# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Hiromitsu Maeda' _publ_contact_author_email maedahir@se.ritsumei.ac.jp _publ_section_title ; Anion-responsive covalently linked and metal-bridged oligomers ; loop_ _publ_author_name H.Maeda K.Kitaguchi Y.Haketa # Attachment '- BF2_ethynyl_HMaeda_CIF.cif' data_90316mae _database_code_depnum_ccdc_archive 'CCDC 819391' #TrackingRef '- BF2_ethynyl_HMaeda_CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H33 B F2 N2 O2' _chemical_formula_weight 562.44 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' F F 0.0171 0.0103 '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 14.470(4) _cell_length_b 10.780(4) _cell_length_c 19.921(7) _cell_angle_alpha 90.00 _cell_angle_beta 108.253(15) _cell_angle_gamma 90.00 _cell_volume 2951.2(18) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 13456 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 27.555 _exptl_crystal_description prism _exptl_crystal_colour red _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 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9500 _exptl_absorpt_correction_T_max 0.9746 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _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 23727 _diffrn_reflns_av_R_equivalents 0.0755 _diffrn_reflns_av_sigmaI/netI 0.0716 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6651 _reflns_number_gt 3943 _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. ISOR was applied for carbons C21, C24, C25, and C26. ; _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^)+(0.0707P)^2^+1.2689P] 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 6651 _refine_ls_number_parameters 403 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.1207 _refine_ls_R_factor_gt 0.0687 _refine_ls_wR_factor_ref 0.1878 _refine_ls_wR_factor_gt 0.1607 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.088 _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 -0.63840(19) 0.3415(3) -0.00806(16) 0.0568(8) Uani 1 1 d . . . H1 H -0.6890 0.3378 0.0129 0.068 Uiso 1 1 calc R . . C2 C -0.57571(18) 0.3461(3) -0.03399(14) 0.0456(7) Uani 1 1 d . . . C3 C -0.49699(16) 0.3534(2) -0.06307(14) 0.0407(6) Uani 1 1 d . . . C4 C -0.50145(18) 0.4319(3) -0.11933(15) 0.0468(7) Uani 1 1 d . . . H2 H -0.5590 0.4779 -0.1414 0.056 Uiso 1 1 calc R . . C5 C -0.42175(18) 0.4427(3) -0.14298(14) 0.0469(7) Uani 1 1 d . . . H3 H -0.4245 0.4970 -0.1811 0.056 Uiso 1 1 calc R . . C6 C -0.33763(18) 0.3749(2) -0.11167(14) 0.0433(6) Uani 1 1 d . . . H4 H -0.2829 0.3845 -0.1279 0.052 Uiso 1 1 calc R . . C7 C -0.33297(16) 0.2935(2) -0.05703(13) 0.0385(6) Uani 1 1 d . . . C8 C -0.41327(17) 0.2844(2) -0.03272(14) 0.0415(6) Uani 1 1 d . . . H5 H -0.4106 0.2299 0.0053 0.050 Uiso 1 1 calc R . . C9 C -0.24542(16) 0.2213(2) -0.02097(13) 0.0382(6) Uani 1 1 d . . . C10 C -0.23515(17) 0.1030(2) 0.00904(13) 0.0394(6) Uani 1 1 d . . . C11 C -0.31554(19) 0.0109(3) 0.00379(15) 0.0483(7) Uani 1 1 d . . . H14 H -0.2943 -0.0711 -0.0082 0.058 Uiso 1 1 calc R . . H15 H -0.3731 0.0361 -0.0359 0.058 Uiso 1 1 calc R . . C12 C -0.3466(2) -0.0037(3) 0.06935(18) 0.0626(8) Uani 1 1 d . . . H16 H -0.2925 -0.0378 0.1079 0.094 Uiso 1 1 calc R . . H17 H -0.4024 -0.0602 0.0592 0.094 Uiso 1 1 calc R . . H18 H -0.3650 0.0774 0.0834 0.094 Uiso 1 1 calc R . . C13 C -0.13509(17) 0.0820(2) 0.04157(13) 0.0382(6) Uani 1 1 d . . . C14 C -0.0929(2) -0.0298(3) 0.08473(15) 0.0489(7) Uani 1 1 d . . . H19 H -0.0315 -0.0530 0.0761 0.059 Uiso 1 1 calc R . . H20 H -0.1388 -0.1002 0.0697 0.059 Uiso 1 1 calc R . . C15 C -0.0730(2) -0.0065(3) 0.16336(16) 0.0644(9) Uani 1 1 d . . . H21 H -0.0258 0.0611 0.1787 0.097 Uiso 1 1 calc R . . H22 H -0.0466 -0.0820 0.1899 0.097 Uiso 1 1 calc R . . H23 H -0.1337 0.0164 0.1721 0.097 Uiso 1 1 calc R . . C16 C -0.08599(17) 0.1879(2) 0.02942(13) 0.0377(6) Uani 1 1 d . . . C17 C 0.01331(17) 0.2239(2) 0.04826(13) 0.0386(6) Uani 1 1 d . . . C18 C 0.09166(17) 0.1578(2) 0.09199(14) 0.0431(6) Uani 1 1 d . . . H6 H 0.0807 0.0814 0.1120 0.052 Uiso 1 1 calc R . . C19 C 0.18499(18) 0.2022(2) 0.10644(14) 0.0425(6) Uani 1 1 d . . . C20 C 0.27101(18) 0.1439(3) 0.15081(16) 0.0516(7) Uani 1 1 d . A . C21 C 0.2892(2) 0.0363(3) 0.1911(3) 0.1021(16) Uani 1 1 d U . . C22 C 0.2124(5) -0.0331(8) 0.2216(4) 0.043(2) Uani 0.534(16) 1 d P A 2 H31 H 0.2429 -0.0568 0.2717 0.052 Uiso 0.534(16) 1 calc PR A 2 H32 H 0.1552 0.0202 0.2177 0.052 Uiso 0.534(16) 1 calc PR A 2 C24 C 0.3894(2) 0.0298(3) 0.2256(2) 0.0884(13) Uani 1 1 d U A . C25 C 0.4415(3) -0.0771(4) 0.2743(3) 0.1176(18) Uani 1 1 d U . . H26 H 0.4803 -0.0439 0.3209 0.141 Uiso 1 1 calc R A . H27 H 0.3929 -0.1360 0.2815 0.141 Uiso 1 1 calc R . . C26 C 0.5051(4) -0.1408(4) 0.2410(3) 0.131(2) Uani 1 1 d U A . H28 H 0.4662 -0.1731 0.1949 0.196 Uiso 1 1 calc R . . H29 H 0.5382 -0.2095 0.2712 0.196 Uiso 1 1 calc R . . H30 H 0.5536 -0.0822 0.2348 0.196 Uiso 1 1 calc R . . C27 C 0.43152(18) 0.1335(3) 0.20612(16) 0.0503(7) Uani 1 1 d . . . C28 C 0.53279(18) 0.1764(2) 0.22854(15) 0.0469(7) Uani 1 1 d . A . C29 C 0.5908(2) 0.1576(3) 0.29784(17) 0.0616(8) Uani 1 1 d . . . H7 H 0.5644 0.1182 0.3304 0.074 Uiso 1 1 calc R A . C30 C 0.6868(2) 0.1961(3) 0.31965(19) 0.0706(10) Uani 1 1 d . A . H8 H 0.7260 0.1821 0.3671 0.085 Uiso 1 1 calc R . . C31 C 0.7259(2) 0.2541(3) 0.27377(18) 0.0627(9) Uani 1 1 d . . . H9 H 0.7922 0.2792 0.2894 0.075 Uiso 1 1 calc R A . C32 C 0.66919(19) 0.2762(3) 0.20460(16) 0.0516(7) Uani 1 1 d . A . C33 C 0.57191(18) 0.2375(3) 0.18253(15) 0.0473(7) Uani 1 1 d . . . H10 H 0.5322 0.2534 0.1354 0.057 Uiso 1 1 calc R A . C34 C 0.7107(2) 0.3390(3) 0.15722(18) 0.0590(8) Uani 1 1 d . . . C35 C 0.7475(2) 0.3904(4) 0.1201(2) 0.0730(10) Uani 1 1 d . A . H11 H 0.7772 0.4320 0.0901 0.088 Uiso 1 1 calc R . . N1 N 0.35922(14) 0.2005(2) 0.16082(11) 0.0424(5) Uani 1 1 d . A . H12 H 0.3677 0.2704 0.1407 0.051 Uiso 1 1 calc R . . N2 N -0.15535(14) 0.2696(2) -0.00969(11) 0.0397(5) Uani 1 1 d . . . H13 H -0.1430 0.3423 -0.0250 0.048 Uiso 1 1 calc R . . O1 O 0.02767(12) 0.33031(17) 0.02135(11) 0.0548(5) Uani 1 1 d . . . O2 O 0.20199(12) 0.30759(18) 0.07879(11) 0.0551(5) Uani 1 1 d . . . B1 B 0.1227(2) 0.3896(3) 0.03778(18) 0.0459(8) Uani 1 1 d . . . F1 F 0.12349(11) 0.49440(16) 0.07722(10) 0.0656(5) Uani 1 1 d . . . F2 F 0.14047(11) 0.4232(2) -0.02327(10) 0.0739(6) Uani 1 1 d . . . C36 C 0.1838(6) -0.1472(9) 0.1747(4) 0.062(2) Uani 0.534(16) 1 d P A 2 H33 H 0.1591 -0.1214 0.1251 0.093 Uiso 0.534(16) 1 calc PR A 2 H34 H 0.1331 -0.1931 0.1872 0.093 Uiso 0.534(16) 1 calc PR A 2 H35 H 0.2409 -0.2005 0.1816 0.093 Uiso 0.534(16) 1 calc PR A 2 C38 C 0.2241(7) -0.0845(10) 0.1699(4) 0.051(3) Uani 0.466(16) 1 d P A 1 H36 H 0.1743 -0.0772 0.1229 0.062 Uiso 0.466(16) 1 calc PR A 1 H37 H 0.2633 -0.1604 0.1719 0.062 Uiso 0.466(16) 1 calc PR A 1 C37 C 0.1813(10) -0.0781(14) 0.2288(6) 0.079(3) Uani 0.466(16) 1 d P A 1 H38 H 0.2336 -0.0804 0.2741 0.119 Uiso 0.466(16) 1 calc PR A 1 H39 H 0.1377 -0.1489 0.2257 0.119 Uiso 0.466(16) 1 calc PR A 1 H40 H 0.1445 -0.0008 0.2252 0.119 Uiso 0.466(16) 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 C1 0.0337(14) 0.077(2) 0.0579(18) -0.0020(16) 0.0122(13) 0.0030(14) C2 0.0277(12) 0.0539(17) 0.0500(16) -0.0005(13) 0.0048(11) 0.0030(12) C3 0.0246(11) 0.0487(15) 