Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Yue Wang' _publ_contact_author_address ; Jilin University Changchun 130012 CHINA ; _publ_contact_author_email YUEWANG@JLU.EDU.CN _publ_section_title ; Polymorphs and Pseudo-Polymorph Based on a Luminescent Boron-Containing Compound: Structural Diversity Arising from Conformational Isomers and Noncovalent Interaction ; loop_ _publ_author_name 'Yue Wang ' 'Hongyu Zhang ' 'Zuolun Zhang ' 'Jingying Zhang ' # Attachment 'Form_A.cif' data_z1_Form_A _database_code_depnum_ccdc_archive 'CCDC 623074' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H22 B N O3' _chemical_formula_weight 407.26 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P(2)1/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.2799(17) _cell_length_b 8.8747(18) _cell_length_c 28.103(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.03(3) _cell_angle_gamma 90.00 _cell_volume 2057.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 17664 _cell_measurement_theta_min 2.405 _cell_measurement_theta_max 27.47 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9626 _exptl_absorpt_correction_T_max 0.9828 _exptl_absorpt_process_details ; Higashi, T. (1995) Progrom for Absorption Correcttion. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method 'Omega scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 4561 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4561 _reflns_number_gt 2938 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction PROCESS-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0751P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef 0 _refine_ls_number_reflns 4561 _refine_ls_number_parameters 368 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0689 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1202 _refine_ls_wR_factor_gt 0.1047 _refine_ls_goodness_of_fit_ref 0.903 _refine_ls_restrained_S_all 0.903 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.3938(2) 0.32716(18) 0.15062(6) 0.0337(4) Uani 1 1 d . . . O1 O 0.25806(12) 0.29441(11) 0.11567(3) 0.0385(3) Uani 1 1 d . . . O2 O 0.32513(12) 0.42634(12) 0.18508(3) 0.0411(3) Uani 1 1 d . . . O3 O 0.91998(15) 0.62815(15) 0.06577(5) 0.0661(4) Uani 1 1 d . . . N1 N 0.44566(14) 0.17224(13) 0.17738(4) 0.0321(3) Uani 1 1 d . . . C1 C 0.27672(17) 0.17717(17) 0.08603(5) 0.0358(3) Uani 1 1 d . . . C2 C 0.1977(2) 0.1806(2) 0.04018(6) 0.0462(4) Uani 1 1 d . . . H2 H 0.128(2) 0.269(2) 0.0311(6) 0.064(6) Uiso 1 1 d . . . C3 C 0.2144(2) 0.0608(2) 0.00959(6) 0.0500(4) Uani 1 1 d . . . H3 H 0.162(2) 0.067(2) -0.0209(7) 0.061(5) Uiso 1 1 d . . . C4 C 0.3083(2) -0.06495(19) 0.02314(5) 0.0446(4) Uani 1 1 d . . . C5 C 0.3837(2) -0.06769(19) 0.06910(5) 0.0413(4) Uani 1 1 d . . . H5 H 0.452(2) -0.1529(19) 0.0791(6) 0.046(5) Uiso 1 1 d . . . C6 C 0.36838(18) 0.05108(16) 0.10141(5) 0.0350(3) Uani 1 1 d . . . C7 C 0.43746(17) 0.04190(16) 0.15144(5) 0.0345(3) Uani 1 1 d . . . C8 C 0.4893(2) -0.09197(19) 0.17331(6) 0.0431(4) Uani 1 1 d . . . H8 H 0.479(2) -0.187(2) 0.1556(6) 0.049(5) Uiso 1 1 d . . . C9 C 0.5517(2) -0.09038(19) 0.22044(6) 0.0470(4) Uani 1 1 d . . . H9 H 0.587(2) -0.185(2) 0.2366(6) 0.060(5) Uiso 1 1 d . . . C10 C 0.5574(2) 0.04136(19) 0.24617(6) 0.0435(4) Uani 1 1 d . . . H10 H 0.595(2) 0.047(2) 0.2770(7) 0.057(5) Uiso 1 1 d . . . C11 C 0.50072(17) 0.17452(17) 0.22460(5) 0.0349(3) Uani 1 1 d . . . C12 C 0.49172(18) 0.31748(17) 0.25025(5) 0.0372(3) Uani 1 1 d . . . C13 C 0.5607(2) 0.3356(2) 0.29763(5) 0.0440(4) Uani 1 1 d . . . H13 H 0.621(2) 0.257(2) 0.3136(6) 0.048(5) Uiso 1 1 d . . . C14 C 0.5413(2) 0.4651(2) 0.32362(5) 0.0464(4) Uani 1 1 d . . . C15 C 0.4492(2) 