data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Hongyu Zhang.' 'Yan Fan.' 'Hongze Gao.' 'Zhong-Min Su.' 'Yue Wang.' 'Dandan Yao.' 'Zuolun Zhang.' 'Shanshan Zhao.' _publ_contact_author_name 'Hongyu Zhang' _publ_contact_author_email HONGYUZHANG@JLU.EDU.CN _publ_section_title ; Carbazolyl-contained phenol-pyridyl boron complexes: syntheses, structures, photoluminescent and electroluminescent properties ; # Attachment 'combined.CIF' data_1 _database_code_depnum_ccdc_archive 'CCDC 757234' #TrackingRef 'combined.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H23 B N2 O2' _chemical_formula_weight 514.36 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)/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 11.376(2) _cell_length_b 19.307(4) _cell_length_c 12.927(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.60(3) _cell_angle_gamma 90.00 _cell_volume 2640.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 14865 _cell_measurement_theta_min 2.995 _cell_measurement_theta_max 27.47 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9632 _exptl_absorpt_correction_T_max 0.9819 _exptl_absorpt_process_details ; Higash,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 'Omega scan' _diffrn_measurement_method 10.0 _diffrn_detector_area_resol_mean none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 25300 _diffrn_reflns_av_R_equivalents 0.0491 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.47 _reflns_number_total 6013 _reflns_number_gt 3551 _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^)+(0.0800P)^2^+0.0800P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6013 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0961 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1473 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _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 O2 O 0.66562(10) 0.16602(5) 0.58145(8) 0.0449(3) Uani 1 1 d . . . O1 O 0.66608(10) 0.04655(5) 0.58630(9) 0.0446(3) Uani 1 1 d . . . N1 N 0.87222(12) 0.10692(7) 0.63871(10) 0.0421(3) Uani 1 1 d . . . N2 N 0.76152(15) 0.11328(7) 1.10761(10) 0.0485(4) Uani 1 1 d . . . C7 C 0.92951(16) 0.04599(9) 0.63378(13) 0.0476(4) Uani 1 1 d . . . C11 C 0.93004(17) 0.16937(9) 0.64116(13) 0.0495(4) Uani 1 1 d . . . C18 C 0.74961(15) 0.10969(7) 0.77516(12) 0.0399(4) Uani 1 1 d . . . C1 C 0.72671(16) -0.01494(8) 0.59967(12) 0.0442(4) Uani 1 1 d . . . C17 C 0.72518(17) 0.22792(8) 0.60044(13) 0.0470(4) Uani 1 1 d . . . C2 C 0.65579(19) -0.07524(9) 0.58164(15) 0.0577(5) Uani 1 1 d . . . H2 H 0.5682 -0.0731 0.5585 0.069 Uiso 1 1 calc R . . C12 C 0.85680(18) 0.23214(9) 0.63804(14) 0.0513(4) Uani 1 1 d . . . C6 C 0.85782(17) -0.01761(8) 0.62783(13) 0.0475(4) Uani 1 1 d . . . B1 B 0.73416(17) 0.10704(9) 0.64571(14) 0.0390(4) Uani 1 1 d . . . C21 C 0.76012(16) 0.11221(8) 0.99640(12) 0.0433(4) Uani 1 1 d . . . C16 C 0.6529(2) 0.28799(10) 0.57719(17) 0.0662(5) Uani 1 1 d . . . H16 H 0.5652 0.2851 0.5484 0.079 Uiso 1 1 calc R . . C35 C 0.79356(16) 0.17059(9) 1.17755(13) 0.0461(4) Uani 1 1 d . . . C24 C 0.70186(17) 0.06498(9) 1.15192(13) 0.0505(4) Uani 1 1 d . . . C22 C 0.69118(18) 0.16077(8) 0.92122(14) 0.0518(4) Uani 1 1 d . . . H22 H 0.6471 0.1947 0.9430 0.062 Uiso 1 1 calc R . . C5 C 0.9157(2) -0.08270(10) 0.64504(17) 0.0652(5) Uani 1 1 d . . . H5 H 1.0030 -0.0856 0.6661 0.078 Uiso 1 1 calc R . . C13 C 0.9119(2) 0.29800(11) 0.65840(17) 0.0706(6) Uani 1 1 d . . . H13 H 0.9995 0.3017 0.6862 0.085 Uiso 1 1 calc R . . C8 C 1.05153(18) 0.04734(11) 0.63176(16) 0.0641(5) Uani 1 1 d . . . H8 H 1.0925 0.0062 0.6284 0.077 Uiso 1 1 calc R . . C3 C 0.7164(3) -0.13845(10) 0.59827(18) 0.0727(6) Uani 1 1 d . . . H3 H 0.6694 -0.1791 0.5871 0.087 Uiso 1 1 calc R . . C10 C 1.05066(19) 0.17041(11) 0.63868(17) 0.0663(5) Uani 1 1 d . . . H10 H 1.0911 0.2124 0.6397 0.080 Uiso 1 1 calc R . . C15 C 0.7110(3) 0.35162(11) 0.5967(2) 0.0815(7) Uani 1 1 d . . . H15 H 0.6620 0.3916 0.5814 0.098 Uiso 1 1 calc R . . C29 C 0.69972(18) 0.09058(10) 1.25281(14) 0.0537(5) Uani 1 1 d . . . C23 C 0.68708(17) 0.15943(8) 0.81285(14) 0.0498(4) Uani 1 1 d . . . H23 H 0.6406 0.1932 0.7634 0.060 Uiso 1 1 calc R . . C9 C 1.1102(2) 0.10942(12) 0.63471(19) 0.0735(6) Uani 1 1 d . . . H9 H 1.1916 0.1103 0.6340 0.088 Uiso 1 1 calc R . . C34 C 0.85055(17) 0.23220(9) 1.16627(15) 0.0562(5) Uani 1 1 d . . . H34 H 0.8728 0.2405 1.1050 0.067 Uiso 1 1 calc R . . C30 C 0.75906(17) 0.15758(10) 1.26951(13) 0.0531(5) Uani 1 1 d . . . C14 C 0.8408(3) 0.35701(12) 0.6387(2) 0.0845(7) Uani 1 1 d . . . H14 H 0.8795 0.4002 0.6534 0.101 Uiso 1 1 calc R . . C4 C 0.8471(2) -0.14177(11) 0.63161(19) 0.0766(6) Uani 1 1 d . . . H4 H 0.8876 -0.1845 0.6448 0.092 Uiso 1 1 calc R . . C19 C 0.8193(2) 0.06205(9) 0.85450(14) 0.0649(6) Uani 1 1 d . . . H19 H 0.8637 0.0279 0.8334 0.078 Uiso 1 1 calc R . . C31 C 0.7828(2) 0.20803(13) 1.35176(16) 0.0752(6) Uani 1 1 d . . . H31 H 0.7606 0.2003 1.4132 0.090 Uiso 1 1 calc R . . C20 C 0.8259(2) 0.06301(10) 