# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Hiromitsu Maeda' _publ_contact_author_address ; 1-1-1 Nojihigashi Kusatsu 525-8577 ; _publ_contact_author_email maedahir@se.ritsumei.ac.jp loop_ _publ_author_name H.Maeda M.Takayama K.Kobayashi H.Shinmori data_1201mae _database_code_depnum_ccdc_archive 'CCDC 759617' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H37 B N2 O4' _chemical_formula_weight 584.50 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 triclinic _symmetry_space_group_name_H-M 'P - 1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.420(4) _cell_length_b 12.575(5) _cell_length_c 14.778(6) _cell_angle_alpha 70.802(18) _cell_angle_beta 82.598(16) _cell_angle_gamma 67.874(15) _cell_volume 1531.4(11) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 620 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9604 _exptl_absorpt_correction_T_max 0.9720 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _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 \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10363 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 23.50 _reflns_number_total 4518 _reflns_number_gt 3893 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4518 _refine_ls_number_parameters 401 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1640 _refine_ls_wR_factor_gt 0.1553 _refine_ls_goodness_of_fit_ref 1.340 _refine_ls_restrained_S_all 1.427 _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 O3 O 0.05532(15) 0.08922(13) 0.28102(10) 0.0212(4) Uani 1 1 d . . . O1 O -0.11824(15) 0.24342(12) 0.34794(9) 0.0209(4) Uani 1 1 d . . . O4 O 0.15197(15) 0.15254(13) 0.38953(10) 0.0206(4) Uani 1 1 d . . . O2 O 0.06533(15) 0.28739(13) 0.23307(10) 0.0208(4) Uani 1 1 d . . . N1 N 0.28573(18) -0.07903(16) 0.61382(12) 0.0194(4) Uani 1 1 d . . . H1 H 0.2507 -0.1366 0.6192 0.023 Uiso 1 1 calc R . . N2 N 0.0081(2) -0.06437(16) 0.21665(12) 0.0223(4) Uani 1 1 d . . . H2 H -0.0210 0.0113 0.1802 0.027 Uiso 1 1 calc R . . C7 C 0.1482(2) -0.04452(19) 0.43243(14) 0.0192(5) Uani 1 1 d . . . H3 H 0.1624 -0.1201 0.4798 0.023 Uiso 1 1 calc R . . C8 C 0.1846(2) 0.04340(18) 0.45269(14) 0.0186(5) Uani 1 1 d . . . C9 C 0.0915(2) -0.02134(19) 0.34343(14) 0.0182(5) Uani 1 1 d . . . C10 C 0.3069(2) -0.2236(2) 0.82597(15) 0.0237(5) Uani 1 1 d . . . H4 H 0.2057 -0.1955 0.8028 0.028 Uiso 1 1 calc R . . C11 C 0.3707(2) -0.07782(19) 0.68064(14) 0.0204(5) Uani 1 1 d . . . C12 C 0.2623(2) 0.02387(19) 0.53587(14) 0.0187(5) Uani 1 1 d . . . C13 C 0.0700(2) -0.10586(18) 0.30657(14) 0.0190(5) Uani 1 1 d . . . C14 C 0.0536(2) -0.26096(19) 0.26799(15) 0.0211(5) Uani 1 1 d . . . C15 C 0.4135(2) -0.17536(19) 0.77136(14) 0.0215(5) Uani 1 1 d . . . C1 C -0.1793(2) 0.35756(19) 0.28582(15) 0.0219(5) Uani 1 1 d . . . C2 C -0.1054(3) 0.4914(2) 0.14628(15) 0.0252(5) Uani 1 1 d . . . H5 H -0.0312 0.5085 0.0996 0.030 Uiso 1 1 calc R . . C3 C -0.0713(2) 0.38329(19) 0.21794(15) 0.0203(5) Uani 1 1 d . . . C16 C -0.0724(2) -0.1322(2) 0.10070(15) 0.0254(5) Uani 1 1 d . . . C17 C 0.3479(3) -0.3118(2) 0.91346(16) 0.0279(5) Uani 1 1 d . . . H6 H 0.2751 -0.3448 0.9497 0.033 Uiso 1 1 calc R . . C4 C -0.3266(3) 0.4386(2) 0.28450(17) 0.0281(5) Uani 1 1 d . . . H7 H -0.4009 0.4203 0.3306 0.034 Uiso 1 1 calc R . . C18 C -0.0022(2) -0.15598(19) 0.19172(15) 0.0217(5) Uani 1 1 d . . . C32 C 0.3534(2) 0.20686(19) 0.49033(15) 0.0234(5) Uani 1 1 d . . . H8 H 0.3637 0.2047 0.4234 0.028 Uiso 1 1 calc R . . H9 H 0.4486 0.2121 0.5069 0.028 Uiso 1 1 calc R . . C19 C 0.0988(2) -0.23027(19) 0.34068(15) 0.0199(5) Uani 1 1 d . . . C20 C 0.4046(2) 0.02809(19) 0.64598(15) 0.0207(5) Uani 1 1 d . . . C21 C 0.3373(2) 0.09172(19) 0.55506(14) 0.0204(5) Uani 1 1 d . . . C36 C 0.1670(2) -0.3163(2) 0.43500(15) 0.0248(5) Uani 1 1 d . . . H10 H 0.1415 -0.3896 0.4489 0.030 Uiso 1 1 calc R . . H11 H 0.1204 -0.2785 0.4860 0.030 Uiso 1 1 calc R . . C30 C 0.0568(2) -0.38405(19) 0.27506(16) 0.0248(5) Uani 1 1 d . . . H12 H -0.0218 -0.3745 0.2316 0.030 Uiso 1 1 calc R . . H13 H 0.0283 -0.4224 0.3412 0.030 Uiso 1 1 calc R . . C22 C -0.0239(3) -0.2161(2) 0.05049(16) 0.0286(5) Uani 1 1 d . . . H14 H 0.0596 -0.2893 0.0740 0.034 Uiso 1 1 calc R . . C23 C 0.4951(3) -0.3522(2) 0.94857(17) 0.0316(6) Uani 1 1 d . . . H15 H 0.5216 -0.4097 1.0101 0.038 Uiso 1 1 calc R . . C5 C -0.2539(3) 0.5751(2) 0.14506(16) 0.0296(6) Uani 1 1 d . . . H16 H -0.2811 0.6514 0.0971 0.036 Uiso 1 1 calc R . . C24 C 0.6023(3) -0.3084(2) 0.89383(16) 0.0299(6) Uani 1 1 d . . . H17 H 0.7041 -0.3382 0.9165 0.036 Uiso 1 1 calc R . . C34 C 0.4938(3) 0.0674(2) 0.69778(17) 0.0303(6) Uani 1 1 d . . . H18 H 0.5737 0.0895 0.6537 0.036 Uiso 1 1 calc R . . H19 H 0.5468 -0.0023 0.7525 0.036 Uiso 1 1 calc R . . C25 C 0.5623(2) -0.2210(2) 0.80581(15) 0.0257(5) Uani 1 1 d . . . H20 H 0.6374 -0.1918 0.7684 0.031 Uiso 1 1 calc R . . C26 C -0.2167(3) -0.0890(3) -0.06789(17) 0.0395(7) Uani 1 1 d . . . H21 H -0.2670 -0.0750 -0.1247 0.047 Uiso 1 1 calc R . . C6 C -0.3619(3) 0.5490(2) 0.21224(17) 0.0320(6) Uani 1 1 d . . . H22 H -0.4623 0.6075 0.2092 0.038 Uiso 1 1 calc R . . C37 C 0.3408(3) -0.3525(2) 0.43731(18) 0.0358(6) Uani 1 1 d . . . H23 H 0.3877 -0.3900 0.3869 0.054 Uiso 1 1 calc R . . H24 H 0.3794 -0.4101 0.4999 0.054 Uiso 1 1 calc R . . H25 H 0.3667 -0.2808 0.4266 0.054 Uiso 1 1 calc R . . C27 C -0.0956(3) -0.1942(2) -0.03294(16) 0.0336(6) Uani 1 1 d . . . H26 H -0.0608 -0.2523 -0.0664 0.040 Uiso 1 1 calc R . . C28 C -0.1931(3) -0.0249(2) 0.06303(18) 0.0401(7) Uani 1 1 d . . . H27 H -0.2264 0.0347 0.0951 0.048 Uiso 1 1 calc R . . C31 C 0.2112(3) -0.4682(2) 0.25017(19) 0.0354(6) Uani 1 1 d . . . H28 H 0.2403 -0.4316 0.1845 0.053 Uiso 1 1 calc R . . H29 H 0.2033 -0.5455 0.2552 0.053 Uiso 1 1 calc R . . H30 H 0.2892 -0.4816 0.2948 0.053 Uiso 1 1 calc R . . B1 B 0.0413(3) 0.1922(2) 0.31335(17) 0.0198(5) Uani 1 1 d . . . C33 C 0.2193(3) 0.3193(2) 0.4965(2) 0.0471(7) Uani 1 1 d . . . H31 H 0.1291 0.3243 0.4665 0.071 Uiso 1 1 calc R . . H32 H 0.2457 0.3908 0.4631 0.071 Uiso 1 1 calc R . . H33 H 0.1965 0.3152 0.5639 0.071 Uiso 1 1 calc R . . C29 C -0.2651(3) -0.0037(3) -0.02002(19) 0.0497(8) Uani 1 1 d . . . H34 H -0.3481 0.0697 -0.0444 0.060 Uiso 1 1 calc R . . C35 C 0.4029(4) 0.1707(4) 0.7347(3) 0.0755(10) Uani 1 1 d U . . H35 H 0.3728 0.2455 0.6810 0.113 Uiso 1 1 calc R . . H36 H 0.4652 0.1768 0.7797 0.113 Uiso 1 1 calc R . . H37 H 0.3109 0.1576 0.7676 0.113 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 O3 0.0268(8) 0.0172(8) 0.0189(8) -0.0038(7) -0.0075(6) -0.0063(6) O1 0.0242(8) 0.0171(8) 0.0190(8) -0.0016(6) -0.0030(6) -0.0072(6) O4 0.0261(8) 0.0181(8) 0.0187(8) -0.0037(6) -0.0067(6) -0.0088(6) O2 0.0227(7) 0.0196(8) 0.0187(8) -0.0036(6) -0.0030(6) -0.0072(6) N1 0.0217(9) 0.0185(10) 0.0185(9) -0.0050(8) -0.0048(7) -0.0068(8) N2 0.0290(9) 0.0168(10) 0.0199(9) -0.0033(8) -0.0088(8) -0.0062(8) C7 0.0209(10) 0.0167(11) 0.0185(11) -0.0036(9) -0.0012(9) -0.0061(9) C8 0.0172(10) 0.0177(11) 0.0176(11) -0.0045(9) -0.0009(8) -0.0032(8) C9 0.0163(10) 0.0188(11) 0.0195(11) -0.0066(9) -0.0001(8) -0.0056(8) C10 0.0232(10) 0.0255(12) 0.0240(12) -0.0103(10) -0.0055(9) -0.0064(9) C11 0.0188(10) 0.0224(12) 0.0195(11) -0.0093(10) -0.0039(9) -0.0029(9) C12 0.0186(10) 0.0187(11) 0.0173(10) -0.0049(9) -0.0029(8) -0.0047(9) C13 0.0205(10) 0.0198(12) 0.0168(11) -0.0058(9) -0.0029(9) -0.0062(9) C14 0.0219(10) 0.0212(12) 0.0208(11) -0.0077(10) -0.0014(9) -0.0071(9) C15 0.0251(11) 0.0211(12) 0.0176(11) -0.0079(9) -0.0043(9) -0.0046(9) C1 0.0292(11) 0.0154(11) 0.0199(11) -0.0024(9) -0.0078(9) -0.0067(9) C2 0.0338(12) 0.0229(12) 0.0206(11) -0.0034(10) -0.0051(10) -0.0132(10) C3 0.0230(11) 0.0190(12) 0.0205(11) -0.0078(9) -0.0056(9) -0.0060(9) C16 0.0320(12) 0.0286(13) 0.0203(11) -0.0071(10) -0.0020(10) -0.0157(10) C17 0.0315(12) 0.0293(13) 0.0224(12) -0.0049(10) -0.0011(10) -0.0125(10) C4 0.0286(12) 0.0271(13) 0.0288(12) -0.0093(11) -0.0021(10) -0.0088(10) C18 0.0252(11) 0.0216(12) 0.0217(11) -0.0101(10) -0.0020(9) -0.0084(9) C32 0.0249(11) 0.0251(12) 0.0236(12) -0.0067(10) -0.0052(9) -0.0114(10) C19 0.0196(10) 0.0201(12) 0.0205(11) -0.0077(9) -0.0022(9) -0.0056(9) C20 0.0212(10) 0.0190(11) 0.0216(11) -0.0063(9) -0.0067(9) -0.0046(9) C21 0.0186(10) 0.0201(12) 0.0213(11) -0.0074(9) -0.0016(9) -0.0042(9) C36 0.0340(12) 0.0193(12) 0.0220(12) -0.0064(10) -0.0035(10) -0.0092(10) C30 0.0317(12) 0.0204(12) 0.0249(12) -0.0084(10) -0.0039(10) -0.0096(10) C22 0.0352(12) 0.0298(13) 0.0247(12) -0.0100(11) 0.0015(10) -0.0150(11) C23 0.0403(13) 0.0274(13) 0.0234(12) -0.0012(10) -0.0127(10) -0.0097(11) C5 0.0398(13) 0.0188(12) 0.0269(12) -0.0007(10) -0.0115(10) -0.0086(10) C24 0.0282(12) 0.0303(14) 0.0287(13) -0.0045(11) -0.0133(10) -0.0073(10) C34 0.0346(12) 0.0276(13) 0.0318(13) -0.0093(11) -0.0162(10) -0.0090(11) C25 0.0255(11) 0.0281(13) 0.0244(12) -0.0072(11) -0.0035(9) -0.0101(10) C26 0.0545(16) 0.0511(17) 0.0221(13) -0.0074(12) -0.0103(12) -0.0288(14) C6 0.0302(12) 0.0240(13) 0.0360(14) -0.0076(11) -0.0098(11) -0.0017(10) C37 0.0353(13) 0.0288(14) 0.0365(14) -0.0121(12) -0.0149(11) 0.0023(11) C27 0.0465(14) 0.0443(16) 0.0217(12) -0.0141(12) 0.0016(11) -0.0260(13) C28 0.0530(16) 0.0320(15) 0.0330(14) -0.0119(12) -0.0164(12) -0.0060(13) C31 0.0412(14) 0.0263(14) 0.0405(14) -0.0174(12) -0.0039(12) -0.0067(11) B1 0.0250(12) 0.0178(13) 0.0168(12) -0.0037(10) -0.0036(10) -0.0079(10) C33 0.0623(18) 0.0217(14) 0.0446(16) -0.0050(12) 0.0113(14) -0.0094(13) C29 0.0595(18) 0.0461(18) 0.0362(15) -0.0103(14) -0.0260(14) -0.0048(14) C35 0.0626(17) 0.115(2) 0.094(2) -0.0780(19) 0.0137(15) -0.0448(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C9 1.334(3) . ? O3 B1 1.477(3) . ? O1 C1 1.372(3) . ? O1 B1 1.491(3) . ? O4 C8 1.328(3) . ? O4 B1 1.465(3) . ? O2 C3 1.374(2) . ? O2 B1 1.447(3) . ? N1 C11 1.356(3) . ? N1 C12 1.386(3) . ? N1 H1 0.8800 . ? N2 C18 1.358(3) . ? N2 C13 1.376(3) . ? N2 H2 0.8800 . ? C7 C9 1.382(3) . ? C7 C8 1.400(3) . ? C7 H3 0.9500 . ? C8 C12 1.416(3) . ? C9 C13 1.428(3) . ? C10 C17 1.383(3) . ? C10 C15 1.398(3) . ? C10 H4 0.9500 . ? C11 C20 1.403(3) . ? C11 C15 1.466(3) . ? C12 C21 1.405(3) . ? C13 C19 1.404(3) . ? C14 C18 1.393(3) . ? C14 C19 1.414(3) . ? C14 C30 1.506(3) . ? C15 C25 1.392(3) . ? C1 C4 1.376(3) . ? C1 C3 1.385(3) . ? C2 C3 1.373(3) . ? C2 C5 1.397(3) . ? C2 H5 0.9500 . ? C16 C22 1.391(3) . ? C16 C28 1.392(3) . ? C16 C18 1.467(3) . ? C17 C23 1.390(3) . ? C17 H6 0.9500 . ? C4 C6 1.396(3) . ? C4 H7 0.9500 . ? C32 C21 1.500(3) . ? C32 C33 1.521(3) . ? C32 H8 0.9900 . ? C32 H9 0.9900 . ? C19 C36 1.497(3) . ? C20 C21 1.406(3) . ? C20 C34 1.505(3) . ? C36 C37 1.526(3) . ? C36 H10 0.9900 . ? C36 H11 0.9900 . ? C30 C31 1.527(3) . ? C30 H12 0.9900 . ? C30 H13 0.9900 . ? C22 C27 1.379(3) . ? C22 H14 0.9500 . ? C23 C24 1.375(3) . ? C23 H15 0.9500 . ? C5 C6 1.380(3) . ? C5 H16 0.9500 . ? C24 C25 1.384(3) . ? C24 H17 0.9500 . ? C34 C35 1.492(4) . ? C34 H18 0.9900 . ? C34 H19 0.9900 . ? C25 H20 0.9500 . ? C26 C27 1.372(4) . ? C26 C29 1.381(4) . ? C26 H21 0.9500 . ? C6 H22 0.9500 . ? C37 H23 0.9800 . ? C37 H24 0.9800 . ? C37 H25 0.9800 . ? C27 H26 0.9500 . ? C28 C29 1.379(4) . ? C28 H27 0.9500 . ? C31 H28 0.9800 . ? C31 H29 0.9800 . ? C31 H30 0.9800 . ? C33 H31 0.9800 . ? C33 H32 0.9800 . ? C33 H33 0.9800 . ? C29 H34 0.9500 . ? C35 H35 0.9800 . ? C35 H36 0.9800 . ? C35 H37 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O3 B1 120.11(16) . . ? C1 O1 B1 105.72(15) . . ? C8 O4 B1 119.82(16) . . ? C3 O2 B1 106.73(16) . . ? C11 N1 C12 109.86(17) . . ? C11 N1 H1 125.1 . . ? C12 N1 H1 125.1 . . ? C18 N2 C13 110.79(18) . . ? C18 N2 H2 124.6 . . ? C13 N2 H2 124.6 . . ? C9 C7 C8 120.0(2) . . ? C9 C7 H3 120.0 . . ? C8 C7 H3 120.0 . . ? O4 C8 C7 119.84(19) . . ? O4 C8 C12 115.49(18) . . ? C7 C8 C12 124.6(2) . . ? O3 C9 C7 119.74(18) . . ? O3 C9 C13 113.32(18) . . ? C7 C9 C13 126.9(2) . . ? C17 C10 C15 120.5(2) . . ? C17 C10 H4 119.8 . . ? C15 C10 H4 119.8 . . ? N1 C11 C20 108.11(18) . . ? N1 C11 C15 122.17(19) . . ? C20 C11 C15 129.72(18) . . ? N1 C12 C21 107.30(18) . . ? N1 C12 C8 122.22(18) . . ? C21 C12 C8 130.3(2) . . ? N2 C13 C19 106.90(18) . . ? N2 C13 C9 118.19(19) . . ? C19 C13 C9 134.91(19) . . ? C18 C14 C19 107.76(19) . . ? C18 C14 C30 126.52(19) . . ? C19 C14 C30 125.63(19) . . ? C25 C15 C10 118.4(2) . . ? C25 C15 C11 120.23(19) . . ? C10 C15 C11 121.38(19) . . ? O1 C1 C4 127.78(19) . . ? O1 C1 C3 110.44(18) . . ? C4 C1 C3 121.7(2) . . ? C3 C2 C5 117.1(2) . . ? C3 C2 H5 121.4 . . ? C5 C2 H5 121.4 . . ? C2 C3 O2 127.57(19) . . ? C2 C3 C1 121.68(19) . . ? O2 C3 C1 110.74(18) . . ? C22 C16 C28 117.9(2) . . ? C22 C16 C18 121.7(2) . . ? C28 C16 C18 120.4(2) . . ? C10 C17 C23 120.2(2) . . ? C10 C17 H6 119.9 . . ? C23 C17 H6 119.9 . . ? C1 C4 C6 116.9(2) . . ? C1 C4 H7 121.6 . . ? C6 C4 H7 121.6 . . ? N2 C18 C14 107.51(18) . . ? N2 C18 C16 120.57(19) . . ? C14 C18 C16 131.79(19) . . ? C21 C32 C33 113.67(18) . . ? C21 C32 H8 108.8 . . ? C33 C32 H8 108.8 . . ? C21 C32 H9 108.8 . . ? C33 C32 H9 108.8 . . ? H8 C32 H9 107.7 . . ? C13 C19 C14 107.03(18) . . ? C13 C19 C36 127.28(19) . . ? C14 C19 C36 125.7(2) . . ? C11 C20 C21 107.50(18) . . ? C11 C20 C34 126.1(2) . . ? C21 C20 C34 126.4(2) . . ? C12 C21 C20 107.22(19) . . ? C12 C21 C32 127.74(19) . . ? C20 C21 C32 124.94(19) . . ? C19 C36 C37 112.95(19) . . ? C19 C36 H10 109.0 . . ? C37 C36 H10 109.0 . . ? C19 C36 H11 109.0 . . ? C37 C36 H11 109.0 . . ? H10 C36 H11 107.8 . . ? C14 C30 C31 114.46(18) . . ? C14 C30 H12 108.6 . . ? C31 C30 H12 108.6 . . ? C14 C30 H13 108.6 . . ? C31 C30 H13 108.6 . . ? H12 C30 H13 107.6 . . ? C27 C22 C16 120.9(2) . . ? C27 C22 H14 119.6 . . ? C16 C22 H14 119.6 . . ? C24 C23 C17 119.7(2) . . ? C24 C23 H15 120.2 . . ? C17 C23 H15 120.2 . . ? C6 C5 C2 121.2(2) . . ? C6 C5 H16 119.4 . . ? C2 C5 H16 119.4 . . ? C23 C24 C25 120.3(2) . . ? C23 C24 H17 119.9 . . ? C25 C24 H17 119.9 . . ? C20 C34 C35 115.9(2) . . ? C20 C34 H18 108.3 . . ? C35 C34 H18 108.3 . . ? C20 C34 H19 108.3 . . ? C35 C34 H19 108.3 . . ? H18 C34 H19 107.4 . . ? C24 C25 C15 120.9(2) . . ? C24 C25 H20 119.6 . . ? C15 C25 H20 119.6 . . ? C27 C26 C29 119.6(2) . . ? C27 C26 H21 120.2 . . ? C29 C26 H21 120.2 . . ? C5 C6 C4 121.4(2) . . ? C5 C6 H22 119.3 . . ? C4 C6 H22 119.3 . . ? C36 C37 H23 109.5 . . ? C36 C37 H24 109.5 . . ? H23 C37 H24 109.5 . . ? C36 C37 H25 109.5 . . ? H23 C37 H25 109.5 . . ? H24 C37 H25 109.5 . . ? C26 C27 C22 120.5(2) . . ? C26 C27 H26 119.8 . . ? C22 C27 H26 119.8 . . ? C29 C28 C16 121.0(2) . . ? C29 C28 H27 119.5 . . ? C16 C28 H27 119.5 . . ? C30 C31 H28 109.5 . . ? C30 C31 H29 109.5 . . ? H28 C31 H29 109.5 . . ? C30 C31 H30 109.5 . . ? H28 C31 H30 109.5 . . ? H29 C31 H30 109.5 . . ? O2 B1 O4 110.92(17) . . ? O2 B1 O3 109.73(17) . . ? O4 B1 O3 109.83(17) . . ? O2 B1 O1 106.24(17) . . ? O4 B1 O1 110.69(16) . . ? O3 B1 O1 109.36(17) . . ? C32 C33 H31 109.5 . . ? C32 C33 H32 109.5 . . ? H31 C33 H32 109.5 . . ? C32 C33 H33 109.5 . . ? H31 C33 H33 109.5 . . ? H32 C33 H33 109.5 . . ? C28 C29 C26 120.1(3) . . ? C28 C29 H34 120.0 . . ? C26 C29 H34 120.0 . . ? C34 C35 H35 109.5 . . ? C34 C35 H36 109.5 . . ? H35 C35 H36 109.5 . . ? C34 C35 H37 109.5 . . ? H35 C35 H37 109.5 . . ? H36 C35 H37 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag B1 O4 C8 C7 17.5(3) . . . . ? B1 O4 C8 C12 -165.26(17) . . . . ? C9 C7 C8 O4 6.0(3) . . . . ? C9 C7 C8 C12 -170.96(18) . . . . ? B1 O3 C9 C7 -14.1(3) . . . . ? B1 O3 C9 C13 167.82(17) . . . . ? C8 C7 C9 O3 -7.6(3) . . . . ? C8 C7 C9 C13 170.19(18) . . . . ? C12 N1 C11 C20 -0.2(2) . . . . ? C12 N1 C11 C15 179.83(17) . . . . ? C11 N1 C12 C21 0.4(2) . . . . ? C11 N1 C12 C8 176.27(17) . . . . ? O4 C8 C12 N1 171.08(16) . . . . ? C7 C8 C12 N1 -11.9(3) . . . . ? O4 C8 C12 C21 -14.1(3) . . . . ? C7 C8 C12 C21 162.9(2) . . . . ? C18 N2 C13 C19 -0.7(2) . . . . ? C18 N2 C13 C9 178.90(17) . . . . ? O3 C9 C13 N2 -3.7(3) . . . . ? C7 C9 C13 N2 178.34(18) . . . . ? O3 C9 C13 C19 175.7(2) . . . . ? C7 C9 C13 C19 -2.2(4) . . . . ? C17 C10 C15 C25 2.0(3) . . . . ? C17 C10 C15 C11 -177.06(18) . . . . ? N1 C11 C15 C25 135.9(2) . . . . ? C20 C11 C15 C25 -44.1(3) . . . . ? N1 C11 C15 C10 -45.0(3) . . . . ? C20 C11 C15 C10 135.0(2) . . . . ? B1 O1 C1 C4 176.0(2) . . . . ? B1 O1 C1 C3 -1.9(2) . . . . ? C5 C2 C3 O2 179.28(19) . . . . ? C5 C2 C3 C1 0.5(3) . . . . ? B1 O2 C3 C2 -176.3(2) . . . . ? B1 O2 C3 C1 2.6(2) . . . . ? O1 C1 C3 C2 178.62(18) . . . . ? C4 C1 C3 C2 0.5(3) . . . . ? O1 C1 C3 O2 -0.4(2) . . . . ? C4 C1 C3 O2 -178.48(19) . . . . ? C15 C10 C17 C23 0.9(3) . . . . ? O1 C1 C4 C6 -178.7(2) . . . . ? C3 C1 C4 C6 -0.9(3) . . . . ? C13 N2 C18 C14 0.5(2) . . . . ? C13 N2 C18 C16 176.75(18) . . . . ? C19 C14 C18 N2 -0.1(2) . . . . ? C30 C14 C18 N2 176.45(19) . . . . ? C19 C14 C18 C16 -175.8(2) . . . . ? C30 C14 C18 C16 0.8(4) . . . . ? C22 C16 C18 N2 148.1(2) . . . . ? C28 C16 C18 N2 -33.3(3) . . . . ? C22 C16 C18 C14 -36.7(3) . . . . ? C28 C16 C18 C14 141.9(3) . . . . ? N2 C13 C19 C14 0.6(2) . . . . ? C9 C13 C19 C14 -178.9(2) . . . . ? N2 C13 C19 C36 179.54(19) . . . . ? C9 C13 C19 C36 0.0(4) . . . . ? C18 C14 C19 C13 -0.3(2) . . . . ? C30 C14 C19 C13 -176.91(18) . . . . ? C18 C14 C19 C36 -179.26(18) . . . . ? C30 C14 C19 C36 4.1(3) . . . . ? N1 C11 C20 C21 -0.2(2) . . . . ? C15 C11 C20 C21 179.84(19) . . . . ? N1 C11 C20 C34 178.65(19) . . . . ? C15 C11 C20 C34 -1.4(3) . . . . ? N1 C12 C21 C20 -0.5(2) . . . . ? C8 C12 C21 C20 -175.9(2) . . . . ? N1 C12 C21 C32 176.11(18) . . . . ? C8 C12 C21 C32 0.7(3) . . . . ? C11 C20 C21 C12 0.4(2) . . . . ? C34 C20 C21 C12 -178.38(19) . . . . ? C11 C20 C21 C32 -176.33(18) . . . . ? C34 C20 C21 C32 4.9(3) . . . . ? C33 C32 C21 C12 86.4(3) . . . . ? C33 C32 C21 C20 -97.5(3) . . . . ? C13 C19 C36 C37 -77.9(3) . . . . ? C14 C19 C36 C37 100.8(2) . . . . ? C18 C14 C30 C31 99.0(2) . . . . ? C19 C14 C30 C31 -85.0(3) . . . . ? C28 C16 C22 C27 -1.3(3) . . . . ? C18 C16 C22 C27 177.3(2) . . . . ? C10 C17 C23 C24 -3.2(3) . . . . ? C3 C2 C5 C6 -1.0(3) . . . . ? C17 C23 C24 C25 2.6(4) . . . . ? C11 C20 C34 C35 -107.7(3) . . . . ? C21 C20 C34 C35 70.9(3) . . . . ? C23 C24 C25 C15 0.4(3) . . . . ? C10 C15 C25 C24 -2.7(3) . . . . ? C11 C15 C25 C24 176.40(19) . . . . ? C2 C5 C6 C4 0.6(3) . . . . ? C1 C4 C6 C5 0.3(3) . . . . ? C29 C26 C27 C22 1.2(4) . . . . ? C16 C22 C27 C26 -0.2(4) . . . . ? C22 C16 C28 C29 1.8(4) . . . . ? C18 C16 C28 C29 -176.9(2) . . . . ? C3 O2 B1 O4 -123.97(17) . . . . ? C3 O2 B1 O3 114.49(17) . . . . ? C3 O2 B1 O1 -3.6(2) . . . . ? C8 O4 B1 O2 -157.21(16) . . . . ? C8 O4 B1 O3 -35.7(2) . . . . ? C8 O4 B1 O1 85.1(2) . . . . ? C9 O3 B1 O2 156.28(16) . . . . ? C9 O3 B1 O4 34.1(2) . . . . ? C9 O3 B1 O1 -87.6(2) . . . . ? C1 O1 B1 O2 3.4(2) . . . . ? C1 O1 B1 O4 123.90(17) . . . . ? C1 O1 B1 O3 -114.96(18) . . . . ? C16 C28 C29 C26 -0.7(4) . . . . ? C27 C26 C29 C28 -0.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.134 _refine_diff_density_min -0.565 _refine_diff_density_rms 0.047 #============================================================================== # End of CIF #============================================================================== data_81203mae _database_code_depnum_ccdc_archive 'CCDC 759618' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H19 B N2 O2' _chemical_formula_sum 'C23 H19 B N2 O2' _chemical_formula_weight 366.21 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 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 11.512(5) _cell_length_b 14.056(4) _cell_length_c 11.554(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.314(16) _cell_angle_gamma 90.00 _cell_volume 1844.9(12) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 14585 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9592 _exptl_absorpt_correction_T_max 0.9753 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _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 \w _diffrn_detector_area_resol_mean 5.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17717 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4211 _reflns_number_gt 3548 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0568P)^2^+0.6106P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4211 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1083 _refine_ls_wR_factor_gt 0.1029 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 C1 C 0.13141(12) -0.07274(10) 0.05845(13) 0.0280(3) Uani 1 1 d . . . H1 H 0.0853 -0.0896 -0.0145 0.034 Uiso 1 1 calc R . . C2 C 0.11461(12) -0.10510(10) 0.16679(13) 0.0296(3) Uani 1 1 d . . . H2 H 0.0554 -0.1482 0.1821 0.036 Uiso 1 1 calc R . . C3 C 0.20079(12) -0.06291(9) 0.25041(13) 0.0261(3) Uani 1 1 d . . . H3 H 0.2107 -0.0719 0.3329 0.031 Uiso 1 1 calc R . . C4 C 0.26910(11) -0.00555(8) 0.19045(11) 0.0208(3) Uani 1 1 d . . . C5 C 0.36878(11) 0.05385(8) 0.23089(11) 0.0190(2) Uani 1 1 d . . . C6 C 0.41299(11) 0.06833(9) 0.34875(11) 0.0213(3) Uani 1 1 d . . . H4 H 0.3877 0.0298 0.4075 0.026 Uiso 1 1 calc R . . C7 C 0.49512(11) 0.14053(8) 0.37880(11) 0.0194(2) Uani 1 1 d . . . C8 C 0.52418(11) 0.17821(9) 0.49507(11) 0.0222(3) Uani 1 1 d . . . C9 C 0.47570(12) 0.16083(9) 0.59477(11) 0.0243(3) Uani 1 1 d . . . H5 H 0.4149 0.1164 0.6014 0.029 Uiso 1 1 calc R . . C10 C 0.53106(14) 0.21934(11) 0.68351(12) 0.0317(3) Uani 1 1 d . . . H6 H 0.5152 0.2222 0.7616 0.038 Uiso 1 1 calc R . . C11 C 0.61297(14) 0.27243(11) 0.63798(13) 0.0345(3) Uani 1 1 d . . . H7 H 0.6638 0.3188 0.6791 0.041 Uiso 1 1 calc R . . N1 N 0.22457(10) -0.01293(8) 0.07325(10) 0.0237(2) Uani 1 1 d . . . H8 H 0.2524 0.0167 0.0165 0.028 Uiso 1 1 calc R . . N2 N 0.60874(11) 0.24720(9) 0.52363(10) 0.0301(3) Uani 1 1 d . . . H9 H 0.6531 0.2712 0.4756 0.036 Uiso 1 1 calc R . . O1 O 0.41217(7) 0.09868(6) 0.14809(8) 0.01906(19) Uani 1 1 d . . . O2 O 0.54706(8) 0.18255(6) 0.29991(7) 0.01940(19) Uani 1 1 d . . . B1 B 0.53698(12) 0.13623(9) 0.17823(12) 0.0180(3) Uani 1 1 d . . . C12 C 0.55273(11) 0.22024(8) 0.08826(10) 0.0181(2) Uani 1 1 d . . . C13 C 0.65203(11) 0.23031(9) 0.03447(12) 0.0235(3) Uani 1 1 d . . . H10 H 0.7129 0.1841 0.0489 0.028 Uiso 1 1 calc R . . C14 C 0.66427(13) 0.30626(10) -0.03978(12) 0.0290(3) Uani 1 1 d . . . H11 H 0.7327 0.3112 -0.0756 0.035 Uiso 1 1 calc R . . C15 C 0.57730(13) 0.37441(10) -0.06159(12) 0.0286(3) Uani 1 1 d . . . H12 H 0.5858 0.4264 -0.1120 0.034 Uiso 1 1 calc R . . C16 C 0.47748(12) 0.36657(9) -0.00953(12) 0.0261(3) Uani 1 1 d . . . H13 H 0.4172 0.4132 -0.0242 0.031 Uiso 1 1 calc R . . C17 C 0.46584(11) 0.29034(9) 0.06415(11) 0.0217(3) Uani 1 1 d . . . H14 H 0.3969 0.2856 0.0992 0.026 Uiso 1 1 calc R . . C18 C 0.62843(11) 0.04846(8) 0.18657(11) 0.0194(2) Uani 1 1 d . . . C19 C 0.59662(11) -0.04143(9) 0.14039(11) 0.0206(3) Uani 1 1 d . . . H15 H 0.5186 -0.0514 0.1007 0.025 Uiso 1 1 calc R . . C20 C 0.67646(12) -0.11709(9) 0.15099(11) 0.0236(3) Uani 1 1 d . . . H16 H 0.6522 -0.1776 0.1191 0.028 Uiso 1 1 calc R . . C21 C 0.79025(13) -0.10415(10) 0.20758(12) 0.0271(3) Uani 1 1 d . . . H17 H 0.8442 -0.1558 0.2162 0.033 Uiso 1 1 calc R . . C22 C 0.82541(13) -0.01504(11) 0.25182(13) 0.0325(3) Uani 1 1 d . . . H18 H 0.9043 -0.0051 0.2890 0.039 Uiso 1 1 calc R . . C23 C 0.74530(12) 0.05974(10) 0.24174(13) 0.0283(3) Uani 1 1 d . . . H19 H 0.7705 0.1201 0.2731 0.034 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 C1 0.0212(6) 0.0294(7) 0.0337(7) -0.0082(6) 0.0052(5) -0.0046(5) C2 0.0235(7) 0.0279(7) 0.0397(8) -0.0054(6) 0.0119(6) -0.0072(5) C3 0.0252(7) 0.0240(6) 0.0309(7) -0.0016(5) 0.0106(5) -0.0043(5) C4 0.0194(6) 0.0185(6) 0.0256(6) -0.0019(5) 0.0071(5) 0.0011(4) C5 0.0180(6) 0.0146(5) 0.0255(6) 0.0003(4) 0.0069(5) 0.0024(4) C6 0.0231(6) 0.0186(6) 0.0234(6) 0.0018(5) 0.0073(5) -0.0007(4) C7 0.0199(6) 0.0176(5) 0.0215(6) 0.0022(4) 0.0055(5) 0.0043(4) C8 0.0242(6) 0.0202(6) 0.0222(6) 0.0015(5) 0.0040(5) 0.0006(5) C9 0.0269(7) 0.0252(6) 0.0211(6) 0.0007(5) 0.0045(5) -0.0053(5) C10 0.0380(8) 0.0369(8) 0.0206(6) -0.0019(6) 0.0058(6) -0.0085(6) C11 0.0399(8) 0.0357(8) 0.0273(7) -0.0051(6) 0.0034(6) -0.0142(6) N1 0.0210(5) 0.0247(5) 0.0263(6) -0.0022(4) 0.0063(4) -0.0032(4) N2 0.0332(6) 0.0330(6) 0.0255(6) -0.0001(5) 0.0085(5) -0.0088(5) O1 0.0176(4) 0.0192(4) 0.0207(4) 0.0005(3) 0.0039(3) -0.0017(3) O2 0.0209(4) 0.0180(4) 0.0200(4) -0.0003(3) 0.0054(3) -0.0024(3) B1 0.0169(6) 0.0180(6) 0.0194(6) -0.0013(5) 0.0036(5) -0.0008(5) C12 0.0197(6) 0.0179(5) 0.0166(5) -0.0026(4) 0.0024(4) -0.0027(4) C13 0.0215(6) 0.0248(6) 0.0249(6) -0.0005(5) 0.0055(5) -0.0004(5) C14 0.0296(7) 0.0340(7) 0.0253(7) 0.0011(6) 0.0102(6) -0.0079(5) C15 0.0398(8) 0.0235(6) 0.0222(6) 0.0043(5) 0.0037(6) -0.0070(5) C16 0.0308(7) 0.0211(6) 0.0247(6) 0.0012(5) -0.0002(5) 0.0027(5) C17 0.0219(6) 0.0220(6) 0.0216(6) -0.0012(5) 0.0045(5) -0.0004(5) C18 0.0205(6) 0.0192(6) 0.0188(6) 0.0011(4) 0.0041(5) 0.0012(4) C19 0.0206(6) 0.0214(6) 0.0206(6) -0.0002(5) 0.0060(5) -0.0012(5) C20 0.0314(7) 0.0190(6) 0.0219(6) -0.0002(5) 0.0090(5) 0.0007(5) C21 0.0321(7) 0.0266(6) 0.0227(6) 0.0013(5) 0.0047(5) 0.0112(5) C22 0.0246(7) 0.0368(8) 0.0328(7) -0.0072(6) -0.0056(6) 0.0068(6) C23 0.0247(7) 0.0246(6) 0.0332(7) -0.0073(5) -0.0027(5) 0.0019(5) _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 C1 N1 1.3517(17) . ? C1 C2 1.375(2) . ? C1 H1 0.9500 . ? C2 C3 1.400(2) . ? C2 H2 0.9500 . ? C3 C4 1.3873(18) . ? C3 H3 0.9500 . ? C4 N1 1.3720(18) . ? C4 C5 1.4349(17) . ? C5 O1 1.3100(15) . ? C5 C6 1.3893(19) . ? C6 C7 1.3922(18) . ? C6 H4 0.9500 . ? C7 O2 1.3090(15) . ? C7 C8 1.4323(18) . ? C8 N2 1.3759(17) . ? C8 C9 1.3805(18) . ? C9 C10 1.3865(19) . ? C9 H5 0.9500 . ? C10 C11 1.372(2) . ? C10 H6 0.9500 . ? C11 N2 1.3611(19) . ? C11 H7 0.9500 . ? N1 H8 0.8800 . ? N2 H9 0.8800 . ? O1 B1 1.5174(16) . ? O2 B1 1.5365(16) . ? B1 C12 1.6027(18) . ? B1 C18 1.6146(18) . ? C12 C13 1.3939(18) . ? C12 C17 1.3997(17) . ? C13 C14 1.3908(19) . ? C13 H10 0.9500 . ? C14 C15 1.379(2) . ? C14 H11 0.9500 . ? C15 C16 1.385(2) . ? C15 H12 0.9500 . ? C16 C17 1.3884(18) . ? C16 H13 0.9500 . ? C17 H14 0.9500 . ? C18 C19 1.3971(17) . ? C18 C23 1.4015(19) . ? C19 C20 1.3980(18) . ? C19 H15 0.9500 . ? C20 C21 1.378(2) . ? C20 H16 0.9500 . ? C21 C22 1.388(2) . ? C21 H17 0.9500 . ? C22 C23 1.3907(19) . ? C22 H18 0.9500 . ? C23 H19 0.9500 . ? 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 N1 C1 C2 108.44(12) . . ? N1 C1 H1 125.8 . . ? C2 C1 H1 125.8 . . ? C1 C2 C3 107.45(12) . . ? C1 C2 H2 126.3 . . ? C3 C2 H2 126.3 . . ? C4 C3 C2 107.30(13) . . ? C4 C3 H3 126.3 . . ? C2 C3 H3 126.3 . . ? N1 C4 C3 107.30(11) . . ? N1 C4 C5 121.11(11) . . ? C3 C4 C5 131.58(12) . . ? O1 C5 C6 121.51(11) . . ? O1 C5 C4 114.93(11) . . ? C6 C5 C4 123.45(11) . . ? C5 C6 C7 118.52(11) . . ? C5 C6 H4 120.7 . . ? C7 C6 H4 120.7 . . ? O2 C7 C6 121.57(11) . . ? O2 C7 C8 115.00(11) . . ? C6 C7 C8 123.34(11) . . ? N2 C8 C9 106.89(11) . . ? N2 C8 C7 122.29(12) . . ? C9 C8 C7 130.73(12) . . ? C8 C9 C10 108.21(12) . . ? C8 C9 H5 125.9 . . ? C10 C9 H5 125.9 . . ? C11 C10 C9 107.53(13) . . ? C11 C10 H6 126.2 . . ? C9 C10 H6 126.2 . . ? N2 C11 C10 108.15(13) . . ? N2 C11 H7 125.9 . . ? C10 C11 H7 125.9 . . ? C1 N1 C4 109.51(11) . . ? C1 N1 H8 125.2 . . ? C4 N1 H8 125.2 . . ? C11 N2 C8 109.21(12) . . ? C11 N2 H9 125.4 . . ? C8 N2 H9 125.4 . . ? C5 O1 B1 117.29(10) . . ? C7 O2 B1 118.07(9) . . ? O1 B1 O2 106.61(9) . . ? O1 B1 C12 108.05(10) . . ? O2 B1 C12 106.35(9) . . ? O1 B1 C18 109.39(10) . . ? O2 B1 C18 108.49(10) . . ? C12 B1 C18 117.42(10) . . ? C13 C12 C17 116.81(11) . . ? C13 C12 B1 123.44(11) . . ? C17 C12 B1 119.70(11) . . ? C14 C13 C12 121.69(12) . . ? C14 C13 H10 119.2 . . ? C12 C13 H10 119.2 . . ? C15 C14 C13 120.18(13) . . ? C15 C14 H11 119.9 . . ? C13 C14 H11 119.9 . . ? C14 C15 C16 119.62(12) . . ? C14 C15 H12 120.2 . . ? C16 C15 H12 120.2 . . ? C15 C16 C17 119.79(13) . . ? C15 C16 H13 120.1 . . ? C17 C16 H13 120.1 . . ? C16 C17 C12 121.91(12) . . ? C16 C17 H14 119.0 . . ? C12 C17 H14 119.0 . . ? C19 C18 C23 116.68(11) . . ? C19 C18 B1 122.70(11) . . ? C23 C18 B1 120.62(11) . . ? C18 C19 C20 121.78(12) . . ? C18 C19 H15 119.1 . . ? C20 C19 H15 119.1 . . ? C21 C20 C19 120.14(12) . . ? C21 C20 H16 119.9 . . ? C19 C20 H16 119.9 . . ? C20 C21 C22 119.47(12) . . ? C20 C21 H17 120.3 . . ? C22 C21 H17 120.3 . . ? C21 C22 C23 120.08(13) . . ? C21 C22 H18 120.0 . . ? C23 C22 H18 120.0 . . ? C22 C23 C18 121.83(12) . . ? C22 C23 H19 119.1 . . ? C18 C23 H19 119.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 0.22(16) . . . . ? C1 C2 C3 C4 -0.25(16) . . . . ? C2 C3 C4 N1 0.19(15) . . . . ? C2 C3 C4 C5 -179.97(13) . . . . ? N1 C4 C5 O1 -0.22(17) . . . . ? C3 C4 C5 O1 179.95(12) . . . . ? N1 C4 C5 C6 176.02(11) . . . . ? C3 C4 C5 C6 -3.8(2) . . . . ? O1 C5 C6 C7 7.92(18) . . . . ? C4 C5 C6 C7 -168.08(11) . . . . ? C5 C6 C7 O2 -12.74(18) . . . . ? C5 C6 C7 C8 163.51(12) . . . . ? O2 C7 C8 N2 -5.93(18) . . . . ? C6 C7 C8 N2 177.59(12) . . . . ? O2 C7 C8 C9 170.29(13) . . . . ? C6 C7 C8 C9 -6.2(2) . . . . ? N2 C8 C9 C10 -0.01(16) . . . . ? C7 C8 C9 C10 -176.66(14) . . . . ? C8 C9 C10 C11 0.11(18) . . . . ? C9 C10 C11 N2 -0.17(18) . . . . ? C2 C1 N1 C4 -0.10(15) . . . . ? C3 C4 N1 C1 -0.06(15) . . . . ? C5 C4 N1 C1 -179.92(11) . . . . ? C10 C11 N2 C8 0.17(18) . . . . ? C9 C8 N2 C11 -0.10(16) . . . . ? C7 C8 N2 C11 176.91(13) . . . . ? C6 C5 O1 B1 22.76(16) . . . . ? C4 C5 O1 B1 -160.92(10) . . . . ? C6 C7 O2 B1 -13.47(16) . . . . ? C8 C7 O2 B1 169.99(10) . . . . ? C5 O1 B1 O2 -43.85(13) . . . . ? C5 O1 B1 C12 -157.82(10) . . . . ? C5 O1 B1 C18 73.27(12) . . . . ? C7 O2 B1 O1 39.34(13) . . . . ? C7 O2 B1 C12 154.45(10) . . . . ? C7 O2 B1 C18 -78.38(13) . . . . ? O1 B1 C12 C13 -136.63(12) . . . . ? O2 B1 C12 C13 109.23(13) . . . . ? C18 B1 C12 C13 -12.41(17) . . . . ? O1 B1 C12 C17 45.97(14) . . . . ? O2 B1 C12 C17 -68.16(13) . . . . ? C18 B1 C12 C17 170.19(11) . . . . ? C17 C12 C13 C14 -0.10(18) . . . . ? B1 C12 C13 C14 -177.56(12) . . . . ? C12 C13 C14 C15 0.3(2) . . . . ? C13 C14 C15 C16 -0.3(2) . . . . ? C14 C15 C16 C17 0.1(2) . . . . ? C15 C16 C17 C12 0.1(2) . . . . ? C13 C12 C17 C16 -0.13(18) . . . . ? B1 C12 C17 C16 177.44(12) . . . . ? O1 B1 C18 C19 16.41(16) . . . . ? O2 B1 C18 C19 132.34(12) . . . . ? C12 B1 C18 C19 -107.13(14) . . . . ? O1 B1 C18 C23 -163.51(12) . . . . ? O2 B1 C18 C23 -47.58(15) . . . . ? C12 B1 C18 C23 72.95(16) . . . . ? C23 C18 C19 C20 1.46(19) . . . . ? B1 C18 C19 C20 -178.47(11) . . . . ? C18 C19 C20 C21 -0.37(19) . . . . ? C19 C20 C21 C22 -1.3(2) . . . . ? C20 C21 C22 C23 1.7(2) . . . . ? C21 C22 C23 C18 -0.6(2) . . . . ? C19 C18 C23 C22 -1.0(2) . . . . ? B1 C18 C23 C22 178.95(13) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.441 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.042 #============================================================================== # End of CIF #============================================================================== data_80924mae _database_code_depnum_ccdc_archive 'CCDC 759619' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H35 B N2 O2' _chemical_formula_weight 478.42 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 orthorhombic _symmetry_space_group_name_H-M 'P c c a' _symmetry_space_group_name_Hall '-P 2a 2ac' _symmetry_Int_Tables_number 54 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' 'x+1/2, -y, -z+1/2' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' '-x-1/2, y, z-1/2' 'x, -y, z-1/2' _cell_length_a 22.300(9) _cell_length_b 17.053(8) _cell_length_c 21.385(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8132(6) _cell_formula_units_Z 12 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 19935 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 296.1 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.172 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3072 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9580 _exptl_absorpt_correction_T_max 0.9787 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71075 _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 \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 42895 _diffrn_reflns_av_R_equivalents 0.0800 _diffrn_reflns_av_sigmaI/netI 0.0780 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.49 _reflns_number_total 9064 _reflns_number_gt 4210 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0621P)^2^+1.4854P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9064 _refine_ls_number_parameters 494 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1893 _refine_ls_R_factor_gt 0.0855 _refine_ls_wR_factor_ref 0.1740 _refine_ls_wR_factor_gt 0.1428 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 C1 C 0.37596(15) 0.37767(17) 0.20800(14) 0.0713(9) Uani 1 1 d . . . H1 H 0.3648 0.3295 0.1913 0.086 Uiso 1 1 calc R . . C2 C 0.40845(13) 0.38841(16) 0.26117(13) 0.0613(8) Uani 1 1 d . . . C3 C 0.41583(13) 0.46934(16) 0.26910(12) 0.0584(7) Uani 1 1 d . . . C4 C 0.38629(12) 0.50662(16) 0.21968(11) 0.0542(7) Uani 1 1 d . . . C5 C 0.37836(12) 0.58580(15) 0.20006(11) 0.0517(7) Uani 1 1 d . . . C6 C 0.40074(12) 0.65148(15) 0.22866(12) 0.0535(7) Uani 1 1 d . . . H2 H 0.4271 0.6457 0.2620 0.064 Uiso 1 1 calc R . . C7 C 0.38527(12) 0.72574(15) 0.20939(11) 0.0492(7) Uani 1 1 d . . . C8 C 0.40222(12) 0.79723(15) 0.23870(11) 0.0509(7) Uani 1 1 d . . . C9 C 0.43169(12) 0.81691(16) 0.29442(12) 0.0551(7) Uani 1 1 d . . . C10 C 0.43130(13) 0.89858(16) 0.29915(13) 0.0590(7) Uani 1 1 d . . . C11 C 0.40360(13) 0.92682(17) 0.24680(14) 0.0646(8) Uani 1 1 d . . . H3 H 0.3975 0.9795 0.2376 0.078 Uiso 1 1 calc R . . C12 C 0.43288(16) 0.32533(17) 0.30297(15) 0.0823(10) Uani 1 1 d . . . H24 H 0.4157 0.3317 0.3443 0.099 Uiso 1 1 calc R . . H25 H 0.4759 0.3324 0.3067 0.099 Uiso 1 1 calc R . . C13 C 0.42077(17) 0.24268(18) 0.2808(2) 0.1040(13) Uani 1 1 d . . . H26 H 0.3783 0.2339 0.2793 0.156 Uiso 1 1 calc R . . H27 H 0.4388 0.2061 0.3093 0.156 Uiso 1 1 calc R . . H28 H 0.4376 0.2356 0.2399 0.156 Uiso 1 1 calc R . . C14 C 0.45083(15) 0.50689(18) 0.32292(14) 0.0768(9) Uani 1 1 d . . . H29 H 0.4813 0.4706 0.3374 0.092 Uiso 1 1 calc R . . H30 H 0.4709 0.5537 0.3079 0.092 Uiso 1 1 calc R . . C15 C 0.41108(17) 0.5279(2) 0.37590(17) 0.1086(13) Uani 1 1 d . . . H31 H 0.3810 0.5641 0.3618 0.163 Uiso 1 1 calc R . . H32 H 0.4344 0.5517 0.4085 0.163 Uiso 1 1 calc R . . H33 H 0.3921 0.4814 0.3917 0.163 Uiso 1 1 calc R . . C16 C 0.45930(14) 0.76276(18) 0.34274(13) 0.0713(9) Uani 1 1 d . . . H34 H 0.4742 0.7159 0.3222 0.086 Uiso 1 1 calc R . . H35 H 0.4931 0.7888 0.3624 0.086 Uiso 1 1 calc R . . C17 C 0.41505(18) 0.7402(2) 0.39138(17) 0.1133(14) Uani 1 1 d . . . H36 H 0.4016 0.7862 0.4131 0.170 Uiso 1 1 calc R . . H37 H 0.4335 0.7048 0.4205 0.170 Uiso 1 1 calc R . . H38 H 0.3814 0.7149 0.3720 0.170 Uiso 1 1 calc R . . C18 C 0.45627(16) 0.94677(18) 0.35196(16) 0.0849(10) Uani 1 1 d . . . H39 H 0.4416 0.9254 0.3911 0.102 Uiso 1 1 calc R . . H40 H 0.4996 0.9417 0.3519 0.102 Uiso 1 1 calc R . . C19 C 0.44078(17) 1.0311(2) 0.34926(19) 0.1108(14) Uani 1 1 d . . . H41 H 0.4600 1.0547 0.3138 0.166 Uiso 1 1 calc R . . H42 H 0.4542 1.0565 0.3868 0.166 Uiso 1 1 calc R . . H43 