Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'G. Parkin' 'Bryte V. Kelly' 'Jospeh M. Tanski' _publ_contact_author_name 'Prof G. Parkin' _publ_contact_author_address ; Department of Chemistry Columbia University New York New York 10027 UNITED STATES OF AMERICA ; _publ_contact_author_email PARKIN@CHEM.COLUMBIA.EDU _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Multidentate Aryloxide and Oxo-Aryloxide Complexes of Antimony: Synthesis and Structural Characterization of [ 4-N(o-C6H4O)3]Sb(OSMe2), {{[ 3-N(o-C6H4OH)(o-C6H4O)2]Sb}2( 2-O)}2 and {[ 3-PhN(o-C6H4O)2]Sb}4( ?-O)2 ; data_lo2sbs10 _database_code_depnum_ccdc_archive 'CCDC 268879' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H34 N2 O6 Sb2' _chemical_formula_weight 882.19 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' Sb Sb -0.5866 1.5461 '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 9.7631(13) _cell_length_b 10.8520(17) _cell_length_c 17.345(3) _cell_angle_alpha 85.217(3) _cell_angle_beta 76.467(3) _cell_angle_gamma 88.987(3) _cell_volume 1780.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 243(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.646 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 1.568 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7988 _exptl_absorpt_correction_T_max 0.9257 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 243(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12313 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.1169 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 28.33 _reflns_number_total 7863 _reflns_number_gt 4574 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.1000P)^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 SHELXL _refine_ls_extinction_coef 0.0058(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7863 _refine_ls_number_parameters 452 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1278 _refine_ls_R_factor_gt 0.0681 _refine_ls_wR_factor_ref 0.2006 _refine_ls_wR_factor_gt 0.1785 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 Sb1 Sb 0.15334(6) -0.91379(6) 0.00938(4) 0.0329(2) Uani 1 1 d . . . Sb2 Sb -0.09171(6) -0.93519(6) 0.18416(4) 0.0380(2) Uani 1 1 d . . . O1 O -0.0245(6) -0.9900(6) 0.0751(4) 0.0342(15) Uani 1 1 d . . . O11 O 0.0411(6) -0.7620(5) -0.0072(4) 0.0356(15) Uani 1 1 d . . . O12 O 0.1641(6) -0.8757(6) 0.1258(4) 0.0373(15) Uani 1 1 d . . . O21 O -0.2697(7) -1.0237(7) 0.1832(4) 0.052(2) Uani 1 1 d . . . O22 O 0.0038(8) -1.0804(7) 0.2257(5) 0.065(2) Uani 1 1 d . . . N1 N 0.3062(7) -0.7058(6) 0.0079(5) 0.0299(17) Uani 1 1 d . . . N2 N -0.2289(9) -1.0005(8) 0.3347(5) 0.048(2) Uani 1 1 d . . . C11 C 0.1054(9) -0.6608(8) -0.0487(6) 0.035(2) Uani 1 1 d . . . C12 C 0.0345(11) -0.5832(9) -0.0949(7) 0.052(3) Uani 1 1 d . . . H12A H -0.0582 -0.6026 -0.0966 0.062 Uiso 1 1 calc R . . C13 C 0.0979(11) -0.4800(10) -0.1374(7) 0.050(3) Uani 1 1 d . . . H13A H 0.0481 -0.4291 -0.1679 0.060 Uiso 1 1 calc R . . C14 C 0.2315(11) -0.4491(10) -0.1366(7) 0.050(3) Uani 1 1 d . . . H14A H 0.2746 -0.3792 -0.1679 0.061 Uiso 1 1 calc R . . C15 C 0.3042(9) -0.5205(9) -0.0899(6) 0.038(2) Uani 1 1 d . . . H15A H 0.3958 -0.4981 -0.0880 0.046 Uiso 1 1 calc R . . C16 C 0.2402(9) -0.6266(8) -0.0453(6) 0.036(2) Uani 1 1 d . . . C17 C 0.1989(9) -0.7626(8) 0.1462(6) 0.034(2) Uani 1 1 d . . . C18 C 0.1639(9) -0.7362(10) 0.2262(6) 0.041(2) Uani 1 1 d . . . H18A H 0.1182 -0.7958 0.2659 0.050 Uiso 1 1 calc R . . C19 C 0.1962(11) -0.6241(10) 0.2458(7) 0.048(3) Uani 1 1 d . . . H19A H 0.1734 -0.6067 0.2995 0.057 Uiso 1 1 calc R . . C21 C -0.3848(10) -1.0044(10) 0.2442(7) 0.048(3) Uani 1 1 d . . . C22 C -0.5230(11) -1.0004(10) 0.2326(8) 0.058(3) Uani 1 1 d . . . H22A H -0.5344 -1.0043 0.1805 0.069 Uiso 1 1 calc R . . C23 C -0.6391(12) -0.9913(12) 0.2909(9) 0.070(4) Uani 1 1 d . . . H23A H -0.7289 -0.9896 0.2798 0.083 Uiso 1 1 calc R . . C24 C -0.6239(15) -0.9842(17) 0.3687(9) 0.103(6) Uani 1 1 d . . . H24A H -0.7037 -0.9795 0.4109 0.124 Uiso 1 1 calc R . . C25 C -0.4878(13) -0.9844(15) 0.3831(8) 0.081(4) Uani 1 1 d . . . H25A H -0.4766 -0.9769 0.4349 0.097 Uiso 1 1 calc R . . C26 C -0.3710(11) -0.9955(10) 0.3217(6) 0.050(3) Uani 1 1 d . . . C27 C -0.0565(12) -1.1596(11) 0.2894(7) 0.053(3) Uani 1 1 d . . . C28 C -0.0008(13) -1.2762(11) 0.2991(8) 0.063(3) Uani 1 1 d . . . H28A H 0.0785 -1.3004 0.2612 0.076 Uiso 1 1 calc R . . C29 C -0.0582(14) -1.3565(12) 0.3621(9) 0.073(4) Uani 1 1 d . . . H29A H -0.0203 -1.4362 0.3673 0.088 Uiso 1 1 calc R . . C110 C 0.2622(10) -0.5343(10) 0.1883(7) 0.045(3) Uani 1 1 d . . . H11A H 0.2832 -0.4564 0.2028 0.054 Uiso 1 1 calc R . . C111 C 0.2961(9) -0.5597(9) 0.1113(6) 0.038(2) Uani 1 1 d . . . H11B H 0.3410 -0.4986 0.0724 0.045 Uiso 1 1 calc R . . C112 C 0.2665(8) -0.6741(8) 0.0878(6) 0.035(2) Uani 1 1 d . . . C113 C 0.4541(8) -0.7363(8) -0.0211(6) 0.032(2) Uani 1 1 d . . . C114 C 0.5419(9) -0.7483(9) 0.0309(6) 0.038(2) Uani 1 1 d . . . H11C H 0.5087 -0.7348 0.0849 0.046 Uiso 1 1 calc R . . C115 C 0.6836(10) -0.7816(10) 0.0000(7) 0.050(3) Uani 1 1 d . . . H11D