 109.55(16) . . ? C31 N32 C38 125.45(17) . . ? C32 N32 C38 124.83(17) . . ? C31 N31 C37 108.01(16) . . ? C31 N31 B 132.34(16) . . ? C37 N31 B 119.57(16) . . ? C11 S1 Na 97.02(7) . . ? C21 S2 Na 99.63(7) . . ? C31 S3 Na 102.71(7) . . ? C41 O1 C41 108.7(2) 2 . ? C41 O1 Na 123.30(10) 2 . ? C41 O1 Na 108.61(10) . . ? C41 O1 Na 108.61(10) 2 2 ? C41 O1 Na 123.30(10) . 2 ? Na O1 Na 83.72(7) . 2 ? C54 O2 C51 108.58(15) . . ? C54 O2 Na 128.40(12) . 2 ? C51 O2 Na 107.46(12) . 2 ? C54 O2 Na 101.02(12) . . ? C51 O2 Na 128.87(12) . . ? Na O2 Na 83.30(6) 2 . ? N11 C11 N12 108.15(16) . . ? N11 C11 S1 128.66(15) . . ? N12 C11 S1 123.18(15) . . ? C17 C12 N12 106.46(17) . . ? C17 C12 C13 122.4(2) . . ? N12 C12 C13 131.1(2) . . ? C14 C13 C12 116.7(2) . . ? C15 C14 C13 121.4(2) . . ? C14 C15 C16 121.7(2) . . ? C17 C16 C15 117.2(2) . . ? C12 C17 C16 120.46(19) . . ? C12 C17 N11 108.05(18) . . ? C16 C17 N11 131.5(2) . . ? N21 C21 N22 108.26(17) . . ? N21 C21 S2 128.75(15) . . ? N22 C21 S2 123.00(15) . . ? N22 C22 C27 106.25(16) . . ? N22 C22 C23 131.47(19) . . ? C27 C22 C23 122.28(19) . . ? C24 C23 C22 116.8(2) . . ? C23 C24 C25 121.3(2) . . ? C26 C25 C24 121.8(2) . . ? C25 C26 C27 117.18(19) . . ? C22 C27 C26 120.62(18) . . ? C22 C27 N21 108.30(17) . . ? C26 C27 N21 131.07(18) . . ? N31 C31 N32 108.11(16) . . ? N31 C31 S3 129.24(15) . . ? N32 C31 S3 122.61(15) . . ? N32 C32 C33 130.68(19) . . ? N32 C32 C37 106.41(17) . . ? C33 C32 C37 122.9(2) . . ? C34 C33 C32 116.4(2) . . ? C33 C34 C35 121.6(2) . . ? C34 C35 C36 121.7(2) . . ? C37 C36 C35 117.0(2) . . ? C36 C37 C32 120.36(19) . . ? C36 C37 N31 131.72(18) . . ? C32 C37 N31 107.91(17) . . ? O1 C41 C55 105.59(19) . . ? O2 C51 C52 105.76(18) . . ? C53 C52 C51 102.62(19) . . ? C54 C53 C52 100.87(19) . . ? O2 C54 C53 105.61(17) . . ? C55 C55 C41 102.01(15) 2 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.55 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.594 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.071 _database_code_depnum_ccdc_archive 'CCDC 794067' ####################################################################### # # 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_bbmcus10 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H25 B Cu N4 P S2' _chemical_formula_weight 478.87 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' B B 0.0013 0.0007 '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' P P 0.1023 0.0942 '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 P2(1)/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 15.943(2) _cell_length_b 8.8788(11) _cell_length_c 16.066(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.346(2) _cell_angle_gamma 90.00 _cell_volume 2212.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9888 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 32.34 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 1.261 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.7866 _exptl_absorpt_correction_T_max 0.8843 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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_reflns_number 37547 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 32.73 _reflns_number_total 7811 _reflns_number_gt 6310 _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^)+(0.0412P)^2^+0.6280P] 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 7811 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0848 _refine_ls_wR_factor_gt 0.0789 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.059 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.353802(11) 0.86552(2) 0.222133(11) 0.02387(5) Uani 1 1 d . . . B B 0.24292(9) 1.10658(16) 0.18783(9) 0.0163(2) Uani 1 1 d . . . H12 H 0.2283(11) 1.2167(19) 0.2170(11) 0.021(4) Uiso 1 1 d . . . H11 H 0.3004(11) 1.0531(19) 0.2343(11) 0.023(4) Uiso 1 1 d . . . S1 S 0.34260(2) 0.88121(4) 0.07534(2) 0.02293(7) Uani 1 1 d . . . S2 S 0.23652(2) 0.73483(4) 0.24248(2) 0.02365(7) Uani 