H 0.3981 1.0368 0.3455 0.166 Uiso 1 1 calc R . . C20 C 0.27337(13) 0.67362(16) 0.08725(11) 0.0529(7) Uani 1 1 d . . . C21 C 0.24757(14) 0.60723(17) 0.06134(13) 0.0639(8) Uani 1 1 d . . . H4 H 0.2699 0.5612 0.0602 0.077 Uiso 1 1 calc R . . C22 C 0.19055(16) 0.6064(2) 0.03731(14) 0.0744(9) Uani 1 1 d . . . H5 H 0.1748 0.5602 0.0209 0.089 Uiso 1 1 calc R . . C23 C 0.15706(15) 0.6729(2) 0.03756(14) 0.0785(10) Uani 1 1 d . . . H6 H 0.1183 0.6726 0.0215 0.094 Uiso 1 1 calc R . . C24 C 0.18102(17) 0.7404(2) 0.06178(14) 0.0791(10) Uani 1 1 d . . . H7 H 0.1586 0.7864 0.0617 0.095 Uiso 1 1 calc R . . C25 C 0.23822(15) 0.74052(18) 0.08624(12) 0.0663(8) Uani 1 1 d . . . H8 H 0.2536 0.7869 0.1025 0.080 Uiso 1 1 calc R . . C26 C 0.39178(13) 0.67337(18) 0.06230(12) 0.0601(8) Uani 1 1 d . . . C27 C 0.42486(17) 0.6107(2) 0.04090(16) 0.0883(10) Uani 1 1 d . . . H9 H 0.4184 0.5615 0.0584 0.106 Uiso 1 1 calc R . . C28 C 0.46761(19) 0.6184(3) -0.0061(2) 0.1062(13) Uani 1 1 d . . . H10 H 0.4892 0.5748 -0.0193 0.127 Uiso 1 1 calc R . . C29 C 0.47783(18) 0.6891(4) -0.03244(17) 0.1040(14) Uani 1 1 d . . . H11 H 0.5062 0.6944 -0.0640 0.125 Uiso 1 1 calc R . . C30 C 0.4466(2) 0.7515(3) -0.0127(2) 0.1157(14) Uani 1 1 d . . . H12 H 0.4536 0.8004 -0.0306 0.139 Uiso 1 1 calc R . . C31 C 0.40435(17) 0.7438(2) 0.03387(16) 0.0925(11) Uani 1 1 d . . . H13 H 0.3834 0.7881 0.0466 0.111 Uiso 1 1 calc R . . N1 N 0.36258(11) 0.44822(14) 0.18354(10) 0.0695(7) Uani 1 1 d . . . H14 H 0.3421 0.4555 0.1500 0.083 Uiso 1 1 calc R . . N2 N 0.38661(10) 0.86654(12) 0.21083(10) 0.0597(6) Uani 1 1 d . . . H15 H 0.3686 0.8707 0.1754 0.072 Uiso 1 1 calc R . . O1 O 0.34440(9) 0.59245(10) 0.14980(8) 0.0667(6) Uani 1 1 d . . . O2 O 0.34936(9) 0.73526(10) 0.16077(7) 0.0582(5) Uani 1 1 d . . . B1 B 0.34025(16) 0.66859(17) 0.11440(13) 0.0552(9) Uani 1 1 d . . . C32 C 0.25291(13) 0.27625(15) 0.28604(13) 0.0575(7) Uani 1 1 d . . . H16 H 0.2501 0.3273 0.2711 0.069 Uiso 1 1 calc R . . C33 C 0.26252(12) 0.25538(15) 0.34735(12) 0.0535(7) Uani 1 1 d . . . C34 C 0.26301(12) 0.17332(15) 0.34967(11) 0.0482(6) Uani 1 1 d . . . C35 C 0.25340(11) 0.14611(14) 0.28877(11) 0.0454(6) Uani 1 1 d . . . C36 C 0.25002(11) 0.07037(14) 0.26067(10) 0.0458(6) Uani 1 1 d . . . C37 C 0.2500 0.0000 0.29224(16) 0.0508(9) Uani 1 2 d S . . H17 H 0.2500 0.0000 0.3357 0.061 Uiso 1 2 calc SR . . C38 C 0.27222(16) 0.31031(17) 0.40111(14) 0.0766(9) Uani 1 1 d . . . H44 H 0.2422 0.2997 0.4328 0.092 Uiso 1 1 calc R . . H45 H 0.3112 0.2995 0.4194 0.092 Uiso 1 1 calc R . . C39 C 0.26938(18) 0.39505(19) 0.38439(17) 0.1019(12) Uani 1 1 d . . . H46 H 0.2987 0.4063 0.3528 0.153 Uiso 1 1 calc R . . H47 H 0.2775 0.4262 0.4208 0.153 Uiso 1 1 calc R . . H48 H 0.2301 0.4073 0.3688 0.153 Uiso 1 1 calc R . . C40 C 0.27048(13) 0.12652(16) 0.40838(11) 0.0609(8) Uani 1 1 d . . . H49 H 0.2932 0.1571 0.4384 0.073 Uiso 1 1 calc R . . H50 H 0.2933 0.0795 0.3991 0.073 Uiso 1 1 calc R . . C41 C 0.21107(15) 0.10332(18) 0.43721(14) 0.0814(10) Uani 1 1 d . . . H51 H 0.1899 0.1496 0.4502 0.122 Uiso 1 1 calc R . . H52 H 0.2181 0.0703 0.4728 0.122 Uiso 1 1 calc R . . H53 H 0.1875 0.0754 0.4069 0.122 Uiso 1 1 calc R . . N3 N 0.24826(10) 0.21104(12) 0.25140(10) 0.0558(6) Uani 1 1 d . . . H18 H 0.2428 0.2101 0.2116 0.067 Uiso 1 1 calc R . . O3 O 0.24563(9) 0.07222(10) 0.19939(7) 0.0617(5) Uani 1 1 d . . . B2 B 0.2500 0.0000 0.15841(18) 0.0524(12) Uani 1 2 d S . . C42 C 0.31055(13) 0.00755(16) 0.11822(11) 0.0525(7) Uani 1 1 d . . . C43 C 0.32407(14) -0.04484(17) 0.07056(12) 0.0638(8) Uani 1 1 d . . . H19 H 0.2973 -0.0853 0.0623 0.077 Uiso 1 1 calc R . . C44 C 0.37552(17) -0.0395(2) 0.03492(15) 0.0809(10) Uani 1 1 d . . . H20 H 0.3831 -0.0759 0.0035 0.097 Uiso 1 1 calc R . . C45 C 0.41533(16) 0.0203(3) 0.04642(19) 0.0904(11) Uani 1 1 d . . . H21 H 0.4500 0.0248 0.0225 0.108 Uiso 1 1 calc R . . C46 C 0.40394(17) 0.0728(2) 0.0927(2) 0.0917(11) Uani 1 1 d . . . H22 H 0.4310 0.1130 0.1007 0.110 Uiso 1 1 calc R . . C47 C 0.35221(15) 0.06652(18) 0.12811(15) 0.0723(9) Uani 1 1 d . . . H23 H 0.3452 0.1031 0.1595 0.087 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 C1 0.097(2) 0.0418(18) 0.075(2) 0.0057(15) -0.0066(19) -0.0032(16) C2 0.073(2) 0.0472(18) 0.0639(18) 0.0116(14) 0.0009(16) 0.0073(15) C3 0.072(2) 0.0518(18) 0.0511(15) 0.0064(13) -0.0021(15) 0.0056(15) C4 0.0674(19) 0.0465(17) 0.0486(14) 0.0021(13) -0.0079(14) 0.0005(14) C5 0.0623(18) 0.0482(17) 0.0445(14) 0.0076(13) -0.0023(14) 0.0081(14) C6 0.0638(18) 0.0492(18) 0.0474(14) 0.0045(13) -0.0126(14) 0.0022(14) C7 0.0595(17) 0.0503(17) 0.0378(13) 0.0022(12) -0.0030(13) 0.0007(14) C8 0.0577(17) 0.0468(17) 0.0482(15) 0.0044(13) -0.0047(14) 0.0039(14) C9 0.0612(18) 0.0532(18) 0.0508(15) 0.0012(13) -0.0087(14) 0.0055(14) C10 0.0611(18) 0.0515(19) 0.0645(18) -0.0050(14) -0.0107(15) -0.0016(15) C11 0.071(2) 0.0448(17) 0.079(2) 0.0003(16) -0.0112(17) -0.0028(15) C12 0.099(3) 0.062(2) 0.086(2) 0.0276(18) -0.0010(19) 0.0166(19) C13 0.094(3) 0.055(2) 0.163(4) 0.032(2) 0.001(3) 0.0074(19) C14 0.100(3) 0.062(2) 0.0685(19) 0.0163(16) -0.0106(19) 0.0115(19) C15 0.113(3) 0.128(4) 0.085(2) -0.009(2) -0.009(2) -0.004(3) C16 0.079(2) 0.069(2) 0.0663(18) -0.0089(16) -0.0106(17) 0.0021(18) C17 0.119(3) 0.135(4) 0.086(2) 0.025(2) 0.015(2) 0.017(3) C18 0.092(3) 0.070(2) 0.092(2) -0.0177(19) -0.023(2) -0.005(2) C19 0.116(3) 0.075(3) 0.141(3) -0.039(2) -0.029(3) 0.008(2) C20 0.074(2) 0.0450(17) 0.0403(13) 0.0070(12) -0.0008(13) 0.0027(15) C21 0.071(2) 0.0542(19) 0.0662(18) 0.0099(14) -0.0084(16) 0.0012(17) C22 0.076(2) 0.072(2) 0.075(2) 0.0125(17) -0.0108(18) -0.011(2) C23 0.062(2) 0.111(3) 0.0630(19) 0.015(2) -0.0041(16) 0.005(2) C24 0.087(3) 0.091(3) 0.0594(18) 0.0059(18) -0.0004(19) 0.032(2) C25 0.089(2) 0.062(2) 0.0483(15) 0.0013(14) -0.0058(16) 0.0123(18) C26 0.069(2) 0.062(2) 0.0488(15) -0.0048(15) -0.0196(15) 0.0091(16) C27 0.103(3) 0.079(2) 0.083(2) -0.0212(19) -0.003(2) 0.017(2) C28 0.097(3) 0.134(4) 0.088(3) -0.038(3) 0.002(2) 0.032(3) C29 0.076(3) 0.170(5) 0.066(2) -0.005(3) -0.004(2) 0.011(3) C30 0.108(3) 0.132(4) 0.107(3) 0.034(3) 0.027(3) 0.017(3) C31 0.099(3) 0.091(3) 0.087(2) 0.017(2) 0.027(2) 0.020(2) N1 0.096(2) 0.0515(16) 0.0609(14) 0.0056(12) -0.0209(14) -0.0016(14) N2 0.0754(17) 0.0472(15) 0.0566(13) 0.0044(12) -0.0163(12) -0.0002(12) O1 0.0988(16) 0.0459(11) 0.0553(11) 0.0049(9) -0.0252(11) 0.0026(10) O2 0.0827(14) 0.0475(11) 0.0445(10) 0.0001(8) -0.0132(10) 0.0069(10) B1 0.082(3) 0.0390(18) 0.0442(16) 0.0018(14) -0.0135(17) 0.0047(17) C32 0.0708(19) 0.0361(16) 0.0656(17) -0.0009(13) 0.0012(15) 0.0008(14) C33 0.0627(18) 0.0447(17) 0.0529(16) -0.0058(13) 0.0050(14) -0.0028(14) C34 0.0535(17) 0.0449(16) 0.0461(14) -0.0027(12) -0.0004(12) 0.0002(13) C35 0.0527(16) 0.0384(15) 0.0450(13) 0.0041(12) -0.0016(12) -0.0009(13) C36 0.0529(16) 0.0460(16) 0.0384(13) -0.0034(12) -0.0011(12) 0.0047(13) C37 0.072(3) 0.039(2) 0.0410(18) 0.000 0.000 -0.0013(19) C38 0.105(3) 0.055(2) 0.0697(19) -0.0167(15) 0.0055(18) -0.0086(18) C39 0.146(4) 0.057(2) 0.103(3) -0.0236(19) 0.022(2) -0.022(2) C40 0.087(2) 0.0513(17) 0.0445(14) -0.0046(13) -0.0107(15) -0.0027(16) C41 0.110(3) 0.073(2) 0.0609(18) 0.0095(16) 0.0186(19) 0.001(2) N3 0.0752(16) 0.0440(14) 0.0482(12) 0.0011(11) -0.0051(11) 0.0021(12) O3 0.1020(15) 0.0442(10) 0.0388(9) 0.0000(8) -0.0049(10) 0.0105(10) B2 0.082(3) 0.038(2) 0.038(2) 0.000 0.000 0.009(2) C42 0.0674(19) 0.0444(16) 0.0457(14) 0.0077(13) -0.0089(14) 0.0085(15) C43 0.074(2) 0.0628(19) 0.0548(16) 0.0040(15) 0.0027(16) 0.0060(16) C44 0.083(3) 0.087(3) 0.072(2) 0.0076(19) 0.014(2) 0.024(2) C45 0.066(2) 0.099(3) 0.106(3) 0.028(2) 0.014(2) 0.020(2) C46 0.065(2) 0.077(3) 0.134(3) 0.014(2) -0.005(2) 0.002(2) C47 0.070(2) 0.061(2) 0.086(2) 0.0025(17) -0.0101(19) 0.0084(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.346(3) . ? C1 C2 1.361(4) . ? C1 H1 0.9300 . ? C2 C3 1.400(4) . ? C2 C12 1.501(4) . ? C3 C4 1.398(3) . ? C3 C14 1.531(4) . ? C4 N1 1.367(3) . ? C4 C5 1.425(3) . ? C5 O1 1.320(3) . ? C5 C6 1.370(3) . ? C6 C7 1.376(3) . ? C6 H2 0.9300 . ? C7 O2 1.322(3) . ? C7 C8 1.422(3) . ? C8 N2 1.369(3) . ? C8 C9 1.402(3) . ? C9 C10 1.396(4) . ? C9 C16 1.516(4) . ? C10 C11 1.366(4) . ? C10 C18 1.504(4) . ? C11 N2 1.339(3) . ? C11 H3 0.9300 . ? C12 C13 1.511(4) . ? C12 H24 0.9700 . ? C12 H25 0.9700 . ? C13 H26 0.9600 . ? C13 H27 0.9600 . ? C13 H28 0.9600 . ? C14 C15 1.482(4) . ? C14 H29 0.9700 . ? C14 H30 0.9700 . ? C15 H31 0.9600 . ? C15 H32 0.9600 . ? C15 H33 0.9600 . ? C16 C17 1.485(4) . ? C16 H34 0.9700 . ? C16 H35 0.9700 . ? C17 H36 0.9600 . ? C17 H37 0.9600 . ? C17 H38 0.9600 . ? C18 C19 1.480(4) . ? C18 H39 0.9700 . ? C18 H40 0.9700 . ? C19 H41 0.9600 . ? C19 H42 0.9600 . ? C19 H43 0.9600 . ? C20 C25 1.384(4) . ? C20 C21 1.386(4) . ? C20 B1 1.603(4) . ? C21 C22 1.372(4) . ? C21 H4 0.9300 . ? C22 C23 1.358(4) . ? C22 H5 0.9300 . ? C23 C24 1.371(4) . ? C23 H6 0.9300 . ? C24 C25 1.379(4) . ? C24 H7 0.9300 . ? C25 H8 0.9300 . ? C26 C31 1.374(4) . ? C26 C27 1.377(4) . ? C26 B1 1.603(4) . ? C27 C28 1.391(5) . ? C27 H9 0.9300 . ? C28 C29 1.350(5) . ? C28 H10 0.9300 . ? C29 C30 1.340(5) . ? C29 H11 0.9300 . ? C30 C31 1.378(5) . ? C30 H12 0.9300 . ? C31 H13 0.9300 . ? N1 H14 0.8600 . ? N2 H15 0.8600 . ? O1 B1 1.506(3) . ? O2 B1 1.522(3) . ? C32 N3 1.340(3) . ? C32 C33 1.375(3) . ? C32 H16 0.9300 . ? C33 C34 1.400(3) . ? C33 C38 1.499(4) . ? C34 C35 1.399(3) . ? C34 C40 1.497(3) . ? C35 N3 1.370(3) . ? C35 C36 1.426(3) . ? C36 O3 1.315(3) . ? C36 C37 1.377(3) . ? C37 C36 1.377(3) 2 ? C37 H17 0.9300 . ? C38 C39 1.490(4) . ? C38 H44 0.9700 . ? C38 H45 0.9700 . ? C39 H46 0.9600 . ? C39 H47 0.9600 . ? C39 H48 0.9600 . ? C40 C41 1.514(4) . ? C40 H49 0.9700 . ? C40 H50 0.9700 . ? C41 H51 0.9600 . ? C41 H52 0.9600 . ? C41 H53 0.9600 . ? N3 H18 0.8600 . ? O3 B2 1.515(3) . ? B2 O3 1.515(3) 2 ? B2 C42 1.606(3) . ? B2 C42 1.606(3) 2 ? C42 C47 1.385(4) . ? C42 C43 1.388(4) . ? C43 C44 1.380(4) . ? C43 H19 0.9300 . ? C44 C45 1.374(5) . ? C44 H20 0.9300 . ? C45 C46 1.358(5) . ? C45 H21 0.9300 . ? C46 C47 1.384(4) . ? C46 H22 0.9300 . ? C47 H23 0.9300 . ? 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 N1 C1 C2 108.8(3) . . ? N1 C1 H1 125.6 . . ? C2 C1 H1 125.6 . . ? C1 C2 C3 107.2(2) . . ? C1 C2 C12 126.5(3) . . ? C3 C2 C12 126.3(3) . . ? C2 C3 C4 107.5(2) . . ? C2 C3 C14 124.3(2) . . ? C4 C3 C14 128.2(3) . . ? N1 C4 C3 106.2(2) . . ? N1 C4 C5 118.4(2) . . ? C3 C4 C5 135.4(3) . . ? O1 C5 C6 120.1(2) . . ? O1 C5 C4 113.1(2) . . ? C6 C5 C4 126.7(2) . . ? C5 C6 C7 121.8(2) . . ? C5 C6 H2 119.1 . . ? C7 C6 H2 119.1 . . ? O2 C7 C6 120.0(2) . . ? O2 C7 C8 113.7(2) . . ? C6 C7 C8 126.2(2) . . ? N2 C8 C9 106.4(2) . . ? N2 C8 C7 118.7(2) . . ? C9 C8 C7 134.8(2) . . ? C10 C9 C8 107.3(2) . . ? C10 C9 C16 124.1(2) . . ? C8 C9 C16 128.6(2) . . ? C11 C10 C9 107.2(2) . . ? C11 C10 C18 126.2(3) . . ? C9 C10 C18 126.7(3) . . ? N2 C11 C10 109.2(2) . . ? N2 C11 H3 125.4 . . ? C10 C11 H3 125.4 . . ? C2 C12 C13 114.6(3) . . ? C2 C12 H24 108.6 . . ? C13 C12 H24 108.6 . . ? C2 C12 H25 108.6 . . ? C13 C12 H25 108.6 . . ? H24 C12 H25 107.6 . . ? C12 C13 H26 109.5 . . ? C12 C13 H27 109.5 . . ? H26 C13 H27 109.5 . . ? C12 C13 H28 109.5 . . ? H26 C13 H28 109.5 . . ? H27 C13 H28 109.5 . . ? C15 C14 C3 111.8(3) . . ? C15 C14 H29 109.3 . . ? C3 C14 H29 109.3 . . ? C15 C14 H30 109.3 . . ? C3 C14 H30 109.3 . . ? H29 C14 H30 107.9 . . ? C14 C15 H31 109.5 . . ? C14 C15 H32 109.5 . . ? H31 C15 H32 109.5 . . ? C14 C15 H33 109.5 . . ? H31 C15 H33 109.5 . . ? H32 C15 H33 109.5 . . ? C17 C16 C9 111.4(3) . . ? C17 C16 H34 109.3 . . ? C9 C16 H34 109.3 . . ? C17 C16 H35 109.3 . . ? C9 C16 H35 109.3 . . ? H34 C16 H35 108.0 . . ? C16 C17 H36 109.5 . . ? C16 C17 H37 109.5 . . ? H36 C17 H37 109.5 . . ? C16 C17 H38 109.5 . . ? H36 C17 H38 109.5 . . ? H37 C17 H38 109.5 . . ? C19 C18 C10 114.5(3) . . ? C19 C18 H39 108.6 . . ? C10 C18 H39 108.6 . . ? C19 C18 H40 108.6 . . ? C10 C18 H40 108.6 . . ? H39 C18 H40 107.6 . . ? C18 C19 H41 109.5 . . ? C18 C19 H42 109.5 . . ? H41 C19 H42 109.5 . . ? C18 C19 H43 109.5 . . ? H41 C19 H43 109.5 . . ? H42 C19 H43 109.5 . . ? C25 C20 C21 115.6(3) . . ? C25 C20 B1 125.2(3) . . ? C21 C20 B1 119.2(2) . . ? C22 C21 C20 122.9(3) . . ? C22 C21 H4 118.5 . . ? C20 C21 H4 118.5 . . ? C23 C22 C21 119.9(3) . . ? C23 C22 H5 120.0 . . ? C21 C22 H5 120.0 . . ? C22 C23 C24 119.3(3) . . ? C22 C23 H6 120.4 . . ? C24 C23 H6 120.4 . . ? C23 C24 C25 120.3(3) . . ? C23 C24 H7 119.8 . . ? C25 C24 H7 119.8 . . ? C24 C25 C20 121.9(3) . . ? C24 C25 H8 119.0 . . ? C20 C25 H8 119.0 . . ? C31 C26 C27 114.9(3) . . ? C31 C26 B1 119.9(3) . . ? C27 C26 B1 125.1(3) . . ? C26 C27 C28 122.3(4) . . ? C26 C27 H9 118.9 . . ? C28 C27 H9 118.9 . . ? C29 C28 C27 120.1(4) . . ? C29 C28 H10 119.9 . . ? C27 C28 H10 119.9 . . ? C30 C29 C28 119.4(4) . . ? C30 C29 H11 120.3 . . ? C28 C29 H11 120.3 . . ? C29 C30 C31 120.4(4) . . ? C29 C30 H12 119.8 . . ? C31 C30 H12 119.8 . . ? C26 C31 C30 122.9(4) . . ? C26 C31 H13 118.5 . . ? C30 C31 H13 118.5 . . ? C1 N1 C4 110.2(2) . . ? C1 N1 H14 124.9 . . ? C4 N1 H14 124.9 . . ? C11 N2 C8 109.9(2) . . ? C11 N2 H15 125.0 . . ? C8 N2 H15 125.0 . . ? C5 O1 B1 121.2(2) . . ? C7 O2 B1 120.1(2) . . ? O1 B1 O2 108.0(2) . . ? O1 B1 C26 110.4(2) . . ? O2 B1 C26 108.6(2) . . ? O1 B1 C20 106.6(2) . . ? O2 B1 C20 108.7(2) . . ? C26 B1 C20 114.4(2) . . ? N3 C32 C33 108.9(2) . . ? N3 C32 H16 125.5 . . ? C33 C32 H16 125.5 . . ? C32 C33 C34 107.1(2) . . ? C32 C33 C38 126.3(3) . . ? C34 C33 C38 126.6(2) . . ? C33 C34 C35 107.3(2) . . ? C33 C34 C40 124.3(2) . . ? C35 C34 C40 128.4(2) . . ? N3 C35 C34 106.7(2) . . ? N3 C35 C36 118.8(2) . . ? C34 C35 C36 134.5(2) . . ? O3 C36 C37 120.6(2) . . ? O3 C36 C35 113.7(2) . . ? C37 C36 C35 125.6(2) . . ? C36 C37 C36 121.3(3) 2 . ? C36 C37 H17 119.4 2 . ? C36 C37 H17 119.4 . . ? C39 C38 C33 114.6(3) . . ? C39 C38 H44 108.6 . . ? C33 C38 H44 108.6 . . ? C39 C38 H45 108.6 . . ? C33 C38 H45 108.6 . . ? H44 C38 H45 107.6 . . ? C38 C39 H46 109.5 . . ? C38 C39 H47 109.5 . . ? H46 C39 H47 109.5 . . ? C38 C39 H48 109.5 . . ? H46 C39 H48 109.5 . . ? H47 C39 H48 109.5 . . ? C34 C40 C41 112.6(2) . . ? C34 C40 H49 109.1 . . ? C41 C40 H49 109.1 . . ? C34 C40 H50 109.1 . . ? C41 C40 H50 109.1 . . ? H49 C40 H50 107.8 . . ? C40 C41 H51 109.5 . . ? C40 C41 H52 109.5 . . ? H51 C41 H52 109.5 . . ? C40 C41 H53 109.5 . . ? H51 C41 H53 109.5 . . ? H52 C41 H53 109.5 . . ? C32 N3 C35 110.0(2) . . ? C32 N3 H18 125.0 . . ? C35 N3 H18 125.0 . . ? C36 O3 B2 123.5(2) . . ? O3 B2 O3 109.3(3) . 2 ? O3 B2 C42 107.37(12) . . ? O3 B2 C42 108.71(11) 2 . ? O3 B2 C42 108.71(11) . 2 ? O3 B2 C42 107.37(12) 2 2 ? C42 B2 C42 115.3(3) . 2 ? C47 C42 C43 115.7(3) . . ? C47 C42 B2 122.7(2) . . ? C43 C42 B2 121.6(3) . . ? C44 C43 C42 122.9(3) . . ? C44 C43 H19 118.6 . . ? C42 C43 H19 118.6 . . ? C45 C44 C43 119.2(3) . . ? C45 C44 H20 120.4 . . ? C43 C44 H20 120.4 . . ? C46 C45 C44 119.9(4) . . ? C46 C45 H21 120.1 . . ? C44 C45 H21 120.1 . . ? C45 C46 C47 120.3(4) . . ? C45 C46 H22 119.9 . . ? C47 C46 H22 119.9 . . ? C46 C47 C42 122.1(3) . . ? C46 C47 H23 119.0 . . ? C42 C47 H23 119.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.7(4) . . . . ? N1 C1 C2 C12 -179.7(3) . . . . ? C1 C2 C3 C4 0.7(3) . . . . ? C12 C2 C3 C4 179.6(3) . . . . ? C1 C2 C3 C14 -178.9(3) . . . . ? C12 C2 C3 C14 0.0(5) . . . . ? C2 C3 C4 N1 -0.4(3) . . . . ? C14 C3 C4 N1 179.2(3) . . . . ? C2 C3 C4 C5 -178.0(3) . . . . ? C14 C3 C4 C5 1.5(5) . . . . ? N1 C4 C5 O1 4.4(4) . . . . ? C3 C4 C5 O1 -178.2(3) . . . . ? N1 C4 C5 C6 -177.3(3) . . . . ? C3 C4 C5 C6 0.2(5) . . . . ? O1 C5 C6 C7 5.0(4) . . . . ? C4 C5 C6 C7 -173.2(3) . . . . ? C5 C6 C7 O2 -2.2(4) . . . . ? C5 C6 C7 C8 174.9(3) . . . . ? O2 C7 C8 N2 -7.5(3) . . . . ? C6 C7 C8 N2 175.3(2) . . . . ? O2 C7 C8 C9 169.9(3) . . . . ? C6 C7 C8 C9 -7.3(5) . . . . ? N2 C8 C9 C10 1.7(3) . . . . ? C7 C8 C9 C10 -176.0(3) . . . . ? N2 C8 C9 C16 -178.8(3) . . . . ? C7 C8 C9 C16 3.5(5) . . . . ? C8 C9 C10 C11 -1.4(3) . . . . ? C16 C9 C10 C11 179.0(3) . . . . ? C8 C9 C10 C18 178.3(3) . . . . ? C16 C9 C10 C18 -1.3(5) . . . . ? C9 C10 C11 N2 0.6(3) . . . . ? C18 C10 C11 N2 -179.1(3) . . . . ? C1 C2 C12 C13 2.1(5) . . . . ? C3 C2 C12 C13 -176.7(3) . . . . ? C2 C3 C14 C15 -93.8(4) . . . . ? C4 C3 C14 C15 86.6(4) . . . . ? C10 C9 C16 C17 89.9(4) . . . . ? C8 C9 C16 C17 -89.5(4) . . . . ? C11 C10 C18 C19 9.1(5) . . . . ? C9 C10 C18 C19 -170.5(3) . . . . ? C25 C20 C21 C22 -1.4(4) . . . . ? B1 C20 C21 C22 179.7(3) . . . . ? C20 C21 C22 C23 0.8(4) . . . . ? C21 C22 C23 C24 0.3(5) . . . . ? C22 C23 C24 C25 -0.7(5) . . . . ? C23 C24 C25 C20 0.2(4) . . . . ? C21 C20 C25 C24 0.9(4) . . . . ? B1 C20 C25 C24 179.7(3) . . . . ? C31 C26 C27 C28 -0.1(5) . . . . ? B1 C26 C27 C28 177.7(3) . . . . ? C26 C27 C28 C29 -0.1(6) . . . . ? C27 C28 C29 C30 0.3(6) . . . . ? C28 C29 C30 C31 -0.2(7) . . . . ? C27 C26 C31 C30 0.2(5) . . . . ? B1 C26 C31 C30 -177.8(3) . . . . ? C29 C30 C31 C26 0.0(6) . . . . ? C2 C1 N1 C4 0.5(4) . . . . ? C3 C4 N1 C1 -0.1(3) . . . . ? C5 C4 N1 C1 178.1(2) . . . . ? C10 C11 N2 C8 0.5(3) . . . . ? C9 C8 N2 C11 -1.4(3) . . . . ? C7 C8 N2 C11 176.8(2) . . . . ? C6 C5 O1 B1 13.6(4) . . . . ? C4 C5 O1 B1 -168.0(2) . . . . ? C6 C7 O2 B1 -18.7(4) . . . . ? C8 C7 O2 B1 164.0(2) . . . . ? C5 O1 B1 O2 -30.2(4) . . . . ? C5 O1 B1 C26 88.4(3) . . . . ? C5 O1 B1 C20 -146.8(2) . . . . ? C7 O2 B1 O1 32.7(3) . . . . ? C7 O2 B1 C26 -87.1(3) . . . . ? C7 O2 B1 C20 147.9(2) . . . . ? C31 C26 B1 O1 -166.2(3) . . . . ? C27 C26 B1 O1 16.1(4) . . . . ? C31 C26 B1 O2 -47.9(3) . . . . ? C27 C26 B1 O2 134.3(3) . . . . ? C31 C26 B1 C20 73.6(3) . . . . ? C27 C26 B1 C20 -104.2(3) . . . . ? C25 C20 B1 O1 138.7(2) . . . . ? C21 C20 B1 O1 -42.5(3) . . . . ? C25 C20 B1 O2 22.6(3) . . . . ? C21 C20 B1 O2 -158.6(2) . . . . ? C25 C20 B1 C26 -98.9(3) . . . . ? C21 C20 B1 C26 79.9(3) . . . . ? N3 C32 C33 C34 -0.7(3) . . . . ? N3 C32 C33 C38 177.9(3) . . . . ? C32 C33 C34 C35 -0.1(3) . . . . ? C38 C33 C34 C35 -178.7(3) . . . . ? C32 C33 C34 C40 -178.2(3) . . . . ? C38 C33 C34 C40 3.3(5) . . . . ? C33 C34 C35 N3 0.8(3) . . . . ? C40 C34 C35 N3 178.8(3) . . . . ? C33 C34 C35 C36 178.8(3) . . . . ? C40 C34 C35 C36 -3.2(5) . . . . ? N3 C35 C36 O3 3.8(3) . . . . ? C34 C35 C36 O3 -174.0(3) . . . . ? N3 C35 C36 C37 -175.0(2) . . . . ? C34 C35 C36 C37 7.2(5) . . . . ? O3 C36 C37 C36 4.97(17) . . . 2 ? C35 C36 C37 C36 -176.3(3) . . . 2 ? C32 C33 C38 C39 1.5(5) . . . . ? C34 C33 C38 C39 179.8(3) . . . . ? C33 C34 C40 C41 94.0(3) . . . . ? C35 C34 C40 C41 -83.7(3) . . . . ? C33 C32 N3 C35 1.2(3) . . . . ? C34 C35 N3 C32 -1.3(3) . . . . ? C36 C35 N3 C32 -179.6(2) . . . . ? C37 C36 O3 B2 -9.9(3) . . . . ? C35 C36 O3 B2 171.27(19) . . . . ? C36 O3 B2 O3 4.99(17) . . . 2 ? C36 O3 B2 C42 -112.8(3) . . . . ? C36 O3 B2 C42 121.9(3) . . . 2 ? O3 B2 C42 C47 7.2(3) . . . . ? O3 B2 C42 C47 -111.0(2) 2 . . . ? C42 B2 C42 C47 128.5(3) 2 . . . ? O3 B2 C42 C43 -172.2(2) . . . . ? O3 B2 C42 C43 69.6(3) 2 . . . ? C42 B2 C42 C43 -50.9(2) 2 . . . ? C47 C42 C43 C44 0.1(4) . . . . ? B2 C42 C43 C44 179.5(2) . . . . ? C42 C43 C44 C45 -0.3(5) . . . . ? C43 C44 C45 C46 0.5(5) . . . . ? C44 C45 C46 C47 -0.4(5) . . . . ? C45 C46 C47 C42 0.1(5) . . . . ? C43 C42 C47 C46 0.0(4) . . . . ? B2 C42 C47 C46 -179.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.216 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.032 #============================================================================== # End of CIF #============================================================================== data_shelxs _database_code_depnum_ccdc_archive 'CCDC 759620' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H33 B I2 N2 O2' _chemical_formula_weight 730.20 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.575(3) _cell_length_b 16.463(6) _cell_length_c 19.426(5) _cell_angle_alpha 97.835(12) _cell_angle_beta 100.782(11) _cell_angle_gamma 98.801(14) _cell_volume 2929.3(16) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour pink _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 2.178 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.425 _exptl_absorpt_correction_T_max 0.635 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _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 \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28712 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.49 _reflns_number_total 13289 _reflns_number_gt 10908 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+2.6880P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13289 _refine_ls_number_parameters 733 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0873 _refine_ls_wR_factor_gt 0.0772 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 I1 I 0.65657(2) 0.164944(13) 0.300534(10) 0.02614(6) Uani 1 1 d . . . I2 I 0.31309(2) 0.331916(12) 0.199137(9) 0.02278(6) Uani 1 1 d . . . I3 I -0.12365(2) 0.110691(15) -0.347990(10) 0.02784(6) Uani 1 1 d . . . I4 I 1.11638(2) 0.380768(15) 0.841039(10) 0.02912(6) Uani 1 1 d . . . O8 O 0.7979(2) 0.30012(12) 0.56924(10) 0.0139(4) Uani 1 1 d . . . O6 O 0.3347(2) 0.20735(12) 0.04634(10) 0.0150(4) Uani 1 1 d . . . O7 O 0.1962(2) 0.19925(12) -0.07491(10) 0.0141(4) Uani 1 1 d . . . C8 C 0.7220(3) 0.15911(17) 0.48797(13) 0.0131(5) Uani 1 1 d . . . C87 C -0.0416(3) 0.0673(2) -0.25677(15) 0.0233(6) Uani 1 1 d . . . O9 O 0.6499(2) 0.29064(12) 0.44991(10) 0.0148(4) Uani 1 1 d . . . C89 C 0.1273(3) 0.34057(18) 0.01625(15) 0.0174(6) Uani 1 1 d . . . H1 H 0.0598 0.2912 0.0042 0.021 Uiso 1 1 calc R . . C74 C 0.8646(3) 0.15739(18) 0.48067(15) 0.0173(6) Uani 1 1 d . . . H2 H 0.9323 0.2067 0.4930 0.021 Uiso 1 1 calc R . . C13 C 0.2632(3) 0.07977(18) -0.03239(14) 0.0166(5) Uani 1 1 d . . . H3 H 0.2671 0.0234 -0.0423 0.020 Uiso 1 1 calc R . . C14 C 0.0944(3) 0.07331(18) -0.14871(15) 0.0180(6) Uani 1 1 d . A . C16 C 0.1872(3) 0.11758(17) -0.08365(14) 0.0144(5) Uani 1 1 d . . . C17 C 0.5253(3) 0.23901(18) 0.61619(16) 0.0189(6) Uani 1 1 d . . . H4 H 0.6124 0.2466 0.6490 0.023 Uiso 1 1 calc R . . C18 C 0.7231(3) 0.41892(17) 0.52868(14) 0.0155(5) Uani 1 1 d . . . H5 H 0.7189 0.4753 0.5386 0.019 Uiso 1 1 calc R . . C19 C 0.2691(3) 0.33946(17) 0.00819(13) 0.0132(5) Uani 1 1 d . . . C20 C 0.4292(3) 0.54232(18) 0.28363(15) 0.0201(6) Uani 1 1 d . . . H6 H 0.4217 0.5901 0.3170 0.024 Uiso 1 1 calc R . . H7 H 0.3349 0.5221 0.2524 0.024 Uiso 1 1 calc R . . C21 C 0.4680(3) 0.26235(16) -0.04418(15) 0.0141(5) Uani 1 1 d . . . C22 C 0.8015(3) 0.38132(17) 0.57926(14) 0.0139(5) Uani 1 1 d . . . C23 C 0.5753(3) 0.40388(17) 0.40465(14) 0.0150(5) Uani 1 1 d . . . C24 C 0.6426(3) 0.56606(17) 0.43436(15) 0.0178(6) Uani 1 1 d . . . H8 H 0.6397 0.5663 0.4840 0.021 Uiso 1 1 calc R . . H9 H 0.5959 0.6106 0.4188 0.021 Uiso 1 1 calc R . . B93 B 0.3185(3) 0.25346(19) -0.01736(16) 0.0140(6) Uani 1 1 d . . . C29 C 1.0256(3) 0.4277(2) 0.75298(15) 0.0227(6) Uani 1 1 d . . . C30 C 0.4240(3) 0.01378(17) 0.10462(14) 0.0159(5) Uani 1 1 d . . . N14 N 0.9464(3) 0.37747(16) 0.69410(12) 0.0183(5) Uani 1 1 d . . . H63 H 0.9321 0.3239 0.6875 0.022 Uiso 1 1 calc R . . C34 C 0.4768(3) 0.26142(17) -0.11506(15) 0.0180(6) Uani 1 1 d . . . H10 H 0.3921 0.2536 -0.1496 0.022 Uiso 1 1 calc R . . C35 C 0.3331(3) 0.12666(17) 0.03361(14) 0.0137(5) Uani 1 1 d . . . C36 C 0.8909(3) 0.42484(18) 0.64525(15) 0.0171(6) Uani 1 1 d . . . C37 C 0.5448(3) 0.10801(18) 0.20033(14) 0.0174(6) Uani 1 1 d . . . N15 N 0.4814(3) 0.15004(15) 0.15180(12) 0.0180(5) Uani 1 1 d . . . H64 H 0.4870 0.2032 0.1573 0.022 Uiso 1 1 calc R . . C39 C 0.5997(3) 0.27542(18) 0.00581(16) 0.0198(6) Uani 1 1 d . . . H11 H 0.5982 0.2766 0.0537 0.024 Uiso 1 1 calc R . . C40 C 0.5579(3) -0.04390(19) 0.21259(16) 0.0228(6) Uani 1 1 d . . . H12 H 0.6512 -0.0226 0.2443 0.027 Uiso 1 1 calc R . . H13 H 0.5682 -0.0908 0.1790 0.027 Uiso 1 1 calc R . . C41 C 0.4324(3) 0.38987(18) 0.29798(14) 0.0166(5) Uani 1 1 d . . . C42 C 0.5128(3) 0.02302(17) 0.17287(14) 0.0165(5) Uani 1 1 d . . . C43 C 0.9074(3) 0.08393(19) 0.45552(16) 0.0209(6) Uani 1 1 d . . . H14 H 1.0028 0.0844 0.4515 0.025 Uiso 1 1 calc R . . C45 C 0.3924(3) 0.22313(19) 0.49706(16) 0.0218(6) Uani 1 1 d . . . H15 H 0.3894 0.2202 0.4486 0.026 Uiso 1 1 calc R . . N12 N 0.0497(3) 0.11846(16) -0.20125(12) 0.0182(5) Uani 1 1 d . . . H65 H 0.0763 0.1713 -0.1988 0.022 Uiso 1 1 calc R . . N13 N 0.4945(3) 0.34774(15) 0.34694(12) 0.0159(5) Uani 1 1 d . . . H66 H 0.4848 0.2944 0.3426 0.019 Uiso 1 1 calc R . . C49 C 0.7368(3) 0.28442(19) -0.0851(2) 0.0270(7) Uani 1 1 d . . . H16 H 0.8253 0.2913 -0.0988 0.032 Uiso 1 1 calc R . . C50 C 0.8068(3) 0.00950(19) 0.43625(16) 0.0227(6) Uani 1 1 d . . . H17 H 0.8347 -0.0397 0.4190 0.027 Uiso 1 1 calc R . . C80 C 0.0209(4) -0.0089(2) -0.17203(17) 0.0331(8) Uani 1 1 d . . . C52 C 0.4064(3) 0.09408(17) 0.09201(14) 0.0146(5) Uani 1 1 d . . . C53 C 1.0973(4) 0.5849(3) 0.79988(19) 0.0373(8) Uani 1 1 d . . . H18 H 1.0354 0.6264 0.7987 0.045 Uiso 1 1 calc R . . H19 H 1.1097 0.5693 0.8467 0.045 Uiso 1 1 calc R . . B92 B 0.6733(3) 0.24548(19) 0.51385(16) 0.0130(6) Uani 1 1 d . . . C55 C 0.5626(3) 0.48433(17) 0.39138(14) 0.0152(5) Uani 1 1 d . . . C57 C 0.6660(3) 0.00935(19) 0.44288(16) 0.0214(6) Uani 1 1 d . . . H20 H 0.5986 -0.0401 0.4302 0.026 Uiso 1 1 calc R . . C58 C 0.7320(3) 0.28657(19) -0.01454(18) 0.0249(7) Uani 1 1 d . . . H21 H 0.8175 0.2955 0.0196 0.030 Uiso 1 1 calc R . . C59 C 0.4487(4) -0.0736(2) 0.25566(18) 0.0332(8) Uani 1 1 d . . . H22 H 0.4426 -0.0281 0.2909 0.050 Uiso 1 1 calc R . . H23 H 0.4791 -0.1179 0.2787 0.050 Uiso 1 1 calc R . . H24 H 0.3556 -0.0935 0.2246 0.050 Uiso 1 1 calc R . . C60 C 0.0851(3) 0.41417(19) 0.04195(15) 0.0210(6) Uani 1 1 d . . . H25 H -0.0102 0.4135 0.0463 0.025 Uiso 1 1 calc R . . C61 C 0.5271(3) 0.23688(16) 0.54428(15) 0.0149(5) Uani 1 1 d . . . C62 C 0.6512(3) 0.37133(17) 0.46320(14) 0.0135(5) Uani 1 1 d . . . C63 C 0.2632(3) 0.2138(2) 0.52054(19) 0.0275(7) Uani 1 1 d . . . H26 H 0.1753 0.2048 0.4881 0.033 Uiso 1 1 calc R . . C64 C 0.1851(3) 0.48885(19) 0.06119(16) 0.0220(6) Uani 1 1 d . . . H27 H 0.1572 0.5379 0.0789 0.026 Uiso 1 1 calc R . . C65 C 0.9070(4) 0.5859(2) 0.64855(18) 0.0289(7) Uani 1 1 d . . . H28 H 0.8090 0.5751 0.6204 0.035 Uiso 1 1 calc R . . H29 H 0.9138 0.6303 0.6880 0.035 Uiso 1 1 calc R . . C66 C 0.2663(3) 0.2179(2) 0.5925(2) 0.0303(8) Uani 1 1 d . . . H30 H 0.1803 0.2124 0.6086 0.036 Uiso 1 1 calc R . . C67 C 0.3958(4) 0.2300(2) 0.63999(19) 0.0272(7) Uani 1 1 d . . . H31 H 0.3975 0.2323 0.6882 0.033 Uiso 1 1 calc R . . C68 C 0.3255(3) 0.48920(18) 0.05370(16) 0.0211(6) Uani 1 1 d . . . H32 H 0.3927 0.5387 0.0661 0.025 Uiso 1 1 calc R . . C69 C 0.8004(3) 0.5816(2) 0.42654(18) 0.0268(7) Uani 1 1 d . . . H33 H 0.8467 0.5376 0.4420 0.040 Uiso 1 1 calc R . . H34 H 0.8499 0.6340 0.4551 0.040 Uiso 1 1 calc R . . H35 H 0.8034 0.5831 0.3776 0.040 Uiso 1 1 calc R . . C70 C 0.6094(3) 0.27195(19) -0.13544(18) 0.0245(6) Uani 1 1 d . . . H36 H 0.6123 0.2706 -0.1832 0.029 Uiso 1 1 calc R . . C71 C 0.9376(3) 0.5085(2) 0.67703(16) 0.0231(6) Uani 1 1 d . . . C72 C 0.3528(3) -0.06791(17) 0.05901(15) 0.0176(6) Uani 1 1 d . . . H37 H 0.4014 -0.1116 0.0751 0.021 Uiso 1 1 calc R . . H38 H 0.3616 -0.0659 0.0103 0.021 Uiso 1 1 calc R . . C73 C 0.3670(3) 0.41534(18) 0.02758(15) 0.0184(6) Uani 1 1 d . . . H39 H 0.4622 0.4166 0.0229 0.022 Uiso 1 1 calc R . . C75 C 0.6242(3) 0.08337(17) 0.46855(14) 0.0170(5) Uani 1 1 d . . . H40 H 0.5288 0.0823 0.4728 0.020 Uiso 1 1 calc R . . C76 C 1.0100(4) 0.6135(3) 0.6037(2) 0.0424(9) Uani 1 1 d . . . H41 H 1.1074 0.6202 0.6302 0.064 Uiso 1 1 calc R . . H42 H 0.9930 0.6657 0.5903 0.064 Uiso 1 1 calc R . . H43 H 0.9958 0.5723 0.5617 0.064 Uiso 1 1 calc R . . C88 C 0.4712(3) 0.47499(17) 0.32386(14) 0.0157(5) Uani 1 1 d . . . C81 C 0.1917(3) -0.0885(2) 0.06179(18) 0.0255(7) Uani 1 1 d . . . H44 H 0.1832 -0.0950 0.1093 0.038 Uiso 1 1 calc R . . H45 H 0.1469 -0.1393 0.0296 0.038 Uiso 1 1 calc R . . H46 H 0.1447 -0.0438 0.0482 0.038 Uiso 1 1 calc R . . C82 C 0.0128(5) -0.0798(3) -0.1293(3) 0.0166(11) Uani 0.730(11) 1 d P A 3 H93 H -0.0816 -0.1155 -0.1453 0.020 Uiso 0.730(11) 1 calc PR A 3 H94 H 0.0232 -0.0568 -0.0795 0.020 Uiso 0.730(11) 1 calc PR A 3 C77 C 0.5389(4) 0.5695(2) 0.23935(18) 0.0308(7) Uani 1 1 d . . . H49 H 0.6325 0.5891 0.2700 0.046 Uiso 1 1 calc R . . H50 H 0.5097 0.6136 0.2156 0.046 Uiso 1 1 calc R . . H51 H 0.5431 0.5230 0.2047 0.046 Uiso 1 1 calc R . . C83 C -0.0665(4) -0.0129(2) -0.24078(18) 0.0374(9) Uani 1 1 d . A . C84 C 0.1296(5) -0.1324(3) -0.1366(2) 0.0253(13) Uani 0.730(11) 1 d P A 3 H95 H 0.1202 -0.1552 -0.1858 0.038 Uiso 0.730(11) 1 calc PR A 3 H96 H 0.1185 -0.1769 -0.1098 0.038 Uiso 0.730(11) 1 calc PR A 3 H97 H 0.2233 -0.0980 -0.1188 0.038 Uiso 0.730(11) 1 calc PR A 3 C85 C -0.1790(5) -0.0863(3) -0.2827(2) 0.0250(11) Uani 0.728(9) 1 d P A 1 H83 H -0.2382 -0.0680 -0.3217 0.030 Uiso 0.728(9) 1 calc PR A 1 H84 H -0.2416 -0.1058 -0.2521 0.030 Uiso 0.728(9) 1 calc PR A 1 C78 C 1.2395(5) 0.6223(3) 0.7886(2) 0.0543(12) Uani 1 1 d . . . H57 H 1.3022 0.5821 0.7909 0.081 Uiso 1 1 calc R . . H58 H 1.2810 0.6701 0.8249 0.081 Uiso 1 1 calc R . . H59 H 1.2279 0.6392 0.7428 0.081 Uiso 1 1 calc R . . C86 C -0.1133(5) -0.1586(3) -0.3125(2) 0.0306(13) Uani 0.728(9) 1 d P A 1 H85 H -0.0412 -0.1382 -0.3375 0.046 Uiso 0.728(9) 1 calc PR A 1 H86 H -0.1877 -0.1994 -0.3446 0.046 Uiso 0.728(9) 1 calc PR A 1 H87 H -0.0694 -0.1838 -0.2742 0.046 Uiso 0.728(9) 1 calc PR A 1 C79 C 1.0242(3) 0.5098(2) 0.74554(16) 0.0273(7) Uani 1 1 d . . . C90 C -0.0955(17) -0.0840(9) -0.3030(7) 0.036(4) Uani 0.272(9) 1 d P A 2 H88 H -0.1011 -0.0651 -0.3485 0.043 Uiso 0.272(9) 1 calc PR A 2 H89 H -0.0271 -0.1217 -0.2976 0.043 Uiso 0.272(9) 1 calc PR A 2 C92 C 0.0930(14) -0.0849(8) -0.1529(7) 0.027(4) Uani 0.270(11) 1 d P A 4 H98 H 0.0875 -0.1265 -0.1942 0.032 Uiso 0.270(11) 1 calc PR A 4 H99 H 0.1921 -0.0680 -0.1264 0.032 Uiso 0.270(11) 1 calc PR A 4 C93 C -0.0082(17) -0.1115(12) -0.1083(9) 0.036(4) Uani 0.270(11) 1 d P A 4 H100 H 0.0172 -0.0752 -0.0631 0.054 Uiso 0.270(11) 1 calc PR A 4 H101 H -0.0028 -0.1677 -0.1014 0.054 Uiso 0.270(11) 1 calc PR A 4 H102 H -0.1049 -0.1090 -0.1314 0.054 Uiso 0.270(11) 1 calc PR A 4 C91 C -0.236(2) -0.1183(14) -0.2908(11) 0.055(5) Uani 0.272(9) 1 d PU A 2 H90 H -0.2238 -0.1390 -0.2466 0.083 Uiso 0.272(9) 1 calc PR A 2 H91 H -0.2839 -0.1631 -0.3289 0.083 Uiso 0.272(9) 1 calc PR A 2 H92 H -0.2937 -0.0754 -0.2888 0.083 Uiso 0.272(9) 1 calc PR A 2 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 I1 0.04108(12) 0.02028(11) 0.01349(9) -0.00039(8) -0.00532(8) 0.01127(9) I2 0.03068(11) 0.02074(11) 0.01409(9) 0.00024(7) -0.00359(8) 0.00868(8) I3 0.02534(11) 0.04087(14) 0.01630(10) 0.01071(9) -0.00153(8) 0.00512(9) I4 0.02405(11) 0.04654(15) 0.01578(10) 0.01169(9) -0.00066(8) 0.00373(9) O8 0.0156(9) 0.0117(9) 0.0134(9) 0.0033(7) -0.0004(7) 0.0020(7) O6 0.0221(10) 0.0102(9) 0.0136(9) 0.0047(7) 0.0025(8) 0.0048(8) O7 0.0157(9) 0.0111(9) 0.0139(9) 0.0025(7) -0.0007(7) 0.0019(7) C8 0.0156(12) 0.0142(13) 0.0107(11) 0.0069(10) 0.0021(10) 0.0038(10) C87 0.0295(16) 0.0250(16) 0.0139(13) 0.0028(12) -0.0006(12) 0.0068(13) O9 0.0200(9) 0.0116(9) 0.0132(9) 0.0040(7) 0.0025(8) 0.0041(7) C89 0.0197(14) 0.0143(14) 0.0175(13) 0.0031(11) 0.0022(11) 0.0026(11) C74 0.0162(13) 0.0151(14) 0.0196(13) 0.0049(11) 0.0017(11) 0.0006(11) C13 0.0227(14) 0.0115(13) 0.0154(13) 0.0024(11) 0.0021(11) 0.0045(11) C14 0.0200(14) 0.0179(14) 0.0162(13) 0.0034(11) 0.0019(11) 0.0057(11) C16 0.0165(13) 0.0117(13) 0.0149(12) 0.0016(10) 0.0046(11) 0.0011(10) C17 0.0225(14) 0.0139(14) 0.0223(14) 0.0057(11) 0.0061(12) 0.0059(11) C18 0.0197(13) 0.0107(13) 0.0156(12) 0.0021(10) 0.0014(11) 0.0039(10) C19 0.0191(13) 0.0118(13) 0.0097(11) 0.0048(10) 0.0027(10) 0.0036(10) C20 0.0255(15) 0.0171(15) 0.0202(14) 0.0087(12) 0.0018(12) 0.0105(12) C21 0.0151(12) 0.0069(12) 0.0195(13) 0.0016(10) 0.0022(11) 0.0022(10) C22 0.0147(12) 0.0129(13) 0.0145(12) 0.0019(10) 0.0059(10) 0.0005(10) C23 0.0194(13) 0.0124(13) 0.0128(12) 0.0014(10) 0.0024(11) 0.0038(10) C24 0.0223(14) 0.0136(14) 0.0187(13) 0.0040(11) 0.0041(12) 0.0065(11) B93 0.0157(14) 0.0107(14) 0.0135(13) 0.0021(11) -0.0007(12) 0.0005(11) C29 0.0228(14) 0.0300(17) 0.0132(13) 0.0029(12) 0.0022(12) 0.0014(12) C30 0.0204(13) 0.0146(14) 0.0162(13) 0.0054(11) 0.0076(11) 0.0077(11) N14 0.0183(12) 0.0201(13) 0.0141(11) 0.0043(10) -0.0003(9) -0.0007(10) C34 0.0221(14) 0.0140(14) 0.0190(13) 0.0044(11) 0.0039(12) 0.0056(11) C35 0.0161(12) 0.0120(13) 0.0134(12) 0.0030(10) 0.0029(10) 0.0034(10) C36 0.0187(13) 0.0171(14) 0.0165(13) 0.0052(11) 0.0050(11) 0.0029(11) C37 0.0259(14) 0.0151(14) 0.0116(12) 0.0040(11) 0.0010(11) 0.0073(11) N15 0.0286(13) 0.0115(12) 0.0138(11) 0.0024(9) 0.0017(10) 0.0068(10) C39 0.0186(14) 0.0172(14) 0.0213(14) 0.0006(12) -0.0006(12) 0.0046(11) C40 0.0341(17) 0.0160(15) 0.0196(14) 0.0057(12) 0.0013(13) 0.0110(13) C41 0.0199(13) 0.0190(14) 0.0122(12) 0.0044(11) 0.0021(11) 0.0074(11) C42 0.0222(14) 0.0139(14) 0.0145(12) 0.0027(11) 0.0032(11) 0.0075(11) C43 0.0200(14) 0.0199(15) 0.0259(15) 0.0062(12) 0.0076(12) 0.0079(12) C45 0.0163(13) 0.0214(15) 0.0238(15) -0.0017(12) -0.0001(12) 0.0019(11) N12 0.0204(12) 0.0181(13) 0.0142(11) 0.0054(10) -0.0009(10) 0.0014(10) N13 0.0238(12) 0.0105(11) 0.0132(10) 0.0034(9) 0.0014(9) 0.0048(9) C49 0.0215(15) 0.0148(15) 0.051(2) 0.0117(14) 0.0178(15) 0.0058(12) C50 0.0309(16) 0.0165(15) 0.0242(15) 0.0054(12) 0.0080(13) 0.0108(12) C80 0.048(2) 0.0186(17) 0.0217(15) -0.0024(13) -0.0137(15) 0.0026(15) C52 0.0198(13) 0.0132(13) 0.0124(12) 0.0031(10) 0.0047(11) 0.0049(10) C53 0.0346(19) 0.041(2) 0.0283(17) -0.0080(16) -0.0005(15) 0.0026(16) B92 0.0137(13) 0.0115(14) 0.0123(13) 0.0028(11) -0.0009(11) 0.0021(11) C55 0.0173(13) 0.0149(14) 0.0168(13) 0.0052(11) 0.0070(11) 0.0068(10) C57 0.0268(15) 0.0131(14) 0.0218(14) 0.0013(11) 0.0036(12) -0.0007(12) C58 0.0174(14) 0.0179(15) 0.0350(17) 0.0006(13) 0.0008(13) -0.0011(11) C59 0.051(2) 0.0269(18) 0.0268(16) 0.0149(14) 0.0095(16) 0.0135(16) C60 0.0203(14) 0.0238(16) 0.0220(14) 0.0077(12) 0.0056(12) 0.0085(12) C61 0.0158(13) 0.0085(13) 0.0190(13) -0.0005(10) 0.0029(11) 0.0013(10) C62 0.0146(12) 0.0113(13) 0.0145(12) 0.0016(10) 0.0039(10) 0.0018(10) C63 0.0153(14) 0.0198(16) 0.0432(19) -0.0013(14) 0.0032(14) -0.0002(12) C64 0.0281(16) 0.0150(15) 0.0251(15) 0.0041(12) 0.0077(13) 0.0075(12) C65 0.0293(17) 0.0219(17) 0.0304(17) -0.0056(14) 0.0023(14) 0.0025(13) C66 0.0244(16) 0.0180(16) 0.056(2) 0.0096(15) 0.0230(16) 0.0063(12) C67 0.0358(18) 0.0202(16) 0.0354(17) 0.0131(14) 0.0214(15) 0.0105(13) C68 0.0276(15) 0.0128(14) 0.0226(14) 0.0026(11) 0.0071(13) 0.0009(12) C69 0.0209(15) 0.0223(16) 0.0363(18) 0.0084(14) 0.0035(14) 0.0014(12) C70 0.0308(16) 0.0185(15) 0.0306(16) 0.0107(13) 0.0144(14) 0.0090(13) C71 0.0243(15) 0.0220(16) 0.0184(14) -0.0005(12) 0.0003(12) -0.0013(12) C72 0.0202(14) 0.0128(14) 0.0206(13) 0.0042(11) 0.0037(11) 0.0052(11) C73 0.0198(14) 0.0151(14) 0.0196(13) 0.0030(11) 0.0045(11) 0.0006(11) C75 0.0197(13) 0.0153(14) 0.0165(13) 0.0037(11) 0.0048(11) 0.0024(11) C76 0.047(2) 0.044(2) 0.040(2) 0.0094(18) 0.0101(18) 0.0143(19) C88 0.0197(13) 0.0140(13) 0.0172(13) 0.0069(11) 0.0068(11) 0.0072(11) C81 0.0215(15) 0.0232(16) 0.0327(17) 0.0085(14) 0.0057(13) 0.0035(12) C82 0.023(2) 0.009(2) 0.015(2) 0.0036(17) 0.0007(19) -0.0024(17) C77 0.044(2) 0.0281(18) 0.0279(16) 0.0188(14) 0.0118(15) 0.0116(15) C83 0.053(2) 0.0233(18) 0.0248(16) 0.0000(14) -0.0154(16) 0.0064(16) C84 0.035(3) 0.017(3) 0.022(2) 0.0009(17) -0.0018(18) 0.0103(19) C85 0.019(2) 0.025(3) 0.024(2) 0.0007(19) -0.003(2) -0.005(2) C78 0.058(3) 0.050(3) 0.047(2) -0.002(2) 0.013(2) -0.009(2) C86 0.035(3) 0.026(3) 0.025(2) -0.0041(19) 0.003(2) 0.000(2) C79 0.0278(16) 0.0300(18) 0.0193(15) 0.0000(13) -0.0003(13) 0.0012(14) C90 0.038(8) 0.032(8) 0.027(7) -0.010(6) -0.002(6) 0.000(6) C92 0.030(7) 0.018(8) 0.026(6) -0.012(5) 0.001(6) 0.007(5) C93 0.039(8) 0.042(10) 0.029(8) 0.013(7) 0.003(6) 0.008(7) C91 0.055(5) 0.055(5) 0.055(5) 0.0093(14) 0.0119(15) 0.0098(14) _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 I1 C37 2.057(3) . ? I2 C41 2.061(3) . ? I3 C87 2.065(3) . ? I4 C29 2.071(3) . ? O8 C22 1.318(3) . ? O8 B92 1.522(3) . ? O6 C35 1.315(3) . ? O6 B93 1.533(3) . ? O7 C16 1.319(3) . ? O7 B93 1.529(3) . ? C8 C75 1.399(4) . ? C8 C74 1.402(4) . ? C8 B92 1.609(4) . ? C87 N12 1.346(4) . ? C87 C83 1.392(5) . ? O9 C62 1.316(3) . ? O9 B92 1.531(3) . ? C89 C60 1.393(4) . ? C89 C19 1.398(4) . ? C89 H1 0.9300 . ? C74 C43 1.391(4) . ? C74 H2 0.9300 . ? C13 C35 1.392(4) . ? C13 C16 1.395(4) . ? C13 H3 0.9300 . ? C14 N12 1.385(4) . ? C14 C80 1.398(4) . ? C14 C16 1.431(4) . ? C17 C61 1.396(4) . ? C17 C67 1.397(4) . ? C17 H4 0.9300 . ? C18 C62 1.393(4) . ? C18 C22 1.394(4) . ? C18 H5 0.9300 . ? C19 C73 1.401(4) . ? C19 B93 1.605(4) . ? C20 C88 1.502(4) . ? C20 C77 1.531(4) . ? C20 H6 0.9700 . ? C20 H7 0.9700 . ? C21 C34 1.393(4) . ? C21 C39 1.408(4) . ? C21 B93 1.605(4) . ? C22 C36 1.429(4) . ? C23 N13 1.373(3) . ? C23 C55 1.402(4) . ? C23 C62 1.444(4) . ? C24 C55 1.495(4) . ? C24 C69 1.533(4) . ? C24 H8 0.9700 . ? C24 H9 0.9700 . ? C29 N14 1.339(4) . ? C29 C79 1.380(5) . ? C30 C52 1.406(4) . ? C30 C42 1.410(4) . ? C30 C72 1.492(4) . ? N14 C36 1.390(4) . ? N14 H63 0.8600 . ? C34 C70 1.393(4) . ? C34 H10 0.9300 . ? C35 C52 1.432(4) . ? C36 C71 1.398(4) . ? C37 N15 1.352(4) . ? C37 C42 1.393(4) . ? N15 C52 1.381(4) . ? N15 H64 0.8600 . ? C39 C58 1.389(4) . ? C39 H11 0.9300 . ? C40 C42 1.499(4) . ? C40 C59 1.521(4) . ? C40 H12 0.9700 . ? C40 H13 0.9700 . ? C41 N13 1.354(3) . ? C41 C88 1.390(4) . ? C43 C50 1.396(4) . ? C43 H14 0.9300 . ? C45 C63 1.391(4) . ? C45 C61 1.403(4) . ? C45 H15 0.9300 . ? N12 H65 0.8600 . ? N13 H66 0.8600 . ? C49 C58 1.376(5) . ? C49 C70 1.381(5) . ? C49 H16 0.9300 . ? C50 C57 1.378(4) . ? C50 H17 0.9300 . ? C80 C83 1.425(4) . ? C80 C82 1.523(6) . ? C80 C92 1.573(14) . ? C53 C78 1.474(5) . ? C53 C79 1.496(5) . ? C53 H18 0.9700 . ? C53 H19 0.9700 . ? B92 C61 1.612(4) . ? C55 C88 1.408(4) . ? C57 C75 1.397(4) . ? C57 H20 0.9300 . ? C58 H21 0.9300 . ? C59 H22 0.9600 . ? C59 H23 0.9600 . ? C59 H24 0.9600 . ? C60 C64 1.396(4) . ? C60 H25 0.9300 . ? C63 C66 1.384(5) . ? C63 H26 0.9300 . ? C64 C68 1.378(4) . ? C64 H27 0.9300 . ? C65 C76 1.494(5) . ? C65 C71 1.504(5) . ? C65 H28 0.9700 . ? C65 H29 0.9700 . ? C66 C67 1.369(5) . ? C66 H30 0.9300 . ? C67 H31 0.9300 . ? C68 C73 1.396(4) . ? C68 H32 0.9300 . ? C69 H33 0.9600 . ? C69 H34 0.9600 . ? C69 H35 0.9600 . ? C70 H36 0.9300 . ? C71 C79 1.426(4) . ? C72 C81 1.541(4) . ? C72 H37 0.9700 . ? C72 H38 0.9700 . ? C73 H39 0.9300 . ? C75 H40 0.9300 . ? C76 H41 0.9600 . ? C76 H42 0.9600 . ? C76 H43 0.9600 . ? C81 H44 0.9600 . ? C81 H45 0.9600 . ? C81 H46 0.9600 . ? C82 C84 1.530(7) . ? C82 H93 0.9700 . ? C82 H94 0.9700 . ? C77 H49 0.9600 . ? C77 H50 0.9600 . ? C77 H51 0.9600 . ? C83 C85 1.513(6) . ? C83 C90 1.516(13) . ? C84 H95 0.9600 . ? C84 H96 0.9600 . ? C84 H97 0.9600 . ? C85 C86 1.525(7) . ? C85 H83 0.9700 . ? C85 H84 0.9700 . ? C78 H57 0.9600 . ? C78 H58 0.9600 . ? C78 H59 0.9600 . ? C86 H85 0.9600 . ? C86 H86 0.9600 . ? C86 H87 0.9600 . ? C90 C91 1.45(2) . ? C90 H88 0.9700 . ? C90 H89 0.9700 . ? C92 C93 1.47(2) . ? C92 H98 0.9700 . ? C92 H99 0.9700 . ? C93 H100 0.9600 . ? C93 H101 0.9600 . ? C93 H102 0.9600 . ? C91 H90 0.9600 . ? C91 H91 0.9600 . ? C91 H92 0.9600 . ? 