H 0.7436 -0.7931 0.0353 0.060 Uiso 1 1 calc R . . C116 C 0.7367(10) -0.7977(9) -0.0772(7) 0.045(3) Uani 1 1 d . . . H11E H 0.8334 -0.8121 -0.0966 0.054 Uiso 1 1 calc R . . C117 C 0.6439(10) -0.7924(9) -0.1279(6) 0.041(2) Uani 1 1 d . . . H11F H 0.6763 -0.8108 -0.1811 0.050 Uiso 1 1 calc R . . C118 C 0.5036(9) -0.7597(9) -0.0995(6) 0.038(2) Uani 1 1 d . . . H11G H 0.4423 -0.7535 -0.1342 0.045 Uiso 1 1 calc R . . C210 C -0.1726(14) -1.3199(12) 0.4185(8) 0.072(4) Uani 1 1 d . . . H21A H -0.2123 -1.3738 0.4632 0.086 Uiso 1 1 calc R . . C211 C -0.2284(12) -1.2038(12) 0.4088(7) 0.062(3) Uani 1 1 d . . . H21B H -0.3067 -1.1794 0.4473 0.074 Uiso 1 1 calc R . . C212 C -0.1730(12) -1.1232(10) 0.3448(7) 0.051(3) Uani 1 1 d . . . C213 C -0.1809(12) -0.9041(10) 0.3749(6) 0.051(3) Uani 1 1 d . . . C214 C -0.2399(15) -0.7872(12) 0.3716(8) 0.074(4) Uani 1 1 d . . . H21C H -0.3144 -0.7718 0.3463 0.089 Uiso 1 1 calc R . . C215 C -0.1869(18) -0.6921(15) 0.4067(11) 0.105(6) Uani 1 1 d . . . H21D H -0.2261 -0.6125 0.4049 0.125 Uiso 1 1 calc R . . C216 C -0.0820(17) -0.7141(14) 0.4424(9) 0.084(4) Uani 1 1 d . . . H21E H -0.0494 -0.6505 0.4672 0.101 Uiso 1 1 calc R . . C217 C -0.0208(14) -0.8277(14) 0.4437(8) 0.071(4) Uani 1 1 d . . . H21F H 0.0558 -0.8413 0.4675 0.085 Uiso 1 1 calc R . . C218 C -0.0710(12) -0.9228(12) 0.4100(8) 0.065(3) Uani 1 1 d . . . H21G H -0.0288 -1.0012 0.4114 0.078 Uiso 1 1 calc R . . O1S O -0.6821(16) -1.4799(16) 0.4067(10) 0.159(6) Uani 1 1 d . . . C1S C -0.649(3) -1.360(2) 0.3832(15) 0.171(11) Uani 1 1 d . . . H1SA H -0.6458 -1.3151 0.4296 0.205 Uiso 1 1 calc R . . H1SB H -0.7218 -1.3216 0.3585 0.205 Uiso 1 1 calc R . . C2S C -0.517(3) -1.351(3) 0.3280(16) 0.191(15) Uani 1 1 d . . . H2SA H -0.4541 -1.2929 0.3437 0.229 Uiso 1 1 calc R . . H2SB H -0.5273 -1.3240 0.2743 0.229 Uiso 1 1 calc R . . C3S C -0.462(2) -1.483(3) 0.3327(16) 0.189(13) Uani 1 1 d . . . H3SA H -0.4461 -1.5167 0.2807 0.227 Uiso 1 1 calc R . . H3SB H -0.3734 -1.4857 0.3499 0.227 Uiso 1 1 calc R . . C4S C -0.567(2) -1.551(2) 0.3884(14) 0.136(8) Uani 1 1 d . . . H4SA H -0.5891 -1.6262 0.3661 0.163 Uiso 1 1 calc R . . H4SB H -0.5329 -1.5757 0.4364 0.163 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 Sb1 0.0275(3) 0.0321(4) 0.0373(4) -0.0020(3) -0.0041(3) -0.0038(2) Sb2 0.0396(4) 0.0397(4) 0.0336(4) -0.0051(3) -0.0056(3) -0.0008(3) O1 0.034(3) 0.044(4) 0.024(3) -0.004(3) -0.003(3) -0.017(3) O11 0.028(3) 0.033(4) 0.047(4) 0.001(3) -0.012(3) -0.003(3) O12 0.049(4) 0.035(4) 0.026(4) -0.006(3) -0.005(3) -0.008(3) O21 0.048(4) 0.061(5) 0.045(5) -0.017(4) 0.001(4) -0.014(4) O22 0.054(4) 0.062(5) 0.064(6) 0.019(4) 0.009(4) 0.022(4) N1 0.023(3) 0.031(4) 0.035(5) 0.001(3) -0.006(3) 0.000(3) N2 0.053(5) 0.059(6) 0.029(5) -0.001(4) -0.005(4) 0.010(4) C11 0.028(4) 0.032(5) 0.043(6) -0.007(4) -0.006(4) -0.001(4) C12 0.054(6) 0.041(6) 0.071(9) -0.002(6) -0.036(6) 0.004(5) C13 0.054(6) 0.051(7) 0.048(7) 0.006(5) -0.022(5) -0.004(5) C14 0.048(6) 0.046(7) 0.053(7) 0.011(5) -0.006(5) 0.004(5) C15 0.032(4) 0.040(6) 0.044(6) 0.000(5) -0.012(4) -0.010(4) C16 0.030(4) 0.032(5) 0.049(6) 0.003(4) -0.019(4) 0.001(4) C17 0.034(4) 0.028(5) 0.042(6) -0.003(4) -0.014(4) 0.002(4) C18 0.036(5) 0.053(7) 0.033(6) 0.000(5) -0.004(4) -0.002(4) C19 0.054(6) 0.054(7) 0.041(7) -0.014(5) -0.018(5) 0.010(5) C21 0.039(5) 0.046(6) 0.056(8) -0.011(5) -0.003(5) 0.000(5) C22 0.054(6) 0.060(8) 0.066(9) -0.013(6) -0.024(6) 0.005(6) C23 0.036(6) 0.075(9) 0.094(11) -0.018(8) -0.006(7) 0.013(6) C24 0.059(8) 0.175(18) 0.059(10) -0.022(11) 0.020(8) 0.033(9) C25 0.057(8) 0.132(14) 0.055(9) -0.016(8) -0.017(7) 0.016(8) C26 0.049(6) 0.063(8) 0.035(6) 0.002(5) -0.005(5) 0.015(5) C27 0.057(7) 0.058(8) 0.039(7) 0.008(5) -0.008(5) -0.001(6) C28 0.061(7) 0.056(8) 0.062(9) 0.008(6) 0.001(6) 0.018(6) C29 0.069(8) 0.051(8) 0.099(12) 0.021(8) -0.029(8) 0.001(6) C110 0.036(5) 0.049(7) 0.056(7) -0.015(6) -0.019(5) -0.003(5) C111 0.029(4) 0.039(6) 0.046(6) -0.006(5) -0.011(4) -0.006(4) C112 0.020(4) 0.037(5) 0.049(7) -0.005(5) -0.008(4) 0.006(4) C113 0.022(4) 0.026(5) 0.047(6) 0.003(4) -0.007(4) -0.012(3) C114 0.031(5) 0.044(6) 0.041(6) -0.004(5) -0.010(4) 0.000(4) C115 0.033(5) 0.056(7) 0.068(8) 0.003(6) -0.029(5) 0.011(5) C116 0.034(5) 0.036(6) 0.061(8) -0.007(5) 0.001(5) 0.006(4) C117 0.041(5) 0.044(6) 0.037(6) -0.005(5) -0.002(5) -0.006(4) C118 0.038(5) 0.042(6) 0.034(6) -0.002(4) -0.010(4) -0.013(4) C210 0.077(9) 0.065(9) 0.070(10) 0.036(7) -0.026(8) -0.019(7) C211 0.051(6) 0.070(9) 0.051(8) 0.006(6) 0.012(6) -0.014(6) C212 0.060(7) 0.047(7) 0.049(7) 0.001(5) -0.020(6) 0.012(5) C213 0.065(7) 0.053(7) 0.032(6) -0.004(5) -0.006(5) 0.007(6) C214 0.094(10) 0.071(9) 0.069(9) -0.031(7) -0.039(8) 0.033(8) C215 0.120(13) 0.073(11) 0.137(17) -0.030(10) -0.057(13) 0.032(10) C216 0.114(12) 0.065(10) 0.084(11) -0.025(8) -0.043(10) 0.015(9) C217 0.065(8) 0.089(11) 0.054(9) 0.002(7) -0.007(7) -0.009(8) C218 0.063(7) 0.065(9) 0.067(9) 0.009(7) -0.017(7) -0.001(6) O1S 0.131(12) 0.133(13) 0.171(16) 0.015(11) 0.042(11) 0.000(10) C1S 0.24(3) 0.104(18) 