# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address S.Yamaguchi 'Department of chemistry, Graduate school of science, Nagoya university Furo, Chikusa, Nagoya 464-8602, Japan' A.Iida 'Department of chemistry, Graduate school of science, Nagoya university Furo, Chikusa, Nagoya 464-8602, Japan' A.Sekioka 'Department of chemistry, Graduate school of science, Nagoya university Furo, Chikusa, Nagoya 464-8602, Japan' _publ_contact_author_address 'Department of chemistry, Graduate school of science, Nagoya university Furo, Chikusa, Nagoya 464-8602, Japan' _publ_contact_author_email yamaguchi.shigehiro@b.mbox.nagoya-u.ac.jp _publ_contact_author_fax +81527895947 _publ_contact_author_phone +81527892291 _publ_contact_author_name 'Shigehiro Yamaguchi' data_cmpd1a _database_code_depnum_ccdc_archive 'CCDC 857120' _audit_creation_method SHELXL-97 _chemical_name_systematic ; dibenzoborole ; _chemical_name_common dibenzoborole _chemical_melting_point 405 _chemical_formula_moiety 'C21 H19 B' _chemical_formula_sum 'C21 H19 B' _chemical_formula_weight 282.17 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 7.9976(10) _cell_length_b 30.448(4) _cell_length_c 13.5205(18) _cell_angle_alpha 90.00 _cell_angle_beta 96.2528(5) _cell_angle_gamma 90.00 _cell_volume 3272.8(7) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 9512 _cell_measurement_theta_min 2.9098 _cell_measurement_theta_max 31.5050 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.145 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9874 _exptl_absorpt_correction_T_max 0.9874 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; 'Saturn70 CCD (4x4 bin mode) with MicroMax-007' ; _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20986 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5691 _reflns_number_gt 5258 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 for windows' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0498P)^2^+1.1718P] 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 none _refine_ls_number_reflns 5691 _refine_ls_number_parameters 403 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1182 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 B1 B -0.0235(2) 0.14250(6) 0.64330(13) 0.0242(4) Uani 1 1 d . . . C1 C -0.11476(19) 0.16758(5) 0.72313(11) 0.0256(3) Uani 1 1 d . . . C2 C -0.18985(19) 0.20574(5) 0.67785(11) 0.0242(3) Uani 1 1 d . . . C3 C -0.14944(18) 0.20910(5) 0.57348(11) 0.0230(3) Uani 1 1 d . . . C4 C -0.05528(18) 0.17216(5) 0.54842(11) 0.0233(3) Uani 1 1 d . . . C5 C -0.00644(19) 0.16911(5) 0.45322(11) 0.0259(3) Uani 1 1 d . . . H1 H 0.0550 0.1442 0.4350 0.031 Uiso 1 1 calc R . . C6 C -0.0477(2) 0.20261(5) 0.38430(11) 0.0283(4) Uani 1 1 d . . . H2 H -0.0144 0.2006 0.3191 0.034 Uiso 1 1 calc R . . C7 C -0.1372(2) 0.23882(5) 0.41112(11) 0.0273(3) Uani 1 1 d . . . H3 H -0.1634 0.2616 0.3641 0.033 Uiso 1 1 calc R . . C8 C -0.18976(19) 0.24247(5) 0.50571(11) 0.0262(3) Uani 1 1 d . . . H4 H -0.2519 0.2673 0.5232 0.031 Uiso 1 1 calc R . . C9 C -0.2850(2) 0.23356(5) 0.72900(12) 0.0307(4) Uani 1 1 d . . . H5 H -0.3352 0.2590 0.6978 0.037 Uiso 1 1 calc R . . C10 C -0.3064(2) 0.22370(6) 0.82743(13) 0.0382(4) Uani 1 1 d . . . H6 H -0.3725 0.2426 0.8634 0.046 Uiso 1 1 calc R . . C11 C -0.2329(2) 0.18685(6) 0.87364(13) 0.0394(4) Uani 1 1 d . . . H7 H -0.2484 0.1808 0.9410 0.047 Uiso 1 1 calc R . . C12 C -0.1364(2) 0.15866(5) 0.82189(12) 0.0329(4) Uani 1 1 d . . . H8 H -0.0856 0.1335 0.8539 0.039 Uiso 1 1 calc R . . C13 C 0.07617(19) 0.09825(5) 0.65551(10) 0.0225(3) Uani 1 1 d . . . C14 C -0.00233(19) 0.05853(5) 0.62417(11) 0.0242(3) Uani 1 1 d . . . C15 C 0.0865(2) 0.01922(5) 0.63708(11) 0.0270(3) Uani 1 1 d . . . H9 H 0.0323 -0.0074 0.6158 0.032 Uiso 1 1 calc R . . C16 C 0.2519(2) 0.01796(5) 0.68014(11) 0.0290(4) Uani 1 1 d . . . C17 C 0.3293(2) 0.05759(5) 0.70854(11) 0.0291(4) Uani 1 1 d . . . H10 H 0.4437 0.0574 0.7363 0.035 Uiso 1 1 calc R . . C18 C 0.2444(2) 0.09744(5) 0.69755(11) 0.0265(3) Uani 1 1 d . . . C19 C -0.1824(2) 0.05890(6) 0.57699(13) 0.0340(4) Uani 1 1 d . . . H11 H -0.2541 0.0725 0.6227 0.051 Uiso 1 1 calc R . . H12 H -0.2198 0.0287 0.5627 0.051 Uiso 1 1 calc R . . H13 H -0.1900 0.0757 0.5149 0.051 Uiso 1 1 calc R . . C20 C 0.3449(3) -0.02496(6) 0.69794(15) 0.0466(5) Uani 1 1 d . . . H14 H 0.4526 -0.0234 0.6698 0.070 Uiso 1 1 calc R . . H15 H 0.2771 -0.0489 0.6659 0.070 Uiso 1 1 calc R . . H16 H 0.3653 -0.0305 0.7696 0.070 Uiso 1 1 calc R . . C21 C 0.3332(2) 0.13972(6) 0.72999(14) 0.0398(4) Uani 1 1 d . . . H17 H 0.4474 0.1331 0.7602 0.060 Uiso 1 1 calc R . . H18 H 0.2710 0.1546 0.7788 0.060 Uiso 1 1 calc R . . H19 H 0.3386 0.1588 0.6721 0.060 Uiso 1 1 calc R . . B2 B 0.2225(2) 0.11995(6) 1.14691(13) 0.0246(4) Uani 1 1 d . . . C22 C 0.27494(19) 0.11032(5) 1.26025(11) 0.0245(3) Uani 1 1 d . . . C23 C 0.39880(18) 0.14137(5) 1.29568(11) 0.0242(3) Uani 1 1 d . . . C24 C 0.43084(19) 0.17230(5) 1.21500(11) 0.0255(3) Uani 1 1 d . . . C25 C 0.33025(19) 0.16118(5) 1.12593(11) 0.0266(3) Uani 1 1 d . . . C26 C 0.3397(2) 0.18690(6) 1.04189(13) 0.0351(4) Uani 1 1 d . . . H20 H 0.2730 0.1798 0.9815 0.042 Uiso 1 1 calc R . . C27 C 0.4470(3) 0.22306(6) 1.04630(14) 0.0427(5) Uani 1 1 d . . . H21 H 0.4525 0.2408 0.9890 0.051 Uiso 1 1 calc R . . C28 C 0.5452(2) 0.23312(6) 1.13365(15) 0.0428(5) Uani 1 1 d . . . H22 H 0.6183 0.2578 1.1357 0.051 Uiso 1 1 calc R . . C29 C 0.5390(2) 0.20777(6) 1.21865(13) 0.0339(4) Uani 1 1 d . . . H23 H 0.6079 0.2147 1.2783 0.041 Uiso 1 1 calc R . . C30 C 0.4714(2) 0.14062(6) 1.39364(12) 0.0312(4) Uani 1 1 d . . . H24 H 0.5549 0.1615 1.4169 0.037 Uiso 1 1 calc R . . C31 C 0.4192(2) 0.10858(6) 1.45716(12) 0.0346(4) Uani 1 1 d . . . H25 H 0.4676 0.1078 1.5245 0.042 Uiso 1 1 calc R . . C32 C 0.2982(2) 0.07790(6) 1.42391(12) 0.0332(4) Uani 1 1 d . . . H26 H 0.2638 0.0564 1.4684 0.040 Uiso 1 1 calc R . . C33 C 0.2268(2) 0.07865(5) 1.32518(12) 0.0288(4) Uani 1 1 d . . . H27 H 0.1448 0.0573 1.3023 0.035 Uiso 1 1 calc R . . C34 C 0.09794(19) 0.09461(5) 1.07063(11) 0.0241(3) Uani 1 1 d . . . C35 C 0.15935(18) 0.07014(5) 0.99403(11) 0.0248(3) Uani 1 1 d . . . C36 C 0.04938(19) 0.04749(5) 0.92562(11) 0.0246(3) Uani 1 1 d . . . H28 H 0.0930 0.0310 0.8746 0.029 Uiso 1 1 calc R . . C37 C -0.12297(19) 0.04852(5) 0.93026(11) 0.0244(3) Uani 1 1 d . . . C38 C -0.18343(19) 0.07281(5) 1.00535(12) 0.0266(3) Uani 1 1 d . . . H29 H -0.3013 0.0738 1.0092 0.032 Uiso 1 1 calc R . . C39 C -0.07697(19) 0.09578(5) 1.07531(11) 0.0253(3) Uani 1 1 d . . . C40 C 0.3467(2) 0.06716(6) 0.98707(13) 0.0338(4) Uani 1 1 d . . . H30 H 0.3706 0.0410 0.9488 0.051 Uiso 1 1 calc R . . H31 H 0.4065 0.0651 1.0541 0.051 Uiso 1 1 calc R . . H32 H 0.3841 0.0934 0.9538 0.051 Uiso 1 1 calc R . . C41 C -0.2399(2) 0.02449(6) 0.85373(12) 0.0347(4) Uani 1 1 d . . . H33 H -0.3528 0.0234 0.8755 0.052 Uiso 1 1 calc R . . H34 H -0.1985 -0.0055 0.8460 0.052 Uiso 1 1 calc R . . H35 H -0.2445 0.0399 0.7899 0.052 Uiso 1 1 calc R . . C42 C -0.1499(2) 0.12340(6) 1.15337(13) 0.0371(4) Uani 1 1 d . . . H36 H -0.1299 0.1546 1.1407 0.056 Uiso 1 1 calc R . . H37 H -0.0959 0.1155 1.2195 0.056 Uiso 1 1 calc R . . H38 H -0.2712 0.1181 1.1503 0.056 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 B1 0.0227(9) 0.0231(9) 0.0260(9) -0.0010(7) -0.0004(7) -0.0021(7) C1 0.0272(8) 0.0214(7) 0.0280(8) -0.0002(6) 0.0022(6) 0.0004(6) C2 0.0235(8) 0.0219(8) 0.0269(8) -0.0007(6) 0.0014(6) -0.0004(6) C3 0.0217(7) 0.0209(7) 0.0254(8) -0.0014(6) -0.0013(6) -0.0009(6) C4 0.0225(8) 0.0211(7) 0.0258(8) -0.0010(6) 0.0002(6) 0.0002(6) C5 0.0276(8) 0.0235(8) 0.0264(8) -0.0034(6) 0.0018(6) 0.0017(6) C6 0.0301(9) 0.0312(9) 0.0232(8) -0.0007(6) 0.0009(6) -0.0039(7) C7 0.0291(8) 0.0249(8) 0.0265(8) 0.0046(6) -0.0031(6) -0.0018(6) C8 0.0259(8) 0.0215(8) 0.0302(8) 0.0012(6) -0.0014(6) 0.0017(6) C9 0.0333(9) 0.0242(8) 0.0353(9) -0.0009(7) 0.0066(7) 0.0058(7) C10 0.0440(11) 0.0354(10) 0.0382(10) -0.0050(8) 0.0176(8) 0.0082(8) C11 0.0541(12) 0.0373(10) 0.0289(9) 0.0005(7) 0.0145(8) 0.0043(8) C12 0.0413(10) 0.0286(9) 0.0293(9) 0.0030(7) 0.0067(7) 0.0043(7) C13 0.0265(8) 0.0233(8) 0.0182(7) 0.0019(6) 0.0049(6) 0.0039(6) C14 0.0263(8) 0.0242(8) 0.0224(8) 0.0015(6) 0.0047(6) 0.0033(6) C15 0.0341(9) 0.0213(8) 0.0262(8) 0.0000(6) 0.0068(7) 0.0010(6) C16 0.0366(9) 0.0269(8) 0.0242(8) 0.0016(6) 0.0068(7) 0.0111(7) C17 0.0250(8) 0.0367(9) 0.0251(8) 0.0014(7) 0.0001(6) 0.0087(7) C18 0.0284(8) 0.0276(8) 0.0235(8) -0.0002(6) 0.0023(6) 0.0026(6) C19 0.0287(9) 0.0325(9) 0.0396(10) -0.0023(7) -0.0012(7) 0.0004(7) C20 0.0533(12) 0.0356(10) 0.0498(12) 0.0006(8) 0.0008(9) 0.0208(9) C21 0.0363(10) 0.0342(9) 0.0469(11) -0.0059(8) -0.0043(8) -0.0013(8) B2 0.0205(8) 0.0281(9) 0.0266(9) -0.0052(7) 0.0082(7) 0.0035(7) C22 0.0233(8) 0.0255(8) 0.0255(8) -0.0043(6) 0.0062(6) 0.0022(6) C23 0.0203(8) 0.0260(8) 0.0267(8) -0.0052(6) 0.0038(6) 0.0035(6) C24 0.0216(8) 0.0263(8) 0.0296(8) -0.0051(6) 0.0079(6) 0.0008(6) C25 0.0253(8) 0.0300(8) 0.0255(8) -0.0031(6) 0.0077(6) 0.0026(6) C26 0.0390(10) 0.0389(10) 0.0294(9) 0.0012(7) 0.0132(7) 0.0049(8) C27 0.0518(12) 0.0369(10) 0.0442(11) 0.0062(8) 0.0272(9) 0.0008(8) C28 0.0412(11) 0.0309(9) 0.0612(13) -0.0044(9) 0.0275(9) -0.0069(8) C29 0.0276(9) 0.0330(9) 0.0427(10) -0.0113(7) 0.0106(7) -0.0040(7) C30 0.0247(8) 0.0380(9) 0.0300(9) -0.0088(7) -0.0008(7) 0.0049(7) C31 0.0333(9) 0.0460(10) 0.0240(8) -0.0006(7) 0.0010(7) 0.0155(8) C32 0.0401(10) 0.0329(9) 0.0284(9) 0.0055(7) 0.0119(7) 0.0121(8) C33 0.0306(9) 0.0260(8) 0.0311(9) -0.0027(7) 0.0096(7) 0.0024(7) C34 0.0215(8) 0.0279(8) 0.0229(8) -0.0004(6) 0.0031(6) 0.0011(6) C35 0.0199(8) 0.0307(8) 0.0239(8) -0.0012(6) 0.0026(6) 0.0021(6) C36 0.0261(8) 0.0270(8) 0.0207(7) -0.0011(6) 0.0032(6) 0.0049(6) C37 0.0250(8) 0.0231(8) 0.0242(8) 0.0026(6) -0.0018(6) -0.0003(6) C38 0.0157(7) 0.0318(8) 0.0324(8) 0.0016(7) 0.0032(6) 0.0025(6) C39 0.0229(8) 0.0272(8) 0.0261(8) -0.0015(6) 0.0043(6) 0.0022(6) C40 0.0222(8) 0.0481(10) 0.0316(9) -0.0098(8) 0.0054(7) 0.0015(7) C41 0.0295(9) 0.0414(10) 0.0317(9) -0.0043(7) -0.0033(7) -0.0041(7) C42 0.0277(9) 0.0454(10) 0.0393(10) -0.0126(8) 0.0082(7) 0.0038(8) _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 B1 C13 1.565(2) . ? B1 C1 1.566(2) . ? B1 C4 1.567(2) . ? C1 C12 1.392(2) . ? C1 C2 1.416(2) . ? C2 C9 1.375(2) . ? C2 C3 1.485(2) . ? C3 C8 1.383(2) . ? C3 C4 1.415(2) . ? C4 C5 1.388(2) . ? C5 C6 1.397(2) . ? C5 H1 0.9500 . ? C6 C7 1.384(2) . ? C6 H2 0.9500 . ? C7 C8 1.393(2) . ? C7 H3 0.9500 . ? C8 H4 0.9500 . ? C9 C10 1.393(2) . ? C9 H5 0.9500 . ? C10 C11 1.384(3) . ? C10 H6 0.9500 . ? C11 C12 1.393(2) . ? C11 H7 0.9500 . ? C12 H8 0.9500 . ? C13 C18 1.403(2) . ? C13 C14 1.406(2) . ? C14 C15 1.393(2) . ? C14 C19 1.510(2) . ? C15 C16 1.387(2) . ? C15 H9 0.9500 . ? C16 C17 1.391(2) . ? C16 C20 1.510(2) . ? C17 C18 1.390(2) . ? C17 H10 0.9500 . ? C18 C21 1.512(2) . ? C19 H11 0.9800 . ? C19 H12 0.9800 . ? C19 H13 0.9800 . ? C20 H14 0.9800 . ? C20 H15 0.9800 . ? C20 H16 0.9800 . ? C21 H17 0.9800 . ? C21 H18 0.9800 . ? C21 H19 0.9800 . ? B2 C34 1.558(2) . ? B2 C25 1.566(2) . ? B2 C22 1.572(2) . ? C22 C33 1.387(2) . ? C22 C23 1.415(2) . ? C23 C30 1.387(2) . ? C23 C24 1.485(2) . ? C24 C29 1.381(2) . ? C24 C25 1.415(2) . ? C25 C26 1.389(2) . ? C26 C27 1.393(3) . ? C26 H20 0.9500 . ? C27 C28 1.380(3) . ? C27 H21 0.9500 . ? C28 C29 1.390(3) . ? C28 H22 0.9500 . ? C29 H23 0.9500 . ? C30 C31 1.393(2) . ? C30 H24 0.9500 . ? C31 C32 1.384(3) . ? C31 H25 0.9500 . ? C32 C33 1.394(2) . ? C32 H26 0.9500 . ? C33 H27 0.9500 . ? C34 C35 1.407(2) . ? C34 C39 1.408(2) . ? C35 C36 1.388(2) . ? C35 C40 1.514(2) . ? C36 C37 1.387(2) . ? C36 H28 0.9500 . ? C37 C38 1.385(2) . ? C37 C41 1.507(2) . ? C38 C39 1.390(2) . ? C38 H29 0.9500 . ? C39 C42 1.515(2) . ? C40 H30 0.9800 . ? C40 H31 0.9800 . ? C40 H32 0.9800 . ? C41 H33 0.9800 . ? C41 H34 0.9800 . ? C41 H35 0.9800 . ? C42 H36 0.9800 . ? C42 H37 0.9800 . ? C42 H38 0.9800 . ? 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 C13 B1 C1 128.13(14) . . ? C13 B1 C4 128.17(14) . . ? C1 B1 C4 103.70(13) . . ? C12 C1 C2 118.93(14) . . ? C12 C1 B1 133.00(14) . . ? C2 C1 B1 108.04(13) . . ? C9 C2 C1 121.34(14) . . ? C9 C2 C3 128.70(14) . . ? C1 C2 C3 109.96(13) . . ? C8 C3 C4 121.15(14) . . ? C8 C3 C2 128.40(14) . . ? C4 C3 C2 110.44(13) . . ? C5 C4 C3 119.07(14) . . ? C5 C4 B1 133.13(14) . . ? C3 C4 B1 107.78(13) . . ? C4 C5 C6 119.99(14) . . ? C4 C5 H1 120.0 . . ? C6 C5 H1 120.0 . . ? C7 C6 C5 119.89(14) . . ? C7 C6 H2 120.1 . . ? C5 C6 H2 120.1 . . ? C6 C7 C8 121.35(14) . . ? C6 C7 H3 119.3 . . ? C8 C7 H3 119.3 . . ? C3 C8 C7 118.54(14) . . ? C3 C8 H4 120.7 . . ? C7 C8 H4 120.7 . . ? C2 C9 C10 118.70(15) . . ? C2 C9 H5 120.6 . . ? C10 C9 H5 120.6 . . ? C11 C10 C9 121.05(15) . . ? C11 C10 H6 119.5 . . ? C9 C10 H6 119.5 . . ? C10 C11 C12 120.28(16) . . ? C10 C11 H7 119.9 . . ? C12 C11 H7 119.9 . . ? C1 C12 C11 119.69(15) . . ? C1 C12 H8 120.2 . . ? C11 C12 H8 120.2 . . ? C18 C13 C14 118.95(13) . . ? C18 C13 B1 120.85(13) . . ? C14 C13 B1 120.20(13) . . ? C15 C14 C13 119.75(14) . . ? C15 C14 C19 120.59(14) . . ? C13 C14 C19 119.65(13) . . ? C16 C15 C14 121.76(15) . . ? C16 C15 H9 119.1 . . ? C14 C15 H9 119.1 . . ? C15 C16 C17 117.87(14) . . ? C15 C16 C20 121.45(15) . . ? C17 C16 C20 120.67(15) . . ? C18 C17 C16 122.01(15) . . ? C18 C17 H10 119.0 . . ? C16 C17 H10 119.0 . . ? C17 C18 C13 119.62(14) . . ? C17 C18 C21 120.24(15) . . ? C13 C18 C21 120.13(14) . . ? C14 C19 H11 109.5 . . ? C14 C19 H12 109.5 . . ? H11 C19 H12 109.5 . . ? C14 C19 H13 109.5 . . ? H11 C19 H13 109.5 . . ? H12 C19 H13 109.5 . . ? C16 C20 H14 109.5 . . ? C16 C20 H15 109.5 . . ? H14 C20 H15 109.5 . . ? C16 C20 H16 109.5 . . ? H14 C20 H16 109.5 . . ? H15 C20 H16 109.5 . . ? C18 