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 C22 O8 B92 117.7(2) . . ? C35 O6 B93 117.8(2) . . ? C16 O7 B93 118.3(2) . . ? C75 C8 C74 116.9(2) . . ? C75 C8 B92 122.1(2) . . ? C74 C8 B92 120.9(2) . . ? N12 C87 C83 109.4(3) . . ? N12 C87 I3 121.3(2) . . ? C83 C87 I3 129.3(2) . . ? C62 O9 B92 117.2(2) . . ? C60 C89 C19 121.4(3) . . ? C60 C89 H1 119.3 . . ? C19 C89 H1 119.3 . . ? C43 C74 C8 121.8(3) . . ? C43 C74 H2 119.1 . . ? C8 C74 H2 119.1 . . ? C35 C13 C16 119.8(3) . . ? C35 C13 H3 120.1 . . ? C16 C13 H3 120.1 . . ? N12 C14 C80 106.9(3) . . ? N12 C14 C16 118.2(3) . . ? C80 C14 C16 134.5(3) . . ? O7 C16 C13 121.2(2) . . ? O7 C16 C14 114.5(2) . . ? C13 C16 C14 124.3(3) . . ? C61 C17 C67 121.5(3) . . ? C61 C17 H4 119.2 . . ? C67 C17 H4 119.2 . . ? C62 C18 C22 119.4(3) . . ? C62 C18 H5 120.3 . . ? C22 C18 H5 120.3 . . ? C89 C19 C73 117.1(2) . . ? C89 C19 B93 120.8(2) . . ? C73 C19 B93 121.9(2) . . ? C88 C20 C77 112.0(2) . . ? C88 C20 H6 109.2 . . ? C77 C20 H6 109.2 . . ? C88 C20 H7 109.2 . . ? C77 C20 H7 109.2 . . ? H6 C20 H7 107.9 . . ? C34 C21 C39 116.7(2) . . ? C34 C21 B93 123.7(2) . . ? C39 C21 B93 119.5(2) . . ? O8 C22 C18 121.4(2) . . ? O8 C22 C36 114.0(2) . . ? C18 C22 C36 124.6(3) . . ? N13 C23 C55 108.0(2) . . ? N13 C23 C62 117.8(2) . . ? C55 C23 C62 134.2(3) . . ? C55 C24 C69 111.0(2) . . ? C55 C24 H8 109.4 . . ? C69 C24 H8 109.4 . . ? C55 C24 H9 109.4 . . ? C69 C24 H9 109.4 . . ? H8 C24 H9 108.0 . . ? O7 B93 O6 106.4(2) . . ? O7 B93 C21 110.5(2) . . ? O6 B93 C21 108.2(2) . . ? O7 B93 C19 108.8(2) . . ? O6 B93 C19 106.9(2) . . ? C21 B93 C19 115.7(2) . . ? N14 C29 C79 109.5(3) . . ? N14 C29 I4 121.6(2) . . ? C79 C29 I4 128.7(2) . . ? C52 C30 C42 107.3(2) . . ? C52 C30 C72 127.8(3) . . ? C42 C30 C72 124.7(3) . . ? C29 N14 C36 109.9(3) . . ? C29 N14 H63 125.1 . . ? C36 N14 H63 125.1 . . ? C70 C34 C21 121.5(3) . . ? C70 C34 H10 119.2 . . ? C21 C34 H10 119.2 . . ? O6 C35 C13 120.2(2) . . ? O6 C35 C52 114.7(2) . . ? C13 C35 C52 125.1(3) . . ? N14 C36 C71 106.8(3) . . ? N14 C36 C22 117.6(3) . . ? C71 C36 C22 135.5(3) . . ? N15 C37 C42 109.2(2) . . ? N15 C37 I1 123.0(2) . . ? C42 C37 I1 127.6(2) . . ? C37 N15 C52 109.3(2) . . ? C37 N15 H64 125.4 . . ? C52 N15 H64 125.4 . . ? C58 C39 C21 121.7(3) . . ? C58 C39 H11 119.2 . . ? C21 C39 H11 119.2 . . ? C42 C40 C59 111.9(3) . . ? C42 C40 H12 109.2 . . ? C59 C40 H12 109.2 . . ? C42 C40 H13 109.2 . . ? C59 C40 H13 109.2 . . ? H12 C40 H13 107.9 . . ? N13 C41 C88 109.1(2) . . ? N13 C41 I2 123.0(2) . . ? C88 C41 I2 127.7(2) . . ? C37 C42 C30 106.8(2) . . ? C37 C42 C40 124.8(3) . . ? C30 C42 C40 128.3(3) . . ? C74 C43 C50 119.8(3) . . ? C74 C43 H14 120.1 . . ? C50 C43 H14 120.1 . . ? C63 C45 C61 121.9(3) . . ? C63 C45 H15 119.0 . . ? C61 C45 H15 119.0 . . ? C87 N12 C14 109.8(3) . . ? C87 N12 H65 125.1 . . ? C14 N12 H65 125.1 . . ? C41 N13 C23 109.1(2) . . ? C41 N13 H66 125.5 . . ? C23 N13 H66 125.5 . . ? C58 C49 C70 119.6(3) . . ? C58 C49 H16 120.2 . . ? C70 C49 H16 120.2 . . ? C57 C50 C43 119.6(3) . . ? C57 C50 H17 120.2 . . ? C43 C50 H17 120.2 . . ? C14 C80 C83 107.7(3) . . ? C14 C80 C82 127.7(3) . . ? C83 C80 C82 123.9(3) . . ? C14 C80 C92 121.4(5) . . ? C83 C80 C92 120.5(5) . . ? C82 C80 C92 36.6(5) . . ? N15 C52 C30 107.4(2) . . ? N15 C52 C35 117.9(2) . . ? C30 C52 C35 134.7(3) . . ? C78 C53 C79 113.2(3) . . ? C78 C53 H18 108.9 . . ? C79 C53 H18 108.9 . . ? C78 C53 H19 108.9 . . ? C79 C53 H19 108.9 . . ? H18 C53 H19 107.8 . . ? O8 B92 O9 106.8(2) . . ? O8 B92 C8 108.6(2) . . ? O9 B92 C8 107.5(2) . . ? O8 B92 C61 110.1(2) . . ? O9 B92 C61 107.8(2) . . ? C8 B92 C61 115.6(2) . . ? C23 C55 C88 106.9(2) . . ? C23 C55 C24 128.2(3) . . ? C88 C55 C24 124.5(3) . . ? C50 C57 C75 120.1(3) . . ? C50 C57 H20 119.9 . . ? C75 C57 H20 119.9 . . ? C49 C58 C39 120.1(3) . . ? C49 C58 H21 119.9 . . ? C39 C58 H21 119.9 . . ? C40 C59 H22 109.5 . . ? C40 C59 H23 109.5 . . ? H22 C59 H23 109.5 . . ? C40 C59 H24 109.5 . . ? H22 C59 H24 109.5 . . ? H23 C59 H24 109.5 . . ? C89 C60 C64 120.3(3) . . ? C89 C60 H25 119.9 . . ? C64 C60 H25 119.9 . . ? C17 C61 C45 116.7(3) . . ? C17 C61 B92 123.5(2) . . ? C45 C61 B92 119.7(2) . . ? O9 C62 C18 120.9(2) . . ? O9 C62 C23 114.3(2) . . ? C18 C62 C23 124.8(2) . . ? C66 C63 C45 119.6(3) . . ? C66 C63 H26 120.2 . . ? C45 C63 H26 120.2 . . ? C68 C64 C60 119.3(3) . . ? C68 C64 H27 120.3 . . ? C60 C64 H27 120.3 . . ? C76 C65 C71 112.0(3) . . ? C76 C65 H28 109.2 . . ? C71 C65 H28 109.2 . . ? C76 C65 H29 109.2 . . ? C71 C65 H29 109.2 . . ? H28 C65 H29 107.9 . . ? C67 C66 C63 120.1(3) . . ? C67 C66 H30 120.0 . . ? C63 C66 H30 120.0 . . ? C66 C67 C17 120.2(3) . . ? C66 C67 H31 119.9 . . ? C17 C67 H31 119.9 . . ? C64 C68 C73 120.1(3) . . ? C64 C68 H32 119.9 . . ? C73 C68 H32 119.9 . . ? C24 C69 H33 109.5 . . ? C24 C69 H34 109.5 . . ? H33 C69 H34 109.5 . . ? C24 C69 H35 109.5 . . ? H33 C69 H35 109.5 . . ? H34 C69 H35 109.5 . . ? C49 C70 C34 120.3(3) . . ? C49 C70 H36 119.8 . . ? C34 C70 H36 119.8 . . ? C36 C71 C79 107.1(3) . . ? C36 C71 C65 129.4(3) . . ? C79 C71 C65 123.5(3) . . ? C30 C72 C81 111.1(2) . . ? C30 C72 H37 109.4 . . ? C81 C72 H37 109.4 . . ? C30 C72 H38 109.4 . . ? C81 C72 H38 109.4 . . ? H37 C72 H38 108.0 . . ? C68 C73 C19 121.7(3) . . ? C68 C73 H39 119.1 . . ? C19 C73 H39 119.1 . . ? C57 C75 C8 121.7(3) . . ? C57 C75 H40 119.1 . . ? C8 C75 H40 119.1 . . ? C65 C76 H41 109.5 . . ? C65 C76 H42 109.5 . . ? H41 C76 H42 109.5 . . ? C65 C76 H43 109.5 . . ? H41 C76 H43 109.5 . . ? H42 C76 H43 109.5 . . ? C41 C88 C55 106.9(2) . . ? C41 C88 C20 125.1(3) . . ? C55 C88 C20 127.9(3) . . ? C72 C81 H44 109.5 . . ? C72 C81 H45 109.5 . . ? H44 C81 H45 109.5 . . ? C72 C81 H46 109.5 . . ? H44 C81 H46 109.5 . . ? H45 C81 H46 109.5 . . ? C80 C82 C84 112.6(4) . . ? C80 C82 H93 109.1 . . ? C84 C82 H93 109.1 . . ? C80 C82 H94 109.1 . . ? C84 C82 H94 109.1 . . ? H93 C82 H94 107.8 . . ? C20 C77 H49 109.5 . . ? C20 C77 H50 109.5 . . ? H49 C77 H50 109.5 . . ? C20 C77 H51 109.5 . . ? H49 C77 H51 109.5 . . ? H50 C77 H51 109.5 . . ? C87 C83 C80 106.0(3) . . ? C87 C83 C85 127.0(3) . . ? C80 C83 C85 126.4(4) . . ? C87 C83 C90 116.2(7) . . ? C80 C83 C90 126.6(7) . . ? C85 C83 C90 36.7(6) . . ? C83 C85 C86 113.1(4) . . ? C83 C85 H83 109.0 . . ? C86 C85 H83 109.0 . . ? C83 C85 H84 109.0 . . ? C86 C85 H84 109.0 . . ? H83 C85 H84 107.8 . . ? C53 C78 H57 109.5 . . ? C53 C78 H58 109.5 . . ? H57 C78 H58 109.5 . . ? C53 C78 H59 109.5 . . ? H57 C78 H59 109.5 . . ? H58 C78 H59 109.5 . . ? C29 C79 C71 106.7(3) . . ? C29 C79 C53 126.2(3) . . ? C71 C79 C53 127.1(3) . . ? C91 C90 C83 93.5(12) . . ? C91 C90 H88 113.0 . . ? C83 C90 H88 113.0 . . ? C91 C90 H89 113.0 . . ? C83 C90 H89 113.0 . . ? H88 C90 H89 110.4 . . ? C93 C92 C80 94.7(11) . . ? C93 C92 H98 112.8 . . ? C80 C92 H98 112.8 . . ? C93 C92 H99 112.8 . . ? C80 C92 H99 112.8 . . ? H98 C92 H99 110.3 . . ? C90 C91 H90 109.5 . . ? C90 C91 H91 109.5 . . ? H90 C91 H91 109.5 . . ? C90 C91 H92 109.5 . . ? H90 C91 H92 109.5 . . ? H91 C91 H92 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C75 C8 C74 C43 -0.2(4) . . . . ? B92 C8 C74 C43 -177.2(3) . . . . ? B93 O7 C16 C13 15.0(4) . . . . ? B93 O7 C16 C14 -165.2(2) . . . . ? C35 C13 C16 O7 9.5(4) . . . . ? C35 C13 C16 C14 -170.4(3) . . . . ? N12 C14 C16 O7 13.5(4) . . . . ? C80 C14 C16 O7 -158.6(3) . . . . ? N12 C14 C16 C13 -166.7(3) . . . . ? C80 C14 C16 C13 21.2(5) . . . . ? C60 C89 C19 C73 0.5(4) . . . . ? C60 C89 C19 B93 176.6(3) . . . . ? B92 O8 C22 C18 -18.7(3) . . . . ? B92 O8 C22 C36 161.2(2) . . . . ? C62 C18 C22 O8 -6.5(4) . . . . ? C62 C18 C22 C36 173.6(2) . . . . ? C16 O7 B93 O6 -39.1(3) . . . . ? C16 O7 B93 C21 78.1(3) . . . . ? C16 O7 B93 C19 -153.9(2) . . . . ? C35 O6 B93 O7 44.6(3) . . . . ? C35 O6 B93 C21 -74.1(3) . . . . ? C35 O6 B93 C19 160.7(2) . . . . ? C34 C21 B93 O7 31.0(4) . . . . ? C39 C21 B93 O7 -151.8(2) . . . . ? C34 C21 B93 O6 147.2(2) . . . . ? C39 C21 B93 O6 -35.7(3) . . . . ? C34 C21 B93 C19 -93.1(3) . . . . ? C39 C21 B93 C19 84.1(3) . . . . ? C89 C19 B93 O7 39.5(3) . . . . ? C73 C19 B93 O7 -144.6(2) . . . . ? C89 C19 B93 O6 -75.1(3) . . . . ? C73 C19 B93 O6 100.8(3) . . . . ? C89 C19 B93 C21 164.5(2) . . . . ? C73 C19 B93 C21 -19.6(4) . . . . ? C79 C29 N14 C36 0.6(3) . . . . ? I4 C29 N14 C36 176.11(19) . . . . ? C39 C21 C34 C70 0.7(4) . . . . ? B93 C21 C34 C70 178.0(3) . . . . ? B93 O6 C35 C13 -25.4(3) . . . . ? B93 O6 C35 C52 154.9(2) . . . . ? C16 C13 C35 O6 -3.9(4) . . . . ? C16 C13 C35 C52 175.7(3) . . . . ? C29 N14 C36 C71 -0.9(3) . . . . ? C29 N14 C36 C22 -179.1(2) . . . . ? O8 C22 C36 N14 -8.4(3) . . . . ? C18 C22 C36 N14 171.5(3) . . . . ? O8 C22 C36 C71 174.1(3) . . . . ? C18 C22 C36 C71 -6.0(5) . . . . ? C42 C37 N15 C52 0.3(3) . . . . ? I1 C37 N15 C52 -175.67(19) . . . . ? C34 C21 C39 C58 -0.2(4) . . . . ? B93 C21 C39 C58 -177.6(3) . . . . ? N15 C37 C42 C30 -0.8(3) . . . . ? I1 C37 C42 C30 175.0(2) . . . . ? N15 C37 C42 C40 -176.8(3) . . . . ? I1 C37 C42 C40 -1.0(4) . . . . ? C52 C30 C42 C37 0.9(3) . . . . ? C72 C30 C42 C37 -173.8(2) . . . . ? C52 C30 C42 C40 176.8(3) . . . . ? C72 C30 C42 C40 2.0(5) . . . . ? C59 C40 C42 C37 87.5(4) . . . . ? C59 C40 C42 C30 -87.7(4) . . . . ? C8 C74 C43 C50 0.5(4) . . . . ? C83 C87 N12 C14 3.4(4) . . . . ? I3 C87 N12 C14 -176.9(2) . . . . ? C80 C14 N12 C87 -3.0(3) . . . . ? C16 C14 N12 C87 -177.1(3) . . . . ? C88 C41 N13 C23 -0.7(3) . . . . ? I2 C41 N13 C23 175.33(18) . . . . ? C55 C23 N13 C41 0.3(3) . . . . ? C62 C23 N13 C41 -179.8(2) . . . . ? C74 C43 C50 C57 -0.5(5) . . . . ? N12 C14 C80 C83 1.5(4) . . . . ? C16 C14 C80 C83 174.2(3) . . . . ? N12 C14 C80 C82 -169.2(4) . . . . ? C16 C14 C80 C82 3.5(7) . . . . ? N12 C14 C80 C92 146.6(6) . . . . ? C16 C14 C80 C92 -40.7(8) . . . . ? C37 N15 C52 C30 0.3(3) . . . . ? C37 N15 C52 C35 -179.0(2) . . . . ? C42 C30 C52 N15 -0.8(3) . . . . ? C72 C30 C52 N15 173.8(2) . . . . ? C42 C30 C52 C35 178.4(3) . . . . ? C72 C30 C52 C35 -7.1(5) . . . . ? O6 C35 C52 N15 -6.1(4) . . . . ? C13 C35 C52 N15 174.3(2) . . . . ? O6 C35 C52 C30 174.8(3) . . . . ? C13 C35 C52 C30 -4.8(5) . . . . ? C22 O8 B92 O9 41.5(3) . . . . ? C22 O8 B92 C8 157.2(2) . . . . ? C22 O8 B92 C61 -75.3(3) . . . . ? C62 O9 B92 O8 -44.2(3) . . . . ? C62 O9 B92 C8 -160.6(2) . . . . ? C62 O9 B92 C61 74.1(3) . . . . ? C75 C8 B92 O8 146.5(2) . . . . ? C74 C8 B92 O8 -36.6(3) . . . . ? C75 C8 B92 O9 -98.3(3) . . . . ? C74 C8 B92 O9 78.6(3) . . . . ? C75 C8 B92 C61 22.2(4) . . . . ? C74 C8 B92 C61 -160.9(2) . . . . ? N13 C23 C55 C88 0.1(3) . . . . ? C62 C23 C55 C88 -179.7(3) . . . . ? N13 C23 C55 C24 -172.7(2) . . . . ? C62 C23 C55 C24 7.5(5) . . . . ? C69 C24 C55 C23 72.4(4) . . . . ? C69 C24 C55 C88 -99.2(3) . . . . ? C43 C50 C57 C75 0.2(5) . . . . ? C70 C49 C58 C39 0.6(5) . . . . ? C21 C39 C58 C49 -0.5(5) . . . . ? C19 C89 C60 C64 -0.8(4) . . . . ? C67 C17 C61 C45 -1.6(4) . . . . ? C67 C17 C61 B92 -179.0(3) . . . . ? C63 C45 C61 C17 1.3(4) . . . . ? C63 C45 C61 B92 178.8(3) . . . . ? O8 B92 C61 C17 -30.7(4) . . . . ? O9 B92 C61 C17 -146.9(3) . . . . ? C8 B92 C61 C17 92.7(3) . . . . ? O8 B92 C61 C45 151.9(2) . . . . ? O9 B92 C61 C45 35.7(3) . . . . ? C8 B92 C61 C45 -84.6(3) . . . . ? B92 O9 C62 C18 24.0(3) . . . . ? B92 O9 C62 C23 -156.9(2) . . . . ? C22 C18 C62 O9 3.6(4) . . . . ? C22 C18 C62 C23 -175.4(3) . . . . ? N13 C23 C62 O9 9.0(3) . . . . ? C55 C23 C62 O9 -171.2(3) . . . . ? N13 C23 C62 C18 -171.9(2) . . . . ? C55 C23 C62 C18 7.9(5) . . . . ? C61 C45 C63 C66 -0.1(5) . . . . ? C89 C60 C64 C68 0.8(5) . . . . ? C45 C63 C66 C67 -0.8(5) . . . . ? C63 C66 C67 C17 0.5(5) . . . . ? C61 C17 C67 C66 0.7(5) . . . . ? C60 C64 C68 C73 -0.5(5) . . . . ? C58 C49 C70 C34 -0.1(5) . . . . ? C21 C34 C70 C49 -0.6(4) . . . . ? N14 C36 C71 C79 0.9(3) . . . . ? C22 C36 C71 C79 178.6(3) . . . . ? N14 C36 C71 C65 -178.7(3) . . . . ? C22 C36 C71 C65 -1.0(6) . . . . ? C76 C65 C71 C36 -85.4(4) . . . . ? C76 C65 C71 C79 95.0(4) . . . . ? C52 C30 C72 C81 -72.1(4) . . . . ? C42 C30 C72 C81 101.5(3) . . . . ? C64 C68 C73 C19 0.2(5) . . . . ? C89 C19 C73 C68 -0.2(4) . . . . ? B93 C19 C73 C68 -176.2(3) . . . . ? C50 C57 C75 C8 0.2(4) . . . . ? C74 C8 C75 C57 -0.2(4) . . . . ? B92 C8 C75 C57 176.9(3) . . . . ? N13 C41 C88 C55 0.8(3) . . . . ? I2 C41 C88 C55 -175.03(19) . . . . ? N13 C41 C88 C20 177.1(2) . . . . ? I2 C41 C88 C20 1.4(4) . . . . ? C23 C55 C88 C41 -0.5(3) . . . . ? C24 C55 C88 C41 172.6(2) . . . . ? C23 C55 C88 C20 -176.8(3) . . . . ? C24 C55 C88 C20 -3.6(4) . . . . ? C77 C20 C88 C41 -89.0(4) . . . . ? C77 C20 C88 C55 86.6(4) . . . . ? C14 C80 C82 C84 -93.0(5) . . . . ? C83 C80 C82 C84 97.7(5) . . . . ? C92 C80 C82 C84 0.8(7) . . . . ? N12 C87 C83 C80 -2.4(4) . . . . ? I3 C87 C83 C80 177.9(3) . . . . ? N12 C87 C83 C85 169.7(4) . . . . ? I3 C87 C83 C85 -10.0(6) . . . . ? N12 C87 C83 C90 -148.7(7) . . . . ? I3 C87 C83 C90 31.5(8) . . . . ? C14 C80 C83 C87 0.5(4) . . . . ? C82 C80 C83 C87 171.6(4) . . . . ? C92 C80 C83 C87 -145.0(7) . . . . ? C14 C80 C83 C85 -171.6(4) . . . . ? C82 C80 C83 C85 -0.5(7) . . . . ? C92 C80 C83 C85 42.9(8) . . . . ? C14 C80 C83 C90 142.2(9) . . . . ? C82 C80 C83 C90 -46.6(10) . . . . ? C92 C80 C83 C90 -3.2(11) . . . . ? C87 C83 C85 C86 116.9(5) . . . . ? C80 C83 C85 C86 -72.6(6) . . . . ? C90 C83 C85 C86 32.0(10) . . . . ? N14 C29 C79 C71 0.0(4) . . . . ? I4 C29 C79 C71 -175.1(2) . . . . ? N14 C29 C79 C53 178.9(3) . . . . ? I4 C29 C79 C53 3.7(5) . . . . ? C36 C71 C79 C29 -0.6(4) . . . . ? C65 C71 C79 C29 179.1(3) . . . . ? C36 C71 C79 C53 -179.4(3) . . . . ? C65 C71 C79 C53 0.3(5) . . . . ? C78 C53 C79 C29 96.9(5) . . . . ? C78 C53 C79 C71 -84.5(5) . . . . ? C87 C83 C90 C91 -121.6(10) . . . . ? C80 C83 C90 C91 100.0(12) . . . . ? C85 C83 C90 C91 -3.9(10) . . . . ? C14 C80 C92 C93 114.0(8) . . . . ? C83 C80 C92 C93 -105.3(9) . . . . ? C82 C80 C92 C93 1.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.248 _refine_diff_density_min -0.889 _refine_diff_density_rms 0.111 #============================================================================== # End of CIF #============================================================================== data_90228mae _database_code_depnum_ccdc_archive 'CCDC 759621' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H29 B Cl2 N2 O2' _chemical_formula_weight 603.32 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' O O 0.0106 0.0060 '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' B B 0.0013 0.0007 '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 triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.615(4) _cell_length_b 13.859(5) _cell_length_c 20.323(7) _cell_angle_alpha 73.013(14) _cell_angle_beta 79.998(12) _cell_angle_gamma 79.432(14) _cell_volume 3050.5(19) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 0.249 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9070 _exptl_absorpt_correction_T_max 0.9519 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _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 \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29747 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0685 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 13828 _reflns_number_gt 5109 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0773P)^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 ? _refine_ls_number_reflns 13828 _refine_ls_number_parameters 803 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1296 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1625 _refine_ls_wR_factor_gt 0.1219 _refine_ls_goodness_of_fit_ref 0.906 _refine_ls_restrained_S_all 0.906 _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 C1 C 0.9109(4) 0.2969(4) 0.1090(2) 0.0310(12) Uani 1 1 d . . . H1 H 0.8868 0.3350 0.1422 0.037 Uiso 1 1 calc R . . C2 C 1.0141(4) 0.3123(4) 0.0634(3) 0.0371(13) Uani 1 1 d . . . H2 H 1.0602 0.3608 0.0659 0.044 Uiso 1 1 calc R . . C3 C 1.0503(5) 0.2577(4) 0.0146(3) 0.0424(16) Uani 1 1 d . . . H3 H 1.1210 0.2685 -0.0163 0.051 Uiso 1 1 calc R . . C4 C 0.9836(4) 0.1879(4) 0.0111(3) 0.0400(15) Uani 1 1 d . . . H4 H 1.0087 0.1506 -0.0226 0.048 Uiso 1 1 calc R . . C5 C 0.8795(4) 0.1705(4) 0.0561(2) 0.0332(13) Uani 1 1 d . . . H5 H 0.8341 0.1218 0.0531 0.040 Uiso 1 1 calc R . . C6 C 0.8427(4) 0.2259(3) 0.1061(2) 0.0271(12) Uani 1 1 d . . . C7 C 0.7321(4) 0.2071(3) 0.1532(2) 0.0237(10) Uani 1 1 d . . . C8 C 0.6813(4) 0.1192(3) 0.1808(2) 0.0280(11) Uani 1 1 d . . . H8 H 0.7128 0.0542 0.1736 0.034 Uiso 1 1 calc R . . C9 C 0.5766(4) 0.1421(3) 0.2208(2) 0.0277(11) Uani 1 1 d . . . H9 H 0.5234 0.0958 0.2463 0.033 Uiso 1 1 calc R . . C10 C 0.5633(4) 0.2453(3) 0.2168(2) 0.0231(10) Uani 1 1 d . . . C11 C 0.4702(4) 0.3110(3) 0.2454(2) 0.0206(10) Uani 1 1 d . . . C12 C 0.3667(4) 0.2777(3) 0.2838(2) 0.0221(10) Uani 1 1 d . . . H12 H 0.3490 0.2123 0.2866 0.027 Uiso 1 1 calc R . . C13 C 0.2899(4) 0.3418(3) 0.3178(2) 0.0200(10) Uani 1 1 d . . . C14 C 0.1922(4) 0.3093(3) 0.3681(2) 0.0208(10) Uani 1 1 d . . . C15 C 0.1573(4) 0.2136(3) 0.3987(2) 0.0249(10) Uani 1 1 d . . . H15 H 0.1954 0.1510 0.3899 0.030 Uiso 1 1 calc R . . C16 C 0.0550(4) 0.2272(3) 0.4453(2) 0.0278(11) Uani 1 1 d . . . H16 H 0.0116 0.1751 0.4742 0.033 Uiso 1 1 calc R . . C17 C 0.0284(4) 0.3308(3) 0.4415(2) 0.0245(10) Uani 1 1 d . . . C18 C -0.0721(4) 0.3849(3) 0.4773(2) 0.0253(11) Uani 1 1 d . . . C19 C -0.1331(4) 0.3334(4) 0.5395(2) 0.0307(12) Uani 1 1 d . . . H19 H -0.1082 0.2630 0.5592 0.037 Uiso 1 1 calc R . . C20 C -0.2289(4) 0.3836(4) 0.5728(2) 0.0329(12) Uani 1 1 d . . . H20 H -0.2699 0.3477 0.6149 0.040 Uiso 1 1 calc R . . C21 C -0.2653(4) 0.4867(4) 0.5446(3) 0.0332(13) Uani 1 1 d . . . H21 H -0.3307 0.5215 0.5675 0.040 Uiso 1 1 calc R . . C22 C -0.2062(4) 0.5379(4) 0.4834(2) 0.0335(12) Uani 1 1 d . . . H22 H -0.2318 0.6081 0.4639 0.040 Uiso 1 1 calc R . . C23 C -0.1097(4) 0.4884(3) 0.4500(2) 0.0289(11) Uani 1 1 d . . . H23 H -0.0689 0.5252 0.4081 0.035 Uiso 1 1 calc R . . C24 C 0.4275(4) 0.5780(3) 0.2580(2) 0.0218(10) Uani 1 1 d . . . C25 C 0.3865(4) 0.6791(3) 0.2271(2) 0.0276(11) Uani 1 1 d . . . H25 H 0.3335 0.6942 0.1936 0.033 Uiso 1 1 calc R . . C26 C 0.4210(4) 0.7586(4) 0.2441(3) 0.0376(13) Uani 1 1 d . . . H26 H 0.3906 0.8270 0.2228 0.045 Uiso 1 1 calc R . . C27 C 0.4986(5) 0.7387(4) 0.2913(3) 0.0415(14) Uani 1 1 d . . . H27 H 0.5223 0.7932 0.3027 0.050 Uiso 1 1 calc R . . C28 C 0.5429(4) 0.6382(4) 0.3227(3) 0.0352(12) Uani 1 1 d . . . H28 H 0.5971 0.6241 0.3554 0.042 Uiso 1 1 calc R . . C29 C 0.5077(4) 0.5591(4) 0.3061(2) 0.0289(12) Uani 1 1 d . . . H29 H 0.5384 0.4908 0.3276 0.035 Uiso 1 1 calc R . . C30 C 0.3148(4) 0.5122(3) 0.1751(2) 0.0229(10) Uani 1 1 d . . . C31 C 0.1918(4) 0.5199(3) 0.1798(2) 0.0287(11) Uani 1 1 d . . . H31 H 0.1467 0.5081 0.2244 0.034 Uiso 1 1 calc R . . C32 C 0.1339(5) 0.5441(4) 0.1223(3) 0.0357(14) Uani 1 1 d . . . H32 H 0.0503 0.5495 0.1274 0.043 Uiso 1 1 calc R . . C33 C 0.1982(5) 0.5608(4) 0.0564(3) 0.0366(13) Uani 1 1 d . . . H33 H 0.1590 0.5761 0.0165 0.044 Uiso 1 1 calc R . . C34 C 0.3196(5) 0.5548(3) 0.0496(2) 0.0359(12) Uani 1 1 d . . . H34 H 0.3639 0.5673 0.0048 0.043 Uiso 1 1 calc R . . C35 C 0.3773(4) 0.5304(3) 0.1082(2) 0.0267(11) Uani 1 1 d . . . H35 H 0.4608 0.5260 0.1027 0.032 Uiso 1 1 calc R . . O1 O 0.3029(3) 0.4374(2) 0.30651(15) 0.0213(7) Uani 1 1 d . . . O2 O 0.4903(3) 0.4050(2) 0.23397(15) 0.0229(7) Uani 1 1 d . . . N1 N 0.1116(3) 0.3785(3) 0.39520(18) 0.0223(8) Uani 1 1 d . . . H1N H 0.1141 0.4444 0.3839 0.027 Uiso 1 1 calc R . . N2 N 0.6605(3) 0.2828(3) 0.17578(18) 0.0237(9) Uani 1 1 d . . . H2N H 0.6743 0.3462 0.1657 0.028 Uiso 1 1 calc R . . B1 B 0.3826(4) 0.4852(4) 0.2424(3) 0.0214(11) Uani 1 1 d . . . C36 C 0.5896(4) 1.2033(4) 0.3914(2) 0.0291(12) Uani 1 1 d . . . H36 H 0.6150 1.1654 0.3581 0.035 Uiso 1 1 calc R . . C37 C 0.4852(4) 1.1867(4) 0.4360(3) 0.0368(13) Uani 1 1 d . . . H37 H 0.4393 1.1383 0.4332 0.044 Uiso 1 1 calc R . . C38 C 0.4496(5) 1.2422(4) 0.4845(3) 0.0440(16) Uani 1 1 d . . . H38 H 0.3785 1.2319 0.5151 0.053 Uiso 1 1 calc R . . C39 C 0.5165(5) 1.3123(4) 0.4888(3) 0.0432(17) Uani 1 1 d . . . H39 H 0.4914 1.3493 0.5227 0.052 Uiso 1 1 calc R . . C40 C 0.6199(4) 1.3291(4) 0.4443(2) 0.0311(12) Uani 1 1 d . . . H40 H 0.6654 1.3776 0.4474 0.037 Uiso 1 1 calc R . . C41 C 0.6569(4) 1.2741(3) 0.3948(2) 0.0253(11) Uani 1 1 d . . . C42 C 0.7649(4) 1.2925(3) 0.3481(2) 0.0242(11) Uani 1 1 d . . . C43 C 0.8167(4) 1.3802(3) 0.3199(2) 0.0279(11) Uani 1 1 d . . . H43 H 0.7850 1.4453 0.3267 0.034 Uiso 1 1 calc R . . C44 C 0.9243(4) 1.3572(3) 0.2793(2) 0.0270(11) Uani 1 1 d . . . H44 H 0.9776 1.4036 0.2541 0.032 Uiso 1 1 calc R . . C45 C 0.9377(4) 1.2546(3) 0.2831(2) 0.0217(10) Uani 1 1 d . . . C46 C 1.0301(4) 1.1894(3) 0.2550(2) 0.0220(10) Uani 1 1 d . . . C47 C 1.1326(4) 1.2225(3) 0.2167(2) 0.0216(10) Uani 1 1 d . . . H47 H 1.1497 1.2882 0.2137 0.026 Uiso 1 1 calc R . . C48 C 1.2108(4) 1.1582(3) 0.1823(2) 0.0208(10) Uani 1 1 d . . . C49 C 1.3078(4) 1.1910(3) 0.1316(2) 0.0218(10) Uani 1 1 d . . . C50 C 1.3421(4) 1.2850(3) 0.1011(2) 0.0262(11) Uani 1 1 d . . . H50 H 1.3031 1.3474 0.1098 0.031 Uiso 1 1 calc R . . C51 C 1.4441(4) 1.2729(3) 0.0551(2) 0.0274(11) Uani 1 1 d . . . H51 H 1.4871 1.3257 0.0269 0.033 Uiso 1 1 calc R . . C52 C 1.4720(4) 1.1703(3) 0.0579(2) 0.0230(10) Uani 1 1 d . . . C53 C 1.5719(4) 1.1149(3) 0.0222(2) 0.0231(10) Uani 1 1 d . . . C54 C 1.6335(4) 1.1671(3) -0.0394(2) 0.0293(11) Uani 1 1 d . . . H54 H 1.6097 1.2378 -0.0585 0.035 Uiso 1 1 calc R . . C55 C 1.7293(4) 1.1161(4) -0.0728(2) 0.0340(13) Uani 1 1 d . . . H55 H 1.7695 1.1520 -0.1152 0.041 Uiso 1 1 calc R . . C56 C 1.7669(4) 1.0141(4) -0.0454(2) 0.0301(12) Uani 1 1 d . . . H56 H 1.8332 0.9799 -0.0682 0.036 Uiso 1 1 calc R . . C57 C 1.7061(4) 0.9617(4) 0.0164(3) 0.0325(12) Uani 1 1 d . . . H57 H 1.7307 0.8912 0.0355 0.039 Uiso 1 1 calc R . . C58 C 1.6100(4) 1.0120(3) 0.0501(2) 0.0300(12) Uani 1 1 d . . . H58 H 1.5700 0.9759 0.0924 0.036 Uiso 1 1 calc R . . C59 C 1.0717(4) 0.9224(3) 0.2421(2) 0.0229(10) Uani 1 1 d . . . C60 C 0.9930(4) 0.9403(3) 0.1940(2) 0.0285(11) Uani 1 1 d . . . H60 H 0.9630 1.0086 0.1721 0.034 Uiso 1 1 calc R . . C61 C 0.9573(4) 0.8616(4) 0.1773(3) 0.0364(13) Uani 1 1 d . . . H61 H 0.9023 0.8761 0.1449 0.044 Uiso 1 1 calc R . . C62 C 1.0015(4) 0.7616(4) 0.2076(3) 0.0416(14) Uani 1 1 d . . . H62 H 0.9787 0.7073 0.1954 0.050 Uiso 1 1 calc R . . C63 C 1.0793(5) 0.7418(4) 0.2557(3) 0.0414(15) Uani 1 1 d . . . H63 H 1.1094 0.6734 0.2772 0.050 Uiso 1 1 calc R . . C64 C 1.1138(4) 0.8209(3) 0.2727(2) 0.0288(11) Uani 1 1 d . . . H64 H 1.1672 0.8058 0.3060 0.035 Uiso 1 1 calc R . . C65 C 1.1853(4) 0.9878(3) 0.3245(2) 0.0228(10) Uani 1 1 d . . . C66 C 1.1231(4) 0.9696(3) 0.3916(2) 0.0306(11) Uani 1 1 d . . . H66 H 1.0397 0.9733 0.3971 0.037 Uiso 1 1 calc R . . C67 C 1.1800(5) 0.9463(4) 0.4501(2) 0.0340(12) Uani 1 1 d . . . H67 H 1.1354 0.9356 0.4948 0.041 Uiso 1 1 calc R . . C68 C 1.3015(5) 0.9385(3) 0.4434(2) 0.0359(13) Uani 1 1 d . . . H68 H 1.3406 0.9209 0.4835 0.043 Uiso 1 1 calc R . . C69 C 1.3659(4) 0.9563(4) 0.3784(3) 0.0368(13) Uani 1 1 d . . . H69 H 1.4493 0.9528 0.3734 0.044 Uiso 1 1 calc R . . C70 C 1.3070(4) 0.9797(3) 0.3198(2) 0.0300(12) Uani 1 1 d . . . H70 H 1.3522 0.9903 0.2752 0.036 Uiso 1 1 calc R . . O3 O 1.0097(3) 1.0955(2) 0.26601(15) 0.0225(7) Uani 1 1 d . . . O4 O 1.1971(3) 1.0628(2) 0.19302(15) 0.0221(7) Uani 1 1 d . . . N3 N 0.8388(3) 1.2171(3) 0.32417(17) 0.0234(9) Uani 1 1 d . . . H3N H 0.8252 1.1537 0.3336 0.028 Uiso 1 1 calc R . . N4 N 1.3882(3) 1.1214(3) 0.10517(18) 0.0215(8) Uani 1 1 d . . . H4N H 1.3861 1.0554 0.1169 0.026 Uiso 1 1 calc R . . B2 B 1.1164(4) 1.0152(4) 0.2580(3) 0.0219(11) Uani 1 1 d . . . C1S C 0.8367(5) 0.8547(5) 0.3757(3) 0.0304(16) Uani 0.692(13) 1 d P A 1 H1S H 0.9029 0.8776 0.3401 0.036 Uiso 0.692(13) 1 calc PR A 1 H2S H 0.8705 0.8050 0.4160 0.036 Uiso 0.692(13) 1 calc PR A 1 Cl1S Cl 0.7553(5) 0.9589(4) 0.4018(3) 0.0841(15) Uani 0.692(13) 1 d P A 1 Cl2S Cl 0.7501(3) 0.7953(3) 0.34207(14) 0.0489(7) Uani 0.692(13) 1 d P A 1 Cl3S Cl 0.7168(12) 0.8447(15) 0.3245(7) 0.086(4) Uani 0.308(13) 1 d P A 2 Cl4S Cl 0.7617(6) 0.9614(5) 0.4100(2) 0.0261(13) Uani 0.308(13) 1 d P A 2 C2S C 0.8180(16) 0.9112(18) 0.3405(12) 0.066(7) Uani 0.308(13) 1 d P A 2 H3S H 0.8922 0.8647 0.3505 0.080 Uiso 0.308(13) 1 calc PR A 2 H4S H 0.8364 0.9671 0.2987 0.080 Uiso 0.308(13) 1 calc PR A 2 C1T C 0.6655(6) 0.6375(6) 0.1288(4) 0.078(2) Uani 1 1 d . . . H1T H 0.6046 0.6098 0.1667 0.094 Uiso 1 1 calc R . . H2T H 0.6245 0.6894 0.0923 0.094 Uiso 1 1 calc R . . Cl1T Cl 0.74163(15) 0.54021(12) 0.09469(9) 0.0632(5) Uani 1 1 d . . . Cl2T Cl 0.75547(18) 0.69590(17) 0.16073(10) 0.0861(7) 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 C1 0.030(3) 0.036(3) 0.023(2) -0.004(2) -0.007(2) 0.002(2) C2 0.026(3) 0.044(3) 0.035(3) 0.001(2) -0.008(2) -0.004(2) C3 0.029(3) 0.053(3) 0.030(3) 0.001(3) 0.004(2) 0.007(3) C4 0.032(3) 0.047(3) 0.028(3) -0.008(2) 0.011(2) 0.009(3) C5 0.031(3) 0.035(3) 0.026(2) -0.004(2) 0.001(2) 0.006(2) C6 0.025(2) 0.028(2) 0.022(2) -0.003(2) -0.003(2) 0.006(2) C7 0.019(2) 0.031(2) 0.020(2) -0.0071(19) -0.0016(18) -0.0005(19) C8 0.029(3) 0.024(2) 0.031(3) -0.013(2) -0.001(2) 0.002(2) C9 0.030(3) 0.025(2) 0.028(2) -0.008(2) -0.002(2) -0.004(2) C10 0.020(2) 0.029(2) 0.017(2) -0.0037(19) 0.0010(18) -0.0025(19) C11 0.022(2) 0.022(2) 0.017(2) -0.0043(18) -0.0011(18) -0.0020(19) C12 0.024(2) 0.018(2) 0.021(2) -0.0020(18) 0.0010(18) -0.0048(18) C13 0.021(2) 0.020(2) 0.018(2) -0.0012(18) -0.0045(18) -0.0058(18) C14 0.022(2) 0.020(2) 0.020(2) -0.0045(18) -0.0022(18) -0.0045(18) C15 0.028(2) 0.021(2) 0.022(2) -0.0005(18) 0.0042(19) -0.0112(18) C16 0.028(2) 0.024(2) 0.027(3) -0.003(2) 0.004(2) -0.006(2) C17 0.025(2) 0.025(2) 0.023(2) -0.0047(19) -0.0008(19) -0.007(2) C18 0.024(2) 0.032(2) 0.020(2) -0.008(2) -0.0012(19) -0.004(2) C19 0.026(2) 0.035(3) 0.024(2) -0.003(2) 0.001(2) 0.001(2) C20 0.030(3) 0.042(3) 0.022(2) -0.007(2) 0.005(2) -0.004(2) C21 0.029(3) 0.041(3) 0.033(3) -0.018(2) -0.002(2) -0.001(2) C22 0.034(3) 0.032(3) 0.032(3) -0.006(2) 0.000(2) -0.004(2) C23 0.024(2) 0.030(3) 0.030(3) -0.008(2) 0.005(2) -0.007(2) C24 0.017(2) 0.025(2) 0.023(2) -0.0100(19) 0.0065(18) -0.0043(18) C25 0.026(2) 0.023(2) 0.031(3) -0.005(2) 0.000(2) -0.005(2) C26 0.033(3) 0.027(3) 0.053(3) -0.012(2) -0.003(3) -0.007(2) C27 0.038(3) 0.036(3) 0.060(4) -0.026(3) -0.001(3) -0.013(2) C28 0.029(3) 0.046(3) 0.034(3) -0.014(2) -0.005(2) -0.006(2) C29 0.025(2) 0.031(3) 0.028(2) -0.010(2) 0.001(2) -0.002(2) C30 0.032(3) 0.0141(19) 0.023(2) -0.0051(18) -0.002(2) -0.0033(19) C31 0.023(2) 0.030(2) 0.032(3) -0.010(2) 0.001(2) 0.000(2) C32 0.036(3) 0.033(3) 0.037(3) -0.012(2) -0.011(2) 0.008(2) C33 0.047(3) 0.029(3) 0.036(3) -0.006(2) -0.019(3) -0.004(2) C34 0.058(4) 0.029(2) 0.021(2) 0.000(2) -0.003(2) -0.022(2) C35 0.031(3) 0.023(2) 0.024(2) -0.0023(19) 0.003(2) -0.013(2) O1 0.0217(16) 0.0192(14) 0.0191(15) -0.0014(12) 0.0028(13) -0.0047(13) O2 0.0219(16) 0.0203(15) 0.0230(16) -0.0038(13) 0.0024(13) -0.0024(13) N1 0.0239(19) 0.0202(18) 0.0210(19) -0.0044(15) 0.0049(16) -0.0077(16) N2 0.026(2) 0.0238(18) 0.0216(19) -0.0089(16) -0.0004(16) -0.0004(17) B1 0.019(2) 0.022(2) 0.019(2) -0.003(2) 0.001(2) -0.003(2) C36 0.023(2) 0.037(3) 0.022(2) -0.002(2) -0.005(2) -0.002(2) C37 0.026(3) 0.045(3) 0.031(3) 0.004(2) -0.003(2) -0.005(2) C38 0.026(3) 0.050(3) 0.038(3) 0.003(3) 0.010(2) 0.000(3) C39 0.046(3) 0.045(3) 0.026(3) -0.008(2) 0.003(3) 0.016(3) C40 0.030(3) 0.034(3) 0.026(2) -0.011(2) -0.002(2) 0.005(2) C41 0.020(2) 0.033(2) 0.018(2) -0.0036(19) -0.0020(18) 0.001(2) C42 0.028(2) 0.025(2) 0.018(2) -0.0066(18) -0.0047(19) 0.004(2) C43 0.025(2) 0.027(2) 0.028(2) -0.007(2) 0.002(2) -0.002(2) C44 0.027(2) 0.028(2) 0.025(2) -0.006(2) 0.003(2) -0.007(2) C45 0.023(2) 0.024(2) 0.017(2) -0.0025(18) -0.0004(18) -0.0046(19) C46 0.025(2) 0.021(2) 0.019(2) -0.0047(18) -0.0061(19) 0.0002(19) C47 0.022(2) 0.024(2) 0.020(2) -0.0063(18) -0.0033(18) -0.0042(19) C48 0.023(2) 0.022(2) 0.015(2) -0.0022(18) -0.0035(18) -0.0023(19) C49 0.023(2) 0.024(2) 0.017(2) -0.0059(18) -0.0003(18) -0.0024(19) C50 0.024(2) 0.024(2) 0.029(2) -0.008(2) 0.000(2) 0.000(2) C51 0.028(2) 0.022(2) 0.028(3) -0.002(2) 0.004(2) -0.009(2) C52 0.021(2) 0.029(2) 0.016(2) -0.0027(19) 0.0033(18) -0.008(2) C53 0.021(2) 0.026(2) 0.023(2) -0.0071(19) 0.0018(19) -0.0083(18) C54 0.028(2) 0.031(2) 0.024(2) -0.001(2) 0.002(2) -0.006(2) C55 0.028(3) 0.046(3) 0.024(2) -0.006(2) 0.005(2) -0.007(2) C56 0.026(2) 0.039(3) 0.025(2) -0.014(2) 0.004(2) -0.003(2) C57 0.032(3) 0.028(2) 0.037(3) -0.014(2) 0.000(2) 0.002(2) C58 0.034(3) 0.029(3) 0.023(2) -0.005(2) 0.006(2) -0.008(2) C59 0.023(2) 0.025(2) 0.016(2) -0.0025(18) 0.0069(18) -0.0055(19) C60 0.030(3) 0.029(2) 0.025(2) -0.005(2) -0.002(2) -0.006(2) C61 0.029(3) 0.046(3) 0.042(3) -0.022(3) -0.003(2) -0.010(2) C62 0.032(3) 0.039(3) 0.062(4) -0.026(3) -0.001(3) -0.011(2) C63 0.041(3) 0.026(3) 0.057(4) -0.014(3) -0.002(3) -0.003(2) C64 0.027(2) 0.027(2) 0.031(3) -0.007(2) 0.000(2) -0.005(2) C65 0.026(2) 0.016(2) 0.025(2) -0.0042(18) 0.0009(19) -0.0058(18) C66 0.036(3) 0.027(2) 0.029(3) -0.005(2) -0.002(2) -0.012(2) C67 0.047(3) 0.032(3) 0.022(2) -0.001(2) -0.003(2) -0.016(2) C68 0.055(3) 0.025(2) 0.025(2) 0.000(2) -0.015(2) -0.002(2) C69 0.030(3) 0.037(3) 0.043(3) -0.011(3) -0.015(2) 0.003(2) C70 0.034(3) 0.028(2) 0.028(2) -0.009(2) -0.007(2) 0.002(2) O3 0.0225(16) 0.0221(15) 0.0212(16) -0.0052(13) 0.0021(13) -0.0040(13) O4 0.0231(16) 0.0197(15) 0.0210(15) -0.0059(13) 0.0047(13) -0.0032(13) N3 0.0217(19) 0.0234(18) 0.0213(19) -0.0028(16) 0.0028(16) -0.0040(16) N4 0.0223(19) 0.0189(18) 0.0212(19) -0.0020(15) 0.0008(16) -0.0060(15) B2 0.023(3) 0.020(2) 0.020(2) -0.004(2) 0.004(2) -0.004(2) C1S 0.017(3) 0.036(3) 0.033(3) 0.000(3) -0.001(2) -0.009(2) Cl1S 0.079(2) 0.063(2) 0.115(3) -0.040(2) 0.021(2) -0.0281(17) Cl2S 0.0581(13) 0.0564(14) 0.0365(11) -0.0149(10) 0.0035(9) -0.0237(11) Cl3S 0.082(5) 0.131(9) 0.078(5) -0.060(6) 0.030(4) -0.083(6) Cl4S 0.037(2) 0.026(2) 0.0137(19) -0.0085(13) 0.0105(13) -0.0088(17) C2S 0.049(9) 0.089(15) 0.084(14) -0.057(13) 0.041(9) -0.059(10) C1T 0.054(4) 0.113(6) 0.087(5) -0.064(5) 0.020(4) -0.029(4) Cl1T 0.0685(11) 0.0480(8) 0.0710(12) -0.0226(8) 0.0209(9) -0.0205(8) Cl2T 0.0894(14) 0.1353(19) 0.0601(12) -0.0519(13) 0.0221(10) -0.0705(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 C1 C2 1.391(7) . ? C1 C6 1.391(8) . ? C1 H1 0.9500 . ? C2 C3 1.383(7) . ? C2 H2 0.9500 . ? C3 C4 1.368(9) . ? C3 H3 0.9500 . ? C4 C5 1.397(7) . ? C4 H4 0.9500 . ? C5 C6 1.410(6) . ? C5 H5 0.9500 . ? C6 C7 1.478(7) . ? C7 N2 1.354(5) . ? C7 C8 1.377(7) . ? C8 C9 1.381(6) . ? C8 H8 0.9500 . ? C9 C10 1.390(6) . ? C9 H9 0.9500 . ? C10 N2 1.369(6) . ? C10 C11 1.437(5) . ? C11 O2 1.313(5) . ? C11 C12 1.391(6) . ? C12 C13 1.384(5) . ? C12 H12 0.9500 . ? C13 O1 1.309(5) . ? C13 C14 1.432(6) . ? C14 N1 1.378(5) . ? C14 C15 1.393(6) . ? C15 C16 1.405(6) . ? C15 H15 0.9500 . ? C16 C17 1.394(6) . ? C16 H16 0.9500 . ? C17 N1 1.345(6) . ? C17 C18 1.469(5) . ? C18 C23 1.395(6) . ? C18 C19 1.400(7) . ? C19 C20 1.383(6) . ? C19 H19 0.9500 . ? C20 C21 1.390(6) . ? C20 H20 0.9500 . ? C21 C22 1.374(7) . ? C21 H21 0.9500 . ? C22 C23 1.383(6) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C25 1.388(6) . ? C24 C29 1.403(6) . ? C24 B1 1.604(7) . ? C25 C26 1.387(7) . ? C25 H25 0.9500 . ? C26 C27 1.365(7) . ? C26 H26 0.9500 . ? C27 C28 1.393(6) . ? C27 H27 0.9500 . ? C28 C29 1.382(7) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 C35 1.400(6) . ? C30 C31 1.402(6) . ? C30 B1 1.613(6) . ? C31 C32 1.376(6) . ? C31 H31 0.9500 . ? C32 C33 1.392(7) . ? C32 H32 0.9500 . ? C33 C34 1.382(7) . ? C33 H33 0.9500 . ? C34 C35 1.393(7) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? O1 B1 1.516(6) . ? O2 B1 1.535(5) . ? N1 H1N 0.8800 . ? N2 H2N 0.8800 . ? C36 C41 1.385(7) . ? C36 C37 1.394(7) . ? C36 H36 0.9500 . ? C37 C38 1.385(7) . ? C37 H37 0.9500 . ? C38 C39 1.380(9) . ? C38 H38 0.9500 . ? C39 C40 1.385(8) . ? C39 H39 0.9500 . ? C40 C41 1.398(6) . ? C40 H40 0.9500 . ? C41 C42 1.450(7) . ? C42 N3 1.374(5) . ? C42 C43 1.381(7) . ? C43 C44 1.412(6) . ? C43 H43 0.9500 . ? C44 C45 1.382(6) . ? C44 H44 0.9500 . ? C45 N3 1.386(6) . ? C45 C46 1.424(5) . ? C46 O3 1.313(5) . ? C46 C47 1.379(7) . ? C47 C48 1.399(5) . ? C47 H47 0.9500 . ? C48 O4 1.310(5) . ? C48 C49 1.431(7) . ? C49 C50 1.369(7) . ? C49 N4 1.374(5) . ? C50 C51 1.393(6) . ? C50 H50 0.9500 . ? C51 C52 1.386(6) . ? C51 H51 0.9500 . ? C52 N4 1.366(6) . ? C52 C53 1.472(5) . ? C53 C58 1.391(6) . ? C53 C54 1.397(6) . ? C54 C55 1.390(6) . ? C54 H54 0.9500 . ? C55 C56 1.377(6) . ? C55 H55 0.9500 . ? C56 C57 1.397(7) . ? C56 H56 0.9500 . ? C57 C58 1.388(6) . ? C57 H57 0.9500 . ? C58 H58 0.9500 . ? C59 C60 1.392(6) . ? C59 C64 1.395(6) . ? C59 B2 1.604(7) . ? C60 C61 1.383(7) . ? C60 H60 0.9500 . ? C61 C62 1.383(7) . ? C61 H61 0.9500 . ? C62 C63 1.380(7) . ? C62 H62 0.9500 . ? C63 C64 1.383(7) . ? C63 H63 0.9500 . ? C64 H64 0.9500 . ? C65 C70 1.386(7) . ? C65 C66 1.403(6) . ? C65 B2 1.605(7) . ? C66 C67 1.387(7) . ? C66 H66 0.9500 . ? C67 C68 1.381(7) . ? C67 H67 0.9500 . ? C68 C69 1.378(7) . ? C68 H68 0.9500 . ? C69 C70 1.404(6) . ? C69 H69 0.9500 . ? C70 H70 0.9500 . ? O3 B2 1.527(5) . ? O4 B2 1.531(6) . ? N3 H3N 0.8800 . ? N4 H4N 0.8800 . ? C1S Cl2S 1.740(8) . ? C1S Cl1S 1.741(7) . ? C1S H1S 0.9900 . ? C1S H2S 0.9900 . ? Cl3S C2S 1.743(16) . ? Cl4S C2S 1.731(15) . ? C2S H3S 0.9900 . ? C2S H4S 0.9900 . ? C1T Cl1T 1.724(6) . ? C1T Cl2T 1.739(8) . ? C1T H1T 0.9900 . ? C1T H2T 0.9900 . ? 