1 1 d . . . N11 N 0.26390(7) 1.14677(12) 0.10067(7) 0.01603(19) Uani 1 1 d . . . N12 N 0.29534(7) 1.12336(13) -0.02637(7) 0.0194(2) Uani 1 1 d . . . N21 N 0.16231(7) 1.00210(12) 0.17496(7) 0.0174(2) Uani 1 1 d . . . N22 N 0.07197(8) 0.81042(14) 0.16944(8) 0.0237(2) Uani 1 1 d . . . P P 0.47726(2) 0.88996(4) 0.31787(2) 0.02220(8) Uani 1 1 d . . . C1 C 0.48216(13) 1.0599(2) 0.38223(12) 0.0424(4) Uani 1 1 d . . . H1A H 0.5366 1.0619 0.4256 0.064 Uiso 1 1 calc R . . H1B H 0.4339 1.0607 0.4105 0.064 Uiso 1 1 calc R . . H1C H 0.4786 1.1486 0.3453 0.064 Uiso 1 1 calc R . . C2 C 0.57512(11) 0.9119(3) 0.27877(12) 0.0441(5) Uani 1 1 d . . . H2A H 0.6217 0.9493 0.3251 0.066 Uiso 1 1 calc R . . H2B H 0.5647 0.9839 0.2313 0.066 Uiso 1 1 calc R . . H2C H 0.5916 0.8143 0.2589 0.066 Uiso 1 1 calc R . . C3 C 0.50831(11) 0.74792(19) 0.40086(11) 0.0348(4) Uani 1 1 d . . . H3A H 0.5598 0.7817 0.4427 0.052 Uiso 1 1 calc R . . H3B H 0.5208 0.6530 0.3750 0.052 Uiso 1 1 calc R . . H3C H 0.4610 0.7325 0.4296 0.052 Uiso 1 1 calc R . . C11 C 0.15644(9) 0.85336(15) 0.19337(8) 0.0189(2) Uani 1 1 d . . . C12 C 0.07874(8) 1.05439(16) 0.14064(8) 0.0198(2) Uani 1 1 d . . . C13 C 0.04842(9) 1.19717(18) 0.11388(10) 0.0270(3) Uani 1 1 d . . . H13A H 0.0866 1.2801 0.1166 0.032 Uiso 1 1 calc R . . C14 C -0.03987(10) 1.2139(2) 0.08300(12) 0.0349(4) Uani 1 1 d . . . H14A H -0.0624 1.3105 0.0646 0.042 Uiso 1 1 calc R . . C15 C -0.09621(10) 1.0926(2) 0.07829(12) 0.0379(4) Uani 1 1 d . . . H15A H -0.1562 1.1082 0.0564 0.046 Uiso 1 1 calc R . . C16 C -0.06690(10) 0.9497(2) 0.10472(11) 0.0332(3) Uani 1 1 d . . . H16A H -0.1052 0.8668 0.1013 0.040 Uiso 1 1 calc R . . C17 C 0.02202(9) 0.93358(17) 0.13676(9) 0.0235(3) Uani 1 1 d . . . C21 C 0.03854(11) 0.65973(18) 0.17753(13) 0.0353(4) Uani 1 1 d . . . H21A H 0.0857 0.5939 0.2063 0.053 Uiso 1 1 calc R . . H21B H 0.0128 0.6196 0.1205 0.053 Uiso 1 1 calc R . . H21C H -0.0054 0.6644 0.2112 0.053 Uiso 1 1 calc R . . C31 C 0.29806(8) 1.05321(14) 0.05017(8) 0.0171(2) Uani 1 1 d . . . C32 C 0.24494(8) 1.28348(14) 0.05711(8) 0.0164(2) Uani 1 1 d . . . C33 C 0.21800(8) 1.42205(15) 0.08285(8) 0.0196(2) Uani 1 1 d . . . H33A H 0.2055 1.4341 0.1375 0.023 Uiso 1 1 calc R . . C34 C 0.21020(9) 1.54148(16) 0.02579(9) 0.0242(3) Uani 1 1 d . . . H34A H 0.1928 1.6372 0.0422 0.029 Uiso 1 1 calc R . . C35 C 0.22731(10) 1.52423(18) -0.05532(10) 0.0285(3) Uani 1 1 d . . . H35A H 0.2201 1.6077 -0.0933 0.034 Uiso 1 1 calc R . . C36 C 0.25470(10) 1.38708(17) -0.08119(9) 0.0254(3) Uani 1 1 d . . . H36A H 0.2666 1.3748 -0.1361 0.030 Uiso 1 1 calc R . . C37 C 0.26395(8) 1.26862(15) -0.02313(8) 0.0187(2) Uani 1 1 d . . . C41 C 0.32955(11) 1.06181(19) -0.09539(9) 0.0294(3) Uani 1 1 d . . . H41A H 0.3175 0.9536 -0.1006 0.044 Uiso 1 1 calc R . . H41B H 0.3920 1.0782 -0.0831 0.044 Uiso 1 1 calc R . . H41C H 0.3023 1.1121 -0.1491 0.044 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 Cu 0.01778(9) 0.02583(10) 0.02479(9) 0.00015(6) -0.00166(6) 0.00426(6) B 0.0157(6) 0.0184(6) 0.0148(6) 0.0003(5) 0.0032(5) 0.0007(5) S1 0.02530(17) 0.01939(15) 0.02522(16) -0.00257(12) 0.00811(13) 0.00313(12) S2 0.02646(17) 0.01903(15) 0.02543(16) 0.00436(12) 0.00593(13) 0.00353(12) N11 0.0153(5) 0.0174(5) 0.0155(5) -0.0006(4) 0.0037(4) -0.0004(4) N12 0.0200(5) 0.0231(5) 0.0162(5) -0.0032(4) 0.0064(4) -0.0023(4) N21 0.0145(5) 0.0192(5) 0.0187(5) 0.0020(4) 0.0040(4) 0.0013(4) N22 0.0203(5) 0.0210(6) 0.0306(6) -0.0020(5) 0.0077(5) -0.0039(4) P 0.01660(15) 0.02603(18) 0.02173(16) -0.00050(13) -0.00015(12) 0.00442(12) C1 0.0487(11) 0.0322(9) 0.0408(10) -0.0084(7) -0.0008(8) 0.0076(8) C2 0.0238(8) 0.0744(14) 0.0339(9) 0.0069(9) 0.0065(7) 0.0061(8) C3 0.0308(8) 0.0303(8) 0.0372(8) 0.0069(7) -0.0048(7) 0.0025(6) C11 0.0202(6) 0.0194(6) 0.0181(5) -0.0008(4) 0.0067(5) -0.0005(4) C12 0.0138(5) 0.0250(6) 0.0204(6) 0.0007(5) 0.0038(4) 0.0007(5) C13 0.0184(6) 0.0276(7) 0.0339(8) 0.0063(6) 0.0036(5) 0.0024(5) C14 