0.13(2) 0.024(15) 0.01(2) 0.027(19) C2S 0.136(19) 0.25(3) 0.18(3) 0.13(2) -0.073(19) -0.12(2) C3S 0.102(16) 0.27(3) 0.16(2) 0.07(2) 0.025(16) 0.062(19) C4S 0.104(14) 0.16(2) 0.13(2) 0.012(16) -0.004(14) 0.016(15) _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 Sb1 O1 1.992(5) . ? Sb1 O11 2.001(6) . ? Sb1 O12 2.121(6) . ? Sb1 O1 2.446(6) 2_535 ? Sb1 N1 2.723(7) . ? Sb2 O22 1.986(7) . ? Sb2 O1 1.989(6) . ? Sb2 O21 2.005(7) . ? Sb2 O12 2.538(6) . ? Sb2 N2 2.684(8) . ? O1 Sb1 2.446(6) 2_535 ? O11 C11 1.341(10) . ? O12 C17 1.375(10) . ? O21 C21 1.377(12) . ? O22 C27 1.363(13) . ? N1 C112 1.419(12) . ? N1 C113 1.455(10) . ? N1 C16 1.461(11) . ? N2 C212 1.443(13) . ? N2 C213 1.446(14) . ? N2 C26 1.456(13) . ? C11 C16 1.389(11) . ? C11 C12 1.398(13) . ? C12 C13 1.362(14) . ? C13 C14 1.355(14) . ? C14 C15 1.381(13) . ? C15 C16 1.401(12) . ? C17 C112 1.390(13) . ? C17 C18 1.402(13) . ? C18 C19 1.352(14) . ? C19 C110 1.385(15) . ? C21 C26 1.394(15) . ? C21 C22 1.409(14) . ? C22 C23 1.340(16) . ? C23 C24 1.401(19) . ? C24 C25 1.408(18) . ? C25 C26 1.377(16) . ? C27 C212 1.382(16) . ? C27 C28 1.382(15) . ? C28 C29 1.357(17) . ? C29 C210 1.379(19) . ? C110 C111 1.350(14) . ? C111 C112 1.394(13) . ? C113 C118 1.375(13) . ? C113 C114 1.381(12) . ? C114 C115 1.414(13) . ? C115 C116 1.343(15) . ? C116 C117 1.400(14) . ? C117 C118 1.394(13) . ? C210 C211 1.376(17) . ? C211 C212 1.366(15) . ? C213 C218 1.357(15) . ? C213 C214 1.386(16) . ? C214 C215 1.40(2) . ? C215 C216 1.323(19) . ? C216 C217 1.361(18) . ? C217 C218 1.378(17) . ? O1S C4S 1.35(2) . ? O1S C1S 1.36(2) . ? C1S C2S 1.42(3) . ? C2S C3S 1.53(3) . ? C3S C4S 1.40(3) . ? 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 Sb1 O11 87.4(2) . . ? O1 Sb1 O12 78.1(2) . . ? O11 Sb1 O12 93.8(3) . . ? O1 Sb1 O1 69.7(3) . 2_535 ? O11 Sb1 O1 85.9(2) . 2_535 ? O12 Sb1 O1 147.8(2) . 2_535 ? O1 Sb1 N1 136.8(2) . . ? O11 Sb1 N1 69.1(2) . . ? O12 Sb1 N1 68.3(2) . . ? O1 Sb1 N1 139.3(2) 2_535 . ? O22 Sb2 O1 89.0(3) . . ? O22 Sb2 O21 96.3(3) . . ? O1 Sb2 O21 84.4(3) . . ? O22 Sb2 O12 79.8(3) . . ? O1 Sb2 O12 68.6(2) . . ? O21 Sb2 O12 152.8(2) . . ? O22 Sb2 N2 71.0(3) . . ? O1 Sb2 N2 145.8(3) . . ? O21 Sb2 N2 71.1(3) . . ? O12 Sb2 N2 130.8(2) . . ? Sb2 O1 Sb1 116.7(3) . . ? Sb2 O1 Sb1 130.2(3) . 2_535 ? Sb1 O1 Sb1 110.3(3) . 2_535 ? C11 O11 Sb1 120.0(5) . . ? C17 O12 Sb1 124.5(6) . . ? C17 O12 Sb2 113.3(5) . . ? Sb1 O12 Sb2 92.8(2) . . ? C21 O21 Sb2 116.6(6) . . ? C27 O22 Sb2 124.8(7) . . ? C112 N1 C113 115.8(7) . . ? C112 N1 C16 112.6(7) . . ? C113 N1 C16 117.2(7) . . ? C112 N1 Sb1 103.5(5) . . ? C113 N1 Sb1 107.5(5) . . ? C16 N1 Sb1 97.3(5) . . ? C212 N2 C213 117.7(9) . . ? C212 N2 C26 115.2(9) . . ? C213 N2 C26 119.7(9) . . ? C212 N2 Sb2 100.0(6) . . ? C213 N2 Sb2 100.0(6) . . ? C26 N2 Sb2 97.3(6) . . ? O11 C11 C16 122.1(8) . . ? O11 C11 C12 120.0(8) . . ? C16 C11 C12 117.9(9) . . ? C13 C12 C11 120.9(9) . . ? C14 C13 C12 121.3(10) . . ? C13 C14 C15 120.0(10) . . ? C14 C15 C16 119.4(8) . . ? C11 C16 C15 120.5(8) . . ? C11 C16 N1 115.9(8) . . ? C15 C16 N1 123.6(7) . . ? O12 C17 C112 120.3(9) . . ? O12 C17 C18 119.7(8) . . ? C112 C17 C18 120.0(9) . . ? C19 C18 C17 119.4(9) . . ? C18 C19 C110 121.3(10) . . ? O21 C21 C26 121.4(9) . . ? O21 C21 C22 121.9(11) . . ? C26 C21 C22 116.5(10) . . ? C23 C22 C21 124.3(12) . . ? C22 C23 C24 118.6(12) . . ? C23 C24 C25 119.3(12) . . ? C26 C25 C24 120.4(13) . . ? C25 C26 C21 120.9(11) . . ? C25 C26 N2 122.0(10) . . ? C21 C26 N2 117.1(9) . . ? O22 C27 C212 120.2(10) . . ? O22 C27 C28 120.1(11) . . ? C212 C27 C28 119.7(10) . . ? C29 C28 C27 121.4(12) . . ? C28 C29 C210 119.2(12) . . ? C111 C110 C19 119.3(10) . . ? C110 C111 C112 121.8(9) . . ? C17 C112 C111 118.1(9) . . ? C17 C112 N1 118.6(8) . . ? C111 C112 N1 123.3(8) . . ? C118 C113 C114 120.4(8) . . ? C118 C113 N1 119.6(8) . . ? C114 C113 N1 119.9(9) . . ? C113 C114 C115 117.6(9) . . ? C116 C115 C114 123.2(9) . . ? C115 C116 C117 118.1(9) . . ? C118 C117 C116 120.1(9) . . ? C113 C118 C117 120.4(9) . . ? C211 C210 C29 119.4(11) . . ? C212 C211 C210 121.8(12) . . ? C211 C212 C27 118.5(11) . . ? C211 C212 N2 122.3(11) . . ? C27 C212 N2 119.2(10) . . ? C218 C213 C214 119.1(12) . . ? C218 C213 N2 121.2(11) . . ? C214 C213 N2 119.5(10) . . ? C213 C214 C215 119.1(13) . . ? C216 C215 C214 120.3(15) . . ? C215 C216 C217 120.8(14) . . ? C216 C217 C218 120.1(13) . . ? C213 C218 C217 120.5(13) . . ? C4S O1S C1S 110.4(18) . . ? O1S C1S C2S 110(2) . . ? C1S C2S C3S 102.2(17) . . ? C4S C3S C2S 106.2(18) . . ? O1S C4S C3S 108.4(19) . . ? _diffrn_measured_fraction_theta_max 0.886 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.886 _refine_diff_density_max 0.973 _refine_diff_density_min -0.783 _refine_diff_density_rms 0.220 data_lo3sbs20 _database_code_depnum_ccdc_archive 'CCDC 268880' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 N O4 S Sb' _chemical_formula_weight 490.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4517(10) _cell_length_b 8.7336(11) _cell_length_c 13.9596(16) _cell_angle_alpha 96.289(2) _cell_angle_beta 90.953(2) _cell_angle_gamma 112.482(2) _cell_volume 944.