0.5807(2) 0.30173(6) 0.0490(4) Uani 1 1 d . . . H15 H 0.430(2) 0.671(2) 0.3186(6) 0.056(5) Uiso 1 1 d . . . C16 C 0.3798(2) 0.56775(19) 0.25561(6) 0.0440(4) Uani 1 1 d . . . H16 H 0.312(2) 0.6476(19) 0.2397(6) 0.048(5) Uiso 1 1 d . . . C17 C 0.40029(17) 0.43676(17) 0.22942(5) 0.0364(3) Uani 1 1 d . . . C18 C 0.54796(17) 0.39798(16) 0.12754(5) 0.0333(3) Uani 1 1 d . . . C19 C 0.70950(19) 0.37534(18) 0.14381(5) 0.0405(4) Uani 1 1 d . . . H19 H 0.739(2) 0.303(2) 0.1714(6) 0.052(5) Uiso 1 1 d . . . C20 C 0.8379(2) 0.44743(18) 0.12434(6) 0.0425(4) Uani 1 1 d . . . H20 H 0.946(2) 0.429(2) 0.1371(6) 0.056(5) Uiso 1 1 d . . . C21 C 0.80555(19) 0.54741(18) 0.08737(6) 0.0436(4) Uani 1 1 d . . . C22 C 0.6470(2) 0.5710(2) 0.06914(7) 0.0552(5) Uani 1 1 d . . . H22 H 0.622(3) 0.636(2) 0.0407(8) 0.081(7) Uiso 1 1 d . . . C23 C 0.5227(2) 0.4976(2) 0.08899(6) 0.0494(4) Uani 1 1 d . . . H23 H 0.410(2) 0.514(2) 0.0739(6) 0.064(5) Uiso 1 1 d . . . C24 C 1.0817(2) 0.6225(3) 0.08654(12) 0.0779(8) Uani 1 1 d . . . H24A H 1.144(3) 0.687(3) 0.0683(9) 0.110(9) Uiso 1 1 d . . . H24B H 1.124(3) 0.512(3) 0.0851(9) 0.108(8) Uiso 1 1 d . . . H24C H 1.089(3) 0.649(3) 0.1210(10) 0.105(10) Uiso 1 1 d . . . C25 C 0.3273(3) -0.1924(3) -0.01135(7) 0.0605(5) Uani 1 1 d . . . H25B H 0.350(3) -0.284(3) 0.0041(10) 0.116(10) Uiso 1 1 d . . . H25A H 0.229(4) -0.212(3) -0.0257(10) 0.112(10) Uiso 1 1 d . . . H25C H 0.400(4) -0.171(4) -0.0346(12) 0.143(12) Uiso 1 1 d . . . C26 C 0.6150(3) 0.4802(3) 0.37458(7) 0.0654(6) Uani 1 1 d . . . H26B H 0.679(3) 0.390(3) 0.3866(9) 0.103(9) Uiso 1 1 d . . . H26A H 0.545(4) 0.507(4) 0.3966(12) 0.140(12) Uiso 1 1 d . . . H26C H 0.702(4) 0.546(4) 0.3771(10) 0.121(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0356(9) 0.0358(9) 0.0291(8) 0.0029(7) -0.0012(7) 0.0038(7) O1 0.0374(6) 0.0403(6) 0.0365(5) 0.0016(5) -0.0040(4) 0.0030(5) O2 0.0431(6) 0.0452(6) 0.0347(6) -0.0012(5) 0.0011(5) 0.0086(5) O3 0.0445(7) 0.0678(9) 0.0877(10) 0.0370(7) 0.0156(7) -0.0002(6) N1 0.0319(6) 0.0360(6) 0.0282(6) 0.0041(5) 0.0016(5) -0.0015(5) C1 0.0339(8) 0.0396(8) 0.0336(7) 0.0034(6) 0.0016(6) -0.0049(6) C2 0.0476(9) 0.0508(10) 0.0381(9) 0.0054(7) -0.0068(7) -0.0008(8) C3 0.0549(10) 0.0616(11) 0.0316(8) 0.0009(8) -0.0075(7) -0.0086(9) C4 0.0510(9) 0.0497(9) 0.0330(8) -0.0011(7) 0.0028(7) -0.0112(8) C5 0.0475(9) 0.0399(9) 0.0363(8) 0.0009(7) 0.0031(7) -0.0040(7) C6 0.0373(8) 0.0382(8) 0.0293(7) 0.0028(6) 0.0006(6) -0.0047(6) C7 0.0350(7) 0.0359(8) 0.0327(7) 0.0022(6) 0.0024(6) -0.0012(6) C8 0.0533(10) 0.0365(8) 0.0385(8) 0.0034(7) -0.0013(7) 0.0010(7) C9 0.0553(10) 0.0414(9) 0.0429(9) 0.0099(7) -0.0031(8) 0.0045(8) C10 0.0519(10) 0.0483(9) 0.0290(8) 0.0060(7) -0.0039(7) 0.0026(8) C11 0.0344(7) 0.0420(8) 0.0281(7) 0.0046(6) 0.0014(6) -0.0012(7) C12 0.0372(8) 0.0431(8) 0.0315(7) -0.0007(6) 0.0039(6) -0.0029(7) C13 0.0470(9) 0.0504(10) 0.0341(8) 0.0012(7) 0.0013(7) -0.0027(8) C14 0.0490(9) 0.0559(10) 0.0345(8) -0.0064(8) 0.0045(7) -0.0087(8) C15 0.0514(10) 0.0507(10) 0.0463(9) -0.0133(8) 0.0127(8) -0.0055(8) C16 0.0430(9) 0.0452(9) 0.0448(9) -0.0038(7) 0.0096(7) 0.0019(7) C17 0.0343(8) 0.0431(8) 0.0322(7) 0.0010(6) 0.0060(6) -0.0017(6) C18 0.0378(8) 0.0312(7) 0.0305(7) 0.0005(6) 0.0014(6) 0.0018(6) C19 0.0419(9) 0.0425(8) 0.0364(8) 0.0082(7) -0.0009(7) -0.0019(7) C20 0.0361(8) 0.0452(9) 0.0455(9) 0.0077(7) -0.0014(7) -0.0018(7) C21 0.0409(9) 0.0401(8) 0.0510(9) 0.0091(7) 0.0104(7) 0.0006(7) C22 0.0456(10) 0.0586(11) 0.0622(11) 0.0311(9) 0.0088(8) 0.0068(8) C23 0.0378(9) 0.0554(10) 0.0547(10) 0.0205(8) 0.0022(8) 0.0059(8) C24 0.0394(11) 0.0728(15) 0.123(2) 0.0372(16) 0.0162(12) -0.0034(10) C25 0.0791(16) 0.0618(13) 