0.96335(15) 0.0663(6) Uani 1 1 d . . . H20 H 0.8747 0.0304 1.0140 0.080 Uiso 1 1 calc R . . C28 C 0.6416(2) 0.05158(13) 1.31186(17) 0.0746(6) Uani 1 1 d . . . H28 H 0.6413 0.0674 1.3797 0.089 Uiso 1 1 calc R . . C25 C 0.6464(2) 0.00279(10) 1.10866(16) 0.0670(5) Uani 1 1 d . . . H25 H 0.6487 -0.0143 1.0421 0.080 Uiso 1 1 calc R . . C32 C 0.8387(2) 0.26871(14) 1.34158(18) 0.0831(7) Uani 1 1 d . . . H32 H 0.8543 0.3025 1.3963 0.100 Uiso 1 1 calc R . . C33 C 0.87282(19) 0.28071(11) 1.25009(18) 0.0713(6) Uani 1 1 d . . . H33 H 0.9115 0.3224 1.2452 0.086 Uiso 1 1 calc R . . C26 C 0.5870(2) -0.03338(11) 1.1684(2) 0.0840(7) Uani 1 1 d . . . H26 H 0.5468 -0.0749 1.1399 0.101 Uiso 1 1 calc R . . C27 C 0.5857(3) -0.00965(14) 1.2693(2) 0.0894(8) Uani 1 1 d . . . H27 H 0.5465 -0.0357 1.3079 0.107 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 O2 0.0479(7) 0.0496(6) 0.0381(6) 0.0064(5) 0.0170(5) 0.0024(5) O1 0.0417(6) 0.0486(6) 0.0430(6) -0.0045(5) 0.0148(5) 0.0014(5) N1 0.0421(8) 0.0563(8) 0.0290(6) -0.0024(6) 0.0143(6) 0.0005(6) N2 0.0685(10) 0.0505(8) 0.0330(7) -0.0008(6) 0.0262(7) 0.0019(7) C7 0.0430(10) 0.0657(11) 0.0335(8) -0.0031(8) 0.0133(7) 0.0061(8) C11 0.0483(10) 0.0633(11) 0.0354(8) -0.0019(8) 0.0136(7) -0.0095(8) C18 0.0476(9) 0.0407(8) 0.0355(8) -0.0010(7) 0.0201(7) 0.0013(7) C1 0.0536(10) 0.0489(9) 0.0315(8) -0.0033(7) 0.0172(7) 0.0039(8) C17 0.0629(11) 0.0480(9) 0.0352(8) 0.0023(7) 0.0241(8) -0.0008(8) C2 0.0644(12) 0.0541(11) 0.0582(11) -0.0049(9) 0.0267(10) -0.0031(9) C12 0.0612(11) 0.0570(10) 0.0376(9) -0.0017(8) 0.0204(8) -0.0084(9) C6 0.0543(10) 0.0545(10) 0.0368(8) -0.0010(7) 0.0204(8) 0.0097(8) B1 0.0407(10) 0.0454(9) 0.0331(9) -0.0005(8) 0.0163(7) 0.0013(8) C21 0.0590(10) 0.0427(8) 0.0331(8) 0.0003(7) 0.0228(7) 0.0034(7) C16 0.0824(15) 0.0572(11) 0.0715(13) 0.0096(10) 0.0429(12) 0.0071(10) C35 0.0472(10) 0.0559(10) 0.0354(8) -0.0040(7) 0.0154(7) 0.0113(8) C24 0.0618(11) 0.0531(10) 0.0381(9) 0.0140(8) 0.0202(8) 0.0134(8) C22 0.0685(12) 0.0516(10) 0.0457(9) 0.0045(8) 0.0332(9) 0.0178(8) C5 0.0685(13) 0.0649(12) 0.0647(13) 0.0019(10) 0.0275(10) 0.0172(10) C13 0.0817(15) 0.0670(13) 0.0634(13) -0.0072(10) 0.0270(11) -0.0222(11) C8 0.0481(11) 0.0871(14) 0.0585(12) -0.0046(10) 0.0212(9) 0.0101(10) C3 0.0998(18) 0.0507(11) 0.0750(14) -0.0059(10) 0.0408(13) -0.0049(11) C10 0.0492(12) 0.0829(14) 0.0669(13) -0.0022(11) 0.0214(10) -0.0135(10) C15 0.115(2) 0.0505(12) 0.0922(17) 0.0079(11) 0.0533(16) 0.0052(13) C29 0.0604(11) 0.0673(11) 0.0368(9) 0.0147(8) 0.0218(8) 0.0219(9) C23 0.0608(11) 0.0538(10) 0.0414(9) 0.0103(7) 0.0267(8) 0.0175(8) C9 0.0431(11) 0.1011(17) 0.0794(15) -0.0054(12) 0.0262(10) -0.0071(11) C34 0.0483(10) 0.0657(11) 0.0556(11) -0.0104(9) 0.0202(9) 0.0034(9) C30 0.0531(11) 0.0737(12) 0.0322(8) 0.0009(8) 0.0153(8) 0.0215(9) C14 0.120(2) 0.0549(12) 0.0855(16) -0.0089(11) 0.0464(16) -0.0189(14) C4 0.0958(18) 0.0567(12) 0.0839(15) 0.0045(11) 0.0406(14) 0.0206(12) C19 0.0962(16) 0.0634(11) 0.0415(10) 0.0063(9) 0.0329(10) 0.0376(11) C31 0.0843(16) 0.1019(17) 0.0365(10) -0.0137(11) 0.0188(10) 0.0245(14) C20 0.0996(16) 0.0637(11) 0.0400(9) 0.0118(9) 0.0309(10) 0.0380(11) C28 0.0846(16) 0.0975(16) 0.0539(12) 0.0329(12) 0.0399(11) 0.0286(13) C25 0.0938(16) 0.0514(10) 0.0547(11) 0.0136(9) 0.0262(11) 0.0038(10) C32 0.0823(16) 0.0972(18) 0.0568(13) -0.0357(13) 0.0103(11) 0.0154(13) C33 0.0556(12) 0.0711(13) 0.0751(14) -0.0263(11) 0.0097(10) 0.0007(10) C26 0.0995(19) 0.0645(13) 0.0861(17) 0.0335(12) 0.0318(14) 0.0002(12) C27 0.0992(19) 0.0904(17) 0.0922(18) 0.0497(15) 0.0514(15) 0.0163(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C17 1.3510(19) . ? O2 B1 1.455(2) . ? O1 C1 1.3518(18) . ? O1 B1 1.454(2) . ? N1 C7 1.358(2) . ? N1 C11 1.368(2) . ? N1 B1 1.606(2) . ? N2 C35 1.390(2) . ? N2 C24 1.395(2) . ? N2 C21 1.4320(18) . ? C7 C8 1.398(2) . ? C7 C6 1.460(2) . ? C11 C10 1.385(3) . ? C11 C12 1.463(3) . ? C18 C23 1.386(2) . ? C18 C19 1.388(2) . ? C18 B1 1.618(2) . ? C1 C2 1.386(2) . ? C1 C6 1.400(2) . ? C17 C16 1.389(2) . ? C17 C12 1.396(3) . ? C2 C3 1.379(3) . ? C12 C13 1.399(3) . ? C6 C5 1.398(2) . ? C21 C22 1.370(2) . ? C21 C20 1.371(2) . ? C16 C15 1.374(3) . ? C35 C34 1.388(3) . ? C35 C30 1.405(2) . ? C24 C25 1.376(3) . ? C24 C29 1.403(2) . ? C22 C23 1.385(2) . ? C5 C4 1.357(3) . ? C13 C14 1.366(3) . ? C8 C9 1.365(3) . ? C3 C4 1.389(3) . ? C10 C9 1.369(3) . ? C15 C14 1.377(4) . ? C29 C28 1.399(3) . ? C29 C30 1.438(3) . ? C34 C33 1.383(3) . ? C30 C31 1.393(3) . ? C19 C20 1.382(2) . ? C31 C32 1.363(3) . ? C28 C27 1.359(3) . ? C25 C26 1.388(3) . ? C32 C33 1.393(3) . ? C26 C27 1.388(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 C17 O2 B1 117.46(13) . . ? C1 O1 B1 119.36(13) . . ? C7 N1 C11 121.98(15) . . ? C7 N1 B1 120.01(13) . . ? C11 N1 B1 117.99(13) . . ? C35 N2 C24 108.41(13) . . ? C35 N2 C21 124.61(13) . . ? C24 N2 C21 125.13(14) . . ? N1 C7 C8 118.80(17) . . ? N1 C7 C6 117.56(15) . . ? C8 C7 C6 123.63(16) . . ? N1 C11 C10 