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 243(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description bulk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.724 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 1.597 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5144 _exptl_absorpt_correction_T_max 0.5971 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 243(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6313 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 28.02 _reflns_number_total 4058 _reflns_number_gt 3747 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0900P)^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 SHELXL _refine_ls_extinction_coef 0.0046(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4058 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1111 _refine_ls_wR_factor_gt 0.1083 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 Sb Sb 0.74871(3) 0.25159(3) 0.101839(14) 0.03206(12) Uani 1 1 d . . . N N 0.6882(3) 0.2638(3) 0.27169(18) 0.0255(5) Uani 1 1 d . . . O1 O 0.9029(3) 0.1523(3) 0.16760(18) 0.0385(5) Uani 1 1 d . . . O2 O 0.8806(3) 0.4961(3) 0.17313(18) 0.0355(5) Uani 1 1 d . . . O3 O 0.5282(3) 0.0438(3) 0.11234(17) 0.0370(5) Uani 1 1 d . . . C11 C 0.8409(4) 0.2567(4) 0.3204(2) 0.0275(6) Uani 1 1 d . . . C12 C 0.9396(4) 0.1901(4) 0.2636(2) 0.0307(6) Uani 1 1 d . . . C13 C 1.0739(4) 0.1645(4) 0.3088(3) 0.0364(7) Uani 1 1 d . . . H13A H 1.1404 0.1176 0.2723 0.044 Uiso 1 1 calc R . . C14 C 1.1097(4) 0.2084(5) 0.4080(3) 0.0382(7) Uani 1 1 d . . . H14A H 1.1988 0.1880 0.4381 0.046 Uiso 1 1 calc R . . C15 C 1.0166(4) 0.2815(4) 0.4632(2) 0.0353(7) Uani 1 1 d . . . H15A H 1.0445 0.3138 0.5298 0.042 Uiso 1 1 calc R . . C16 C 0.8807(4) 0.3065(4) 0.4189(2) 0.0310(6) Uani 1 1 d . . . H16A H 0.8167 0.3566 0.4552 0.037 Uiso 1 1 calc R . . C21 C 0.6795(4) 0.4274(4) 0.2937(2) 0.0276(6) Uani 1 1 d . . . C22 C 0.7918(4) 0.5467(4) 0.2398(2) 0.0307(6) Uani 1 1 d . . . C23 C 0.8033(5) 0.7118(4) 0.2572(3) 0.0375(7) Uani 1 1 d . . . H23A H 0.8812 0.7948 0.2246 0.045 Uiso 1 1 calc R . . C24 C 0.6990(5) 0.7525(4) 0.3226(3) 0.0413(8) Uani 1 1 d . . . H24A H 0.7074 0.8635 0.3342 0.050 Uiso 1 1 calc R . . C25 C 0.5816(5) 0.6304(5) 0.3714(3) 0.0389(8) Uani 1 1 d . . . H25A H 0.5089 0.6585 0.4138 0.047 Uiso 1 1 calc R . . C26 C 0.5732(4) 0.4677(4) 0.3570(2) 0.0311(6) Uani 1 1 d . . . H26A H 0.4956 0.3853 0.3901 0.037 Uiso 1 1 calc R . . C31 C 0.5362(4) 0.1150(4) 0.2832(2) 0.0264(6) Uani 1 1 d . . . C32 C 0.4621(4) 0.0076(4) 0.1979(2) 0.0296(6) Uani 1 1 d . . . C33 C 0.3185(5) -0.1392(4) 0.2037(3) 0.0366(7) Uani 1 1 d . . . H33A H 0.2654 -0.2113 0.1472 0.044 Uiso 1 1 calc R . . C34 C 0.2541(5) -0.1789(4) 0.2929(3) 0.0380(8) Uani 1 1 d . . . H34A H 0.1571 -0.2774 0.2961 0.046 Uiso 1 1 calc R . . C35 C 0.3315(4) -0.0749(4) 0.3768(3) 0.0366(7) Uani 1 1 d . . . H35A H 0.2889 -0.1036 0.4369 0.044 Uiso 1 1 calc R . . C36 C 0.4727(4) 0.0725(4) 0.3718(2) 0.0302(6) Uani 1 1 d . . . H36A H 0.5253 0.1437 0.4287 0.036 Uiso 1 1 calc R . . O1S O 0.5473(3) 0.3658(3) 0.08173(18) 0.0375(5) Uani 1 1 d . . . S S 0.35773(12) 0.29328(11) 0.10562(7) 0.0369(2) Uani 1 1 d . . . C1S C 0.2442(6) 0.2274(6) -0.0101(3) 0.0563(11) Uani 1 1 d . . . H1SA H 0.2691 0.1360 -0.0428 0.084 Uiso 1 1 calc R . . H1SB H 0.2799 0.3199 -0.0482 0.084 Uiso 1 1 calc R . . H1SC H 0.1219 0.1903 -0.0021 0.084 Uiso 1 1 calc R . . C2S C 0.3136(5) 0.4745(5) 0.1379(3) 0.0434(8) Uani 1 1 d . . . H2SA H 0.3761 0.5329 0.1986 0.065 Uiso 1 1 calc R . . H2SB H 0.1915 0.4424 0.1448 0.065 Uiso 1 1 calc R . . H2SC H 0.3492 0.5475 0.0879 0.065 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 Sb 0.03760(17) 0.03605(17) 0.02812(16) 0.00848(9) 0.00657(9) 0.01906(11) N 0.0268(13) 0.0258(12) 0.0281(12) 0.0072(9) 0.0021(10) 0.0138(10) O1 0.0440(14) 0.0459(14) 0.0357(12) 0.0042(10) 0.0044(10) 0.0288(12) O2 0.0337(12) 0.0333(12) 0.0395(12) 0.0110(10) 0.0090(10) 0.0111(10) O3 0.0462(14) 0.0339(12) 0.0296(11) 0.0036(9) 0.0016(10) 0.0144(11) C11 0.0259(15) 0.0258(14) 0.0355(15) 0.0117(12) 0.0025(12) 0.0131(12) C12 0.0314(16) 0.0278(15) 0.0352(16) 0.0099(12) 0.0044(12) 0.0125(12) C13 0.0313(17) 0.0396(18) 0.0477(19) 0.0122(15) 0.0083(14) 0.0220(15) C14 0.0296(17) 0.0408(18) 0.0485(19) 0.0129(15) -0.0003(14) 0.0166(14) C15 0.0326(17) 0.0375(17) 0.0360(16) 0.0062(13) -0.0032(13) 0.0134(14) C16 0.0279(15) 0.0314(16) 0.0350(15) 0.0063(12) 0.0019(12) 0.0122(13) C21 0.0281(15) 0.0255(14) 0.0307(14) 0.0043(11) -0.0023(11) 0.0122(12) C22 0.0277(15) 0.0287(15) 0.0358(16) 0.0058(12) -0.0023(12) 0.0108(12) C23 0.0398(19) 0.0280(16) 0.0439(18) 0.0085(13) -0.0060(15) 0.0115(14) C24 0.054(2) 0.0274(16) 0.047(2) 0.0008(14) -0.0119(16) 0.0221(16) C25 0.048(2) 0.0404(18) 0.0361(17) -0.0006(14) 0.0007(15) 0.0271(16) C26 0.0339(16) 0.0330(16) 0.0306(14) 0.0047(12) 0.0004(12) 0.0173(13) C31 0.0275(14) 0.0238(14) 0.0325(15) 0.0074(11) 0.0010(11) 0.0140(12) C32 0.0328(16) 0.0293(15) 0.0319(15) 0.0062(12) 0.0001(12) 0.0172(13) C33 0.0366(18) 