0.0445(15) -0.0045(12) 0.0046(10) -0.0023(11) C4 0.0334(13) 0.0496(16) 0.0521(16) 0.0004(13) 0.0060(12) 0.0049(12) C5 0.0400(14) 0.0491(16) 0.0484(16) 0.0083(13) 0.0092(12) 0.0015(12) C6 0.0332(13) 0.0482(16) 0.0472(15) 0.0006(12) 0.0110(11) -0.0008(12) C7 0.0275(12) 0.0430(14) 0.0416(14) -0.0011(11) 0.0057(10) -0.0013(10) C8 0.0288(12) 0.0504(16) 0.0420(14) 0.0007(12) 0.0063(11) -0.0015(11) C9 0.0271(12) 0.0447(15) 0.0409(14) -0.0018(11) 0.0078(10) -0.0001(10) C10 0.0327(13) 0.0399(14) 0.0449(14) -0.0026(11) 0.0110(11) -0.0019(11) C11 0.0375(14) 0.0423(15) 0.0640(18) -0.0026(13) 0.0145(13) -0.0082(12) C12 0.0569(18) 0.0581(19) 0.080(2) 0.0060(16) 0.0316(17) -0.0109(15) C13 0.0344(13) 0.0377(14) 0.0416(14) 0.0015(11) 0.0107(11) -0.0011(11) C14 0.0399(14) 0.0429(15) 0.0592(18) 0.0065(13) 0.0087(13) -0.0024(12) C15 0.0580(19) 0.068(2) 0.061(2) 0.0177(16) 0.0097(15) -0.0081(16) C16 0.0282(12) 0.0400(14) 0.0427(14) 0.0016(11) 0.0078(10) 0.0036(10) C17 0.0308(12) 0.0390(14) 0.0461(15) 0.0034(11) 0.0120(11) 0.0016(10) C18 0.0325(13) 0.0407(15) 0.0532(16) 0.0119(12) 0.0094(11) 0.0018(11) C19 0.0329(13) 0.0386(14) 0.0543(16) 0.0089(12) 0.0113(12) 0.0061(11) C20 0.0293(13) 0.0491(17) 0.0685(19) 0.0130(14) 0.0039(12) 0.0019(12) C21 0.0389(17) 0.070(2) 0.168(4) 0.066(3) -0.010(2) -0.0037(16) C22 0.032(3) 0.045(4) 0.052(4) 0.005(3) 0.014(3) 0.005(3) C24 0.0401(16) 0.061(2) 0.140(3) 0.043(2) -0.0059(19) 0.0010(15) C25 0.049(2) 0.079(3) 0.202(5) 0.051(3) 0.007(3) 0.002(2) C26 0.105(3) 0.067(3) 0.182(5) -0.009(3) -0.010(3) 0.003(3) C27 0.0321(13) 0.0455(16) 0.0632(18) 0.0072(13) 0.0004(12) 0.0083(12) C28 0.0353(13) 0.0384(14) 0.0560(17) 0.0005(12) -0.0013(12) 0.0068(11) C29 0.0507(17) 0.0550(19) 0.063(2) 0.0119(15) -0.0051(15) 0.0020(14) C30 0.0514(18) 0.066(2) 0.067(2) 0.0086(17) -0.0218(16) -0.0016(16) C31 0.0365(15) 0.0578(19) 0.075(2) -0.0037(17) -0.0091(15) -0.0007(14) C32 0.0364(14) 0.0466(16) 0.0632(19) -0.0113(14) 0.0032(13) 0.0041(12) C33 0.0316(13) 0.0489(16) 0.0497(16) -0.0088(13) -0.0040(11) 0.0055(12) C34 0.0395(16) 0.063(2) 0.068(2) -0.0171(17) 0.0075(15) -0.0059(14) C35 0.056(2) 0.085(3) 0.078(2) -0.019(2) 0.0210(18) -0.0164(19) N1 0.0292(11) 0.0405(12) 0.0514(13) 0.0076(10) 0.0037(9) 0.0030(9) N2 0.0280(10) 0.0389(12) 0.0503(13) 0.0054(10) 0.0097(9) 0.0007(9) O1 0.0267(9) 0.0474(11) 0.0826(15) 0.0249(10) 0.0057(9) 0.0020(8) O2 0.0268(9) 0.0501(11) 0.0821(15) 0.0270(10) 0.0079(9) 0.0034(8) B1 0.0255(14) 0.0461(18) 0.063(2) 0.0177(15) 0.0093(14) 0.0038(13) F1 0.0410(9) 0.0559(11) 0.0935(14) 0.0025(10) 0.0118(9) 0.0043(8) F2 0.0386(9) 0.1114(16) 0.0723(12) 0.0345(11) 0.0183(8) 0.0082(9) C36 0.067(5) 0.045(5) 0.080(5) -0.006(3) 0.031(3) -0.012(4) C38 0.051(5) 0.045(5) 0.054(4) 0.003(3) 0.011(3) 0.009(4) C37 0.066(7) 0.096(9) 0.073(6) 0.017(6) 0.017(5) -0.004(6) _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 1.177(4) . ? C1 H1 0.9500 . ? C2 C3 1.433(4) . ? C3 C8 1.389(3) . ? C3 C4 1.389(4) . ? C4 C5 1.381(4) . ? C4 H2 0.9500 . ? C5 C6 1.389(3) . ? C5 H3 0.9500 . ? C6 C7 1.383(4) . ? C6 H4 0.9500 . ? C7 C8 1.395(3) . ? C7 C9 1.469(3) . ? C8 H5 0.9500 . ? C9 N2 1.355(3) . ? C9 C10 1.396(4) . ? C10 C13 1.407(3) . ? C10 C11 1.508(3) . ? C11 C12 1.517(4) . ? C11 H14 0.9900 . ? C11 H15 0.9900 . ? C12 H16 0.9800 . ? C12 H17 0.9800 . ? C12 H18 0.9800 . ? C13 C16 1.405(3) . ? C13 C14 1.495(4) . ? C14 C15 1.522(4) . ? C14 H19 0.9900 . ? C14 H20 0.9900 . ? C15 H21 0.9800 . ? C15 H22 0.9800 . ? C15 H23 0.9800 . ? C16 N2 1.379(3) . ? C16 C17 1.421(3) . ? C17 O1 1.310(3) . ? C17 C18 1.391(3) . ? C18 C19 1.376(3) . ? C18 H6 0.9500 . ? C19 O2 1.319(3) . ? C19 C20 