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 C2 C1 C6 120.2(5) . . ? C2 C1 H1 119.9 . . ? C6 C1 H1 119.9 . . ? C3 C2 C1 120.7(6) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C4 C3 C2 119.6(5) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 121.3(5) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C4 C5 C6 119.2(6) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C1 C6 C5 119.0(5) . . ? C1 C6 C7 122.3(4) . . ? C5 C6 C7 118.7(5) . . ? N2 C7 C8 108.1(4) . . ? N2 C7 C6 121.5(5) . . ? C8 C7 C6 130.4(4) . . ? C7 C8 C9 107.9(4) . . ? C7 C8 H8 126.1 . . ? C9 C8 H8 126.1 . . ? C8 C9 C10 107.5(5) . . ? C8 C9 H9 126.3 . . ? C10 C9 H9 126.3 . . ? N2 C10 C9 107.2(4) . . ? N2 C10 C11 120.9(4) . . ? C9 C10 C11 131.9(5) . . ? O2 C11 C12 121.8(4) . . ? O2 C11 C10 115.3(4) . . ? C12 C11 C10 122.9(4) . . ? C13 C12 C11 118.8(4) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? O1 C13 C12 121.7(4) . . ? O1 C13 C14 115.0(3) . . ? C12 C13 C14 123.3(4) . . ? N1 C14 C15 107.3(4) . . ? N1 C14 C13 120.9(4) . . ? C15 C14 C13 131.8(4) . . ? C14 C15 C16 106.9(4) . . ? C14 C15 H15 126.6 . . ? C16 C15 H15 126.6 . . ? C17 C16 C15 107.8(4) . . ? C17 C16 H16 126.1 . . ? C15 C16 H16 126.1 . . ? N1 C17 C16 107.7(4) . . ? N1 C17 C18 123.0(4) . . ? C16 C17 C18 129.3(5) . . ? C23 C18 C19 118.4(4) . . ? C23 C18 C17 121.0(4) . . ? C19 C18 C17 120.6(4) . . ? C20 C19 C18 120.8(4) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C21 119.9(5) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C22 C21 C20 119.8(4) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C21 C22 C23 120.8(4) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C22 C23 C18 120.4(5) . . ? C22 C23 H23 119.8 . . ? C18 C23 H23 119.8 . . ? C25 C24 C29 117.4(5) . . ? C25 C24 B1 122.2(4) . . ? C29 C24 B1 120.3(4) . . ? C26 C25 C24 121.6(5) . . ? C26 C25 H25 119.2 . . ? C24 C25 H25 119.2 . . ? C27 C26 C25 120.1(4) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C26 C27 C28 119.9(5) . . ? C26 C27 H27 120.1 . . ? C28 C27 H27 120.1 . . ? C29 C28 C27 119.9(5) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C28 C29 C24 121.1(4) . . ? C28 C29 H29 119.5 . . ? C24 C29 H29 119.5 . . ? C35 C30 C31 116.6(4) . . ? C35 C30 B1 120.9(4) . . ? C31 C30 B1 122.5(4) . . ? C32 C31 C30 122.4(4) . . ? C32 C31 H31 118.8 . . ? C30 C31 H31 118.8 . . ? C31 C32 C33 119.8(5) . . ? C31 C32 H32 120.1 . . ? C33 C32 H32 120.1 . . ? C34 C33 C32 119.4(5) . . ? C34 C33 H33 120.3 . . ? C32 C33 H33 120.3 . . ? C33 C34 C35 120.3(5) . . ? C33 C34 H34 119.9 . . ? C35 C34 H34 119.9 . . ? C34 C35 C30 121.4(5) . . ? C34 C35 H35 119.3 . . ? C30 C35 H35 119.3 . . ? C13 O1 B1 118.3(3) . . ? C11 O2 B1 116.9(4) . . ? C17 N1 C14 110.4(4) . . ? C17 N1 H1N 124.8 . . ? C14 N1 H1N 124.8 . . ? C7 N2 C10 109.3(4) . . ? C7 N2 H2N 125.3 . . ? C10 N2 H2N 125.3 . . ? O1 B1 O2 107.2(3) . . ? O1 B1 C24 107.0(4) . . ? O2 B1 C24 107.9(4) . . ? O1 B1 C30 109.6(4) . . ? O2 B1 C30 108.1(3) . . ? C24 B1 C30 116.7(3) . . ? C41 C36 C37 121.1(5) . . ? C41 C36 H36 119.4 . . ? C37 C36 H36 119.4 . . ? C38 C37 C36 118.8(6) . . ? C38 C37 H37 120.6 . . ? C36 C37 H37 120.6 . . ? C39 C38 C37 120.6(5) . . ? C39 C38 H38 119.7 . . ? C37 C38 H38 119.7 . . ? C38 C39 C40 120.6(5) . . ? C38 C39 H39 119.7 . . ? C40 C39 H39 119.7 . . ? C39 C40 C41 119.6(6) . . ? C39 C40 H40 120.2 . . ? C41 C40 H40 120.2 . . ? C36 C41 C40 119.3(5) . . ? C36 C41 C42 121.4(4) . . ? C40 C41 C42 119.3(5) . . ? N3 C42 C43 106.3(4) . . ? N3 C42 C41 122.7(5) . . ? C43 C42 C41 131.0(4) . . ? C42 C43 C44 108.9(4) . . ? C42 C43 H43 125.6 . . ? C44 C43 H43 125.6 . . ? C45 C44 C43 107.2(4) . . ? C45 C44 H44 126.4 . . ? C43 C44 H44 126.4 . . ? C44 C45 N3 107.0(4) . . ? C44 C45 C46 132.0(5) . . ? N3 C45 C46 121.0(4) . . ? O3 C46 C47 121.8(4) . . ? O3 C46 C45 115.3(4) . . ? C47 C46 C45 122.8(4) . . ? C46 C47 C48 119.2(5) . . ? C46 C47 H47 120.4 . . ? C48 C47 H47 120.4 . . ? O4 C48 C47 121.4(4) . . ? O4 C48 C49 115.0(3) . . ? C47 C48 C49 123.6(4) . . ? C50 C49 N4 107.5(4) . . ? C50 C49 C48 132.2(4) . . ? N4 C49 C48 120.4(4) . . ? C49 C50 C51 107.9(4) . . ? C49 C50 H50 126.0 . . ? C51 C50 H50 126.0 . . ? C52 C51 C50 108.0(4) . . ? C52 C51 H51 126.0 . . ? C50 C51 H51 126.0 . . ? N4 C52 C51 106.9(4) . . ? N4 C52 C53 122.1(4) . . ? C51 C52 C53 131.0(4) . . ? C58 C53 C54 118.8(4) . . ? C58 C53 C52 121.4(4) . . ? C54 C53 C52 119.7(4) . . ? C55 C54 C53 120.3(4) . . ? C55 C54 H54 119.9 . . ? C53 C54 H54 119.9 . . ? C56 C55 C54 120.9(5) . . ? C56 C55 H55 119.6 . . ? C54 C55 H55 119.6 . . ? C55 C56 C57 119.1(4) . . ? C55 C56 H56 120.5 . . ? C57 C56 H56 120.5 . . ? C58 C57 C56 120.4(4) . . ? C58 C57 H57 119.8 . . ? C56 C57 H57 119.8 . . ? C57 C58 C53 120.5(5) . . ? C57 C58 H58 119.8 . . ? C53 C58 H58 119.8 . . ? C60 C59 C64 116.9(5) . . ? C60 C59 B2 120.9(4) . . ? C64 C59 B2 122.1(4) . . ? C61 C60 C59 121.9(4) . . ? C61 C60 H60 119.0 . . ? C59 C60 H60 119.0 . . ? C62 C61 C60 120.1(5) . . ? C62 C61 H61 120.0 . . ? C60 C61 H61 120.0 . . ? C63 C62 C61 119.2(5) . . ? C63 C62 H62 120.4 . . ? C61 C62 H62 120.4 . . ? C62 C63 C64 120.5(4) . . ? C62 C63 H63 119.8 . . ? C64 C63 H63 119.8 . . ? C63 C64 C59 121.5(5) . . ? C63 C64 H64 119.3 . . ? C59 C64 H64 119.3 . . ? C70 C65 C66 116.4(4) . . ? C70 C65 B2 123.1(4) . . ? C66 C65 B2 120.6(4) . . ? C67 C66 C65 121.9(5) . . ? C67 C66 H66 119.0 . . ? C65 C66 H66 119.0 . . ? C68 C67 C66 120.1(5) . . ? C68 C67 H67 120.0 . . ? C66 C67 H67 120.0 . . ? C69 C68 C67 119.9(5) . . ? C69 C68 H68 120.1 . . ? C67 C68 H68 120.1 . . ? C68 C69 C70 119.3(5) . . ? C68 C69 H69 120.4 . . ? C70 C69 H69 120.4 . . ? C65 C70 C69 122.4(5) . . ? C65 C70 H70 118.8 . . ? C69 C70 H70 118.8 . . ? C46 O3 B2 117.1(4) . . ? C48 O4 B2 117.7(3) . . ? C42 N3 C45 110.6(4) . . ? C42 N3 H3N 124.7 . . ? C45 N3 H3N 124.7 . . ? C52 N4 C49 109.8(4) . . ? C52 N4 H4N 125.1 . . ? C49 N4 H4N 125.1 . . ? O3 B2 O4 107.2(3) . . ? O3 B2 C59 108.2(4) . . ? O4 B2 C59 106.4(3) . . ? O3 B2 C65 108.8(3) . . ? O4 B2 C65 109.3(4) . . ? C59 B2 C65 116.6(3) . . ? Cl2S C1S Cl1S 111.7(4) . . ? Cl2S C1S H1S 109.3 . . ? Cl1S C1S H1S 109.3 . . ? Cl2S C1S H2S 109.3 . . ? Cl1S C1S H2S 109.3 . . ? H1S C1S H2S 107.9 . . ? Cl4S C2S Cl3S 110.8(8) . . ? Cl4S C2S H3S 109.5 . . ? Cl3S C2S H3S 109.5 . . ? Cl4S C2S H4S 109.5 . . ? Cl3S C2S H4S 109.5 . . ? H3S C2S H4S 108.1 . . ? Cl1T C1T Cl2T 113.4(4) . . ? Cl1T C1T H1T 108.9 . . ? Cl2T C1T H1T 108.9 . . ? Cl1T C1T H2T 108.9 . . ? Cl2T C1T H2T 108.9 . . ? H1T C1T H2T 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.2(7) . . . . ? C1 C2 C3 C4 0.1(7) . . . . ? C2 C3 C4 C5 -0.1(7) . . . . ? C3 C4 C5 C6 -0.1(7) . . . . ? C2 C1 C6 C5 -0.4(6) . . . . ? C2 C1 C6 C7 -179.7(4) . . . . ? C4 C5 C6 C1 0.3(6) . . . . ? C4 C5 C6 C7 179.6(4) . . . . ? C1 C6 C7 N2 33.3(6) . . . . ? C5 C6 C7 N2 -146.0(4) . . . . ? C1 C6 C7 C8 -147.6(5) . . . . ? C5 C6 C7 C8 33.1(7) . . . . ? N2 C7 C8 C9 0.3(5) . . . . ? C6 C7 C8 C9 -178.9(5) . . . . ? C7 C8 C9 C10 0.5(5) . . . . ? C8 C9 C10 N2 -1.0(5) . . . . ? C8 C9 C10 C11 177.3(5) . . . . ? N2 C10 C11 O2 -5.3(6) . . . . ? C9 C10 C11 O2 176.5(4) . . . . ? N2 C10 C11 C12 176.0(4) . . . . ? C9 C10 C11 C12 -2.1(8) . . . . ? O2 C11 C12 C13 -8.1(6) . . . . ? C10 C11 C12 C13 170.5(4) . . . . ? C11 C12 C13 O1 10.5(6) . . . . ? C11 C12 C13 C14 -168.8(4) . . . . ? O1 C13 C14 N1 7.3(6) . . . . ? C12 C13 C14 N1 -173.4(4) . . . . ? O1 C13 C14 C15 -172.5(5) . . . . ? C12 C13 C14 C15 6.8(8) . . . . ? N1 C14 C15 C16 -0.7(5) . . . . ? C13 C14 C15 C16 179.1(5) . . . . ? C14 C15 C16 C17 0.8(5) . . . . ? C15 C16 C17 N1 -0.7(5) . . . . ? C15 C16 C17 C18 177.1(5) . . . . ? N1 C17 C18 C23 21.6(8) . . . . ? C16 C17 C18 C23 -155.8(5) . . . . ? N1 C17 C18 C19 -158.9(5) . . . . ? C16 C17 C18 C19 23.7(8) . . . . ? C23 C18 C19 C20 0.6(8) . . . . ? C17 C18 C19 C20 -178.9(5) . . . . ? C18 C19 C20 C21 -0.4(8) . . . . ? C19 C20 C21 C22 0.5(8) . . . . ? C20 C21 C22 C23 -0.9(9) . . . . ? C21 C22 C23 C18 1.1(8) . . . . ? C19 C18 C23 C22 -0.9(8) . . . . ? C17 C18 C23 C22 178.6(5) . . . . ? C29 C24 C25 C26 -1.4(7) . . . . ? B1 C24 C25 C26 176.3(4) . . . . ? C24 C25 C26 C27 1.1(8) . . . . ? C25 C26 C27 C28 -0.2(8) . . . . ? C26 C27 C28 C29 -0.2(8) . . . . ? C27 C28 C29 C24 -0.1(8) . . . . ? C25 C24 C29 C28 0.9(7) . . . . ? B1 C24 C29 C28 -176.8(4) . . . . ? C35 C30 C31 C32 0.0(6) . . . . ? B1 C30 C31 C32 179.3(4) . . . . ? C30 C31 C32 C33 0.7(7) . . . . ? C31 C32 C33 C34 -1.3(7) . . . . ? C32 C33 C34 C35 1.2(7) . . . . ? C33 C34 C35 C30 -0.5(7) . . . . ? C31 C30 C35 C34 -0.1(6) . . . . ? B1 C30 C35 C34 -179.4(4) . . . . ? C12 C13 O1 B1 16.0(6) . . . . ? C14 C13 O1 B1 -164.6(4) . . . . ? C12 C11 O2 B1 -20.1(6) . . . . ? C10 C11 O2 B1 161.2(4) . . . . ? C16 C17 N1 C14 0.2(5) . . . . ? C18 C17 N1 C14 -177.7(4) . . . . ? C15 C14 N1 C17 0.3(5) . . . . ? C13 C14 N1 C17 -179.5(4) . . . . ? C8 C7 N2 C10 -0.9(5) . . . . ? C6 C7 N2 C10 178.3(4) . . . . ? C9 C10 N2 C7 1.2(5) . . . . ? C11 C10 N2 C7 -177.3(4) . . . . ? C13 O1 B1 O2 -39.8(5) . . . . ? C13 O1 B1 C24 -155.3(3) . . . . ? C13 O1 B1 C30 77.4(4) . . . . ? C11 O2 B1 O1 41.6(5) . . . . ? C11 O2 B1 C24 156.5(3) . . . . ? C11 O2 B1 C30 -76.5(5) . . . . ? C25 C24 B1 O1 -107.4(4) . . . . ? C29 C24 B1 O1 70.2(5) . . . . ? C25 C24 B1 O2 137.6(4) . . . . ? C29 C24 B1 O2 -44.8(5) . . . . ? C25 C24 B1 C30 15.7(6) . . . . ? C29 C24 B1 C30 -166.7(4) . . . . ? C35 C30 B1 O1 -162.2(4) . . . . ? C31 C30 B1 O1 18.5(5) . . . . ? C35 C30 B1 O2 -45.7(6) . . . . ? C31 C30 B1 O2 135.1(4) . . . . ? C35 C30 B1 C24 76.1(5) . . . . ? C31 C30 B1 C24 -103.2(5) . . . . ? C41 C36 C37 C38 -0.4(6) . . . . ? C36 C37 C38 C39 -0.3(7) . . . . ? C37 C38 C39 C40 0.6(7) . . . . ? C38 C39 C40 C41 -0.3(7) . . . . ? C37 C36 C41 C40 0.7(6) . . . . ? C37 C36 C41 C42 -179.4(4) . . . . ? C39 C40 C41 C36 -0.4(6) . . . . ? C39 C40 C41 C42 179.7(4) . . . . ? C36 C41 C42 N3 -33.6(6) . . . . ? C40 C41 C42 N3 146.3(4) . . . . ? C36 C41 C42 C43 147.6(5) . . . . ? C40 C41 C42 C43 -32.4(7) . . . . ? N3 C42 C43 C44 -1.0(5) . . . . ? C41 C42 C43 C44 177.9(5) . . . . ? C42 C43 C44 C45 0.0(5) . . . . ? C43 C44 C45 N3 1.0(5) . . . . ? C43 C44 C45 C46 -177.3(4) . . . . ? C44 C45 C46 O3 -176.3(4) . . . . ? N3 C45 C46 O3 5.6(6) . . . . ? C44 C45 C46 C47 1.4(8) . . . . ? N3 C45 C46 C47 -176.7(4) . . . . ? O3 C46 C47 C48 7.1(6) . . . . ? C45 C46 C47 C48 -170.4(4) . . . . ? C46 C47 C48 O4 -9.2(6) . . . . ? C46 C47 C48 C49 168.3(4) . . . . ? O4 C48 C49 C50 171.5(5) . . . . ? C47 C48 C49 C50 -6.1(8) . . . . ? O4 C48 C49 N4 -9.0(6) . . . . ? C47 C48 C49 N4 173.3(4) . . . . ? N4 C49 C50 C51 0.4(5) . . . . ? C48 C49 C50 C51 179.9(5) . . . . ? C49 C50 C51 C52 0.0(5) . . . . ? C50 C51 C52 N4 -0.4(5) . . . . ? C50 C51 C52 C53 -177.7(5) . . . . ? N4 C52 C53 C58 -22.3(7) . . . . ? C51 C52 C53 C58 154.6(5) . . . . ? N4 C52 C53 C54 160.4(5) . . . . ? C51 C52 C53 C54 -22.7(8) . . . . ? C58 C53 C54 C55 1.5(8) . . . . ? C52 C53 C54 C55 178.8(5) . . . . ? C53 C54 C55 C56 -1.3(8) . . . . ? C54 C55 C56 C57 0.9(8) . . . . ? C55 C56 C57 C58 -0.7(8) . . . . ? C56 C57 C58 C53 0.9(8) . . . . ? C54 C53 C58 C57 -1.3(8) . . . . ? C52 C53 C58 C57 -178.6(5) . . . . ? C64 C59 C60 C61 0.3(7) . . . . ? B2 C59 C60 C61 177.1(4) . . . . ? C59 C60 C61 C62 -1.2(8) . . . . ? C60 C61 C62 C63 1.5(8) . . . . ? C61 C62 C63 C64 -0.8(8) . . . . ? C62 C63 C64 C59 -0.1(8) . . . . ? C60 C59 C64 C63 0.3(7) . . . . ? B2 C59 C64 C63 -176.3(4) . . . . ? C70 C65 C66 C67 1.0(7) . . . . ? B2 C65 C66 C67 -179.7(4) . . . . ? C65 C66 C67 C68 -1.2(7) . . . . ? C66 C67 C68 C69 1.5(7) . . . . ? C67 C68 C69 C70 -1.6(7) . . . . ? C66 C65 C70 C69 -1.1(7) . . . . ? B2 C65 C70 C69 179.6(4) . . . . ? C68 C69 C70 C65 1.4(7) . . . . ? C47 C46 O3 B2 21.0(6) . . . . ? C45 C46 O3 B2 -161.3(4) . . . . ? C47 C48 O4 B2 -17.1(6) . . . . ? C49 C48 O4 B2 165.1(4) . . . . ? C43 C42 N3 C45 1.7(5) . . . . ? C41 C42 N3 C45 -177.3(4) . . . . ? C44 C45 N3 C42 -1.7(5) . . . . ? C46 C45 N3 C42 176.8(4) . . . . ? C51 C52 N4 C49 0.6(5) . . . . ? C53 C52 N4 C49 178.2(4) . . . . ? C50 C49 N4 C52 -0.6(5) . . . . ? C48 C49 N4 C52 179.8(4) . . . . ? C46 O3 B2 O4 -42.4(5) . . . . ? C46 O3 B2 C59 -156.8(3) . . . . ? C46 O3 B2 C65 75.6(5) . . . . ? C48 O4 B2 O3 40.6(5) . . . . ? C48 O4 B2 C59 156.1(3) . . . . ? C48 O4 B2 C65 -77.2(4) . . . . ? C60 C59 B2 O3 45.1(5) . . . . ? C64 C59 B2 O3 -138.4(4) . . . . ? C60 C59 B2 O4 -69.8(5) . . . . ? C64 C59 B2 O4 106.8(4) . . . . ? C60 C59 B2 C65 168.0(4) . . . . ? C64 C59 B2 C65 -15.4(6) . . . . ? C70 C65 B2 O3 -134.8(4) . . . . ? C66 C65 B2 O3 45.9(6) . . . . ? C70 C65 B2 O4 -18.1(5) . . . . ? C66 C65 B2 O4 162.6(4) . . . . ? C70 C65 B2 C59 102.6(5) . . . . ? C66 C65 B2 C59 -76.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.320 _refine_diff_density_min -0.390 _refine_diff_density_rms 0.052 #============================================================================== # End of CIF #============================================================================== data_90513 _database_code_depnum_ccdc_archive 'CCDC 759622' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H39 B N2 O4' _chemical_formula_weight 634.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 10.102(2) _cell_length_b 18.284(5) _cell_length_c 18.278(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.046(10) _cell_angle_gamma 90.00 _cell_volume 3363.1(14) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9611 _exptl_absorpt_correction_T_max 0.9687 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _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 \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32199 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.47 _reflns_number_total 7684 _reflns_number_gt 5672 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0391P)^2^+1.3853P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7684 _refine_ls_number_parameters 437 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.1032 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 C1 C 1.40241(16) -0.18363(9) 0.19355(9) 0.0268(4) Uani 1 1 d . . . H1 H 1.4540 -0.1856 0.2395 0.032 Uiso 1 1 calc R . . C2 C 1.43883(18) -0.22578(10) 0.13569(10) 0.0315(4) Uani 1 1 d . . . H2 H 1.5146 -0.2566 0.1423 0.038 Uiso 1 1 calc R . . C3 C 1.3655(2) -0.22318(10) 0.06842(10) 0.0362(4) Uani 1 1 d . . . H3 H 1.3909 -0.2517 0.0285 0.043 Uiso 1 1 calc R . . C4 C 1.2546(2) -0.17851(11) 0.05967(10) 0.0381(5) Uani 1 1 d . . . H4 H 1.2034 -0.1768 0.0135 0.046 Uiso 1 1 calc R . . C5 C 1.21716(18) -0.13629(10) 0.11720(9) 0.0309(4) Uani 1 1 d . . . H5 H 1.1409 -0.1059 0.1102 0.037 Uiso 1 1 calc R . . C6 C 1.29081(16) -0.13820(9) 0.18532(8) 0.0226(3) Uani 1 1 d . . . C7 C 1.25489(15) -0.09469(8) 0.24804(8) 0.0204(3) Uani 1 1 d . . . C8 C 1.32886(16) -0.08189(9) 0.31432(9) 0.0232(3) Uani 1 1 d . . . H6 H 1.4155 -0.1001 0.3283 0.028 Uiso 1 1 calc R . . C9 C 1.25376(15) -0.03763(9) 0.35687(8) 0.0224(3) Uani 1 1 d . . . H7 H 1.2800 -0.0202 0.4049 0.027 Uiso 1 1 calc R . . C10 C 1.13395(15) -0.02362(8) 0.31651(8) 0.0197(3) Uani 1 1 d . . . C11 C 1.01962(15) 0.01562(8) 0.33602(8) 0.0191(3) Uani 1 1 d . . . C12 C 1.01296(15) 0.04663(8) 0.40486(8) 0.0206(3) Uani 1 1 d . . . H39 H 1.0794 0.0362 0.4435 0.025 Uiso 1 1 calc R . . C13 C 0.90815(15) 0.09314(8) 0.41676(8) 0.0187(3) Uani 1 1 d . . . C14 C 0.90288(15) 0.13514(8) 0.48240(8) 0.0183(3) Uani 1 1 d . . . C15 C 0.99008(15) 0.14045(8) 0.54534(8) 0.0201(3) Uani 1 1 d . . . H8 H 1.0723 0.1155 0.5545 0.024 Uiso 1 1 calc R . . C16 C 0.93450(15) 0.18921(8) 0.59260(8) 0.0202(3) Uani 1 1 d . . . H9 H 0.9721 0.2032 0.6400 0.024 Uiso 1 1 calc R . . C17 C 0.81407(15) 0.21382(8) 0.55819(8) 0.0196(3) Uani 1 1 d . . . C18 C 0.72047(15) 0.26822(8) 0.58128(8) 0.0198(3) Uani 1 1 d . . . C19 C 0.64048(16) 0.30852(9) 0.52985(8) 0.0245(3) Uani 1 1 d . . . H10 H 0.6424 0.2981 0.4790 0.029 Uiso 1 1 calc R . . C20 C 0.55834(17) 0.36346(9) 0.55178(9) 0.0279(4) Uani 1 1 d . . . H11 H 0.5056 0.3908 0.5159 0.033 Uiso 1 1 calc R . . C21 C 0.55245(16) 0.37898(10) 0.62551(9) 0.0275(4) Uani 1 1 d . . . H12 H 0.4971 0.4172 0.6405 0.033 Uiso 1 1 calc R . . C22 C 0.62812(17) 0.33809(10) 0.67694(9) 0.0301(4) Uani 1 1 d . . . H13 H 0.6229 0.3474 0.7277 0.036 Uiso 1 1 calc R . . C23 C 0.71163(16) 0.28361(9) 0.65545(8) 0.0260(4) Uani 1 1 d . . . H14 H 0.7636 0.2563 0.6917 0.031 Uiso 1 1 calc R . . C24 C 0.69008(15) 0.06975(8) 0.24200(8) 0.0195(3) Uani 1 1 d . . . C25 C 0.73152(16) 0.12532(9) 0.19670(8) 0.0223(3) Uani 1 1 d . . . H15 H 0.8176 0.1458 0.2070 0.027 Uiso 1 1 calc R . . C26 C 0.65090(17) 0.15141(9) 0.13728(8) 0.0271(4) Uani 1 1 d . . . H16 H 0.6820 0.1892 0.1075 0.033 Uiso 1 1 calc R . . C27 C 0.52479(18) 0.12259(10) 0.12115(9) 0.0293(4) Uani 1 1 d . . . H17 H 0.4695 0.1401 0.0802 0.035 Uiso 1 1 calc R . . C28 C 0.48026(17) 0.06817(10) 0.16519(10) 0.0315(4) Uani 1 1 d . . . H18 H 0.3936 0.0485 0.1549 0.038 Uiso 1 1 calc R . . C29 C 0.56231(16) 0.04215(9) 0.22470(9) 0.0262(4) Uani 1 1 d . . . H19 H 0.5304 0.0045 0.2544 0.031 Uiso 1 1 calc R . . C30 C 0.72977(15) -0.03063(9) 0.35132(8) 0.0208(3) Uani 1 1 d . . . C31 C 0.74021(17) -0.10014(9) 0.32107(9) 0.0276(4) Uani 1 1 d . . . H20 H 0.7837 -0.1056 0.2774 0.033 Uiso 1 1 calc R . . C32 C 0.68881(18) -0.16180(10) 0.35304(11) 0.0374(5) Uani 1 1 d . . . H21 H 0.6962 -0.2084 0.3307 0.045 Uiso 1 1 calc R . . C33 C 0.62698(19) -0.15544(11) 0.41733(11) 0.0407(5) Uani 1 1 d . . . H22 H 0.5931 -0.1976 0.4396 0.049 Uiso 1 1 calc R . . C34 C 0.61483(18) -0.08732(11) 0.44890(10) 0.0365(4) Uani 1 1 d . . . H23 H 0.5723 -0.0824 0.4930 0.044 Uiso 1 1 calc R . . C35 C 0.66514(16) -0.02596(10) 0.41584(9) 0.0268(4) Uani 1 1 d . . . H24 H 0.6553 0.0206 0.4378 0.032 Uiso 1 1 calc R . . C36 C 0.7666(2) -0.00454(11) 0.03576(12) 0.0460(5) Uani 1 1 d . . . H25 H 0.7067 0.0325 0.0531 0.069 Uiso 1 1 calc R . . H26 H 0.7239 -0.0284 -0.0082 0.069 Uiso 1 1 calc R . . H27 H 0.8492 0.0189 0.0238 0.069 Uiso 1 1 calc R . . C37 C 0.79695(18) -0.06006(10) 0.09434(10) 0.0333(4) Uani 1 1 d . . . C38 C 0.6836(2) -0.10758(12) 0.11218(11) 0.0445(5) Uani 1 1 d . . . H28 H 0.7157 -0.1446 0.1482 0.067 Uiso 1 1 calc R . . H29 H 0.6453 -0.1317 0.0674 0.067 Uiso 1 1 calc R . . H30 H 0.6156 -0.0775 0.1327 0.067 Uiso 1 1 calc R . . C39 C 0.34783(18) 0.15645(11) 0.34061(10) 0.0375(4) Uani 1 1 d . . . H31 H 0.3157 0.1309 0.3827 0.056 Uiso 1 1 calc R . . H32 H 0.3523 0.1221 0.2997 0.056 Uiso 1 1 calc R . . H33 H 0.2868 0.1964 0.3255 0.056 Uiso 1 1 calc R . . C40 C 0.48270(17) 0.18683(9) 0.36166(9) 0.0258(4) Uani 1 1 d . . . C41 C 0.5418(2) 0.23566(11) 0.30798(10) 0.0405(5) Uani 1 1 d . . . H34 H 0.4983 0.2836 0.3078 0.061 Uiso 1 1 calc R . . H35 H 0.5288 0.2140 0.2588 0.061 Uiso 1 1 calc R . . H36 H 0.6371 0.2415 0.3220 0.061 Uiso 1 1 calc R . . O1 O 0.92067(10) 0.02197(6) 0.28454(5) 0.0206(2) Uani 1 1 d . . . O2 O 0.80797(10) 0.10214(6) 0.36640(5) 0.0198(2) Uani 1 1 d . . . O3 O 0.90714(13) -0.06652(8) 0.12619(7) 0.0453(4) Uani 1 1 d . . . O4 O 0.54118(12) 0.17238(7) 0.42060(6) 0.0335(3) Uani 1 1 d . . . N1 N 1.13673(12) -0.05861(7) 0.25003(7) 0.0198(3) Uani 1 1 d . . . H37 H 1.0724 -0.0579 0.2143 0.024 Uiso 1 1 calc R . . N2 N 0.79702(12) 0.18057(7) 0.49146(6) 0.0191(3) Uani 1 1 d . . . H38 H 0.7285 0.1871 0.4589 0.023 Uiso 1 1 calc R . . B1 B 0.78473(17) 0.04027(10) 0.31102(9) 0.0194(3) 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 C1 0.0226(8) 0.0279(9) 0.0300(8) -0.0030(7) 0.0036(7) 0.0006(7) C2 0.0273(9) 0.0293(9) 0.0394(10) -0.0033(8) 0.0107(8) 0.0059(7) C3 0.0473(11) 0.0343(10) 0.0289(9) -0.0050(8) 0.0142(8) 0.0094(9) C4 0.0495(12) 0.0421(11) 0.0230(8) -0.0033(8) 0.0040(8) 0.0128(9) C5 0.0354(10) 0.0322(9) 0.0252(8) -0.0002(7) 0.0039(7) 0.0107(8) C6 0.0229(8) 0.0214(8) 0.0243(8) -0.0002(6) 0.0059(6) -0.0001(6) C7 0.0182(7) 0.0195(7) 0.0238(7) 0.0015(6) 0.0048(6) 0.0000(6) C8 0.0186(8) 0.0235(8) 0.0274(8) 0.0009(6) 0.0009(6) 0.0009(6) C9 0.0224(8) 0.0231(8) 0.0216(7) -0.0019(6) 0.0008(6) -0.0014(7) C10 0.0214(8) 0.0190(7) 0.0189(7) -0.0003(6) 0.0026(6) -0.0025(6) C11 0.0189(8) 0.0172(7) 0.0212(7) 0.0016(6) 0.0015(6) -0.0019(6) C12 0.0200(8) 0.0222(8) 0.0190(7) -0.0009(6) -0.0006(6) 0.0002(6) C13 0.0202(7) 0.0177(7) 0.0181(7) 0.0022(6) 0.0009(6) -0.0027(6) C14 0.0195(7) 0.0162(7) 0.0192(7) 0.0010(6) 0.0024(6) -0.0009(6) C15 0.0190(7) 0.0186(7) 0.0221(7) 0.0004(6) -0.0005(6) -0.0011(6) C16 0.0219(8) 0.0202(8) 0.0180(7) -0.0012(6) -0.0015(6) -0.0016(6) C17 0.0222(8) 0.0194(7) 0.0171(7) 0.0000(6) 0.0014(6) -0.0041(6) C18 0.0193(7) 0.0187(7) 0.0214(7) -0.0009(6) 0.0022(6) -0.0030(6) C19 0.0285(9) 0.0254(8) 0.0198(7) 0.0003(6) 0.0027(6) 0.0014(7) C20 0.0282(9) 0.0284(9) 0.0267(8) 0.0036(7) 0.0006(7) 0.0051(7) C21 0.0226(8) 0.0281(9) 0.0323(9) -0.0033(7) 0.0052(7) 0.0043(7) C22 0.0314(9) 0.0379(10) 0.0212(8) -0.0060(7) 0.0030(7) 0.0052(8) C23 0.0268(9) 0.0297(9) 0.0210(8) -0.0009(7) -0.0014(6) 0.0051(7) C24 0.0222(8) 0.0191(7) 0.0173(7) -0.0032(6) 0.0026(6) 0.0042(6) C25 0.0235(8) 0.0230(8) 0.0206(7) -0.0006(6) 0.0023(6) 0.0005(7) C26 0.0365(10) 0.0253(9) 0.0200(8) 0.0026(7) 0.0046(7) 0.0045(7) C27 0.0344(10) 0.0310(9) 0.0210(8) -0.0004(7) -0.0052(7) 0.0095(8) C28 0.0248(9) 0.0333(9) 0.0346(9) -0.0002(8) -0.0079(7) 0.0002(8) C29 0.0257(8) 0.0256(8) 0.0267(8) 0.0032(7) -0.0016(6) -0.0007(7) C30 0.0175(7) 0.0235(8) 0.0202(7) 0.0020(6) -0.0052(6) 0.0009(6) C31 0.0275(9) 0.0243(8) 0.0295(8) 0.0009(7) -0.0066(7) 0.0012(7) C32 0.0325(10) 0.0219(9) 0.0537(12) 0.0038(8) -0.0184(9) -0.0013(8) C33 0.0291(10) 0.0383(11) 0.0520(12) 0.0239(9) -0.0123(9) -0.0091(8) C34 0.0274(9) 0.0487(12) 0.0326(9) 0.0153(9) -0.0020(7) -0.0066(8) C35 0.0237(8) 0.0323(9) 0.0238(8) 0.0035(7) -0.0011(6) -0.0027(7) C36 0.0484(13) 0.0330(11) 0.0559(13) -0.0043(9) 0.0001(10) -0.0012(9) C37 0.0336(10) 0.0344(10) 0.0316(9) -0.0156(8) 0.0004(8) 0.0005(8) C38 0.0426(12) 0.0523(13) 0.0391(11) -0.0055(10) 0.0068(9) -0.0055(10) C39 0.0323(10) 0.0426(11) 0.0356(10) -0.0010(8) -0.0085(8) 0.0001(9) C40 0.0273(9) 0.0255(8) 0.0245(8) -0.0041(7) 0.0014(7) 0.0048(7) C41 0.0484(12) 0.0374(11) 0.0376(10) 0.0035(9) 0.0136(9) 0.0038(9) O1 0.0194(5) 0.0243(6) 0.0180(5) -0.0022(4) 0.0003(4) 0.0027(4) O2 0.0199(5) 0.0206(5) 0.0184(5) -0.0019(4) -0.0010(4) 0.0018(4) O3 0.0346(8) 0.0559(9) 0.0437(8) -0.0207(7) -0.0054(6) 0.0042(7) O4 0.0259(6) 0.0479(8) 0.0257(6) -0.0002(6) -0.0026(5) -0.0008(6) N1 0.0184(6) 0.0221(7) 0.0188(6) -0.0013(5) 0.0016(5) 0.0013(5) N2 0.0202(6) 0.0196(6) 0.0171(6) -0.0016(5) -0.0004(5) 0.0003(5) B1 0.0202(8) 0.0205(8) 0.0176(8) -0.0021(7) 0.0016(6) 0.0016(7) _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 C1 C2 1.384(2) . ? C1 C6 1.398(2) . ? C1 H1 0.9500 . ? C2 C3 1.379(3) . ? C2 H2 0.9500 . ? C3 C4 1.385(3) . ? C3 H3 0.9500 . ? C4 C5 1.384(2) . ? C4 H4 0.9500 . ? C5 C6 1.394(2) . ? C5 H5 0.9500 . ? C6 C7 1.467(2) . ? C7 N1 1.367(2) . ? C7 C8 1.386(2) . ? C8 C9 1.393(2) . ? C8 H6 0.9500 . ? C9 C10 1.385(2) . ? C9 H7 0.9500 . ? C10 N1 1.3757(19) . ? C10 C11 1.431(2) . ? C11 O1 1.3163(18) . ? C11 C12 1.387(2) . ? C12 C13 1.390(2) . ? C12 H39 0.9500 . ? C13 O2 1.3171(18) . ? C13 C14 1.429(2) . ? C14 N2 1.3756(19) . ? C14 C15 1.389(2) . ? C15 C16 1.393(2) . ? C15 H8 0.9500 . ? C16 C17 1.394(2) . ? C16 H9 0.9500 . ? C17 N2 1.3602(19) . ? C17 C18 1.460(2) . ? C18 C19 1.395(2) . ? C18 C23 1.395(2) . ? C19 C20 1.385(2) . ? C19 H10 0.9500 . ? C20 C21 1.383(2) . ? C20 H11 0.9500 . ? C21 C22 1.379(2) . ? C21 H12 0.9500 . ? C22 C23 1.384(2) . ? C22 H13 0.9500 . ? C23 H14 0.9500 . ? C24 C29 1.396(2) . ? C24 C25 1.398(2) . ? C24 B1 1.608(2) . ? C25 C26 1.384(2) . ? C25 H15 0.9500 . ? C26 C27 1.386(3) . ? C26 H16 0.9500 . ? C27 C28 1.380(3) . ? C27 H17 0.9500 . ? C28 C29 1.392(2) . ? C28 H18 0.9500 . ? C29 H19 0.9500 . ? C30 C31 1.394(2) . ? C30 C35 1.400(2) . ? C30 B1 1.614(2) . ? C31 C32 1.391(3) . ? C31 H20 0.9500 . ? C32 C33 1.383(3) . ? C32 H21 0.9500 . ? C33 C34 1.383(3) . ? C33 H22 0.9500 . ? C34 C35 1.391(2) . ? C34 H23 0.9500 . ? C35 H24 0.9500 . ? C36 C37 1.488(3) . ? C36 H25 0.9800 . ? C36 H26 0.9800 . ? C36 H27 0.9800 . ? C37 O3 1.216(2) . ? C37 C38 1.496(3) . ? C38 H28 0.9800 . ? C38 H29 0.9800 . ? C38 H30 0.9800 . ? C39 C40 1.490(2) . ? C39 H31 0.9800 . ? C39 H32 0.9800 . ? C39 H33 0.9800 . ? C40 O4 1.2116(19) . ? C40 C41 1.490(2) . ? C41 H34 0.9800 . ? C41 H35 0.9800 . ? C41 H36 0.9800 . ? O1 B1 1.533(2) . ? O2 B1 1.522(2) . ? N1 H37 0.8800 . ? N2 H38 0.8800 . ? 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 C2 C1 C6 120.98(16) . . ? C2 C1 H1 119.5 . . ? C6 C1 H1 119.5 . . ? C3 C2 C1 120.27(16) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 119.26(16) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 120.91(17) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 120.33(16) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C1 118.24(15) . . ? C5 C6 C7 122.37(15) . . ? C1 C6 C7 119.39(14) . . ? N1 C7 C8 107.46(13) . . ? N1 C7 C6 123.99(14) . . ? C8 C7 C6 128.55(14) . . ? C7 C8 C9 107.93(14) . . ? C7 C8 H6 126.0 . . ? C9 C8 H6 126.0 . . ? C10 C9 C8 107.68(14) . . ? C10 C9 H7 126.2 . . ? C8 C9 H7 126.2 . . ? N1 C10 C9 107.44(13) . . ? N1 C10 C11 122.20(13) . . ? C9 C10 C11 130.29(14) . . ? O1 C11 C12 121.20(14) . . ? O1 C11 C10 116.41(13) . . ? C12 C11 C10 122.38(14) . . ? C11 C12 C13 119.37(14) . . ? C11 C12 H39 120.3 . . ? C13 C12 H39 120.3 . . ? O2 C13 C12 121.07(13) . . ? O2 C13 C14 115.87(13) . . ? C12 C13 C14 123.04(14) . . ? N2 C14 C15 107.52(13) . . ? N2 C14 C13 120.82(13) . . ? C15 C14 C13 131.66(14) . . ? C14 C15 C16 107.30(14) . . ? C14 C15 H8 126.4 . . ? C16 C15 H8 126.4 . . ? C15 C16 C17 108.06(13) . . ? C15 C16 H9 126.0 . . ? C17 C16 H9 126.0 . . ? N2 C17 C16 107.28(13) . . ? N2 C17 C18 121.97(13) . . ? C16 C17 C18 130.63(13) . . ? C19 C18 C23 117.74(14) . . ? C19 C18 C17 121.10(13) . . ? C23 C18 C17 121.11(14) . . ? C20 C19 C18 120.97(14) . . ? C20 C19 H10 119.5 . . ? C18 C19 H10 119.5 . . ? C21 C20 C19 120.60(15) . . ? C21 C20 H11 119.7 . . ? C19 C20 H11 119.7 . . ? C22 C21 C20 118.96(15) . . ? C22 C21 H12 120.5 . . ? C20 C21 H12 120.5 . . ? C21 C22 C23 120.80(15) . . ? C21 C22 H13 119.6 . . ? C23 C22 H13 119.6 . . ? C22 C23 C18 120.89(15) . . ? C22 C23 H14 119.6 . . ? C18 C23 H14 119.6 . . ? C29 C24 C25 116.59(14) . . ? C29 C24 B1 122.06(14) . . ? C25 C24 B1 121.34(14) . . ? C26 C25 C24 121.95(15) . . ? C26 C25 H15 119.0 . . ? C24 C25 H15 119.0 . . ? C25 C26 C27 120.15(16) . . ? C25 C26 H16 119.9 . . ? C27 C26 H16 119.9 . . ? C28 C27 C26 119.39(15) . . ? C28 C27 H17 120.3 . . ? C26 C27 H17 120.3 . . ? C27 C28 C29 120.00(16) . . ? C27 C28 H18 120.0 . . ? C29 C28 H18 120.0 . . ? C28 C29 C24 121.91(16) . . ? C28 C29 H19 119.0 . . ? C24 C29 H19 119.0 . . ? C31 C30 C35 116.56(15) . . ? C31 C30 B1 120.69(14) . . ? C35 C30 B1 122.70(14) . . ? C32 C31 C30 121.89(17) . . ? C32 C31 H20 119.1 . . ? C30 C31 H20 119.1 . . ? C33 C32 C31 120.11(18) . . ? C33 C32 H21 119.9 . . ? C31 C32 H21 119.9 . . ? C34 C33 C32 119.57(17) . . ? C34 C33 H22 120.2 . . ? C32 C33 H22 120.2 . . ? C33 C34 C35 119.73(17) . . ? C33 C34 H23 120.1 . . ? C35 C34 H23 120.1 . . ? C34 C35 C30 122.13(17) . . ? C34 C35 H24 118.9 . . ? C30 C35 H24 118.9 . . ? C37 C36 H25 109.5 . . ? C37 C36 H26 109.5 . . ? H25 C36 H26 109.5 . . ? C37 C36 H27 109.5 . . ? H25 C36 H27 109.5 . . ? H26 C36 H27 109.5 . . ? O3 C37 C36 122.21(18) . . ? O3 C37 C38 121.69(19) . . ? C36 C37 C38 116.10(17) . . ? C37 C38 H28 109.5 . . ? C37 C38 H29 109.5 . . ? H28 C38 H29 109.5 . . ? C37 C38 H30 109.5 . . ? H28 C38 H30 109.5 . . ? H29 C38 H30 109.5 . . ? C40 C39 H31 109.5 . . ? C40 C39 H32 109.5 . . ? H31 C39 H32 109.5 . . ? C40 C39 H33 109.5 . . ? H31 C39 H33 109.5 . . ? H32 C39 H33 109.5 . . ? O4 C40 C41 121.62(17) . . ? O4 C40 C39 120.77(16) . . ? C41 C40 C39 117.61(16) . . ? C40 C41 H34 109.5 . . ? C40 C41 H35 109.5 . . ? H34 C41 H35 109.5 . . ? C40 C41 H36 109.5 . . ? H34 C41 H36 109.5 . . ? H35 C41 H36 109.5 . . ? C11 O1 B1 116.01(11) . . ? C13 O2 B1 115.85(12) . . ? C7 N1 C10 109.49(13) . . ? C7 N1 H37 125.3 . . ? C10 N1 H37 125.3 . . ? C17 N2 C14 109.84(13) . . ? C17 N2 H38 125.1 . . ? C14 N2 H38 125.1 . . ? O2 B1 O1 106.39(12) . . ? O2 B1 C24 108.60(12) . . ? O1 B1 C24 108.23(12) . . ? O2 B1 C30 109.43(12) . . ? O1 B1 C30 108.82(12) . . ? C24 B1 C30 115.01(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.5(3) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? C3 C4 C5 C6 -0.2(3) . . . . ? C4 C5 C6 C1 0.0(3) . . . . ? C4 C5 C6 C7 -179.77(17) . . . . ? C2 C1 C6 C5 -0.1(3) . . . . ? C2 C1 C6 C7 179.63(15) . . . . ? C5 C6 C7 N1 11.5(2) . . . . ? C1 C6 C7 N1 -168.29(15) . . . . ? C5 C6 C7 C8 -168.53(17) . . . . ? C1 C6 C7 C8 11.7(3) . . . . ? N1 C7 C8 C9 0.19(18) . . . . ? C6 C7 C8 C9 -179.81(15) . . . . ? C7 C8 C9 C10 0.13(18) . . . . ? C8 C9 C10 N1 -0.39(17) . . . . ? C8 C9 C10 C11 176.50(16) . . . . ? N1 C10 C11 O1 -5.7(2) . . . . ? C9 C10 C11 O1 177.83(15) . . . . ? N1 C10 C11 C12 175.39(14) . . . . ? C9 C10 C11 C12 -1.1(3) . . . . ? O1 C11 C12 C13 -8.5(2) . . . . ? C10 C11 C12 C13 170.35(14) . . . . ? C11 C12 C13 O2 7.3(2) . . . . ? C11 C12 C13 C14 -171.19(14) . . . . ? O2 C13 C14 N2 1.3(2) . . . . ? C12 C13 C14 N2 179.83(14) . . . . ? O2 C13 C14 C15 -178.85(15) . . . . ? C12 C13 C14 C15 -0.3(3) . . . . ? N2 C14 C15 C16 0.53(17) . . . . ? C13 C14 C15 C16 -179.35(15) . . . . ? C14 C15 C16 C17 -0.36(17) . . . . ? C15 C16 C17 N2 0.06(17) . . . . ? C15 C16 C17 C18 -175.87(15) . . . . ? N2 C17 C18 C19 -24.3(2) . . . . ? C16 C17 C18 C19 151.11(17) . . . . ? N2 C17 C18 C23 158.14(15) . . . . ? C16 C17 C18 C23 -26.4(3) . . . . ? C23 C18 C19 C20 2.0(2) . . . . ? C17 C18 C19 C20 -175.62(15) . . . . ? C18 C19 C20 C21 -0.9(3) . . . . ? C19 C20 C21 C22 -1.0(3) . . . . ? C20 C21 C22 C23 1.8(3) . . . . ? C21 C22 C23 C18 -0.6(3) . . . . ? C19 C18 C23 C22 -1.3(2) . . . . ? C17 C18 C23 C22 176.36(15) . . . . ? C29 C24 C25 C26 -0.6(2) . . . . ? B1 C24 C25 C26 -179.75(14) . . . . ? C24 C25 C26 C27 0.1(2) . . . . ? C25 C26 C27 C28 0.5(2) . . . . ? C26 C27 C28 C29 -0.7(3) . . . . ? C27 C28 C29 C24 0.3(3) . . . . ? C25 C24 C29 C28 0.4(2) . . . . ? B1 C24 C29 C28 179.53(15) . . . . ? C35 C30 C31 C32 0.2(2) . . . . ? B1 C30 C31 C32 -177.32(15) . . . . ? C30 C31 C32 C33 -1.0(3) . . . . ? C31 C32 C33 C34 1.0(3) . . . . ? C32 C33 C34 C35 -0.2(3) . . . . ? C33 C34 C35 C30 -0.7(3) . . . . ? C31 C30 C35 C34 0.7(2) . . . . ? B1 C30 C35 C34 178.12(15) . . . . ? C12 C11 O1 B1 -20.7(2) . . . . ? C10 C11 O1 B1 160.38(13) . . . . ? C12 C13 O2 B1 23.18(19) . . . . ? C14 C13 O2 B1 -158.25(13) . . . . ? C8 C7 N1 C10 -0.43(17) . . . . ? C6 C7 N1 C10 179.56(14) . . . . ? C9 C10 N1 C7 0.51(17) . . . . ? C11 C10 N1 C7 -176.69(14) . . . . ? C16 C17 N2 C14 0.28(17) . . . . ? C18 C17 N2 C14 176.64(13) . . . . ? C15 C14 N2 C17 -0.50(17) . . . . ? C13 C14 N2 C17 179.39(13) . . . . ? C13 O2 B1 O1 -47.42(16) . . . . ? C13 O2 B1 C24 -163.72(12) . . . . ? C13 O2 B1 C30 70.00(16) . . . . ? C11 O1 B1 O2 46.22(16) . . . . ? C11 O1 B1 C24 162.77(12) . . . . ? C11 O1 B1 C30 -71.59(16) . . . . ? C29 C24 B1 O2 -114.67(16) . . . . ? C25 C24 B1 O2 64.46(17) . . . . ? C29 C24 B1 O1 130.22(15) . . . . ? C25 C24 B1 O1 -50.65(18) . . . . ? C29 C24 B1 C30 8.3(2) . . . . ? C25 C24 B1 C30 -172.56(14) . . . . ? C31 C30 B1 O2 -159.38(14) . . . . ? C35 C30 B1 O2 23.3(2) . . . . ? C31 C30 B1 O1 -43.51(18) . . . . ? C35 C30 B1 O1 139.13(14) . . . . ? C31 C30 B1 C24 78.08(18) . . . . ? C35 C30 B1 C24 -99.28(17) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.287 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.042 #============================================================================== # End of CIF #============================================================================== data_90528mae _database_code_depnum_ccdc_archive 'CCDC 759623' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43 H43 B N2 O2' _chemical_formula_weight 630.60 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' O O 0.0106 0.0060 '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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P - 1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.827(4) _cell_length_b 11.506(3) _cell_length_c 15.784(5) _cell_angle_alpha 78.919(11) _cell_angle_beta 88.635(14) _cell_angle_gamma 