C21 H17 109.5 . . ? C18 C21 H18 109.5 . . ? H17 C21 H18 109.5 . . ? C18 C21 H19 109.5 . . ? H17 C21 H19 109.5 . . ? H18 C21 H19 109.5 . . ? C34 B2 C25 127.00(14) . . ? C34 B2 C22 129.54(14) . . ? C25 B2 C22 103.44(13) . . ? C33 C22 C23 118.86(14) . . ? C33 C22 B2 133.16(14) . . ? C23 C22 B2 107.96(13) . . ? C30 C23 C22 121.15(15) . . ? C30 C23 C24 128.62(15) . . ? C22 C23 C24 110.22(13) . . ? C29 C24 C25 120.89(15) . . ? C29 C24 C23 128.86(15) . . ? C25 C24 C23 110.25(13) . . ? C26 C25 C24 119.02(15) . . ? C26 C25 B2 132.86(15) . . ? C24 C25 B2 108.11(13) . . ? C25 C26 C27 119.91(17) . . ? C25 C26 H20 120.0 . . ? C27 C26 H20 120.0 . . ? C28 C27 C26 120.18(17) . . ? C28 C27 H21 119.9 . . ? C26 C27 H21 119.9 . . ? C27 C28 C29 121.08(17) . . ? C27 C28 H22 119.5 . . ? C29 C28 H22 119.5 . . ? C24 C29 C28 118.91(17) . . ? C24 C29 H23 120.5 . . ? C28 C29 H23 120.5 . . ? C23 C30 C31 118.53(16) . . ? C23 C30 H24 120.7 . . ? C31 C30 H24 120.7 . . ? C32 C31 C30 121.19(15) . . ? C32 C31 H25 119.4 . . ? C30 C31 H25 119.4 . . ? C31 C32 C33 119.93(15) . . ? C31 C32 H26 120.0 . . ? C33 C32 H26 120.0 . . ? C22 C33 C32 120.33(15) . . ? C22 C33 H27 119.8 . . ? C32 C33 H27 119.8 . . ? C35 C34 C39 118.34(14) . . ? C35 C34 B2 120.02(13) . . ? C39 C34 B2 121.64(13) . . ? C36 C35 C34 120.46(14) . . ? C36 C35 C40 119.22(13) . . ? C34 C35 C40 120.30(13) . . ? C37 C36 C35 121.28(14) . . ? C37 C36 H28 119.4 . . ? C35 C36 H28 119.4 . . ? C38 C37 C36 118.25(14) . . ? C38 C37 C41 121.50(14) . . ? C36 C37 C41 120.24(14) . . ? C37 C38 C39 122.04(14) . . ? C37 C38 H29 119.0 . . ? C39 C38 H29 119.0 . . ? C38 C39 C34 119.65(14) . . ? C38 C39 C42 119.95(14) . . ? C34 C39 C42 120.35(14) . . ? C35 C40 H30 109.5 . . ? C35 C40 H31 109.5 . . ? H30 C40 H31 109.5 . . ? C35 C40 H32 109.5 . . ? H30 C40 H32 109.5 . . ? H31 C40 H32 109.5 . . ? C37 C41 H33 109.5 . . ? C37 C41 H34 109.5 . . ? H33 C41 H34 109.5 . . ? C37 C41 H35 109.5 . . ? H33 C41 H35 109.5 . . ? H34 C41 H35 109.5 . . ? C39 C42 H36 109.5 . . ? C39 C42 H37 109.5 . . ? H36 C42 H37 109.5 . . ? C39 C42 H38 109.5 . . ? H36 C42 H38 109.5 . . ? H37 C42 H38 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C13 B1 C1 C12 -1.1(3) . . . . ? C4 B1 C1 C12 178.91(17) . . . . ? C13 B1 C1 C2 -179.13(15) . . . . ? C4 B1 C1 C2 0.91(16) . . . . ? C12 C1 C2 C9 -0.9(2) . . . . ? B1 C1 C2 C9 177.41(14) . . . . ? C12 C1 C2 C3 179.37(14) . . . . ? B1 C1 C2 C3 -2.30(17) . . . . ? C9 C2 C3 C8 4.4(3) . . . . ? C1 C2 C3 C8 -175.92(15) . . . . ? C9 C2 C3 C4 -176.71(16) . . . . ? C1 C2 C3 C4 2.97(17) . . . . ? C8 C3 C4 C5 -1.5(2) . . . . ? C2 C3 C4 C5 179.47(13) . . . . ? C8 C3 C4 B1 176.71(14) . . . . ? C2 C3 C4 B1 -2.27(16) . . . . ? C13 B1 C4 C5 -1.2(3) . . . . ? C1 B1 C4 C5 178.76(16) . . . . ? C13 B1 C4 C3 -179.11(15) . . . . ? C1 B1 C4 C3 0.86(16) . . . . ? C3 C4 C5 C6 1.1(2) . . . . ? B1 C4 C5 C6 -176.57(15) . . . . ? C4 C5 C6 C7 0.0(2) . . . . ? C5 C6 C7 C8 -0.9(2) . . . . ? C4 C3 C8 C7 0.7(2) . . . . ? C2 C3 C8 C7 179.50(14) . . . . ? C6 C7 C8 C3 0.5(2) . . . . ? C1 C2 C9 C10 0.2(2) . . . . ? C3 C2 C9 C10 179.88(16) . . . . ? C2 C9 C10 C11 0.4(3) . . . . ? C9 C10 C11 C12 -0.4(3) . . . . ? C2 C1 C12 C11 1.0(2) . . . . ? B1 C1 C12 C11 -176.87(17) . . . . ? C10 C11 C12 C1 -0.3(3) . . . . ? C1 B1 C13 C18 -82.5(2) . . . . ? C4 B1 C13 C18 97.50(19) . . . . ? C1 B1 C13 C14 97.60(19) . . . . ? C4 B1 C13 C14 -82.4(2) . . . . ? C18 C13 C14 C15 1.3(2) . . . . ? B1 C13 C14 C15 -178.79(14) . . . . ? C18 C13 C14 C19 -178.85(14) . . . . ? B1 C13 C14 C19 1.1(2) . . . . ? C13 C14 C15 C16 -0.2(2) . . . . ? C19 C14 C15 C16 179.96(14) . . . . ? C14 C15 C16 C17 -1.4(2) . . . . ? C14 C15 C16 C20 177.31(15) . . . . ? C15 C16 C17 C18 1.9(2) . . . . ? C20 C16 C17 C18 -176.83(15) . . . . ? C16 C17 C18 C13 -0.8(2) . . . . ? C16 C17 C18 C21 179.63(15) . . . . ? C14 C13 C18 C17 -0.8(2) . . . . ? B1 C13 C18 C17 179.26(14) . . . . ? C14 C13 C18 C21 178.76(14) . . . . ? B1 C13 C18 C21 -1.2(2) . . . . ? C34 B2 C22 C33 -1.7(3) . . . . ? C25 B2 C22 C33 179.91(16) . . . . ? C34 B2 C22 C23 176.82(15) . . . . ? C25 B2 C22 C23 -1.58(16) . . . . ? C33 C22 C23 C30 -0.3(2) . . . . ? B2 C22 C23 C30 -179.02(14) . . . . ? C33 C22 C23 C24 -179.62(13) . . . . ? B2 C22 C23 C24 1.62(16) . . . . ? C30 C23 C24 C29 -0.7(3) . . . . ? C22 C23 C24 C29 178.60(15) . . . . ? C30 C23 C24 C25 179.69(15) . . . . ? C22 C23 C24 C25 -1.02(17) . . . . ? C29 C24 C25 C26 -0.9(2) . . . . ? C23 C24 C25 C26 178.73(14) . . . . ? C29 C24 C25 B2 -179.71(14) . . . . ? C23 C24 C25 B2 -0.05(17) . . . . ? C34 B2 C25 C26 4.0(3) . . . . ? C22 B2 C25 C26 -177.58(16) . . . . ? C34 B2 C25 C24 -177.49(14) . . . . ? C22 B2 C25 C24 0.97(16) . . . . ? C24 C25 C26 C27 -0.1(2) . . . . ? B2 C25 C26 C27 178.35(16) . . . . ? C25 C26 C27 C28 0.7(3) . . . . ? C26 C27 C28 C29 -0.3(3) . . . . ? C25 C24 C29 C28 1.3(2) . . . . ? C23 C24 C29 C28 -178.28(15) . . . . ? C27 C28 C29 C24 -0.7(3) . . . . ? C22 C23 C30 C31 -0.3(2) . . . . ? C24 C23 C30 C31 178.97(15) . . . . ? C23 C30 C31 C32 0.2(2) . . . . ? C30 C31 C32 C33 0.3(2) . . . . ? C23 C22 C33 C32 0.8(2) . . . . ? B2 C22 C33 C32 179.18(15) . . . . ? C31 C32 C33 C22 -0.8(2) . . . . ? C25 B2 C34 C35 68.5(2) . . . . ? C22 B2 C34 C35 -109.51(18) . . . . ? C25 B2 C34 C39 -110.79(18) . . . . ? C22 B2 C34 C39 71.2(2) . . . . ? C39 C34 C35 C36 -0.6(2) . . . . ? B2 C34 C35 C36 -179.92(14) . . . . ? C39 C34 C35 C40 -178.80(15) . . . . ? B2 C34 C35 C40 1.8(2) . . . . ? C34 C35 C36 C37 0.4(2) . . . . ? C40 C35 C36 C37 178.69(14) . . . . ? C35 C36 C37 C38 -0.1(2) . . . . ? C35 C36 C37 C41 178.61(15) . . . . ? C36 C37 C38 C39 -0.1(2) . . . . ? C41 C37 C38 C39 -178.80(15) . . . . ? C37 C38 C39 C34 0.0(2) . . . . ? C37 C38 C39 C42 177.44(15) . . . . ? C35 C34 C39 C38 0.4(2) . . . . ? B2 C34 C39 C38 179.71(14) . . . . ? C35 C34 C39 C42 -177.08(15) . . . . ? B2 C34 C39 C42 2.