# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'David G. Churchill' _publ_contact_author_email dchurchill@kaist.ac.kr loop_ _publ_author_name A.P.Singh D.Murale 'Kang Lee' 'Taehong Jun' 'Hyunjeong Liew' 'Yoo-Hun Suh' D.Churchill data_nchu66-1 _database_code_depnum_ccdc_archive 'CCDC 860722' #TrackingRef '- nchu66-1_7_.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C31H29BF2N2O3S3 _chemical_formula_sum 'C31 H29 B F2 N2 O3 S3' _chemical_formula_weight 622.55 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' F F 0.0171 0.0103 '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 37.899(9) _cell_length_b 7.743(2) _cell_length_c 25.029(7) _cell_angle_alpha 90.00 _cell_angle_beta 122.015(11) _cell_angle_gamma 90.00 _cell_volume 6227(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7373 _cell_measurement_theta_min 1.65 _cell_measurement_theta_max 27.90 _exptl_crystal_description platy _exptl_crystal_colour Red _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2592 _exptl_absorpt_coefficient_mu 0.285 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.930 _exptl_absorpt_correction_T_max 0.941 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 28247 _diffrn_reflns_av_R_equivalents 0.1082 _diffrn_reflns_av_sigmaI/netI 0.0959 _diffrn_reflns_limit_h_min -46 _diffrn_reflns_limit_h_max 49 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 27.90 _reflns_number_total 7373 _reflns_number_gt 2917 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker APEX II' _computing_data_reduction 'Bruker APEX II' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP3 _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^)+(0.1279P)^2^+2.2279P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7373 _refine_ls_number_parameters 385 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.2123 _refine_ls_R_factor_gt 0.0888 _refine_ls_wR_factor_ref 0.2866 _refine_ls_wR_factor_gt 0.2208 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.005 _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 B B 0.17731(19) 0.6891(9) 0.5471(3) 0.0700(17) Uani 1 1 d . . . F1 F 0.19144(10) 0.8571(5) 0.56529(16) 0.1001(11) Uani 1 1 d . . . F2 F 0.18272(10) 0.5976(6) 0.59762(14) 0.1137(13) Uani 1 1 d . . . N1 N 0.20039(12) 0.6030(5) 0.51898(17) 0.0623(10) Uani 1 1 d . . . N2 N 0.13024(11) 0.6932(5) 0.49426(16) 0.0586(10) Uani 1 1 d . . . S1 S 0.09441(5) 0.34519(19) 0.24527(7) 0.0860(5) Uani 1 1 d . . . S2 S 0.07796(5) 0.6653(2) 0.16638(7) 0.0869(5) Uani 1 1 d . . . S3 S 0.12729(6) 0.16644(19) 0.36986(9) 0.1015(6) Uani 1 1 d . . . O1 O 0.04935(13) 0.7924(7) 0.1583(2) 0.1210(16) Uani 1 1 d . . . O2 O 0.06576(15) 0.5294(7) 0.12077(18) 0.1293(18) Uani 1 1 d . . . O3 O 0.1146(2) 0.0320(6) 0.3224(3) 0.168(2) Uani 1 1 d . . . C1 C 0.24213(17) 0.5698(7) 0.5503(3) 0.0755(15) Uani 1 1 d . . . C2 C 0.25178(17) 0.5045(7) 0.5079(3) 0.0802(15) Uani 1 1 d . . . H2 H 0.2782 0.4725 0.5177 0.096 Uiso 1 1 calc R . . C3 C 0.21604(16) 0.4944(7) 0.4489(3) 0.0721(14) Uani 1 1 d . . . C4 C 0.18316(15) 0.5580(6) 0.4560(2) 0.0604(12) Uani 1 1 d . . . C5 C 0.14016(14) 0.5793(6) 0.4130(2) 0.0555(11) Uani 1 1 d . . . C6 C 0.11403(14) 0.6445(6) 0.4319(2) 0.0572(11) Uani 1 1 d . . . C7 C 0.06973(15) 0.6690(6) 0.3984(2) 0.0650(13) Uani 1 1 d . . . C8 C 0.06151(16) 0.7287(7) 0.4416(3) 0.0728(14) Uani 1 1 d . . . H8 H 0.0352 0.7547 0.4335 0.087 Uiso 1 1 calc R . . C9 C 0.09848(16) 0.7454(7) 0.4998(2) 0.0663(13) Uani 1 1 d . . . C10 C 0.11446(16) 0.3629(6) 0.3246(2) 0.0687(13) Uani 1 1 d . . . C11 C 0.12213(14) 0.5274(6) 0.3465(2) 0.0577(12) Uani 1 1 d . . . C12 C 0.11064(15) 0.6456(6) 0.2959(2) 0.0636(13) Uani 1 1 d . . . H12 H 0.1132 0.7648 0.3011 0.076 Uiso 1 1 calc R . . C13 C 0.09567(15) 0.5657(7) 