1.427(3) . ? C20 N1 1.372(3) . ? C20 C21 1.388(4) . ? C21 C24 1.399(4) . ? C21 C38 1.585(13) . ? C21 C22 1.609(10) . ? C22 C36 1.522(13) . ? C22 H31 0.9900 . ? C22 H32 0.9900 . ? C24 C27 1.385(4) . ? C24 C25 1.542(5) . ? C25 C26 1.463(7) . ? C25 H26 0.9900 . ? C25 H27 0.9900 . ? C26 H28 0.9800 . ? C26 H29 0.9800 . ? C26 H30 0.9800 . ? C27 N1 1.356(3) . ? C27 C28 1.467(4) . ? C28 C33 1.385(4) . ? C28 C29 1.388(4) . ? C29 C30 1.383(4) . ? C29 H7 0.9500 . ? C30 C31 1.368(5) . ? C30 H8 0.9500 . ? C31 C32 1.386(4) . ? C31 H9 0.9500 . ? C32 C33 1.400(4) . ? C32 C34 1.437(5) . ? C33 H10 0.9500 . ? C34 C35 1.176(5) . ? C35 H11 0.9500 . ? N1 H12 0.8800 . ? N2 H13 0.8800 . ? O1 B1 1.458(3) . ? O2 B1 1.476(3) . ? B1 F1 1.374(4) . ? B1 F2 1.368(4) . ? C36 H33 0.9800 . ? C36 H34 0.9800 . ? C36 H35 0.9800 . ? C38 C37 1.489(18) . ? C38 H36 0.9900 . ? C38 H37 0.9900 . ? C37 H38 0.9800 . ? C37 H39 0.9800 . ? C37 H40 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 C2 C1 H1 180.0 . . ? C1 C2 C3 177.8(3) . . ? C8 C3 C4 119.4(2) . . ? C8 C3 C2 119.3(2) . . ? C4 C3 C2 121.2(2) . . ? C5 C4 C3 119.6(2) . . ? C5 C4 H2 120.2 . . ? C3 C4 H2 120.2 . . ? C4 C5 C6 120.7(3) . . ? C4 C5 H3 119.6 . . ? C6 C5 H3 119.6 . . ? C7 C6 C5 120.5(2) . . ? C7 C6 H4 119.8 . . ? C5 C6 H4 119.8 . . ? C6 C7 C8 118.5(2) . . ? C6 C7 C9 122.9(2) . . ? C8 C7 C9 118.5(2) . . ? C3 C8 C7 121.3(2) . . ? C3 C8 H5 119.4 . . ? C7 C8 H5 119.4 . . ? N2 C9 C10 108.2(2) . . ? N2 C9 C7 121.0(2) . . ? C10 C9 C7 130.8(2) . . ? C9 C10 C13 107.5(2) . . ? C9 C10 C11 126.5(2) . . ? C13 C10 C11 125.9(2) . . ? C10 C11 C12 116.0(2) . . ? C10 C11 H14 108.3 . . ? C12 C11 H14 108.3 . . ? C10 C11 H15 108.3 . . ? C12 C11 H15 108.3 . . ? H14 C11 H15 107.4 . . ? C11 C12 H16 109.5 . . ? C11 C12 H17 109.5 . . ? H16 C12 H17 109.5 . . ? C11 C12 H18 109.5 . . ? H16 C12 H18 109.5 . . ? H17 C12 H18 109.5 . . ? C16 C13 C10 107.0(2) . . ? C16 C13 C14 128.1(2) . . ? C10 C13 C14 124.8(2) . . ? C13 C14 C15 111.7(2) . . ? C13 C14 H19 109.3 . . ? C15 C14 H19 109.3 . . ? C13 C14 H20 109.3 . . ? C15 C14 H20 109.3 . . ? H19 C14 H20 107.9 . . ? C14 C15 H21 109.5 . . ? C14 C15 H22 109.5 . . ? H21 C15 H22 109.5 . . ? C14 C15 H23 109.5 . . ? H21 C15 H23 109.5 . . ? H22 C15 H23 109.5 . . ? N2 C16 C13 107.4(2) . . ? N2 C16 C17 118.2(2) . . ? C13 C16 C17 134.5(2) . . ? O1 C17 C18 120.2(2) . . ? O1 C17 C16 114.1(2) . . ? C18 C17 C16 125.8(2) . . ? C19 C18 C17 120.4(2) . . ? C19 C18 H6 119.8 . . ? C17 C18 H6 119.8 . . ? O2 C19 C18 120.8(2) . . ? O2 C19 C20 113.4(2) . . ? C18 C19 C20 125.7(2) . . ? N1 C20 C21 106.8(2) . . ? N1 C20 C19 119.0(2) . . ? C21 C20 C19 134.2(3) . . ? C20 C21 C24 107.8(3) . . ? C20 C21 C38 122.9(4) . . ? C24 C21 C38 121.9(4) . . ? C20 C21 C22 125.4(4) . . ? C24 C21 C22 121.5(4) . . ? C38 C21 C22 45.2(4) . . ? C36 C22 C21 103.3(7) . . ? C36 C22 H31 111.1 . . ? C21 C22 H31 111.1 . . ? C36 C22 H32 111.1 . . ? C21 C22 H32 111.1 . . ? H31 C22 H32 109.1 . . ? C27 C24 C21 107.5(3) . . ? C27 C24 C25 127.5(3) . . ? C21 C24 C25 125.0(3) . . ? C26 C25 C24 108.6(5) . . ? C26 C25 H26 110.0 . . ? C24 C25 H26 110.0 . . ? C26 C25 H27 110.0 . . ? C24 C25 H27 110.0 . . ? H26 C25 H27 108.4 . . ? C25 C26 H28 109.5 . . ? C25 C26 H29 109.5 . . ? H28 C26 H29 109.5 . . ? C25 C26 H30 109.5 . . ? H28 C26 H30 109.5 . . ? H29 C26 H30 109.5 . . ? N1 C27 C24 107.5(2) . . ? N1 C27 C28 121.6(2) . . ? C24 C27 C28 130.9(2) . . ? C33 C28 C29 118.9(3) . . ? C33 C28 C27 121.7(2) . . ? C29 C28 C27 119.5(3) . . ? C30 C29 C28 120.2(3) . . ? C30 C29 H7 119.9 . . ? C28 C29 H7 119.9 . . ? C31 C30 C29 120.8(3) . . ? C31 C30 H8 119.6 . . ? C29 C30 H8 119.6 . . ? C30 C31 