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.197 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.040 # Attachment 'compound2.CIF' data_cmpd2 _database_code_depnum_ccdc_archive 'CCDC 857121' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (indolo)(benzo)borole ; _chemical_name_common (indolo)(benzo)borole _chemical_melting_point 398 _chemical_formula_moiety 'C24 H22 B N' _chemical_formula_sum 'C24 H22 B N' _chemical_formula_weight 335.24 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' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M P4/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y+1/2, x, z' 'y, -x+1/2, z' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y-1/2, -x, -z' '-y, x-1/2, -z' _cell_length_a 22.546(4) _cell_length_b 22.546(4) _cell_length_c 7.1203(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3619.3(11) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 9357 _cell_measurement_theta_min 2.5554 _cell_measurement_theta_max 31.5050 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9862 _exptl_absorpt_correction_T_max 0.9862 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; 'Saturn70 CCD (4x4 bin mode) with MicroMax-007' ; _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23169 _diffrn_reflns_av_R_equivalents 0.0458 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3192 _reflns_number_gt 3103 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 for windows' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0490P)^2^+2.8042P] 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 none _refine_ls_number_reflns 3192 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1355 _refine_ls_wR_factor_gt 0.1343 _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_restrained_S_all 1.152 _refine_ls_shift/su_max 0.005 _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 B1 B 0.83192(10) 0.00311(10) 0.9398(3) 0.0250(5) Uani 1 1 d . . . C1 C 0.82079(9) 0.07098(9) 0.8775(3) 0.0261(5) Uani 1 1 d . . . C2 C 0.87245(9) 0.09197(9) 0.7850(3) 0.0255(5) Uani 1 1 d . . . C3 C 0.91500(8) 0.04250(8) 0.7858(3) 0.0215(4) Uani 1 1 d . . . C4 C 0.89214(9) -0.01101(9) 0.8521(3) 0.0232(4) Uani 1 1 d . . . C5 C 0.93991(9) -0.05274(9) 0.8387(3) 0.0236(4) Uani 1 1 d . . . C6 C 0.99039(9) -0.02120(8) 0.7701(3) 0.0223(4) Uani 1 1 d . . . N1 N 0.97333(7) 0.03775(7) 0.7400(2) 0.0243(4) Uani 1 1 d . . . C7 C 0.87440(10) 0.14716(9) 0.7041(3) 0.0298(5) Uani 1 1 d . . . H1 H 0.9091 0.1604 0.6411 0.036 Uiso 1 1 calc R . . C8 C 0.82411(11) 0.18380(10) 0.7163(3) 0.0371(6) Uani 1 1 d . . . H2 H 0.8249 0.2221 0.6609 0.045 Uiso 1 1 calc R . . C9 C 0.77364(10) 0.16471(10) 0.8078(3) 0.0349(5) Uani 1 1 d . . . H3 H 0.7400 0.1900 0.8159 0.042 Uiso 1 1 calc R . . C10 C 0.77200(9) 0.10811(9) 0.8887(3) 0.0296(5) Uani 1 1 d . . . H4 H 0.7372 0.0951 0.9516 0.036 Uiso 1 1 calc R . . C11 C 0.94649(9) -0.11359(9) 0.8732(3) 0.0256(5) Uani 1 1 d . . . H5 H 0.9140 -0.1364 0.9176 0.031 Uiso 1 1 calc R . . C12 C 1.00106(9) -0.14007(9) 0.8416(3) 0.0293(5) Uani 1 1 d . . . H6 H 1.0055 -0.1814 0.8638 0.035 Uiso 1 1 calc R . . C13 C 1.04983(9) -0.10738(10) 0.7778(3) 0.0301(5) Uani 1 1 d . . . H7 H 1.0868 -0.1267 0.7592 0.036 Uiso 1 1 calc R . . C14 C 1.04506(9) -0.04744(9) 0.7414(3) 0.0275(5) Uani 1 1 d . . . H8 H 1.0781 -0.0251 0.6984 0.033 Uiso 1 1 calc R . . C15 C 0.79051(8) -0.03548(8) 1.0695(3) 0.0220(4) Uani 1 1 d . . . C16 C 0.76935(8) -0.09115(9) 1.0071(3) 0.0226(4) Uani 1 1 d . . . C17 C 0.73133(8) -0.12441(9) 1.1204(3) 0.0236(4) Uani 1 1 d . . . H9 H 0.7177 -0.1618 1.0763 0.028 Uiso 1 1 calc R . . C18 C 0.71279(8) -0.10459(9) 1.2956(3) 0.0229(4) Uani 1 1 d . . . C19 C 0.73421(8) -0.05013(9) 1.3569(3) 0.0230(4) Uani 1 1 d . . . H10 H 0.7222 -0.0358 1.4765 0.028 Uiso 1 1 calc R . . C20 C 0.77265(8) -0.01575(9) 1.2488(3) 0.0231(4) Uani 1 1 d . . . C21 C 0.78397(9) -0.11473(9) 0.8147(3) 0.0276(5) Uani 1 1 d . . . H11 H 0.7900 -0.1577 0.8217 0.041 Uiso 1 1 calc R . . H12 H 0.8203 -0.0957 0.7686 0.041 Uiso 1 1 calc R . . H13 H 0.7512 -0.1061 0.7287 0.041 Uiso 1 1 calc R . . C22 C 0.67130(9) -0.14113(9) 1.4141(3) 0.0299(5) Uani 1 1 d . . . H14 H 0.6923 -0.1761 1.4615 0.045 Uiso 1 1 calc R . . H15 H 0.6374 -0.1538 1.3379 0.045 Uiso 1 1 calc R . . H16 H 0.6572 -0.1173 1.5202 0.045 Uiso 1 1 calc R . . C23 C 0.79549(9) 0.04101(9) 1.3356(3) 0.0299(5) Uani 1 1 d . . . H17 H 0.7626 0.0621 1.3961 0.045 Uiso 1 1 calc R . . H18 H 0.8128 0.0661 1.2376 0.045 Uiso 1 1 calc R . . H19 H 0.8258 0.0316 1.4295 0.045 Uiso 1 1 calc R . . C24 C 1.01408(9) 0.08499(9) 0.6845(3) 0.0303(5) Uani 1 1 d . . . H20 H 1.0176 0.0857 0.5473 0.045 Uiso 1 1 calc R . . H21 H 1.0532 0.0777 0.7402 0.045 Uiso 1 1 calc R . . H22 H 0.9988 0.1232 0.7286 0.045 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 B1 0.0264(12) 0.0288(12) 0.0198(11) -0.0026(9) -0.0032(9) -0.0033(9) C1 0.0272(11) 0.0271(11) 0.0242(10) -0.0050(8) -0.0019(8) -0.0027(8) C2 0.0298(11) 0.0241(10) 0.0227(10) -0.0031(8) -0.0016(8) -0.0030(8) C3 0.0241(10) 0.0235(10) 0.0169(9) -0.0014(8) 0.0006(8) -0.0020(8) C4 0.0234(10) 0.0243(10) 0.0219(10) -0.0002(8) -0.0002(8) -0.0042(8) C5 0.0263(10) 0.0251(10) 0.0194(10) -0.0025(8) -0.0031(8) -0.0017(8) C6 0.0273(10) 0.0228(10) 0.0168(9) -0.0020(8) -0.0018(8) -0.0033(8) N1 0.0254(9) 0.0241(9) 0.0236(9) 0.0002(7) 0.0017(7) -0.0052(7) C7 0.0336(12) 0.0257(11) 0.0301(11) -0.0010(9) 0.0031(9) -0.0027(9) C8 0.0488(14) 0.0220(11) 0.0405(13) 0.0020(10) -0.0031(11) 0.0006(10) C9 0.0353(12) 0.0275(11) 0.0419(13) -0.0021(10) 0.0004(10) 0.0053(9) C10 0.0266(11) 0.0266(11) 0.0356(12) -0.0032(9) 0.0000(9) -0.0016(8) C11 0.0281(11) 0.0248(10) 0.0239(10) 0.0003(8) -0.0042(8) -0.0025(8) C12 0.0336(12) 0.0256(11) 0.0286(11) 0.0006(9) -0.0070(9) 0.0019(9) C13 0.0269(11) 0.0342(12) 0.0292(11) -0.0038(9) -0.0039(9) 0.0033(9) C14 0.0245(10) 0.0342(12) 0.0237(10) -0.0029(9) -0.0013(8) -0.0038(9) C15 0.0181(9) 0.0253(10) 0.0226(10) 0.0008(8) -0.0025(8) 0.0008(8) C16 0.0184(9) 0.0278(10) 0.0216(10) 0.0009(8) -0.0022(8) 0.0026(8) C17 0.0227(10) 0.0233(10) 0.0246(10) 0.0013(8) -0.0045(8) -0.0016(8) C18 0.0183(9) 0.0266(10) 0.0237(10) 0.0045(8) -0.0010(8) 0.0015(8) C19 0.0216(10) 0.0281(10) 0.0191(9) 0.0002(8) 0.0007(8) 0.0036(8) C20 0.0187(9) 0.0265(10) 0.0243(10) 0.0006(8) -0.0018(8) 0.0023(8) C21 0.0287(11) 0.0304(11) 0.0237(11) -0.0019(9) -0.0009(9) -0.0041(9) C22 0.0304(11) 0.0323(11) 0.0269(11) 0.0037(9) 0.0032(9) -0.0025(9) C23 0.0269(11) 0.0314(11) 0.0313(12) -0.0070(9) 0.0026(9) -0.0029(9) C24 0.0303(11) 0.0304(11) 0.0302(12) 0.0010(9) 0.0016(9) -0.0120(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 C4 1.528(3) . ? B1 C15 1.575(3) . ? B1 C1 1.613(3) . ? C1 C10 1.385(3) . ? C1 C2 1.419(3) . ? C2 C7 1.372(3) . ? C2 C3 1.471(3) . ? C3 N1 1.359(3) . ? C3 C4 1.394(3) . ? C4 C5 1.433(3) . ? C5 C11 1.402(3) . ? C5 C6 1.428(3) . ? C6 C14 1.382(3) . ? C6 N1 1.400(3) . ? N1 C24 1.461(2) . ? C7 C8 1.406(3) . ? C7 H1 0.9500 . ? C8 C9 1.380(3) . ? C8 H2 0.9500 . ? C9 C10 1.401(3) . ? C9 H3 0.9500 . ? C10 H4 0.9500 . ? C11 C12 1.386(3) . ? C11 H5 0.9500 . ? C12 C13 1.400(3) . ? C12 H6 0.9500 . ? C13 C14 1.380(3) . ? C13 H7 0.9500 . ? C14 H8 0.9500 . ? C15 C20 1.411(3) . ? C15 C16 1.414(3) . ? C16 C17 1.396(3) . ? C16 C21 1.506(3) . ? C17 C18 1.390(3) . ? C17 H9 0.9500 . ? C18 C19 1.390(3) . ? C18 C22 1.505(3) . ? C19 C20 1.394(3) . ? C19 H10 0.9500 . ? C20 C23 1.512(3) . ? C21 H11 0.9800 . ? C21 H12 0.9800 . ? C21 H13 0.9800 . ? C22 H14 0.9800 . ? C22 H15 0.9800 . ? C22 H16 0.9800 . ? C23 H17 0.9800 . ? C23 H18 0.9800 . ? C23 H19 0.9800 . ? C24 H20 0.9800 . ? C24 H21 0.9800 . ? C24 H22 0.9800 . ? 