77.553(13) _cell_volume 1710.0(10) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9782 _exptl_absorpt_correction_T_max 0.9926 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _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 \w _diffrn_detector_area_resol_mean 10 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16251 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.0700 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7743 _reflns_number_gt 5051 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0703P)^2^+0.0831P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7743 _refine_ls_number_parameters 437 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0946 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1470 _refine_ls_wR_factor_gt 0.1221 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 O1 O 0.54604(13) 0.79976(10) 0.32118(8) 0.0224(3) Uani 1 1 d . . . O2 O 0.68243(12) 0.74076(10) 0.19794(8) 0.0215(3) Uani 1 1 d . . . N1 N 0.79885(15) 0.78193(13) 0.04634(9) 0.0214(3) Uani 1 1 d . . . H1 H 0.8218 0.7075 0.0764 0.026 Uiso 1 1 calc R . . N2 N 0.38210(15) 0.95202(13) 0.40262(9) 0.0219(3) Uani 1 1 d . . . H2 H 0.3929 0.8744 0.4253 0.026 Uiso 1 1 calc R . . C5 C 0.51811(18) 0.91271(15) 0.27829(11) 0.0194(4) Uani 1 1 d . . . C6 C 0.64996(18) 0.85495(15) 0.15724(11) 0.0191(4) Uani 1 1 d . . . C7 C 0.43850(18) 0.99748(15) 0.32579(11) 0.0202(4) Uani 1 1 d . . . C8 C 0.94147(18) 0.73246(16) -0.07700(12) 0.0220(4) Uani 1 1 d . . . C9 C 0.84345(18) 0.81851(16) -0.03463(11) 0.0209(4) Uani 1 1 d . . . C10 C 0.56475(18) 0.94240(15) 0.19510(11) 0.0215(4) Uani 1 1 d . . . H3 H 0.5381 1.0233 0.1638 0.026 Uiso 1 1 calc R . . C11 C 0.22864(18) 1.01801(16) 0.51744(12) 0.0228(4) Uani 1 1 d . . . C12 C 0.71265(18) 0.87758(15) 0.07488(11) 0.0198(4) Uani 1 1 d . . . C13 C 0.69208(18) 0.58835(15) 0.33754(11) 0.0187(4) Uani 1 1 d . . . C14 C 0.39748(18) 1.12420(16) 0.31302(12) 0.0221(4) Uani 1 1 d . . . C15 C 0.78463(18) 0.94194(16) -0.06021(11) 0.0217(4) Uani 1 1 d . . . C16 C 0.30757(18) 1.04350(15) 0.43845(12) 0.0214(4) Uani 1 1 d . . . C17 C 0.70230(18) 0.97937(16) 0.00806(11) 0.0211(4) Uani 1 1 d . . . C18 C 0.31521(18) 1.15200(15) 0.38351(11) 0.0213(4) Uani 1 1 d . . . C19 C 0.2460(2) 1.27665(16) 0.39601(12) 0.0256(4) Uani 1 1 d . . . H24 H 0.1652 1.2711 0.4341 0.031 Uiso 1 1 calc R . . H25 H 0.2103 1.3265 0.3395 0.031 Uiso 1 1 calc R . . C20 C 0.8609(2) 0.40301(16) 0.45721(12) 0.0275(4) Uani 1 1 d . . . H4 H 0.9179 0.3404 0.4974 0.033 Uiso 1 1 calc R . . C21 C 0.83504(19) 0.58179(16) 0.34617(12) 0.0234(4) Uani 1 1 d . . . H5 H 0.8761 0.6412 0.3109 0.028 Uiso 1 1 calc R . . C22 C 0.81516(19) 1.02533(17) -0.14099(12) 0.0257(4) Uani 1 1 d . . . H26 H 0.7380 1.0979 -0.1527 0.031 Uiso 1 1 calc R . . H27 H 0.8198 0.9832 -0.1904 0.031 Uiso 1 1 calc R . . C23 C 0.4594(2) 0.66023(16) 0.23749(12) 0.0267(4) Uani 1 1 d . . . C24 C 0.2114(2) 1.09422(17) 0.57778(12) 0.0274(4) Uani 1 1 d . . . H6 H 0.2535 1.1625 0.5689 0.033 Uiso 1 1 calc R . . C25 C 0.1671(2) 0.91800(16) 0.53301(12) 0.0270(4) Uani 1 1 d . . . H7 H 0.1784 0.8652 0.4927 0.032 Uiso 1 1 calc R . . C26 C 0.4391(2) 1.21652(16) 0.24221(12) 0.0260(4) Uani 1 1 d . . . H28 H 0.3725 1.2952 0.2392 0.031 Uiso 1 1 calc R . . H29 H 0.4343 1.1906 0.1863 0.031 Uiso 1 1 calc R . . C27 C 0.62104(19) 1.10586(16) 0.00689(12) 0.0244(4) Uani 1 1 d . . . H30 H 0.5329 1.1019 0.0380 0.029 Uiso 1 1 calc R . . H31 H 0.5968 1.1464 -0.0537 0.029 Uiso 1 1 calc R . . C28 C 0.9183(2) 0.49072(16) 0.40497(12) 0.0261(4) Uani 1 1 d . . . H8 H 1.0151 0.4884 0.4095 0.031 Uiso 1 1 calc R . . C29 C 0.6376(2) 0.49868(16) 0.39082(12) 0.0261(4) Uani 1 1 d . . . H9 H 0.5410 0.4999 0.3864 0.031 Uiso 1 1 calc R . . C30 C 1.1309(2) 0.56763(17) -0.15488(13) 0.0315(5) Uani 1 1 d . . . H10 H 1.1955 0.5120 -0.1814 0.038 Uiso 1 1 calc R . . C31 C 1.1408(2) 0.56510(17) -0.06756(13) 0.0294(4) Uani 1 1 d . . . H11 H 1.2125 0.5073 -0.0338 0.035 Uiso 1 1 calc R . . B1 B 0.5939(2) 0.69690(18) 0.27224(13) 0.0197(4) Uani 1 1 d . . . C33 C 0.0720(2) 0.97057(19) 0.66483(14) 0.0362(5) Uani 1 1 d . . . H12 H 0.0181 0.9549 0.7148 0.043 Uiso 1 1 calc R . . C34 C 0.7201(2) 0.40766(16) 0.45009(12) 0.0296(5) Uani 1 1 d . . . H13 H 0.6795 0.3483 0.4859 0.036 Uiso 1 1 calc R . . C35 C 1.0259(2) 0.65193(18) -0.20364(13) 0.0310(5) Uani 1 1 d . . . H14 H 1.0185 0.6540 -0.2638 0.037 Uiso 1 1 calc R . . C36 C 0.5859(2) 1.23310(19) 0.25657(15) 0.0380(5) Uani 1 1 d . . . H32 H 0.5920 1.2563 0.3127 0.057 Uiso 1 1 calc R . . H33 H 0.6073 1.2968 0.2108 0.057 Uiso 1 1 calc R . . H34 H 0.6530 1.1568 0.2555 0.057 Uiso 1 1 calc R . . C37 C 0.0901(2) 0.89416(18) 0.60602(13) 0.0336(5) Uani 1 1 d . . . H15 H 0.0495 0.8251 0.6158 0.040 Uiso 1 1 calc R . . C38 C 0.9318(2) 0.73322(17) -0.16535(12) 0.0284(4) Uani 1 1 d . . . H16 H 0.8598 0.7902 -0.1994 0.034 Uiso 1 1 calc R . . C39 C 0.3426(2) 1.33981(18) 0.43511(15) 0.0364(5) Uani 1 1 d . . . H35 H 0.3763 1.2923 0.4919 0.055 Uiso 1 1 calc R . . H36 H 0.2918 1.4208 0.4414 0.055 Uiso 1 1 calc R . . H37 H 0.4221 1.3470 0.3973 0.055 Uiso 1 1 calc R . . C40 C 0.9516(2) 1.0651(2) -0.13335(13) 0.0365(5) Uani 1 1 d . . . H38 H 0.9495 1.1027 -0.0825 0.055 Uiso 1 1 calc R . . H39 H 0.9638 1.1239 -0.1853 0.055 Uiso 1 1 calc R . . H40 H 1.0293 0.9944 -0.1274 0.055 Uiso 1 1 calc R . . C41 C 0.6994(2) 1.18140(18) 0.04785(14) 0.0357(5) Uani 1 1 d . . . H41 H 0.7250 1.1413 0.1076 0.054 Uiso 1 1 calc R . . H42 H 0.6398 1.2617 0.0472 0.054 Uiso 1 1 calc R . . H43 H 0.7839 1.1901 0.0152 0.054 Uiso 1 1 calc R . . C42 C 0.1331(2) 1.07003(18) 0.65046(13) 0.0340(5) Uani 1 1 d . . . H17 H 0.1211 1.1225 0.6910 0.041 Uiso 1 1 calc R . . C43 C 0.3344(2) 0.6723(2) 0.28172(16) 0.0431(6) Uani 1 1 d . . . H18 H 0.3244 0.7131 0.3291 0.052 Uiso 1 1 calc R . . C44 C 0.4667(3) 0.60157(18) 0.16741(15) 0.0408(6) Uani 1 1 d . . . H19 H 0.5495 0.5924 0.1348 0.049 Uiso 1 1 calc R . . C45 C 0.2242(3) 0.6266(3) 0.2587(2) 0.0697(10) Uani 1 1 d . . . H20 H 0.1407 0.6362 0.2906 0.084 Uiso 1 1 calc R . . C46 C 0.2346(4) 0.5678(3) 0.1902(2) 0.0801(12) Uani 1 1 d . . . H21 H 0.1594 0.5356 0.1749 0.096 Uiso 1 1 calc R . . C47 C 0.3559(4) 0.5562(2) 0.1442(2) 0.0675(9) Uani 1 1 d . . . H22 H 0.3639 0.5169 0.0960 0.081 Uiso 1 1 calc R . . C48 C 1.04687(19) 0.64628(16) -0.02875(12) 0.0250(4) Uani 1 1 d . . . H23 H 1.0545 0.6431 0.0316 0.030 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 O1 0.0262(7) 0.0176(7) 0.0213(7) -0.0023(5) 0.0080(5) -0.0024(5) O2 0.0246(7) 0.0178(7) 0.0208(7) -0.0021(5) 0.0051(5) -0.0035(5) N1 0.0239(8) 0.0211(8) 0.0189(8) -0.0027(6) 0.0041(6) -0.0058(6) N2 0.0243(8) 0.0158(8) 0.0236(8) -0.0020(6) 0.0064(6) -0.0024(6) C5 0.0166(9) 0.0168(9) 0.0233(9) -0.0007(7) -0.0008(7) -0.0032(7) C6 0.0182(9) 0.0184(9) 0.0208(9) -0.0012(7) -0.0011(7) -0.0067(7) C7 0.0207(9) 0.0188(9) 0.0207(9) -0.0022(7) 0.0041(7) -0.0048(7) C8 0.0214(9) 0.0256(10) 0.0227(10) -0.0068(7) 0.0048(7) -0.0116(7) C9 0.0218(9) 0.0259(10) 0.0167(9) -0.0030(7) 0.0023(7) -0.0103(7) C10 0.0234(9) 0.0176(9) 0.0219(9) -0.0011(7) 0.0036(7) -0.0038(7) C11 0.0197(9) 0.0213(10) 0.0248(10) -0.0026(7) 0.0043(8) -0.0006(7) C12 0.0194(9) 0.0210(9) 0.0197(9) -0.0044(7) 0.0026(7) -0.0057(7) C13 0.0222(9) 0.0182(9) 0.0177(9) -0.0079(7) 0.0037(7) -0.0051(7) C14 0.0196(9) 0.0214(10) 0.0234(10) -0.0023(7) 0.0013(7) -0.0025(7) C15 0.0205(9) 0.0273(10) 0.0192(9) -0.0034(7) 0.0009(7) -0.0101(7) C16 0.0186(9) 0.0219(10) 0.0235(10) -0.0066(7) 0.0026(7) -0.0024(7) C17 0.0204(9) 0.0237(10) 0.0202(9) -0.0029(7) 0.0003(7) -0.0083(7) C18 0.0185(9) 0.0200(9) 0.0240(10) -0.0021(7) 0.0010(7) -0.0026(7) C19 0.0266(10) 0.0216(10) 0.0268(10) -0.0053(8) 0.0081(8) -0.0019(8) C20 0.0321(11) 0.0223(10) 0.0261(10) -0.0058(8) -0.0045(8) 0.0003(8) C21 0.0243(10) 0.0244(10) 0.0222(9) -0.0061(7) 0.0040(8) -0.0057(8) C22 0.0254(10) 0.0315(11) 0.0187(9) -0.0009(8) 0.0038(8) -0.0068(8) C23 0.0259(10) 0.0210(10) 0.0286(11) 0.0079(7) -0.0056(8) -0.0059(8) C24 0.0282(10) 0.0267(10) 0.0287(11) -0.0075(8) 0.0078(8) -0.0080(8) C25 0.0326(11) 0.0191(10) 0.0294(11) -0.0060(8) 0.0076(9) -0.0056(8) C26 0.0298(10) 0.0204(10) 0.0253(10) -0.0031(7) 0.0071(8) -0.0023(8) C27 0.0236(10) 0.0256(10) 0.0224(10) -0.0007(7) 0.0030(8) -0.0055(8) C28 0.0203(9) 0.0298(11) 0.0283(10) -0.0104(8) -0.0008(8) -0.0008(8) C29 0.0234(10) 0.0232(10) 0.0301(11) -0.0010(8) -0.0002(8) -0.0051(8) C30 0.0325(11) 0.0305(11) 0.0354(12) -0.0140(9) 0.0119(9) -0.0096(9) C31 0.0273(10) 0.0290(11) 0.0334(11) -0.0080(8) 0.0030(9) -0.0080(8) B1 0.0206(10) 0.0204(11) 0.0184(10) -0.0039(8) 0.0044(8) -0.0050(8) C33 0.0406(13) 0.0387(12) 0.0317(12) -0.0094(9) 0.0200(10) -0.0135(10) C34 0.0365(11) 0.0207(10) 0.0295(11) 0.0012(8) 0.0002(9) -0.0068(8) C35 0.0381(12) 0.0377(12) 0.0205(10) -0.0096(8) 0.0071(9) -0.0130(9) C36 0.0389(13) 0.0389(12) 0.0409(13) -0.0113(10) 0.0148(10) -0.0167(10) C37 0.0365(12) 0.0314(11) 0.0347(12) -0.0063(9) 0.0118(9) -0.0126(9) C38 0.0293(11) 0.0330(11) 0.0239(10) -0.0058(8) 0.0027(8) -0.0090(8) C39 0.0384(12) 0.0260(11) 0.0490(14) -0.0163(9) 0.0138(10) -0.0093(9) C40 0.0389(12) 0.0483(13) 0.0258(11) -0.0021(9) 0.0084(9) -0.0224(10) C41 0.0330(12) 0.0327(12) 0.0445(13) -0.0132(9) 0.0043(10) -0.0090(9) C42 0.0385(12) 0.0338(12) 0.0320(12) -0.0125(9) 0.0145(9) -0.0089(9) C43 0.0266(11) 0.0459(14) 0.0484(14) 0.0152(11) -0.0040(10) -0.0105(10) C44 0.0495(14) 0.0315(12) 0.0415(13) -0.0002(9) -0.0184(11) -0.0130(10) C45 0.0331(14) 0.077(2) 0.084(2) 0.0435(17) -0.0218(14) -0.0315(14) C46 0.073(2) 0.063(2) 0.098(3) 0.0503(18) -0.062(2) -0.0510(17) C47 0.090(2) 0.0470(16) 0.068(2) 0.0082(13) -0.0504(19) -0.0304(15) C48 0.0286(10) 0.0282(10) 0.0211(10) -0.0064(8) 0.0036(8) -0.0115(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.319(2) . ? O1 B1 1.521(2) . ? O2 C6 1.321(2) . ? O2 B1 1.517(2) . ? N1 C9 1.360(2) . ? N1 C12 1.379(2) . ? N1 H1 0.8800 . ? N2 C16 1.357(2) . ? N2 C7 1.379(2) . ? N2 H2 0.8800 . ? C5 C10 1.385(2) . ? C5 C7 1.432(2) . ? C6 C10 1.384(2) . ? C6 C12 1.428(2) . ? C7 C14 1.402(2) . ? C8 C48 1.393(3) . ? C8 C38 1.398(3) . ? C8 C9 1.472(2) . ? C9 C15 1.397(3) . ? C10 H3 0.9500 . ? C11 C25 1.391(3) . ? C11 C24 1.398(3) . ? C11 C16 1.467(3) . ? C12 C17 1.405(2) . ? C13 C29 1.393(2) . ? C13 C21 1.399(3) . ? C13 B1 1.608(3) . ? C14 C18 1.406(2) . ? C14 C26 1.502(3) . ? C15 C17 1.410(2) . ? C15 C22 1.507(2) . ? C16 C18 1.392(2) . ? C17 C27 1.499(2) . ? C18 C19 1.497(2) . ? C19 C39 1.519(3) . ? C19 H24 0.9900 . ? C19 H25 0.9900 . ? C20 C34 1.380(3) . ? C20 C28 1.386(3) . ? C20 H4 0.9500 . ? C21 C28 1.386(2) . ? C21 H5 0.9500 . ? C22 C40 1.522(3) . ? C22 H26 0.9900 . ? C22 H27 0.9900 . ? C23 C43 1.392(3) . ? C23 C44 1.395(3) . ? C23 B1 1.610(3) . ? C24 C42 1.383(3) . ? C24 H6 0.9500 . ? C25 C37 1.379(3) . ? C25 H7 0.9500 . ? C26 C36 1.523(3) . ? C26 H28 0.9900 . ? C26 H29 0.9900 . ? C27 C41 1.515(3) . ? C27 H30 0.9900 . ? C27 H31 0.9900 . ? C28 H8 0.9500 . ? C29 C34 1.387(2) . ? C29 H9 0.9500 . ? C30 C31 1.378(3) . ? C30 C35 1.384(3) . ? C30 H10 0.9500 . ? C31 C48 1.386(3) . ? C31 H11 0.9500 . ? C33 C37 1.380(3) . ? C33 C42 1.383(3) . ? C33 H12 0.9500 . ? C34 H13 0.9500 . ? C35 C38 1.383(3) . ? C35 H14 0.9500 . ? C36 H32 0.9800 . ? C36 H33 0.9800 . ? C36 H34 0.9800 . ? C37 H15 0.9500 . ? C38 H16 0.9500 . ? C39 H35 0.9800 . ? C39 H36 0.9800 . ? C39 H37 0.9800 . ? C40 H38 0.9800 . ? C40 H39 0.9800 . ? C40 H40 0.9800 . ? C41 H41 0.9800 . ? C41 H42 0.9800 . ? C41 H43 0.9800 . ? C42 H17 0.9500 . ? C43 C45 1.385(4) . ? C43 H18 0.9500 . ? C44 C47 1.389(3) . ? C44 H19 0.9500 . ? C45 C46 1.372(5) . ? C45 H20 0.9500 . ? C46 C47 1.377(5) . ? C46 H21 0.9500 . ? C47 H22 0.9500 . ? C48 H23 0.9500 . ? 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 C5 O1 B1 119.37(14) . . ? C6 O2 B1 119.53(13) . . ? C9 N1 C12 110.60(14) . . ? C9 N1 H1 124.7 . . ? C12 N1 H1 124.7 . . ? C16 N2 C7 110.59(15) . . ? C16 N2 H2 124.7 . . ? C7 N2 H2 124.7 . . ? O1 C5 C10 121.13(15) . . ? O1 C5 C7 113.93(15) . . ? C10 C5 C7 124.94(16) . . ? O2 C6 C10 120.72(16) . . ? O2 C6 C12 114.33(15) . . ? C10 C6 C12 124.92(16) . . ? N2 C7 C14 106.88(15) . . ? N2 C7 C5 117.91(16) . . ? C14 C7 C5 135.21(17) . . ? C48 C8 C38 118.05(17) . . ? C48 C8 C9 120.04(17) . . ? C38 C8 C9 121.90(16) . . ? N1 C9 C15 107.60(15) . . ? N1 C9 C8 120.19(15) . . ? C15 C9 C8 132.16(16) . . ? C6 C10 C5 120.38(16) . . ? C6 C10 H3 119.8 . . ? C5 C10 H3 119.8 . . ? C25 C11 C24 118.55(17) . . ? C25 C11 C16 120.36(17) . . ? C24 C11 C16 121.09(17) . . ? N1 C12 C17 106.82(15) . . ? N1 C12 C6 118.57(15) . . ? C17 C12 C6 134.49(16) . . ? C29 C13 C21 116.71(16) . . ? C29 C13 B1 121.43(16) . . ? C21 C13 B1 121.82(16) . . ? C7 C14 C18 107.08(15) . . ? C7 C14 C26 128.12(16) . . ? C18 C14 C26 124.67(15) . . ? C9 C15 C17 107.63(15) . . ? C9 C15 C22 127.05(17) . . ? C17 C15 C22 124.96(16) . . ? N2 C16 C18 107.41(16) . . ? N2 C16 C11 120.91(16) . . ? C18 C16 C11 131.47(16) . . ? C12 C17 C15 107.35(15) . . ? C12 C17 C27 127.88(16) . . ? C15 C17 C27 124.77(16) . . ? C16 C18 C14 108.05(15) . . ? C16 C18 C19 126.23(16) . . ? C14 C18 C19 125.71(16) . . ? C18 C19 C39 113.26(16) . . ? C18 C19 H24 108.9 . . ? C39 C19 H24 108.9 . . ? C18 C19 H25 108.9 . . ? C39 C19 H25 108.9 . . ? H24 C19 H25 107.7 . . ? C34 C20 C28 119.21(17) . . ? C34 C20 H4 120.4 . . ? C28 C20 H4 120.4 . . ? C28 C21 C13 121.64(18) . . ? C28 C21 H5 119.2 . . ? C13 C21 H5 119.2 . . ? C15 C22 C40 112.15(15) . . ? C15 C22 H26 109.2 . . ? C40 C22 H26 109.2 . . ? C15 C22 H27 109.2 . . ? C40 C22 H27 109.2 . . ? H26 C22 H27 107.9 . . ? C43 C23 C44 116.3(2) . . ? C43 C23 B1 121.68(19) . . ? C44 C23 B1 121.59(18) . . ? C42 C24 C11 119.89(19) . . ? C42 C24 H6 120.1 . . ? C11 C24 H6 120.1 . . ? C37 C25 C11 121.11(18) . . ? C37 C25 H7 119.4 . . ? C11 C25 H7 119.4 . . ? C14 C26 C36 111.98(16) . . ? C14 C26 H28 109.2 . . ? C36 C26 H28 109.2 . . ? C14 C26 H29 109.2 . . ? C36 C26 H29 109.2 . . ? H28 C26 H29 107.9 . . ? C17 C27 C41 113.24(15) . . ? C17 C27 H30 108.9 . . ? C41 C27 H30 108.9 . . ? C17 C27 H31 108.9 . . ? C41 C27 H31 108.9 . . ? H30 C27 H31 107.7 . . ? C20 C28 C21 120.26(18) . . ? C20 C28 H8 119.9 . . ? C21 C28 H8 119.9 . . ? C34 C29 C13 122.00(18) . . ? C34 C29 H9 119.0 . . ? C13 C29 H9 119.0 . . ? C31 C30 C35 119.41(18) . . ? C31 C30 H10 120.3 . . ? C35 C30 H10 120.3 . . ? C30 C31 C48 120.44(18) . . ? C30 C31 H11 119.8 . . ? C48 C31 H11 119.8 . . ? O2 B1 O1 107.93(14) . . ? O2 B1 C13 107.98(14) . . ? O1 B1 C13 106.82(14) . . ? O2 B1 C23 111.02(15) . . ? O1 B1 C23 109.11(14) . . ? C13 B1 C23 113.75(15) . . ? C37 C33 C42 119.48(19) . . ? C37 C33 H12 120.3 . . ? C42 C33 H12 120.3 . . ? C20 C34 C29 120.18(18) . . ? C20 C34 H13 119.9 . . ? C29 C34 H13 119.9 . . ? C38 C35 C30 120.48(19) . . ? C38 C35 H14 119.8 . . ? C30 C35 H14 119.8 . . ? C26 C36 H32 109.5 . . ? C26 C36 H33 109.5 . . ? H32 C36 H33 109.5 . . ? C26 C36 H34 109.5 . . ? H32 C36 H34 109.5 . . ? H33 C36 H34 109.5 . . ? C25 C37 C33 120.1(2) . . ? C25 C37 H15 120.0 . . ? C33 C37 H15 120.0 . . ? C35 C38 C8 120.71(18) . . ? C35 C38 H16 119.6 . . ? C8 C38 H16 119.6 . . ? C19 C39 H35 109.5 . . ? C19 C39 H36 109.5 . . ? H35 C39 H36 109.5 . . ? C19 C39 H37 109.5 . . ? H35 C39 H37 109.5 . . ? H36 C39 H37 109.5 . . ? C22 C40 H38 109.5 . . ? C22 C40 H39 109.5 . . ? H38 C40 H39 109.5 . . ? C22 C40 H40 109.5 . . ? H38 C40 H40 109.5 . . ? H39 C40 H40 109.5 . . ? C27 C41 H41 109.5 . . ? C27 C41 H42 109.5 . . ? H41 C41 H42 109.5 . . ? C27 C41 H43 109.5 . . ? H41 C41 H43 109.5 . . ? H42 C41 H43 109.5 . . ? C33 C42 C24 120.88(19) . . ? C33 C42 H17 119.6 . . ? C24 C42 H17 119.6 . . ? C45 C43 C23 122.0(3) . . ? C45 C43 H18 119.0 . . ? C23 C43 H18 119.0 . . ? C47 C44 C23 121.6(3) . . ? C47 C44 H19 119.2 . . ? C23 C44 H19 119.2 . . ? C46 C45 C43 120.6(3) . . ? C46 C45 H20 119.7 . . ? C43 C45 H20 119.7 . . ? C45 C46 C47 118.8(3) . . ? C45 C46 H21 120.6 . . ? C47 C46 H21 120.6 . . ? C46 C47 C44 120.6(3) . . ? C46 C47 H22 119.7 . . ? C44 C47 H22 119.7 . . ? C31 C48 C8 120.90(18) . . ? C31 C48 H23 119.5 . . ? C8 C48 H23 119.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag B1 O1 C5 C10 -17.0(2) . . . . ? B1 O1 C5 C7 163.45(15) . . . . ? B1 O2 C6 C10 18.9(2) . . . . ? B1 O2 C6 C12 -162.73(15) . . . . ? C16 N2 C7 C14 0.2(2) . . . . ? C16 N2 C7 C5 -178.63(16) . . . . ? O1 C5 C7 N2 -10.0(2) . . . . ? C10 C5 C7 N2 170.44(17) . . . . ? O1 C5 C7 C14 171.5(2) . . . . ? C10 C5 C7 C14 -8.0(3) . . . . ? C12 N1 C9 C15 -0.1(2) . . . . ? C12 N1 C9 C8 177.54(16) . . . . ? C48 C8 C9 N1 -37.0(3) . . . . ? C38 C8 C9 N1 142.34(19) . . . . ? C48 C8 C9 C15 139.9(2) . . . . ? C38 C8 C9 C15 -40.7(3) . . . . ? O2 C6 C10 C5 3.5(3) . . . . ? C12 C6 C10 C5 -174.79(17) . . . . ? O1 C5 C10 C6 -4.4(3) . . . . ? C7 C5 C10 C6 175.12(17) . . . . ? C9 N1 C12 C17 0.2(2) . . . . ? C9 N1 C12 C6 176.92(15) . . . . ? O2 C6 C12 N1 -0.3(2) . . . . ? C10 C6 C12 N1 178.05(17) . . . . ? O2 C6 C12 C17 175.26(19) . . . . ? C10 C6 C12 C17 -6.4(3) . . . . ? N2 C7 C14 C18 -0.4(2) . . . . ? C5 C7 C14 C18 178.2(2) . . . . ? N2 C7 C14 C26 175.48(18) . . . . ? C5 C7 C14 C26 -6.0(4) . . . . ? N1 C9 C15 C17 -0.1(2) . . . . ? C8 C9 C15 C17 -177.33(19) . . . . ? N1 C9 C15 C22 173.23(17) . . . . ? C8 C9 C15 C22 -4.0(3) . . . . ? C7 N2 C16 C18 0.1(2) . . . . ? C7 N2 C16 C11 175.43(16) . . . . ? C25 C11 C16 N2 -33.7(3) . . . . ? C24 C11 C16 N2 147.45(18) . . . . ? C25 C11 C16 C18 140.4(2) . . . . ? C24 C11 C16 C18 -38.4(3) . . . . ? N1 C12 C17 C15 -0.3(2) . . . . ? C6 C12 C17 C15 -176.20(19) . . . . ? N1 C12 C17 C27 -179.94(17) . . . . ? C6 C12 C17 C27 4.2(3) . . . . ? C9 C15 C17 C12 0.2(2) . . . . ? C22 C15 C17 C12 -173.26(17) . . . . ? C9 C15 C17 C27 179.90(17) . . . . ? C22 C15 C17 C27 6.4(3) . . . . ? N2 C16 C18 C14 -0.3(2) . . . . ? C11 C16 C18 C14 -175.02(19) . . . . ? N2 C16 C18 C19 178.61(17) . . . . ? C11 C16 C18 C19 3.9(3) . . . . ? C7 C14 C18 C16 0.4(2) . . . . ? C26 C14 C18 C16 -175.62(17) . . . . ? C7 C14 C18 C19 -178.49(18) . . . . ? C26 C14 C18 C19 5.4(3) . . . . ? C16 C18 C19 C39 98.3(2) . . . . ? C14 C18 C19 C39 -83.0(2) . . . . ? C29 C13 C21 C28 -0.1(3) . . . . ? B1 C13 C21 C28 177.42(16) . . . . ? C9 C15 C22 C40 -78.3(2) . . . . ? C17 C15 C22 C40 94.0(2) . . . . ? C25 C11 C24 C42 -0.8(3) . . . . ? C16 C11 C24 C42 178.11(17) . . . . ? C24 C11 C25 C37 0.3(3) . . . . ? C16 C11 C25 C37 -178.61(17) . . . . ? C7 C14 C26 C36 -76.7(2) . . . . ? C18 C14 C26 C36 98.5(2) . . . . ? C12 C17 C27 C41 85.0(2) . . . . ? C15 C17 C27 C41 -94.6(2) . . . . ? C34 C20 C28 C21 -0.2(3) . . . . ? C13 C21 C28 C20 0.0(3) . . . . ? C21 C13 C29 C34 0.5(3) . . . . ? B1 C13 C29 C34 -177.10(17) . . . . ? C35 C30 C31 C48 -0.1(3) . . . . ? C6 O2 B1 O1 -35.8(2) . . . . ? C6 O2 B1 C13 -150.92(14) . . . . ? C6 O2 B1 C23 83.74(19) . . . . ? C5 O1 B1 O2 34.8(2) . . . . ? C5 O1 B1 C13 150.70(15) . . . . ? C5 O1 B1 C23 -85.93(18) . . . . ? C29 C13 B1 O2 -153.71(16) . . . . ? C21 C13 B1 O2 28.8(2) . . . . ? C29 C13 B1 O1 90.4(2) . . . . ? C21 C13 B1 O1 -87.02(19) . . . . ? C29 C13 B1 C23 -30.0(2) . . . . ? C21 C13 B1 C23 152.54(16) . . . . ? C43 C23 B1 O2 -149.28(16) . . . . ? C44 C23 B1 O2 38.4(2) . . . . ? C43 C23 B1 O1 -30.5(2) . . . . ? C44 C23 B1 O1 157.24(16) . . . . ? C43 C23 B1 C13 88.7(2) . . . . ? C44 C23 B1 C13 -83.6(2) . . . . ? C28 C20 C34 C29 0.5(3) . . . . ? C13 C29 C34 C20 -0.6(3) . . . . ? C31 C30 C35 C38 0.1(3) . . . . ? C11 C25 C37 C33 0.5(3) . . . . ? C42 C33 C37 C25 -0.8(3) . . . . ? C30 C35 C38 C8 0.5(3) . . . . ? C48 C8 C38 C35 -1.1(3) . . . . ? C9 C8 C38 C35 179.51(18) . . . . ? C37 C33 C42 C24 0.3(3) . . . . ? C11 C24 C42 C33 0.5(3) . . . . ? C44 C23 C43 C45 1.2(3) . . . . ? B1 C23 C43 C45 -171.45(18) . . . . ? C43 C23 C44 C47 -1.0(3) . . . . ? B1 C23 C44 C47 171.73(18) . . . . ? C23 C43 C45 C46 -0.4(3) . . . . ? C43 C45 C46 C47 -0.8(4) . . . . ? C45 C46 C47 C44 1.0(4) . . . . ? C23 C44 C47 C46 -0.2(3) . . . . ? C30 C31 C48 C8 -0.5(3) . . . . ? C38 C8 C48 C31 1.1(3) . . . . ? C9 C8 C48 C31 -179.51(17) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.331 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.056 #============================================================================== # End of CIF #============================================================================== data_90919mae _database_code_depnum_ccdc_archive 'CCDC 759624' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C39 H55 B Br N3 O2' _chemical_formula_sum 'C39 H55 B Br N3 O2' _chemical_formula_weight 688.58 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' Br Br -0.2901 2.4595 '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 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.662(3) _cell_length_b 16.559(3) _cell_length_c 19.055(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.376(9) _cell_angle_gamma 90.00 _cell_volume 3813.0(13) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.4 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 1.113 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.6060 _exptl_absorpt_correction_T_max 0.8968 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _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 \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36595 _diffrn_reflns_av_R_equivalents 0.0749 _diffrn_reflns_av_sigmaI/netI 0.1333 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 17049 _reflns_number_gt 8507 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.8' _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^)+(0.0772P)^2^+1.0862P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.065(10) _refine_ls_number_reflns 17049 _refine_ls_number_parameters 837 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1600 _refine_ls_R_factor_gt 0.0737 _refine_ls_wR_factor_ref 0.1951 _refine_ls_wR_factor_gt 0.1593 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.030 _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 C1 C 0.0076(7) 0.2716(4) 0.1103(6) 0.084(3) Uani 1 1 d . . . H1 H -0.0682 0.2749 0.1081 0.101 Uiso 1 1 calc R . . C2 C 0.0475(6) 0.2599(5) 0.0519(5) 0.077(3) Uani 1 1 d . . . H2 H 0.0043 0.2533 0.0021 0.093 Uiso 1 1 calc R . . C3 C 0.1621(5) 0.2596(4) 0.0780(4) 0.0517(17) Uani 1 1 d . . . H3 H 0.2114 0.2531 0.0494 0.062 Uiso 1 1 calc R . . C4 C 0.1914(5) 0.2704(3) 0.1527(4) 0.0437(15) Uani 1 1 d . . . C5 C 0.2983(5) 0.2784(3) 0.2028(3) 0.0370(13) Uani 1 1 d . . . C6 C 0.3179(6) 0.2881(3) 0.2782(3) 0.0493(16) Uani 1 1 d . . . H4 H 0.2602 0.2788 0.2996 0.059 Uiso 1 1 calc R . . C7 C 0.4211(6) 0.3112(4) 0.3216(3) 0.0526(16) Uani 1 1 d . . . C8 C 0.4423(9) 0.3390(4) 0.3960(4) 0.076(3) Uani 1 1 d . . . C9 C 0.5407(11) 0.3568(4) 0.4481(5) 0.104(4) Uani 1 1 d . . . H5 H 0.6125 0.3550 0.4422 0.124 Uiso 1 1 calc R . . C10 C 0.5137(19) 0.3784(7) 0.5126(6) 0.161(9) Uani 1 1 d . . . H6 H 0.5637 0.3988 0.5567 0.193 Uiso 1 1 calc R . . C11 C 0.4061(18) 0.3652(7) 0.5009(7) 0.151(8) Uani 1 1 d . . . H7 H 0.3685 0.3698 0.5370 0.181 Uiso 1 1 calc R . . N1 N 0.0940(5) 0.2774(3) 0.1713(4) 0.0593(16) Uani 1 1 d . . . H8 H 0.0896 0.2847 0.2161 0.071 Uiso 1 1 calc R . . N2 N 0.3573(8) 0.3439(3) 0.4282(4) 0.097(3) Uani 1 1 d . . . H109 H 0.2865 0.3352 0.4066 0.117 Uiso 1 1 calc R . . O1 O 0.3795(3) 0.2806(2) 0.1740(2) 0.0367(9) Uani 1 1 d . . . O2 O 0.5068(3) 0.3142(2) 0.2955(2) 0.0487(10) Uani 1 1 d . . . B1 B 0.4965(6) 0.2674(4) 0.2250(4) 0.0389(16) Uani 1 1 d . . . C12 C 0.5117(5) 0.1717(3) 0.2441(3) 0.0434(15) Uani 1 1 d . . . C13 C 0.4423(6) 0.1125(4) 0.1996(4) 0.0502(18) Uani 1 1 d . . . H9 H 0.3833 0.1288 0.1581 0.060 Uiso 1 1 calc R . . C14 C 0.4595(7) 0.0322(4) 0.2156(4) 0.062(2) Uani 1 1 d . . . H10 H 0.4122 -0.0067 0.1851 0.075 Uiso 1 1 calc R . . C15 C 0.5449(7) 0.0067(4) 0.2758(5) 0.077(3) Uani 1 1 d . . . H11 H 0.5563 -0.0491 0.2870 0.092 Uiso 1 1 calc R . . C16 C 0.6113(8) 0.0628(4) 0.3178(5) 0.079(3) Uani 1 1 d . . . H12 H 0.6712 0.0460 0.3584 0.095 Uiso 1 1 calc R . . C17 C 0.5945(6) 0.1438(4) 0.3035(4) 0.069(2) Uani 1 1 d . . . H13 H 0.6414 0.1817 0.3356 0.083 Uiso 1 1 calc R . . C18 C 0.5800(4) 0.3050(4) 0.1868(3) 0.0420(13) Uani 1 1 d . . . C19 C 0.5483(5) 0.3225(3) 0.1117(4) 0.0456(15) Uani 1 1 d . . . H14 H 0.4742 0.3127 0.0826 0.055 Uiso 1 1 calc R . . C20 C 0.6240(7) 0.3543(4) 0.0791(4) 0.0598(19) Uani 1 1 d . . . H15 H 0.6015 0.3661 0.0279 0.072 Uiso 1 1 calc R . . C21 C 0.7326(7) 0.3687(4) 0.1214(6) 0.072(2) Uani 1 1 d . . . H16 H 0.7840 0.3903 0.0989 0.087 Uiso 1 1 calc R . . C22 C 0.7657(7) 0.3524(4) 0.1939(6) 0.068(2) Uani 1 1 d . . . H17 H 0.8399 0.3626 0.2225 0.082 Uiso 1 1 calc R . . C23 C 0.6903(5) 0.3205(4) 0.2266(4) 0.0578(18) Uani 1 1 d . . . H18 H 0.7144 0.3088 0.2778 0.069 Uiso 1 1 calc R . . Br1 Br 0.07582(8) 0.29870(5) 0.34237(5) 0.0974(3) Uani 1 1 d . . . N3 N 0.0297(5) 0.0410(3) 0.2635(4) 0.076(2) Uani 1 1 d . . . C24 C -0.0136(7) -0.0079(4) 0.3168(5) 0.082(3) Uani 1 1 d . . . H19 H -0.0792 -0.0389 0.2882 0.098 Uiso 1 1 calc R . . H20 H 0.0439 -0.0473 0.3423 0.098 Uiso 1 1 calc R . . C25 C -0.0451(8) 0.0415(5) 0.3736(5) 0.089(3) Uani 1 1 d . . . H21 H -0.1079 0.0774 0.3492 0.107 Uiso 1 1 calc R . . H22 H 0.0181 0.0756 0.4006 0.107 Uiso 1 1 calc R . . C26 C -0.0776(8) -0.0138(6) 0.4267(6) 0.103(4) Uani 1 1 d . . . H23 H -0.1391 -0.0487 0.3985 0.124 Uiso 1 1 calc R . . H24 H -0.0140 -0.0493 0.4504 0.124 Uiso 1 1 calc R . . C27 C -0.1129(8) 0.0285(7) 0.4860(6) 0.110(4) Uani 1 1 d . . . H25 H -0.0513 0.0609 0.5163 0.166 Uiso 1 1 calc R . . H26 H -0.1343 -0.0118 0.5170 0.166 Uiso 1 1 calc R . . H27 H -0.1761 0.0637 0.4635 0.166 Uiso 1 1 calc R . . C28 C -0.0546(6) 0.1036(4) 0.2237(5) 0.077(3) Uani 1 1 d . . . H28 H -0.0238 0.1334 0.1892 0.092 Uiso 1 1 calc R . . H29 H -0.0646 0.1429 0.2603 0.092 Uiso 1 1 calc R . . C29 C -0.1693(6) 0.0705(4) 0.1802(5) 0.067(2) Uani 1 1 d . . . H30 H -0.1608 0.0243 0.1493 0.081 Uiso 1 1 calc R . . H31 H -0.2091 0.0515 0.2145 0.081 Uiso 1 1 calc R . . C30 C -0.2346(6) 0.1375(4) 0.1318(5) 0.073(2) Uani 1 1 d . . . H32 H -0.2407 0.1840 0.1630 0.088 Uiso 1 1 calc R . . H33 H -0.1943 0.1558 0.0975 0.088 Uiso 1 1 calc R . . C31 C -0.3485(6) 0.1102(5) 0.0886(5) 0.080(3) Uani 1 1 d . . . H34 H -0.3427 0.0663 0.0554 0.120 Uiso 1 1 calc R . . H35 H -0.3890 0.1555 0.0597 0.120 Uiso 1 1 calc R . . H36 H -0.3881 0.0909 0.1223 0.120 Uiso 1 1 calc R . . C32 C 0.0525(7) -0.0194(4) 0.2109(5) 0.073(3) Uani 1 1 d . . . H37 H -0.0168 -0.0488 0.1864 0.088 Uiso 1 1 calc R . . H38 H 0.1069 -0.0593 0.2393 0.088 Uiso 1 1 calc R . . C33 C 0.0979(7) 0.0184(5) 0.1510(6) 0.090(3) Uani 1 1 d . . . H39 H 0.0437 0.0578 0.1216 0.108 Uiso 1 1 calc R . . H40 H 0.1676 0.0477 0.1748 0.108 Uiso 1 1 calc R . . C34 C 0.1190(7) -0.0458(4) 0.1012(5) 0.080(3) Uani 1 1 d . . . H41 H 0.1713 -0.0860 0.1310 0.096 Uiso 1 1 calc R . . H42 H 0.0487 -0.0739 0.0766 0.096 Uiso 1 1 calc R . . C35 C 0.1650(8) -0.0122(6) 0.0453(6) 0.103(3) Uani 1 1 d . . . H43 H 0.1254 0.0374 0.0252 0.155 Uiso 1 1 calc R . . H44 H 0.1567 -0.0517 0.0056 0.155 Uiso 1 1 calc R . . H45 H 0.2437 -0.0001 0.0677 0.155 Uiso 1 1 calc R . . C36 C 0.1345(7) 0.0858(4) 0.3044(6) 0.095(4) Uani 1 1 d . . . H46 H 0.1587 0.1184 0.2685 0.114 Uiso 1 1 calc R . . H47 H 0.1167 0.1237 0.3394 0.114 Uiso 1 1 calc R . . C37 C 0.2303(8) 0.0331(5) 0.3465(7) 0.121(4) Uani 1 1 d . . . H48 H 0.2449 -0.0084 0.3132 0.145 Uiso 1 1 calc R . . H49 H 0.2108 0.0051 0.3868 0.145 Uiso 1 1 calc R . . C38 C 0.3364(9) 0.0851(5) 0.3790(6) 0.108(4) Uani 1 1 d . . . H50 H 0.4035 0.0511 0.3964 0.130 Uiso 1 1 calc R . . H51 H 0.3468 0.1251 0.3430 0.130 Uiso 1 1 calc R . . C39 C 0.3085(10) 0.1245(10) 0.4406(7) 0.168(6) Uani 1 1 d . . . H52 H 0.2308 0.1414 0.4245 0.252 Uiso 1 1 calc R . . H53 H 0.3560 0.1718 0.4567 0.252 Uiso 1 1 calc R . . H54 H 0.3203 0.0863 0.4815 0.252 Uiso 1 1 calc R . . C40 C -0.3453(6) 0.8836(4) 0.1302(4) 0.0539(17) Uani 1 1 d . . . H55 H -0.4146 0.9026 0.1332 0.065 Uiso 1 1 calc R . . C41 C -0.3106(6) 0.8859(4) 0.0685(4) 0.0558(18) Uani 1 1 d . . . H56 H -0.3511 0.9068 0.0218 0.067 Uiso 1 1 calc R . . C42 C -0.2047(5) 0.8517(3) 0.0871(4) 0.0479(16) Uani 1 1 d . . . H57 H -0.1596 0.8454 0.0556 0.057 Uiso 1 1 calc R . . C43 C -0.1787(5) 0.8289(3) 0.1591(4) 0.0441(16) Uani 1 1 d . . . C44 C -0.0771(5) 0.7954(4) 0.2063(3) 0.0472(14) Uani 1 1 d . . . C45 C -0.0605(6) 0.7756(3) 0.2790(4) 0.0554(18) Uani 1 1 d . . . H58 H -0.1219 0.7666 0.2969 0.066 Uiso 1 1 calc R . . C46 C 0.0462(7) 0.7690(3) 0.3256(4) 0.0546(19) Uani 1 1 d . . . C47 C 0.0741(9) 0.7698(4) 0.4037(4) 0.076(3) Uani 1 1 d . . . C48 C 0.1760(11) 0.7709(5) 0.4549(4) 0.108(4) Uani 1 1 d . . . H59 H 0.2461 0.7721 0.4463 0.129 Uiso 1 1 calc R . . C49 C 0.1534(15) 0.7697(7) 0.5264(6) 0.153(7) Uani 1 1 d . . . H60 H 0.2057 0.7665 0.5739 0.184 Uiso 1 1 calc R . . C50 C 0.0431(18) 0.7742(7) 0.5097(8) 0.172(9) Uani 1 1 d . . . H61 H 0.0054 0.7791 0.5458 0.207 Uiso 1 1 calc R . . N4 N -0.2656(4) 0.8505(3) 0.1856(3) 0.0502(14) Uani 1 1 d . . . H62 H -0.2680 0.8436 0.2309 0.060 Uiso 1 1 calc R . . N5 N -0.0071(9) 0.7714(4) 0.4401(5) 0.120(4) Uani 1 1 d . . . H110 H -0.0792 0.7706 0.4193 0.144 Uiso 1 1 calc R . . O3 O 0.0035(3) 0.7877(2) 0.1770(2) 0.0405(9) Uani 1 1 d . . . O4 O 0.1320(4) 0.7668(2) 0.2999(2) 0.0464(10) Uani 1 1 d . . . B2 B 0.1042(6) 0.7378(4) 0.2206(4) 0.0397(16) Uani 1 1 d . . . C51 C 0.0729(5) 0.6441(3) 0.2165(3) 0.0385(14) Uani 1 1 d . . . C52 C -0.0173(6) 0.6122(4) 0.1621(4) 0.0563(18) Uani 1 1 d . . . H63 H -0.0617 0.6471 0.1255 0.068 Uiso 1 1 calc R . . C53 C -0.0435(7) 0.5307(4) 0.1599(5) 0.070(2) Uani 1 1 d . . . H64 H -0.1051 0.5103 0.1223 0.084 Uiso 1 1 calc R . . C54 C 0.0208(6) 0.4789(4) 0.2132(4) 0.0570(19) Uani 1 1 d . . . H65 H 0.0036 0.4230 0.2116 0.068 Uiso 1 1 calc R . . C55 C 0.1079(6) 0.5081(4) 0.2672(5) 0.063(2) Uani 1 1 d . . . H66 H 0.1519 0.4727 0.3035 0.076 Uiso 1 1 calc R . . C56 C 0.1333(6) 0.5909(3) 0.2695(4) 0.0534(17) Uani 1 1 d . . . H67 H 0.1935 0.6109 0.3084 0.064 Uiso 1 1 calc R . . C57 C 0.2055(5) 0.7592(3) 0.1900(3) 0.0382(14) Uani 1 1 d . . . C58 C 0.1976(5) 0.7360(4) 0.1177(4) 0.0443(15) Uani 1 1 d . . . H68 H 0.1345 0.7068 0.0897 0.053 Uiso 1 1 calc R . . C59 C 0.2809(5) 0.7552(4) 0.0866(4) 0.0530(17) Uani 1 1 d . . . H69 H 0.2727 0.7404 0.0371 0.064 Uiso 1 1 calc R . . C60 C 0.3738(5) 0.7948(5) 0.1261(4) 0.0612(18) Uani 1 1 d . . . H70 H 0.4294 0.8088 0.1041 0.073 Uiso 1 1 calc R . . C61 C 0.3862(5) 0.8142(4) 0.1977(4) 0.0570(18) Uani 1 1 d . . . H71 H 0.4528 0.8390 0.2262 0.068 Uiso 1 1 calc R . . C62 C 0.3019(5) 0.7979(4) 0.2302(3) 0.0497(14) Uani 1 1 d . . . H72 H 0.3111 0.8135 0.2797 0.060 Uiso 1 1 calc R . . Br2 Br -0.30633(6) 0.80316(4) 0.34513(3) 0.05726(19) Uani 1 1 d . . . N6 N 0.5289(5) 0.5676(3) 0.2511(3) 0.0568(17) Uani 1 1 d . . . C63 C 0.4832(6) 0.6192(4) 0.2985(4) 0.0557(19) Uani 1 1 d . . . H73 H 0.4188 0.6488 0.2666 0.067 Uiso 1 1 calc R . . H74 H 0.5399 0.6598 0.3225 0.067 Uiso 1 1 calc R . . C64 C 0.4465(7) 0.5764(4) 0.3583(4) 0.068(2) Uani 1 1 d . . . H75 H 0.3815 0.5419 0.3355 0.082 Uiso 1 1 calc R . . H76 H 0.5070 0.5415 0.3878 0.082 Uiso 1 1 calc R . . C65 C 0.4169(7) 0.6390(4) 0.4076(4) 0.074(2) Uani 1 1 d . . . H77 H 0.3606 0.6763 0.3773 0.089 Uiso 1 1 calc R . . H78 H 0.4835 0.6709 0.4329 0.089 Uiso 1 1 calc R . . C66 C 0.3721(8) 0.5986(5) 0.4647(4) 0.093(3) Uani 1 1 d . . . H79 H 0.3034 0.5700 0.4398 0.140 Uiso 1 1 calc R . . H80 H 0.3572 0.6398 0.4975 0.140 Uiso 1 1 calc R . . H81 H 0.4268 0.5602 0.4935 0.140 Uiso 1 1 calc R . . C67 C 0.4467(6) 0.5058(4) 0.2093(4) 0.0539(19) Uani 1 1 d . . . H82 H 0.4223 0.4730 0.2451 0.065 Uiso 1 1 calc R . . H83 H 0.4847 0.4690 0.1837 0.065 Uiso 1 1 calc R . . C68 C 0.3440(5) 0.5404(3) 0.1525(4) 0.0453(15) Uani 1 1 d . . . H84 H 0.3080 0.5806 0.1763 0.054 Uiso 1 1 calc R . . H85 H 0.3660 0.5679 0.1129 0.054 Uiso 1 1 calc R . . C69 C 0.2632(5) 0.4724(3) 0.1200(4) 0.0480(16) Uani 1 1 d . . . H86 H 0.3024 0.4297 0.1012 0.058 Uiso 1 1 calc R . . H87 H 0.2368 0.4484 0.1593 0.058 Uiso 1 1 calc R . . C70 C 0.1645(6) 0.5010(4) 0.0581(4) 0.0615(19) Uani 1 1 d . . . H88 H 0.1280 0.5455 0.0756 0.092 Uiso 1 1 calc R . . H89 H 0.1122 0.4563 0.0418 0.092 Uiso 1 1 calc R . . H90 H 0.1895 0.5196 0.0169 0.092 Uiso 1 1 calc R . . C71 C 0.5605(6) 0.6255(4) 0.1973(4) 0.061(2) Uani 1 1 d . . . H91 H 0.4934 0.6560 0.1705 0.073 Uiso 1 1 calc R . . H92 H 0.6145 0.6650 0.2266 0.073 Uiso 1 1 calc R . . C72 C 0.6084(7) 0.5893(4) 0.1418(5) 0.076(2) Uani 1 1 d . . . H93 H 0.5617 0.5437 0.1169 0.091 Uiso 1 1 calc R . . H94 H 0.6834 0.5682 0.1668 0.091 Uiso 1 1 calc R . . C73 C 0.6150(7) 0.6513(5) 0.0861(5) 0.085(3) Uani 1 1 d . . . H95 H 0.6635 0.6958 0.1118 0.102 Uiso 1 1 calc R . . H96 H 0.5402 0.6741 0.0638 0.102 Uiso 1 1 calc R . . C74 C 0.6582(7) 0.6206(6) 0.0252(5) 0.093(3) Uani 1 1 d . . . H97 H 0.7336 0.6001 0.0463 0.139 Uiso 1 1 calc R . . H98 H 0.6585 0.6647 -0.0090 0.139 Uiso 1 1 calc R . . H99 H 0.6103 0.5769 -0.0012 0.139 Uiso 1 1 calc R . . C75 C 0.6302(7) 0.5200(4) 0.2961(6) 0.089(3) Uani 1 1 d . . . H100 H 0.6053 0.4778 0.3244 0.107 Uiso 1 1 calc R . . H101 H 0.6633 0.4923 0.2617 0.107 Uiso 1 1 calc R . . C76 C 0.7181(9) 0.5696(5) 0.3485(7) 0.147(6) Uani 1 1 d D . . H102 H 0.6860 0.6023 0.3805 0.176 Uiso 1 1 calc R . . H103 H 0.7535 0.6064 0.3213 0.176 Uiso 1 1 calc R . . C77 C 0.8120(9) 0.5029(10) 0.3993(6) 0.177(8) Uani 1 1 d D . . H104 H 0.8532 0.5230 0.4488 0.213 Uiso 1 1 calc R . . H105 H 0.7813 0.4484 0.4021 0.213 Uiso 1 1 calc R . . C78 C 0.8717(10) 0.5096(10) 0.3465(6) 0.167(7) Uani 1 1 d D . . H106 H 0.8196 0.5075 0.2967 0.250 Uiso 1 1 calc R . . H107 H 0.9244 0.4648 0.3531 0.250 Uiso 1 1 calc R . . H108 H 0.9119 0.5610 0.3534 0.250 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 C1 0.032(5) 0.052(4) 0.169(10) -0.008(5) 0.030(6) -0.009(3) C2 0.038(5) 0.063(5) 0.113(7) -0.014(5) -0.005(5) 0.000(4) C3 0.033(4) 0.048(3) 0.072(5) -0.003(3) 0.012(4) -0.005(3) C4 0.040(4) 0.033(3) 0.062(4) 0.003(3) 0.022(3) 0.000(3) C5 0.038(4) 0.029(3) 0.048(4) 0.002(2) 0.018(3) 0.001(2) C6 0.073(5) 0.035(4) 0.050(4) 0.009(3) 0.034(4) 0.003(3) C7 0.088(5) 0.029(3) 0.039(3) 0.006(3) 0.017(4) 0.003(4) C8 0.140(8) 0.042(4) 0.045(5) 0.003(3) 0.027(6) -0.017(4) C9 0.190(12) 0.051(4) 0.051(5) 0.007(4) 0.008(6) -0.015(6) C10 0.38(3) 0.047(6) 0.048(6) -0.005(4) 0.055(12) -0.038(11) C11 0.36(3) 0.044(5) 0.079(8) -0.008(5) 0.115(13) -0.030(10) N1 0.048(4) 0.036(3) 0.106(5) 0.002(3) 0.041(4) -0.002(2) N2 0.205(9) 0.050(3) 0.057(4) 0.004(3) 0.070(6) -0.002(5) O1 0.034(2) 0.037(2) 0.043(2) 0.0030(15) 0.0172(19) 0.0001(16) O2 0.055(3) 0.037(2) 0.050(2) -0.001(2) 0.010(2) -0.003(2) B1 0.034(4) 0.035(3) 0.041(4) -0.009(3) 0.001(3) 0.002(3) C12 0.037(4) 0.039(3) 0.047(4) 0.002(3) 0.003(3) -0.001(3) C13 0.053(5) 0.034(3) 0.053(5) 0.005(3) 0.001(4) 0.005(3) C14 0.072(6) 0.031(3) 0.064(5) 0.001(3) -0.011(4) 0.000(3) C15 0.080(6) 0.040(4) 0.088(6) 0.004(4) -0.007(5) 0.010(4) C16 0.085(7) 0.048(4) 0.073(5) -0.005(4) -0.026(5) 0.001(4) C17 0.075(6) 0.034(3) 0.073(5) 0.000(3) -0.018(4) -0.003(3) C18 0.034(3) 0.025(2) 0.068(4) 0.005(4) 0.016(3) 0.003(3) C19 0.040(4) 0.039(4) 0.063(4) 0.003(3) 