C32 120.2(3) . . ? C30 C31 H9 119.9 . . ? C32 C31 H9 119.9 . . ? C31 C32 C33 119.0(3) . . ? C31 C32 C34 119.7(3) . . ? C33 C32 C34 121.3(3) . . ? C28 C33 C32 120.9(3) . . ? C28 C33 H10 119.6 . . ? C32 C33 H10 119.6 . . ? C35 C34 C32 177.9(3) . . ? C34 C35 H11 180.0 . . ? C27 N1 C20 110.4(2) . . ? C27 N1 H12 124.8 . . ? C20 N1 H12 124.8 . . ? C9 N2 C16 109.9(2) . . ? C9 N2 H13 125.1 . . ? C16 N2 H13 125.1 . . ? C17 O1 B1 123.5(2) . . ? C19 O2 B1 122.2(2) . . ? F1 B1 F2 108.7(2) . . ? F1 B1 O1 109.1(2) . . ? F2 B1 O1 110.1(2) . . ? F1 B1 O2 108.1(2) . . ? F2 B1 O2 108.7(2) . . ? O1 B1 O2 112.1(2) . . ? C22 C36 H33 109.5 . . ? C22 C36 H34 109.5 . . ? H33 C36 H34 109.5 . . ? C22 C36 H35 109.5 . . ? H33 C36 H35 109.5 . . ? H34 C36 H35 109.5 . . ? C37 C38 C21 96.4(9) . . ? C37 C38 H36 112.5 . . ? C21 C38 H36 112.5 . . ? C37 C38 H37 112.5 . . ? C21 C38 H37 112.5 . . ? H36 C38 H37 110.0 . . ? 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 C1 C2 C3 C8 61(8) . . . . ? C1 C2 C3 C4 -117(8) . . . . ? C8 C3 C4 C5 -1.7(4) . . . . ? C2 C3 C4 C5 175.8(3) . . . . ? C3 C4 C5 C6 0.7(4) . . . . ? C4 C5 C6 C7 1.2(4) . . . . ? C5 C6 C7 C8 -2.1(4) . . . . ? C5 C6 C7 C9 -178.7(2) . . . . ? C4 C3 C8 C7 0.9(4) . . . . ? C2 C3 C8 C7 -176.7(2) . . . . ? C6 C7 C8 C3 1.1(4) . . . . ? C9 C7 C8 C3 177.9(2) . . . . ? C6 C7 C9 N2 35.6(4) . . . . ? C8 C7 C9 N2 -141.1(2) . . . . ? C6 C7 C9 C10 -147.1(3) . . . . ? C8 C7 C9 C10 36.3(4) . . . . ? N2 C9 C10 C13 2.1(3) . . . . ? C7 C9 C10 C13 -175.5(2) . . . . ? N2 C9 C10 C11 -174.3(2) . . . . ? C7 C9 C10 C11 8.1(4) . . . . ? C9 C10 C11 C12 -104.6(3) . . . . ? C13 C10 C11 C12 79.6(4) . . . . ? C9 C10 C13 C16 -1.1(3) . . . . ? C11 C10 C13 C16 175.3(2) . . . . ? C9 C10 C13 C14 175.0(2) . . . . ? C11 C10 C13 C14 -8.5(4) . . . . ? C16 C13 C14 C15 79.9(3) . . . . ? C10 C13 C14 C15 -95.5(3) . . . . ? C10 C13 C16 N2 -0.2(3) . . . . ? C14 C13 C16 N2 -176.2(2) . . . . ? C10 C13 C16 C17 179.7(3) . . . . ? C14 C13 C16 C17 3.7(5) . . . . ? N2 C16 C17 O1 -4.4(3) . . . . ? C13 C16 C17 O1 175.7(3) . . . . ? N2 C16 C17 C18 174.5(2) . . . . ? C13 C16 C17 C18 -5.4(5) . . . . ? O1 C17 C18 C19 -1.1(4) . . . . ? C16 C17 C18 C19 -180.0(3) . . . . ? C17 C18 C19 O2 -0.5(4) . . . . ? C17 C18 C19 C20 179.4(3) . . . . ? O2 C19 C20 N1 0.7(4) . . . . ? C18 C19 C20 N1 -179.3(3) . . . . ? O2 C19 C20 C21 178.8(4) . . . . ? C18 C19 C20 C21 -1.1(6) . . . . ? N1 C20 C21 C24 0.4(5) . . . . ? C19 C20 C21 C24 -177.9(4) . . . . ? N1 C20 C21 C38 -150.0(5) . . . . ? C19 C20 C21 C38 31.7(8) . . . . ? N1 C20 C21 C22 154.7(5) . . . . ? C19 C20 C21 C22 -23.6(8) . . . . ? C20 C21 C22 C36 106.2(6) . . . . ? C24 C21 C22 C36 -102.7(6) . . . . ? C38 C21 C22 C36 2.6(5) . . . . ? C20 C21 C24 C27 0.0(6) . . . . ? C38 C21 C24 C27 150.7(5) . . . . ? C22 C21 C24 C27 -155.6(5) . . . . ? C20 C21 C24 C25 -178.2(5) . . . . ? C38 C21 C24 C25 -27.4(8) . . . . ? C22 C21 C24 C25 26.3(8) . . . . ? C27 C24 C25 C26 -63.4(6) . . . . ? C21 C24 C25 C26 114.4(5) . . . . ? C21 C24 C27 N1 -0.3(5) . . . . ? C25 C24 C27 N1 177.8(5) . . . . ? C21 C24 C27 C28 177.1(4) . . . . ? C25 C24 C27 C28 -4.8(8) . . . . ? N1 C27 C28 C33 -37.1(4) . . . . ? C24 C27 C28 C33 145.8(4) . . . . ? N1 C27 C28 C29 141.7(3) . . . . ? C24 C27 C28 C29 -35.4(5) . . . . ? C33 C28 C29 C30 -2.0(5) . . . . ? C27 C28 C29 C30 179.2(3) . . . . ? C28 C29 C30 C31 0.6(5) . . . . ? C29 C30 C31 C32 0.7(5) . . . . ? C30 C31 C32 C33 -0.5(5) . . . . ? C30 C31 C32 C34 179.0(3) . . . . ? C29 C28 C33 C32 2.1(4) . . . . ? C27 C28 C33 C32 -179.1(3) . . . . ? C31 C32 C33 C28 -0.9(4) . . . . ? C34 C32 C33 C28 179.6(3) . . . . ? C31 C32 C34 C35 3(10) . . . . ? C33 