0.0198(7) 0.0369(9) 0.0451(9) 0.0069(7) 0.0018(6) 0.0066(6) C15 0.0153(6) 0.0458(10) 0.0489(10) -0.0005(8) -0.0003(6) 0.0034(6) C16 0.0179(6) 0.0358(8) 0.0439(9) -0.0054(7) 0.0033(6) -0.0046(6) C17 0.0179(6) 0.0257(7) 0.0272(7) -0.0032(5) 0.0059(5) -0.0023(5) C21 0.0319(8) 0.0234(7) 0.0521(10) -0.0011(7) 0.0129(7) -0.0089(6) C31 0.0136(5) 0.0197(6) 0.0176(5) -0.0031(4) 0.0030(4) -0.0034(4) C32 0.0134(5) 0.0186(6) 0.0164(5) 0.0009(4) 0.0019(4) -0.0022(4) C33 0.0179(6) 0.0204(6) 0.0202(6) 0.0010(5) 0.0040(5) 0.0009(5) C34 0.0240(6) 0.0197(6) 0.0276(7) 0.0041(5) 0.0029(5) 0.0009(5) C35 0.0316(7) 0.0265(7) 0.0268(7) 0.0094(6) 0.0057(6) -0.0009(6) C36 0.0265(7) 0.0321(7) 0.0182(6) 0.0039(5) 0.0065(5) -0.0026(6) C37 0.0167(5) 0.0224(6) 0.0164(5) -0.0002(4) 0.0023(4) -0.0031(4) C41 0.0374(8) 0.0326(8) 0.0220(6) -0.0049(6) 0.0146(6) -0.0001(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu P 2.2112(4) . ? Cu S2 2.2873(5) . ? Cu S1 2.3278(5) . ? Cu B 2.7495(14) . ? B H12 1.132(17) . ? B H11 1.143(17) . ? B N11 1.5544(17) . ? B N21 1.5596(18) . ? S1 C31 1.6932(14) . ? S2 C11 1.7014(14) . ? N11 C31 1.3598(16) . ? N11 C32 1.3989(16) . ? N12 C31 1.3701(17) . ? N12 C37 1.3888(17) . ? N12 C41 1.4508(17) . ? N21 C11 1.3613(16) . ? N21 C12 1.3984(16) . ? N22 C11 1.3667(17) . ? N22 C17 1.3829(19) . ? N22 C21 1.4570(19) . ? P C3 1.8190(16) . ? P C1 1.8207(18) . ? P C2 1.8218(18) . ? C12 C13 1.389(2) . ? C12 C17 1.3951(19) . ? C13 C14 1.388(2) . ? C14 C15 1.394(2) . ? C15 C16 1.384(3) . ? C16 C17 1.399(2) . ? C32 C33 1.3968(18) . ? C32 C37 1.3969(18) . ? C33 C34 1.3883(19) . ? C34 C35 1.400(2) . ? C35 C36 1.389(2) . ? C36 C37 1.3909(19) . ? 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 P Cu S2 125.183(17) . . ? P Cu S1 123.136(17) . . ? S2 Cu S1 107.524(15) . . ? P Cu B 119.40(3) . . ? S2 Cu B 85.10(3) . . ? S1 Cu B 81.66(3) . . ? H12 B H11 107.4(12) . . ? H12 B N11 106.4(8) . . ? H11 B N11 112.2(8) . . ? H12 B N21 109.1(8) . . ? H11 B N21 110.5(9) . . ? N11 B N21 111.04(10) . . ? H12 B Cu 140.7(9) . . ? H11 B Cu 33.3(9) . . ? N11 B Cu 95.58(7) . . ? N21 B Cu 92.04(7) . . ? C31 S1 Cu 103.05(4) . . ? C11 S2 Cu 99.82(5) . . ? C31 N11 C32 107.56(10) . . ? C31 N11 B 126.60(11) . . ? C32 N11 B 125.69(10) . . ? C31 N12 C37 109.00(10) . . ? C31 N12 C41 125.11(12) . . ? C37 N12 C41 125.50(12) . . ? C11 N21 C12 107.50(11) . . ? C11 N21 B 130.10(11) . . ? C12 N21 B 122.40(11) . . ? C11 N22 C17 109.26(11) . . ? C11 N22 C21 126.01(13) . . ? C17 N22 C21 124.72(13) . . ? C3 P C1 100.93(9) . . ? C3 P C2 102.54(9) . . ? C1 P C2 100.33(10) . . ? C3 P Cu 119.32(6) . . ? C1 P Cu 113.01(6) . . ? C2 P Cu 117.79(6) . . ? N21 C11 N22 108.80(11) . . ? N21 C11 S2 128.24(10) . . ? N22 C11 S2 122.89(10) . . ? C13 C12 C17 120.81(13) . . ? C13 C12 N21 131.06(13) . . ? C17 C12 N21 108.13(12) . . ? C14 C13 C12 117.40(14) . . ? C13 C14 C15 121.60(15) . . ? C16 C15 C14 121.62(14) . . ? C15 C16 C17 116.62(15) . . ? N22 C17 C12 106.29(12) . . ? N22 C17 C16 131.76(14) . . ? C12 C17 C16 121.94(14) . . ? N11 C31 N12 108.88(11) . . ? N11 C31 S1 127.75(10) . . ? N12 C31 S1 123.30(10) . . ? C33 C32 C37 120.22(12) . . ? C33 C32 N11 131.44(11) . . ? C37 C32 N11 108.17(11) . . ? C34 C33 C32 117.65(12) . . ? C33 C34 C35 121.60(14) . . ? C36 C35 C34 121.11(13) . . ? C35 C36 C37 117.01(13) . . ? N12 C37 C36 131.33(12) . . ? N12 C37 C32 106.21(11) . . ? C36 C37 C32 122.38(13) . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 32.73 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.525 _refine_diff_density_min -0.390 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 936322' ####################################################################### # # 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_mebmnas10 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H64 B2 N8 Na2 O4 S4' _chemical_formula_weight 1012.91 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 '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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2914(9) _cell_length_b 10.6050(9) _cell_length_c 12.5970(11) _cell_angle_alpha 111.1290(10) _cell_angle_beta 94.9240(10) _cell_angle_gamma 95.1530(10) _cell_volume 1266.85(19) _cell_formula_units_Z 1 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 8684 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 32.34 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.257 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9386 _exptl_absorpt_correction_T_max 0.9748 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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_reflns_number 20510 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 30.51 _reflns_number_total 7686 _reflns_number_gt 5573 _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^)+(0.0680P)^2^+0.3091P] 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 7686 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1396 _refine_ls_wR_factor_gt 0.1268 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Na Na 0.84111(7) 1.74568(7) 0.41595(6) 0.02473(17) Uani 1 1 d . . . B B 1.06455(18) 1.9580(2) 0.33752(17) 0.0212(4) Uani 1 1 d . . . H11 H 1.0210(18) 1.872(2) 0.3609(17) 0.020(5) Uiso 1 1 d . . . H12 H 1.077(2) 2.059(2) 0.4075(19) 0.028(5) Uiso 1 1 d . . . S1 S 0.79375(4) 1.73822(4) 0.18825(4) 0.02353(11) Uani 1 1 d . . . S2 S 1.35592(4) 2.16833(5) 0.44384(4) 0.02544(12) Uani 1 1 d . . . N11 N 0.97489(13) 1.96427(14) 0.23354(12) 0.0196(3) Uani 1 1 d . . . N12 N 0.80814(14) 1.93561(15) 0.10017(13) 0.0227(3) Uani 1 1 d . . . N21 N 1.20397(14) 1.92697(14) 0.30353(12) 0.0196(3) Uani 1 1 d . . . N22 N 1.41911(14) 1.93379(15) 0.29787(13) 0.0213(3) Uani 1 1 d . . . C11 C 0.86187(16) 1.88298(17) 0.17596(14) 0.0201(3) Uani 1 1 d . . . C12 C 0.99340(16) 2.06882(17) 0.19164(14) 0.0202(3) Uani 1 1 d . . . C13 C 1.09427(17) 2.17641(18) 0.22012(15) 0.0237(4) Uani 1 1 d . . . H13A H 1.1651 2.1906 0.2785 0.028 Uiso 1 1 calc R . . C14 C 1.08645(19) 2.26199(19) 0.15924(16) 0.0268(4) Uani 1 1 d . . . H14A H 1.1543 2.3357 0.1756 0.032 Uiso 1 1 calc R . . C15 C 0.98153(19) 2.24287(19) 0.07439(16) 0.0277(4) Uani 1 1 d . . . H15A H 0.9796 2.3040 0.0348 0.033 Uiso 1 1 calc R . . C16 C 0.88074(19) 2.1369(2) 0.04692(16) 0.0266(4) Uani 1 1 d . . . H16A H 0.8092 2.1238 -0.0105 0.032 Uiso 1 1 calc R . . C17 C 0.88886(17) 2.05088(18) 0.10695(15) 0.0225(3) Uani 1 1 d . . . C21 C 0.68698(18) 1.8795(2) 0.02247(17) 0.0309(4) Uani 1 1 d . . . H21A H 0.6647 1.7836 0.0120 0.046 Uiso 1 1 calc R . . H21B H 0.6986 1.8861 -0.0518 0.046 Uiso 1 1 calc R . . H21C H 0.6159 1.9308 0.0547 0.046 Uiso 1 1 calc R . . C31 C 1.32224(16) 2.00653(17) 0.34716(15) 0.0201(3) Uani 1 1 d . . . C32 C 1.22815(16) 1.80187(17) 0.22584(14) 0.0198(3) Uani 1 1 d . . . C33 C 1.14280(17) 1.68486(17) 0.16060(15) 0.0216(3) Uani 1 1 d . . . H33A H 1.0508 1.6804 0.1642 0.026 Uiso 1 1 calc R . . C34 C 1.19763(18) 1.57468(18) 0.08992(16) 0.0248(4) Uani 1 1 d . . . H34A H 1.1416 1.4938 0.0435 0.030 Uiso 1 1 calc R . . C35 C 1.33328(18) 1.57983(19) 0.08540(16) 0.0264(4) Uani 1 1 d . . . H35A H 1.3672 1.5027 0.0357 0.032 Uiso 1 1 calc R . . C36 C 1.41946(18) 1.69586(19) 0.15234(16) 0.0254(4) Uani 1 1 d . . . H36A H 1.5118 1.6995 0.1506 0.031 Uiso 1 1 calc R . . C37 C 1.36352(17) 1.80618(17) 0.22193(15) 0.0209(3) Uani 1 1 d . . . C41 C 1.55859(16) 1.98367(19) 0.32443(17) 0.0272(4) Uani 1 1 d . . . H41A H 1.5834 2.0193 0.4078 0.041 Uiso 1 1 calc R . . H41B H 1.5776 2.0565 0.2953 0.041 Uiso 1 1 calc R . . H41C H 1.6090 1.9089 0.2882 0.041 Uiso 1 1 calc R . . C51 C 0.56636(19) 1.5125(2) 0.34396(18) 0.0337(4) Uani 1 1 d . . . H51A H 0.5223 1.5888 0.3367 0.040 Uiso 1 1 calc R . . H51B H 0.5587 1.5107 0.4212 0.040 Uiso 1 1 calc R . . C52 C 0.5033(2) 1.3793(2) 0.2529(2) 0.0417(5) Uani 1 1 d . . . H52A H 0.4570 1.3210 0.2877 0.050 Uiso 1 1 calc R . . H52B H 0.4394 1.3953 0.1971 0.050 Uiso 1 1 calc R . . C53 C 0.6145(3) 1.3138(3) 0.1955(3) 0.0681(9) Uani 1 1 d . . . H53A H 0.6385 1.2420 0.2236 0.082 Uiso 1 1 calc R . . H53B H 0.5898 1.2722 0.1113 0.082 Uiso 1 1 calc R . . C54 C 0.7249(2) 1.4237(2) 0.2252(2) 0.0407(5) Uani 1 1 d . . . H54A H 0.8089 1.3894 0.2377 0.049 Uiso 1 1 calc R . . H54B H 0.7296 1.4584 0.1622 0.049 Uiso 1 1 calc R . . C61 C 1.06574(19) 1.5479(2) 0.38688(17) 0.0286(4) Uani 1 1 d . . . H61A H 1.0518 1.5487 0.3084 0.034 Uiso 1 1 calc R . . H61B H 1.0117 1.4668 0.3887 0.034 Uiso 1 1 calc R . . C62 C 1.2094(2) 1.5460(2) 0.4218(2) 0.0468(6) Uani 1 1 d . . . H62A H 1.2204 1.4979 0.4757 0.056 Uiso 1 1 calc R . . H62B H 1.2543 1.5015 0.3541 0.056 Uiso 1 1 calc R . . C63 C 1.2613(2) 1.6946(2) 0.4791(2) 0.0375(5) Uani 1 1 d . . . H63A H 1.3396 1.7088 0.5355 0.045 Uiso 1 1 calc R . . H63B H 1.2847 1.7341 0.4220 0.045 Uiso 1 1 calc R . . C64 C 1.1489(2) 1.7556(2) 0.5371(2) 0.0392(5) Uani 1 1 d . . . H64A H 1.1551 1.7567 0.6162 0.047 Uiso 1 1 calc R . . H64B H 1.1487 1.8503 0.5404 0.047 Uiso 1 1 calc R . . O1 O 0.70238(13) 1.53024(14) 0.32803(12) 0.0316(3) Uani 1 1 d . . . O2 O 1.03119(13) 1.67065(14) 0.46898(12) 0.0298(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Na 0.0207(3) 0.0247(4) 0.0252(4) 0.0052(3) 0.0029(3) 0.0021(3) B 0.0170(8) 0.0249(9) 0.0192(9) 0.0056(7) 0.0024(7) 0.0011(7) S1 0.0184(2) 0.0218(2) 0.0265(2) 0.00542(17) 0.00203(16) -0.00140(16) S2 0.0200(2) 0.0212(2) 0.0274(2) 0.00054(17) 0.00266(16) -0.00028(16) N11 0.0171(6) 0.0187(7) 0.0204(7) 0.0044(5) 0.0021(5) 0.0010(5) N12 0.0179(7) 0.0253(7) 0.0214(7) 0.0055(6) -0.0012(5) 0.0013(6) N21 0.0172(6) 0.0197(7) 0.0201(7) 0.0057(6) 0.0021(5) 0.0016(5) N22 0.0162(6) 0.0196(7) 0.0244(7) 0.0041(6) 0.0022(5) 0.0014(5) C11 0.0163(7) 0.0212(8) 0.0194(8) 0.0031(6) 0.0034(6) 0.0032(6) C12 0.0203(8) 0.0200(8) 0.0180(7) 0.0038(6) 0.0038(6) 0.0038(6) C13 0.0233(8) 0.0229(8) 0.0216(8) 0.0050(7) 0.0017(7) 0.0009(7) C14 0.0295(9) 0.0222(8) 0.0261(9) 0.0061(7) 0.0057(7) 0.0001(7) C15 0.0329(10) 0.0264(9) 0.0258(9) 0.0112(8) 0.0056(7) 0.0060(8) C16 0.0264(9) 0.0296(9) 0.0235(9) 0.0087(7) 0.0030(7) 0.0067(7) C17 0.0204(8) 0.0225(8) 0.0212(8) 0.0038(7) 0.0033(6) 0.0044(6) C21 0.0201(9) 0.0402(11) 0.0279(9) 0.0104(8) -0.0051(7) -0.0019(8) C31 0.0188(8) 0.0200(8) 0.0207(8) 0.0071(6) 0.0015(6) 0.0013(6) C32 0.0203(8) 0.0196(8) 0.0197(8) 0.0074(6) 0.0016(6) 0.0030(6) C33 0.0210(8) 0.0208(8) 0.0217(8) 0.0076(7) 0.0005(6) -0.0004(6) C34 0.0268(9) 0.0202(8) 0.0237(9) 0.0054(7) -0.0007(7) -0.0011(7) C35 0.0273(9) 0.0210(8) 0.0269(9) 0.0036(7) 0.0039(7) 0.0047(7) C36 0.0206(8) 0.0248(9) 0.0288(9) 0.0067(7) 0.0044(7) 0.0045(7) C37 0.0200(8) 0.0189(8) 0.0217(8) 0.0052(6) 0.0025(6) 0.0011(6) C41 0.0157(8) 0.0273(9) 0.0325(10) 0.0048(8) 0.0023(7) -0.0002(7) C51 0.0262(10) 0.0341(11) 0.0340(10) 0.0058(9) 0.0021(8) 0.0004(8) C52 0.0314(11) 0.0337(11) 0.0468(13) 0.0029(10) -0.0016(9) -0.0048(9) C53 0.0440(15) 0.0519(16) 0.0696(19) -0.0203(14) 0.0123(13) -0.0130(12) C54 0.0430(12) 0.0306(11) 0.0362(11) -0.0012(9) 0.0120(9) -0.0058(9) C61 0.0267(9) 0.0258(9) 0.0293(10) 0.0068(8) 0.0007(7) 0.0009(7) C62 0.0290(11) 0.0390(12) 0.0537(14) -0.0040(11) -0.0060(10) 0.0103(9) C63 0.0261(10) 0.0413(12) 0.0389(11) 0.0093(10) 0.0003(8) -0.0002(9) C64 0.0280(10) 0.0317(11) 0.0448(12) 0.0010(9) -0.0073(9) 0.0054(8) O1 0.0288(7) 0.0286(7) 0.0283(7) 0.0016(6) 0.0049(5) -0.0052(6) O2 0.0219(6) 0.0271(7) 0.0359(8) 0.0068(6) -0.0001(5) 0.0040(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 Na O2 2.3118(15) . ? Na O1 2.4090(15) . ? Na S2 2.8016(9) 2_796 ? Na S1 2.8391(9) . ? B H12 1.10(2) . ? B H11 1.13(2) . ? B N21 1.562(2) . ? B N11 1.561(2) . ? S1 C11 1.6938(18) . ? S2 C31 1.6917(17) . ? S2 Na 2.8016(9) 2_796 ? N11 C11 1.359(2) . ? N11 C12 1.395(2) . ? N12 C11 1.370(2) . ? N12 C17 1.386(2) . ? N12 C21 1.451(2) . ? N21 C31 1.364(2) . ? N21 C32 1.395(2) . ? N22 C31 1.369(2) . ? N22 C37 1.381(2) . ? N22 C41 1.451(2) . ? C12 C13 1.392(2) . ? C12 C17 1.397(2) . ? C13 C14 1.387(3) . ? C14 C15 1.399(3) . ? C15 C16 1.381(3) . ? C16 C17 1.383(3) . ? C32 C33 1.390(2) . ? C32 C37 1.395(2) . ? C33 C34 1.390(3) . ? C34 C35 1.399(3) . ? C35 C36 1.393(3) . ? C36 C37 1.392(2) . ? C51 O1 1.436(2) . ? C51 C52 1.508(3) . ? C52 C53 1.495(4) . ? C53 C54 1.471(3) . ? C54 O1 1.432(2) . ? C61 O2 1.438(2) . ? C61 C62 1.510(3) . ? C62 C63 1.501(3) . ? C63 C64 1.493(3) . ? C64 O2 1.443(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Na O1 99.46(6) . . ? O2 Na S2 124.95(5) . 