118.97(17) . . ? N1 C11 C12 117.73(16) . . ? C10 C11 C12 123.15(17) . . ? C23 C18 C19 115.27(14) . . ? C23 C18 B1 120.74(14) . . ? C19 C18 B1 123.92(13) . . ? O1 C1 C2 118.56(16) . . ? O1 C1 C6 120.67(15) . . ? C2 C1 C6 120.74(16) . . ? O2 C17 C16 118.82(17) . . ? O2 C17 C12 121.11(15) . . ? C16 C17 C12 120.01(17) . . ? C3 C2 C1 119.4(2) . . ? C17 C12 C13 117.85(18) . . ? C17 C12 C11 119.23(15) . . ? C13 C12 C11 122.45(18) . . ? C5 C6 C1 117.96(17) . . ? C5 C6 C7 121.75(17) . . ? C1 C6 C7 120.24(14) . . ? O1 B1 O2 104.93(13) . . ? O1 B1 N1 108.10(12) . . ? O2 B1 N1 107.36(12) . . ? O1 B1 C18 113.93(13) . . ? O2 B1 C18 113.40(12) . . ? N1 B1 C18 108.80(13) . . ? C22 C21 C20 119.24(15) . . ? C22 C21 N2 119.61(14) . . ? C20 C21 N2 121.15(15) . . ? C15 C16 C17 120.0(2) . . ? C34 C35 N2 129.39(15) . . ? C34 C35 C30 121.94(16) . . ? N2 C35 C30 108.67(15) . . ? C25 C24 N2 129.51(16) . . ? C25 C24 C29 121.54(17) . . ? N2 C24 C29 108.90(15) . . ? C21 C22 C23 120.14(15) . . ? C4 C5 C6 121.3(2) . . ? C14 C13 C12 122.0(2) . . ? C9 C8 C7 119.62(19) . . ? C2 C3 C4 120.4(2) . . ? C9 C10 C11 119.79(19) . . ? C16 C15 C14 120.9(2) . . ? C28 C29 C24 119.39(19) . . ? C28 C29 C30 133.80(18) . . ? C24 C29 C30 106.76(15) . . ? C22 C23 C18 122.56(15) . . ? C8 C9 C10 120.8(2) . . ? C33 C34 C35 117.12(19) . . ? C31 C30 C35 119.0(2) . . ? C31 C30 C29 133.76(19) . . ? C35 C30 C29 107.20(15) . . ? C13 C14 C15 119.1(2) . . ? C5 C4 C3 120.1(2) . . ? C20 C19 C18 123.05(15) . . ? C32 C31 C30 119.6(2) . . ? C21 C20 C19 119.72(16) . . ? C27 C28 C29 119.5(2) . . ? C24 C25 C26 117.2(2) . . ? C31 C32 C33 120.72(19) . . ? C34 C33 C32 121.6(2) . . ? C25 C26 C27 122.2(2) . . ? C28 C27 C26 120.1(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2 O1 0.93 2.68 3.546(3) 154.7 3_656 C28 H28 O1 0.93 2.61 3.456(2) 151.3 1_556 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.255 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.079 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 757235' #TrackingRef 'combined.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H28 B Cl3 N2 O2' _chemical_formula_weight 661.78 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 10.324(2) _cell_length_b 29.638(6) _cell_length_c 11.364(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.61(3) _cell_angle_gamma 90.00 _cell_volume 3332.3(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 18042 _cell_measurement_theta_min 3.13 _cell_measurement_theta_max 27.415 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 0.312 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8657 _exptl_absorpt_correction_T_max 0.9155 _exptl_absorpt_process_details ; Higash,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 'Omega scan' _diffrn_measurement_method 10.0 _diffrn_detector_area_resol_mean none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 25586 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5764 _reflns_number_gt 3137 _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^)+(0.2300P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5764 _refine_ls_number_parameters 417 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1322 _refine_ls_R_factor_gt 0.0833 _refine_ls_wR_factor_ref 0.3101 _refine_ls_wR_factor_gt 0.2607 _refine_ls_goodness_of_fit_ref 0.939 _refine_ls_restrained_S_all 0.939 _refine_ls_shift/su_max 0.006 _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 N1 N 0.6514(3) 0.17679(10) 0.6135(3) 0.0505(7) Uani 1 1 d . . . O1 O 0.7620(3) 0.10758(9) 0.5682(2) 0.0618(7) Uani 1 1 d . . . O2 O 0.8299(2) 0.17528(9) 0.5057(2) 0.0621(7) Uani 1 1 d . . . C7 C 0.5809(3) 0.15249(13) 0.6756(3) 0.0548(9) Uani 1 1 d . . . C11 C 0.6642(3) 0.22229(12) 0.6262(3) 0.0505(9) Uani 1 1 d . . . C12 C 0.7436(3) 0.24611(13) 0.5573(3) 0.0550(9) Uani 1 1 d . . . C17 C 0.8251(4) 0.22055(15) 0.5006(3) 0.0611(10) Uani 1 1 d . . . C6 C 0.5813(4) 0.10315(13) 0.6609(4) 0.0589(10) Uani 1 1 d . . . C18 C 0.5951(3) 0.14668(11) 0.3864(3) 0.0468(8) Uani 1 1 d . . . C8 C 0.5183(4) 0.17426(15) 0.7513(4) 0.0667(11) Uani 1 1 d . . . H8 H 0.4689 0.1580 0.7935 0.080 Uiso 1 1 calc R . . N2 N 0.3066(3) 0.13252(11) 0.0379(3) 0.0641(9) Uani 1 1 d . . . C21 C 0.4033(4) 0.13684(12) 0.1554(3) 0.0542(9) Uani 1 1 d . . . C1 C 0.6763(4) 0.08247(14) 0.6106(4) 0.0619(10) Uani 1 1 d . . . C10 C 0.6040(4) 0.24404(14) 0.7051(3) 0.0628(10) Uani 1 1 d . . . H10 H 0.6150 0.2750 0.7175 0.075 Uiso 1 1 calc R . . C5 C 0.4932(4) 0.07482(14) 0.7022(4) 0.0730(12) Uani 1 1 d . . . H5 H 0.4287 0.0882 0.7337 0.088 Uiso 1 1 calc R . . C35 C 0.2628(4) 0.16675(15) -0.0468(3) 0.0634(10) Uani 1 1 d . . . C30 C 0.1707(4) 0.14928(19) -0.1536(4) 0.0744(13) Uani 1 1 d . . . C23 C 0.6252(4) 0.12579(13) 0.2894(4) 0.0588(10) Uani 1 1 d . . . H23 H 0.7121 0.1145 0.3011 0.071 Uiso 1 1 calc R . . C19 C 0.4645(4) 0.16343(16) 0.3625(4) 0.0739(12) Uani 1 1 d . . . H19 H 0.4400 0.1785 0.4246 0.089 Uiso 1 1 calc R . . C22 C 0.5331(4) 0.12081(14) 0.1761(4) 0.0643(11) Uani 1 1 d . . . H22 H 0.5584 0.1066 0.1131 0.077 Uiso 1 1 calc R . . C29 C 0.1563(4) 0.10266(19) -0.1306(4) 0.0782(13) Uani 1 1 d . . . B1 B 0.7111(4) 0.15075(14) 0.5164(4) 0.0509(10) Uani 1 1 d . . . C24 C 0.2414(4) 0.09299(16) -0.0124(4) 0.0718(12) Uani 1 1 d . . . C34 C 0.2928(4) 0.21218(18) -0.0347(4) 0.0780(13) Uani 1 1 d . . . H34 H 0.3520 0.2236 0.0369 0.094 Uiso 1 1 calc R . . C13 C 0.7453(5) 0.29250(16) 0.5495(4) 0.0722(12) Uani 1 1 d . . . H13 H 0.6904 0.3089 0.5860 0.087 Uiso 1 1 calc R . . C20 C 0.3696(4) 0.15846(17) 0.2493(4) 0.0768(13) Uani 1 1 d . . . H20 H 0.2827 0.1698 0.2369 0.092 Uiso 1 1 calc R . . C2 C 0.6843(5) 0.03584(16) 0.6085(5) 0.0841(14) Uani 1 1 d . . . H2 H 0.7487 0.0219 0.5780 0.101 Uiso 1 1 calc R . . C15 C 0.9055(5) 0.2896(2) 0.4372(5) 0.0967(18) Uani 1 1 d . . . H15 H 0.9622 0.3038 0.3983 0.116 Uiso 1 1 calc R . . C31 C 0.1155(5) 0.1783(3) -0.2509(4) 0.0989(19) Uani 1 1 d . . . H31 H 0.0578 0.1672 -0.3237 0.119 Uiso 1 1 calc R . . C16 C 0.9055(4) 0.24320(18) 0.4400(5) 0.0795(13) Uani 1 1 d . . . H16 H 0.9591 0.2270 0.4016 0.095 Uiso 1 1 calc R . . C4 C 0.4976(6) 0.02955(18) 0.6982(5) 0.0909(15) Uani 1 1 d . . . C9 C 0.5296(5) 0.22034(15) 0.7639(4) 0.0700(11) Uani 1 1 d . . . H9 H 0.4855 0.2353 0.8133 0.084 Uiso 1 1 calc R . . C3 C 0.5963(6) 0.01005(17) 0.6519(5) 0.0928(16) Uani 1 1 d . . . H3 H 0.6029 -0.0212 0.6502 0.111 Uiso 1 1 calc R . . C14 C 0.8255(6) 0.31650(17) 0.4891(5) 0.0867(15) Uani 1 1 d . . . C32 C 0.1464(6) 0.2234(3) -0.2393(5) 0.110(2) Uani 1 1 d . . . H32 H 0.1089 0.2428 -0.3044 0.132 Uiso 1 1 calc R . . C25 C 0.2480(6) 0.05066(17) 0.0399(6) 0.0984(17) Uani 1 1 d . . . H25 H 0.3052 0.0448 0.1178 0.118 Uiso 1 1 calc R . . C33 C 0.2323(5) 0.2404(2) -0.1322(6) 0.0991(17) Uani 1 1 d . . . H33 H 0.2499 0.2712 -0.1253 0.119 Uiso 1 1 calc R . . C28 C 0.0725(6) 0.0694(3) -0.1970(6) 0.112(2) Uani 1 1 d . . . H28 H 0.0138 0.0753 -0.2743 0.135 Uiso 1 1 calc R . . C37 C 0.8203(7) 0.36676(17) 0.4780(6) 0.114(2) Uani 1 1 d . . . H37A H 0.7754 0.3790 0.5341 0.171 Uiso 1 1 calc R . . H37B H 0.7716 0.3751 0.3956 0.171 Uiso 1 1 calc R . . H37C H 0.9106 0.3785 0.4973 0.171 Uiso 1 1 calc R . . C27 C 0.0793(8) 0.0277(3) -0.1449(8) 0.146(3) Uani 1 1 d . . . H27 H 0.0236 0.0051 -0.1890 0.175 Uiso 1 1 calc R . . C26 C 0.1652(9) 0.0169(3) -0.0289(8) 0.144(3) Uani 1 1 d . . . H26 H 0.1674 -0.0122 0.0021 0.173 Uiso 1 1 calc R . . C36 C 0.3998(7) -0.0006(2) 0.7403(8) 0.139(3) Uani 1 1 d . . . H36A H 0.4220 0.0001 0.8283 0.208 Uiso 1 1 calc R . . H36B H 0.4068 -0.0310 0.7133 0.208 Uiso 1 1 calc R . . H36C H 0.3091 0.0102 0.7057 0.208 Uiso 1 1 calc R . . Cl1 Cl 0.0103(3) 0.13005(15) 0.2843(2) 0.2348(18) Uani 1 1 d . . . Cl2 Cl 0.2045(2) 0.11162(15) 0.5050(2) 0.2382(18) Uani 1 1 d . . . Cl3 Cl -0.0134(4) 0.05096(10) 0.4120(5) 0.269(2) Uani 1 1 d . . . C38 C 0.0391(6) 0.1056(2) 0.4238(6) 0.1075(19) Uani 1 1 d . . . H38 H -0.0147 0.1220 0.4683 0.129 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 N1 0.0404(15) 0.0691(19) 0.0341(15) -0.0003(13) -0.0020(12) 0.0060(13) O1 0.0524(15) 0.0763(17) 0.0506(16) 0.0048(12) 0.0050(12) 0.0177(12) O2 0.0379(13) 0.089(2) 0.0548(16) -0.0096(13) 0.0052(11) -0.0035(12) C7 0.0449(19) 0.074(2) 0.0396(19) 0.0085(16) 0.0029(16) 0.0052(16) C11 0.0448(18) 0.062(2) 0.0355(18) -0.0021(15) -0.0034(15) 0.0031(15) C12 0.0472(19) 0.069(2) 0.0395(19) -0.0021(16) -0.0024(16) -0.0083(16) C17 0.0415(19) 0.084(3) 0.049(2) -0.0029(19) -0.0009(16) -0.0102(18) C6 0.051(2) 0.066(2) 0.050(2) 0.0072(17) -0.0019(17) 0.0058(17) C18 0.0402(17) 0.059(2) 0.0369(18) 0.0018(14) 0.0033(14) 0.0015(14) C8 0.066(2) 0.088(3) 0.048(2) 0.0074(19) 0.0204(19) 0.007(2) N2 0.0568(18) 0.082(2) 0.0406(17) -0.0087(15) -0.0074(14) -0.0041(16) C21 0.049(2) 0.063(2) 0.043(2) -0.0029(16) 0.0007(16) -0.0031(16) C1 0.056(2) 0.072(3) 0.047(2) 0.0101(18) -0.0017(18) 0.0102(19) C10 0.063(2) 0.073(2) 0.045(2) -0.0014(18) 0.0053(19) 0.0064(19) C5 0.066(3) 0.073(3) 0.072(3) 0.016(2) 0.006(2) -0.001(2) C35 0.045(2) 0.098(3) 0.040(2) -0.0011(19) 0.0010(16) 0.0005(19) C30 0.045(2) 0.136(4) 0.038(2) -0.014(2) 0.0042(17) 0.009(2) C23 0.0450(19) 0.075(2) 0.052(2) -0.0091(18) 0.0058(17) 0.0133(16) C19 0.053(2) 0.119(3) 0.043(2) -0.018(2) 0.0019(17) 0.024(2) C22 0.057(2) 0.088(3) 0.042(2) -0.0152(18) 0.0049(17) 0.0084(19) C29 0.055(2) 0.121(4) 0.049(2) -0.029(2) 0.0009(19) -0.001(2) B1 0.042(2) 0.071(3) 0.036(2) 0.0003(18) 0.0059(16) 0.0047(18) C24 0.057(2) 0.090(3) 0.061(3) -0.026(2) 0.005(2) -0.011(2) C34 0.055(2) 0.110(4) 0.059(3) 0.015(2) 0.001(2) -0.006(2) C13 0.074(3) 0.085(3) 0.050(2) -0.005(2) 0.006(2) -0.012(2) C20 0.045(2) 0.129(4) 0.046(2) -0.018(2) -0.0022(17) 0.020(2) C2 0.094(3) 0.073(3) 0.073(3) 0.003(2) 0.004(3) 0.016(3) C15 0.077(3) 0.130(5) 0.074(3) 0.011(3) 0.006(3) -0.047(3) C31 0.061(3) 0.185(6) 0.041(3) 0.002(3) -0.002(2) 0.012(3) C16 0.053(2) 0.107(4) 0.078(3) -0.004(3) 0.018(2) -0.023(2) C4 0.088(3) 0.082(3) 0.091(4) 0.024(3) 0.006(3) -0.015(3) C9 0.077(3) 