0.0398(10) -0.0110(9) 0.0012(10) -0.0080(11) C26 0.0789(16) 0.0764(15) 0.0387(10) -0.0140(10) -0.0063(10) -0.0081(13) _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 O1 1.4558(19) . ? B1 O2 1.4605(19) . ? B1 N1 1.6073(19) . ? B1 C18 1.609(2) . ? O1 C1 1.3502(18) . ? O2 C17 1.3465(17) . ? O3 C21 1.3713(19) . ? O3 C24 1.414(3) . ? N1 C11 1.3651(18) . ? N1 C7 1.3658(18) . ? C1 C2 1.393(2) . ? C1 C6 1.399(2) . ? C2 C3 1.381(2) . ? C3 C4 1.394(2) . ? C4 C5 1.385(2) . ? C4 C25 1.507(3) . ? C5 C6 1.404(2) . ? C6 C7 1.473(2) . ? C7 C8 1.388(2) . ? C8 C9 1.379(2) . ? C9 C10 1.373(2) . ? C10 C11 1.391(2) . ? C11 C12 1.464(2) . ? C12 C17 1.399(2) . ? C12 C13 1.411(2) . ? C13 C14 1.379(2) . ? C14 C15 1.390(3) . ? C14 C26 1.513(2) . ? C15 C16 1.376(2) . ? C16 C17 1.394(2) . ? C18 C19 1.390(2) . ? C18 C23 1.400(2) . ? C19 C20 1.393(2) . ? C20 C21 1.375(2) . ? C21 C22 1.382(2) . ? C22 C23 1.377(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 B1 O2 104.18(12) . . ? O1 B1 N1 107.67(11) . . ? O2 B1 N1 107.99(11) . . ? O1 B1 C18 113.52(12) . . ? O2 B1 C18 113.62(12) . . ? N1 B1 C18 109.51(11) . . ? C1 O1 B1 116.53(11) . . ? C17 O2 B1 118.67(11) . . ? C21 O3 C24 117.70(15) . . ? C11 N1 C7 121.88(12) . . ? C11 N1 B1 119.66(11) . . ? C7 N1 B1 118.43(11) . . ? O1 C1 C2 118.95(14) . . ? O1 C1 C6 120.95(12) . . ? C2 C1 C6 120.05(14) . . ? C3 C2 C1 119.64(16) . . ? C2 C3 C4 121.98(15) . . ? C5 C4 C3 117.65(15) . . ? C5 C4 C25 121.52(17) . . ? C3 C4 C25 120.83(16) . . ? C4 C5 C6 122.07(15) . . ? C1 C6 C5 118.56(13) . . ? C1 C6 C7 119.58(13) . . ? C5 C6 C7 121.74(14) . . ? N1 C7 C8 119.31(13) . . ? N1 C7 C6 117.36(12) . . ? C8 C7 C6 123.30(14) . . ? C9 C8 C7 119.46(15) . . ? C10 C9 C8 120.47(15) . . ? C9 C10 C11 119.94(14) . . ? N1 C11 C10 118.84(13) . . ? N1 C11 C12 117.67(12) . . ? C10 C11 C12 123.46(13) . . ? C17 C12 C13 117.91(14) . . ? C17 C12 C11 119.90(13) . . ? C13 C12 C11 121.94(14) . . ? C14 C13 C12 122.56(16) . . ? C13 C14 C15 117.78(15) . . ? C13 C14 C26 121.28(17) . . ? C15 C14 C26 120.93(17) . . ? C16 C15 C14 121.55(16) . . ? C15 C16 C17 120.45(16) . . ? O2 C17 C16 118.56(14) . . ? O2 C17 C12 121.63(13) . . ? C16 C17 C12 119.75(14) . . ? C19 C18 C23 114.85(14) . . ? C19 C18 B1 125.83(13) . . ? C23 C18 B1 119.25(13) . . ? C18 C19 C20 123.36(14) . . ? C21 C20 C19 119.26(15) . . ? O3 C21 C20 125.14(14) . . ? O3 C21 C22 115.30(14) . . ? C20 C21 C22 119.56(15) . . ? C23 C22 C21 119.84(15) . . ? C22 C23 C18 123.09(16) . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.278 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.086 # Attachment 'Form_B.cif' data_z1_Form_B _database_code_depnum_ccdc_archive 'CCDC 623075' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H22 B N O3' _chemical_formula_weight 407.26 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' _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 13.100(3) _cell_length_b 8.6206(17) _cell_length_c 18.923(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.70(3) _cell_angle_gamma 90.00 _cell_volume 2046.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8650 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 27.465 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9717 _exptl_absorpt_correction_T_max 0.9866 _exptl_absorpt_process_details ; Higashi, T. (1995) Progrom for Absorption Correcttion. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method 'Omega scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 4657 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0949 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4657 _reflns_number_gt 2102 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction PROCESS-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0562P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef 0 _refine_ls_number_reflns 4657 _refine_ls_number_parameters 368 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1195 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1175 _refine_ls_wR_factor_gt 0.1029 _refine_ls_goodness_of_fit_ref 0.812 _refine_ls_restrained_S_all 0.812 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.11013(19) 0.7138(3) 0.07785(13) 0.0365(6) Uani 1 1 d . . . O1 O 0.14825(11) 0.68389(16) 0.01386(7) 0.0417(4) Uani 1 1 d . . . O2 O 0.01965(11) 0.81605(16) 0.05084(8) 0.0451(4) Uani 1 1 d . . . O3 O 0.44240(12) 0.9696(2) 0.32334(8) 0.0588(5) Uani 1 1 d . . . N1 N 0.06886(13) 0.55239(19) 0.10196(8) 0.0356(4) Uani 1 1 d . . . C1 C 0.21576(16) 0.5633(2) 0.01895(10) 0.0394(5) Uani 1 1 d . . . C2 C 0.29019(19) 0.5684(3) -0.02048(12) 0.0474(6) Uani 1 1 d . . . H2 H 0.2938(17) 0.661(3) -0.0478(12) 0.058(7) Uiso 1 1 d . . . C3 C 0.3594(2) 0.4455(3) -0.01729(13) 0.0524(6) Uani 1 1 d . . . H3 H 0.4115(18) 0.458(3) -0.0459(13) 0.065(7) Uiso 1 1 d . . . C4 C 0.35714(18) 0.3162(3) 0.02530(13) 0.0505(6) Uani 1 1 d . . . C5 C 0.28168(19) 0.3117(3) 0.06391(13) 0.0481(6) Uani 1 1 d . . . H5 H 0.2808(15) 0.220(2) 0.0929(11) 0.042(6) Uiso 1 1 d . . . C6 C 0.20897(16) 0.4322(2) 0.06131(11) 0.0386(5) Uani 1 1 d . . . C7 C 0.12404(16) 0.4200(2) 0.09733(11) 0.0379(5) Uani 1 1 d . . . C8 C 0.09638(19) 0.2826(3) 0.12525(12) 0.0444(6) Uani 1 1 d . . . H8 H 0.1339(17) 0.187(2) 0.1208(12) 0.055(7) Uiso 1 1 d . . . C9 C 0.01610(19) 0.2836(3) 0.15936(12) 0.0481(6) Uani 1 1 d . . . H9 H -0.0028(16) 0.189(2) 0.1812(11) 0.049(6) Uiso 1 1 d . . . C10 C -0.03907(19) 0.4169(3) 0.16261(12) 0.0448(6) Uani 1 1 d . . . H10 H -0.0959(17) 0.413(2) 0.1841(11) 0.050(7) Uiso 1 1 d . . . C11 C -0.01426(16) 0.5530(2) 0.13227(11) 0.0382(5) Uani 1 1 d . . . C12 C -0.07347(16) 0.6989(2) 0.12923(11) 0.0398(5) Uani 1 1 d . . . C13 C -0.15549(18) 0.7133(3) 0.16308(13) 0.0478(6) Uani 1 1 d . . . H13 H -0.1708(15) 0.625(2) 0.1939(11) 0.049(6) Uiso 1 1 d . . . C14 C -0.21794(19) 0.8448(3) 0.15564(14) 0.0529(6) Uani 1 1 d . . . C15 C -0.1980(2) 0.9645(3) 0.11206(15) 0.0566(7) Uani 1 1 d . . . H15 H -0.2406(17) 1.058(2) 0.1066(11) 0.053(7) Uiso 1 1 d . . . C16 C -0.1191(2) 0.9551(3) 0.07776(14) 0.0495(6) Uani 1 1 d . . . H16 H -0.1054(17) 1.033(3) 0.0503(12) 0.055(7) Uiso 1 1 d . . . C17 C -0.05562(16) 0.8227(3) 0.08672(11) 0.0408(5) Uani 1 1 d . . . C18 C 0.20231(16) 0.7814(2) 0.14681(11) 0.0341(5) Uani 1 1 d . . . C19 C 0.21319(19) 0.7495(3) 0.22081(12) 0.0461(6) Uani 1 1 d . . . H19 H 0.1613(16) 0.679(2) 0.2339(11) 0.049(6) Uiso 1 1 d . . . C20 C 0.29249(19) 0.8141(3) 0.27761(13) 0.0508(6) Uani 1 1 d . . . H20 H 0.2986(18) 0.790(3) 0.3281(13) 0.070(7) Uiso 1 1 d . . . C21 C 0.36619(16) 0.9137(3) 0.26315(12) 0.0411(5) Uani 1 1 d . . . C22 C 0.35939(18) 0.9486(3) 0.19115(12) 0.0466(6) Uani 1 1 d . . . H22 H 0.4131(17) 1.015(3) 0.1801(12) 0.060(7) Uiso 1 1 d . . . C23 C 0.27838(19) 0.8822(3) 0.13494(13) 0.0468(6) Uani 1 1 d . . . H23 H 0.2753(15) 0.909(2) 0.0848(11) 0.049(6) Uiso 1 1 d . . . C24 C 0.5258(2) 1.0618(4) 0.31113(19) 0.0638(8) Uani 1 1 d . . . H24A H 0.496(2) 1.156(3) 0.2784(14) 0.078(9) Uiso 1 1 d . . . H24B H 0.568(2) 1.091(3) 0.3596(16) 0.093(10) Uiso 1 1 d . . . H24C H 0.564(2) 1.001(3) 0.2817(15) 0.091(10) Uiso 1 1 d . . . C25 C 0.4353(3) 0.1854(4) 0.0306(2) 0.0729(9) Uani 1 1 d . . . H25A H 0.411(2) 0.084(4) 0.0308(17) 0.107(13) Uiso 1 1 d . . . H25B H 0.466(3) 0.184(4) -0.009(2) 0.135(15) Uiso 1 1 d . . . C26 C -0.3055(3) 0.8559(5) 0.1927(3) 