0.2397(2) 0.0697(14) Uani 1 1 d . . . C14 C 0.21430(17) 0.4300(9) 0.3910(3) 0.0931(18) Uani 1 1 d . . . H14A H 0.2419 0.4257 0.3986 0.140 Uiso 1 1 calc R . . H14B H 0.1975 0.5066 0.3564 0.140 Uiso 1 1 calc R . . H14C H 0.2023 0.3164 0.3808 0.140 Uiso 1 1 calc R . . C15 C 0.27081(17) 0.5987(9) 0.6199(2) 0.0974(19) Uani 1 1 d . . . H15A H 0.2673 0.7143 0.6303 0.146 Uiso 1 1 calc R . . H15B H 0.2991 0.5823 0.6314 0.146 Uiso 1 1 calc R . . H15C H 0.2643 0.5179 0.6426 0.146 Uiso 1 1 calc R . . C16 C 0.03767(16) 0.6366(8) 0.3302(3) 0.0924(18) Uani 1 1 d . . . H16A H 0.0104 0.6519 0.3231 0.139 Uiso 1 1 calc R . . H16B H 0.0405 0.5207 0.3194 0.139 Uiso 1 1 calc R . . H16C H 0.0417 0.7166 0.3045 0.139 Uiso 1 1 calc R . . C17 C 0.10443(18) 0.8108(8) 0.5600(2) 0.0899(18) Uani 1 1 d . . . H17A H 0.1108 0.7160 0.5884 0.135 Uiso 1 1 calc R . . H17B H 0.0794 0.8664 0.5518 0.135 Uiso 1 1 calc R . . H17C H 0.1269 0.8923 0.5786 0.135 Uiso 1 1 calc R . . C18 C 0.12220(15) 0.7677(7) 0.1767(2) 0.0689(14) Uani 1 1 d . . . C19 C 0.13380(19) 0.9265(8) 0.2051(2) 0.0824(16) Uani 1 1 d . . . H19 H 0.1176 0.9832 0.2174 0.099 Uiso 1 1 calc R . . C20 C 0.1701(2) 1.0011(9) 0.2151(2) 0.097(2) Uani 1 1 d . . . H20 H 0.1780 1.1085 0.2346 0.117 Uiso 1 1 calc R . . C21 C 0.19456(19) 0.9227(11) 0.1975(3) 0.097(2) Uani 1 1 d . . . C22 C 0.1815(2) 0.7676(11) 0.1670(3) 0.099(2) Uani 1 1 d . . . H22 H 0.1967 0.7157 0.1520 0.119 Uiso 1 1 calc R . . C23 C 0.1468(2) 0.6868(9) 0.1580(3) 0.0890(18) Uani 1 1 d . . . H23 H 0.1396 0.5781 0.1394 0.107 Uiso 1 1 calc R . . C24 C 0.2348(2) 1.0068(14) 0.2108(3) 0.162(4) Uani 1 1 d . . . H24A H 0.2560 0.9914 0.2544 0.243 Uiso 1 1 calc R . . H24B H 0.2302 1.1280 0.2015 0.243 Uiso 1 1 calc R . . H24C H 0.2436 0.9542 0.1850 0.243 Uiso 1 1 calc R . . C25 C 0.08932(19) 0.1778(6) 0.3918(3) 0.0734(14) Uani 1 1 d . . . C26 C 0.1041(2) 0.2196(8) 0.4530(3) 0.0868(16) Uani 1 1 d . . . H26 H 0.1324 0.2391 0.4809 0.104 Uiso 1 1 calc R . . C27 C 0.0771(3) 0.2321(9) 0.4723(3) 0.113(2) Uani 1 1 d . . . H27 H 0.0869 0.2657 0.5136 0.136 Uiso 1 1 calc R . . C28 C 0.0357(3) 0.1970(11) 0.4331(5) 0.123(3) Uani 1 1 d . . . C29 C 0.0212(2) 0.1522(11) 0.3708(4) 0.134(3) Uani 1 1 d . . . H29 H -0.0068 0.1286 0.3430 0.161 Uiso 1 1 calc R . . C30 C 0.0483(2) 0.1430(9) 0.3509(3) 0.105(2) Uani 1 1 d . . . H30 H 0.0388 0.1131 0.3094 0.126 Uiso 1 1 calc R . . C31 C 0.0043(3) 0.2102(15) 0.4538(5) 0.177(4) Uani 1 1 d U . . H31A H -0.0134 0.3084 0.4340 0.266 Uiso 1 1 calc R . . H31B H 0.0189 0.2232 0.4988 0.266 Uiso 1 1 calc R . . H31C H -0.0123 0.1072 0.4416 0.266 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 B 0.064(4) 0.086(5) 0.064(3) 0.010(3) 0.037(3) -0.001(3) F1 0.082(2) 0.109(3) 0.114(2) -0.042(2) 0.0549(19) -0.0254(19) F2 0.090(2) 0.181(4) 0.080(2) 0.048(2) 0.0511(18) 0.024(2) N1 0.053(2) 0.065(3) 0.067(2) 0.013(2) 0.031(2) 0.006(2) N2 0.060(3) 0.059(3) 0.061(2) 0.0028(18) 0.035(2) 0.0013(19) S1 0.1092(12) 0.0663(10) 0.1017(11) -0.0304(8) 0.0689(10) -0.0205(8) S2 0.0751(10) 0.1110(14) 0.0676(8) -0.0071(8) 0.0330(8) -0.0121(9) S3 0.1375(16) 0.0523(9) 0.1578(16) 0.0107(9) 0.1076(14) 0.0132(9) O1 0.083(3) 0.168(5) 0.112(3) 0.034(3) 0.052(3) 0.031(3) O2 0.140(4) 0.162(5) 0.073(2) -0.050(3) 0.047(3) -0.063(3) O3 0.323(8) 0.052(3) 0.248(6) -0.015(3) 0.231(6) -0.012(4) C1 0.066(4) 0.073(4) 0.083(4) 0.011(3) 0.037(3) 0.002(3) C2 0.059(3) 0.086(4) 0.094(4) 0.011(3) 0.039(3) 0.015(3) C3 0.070(4) 0.068(3) 0.090(4) 0.009(3) 0.051(3) 0.004(3) C4 0.059(3) 0.053(3) 0.076(3) 0.009(2) 0.040(3) 0.004(2) C5 0.056(3) 0.047(3) 0.066(3) 0.008(2) 0.034(2) 0.001(2) C6 0.051(3) 0.049(3) 0.069(3) 0.001(2) 0.030(2) 0.001(2) C7 0.054(3) 0.058(3) 0.077(3) 0.000(2) 0.030(3) 0.009(2) C8 0.060(3) 0.070(4) 0.094(4) -0.005(3) 