0.024(3) 0.001(3) C20 0.064(5) 0.044(4) 0.083(5) -0.001(3) 0.041(4) 0.001(3) C21 0.058(6) 0.042(4) 0.140(8) -0.012(4) 0.064(6) -0.010(3) C22 0.044(5) 0.056(4) 0.104(7) -0.023(4) 0.019(5) -0.008(4) C23 0.042(4) 0.043(4) 0.088(5) -0.016(3) 0.018(4) -0.002(3) Br1 0.1434(8) 0.0489(4) 0.1475(8) 0.0235(6) 0.1161(7) 0.0196(6) N3 0.049(4) 0.031(3) 0.136(6) 0.001(3) 0.008(4) -0.011(3) C24 0.063(6) 0.049(4) 0.113(7) -0.023(4) -0.005(5) -0.002(4) C25 0.088(7) 0.054(4) 0.094(7) 0.004(5) -0.018(5) -0.013(4) C26 0.055(6) 0.095(7) 0.124(9) -0.030(7) -0.028(6) 0.014(5) C27 0.073(7) 0.109(8) 0.124(9) 0.016(7) -0.010(6) 0.012(6) C28 0.047(5) 0.022(3) 0.146(8) -0.003(4) 0.006(5) 0.003(3) C29 0.038(4) 0.043(4) 0.115(6) 0.000(4) 0.013(4) -0.004(3) C30 0.049(5) 0.039(3) 0.123(7) -0.010(4) 0.013(5) 0.006(3) C31 0.043(5) 0.066(5) 0.128(8) -0.010(5) 0.020(5) 0.009(4) C32 0.055(5) 0.032(3) 0.124(8) -0.009(4) 0.014(5) 0.003(3) C33 0.067(6) 0.048(4) 0.151(9) -0.001(5) 0.029(6) -0.012(4) C34 0.071(6) 0.051(4) 0.102(7) 0.017(4) 0.000(5) 0.008(4) C35 0.076(7) 0.088(6) 0.128(9) 0.043(6) 0.003(6) 0.000(5) C36 0.041(5) 0.043(4) 0.174(10) -0.010(5) -0.010(6) -0.013(4) C37 0.061(6) 0.057(5) 0.197(12) -0.023(6) -0.035(7) -0.007(4) C38 0.111(8) 0.066(5) 0.089(7) -0.004(5) -0.059(6) -0.003(5) C39 0.106(10) 0.226(16) 0.112(10) 0.025(11) -0.059(8) -0.012(10) C40 0.038(4) 0.050(4) 0.071(5) -0.016(3) 0.011(4) -0.005(3) C41 0.041(4) 0.050(4) 0.073(5) -0.017(3) 0.013(4) -0.010(3) C42 0.042(4) 0.037(3) 0.071(5) -0.016(3) 0.027(4) -0.005(3) C43 0.034(4) 0.030(3) 0.077(5) -0.017(3) 0.029(4) -0.006(2) C44 0.049(4) 0.031(3) 0.069(4) -0.009(3) 0.029(3) -0.012(3) C45 0.059(5) 0.032(3) 0.091(6) 0.000(3) 0.046(4) 0.003(3) C46 0.095(6) 0.025(3) 0.048(4) -0.005(3) 0.028(4) 0.000(3) C47 0.141(8) 0.036(3) 0.061(5) 0.006(3) 0.046(6) 0.018(4) C48 0.212(12) 0.072(5) 0.030(4) 0.015(3) 0.021(6) 0.079(6) C49 0.29(2) 0.098(8) 0.044(6) 0.022(5) 0.009(9) 0.110(11) C50 0.38(3) 0.072(7) 0.082(9) 0.029(6) 0.094(14) 0.094(12) N4 0.039(3) 0.047(3) 0.073(4) -0.023(3) 0.030(3) -0.017(2) N5 0.223(11) 0.055(4) 0.133(7) -0.013(4) 0.132(8) -0.003(5) O3 0.035(2) 0.033(2) 0.056(2) -0.0037(17) 0.0182(19) -0.0042(18) O4 0.057(3) 0.0339(19) 0.049(3) -0.0077(17) 0.019(2) -0.0065(19) B2 0.039(4) 0.033(3) 0.049(4) -0.003(3) 0.016(3) 0.004(3) C51 0.031(4) 0.036(3) 0.051(4) -0.005(3) 0.017(3) -0.009(3) C52 0.066(5) 0.040(3) 0.067(5) -0.010(3) 0.025(4) -0.008(3) C53 0.067(5) 0.038(3) 0.101(6) -0.024(4) 0.019(5) -0.021(4) C54 0.051(5) 0.027(3) 0.099(6) -0.011(3) 0.032(4) -0.005(3) C55 0.056(5) 0.036(3) 0.096(6) 0.013(4) 0.021(5) -0.005(3) C56 0.053(4) 0.032(3) 0.074(5) 0.010(3) 0.018(4) -0.005(3) C57 0.028(3) 0.026(3) 0.055(4) 0.005(2) 0.003(3) 0.003(2) C58 0.023(3) 0.046(3) 0.065(4) 0.004(3) 0.014(3) 0.005(3) C59 0.037(4) 0.049(4) 0.077(5) 0.012(3) 0.023(4) 0.009(3) C60 0.043(4) 0.049(4) 0.097(6) 0.025(4) 0.029(4) 0.003(4) C61 0.023(3) 0.040(4) 0.097(5) 0.015(4) 0.001(3) -0.002(3) C62 0.040(3) 0.033(3) 0.064(4) 0.013(4) -0.002(3) -0.001(3) Br2 0.0736(5) 0.0436(3) 0.0537(4) -0.0022(4) 0.0178(3) 0.0016(4) N6 0.048(4) 0.030(3) 0.073(4) -0.013(3) -0.011(3) 0.007(2) C63 0.046(4) 0.034(3) 0.065(5) -0.009(3) -0.018(4) 0.005(3) C64 0.079(6) 0.046(4) 0.056(5) 0.008(3) -0.016(4) 0.003(4) C65 0.093(6) 0.053(4) 0.061(5) -0.003(4) -0.001(5) 0.007(4) C66 0.115(8) 0.081(6) 0.058(5) 0.018(4) -0.014(5) 0.019(5) C67 0.053(5) 0.035(3) 0.064(5) -0.011(3) 0.002(4) -0.008(3) C68 0.034(4) 0.036(3) 0.060(4) 0.000(3) 0.006(3) -0.001(3) C69 0.033(4) 0.038(3) 0.066(4) -0.005(3) 0.004(3) -0.009(3) C70 0.048(5) 0.050(4) 0.081(5) -0.012(3) 0.012(4) 0.001(3) C71 0.044(4) 0.034(3) 0.103(6) -0.020(3) 0.018(4) -0.006(3) C72 0.052(5) 0.045(4) 0.129(7) -0.024(4) 0.024(5) -0.002(3) C73 0.063(6) 0.058(5) 0.137(8) -0.036(5) 0.036(6) -0.018(4) C74 0.061(6) 0.095(6) 0.127(8) -0.043(6) 0.035(6) -0.008(5) C75 0.049(5) 0.037(4) 0.140(9) -0.024(4) -0.035(5) 0.021(3) C76 0.088(8) 0.075(6) 0.191(12) -0.055(7) -0.090(8) 0.038(5) C77 0.094(9) 0.36(2) 0.056(7) 0.011(9) -0.012(6) -0.105(12) C78 0.101(10) 0.271(18) 0.107(10) -0.117(11) -0.002(8) -0.055(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.340(10) . ? C1 C2 1.366(12) . ? C1 H1 0.9500 . ? C2 C3 1.386(9) . ? C2 H2 0.9500 . ? C3 C4 1.370(9) . ? C3 H3 0.9500 . ? C4 N1 1.386(8) . ? C4 C5 1.411(8) . ? C5 O1 1.302(6) . ? C5 C6 1.392(8) . ? C6 C7 1.375(9) . ? C6 H4 0.9500 . ? C7 O2 1.323(7) . ? C7 C8 1.438(9) . ? C8 C9 1.374(13) . ? C8 N2 1.392(11) . ? C9 C10 1.416(17) . ? C9 H5 0.9500 . ? C10 C11 1.33(3) . ? C10 H6 0.9500 . ? C11 N2 1.384(15) . ? C11 H7 0.9500 . ? N1 H8 0.8800 . ? N2 H109 0.8800 . ? O1 B1 1.525(8) . ? O2 B1 1.522(7) . ? B1 C18 1.580(9) . ? B1 C12 1.624(8) . ? C12 C17 1.372(9) . ? C12 C13 1.417(9) . ? C13 C14 1.367(8) . ? C13 H9 0.9500 . ? C14 C15 1.386(10) . ? C14 H10 0.9500 . ? C15 C16 1.345(10) . ? C15 H11 0.9500 . ? C16 C17 1.373(9) . ? C16 H12 0.9500 . ? C17 H13 0.9500 . ? C18 C19 1.396(8) . ? C18 C23 1.400(8) . ? C19 C20 1.392(9) . ? C19 H14 0.9500 . ? C20 C21 1.392(11) . ? C20 H15 0.9500 . ? C21 C22 1.345(11) . ? C21 H16 0.9500 . ? C22 C23 1.392(10) . ? C22 H17 0.9500 . ? C23 H18 0.9500 . ? N3 C32 1.504(10) . ? N3 C36 1.517(9) . ? N3 C28 1.518(9) . ? N3 C24 1.523(11) . ? C24 C25 1.502(12) . ? C24 H19 0.9900 . ? C24 H20 0.9900 . ? C25 C26 1.509(14) . ? C25 H21 0.9900 . ? C25 H22 0.9900 . ? C26 C27 1.506(14) . ? C26 H23 0.9900 . ? C26 H24 0.9900 . ? C27 H25 0.9800 . ? C27 H26 0.9800 . ? C27 H27 0.9800 . ? C28 C29 1.542(10) . ? C28 H28 0.9900 . ? C28 H29 0.9900 . ? C29 C30 1.520(10) . ? C29 H30 0.9900 . ? C29 H31 0.9900 . ? C30 C31 1.501(10) . ? C30 H32 0.9900 . ? C30 H33 0.9900 . ? C31 H34 0.9800 . ? C31 H35 0.9800 . ? C31 H36 0.9800 . ? C32 C33 1.556(12) . ? C32 H37 0.9900 . ? C32 H38 0.9900 . ? C33 C34 1.500(12) . ? C33 H39 0.9900 . ? C33 H40 0.9900 . ? C34 C35 1.468(12) . ? C34 H41 0.9900 . ? C34 H42 0.9900 . ? C35 H43 0.9800 . ? C35 H44 0.9800 . ? C35 H45 0.9800 . ? C36 C37 1.515(12) . ? C36 H46 0.9900 . ? C36 H47 0.9900 . ? C37 C38 1.560(12) . ? C37 H48 0.9900 . ? C37 H49 0.9900 . ? C38 C39 1.474(17) . ? C38 H50 0.9900 . ? C38 H51 0.9900 . ? C39 H52 0.9800 . ? C39 H53 0.9800 . ? C39 H54 0.9800 . ? C40 N4 1.340(8) . ? C40 C41 1.372(9) . ? C40 H55 0.9500 . ? C41 C42 1.401(9) . ? C41 H56 0.9500 . ? C42 C43 1.365(9) . ? C42 H57 0.9500 . ? C43 N4 1.388(7) . ? C43 C44 1.443(9) . ? C44 O3 1.306(6) . ? C44 C45 1.377(9) . ? C45 C46 1.382(10) . ? C45 H58 0.9500 . ? C46 O4 1.319(8) . ? C46 C47 1.423(10) . ? C47 C48 1.366(13) . ? C47 N5 1.402(11) . ? C48 C49 1.474(15) . ? C48 H59 0.9500 . ? C49 C50 1.34(2) . ? C49 H60 0.9500 . ? C50 N5 1.289(15) . ? C50 H61 0.9500 . ? N4 H62 0.8800 . ? N5 H110 0.8800 . ? O3 B2 1.538(8) . ? O4 B2 1.523(8) . ? B2 C51 1.598(8) . ? B2 C57 1.599(9) . ? C51 C56 1.385(9) . ? C51 C52 1.397(9) . ? C52 C53 1.387(9) . ? C52 H63 0.9500 . ? C53 C54 1.391(11) . ? C53 H64 0.9500 . ? C54 C55 1.354(10) . ? C54 H65 0.9500 . ? C55 C56 1.405(8) . ? C55 H66 0.9500 . ? C56 H67 0.9500 . ? C57 C62 1.389(8) . ? C57 C58 1.404(8) . ? C58 C59 1.393(8) . ? C58 H68 0.9500 . ? C59 C60 1.362(9) . ? C59 H69 0.9500 . ? C60 C61 1.363(9) . ? C60 H70 0.9500 . ? C61 C62 1.411(8) . ? C61 H71 0.9500 . ? C62 H72 0.9500 . ? N6 C63 1.481(9) . ? N6 C67 1.507(8) . ? N6 C75 1.532(9) . ? N6 C71 1.541(9) . ? C63 C64 1.526(10) . ? C63 H73 0.9900 . ? C63 H74 0.9900 . ? C64 C65 1.520(10) . ? C64 H75 0.9900 . ? C64 H76 0.9900 . ? C65 C66 1.523(12) . ? C65 H77 0.9900 . ? C65 H78 0.9900 . ? C66 H79 0.9800 . ? C66 H80 0.9800 . ? C66 H81 0.9800 . ? C67 C68 1.533(9) . ? C67 H82 0.9900 . ? C67 H83 0.9900 . ? C68 C69 1.523(8) . ? C68 H84 0.9900 . ? C68 H85 0.9900 . ? C69 C70 1.516(9) . ? C69 H86 0.9900 . ? C69 H87 0.9900 . ? C70 H88 0.9800 . ? C70 H89 0.9800 . ? C70 H90 0.9800 . ? C71 C72 1.492(10) . ? C71 H91 0.9900 . ? C71 H92 0.9900 . ? C72 C73 1.497(12) . ? C72 H93 0.9900 . ? C72 H94 0.9900 . ? C73 C74 1.511(11) . ? C73 H95 0.9900 . ? C73 H96 0.9900 . ? C74 H97 0.9800 . ? C74 H98 0.9800 . ? C74 H99 0.9800 . ? C75 C76 1.500(11) . ? C75 H100 0.9900 . ? C75 H101 0.9900 . ? C76 C77 1.698(14) . ? C76 H102 0.9900 . ? C76 H103 0.9900 . ? C77 C78 1.433(12) . ? C77 H104 0.9900 . ? C77 H105 0.9900 . ? C78 H106 0.9800 . ? C78 H107 0.9800 . ? C78 H108 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 108.2(7) . . ? N1 C1 H1 125.9 . . ? C2 C1 H1 125.9 . . ? C1 C2 C3 108.1(8) . . ? C1 C2 H2 126.0 . . ? C3 C2 H2 126.0 . . ? C4 C3 C2 107.5(7) . . ? C4 C3 H3 126.2 . . ? C2 C3 H3 126.2 . . ? C3 C4 N1 107.0(6) . . ? C3 C4 C5 128.5(6) . . ? N1 C4 C5 124.4(6) . . ? O1 C5 C6 120.7(6) . . ? O1 C5 C4 115.9(5) . . ? C6 C5 C4 123.3(6) . . ? C7 C6 C5 119.8(5) . . ? C7 C6 H4 120.1 . . ? C5 C6 H4 120.1 . . ? O2 C7 C6 121.5(5) . . ? O2 C7 C8 115.2(7) . . ? C6 C7 C8 123.1(7) . . ? C9 C8 N2 108.8(8) . . ? C9 C8 C7 130.1(10) . . ? N2 C8 C7 120.8(9) . . ? C8 C9 C10 106.2(13) . . ? C8 C9 H5 126.9 . . ? C10 C9 H5 126.9 . . ? C11 C10 C9 108.3(13) . . ? C11 C10 H6 125.9 . . ? C9 C10 H6 125.9 . . ? C10 C11 N2 109.8(13) . . ? C10 C11 H7 125.1 . . ? N2 C11 H7 125.1 . . ? C1 N1 C4 109.2(7) . . ? C1 N1 H8 125.4 . . ? C4 N1 H8 125.4 . . ? C11 N2 C8 106.5(11) . . ? C11 N2 H109 126.8 . . ? C8 N2 H109 126.8 . . ? C5 O1 B1 117.8(4) . . ? C7 O2 B1 116.7(5) . . ? O2 B1 O1 107.4(4) . . ? O2 B1 C18 108.2(5) . . ? O1 B1 C18 107.8(5) . . ? O2 B1 C12 109.0(5) . . ? O1 B1 C12 108.1(5) . . ? C18 B1 C12 115.9(5) . . ? C17 C12 C13 116.4(5) . . ? C17 C12 B1 121.6(5) . . ? C13 C12 B1 122.0(5) . . ? C14 C13 C12 120.7(6) . . ? C14 C13 H9 119.7 . . ? C12 C13 H9 119.7 . . ? C13 C14 C15 120.9(6) . . ? C13 C14 H10 119.6 . . ? C15 C14 H10 119.6 . . ? C16 C15 C14 118.5(7) . . ? C16 C15 H11 120.8 . . ? C14 C15 H11 120.8 . . ? C15 C16 C17 121.6(7) . . ? C15 C16 H12 119.2 . . ? C17 C16 H12 119.2 . . ? C12 C17 C16 121.8(6) . . ? C12 C17 H13 119.1 . . ? C16 C17 H13 119.1 . . ? C19 C18 C23 116.9(6) . . ? C19 C18 B1 121.8(5) . . ? C23 C18 B1 121.2(6) . . ? C20 C19 C18 120.7(6) . . ? C20 C19 H14 119.6 . . ? C18 C19 H14 119.6 . . ? C21 C20 C19 119.9(7) . . ? C21 C20 H15 120.0 . . ? C19 C20 H15 120.0 . . ? C22 C21 C20 120.8(7) . . ? C22 C21 H16 119.6 . . ? C20 C21 H16 119.6 . . ? C21 C22 C23 119.4(7) . . ? C21 C22 H17 120.3 . . ? C23 C22 H17 120.3 . . ? C22 C23 C18 122.2(7) . . ? C22 C23 H18 118.9 . . ? C18 C23 H18 118.9 . . ? C32 N3 C36 110.8(7) . . ? C32 N3 C28 111.6(7) . . ? C36 N3 C28 107.4(5) . . ? C32 N3 C24 105.7(5) . . ? C36 N3 C24 110.6(7) . . ? C28 N3 C24 110.9(6) . . ? C25 C24 N3 114.7(6) . . ? C25 C24 H19 108.6 . . ? N3 C24 H19 108.6 . . ? C25 C24 H20 108.6 . . ? N3 C24 H20 108.6 . . ? H19 C24 H20 107.6 . . ? C24 C25 C26 109.7(7) . . ? C24 C25 H21 109.7 . . ? C26 C25 H21 109.7 . . ? C24 C25 H22 109.7 . . ? C26 C25 H22 109.7 . . ? H21 C25 H22 108.2 . . ? C27 C26 C25 115.0(8) . . ? C27 C26 H23 108.5 . . ? C25 C26 H23 108.5 . . ? C27 C26 H24 108.5 . . ? C25 C26 H24 108.5 . . ? H23 C26 H24 107.5 . . ? C26 C27 H25 109.5 . . ? C26 C27 H26 109.5 . . ? H25 C27 H26 109.5 . . ? C26 C27 H27 109.5 . . ? H25 C27 H27 109.5 . . ? H26 C27 H27 109.5 . . ? N3 C28 C29 115.8(5) . . ? N3 C28 H28 108.3 . . ? C29 C28 H28 108.3 . . ? N3 C28 H29 108.3 . . ? C29 C28 H29 108.3 . . ? H28 C28 H29 107.4 . . ? C30 C29 C28 108.7(5) . . ? C30 C29 H30 110.0 . . ? C28 C29 H30 110.0 . . ? C30 C29 H31 110.0 . . ? C28 C29 H31 110.0 . . ? H30 C29 H31 108.3 . . ? C31 C30 C29 111.8(6) . . ? C31 C30 H32 109.3 . . ? C29 C30 H32 109.3 . . ? C31 C30 H33 109.3 . . ? C29 C30 H33 109.3 . . ? H32 C30 H33 107.9 . . ? C30 C31 H34 109.5 . . ? C30 C31 H35 109.5 . . ? H34 C31 H35 109.5 . . ? C30 C31 H36 109.5 . . ? H34 C31 H36 109.5 . . ? H35 C31 H36 109.5 . . ? N3 C32 C33 114.1(6) . . ? N3 C32 H37 108.7 . . ? C33 C32 H37 108.7 . . ? N3 C32 H38 108.7 . . ? C33 C32 H38 108.7 . . ? H37 C32 H38 107.6 . . ? C34 C33 C32 110.7(6) . . ? C34 C33 H39 109.5 . . ? C32 C33 H39 109.5 . . ? C34 C33 H40 109.5 . . ? C32 C33 H40 109.5 . . ? H39 C33 H40 108.1 . . ? C35 C34 C33 112.0(7) . . ? C35 C34 H41 109.2 . . ? C33 C34 H41 109.2 . . ? C35 C34 H42 109.2 . . ? C33 C34 H42 109.2 . . ? H41 C34 H42 107.9 . . ? C34 C35 H43 109.5 . . ? C34 C35 H44 109.5 . . ? H43 C35 H44 109.5 . . ? C34 C35 H45 109.5 . . ? H43 C35 H45 109.5 . . ? H44 C35 H45 109.5 . . ? C37 C36 N3 115.4(6) . . ? C37 C36 H46 108.4 . . ? N3 C36 H46 108.4 . . ? C37 C36 H47 108.4 . . ? N3 C36 H47 108.4 . . ? H46 C36 H47 107.5 . . ? C36 C37 C38 110.5(7) . . ? C36 C37 H48 109.5 . . ? C38 C37 H48 109.5 . . ? C36 C37 H49 109.5 . . ? C38 C37 H49 109.5 . . ? H48 C37 H49 108.1 . . ? C39 C38 C37 100.3(11) . . ? C39 C38 H50 111.7 . . ? C37 C38 H50 111.7 . . ? C39 C38 H51 111.7 . . ? C37 C38 H51 111.7 . . ? H50 C38 H51 109.5 . . ? C38 C39 H52 109.5 . . ? C38 C39 H53 109.5 . . ? H52 C39 H53 109.5 . . ? C38 C39 H54 109.5 . . ? H52 C39 H54 109.5 . . ? H53 C39 H54 109.5 . . ? N4 C40 C41 109.1(6) . . ? N4 C40 H55 125.4 . . ? C41 C40 H55 125.4 . . ? C40 C41 C42 107.5(7) . . ? C40 C41 H56 126.3 . . ? C42 C41 H56 126.3 . . ? C43 C42 C41 106.9(6) . . ? C43 C42 H57 126.6 . . ? C41 C42 H57 126.6 . . ? C42 C43 N4 108.4(6) . . ? C42 C43 C44 129.4(6) . . ? N4 C43 C44 122.0(6) . . ? O3 C44 C45 120.2(6) . . ? O3 C44 C43 115.8(5) . . ? C45 C44 C43 123.9(6) . . ? C44 C45 C46 119.4(6) . . ? C44 C45 H58 120.3 . . ? C46 C45 H58 120.3 . . ? O4 C46 C45 121.3(6) . . ? O4 C46 C47 114.5(8) . . ? C45 C46 C47 124.1(8) . . ? C48 C47 N5 108.8(8) . . ? C48 C47 C46 129.3(9) . . ? N5 C47 C46 121.9(10) . . ? C47 C48 C49 105.0(11) . . ? C47 C48 H59 127.5 . . ? C49 C48 H59 127.5 . . ? C50 C49 C48 104.8(11) . . ? C50 C49 H60 127.6 . . ? C48 C49 H60 127.6 . . ? N5 C50 C49 113.7(14) . . ? N5 C50 H61 123.1 . . ? C49 C50 H61 123.1 . . ? C40 N4 C43 108.2(6) . . ? C40 N4 H62 125.9 . . ? C43 N4 H62 125.9 . . ? C50 N5 C47 107.5(13) . . ? C50 N5 H110 126.3 . . ? C47 N5 H110 126.3 . . ? C44 O3 B2 116.7(5) . . ? C46 O4 B2 113.9(5) . . ? O4 B2 O3 105.9(4) . . ? O4 B2 C51 109.5(5) . . ? O3 B2 C51 110.0(5) . . ? O4 B2 C57 108.6(5) . . ? O3 B2 C57 108.1(5) . . ? C51 B2 C57 114.4(5) . . ? C56 C51 C52 116.9(6) . . ? C56 C51 B2 120.4(6) . . ? C52 C51 B2 122.6(6) . . ? C53 C52 C51 121.7(7) . . ? C53 C52 H63 119.2 . . ? C51 C52 H63 119.2 . . ? C52 C53 C54 119.7(7) . . ? C52 C53 H64 120.2 . . ? C54 C53 H64 120.2 . . ? C55 C54 C53 120.1(6) . . ? C55 C54 H65 120.0 . . ? C53 C54 H65 120.0 . . ? C54 C55 C56 120.0(7) . . ? C54 C55 H66 120.0 . . ? C56 C55 H66 120.0 . . ? C51 C56 C55 121.7(7) . . ? C51 C56 H67 119.1 . . ? C55 C56 H67 119.1 . . ? C62 C57 C58 117.5(6) . . ? C62 C57 B2 124.7(6) . . ? C58 C57 B2 117.8(5) . . ? C59 C58 C57 120.9(6) . . ? C59 C58 H68 119.5 . . ? C57 C58 H68 119.5 . . ? C60 C59 C58 120.9(7) . . ? C60 C59 H69 119.5 . . ? C58 C59 H69 119.5 . . ? C59 C60 C61 119.3(6) . . ? C59 C60 H70 120.4 . . ? C61 C60 H70 120.4 . . ? C60 C61 C62 121.3(6) . . ? C60 C61 H71 119.4 . . ? C62 C61 H71 119.4 . . ? C57 C62 C61 120.0(6) . . ? C57 C62 H72 120.0 . . ? C61 C62 H72 120.0 . . ? C63 N6 C67 112.3(6) . . ? C63 N6 C75 111.8(6) . . ? C67 N6 C75 106.0(5) . . ? C63 N6 C71 105.9(5) . . ? C67 N6 C71 110.3(6) . . ? C75 N6 C71 110.6(6) . . ? N6 C63 C64 116.7(5) . . ? N6 C63 H73 108.1 . . ? C64 C63 H73 108.1 . . ? N6 C63 H74 108.1 . . ? C64 C63 H74 108.1 . . ? H73 C63 H74 107.3 . . ? C65 C64 C63 109.4(6) . . ? C65 C64 H75 109.8 . . ? C63 C64 H75 109.8 . . ? C65 C64 H76 109.8 . . ? C63 C64 H76 109.8 . . ? H75 C64 H76 108.2 . . ? C64 C65 C66 110.9(6) . . ? C64 C65 H77 109.5 . . ? C66 C65 H77 109.5 . . ? C64 C65 H78 109.5 . . ? C66 C65 H78 109.5 . . ? H77 C65 H78 108.1 . . ? C65 C66 H79 109.5 . . ? C65 C66 H80 109.5 . . ? H79 C66 H80 109.5 . . ? C65 C66 H81 109.5 . . ? H79 C66 H81 109.5 . . ? H80 C66 H81 109.5 . . ? N6 C67 C68 115.1(5) . . ? N6 C67 H82 108.5 . . ? C68 C67 H82 108.5 . . ? N6 C67 H83 108.5 . . ? C68 C67 H83 108.5 . . ? H82 C67 H83 107.5 . . ? C69 C68 C67 109.6(5) . . ? C69 C68 H84 109.8 . . ? C67 C68 H84 109.8 . . ? C69 C68 H85 109.8 . . ? C67 C68 H85 109.8 . . ? H84 C68 H85 108.2 . . ? C70 C69 C68 112.5(5) . . ? C70 C69 H86 109.1 . . ? C68 C69 H86 109.1 . . ? C70 C69 H87 109.1 . . ? C68 C69 H87 109.1 . . ? H86 C69 H87 107.8 . . ? C69 C70 H88 109.5 . . ? C69 C70 H89 109.5 . . ? H88 C70 H89 109.5 . . ? C69 C70 H90 109.5 . . ? H88 C70 H90 109.5 . . ? H89 C70 H90 109.5 . . ? C72 C71 N6 117.6(5) . . ? C72 C71 H91 107.9 . . ? N6 C71 H91 107.9 . . ? C72 C71 H92 107.9 . . ? N6 C71 H92 107.9 . . ? H91 C71 H92 107.2 . . ? C71 C72 C73 110.4(6) . . ? C71 C72 H93 109.6 . . ? C73 C72 H93 109.6 . . ? C71 C72 H94 109.6 . . ? C73 C72 H94 109.6 . . ? H93 C72 H94 108.1 . . ? C72 C73 C74 115.1(7) . . ? C72 C73 H95 108.5 . . ? C74 C73 H95 108.5 . . ? C72 C73 H96 108.5 . . ? C74 C73 H96 108.5 . . ? H95 C73 H96 107.5 . . ? C73 C74 H97 109.5 . . ? C73 C74 H98 109.5 . . ? H97 C74 H98 109.5 . . ? C73 C74 H99 109.5 . . ? H97 C74 H99 109.5 . . ? H98 C74 H99 109.5 . . ? C76 C75 N6 114.9(6) . . ? C76 C75 H100 108.5 . . ? N6 C75 H100 108.5 . . ? C76 C75 H101 108.5 . . ? N6 C75 H101 108.5 . . ? H100 C75 H101 107.5 . . ? C75 C76 C77 106.1(7) . . ? C75 C76 H102 110.5 . . ? C77 C76 H102 110.5 . . ? C75 C76 H103 110.5 . . ? C77 C76 H103 110.5 . . ? H102 C76 H103 108.7 . . ? C78 C77 C76 88.6(10) . . ? C78 C77 H104 113.9 . . ? C76 C77 H104 113.9 . . ? C78 C77 H105 113.9 . . ? C76 C77 H105 113.9 . . ? H104 C77 H105 111.1 . . ? C77 C78 H106 109.5 . . ? C77 C78 H107 109.5 . . ? H106 C78 H107 109.5 . . ? C77 C78 H108 109.5 . . ? H106 C78 H108 109.5 . . ? H107 C78 H108 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.7(9) . . . . ? C1 C2 C3 C4 0.5(8) . . . . ? C2 C3 C4 N1 -0.2(7) . . . . ? C2 C3 C4 C5 -176.4(6) . . . . ? C3 C4 C5 O1 4.5(8) . . . . ? N1 C4 C5 O1 -171.1(5) . . . . ? C3 C4 C5 C6 -179.2(6) . . . . ? N1 C4 C5 C6 5.2(8) . . . . ? O1 C5 C6 C7 8.9(8) . . . . ? C4 C5 C6 C7 -167.2(5) . . . . ? C5 C6 C7 O2 -9.1(9) . . . . ? C5 C6 C7 C8 166.4(6) . . . . ? O2 C7 C8 C9 -11.0(10) . . . . ? C6 C7 C8 C9 173.2(7) . . . . ? O2 C7 C8 N2 175.7(6) . . . . ? C6 C7 C8 N2 -0.1(10) . . . . ? N2 C8 C9 C10 -3.9(9) . . . . ? C7 C8 C9 C10 -177.8(8) . . . . ? C8 C9 C10 C11 6.4(14) . . . . ? C9 C10 C11 N2 -6.5(17) . . . . ? C2 C1 N1 C4 0.5(8) . . . . ? C3 C4 N1 C1 -0.2(7) . . . . ? C5 C4 N1 C1 176.2(5) . . . . ? C10 C11 N2 C8 4.1(14) . . . . ? C9 C8 N2 C11 0.1(9) . . . . ? C7 C8 N2 C11 174.7(7) . . . . ? C6 C5 O1 B1 19.0(7) . . . . ? C4 C5 O1 B1 -164.6(4) . . . . ? C6 C7 O2 B1 -18.4(8) . . . . ? C8 C7 O2 B1 165.7(5) . . . . ? C7 O2 B1 O1 41.4(6) . . . . ? C7 O2 B1 C18 157.6(5) . . . . ? C7 O2 B1 C12 -75.5(6) . . . . ? C5 O1 B1 O2 -42.1(6) . . . . ? C5 O1 B1 C18 -158.6(4) . . . . ? C5 O1 B1 C12 75.4(6) . . . . ? O2 B1 C12 C17 -45.0(9) . . . . ? O1 B1 C12 C17 -161.5(6) . . . . ? C18 B1 C12 C17 77.4(8) . . . . ? O2 B1 C12 C13 136.6(6) . . . . ? O1 B1 C12 C13 20.1(8) . . . . ? C18 B1 C12 C13 -101.0(7) . . . . ? C17 C12 C13 C14 -0.7(11) . . . . ? B1 C12 C13 C14 177.8(7) . . . . ? C12 C13 C14 C15 0.1(13) . . . . ? C13 C14 C15 C16 -0.5(15) . . . . ? C14 C15 C16 C17 1.7(16) . . . . ? C13 C12 C17 C16 1.9(12) . . . . ? B1 C12 C17 C16 -176.6(8) . . . . ? C15 C16 C17 C12 -2.4(16) . . . . ? O2 B1 C18 C19 -133.5(6) . . . . ? O1 B1 C18 C19 -17.6(7) . . . . ? C12 B1 C18 C19 103.7(7) . . . . ? O2 B1 C18 C23 48.0(7) . . . . ? O1 B1 C18 C23 164.0(5) . . . . ? C12 B1 C18 C23 -74.8(7) . . . . ? C23 C18 C19 C20 -0.3(8) . . . . ? B1 C18 C19 C20 -178.8(5) . . . . ? C18 C19 C20 C21 0.1(9) . . . . ? C19 C20 C21 C22 -0.1(10) . . . . ? C20 C21 C22 C23 0.3(10) . . . . ? C21 C22 C23 C18 -0.5(10) . . . . ? C19 C18 C23 C22 0.5(9) . . . . ? B1 C18 C23 C22 179.0(6) . . . . ? C32 N3 C24 C25 -178.4(7) . . . . ? C36 N3 C24 C25 61.7(8) . . . . ? C28 N3 C24 C25 -57.3(8) . . . . ? N3 C24 C25 C26 -175.4(6) . . . . ? C24 C25 C26 C27 -179.1(7) . . . . ? C32 N3 C28 C29 60.2(10) . . . . ? C36 N3 C28 C29 -178.3(8) . . . . ? C24 N3 C28 C29 -57.3(10) . . . . ? N3 C28 C29 C30 -168.6(8) . . . . ? C28 C29 C30 C31 -179.0(7) . . . . ? C36 N3 C32 C33 -60.3(9) . . . . ? C28 N3 C32 C33 59.3(9) . . . . ? C24 N3 C32 C33 179.9(7) . . . . ? N3 C32 C33 C34 179.7(7) . . . . ? C32 C33 C34 C35 -178.3(7) . . . . ? C32 N3 C36 C37 -56.5(12) . . . . ? C28 N3 C36 C37 -178.6(10) . . . . ? C24 N3 C36 C37 60.3(11) . . . . ? N3 C36 C37 C38 174.0(9) . . . . ? C36 C37 C38 C39 74.9(12) . . . . ? N4 C40 C41 C42 0.5(7) . . . . ? C40 C41 C42 C43 0.6(7) . . . . ? C41 C42 C43 N4 -1.5(6) . . . . ? C41 C42 C43 C44 -175.8(6) . . . . ? C42 C43 C44 O3 2.4(9) . . . . ? N4 C43 C44 O3 -171.2(5) . . . . ? C42 C43 C44 C45 179.2(6) . . . . ? N4 C43 C44 C45 5.6(9) . . . . ? O3 C44 C45 C46 17.5(9) . . . . ? C43 C44 C45 C46 -159.2(5) . . . . ? C44 C45 C46 O4 -12.3(9) . . . . ? C44 C45 C46 C47 163.0(6) . . . . ? O4 C46 C47 C48 1.9(10) . . . . ? C45 C46 C47 C48 -173.7(7) . . . . ? O4 C46 C47 N5 -179.4(6) . . . . ? C45 C46 C47 N5 5.0(10) . . . . ? N5 C47 C48 C49 2.3(9) . . . . ? C46 C47 C48 C49 -178.9(7) . . . . ? C47 C48 C49 C50 -4.4(12) . . . . ? C48 C49 C50 N5 5.3(15) . . . . ? C41 C40 N4 C43 -1.4(7) . . . . ? C42 C43 N4 C40 1.9(6) . . . . ? C44 C43 N4 C40 176.7(5) . . . . ? C49 C50 N5 C47 -4.0(14) . . . . ? C48 C47 N5 C50 0.8(9) . . . . ? C46 C47 N5 C50 -178.2(7) . . . . ? C45 C44 O3 B2 14.2(8) . . . . ? C43 C44 O3 B2 -168.8(5) . . . . ? C45 C46 O4 B2 -23.8(7) . . . . ? C47 C46 O4 B2 160.5(5) . . . . ? C46 O4 B2 O3 49.8(6) . . . . ? C46 O4 B2 C51 -68.8(6) . . . . ? C46 O4 B2 C57 165.7(5) . . . . ? C44 O3 B2 O4 -45.8(6) . . . . ? C44 O3 B2 C51 72.5(6) . . . . ? C44 O3 B2 C57 -162.0(5) . . . . ? O4 B2 C51 C56 -41.8(8) . . . . ? O3 B2 C51 C56 -157.9(6) . . . . ? C57 B2 C51 C56 80.3(8) . . . . ? O4 B2 C51 C52 136.0(6) . . . . ? O3 B2 C51 C52 20.0(8) . . . . ? C57 B2 C51 C52 -101.8(7) . . . . ? C56 C51 C52 C53 -1.6(10) . . . . ? B2 C51 C52 C53 -179.5(6) . . . . ? C51 C52 C53 C54 0.1(12) . . . . ? C52 C53 C54 C55 0.6(12) . . . . ? C53 C54 C55 C56 0.1(12) . . . . ? C52 C51 C56 C55 2.3(10) . . . . ? B2 C51 C56 C55 -179.7(6) . . . . ? C54 C55 C56 C51 -1.6(11) . . . . ? O4 B2 C57 C62 0.0(8) . . . . ? O3 B2 C57 C62 114.5(6) . . . . ? C51 B2 C57 C62 -122.7(6) . . . . ? O4 B2 C57 C58 178.8(4) . . . . ? O3 B2 C57 C58 -66.7(6) . . . . ? C51 B2 C57 C58 56.1(7) . . . . ? C62 C57 C58 C59 -3.4(8) . . . . ? B2 C57 C58 C59 177.7(5) . . . . ? C57 C58 C59 C60 2.0(9) . . . . ? C58 C59 C60 C61 1.5(10) . . . . ? C59 C60 C61 C62 -3.6(10) . . . . ? C58 C57 C62 C61 1.4(9) . . . . ? B2 C57 C62 C61 -179.8(5) . . . . ? C60 C61 C62 C57 2.1(10) . . . . ? C67 N6 C63 C64 60.4(7) . . . . ? C75 N6 C63 C64 -58.6(8) . . . . ? C71 N6 C63 C64 -179.1(6) . . . . ? N6 C63 C64 C65 172.4(6) . . . . ? C63 C64 C65 C66 176.0(6) . . . . ? C63 N6 C67 C68 65.3(8) . . . . ? C75 N6 C67 C68 -172.4(7) . . . . ? C71 N6 C67 C68 -52.6(8) . . . . ? N6 C67 C68 C69 -174.5(6) . . . . ? C67 C68 C69 C70 -174.5(6) . . . . ? C63 N6 C71 C72 -179.4(6) . . . . ? C67 N6 C71 C72 -57.7(8) . . . . ? C75 N6 C71 C72 59.3(8) . . . . ? N6 C71 C72 C73 169.8(6) . . . . ? C71 C72 C73 C74 -177.6(7) . . . . ? C63 N6 C75 C76 -51.0(12) . . . . ? C67 N6 C75 C76 -173.7(10) . . . . ? C71 N6 C75 C76 66.8(12) . . . . ? N6 C75 C76 C77 172.6(9) . . . . ? C75 C76 C77 C78 91.4(12) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.179 _refine_diff_density_min -1.093 _refine_diff_density_rms 0.067 #============================================================================== # End of CIF #============================================================================== data_90915mae _database_code_depnum_ccdc_archive 'CCDC 759625' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C47 H71 B Br N3 O2' _chemical_formula_weight 800.79 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P - 1' _symmetry_space_group_name_Hall -P1 _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.031(2) _cell_length_b 13.255(5) _cell_length_c 19.555(6) _cell_angle_alpha 96.453(13) _cell_angle_beta 90.315(11) _cell_angle_gamma 106.498(11) _cell_volume 2228.6(12) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 0.962 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.6715 _exptl_absorpt_correction_T_max 0.7613 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _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 \w _diffrn_detector_area_resol_mean 10 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15048 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 23.50 _reflns_number_total 6516 _reflns_number_gt 5764 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0774P)^2^+6.0207P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6516 _refine_ls_number_parameters 516 _refine_ls_number_restraints 45 _refine_ls_R_factor_all 0.0703 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.1711 _refine_ls_wR_factor_gt 0.1646 _refine_ls_goodness_of_fit_ref 1.165 _refine_ls_restrained_S_all 1.241 _refine_ls_shift/su_max 0.030 _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 O1 O 0.3896(3) 0.0965(2) 0.30270(15) 0.0194(7) Uani 1 1 d . . . O2 O 0.5133(3) 0.1378(2) 0.19227(15) 0.0218(7) Uani 1 1 d . . . C55 C 0.3989(5) 0.1973(3) 0.3173(2) 0.0178(9) Uani 1 1 d . . . N2 N 0.6163(5) 0.4192(4) 0.1808(2) 0.0388(8) Uani 1 1 d U . . H1 H 0.5971 0.4495 0.2208 0.047 Uiso 1 1 calc R . . C57 C 0.2561(5) 0.1697(4) 0.4306(2) 0.0195(10) Uani 1 1 d . . . N3 N 0.3793(4) 0.3352(3) 0.40875(19) 0.0213(8) Uani 1 1 d . . . H2 H 0.4349 0.3890 0.3888 0.026 Uiso 1 1 calc R . . C59 C 0.2286(5) 0.0317(3) 0.1898(2) 0.0207(10) Uani 1 1 d . . . C60 C 0.2286(5) 0.2423(4) 0.4840(2) 0.0207(10) Uani 1 1 d . . . C61 C 0.4549(5) 0.2686(4) 0.2699(2) 0.0210(10) Uani 1 1 d . . . H3 H 0.4498 0.3394 0.2791 0.025 Uiso 1 1 calc R . . N1 N 1.0620(4) 0.4553(3) 0.2771(2) 0.0229(9) Uani 1 1 d . . . C63 C 0.3505(5) 0.2289(3) 0.3834(2) 0.0186(9) Uani 1 1 d . . . C64 C 0.1040(5) 0.0578(4) 0.2204(2) 0.0240(10) Uani 1 1 d . . . H4 H 0.1153 0.0887 0.2670 0.029 Uiso 1 1 calc R . . C65 C 0.4591(5) -0.0491(4) 0.2251(2) 0.0213(10) Uani 1 1 d . . . C66 C 0.0659(6) -0.0314(4) 0.0850(3) 0.0311(12) Uani 1 1 d . . . H5 H 0.0541 -0.0622 0.0383 0.037 Uiso 1 1 calc R . . C67 C 0.3084(5) 0.3424(4) 0.4688(2) 0.0218(10) Uani 1 1 d . . . H6 H 0.3126 0.4067 0.4967 0.026 Uiso 1 1 calc R . . C68 C 0.5177(5) 0.2373(4) 0.2097(2) 0.0199(10) Uani 1 1 d . . . C69 C -0.0372(6) 0.0402(4) 0.1849(3) 0.0296(11) Uani 1 1 d . . . H7 H -0.1205 0.0585 0.2074 0.036 Uiso 1 1 calc R . . C70 C 0.5918(6) 0.3119(4) 0.1632(2) 0.0257(11) Uani 1 1 d . A . C71 C 0.4346(5) -0.1131(4) 0.2788(2) 0.0246(10) Uani 1 1 d . . . H8 H 0.3813 -0.0948 0.3179 0.029 Uiso 1 1 calc R . . C72 C 0.1992(5) 0.0513(4) 0.4263(2) 0.0242(10) Uani 1 1 d . . . H28 H 0.1683 0.0212 0.3779 0.029 Uiso 1 1 calc R . . H29 H 0.1070 0.0308 0.4544 0.029 Uiso 1 1 calc R . . C73 C 0.4863(6) -0.2024(4) 0.2763(3) 0.0300(12) Uani 1 1 d . . . H9 H 0.4693 -0.2436 0.3138 0.036 Uiso 1 1 calc R . . C74 C 0.9177(5) 0.3702(4) 0.2927(3) 0.0249(10) Uani 1 1 d . . . H34 H 0.8502 0.4050 0.3202 0.030 Uiso 1 1 calc R . . H35 H 0.8611 0.3371 0.2486 0.030 Uiso 1 1 calc R . . B1 B 0.3966(6) 0.0527(4) 0.2277(3) 0.0203(11) Uani 1 1 d . . . C76 C 1.1662(5) 0.4071(4) 0.2316(2) 0.0243(10) Uani 1 1 d . . . H36 H 1.2625 0.4636 0.2259 0.029 Uiso 1 1 calc R . . H37 H 1.1948 0.3535 0.2562 0.029 Uiso 1 1 calc R . . C77 C 0.7888(5) 0.2014(4) 0.3397(3) 0.0274(11) Uani 1 1 d . . . H38 H 0.7211 0.2369 0.3664 0.033 Uiso 1 1 calc R . . H39 H 0.7381 0.1733 0.2938 0.033 Uiso 1 1 calc R . . C78 C -0.0550(6) -0.0041(4) 0.1167(3) 0.0306(12) Uani 1 1 d . . . H10 H -0.1503 -0.0155 0.0920 0.037 Uiso 1 1 calc R . . C79 C 0.3243(6) 0.0051(4) 0.4520(3) 0.0329(12) Uani 1 1 d . . . H11 H 0.4135 0.0219 0.4226 0.049 Uiso 1 1 calc R . . H12 H 0.2827 -0.0720 0.4503 0.049 Uiso 1 1 calc R . . H13 H 0.3568 0.0359 0.4995 0.049 Uiso 1 1 calc R . . C80 C 0.1304(6) 0.2186(4) 0.5449(2) 0.0268(11) Uani 1 1 d . . . H30 H 0.0264 0.1733 0.5284 0.032 Uiso 1 1 calc R . . H31 H 0.1185 0.2858 0.5683 0.032 Uiso 1 1 calc R . . C81 C 0.5614(6) -0.2316(4) 0.2204(3) 0.0353(13) Uani 1 1 d . . . H14 H 0.5965 -0.2929 0.2187 0.042 Uiso 1 1 calc R . . C82 C 0.9439(5) 0.2830(4) 0.3311(3) 0.0261(11) Uani 1 1 d . . . H40 H 0.9938 0.3137 0.3769 0.031 Uiso 1 1 calc R . . H41 H 1.0133 0.2482 0.3051 0.031 Uiso 1 1 calc R . . C83 C 1.0075(5) 0.5349(4) 0.2409(3) 0.0264(11) Uani 1 1 d . . . H42 H 0.9469 0.4974 0.1986 0.032 Uiso 1 1 calc R . . H43 H 0.9375 0.5628 0.2714 0.032 Uiso 1 1 calc R . . C84 C 1.0723(6) 0.7007(4) 0.1822(3) 0.0376(13) Uani 1 1 d . . . H44 H 1.1595 0.7527 0.1634 0.045 Uiso 1 1 calc R . . H45 H 1.0057 0.6580 0.1427 0.045 Uiso 1 1 calc R . . C85 C 1.0759(6) 0.5707(4) 0.3933(3) 0.0348(12) Uani 1 1 d . . . H46 H 0.9709 0.5254 0.4009 0.042 Uiso 1 1 calc R . . H47 H 1.0652 0.6335 0.3731 0.042 Uiso 1 1 calc R . . C86 C 0.5856(6) -0.1709(4) 0.1663(3) 0.0382(13) Uani 1 1 d . . . H15 H 0.6365 -0.1911 0.1270 0.046 Uiso 1 1 calc R . . C87 C 1.1563(5) 0.5091(4) 0.3431(3) 0.0261(11) Uani 1 1 d . . . H48 H 1.1831 0.4542 0.3669 0.031 Uiso 1 1 calc R . . H49 H 1.2541 0.5583 0.3303 0.031 Uiso 1 1 calc R . . C88 C 0.6743(7) 0.4704(5) 0.1265(3) 0.0464(8) Uani 1 1 d U . . H16 H 0.6985 0.5446 0.1246 0.056 Uiso 1 1 calc R . . C89 C 0.5361(6) -0.0808(4) 0.1693(3) 0.0296(11) Uani 1 1 d . . . H17 H 0.5554 -0.0395 0.1319 0.035 Uiso 1 1 calc R . . C90 C 1.1006(6) 0.3550(4) 0.1608(3) 0.0309(11) Uani 1 1 d . . . H50 H 1.0072 0.2955 0.1653 0.037 Uiso 1 1 calc R . . H51 H 1.0701 0.4070 0.1354 0.037 Uiso 1 1 calc R . . C91 C 0.1945(6) 0.1633(4) 0.5970(3) 0.0313(11) Uani 1 1 d . . . H18 H 0.1997 0.0941 0.5753 0.047 Uiso 1 1 calc R . . H19 H 0.1268 0.1534 0.6362 0.047 Uiso 1 1 calc R . . H20 H 0.2984 0.2068 0.6132 0.047 Uiso 1 1 calc R . . C92 C 1.2195(6) 0.3141(4) 0.1211(3) 0.0325(12) Uani 1 1 d . . . H52 H 1.2451 0.2595 0.1457 0.039 Uiso 1 1 calc R . . H53 H 1.3151 0.3732 0.1198 0.039 Uiso 1 1 calc R . . C93 C 0.2048(5) -0.0141(4) 0.1211(2) 0.0264(11) Uani 1 1 d . . . H21 H 0.2868 -0.0339 0.0985 0.032 Uiso 1 1 calc R . . C94 C 1.1655(6) 0.6063(4) 0.4620(3) 0.0358(12) Uani 1 1 d . . . H54 H 1.1050 0.6408 0.4940 0.043 Uiso 1 1 calc R . . H55 H 1.1758 0.5429 0.4817 0.043 Uiso 1 1 calc R . . C95 C 1.1360(6) 0.6275(4) 0.2215(3) 0.0378(13) Uani 1 1 d . . . H56 H 1.2092 0.6004 0.1925 0.045 Uiso 1 1 calc R . . H57 H 1.1934 0.6683 0.2638 0.045 Uiso 1 1 calc R . . C96 C 0.8059(6) 0.1101(4) 0.3760(3) 0.0370(13) Uani 1 1 d . . . H58 H 0.8727 0.0745 0.3498 0.056 Uiso 1 1 calc R . . H59 H 0.7040 0.0596 0.3794 0.056 Uiso 1 1 calc R . . H60 H 0.8521 0.1370 0.4223 0.056 Uiso 1 1 calc R . . C97 C 0.9800(7) 0.7599(5) 0.2265(4) 0.0569(18) Uani 1 1 d . . . H61 H 0.8919 0.7089 0.2443 0.085 Uiso 1 1 calc R . . H62 H 0.9423 0.8053 0.1988 0.085 Uiso 1 1 calc R . . H63 H 1.0459 0.8036 0.2650 0.085 Uiso 1 1 calc R . . C101 C 1.1640(7) 0.2663(5) 0.0473(3) 0.0433(14) Uani 1 1 d . . . H64 H 1.0695 0.2076 0.0481 0.065 Uiso 1 1 calc R . . H65 H 1.2443 0.2400 0.0244 0.065 Uiso 1 1 calc R . . H66 H 1.1426 0.3208 0.0220 0.065 Uiso 1 1 calc R . . C102 C 1.3250(7) 0.6822(5) 0.4579(3) 0.0434(14) Uani 1 1 d . . . H67 H 1.3906 0.6457 0.4316 0.065 Uiso 1 1 calc R . . H68 H 1.3705 0.7074 0.5045 0.065 Uiso 1 1 calc R . . H69 H 1.3172 0.7426 0.4350 0.065 Uiso 1 1 calc R . . C116 C 0.6922(8) 0.3970(5) 0.0751(3) 0.0565(8) Uani 1 1 d DU A . C106 C 0.6350(10) 0.2972(4) 0.0955(3) 0.064(2) Uani 1 1 d . . . Br1 Br 0.61115(6) 0.54408(4) 0.33815(2) 0.0294(2) Uani 1 1 d . . . C109 C 0.667(3) 0.1930(13) 0.0615(8) 0.035(5) Uani 0.47(3) 1 d P A 2 H70 H 0.7541 0.2101 0.0303 0.042 Uiso 0.47(3) 1 calc PR A 2 H71 H 0.6930 0.1532 0.0973 0.042 Uiso 0.47(3) 1 calc PR A 2 C110 C 0.524(2) 0.1290(17) 0.0221(9) 0.054(5) Uani 0.47(3) 1 d P A 2 H72 H 0.4405 0.1069 0.0540 0.082 Uiso 0.47(3) 1 calc PR A 2 H73 H 0.5426 0.0662 -0.0035 0.082 Uiso 0.47(3) 1 calc PR A 2 H74 H 0.4934 0.1716 -0.0103 0.082 Uiso 0.47(3) 1 calc PR A 2 C111 C 0.5773(19) 0.1928(14) 0.0470(7) 0.032(6) Uani 0.53(3) 1 d P A 1 H75 H 0.4845 0.1437 0.0641 0.038 Uiso 0.53(3) 1 calc PR A 1 H76 H 0.5560 0.2051 -0.0006 0.038 Uiso 0.53(3) 1 calc PR A 1 C112 C 0.7196(17) 0.1538(15) 0.0524(7) 0.037(4) Uani 0.53(3) 1 d P A 1 H77 H 0.8081 0.2037 0.0341 0.056 Uiso 0.53(3) 1 calc PR A 1 H78 H 0.7003 0.0838 0.0257 0.056 Uiso 0.53(3) 1 calc PR A 1 H79 H 0.7421 0.1488 0.1008 0.056 Uiso 0.53(3) 1 calc PR A 1 C117 C 0.7407(8) 0.4229(6) 0.0017(3) 0.0656(9) Uani 1 1 d DU . . H80 H 0.8173 0.4938 0.0063 0.079 Uiso 1 1 calc R A . H81 H 0.7945 0.3713 -0.0176 0.079 Uiso 1 1 calc R . . C118 C 0.6136(9) 0.4229(6) -0.0519(3) 0.0712(10) Uani 1 1 d DU A . H82 H 0.5381 0.3527 -0.0587 0.107 Uiso 1 1 calc R . . H83 H 0.6609 0.4401 -0.0957 0.107 Uiso 1 1 calc R . . H84 H 0.5617 0.4760 -0.0351 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 O1 0.0232(16) 0.0166(16) 0.0171(15) 0.0016(12) -0.0001(13) 0.0036(13) O2 0.0236(17) 0.0189(17) 0.0203(16) 0.0014(13) 0.0014(13) 0.0023(13) C55 0.013(2) 0.019(2) 0.021(2) 0.0018(18) -0.0041(18) 0.0031(17) N2 0.0447(15) 0.0378(14) 0.0372(14) 0.0131(13) 0.0060(13) 0.0139(13) C57 0.016(2) 0.024(2) 0.019(2) 0.0034(19) -0.0051(18) 0.0056(18) N3 0.027(2) 0.0161(19) 0.020(2) 0.0029(16) 0.0001(16) 0.0037(16) C59 0.028(2) 0.014(2) 0.020(2) 0.0064(18) -0.0002(19) 0.0026(19) C60 0.021(2) 0.026(2) 0.018(2) 0.0027(19) 0.0001(18) 0.0105(19) C61 0.021(2) 0.018(2) 0.022(2) 0.0026(19) -0.0031(19) 0.0032(19) N1 0.0167(19) 0.022(2) 0.031(2) 0.0055(17) 0.0005(16) 0.0063(16) C63 0.018(2) 0.018(2) 0.020(2) 0.0027(18) -0.0018(18) 0.0056(18) C64 0.025(2) 0.019(2) 0.026(2) 0.0020(19) -0.001(2) 0.0038(19) C65 0.018(2) 0.020(2) 0.023(2) 0.0012(19) -0.0040(19) 0.0018(18) C66 0.035(3) 0.032(3) 0.021(2) 0.000(2) -0.006(2) 0.002(2) C67 0.028(2) 0.021(2) 0.019(2) 0.0001(19) -0.0014(19) 0.012(2) C68 0.017(2) 0.023(2) 0.018(2) 0.0010(19) -0.0028(18) 0.0026(18) C69 0.024(3) 0.029(3) 0.038(3) 0.006(2) 0.003(2) 0.009(2) C70 0.033(3) 0.017(2) 0.024(2) 0.0035(19) 0.003(2) 0.001(2) C71 0.025(2) 0.023(2) 0.023(2) 0.002(2) -0.003(2) 0.003(2) C72 0.028(2) 0.021(2) 0.022(2) 0.0043(19) 0.006(2) 0.003(2) C73 0.026(3) 0.024(3) 0.037(3) 0.011(2) -0.009(2) 0.001(2) C74 0.017(2) 0.022(2) 0.036(3) 0.007(2) 0.002(2) 0.0050(19) B1 0.024(3) 0.017(3) 0.017(3) 0.002(2) 0.003(2) 0.000(2) C76 0.020(2) 0.024(2) 0.030(3) 0.006(2) 0.002(2) 0.0076(19) C77 0.023(2) 0.029(3) 0.032(3) 0.012(2) 0.002(2) 0.007(2) C78 0.022(3) 0.032(3) 0.035(3) 0.006(2) -0.008(2) 0.003(2) C79 0.049(3) 0.029(3) 0.028(3) 0.012(2) 0.011(2) 0.020(2) C80 0.028(3) 0.029(3) 0.025(2) 0.003(2) 0.003(2) 0.010(2) C81 0.025(3) 0.024(3) 0.060(4) 0.010(3) 0.001(3) 0.011(2) C82 0.023(2) 0.026(3) 0.032(3) 0.009(2) -0.002(2) 0.008(2) C83 0.022(2) 0.022(2) 0.038(3) 0.012(2) -0.001(2) 0.009(2) C84 0.037(3) 0.027(3) 0.049(3) 0.019(2) 0.007(3) 0.004(2) C85 0.028(3) 0.036(3) 0.040(3) 0.000(2) 0.005(2) 0.011(2) C86 0.036(3) 0.032(3) 0.051(3) 0.005(3) 0.016(3) 0.016(2) C87 0.019(2) 0.024(2) 0.034(3) 0.001(2) -0.001(2) 0.006(2) C88 0.0516(13) 0.0444(13) 0.0442(12) 0.0117(11) 0.0063(11) 0.0129(11) C89 0.031(3) 0.026(3) 0.034(3) 0.008(2) 0.005(2) 0.010(2) C90 0.027(3) 0.031(3) 0.034(3) 0.002(2) -0.006(2) 0.008(2) C91 0.038(3) 0.032(3) 0.024(3) 0.005(2) 0.004(2) 0.009(2) C92 0.035(3) 