0.0271(15) 0.0461(18) 0.0020(13) -0.0082(14) 0.0133(14) C34 0.0326(17) 0.0309(16) 0.051(2) 0.0145(15) 0.0009(15) 0.0102(14) C35 0.0321(17) 0.0394(18) 0.0438(18) 0.0187(15) 0.0080(14) 0.0160(14) C36 0.0279(15) 0.0348(16) 0.0324(15) 0.0087(12) 0.0023(12) 0.0157(13) O1S 0.0342(13) 0.0416(13) 0.0433(13) 0.0161(11) 0.0030(10) 0.0190(11) S 0.0387(5) 0.0335(4) 0.0434(5) 0.0145(3) 0.0049(4) 0.0168(4) C1S 0.052(2) 0.051(2) 0.056(2) -0.009(2) -0.011(2) 0.014(2) C2S 0.047(2) 0.0420(19) 0.046(2) 0.0038(16) 0.0022(16) 0.0238(17) _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 Sb O3 2.066(2) . ? Sb O1 2.072(2) . ? Sb O2 2.114(2) . ? Sb O1S 2.305(2) . ? Sb N 2.433(2) . ? N C21 1.459(4) . ? N C31 1.463(4) . ? N C11 1.474(4) . ? O1 C12 1.347(4) . ? O2 C22 1.346(4) . ? O3 C32 1.344(4) . ? C11 C16 1.391(4) . ? C11 C12 1.398(4) . ? C12 C13 1.392(4) . ? C13 C14 1.392(5) . ? C14 C15 1.385(5) . ? C15 C16 1.395(4) . ? C21 C26 1.382(5) . ? C21 C22 1.411(4) . ? C22 C23 1.401(5) . ? C23 C24 1.390(6) . ? C24 C25 1.399(6) . ? C25 C26 1.386(5) . ? C31 C36 1.388(4) . ? C31 C32 1.404(4) . ? C32 C33 1.400(5) . ? C33 C34 1.393(5) . ? C34 C35 1.382(5) . ? C35 C36 1.390(5) . ? O1S S 1.539(3) . ? S C2S 1.774(4) . ? S C1S 1.784(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 O3 Sb O1 92.82(10) . . ? O3 Sb O2 139.46(9) . . ? O1 Sb O2 94.45(10) . . ? O3 Sb O1S 80.65(9) . . ? O1 Sb O1S 160.32(10) . . ? O2 Sb O1S 79.26(10) . . ? O3 Sb N 74.16(9) . . ? O1 Sb N 74.26(9) . . ? O2 Sb N 69.67(9) . . ? O1S Sb N 86.08(9) . . ? C21 N C31 118.6(2) . . ? C21 N C11 111.6(2) . . ? C31 N C11 110.3(2) . . ? C21 N Sb 103.56(17) . . ? C31 N Sb 107.74(18) . . ? C11 N Sb 103.62(18) . . ? C12 O1 Sb 118.9(2) . . ? C22 O2 Sb 114.66(19) . . ? C32 O3 Sb 121.6(2) . . ? C16 C11 C12 121.4(3) . . ? C16 C11 N 121.8(3) . . ? C12 C11 N 116.7(3) . . ? O1 C12 C13 121.8(3) . . ? O1 C12 C11 119.7(3) . . ? C13 C12 C11 118.5(3) . . ? C12 C13 C14 120.0(3) . . ? C15 C14 C13 121.3(3) . . ? C14 C15 C16 119.2(3) . . ? C11 C16 C15 119.4(3) . . ? C26 C21 C22 121.4(3) . . ? C26 C21 N 126.4(3) . . ? C22 C21 N 112.1(3) . . ? O2 C22 C23 123.1(3) . . ? O2 C22 C21 118.6(3) . . ? C23 C22 C21 118.3(3) . . ? C24 C23 C22 119.8(3) . . ? C23 C24 C25 120.9(3) . . ? C26 C25 C24 119.7(3) . . ? C21 C26 C25 119.7(3) . . ? C36 C31 C32 120.5(3) . . ? C36 C31 N 123.9(3) . . ? C32 C31 N 115.5(3) . . ? O3 C32 C33 120.5(3) . . ? O3 C32 C31 120.9(3) . . ? C33 C32 C31 118.6(3) . . ? C34 C33 C32 120.3(3) . . ? C35 C34 C33 120.6(3) . . ? C34 C35 C36 119.7(3) . . ? C31 C36 C35 120.3(3) . . ? S O1S Sb 127.26(14) . . ? O1S S C2S 102.95(17) . . ? O1S S C1S 103.69(19) . . ? C2S S C1S 98.7(2) . . ? _diffrn_measured_fraction_theta_max 0.887 _diffrn_reflns_theta_full 28.02 _diffrn_measured_fraction_theta_full 0.887 _refine_diff_density_max 1.372 _refine_diff_density_min -1.627 _refine_diff_density_rms 0.146 data_sb2os20 _database_code_depnum_ccdc_archive 'CCDC 268881' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44.72 H43.44 N2 O9.18 Sb2' _chemical_formula_weight 999.27 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' Sb Sb -0.5866 1.5461 '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 13.1256(7) _cell_length_b 13.3738(8) _cell_length_c 14.4188(8) _cell_angle_alpha 111.5440(10) _cell_angle_beta 99.9690(10) _cell_angle_gamma 108.3350(10) _cell_volume 2111.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 243(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.571 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1002 _exptl_absorpt_coefficient_mu 1.337 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6898 _exptl_absorpt_correction_T_max 0.7310 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 243(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14427 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 28.30 _reflns_number_total 9236 _reflns_number_gt 7295 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0625P)^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 constrained _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0003(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9236 _refine_ls_number_parameters 532 _refine_ls_number_restraints 33 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0962 _refine_ls_wR_factor_gt 0.0880 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 Sb1 Sb 0.316967(16) 0.589143(19) 0.257949(16) 0.03332(8) Uani 1 1 d . . . Sb2 Sb 0.452734(18) 0.612284(19) 0.081910(16) 0.03546(8) Uani 1 1 d . . . O1 O 0.38441(19) 0.5185(2) 0.15141(17) 0.0383(5) Uani 1 1 d . . . O13 O 0.09433(19) 0.6006(2) 0.28539(19) 0.0470(6) Uani 1 1 d . . . H13A H 0.0765 0.6224 0.2404 0.070 Uiso 1 1 calc R . . O21 O 0.29690(19) 0.6000(2) 0.02035(19) 0.0470(6) Uani 1 1 d . . . O22 O 0.4881(2) 0.7534(2) 0.21803(17) 0.0428(5) Uani 1 1 d . . . O23 O 0.53275(18) 0.64238(19) -0.10122(17) 0.0378(5) Uani 1 1 d . . . H23A H 0.5670 0.5988 -0.1126 0.057 Uiso 1 1 calc R . . N1 N 0.2637(2) 0.6021(2) 0.42629(19) 0.0337(6) Uani 1 1 d . . . N2 N 0.4700(2) 0.7910(2) 0.04076(19) 0.0313(5) Uani 1 1 d . . . C13 C 