0.044(3) 0.010(3) C9 0.066(3) 0.065(3) 0.082(3) 0.004(3) 0.049(3) 0.006(3) C10 0.082(4) 0.048(3) 0.094(4) 0.001(3) 0.059(3) 0.004(3) C11 0.053(3) 0.048(3) 0.077(3) -0.005(2) 0.038(2) 0.000(2) C12 0.069(3) 0.055(3) 0.065(3) -0.008(2) 0.035(3) -0.006(2) C13 0.071(3) 0.069(3) 0.074(3) -0.013(3) 0.041(3) -0.006(3) C14 0.085(4) 0.102(5) 0.113(4) -0.010(4) 0.066(4) 0.005(4) C15 0.064(4) 0.118(5) 0.080(4) 0.013(4) 0.018(3) 0.011(4) C16 0.059(3) 0.108(5) 0.091(4) -0.019(3) 0.027(3) 0.010(3) C17 0.097(4) 0.108(5) 0.084(4) 0.002(3) 0.061(3) 0.011(4) C18 0.073(3) 0.082(4) 0.049(3) -0.005(3) 0.031(2) 0.000(3) C19 0.107(5) 0.083(4) 0.070(3) -0.003(3) 0.056(3) -0.001(4) C20 0.122(6) 0.098(5) 0.066(3) -0.003(3) 0.046(4) -0.032(4) C21 0.085(4) 0.139(7) 0.066(3) 0.013(4) 0.041(3) -0.017(4) C22 0.092(5) 0.132(6) 0.089(4) -0.003(4) 0.058(4) 0.004(5) C23 0.096(5) 0.096(5) 0.084(4) -0.022(3) 0.053(4) -0.008(4) C24 0.120(6) 0.243(12) 0.116(6) 0.011(6) 0.058(5) -0.064(7) C25 0.092(4) 0.049(3) 0.092(4) 0.002(3) 0.057(4) 0.000(3) C26 0.090(4) 0.077(4) 0.089(4) 0.010(3) 0.044(4) 0.000(3) C27 0.173(8) 0.096(5) 0.095(5) 0.014(4) 0.087(6) 0.000(5) C28 0.149(8) 0.109(6) 0.173(8) 0.071(6) 0.129(7) 0.057(6) C29 0.088(5) 0.169(9) 0.144(7) 0.077(6) 0.061(5) 0.022(5) C30 0.098(5) 0.124(6) 0.086(4) 0.014(4) 0.043(4) -0.021(4) C31 0.180(5) 0.194(6) 0.194(5) 0.037(4) 0.124(4) 0.017(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B F2 1.367(6) . ? B F1 1.388(7) . ? B N1 1.535(7) . ? B N2 1.559(7) . ? N1 C1 1.367(6) . ? N1 C4 1.392(6) . ? N2 C9 1.345(6) . ? N2 C6 1.394(5) . ? S1 C10 1.715(5) . ? S1 C13 1.716(6) . ? S2 O1 1.398(5) . ? S2 O2 1.436(4) . ? S2 C18 1.746(5) . ? S2 C13 1.762(5) . ? S3 O3 1.457(5) . ? S3 C25 1.794(6) . ? S3 C10 1.803(5) . ? C1 C2 1.388(7) . ? C1 C15 1.504(7) . ? C2 C3 1.379(7) . ? C3 C4 1.437(7) . ? C3 C14 1.501(7) . ? C4 C5 1.408(6) . ? C5 C6 1.398(6) . ? C5 C11 1.479(6) . ? C6 C7 1.437(6) . ? C7 C8 1.355(6) . ? C7 C16 1.501(7) . ? C8 C9 1.393(7) . ? C9 C17 1.488(7) . ? C10 C11 1.356(6) . ? C11 C12 1.431(6) . ? C12 C13 1.357(6) . ? C18 C19 1.370(8) . ? C18 C23 1.395(7) . ? C19 C20 1.385(8) . ? C20 C21 1.365(9) . ? C21 C22 1.366(10) . ? C21 C24 1.524(9) . ? C22 C23 1.362(8) . ? C25 C30 1.360(8) . ? C25 C26 1.361(8) . ? C26 C27 1.349(10) . ? C27 C28 1.365(11) . ? C28 C29 1.394(12) . ? C28 C31 1.535(10) . ? C29 C30 1.360(10) . ? 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 F2 B F1 109.8(5) . . ? F2 B N1 110.9(5) . . ? F1 B N1 110.1(4) . . ? F2 B N2 109.7(4) . . ? F1 B N2 109.1(5) . . ? N1 B N2 107.1(4) . . ? C1 N1 C4 107.9(4) . . ? C1 N1 B 125.9(4) . . ? C4 N1 B 126.0(4) . . ? C9 N2 C6 108.1(4) . . ? C9 N2 B 127.1(4) . . ? C6 N2 B 124.8(4) . . ? C10 S1 C13 90.0(2) . . ? O1 S2 O2 120.2(3) . . ? O1 S2 C18 108.2(3) . . ? O2 S2 C18 109.3(3) . . ? O1 S2 C13 107.3(3) . . ? O2 S2 C13 106.9(3) . . ? C18 S2 C13 103.8(2) . . ? O3 S3 C25 108.3(3) . . ? O3 S3 C10 103.2(3) . . ? C25 S3 C10 99.1(2) . . ? N1 C1 C2 108.9(5) . . ? N1 C1 C15 122.8(5) . . ? C2 C1 C15 128.2(5) . . ? C3 C2 C1 109.4(5) . . ? C2 C3 C4 105.7(5) . . ? C2 C3 C14 124.7(5) . . ? C4 C3 C14 129.6(5) . . ? N1 C4 C5 119.7(4) . . ? N1 C4 C3 108.0(4) . . ? C5 C4 C3 132.3(5) . . ? C6 C5 C4 121.5(4) . . ? C6 C5 C11 119.3(4) . . ? C4 C5 C11 119.1(4) . . ? N2 C6 C5 120.4(4) . . ? N2 C6 C7 107.6(4) . . ? C5 C6 C7 132.0(4) . . ? C8 C7 C6 105.8(4) . . ? C8 C7 C16 125.0(5) . . ? C6 C7 C16 129.2(5) . . ? C7 C8 C9 109.7(4) . . ? N2 C9 C8 108.8(4) . . ? N2 C9 C17 122.9(5) . . ? C8 C9 C17 128.3(5) . . ? C11 C10 S1 114.3(4) . . ? C11 C10 S3 127.6(4) . . ? S1 C10 S3 117.8(3) . . ? C10 C11 C12 110.1(4) . . ? C10 C11 C5 125.6(4) . . ? C12 C11 C5 124.3(4) . . ? C13 C12 C11 113.0(5) . . ? C12 C13 S1 112.6(4) . . ? C12 C13 