0.081(3) 0.053(2) 0.000(2) 0.021(2) 0.017(2) C3 0.101(4) 0.064(3) 0.092(4) 0.019(3) -0.006(3) -0.007(3) C14 0.090(4) 0.087(3) 0.068(3) 0.001(2) 0.000(3) -0.030(3) C32 0.074(3) 0.175(6) 0.070(4) 0.046(4) 0.003(3) 0.019(4) C25 0.096(4) 0.082(3) 0.105(4) -0.023(3) 0.008(3) -0.013(3) C33 0.062(3) 0.131(4) 0.093(4) 0.043(3) 0.004(3) 0.003(3) C28 0.088(4) 0.142(6) 0.088(4) -0.051(4) -0.004(3) -0.011(4) C37 0.141(5) 0.080(3) 0.102(4) 0.008(3) 0.003(4) -0.045(3) C27 0.120(6) 0.169(8) 0.124(6) -0.076(6) -0.006(5) -0.035(5) C26 0.149(7) 0.120(5) 0.161(8) -0.052(5) 0.041(6) -0.046(5) C36 0.126(5) 0.113(5) 0.165(7) 0.041(4) 0.022(5) -0.038(4) Cl1 0.1202(18) 0.472(6) 0.1026(17) 0.056(2) 0.0160(13) 0.011(2) Cl2 0.0836(13) 0.499(6) 0.1106(18) -0.021(2) -0.0069(11) -0.002(2) Cl3 0.278(4) 0.150(2) 0.450(7) -0.110(3) 0.217(4) -0.028(2) C38 0.092(4) 0.138(5) 0.087(4) -0.025(3) 0.018(3) 0.027(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C7 1.356(5) . ? N1 C11 1.359(5) . ? N1 B1 1.607(5) . ? O1 C1 1.346(5) . ? O1 B1 1.443(5) . ? O2 C17 1.343(5) . ? O2 B1 1.460(5) . ? C7 C8 1.375(6) . ? C7 C6 1.472(5) . ? C11 C10 1.387(5) . ? C11 C12 1.466(5) . ? C12 C13 1.378(6) . ? C12 C17 1.417(6) . ? C17 C16 1.394(6) . ? C6 C1 1.409(6) . ? C6 C5 1.413(6) . ? C18 C23 1.375(5) . ? C18 C19 1.389(5) . ? C18 B1 1.619(5) . ? C8 C9 1.375(6) . ? N2 C35 1.382(5) . ? N2 C24 1.390(5) . ? N2 C21 1.426(5) . ? C21 C20 1.372(6) . ? C21 C22 1.378(5) . ? C1 C2 1.385(6) . ? C10 C9 1.350(6) . ? C5 C4 1.343(7) . ? C35 C34 1.380(6) . ? C35 C30 1.410(5) . ? C30 C31 1.388(7) . ? C30 C29 1.422(7) . ? C23 C22 1.373(5) . ? C19 C20 1.384(5) . ? C29 C28 1.384(7) . ? C29 C24 1.408(6) . ? C24 C25 1.382(7) . ? C34 C33 1.386(7) . ? C13 C14 1.409(7) . ? C2 C3 1.381(8) . ? C15 C16 1.375(7) . ? C15 C14 1.395(8) . ? C31 C32 1.371(9) . ? C4 C3 1.399(8) . ? C4 C36 1.523(8) . ? C14 C37 1.495(7) . ? C32 C33 1.380(8) . ? C25 C26 1.400(8) . ? C28 C27 1.365(11) . ? C27 C26 1.400(12) . ? Cl1 C38 1.691(7) . ? Cl2 C38 1.702(6) . ? Cl3 C38 1.701(7) . ? 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 C7 N1 C11 121.5(3) . . ? C7 N1 B1 118.1(3) . . ? C11 N1 B1 120.3(3) . . ? C1 O1 B1 115.9(3) . . ? C17 O2 B1 118.6(3) . . ? N1 C7 C8 119.6(4) . . ? N1 C7 C6 116.7(3) . . ? C8 C7 C6 123.6(4) . . ? N1 C11 C10 118.8(3) . . ? N1 C11 C12 118.3(3) . . ? C10 C11 C12 122.9(3) . . ? C13 C12 C17 118.9(4) . . ? C13 C12 C11 122.3(4) . . ? C17 C12 C11 118.7(3) . . ? O2 C17 C16 118.8(4) . . ? O2 C17 C12 122.3(3) . . ? C16 C17 C12 118.9(4) . . ? C1 C6 C5 117.7(4) . . ? C1 C6 C7 120.2(4) . . ? C5 C6 C7 122.0(4) . . ? C23 C18 C19 115.7(3) . . ? C23 C18 B1 119.2(3) . . ? C19 C18 B1 125.1(3) . . ? C9 C8 C7 119.4(4) . . ? C35 N2 C24 108.0(3) . . ? C35 N2 C21 126.0(3) . . ? C24 N2 C21 126.0(3) . . ? C20 C21 C22 118.7(3) . . ? C20 C21 N2 120.3(3) . . ? C22 C21 N2 121.0(3) . . ? O1 C1 C2 119.8(4) . . ? O1 C1 C6 120.6(4) . . ? C2 C1 C6 119.5(4) . . ? C9 C10 C11 120.1(4) . . ? C4 C5 C6 123.5(5) . . ? C34 C35 N2 128.8(4) . . ? C34 C35 C30 121.4(4) . . ? N2 C35 C30 109.6(4) . . ? C31 C30 C35 118.7(5) . . ? C31 C30 C29 135.1(5) . . ? C35 C30 C29 106.2(4) . . ? C22 C23 C18 123.1(3) . . ? C20 C19 C18 122.3(4) . . ? C23 C22 C21 120.1(3) . . ? C28 C29 C24 119.8(6) . . ? C28 C29 C30 132.3(5) . . ? C24 C29 C30 107.7(4) . . ? O1 B1 O2 105.0(3) . . ? O1 B1 N1 108.1(3) . . ? O2 B1 N1 108.3(3) . . ? O1 B1 C18 113.2(3) . . ? O2 B1 C18 112.4(3) . . ? N1 B1 C18 109.5(3) . . ? C25 C24 N2 129.0(4) . . ? C25 C24 C29 122.4(4) . . ? N2 C24 C29 108.5(4) . . ? C35 C34 C33 118.1(5) . . ? C12 C13 C14 123.7(5) . . ? C21 C20 C19 120.2(4) . . ? C3 C2 C1 119.9(5) . . ? C16 C15 C14 123.9(5) . . ? C32 C31 C30 119.7(5) . . ? C15 C16 C17 119.8(5) . . ? C5 C4 C3 117.4(5) . . ? C5 C4 C36 122.9(6) . . ? C3 C4 C36 119.7(5) . . ? C10 C9 C8 120.5(4) . . ? C2 C3 C4 122.0(5) . . ? C15 C14 C13 114.7(5) . . ? C15 C14 C37 123.1(5) . . ? C13 C14 C37 122.2(6) . . ? C31 C32 C33 120.9(5) . . ? C24 C25 C26 117.5(7) . . ? C32 C33 C34 121.0(6) . . ? C27 C28 C29 117.6(6) . . ? C28 C27 C26 123.7(6) . . ? C27 C26 C25 119.0(8) . . ? Cl1 C38 Cl3 111.5(4) . . ? Cl1 C38 Cl2 110.1(4) . . ? Cl3 C38 Cl2 113.0(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C31 H31 O2 0.93 2.60 3.420(5) 147.6 1_454 C38 H38 O2 0.98 2.37 3.308(6) 159.0 1_455 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.528 _refine_diff_density_min -0.599 _refine_diff_density_rms 0.055 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 757236' #TrackingRef 'combined.