C32 C34 C35 -177(100) . . . . ? C24 C27 N1 C20 0.6(4) . . . . ? C28 C27 N1 C20 -177.1(3) . . . . ? C21 C20 N1 C27 -0.6(4) . . . . ? C19 C20 N1 C27 178.0(3) . . . . ? C10 C9 N2 C16 -2.3(3) . . . . ? C7 C9 N2 C16 175.6(2) . . . . ? C13 C16 N2 C9 1.6(3) . . . . ? C17 C16 N2 C9 -178.4(2) . . . . ? C18 C17 O1 B1 -3.7(4) . . . . ? C16 C17 O1 B1 175.3(3) . . . . ? C18 C19 O2 B1 6.8(4) . . . . ? C20 C19 O2 B1 -173.1(3) . . . . ? C17 O1 B1 F1 -110.8(3) . . . . ? C17 O1 B1 F2 130.0(3) . . . . ? C17 O1 B1 O2 8.9(4) . . . . ? C19 O2 B1 F1 109.8(3) . . . . ? C19 O2 B1 F2 -132.3(3) . . . . ? C19 O2 B1 O1 -10.4(4) . . . . ? C20 C21 C38 C37 -111.4(7) . . . . ? C24 C21 C38 C37 102.2(7) . . . . ? C22 C21 C38 C37 -2.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.478 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.050 #============================================================================== # End of CIF #============================================================================== data_0817maed _database_code_depnum_ccdc_archive 'CCDC 819392' #TrackingRef '- BF2_ethynyl_HMaeda_CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H29 B F2 N2 O2' _chemical_formula_weight 462.33 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' F F 0.0171 0.0103 '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 12.211(5) _cell_length_b 13.253(5) _cell_length_c 16.614(5) _cell_angle_alpha 102.298(14) _cell_angle_beta 97.612(13) _cell_angle_gamma 105.900(15) _cell_volume 2473.7(15) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 17881 _cell_measurement_theta_min 3.195 _cell_measurement_theta_max 27.52 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9493 _exptl_absorpt_correction_T_max 0.9827 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _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 23491 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 27.48 _reflns_number_total 11100 _reflns_number_gt 8088 _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^)+(0.1180P)^2^+0.5727P] 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 11100 _refine_ls_number_parameters 621 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0726 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1699 _refine_ls_wR_factor_gt 0.1552 _refine_ls_goodness_of_fit_ref 0.926 _refine_ls_restrained_S_all 0.926 _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 F2 F 0.21222(9) 0.26384(9) 0.33459(6) 0.0269(2) Uani 1 1 d . . . F1 F 0.36911(8) 0.39321(8) 0.31947(6) 0.0244(2) Uani 1 1 d . . . F3 F 0.51727(10) 0.12520(10) 0.10034(7) 0.0332(3) Uani 1 1 d . . . O2 O 0.21646(10) 0.30623(10) 0.20514(7) 0.0233(3) Uani 1 1 d . . . O3 O 0.19766(10) 0.43413(10) 0.32715(7) 0.0215(3) Uani 1 1 d . . . N4 N 0.58226(12) 0.12360(12) -0.16564(8) 0.0205(3) Uani 1 1 d . . . H1 H 0.5420 0.0674 -0.1503 0.025 Uiso 1 1 calc R . . N2 N 0.09841(12) 0.56281(11) 0.41080(8) 0.0192(3) Uani 1 1 d . . . H3 H 0.1699 0.5687 0.4335 0.023 Uiso 1 1 calc R . . N1 N 0.14420(13) 0.17463(13) 0.04987(9) 0.0243(3) Uani 1 1 d . . . H9 H 0.2138 0.1790 0.0756 0.029 Uiso 1 1 calc R . . C12 C 0.10932(14) 0.29540(13) 0.16780(10) 0.0191(3) Uani 1 1 d . . . C13 C 0.04113(15) 0.34741(14) 0.21150(10) 0.0205(3) Uani 1 1 d . . . H63 H -0.0386 0.3323 0.1877 0.025 Uiso 1 1 calc R . . C14 C 0.54153(15) 0.36763(14) 0.08005(10) 0.0212(3) Uani 1 1 d . . . C15 C 0.08498(14) 0.71110(13) 0.52237(10) 0.0190(3) Uani 1 1 d . . . C16 C 0.08991(14) 0.42114(13) 0.28970(10) 0.0195(3) Uani 1 1 d . . . C17 C 0.01628(15) 0.74015(14) 0.57896(10) 0.0210(3) Uani 1 1 d . . . H4 H -0.0647 0.7025 0.5671 0.025 Uiso 1 1 calc R . . C18 C 0.62394(15) 