2_796 ? O1 Na S2 86.61(4) . 2_796 ? O2 Na S1 118.40(5) . . ? O1 Na S1 80.31(4) . . ? S2 Na S1 116.56(3) 2_796 . ? H12 B H11 114.8(15) . . ? H12 B N21 107.2(11) . . ? H11 B N21 107.3(10) . . ? H12 B N11 108.4(11) . . ? H11 B N11 109.0(10) . . ? N21 B N11 110.11(14) . . ? C11 S1 Na 112.01(6) . . ? C31 S2 Na 114.48(6) . 2_796 ? C11 N11 C12 107.78(14) . . ? C11 N11 B 128.60(15) . . ? C12 N11 B 123.31(14) . . ? C11 N12 C17 109.56(14) . . ? C11 N12 C21 125.99(16) . . ? C17 N12 C21 124.44(16) . . ? C31 N21 C32 107.65(14) . . ? C31 N21 B 128.73(14) . . ? C32 N21 B 123.43(14) . . ? C31 N22 C37 109.52(14) . . ? C31 N22 C41 124.56(15) . . ? C37 N22 C41 125.91(15) . . ? N11 C11 N12 108.46(15) . . ? N11 C11 S1 128.42(14) . . ? N12 C11 S1 123.11(13) . . ? C13 C12 N11 130.69(16) . . ? C13 C12 C17 120.86(17) . . ? N11 C12 C17 108.44(15) . . ? C14 C13 C12 116.78(17) . . ? C13 C14 C15 121.88(18) . . ? C16 C15 C14 121.34(18) . . ? C15 C16 C17 116.86(17) . . ? C16 C17 N12 131.99(17) . . ? C16 C17 C12 122.26(17) . . ? N12 C17 C12 105.74(15) . . ? N21 C31 N22 108.41(14) . . ? N21 C31 S2 129.60(13) . . ? N22 C31 S2 121.99(13) . . ? C33 C32 N21 130.86(16) . . ? C33 C32 C37 120.86(16) . . ? N21 C32 C37 108.27(14) . . ? C32 C33 C34 117.27(16) . . ? C33 C34 C35 121.69(16) . . ? C36 C35 C34 121.25(17) . . ? C37 C36 C35 116.64(16) . . ? N22 C37 C36 131.58(16) . . ? N22 C37 C32 106.15(14) . . ? C36 C37 C32 122.27(16) . . ? O1 C51 C52 107.55(17) . . ? C53 C52 C51 105.15(18) . . ? C54 C53 C52 105.9(2) . . ? O1 C54 C53 107.42(19) . . ? O2 C61 C62 105.70(16) . . ? C63 C62 C61 102.99(18) . . ? C64 C63 C62 103.37(18) . . ? O2 C64 C63 106.07(17) . . ? C54 O1 C51 109.18(15) . . ? C54 O1 Na 124.06(12) . . ? C51 O1 Na 122.83(12) . . ? C61 O2 C64 109.62(14) . . ? C61 O2 Na 116.15(11) . . ? C64 O2 Na 126.17(12) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.126 _refine_diff_density_min -0.744 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 936323' ####################################################################### # # 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_btmcups10 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C96 H104 B2 Cu2 N12 P2 S6' _chemical_formula_weight 1828.91 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 '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' P P 0.1023 0.0942 '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 P-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' _cell_length_a 15.4166(7) _cell_length_b 15.4166(7) _cell_length_c 11.4883(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2364.6(2) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9928 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 32.41 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 958 _exptl_absorpt_coefficient_mu 0.668 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.7313 _exptl_absorpt_correction_T_max 0.9674 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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_reflns_number 40931 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0169 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 32.60 _reflns_number_total 5563 _reflns_number_gt 4563 _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^)+(0.0416P)^2^+0.7530P] 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 5563 _refine_ls_number_parameters 215 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0890 _refine_ls_wR_factor_gt 0.0804 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.050 _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 Cu Cu 0.3333 -0.3333 0.83205(2) 0.02601(7) Uani 1 3 d S . . B B 0.3333 -0.3333 0.52274(16) 0.0180(3) Uani 1 3 d S . . H1 H 0.3333 -0.3333 0.426(2) 0.022 Uiso 1 3 d S . . S S 0.18621(2) -0.34512(2) 0.75529(2) 0.02638(7) Uani 1 1 d . . . N1 N 0.22778(6) -0.41872(6) 0.55789(7) 0.01852(15) Uani 1 1 d . . . N2 N 0.07401(7) -0.51161(7) 0.62765(8) 0.02330(17) Uani 1 1 d . . . P P 0.3333 -0.3333 1.02485(5) 0.03897(14) Uani 1 3 d S . . C10 C 0.4242(2) -0.2169(2) 1.09446(18) 0.0907(9) Uani 1 1 d . . . H10A H 0.4162 -0.2241 1.1791 0.136 Uiso 1 1 calc R . . H10B H 0.4132 -0.1625 1.0685 0.136 Uiso 1 1 calc R . . H10C H 0.4920 -0.2012 1.0732 0.136 Uiso 1 1 calc R . . C11 C 0.16370(7) -0.42531(8) 0.64391(9) 0.02026(18) Uani 1 1 d . . . C12 C 0.17767(7) -0.50407(7) 0.48789(9) 0.02026(18) Uani 1 1 d . . . C13 C 0.20866(8) -0.53382(8) 0.38970(10) 0.0255(2) Uani 1 1 d . . . H13A H 0.2749 -0.4953 0.3605 0.031 Uiso 1 1 calc R . . C14 C 0.13865(10) -0.62253(10) 0.33572(12) 0.0351(3) Uani 1 1 d . . . H14A H 0.1575 -0.6447 0.2682 0.042 Uiso 1 1 calc R . . C15 C 0.04162(11) -0.67933(10) 0.37884(13) 0.0391(3) Uani 1 1 d . . . H15A H -0.0044 -0.7391 0.3395 0.047 Uiso 1 1 calc R . . C16 C 0.01027(9) -0.65089(9) 0.47784(12) 0.0331(3) Uani 1 1 d . . . H16A H -0.0558 -0.6899 0.5075 0.040 Uiso 1 1 calc R . . C17 C 0.08065(8) -0.56216(8) 0.53132(10) 0.02332(19) Uani 1 1 d . . . C18 C -0.01487(8) -0.54523(10) 0.69933(11) 0.0307(2) Uani 1 1 d . . . H18A H 0.0030 -0.5056 0.7711 0.046 Uiso 1 1 calc R . . H18B H -0.0425 -0.6161 0.7188 0.046 Uiso 1 1 calc R . . H18C H -0.0650 -0.5366 0.6564 0.046 Uiso 1 1 calc R . . C20 C 0.10292(16) 0.04570(18) 0.5001(3) 0.0923(9) Uani 1 1 d D . . H20A H 0.1739 0.0772 0.5004 0.111 Uiso 1 1 calc R . . C21 C -0.03077(19) -0.8396(2) 0.8716(3) 0.0730(14) Uani 0.620(6) 1 d PG A 1 H21A H -0.0740 -0.9102 0.8717 0.088 Uiso 0.620(6) 1 calc PR A 1 C22 C 0.0372(2) -0.7940(2) 0.7813(3) 0.0663(11) Uani 0.620(6) 1 d PG A 1 H22A H 0.0405 -0.8334 0.7197 0.080 Uiso 0.620(6) 1 calc PR A 1 C23 C 0.1004(2) -0.6908(2) 0.7811(3) 0.0618(12) Uani 0.620(6) 1 d PG A 1 H23A H 0.1469 -0.6596 0.7193 0.074 Uiso 0.620(6) 1 calc PR A 1 C24 C 0.0956(2) -0.6331(2) 0.8711(3) 0.0573(12) Uani 0.620(6) 1 d PG A 1 H24A H 0.1388 -0.5626 0.8710 0.069 Uiso 0.620(6) 1 calc PR A 1 C25 C 0.0276(2) -0.6787(3) 0.9614(3) 0.0652(12) Uani 0.620(6) 1 d PG A 1 H25A H 0.0243 -0.6393 1.0230 0.078 Uiso 0.620(6) 1 calc PR A 1 C26 C -0.03559(18) -0.7820(3) 0.9616(3) 0.0684(19) Uani 0.620(6) 1 d PG A 1 H26A H -0.0821 -0.8131 1.0233 0.082 Uiso 0.620(6) 1 calc PR A 1 C31A C -0.0505(3) -0.7988(3) 0.9293(5) 0.055(2) Uani 0.380(6) 1 d PG A 2 H31A H -0.1042 -0.8652 0.9405 0.066 Uiso 0.380(6) 1 calc PR A 2 C32A C 0.0118(3) -0.7760(3) 0.8329(4) 0.0533(14) Uani 0.380(6) 1 d PG A 2 H32A H 0.0006 -0.8268 0.7783 0.064 Uiso 0.380(6) 1 calc PR A 2 C33A C 0.0903(3) -0.6788(3) 0.8165(4) 0.0420(13) Uani 0.380(6) 1 d PG A 2 H33A H 0.1329 -0.6632 0.7507 0.050 Uiso 0.380(6) 1 calc PR A 2 C34A C 0.1066(3) -0.6045(2) 0.8964(4) 0.0508(14) Uani 0.380(6) 1 d PG A 2 H34A H 0.1603 -0.5381 0.8852 0.061 Uiso 0.380(6) 1 calc PR A 2 C35A C 0.0443(3) -0.6273(3) 0.9927(4) 0.0523(13) Uani 0.380(6) 1 d PG A 2 H35A H 0.0555 -0.5764 1.0473 0.063 Uiso 0.380(6) 1 calc PR A 2 C36A C -0.0342(2) -0.7244(4) 1.0092(4) 0.0540(15) Uani 0.380(6) 1 d PG A 2 H36A H -0.0767 -0.7400 1.0750 0.065 Uiso 0.380(6) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.03013(9) 0.03013(9) 0.01777(11) 0.000 0.000 0.01507(4) B 0.0171(5) 0.0171(5) 0.0198(8) 0.000 0.000 0.0085(2) S 0.02526(13) 0.03105(14) 0.02434(13) -0.00544(10) 0.00146(9) 0.01520(11) N1 0.0171(3) 0.0171(3) 0.0206(4) -0.0011(3) -0.0004(3) 0.0080(3) N2 0.0178(4) 0.0233(4) 0.0267(4) 0.0025(3) 0.0024(3) 0.0087(3) P 0.0494(2) 0.0494(2) 0.0180(2) 0.000 