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H44 B Cl3 N2 O2' _chemical_formula_weight 822.03 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 32.791(7) _cell_length_b 11.692(2) _cell_length_c 11.615(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.69(3) _cell_angle_gamma 90.00 _cell_volume 4452.8(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 18561 _cell_measurement_theta_min 3.025 _cell_measurement_theta_max 27.495 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1720 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8973 _exptl_absorpt_correction_T_max 0.9708 _exptl_absorpt_process_details ; Higash,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 'Omega scan' _diffrn_measurement_method 10.0 _diffrn_detector_area_resol_mean none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 32755 _diffrn_reflns_av_R_equivalents 0.0994 _diffrn_reflns_av_sigmaI/netI 0.0814 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7586 _reflns_number_gt 3148 _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^)+(0.1500P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7586 _refine_ls_number_parameters 529 _refine_ls_number_restraints 52 _refine_ls_R_factor_all 0.2090 _refine_ls_R_factor_gt 0.1057 _refine_ls_wR_factor_ref 0.3160 _refine_ls_wR_factor_gt 0.2585 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.133 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.1353(2) 1.0637(5) 1.2418(6) 0.0601(17) Uani 1 1 d . . . C1 C 0.08070(17) 1.1023(6) 1.1108(5) 0.0676(17) Uani 1 1 d . . . C2 C 0.0548(2) 1.0482(8) 1.0308(7) 0.093(2) Uani 1 1 d . . . H2 H 0.0468 0.9727 1.0407 0.112 Uiso 1 1 calc R . . C3 C 0.0419(2) 1.1106(10) 0.9373(7) 0.103(3) Uani 1 1 d . . . H3 H 0.0241 1.0771 0.8842 0.124 Uiso 1 1 calc R . . C4 C 0.0541(2) 1.2185(10) 0.9204(6) 0.100(3) Uani 1 1 d . . . H4 H 0.0455 1.2567 0.8543 0.120 Uiso 1 1 calc R . . C5 C 0.0786(2) 1.2733(7) 0.9966(6) 0.081(2) Uani 1 1 d . . . H5 H 0.0857 1.3493 0.9845 0.098 Uiso 1 1 calc R . . C6 C 0.09339(17) 1.2141(6) 1.0951(5) 0.0677(17) Uani 1 1 d . . . C7 C 0.11972(17) 1.2692(5) 1.1804(5) 0.0610(15) Uani 1 1 d . . . C8 C 0.1220(2) 1.3846(5) 1.1920(5) 0.0741(17) Uani 1 1 d . . . H8 H 0.1069 1.4324 1.1438 0.089 Uiso 1 1 calc R . . C9 C 0.1472(3) 1.4296(6) 1.2761(6) 0.096(2) Uani 1 1 d . . . H9 H 0.1500 1.5085 1.2826 0.115 Uiso 1 1 calc R . . C10 C 0.1684(2) 1.3593(6) 1.3509(6) 0.0780(18) Uani 1 1 d . . . H10 H 0.1849 1.3897 1.4088 0.094 Uiso 1 1 calc R . . C11 C 0.16439(18) 1.2429(5) 1.3376(5) 0.0628(16) Uani 1 1 d . . . C12 C 0.1861(2) 1.1600(6) 1.4128(5) 0.0748(18) Uani 1 1 d . . . C13 C 0.2199(2) 1.1906(8) 1.4801(6) 0.095(2) Uani 1 1 d . . . H13 H 0.2304 1.2643 1.4751 0.114 Uiso 1 1 calc R . . C14 C 0.2377(3) 1.1130(12) 1.5536(8) 0.122(3) Uani 1 1 d . . . H14 H 0.2604 1.1336 1.5979 0.146 Uiso 1 1 calc R . . C15 C 0.2221(4) 1.0064(11) 1.5610(8) 0.128(4) Uani 1 1 d . . . H15 H 0.2338 0.9540 1.6117 0.153 Uiso 1 1 calc R . . C16 C 0.1896(3) 0.9747(8) 1.4959(7) 0.106(3) Uani 1 1 d . . . H16 H 0.1795 0.9007 1.5027 0.128 Uiso 1 1 calc R . . C17 C 0.1710(2) 1.0492(6) 1.4197(5) 0.0716(17) Uani 1 1 d . . . C18 C 0.16763(15) 1.0139(4) 1.1530(4) 0.0523(13) Uani 1 1 d . . . C19 C 0.20773(16) 1.0560(5) 1.1403(4) 0.0554(14) Uani 1 1 d . . . H19 H 0.2162 1.1192 1.1830 0.066 Uiso 1 1 calc R . . C20 C 0.23485(15) 1.0044(4) 1.0650(4) 0.0502(13) Uani 1 1 d . . . H20 H 0.2611 1.0337 1.0590 0.060 Uiso 1 1 calc R . . C21 C 0.22387(15) 0.9115(4) 0.9994(4) 0.0504(13) Uani 1 1 d . . . C22 C 0.18430(18) 0.8701(5) 1.0129(5) 0.0643(16) Uani 1 1 d . . . H22 H 0.1759 0.8064 0.9710 0.077 Uiso 1 1 calc R . . C23 C 0.15739(18) 0.9213(5) 1.0867(5) 0.0649(16) Uani 1 1 d . . . H23 H 0.1311 0.8917 1.0917 0.078 Uiso 1 1 calc R . . C24 C 0.25234(16) 0.8534(5) 0.9194(4) 0.0546(14) Uani 1 1 d . . . C25 C 0.29428(18) 0.8634(5) 0.9335(5) 0.0662(16) Uani 1 1 d . . . H25 H 0.3046 0.9128 0.9895 0.079 Uiso 1 1 calc R . . C26 C 0.32069(17) 0.8028(5) 0.8678(5) 0.0683(16) Uani 1 1 d . . . H26 H 0.3486 0.8107 0.8798 0.082 Uiso 1 1 calc R . . C27 C 0.30629(17) 0.7300(5) 0.7839(5) 0.0582(14) Uani 1 1 d . . . C28 C 0.26485(19) 0.7256(5) 0.7641(6) 0.0777(19) Uani 1 1 d . . . H28 H 0.2548 0.6821 0.7030 0.093 Uiso 1 1 calc R . . C29 C 0.23805(19) 0.7836(6) 0.8323(5) 0.0754(18) Uani 1 1 d . . . H29 H 0.2101 0.7758 0.8197 0.091 Uiso 1 1 calc R . . C30 C 0.36452(17) 0.6964(5) 0.6507(5) 0.0625(15) Uani 1 1 d . . . C31 C 0.3731(2) 0.8050(5) 0.6126(6) 0.0799(19) Uani 1 1 d . . . H31 H 0.3573 0.8674 0.6342 0.096 Uiso 1 1 calc R . . C32 C 0.4067(2) 0.8178(5) 0.5392(6) 0.0793(19) Uani 1 1 d . . . H32 H 0.4132 0.8904 0.5125 0.095 Uiso 1 1 calc R . . C33 C 0.43046(17) 0.7257(5) 0.5053(5) 0.0625(15) Uani 1 1 d . . . C34 C 0.42101(16) 0.6182(5) 0.5459(5) 0.0616(15) Uani 1 1 d . . . H34 H 0.4370 0.5561 0.5251 0.074 Uiso 1 1 calc R . . C35 C 0.38786(16) 0.6011(5) 0.6175(4) 0.0559(14) Uani 1 1 d . . . C36 C 0.37026(16) 0.5018(5) 0.6724(4) 0.0577(14) Uani 1 1 d . . . C37 C 0.37983(16) 0.3868(5) 0.6761(5) 0.0594(14) Uani 1 1 d . . . H37 H 0.4019 0.3593 0.6348 0.071 Uiso 1 1 calc R . . C38 C 0.35687(18) 0.3127(5) 0.7409(5) 0.0661(15) Uani 1 1 d . . . C39 C 0.32431(19) 0.3563(6) 0.8022(5) 0.0731(17) Uani 1 1 d . . . H39 H 0.3089 0.3060 0.8458 0.088 Uiso 1 1 calc R . . C40 C 0.31384(18) 0.4685(5) 0.8018(5) 0.0696(17) Uani 1 1 d . . . H40 H 0.2918 0.4942 0.8444 0.083 Uiso 1 1 calc R . . C41 C 0.33648(16) 0.5441(5) 0.7370(5) 