0.0270(3) 0.2541(4) 0.3184(3) 0.0583(10) Uani 1 1 d . . . H13B H -0.0227 0.1752 0.2950 0.070 Uiso 1 1 calc R . . C14 C 0.0298(3) 0.3401(4) 0.4073(3) 0.0558(10) Uani 1 1 d . . . H14A H -0.0195 0.3207 0.4441 0.067 Uiso 1 1 calc R . . C15 C 0.1049(3) 0.4564(4) 0.4442(3) 0.0478(9) Uani 1 1 d . . . H15A H 0.1069 0.5157 0.5060 0.057 Uiso 1 1 calc R . . C16 C 0.1773(3) 0.4846(3) 0.3891(2) 0.0367(7) Uani 1 1 d . . . C17 C 0.4648(3) 0.6421(3) 0.4640(2) 0.0381(7) Uani 1 1 d . . . C18 C 0.5671(3) 0.6619(3) 0.5298(3) 0.0477(9) Uani 1 1 d . . . H18A H 0.6325 0.6781 0.5096 0.057 Uiso 1 1 calc R . . C19 C 0.5733(3) 0.6579(3) 0.6242(3) 0.0523(9) Uani 1 1 d . . . H19A H 0.6431 0.6718 0.6684 0.063 Uiso 1 1 calc R . . C21 C 0.4654(3) 0.8459(3) 0.2195(3) 0.0377(7) Uani 1 1 d . . . C22 C 0.4510(3) 0.9191(3) 0.3097(3) 0.0493(9) Uani 1 1 d . . . H22A H 0.4591 0.9053 0.3694 0.059 Uiso 1 1 calc R . . C23 C 0.4249(3) 1.0112(4) 0.3110(3) 0.0599(11) Uani 1 1 d . . . H23B H 0.4173 1.0613 0.3726 0.072 Uiso 1 1 calc R . . C24 C 0.4096(3) 1.0316(3) 0.2237(3) 0.0566(10) Uani 1 1 d . . . H24A H 0.3899 1.0937 0.2250 0.068 Uiso 1 1 calc R . . C25 C 0.4237(3) 0.9598(3) 0.1345(3) 0.0450(8) Uani 1 1 d . . . H25A H 0.4126 0.9724 0.0742 0.054 Uiso 1 1 calc R . . C26 C 0.4542(2) 0.8690(3) 0.1332(2) 0.0347(7) Uani 1 1 d . . . C27 C 0.2818(3) 0.6373(3) -0.0554(3) 0.0392(7) Uani 1 1 d . . . C28 C 0.1792(3) 0.5818(4) -0.1366(3) 0.0511(9) Uani 1 1 d . . . H28A H 0.1199 0.5171 -0.1405 0.061 Uiso 1 1 calc R . . C29 C 0.1640(3) 0.6215(4) -0.2116(3) 0.0499(9) Uani 1 1 d . . . H29A H 0.0935 0.5853 -0.2651 0.060 Uiso 1 1 calc R . . C110 C 0.4789(3) 0.6338(4) 0.6551(3) 0.0529(9) Uani 1 1 d . . . H11A H 0.4841 0.6304 0.7195 0.063 Uiso 1 1 calc R . . C111 C 0.3766(3) 0.6148(3) 0.5914(3) 0.0433(8) Uani 1 1 d . . . H11B H 0.3117 0.5980 0.6122 0.052 Uiso 1 1 calc R . . C112 C 0.3695(3) 0.6206(3) 0.4963(2) 0.0358(7) Uani 1 1 d . . . C113 C 0.1421(3) 0.6947(3) 0.3824(3) 0.0418(8) Uani 1 1 d . . . C114 C 0.1089(3) 0.7871(4) 0.4096(3) 0.0582(10) Uani 1 1 d . . . H11C H 0.0507 0.7852 0.3598 0.070 Uiso 1 1 calc R . . C115 C 0.1600(4) 0.8822(4) 0.5088(4) 0.0699(12) Uani 1 1 d . . . H11D H 0.1358 0.9438 0.5267 0.084 Uiso 1 1 calc R . . C116 C 0.2459(4) 0.8863(4) 0.5806(3) 0.0635(11) Uani 1 1 d . . . H11E H 0.2822 0.9519 0.6475 0.076 Uiso 1 1 calc R . . C117 C 0.2800(3) 0.7949(3) 0.5557(3) 0.0478(8) Uani 1 1 d . . . H11F H 0.3391 0.7986 0.6059 0.057 Uiso 1 1 calc R . . C118 C 0.2280(3) 0.6976(3) 0.4573(3) 0.0379(7) Uani 1 1 d . . . C210 C 0.2518(3) 0.7139(3) -0.2085(3) 0.0439(8) Uani 1 1 d . . . H21A H 0.2414 0.7397 -0.2604 0.053 Uiso 1 1 calc R . . C211 C 0.3550(3) 0.7684(3) -0.1290(3) 0.0384(7) Uani 1 1 d . . . H21B H 0.4156 0.8299 -0.1279 0.046 Uiso 1 1 calc R . . C212 C 0.3689(2) 0.7323(3) -0.0512(2) 0.0329(6) Uani 1 1 d . . . C213 C 0.6093(2) 0.7570(3) -0.0459(2) 0.0331(6) Uani 1 1 d . . . C214 C 0.7144(3) 0.7970(3) -0.0590(3) 0.0439(8) Uani 1 1 d . . . H21C H 0.7342 0.7445 -0.1087 0.053 Uiso 1 1 calc R . . C215 C 0.7895(3) 0.9132(4) 0.0003(3) 0.0540(10) Uani 1 1 d . . . H21D H 0.8605 0.9397 -0.0091 0.065 Uiso 1 1 calc R . . C216 C 0.7619(3) 0.9917(3) 0.0737(3) 0.0515(9) Uani 1 1 d . . . H21E H 0.8140 1.0709 0.1147 0.062 Uiso 1 1 calc R . . C217 C 0.6568(3) 0.9525(3) 0.0861(3) 0.0389(7) Uani 1 1 d . . . H21F H 0.6377 1.0059 0.1358 0.047 Uiso 1 1 calc R . . C218 C 0.5791(2) 0.8362(3) 0.0268(2) 0.0320(6) Uani 1 1 d . . . O1S O 0.6636(3) 0.6301(4) 0.1861(4) 0.1131(15) Uani 1 1 d D . . C1S C 0.7564(7) 0.7284(10) 0.2022(10) 0.219(6) Uani 1 1 d D . . H1SA H 0.7348 0.7725 0.1670 0.262 Uiso 1 1 calc R . . H1SB H 0.8168 0.7080 0.1806 0.262 Uiso 1 1 calc R . . C2S C 0.7874(13) 0.7921(9) 0.3185(10) 0.293(11) Uani 1 1 d D . . H2SA H 0.8630 0.8573 0.3485 0.351 Uiso 1 1 calc R . . H2SB H 0.7325 0.8246 0.3372 0.351 Uiso 1 1 calc R . . C3S C 0.7869(8) 0.7102(13) 0.3574(8) 0.262(9) Uani 1 1 d D . . H3SA H 0.7786 0.7347 0.4276 0.314 Uiso 1 1 calc R . . H3SB H 0.8542 0.6930 0.3583 0.314 Uiso 1 1 calc R . . C4S C 0.6842(5) 0.6122(6) 0.2750(4) 0.0954(18) Uani 1 1 d D . . H4SA H 0.6934 0.5381 0.2569 0.114 Uiso 1 1 calc R . . H4SB H 0.6193 0.6060 0.3010 0.114 Uiso 1 1 calc R . . O2S O 0.0373(2) 0.6798(3) 0.1421(2) 0.0734(9) Uani 1 1 d D . . C5S C 0.1363(4) 0.7634(6) 0.1464(5) 0.118(3) Uani 1 1 d D . . H5SA H 0.1885 0.7271 0.1268 0.142 Uiso 1 1 calc R . . H5SB H 0.1745 0.8282 0.2181 0.142 Uiso 1 1 calc R . . C6S C 0.1037(5) 0.8081(7) 0.0722(6) 0.137(3) Uani 1 1 d D . . H6SA H 0.1072 0.8874 0.1102 0.164 Uiso 1 1 calc R . . H6SB H 0.1545 0.8115 0.0298 0.164 Uiso 1 1 calc R . . C7S C -0.0108(5) 0.7261(7) 0.0060(6) 0.131(3) Uani 1 1 d D . . H7SA H -0.0621 0.7661 0.0113 0.158 Uiso 1 1 calc R . . H7SB H -0.0148 0.6888 -0.0679 0.158 Uiso 1 1 calc R . . C8S C -0.0400(6) 0.6411(7) 0.0443(5) 0.148(4) Uani 1 1 d D . . H8SA H -0.1161 0.6258 0.0503 0.177 Uiso 1 1 calc R . . H8SB H -0.0417 0.5670 -0.0058 0.177 Uiso 1 1 calc R . . O3S O 0.0477(19) 0.014(2) 0.1993(19) 0.110(6) Uiso 0.180(5) 1 d PD . . C9S C -0.010(3) -0.030(3) 0.259(2) 0.110(6) Uiso 