0.0797(10) Uani 1 1 d . . . H26A H -0.369(3) 0.857(4) 0.163(2) 0.131(17) Uiso 1 1 d . . . H26B H -0.305(3) 0.782(4) 0.228(2) 0.135(16) Uiso 1 1 d . . . H26C H -0.318(4) 0.960(6) 0.207(3) 0.21(2) Uiso 1 1 d . . . H25C H 0.495(3) 0.191(4) 0.075(2) 0.156(18) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0395(14) 0.0356(14) 0.0327(13) 0.0049(11) 0.0077(11) -0.0010(12) O1 0.0505(9) 0.0427(9) 0.0309(8) 0.0038(7) 0.0101(7) 0.0017(8) O2 0.0435(9) 0.0462(9) 0.0447(9) 0.0101(7) 0.0113(7) 0.0040(8) O3 0.0517(10) 0.0752(12) 0.0442(9) -0.0087(8) 0.0053(8) -0.0230(9) N1 0.0366(10) 0.0368(10) 0.0302(9) -0.0005(7) 0.0045(8) -0.0050(9) C1 0.0401(13) 0.0443(14) 0.0299(11) -0.0048(10) 0.0035(10) -0.0016(11) C2 0.0519(15) 0.0551(16) 0.0357(13) 0.0014(12) 0.0130(11) -0.0041(14) C3 0.0488(15) 0.0642(18) 0.0462(14) -0.0066(13) 0.0167(12) -0.0030(14) C4 0.0468(14) 0.0526(16) 0.0513(14) -0.0044(12) 0.0128(12) 0.0019(13) C5 0.0487(15) 0.0442(15) 0.0481(14) 0.0008(12) 0.0085(12) -0.0039(13) C6 0.0394(13) 0.0414(13) 0.0321(11) -0.0029(10) 0.0055(10) -0.0025(11) C7 0.0397(13) 0.0365(13) 0.0325(11) -0.0020(9) 0.0023(10) -0.0034(11) C8 0.0480(14) 0.0360(13) 0.0460(14) 0.0021(11) 0.0085(11) -0.0024(12) C9 0.0493(15) 0.0452(15) 0.0457(14) 0.0081(12) 0.0073(12) -0.0103(13) C10 0.0415(14) 0.0493(15) 0.0432(13) 0.0026(11) 0.0114(12) -0.0065(13) C11 0.0361(12) 0.0437(13) 0.0302(11) -0.0025(10) 0.0025(10) -0.0065(11) C12 0.0372(12) 0.0419(13) 0.0360(12) -0.0034(10) 0.0037(10) -0.0046(11) C13 0.0447(14) 0.0507(15) 0.0478(14) -0.0075(12) 0.0127(12) -0.0086(13) C14 0.0452(14) 0.0526(16) 0.0608(16) -0.0123(12) 0.0152(12) -0.0017(13) C15 0.0518(16) 0.0466(16) 0.0700(18) -0.0095(14) 0.0152(14) 0.0067(14) C16 0.0499(15) 0.0422(15) 0.0522(15) -0.0010(12) 0.0078(12) -0.0025(13) C17 0.0359(12) 0.0458(14) 0.0360(12) -0.0033(10) 0.0026(10) -0.0019(11) C18 0.0388(12) 0.0296(11) 0.0346(11) 0.0010(9) 0.0121(10) -0.0005(10) C19 0.0473(14) 0.0547(15) 0.0383(13) -0.0032(11) 0.0157(11) -0.0171(13) C20 0.0535(15) 0.0671(17) 0.0327(13) -0.0032(12) 0.0140(11) -0.0171(14) C21 0.0366(13) 0.0438(13) 0.0409(13) -0.0063(10) 0.0082(11) -0.0023(11) C22 0.0458(14) 0.0466(14) 0.0459(14) 0.0028(11) 0.0108(12) -0.0155(13) C23 0.0531(15) 0.0514(15) 0.0337(13) 0.0062(11) 0.0089(12) -0.0082(12) C24 0.0460(16) 0.077(2) 0.0632(19) -0.0068(18) 0.0081(15) -0.0206(17) C25 0.067(2) 0.068(2) 0.091(3) -0.0002(19) 0.035(2) 0.0167(19) C26 0.063(2) 0.079(3) 0.111(3) -0.005(2) 0.047(2) 0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 O2 1.447(3) . ? B1 O1 1.459(3) . ? B1 N1 1.606(3) . ? B1 C18 1.611(3) . ? O1 C1 1.350(2) . ? O2 C17 1.350(2) . ? O3 C21 1.368(2) . ? O3 C24 1.423(3) . ? N1 C7 1.367(2) . ? N1 C11 1.369(2) . ? C1 C2 1.389(3) . ? C1 C6 1.403(3) . ? C2 C3 1.384(3) . ? C3 C4 1.381(3) . ? C4 C5 1.388(3) . ? C4 C25 1.508(4) . ? C5 C6 1.401(3) . ? C6 C7 1.466(3) . ? C7 C8 1.387(3) . ? C8 C9 1.383(3) . ? C9 C10 1.368(3) . ? C10 C11 1.385(3) . ? C11 C12 1.470(3) . ? C12 C17 1.396(3) . ? C12 C13 1.406(3) . ? C13 C14 1.381(3) . ? C14 C15 1.391(3) . ? C14 C26 1.510(4) . ? C15 C16 1.372(3) . ? C16 C17 1.393(3) . ? C18 C23 1.389(3) . ? C18 C19 1.394(3) . ? C19 C20 1.379(3) . ? C20 C21 1.377(3) . ? C21 C22 1.373(3) . ? C22 C23 1.391(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 B1 O1 104.80(17) . . ? O2 B1 N1 108.64(17) . . ? O1 B1 N1 107.84(17) . . ? O2 B1 C18 114.38(17) . . ? O1 B1 C18 112.36(17) . . ? N1 B1 C18 108.58(16) . . ? C1 O1 B1 116.75(16) . . ? C17 O2 B1 119.40(16) . . ? C21 O3 C24 118.2(2) . . ? C7 N1 C11 121.93(18) . . ? C7 N1 B1 118.54(16) . . ? C11 N1 B1 119.29(17) . . ? O1 C1 C2 119.0(2) . . ? O1 C1 C6 120.87(18) . . ? C2 C1 C6 