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 C4 B1 C15 130.63(19) . . ? C4 B1 C1 102.90(17) . . ? C15 B1 C1 126.39(18) . . ? C10 C1 C2 118.50(19) . . ? C10 C1 B1 132.94(19) . . ? C2 C1 B1 108.45(17) . . ? C7 C2 C1 121.57(19) . . ? C7 C2 C3 131.94(19) . . ? C1 C2 C3 106.29(17) . . ? N1 C3 C4 111.76(17) . . ? N1 C3 C2 133.61(18) . . ? C4 C3 C2 114.59(17) . . ? C3 C4 C5 105.52(17) . . ? C3 C4 B1 106.66(17) . . ? C5 C4 B1 146.27(19) . . ? C11 C5 C6 117.58(18) . . ? C11 C5 C4 135.26(19) . . ? C6 C5 C4 107.15(17) . . ? C14 C6 N1 128.95(18) . . ? C14 C6 C5 123.23(18) . . ? N1 C6 C5 107.82(17) . . ? C3 N1 C6 107.70(16) . . ? C3 N1 C24 128.02(17) . . ? C6 N1 C24 124.10(17) . . ? C2 C7 C8 118.8(2) . . ? C2 C7 H1 120.6 . . ? C8 C7 H1 120.6 . . ? C9 C8 C7 120.7(2) . . ? C9 C8 H2 119.6 . . ? C7 C8 H2 119.6 . . ? C8 C9 C10 120.0(2) . . ? C8 C9 H3 120.0 . . ? C10 C9 H3 120.0 . . ? C1 C10 C9 120.4(2) . . ? C1 C10 H4 119.8 . . ? C9 C10 H4 119.8 . . ? C12 C11 C5 119.16(19) . . ? C12 C11 H5 120.4 . . ? C5 C11 H5 120.4 . . ? C11 C12 C13 121.56(19) . . ? C11 C12 H6 119.2 . . ? C13 C12 H6 119.2 . . ? C14 C13 C12 121.0(2) . . ? C14 C13 H7 119.5 . . ? C12 C13 H7 119.5 . . ? C13 C14 C6 117.44(19) . . ? C13 C14 H8 121.3 . . ? C6 C14 H8 121.3 . . ? C20 C15 C16 117.89(18) . . ? C20 C15 B1 121.70(17) . . ? C16 C15 B1 120.41(18) . . ? C17 C16 C15 120.18(18) . . ? C17 C16 C21 118.05(18) . . ? C15 C16 C21 121.68(18) . . ? C18 C17 C16 122.05(18) . . ? C18 C17 H9 119.0 . . ? C16 C17 H9 119.0 . . ? C19 C18 C17 117.47(18) . . ? C19 C18 C22 121.59(18) . . ? C17 C18 C22 120.94(18) . . ? C18 C19 C20 122.28(18) . . ? C18 C19 H10 118.9 . . ? C20 C19 H10 118.9 . . ? C19 C20 C15 120.11(18) . . ? C19 C20 C23 117.15(18) . . ? C15 C20 C23 122.69(18) . . ? C16 C21 H11 109.5 . . ? C16 C21 H12 109.5 . . ? H11 C21 H12 109.5 . . ? C16 C21 H13 109.5 . . ? H11 C21 H13 109.5 . . ? H12 C21 H13 109.5 . . ? C18 C22 H14 109.5 . . ? C18 C22 H15 109.5 . . ? H14 C22 H15 109.5 . . ? C18 C22 H16 109.5 . . ? H14 C22 H16 109.5 . . ? H15 C22 H16 109.5 . . ? C20 C23 H17 109.5 . . ? C20 C23 H18 109.5 . . ? H17 C23 H18 109.5 . . ? C20 C23 H19 109.5 . . ? H17 C23 H19 109.5 . . ? H18 C23 H19 109.5 . . ? N1 C24 H20 109.5 . . ? N1 C24 H21 109.5 . . ? H20 C24 H21 109.5 . . ? N1 C24 H22 109.5 . . ? H20 C24 H22 109.5 . . ? H21 C24 H22 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 B1 C1 C10 170.3(2) . . . . ? C15 B1 C1 C10 -12.7(4) . . . . ? C4 B1 C1 C2 -5.7(2) . . . . ? C15 B1 C1 C2 171.29(19) . . . . ? C10 C1 C2 C7 -1.4(3) . . . . ? B1 C1 C2 C7 175.24(19) . . . . ? C10 C1 C2 C3 -176.93(18) . . . . ? B1 C1 C2 C3 -0.3(2) . . . . ? C7 C2 C3 N1 14.6(4) . . . . ? C1 C2 C3 N1 -170.6(2) . . . . ? C7 C2 C3 C4 -167.6(2) . . . . ? C1 C2 C3 C4 7.2(2) . . . . ? N1 C3 C4 C5 -2.5(2) . . . . ? C2 C3 C4 C5 179.25(16) . . . . ? N1 C3 C4 B1 167.29(16) . . . . ? C2 C3 C4 B1 -11.0(2) . . . . ? C15 B1 C4 C3 -167.2(2) . . . . ? C1 B1 C4 C3 9.7(2) . . . . ? C15 B1 C4 C5 -5.2(5) . . . . ? C1 B1 C4 C5 171.7(3) . . . . ? C3 C4 C5 C11 -176.7(2) . . . . ? B1 C4 C5 C11 21.2(5) . . . . ? C3 C4 C5 C6 2.0(2) . . . . ? B1 C4 C5 C6 -160.1(3) . . . . ? C11 C5 C6 C14 -1.8(3) . . . . ? C4 C5 C6 C14 179.28(18) . . . . ? C11 C5 C6 N1 178.05(17) . . . . ? C4 C5 C6 N1 -0.9(2) . . . . ? C4 C3 N1 C6 1.9(2) . . . . ? C2 C3 N1 C6 179.8(2) . . . . ? C4 C3 N1 C24 -173.18(19) . . . . ? C2 C3 N1 C24 4.7(4) . . . . ? C14 C6 N1 C3 179.22(19) . . . . ? C5 C6 N1 C3 -0.6(2) . . . . ? C14 C6 N1 C24 -5.4(3) . . . . ? C5 C6 N1 C24 174.76(17) . . . . ? C1 C2 C7 C8 1.0(3) . . . . ? C3 C2 C7 C8 175.2(2) . . . . ? C2 C7 C8 C9 0.0(3) . . . . ? C7 C8 C9 C10 -0.4(4) . . . . ? C2 C1 C10 C9 0.9(3) . . . . ? B1 C1 C10 C9 -174.7(2) . . . . ? C8 C9 C10 C1 0.0(3) . . . . ? C6 C5 C11 C12 0.7(3) . . . . ? C4 C5 C11 C12 179.3(2) . . . . ? C5 C11 C12 C13 0.6(3) . . . . ? C11 C12 C13 C14 -0.9(3) . . . . ? C12 C13 C14 C6 -0.1(3) . . . . ? N1 C6 C14 C13 -178.30(19) . . . . ? C5 C6 C14 C13 1.5(3) . . . . ? C4 B1 C15 C20 122.5(2) . . . . ? C1 B1 C15 C20 -53.6(3) . . . . ? C4 B1 C15 C16 -58.4(3) . . . . ? C1 B1 C15 C16 125.5(2) . . . . ? C20 C15 C16 C17 0.9(3) . . . . ? B1 C15 C16 C17 -178.20(18) . . . . ? C20 C15 C16 C21 177.44(17) . . . . ? B1 C15 C16 C21 -1.7(3) . . . . ? C15 C16 C17 C18 0.2(3) . . . . ? C21 C16 C17 C18 -176.39(18) . . . . ? C16 C17 C18 C19 -0.9(3) . . . . ? C16 C17 C18 C22 179.42(18) . . . . ? C17 C18 C19 C20 0.3(3) . . . . ? C22 C18 C19 C20 -179.99(18) . . . . ? C18 C19 C20 C15 0.9(3) . . . . ? C18 C19 C20 C23 -176.67(18) . . . . ? C16 C15 C20 C19 -1.5(3) . . . . ? B1 C15 C20 C19 177.64(18) . . . . ? C16 C15 C20 C23 175.94(18) . . . . ? B1 C15 C20 C23 -4.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.271 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.045 # Attachment 'compound3.cif' data_cmpd3 _database_code_depnum_ccdc_archive 'CCDC 857122' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (benzofrano)(benzo)borole ; _chemical_name_common (benzofrano)(benzo)borole _chemical_melting_point 390 _chemical_formula_moiety 'C23 H19 B O' _chemical_formula_sum 'C23 H19 B O' _chemical_formula_weight 322.19 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' B B 0.0013 0.0007 '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' _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 25.956(8) _cell_length_b 8.077(3) _cell_length_c 16.850(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.8586(11) _cell_angle_gamma 90.00 _cell_volume 3398.0(18) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5063 _cell_measurement_theta_min 2.5945 _cell_measurement_theta_max 31.5050 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9853 _exptl_absorpt_correction_T_max 0.9926 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; 'Saturn70 CCD (4x4 bin mode) with MicroMax-007' ; _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10888 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2963 _reflns_number_gt 2543 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 for windows' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0856P)^2^+6.9336P] 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 none _refine_ls_number_reflns 2963 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0654 _refine_ls_wR_factor_ref 0.1748 _refine_ls_wR_factor_gt 0.1669 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.83967(12) -0.2441(3) 0.42423(17) 0.0275(6) Uani 1 1 d . . . C1 C 0.78028(10) -0.2674(3) 0.36340(14) 0.0278(6) Uani 1 1 d . . . C2 C 0.74483(10) -0.1610(3) 0.38871(14) 0.0279(6) Uani 1 1 d . . . C3 C 0.77838(9) -0.0731(3) 0.46257(13) 0.0211(5) Uani 1 1 d . . . C4 C 0.83089(10) -0.1112(3) 0.48550(15) 0.0268(5) Uani 1 1 d . . . C5 C 0.85217(10) -0.0114(3) 0.55812(14) 0.0277(6) Uani 1 1 d . . . C6 C 0.80914(9) 0.0806(3) 0.57077(15) 0.0265(5) Uani 1 1 d . . . O1 O 0.76176(6) 0.0409(2) 0.50874(10) 0.0288(4) Uani 1 1 d . . . C7 C 0.69169(11) -0.1502(3) 0.34879(16) 0.0324(6) Uani 1 1 d . . . H1 H 0.6689 -0.0775 0.3679 0.039 Uiso 1 1 calc R . . C8 C 0.67116(11) -0.2510(3) 0.27741(16) 0.0327(6) Uani 1 1 d . . . H2 H 0.6343 -0.2464 0.2482 0.039 