0.0610(15) Uani 1 1 d . . . C42 C 0.4680(2) 0.7448(8) 0.4323(7) 0.109(2) Uani 1 1 d U . . C43 C 0.4657(3) 0.8419(10) 0.3559(9) 0.145(3) Uani 1 1 d U . . H43A H 0.4604 0.9098 0.3997 0.218 Uiso 1 1 calc R . . H43B H 0.4441 0.8304 0.3006 0.218 Uiso 1 1 calc R . . H43C H 0.4911 0.8502 0.3165 0.218 Uiso 1 1 calc R . . C44 C 0.5046(3) 0.7495(11) 0.5052(9) 0.154(3) Uani 1 1 d U . . H44A H 0.5021 0.6959 0.5674 0.232 Uiso 1 1 calc R . . H44B H 0.5078 0.8252 0.5359 0.232 Uiso 1 1 calc R . . H44C H 0.5281 0.7303 0.4603 0.232 Uiso 1 1 calc R . . C45 C 0.4772(3) 0.6390(10) 0.3547(10) 0.164(3) Uani 1 1 d U . . H45A H 0.4585 0.6378 0.2906 0.246 Uiso 1 1 calc R . . H45B H 0.4743 0.5702 0.3989 0.246 Uiso 1 1 calc R . . H45C H 0.5046 0.6441 0.3270 0.246 Uiso 1 1 calc R . . C46 C 0.3689(3) 0.1855(7) 0.7488(9) 0.119(2) Uani 1 1 d U . . C47 C 0.3402(3) 0.1171(8) 0.8152(10) 0.163(3) Uani 1 1 d U . . H47A H 0.3389 0.0412 0.7838 0.244 Uiso 1 1 calc R . . H47B H 0.3137 0.1516 0.8115 0.244 Uiso 1 1 calc R . . H47C H 0.3494 0.1134 0.8940 0.244 Uiso 1 1 calc R . . C48 C 0.4111(3) 0.1779(9) 0.7956(11) 0.166(3) Uani 1 1 d U . . H48A H 0.4113 0.1996 0.8753 0.248 Uiso 1 1 calc R . . H48B H 0.4285 0.2283 0.7533 0.248 Uiso 1 1 calc R . . H48C H 0.4208 0.1007 0.7885 0.248 Uiso 1 1 calc RD . . C49 C 0.3739(4) 0.1386(7) 0.6290(9) 0.156(3) Uani 1 1 d U . . H49A H 0.3611 0.0649 0.6237 0.234 Uiso 1 1 calc R . . H49B H 0.4024 0.1314 0.6127 0.234 Uiso 1 1 calc RD . . H49C H 0.3614 0.1897 0.5744 0.234 Uiso 1 1 calc R . . C50 C 0.0612(3) 0.8415(11) 0.3803(8) 0.147(4) Uani 1 1 d D . . H50 H 0.0765 0.9067 0.3501 0.177 Uiso 1 1 calc R . . Cl1 Cl 0.01471(15) 0.8581(12) 0.3469(5) 0.519(9) Uani 1 1 d D . . Cl2 Cl 0.07018(13) 0.8329(4) 0.5235(2) 0.1880(16) Uani 1 1 d D . . Cl3 Cl 0.0782(5) 0.7241(6) 0.3183(5) 0.515(9) Uani 1 1 d D . . N1 N 0.14034(14) 1.2014(4) 1.2547(4) 0.0558(12) Uani 1 1 d . . . N2 N 0.33327(14) 0.6600(4) 0.7219(4) 0.0658(13) Uani 1 1 d . . . O1 O 0.09336(12) 1.0427(4) 1.2050(4) 0.0699(11) Uani 1 1 d . . . O2 O 0.13866(14) 1.0155(3) 1.3561(3) 0.0742(12) 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 0.078(5) 0.039(4) 0.064(4) 0.002(3) 0.016(3) 0.005(3) C1 0.052(3) 0.077(5) 0.075(4) -0.008(4) 0.026(3) -0.004(3) C2 0.061(4) 0.119(7) 0.100(5) -0.025(5) 0.020(4) -0.023(4) C3 0.075(5) 0.141(9) 0.093(6) -0.014(6) 0.004(4) -0.027(5) C4 0.055(4) 0.168(9) 0.077(5) 0.008(5) 0.001(4) -0.007(5) C5 0.071(4) 0.093(5) 0.080(4) 0.004(4) 0.019(4) 0.002(4) C6 0.062(3) 0.076(5) 0.066(4) 0.000(3) 0.022(3) 0.002(3) C7 0.064(3) 0.061(4) 0.058(3) 0.001(3) 0.021(3) -0.003(3) C8 0.100(5) 0.044(4) 0.078(4) 0.003(3) 0.011(4) 0.007(3) C9 0.153(7) 0.050(4) 0.085(5) -0.001(4) 0.021(5) -0.018(5) C10 0.090(4) 0.064(5) 0.080(4) -0.015(4) 0.003(4) -0.001(4) C11 0.079(4) 0.048(4) 0.062(3) -0.008(3) 0.019(3) 0.002(3) C12 0.091(5) 0.076(5) 0.058(4) -0.019(3) 0.012(4) 0.018(4) C13 0.107(5) 0.098(6) 0.079(5) -0.024(5) 0.000(4) 0.016(5) C14 0.132(7) 0.142(10) 0.090(6) -0.019(6) -0.025(5) 0.043(8) C15 0.176(10) 0.122(10) 0.085(6) 0.011(6) -0.004(7) 0.042(8) C16 0.159(8) 0.078(6) 0.082(5) 0.006(5) 0.018(6) 0.037(6) C17 0.099(5) 0.059(4) 0.057(4) -0.008(3) 0.018(4) 0.011(4) C18 0.061(3) 0.040(3) 0.056(3) -0.003(3) 0.014(3) -0.005(2) C19 0.073(4) 0.047(3) 0.047(3) -0.011(2) 0.002(3) -0.002(3) C20 0.053(3) 0.047(3) 0.051(3) -0.001(3) 0.003(2) 0.007(2) C21 0.055(3) 0.041(3) 0.055(3) -0.004(3) 0.004(2) 0.010(2) C22 0.077(4) 0.048(4) 0.068(3) -0.016(3) 0.017(3) -0.007(3) C23 0.070(3) 0.043(3) 0.082(4) -0.007(3) 0.026(3) -0.003(3) C24 0.064(3) 0.042(3) 0.059(3) -0.004(3) 0.006(3) 0.008(3) C25 0.072(4) 0.065(4) 0.061(3) -0.023(3) -0.003(3) 0.004(3) C26 0.056(3) 0.071(4) 0.078(4) -0.019(3) 0.011(3) 0.006(3) C27 0.063(3) 0.052(4) 0.060(3) -0.011(3) 0.010(3) 0.012(3) C28 0.081(4) 0.067(4) 0.086(4) -0.035(4) 0.020(4) 0.000(3) C29 0.063(3) 0.085(5) 0.079(4) -0.033(4) 0.007(3) 0.005(3) C30 0.062(3) 0.052(4) 0.074(4) -0.013(3) 0.017(3) 0.001(3) C31 0.099(4) 0.038(4) 0.103(5) -0.006(3) 0.034(4) 0.008(3) C32 0.085(4) 0.048(4) 0.105(5) 0.005(4) 0.019(4) -0.009(3) C33 0.062(3) 0.051(4) 0.075(4) 0.001(3) 0.011(3) -0.003(3) C34 0.052(3) 0.066(4) 0.067(3) -0.010(3) 0.008(3) 0.003(3) C35 0.062(3) 0.042(3) 0.064(3) -0.003(3) 0.007(3) 0.002(3) C36 0.061(3) 0.054(4) 0.058(3) -0.004(3) 0.012(3) 0.000(3) C37 0.062(3) 0.048(4) 0.069(3) -0.001(3) 0.010(3) 0.009(3) C38 0.072(4) 0.053(4) 0.074(4) 0.004(3) 0.009(3) 0.006(3) C39 0.077(4) 0.065(5) 0.078(4) 0.013(3) 0.017(3) 0.004(3) C40 0.077(4) 0.061(4) 0.071(4) 0.000(3) 0.030(3) 0.004(3) C41 0.066(3) 0.050(4) 0.067(3) -0.005(3) 0.010(3) 0.010(3) C42 0.085(4) 0.144(6) 0.100(5) 0.016(4) 0.043(4) -0.006(4) C43 0.115(5) 0.169(7) 0.153(7) 0.055(5) 0.062(5) 0.007(5) C44 0.090(5) 0.230(9) 0.144(6) 0.025(6) 0.027(4) -0.022(6) C45 0.157(7) 0.167(7) 0.170(7) -0.019(6) 0.081(6) -0.024(6) C46 0.126(5) 0.058(4) 0.173(6) 0.027(4) 0.071(5) 0.029(4) C47 0.180(7) 0.083(6) 0.228(8) 0.042(6) 0.083(7) 0.012(5) C48 0.150(6) 0.096(6) 