120.1(2) . . ? C3 C2 C1 120.4(2) . . ? C4 C3 C2 121.3(2) . . ? C3 C4 C5 117.9(2) . . ? C3 C4 C25 120.9(2) . . ? C5 C4 C25 121.2(3) . . ? C4 C5 C6 122.7(2) . . ? C5 C6 C1 117.6(2) . . ? C5 C6 C7 122.0(2) . . ? C1 C6 C7 120.3(2) . . ? N1 C7 C8 119.20(19) . . ? N1 C7 C6 117.10(18) . . ? C8 C7 C6 123.7(2) . . ? C9 C8 C7 119.3(2) . . ? C10 C9 C8 120.6(2) . . ? C9 C10 C11 120.2(2) . . ? N1 C11 C10 118.7(2) . . ? N1 C11 C12 117.46(18) . . ? C10 C11 C12 123.8(2) . . ? C17 C12 C13 118.1(2) . . ? C17 C12 C11 120.18(19) . . ? C13 C12 C11 121.4(2) . . ? C14 C13 C12 122.3(2) . . ? C13 C14 C15 117.5(2) . . ? C13 C14 C26 120.7(3) . . ? C15 C14 C26 121.7(3) . . ? C16 C15 C14 122.1(3) . . ? C15 C16 C17 119.7(3) . . ? O2 C17 C16 118.1(2) . . ? O2 C17 C12 121.7(2) . . ? C16 C17 C12 120.2(2) . . ? C23 C18 C19 114.5(2) . . ? C23 C18 B1 120.09(18) . . ? C19 C18 B1 125.37(19) . . ? C20 C19 C18 122.7(2) . . ? C21 C20 C19 120.7(2) . . ? O3 C21 C22 125.0(2) . . ? O3 C21 C20 116.1(2) . . ? C22 C21 C20 119.0(2) . . ? C21 C22 C23 119.1(2) . . ? C18 C23 C22 124.0(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.221 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.091 # Attachment 'Form_C.cif' data_z1_Form_C _database_code_depnum_ccdc_archive 'CCDC 623076' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H23 B Cl3 N O3' _chemical_formula_weight 526.62 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' Cl Cl 0.1484 0.1585 '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 9.802(2) _cell_length_b 22.740(5) _cell_length_c 11.474(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.32(3) _cell_angle_gamma 90.00 _cell_volume 2555.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9662 _cell_measurement_theta_min 1.775 _cell_measurement_theta_max 27.455 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.389 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8828 _exptl_absorpt_correction_T_max 0.9651 _exptl_absorpt_process_details ; Higashi, T. (1995) Progrom for Absorption Correcttion. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method 'Omega scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 5580 _diffrn_reflns_av_R_equivalents 0.0687 _diffrn_reflns_av_sigmaI/netI 0.1786 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5580 _reflns_number_gt 1755 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction PROCESS-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0962P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef 0 _refine_ls_number_reflns 5580 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1889 _refine_ls_R_factor_gt 0.0648 _refine_ls_wR_factor_ref 0.2107 _refine_ls_wR_factor_gt 0.1610 _refine_ls_goodness_of_fit_ref 0.790 _refine_ls_restrained_S_all 0.790 _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 0.3090(6) 0.3556(2) 0.1668(4) 0.0387(13) Uani 1 1 d . . . O1 O 0.3114(3) 0.38453(12) 0.2806(2) 0.0470(8) Uani 1 1 d . . . O2 O 0.4415(3) 0.36874(12) 0.1215(2) 0.0438(8) Uani 1 1 d . . . O3 O -0.1404(4) 0.43131(15) -0.1359(3) 0.0696(10) Uani 1 1 d . . . N1 N 0.3030(3) 0.28605(14) 0.1921(2) 0.0354(8) Uani 1 1 d . . . C1 C 0.2171(5) 0.36809(19) 0.3548(3) 0.0432(11) Uani 1 1 d . . . C2 C 0.1672(5) 0.4090(2) 0.4329(4) 0.0550(13) Uani 1 1 d . . . H2 H 0.2024 0.4470 0.4353 0.066 Uiso 1 1 calc R . . C3 C 0.0658(6) 0.3931(3) 0.5064(4) 0.0687(17) Uani 1 1 d . . . H3 H 0.0326 0.4210 0.5574 0.082 Uiso 1 1 calc R . . C4 C 0.0125(6) 0.3373(2) 0.5066(4) 0.0578(14) Uani 1 1 d . . . C5 C 0.0628(5) 0.2961(2) 0.4309(3) 0.0516(13) Uani 1 1 d . . . H5 H 0.0273 0.2582 0.4300 0.062 Uiso 1 1 calc R . . C6 C 0.1671(5) 0.31081(19) 0.3551(3) 0.0444(12) Uani 1 1 d . . . C7 C 