S2 126.9(4) . . ? S1 C13 S2 120.6(3) . . ? C19 C18 C23 119.2(5) . . ? C19 C18 S2 120.3(4) . . ? C23 C18 S2 120.4(5) . . ? C18 C19 C20 118.9(6) . . ? C21 C20 C19 122.4(6) . . ? C20 C21 C22 117.6(6) . . ? C20 C21 C24 120.8(8) . . ? C22 C21 C24 121.5(7) . . ? C23 C22 C21 121.9(6) . . ? C22 C23 C18 119.8(6) . . ? C30 C25 C26 121.3(6) . . ? C30 C25 S3 122.9(5) . . ? C26 C25 S3 115.8(5) . . ? C27 C26 C25 118.8(6) . . ? C26 C27 C28 121.9(7) . . ? C27 C28 C29 118.4(6) . . ? C27 C28 C31 123.0(10) . . ? C29 C28 C31 118.6(10) . . ? C30 C29 C28 119.8(7) . . ? C25 C30 C29 119.8(7) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.800 _refine_diff_density_min -0.558 _refine_diff_density_rms 0.083 # Attachment '- nchu82-1_8_.cif' data_nchu82-1 _database_code_depnum_ccdc_archive 'CCDC 869054' #TrackingRef '- nchu82-1_8_.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C12H13B1F2N2 _chemical_formula_sum 'C12 H13 B F2 N2' _chemical_formula_weight 234.05 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' F F 0.0171 0.0103 '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 6.350(3) _cell_length_b 13.032(7) _cell_length_c 14.253(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.75(2) _cell_angle_gamma 90.00 _cell_volume 1175.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4133 _cell_measurement_theta_min 2.12 _cell_measurement_theta_max 32.15 _exptl_crystal_description platy _exptl_crystal_colour Darkred _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.930 _exptl_absorpt_correction_T_max 0.941 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 16333 _diffrn_reflns_av_R_equivalents 0.0857 _diffrn_reflns_av_sigmaI/netI 0.1658 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 32.15 _reflns_number_total 4133 _reflns_number_gt 1720 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker APEX II' _computing_data_reduction 'Bruker APEX II' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP3 _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^)+(0.0692P)^2^+0.2425P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4133 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2216 _refine_ls_R_factor_gt 0.0992 _refine_ls_wR_factor_ref 0.2524 _refine_ls_wR_factor_gt 0.2003 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.075 _refine_ls_shift/su_mean 0.002 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 B B 0.2057(5) 0.2339(3) 0.4822(2) 0.0527(8) Uani 1 1 d . . . F1 F 0.1192(3) 0.30817(15) 0.53913(12) 0.0802(6) Uani 1 1 d . . . F2 F 0.3213(3) 0.16538(16) 0.53975(13) 0.0843(7) Uani 1 1 d . . . N1 N 0.3474(4) 0.28589(16) 0.41335(15) 0.0474(6) Uani 1 1 d . . . N2 N 0.0251(3) 0.17820(16) 0.42308(15) 0.0467(6) Uani 1 1 d . . . C1 C 0.5228(5) 0.3437(2) 0.4337(2) 0.0565(8) Uani 1 1 d . . . H1 H 0.5778 0.3594 0.4945 0.068 Uiso 1 1 calc R . . C2 C 0.6105(4) 0.37696(19) 0.3528(2) 0.0513(7) Uani 1 1 d . . . C3 C 0.4817(5) 0.3365(2) 0.2785(2) 0.0522(7) Uani 1 1 d . . . H3 H 0.4998 0.3454 0.2150 0.063 Uiso 1 1 calc R . . C4 C 0.3191(4) 0.27972(19) 0.31542(17) 0.0456(6) Uani 1 1 d . . . C5 C 0.1482(4) 0.22561(19) 0.27307(17) 0.0459(7) Uani 1 1 d . . . H5 H 0.1310 0.2226 0.2077 0.055 Uiso 1 1 calc R . . C6 C 0.0036(4) 0.17632(18) 0.32398(17) 0.0438(6) Uani 1 1 d . . . C7 C -0.1833(4) 0.1200(2) 0.2947(2) 0.0498(7) Uani 1 1 d . . . C8 C -0.2681(5) 0.0882(2) 0.3757(2) 0.0568(8) Uani 1 1 d . . . H8 H -0.3900 0.0492 0.3785 0.068 Uiso 1 1 calc R . . C9 C -0.1392(4) 0.1248(2) 0.45317(19) 0.0520(7) Uani 1 1 d . . . C10 C 0.8024(5) 0.4439(3) 0.3494(3) 0.0740(9) Uani 1 1 d . . . H21A H 0.7629 0.5144 0.3564 0.111 Uiso 1 1 calc R . . H21B H 0.8614 0.4348 0.2901 0.111 Uiso 1 1 calc R . . H21C H 0.9054 0.4253 0.3996 0.111 Uiso 1 1 calc R . . C11 C -0.2663(5) 0.1023(2) 