0.000 0.02472(11) C10 0.116(2) 0.0798(15) 0.0431(10) -0.0232(10) -0.0325(12) 0.0236(15) C11 0.0182(4) 0.0212(4) 0.0221(4) 0.0011(3) 0.0006(3) 0.0104(4) C12 0.0198(4) 0.0177(4) 0.0238(4) -0.0011(3) -0.0031(3) 0.0098(3) C13 0.0260(5) 0.0246(5) 0.0278(5) -0.0047(4) -0.0019(4) 0.0141(4) C14 0.0386(6) 0.0294(6) 0.0372(6) -0.0125(5) -0.0057(5) 0.0170(5) C15 0.0359(6) 0.0247(5) 0.0483(8) -0.0129(5) -0.0093(6) 0.0089(5) C16 0.0245(5) 0.0225(5) 0.0430(7) -0.0026(5) -0.0039(5) 0.0047(4) C17 0.0206(4) 0.0197(4) 0.0276(5) 0.0009(4) -0.0016(4) 0.0085(4) C18 0.0193(5) 0.0343(6) 0.0354(6) 0.0074(5) 0.0070(4) 0.0110(4) C20 0.0441(10) 0.0537(12) 0.177(3) -0.0011(15) -0.0007(14) 0.0227(10) C21 0.0411(16) 0.073(3) 0.082(3) 0.025(2) -0.0051(16) 0.0115(17) C22 0.0476(17) 0.086(3) 0.060(2) 0.0111(19) -0.0055(15) 0.0296(17) C23 0.0449(17) 0.088(3) 0.060(3) 0.038(2) 0.0134(16) 0.0380(19) C24 0.0389(17) 0.068(3) 0.073(3) 0.039(2) 0.0147(18) 0.0324(17) C25 0.057(2) 0.088(3) 0.066(2) 0.025(2) 0.0107(17) 0.047(2) C26 0.0361(17) 0.098(4) 0.060(2) 0.036(3) 0.0149(16) 0.0250(19) C31A 0.036(3) 0.045(3) 0.063(4) 0.010(3) -0.008(3) 0.005(2) C32A 0.049(3) 0.057(3) 0.050(3) -0.004(2) -0.014(2) 0.024(2) C33A 0.032(2) 0.055(3) 0.038(3) 0.018(2) 0.0042(18) 0.021(2) C34A 0.045(3) 0.048(3) 0.055(3) 0.014(2) 0.000(2) 0.020(2) C35A 0.047(2) 0.051(3) 0.057(3) 0.012(2) 0.011(2) 0.023(2) C36A 0.040(2) 0.059(3) 0.052(3) 0.016(2) 0.0133(19) 0.016(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu P 2.2149(6) . ? Cu S 2.3544(3) 2_545 ? Cu S 2.3544(3) . ? Cu S 2.3544(3) 3_655 ? B H1 1.11(2) . ? B N1 1.5498(10) . ? B N1 1.5498(10) 3_655 ? B N1 1.5498(10) 2_545 ? S C11 1.6902(11) . ? N1 C11 1.3648(13) . ? N1 C12 1.3995(13) . ? N2 C11 1.3701(13) . ? N2 C17 1.3864(14) . ? N2 C18 1.4541(14) . ? P C10 1.819(2) 2_545 ? P C10 1.819(2) 3_655 ? P C10 1.819(2) . ? C12 C13 1.3892(15) . ? C12 C17 1.3960(15) . ? C13 C14 1.3941(16) . ? C14 C15 1.393(2) . ? C15 C16 1.390(2) . ? C16 C17 1.3935(15) . ? C20 C20 1.377(2) 5_556 ? C20 C20 1.377(2) 6_556 ? C21 C22 1.3900 . ? C21 C26 1.3900 . ? C22 C23 1.3900 . ? C23 C24 1.3900 . ? C24 C25 1.3900 . ? C25 C26 1.3900 . ? C31A C32A 1.3900 . ? C31A C36A 1.3900 . ? C32A C33A 1.3900 . ? C33A C34A 1.3900 . ? C34A C35A 1.3900 . ? C35A C36A 1.3900 . ? 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 P Cu S 111.997(8) . 2_545 ? P Cu S 111.996(8) . . ? S Cu S 106.832(9) 2_545 . ? P Cu S 111.996(8) . 3_655 ? S Cu S 106.834(9) 2_545 3_655 ? S Cu S 106.831(9) . 3_655 ? H1 B N1 105.10(7) . . ? H1 B N1 105.10(7) . 3_655 ? N1 B N1 113.47(6) . 3_655 ? H1 B N1 105.10(7) . 2_545 ? N1 B N1 113.47(6) . 2_545 ? N1 B N1 113.47(6) 3_655 2_545 ? C11 S Cu 100.23(4) . . ? C11 N1 C12 107.90(8) . . ? C11 N1 B 131.72(9) . . ? C12 N1 B 120.03(9) . . ? C11 N2 C17 109.42(9) . . ? C11 N2 C18 125.63(10) . . ? C17 N2 C18 124.96(9) . . ? C10 P C10 102.13(10) 2_545 3_655 ? C10 P C10 102.13(10) 2_545 . ? C10 P C10 102.13(10) 3_655 . ? C10 P Cu 116.07(8) 2_545 . ? C10 P Cu 116.07(8) 3_655 . ? C10 P Cu 116.08(8) . . ? N1 C11 N2 108.36(9) . . ? N1 C11 S 128.13(8) . . ? N2 C11 S 123.50(8) . . ? C13 C12 C17 120.89(10) . . ? C13 C12 N1 131.13(10) . . ? C17 C12 N1 107.96(9) . . ? C12 C13 C14 117.37(11) . . ? C15 C14 C13 121.33(12) . . ? C16 C15 C14 121.75(11) . . ? C15 C16 C17 116.60(11) . . ? N2 C17 C16 131.58(11) . . ? N2 C17 C12 106.34(9) . . ? C16 C17 C12 122.06(11) . . ? C20 C20 C20 120.001(3) 5_556 6_556 ? C22 C21 C26 120.0 . . ? C21 C22 C23 120.0 . . ? C24 C23 C22 120.0 . . ? C23 C24 C25 120.0 . . ? C24 C25 C26 120.0 . . ? C25 C26 C21 120.0 . . ? C32A C31A C36A 120.0 . . ? C33A C32A C31A 120.0 . . ? C32A C33A C34A 120.0 . . ? C35A C34A C33A 120.0 . . ? C36A C35A C34A 120.0 . . ? C35A C36A C31A 120.0 . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 32.60 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.634 _refine_diff_density_min -0.593 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 936324'