0.2278(4) 0.26625(18) 0.2808(3) 0.0385(11) Uani 1 1 d . . . C8 C 0.2152(5) 0.20660(19) 0.2983(3) 0.0458(12) Uani 1 1 d . . . H8 H 0.1617 0.1927 0.3575 0.055 Uiso 1 1 calc R . . C9 C 0.2823(6) 0.1672(2) 0.2279(4) 0.0595(15) Uani 1 1 d . . . H9 H 0.2744 0.1269 0.2401 0.071 Uiso 1 1 calc R . . C10 C 0.3594(5) 0.18782(19) 0.1414(3) 0.0461(12) Uani 1 1 d . . . H10 H 0.4051 0.1616 0.0946 0.055 Uiso 1 1 calc R . . C11 C 0.3703(5) 0.24815(18) 0.1223(3) 0.0394(11) Uani 1 1 d . . . C12 C 0.4558(5) 0.27363(19) 0.0324(3) 0.0405(11) Uani 1 1 d . . . C13 C 0.5140(5) 0.2391(2) -0.0531(3) 0.0455(12) Uani 1 1 d . . . H13 H 0.4903 0.1996 -0.0586 0.055 Uiso 1 1 calc R . . C14 C 0.6058(5) 0.2617(2) -0.1300(3) 0.0487(12) Uani 1 1 d . . . C15 C 0.6315(5) 0.3218(2) -0.1244(4) 0.0528(13) Uani 1 1 d . . . H15 H 0.6885 0.3386 -0.1780 0.063 Uiso 1 1 calc R . . C16 C 0.5752(5) 0.3569(2) -0.0425(4) 0.0488(12) Uani 1 1 d . . . H16 H 0.5953 0.3969 -0.0405 0.059 Uiso 1 1 calc R . . C17 C 0.4899(5) 0.33374(19) 0.0363(3) 0.0414(11) Uani 1 1 d . . . C18 C 0.1861(5) 0.37407(17) 0.0808(3) 0.0365(10) Uani 1 1 d . . . C19 C 0.0565(5) 0.35118(19) 0.0825(3) 0.0470(12) Uani 1 1 d . . . H19 H 0.0399 0.3209 0.1344 0.056 Uiso 1 1 calc R . . C20 C -0.0504(5) 0.3710(2) 0.0108(4) 0.0545(13) Uani 1 1 d . . . H20 H -0.1370 0.3547 0.0163 0.065 Uiso 1 1 calc R . . C21 C -0.0281(5) 0.4148(2) -0.0689(4) 0.0461(12) Uani 1 1 d . . . C22 C 0.0985(6) 0.43874(19) -0.0758(4) 0.0494(12) Uani 1 1 d . . . H22 H 0.1145 0.4685 -0.1292 0.059 Uiso 1 1 calc R . . C23 C 0.2029(5) 0.41829(18) -0.0023(3) 0.0456(12) Uani 1 1 d . . . H23 H 0.2892 0.4348 -0.0083 0.055 Uiso 1 1 calc R . . C24 C -0.1261(6) 0.4780(2) -0.2162(4) 0.0692(16) Uani 1 1 d . . . H24A H -0.0899 0.5119 -0.1760 0.104 Uiso 1 1 calc R . . H24B H -0.2137 0.4874 -0.2519 0.104 Uiso 1 1 calc R . . H24C H -0.0650 0.4663 -0.2753 0.104 Uiso 1 1 calc R . . C25 C -0.0978(6) 0.3204(3) 0.5868(4) 0.0830(19) Uani 1 1 d . . . H25A H -0.0700 0.3304 0.6655 0.124 Uiso 1 1 calc R . . H25B H -0.1140 0.2789 0.5814 0.124 Uiso 1 1 calc R . . H25C H -0.1801 0.3413 0.5649 0.124 Uiso 1 1 calc R . . C26 C 0.6774(6) 0.2226(2) -0.2148(4) 0.0651(15) Uani 1 1 d . . . H26A H 0.6805 0.2419 -0.2890 0.098 Uiso 1 1 calc R . . H26B H 0.6285 0.1862 -0.2237 0.098 Uiso 1 1 calc R . . H26C H 0.7687 0.2148 -0.1855 0.098 Uiso 1 1 calc R . . C27 C 0.3855(7) 0.5515(2) 0.6956(4) 0.0776(18) Uani 1 1 d . . . H27 H 0.4496 0.5797 0.7321 0.093 Uiso 1 1 calc R . . Cl1 Cl 0.2280(3) 0.56579(11) 0.7466(3) 0.1816(13) Uani 1 1 d . . . Cl2 Cl 0.3889(3) 0.56137(10) 0.54620(17) 0.1579(11) Uani 1 1 d . . . Cl3 Cl 0.4409(3) 0.48137(8) 0.7348(2) 0.1359(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.040(4) 0.036(3) 0.041(2) 0.001(2) 0.003(2) -0.008(3) O1 0.060(2) 0.0403(17) 0.0406(15) -0.0024(13) 0.0039(15) -0.0050(16) O2 0.044(2) 0.0376(16) 0.0494(16) -0.0043(14) 0.0028(14) -0.0051(15) O3 0.051(3) 0.073(2) 0.083(2) 0.0257(19) -0.0147(19) 0.004(2) N1 0.033(2) 0.0352(19) 0.0383(18) 0.0007(15) -0.0018(16) -0.0006(17) C1 0.047(3) 0.044(3) 0.038(2) 0.001(2) 0.001(2) -0.002(2) C2 0.068(4) 0.048(3) 0.049(2) 0.000(2) 0.006(2) 0.005(3) C3 0.089(5) 0.070(4) 0.048(3) -0.005(3) 0.020(3) 0.023(3) C4 0.056(4) 0.069(4) 0.049(3) 0.007(3) 0.012(2) 0.014(3) C5 0.049(4) 0.059(3) 0.047(2) 0.011(2) 0.006(2) -0.002(3) C6 0.055(3) 0.042(3) 0.036(2) 0.0041(19) -0.003(2) 0.005(2) C7 0.036(3) 0.043(3) 0.037(2) 0.0054(19) -0.0010(19) 0.000(2) C8 0.048(3) 0.045(3) 0.044(2) 0.009(2) 0.004(2) -0.004(2) C9 0.086(5) 0.034(3) 0.058(3) 0.005(2) 0.004(3) -0.006(3) C10 0.048(3) 0.041(3) 0.051(2) 0.000(2) 0.008(2) -0.002(2) C11 0.040(3) 0.042(3) 0.036(2) -0.003(2) -0.0065(19) -0.002(2) C12 