0.180(5) 1 d PD . . H9SA H -0.0289 -0.1144 0.2317 0.132 Uiso 0.180(5) 1 calc PR . . H9SB H -0.0814 -0.0197 0.2517 0.132 Uiso 0.180(5) 1 calc PR . . C10S C 0.058(2) 0.031(3) 0.371(2) 0.110(6) Uiso 0.180(5) 1 d PD . . H10A H 0.0429 0.0985 0.4101 0.132 Uiso 0.180(5) 1 calc PR . . H10B H 0.0445 -0.0230 0.4033 0.132 Uiso 0.180(5) 1 calc PR . . O11 O 0.24314(19) 0.4241(2) 0.24154(18) 0.0412(5) Uani 1 1 d . . . C11 C 0.1731(3) 0.3976(3) 0.2964(3) 0.0384(7) Uani 1 1 d . . . C11S C 0.170(3) 0.067(3) 0.366(2) 0.110(6) Uiso 0.180(5) 1 d PD . . H11G H 0.2018 0.0111 0.3710 0.132 Uiso 0.180(5) 1 calc PR . . H11H H 0.2188 0.1453 0.4236 0.132 Uiso 0.180(5) 1 calc PR . . O12 O 0.46057(18) 0.6429(2) 0.37008(18) 0.0474(6) Uani 1 1 d . . . C12 C 0.0976(3) 0.2825(3) 0.2614(3) 0.0508(9) Uani 1 1 d . . . H12A H 0.0936 0.2227 0.1988 0.061 Uiso 1 1 calc R . . C12S C 0.162(2) 0.069(3) 0.265(2) 0.110(6) Uiso 0.180(5) 1 d PD . . H12B H 0.1954 0.1504 0.2763 0.132 Uiso 0.180(5) 1 calc PR . . H12C H 0.2041 0.0271 0.2300 0.132 Uiso 0.180(5) 1 calc PR . . 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 Sb1 0.03443(12) 0.04336(14) 0.03001(12) 0.02185(10) 0.01428(9) 0.01724(9) Sb2 0.04515(13) 0.03934(14) 0.03394(13) 0.02274(10) 0.02210(10) 0.01971(10) O1 0.0496(13) 0.0445(13) 0.0374(12) 0.0272(11) 0.0255(10) 0.0233(11) O13 0.0395(12) 0.0600(16) 0.0412(13) 0.0272(12) 0.0078(10) 0.0178(11) O21 0.0405(12) 0.0579(16) 0.0425(14) 0.0354(13) 0.0109(10) 0.0063(11) O22 0.0564(14) 0.0460(14) 0.0274(11) 0.0184(10) 0.0128(10) 0.0211(11) O23 0.0424(12) 0.0353(12) 0.0366(12) 0.0172(10) 0.0165(10) 0.0140(10) N1 0.0325(12) 0.0459(15) 0.0274(13) 0.0193(12) 0.0125(10) 0.0170(12) N2 0.0322(12) 0.0347(14) 0.0295(13) 0.0172(11) 0.0131(10) 0.0119(11) C13 0.049(2) 0.060(3) 0.058(3) 0.035(2) 0.0152(19) 0.0052(19) C14 0.0425(19) 0.075(3) 0.057(2) 0.043(2) 0.0245(18) 0.0122(19) C15 0.0425(18) 0.070(3) 0.042(2) 0.0316(19) 0.0220(16) 0.0253(18) C16 0.0346(15) 0.051(2) 0.0332(17) 0.0254(15) 0.0135(13) 0.0183(14) C17 0.0382(16) 0.0484(19) 0.0300(16) 0.0182(15) 0.0128(13) 0.0193(15) C18 0.0374(17) 0.063(2) 0.041(2) 0.0217(18) 0.0105(15) 0.0224(17) C19 0.052(2) 0.058(2) 0.039(2) 0.0150(18) -0.0003(16) 0.0285(19) C21 0.0378(16) 0.0360(17) 0.0330(17) 0.0132(14) 0.0123(13) 0.0100(14) C22 0.054(2) 0.048(2) 0.0359(19) 0.0107(16) 0.0209(16) 0.0156(17) C23 0.060(2) 0.048(2) 0.053(2) 0.0042(19) 0.028(2) 0.0182(19) C24 0.059(2) 0.043(2) 0.070(3) 0.020(2) 0.028(2) 0.0261(18) C25 0.0440(18) 0.0365(18) 0.052(2) 0.0200(16) 0.0149(16) 0.0132(15) C26 0.0348(15) 0.0319(16) 0.0346(16) 0.0134(14) 0.0130(13) 0.0112(13) C27 0.0354(15) 0.051(2) 0.0350(17) 0.0268(16) 0.0118(13) 0.0131(15) C28 0.0362(17) 0.058(2) 0.048(2) 0.0291(19) 0.0076(15) 0.0025(16) C29 0.0403(18) 0.065(2) 0.041(2) 0.0267(18) 0.0063(15) 0.0181(17) C110 0.067(2) 0.062(2) 0.0330(19) 0.0253(18) 0.0086(17) 0.029(2) C111 0.0500(19) 0.055(2) 0.0337(18) 0.0249(16) 0.0176(15) 0.0241(17) C112 0.0366(15) 0.0465(19) 0.0265(15) 0.0177(14) 0.0092(12) 0.0191(14) C113 0.0355(16) 0.054(2) 0.0427(19) 0.0272(17) 0.0164(14) 0.0183(15) C114 0.052(2) 0.070(3) 0.067(3) 0.038(2) 0.020(2) 0.035(2) C115 0.078(3) 0.068(3) 0.080(3) 0.033(3) 0.031(3) 0.048(3) C116 0.069(3) 0.056(3) 0.056(3) 0.016(2) 0.017(2) 0.028(2) C117 0.0454(18) 0.056(2) 0.043(2) 0.0230(18) 0.0157(16) 0.0217(17) C118 0.0344(15) 0.051(2) 0.0370(17) 0.0246(16) 0.0181(13) 0.0187(14) C210 0.0514(19) 0.056(2) 0.0384(19) 0.0306(17) 0.0170(15) 0.0267(17) C211 0.0400(16) 0.0409(18) 0.0406(18) 0.0240(15) 0.0166(14) 0.0157(14) C212 0.0340(14) 0.0356(16) 0.0304(16) 0.0157(13) 0.0121(12) 0.0141(13) C213 0.0359(15) 0.0385(17) 0.0291(15) 0.0203(14) 0.0105(12) 0.0146(13) C214 0.0418(17) 0.053(2) 0.048(2) 0.0276(18) 0.0235(16) 0.0219(16) C215 0.0377(18) 0.059(2) 0.070(3) 0.035(2) 0.0240(18) 0.0155(17) C216 0.0389(18) 0.041(2) 0.063(2) 0.0210(19) 0.0145(17) 0.0070(15) C217 0.0394(16) 0.0351(17) 0.0400(18) 0.0170(15) 0.0121(14) 0.0134(14) C218 0.0336(14) 0.0363(16) 0.0335(16) 0.0220(14) 0.0142(12) 0.0140(13) O1S 0.074(2) 0.157(4) 0.139(4) 0.107(3) 0.031(2) 0.039(3) C1S 0.113(7) 0.289(14) 0.369(18) 0.275(15) 0.087(9) 0.065(8) C2S 0.328(18) 0.097(7) 0.225(15) -0.068(8) -0.116(13) 0.088(9) C3S 0.103(6) 0.48(3) 0.128(8) 0.146(13) 0.027(6) 0.015(11) C4S 0.078(3) 0.143(6) 0.074(4) 0.052(4) 0.020(3) 0.055(4) O2S 0.0583(17) 0.090(2) 0.071(2) 0.0564(18) 0.0054(15) 0.0142(16) C5S 0.062(3) 0.160(6) 0.139(6) 0.114(5) 0.008(3) 0.010(4) C6S 0.092(4) 0.175(7) 0.172(7) 0.139(7) 0.025(5) 0.026(5) C7S 0.087(4) 0.199(8) 0.136(6) 0.131(6) 0.019(4) 0.036(5) C8S 0.128(6) 0.136(6) 0.113(5) 0.089(5) -0.036(4) -0.024(5) O11 0.0466(13) 0.0455(13) 0.0365(13) 0.0220(11) 0.0216(10) 0.0165(11) C11 0.0349(15) 0.052(2) 0.0334(17) 0.0264(16) 0.0133(13) 0.0144(15) O12 0.0299(11) 0.0782(18) 0.0360(13) 0.0313(13) 0.0136(10) 0.0162(11) C12 0.053(2) 0.051(2) 0.042(2) 0.0243(18) 0.0150(17) 0.0100(18) _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 Sb1 O12 1.980(2) . ? Sb1 O1 1.992(2) . ? Sb1 O11 2.015(2) . ? Sb1 N1 2.601(2) . ? Sb1 O22 2.912(2) . ? Sb2 O1 1.976(2) . ? Sb2 