0.1946(2) 0.0655(9) Uani 1 1 d . . . H10A H -0.2838 0.0300 0.1836 0.098 Uiso 1 1 calc R . . H10B H -0.1681 0.1293 0.1532 0.098 Uiso 1 1 calc R . . H10C H -0.4001 0.1361 0.1827 0.098 Uiso 1 1 calc R . . C12 C -0.1683(5) 0.1092(3) 0.5549(2) 0.0674(9) Uani 1 1 d . . . H13A H -0.0329 0.1002 0.5892 0.101 Uiso 1 1 calc R . . H13B H -0.2532 0.0492 0.5623 0.101 Uiso 1 1 calc R . . H13C H -0.2375 0.1680 0.5788 0.101 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 B 0.058(2) 0.0614(19) 0.0388(16) 0.0044(14) 0.0013(14) 0.0012(16) F1 0.1000(15) 0.0841(13) 0.0596(11) -0.0255(9) 0.0257(10) -0.0154(11) F2 0.0729(13) 0.1062(15) 0.0702(12) 0.0412(11) -0.0151(10) -0.0094(11) N1 0.0512(14) 0.0501(12) 0.0402(12) -0.0004(9) -0.0013(10) -0.0022(10) N2 0.0511(14) 0.0470(12) 0.0424(12) 0.0019(9) 0.0070(10) 0.0039(10) C1 0.0560(19) 0.0531(16) 0.0581(18) -0.0037(13) -0.0092(14) -0.0022(14) C2 0.0511(16) 0.0435(14) 0.0595(18) 0.0021(12) 0.0048(14) 0.0002(12) C3 0.0600(18) 0.0479(15) 0.0498(16) 0.0028(12) 0.0111(14) 0.0016(13) C4 0.0522(17) 0.0446(14) 0.0401(14) -0.0012(11) 0.0045(12) 0.0035(12) C5 0.0532(17) 0.0476(14) 0.0368(13) -0.0034(11) 0.0034(12) 0.0016(12) C6 0.0510(16) 0.0409(13) 0.0392(14) -0.0022(10) 0.0023(12) 0.0041(12) C7 0.0491(16) 0.0436(14) 0.0564(17) -0.0045(12) 0.0016(13) 0.0004(12) C8 0.0496(17) 0.0525(16) 0.069(2) 0.0035(14) 0.0075(14) -0.0057(13) C9 0.0513(17) 0.0501(15) 0.0566(17) 0.0089(12) 0.0157(14) 0.0058(13) C10 0.063(2) 0.0603(18) 0.098(3) 0.0052(17) 0.0060(18) -0.0118(16) C11 0.065(2) 0.0609(18) 0.069(2) -0.0079(15) -0.0081(16) -0.0085(15) C12 0.067(2) 0.0719(19) 0.065(2) 0.0135(15) 0.0189(16) -0.0004(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B F2 1.382(4) . ? B F1 1.404(4) . ? B N1 1.542(4) . ? B N2 1.547(4) . ? N1 C1 1.356(4) . ? N1 C4 1.395(3) . ? N2 C9 1.353(3) . ? N2 C6 1.408(3) . ? C1 C2 1.390(4) . ? C2 C3 1.388(4) . ? C2 C10 1.502(4) . ? C3 C4 1.407(4) . ? C4 C5 1.389(4) . ? C5 C6 1.376(4) . ? C6 C7 1.428(4) . ? C7 C8 1.377(4) . ? C7 C11 1.497(4) . ? C8 C9 1.403(4) . ? C9 C12 1.491(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 F2 B F1 108.5(2) . . ? F2 B N1 110.6(3) . . ? F1 B N1 110.0(2) . . ? F2 B N2 110.7(3) . . ? F1 B N2 109.3(2) . . ? N1 B N2 107.8(2) . . ? C1 N1 C4 106.4(2) . . ? C1 N1 B 128.3(2) . . ? C4 N1 B 125.3(2) . . ? C9 N2 C6 107.2(2) . . ? C9 N2 B 128.7(2) . . ? C6 N2 B 124.1(2) . . ? N1 C1 C2 112.0(2) . . ? C3 C2 C1 105.2(2) . . ? C3 C2 C10 128.7(3) . . ? C1 C2 C10 126.1(3) . . ? C2 C3 C4 108.6(2) . . ? C5 C4 N1 119.7(2) . . ? C5 C4 C3 132.5(2) . . ? N1 C4 C3 107.8(2) . . ? C6 C5 C4 122.6(2) . . ? C5 C6 N2 120.5(2) . . ? C5 C6 C7 131.3(2) . . ? N2 C6 C7 108.1(2) . . ? C8 C7 C6 106.4(2) . . ? C8 C7 C11 128.4(3) . . ? C6 C7 C11 125.2(3) . . ? C7 C8 C9 108.3(3) . . ? N2 C9 C8 109.9(2) . . ? N2 C9 C12 122.7(3) . . ? C8 C9 C12 127.5(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 32.15 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.287 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.060 # Attachment '- nchu85-1_9_.cif' data_nchu85-1 _database_code_depnum_ccdc_archive 'CCDC 869055' #TrackingRef '- nchu85-1_9_.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C31H29B1F2N2O4S3 _chemical_formula_sum 'C31 H29 B F2 N2 O4 S3' _chemical_formula_weight 638.55 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' F F 0.0171 0.0103 '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 38.241(9) _cell_length_b 7.6428(18) _cell_length_c 25.192(7) _cell_angle_alpha 90.00 _cell_angle_beta 121.40(2) _cell_angle_gamma 90.00 _cell_volume 6285(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4422 _cell_measurement_theta_min 1.25 _cell_measurement_theta_max 23.21 _exptl_crystal_description Cubic _exptl_crystal_colour Darkgreen _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2656 _exptl_absorpt_coefficient_mu 0.286 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.930 _exptl_absorpt_correction_T_max 0.941 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 27214 _diffrn_reflns_av_R_equivalents 0.0713 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 23.21 _reflns_number_total 4422 _reflns_number_gt 2432 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker APEX II' _computing_data_reduction 'Bruker APEX II' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP3 _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^)+(0.1218P)^2^+5.4792P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4422 _refine_ls_number_parameters 394 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0709 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1770 _refine_ls_wR_factor_gt 0.1466 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.008 _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 B B 0.17537(18) 0.3272(8) 0.5435(3) 0.0734(17) Uani 1 1 d . . . F1 F 0.18028(9) 0.4327(5) 0.59166(13) 0.1110(11) Uani 1 1 d . . . F2 F 0.19042(9) 0.1600(4) 0.56651(14) 0.1010(10) Uani 1 1 d . . . N1 N 0.12973(11) 0.3153(5) 0.49200(16) 0.0610(10) Uani 1 1 d . . . N2 N 0.19859(11) 0.4046(5) 0.51428(17) 0.0678(10) Uani 1 1 d . . . S1 S 0.08686(4) 0.65083(17) 0.23940(7) 0.0852(5) Uani 1 1 d . . . S2 S 0.11023(5) 0.84799(17) 0.35469(9) 0.0979(6) Uani 1 1 d . . . O1 O 0.08860(17) 0.9681(5) 0.3020(2) 0.1415(19) Uani 1 1 d . . . O2 O 0.15176(14) 0.8787(6) 0.4019(3) 0.153(2) Uani 1 1 d . . . S3 S 0.07961(4) 0.32731(19) 0.16734(6) 0.0816(5) Uani 1 1 d . . . O3 O 0.04962(11) 0.2010(6) 0.15761(17) 0.1057(13) Uani 1 1 d . . . O4 O 0.06918(12) 0.4646(6) 0.12231(16) 0.1130(14) Uani 1 1 d . . . C1 C 0.09868(15) 0.2587(6) 0.4985(2) 0.0676(13) Uani 1 1 d . . . C2 C 0.06223(15) 0.2684(6) 0.4411(2) 0.0729(13) Uani 1 1 d . . . H2 H 0.0365 0.2366 0.4335 0.087 Uiso 1 1 calc R . . C3 C 0.07011(14) 0.3325(5) 0.3973(2) 0.0649(12) Uani 1 1 d . . . C4 C 0.11323(13) 0.3630(5) 0.4296(2) 0.0591(12) Uani 1 1 d . . . C5 C 0.13866(13) 0.4305(5) 0.4101(2) 0.0604(12) Uani 1 1 d . . . C6 C 0.18096(14) 0.4512(6) 0.4512(2) 0.0644(12) Uani 1 1 d . . . C7 C 0.21325(15) 0.5120(6) 0.4430(2) 0.0746(14) Uani 1 1 d . . . C8 C 0.24878(16) 0.5019(7) 0.5006(3) 0.0844(15) Uani 1 1 d . . . H8 H 0.2748 0.5331 0.5094 0.101 Uiso 1 1 calc R . . C9 C 0.23940(15) 0.4374(7) 0.5436(2) 0.0759(14) Uani 1 1 d . . . C10 C 0.10722(15) 0.6453(6) 0.3185(2) 0.0717(13) Uani 1 1 d . . . C11 C 0.12033(13) 0.4800(6) 0.3434(2) 0.0600(12) Uani 1 1 d . . . C12 C 0.11333(13) 0.3587(6) 0.2967(2) 0.0637(12) Uani 1 1 d . . . H12 H 0.1201 0.2408 0.3045 0.076 Uiso 1 1 calc R . . C13 C 0.09556(13) 0.4321(6) 0.2389(2) 0.0677(13) Uani 1 1 d . . . C14 C 0.08143(15) 0.8253(5) 0.3892(2) 0.0681(13) Uani 1 1 d . . . C15 C 0.09980(17) 0.7775(7) 0.4515(3) 0.0857(16) Uani 1 1 d . . . H15 H 0.1280 0.7595 0.4754 0.103 Uiso 1 1 calc R . . C16 C 0.0764(3) 0.7576(8) 0.4769(3) 0.1032(19) Uani 1 1 d . . . H16 H 0.0892 0.7249 0.5184 0.124 Uiso 1 1 calc R . . C17 C 0.0355(3) 0.7827(8) 0.4448(4) 0.0984(18) Uani 1 1 d . . . C18 C 0.01698(17) 0.8338(8) 0.3829(3) 0.1004(19) Uani 1 1 d . . . H18 H -0.0111 0.8550 0.3600 0.120 Uiso 1 1 calc R . . C19 C 0.03980(17) 0.8534(7) 0.3551(2) 0.0830(15) Uani 1 1 d . . . H19 H 0.0270 0.8856 0.3135 0.100 Uiso 1 1 calc R . . C20 C 0.0093(3) 0.7586(13) 0.4742(4) 0.183(4) Uani 1 1 d . . . H20A H 0.0007 0.6388 0.4700 0.274 Uiso 1 1 calc R . . H20B H -0.0143 0.8330 0.4535 0.274 Uiso 1 1 calc R . . H20C H 0.0252 0.7890 0.5175 0.274 Uiso 1 1 calc R . . C21 C 0.12327(14) 0.2194(7) 0.1789(2) 0.0708(13) Uani 1 1 d . . . C22 C 0.13305(19) 