0.036(3) 0.044(3) 0.041(2) 0.002(2) -0.0019(19) 0.001(2) C13 0.044(3) 0.046(3) 0.046(2) -0.006(2) -0.004(2) 0.003(2) C14 0.037(3) 0.067(3) 0.041(2) -0.003(2) -0.001(2) 0.002(3) C15 0.046(4) 0.069(3) 0.045(2) 0.004(2) 0.009(2) -0.012(3) C16 0.036(3) 0.053(3) 0.058(3) 0.005(2) 0.007(2) -0.003(3) C17 0.037(3) 0.046(3) 0.041(2) 0.002(2) -0.003(2) -0.005(2) C18 0.041(3) 0.031(2) 0.038(2) -0.0025(18) 0.0079(19) -0.002(2) C19 0.049(4) 0.045(3) 0.048(2) 0.010(2) 0.003(2) -0.010(3) C20 0.048(4) 0.055(3) 0.060(3) 0.011(2) -0.001(2) -0.004(3) C21 0.047(4) 0.042(3) 0.049(2) 0.002(2) -0.003(2) 0.010(2) C22 0.052(4) 0.038(3) 0.058(3) 0.010(2) 0.006(2) 0.002(3) C23 0.045(3) 0.039(2) 0.054(2) 0.008(2) 0.006(2) -0.002(2) C24 0.070(4) 0.072(4) 0.065(3) 0.019(3) -0.004(3) 0.018(3) C25 0.072(5) 0.098(4) 0.082(3) 0.004(3) 0.034(3) 0.014(4) C26 0.061(4) 0.080(4) 0.055(3) -0.011(3) 0.012(2) -0.005(3) C27 0.078(5) 0.062(4) 0.093(4) -0.010(3) 0.010(3) -0.024(3) Cl1 0.116(2) 0.1158(18) 0.321(3) 0.034(2) 0.099(2) -0.0162(15) Cl2 0.239(3) 0.1331(18) 0.1002(14) -0.0157(12) -0.0142(16) -0.0225(19) Cl3 0.134(2) 0.0779(12) 0.196(2) 0.0235(13) 0.0059(16) -0.0140(13) _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 O2 1.449(6) . ? B1 O1 1.461(5) . ? B1 C18 1.582(6) . ? B1 N1 1.610(6) . ? O1 C1 1.335(5) . ? O2 C17 1.361(5) . ? O3 C21 1.369(5) . ? O3 C24 1.416(5) . ? N1 C7 1.358(5) . ? N1 C11 1.365(5) . ? C1 C6 1.392(6) . ? C1 C2 1.394(6) . ? C2 C3 1.378(7) . ? C3 C4 1.373(7) . ? C4 C5 1.381(6) . ? C4 C25 1.497(7) . ? C5 C6 1.410(6) . ? C6 C7 1.465(6) . ? C7 C8 1.378(6) . ? C8 C9 1.390(6) . ? C9 C10 1.355(6) . ? C10 C11 1.394(6) . ? C11 C12 1.473(6) . ? C12 C13 1.396(6) . ? C12 C17 1.407(6) . ? C13 C14 1.384(6) . ? C14 C15 1.390(7) . ? C14 C26 1.512(6) . ? C15 C16 1.366(6) . ? C16 C17 1.361(6) . ? C18 C19 1.374(6) . ? C18 C23 1.400(5) . ? C19 C20 1.381(6) . ? C20 C21 1.376(6) . ? C21 C22 1.360(6) . ? C22 C23 1.380(6) . ? C27 Cl1 1.705(6) . ? C27 Cl2 1.730(5) . ? C27 Cl3 1.738(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 B1 O1 104.2(3) . . ? O2 B1 C18 113.1(3) . . ? O1 B1 C18 115.0(4) . . ? O2 B1 N1 107.8(4) . . ? O1 B1 N1 106.3(3) . . ? C18 B1 N1 109.9(3) . . ? C1 O1 B1 117.2(3) . . ? C17 O2 B1 118.8(3) . . ? C21 O3 C24 118.2(4) . . ? C7 N1 C11 121.4(3) . . ? C7 N1 B1 119.1(3) . . ? C11 N1 B1 119.5(3) . . ? O1 C1 C6 121.1(4) . . ? O1 C1 C2 119.5(4) . . ? C6 C1 C2 119.4(4) . . ? C3 C2 C1 119.9(5) . . ? C4 C3 C2 121.9(5) . . ? C3 C4 C5 118.7(5) . . ? C3 C4 C25 121.5(5) . . ? C5 C4 C25 119.9(5) . . ? C4 C5 C6 120.9(5) . . ? C1 C6 C5 119.2(4) . . ? C1 C6 C7 119.7(4) . . ? C5 C6 C7 121.1(4) . . ? N1 C7 C8 119.4(4) . . ? N1 C7 C6 116.9(4) . . ? C8 C7 C6 123.8(4) . . ? C7 C8 C9 120.2(4) . . ? C10 C9 C8 119.6(4) . . ? C9 C10 C11 120.3(4) . . ? N1 C11 C10 119.1(4) . . ? N1 C11 C12 117.7(4) . . ? C10 C11 C12 123.2(4) . . ? C13 C12 C17 117.7(4) . . ? C13 C12 C11 122.1(4) . . ? C17 C12 C11 120.1(4) . . ? C14 C13 C12 122.3(4) . . ? C13 C14 C15 117.1(4) . . ? C13 C14 C26 121.5(5) . . ? C15 C14 C26 121.3(4) . . ? C16 C15 C14 121.9(4) . . ? C17 C16 C15 120.4(4) . . ? O2 C17 C16 119.5(4) . . ? O2 C17 C12 120.1(4) . . ? C16 C17 C12 120.4(4) . . ? C19 C18 C23 114.6(4) . . ? C19 C18 B1 124.9(4) . . ? C23 C18 B1 120.5(4) . . ? C18 C19 C20 123.2(4) . . ? C21 C20 C19 119.6(5) . . ? C22 C21 O3 124.9(4) . . ? C22 C21 C20 119.9(4) . . ? O3 C21 C20 115.2(5) . . ? C21 C22 C23 119.1(4) . . ? C22 C23 C18 123.6(5) . . ? Cl1 C27 Cl2 111.7(4) . . ? Cl1 C27 Cl3 111.3(3) . . ? Cl2 C27 Cl3 111.0(3) . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.444 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.097