0.251(8) 0.038(6) 0.021(6) 0.037(6) C49 0.213(8) 0.064(5) 0.193(7) 0.001(5) 0.072(6) 0.023(6) C50 0.148(8) 0.170(11) 0.123(7) 0.034(7) -0.002(6) -0.073(8) Cl1 0.154(3) 1.13(3) 0.270(6) 0.319(11) -0.061(4) -0.201(8) Cl2 0.259(4) 0.195(4) 0.1097(19) 0.031(2) -0.024(2) -0.056(3) Cl3 1.17(3) 0.176(5) 0.202(5) -0.048(4) -0.001(10) -0.096(10) N1 0.066(3) 0.048(3) 0.054(3) -0.009(2) 0.022(2) -0.003(2) N2 0.075(3) 0.047(3) 0.076(3) -0.012(2) 0.025(3) 0.006(2) O1 0.070(3) 0.062(3) 0.079(3) -0.004(2) 0.029(2) -0.012(2) O2 0.107(3) 0.052(3) 0.064(2) 0.005(2) 0.032(2) -0.003(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 1.445(7) . ? B1 O1 1.455(8) . ? B1 C18 1.598(8) . ? B1 N1 1.625(8) . ? C1 O1 1.358(7) . ? C1 C6 1.384(9) . ? C1 C2 1.402(9) . ? C2 C3 1.372(11) . ? C3 C4 1.338(12) . ? C4 C5 1.350(10) . ? C5 C6 1.418(9) . ? C6 C7 1.457(9) . ? C7 N1 1.348(7) . ? C7 C8 1.359(8) . ? C8 C9 1.377(9) . ? C9 C10 1.377(10) . ? C10 C11 1.376(8) . ? C11 N1 1.329(7) . ? C11 C12 1.482(9) . ? C12 C17 1.389(9) . ? C12 C13 1.394(10) . ? C13 C14 1.372(12) . ? C14 C15 1.352(14) . ? C15 C16 1.349(13) . ? C16 C17 1.378(10) . ? C17 O2 1.346(8) . ? C18 C23 1.368(7) . ? C18 C19 1.414(7) . ? C19 C20 1.392(7) . ? C20 C21 1.373(7) . ? C21 C22 1.396(7) . ? C21 C24 1.488(7) . ? C22 C23 1.374(7) . ? C24 C29 1.379(8) . ? C24 C25 1.388(8) . ? C25 C26 1.360(7) . ? C26 C27 1.374(8) . ? C27 C28 1.376(8) . ? C27 N2 1.409(6) . ? C28 C29 1.370(8) . ? C30 C31 1.374(8) . ? C30 N2 1.391(7) . ? C30 C35 1.408(8) . ? C31 C32 1.410(8) . ? C32 C33 1.388(8) . ? C33 C34 1.379(8) . ? C33 C42 1.521(8) . ? C34 C35 1.391(7) . ? C35 C36 1.448(7) . ? C36 C37 1.382(8) . ? C36 C41 1.433(7) . ? C37 C38 1.377(8) . ? C38 C39 1.388(8) . ? C38 C46 1.541(9) . ? C39 C40 1.355(8) . ? C40 C41 1.383(8) . ? C41 N2 1.371(7) . ? C42 C43 1.442(12) . ? C42 C44 1.462(12) . ? C42 C45 1.562(13) . ? C46 C47 1.460(11) . ? C46 C48 1.484(14) . ? C46 C49 1.506(13) . ? C50 Cl1 1.579(12) . ? C50 Cl3 1.650(14) . ? C50 Cl2 1.689(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 B1 O1 105.4(5) . . ? O2 B1 C18 114.0(5) . . ? O1 B1 C18 112.4(5) . . ? O2 B1 N1 107.1(5) . . ? O1 B1 N1 106.8(5) . . ? C18 B1 N1 110.6(4) . . ? O1 C1 C6 120.1(6) . . ? O1 C1 C2 118.6(7) . . ? C6 C1 C2 121.3(7) . . ? C3 C2 C1 117.7(8) . . ? C4 C3 C2 121.8(8) . . ? C3 C4 C5 121.9(8) . . ? C4 C5 C6 119.5(8) . . ? C1 C6 C5 117.8(6) . . ? C1 C6 C7 120.3(6) . . ? C5 C6 C7 121.8(6) . . ? N1 C7 C8 119.6(6) . . ? N1 C7 C6 117.6(6) . . ? C8 C7 C6 122.6(6) . . ? C7 C8 C9 118.8(6) . . ? C10 C9 C8 120.9(7) . . ? C11 C10 C9 118.3(7) . . ? N1 C11 C10 119.8(6) . . ? N1 C11 C12 117.7(5) . . ? C10 C11 C12 122.5(6) . . ? C17 C12 C13 119.2(7) . . ? C17 C12 C11 118.3(7) . . ? C13 C12 C11 122.4(7) . . ? C14 C13 C12 120.6(9) . . ? C15 C14 C13 119.3(10) . . ? C16 C15 C14 121.0(10) . . ? C15 C16 C17 121.7(10) . . ? O2 C17 C16 120.5(8) . . ? O2 C17 C12 121.4(6) . . ? C16 C17 C12 118.1(8) . . ? C23 C18 C19 116.0(4) . . ? C23 C18 B1 119.4(5) . . ? C19 C18 B1 124.5(5) . . ? C20 C19 C18 121.1(5) . . ? C21 C20 C19 121.8(5) . . ? C20 C21 C22 116.7(4) . . ? C20 C21 C24 123.0(5) . . ? C22 C21 C24 120.2(5) . . ? C23 C22 C21 121.6(5) . . ? C18 C23 C22 122.7(5) . . ? C29 C24 C25 117.6(5) . . ? C29 C24 C21 121.2(5) . . ? C25 C24 C21 121.1(5) . . ? C26 C25 C24 121.8(5) . . ? C25 C26 C27 120.3(5) . . ? C26 C27 C28 118.2(5) . . ? C26 C27 N2 120.7(5) . . ? C28 C27 N2 121.2(5) . . ? C29 C28 C27 121.6(6) . . ? C28 C29 C24 120.2(6) . . ? C31 C30 N2 128.9(5) . . ? C31 C30 C35 121.9(5) . . ? N2 C30 C35 109.1(5) . . ? C30 C31 C32 117.1(5) . . ? C33 C32 C31 122.3(6) . . ? C34 C33 C32 118.7(5) . . ? C34 C33 C42 120.8(6) . . ? C32 C33 C42 120.3(6) . . ? C33 C34 C35 121.0(5) . . ? C34 C35 C30 118.8(5) . . ? C34 C35 C36 134.2(5) . . ? C30 C35 C36 107.1(4) . . ? C37 C36 C41 119.7(5) . . ? C37 C36 C35 134.7(5) . . ? C41 C36 C35 105.6(5) . . ? C38 C37 C36 120.3(5) . . ? C37 C38 C39 118.6(6) . . ? C37 C38 C46 119.9(5) . . ? C39 C38 C46 121.4(5) . . ? C40 C39 C38 123.4(6) . . ? C39 C40 C41 118.8(5) . . ? N2 C41 C40 131.4(5) . . ? N2 C41 C36 109.4(5) . . ? C40 C41 C36 119.2(5) . . ? C43 C42 C44 111.3(9) . . ? C43 C42 C33 115.0(7) . . ? C44 C42 C33 110.3(6) . . ? C43 C42 C45 106.1(8) . . ? C44 C42 C45 101.6(8) . . ? C33 C42 C45 111.7(7) . . ? C47 C46 C48 112.1(9) . . ? C47 C46 C49 111.5(9) . . ? C48 C46 C49 101.8(8) . . ? C47 C46 C38 113.3(6) . . ? C48 C46 C38 108.4(8) . . ? C49 C46 C38 109.0(7) . . ? Cl1 C50 Cl3 109.0(9) . . ? Cl1 C50 Cl2 113.9(7) . . ? Cl3 C50 Cl2 108.9(7) . . ? C11 N1 C7 122.5(5) . . ? C11 N1 B1 119.2(5) . . ? C7 N1 B1 118.3(5) . . ? C41 N2 C30 108.8(4) . . ? C41 N2 C27 123.8(5) . . ? C30 N2 C27 126.7(5) . . ? C1 O1 B1 115.4(4) . . ? C17 O2 B1 116.3(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C50 H50 O1 0.98 2.39 3.293(10) 153.5 1_554 C50 H50 O2 0.98 2.40 3.270(10) 147.1 1_554 _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.562 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.064