0.0569(8) 0.2077(2) 0.0871(16) Uani 1 1 d . . . H22 H 0.1162 0.0046 0.2195 0.105 Uiso 1 1 calc R . . C23 C 0.1682(2) -0.0257(8) 0.2185(2) 0.1016(19) Uani 1 1 d . . . H23 H 0.1752 -0.1332 0.2388 0.122 Uiso 1 1 calc R . . C24 C 0.19335(18) 0.0462(11) 0.2002(3) 0.1012(19) Uani 1 1 d . . . C25 C 0.18214(19) 0.2045(10) 0.1691(3) 0.1002(19) Uani 1 1 d . . . H25 H 0.1978 0.2518 0.1542 0.120 Uiso 1 1 calc R . . C26 C 0.14823(18) 0.2924(8) 0.1601(2) 0.0877(16) Uani 1 1 d . . . H26 H 0.1419 0.4018 0.1412 0.105 Uiso 1 1 calc R . . C27 C 0.2321(2) -0.0451(13) 0.2121(3) 0.153(3) Uani 1 1 d . . . H27A H 0.2329 -0.0448 0.1747 0.229 Uiso 1 1 calc R . . H27B H 0.2322 -0.1636 0.2248 0.229 Uiso 1 1 calc R . . H27C H 0.2556 0.0155 0.2443 0.229 Uiso 1 1 calc R . . C28 C 0.03833(14) 0.3570(7) 0.3295(2) 0.0804(15) Uani 1 1 d . . . H28A H 0.0118 0.3289 0.3225 0.121 Uiso 1 1 calc R . . H28B H 0.0444 0.2812 0.3049 0.121 Uiso 1 1 calc R . . H28C H 0.0386 0.4764 0.3179 0.121 Uiso 1 1 calc R . . C29 C 0.10522(17) 0.1951(7) 0.5591(2) 0.0891(16) Uani 1 1 d . . . H29A H 0.1249 0.1017 0.5745 0.134 Uiso 1 1 calc R . . H29B H 0.0797 0.1534 0.5532 0.134 Uiso 1 1 calc R . . H29C H 0.1152 0.2894 0.5886 0.134 Uiso 1 1 calc R . . C30 C 0.21064(16) 0.5785(8) 0.3847(2) 0.0913(16) Uani 1 1 d . . . H30A H 0.1975 0.6908 0.3740 0.137 Uiso 1 1 calc R . . H30B H 0.1950 0.4978 0.3513 0.137 Uiso 1 1 calc R . . H30C H 0.2377 0.5892 0.3916 0.137 Uiso 1 1 calc R . . C31 C 0.26781(16) 0.4065(8) 0.6115(2) 0.0966(17) Uani 1 1 d . . . H31A H 0.2616 0.4872 0.6347 0.145 Uiso 1 1 calc R . . H31B H 0.2956 0.4237 0.6219 0.145 Uiso 1 1 calc R . . H31C H 0.2645 0.2889 0.6215 0.145 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 B 0.068(4) 0.085(5) 0.071(4) -0.014(3) 0.039(3) -0.002(3) F1 0.094(2) 0.158(3) 0.088(2) -0.051(2) 0.0529(17) -0.025(2) F2 0.083(2) 0.110(3) 0.108(2) 0.0330(19) 0.0483(17) 0.0134(17) N1 0.061(2) 0.066(2) 0.060(2) -0.0072(18) 0.034(2) -0.0062(18) N2 0.059(3) 0.068(2) 0.075(3) -0.015(2) 0.034(2) -0.010(2) S1 0.0978(10) 0.0636(9) 0.1000(10) 0.0256(7) 0.0555(9) 0.0114(7) S2 0.1181(13) 0.0528(9) 0.1585(15) -0.0138(9) 0.0970(12) -0.0158(8) O1 0.255(6) 0.050(2) 0.203(5) 0.031(3) 0.177(5) 0.019(3) O2 0.106(3) 0.122(4) 0.260(6) -0.106(4) 0.115(4) -0.063(3) S3 0.0745(9) 0.0944(11) 0.0660(8) 0.0071(7) 0.0296(7) -0.0010(8) O3 0.080(2) 0.132(3) 0.102(3) -0.025(2) 0.045(2) -0.034(2) O4 0.117(3) 0.131(3) 0.070(2) 0.041(2) 0.034(2) 0.028(3) C1 0.072(3) 0.065(3) 0.080(4) -0.010(2) 0.050(3) -0.007(3) C2 0.064(3) 0.069(3) 0.091(4) -0.004(3) 0.045(3) -0.009(3) C3 0.062(3) 0.052(3) 0.082(3) -0.003(2) 0.039(3) -0.005(2) C4 0.057(3) 0.055(3) 0.070(3) -0.007(2) 0.037(2) -0.005(2) C5 0.062(3) 0.046(3) 0.073(3) -0.009(2) 0.035(3) -0.002(2) C6 0.064(3) 0.062(3) 0.072(3) -0.008(2) 0.038(3) -0.006(2) C7 0.070(3) 0.069(3) 0.100(4) -0.007(3) 0.055(3) -0.010(3) C8 0.059(3) 0.085(4) 0.104(4) -0.010(3) 0.039(3) -0.012(3) C9 0.064(3) 0.074(3) 0.087(4) -0.013(3) 0.037(3) -0.010(3) C10 0.079(3) 0.053(3) 0.096(3) -0.002(3) 0.055(3) -0.007(2) C11 0.059(3) 0.051(3) 0.076(3) 0.001(3) 0.039(2) -0.007(2) C12 0.065(3) 0.053(3) 0.068(3) 0.001(3) 0.032(2) -0.001(2) C13 0.064(3) 0.066(3) 0.071(3) 0.011(2) 0.033(2) 0.001(2) C14 0.067(3) 0.047(3) 0.082(3) -0.008(2) 0.033(3) -0.001(2) C15 0.079(4) 0.078(4) 0.079(4) -0.013(3) 0.026(3) 0.012(3) C16 0.134(6) 0.093(5) 0.078(4) -0.009(3) 0.052(5) 0.005(4) C17 0.121(6) 0.088(4) 0.108(5) -0.037(4) 0.075(5) -0.035(4) C18 0.063(3) 0.111(5) 0.115(5) -0.031(4) 0.038(4) -0.015(3) C19 0.073(4) 0.090(4) 0.072(3) -0.003(3) 0.027(3) 0.002(3) C20 0.241(10) 0.182(8) 0.229(10) -0.091(8) 0.194(9) -0.096(8) C21 0.075(3) 0.085(4) 0.050(3) 0.003(3) 0.031(2) -0.009(3) C22 0.109(4) 0.088(4) 0.073(3) 0.005(3) 0.053(3) 