O22 2.011(2) . ? Sb2 O21 2.013(2) . ? Sb2 N2 2.619(2) . ? Sb2 O1S 2.804(4) . ? O13 C113 1.357(4) . ? O21 C27 1.367(4) . ? O22 C21 1.354(4) . ? O23 C213 1.360(4) . ? N1 C118 1.442(4) . ? N1 C16 1.446(4) . ? N1 C112 1.458(4) . ? N2 C218 1.450(4) . ? N2 C212 1.451(4) . ? N2 C26 1.455(4) . ? C13 C14 1.357(6) . ? C13 C12 1.395(5) . ? C14 C15 1.385(6) . ? C15 C16 1.391(4) . ? C16 C11 1.391(5) . ? C17 O12 1.350(4) . ? C17 C18 1.387(4) . ? C17 C112 1.391(4) . ? C18 C19 1.371(5) . ? C19 C110 1.371(5) . ? C21 C26 1.383(4) . ? C21 C22 1.398(5) . ? C22 C23 1.374(6) . ? C23 C24 1.378(6) . ? C24 C25 1.377(5) . ? C25 C26 1.389(5) . ? C27 C28 1.386(4) . ? C27 C212 1.389(4) . ? C28 C29 1.380(5) . ? C29 C210 1.379(5) . ? C110 C111 1.378(5) . ? C111 C112 1.390(4) . ? C113 C114 1.383(5) . ? C113 C118 1.400(4) . ? C114 C115 1.382(6) . ? C115 C116 1.364(6) . ? C116 C117 1.378(5) . ? C117 C118 1.386(5) . ? C210 C211 1.381(5) . ? C211 C212 1.382(4) . ? C213 C214 1.388(4) . ? C213 C218 1.404(4) . ? C214 C215 1.374(5) . ? C215 C216 1.382(5) . ? C216 C217 1.382(5) . ? C217 C218 1.383(4) . ? O1S C4S 1.386(6) . ? O1S C1S 1.391(8) . ? C1S C2S 1.483(11) . ? C2S C3S 1.401(13) . ? C3S C4S 1.462(10) . ? O2S C8S 1.387(6) . ? O2S C5S 1.396(5) . ? C5S C6S 1.470(7) . ? C6S C7S 1.439(8) . ? C7S C8S 1.416(7) . ? O3S C12S 1.406(15) . ? O3S C9S 1.409(15) . ? C9S C10S 1.462(16) . ? C10S C11S 1.416(18) . ? O11 C11 1.360(4) . ? C11 C12 1.380(5) . ? C11S C12S 1.450(16) . ? 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 O12 Sb1 O1 88.76(9) . . ? O12 Sb1 O11 97.87(10) . . ? O1 Sb1 O11 84.74(9) . . ? O12 Sb1 N1 73.70(8) . . ? O1 Sb1 N1 147.87(8) . . ? O11 Sb1 N1 71.67(9) . . ? O12 Sb1 O22 75.14(8) . . ? O1 Sb1 O22 63.59(8) . . ? O11 Sb1 O22 147.40(8) . . ? N1 Sb1 O22 132.96(7) . . ? O1 Sb2 O22 85.21(9) . . ? O1 Sb2 O21 87.59(9) . . ? O22 Sb2 O21 93.74(10) . . ? O1 Sb2 N2 146.45(8) . . ? O22 Sb2 N2 71.99(8) . . ? O21 Sb2 N2 70.20(8) . . ? O1 Sb2 O1S 87.52(10) . . ? O22 Sb2 O1S 82.56(12) . . ? O21 Sb2 O1S 174.09(11) . . ? N2 Sb2 O1S 112.69(10) . . ? Sb2 O1 Sb1 117.52(11) . . ? C27 O21 Sb2 117.79(19) . . ? C21 O22 Sb2 121.62(19) . . ? C21 O22 Sb1 113.55(19) . . ? Sb2 O22 Sb1 85.05(8) . . ? C118 N1 C16 116.7(2) . . ? C118 N1 C112 116.7(3) . . ? C16 N1 C112 111.4(2) . . ? C118 N1 Sb1 105.89(18) . . ? C16 N1 Sb1 101.96(18) . . ? C112 N1 Sb1 101.44(17) . . ? C218 N2 C212 117.9(2) . . ? C218 N2 C26 115.9(2) . . ? C212 N2 C26 111.5(2) . . ? C218 N2 Sb2 108.99(17) . . ? C212 N2 Sb2 98.64(17) . . ? C26 N2 Sb2 100.91(17) . . ? C14 C13 C12 120.3(4) . . ? C13 C14 C15 120.5(4) . . ? C14 C15 C16 119.4(4) . . ? C15 C16 C11 120.5(3) . . ? C15 C16 N1 122.9(3) . . ? C11 C16 N1 116.6(3) . . ? O12 C17 C18 118.9(3) . . ? O12 C17 C112 122.1(3) . . ? C18 C17 C112 119.0(3) . . ? C19 C18 C17 120.2(3) . . ? C110 C19 C18 120.9(3) . . ? O22 C21 C26 121.7(3) . . ? O22 C21 C22 119.4(3) . . ? C26 C21 C22 118.9(3) . . ? C23 C22 C21 119.8(4) . . ? C22 C23 C24 121.3(4) . . ? C25 C24 C23 119.2(4) . . ? C24 C25 C26 120.3(4) . . ? C21 C26 C25 120.4(3) . . ? C21 C26 N2 117.3(3) . . ? C25 C26 N2 122.2(3) . . ? O21 C27 C28 120.5(3) . . ? O21 C27 C212 120.3(3) . . ? C28 C27 C212 119.2(3) . . ? C29 C28 C27 120.1(3) . . ? C210 C29 C28 120.4(3) . . ? C19 C110 C111 119.9(3) . . ? C110 C111 C112 119.9(3) . . ? C111 C112 C17 120.1(3) . . ? C111 C112 N1 122.1(3) . . ? C17 C112 N1 117.8(3) . . ? O13 C113 C114 122.4(3) . . ? O13 C113 C118 118.4(3) . . ? C114 C113 C118 119.2(3) . . ? C115 C114 C113 121.0(4) . . ? C116 C115 C114 119.6(4) . . ? C115 C116 C117 120.5(4) . . ? C116 C117 C118 120.7(4) . . ? C117 C118 C113 119.0(3) . . ? C117 C118 N1 122.6(3) . . ? C113 C118 N1 118.2(3) . . ? C29 C210 C211 119.9(3) . . ? C210 C211 C212 119.8(3) . . ? C211 C212 C27 120.4(3) . . ? C211 C212 N2 124.0(3) . . ? C27 C212 N2 115.6(3) . . ? O23 C213 C214 122.5(3) . . ? O23 C213 C218 117.8(3) . . ? C214 C213 C218 119.7(3) . . ? C215 C214 C213 120.1(3) . . ? C214 C215 C216 120.8(3) . . ? C215 C216 C217 119.3(3) . . ? C216 C217 C218 121.2(3) . . ? C217 C218 C213 118.9(3) . . ? C217 C218 N2 122.7(3) . . ? C213 C218 N2 118.3(3) . . ? C4S O1S C1S 107.7(6) . . ? C4S O1S Sb2 123.4(3) . . ? C1S O1S Sb2 114.6(5) . . ? O1S C1S C2S 97.2(8) . . ? C3S C2S C1S 107.0(9) . . ? C2S C3S C4S 96.5(8) . . ? O1S C4S C3S 110.1(7) . . ? C8S O2S C5S 104.9(4) . . ? O2S C5S C6S 107.7(4) . . ? C7S C6S C5S 105.7(5) . . ? C8S C7S C6S 105.1(5) . . ? O2S C8S C7S 111.1(5) . . ? C12S O3S C9S 102(2) . . ? O3S C9S C10S 112(3) . . ? C11S C10S C9S 102(3) . . ? C11 O11 Sb1 121.9(2) . . ? O11 C11 C12 120.1(3) . . ? O11 C11 C16 121.1(3) . . ? C12 C11 C16 118.9(3) . . ? C10S C11S C12S 107(3) . . ? C17 O12 Sb1 123.40(19) . . ? C11 C12 C13 120.4(4) . . ? O3S C12S C11S 111(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O13 H13A O2S 0.83 1.91 2.742(4) 177.2 . O23 H23A O1 0.83 1.81 2.634(3) 169.3 2_665 _diffrn_measured_fraction_theta_max 0.879 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.879 _refine_diff_density_max 1.037 _refine_diff_density_min -0.898 _refine_diff_density_rms 0.087