Uiso 1 1 calc R . . C9 C 0.70536(10) -0.3549(3) 0.25134(14) 0.0300(6) Uani 1 1 d . . . H3 H 0.6920 -0.4213 0.2036 0.036 Uiso 1 1 calc R . . C10 C 0.75981(10) -0.3635(3) 0.29464(14) 0.0286(6) Uani 1 1 d . . . H4 H 0.7828 -0.4366 0.2762 0.034 Uiso 1 1 calc R . . C11 C 0.90249(10) 0.0105(3) 0.61522(14) 0.0279(6) Uani 1 1 d . . . H5 H 0.9331 -0.0485 0.6101 0.033 Uiso 1 1 calc R . . C12 C 0.90587(10) 0.1208(3) 0.67901(15) 0.0293(6) Uani 1 1 d . . . H6 H 0.9395 0.1370 0.7184 0.035 Uiso 1 1 calc R . . C13 C 0.86127(10) 0.2098(3) 0.68748(15) 0.0320(6) Uani 1 1 d . . . H7 H 0.8655 0.2854 0.7320 0.038 Uiso 1 1 calc R . . C14 C 0.81151(10) 0.1901(3) 0.63267(15) 0.0315(6) Uani 1 1 d . . . H8 H 0.7809 0.2491 0.6379 0.038 Uiso 1 1 calc R . . C15 C 0.89217(10) -0.3292(3) 0.41620(14) 0.0257(5) Uani 1 1 d . . . C16 C 0.93477(9) -0.2338(3) 0.40280(14) 0.0254(5) Uani 1 1 d . . . C17 C 0.97865(9) -0.3119(3) 0.38678(14) 0.0260(5) Uani 1 1 d . . . H9 H 1.0067 -0.2464 0.3770 0.031 Uiso 1 1 calc R . . C18 C 0.98252(9) -0.4836(3) 0.38472(14) 0.0260(5) Uani 1 1 d . . . C19 C 0.94174(10) -0.5757(3) 0.40206(14) 0.0279(6) Uani 1 1 d . . . H10 H 0.9445 -0.6930 0.4031 0.033 Uiso 1 1 calc R . . C20 C 0.89723(10) -0.5030(3) 0.41790(14) 0.0263(5) Uani 1 1 d . . . C21 C 0.93314(10) -0.0465(3) 0.40220(16) 0.0306(6) Uani 1 1 d . . . H11 H 0.9681 -0.0031 0.4004 0.046 Uiso 1 1 calc R . . H12 H 0.9248 -0.0069 0.4523 0.046 Uiso 1 1 calc R . . H13 H 0.9055 -0.0083 0.3536 0.046 Uiso 1 1 calc R . . C22 C 1.03002(10) -0.5668(3) 0.36674(18) 0.0376(6) Uani 1 1 d . . . H14 H 1.0473 -0.4897 0.3372 0.056 Uiso 1 1 calc R . . H15 H 1.0180 -0.6651 0.3326 0.056 Uiso 1 1 calc R . . H16 H 1.0556 -0.5996 0.4187 0.056 Uiso 1 1 calc R . . C23 C 0.85642(11) -0.6107(3) 0.44228(17) 0.0354(6) Uani 1 1 d . . . H17 H 0.8566 -0.7214 0.4186 0.053 Uiso 1 1 calc R . . H18 H 0.8207 -0.5615 0.4215 0.053 Uiso 1 1 calc R . . H19 H 0.8655 -0.6188 0.5025 0.053 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 B1 0.0407(16) 0.0196(13) 0.0262(14) 0.0047(10) 0.0160(12) -0.0007(11) C1 0.0434(14) 0.0206(11) 0.0226(12) 0.0010(9) 0.0142(10) -0.0059(10) C2 0.0381(14) 0.0238(12) 0.0221(12) 0.0050(9) 0.0090(10) -0.0056(10) C3 0.0315(13) 0.0149(10) 0.0208(11) 0.0000(9) 0.0135(9) 0.0013(9) C4 0.0334(14) 0.0233(12) 0.0260(12) 0.0021(10) 0.0118(10) -0.0006(10) C5 0.0460(15) 0.0179(11) 0.0207(11) 0.0025(9) 0.0116(10) -0.0057(10) C6 0.0292(13) 0.0243(12) 0.0271(12) 0.0079(10) 0.0095(10) -0.0005(9) O1 0.0352(10) 0.0255(9) 0.0270(9) -0.0012(7) 0.0106(8) 0.0035(7) C7 0.0498(16) 0.0215(12) 0.0324(13) 0.0049(10) 0.0225(12) 0.0020(11) C8 0.0406(15) 0.0262(13) 0.0316(13) 0.0060(10) 0.0103(11) -0.0032(11) C9 0.0441(15) 0.0234(12) 0.0219(12) -0.0014(9) 0.0081(11) -0.0064(10) C10 0.0413(15) 0.0229(12) 0.0227(12) -0.0011(9) 0.0106(11) -0.0065(10) C11 0.0321(13) 0.0258(12) 0.0258(12) 0.0011(10) 0.0082(10) -0.0041(10) C12 0.0329(13) 0.0294(13) 0.0249(12) 0.0009(10) 0.0065(10) -0.0051(10) C13 0.0427(15) 0.0276(13) 0.0278(13) 0.0015(10) 0.0130(11) -0.0018(11) C14 0.0394(15) 0.0270(13) 0.0309(13) 0.0033(11) 0.0143(11) 0.0029(11) C15 0.0353(13) 0.0222(12) 0.0218(11) 0.0024(9) 0.0117(10) 0.0026(10) C16 0.0353(13) 0.0199(12) 0.0221(11) 0.0028(9) 0.0099(10) 0.0040(9) C17 0.0289(12) 0.0252(12) 0.0244(12) 0.0005(10) 0.0082(10) 0.0007(10) C18 0.0290(13) 0.0252(12) 0.0228(11) -0.0012(9) 0.0054(10) 0.0065(10) C19 0.0368(14) 0.0196(12) 0.0257(12) 0.0015(9) 0.0057(10) 0.0044(10) C20 0.0338(13) 0.0227(12) 0.0234(12) 0.0037(9) 0.0092(10) 0.0022(10) C21 0.0394(14) 0.0204(12) 0.0360(14) 0.0022(10) 0.0172(11) 0.0031(10) C22 0.0338(14) 0.0347(14) 0.0431(15) -0.0025(12) 0.0088(12) 0.0115(11) C23 0.0452(16) 0.0264(13) 0.0395(15) 0.0055(11) 0.0197(12) -0.0020(11) _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 B1 C4 1.549(4) . ? B1 C15 1.565(4) . ? B1 C1 1.612(4) . ? C1 C10 1.375(3) . ? C1 C2 1.408(4) . ? C2 C7 1.362(4) . ? C2 C3 1.490(3) . ? C3 C4 1.347(3) . ? C3 O1 1.350(3) . ? C4 C5 1.443(3) . ? C5 C6 1.405(3) . ? C5 C11 1.406(3) . ? C6 C14 1.356(4) . ? C6 O1 1.416(3) . ? C7 C8 1.430(4) . ? C7 H1 0.9500 . ? C8 C9 1.378(4) . ? C8 H2 0.9500 . ? C9 C10 1.404(4) . ? C9 H3 0.9500 . ? C10 H4 0.9500 . ? C11 C12 1.380(3) . ? C11 H5 0.9500 . ? C12 C13 1.403(4) . ? C12 H6 0.9500 . ? C13 C14 1.376(4) . ? C13 H7 0.9500 . ? C14 H8 0.9500 . ? C15 C20 1.410(3) . ? C15 C16 1.415(3) . ? C16 C17 1.392(3) . ? C16 C21 1.513(3) . ? C17 C18 1.391(3) . ? C17 H9 0.9500 . ? C18 C19 1.389(3) . ? C18 C22 1.506(3) . ? C19 C20 1.386(3) . ? C19 H10 0.9500 . ? C20 C23 1.512(3) . ? C21 H11 0.9800 . ? C21 H12 0.9800 . ? C21 H13 0.9800 . ? C22 H14 0.9800 . ? C22 H15 0.9800 . ? C22 H16 0.9800 . ? C23 H17 0.9800 . ? C23 H18 0.9800 . ? C23 H19 0.9800 . ? 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 C4 B1 C15 130.7(2) . . ? C4 B1 C1 102.4(2) . . ? C15 B1 C1 126.7(2) . . ? C10 C1 C2 117.8(2) . . ? C10 C1 B1 133.1(2) . . ? C2 C1 B1 109.1(2) . . ? C7 C2 C1 123.2(2) . . ? C7 C2 C3 131.6(2) . . ? C1 C2 C3 105.2(2) . . ? C4 C3 O1 116.6(2) . . ? C4 C3 C2 116.5(2) . . ? O1 C3 C2 126.9(2) . . ? C3 C4 C5 103.8(2) . . ? C3 C4 B1 106.8(2) . . ? C5 C4 B1 149.4(2) . . ? C6 C5 C11 117.2(2) . . ? C6 C5 C4 106.7(2) . . ? C11 C5 C4 136.0(2) . . ? C14 C6 C5 126.2(2) . . ? C14 C6 O1 124.3(2) . . ? C5 C6 O1 109.5(2) . . ? C3 O1 C6 103.29(17) . . ? C2 C7 C8 118.2(2) . . ? C2 C7 H1 120.9 . . ? C8 C7 H1 120.9 . . ? C9 C8 C7 119.4(2) . . ? C9 C8 H2 120.3 . . ? C7 C8 H2 120.3 . . ? C8 C9 C10 120.6(2) . . ? C8 C9 H3 119.7 . . ? C10 C9 H3 119.7 . . ? C1 C10 C9 120.8(2) . . ? C1 C10 H4 119.6 . . ? C9 C10 H4 119.6 . . ? C12 C11 C5 117.6(2) . . ? C12 C11 H5 121.2 . . ? C5 C11 H5 121.2 . . ? C11 C12 C13 122.1(2) . . ? C11 C12 H6 118.9 . . ? C13 C12 H6 118.9 . . ? C14 C13 C12 121.4(2) . . ? C14 C13 H7 119.3 . . ? C12 C13 H7 119.3 . . ? C6 C14 C13 115.4(2) . . ? C6 C14 H8 122.3 . . ? C13 C14 H8 122.3 . . ? C20 C15 C16 118.2(2) . . ? C20 C15 B1 120.9(2) . . ? C16 C15 B1 120.8(2) . . ? C17 C16 C15 120.0(2) . . ? C17 C16 C21 118.4(2) . . ? C15 C16 C21 121.6(2) . . ? C18 C17 C16 121.7(2) . . ? C18 C17 H9 119.2 . . ? C16 C17 H9 119.2 . . ? C19 C18 C17 117.7(2) . . ? C19 C18 C22 121.1(2) . . ? C17 C18 C22 121.2(2) . . ? C20 C19 C18 122.5(2) . . ? C20 C19 H10 118.8 . . ? C18 C19 H10 118.8 . . ? C19 C20 C15 119.8(2) . . ? C19 C20 C23 119.4(2) . . ? C15 C20 C23 120.7(2) . . ? C16 C21 H11 109.5 . . ? C16 C21 H12 109.5 . . ? H11 C21 H12 109.5 . . ? C16 C21 H13 109.5 . . ? H11 C21 H13 109.5 . . ? H12 C21 H13 109.5 . . ? C18 C22 H14 109.5 . . ? C18 C22 H15 109.5 . . ? H14 C22 H15 109.5 . . ? C18 C22 H16 109.5 . . ? H14 C22 H16 109.5 . . ? H15 C22 H16 109.5 . . ? C20 C23 H17 109.5 . . ? C20 C23 H18 109.5 . . ? H17 C23 H18 109.5 . . ? C20 C23 H19 109.5 . . ? H17 C23 H19 109.5 . . ? H18 C23 H19 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 B1 C1 C10 178.5(2) . . . . ? C15 B1 C1 