0.001(4) C23 0.134(6) 0.095(4) 0.074(4) 0.013(3) 0.053(4) 0.029(4) C24 0.090(4) 0.140(6) 0.060(3) -0.010(4) 0.029(3) 0.016(4) C25 0.077(4) 0.145(6) 0.072(4) 0.002(4) 0.034(3) -0.001(4) C26 0.091(4) 0.096(4) 0.071(3) 0.012(3) 0.040(3) -0.009(4) C27 0.110(5) 0.211(9) 0.121(5) -0.009(5) 0.049(4) 0.055(6) C28 0.060(3) 0.078(4) 0.087(4) 0.013(3) 0.026(3) -0.005(2) C29 0.100(4) 0.101(4) 0.084(4) 0.001(3) 0.061(3) -0.005(3) C30 0.082(4) 0.098(4) 0.112(4) 0.001(3) 0.064(3) -0.012(3) C31 0.073(3) 0.102(4) 0.086(4) -0.005(3) 0.021(3) -0.010(3) _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 B F1 1.386(6) . ? B F2 1.397(7) . ? B N2 1.536(7) . ? B N1 1.542(7) . ? N1 C1 1.352(5) . ? N1 C4 1.404(5) . ? N2 C9 1.358(6) . ? N2 C6 1.412(5) . ? S1 C13 1.706(5) . ? S1 C10 1.720(5) . ? S2 O2 1.423(5) . ? S2 O1 1.465(5) . ? S2 C14 1.730(5) . ? S2 C10 1.771(5) . ? S3 O3 1.419(4) . ? S3 O4 1.440(4) . ? S3 C21 1.745(5) . ? S3 C13 1.765(5) . ? C1 C2 1.393(6) . ? C1 C29 1.494(7) . ? C2 C3 1.377(6) . ? C3 C4 1.428(6) . ? C3 C28 1.505(6) . ? C4 C5 1.396(6) . ? C5 C6 1.403(6) . ? C5 C11 1.494(6) . ? C6 C7 1.432(6) . ? C7 C8 1.380(7) . ? C7 C30 1.507(7) . ? C8 C9 1.395(7) . ? C9 C31 1.492(7) . ? C10 C11 1.383(6) . ? C11 C12 1.409(6) . ? C12 C13 1.368(6) . ? C14 C19 1.376(7) . ? C14 C15 1.394(7) . ? C15 C16 1.350(8) . ? C16 C17 1.350(8) . ? C17 C18 1.391(9) . ? C17 C20 1.535(9) . ? C18 C19 1.383(8) . ? C21 C26 1.385(7) . ? C21 C22 1.388(7) . ? C22 C23 1.379(8) . ? C23 C24 1.378(8) . ? C24 C25 1.382(9) . ? C24 C27 1.519(8) . ? C25 C26 1.370(8) . ? 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 F1 B F2 109.2(5) . . ? F1 B N2 110.3(4) . . ? F2 B N2 109.6(4) . . ? F1 B N1 110.4(4) . . ? F2 B N1 109.7(4) . . ? N2 B N1 107.7(4) . . ? C1 N1 C4 108.0(4) . . ? C1 N1 B 126.7(4) . . ? C4 N1 B 125.3(4) . . ? C9 N2 C6 107.7(4) . . ? C9 N2 B 126.8(4) . . ? C6 N2 B 125.5(4) . . ? C13 S1 C10 90.7(2) . . ? O2 S2 O1 120.8(3) . . ? O2 S2 C14 108.8(3) . . ? O1 S2 C14 108.1(3) . . ? O2 S2 C10 108.6(3) . . ? O1 S2 C10 103.1(3) . . ? C14 S2 C10 106.5(2) . . ? O3 S3 O4 119.5(2) . . ? O3 S3 C21 108.9(3) . . ? O4 S3 C21 108.9(2) . . ? O3 S3 C13 107.7(2) . . ? O4 S3 C13 106.3(2) . . ? C21 S3 C13 104.6(2) . . ? N1 C1 C2 108.9(4) . . ? N1 C1 C29 122.5(4) . . ? C2 C1 C29 128.5(5) . . ? C3 C2 C1 109.4(4) . . ? C2 C3 C4 105.8(4) . . ? C2 C3 C28 124.7(4) . . ? C4 C3 C28 129.5(4) . . ? C5 C4 N1 120.1(4) . . ? C5 C4 C3 132.0(4) . . ? N1 C4 C3 107.9(4) . . ? C4 C5 C6 121.9(4) . . ? C4 C5 C11 119.0(4) . . ? C6 C5 C11 119.1(4) . . ? C5 C6 N2 119.5(4) . . ? C5 C6 C7 132.9(5) . . ? N2 C6 C7 107.6(4) . . ? C8 C7 C6 106.3(4) . . ? C8 C7 C30 125.0(5) . . ? C6 C7 C30 128.7(5) . . ? C7 C8 C9 109.0(5) . . ? N2 C9 C8 109.3(4) . . ? N2 C9 C31 122.5(5) . . ? C8 C9 C31 128.1(5) . . ? C11 C10 S1 112.7(3) . . ? C11 C10 S2 130.8(4) . . ? S1 C10 S2 116.3(3) . . ? C10 C11 C12 110.9(4) . . ? C10 C11 C5 126.1(4) . . ? C12 C11 C5 123.1(4) . . ? C13 C12 C11 113.1(4) . . ? C12 C13 S1 112.6(4) . . ? C12 C13 S3 128.2(4) . . ? S1 C13 S3 119.2(3) . . ? C19 C14 C15 118.9(5) . . ? C19 C14 S2 120.2(4) . . ? C15 C14 S2 120.8(4) . . ? C16 C15 C14 119.5(5) . . ? C17 C16 C15 123.3(6) . . ? C16 C17 C18 117.7(6) . . ? C16 C17 C20 122.7(8) . . ? C18 C17 C20 119.6(8) . . ? C19 C18 C17 120.7(5) . . ? C14 C19 C18 119.8(5) . . ? C26 C21 C22 119.6(5) . . ? C26 C21 S3 121.5(4) . . ? C22 C21 S3 119.0(4) . . ? C23 C22 C21 118.9(5) . . ? C24 C23 C22 122.0(6) . . ? C23 C24 C25 118.3(6) . . ? C23 C24 C27 121.9(8) . . ? C25 C24 C27 119.8(7) . . ? C26 C25 C24 120.7(6) . . ? C25 C26 C21 120.4(6) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 23.21 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.331 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.088