0.036(3) 0.028(3) 0.002(2) 0.000(2) 0.011(2) C93 0.025(3) 0.030(3) 0.023(3) 0.004(2) 0.001(2) 0.005(2) C94 0.042(3) 0.039(3) 0.033(3) 0.006(2) 0.007(2) 0.022(3) C95 0.025(3) 0.030(3) 0.061(4) 0.019(3) 0.009(3) 0.006(2) C96 0.032(3) 0.037(3) 0.044(3) 0.021(3) 0.004(2) 0.006(2) C97 0.049(4) 0.035(3) 0.096(5) 0.030(4) 0.020(4) 0.018(3) C101 0.047(3) 0.042(3) 0.036(3) -0.003(3) -0.006(3) 0.007(3) C102 0.044(3) 0.049(4) 0.036(3) -0.006(3) -0.002(3) 0.017(3) C116 0.0599(11) 0.0542(11) 0.0541(11) 0.0087(8) 0.0060(8) 0.0133(8) C106 0.122(6) 0.021(3) 0.035(3) 0.002(3) 0.038(4) -0.003(3) Br1 0.0335(3) 0.0179(3) 0.0321(3) -0.0013(2) 0.0074(2) 0.0015(2) C109 0.051(13) 0.028(9) 0.031(8) 0.011(6) 0.025(9) 0.014(9) C110 0.056(10) 0.046(10) 0.038(8) -0.015(8) 0.000(7) -0.016(9) C111 0.020(7) 0.062(14) 0.022(7) 0.019(8) 0.001(6) 0.019(9) C112 0.032(7) 0.044(9) 0.035(7) 0.008(6) 0.003(5) 0.008(6) C117 0.0683(11) 0.0630(11) 0.0632(11) 0.0081(7) 0.0057(7) 0.0145(7) C118 0.0730(13) 0.0689(12) 0.0685(13) 0.0081(8) 0.0047(8) 0.0151(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C55 1.312(5) . ? O1 B1 1.524(6) . ? O2 C68 1.314(5) . ? O2 B1 1.540(6) . ? C55 C61 1.392(6) . ? C55 C63 1.425(6) . ? N2 C88 1.351(7) . ? N2 C70 1.379(7) . ? N2 H1 0.8800 . ? C57 C63 1.409(6) . ? C57 C60 1.412(6) . ? C57 C72 1.499(6) . ? N3 C67 1.348(6) . ? N3 C63 1.389(6) . ? N3 H2 0.8800 . ? C59 C64 1.388(7) . ? C59 C93 1.398(7) . ? C59 B1 1.622(7) . ? C60 C67 1.383(7) . ? C60 C80 1.497(6) . ? C61 C68 1.383(6) . ? C61 H3 0.9500 . ? N1 C76 1.519(6) . ? N1 C74 1.520(6) . ? N1 C83 1.521(6) . ? N1 C87 1.527(6) . ? C64 C69 1.395(7) . ? C64 H4 0.9500 . ? C65 C89 1.386(7) . ? C65 C71 1.403(7) . ? C65 B1 1.600(7) . ? C66 C78 1.375(7) . ? C66 C93 1.384(7) . ? C66 H5 0.9500 . ? C67 H6 0.9500 . ? C68 C70 1.443(6) . ? C69 C78 1.384(7) . ? C69 H7 0.9500 . ? C70 C106 1.392(7) . ? C71 C73 1.386(7) . ? C71 H8 0.9500 . ? C72 C79 1.536(7) . ? C72 H28 0.9900 . ? C72 H29 0.9900 . ? C73 C81 1.367(8) . ? C73 H9 0.9500 . ? C74 C82 1.517(6) . ? C74 H34 0.9900 . ? C74 H35 0.9900 . ? C76 C90 1.513(7) . ? C76 H36 0.9900 . ? C76 H37 0.9900 . ? C77 C96 1.514(7) . ? C77 C82 1.531(6) . ? C77 H38 0.9900 . ? C77 H39 0.9900 . ? C78 H10 0.9500 . ? C79 H11 0.9800 . ? C79 H12 0.9800 . ? C79 H13 0.9800 . ? C80 C91 1.520(7) . ? C80 H30 0.9900 . ? C80 H31 0.9900 . ? C81 C86 1.380(8) . ? C81 H14 0.9500 . ? C82 H40 0.9900 . ? C82 H41 0.9900 . ? C83 C95 1.516(7) . ? C83 H42 0.9900 . ? C83 H43 0.9900 . ? C84 C97 1.512(9) . ? C84 C95 1.532(7) . ? C84 H44 0.9900 . ? C84 H45 0.9900 . ? C85 C87 1.524(7) . ? C85 C94 1.520(8) . ? C85 H46 0.9900 . ? C85 H47 0.9900 . ? C86 C89 1.385(7) . ? C86 H15 0.9500 . ? C87 H48 0.9900 . ? C87 H49 0.9900 . ? C88 C116 1.363(9) . ? C88 H16 0.9500 . ? C89 H17 0.9500 . ? C90 C92 1.515(7) . ? C90 H50 0.9900 . ? C90 H51 0.9900 . ? C91 H18 0.9800 . ? C91 H19 0.9800 . ? C91 H20 0.9800 . ? C92 C101 1.531(7) . ? C92 H52 0.9900 . ? C92 H53 0.9900 . ? C93 H21 0.9500 . ? C94 C102 1.513(8) . ? C94 H54 0.9900 . ? C94 H55 0.9900 . ? C95 H56 0.9900 . ? C95 H57 0.9900 . ? C96 H58 0.9800 . ? C96 H59 0.9800 . ? C96 H60 0.9800 . ? C97 H61 0.9800 . ? C97 H62 0.9800 . ? C97 H63 0.9800 . ? C101 H64 0.9800 . ? C101 H65 0.9800 . ? C101 H66 0.9800 . ? C102 H67 0.9800 . ? C102 H68 0.9800 . ? C102 H69 0.9800 . ? C116 C106 1.381(9) . ? C116 C117 1.550(5) . ? C106 C111 1.54(2) . ? C106 C109 1.57(2) . ? C109 C110 1.48(2) . ? C109 H70 0.9900 . ? C109 H71 0.9900 . ? C110 H72 0.9800 . ? C110 H73 0.9800 . ? C110 H74 0.9800 . ? C111 C112 1.52(2) . ? C111 H75 0.9900 . ? C111 H76 0.9900 . ? C112 H77 0.9800 . ? C112 H78 0.9800 . ? C112 H79 0.9800 . ? C117 C118 1.549(5) . ? C117 H80 0.9900 . ? C117 H81 0.9900 . ? C118 H82 0.9800 . ? C118 H83 0.9800 . ? C118 H84 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C55 O1 B1 118.7(3) . . ? C68 O2 B1 117.8(3) . . ? O1 C55 C61 120.8(4) . . ? O1 C55 C63 116.8(4) . . ? C61 C55 C63 122.5(4) . . ? C88 N2 C70 109.0(5) . . ? C88 N2 H1 125.5 . . ? C70 N2 H1 125.5 . . ? C63 C57 C60 107.4(4) . . ? C63 C57 C72 126.5(4) . . ? C60 C57 C72 126.1(4) . . ? C67 N3 C63 108.9(4) . . ? C67 N3 H2 125.5 . . ? C63 N3 H2 125.5 . . ? C64 C59 C93 116.2(4) . . ? C64 C59 B1 124.5(4) . . ? C93 C59 B1 119.3(4) . . ? C67 C60 C57 106.5(4) . . ? C67 C60 C80 125.6(4) . . ? C57 C60 C80 127.8(4) . . ? C68 C61 C55 120.6(4) . . ? C68 C61 H3 119.7 . . ? C55 C61 H3 119.7 . . ? C76 N1 C74 110.6(3) . . ? C76 N1 C83 110.9(4) . . ? C74 N1 C83 106.6(3) . . ? C76 N1 C87 107.0(3) . . ? C74 N1 C87 111.1(4) . . ? C83 N1 C87 110.8(4) . . ? N3 C63 C57 107.0(4) . . ? N3 C63 C55 121.5(4) . . ? C57 C63 C55 131.1(4) . . ? C69 C64 C59 122.3(4) . . ? C69 C64 H4 118.9 . . ? C59 C64 H4 118.9 . . ? C89 C65 C71 116.3(4) . . ? C89 C65 B1 122.3(4) . . ? C71 C65 B1 121.4(4) . . ? C78 C66 C93 120.0(5) . . ? C78 C66 H5 120.0 . . ? C93 C66 H5 120.0 . . ? N3 C67 C60 110.1(4) . . ? N3 C67 H6 125.0 . . ? C60 C67 H6 125.0 . . ? O2 C68 C61 121.3(4) . . ? O2 C68 C70 116.8(4) . . ? C61 C68 C70 121.9(4) . . ? C64 C69 C78 119.6(5) . . ? C64 C69 H7 120.2 . . ? C78 C69 H7 120.2 . . ? N2 C70 C106 107.2(4) . . ? N2 C70 C68 120.8(4) . . ? C106 C70 C68 131.6(4) . . ? C73 C71 C65 121.6(5) . . ? C73 C71 H8 119.2 . . ? C65 C71 H8 119.2 . . ? C57 C72 C79 111.3(4) . . ? C57 C72 H28 109.4 . . ? C79 C72 H28 109.4 . . ? C57 C72 H29 109.4 . . ? C79 C72 H29 109.4 . . ? H28 C72 H29 108.0 . . ? C81 C73 C71 120.5(5) . . ? C81 C73 H9 119.8 . . ? C71 C73 H9 119.8 . . ? C82 C74 N1 116.0(4) . . ? C82 C74 H34 108.3 . . ? N1 C74 H34 108.3 . . ? C82 C74 H35 108.3 . . ? N1 C74 H35 108.3 . . ? H34 C74 H35 107.4 . . ? O1 B1 O2 108.1(3) . . ? O1 B1 C65 108.9(4) . . ? O2 B1 C65 108.1(4) . . ? O1 B1 C59 109.0(4) . . ? O2 B1 C59 107.7(4) . . ? C65 B1 C59 114.9(4) . . ? C90 C76 N1 116.6(4) . . ? C90 C76 H36 108.1 . . ? N1 C76 H36 108.1 . . ? C90 C76 H37 108.1 . . ? N1 C76 H37 108.1 . . ? H36 C76 H37 107.3 . . ? C96 C77 C82 112.7(4) . . ? C96 C77 H38 109.1 . . ? C82 C77 H38 109.1 . . ? C96 C77 H39 109.1 . . ? C82 C77 H39 109.1 . . ? H38 C77 H39 107.8 . . ? C66 C78 C69 119.6(4) . . ? C66 C78 H10 120.2 . . ? C69 C78 H10 120.2 . . ? C72 C79 H11 109.5 . . ? C72 C79 H12 109.5 . . ? H11 C79 H12 109.5 . . ? C72 C79 H13 109.5 . . ? H11 C79 H13 109.5 . . ? H12 C79 H13 109.5 . . ? C60 C80 C91 114.2(4) . . ? C60 C80 H30 108.7 . . ? C91 C80 H30 108.7 . . ? C60 C80 H31 108.7 . . ? C91 C80 H31 108.7 . . ? H30 C80 H31 107.6 . . ? C73 C81 C86 119.2(5) . . ? C73 C81 H14 120.4 . . ? C86 C81 H14 120.4 . . ? C74 C82 C77 109.6(4) . . ? C74 C82 H40 109.8 . . ? C77 C82 H40 109.8 . . ? C74 C82 H41 109.8 . . ? C77 C82 H41 109.8 . . ? H40 C82 H41 108.2 . . ? C95 C83 N1 114.7(4) . . ? C95 C83 H42 108.6 . . ? N1 C83 H42 108.6 . . ? C95 C83 H43 108.6 . . ? N1 C83 H43 108.6 . . ? H42 C83 H43 107.6 . . ? C97 C84 C95 113.0(5) . . ? C97 C84 H44 109.0 . . ? C95 C84 H44 109.0 . . ? C97 C84 H45 109.0 . . ? C95 C84 H45 109.0 . . ? H44 C84 H45 107.8 . . ? C87 C85 C94 111.6(4) . . ? C87 C85 H46 109.3 . . ? C94 C85 H46 109.3 . . ? C87 C85 H47 109.3 . . ? C94 C85 H47 109.3 . . ? H46 C85 H47 108.0 . . ? C81 C86 C89 120.2(5) . . ? C81 C86 H15 119.9 . . ? C89 C86 H15 119.9 . . ? C85 C87 N1 115.0(4) . . ? C85 C87 H48 108.5 . . ? N1 C87 H48 108.5 . . ? C85 C87 H49 108.5 . . ? N1 C87 H49 108.5 . . ? H48 C87 H49 107.5 . . ? N2 C88 C116 108.0(5) . . ? N2 C88 H16 126.0 . . ? C116 C88 H16 126.0 . . ? C65 C89 C86 122.1(5) . . ? C65 C89 H17 119.0 . . ? C86 C89 H17 119.0 . . ? C92 C90 C76 110.2(4) . . ? C92 C90 H50 109.6 . . ? C76 C90 H50 109.6 . . ? C92 C90 H51 109.6 . . ? C76 C90 H51 109.6 . . ? H50 C90 H51 108.1 . . ? C80 C91 H18 109.5 . . ? C80 C91 H19 109.5 . . ? H18 C91 H19 109.5 . . ? C80 C91 H20 109.5 . . ? H18 C91 H20 109.5 . . ? H19 C91 H20 109.5 . . ? C90 C92 C101 113.0(4) . . ? C90 C92 H52 109.0 . . ? C101 C92 H52 109.0 . . ? C90 C92 H53 109.0 . . ? C101 C92 H53 109.0 . . ? H52 C92 H53 107.8 . . ? C66 C93 C59 122.3(5) . . ? C66 C93 H21 118.9 . . ? C59 C93 H21 118.9 . . ? C102 C94 C85 114.4(5) . . ? C102 C94 H54 108.7 . . ? C85 C94 H54 108.7 . . ? C102 C94 H55 108.7 . . ? C85 C94 H55 108.7 . . ? H54 C94 H55 107.6 . . ? C83 C95 C84 111.4(4) . . ? C83 C95 H56 109.3 . . ? C84 C95 H56 109.3 . . ? C83 C95 H57 109.3 . . ? C84 C95 H57 109.3 . . ? H56 C95 H57 108.0 . . ? C77 C96 H58 109.5 . . ? C77 C96 H59 109.5 . . ? H58 C96 H59 109.5 . . ? C77 C96 H60 109.5 . . ? H58 C96 H60 109.5 . . ? H59 C96 H60 109.5 . . ? C84 C97 H61 109.5 . . ? C84 C97 H62 109.5 . . ? H61 C97 H62 109.5 . . ? C84 C97 H63 109.5 . . ? H61 C97 H63 109.5 . . ? H62 C97 H63 109.5 . . ? C92 C101 H64 109.5 . . ? C92 C101 H65 109.5 . . ? H64 C101 H65 109.5 . . ? C92 C101 H66 109.5 . . ? H64 C101 H66 109.5 . . ? H65 C101 H66 109.5 . . ? C94 C102 H67 109.5 . . ? C94 C102 H68 109.5 . . ? H67 C102 H68 109.5 . . ? C94 C102 H69 109.5 . . ? H67 C102 H69 109.5 . . ? H68 C102 H69 109.5 . . ? C88 C116 C106 109.0(5) . . ? C88 C116 C117 123.7(6) . . ? C106 C116 C117 126.4(6) . . ? C70 C106 C116 106.6(5) . . ? C70 C106 C111 124.6(6) . . ? C116 C106 C111 125.7(6) . . ? C70 C106 C109 123.8(7) . . ? C116 C106 C109 126.3(7) . . ? C111 C106 C109 31.8(7) . . ? C110 C109 C106 107(2) . . ? C110 C109 H70 110.3 . . ? C106 C109 H70 110.3 . . ? C110 C109 H71 110.3 . . ? C106 C109 H71 110.3 . . ? H70 C109 H71 108.5 . . ? C109 C110 H72 109.5 . . ? C109 C110 H73 109.5 . . ? H72 C110 H73 109.5 . . ? C109 C110 H74 109.5 . . ? H72 C110 H74 109.5 . . ? H73 C110 H74 109.5 . . ? C112 C111 C106 98.4(14) . . ? C112 C111 H75 112.1 . . ? C106 C111 H75 112.1 . . ? C112 C111 H76 112.1 . . ? C106 C111 H76 112.1 . . ? H75 C111 H76 109.7 . . ? C118 C117 C116 118.5(6) . . ? C118 C117 H80 107.7 . . ? C116 C117 H80 107.7 . . ? C118 C117 H81 107.7 . . ? C116 C117 H81 107.7 . . ? H80 C117 H81 107.1 . . ? C117 C118 H82 109.5 . . ? C117 C118 H83 109.5 . . ? H82 C118 H83 109.5 . . ? C117 C118 H84 109.5 . . ? H82 C118 H84 109.5 . . ? H83 C118 H84 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag B1 O1 C55 C61 -17.1(6) . . . . ? B1 O1 C55 C63 163.3(4) . . . . ? C63 C57 C60 C67 -1.2(5) . . . . ? C72 C57 C60 C67 177.1(4) . . . . ? C63 C57 C60 C80 177.7(4) . . . . ? C72 C57 C60 C80 -4.0(7) . . . . ? O1 C55 C61 C68 -7.2(6) . . . . ? C63 C55 C61 C68 172.3(4) . . . . ? C67 N3 C63 C57 0.6(5) . . . . ? C67 N3 C63 C55 174.1(4) . . . . ? C60 C57 C63 N3 0.4(5) . . . . ? C72 C57 C63 N3 -177.9(4) . . . . ? C60 C57 C63 C55 -172.2(4) . . . . ? C72 C57 C63 C55 9.5(7) . . . . ? O1 C55 C63 N3 169.0(4) . . . . ? C61 C55 C63 N3 -10.5(6) . . . . ? O1 C55 C63 C57 -19.3(7) . . . . ? C61 C55 C63 C57 161.2(4) . . . . ? C93 C59 C64 C69 -0.3(7) . . . . ? B1 C59 C64 C69 178.5(4) . . . . ? C63 N3 C67 C60 -1.3(5) . . . . ? C57 C60 C67 N3 1.6(5) . . . . ? C80 C60 C67 N3 -177.3(4) . . . . ? B1 O2 C68 C61 18.0(6) . . . . ? B1 O2 C68 C70 -162.3(4) . . . . ? C55 C61 C68 O2 6.5(6) . . . . ? C55 C61 C68 C70 -173.1(4) . . . . ? C59 C64 C69 C78 -0.4(7) . . . . ? C88 N2 C70 C106 -0.7(7) . . . . ? C88 N2 C70 C68 -174.6(5) . . . . ? O2 C68 C70 N2 -173.1(4) . . . . ? C61 C68 C70 N2 6.5(7) . . . . ? O2 C68 C70 C106 14.7(9) . . . . ? C61 C68 C70 C106 -165.7(7) . . . . ? C89 C65 C71 C73 0.7(7) . . . . ? B1 C65 C71 C73 178.9(4) . . . . ? C63 C57 C72 C79 80.1(5) . . . . ? C60 C57 C72 C79 -97.8(5) . . . . ? C65 C71 C73 C81 -0.9(7) . . . . ? C76 N1 C74 C82 61.2(5) . . . . ? C83 N1 C74 C82 -178.3(4) . . . . ? C87 N1 C74 C82 -57.5(5) . . . . ? C55 O1 B1 O2 37.4(5) . . . . ? C55 O1 B1 C65 154.6(4) . . . . ? C55 O1 B1 C59 -79.4(4) . . . . ? C68 O2 B1 O1 -37.8(5) . . . . ? C68 O2 B1 C65 -155.5(4) . . . . ? C68 O2 B1 C59 79.8(4) . . . . ? C89 C65 B1 O1 -153.3(4) . . . . ? C71 C65 B1 O1 28.5(6) . . . . ? C89 C65 B1 O2 -36.1(6) . . . . ? C71 C65 B1 O2 145.8(4) . . . . ? C89 C65 B1 C59 84.1(5) . . . . ? C71 C65 B1 C59 -94.0(5) . . . . ? C64 C59 B1 O1 4.5(6) . . . . ? C93 C59 B1 O1 -176.6(4) . . . . ? C64 C59 B1 O2 -112.5(5) . . . . ? C93 C59 B1 O2 66.3(5) . . . . ? C64 C59 B1 C65 127.0(5) . . . . ? C93 C59 B1 C65 -54.1(6) . . . . ? C74 N1 C76 C90 62.7(5) . . . . ? C83 N1 C76 C90 -55.3(5) . . . . ? C87 N1 C76 C90 -176.2(4) . . . . ? C93 C66 C78 C69 -0.4(8) . . . . ? C64 C69 C78 C66 0.8(7) . . . . ? C67 C60 C80 C91 -112.7(5) . . . . ? C57 C60 C80 C91 68.7(6) . . . . ? C71 C73 C81 C86 0.1(7) . . . . ? N1 C74 C82 C77 -177.3(4) . . . . ? C96 C77 C82 C74 178.5(4) . . . . ? C76 N1 C83 C95 -60.2(5) . . . . ? C74 N1 C83 C95 179.5(4) . . . . ? C87 N1 C83 C95 58.4(5) . . . . ? C73 C81 C86 C89 0.9(8) . . . . ? C94 C85 C87 N1 170.7(4) . . . . ? C76 N1 C87 C85 175.1(4) . . . . ? C74 N1 C87 C85 -64.2(5) . . . . ? C83 N1 C87 C85 54.1(5) . . . . ? C70 N2 C88 C116 -2.0(7) . . . . ? C71 C65 C89 C86 0.3(7) . . . . ? B1 C65 C89 C86 -177.9(5) . . . . ? C81 C86 C89 C65 -1.1(8) . . . . ? N1 C76 C90 C92 178.2(4) . . . . ? C76 C90 C92 C101 -176.5(4) . . . . ? C78 C66 C93 C59 -0.5(8) . . . . ? C64 C59 C93 C66 0.8(7) . . . . ? B1 C59 C93 C66 -178.1(4) . . . . ? C87 C85 C94 C102 62.8(6) . . . . ? N1 C83 C95 C84 177.1(4) . . . . ? C97 C84 C95 C83 68.4(7) . . . . ? N2 C88 C116 C106 4.0(8) . . . . ? N2 C88 C116 C117 173.7(6) . . . . ? N2 C70 C106 C116 3.1(8) . . . . ? C68 C70 C106 C116 176.1(6) . . . . ? N2 C70 C106 C111 -157.8(9) . . . . ? C68 C70 C106 C111 15.2(14) . . . . ? N2 C70 C106 C109 163.5(12) . . . . ? C68 C70 C106 C109 -23.5(16) . . . . ? C88 C116 C106 C70 -4.4(9) . . . . ? C117 C116 C106 C70 -173.7(6) . . . . ? C88 C116 C106 C111 156.2(9) . . . . ? C117 C116 C106 C111 -13.1(14) . . . . ? C88 C116 C106 C109 -164.1(13) . . . . ? C117 C116 C106 C109 26.5(16) . . . . ? C70 C106 C109 C110 97.4(13) . . . . ? C116 C106 C109 C110 -106.1(12) . . . . ? C111 C106 C109 C110 -5.0(10) . . . . ? C70 C106 C111 C112 -101.7(11) . . . . ? C116 C106 C111 C112 101.1(11) . . . . ? C109 C106 C111 C112 -1.8(11) . . . . ? C88 C116 C117 C118 -85.3(9) . . . . ? C106 C116 C117 C118 82.6(10) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 23.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.559 _refine_diff_density_min -2.507 _refine_diff_density_rms 0.098 #============================================================================== # End of CIF #============================================================================== data_90916mae _database_code_depnum_ccdc_archive 'CCDC 759626' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C51 H63 B Br N3 O2' _chemical_formula_weight 840.76 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' Br Br -0.2901 2.4595 '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 21/c' _symmetry_space_group_name_Hall '-P 2yc' _symmetry_Int_Tables_number 14 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 13.723(3) _cell_length_b 14.488(2) _cell_length_c 23.592(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.643(8) _cell_angle_gamma 90.00 _cell_volume 4558.3(16) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1784 _exptl_absorpt_coefficient_mu 0.944 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.6497 _exptl_absorpt_correction_T_max 0.8337 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _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 \w _diffrn_detector_area_resol_mean 10 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38565 _diffrn_reflns_av_R_equivalents 0.0544 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 26.00 _reflns_number_total 8931 _reflns_number_gt 6614 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^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 ? _refine_ls_number_reflns 8931 _refine_ls_number_parameters 551 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.1549 _refine_ls_R_factor_gt 0.1291 _refine_ls_wR_factor_ref 0.4262 _refine_ls_wR_factor_gt 0.3975 _refine_ls_goodness_of_fit_ref 1.795 _refine_ls_restrained_S_all 1.796 _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 O1 O 0.1575(3) 0.1521(2) -0.00162(15) 0.0092(7) Uani 1 1 d . . . O2 O 0.3219(3) 0.2242(2) 0.00515(15) 0.0107(8) Uani 1 1 d . . . N1 N 0.3135(3) 0.4086(3) -0.09925(19) 0.0122(9) Uani 1 1 d . . . H1 H 0.2515 0.4153 -0.1199 0.015 Uiso 1 1 calc R . . C5 C 0.2821(4) 0.2739(3) -0.0411(2) 0.0107(10) Uani 1 1 d . . . C6 C -0.1359(4) 0.2694(4) -0.1102(2) 0.0136(11) Uani 1 1 d . . . N3 N 0.0836(4) 0.2664(3) 0.15131(19) 0.0147(10) Uani 1 1 d . A . N2 N -0.0355(3) 0.2787(3) -0.10351(19) 0.0108(9) Uani 1 1 d . . . H2 H -0.0061 0.3189 -0.1220 0.013 Uiso 1 1 calc R . . C9 C 0.3087(4) 0.0989(3) 0.0763(2) 0.0103(10) Uani 1 1 d . . . C10 C 0.0141(4) 0.2140(3) -0.0624(2) 0.0101(10) Uani 1 1 d . . . C11 C -0.0603(4) 0.1641(4) -0.0442(2) 0.0141(11) Uani 1 1 d . . . H3 H -0.0497 0.1148 -0.0169 0.017 Uiso 1 1 calc R . . C12 C 0.1822(4) 0.2614(4) -0.0711(2) 0.0119(10) Uani 1 1 d . . . H4 H 0.1570 0.2891 -0.1082 0.014 Uiso 1 1 calc R . . C13 C 0.1205(4) 0.2074(3) -0.0454(2) 0.0092(10) Uani 1 1 d . . . C14 C 0.2959(4) 0.0622(4) -0.0365(2) 0.0119(11) Uani 1 1 d . . . C15 C 0.3927(4) 0.4618(4) -0.1039(2) 0.0129(11) Uani 1 1 d . . . C16 C -0.2084(4) 0.3274(4) -0.1512(2) 0.0163(12) Uani 1 1 d . . . C17 C 0.2870(5) 0.6320(4) -0.2240(3) 0.0229(13) Uani 1 1 d . . . H5 H 0.2249 0.6465 -0.2501 0.027 Uiso 1 1 calc R . . C18 C -0.1529(4) 0.2000(4) -0.0734(2) 0.0145(11) Uani 1 1 d . . . H6 H -0.2166 0.1801 -0.0689 0.017 Uiso 1 1 calc R . . C19 C 0.3778(4) 0.1478(4) 0.1182(2) 0.0154(11) Uani 1 1 d . . . H7 H 0.4012 0.2059 0.1082 0.018 Uiso 1 1 calc R . . C20 C -0.1807(4) 0.3709(4) -0.1979(3) 0.0185(12) Uani 1 1 d . . . H8 H -0.1155 0.3617 -0.2041 0.022 Uiso 1 1 calc R . . C21 C 0.3461(4) 0.3418(4) -0.0567(2) 0.0144(11) Uani 1 1 d . . . C22 C 0.4776(5) 0.4291(4) -0.0648(3) 0.0192(12) Uani 1 1 d . . . H9 H 0.5437 0.4527 -0.0595 0.023 Uiso 1 1 calc R . . C23 C -0.2493(5) 0.4281(4) -0.2357(3) 0.0233(13) Uani 1 1 d . . . H10 H -0.2301 0.4582 -0.2671 0.028 Uiso 1 1 calc R . . C24 C 0.3834(4) 0.0283(4) 0.1900(2) 0.0149(11) Uani 1 1 d . . . H11 H 0.4090 0.0043 0.2281 0.018 Uiso 1 1 calc R . . B1 B 0.2710(4) 0.1330(4) 0.0108(2) 0.0102(11) Uani 1 1 d . . . C26 C 0.3837(4) 0.5377(4) -0.1460(2) 0.0146(11) Uani 1 1 d . . . C27 C 0.3557(5) -0.0715(5) -0.1086(3) 0.0284(15) Uani 1 1 d . . . H12 H 0.3761 -0.1169 -0.1325 0.034 Uiso 1 1 calc R . . C58 C -0.0937(5) 0.2875(4) 0.0837(3) 0.0233(13) Uani 1 1 d . . . H27 H -0.0662 0.3178 0.0532 0.028 Uiso 1 1 calc R . . H28 H -0.1015 0.2208 0.0747 0.028 Uiso 1 1 calc R . . C59 C 0.0858(5) 0.1623(4) 0.1409(3) 0.0176(12) Uani 1 1 d . . . H29 H 0.0561 0.1505 0.0990 0.021 Uiso 1 1 calc R . . H30 H 0.1567 0.1423 0.1490 0.021 Uiso 1 1 calc R . . C60 C -0.0234(4) 0.3021(4) 0.1437(2) 0.0170(11) Uani 1 1 d . . . H31 H -0.0202 0.3690 0.1523 0.020 Uiso 1 1 calc R . . H32 H -0.0533 0.2717 0.1731 0.020 Uiso 1 1 calc R . . C31 C -0.3439(5) 0.4404(4) -0.2273(3) 0.0230(13) Uani 1 1 d . . . H13 H -0.3897 0.4798 -0.2527 0.028 Uiso 1 1 calc R . . C61 C 0.2895(5) 0.2991(5) 0.2941(3) 0.0257(14) Uani 1 1 d . . . H33 H 0.2496 0.2744 0.3206 0.031 Uiso 1 1 calc R . . H34 H 0.2838 0.3672 0.2940 0.031 Uiso 1 1 calc R . . C33 C -0.3050(4) 0.3394(4) -0.1433(2) 0.0182(12) Uani 1 1 d D . . H14 H -0.3251 0.3096 -0.1120 0.022 Uiso 1 1 calc R . . C34 C 0.2939(5) 0.5574(4) -0.1860(2) 0.0192(12) Uani 1 1 d . . . H15 H 0.2368 0.5196 -0.1874 0.023 Uiso 1 1 calc R . . C35 C 0.4139(4) 0.1136(4) 0.1750(2) 0.0166(12) Uani 1 1 d . . . H16 H 0.4594 0.1494 0.2031 0.020 Uiso 1 1 calc R . . C36 C -0.3731(4) 0.3966(4) -0.1826(3) 0.0244(14) Uani 1 1 d DU . . H17 H -0.4394 0.4046 -0.1778 0.029 Uiso 1 1 calc R . . C37 C 0.3915(5) 0.0615(4) -0.0478(3) 0.0204(13) Uani 1 1 d . . . H18 H 0.4383 0.1073 -0.0301 0.025 Uiso 1 1 calc R . . C62 C 0.1344(5) 0.3098(4) 0.1070(3) 0.0205(13) Uani 1 1 d . . . H71 H 0.1058 0.2827 0.0681 0.025 Uiso 0.47(3) 1 calc PR A 1 H72 H 0.2068 0.2947 0.1178 0.025 Uiso 0.47(3) 1 calc PR A 1 H73 H 0.1944 0.2726 0.1058 0.025 Uiso 0.53(3) 1 calc PR A 2 H74 H 0.0879 0.3055 0.0680 0.025 Uiso 0.53(3) 1 calc PR A 2 C39 C 0.2797(5) 0.0134(4) 0.0927(2) 0.0263(15) Uani 1 1 d . . . H19 H 0.2342 -0.0226 0.0648 0.032 Uiso 1 1 calc R . . C63 C -0.1944(5) 0.3297(5) 0.0854(3) 0.0267(14) Uani 1 1 d . . . H37 H -0.2206 0.2985 0.1161 0.032 Uiso 1 1 calc R . . H38 H -0.1844 0.3957 0.0962 0.032 Uiso 1 1 calc R . . C41 C 0.4207(5) -0.0035(5) -0.0838(3) 0.0259(14) Uani 1 1 d . . . H20 H 0.4859 -0.0007 -0.0910 0.031 Uiso 1 1 calc R . . C42 C 0.4480(4) 0.3550(4) -0.0346(3) 0.0205(12) Uani 1 1 d . . . H70 H 0.4901 0.3202 -0.0044 0.025 Uiso 1 1 calc R . . C64 C 0.1371(4) 0.2915(4) 0.2138(2) 0.0200(12) Uani 1 1 d . . . H39 H 0.1003 0.2628 0.2406 0.024 Uiso 1 1 calc R A . H40 H 0.1331 0.3593 0.2183 0.024 Uiso 1 1 calc R . . C65 C 0.0480(6) 0.0018(4) 0.1628(3) 0.0313(15) Uani 1 1 d . . . H41 H 0.1204 -0.0126 0.1757 0.038 Uiso 1 1 calc R . . H42 H 0.0278 -0.0075 0.1201 0.038 Uiso 1 1 calc R . . C45 C 0.3151(5) -0.0221(5) 0.1491(3) 0.0297(16) Uani 1 1 d . . . H21 H 0.2923 -0.0803 0.1592 0.036 Uiso 1 1 calc R . . C46 C -0.2716(5) 0.3223(6) 0.0279(3) 0.0353(16) Uani 1 1 d . . . H43 H -0.2407 0.3392 -0.0041 0.053 Uiso 1 1 calc R . . H44 H -0.3276 0.3641 0.0282 0.053 Uiso 1 1 calc R . . H45 H -0.2964 0.2587 0.0224 0.053 Uiso 1 1 calc R . . C66 C 0.2472(5) 0.2628(5) 0.2330(3) 0.0306(15) Uani 1 1 d . A . H46 H 0.2528 0.1947 0.2325 0.037 Uiso 1 1 calc R . . H47 H 0.2853 0.2886 0.2058 0.037 Uiso 1 1 calc R . . C67 C 0.0316(5) 0.1022(4) 0.1764(3) 0.0239(13) Uiso 1 1 d . . . H48 H 0.0581 0.1142 0.2185 0.029 Uiso 1 1 calc R . . H49 H -0.0410 0.1166 0.1663 0.029 Uiso 1 1 calc R . . C49 C 0.3727(7) 0.6857(4) -0.2236(3) 0.0348(18) Uani 1 1 d . . . H22 H 0.3682 0.7374 -0.2488 0.042 Uiso 1 1 calc R . . C50 C 0.2305(5) -0.0071(4) -0.0634(3) 0.0235(13) Uani 1 1 d . . . H23 H 0.1645 -0.0086 -0.0573 0.028 Uiso 1 1 calc R . . C51 C 0.2589(6) -0.0743(5) -0.0990(3) 0.0344(16) Uani 1 1 d . . . H24 H 0.2131 -0.1212 -0.1163 0.041 Uiso 1 1 calc R . . C52 C 0.4697(6) 0.5902(5) -0.1465(3) 0.0355(18) Uani 1 1 d . . . H25 H 0.5317 0.5765 -0.1201 0.043 Uiso 1 1 calc R . . C53 C 0.4000(5) 0.2717(6) 0.3172(3) 0.0384(18) Uani 1 1 d . . . H50 H 0.4046 0.2050 0.3241 0.058 Uiso 1 1 calc R . . H51 H 0.4277 0.3044 0.3538 0.058 Uiso 1 1 calc R . . H52 H 0.4381 0.2883 0.2884 0.058 Uiso 1 1 calc R . . C54 C 0.4631(7) 0.6631(5) -0.1865(3) 0.043(2) Uani 1 1 d . . . H26 H 0.5216 0.6972 -0.1880 0.051 Uiso 1 1 calc R . . C55 C -0.0114(7) -0.0660(5) 0.1926(3) 0.0383(18) Uani 1 1 d . . . H53 H 0.0085 -0.0575 0.2350 0.058 Uiso 1 1 calc R . . H54 H 0.0031 -0.1296 0.1829 0.058 Uiso 1 1 calc R . . H55 H -0.0834 -0.0540 0.1787 0.058 Uiso 1 1 calc R . . C68 C 0.1663(18) 0.4089(10) 0.1175(7) 0.018(4) Uani 0.53(3) 1 d P A 2 H75 H 0.2200 0.4140 0.1537 0.021 Uiso 0.53(3) 1 calc PR A 2 H76 H 0.1088 0.4470 0.1220 0.021 Uiso 0.53(3) 1 calc PR A 2 C69 C 0.2046(17) 0.4425(10) 0.0657(7) 0.019(4) Uani 0.53(3) 1 d P A 2 H60 H 0.2484 0.3946 0.0549 0.023 Uiso 0.57 1 calc PR A 2 H61 H 0.2455 0.4988 0.0771 0.023 Uiso 0.57 1 calc PR A 2 C70 C 0.1182(15) 0.4646(9) 0.0118(8) 0.040(5) Uani 0.53(3) 1 d P A 2 H62 H 0.0675 0.4158 0.0068 0.060 Uiso 0.57 1 calc PR A 2 H63 H 0.1451 0.4680 -0.0231 0.060 Uiso 0.57 1 calc PR A 2 H64 H 0.0877 0.5239 0.0177 0.060 Uiso 0.57 1 calc PR A 2 C71 C 0.266(2) 0.4412(10) 0.0578(7) 0.033(6) Uani 0.47(3) 1 d P A 1 H65 H 0.3028 0.4544 0.0979 0.049 Uiso 0.43 1 calc PR A 1 H66 H 0.2900 0.4821 0.0309 0.049 Uiso 0.43 1 calc PR A 1 H67 H 0.2774 0.3768 0.0483 0.049 Uiso 0.43 1 calc PR A 1 C72 C 0.157(2) 0.4567(12) 0.0522(9) 0.026(6) Uani 0.47(3) 1 d P A 1 H68 H 0.1193 0.4262 0.0161 0.031 Uiso 0.43 1 calc PR A 1 H69 H 0.1434 0.5237 0.0482 0.031 Uiso 0.43 1 calc PR A 1 Br1 Br 0.07327(8) 0.44180(7) -0.16164(5) 0.0592(4) Uani 1 1 d . . . C73 C 0.121(2) 0.4206(13) 0.1030(11) 0.025(4) Uani 0.47(3) 1 d P A 1 H77 H 0.0498 0.4368 0.0985 0.030 Uiso 0.47(3) 1 calc PR A 1 H78 H 0.1602 0.4492 0.1395 0.030 Uiso 0.47(3) 1 calc PR A 1 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 O1 0.0037(18) 0.0143(17) 0.0083(16) 0.0038(13) -0.0010(13) 0.0024(13) O2 0.0074(18) 0.0144(17) 0.0081(17) 0.0060(14) -0.0022(14) -0.0005(13) N1 0.012(2) 0.015(2) 0.010(2) 0.0059(17) 0.0035(17) 0.0040(17) C5 0.010(3) 0.012(2) 0.008(2) 0.0025(19) -0.0002(19) 0.0031(19) C6 0.008(3) 0.019(3) 0.012(2) -0.009(2) -0.002(2) 0.002(2) N3 0.019(3) 0.017(2) 0.009(2) -0.0036(17) 0.0053(18) -0.0006(18) N2 0.005(2) 0.016(2) 0.010(2) -0.0029(17) -0.0017(16) 0.0036(16) C9 0.006(2) 0.016(2) 0.009(2) 0.000(2) 0.0012(19) -0.0014(19) C10 0.006(2) 0.016(2) 0.007(2) -0.0015(19) 0.0001(19) -0.0012(19) C11 0.012(3) 0.015(2) 0.015(2) -0.004(2) 0.001(2) -0.002(2) C12 0.008(3) 0.017(2) 0.009(2) 0.005(2) -0.0006(19) 0.0022(19) C13 0.009(3) 0.012(2) 0.006(2) -0.0037(18) 0.0006(19) 0.0014(19) C14 0.007(3) 0.022(3) 0.006(2) 0.0060(19) 0.0003(19) 0.0031(19) C15 0.017(3) 0.014(2) 0.007(2) -0.001(2) 0.001(2) 0.000(2) C16 0.008(3) 0.018(3) 0.018(3) -0.011(2) -0.008(2) 0.002(2) C17 0.036(4) 0.018(3) 0.017(3) 0.006(2) 0.010(3) 0.012(3) C18 0.008(3) 0.017(2) 0.019(3) -0.005(2) 0.002(2) 0.000(2) C19 0.019(3) 0.012(2) 0.011(2) 0.002(2) -0.005(2) -0.001(2) C20 0.006(3) 0.025(3) 0.020(3) 0.000(2) -0.006(2) 0.004(2) C21 0.009(3) 0.022(3) 0.010(2) 0.008(2) -0.001(2) 0.000(2) C22 0.013(3) 0.023(3) 0.021(3) 0.009(2) 0.003(2) -0.005(2) C23 0.017(3) 0.022(3) 0.021(3) 0.000(2) -0.015(2) 0.001(2) C24 0.014(3) 0.022(3) 0.007(2) 0.007(2) -0.002(2) -0.004(2) B1 0.002(3) 0.015(3) 0.012(3) 0.002(2) -0.002(2) -0.001(2) C26 0.025(3) 0.009(2) 0.011(2) -0.001(2) 0.006(2) -0.002(2) C27 0.027(4) 0.033(3) 0.025(3) -0.005(3) 0.006(3) 0.014(3) C58 0.019(3) 0.032(3) 0.017(3) -0.006(2) 0.001(2) 0.007(2) C59 0.023(3) 0.010(2) 0.021(3) -0.005(2) 0.008(2) 0.000(2) C60 0.015(3) 0.022(3) 0.013(3) -0.006(2) 0.001(2) 0.005(2) C31 0.012(3) 0.020(3) 0.028(3) -0.006(2) -0.013(2) 0.004(2) C61 0.020(3) 0.042(4) 0.015(3) 0.000(3) 0.003(2) 0.007(3) C33 0.010(3) 0.023(3) 0.017(3) -0.013(2) -0.005(2) 0.004(2) C34 0.023(3) 0.024(3) 0.014(3) 0.008(2) 0.011(2) 0.007(2) C35 0.019(3) 0.017(3) 0.008(2) 0.000(2) -0.006(2) 0.001(2) C36 0.008(3) 0.028(3) 0.030(3) -0.016(3) -0.009(2) 0.010(2) C37 0.012(3) 0.033(3) 0.018(3) -0.003(2) 0.007(2) 0.000(2) C62 0.028(3) 0.020(3) 0.018(3) -0.005(2) 0.015(3) -0.009(2) C39 0.032(4) 0.028(3) 0.013(3) 0.011(2) -0.008(2) -0.021(3) C63 0.018(3) 0.034(3) 0.026(3) -0.010(3) 0.003(3) 0.001(3) C41 0.012(3) 0.042(4) 0.025(3) -0.001(3) 0.007(2) 0.011(3) C42 0.010(3) 0.030(3) 0.018(3) 0.012(2) -0.002(2) -0.004(2) C64 0.017(3) 0.031(3) 0.011(3) -0.011(2) 0.002(2) 0.002(2) C65 0.046(4) 0.019(3) 0.031(3) 0.001(3) 0.013(3) -0.004(3) C45 0.039(4) 0.031(3) 0.013(3) 0.015(3) -0.006(3) -0.021(3) C46 0.020(4) 0.053(4) 0.029(4) -0.007(3) 0.000(3) 0.002(3) C66 0.018(3) 0.050(4) 0.025(3) -0.012(3) 0.006(3) 0.005(3) C49 0.072(6) 0.015(3) 0.014(3) 0.003(2) 0.002(3) -0.013(3) C50 0.016(3) 0.030(3) 0.026(3) -0.013(3) 0.007(2) -0.006(2) C51 0.033(4) 0.036(4) 0.035(4) -0.021(3) 0.011(3) -0.009(3) C52 0.047(5) 0.029(3) 0.019(3) 0.007(3) -0.013(3) -0.028(3) C53 0.021(4) 0.066(5) 0.026(3) -0.003(3) 0.001(3) 0.012(3) C54 0.067(6) 0.023(3) 0.028(4) 0.011(3) -0.009(4) -0.026(3) C55 0.056(5) 0.028(3) 0.032(4) -0.004(3) 0.012(4) -0.014(3) C68 0.022(10) 0.013(6) 0.022(7) -0.011(5) 0.011(7) -0.009(6) C69 0.014(11) 0.023(7) 0.024(8) -0.007(5) 0.010(8) -0.010(6) C70 0.072(12) 0.022(7) 0.028(11) -0.005(6) 0.013(9) -0.008(7) C71 0.042(15) 0.029(8) 0.026(8) -0.007(6) 0.006(8) -0.003(7) C72 0.022(11) 0.021(8) 0.037(18) -0.008(8) 0.011(12) -0.008(8) Br1 0.0488(7) 0.0561(7) 0.0674(7) 0.0113(4) 0.0034(5) 0.0023(4) C73 0.019(10) 0.027(8) 0.032(11) -0.005(7) 0.013(9) -0.001(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.312(6) . ? O1 B1 1.540(6) . ? O2 C5 1.314(6) . ? O2 B1 1.515(6) . ? N1 C15 1.358(7) . ? N1 C21 1.390(7) . ? N1 H1 0.8800 . ? C5 C12 1.399(7) . ? C5 C21 1.422(8) . ? C6 N2 1.357(7) . ? C6 C18 1.382(8) . ? C6 C16 1.476(8) . ? N3 C62 1.524(7) . ? N3 C60 1.526(7) . ? N3 C64 1.528(7) . ? N3 C59 1.530(7) . ? N2 C10 1.403(7) . ? N2 H2 0.8800 . ? C9 C39 1.384(8) . ? C9 C19 1.393(7) . ? C9 B1 1.589(7) . ? C10 C11 1.398(8) . ? C10 C13 1.424(7) . ? C11 C18 1.395(8) . ? C11 H3 0.9500 . ? C12 C13 1.393(7) . ? C12 H4 0.9500 . ? C14 C50 1.395(8) . ? C14 C37 1.398(8) . ? C14 B1 1.611(8) . ? C15 C22 1.388(8) . ? C15 C26 1.467(7) . ? C16 C33 1.393(8) . ? C16 C20 1.398(9) . ? C17 C34 1.393(8) . ? C17 C49 1.408(10) . ? C17 H5 0.9500 . ? C18 H6 0.9500 . ? C19 C35 1.404(7) . ? C19 H7 0.9500 . ? C20 C23 1.404(8) . ? C20 H8 0.9500 . ? C21 C42 1.386(8) . ? C22 C42 1.400(8) . ? C22 H9 0.9500 . ? C23 C31 1.371(9) . ? C23 H10 0.9500 . ? C24 C35 1.378(8) . ? C24 C45 1.384(8) . ? C24 H11 0.9500 . ? C26 C34 1.394(9) . ? C26 C52 1.407(9) . ? C27 C41 1.365(10) . ? C27 C51 1.401(10) . ? C27 H12 0.9500 . ? C58 C63 1.521(9) . ? C58 C60 1.529(8) . ? C58 H27 0.9900 . ? C58 H28 0.9900 . ? C59 C67 1.519(8) . ? C59 H29 0.9900 . ? C59 H30 0.9900 . ? C60 H31 0.9900 . ? C60 H32 0.9900 . ? C31 C36 1.369(10) . ? C31 H13 0.9500 . ? C61 C66 1.517(9) . ? C61 C53 1.537(9) . ? C61 H33 0.9900 . ? C61 H34 0.9900 . ? C33 C36 1.417(8) . ? C33 H14 0.9500 . ? C34 H15 0.9500 . ? C35 H16 0.9500 . ? C36 H17 0.9500 . ? C37 C41 1.389(9) . ? C37 H18 0.9500 . ? C62 C68 1.503(14) . ? C62 C73 1.61(2) . ? C62 H71 0.9900 . ? C62 H72 0.9900 . ? C62 H73 0.9900 . ? C62 H74 0.9900 . ? C39 C45 1.402(8) . ? C39 H19 0.9500 . ? C63 C46 1.515(9) . ? C63 H37 0.9900 . ? C63 H38 0.9900 . ? C41 H20 0.9500 . ? C42 H70 0.9500 . ? C64 C66 1.529(9) . ? C64 H39 0.9900 . ? C64 H40 0.9900 . ? C65 C67 1.518(9) . ? C65 C55 1.547(10) . ? C65 H41 0.9900 . ? C65 H42 0.9900 . ? C45 H21 0.9500 . ? C46 H43 0.9800 . ? C46 H44 0.9800 . ? C46 H45 0.9800 . ? C66 H46 0.9900 . ? C66 H47 0.9900 . ? C67 H48 0.9900 . ? C67 H49 0.9900 . ? C49 C54 1.379(12) . ? C49 H22 0.9500 . ? C50 C51 1.401(9) . ? C50 H23 0.9500 . ? C51 H24 0.9500 . ? C52 C54 1.404(9) . ? C52 H25 0.9500 . ? C53 H50 0.9800 . ? C53 H51 0.9800 . ? C53 H52 0.9800 . ? C54 H26 0.9500 . ? C55 H53 0.9800 . ? C55 H54 0.9800 . ? C55 H55 0.9800 . ? C68 C69 1.52(2) . ? C68 H75 0.9900 . ? C68 H76 0.9900 . ? C69 C70 1.55(2) . ? C69 H60 0.9900 . ? C69 H61 0.9900 . ? C70 H62 0.9800 . ? C70 H63 0.9800 . ? C70 H64 0.9800 . ? C71 C72 1.48(3) . ? C71 H65 0.9800 . ? C71 H66 0.9800 . ? C71 H67 0.9800 . ? C72 C73 1.50(3) . ? C72 H68 0.9900 . ? C72 H69 0.9900 . ? C73 H77 0.9900 . ? C73 H78 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O1 B1 116.5(4) . . ? C5 O2 B1 116.2(4) . . ? C15 N1 C21 109.0(4) . . ? C15 N1 H1 125.5 . . ? C21 N1 H1 125.5 . . ? O2 C5 C12 121.0(5) . . ? O2 C5 C21 115.6(5) . . ? C12 C5 C21 123.4(5) . . ? N2 C6 C18 108.5(5) . . ? N2 C6 C16 121.9(5) . . ? C18 C6 C16 129.7(5) . . ? C62 N3 C60 111.3(4) . . ? C62 N3 C64 111.7(4) . . ? C60 N3 C64 105.2(4) . . ? C62 N3 C59 105.5(4) . . ? C60 N3 C59 111.7(4) . . ? C64 N3 C59 111.6(4) . . ? C6 N2 C10 109.1(4) . . ? C6 N2 H2 125.5 . . ? C10 N2 H2 125.5 . . ? C39 C9 C19 116.7(5) . . ? C39 C9 B1 120.1(5) . . ? C19 C9 B1 122.9(5) . . ? C11 C10 N2 106.7(4) . . ? C11 C10 C13 130.8(5) . . ? N2 C10 C13 122.5(5) . . ? C18 C11 C10 107.6(5) . . ? C18 C11 H3 126.2 . . ? C10 C11 H3 126.2 . . ? C13 C12 C5 118.5(5) . . ? C13 C12 H4 120.8 . . ? C5 C12 H4 120.8 . . ? O1 C13 C12 121.6(5) . . ? O1 C13 C10 116.4(4) . . ? C12 C13 C10 121.9(5) . . ? C50 C14 C37 116.1(5) . . ? C50 C14 B1 123.6(5) . . ? C37 C14 B1 119.9(5) . . ? N1 C15 C22 108.4(5) . . ? N1 C15 C26 122.6(5) . . ? C22 C15 C26 129.0(5) . . ? C33 C16 C20 119.6(5) . . ? C33 C16 C6 119.9(5) . . ? C20 C16 C6 120.5(5) . . ? C34 C17 C49 119.7(6) . . ? C34 C17 H5 120.2 . . ? C49 C17 H5 120.2 . . ? C6 C18 C11 108.2(5) . . ? C6 C18 H6 125.9 . . ? C11 C18 H6 125.9 . . ? C9 C19 C35 121.7(5) . . ? C9 C19 H7 119.1 . . ? C35 C19 H7 119.1 . . ? C16 C20 C23 120.0(6) . . ? C16 C20 H8 120.0 . . ? C23 C20 H8 120.0 . . ? C42 C21 N1 107.5(5) . . ? C42 C21 C5 128.9(5) . . ? N1 C21 C5 123.6(5) . . ? C15 C22 C42 107.5(5) . . ? C15 C22 H9 126.2 . . ? C42 C22 H9 126.2 . . ? C31 C23 C20 120.1(6) . . ? C31 C23 H10 119.9 . . ? C20 C23 H10 119.9 . . ? C35 C24 C45 119.4(5) . . ? C35 C24 H11 120.3 . . ? C45 C24 H11 120.3 . . ? O2 B1 O1 107.1(4) . . ? O2 B1 C9 107.8(4) . . ? O1 B1 C9 108.9(4) . . ? O2 B1 C14 108.5(4) . . ? O1 B1 C14 110.7(4) . . ? C9 B1 C14 113.7(4) . . ? C34 C26 C52 119.5(5) . . ? C34 C26 C15 122.1(5) . . ? C52 C26 C15 118.4(5) . . ? C41 C27 C51 120.0(6) . . ? C41 C27 H12 120.0 . . ? C51 C27 H12 120.0 . . ? C63 C58 C60 107.4(5) . . ? C63 C58 H27 110.2 . . ? C60 C58 H27 110.2 . . ? C63 C58 H28 110.2 . . ? C60 C58 H28 110.2 . . ? H27 C58 H28 108.5 . . ? C67 C59 N3 116.4(5) . . ? C67 C59 H29 108.2 . . ? N3 C59 H29 108.2 . . ? C67 C59 H30 108.2 . . ? N3 C59 H30 108.2 . . ? H29 C59 H30 107.3 . . ? N3 C60 C58 116.2(4) . . ? N3 C60 H31 108.2 . . ? C58 C60 H31 108.2 . . ? N3 C60 H32 108.2 . . ? C58 C60 H32 108.2 . . ? H31 C60 H32 107.4 . . ? C36 C31 C23 120.6(5) . . ? C36 C31 H13 119.7 . . ? C23 C31 H13 119.7 . . ? C66 C61 C53 111.8(5) . . ? C66 C61 H33 109.2 . . ? C53 C61 H33 109.2 . . ? C66 C61 H34 109.2 . . ? C53 C61 H34 109.2 . . ? H33 C61 H34 107.9 . . ? C16 C33 C36 119.2(6) . . ? C16 C33 H14 120.4 . . ? C36 C33 H14 120.4 . . ? C17 C34 C26 120.7(6) . . ? C17 C34 H15 119.7 . . ? C26 C34 H15 119.7 . . ? C24 C35 C19 120.1(5) . . ? C24 C35 H16 119.9 . . ? C19 C35 H16 119.9 . . ? C31 C36 C33 120.5(6) . . ? C31 C36 H17 119.7 . . ? C33 C36 H17 119.7 . . ? C41 C37 C14 122.7(6) . . ? C41 C37 H18 118.6 . . ? C14 C37 H18 118.6 . . ? C68 C62 N3 116.4(7) . . ? C68 C62 C73 23.9(6) . . ? N3 C62 C73 112.8(8) . . ? C68 C62 H71 124.6 . . ? N3 C62 H71 109.0 . . ? C73 C62 H71 109.0 . . ? C68 C62 H72 86.1 . . ? N3 C62 H72 109.0 . . ? C73 C62 H72 109.0 . . ? H71 C62 H72 107.8 . . ? C68 C62 H73 108.2 . . ? N3 C62 H73 108.2 . . ? C73 C62 H73 128.5 . . ? H71 C62 H73 84.8 . . ? H72 C62 H73 25.3 . . ? C68 C62 H74 108.2 . . ? N3 C62 H74 108.2 . . ? C73 C62 H74 88.3 . . ? H71 C62 H74 24.0 . . ? H72 C62 H74 127.8 . . ? H73 C62 H74 107.3 . . ? C9 C39 C45 122.4(5) . . ? C9 C39 H19 118.8 . . ? C45 C39 H19 118.8 . . ? C46 C63 C58 113.3(5) . . ? C46 C63 H37 108.9 . . ? C58 C63 H37 108.9 . . ? C46 C63 H38 108.9 . . ? C58 C63 H38 108.9 . . ? H37 C63 H38 107.7 . . ? C27 C41 C37 119.8(6) . . ? C27 C41 H20 120.1 . . ? C37 C41 H20 120.1 . . ? C21 C42 C22 107.6(5) . . ? C21 C42 H70 126.2 . . ? C22 C42 H70 126.2 . . ? N3 C64 C66 115.9(5) . . ? N3 C64 H39 108.3 . . ? C66 C64 H39 108.3 . . ? N3 C64 H40 108.3 . . ? C66 C64 H40 108.3 . . ? H39 C64 H40 107.4 . . ? C67 C65 C55 113.1(6) . . ? C67 C65 H41 109.0 . . ? C55 C65 H41 109.0 . . ? C67 C65 H42 109.0 . . ? C55 C65 H42 109.0 . . ? H41 C65 H42 107.8 . . ? C24 C45 C39 119.6(5) . . ? C24 C45 H21 120.2 . . ? C39 C45 H21 120.2 . . ? C63 C46 H43 109.5 . . ? C63 C46 H44 109.5 . . ? H43 C46 H44 109.5 . . ? C63 C46 H45 109.5 . . ? H43 C46 H45 109.5 . . ? H44 C46 H45 109.5 . . ? C61 C66 C64 108.5(5) . . ? C61 C66 H46 110.0 . . ? C64 C66 H46 110.0 . . ? C61 C66 H47 110.0 . . ? C64 C66 H47 110.0 . . ? H46 C66 H47 108.4 . . ? C65 C67 C59 108.4(5) . . ? C65 C67 H48 110.0 . . ? C59 C67 H48 110.0 . . ? C65 C67 H49 110.0 . . ? C59 C67 H49 110.0 . . ? H48 C67 H49 108.4 . . ? C54 C49 C17 119.9(6) . . ? C54 C49 H22 120.1 . . ? C17 C49 H22 120.1 . . ? C14 C50 C51 122.2(6) . . ? C14 C50 H23 118.9 . . ? C51 C50 H23 118.9 . . ? C27 C51 C50 119.1(6) . . ? C27 C51 H24 120.5 . . ? C50 C51 H24 120.5 . . ? C54 C52 C26 119.5(7) . . ? C54 C52 H25 120.3 . . ? C26 C52 H25 120.3 . . ? C61 C53 H50 109.5 . . ? C61 C53 H51 109.5 . . ? H50 C53 H51 109.5 . . ? C61 C53 H52 109.5 . . ? H50 C53 H52 109.5 . . ? H51 C53 H52 109.5 . . ? C49 C54 C52 120.7(7) . . ? C49 C54 H26 119.7 . . ? C52 C54 H26 119.7 . . ? C65 C55 H53 109.5 . . ? C65 C55 H54 109.5 . . ? H53 C55 H54 109.5 . . ? C65 C55 H55 109.5 . . ? H53 C55 H55 109.5 . . ? H54 C55 H55 109.5 . . ? C62 C68 C69 108.4(10) . . ? C62 C68 H75 110.0 . . ? C69 C68 H75 110.0 . . ? C62 C68 H76 110.0 . . ? C69 C68 H76 110.0 . . ? H75 C68 H76 108.4 . . ? C68 C69 C70 112.5(18) . . ? C68 C69 H60 109.1 . . ? C70 C69 H60 109.1 . . ? C68 C69 H61 109.1 . . ? C70 C69 H61 109.1 . . ? H60 C69 H61 107.8 . . ? C69 C70 H62 109.5 . . ? C69 C70 H63 109.5 . . ? H62 C70 H63 109.5 . . ? C69 C70 H64 109.5 . . ? H62 C70 H64 109.5 . . ? H63 C70 H64 109.5 . . ? C71 C72 C73 113(2) . . ? C71 C72 H68 109.0 . . ? C73 C72 H68 109.0 . . ? C71 C72 H69 109.0 . . ? C73 C72 H69 109.0 . . ? H68 C72 H69 107.8 . . ? C72 C73 C62 109.9(13) . . ? C72 C73 H77 109.7 . . ? C62 C73 H77 109.7 . . ? C72 C73 H78 109.7 . . ? C62 C73 H78 109.7 . . ? H77 C73 H78 108.