C10 2.3(4) . . . . ? C4 B1 C1 C2 0.2(2) . . . . ? C15 B1 C1 C2 -176.0(2) . . . . ? C10 C1 C2 C7 0.4(3) . . . . ? B1 C1 C2 C7 179.0(2) . . . . ? C10 C1 C2 C3 -179.1(2) . . . . ? B1 C1 C2 C3 -0.5(2) . . . . ? C7 C2 C3 C4 -178.7(2) . . . . ? C1 C2 C3 C4 0.8(3) . . . . ? C7 C2 C3 O1 1.1(4) . . . . ? C1 C2 C3 O1 -179.4(2) . . . . ? O1 C3 C4 C5 1.3(3) . . . . ? C2 C3 C4 C5 -178.84(19) . . . . ? O1 C3 C4 B1 179.47(19) . . . . ? C2 C3 C4 B1 -0.7(3) . . . . ? C15 B1 C4 C3 176.3(2) . . . . ? C1 B1 C4 C3 0.3(2) . . . . ? C15 B1 C4 C5 -7.2(6) . . . . ? C1 B1 C4 C5 176.8(4) . . . . ? C3 C4 C5 C6 -0.9(2) . . . . ? B1 C4 C5 C6 -177.4(4) . . . . ? C3 C4 C5 C11 178.1(3) . . . . ? B1 C4 C5 C11 1.5(6) . . . . ? C11 C5 C6 C14 0.6(4) . . . . ? C4 C5 C6 C14 179.8(2) . . . . ? C11 C5 C6 O1 -178.92(19) . . . . ? C4 C5 C6 O1 0.3(2) . . . . ? C4 C3 O1 C6 -1.1(2) . . . . ? C2 C3 O1 C6 179.0(2) . . . . ? C14 C6 O1 C3 -179.0(2) . . . . ? C5 C6 O1 C3 0.5(2) . . . . ? C1 C2 C7 C8 -0.5(3) . . . . ? C3 C2 C7 C8 179.0(2) . . . . ? C2 C7 C8 C9 -0.1(3) . . . . ? C7 C8 C9 C10 0.6(3) . . . . ? C2 C1 C10 C9 0.1(3) . . . . ? B1 C1 C10 C9 -178.0(2) . . . . ? C8 C9 C10 C1 -0.7(4) . . . . ? C6 C5 C11 C12 -0.2(3) . . . . ? C4 C5 C11 C12 -179.1(2) . . . . ? C5 C11 C12 C13 -0.3(4) . . . . ? C11 C12 C13 C14 0.7(4) . . . . ? C5 C6 C14 C13 -0.2(4) . . . . ? O1 C6 C14 C13 179.2(2) . . . . ? C12 C13 C14 C6 -0.4(4) . . . . ? C4 B1 C15 C20 124.8(3) . . . . ? C1 B1 C15 C20 -60.1(3) . . . . ? C4 B1 C15 C16 -58.4(3) . . . . ? C1 B1 C15 C16 116.7(3) . . . . ? C20 C15 C16 C17 3.9(3) . . . . ? B1 C15 C16 C17 -172.9(2) . . . . ? C20 C15 C16 C21 -178.5(2) . . . . ? B1 C15 C16 C21 4.7(3) . . . . ? C15 C16 C17 C18 -1.0(3) . . . . ? C21 C16 C17 C18 -178.8(2) . . . . ? C16 C17 C18 C19 -2.2(3) . . . . ? C16 C17 C18 C22 179.6(2) . . . . ? C17 C18 C19 C20 2.5(3) . . . . ? C22 C18 C19 C20 -179.2(2) . . . . ? C18 C19 C20 C15 0.4(4) . . . . ? C18 C19 C20 C23 -175.6(2) . . . . ? C16 C15 C20 C19 -3.6(3) . . . . ? B1 C15 C20 C19 173.3(2) . . . . ? C16 C15 C20 C23 172.4(2) . . . . ? B1 C15 C20 C23 -10.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.971 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.055 # Attachment 'compound4.CIF' data_cmpd4 _database_code_depnum_ccdc_archive 'CCDC 857123' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (benzothieno)(benzo)borole ; _chemical_name_common (benzothieno)(benzo)borole _chemical_melting_point 388 _chemical_formula_moiety 'C23 H19 B S' _chemical_formula_sum 'C23 H19 B S' _chemical_formula_weight 338.25 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' S S 0.1246 0.1234 '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' H H 0.0000 0.0000 '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 32.132(14) _cell_length_b 7.890(3) _cell_length_c 14.955(7) _cell_angle_alpha 90.00 _cell_angle_beta 106.728(7) _cell_angle_gamma 90.00 _cell_volume 3631(3) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5367 _cell_measurement_theta_min 1.3231 _cell_measurement_theta_max 31.5050 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.180 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9823 _exptl_absorpt_correction_T_max 0.9823 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; 'Saturn70 CCD (4x4 bin mode) with MicroMax-007' ; _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11707 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0412 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3190 _reflns_number_gt 2688 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 for windows' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0888P)^2^+11.2448P] 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 none _refine_ls_number_reflns 3190 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0883 _refine_ls_R_factor_gt 0.0748 _refine_ls_wR_factor_ref 0.1943 _refine_ls_wR_factor_gt 0.1841 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.139 _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 B1 B 0.12069(12) 0.4164(5) 0.5232(3) 0.0214(8) Uani 1 1 d . . . C1 C 0.08287(11) 0.4133(4) 0.5727(2) 0.0257(8) Uani 1 1 d . . . C2 C 0.04997(11) 0.3039(4) 0.5231(2) 0.0239(8) Uani 1 1 d . . . C3 C 0.06371(11) 0.2319(4) 0.4436(2) 0.0243(8) Uani 1 1 d . . . C4 C 0.10391(11) 0.2887(4) 0.4417(2) 0.0236(8) Uani 1 1 d . . . C5 C 0.11517(11) 0.2175(4) 0.3624(2) 0.0250(8) Uani 1 1 d . . . C6 C 0.08226(11) 0.1093(4) 0.3084(2) 0.0250(8) Uani 1 1 d . . . S1 S 0.03799(3) 0.09772(11) 0.35567(6) 0.0266(3) Uani 1 1 d . . . C7 C 0.01175(11) 0.2785(4) 0.5475(2) 0.0270(8) Uani 1 1 d . . . H1 H -0.0104 0.2051 0.5124 0.032 Uiso 1 1 calc R . . C8 C 0.00721(11) 0.3662(4) 0.6267(2) 0.0273(8) Uani 1 1 d . . . H2 H -0.0183 0.3516 0.6458 0.033 Uiso 1 1 calc R . . C9 C 0.03977(12) 0.4733(5) 0.6762(3) 0.0291(8) Uani 1 1 d . . . H3 H 0.0364 0.5316 0.7293 0.035 Uiso 1 1 calc R . . C10 C 0.07758(11) 0.4968(5) 0.6490(2) 0.0289(8) Uani 1 1 d . . . H4 H 0.0997 0.5709 0.6836 0.035 Uiso 1 1 calc R . . C11 C 0.15298(11) 0.2393(4) 0.3332(2) 0.0253(8) Uani 1 1 d . . . H5 H 0.1760 0.3098 0.3678 0.030 Uiso 1 1 calc R . . C12 C 0.15611(11) 0.1565(5) 0.2535(2) 0.0287(8) Uani 1 1 d . . . H6 H 0.1811 0.1726 0.2328 0.034 Uiso 1 1 calc R . . C13 C 0.12272(12) 0.0493(5) 0.2034(2) 0.0304(8) Uani 1 1 d . . . H7 H 0.1257 -0.0079 0.1497 0.036 Uiso 1 1 calc R . . C14 C 0.08589(12) 0.0257(5) 0.2305(3) 0.0302(8) Uani 1 1 d . . . H8 H 0.0634 -0.0469 0.1961 0.036 Uiso 1 1 calc R . . C15 C 0.16252(10) 0.5296(4) 0.5493(2) 0.0223(7) Uani 1 1 d . . . C16 C 0.20338(11) 0.4635(4) 0.5971(2) 0.0248(8) Uani 1 1 d . . . C17 C 0.23951(11) 0.5715(4) 0.6248(2) 0.0244(8) Uani 1 1 d . . . H9 H 0.2669 0.5260 0.6584 0.029 Uiso 1 1 calc R . . C18 C 0.23605(11) 0.7432(4) 0.6043(2) 0.0226(8) Uani 1 1 d . . . C19 C 0.19566(11) 0.8052(4) 0.5536(2) 0.0237(8) Uani 1 1 d . . . H10 H 0.1930 0.9215 0.5366 0.028 Uiso 1 1 calc R . . C20 C 0.15910(11) 0.7022(4) 0.5269(2) 0.0228(7) Uani 1 1 d . . . C21 C 0.20905(13) 0.2759(5) 0.6170(3) 0.0386(10) Uani 1 1 d . . . H11 H 0.2102 0.2161 0.5603 0.058 Uiso 1 1 calc R . . H12 H 0.1845 0.2334 0.6370 0.058 Uiso 1 1 calc R . . H13 H 0.2361 0.2564 0.6666 0.058 Uiso 1 1 calc R . . C22 C 0.27504(12) 0.8597(5) 0.6344(3) 0.0309(9) Uani 1 1 d . . . H14 H 0.2761 0.9322 0.5819 0.046 Uiso 1 1 calc R . . H15 H 0.3017 0.7918 0.6544 0.046 Uiso 1 1 calc R . . H16 H 0.2726 0.9306 0.6865 0.046 Uiso 1 1 calc R . . C23 C 0.11609(12) 0.7753(5) 0.4702(3) 0.0369(10) Uani 1 1 d . . . H17 H 0.1085 0.7287 0.4068 0.055 Uiso 1 1 calc R . . H18 H 0.1185 0.8989 0.4674 0.055 Uiso 1 1 calc R . . H19 H 0.0935 0.7456 0.4996 0.055 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 B1 0.0216(19) 0.0180(19) 0.0234(19) 0.0033(15) 0.0044(16) 0.0016(15) C1 0.0251(18) 0.0236(18) 0.0267(18) 0.0056(15) 0.0047(15) -0.0006(14) C2 0.0306(19) 0.0214(17) 0.0211(17) 0.0071(14) 0.0095(15) 