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag B1 O2 C5 C12 22.1(7) . . . . ? B1 O2 C5 C21 -159.9(5) . . . . ? C18 C6 N2 C10 0.6(6) . . . . ? C16 C6 N2 C10 -179.3(5) . . . . ? C6 N2 C10 C11 0.3(5) . . . . ? C6 N2 C10 C13 -179.2(5) . . . . ? N2 C10 C11 C18 -1.0(6) . . . . ? C13 C10 C11 C18 178.4(5) . . . . ? O2 C5 C12 C13 11.3(8) . . . . ? C21 C5 C12 C13 -166.6(5) . . . . ? B1 O1 C13 C12 -13.5(7) . . . . ? B1 O1 C13 C10 170.8(4) . . . . ? C5 C12 C13 O1 -15.7(7) . . . . ? C5 C12 C13 C10 159.7(5) . . . . ? C11 C10 C13 O1 -7.4(8) . . . . ? N2 C10 C13 O1 171.9(4) . . . . ? C11 C10 C13 C12 176.9(5) . . . . ? N2 C10 C13 C12 -3.8(8) . . . . ? C21 N1 C15 C22 0.7(6) . . . . ? C21 N1 C15 C26 178.7(5) . . . . ? N2 C6 C16 C33 -157.9(5) . . . . ? C18 C6 C16 C33 22.1(8) . . . . ? N2 C6 C16 C20 21.9(8) . . . . ? C18 C6 C16 C20 -158.1(5) . . . . ? N2 C6 C18 C11 -1.3(6) . . . . ? C16 C6 C18 C11 178.7(5) . . . . ? C10 C11 C18 C6 1.4(6) . . . . ? C39 C9 C19 C35 -2.1(9) . . . . ? B1 C9 C19 C35 -176.5(5) . . . . ? C33 C16 C20 C23 1.7(8) . . . . ? C6 C16 C20 C23 -178.2(5) . . . . ? C15 N1 C21 C42 0.3(6) . . . . ? C15 N1 C21 C5 -179.4(5) . . . . ? O2 C5 C21 C42 9.2(9) . . . . ? C12 C5 C21 C42 -172.9(6) . . . . ? O2 C5 C21 N1 -171.1(5) . . . . ? C12 C5 C21 N1 6.8(9) . . . . ? N1 C15 C22 C42 -1.4(7) . . . . ? C26 C15 C22 C42 -179.3(5) . . . . ? C16 C20 C23 C31 -0.9(9) . . . . ? C5 O2 B1 O1 -46.7(6) . . . . ? C5 O2 B1 C9 -163.7(4) . . . . ? C5 O2 B1 C14 72.8(5) . . . . ? C13 O1 B1 O2 42.4(5) . . . . ? C13 O1 B1 C9 158.7(4) . . . . ? C13 O1 B1 C14 -75.6(5) . . . . ? C39 C9 B1 O2 -175.1(5) . . . . ? C19 C9 B1 O2 -0.9(7) . . . . ? C39 C9 B1 O1 69.1(7) . . . . ? C19 C9 B1 O1 -116.7(5) . . . . ? C39 C9 B1 C14 -54.8(7) . . . . ? C19 C9 B1 C14 119.4(6) . . . . ? C50 C14 B1 O2 -148.4(5) . . . . ? C37 C14 B1 O2 38.8(6) . . . . ? C50 C14 B1 O1 -31.2(7) . . . . ? C37 C14 B1 O1 156.0(5) . . . . ? C50 C14 B1 C9 91.7(6) . . . . ? C37 C14 B1 C9 -81.1(6) . . . . ? N1 C15 C26 C34 -3.1(8) . . . . ? C22 C15 C26 C34 174.5(6) . . . . ? N1 C15 C26 C52 178.5(5) . . . . ? C22 C15 C26 C52 -3.9(9) . . . . ? C62 N3 C59 C67 -175.1(5) . . . . ? C60 N3 C59 C67 -54.1(6) . . . . ? C64 N3 C59 C67 63.4(7) . . . . ? C62 N3 C60 C58 57.7(6) . . . . ? C64 N3 C60 C58 178.8(5) . . . . ? C59 N3 C60 C58 -60.0(6) . . . . ? C63 C58 C60 N3 -178.8(5) . . . . ? C20 C23 C31 C36 -0.7(9) . . . . ? C20 C16 C33 C36 -0.8(8) . . . . ? C6 C16 C33 C36 179.0(5) . . . . ? C49 C17 C34 C26 2.5(9) . . . . ? C52 C26 C34 C17 -3.9(9) . . . . ? C15 C26 C34 C17 177.7(5) . . . . ? C45 C24 C35 C19 -1.6(9) . . . . ? C9 C19 C35 C24 2.0(9) . . . . ? C23 C31 C36 C33 1.6(9) . . . . ? C16 C33 C36 C31 -0.8(8) . . . . ? C50 C14 C37 C41 0.4(9) . . . . ? B1 C14 C37 C41 173.7(5) . . . . ? C60 N3 C62 C68 74.0(12) . . . . ? C64 N3 C62 C68 -43.3(13) . . . . ? C59 N3 C62 C68 -164.7(12) . . . . ? C60 N3 C62 C73 48.0(13) . . . . ? C64 N3 C62 C73 -69.3(13) . . . . ? C59 N3 C62 C73 169.3(12) . . . . ? C19 C9 C39 C45 1.9(10) . . . . ? B1 C9 C39 C45 176.5(6) . . . . ? C60 C58 C63 C46 178.7(6) . . . . ? C51 C27 C41 C37 1.5(10) . . . . ? C14 C37 C41 C27 -1.5(10) . . . . ? N1 C21 C42 C22 -1.2(7) . . . . ? C5 C21 C42 C22 178.5(6) . . . . ? C15 C22 C42 C21 1.6(7) . . . . ? C62 N3 C64 C66 -59.3(7) . . . . ? C60 N3 C64 C66 179.8(5) . . . . ? C59 N3 C64 C66 58.5(7) . . . . ? C35 C24 C45 C39 1.4(11) . . . . ? C9 C39 C45 C24 -1.7(12) . . . . ? C53 C61 C66 C64 179.0(6) . . . . ? N3 C64 C66 C61 176.1(5) . . . . ? C55 C65 C67 C59 -175.0(6) . . . . ? N3 C59 C67 C65 -176.3(5) . . . . ? C34 C17 C49 C54 1.4(10) . . . . ? C37 C14 C50 C51 0.8(9) . . . . ? B1 C14 C50 C51 -172.2(6) . . . . ? C41 C27 C51 C50 -0.3(11) . . . . ? C14 C50 C51 C27 -0.8(11) . . . . ? C34 C26 C52 C54 1.5(10) . . . . ? C15 C26 C52 C54 179.8(6) . . . . ? C17 C49 C54 C52 -3.9(12) . . . . ? C26 C52 C54 C49 2.4(12) . . . . ? N3 C62 C68 C69 -173.9(13) . . . . ? C73 C62 C68 C69 -87(3) . . . . ? C62 C68 C69 C70 77.1(18) . . . . ? C71 C72 C73 C62 -64(2) . . . . ? C68 C62 C73 C72 86(3) . . . . ? N3 C62 C73 C72 -170.4(16) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.419 _refine_diff_density_min -2.800 _refine_diff_density_rms 0.231 #============================================================================== # End of CIF #============================================================================== data_91007mae _database_code_depnum_ccdc_archive 'CCDC 759627' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C43 H43 B N2 O2, C16 H36 N, Cl ' _chemical_formula_sum 'C59 H79 B Cl N3 O2' _chemical_formula_weight 908.51 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' Cl Cl 0.1484 0.1585 '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 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.475(3) _cell_length_b 23.006(6) _cell_length_c 13.458(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.080(10) _cell_angle_gamma 90.00 _cell_volume 2598.2(12) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.161 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9324 _exptl_absorpt_correction_T_max 0.9883 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _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 \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25671 _diffrn_reflns_av_R_equivalents 0.0469 _diffrn_reflns_av_sigmaI/netI 0.0695 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 11812 _reflns_number_gt 9715 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.8' _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^)+(0.0473P)^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 ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.10(4) _refine_ls_number_reflns 11812 _refine_ls_number_parameters 603 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1019 _refine_ls_wR_factor_gt 0.0957 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.038 _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 C1 C 0.0557(2) 0.09290(9) 0.09926(13) 0.0202(4) Uani 1 1 d . . . C2 C -0.0074(2) 0.13312(8) 0.02608(13) 0.0206(4) Uani 1 1 d . . . C3 C -0.0201(2) 0.18698(8) 0.07440(13) 0.0198(4) Uani 1 1 d . . . C4 C 0.0297(2) 0.17844(8) 0.17683(13) 0.0188(4) Uani 1 1 d . . . C5 C 0.0402(2) 0.21817(8) 0.26003(13) 0.0170(4) Uani 1 1 d . . . C6 C 0.0833(2) 0.19982(8) 0.35818(13) 0.0205(4) Uani 1 1 d . . . H1 H 0.0962 0.1595 0.3725 0.025 Uiso 1 1 calc R . . C7 C 0.1076(2) 0.24032(8) 0.43591(13) 0.0176(4) Uani 1 1 d . . . C8 C 0.1852(2) 0.22635(8) 0.53424(13) 0.0184(4) Uani 1 1 d . . . C9 C 0.2308(2) 0.26271(8) 0.61681(14) 0.0227(4) Uani 1 1 d . . . C10 C 0.3095(2) 0.22781(9) 0.69427(14) 0.0225(4) Uani 1 1 d . . . C11 C 0.3106(2) 0.17068(9) 0.65857(14) 0.0213(4) Uani 1 1 d . . . C12 C 0.1062(2) 0.03221(8) 0.09064(14) 0.0222(4) Uani 1 1 d . . . C13 C 0.1211(2) -0.00513(9) 0.17355(15) 0.0250(4) Uani 1 1 d . . . H2 H 0.0979 0.0089 0.2363 0.030 Uiso 1 1 calc R . . C14 C 0.1694(3) -0.06255(9) 0.16549(17) 0.0308(5) Uani 1 1 d . . . H3 H 0.1805 -0.0871 0.2228 0.037 Uiso 1 1 calc R . . C15 C 0.2012(3) -0.08396(9) 0.07444(17) 0.0320(5) Uani 1 1 d . . . H4 H 0.2316 -0.1234 0.0684 0.038 Uiso 1 1 calc R . . C16 C 0.1884(3) -0.04749(10) -0.00764(17) 0.0358(5) Uani 1 1 d . . . H5 H 0.2108 -0.0619 -0.0703 0.043 Uiso 1 1 calc R . . C17 C 0.1434(3) 0.00977(10) 0.00037(16) 0.0319(5) Uani 1 1 d . . . H6 H 0.1376 0.0344 -0.0567 0.038 Uiso 1 1 calc R . . C18 C 0.3649(3) 0.11616(9) 0.70901(14) 0.0234(4) Uani 1 1 d . . . C19 C 0.4838(3) 0.11540(10) 0.79293(15) 0.0282(4) Uani 1 1 d . . . H7 H 0.5354 0.1506 0.8157 0.034 Uiso 1 1 calc R . . C20 C 0.5264(3) 0.06416(11) 0.84271(16) 0.0359(5) Uani 1 1 d . . . H8 H 0.6053 0.0644 0.9003 0.043 Uiso 1 1 calc R . . C21 C 0.4549(3) 0.01244(11) 0.80941(19) 0.0392(6) Uani 1 1 d . . . H9 H 0.4853 -0.0228 0.8437 0.047 Uiso 1 1 calc R . . C22 C 0.3396(3) 0.01212(10) 0.72638(18) 0.0362(5) Uani 1 1 d . . . H10 H 0.2910 -0.0235 0.7030 0.043 Uiso 1 1 calc R . . C23 C 0.2945(3) 0.06347(10) 0.67711(14) 0.0279(4) Uani 1 1 d . . . H11 H 0.2140 0.0628 0.6204 0.034 Uiso 1 1 calc R . . N1 N 0.07492(19) 0.12095(7) 0.18995(11) 0.0181(3) Uani 1 1 d . . . H12 H 0.1108 0.1047 0.2480 0.022 Uiso 1 1 calc R . . N2 N 0.2359(2) 0.17081(7) 0.56189(11) 0.0197(3) Uani 1 1 d . . . H13 H 0.2219 0.1400 0.5228 0.024 Uiso 1 1 calc R . . O1 O 0.01190(16) 0.27337(5) 0.23868(9) 0.0190(3) Uani 1 1 d . . . O2 O 0.06413(17) 0.29431(5) 0.42058(9) 0.0208(3) Uani 1 1 d . . . B1 B -0.0306(3) 0.31375(9) 0.32150(15) 0.0184(4) Uani 1 1 d . . . C24 C 0.0281(2) 0.37862(8) 0.30315(13) 0.0199(4) Uani 1 1 d . . . C25 C 0.0940(3) 0.39633(9) 0.21861(15) 0.0259(4) Uani 1 1 d . . . H14 H 0.1038 0.3690 0.1669 0.031 Uiso 1 1 calc R . . C26 C 0.1458(3) 0.45333(10) 0.20851(17) 0.0331(5) Uani 1 1 d . . . H15 H 0.1911 0.4642 0.1506 0.040 Uiso 1 1 calc R . . C27 C 0.1318(3) 0.49384(9) 0.28194(17) 0.0320(5) Uani 1 1 d . . . H16 H 0.1685 0.5325 0.2753 0.038 Uiso 1 1 calc R . . C28 C 0.0639(3) 0.47789(9) 0.36551(16) 0.0286(5) Uani 1 1 d . . . H17 H 0.0519 0.5058 0.4160 0.034 Uiso 1 1 calc R . . C29 C 0.0132(3) 0.42115(9) 0.37547(15) 0.0265(4) Uani 1 1 d . . . H18 H -0.0330 0.4108 0.4333 0.032 Uiso 1 1 calc R . . C30 C -0.2191(2) 0.30891(8) 0.32490(14) 0.0207(4) Uani 1 1 d . . . C31 C -0.3251(3) 0.33817(10) 0.25275(15) 0.0304(5) Uani 1 1 d . . . H19 H -0.2836 0.3603 0.2028 0.037 Uiso 1 1 calc R . . C32 C -0.4885(3) 0.33585(11) 0.25177(18) 0.0395(6) Uani 1 1 d . . . H20 H -0.5567 0.3566 0.2019 0.047 Uiso 1 1 calc R . . C33 C -0.5531(3) 0.30374(10) 0.32245(18) 0.0356(5) Uani 1 1 d . . . H21 H -0.6653 0.3019 0.3215 0.043 Uiso 1 1 calc R . . C34 C -0.4518(3) 0.27435(10) 0.39471(18) 0.0359(5) Uani 1 1 d . . . H22 H -0.4944 0.2520 0.4440 0.043 Uiso 1 1 calc R . . C35 C -0.2888(3) 0.27735(9) 0.39563(16) 0.0300(5) Uani 1 1 d . . . H23 H -0.2215 0.2571 0.4465 0.036 Uiso 1 1 calc R . . C36 C -0.0589(3) 0.12186(9) -0.08400(14) 0.0256(4) Uani 1 1 d . . . H24 H -0.1587 0.1436 -0.1055 0.031 Uiso 1 1 calc R . . H25 H -0.0831 0.0800 -0.0933 0.031 Uiso 1 1 calc R . . C37 C 0.0631(3) 0.13882(11) -0.15212(14) 0.0338(5) Uani 1 1 d . . . H26 H 0.0712 0.1813 -0.1547 0.051 Uiso 1 1 calc R . . H27 H 0.0292 0.1237 -0.2198 0.051 Uiso 1 1 calc R . . H28 H 0.1672 0.1224 -0.1256 0.051 Uiso 1 1 calc R . . C38 C -0.0711(2) 0.24365(9) 0.02367(14) 0.0237(4) Uani 1 1 d . . . H29 H -0.1334 0.2663 0.0672 0.028 Uiso 1 1 calc R . . H30 H -0.1411 0.2356 -0.0401 0.028 Uiso 1 1 calc R . . C39 C 0.0719(3) 0.27973(10) 0.00200(16) 0.0314(5) Uani 1 1 d . . . H31 H 0.1417 0.2876 0.0650 0.047 Uiso 1 1 calc R . . H32 H 0.0343 0.3166 -0.0294 0.047 Uiso 1 1 calc R . . H33 H 0.1312 0.2581 -0.0434 0.047 Uiso 1 1 calc R . . C40 C 0.1996(3) 0.32677(9) 0.62444(15) 0.0292(5) Uani 1 1 d . . . H34 H 0.2132 0.3457 0.5601 0.035 Uiso 1 1 calc R . . H35 H 0.2791 0.3437 0.6775 0.035 Uiso 1 1 calc R . . C41 C 0.0335(4) 0.33955(11) 0.64852(19) 0.0452(6) Uani 1 1 d . . . H36 H -0.0457 0.3238 0.5952 0.068 Uiso 1 1 calc R . . H37 H 0.0191 0.3817 0.6532 0.068 Uiso 1 1 calc R . . H38 H 0.0199 0.3214 0.7126 0.068 Uiso 1 1 calc R . . C42 C 0.3754(3) 0.25006(9) 0.79695(14) 0.0264(4) Uani 1 1 d . . . H39 H 0.3754 0.2180 0.8460 0.032 Uiso 1 1 calc R . . H40 H 0.3045 0.2810 0.8162 0.032 Uiso 1 1 calc R . . C43 C 0.5449(3) 0.27429(10) 0.80292(15) 0.0336(5) Uani 1 1 d . . . H41 H 0.6164 0.2437 0.7850 0.050 Uiso 1 1 calc R . . H42 H 0.5814 0.2877 0.8714 0.050 Uiso 1 1 calc R . . H43 H 0.5454 0.3069 0.7562 0.050 Uiso 1 1 calc R . . Cl1 Cl 0.14905(6) 0.05677(2) 0.41508(3) 0.02264(10) Uani 1 1 d . . . N3 N 0.6178(2) 0.05155(8) 0.31340(12) 0.0263(4) Uani 1 1 d . . . C44 C 0.5015(3) 0.09431(10) 0.25569(16) 0.0300(5) Uani 1 1 d . . . H44 H 0.4206 0.0719 0.2112 0.036 Uiso 1 1 calc R . . H45 H 0.4454 0.1154 0.3044 0.036 Uiso 1 1 calc R . . C45 C 0.5745(3) 0.13846(11) 0.19271(18) 0.0363(5) Uani 1 1 d . . . H46 H 0.6358 0.1181 0.1457 0.044 Uiso 1 1 calc R . . H47 H 0.6491 0.1636 0.2368 0.044 Uiso 1 1 calc R . . C46 C 0.4462(3) 0.17573(11) 0.13372(16) 0.0351(5) Uani 1 1 d . . . H48 H 0.3694 0.1504 0.0918 0.042 Uiso 1 1 calc R . . H49 H 0.3875 0.1970 0.1810 0.042 Uiso 1 1 calc R . . C47 C 0.5162(3) 0.21893(11) 0.06714(17) 0.0392(6) Uani 1 1 d . . . H50 H 0.5946 0.2434 0.1082 0.059 Uiso 1 1 calc R . . H51 H 0.4309 0.2435 0.0327 0.059 Uiso 1 1 calc R . . H52 H 0.5683 0.1980 0.0173 0.059 Uiso 1 1 calc R . . C48 C 0.7397(3) 0.08376(9) 0.38801(15) 0.0268(4) Uani 1 1 d . . . H53 H 0.8229 0.0557 0.4158 0.032 Uiso 1 1 calc R . . H54 H 0.7919 0.1136 0.3507 0.032 Uiso 1 1 calc R . . C49 C 0.6765(3) 0.11319(10) 0.47448(16) 0.0305(5) Uani 1 1 d . . . H55 H 0.6249 0.0842 0.5137 0.037 Uiso 1 1 calc R . . H56 H 0.5959 0.1427 0.4487 0.037 Uiso 1 1 calc R . . C50 C 0.8147(3) 0.14231(10) 0.54158(15) 0.0284(5) Uani 1 1 d . . . H57 H 0.8901 0.1120 0.5711 0.034 Uiso 1 1 calc R . . H58 H 0.8724 0.1680 0.5000 0.034 Uiso 1 1 calc R . . C51 C 0.7603(3) 0.17777(11) 0.62568(16) 0.0378(5) Uani 1 1 d . . . H59 H 0.6854 0.2078 0.5970 0.057 Uiso 1 1 calc R . . H60 H 0.8528 0.1962 0.6652 0.057 Uiso 1 1 calc R . . H61 H 0.7076 0.1522 0.6691 0.057 Uiso 1 1 calc R . . C52 C 0.5188(3) 0.01047(9) 0.36803(16) 0.0282(4) Uani 1 1 d . . . H62 H 0.4606 0.0336 0.4132 0.034 Uiso 1 1 calc R . . H63 H 0.4385 -0.0086 0.3180 0.034 Uiso 1 1 calc R . . C53 C 0.6139(3) -0.03613(11) 0.4292(2) 0.0398(6) Uani 1 1 d . . . H64 H 0.7120 -0.0187 0.4659 0.048 Uiso 1 1 calc R . . H65 H 0.6459 -0.0663 0.3836 0.048 Uiso 1 1 calc R . . C54 C 0.5176(4) -0.06421(12) 0.5041(2) 0.0508(7) Uani 1 1 d . . . H66 H 0.5856 -0.0931 0.5445 0.061 Uiso 1 1 calc R . . H67 H 0.4884 -0.0339 0.5505 0.061 Uiso 1 1 calc R . . C55 C 0.3692(4) -0.09371(13) 0.4561(3) 0.0615(8) Uani 1 1 d . . . H68 H 0.3014 -0.0656 0.4154 0.092 Uiso 1 1 calc R . . H69 H 0.3116 -0.1096 0.5082 0.092 Uiso 1 1 calc R . . H70 H 0.3973 -0.1253 0.4130 0.092 Uiso 1 1 calc R . . C56 C 0.7114(3) 0.01816(11) 0.24390(17) 0.0335(5) Uani 1 1 d . . . H71 H 0.7908 -0.0064 0.2855 0.040 Uiso 1 1 calc R . . H72 H 0.7709 0.0465 0.2080 0.040 Uiso 1 1 calc R . . C57 C 0.6143(3) -0.02047(13) 0.16635(19) 0.0439(6) Uani 1 1 d . . . H73 H 0.5361 0.0036 0.1229 0.053 Uiso 1 1 calc R . . H74 H 0.5545 -0.0493 0.2010 0.053 Uiso 1 1 calc R . . C58 C 0.7203(4) -0.05224(15) 0.1017(2) 0.0536(7) Uani 1 1 d . . . H75 H 0.7690 -0.0234 0.0607 0.064 Uiso 1 1 calc R . . H76 H 0.8078 -0.0716 0.1461 0.064 Uiso 1 1 calc R . . C59 C 0.6344(4) -0.09675(12) 0.0333(2) 0.0469(6) Uani 1 1 d . . . H77 H 0.5950 -0.1277 0.0734 0.070 Uiso 1 1 calc R . . H78 H 0.7076 -0.1133 -0.0094 0.070 Uiso 1 1 calc R . . H79 H 0.5444 -0.0784 -0.0088 0.070 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 C1 0.0170(10) 0.0239(9) 0.0201(9) -0.0020(7) 0.0045(7) -0.0028(7) C2 0.0153(9) 0.0243(10) 0.0223(9) -0.0019(7) 0.0029(7) -0.0013(7) C3 0.0134(9) 0.0246(10) 0.0216(8) 0.0011(7) 0.0031(7) -0.0018(7) C4 0.0165(10) 0.0193(9) 0.0216(8) 0.0019(7) 0.0064(7) 0.0007(7) C5 0.0116(9) 0.0192(9) 0.0207(8) 0.0013(7) 0.0038(7) -0.0004(7) C6 0.0224(10) 0.0161(9) 0.0233(9) 0.0016(7) 0.0045(8) 0.0003(7) C7 0.0135(9) 0.0182(9) 0.0219(8) 0.0031(7) 0.0056(7) 0.0000(7) C8 0.0171(9) 0.0176(9) 0.0209(8) -0.0002(7) 0.0040(7) -0.0007(7) C9 0.0211(10) 0.0225(10) 0.0251(9) -0.0007(7) 0.0053(8) -0.0017(8) C10 0.0213(10) 0.0252(10) 0.0211(9) 0.0013(7) 0.0033(7) -0.0030(8) C11 0.0183(10) 0.0252(10) 0.0207(8) 0.0020(8) 0.0037(7) -0.0015(8) C12 0.0157(10) 0.0252(10) 0.0256(9) -0.0055(8) 0.0028(8) -0.0031(8) C13 0.0231(11) 0.0225(10) 0.0294(10) -0.0027(8) 0.0035(8) -0.0032(8) C14 0.0286(12) 0.0225(10) 0.0409(12) 0.0025(9) 0.0038(10) -0.0002(9) C15 0.0289(12) 0.0199(10) 0.0458(12) -0.0076(9) 0.0007(10) 0.0025(9) C16 0.0393(14) 0.0335(12) 0.0340(11) -0.0147(10) 0.0027(10) 0.0072(10) C17 0.0345(13) 0.0314(11) 0.0296(10) -0.0036(9) 0.0035(9) 0.0054(10) C18 0.0226(10) 0.0270(10) 0.0209(9) 0.0043(8) 0.0043(8) 0.0004(8) C19 0.0195(11) 0.0335(11) 0.0306(10) 0.0053(9) 0.0003(8) -0.0014(9) C20 0.0258(11) 0.0460(14) 0.0336(10) 0.0161(11) -0.0041(9) 0.0009(10) C21 0.0333(13) 0.0341(13) 0.0494(14) 0.0217(11) 0.0027(11) 0.0067(10) C22 0.0394(14) 0.0261(11) 0.0423(12) 0.0093(10) 0.0024(11) -0.0021(10) C23 0.0307(11) 0.0262(11) 0.0254(9) 0.0018(8) -0.0011(8) 0.0025(9) N1 0.0188(8) 0.0182(8) 0.0174(7) -0.0011(6) 0.0025(6) -0.0003(6) N2 0.0206(9) 0.0190(8) 0.0190(7) 0.0007(6) 0.0014(6) 0.0010(6) O1 0.0223(7) 0.0162(6) 0.0188(6) 0.0012(5) 0.0038(5) 0.0027(5) O2 0.0250(8) 0.0170(6) 0.0195(6) -0.0004(5) 0.0007(5) 0.0015(5) B1 0.0208(11) 0.0160(10) 0.0185(9) -0.0004(8) 0.0030(8) 0.0013(8) C24 0.0140(9) 0.0208(9) 0.0232(9) 0.0017(7) -0.0032(7) 0.0016(7) C25 0.0286(12) 0.0226(10) 0.0264(10) 0.0018(8) 0.0041(8) -0.0004(8) C26 0.0358(13) 0.0286(11) 0.0360(11) 0.0085(9) 0.0093(10) -0.0050(10) C27 0.0323(12) 0.0164(9) 0.0446(12) 0.0047(9) -0.0035(10) -0.0034(9) C28 0.0303(12) 0.0209(10) 0.0329(11) -0.0042(8) -0.0016(9) 0.0002(9) C29 0.0295(12) 0.0234(10) 0.0266(10) 0.0024(8) 0.0043(8) 0.0002(9) C30 0.0238(11) 0.0136(8) 0.0250(9) -0.0049(7) 0.0045(8) -0.0003(7) C31 0.0239(11) 0.0377(12) 0.0288(10) 0.0095(9) 0.0005(8) -0.0026(9) C32 0.0260(12) 0.0437(14) 0.0461(13) 0.0100(11) -0.0045(10) 0.0018(10) C33 0.0209(12) 0.0326(12) 0.0536(14) -0.0035(10) 0.0058(10) -0.0018(9) C34 0.0301(13) 0.0293(11) 0.0516(13) 0.0078(10) 0.0167(10) 0.0007(10) C35 0.0274(12) 0.0228(10) 0.0412(12) 0.0082(9) 0.0102(9) 0.0060(9) C36 0.0238(11) 0.0295(11) 0.0225(9) -0.0042(8) -0.0003(8) -0.0006(9) C37 0.0390(14) 0.0416(13) 0.0209(9) -0.0026(9) 0.0051(9) -0.0056(10) C38 0.0253(11) 0.0254(10) 0.0200(9) 0.0005(8) 0.0014(8) 0.0034(8) C39 0.0396(13) 0.0246(11) 0.0324(10) 0.0067(9) 0.0130(9) 0.0021(9) C40 0.0407(13) 0.0222(10) 0.0230(9) -0.0034(8) -0.0008(9) -0.0011(9) C41 0.0554(17) 0.0339(13) 0.0471(13) -0.0093(11) 0.0104(12) 0.0132(12) C42 0.0279(11) 0.0284(10) 0.0223(9) -0.0025(8) 0.0015(8) -0.0029(9) C43 0.0357(13) 0.0352(12) 0.0271(10) -0.0013(9) -0.0051(9) -0.0083(10) Cl1 0.0231(2) 0.0214(2) 0.0236(2) 0.00067(19) 0.00389(17) 0.0051(2) N3 0.0164(8) 0.0327(9) 0.0299(8) 0.0016(8) 0.0035(6) -0.0003(8) C44 0.0198(11) 0.0373(12) 0.0324(11) 0.0083(9) 0.0017(9) 0.0011(9) C45 0.0228(12) 0.0466(14) 0.0396(12) 0.0141(11) 0.0043(9) -0.0039(10) C46 0.0265(12) 0.0458(13) 0.0325(11) 0.0096(10) 0.0026(9) -0.0010(10) C47 0.0334(13) 0.0485(15) 0.0362(12) 0.0125(11) 0.0059(10) -0.0024(11) C48 0.0182(10) 0.0315(11) 0.0303(10) 0.0046(9) 0.0020(8) -0.0016(8) C49 0.0246(11) 0.0320(11) 0.0362(11) 0.0012(9) 0.0089(9) -0.0013(9) C50 0.0270(12) 0.0277(10) 0.0303(10) 0.0046(9) 0.0031(9) -0.0003(9) C51 0.0453(15) 0.0396(13) 0.0298(10) 0.0000(10) 0.0094(10) -0.0007(11) C52 0.0197(11) 0.0320(11) 0.0335(10) 0.0033(9) 0.0062(8) -0.0015(9) C53 0.0271(13) 0.0349(13) 0.0575(15) 0.0117(11) 0.0065(11) 0.0032(10) C54 0.0534(18) 0.0443(15) 0.0542(15) 0.0156(12) 0.0055(13) 0.0024(13) C55 0.055(2) 0.0458(17) 0.086(2) 0.0231(15) 0.0180(17) -0.0022(14) C56 0.0210(11) 0.0424(13) 0.0384(11) -0.0083(10) 0.0087(9) -0.0039(10) C57 0.0337(14) 0.0531(16) 0.0460(14) -0.0108(12) 0.0101(11) -0.0073(12) C58 0.0337(15) 0.076(2) 0.0530(15) -0.0258(14) 0.0141(12) -0.0086(13) C59 0.0469(17) 0.0476(15) 0.0456(13) -0.0009(12) 0.0046(12) 0.0032(12) _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 C1 N1 1.370(2) . ? C1 C2 1.401(3) . ? C1 C12 1.470(3) . ? C2 C3 1.410(3) . ? C2 C36 1.507(3) . ? C3 C4 1.398(3) . ? C3 C38 1.507(3) . ? C4 N1 1.381(2) . ? C4 C5 1.438(3) . ? C5 O1 1.317(2) . ? C5 C6 1.386(3) . ? C6 C7 1.394(3) . ? C6 H1 0.9500 . ? C7 O2 1.304(2) . ? C7 C8 1.429(3) . ? C8 N2 1.382(2) . ? C8 C9 1.401(3) . ? C9 C10 1.407(3) . ? C9 C40 1.504(3) . ? C10 C11 1.400(3) . ? C10 C42 1.506(3) . ? C11 N2 1.365(2) . ? C11 C18 1.469(3) . ? C12 C17 1.396(3) . ? C12 C13 1.400(3) . ? C13 C14 1.392(3) . ? C13 H2 0.9500 . ? C14 C15 1.382(3) . ? C14 H3 0.9500 . ? C15 C16 1.379(3) . ? C15 H4 0.9500 . ? C16 C17 1.380(3) . ? C16 H5 0.9500 . ? C17 H6 0.9500 . ? C18 C23 1.392(3) . ? C18 C19 1.404(3) . ? C19 C20 1.379(3) . ? C19 H7 0.9500 . ? C20 C21 1.381(4) . ? C20 H8 0.9500 . ? C21 C22 1.377(3) . ? C21 H9 0.9500 . ? C22 C23 1.382(3) . ? C22 H10 0.9500 . ? C23 H11 0.9500 . ? N1 H12 0.8800 . ? N2 H13 0.8800 . ? O1 B1 1.532(2) . ? O2 B1 1.524(2) . ? B1 C24 1.603(3) . ? B1 C30 1.609(3) . ? C24 C25 1.397(3) . ? C24 C29 1.398(3) . ? C25 C26 1.396(3) . ? C25 H14 0.9500 . ? C26 C27 1.376(3) . ? C26 H15 0.9500 . ? C27 C28 1.383(3) . ? C27 H16 0.9500 . ? C28 C29 1.387(3) . ? C28 H17 0.9500 . ? C29 H18 0.9500 . ? C30 C35 1.393(3) . ? C30 C31 1.399(3) . ? C31 C32 1.384(3) . ? C31 H19 0.9500 . ? C32 C33 1.377(4) . ? C32 H20 0.9500 . ? C33 C34 1.380(3) . ? C33 H21 0.9500 . ? C34 C35 1.382(3) . ? C34 H22 0.9500 . ? C35 H23 0.9500 . ? C36 C37 1.526(3) . ? C36 H24 0.9900 . ? C36 H25 0.9900 . ? C37 H26 0.9800 . ? C37 H27 0.9800 . ? C37 H28 0.9800 . ? C38 C39 1.531(3) . ? C38 H29 0.9900 . ? C38 H30 0.9900 . ? C39 H31 0.9800 . ? C39 H32 0.9800 . ? C39 H33 0.9800 . ? C40 C41 1.517(4) . ? C40 H34 0.9900 . ? C40 H35 0.9900 . ? C41 H36 0.9800 . ? C41 H37 0.9800 . ? C41 H38 0.9800 . ? C42 C43 1.533(3) . ? C42 H39 0.9900 . ? C42 H40 0.9900 . ? C43 H41 0.9800 . ? C43 H42 0.9800 . ? C43 H43 0.9800 . ? N3 C56 1.517(3) . ? N3 C52 1.520(3) . ? N3 C44 1.525(3) . ? N3 C48 1.527(3) . ? C44 C45 1.510(3) . ? C44 H44 0.9900 . ? C44 H45 0.9900 . ? C45 C46 1.519(3) . ? C45 H46 0.9900 . ? C45 H47 0.9900 . ? C46 C47 1.514(3) . ? C46 H48 0.9900 . ? C46 H49 0.9900 . ? C47 H50 0.9800 . ? C47 H51 0.9800 . ? C47 H52 0.9800 . ? C48 C49 1.508(3) . ? C48 H53 0.9900 . ? C48 H54 0.9900 . ? C49 C50 1.530(3) . ? C49 H55 0.9900 . ? C49 H56 0.9900 . ? C50 C51 1.519(3) . ? C50 H57 0.9900 . ? C50 H58 0.9900 . ? C51 H59 0.9800 . ? C51 H60 0.9800 . ? C51 H61 0.9800 . ? C52 C53 1.514(3) . ? C52 H62 0.9900 . ? C52 H63 0.9900 . ? C53 C54 1.526(4) . ? C53 H64 0.9900 . ? C53 H65 0.9900 . ? C54 C55 1.494(4) . ? C54 H66 0.9900 . ? C54 H67 0.9900 . ? C55 H68 0.9800 . ? C55 H69 0.9800 . ? C55 H70 0.9800 . ? C56 C57 1.521(3) . ? C56 H71 0.9900 . ? C56 H72 0.9900 . ? C57 C58 1.523(4) . ? C57 H73 0.9900 . ? C57 H74 0.9900 . ? C58 C59 1.495(4) . ? C58 H75 0.9900 . ? C58 H76 0.9900 . ? C59 H77 0.9800 . ? C59 H78 0.9800 . ? C59 H79 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 107.52(17) . . ? N1 C1 C12 121.21(17) . . ? C2 C1 C12 131.18(17) . . ? C1 C2 C3 107.60(16) . . ? C1 C2 C36 127.35(18) . . ? C3 C2 C36 125.02(17) . . ? C4 C3 C2 107.41(16) . . ? C4 C3 C38 126.60(16) . . ? C2 C3 C38 125.94(16) . . ? N1 C4 C3 107.49(16) . . ? N1 C4 C5 121.54(16) . . ? C3 C4 C5 130.96(17) . . ? O1 C5 C6 121.15(16) . . ? O1 C5 C4 116.98(15) . . ? C6 C5 C4 121.84(17) . . ? C5 C6 C7 120.19(17) . . ? C5 C6 H1 119.9 . . ? C7 C6 H1 119.9 . . ? O2 C7 C6 120.61(16) . . ? O2 C7 C8 116.34(15) . . ? C6 C7 C8 123.02(17) . . ? N2 C8 C9 107.32(16) . . ? N2 C8 C7 122.83(15) . . ? C9 C8 C7 129.80(17) . . ? C8 C9 C10 107.23(17) . . ? C8 C9 C40 127.42(18) . . ? C10 C9 C40 125.33(18) . . ? C11 C10 C9 107.87(16) . . ? C11 C10 C42 127.93(17) . . ? C9 C10 C42 124.19(18) . . ? N2 C11 C10 107.49(16) . . ? N2 C11 C18 121.04(17) . . ? C10 C11 C18 131.29(17) . . ? C17 C12 C13 117.43(19) . . ? C17 C12 C1 121.59(18) . . ? C13 C12 C1 120.98(18) . . ? C14 C13 C12 121.00(19) . . ? C14 C13 H2 119.5 . . ? C12 C13 H2 119.5 . . ? C15 C14 C13 120.2(2) . . ? C15 C14 H3 119.9 . . ? C13 C14 H3 119.9 . . ? C16 C15 C14 119.4(2) . . ? C16 C15 H4 120.3 . . ? C14 C15 H4 120.3 . . ? C15 C16 C17 120.6(2) . . ? C15 C16 H5 119.7 . . ? C17 C16 H5 119.7 . . ? C16 C17 C12 121.3(2) . . ? C16 C17 H6 119.3 . . ? C12 C17 H6 119.3 . . ? C23 C18 C19 117.72(18) . . ? C23 C18 C11 120.56(17) . . ? C19 C18 C11 121.67(19) . . ? C20 C19 C18 120.7(2) . . ? C20 C19 H7 119.6 . . ? C18 C19 H7 119.6 . . ? C19 C20 C21 120.41(19) . . ? C19 C20 H8 119.8 . . ? C21 C20 H8 119.8 . . ? C22 C21 C20 119.8(2) . . ? C22 C21 H9 120.1 . . ? C20 C21 H9 120.1 . . ? C21 C22 C23 120.1(2) . . ? C21 C22 H10 120.0 . . ? C23 C22 H10 120.0 . . ? C22 C23 C18 121.26(18) . . ? C22 C23 H11 119.4 . . ? C18 C23 H11 119.4 . . ? C1 N1 C4 109.93(15) . . ? C1 N1 H12 125.0 . . ? C4 N1 H12 125.0 . . ? C11 N2 C8 110.10(15) . . ? C11 N2 H13 125.0 . . ? C8 N2 H13 125.0 . . ? C5 O1 B1 118.71(14) . . ? C7 O2 B1 121.37(14) . . ? O2 B1 O1 108.05(14) . . ? O2 B1 C24 105.76(15) . . ? O1 B1 C24 110.04(15) . . ? O2 B1 C30 110.97(15) . . ? O1 B1 C30 108.34(15) . . ? C24 B1 C30 113.55(16) . . ? C25 C24 C29 116.63(18) . . ? C25 C24 B1 124.42(17) . . ? C29 C24 B1 118.95(17) . . ? C26 C25 C24 121.38(19) . . ? C26 C25 H14 119.3 . . ? C24 C25 H14 119.3 . . ? C27 C26 C25 120.4(2) . . ? C27 C26 H15 119.8 . . ? C25 C26 H15 119.8 . . ? C26 C27 C28 119.49(19) . . ? C26 C27 H16 120.3 . . ? C28 C27 H16 120.3 . . ? C27 C28 C29 119.9(2) . . ? C27 C28 H17 120.1 . . ? C29 C28 H17 120.1 . . ? C28 C29 C24 122.2(2) . . ? C28 C29 H18 118.9 . . ? C24 C29 H18 118.9 . . ? C35 C30 C31 115.6(2) . . ? C35 C30 B1 125.01(18) . . ? C31 C30 B1 119.36(17) . . ? C32 C31 C30 122.1(2) . . ? C32 C31 H19 118.9 . . ? C30 C31 H19 118.9 . . ? C33 C32 C31 120.6(2) . . ? C33 C32 H20 119.7 . . ? C31 C32 H20 119.7 . . ? C32 C33 C34 118.8(2) . . ? C32 C33 H21 120.6 . . ? C34 C33 H21 120.6 . . ? C33 C34 C35 120.3(2) . . ? C33 C34 H22 119.9 . . ? C35 C34 H22 119.9 . . ? C34 C35 C30 122.6(2) . . ? C34 C35 H23 118.7 . . ? C30 C35 H23 118.7 . . ? C2 C36 C37 114.83(17) . . ? C2 C36 H24 108.6 . . ? C37 C36 H24 108.6 . . ? C2 C36 H25 108.6 . . ? C37 C36 H25 108.6 . . ? H24 C36 H25 107.5 . . ? C36 C37 H26 109.5 . . ? C36 C37 H27 109.5 . . ? H26 C37 H27 109.5 . . ? C36 C37 H28 109.5 . . ? H26 C37 H28 109.5 . . ? H27 C37 H28 109.5 . . ? C3 C38 C39 111.78(17) . . ? C3 C38 H29 109.3 . . ? C39 C38 H29 109.3 . . ? C3 C38 H30 109.3 . . ? C39 C38 H30 109.3 . . ? H29 C38 H30 107.9 . . ? C38 C39 H31 109.5 . . ? C38 C39 H32 109.5 . . ? H31 C39 H32 109.5 . . ? C38 C39 H33 109.5 . . ? H31 C39 H33 109.5 . . ? H32 C39 H33 109.5 . . ? C9 C40 C41 112.47(19) . . ? C9 C40 H34 109.1 . . ? C41 C40 H34 109.1 . . ? C9 C40 H35 109.1 . . ? C41 C40 H35 109.1 . . ? H34 C40 H35 107.8 . . ? C40 C41 H36 109.5 . . ? C40 C41 H37 109.5 . . ? H36 C41 H37 109.5 . . ? C40 C41 H38 109.5 . . ? H36 C41 H38 109.5 . . ? H37 C41 H38 109.5 . . ? C10 C42 C43 113.34(17) . . ? C10 C42 H39 108.9 . . ? C43 C42 H39 108.9 . . ? C10 C42 H40 108.9 . . ? C43 C42 H40 108.9 . . ? H39 C42 H40 107.7 . . ? C42 C43 H41 109.5 . . ? C42 C43 H42 109.5 . . ? H41 C43 H42 109.5 . . ? C42 C43 H43 109.5 . . ? H41 C43 H43 109.5 . . ? H42 C43 H43 109.5 . . ? C56 N3 C52 110.81(18) . . ? C56 N3 C44 111.64(16) . . ? C52 N3 C44 106.63(16) . . ? C56 N3 C48 106.68(16) . . ? C52 N3 C48 110.61(15) . . ? C44 N3 C48 110.52(17) . . ? C45 C44 N3 115.68(18) . . ? C45 C44 H44 108.4 . . ? N3 C44 H44 108.4 . . ? C45 C44 H45 108.4 . . ? N3 C44 H45 108.4 . . ? H44 C44 H45 107.4 . . ? C44 C45 C46 110.70(19) . . ? C44 C45 H46 109.5 . . ? C46 C45 H46 109.5 . . ? C44 C45 H47 109.5 . . ? C46 C45 H47 109.5 . . ? H46 C45 H47 108.1 . . ? C47 C46 C45 111.6(2) . . ? C47 C46 H48 109.3 . . ? C45 C46 H48 109.3 . . ? C47 C46 H49 109.3 . . ? C45 C46 H49 109.3 . . ? H48 C46 H49 108.0 . . ? C46 C47 H50 109.5 . . ? C46 C47 H51 109.5 . . ? H50 C47 H51 109.5 . . ? C46 C47 H52 109.5 . . ? H50 C47 H52 109.5 . . ? H51 C47 H52 109.5 . . ? C49 C48 N3 116.38(17) . . ? C49 C48 H53 108.2 . . ? N3 C48 H53 108.2 . . ? C49 C48 H54 108.2 . . ? N3 C48 H54 108.2 . . ? H53 C48 H54 107.3 . . ? C48 C49 C50 109.06(18) . . ? C48 C49 H55 109.9 . . ? C50 C49 H55 109.9 . . ? C48 C49 H56 109.9 . . ? C50 C49 H56 109.9 . . ? H55 C49 H56 108.3 . . ? C51 C50 C49 112.8(2) . . ? C51 C50 H57 109.0 . . ? C49 C50 H57 109.0 . . ? C51 C50 H58 109.0 . . ? C49 C50 H58 109.0 . . ? H57 C50 H58 107.8 . . ? C50 C51 H59 109.5 . . ? C50 C51 H60 109.5 . . ? H59 C51 H60 109.5 . . ? C50 C51 H61 109.5 . . ? H59 C51 H61 109.5 . . ? H60 C51 H61 109.5 . . ? C53 C52 N3 114.55(18) . . ? C53 C52 H62 108.6 . . ? N3 C52 H62 108.6 . . ? C53 C52 H63 108.6 . . ? N3 C52 H63 108.6 . . ? H62 C52 H63 107.6 . . ? C52 C53 C54 111.5(2) . . ? C52 C53 H64 109.3 . . ? C54 C53 H64 109.3 . . ? C52 C53 H65 109.3 . . ? C54 C53 H65 109.3 . . ? H64 C53 H65 108.0 . . ? C55 C54 C53 113.7(2) . . ? C55 C54 H66 108.8 . . ? C53 C54 H66 108.8 . . ? C55 C54 H67 108.8 . . ? C53 C54 H67 108.8 . . ? H66 C54 H67 107.7 . . ? C54 C55 H68 109.5 . . ? C54 C55 H69 109.5 . . ? H68 C55 H69 109.5 . . ? C54 C55 H70 109.5 . . ? H68 C55 H70 109.5 . . ? H69 C55 H70 109.5 . . ? N3 C56 C57 116.07(19) . . ? N3 C56 H71 108.3 . . ? C57 C56 H71 108.3 . . ? N3 C56 H72 108.3 . . ? C57 C56 H72 108.3 . . ? H71 C56 H72 107.4 . . ? C56 C57 C58 111.5(2) . . ? C56 C57 H73 109.3 . . ? C58 C57 H73 109.3 . . ? C56 C57 H74 109.3 . . ? C58 C57 H74 109.3 . . ? H73 C57 H74 108.0 . . ? C59 C58 C57 113.9(2) . . ? C59 C58 H75 108.8 . . ? C57 C58 H75 108.8 . . ? C59 C58 H76 108.8 . . ? C57 C58 H76 108.8 . . ? H75 C58 H76 107.7 . . ? C58 C59 H77 109.5 . . ? C58 C59 H78 109.5 . . ? H77 C59 H78 109.5 . . ? C58 C59 H79 109.5 . . ? H77 C59 H79 109.5 . . ? H78 C59 H79 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 2.3(2) . . . . ? C12 C1 C2 C3 -174.2(2) . . . . ? N1 C1 C2 C36 -175.80(19) . . . . ? C12 C1 C2 C36 7.7(4) . . . . ? C1 C2 C3 C4 -2.2(2) . . . . ? C36 C2 C3 C4 175.92(19) . . . . ? C1 C2 C3 C38 175.35(18) . . . . ? C36 C2 C3 C38 -6.5(3) . . . . ? C2 C3 C4 N1 1.3(2) . . . . ? C38 C3 C4 N1 -176.23(18) . . . . ? C2 C3 C4 C5 -179.7(2) . . . . ? C38 C3 C4 C5 2.8(3) . . . . ? N1 C4 C5 O1 172.40(17) . . . . ? C3 C4 C5 O1 -6.5(3) . . . . ? N1 C4 C5 C6 -5.5(3) . . . . ? C3 C4 C5 C6 175.5(2) . . . . ? O1 C5 C6 C7 -4.2(3) . . . . ? C4 C5 C6 C7 173.63(18) . . . . ? C5 C6 C7 O2 12.0(3) . . . . ? C5 C6 C7 C8 -165.70(18) . . . . ? O2 C7 C8 N2 179.05(17) . . . . ? C6 C7 C8 N2 -3.2(3) . . . . ? O2 C7 C8 C9 -4.1(3) . . . . ? C6 C7 C8 C9 173.7(2) . . . . ? N2 C8 C9 C10 -0.1(2) . . . . ? C7 C8 C9 C10 -177.33(19) . . . . ? N2 C8 C9 C40 -178.6(2) . . . . ? C7 C8 C9 C40 4.2(3) . . . . ? C8 C9 C10 C11 -0.2(2) . . . . ? C40 C9 C10 C11 178.3(2) . . . . ? C8 C9 C10 C42 -179.01(18) . . . . ? C40 C9 C10 C42 -0.5(3) . . . . ? C9 C10 C11 N2 0.4(2) . . . . ? C42 C10 C11 N2 179.17(19) . . . . ? C9 C10 C11 C18 -174.6(2) . . . . ? C42 C10 C11 C18 4.1(4) . . . . ? N1 C1 C12 C17 -155.8(2) . . . . ? C2 C1 C12 C17 20.2(3) . . . . ? N1 C1 C12 C13 23.2(3) . . . . ? C2 C1 C12 C13 -160.7(2) . . . . ? C17 C12 C13 C14 -0.7(3) . . . . ? C1 C12 C13 C14 -179.82(19) . . . . ? C12 C13 C14 C15 -1.0(3) . . . . ? C13 C14 C15 C16 1.6(3) . . . . ? C14 C15 C16 C17 -0.4(4) . . . . ? C15 C16 C17 C12 -1.4(4) . . . . ? C13 C12 C17 C16 1.9(3) . . . . ? C1 C12 C17 C16 -179.0(2) . . . . ? N2 C11 C18 C23 -23.7(3) . . . . ? C10 C11 C18 C23 150.8(2) . . . . ? N2 C11 C18 C19 158.97(19) . . . . ? C10 C11 C18 C19 -26.6(3) . . . . ? C23 C18 C19 C20 -1.2(3) . . . . ? C11 C18 C19 C20 176.2(2) . . . . ? C18 C19 C20 C21 1.4(3) . . . . ? C19 C20 C21 C22 -0.5(4) . . . . ? C20 C21 C22 C23 -0.6(4) . . . . ? C21 C22 C23 C18 0.7(4) . . . . ? C19 C18 C23 C22 0.2(3) . . . . ? C11 C18 C23 C22 -177.3(2) . . . . ? C2 C1 N1 C4 -1.5(2) . . . . ? C12 C1 N1 C4 175.40(17) . . . . ? C3 C4 N1 C1 0.1(2) . . . . ? C5 C4 N1 C1 -179.03(17) . . . . ? C10 C11 N2 C8 -0.5(2) . . . . ? C18 C11 N2 C8 175.16(18) . . . . ? C9 C8 N2 C11 0.4(2) . . . . ? C7 C8 N2 C11 177.84(18) . . . . ? C6 C5 O1 B1 -21.2(2) . . . . ? C4 C5 O1 B1 160.84(16) . . . . ? C6 C7 O2 B1 6.8(3) . . . . ? C8 C7 O2 B1 -175.36(16) . . . . ? C7 O2 B1 O1 -28.4(2) . . . . ? C7 O2 B1 C24 -146.22(17) . . . . ? C7 O2 B1 C30 90.2(2) . . . . ? C5 O1 B1 O2 35.3(2) . . . . ? C5 O1 B1 C24 150.33(16) . . . . ? C5 O1 B1 C30 -84.99(18) . . . . ? O2 B1 C24 C25 122.20(19) . . . . ? O1 B1 C24 C25 5.7(3) . . . . ? C30 B1 C24 C25 -115.9(2) . . . . ? O2 B1 C24 C29 -57.9(2) . . . . ? O1 B1 C24 C29 -174.37(16) . . . . ? C30 B1 C24 C29 64.0(2) . . . . ? C29 C24 C25 C26 1.5(3) . . . . ? B1 C24 C25 C26 -178.6(2) . . . . ? C24 C25 C26 C27 -0.5(3) . . . . ? C25 C26 C27 C28 -0.9(4) . . . . ? C26 C27 C28 C29 1.2(3) . . . . ? C27 C28 C29 C24 -0.1(3) . . . . ? C25 C24 C29 C28 -1.2(3) . . . . ? B1 C24 C29 C28 178.88(19) . . . . ? O2 B1 C30 C35 -16.1(3) . . . . ? O1 B1 C30 C35 102.3(2) . . . . ? C24 B1 C30 C35 -135.10(19) . . . . ? O2 B1 C30 C31 163.67(17) . . . . ? O1 B1 C30 C31 -77.9(2) . . . . ? C24 B1 C30 C31 44.7(2) . . . . ? C35 C30 C31 C32 0.0(3) . . . . ? B1 C30 C31 C32 -179.8(2) . . . . ? C30 C31 C32 C33 -0.6(4) . . . . ? C31 C32 C33 C34 0.5(4) . . . . ? C32 C33 C34 C35 0.1(4) . . . . ? C33 C34 C35 C30 -0.7(4) . . . . ? C31 C30 C35 C34 0.6(3) . . . . ? B1 C30 C35 C34 -179.6(2) . . . . ? C1 C2 C36 C37 -99.0(3) . . . . ? C3 C2 C36 C37 83.3(3) . . . . ? C4 C3 C38 C39 82.7(2) . . . . ? C2 C3 C38 C39 -94.4(2) . . . . ? C8 C9 C40 C41 81.5(3) . . . . ? C10 C9 C40 C41 -96.7(2) . . . . ? C11 C10 C42 C43 95.1(3) . . . . ? C9 C10 C42 C43 -86.3(3) . . . . ? C56 N3 C44 C45 -57.0(3) . . . . ? C52 N3 C44 C45 -178.16(19) . . . . ? C48 N3 C44 C45 61.6(2) . . . . ? N3 C44 C45 C46 176.18(19) . . . . ? C44 C45 C46 C47 -178.0(2) . . . . ? C56 N3 C48 C49 -171.34(18) . . . . ? C52 N3 C48 C49 -50.7(2) . . . . ? C44 N3 C48 C49 67.1(2) . . . . ? N3 C48 C49 C50 179.26(17) . . . . ? C48 C49 C50 C51 174.77(18) . . . . ? C56 N3 C52 C53 57.6(2) . . . . ? C44 N3 C52 C53 179.31(19) . . . . ? C48 N3 C52 C53 -60.5(2) . . . . ? N3 C52 C53 C54 163.8(2) . . . . ? C52 C53 C54 C55 61.1(3) . . . . ? C52 N3 C56 C57 56.0(3) . . . . ? C44 N3 C56 C57 -62.7(3) . . . . ? C48 N3 C56 C57 176.5(2) . . . . ? N3 C56 C57 C58 -179.4(2) . . . . ? C56 C57 C58 C59 172.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.405 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.041 #============================================================================== # End of CIF #==============================================================================