0.0046(14) C3 0.0218(17) 0.0166(16) 0.0293(18) 0.0067(14) -0.0008(14) -0.0022(13) C4 0.0209(17) 0.0192(17) 0.0269(18) 0.0025(14) 0.0010(14) -0.0043(13) C5 0.0314(19) 0.0211(17) 0.0219(17) 0.0072(14) 0.0065(15) 0.0104(15) C6 0.0196(17) 0.0236(18) 0.0285(18) 0.0058(15) 0.0017(14) 0.0019(14) S1 0.0209(5) 0.0268(5) 0.0285(5) -0.0027(4) 0.0015(4) -0.0060(3) C7 0.0260(18) 0.0204(17) 0.0286(19) 0.0054(14) -0.0019(15) -0.0032(14) C8 0.0259(18) 0.0274(19) 0.033(2) 0.0036(15) 0.0146(16) -0.0019(15) C9 0.032(2) 0.0287(19) 0.0292(19) -0.0017(16) 0.0128(16) -0.0027(16) C10 0.0266(19) 0.0268(19) 0.032(2) 0.0022(16) 0.0073(16) -0.0065(15) C11 0.0207(17) 0.0222(17) 0.0282(18) 0.0016(14) -0.0005(15) -0.0032(14) C12 0.0222(18) 0.036(2) 0.0289(19) 0.0037(16) 0.0089(15) 0.0047(15) C13 0.034(2) 0.031(2) 0.0249(18) -0.0030(15) 0.0053(16) 0.0076(16) C14 0.0281(19) 0.0243(19) 0.033(2) -0.0025(16) -0.0002(16) 0.0024(15) C15 0.0205(17) 0.0202(17) 0.0232(17) 0.0025(14) 0.0017(14) -0.0042(14) C16 0.0255(18) 0.0163(17) 0.0289(18) 0.0010(14) 0.0018(15) -0.0016(14) C17 0.0173(16) 0.0241(18) 0.0276(18) -0.0022(15) -0.0004(14) -0.0004(14) C18 0.0227(17) 0.0224(18) 0.0237(17) -0.0051(14) 0.0082(14) -0.0067(14) C19 0.0259(18) 0.0152(16) 0.0316(18) 0.0033(14) 0.0109(15) -0.0012(14) C20 0.0222(17) 0.0194(17) 0.0277(17) 0.0026(14) 0.0089(14) 0.0000(14) C21 0.034(2) 0.0216(19) 0.050(2) 0.0059(17) -0.0047(18) -0.0026(16) C22 0.0264(19) 0.029(2) 0.039(2) -0.0081(16) 0.0109(17) -0.0113(15) C23 0.026(2) 0.027(2) 0.052(2) 0.0127(18) 0.0031(18) 0.0011(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 B1 C4 1.554(5) . ? B1 C15 1.567(5) . ? B1 C1 1.595(5) . ? C1 C10 1.369(5) . ? C1 C2 1.400(5) . ? C2 C7 1.393(5) . ? C2 C3 1.495(5) . ? C3 C4 1.375(5) . ? C3 S1 1.706(3) . ? C4 C5 1.448(5) . ? C5 C11 1.415(5) . ? C5 C6 1.417(5) . ? C6 C14 1.373(5) . ? C6 S1 1.763(4) . ? C7 C8 1.414(5) . ? C7 H1 0.9500 . ? C8 C9 1.382(5) . ? C8 H2 0.9500 . ? C9 C10 1.400(5) . ? C9 H3 0.9500 . ? C10 H4 0.9500 . ? C11 C12 1.388(5) . ? C11 H5 0.9500 . ? C12 C13 1.402(5) . ? C12 H6 0.9500 . ? C13 C14 1.369(5) . ? C13 H7 0.9500 . ? C14 H8 0.9500 . ? C15 C20 1.399(5) . ? C15 C16 1.402(5) . ? C16 C17 1.403(5) . ? C16 C21 1.510(5) . ? C17 C18 1.386(5) . ? C17 H9 0.9500 . ? C18 C19 1.390(5) . ? C18 C22 1.514(5) . ? C19 C20 1.389(5) . ? C19 H10 0.9500 . ? C20 C23 1.512(5) . ? C21 H11 0.9800 . ? C21 H12 0.9800 . ? C21 H13 0.9800 . ? C22 H14 0.9800 . ? C22 H15 0.9800 . ? C22 H16 0.9800 . ? C23 H17 0.9800 . ? C23 H18 0.9800 . ? C23 H19 0.9800 . ? 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 C4 B1 C15 130.1(3) . . ? C4 B1 C1 102.5(3) . . ? C15 B1 C1 127.3(3) . . ? C10 C1 C2 118.8(3) . . ? C10 C1 B1 132.3(3) . . ? C2 C1 B1 108.9(3) . . ? C7 C2 C1 122.6(3) . . ? C7 C2 C3 129.7(3) . . ? C1 C2 C3 107.7(3) . . ? C4 C3 C2 112.8(3) . . ? C4 C3 S1 115.8(3) . . ? C2 C3 S1 131.4(3) . . ? C3 C4 C5 110.4(3) . . ? C3 C4 B1 108.1(3) . . ? C5 C4 B1 141.4(3) . . ? C11 C5 C6 117.6(3) . . ? C11 C5 C4 130.1(3) . . ? C6 C5 C4 112.3(3) . . ? C14 C6 C5 122.8(3) . . ? C14 C6 S1 126.2(3) . . ? C5 C6 S1 111.0(3) . . ? C3 S1 C6 90.52(17) . . ? C2 C7 C8 117.4(3) . . ? C2 C7 H1 121.3 . . ? C8 C7 H1 121.3 . . ? C9 C8 C7 120.2(3) . . ? C9 C8 H2 119.9 . . ? C7 C8 H2 119.9 . . ? C8 C9 C10 120.8(3) . . ? C8 C9 H3 119.6 . . ? C10 C9 H3 119.6 . . ? C1 C10 C9 120.3(3) . . ? C1 C10 H4 119.9 . . ? C9 C10 H4 119.9 . . ? C12 C11 C5 119.3(3) . . ? C12 C11 H5 120.4 . . ? C5 C11 H5 120.4 . . ? C11 C12 C13 120.7(3) . . ? C11 C12 H6 119.7 . . ? C13 C12 H6 119.7 . . ? C14 C13 C12 121.2(3) . . ? C14 C13 H7 119.4 . . ? C12 C13 H7 119.4 . . ? C13 C14 C6 118.5(3) . . ? C13 C14 H8 120.7 . . ? C6 C14 H8 120.7 . . ? C20 C15 C16 118.8(3) . . ? C20 C15 B1 119.5(3) . . ? C16 C15 B1 121.7(3) . . ? C15 C16 C17 119.9(3) . . ? C15 C16 C21 120.5(3) . . ? C17 C16 C21 119.6(3) . . ? C18 C17 C16 121.4(3) . . ? C18 C17 H9 119.3 . . ? C16 C17 H9 119.3 . . ? C17 C18 C19 117.8(3) . . ? C17 C18 C22 121.4(3) . . ? C19 C18 C22 120.8(3) . . ? C20 C19 C18 122.1(3) . . ? C20 C19 H10 119.0 . . ? C18 C19 H10 119.0 . . ? C19 C20 C15 119.9(3) . . ? C19 C20 C23 119.9(3) . . ? C15 C20 C23 120.1(3) . . ? C16 C21 H11 109.5 . . ? C16 C21 H12 109.5 . . ? H11 C21 H12 109.5 . . ? C16 C21 H13 109.5 . . ? H11 C21 H13 109.5 . . ? H12 C21 H13 109.5 . . ? C18 C22 H14 109.5 . . ? C18 C22 H15 109.5 . . ? H14 C22 H15 109.5 . . ? C18 C22 H16 109.5 . . ? H14 C22 H16 109.5 . . ? H15 C22 H16 109.5 . . ? C20 C23 H17 109.5 . . ? C20 C23 H18 109.5 . . ? H17 C23 H18 109.5 . . ? C20 C23 H19 109.5 . . ? H17 C23 H19 109.5 . . ? H18 C23 H19 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 B1 C1 C10 179.7(4) . . . . ? C15 B1 C1 C10 -3.2(6) . . . . ? C4 B1 C1 C2 -1.6(4) . . . . ? C15 B1 C1 C2 175.4(3) . . . . ? C10 C1 C2 C7 1.0(5) . . . . ? B1 C1 C2 C7 -177.9(3) . . . . ? C10 C1 C2 C3 179.4(3) . . . . ? B1 C1 C2 C3 0.5(4) . . . . ? C7 C2 C3 C4 179.2(3) . . . . ? C1 C2 C3 C4 1.0(4) . . . . ? C7 C2 C3 S1 0.7(5) . . . . ? C1 C2 C3 S1 -177.6(3) . . . . ? C2 C3 C4 C5 -178.9(3) . . . . ? S1 C3 C4 C5 -0.2(4) . . . . ? C2 C3 C4 B1 -2.0(4) . . . . ? S1 C3 C4 B1 176.7(2) . . . . ? C15 B1 C4 C3 -174.7(3) . . . . ? C1 B1 C4 C3 2.2(4) . . . . ? C15 B1 C4 C5 0.6(7) . . . . ? C1 B1 C4 C5 177.5(4) . . . . ? C3 C4 C5 C11 -179.6(3) . . . . ? B1 C4 C5 C11 5.1(7) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? B1 C4 C5 C6 -175.4(4) . . . . ? C11 C5 C6 C14 0.4(5) . . . . ? C4 C5 C6 C14 -179.2(3) . . . . ? C11 C5 C6 S1 179.9(2) . . . . ? C4 C5 C6 S1 0.3(4) . . . . ? C4 C3 S1 C6 0.3(3) . . . . ? C2 C3 S1 C6 178.8(3) . . . . ? C14 C6 S1 C3 179.1(3) . . . . ? C5 C6 S1 C3 -0.3(3) . . . . ? C1 C2 C7 C8 -1.0(5) . . . . ? C3 C2 C7 C8 -179.1(3) . . . . ? C2 C7 C8 C9 0.5(5) . . . . ? C7 C8 C9 C10 0.1(5) . . . . ? C2 C1 C10 C9 -0.4(5) . . . . ? B1 C1 C10 C9 178.1(3) . . . . ? C8 C9 C10 C1 -0.1(6) . . . . ? C6 C5 C11 C12 0.7(5) . . . . ? C4 C5 C11 C12 -179.9(3) . . . . ? C5 C11 C12 C13 -1.4(5) . . . . ? C11 C12 C13 C14 1.2(6) . . . . ? C12 C13 C14 C6 -0.1(5) . . . . ? C5 C6 C14 C13 -0.6(5) . . . . ? S1 C6 C14 C13 180.0(3) . . . . ? C4 B1 C15 C20 102.2(4) . . . . ? C1 B1 C15 C20 -74.0(5) . . . . ? C4 B1 C15 C16 -79.6(5) . . . . ? C1 B1 C15 C16 104.2(4) . . . . ? C20 C15 C16 C17 2.6(5) . . . . ? B1 C15 C16 C17 -175.6(3) . . . . ? C20 C15 C16 C21 -175.9(3) . . . . ? B1 C15 C16 C21 5.8(5) . . . . ? C15 C16 C17 C18 -1.4(5) . . . . ? C21 C16 C17 C18 177.2(3) . . . . ? C16 C17 C18 C19 -1.2(5) . . . . ? C16 C17 C18 C22 179.9(3) . . . . ? C17 C18 C19 C20 2.7(5) . . . . ? C22 C18 C19 C20 -178.4(3) . . . . ? C18 C19 C20 C15 -1.4(5) . . . . ? C18 C19 C20 C23 -178.9(3) . . . . ? C16 C15 C20 C19 -1.3(5) . . . . ? B1 C15 C20 C19 177.1(3) . . . . ? C16 C15 C20 C23 176.2(3) . . . . ? B1 C15 C20 C23 -5.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.714 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.071