0.11706(15) -0.23765(10) 0.0227(4) Uani 1 1 d . . . N3 N 0.50463(14) 0.46776(13) 0.20690(9) 0.0249(3) Uani 1 1 d . . . H5 H 0.4616 0.4091 0.2178 0.030 Uiso 1 1 calc R . . C20 C 0.06510(16) 0.82281(14) 0.65164(10) 0.0226(3) Uani 1 1 d . . . H10 H 0.0172 0.8419 0.6890 0.027 Uiso 1 1 calc R . . C21 C 0.56953(14) 0.25302(14) -0.04385(10) 0.0201(3) Uani 1 1 d . . . C22 C 0.23611(16) 0.95677(15) 0.75054(11) 0.0250(4) Uani 1 1 d . . . C23 C 0.59602(15) 0.35472(14) 0.01195(11) 0.0233(4) Uani 1 1 d . . . H6 H 0.6515 0.4156 0.0035 0.028 Uiso 1 1 calc R . . C24 C 0.55537(15) 0.46857(14) 0.13744(10) 0.0224(3) Uani 1 1 d . . . C25 C 0.59707(15) 0.01102(14) -0.29849(11) 0.0219(3) Uani 1 1 d . . . C26 C -0.01671(16) 0.12733(14) -0.04846(10) 0.0230(4) Uani 1 1 d . . . C27 C 0.53522(17) -0.18543(15) -0.32968(11) 0.0274(4) Uani 1 1 d . . . H11 H 0.5174 -0.2495 -0.3104 0.033 Uiso 1 1 calc R . . C28 C 0.52579(16) -0.19411(15) -0.41543(11) 0.0262(4) Uani 1 1 d . . . C29 C 0.03414(14) 0.62320(13) 0.44514(10) 0.0193(3) Uani 1 1 d . . . C30 C -0.17488(15) 0.44830(14) 0.24972(11) 0.0230(3) Uani 1 1 d . . . H12 H -0.1458 0.4350 0.1968 0.028 Uiso 1 1 calc R . . H13 H -0.2252 0.4948 0.2448 0.028 Uiso 1 1 calc R . . C31 C 0.61156(15) 0.23016(14) -0.11981(10) 0.0214(3) Uani 1 1 d . . . C32 C -0.07350(14) 0.50740(13) 0.32161(10) 0.0190(3) Uani 1 1 d . . . C33 C 0.18388(15) 0.87864(14) 0.67091(10) 0.0213(3) Uani 1 1 d . . . C34 C 0.59940(16) 0.64093(15) 0.21861(11) 0.0248(4) Uani 1 1 d . . . C35 C 0.20366(15) 0.76956(14) 0.54077(11) 0.0229(4) Uani 1 1 d . . . H14 H 0.2513 0.7522 0.5025 0.027 Uiso 1 1 calc R . . C36 C 0.68452(15) 0.22330(15) -0.23866(11) 0.0229(4) Uani 1 1 d . . . C37 C 0.25251(15) 0.85217(14) 0.61379(11) 0.0229(4) Uani 1 1 d . . . H15 H 0.3331 0.8912 0.6252 0.027 Uiso 1 1 calc R . . C38 C -0.02797(15) 0.20237(14) 0.02127(10) 0.0203(3) Uani 1 1 d . . . C39 C 0.07332(15) 0.23011(14) 0.08360(10) 0.0211(3) Uani 1 1 d . . . C40 C 0.61453(16) 0.57826(14) 0.14370(11) 0.0233(4) Uani 1 1 d . . . C41 C 0.72873(17) 0.41606(15) -0.14137(11) 0.0276(4) Uani 1 1 d . . . H16 H 0.6787 0.4491 -0.1094 0.033 Uiso 1 1 calc R . . H17 H 0.7301 0.4411 -0.1934 0.033 Uiso 1 1 calc R . . C42 C -0.07423(15) 0.59021(14) 0.39089(10) 0.0199(3) Uani 1 1 d . . . C43 C 0.67618(15) 0.29462(14) -0.16497(10) 0.0220(3) Uani 1 1 d . . . C44 C 0.03554(14) 0.49111(13) 0.33532(10) 0.0187(3) Uani 1 1 d . . . C45 C -0.13233(15) 0.23980(15) 0.02661(11) 0.0230(3) Uani 1 1 d . . . H18 H -0.1704 0.2373 -0.0306 0.028 Uiso 1 1 calc R . . H19 H -0.1074 0.3161 0.0609 0.028 Uiso 1 1 calc R . . C46 C -0.17149(15) 0.63764(15) 0.40147(11) 0.0234(4) Uani 1 1 d . . . H20 H -0.2079 0.6415 0.3458 0.028 Uiso 1 1 calc R . . H21 H -0.1386 0.7128 0.4379 0.028 Uiso 1 1 calc R . . C47 C 0.57032(16) -0.08461(15) -0.27198(11) 0.0256(4) Uani 1 1 d . . . H22 H 0.5763 -0.0804 -0.2137 0.031 Uiso 1 1 calc R . . C49 C 0.68492(17) 0.62532(15) 0.08466(12) 0.0288(4) Uani 1 1 d . . . H25 H 0.6786 0.6986 0.0862 0.035 Uiso 1 1 calc R . . H26 H 0.6515 0.5791 0.0266 0.035 Uiso 1 1 calc R . . C50 C 0.75352(17) 0.25712(16) -0.30253(12) 0.0288(4) Uani 1 1 d . . . H27 H 0.7809 0.3375 -0.2893 0.035 Uiso 1 1 calc R . . H28 H 0.7017 0.2297 -0.3589 0.035 Uiso 1 1 calc R . . C51 C 0.48291(17) -0.29916(17) -0.47569(12) 0.0306(4) Uani 1 1 d . . . C52 C 0.27875(18) 1.01550(16) 0.81882(12) 0.0313(4) Uani 1 1 d . . . H29 H 0.3129 1.0625 0.8735 0.038 Uiso 1 1 calc R . . C53 C 0.53061(16) 0.56996(15) 0.25550(11) 0.0263(4) Uani 1 1 d . . . H30 H 0.5058 0.5900 0.3067 0.032 Uiso 1 1 calc R . . C54 C 0.55551(19) -0.09929(17) -0.44191(12) 0.0322(4) Uani 1 1 d . . . H31 H 0.5521 -0.1037 -0.5001 0.039 Uiso 1 1 calc R . . C55 C -0.26567(17) 0.57321(17) 0.43971(12) 0.0319(4) Uani 1 1 d . . . H32 H -0.3040 0.5007 0.4015 0.048 Uiso 1 1 calc R . . H33 H -0.3232 0.6114 0.4483 0.048 Uiso 1 1 calc R . . H34 H -0.2301 0.5663 0.4939 0.048 Uiso 1 1 calc R . . C56 C -0.10630(17) 0.07181(16) -0.12831(11) 0.0297(4) Uani 1 1 d . . . H35 H -0.1305 0.1276 -0.1507 0.036 Uiso 1 1 calc R . . H36 H -0.1756 0.0241 -0.1151 0.036 Uiso 1 1 calc R . . C57 C -0.21931(17) 0.16948(18) 0.06568(13) 0.0345(4) Uani 1 1 d . . . H37 H -0.2489 0.0950 0.0295 0.052 Uiso 1 1 calc R . . H38 H -0.2841 0.1989 0.0714 0.052 Uiso 1 1 calc R . . H39 H -0.1809 0.1693 0.1213 0.052 Uiso 1 1 calc R . . C58 C 0.09073(17) 0.11259(15) -0.02853(11) 0.0260(4) Uani 1 1 d . . . H40 H 0.1217 0.0663 -0.0642 0.031 Uiso 1 1 calc R . . C59 C 0.59006(18) 0.00136(16) -0.38446(12) 0.0308(4) Uani 1 1 d . . . H41 H 0.6094 0.0652 -0.4039 0.037 Uiso 1 1 calc R . . B1 B 0.24980(17) 0.34718(17) 0.29805(12) 0.0215(4) Uani 1 1 d . . . C61 C 0.44473(18) -0.38612(18) -0.52472(13) 0.0357(5) Uani 1 1 d . . . H42 H 0.4142 -0.4556 -0.5639 0.043 Uiso 1 1 calc R . . C62 C 0.85757(19) 0.2160(2) -0.30565(14) 0.0404(5) Uani 1 1 d . . . H43 H 0.9121 0.2470 -0.2513 0.061 Uiso 1 1 calc R . . H44 H 0.8963 0.2380 -0.3500 0.061 Uiso 1 1 calc R . . H45 H 0.8315 0.1366 -0.3176 0.061 Uiso 1 1 calc R . . C70 C -0.24710(17) 0.33999(16) 0.26045(12) 0.0300(4) Uani 1 1 d . . . H46 H -0.1995 0.2912 0.2605 0.045 Uiso 1 1 calc R . . H47 H -0.3148 0.3069 0.2139 0.045 Uiso 1 1 calc R . . H48 H -0.2734 0.3522 0.3139 0.045 Uiso 1 1 calc R . . C69 C 0.62041(19) 0.80569(17) 0.33669(13) 0.0350(5) Uani 1 1 d . . . H49 H 0.5360 0.7864 0.3322 0.053 Uiso 1 1 calc R . . H50 H 0.6548 0.8850 0.3543 0.053 Uiso 1 1 calc R . . H51 H 0.6534 0.7739 0.3783 0.053 Uiso 1 1 calc R . . C65 C -0.0643(2) 0.00406(18) -0.19625(12) 0.0379(5) Uani 1 1 d . . . H52 H 0.0015 0.0513 -0.2122 0.057 Uiso 1 1 calc R . . H53 H -0.1277 -0.0315 -0.2456 0.057 Uiso 1 1 calc R . . H54 H -0.0397 -0.0513 -0.1747 0.057 Uiso 1 1 calc R . . B2 B 0.45687(17) 0.17011(16) 0.05010(12) 0.0215(4) Uani 1 1 d . . . C67 C 0.81328(19) 0.63406(19) 0.10617(14) 0.0398(5) Uani 1 1 d . . . H55 H 0.8470 0.6792 0.1638 0.060 Uiso 1 1 calc R . . H56 H 0.8546 0.6672 0.0670 0.060 Uiso 1 1 calc R . . H57 H 0.8206 0.5613 0.1016 0.060 Uiso 1 1 calc R . . C68 C 0.8520(2) 0.45612(18) -0.08864(14) 0.0412(5) Uani 1 1 d . . . H58 H 0.8507 0.4362 -0.0352 0.062 Uiso 1 1 calc R . . H59 H 0.8827 0.5353 -0.0775 0.062 Uiso 1 1 calc R . . H60 H 0.9018 0.4226 -0.1193 0.062 Uiso 1 1 calc R . . C72 C 0.64694(19) 0.76188(15) 0.25167(12) 0.0317(4) Uani 1 1 d . . . H66 H 0.6145 0.7955 0.2104 0.038 Uiso 1 1 calc R . . H77 H 0.7323 0.7842 0.2565 0.038 Uiso 1 1 calc R . . O4 O 0.49813(11) 0.16638(10) -0.02976(7) 0.0250(3) Uani 1 1 d . . . O5 O 0.46955(12) 0.28283(10) 0.09551(8) 0.0287(3) Uani 1 1 d . . . F5 F 0.34011(9) 0.11193(9) 0.03130(7) 0.0317(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 F2 0.0251(5) 0.0259(5) 0.0309(5) 0.0091(4) 0.0088(4) 0.0073(4) F1 0.0151(5) 0.0273(5) 0.0275(5) 0.0021(4) 0.0037(4) 0.0056(4) F3 0.0347(6) 0.0473(7) 0.0283(5) 0.0168(5) 0.0132(4) 0.0215(5) O2 0.0177(6) 0.0278(7) 0.0234(6) 0.0025(5) 0.0044(4) 0.0090(5) O3 0.0167(6) 0.0233(6) 0.0226(6) 0.0010(4) 0.0030(4) 0.0073(5) N4 0.0198(7) 0.0200(7) 0.0204(7) 0.0050(5) 0.0056(5) 0.0040(6) N2 0.0163(7) 0.0204(7) 0.0211(7) 0.0036(5) 0.0040(5) 0.0070(5) N1 0.0208(7) 0.0297(8) 0.0222(7) 0.0029(6) 0.0042(5) 0.0106(6) C12 0.0178(8) 0.0172(8) 0.0223(8) 0.0063(6) 0.0042(6) 0.0048(6) C13 0.0173(8) 0.0219(8) 0.0215(8) 0.0043(6) 0.0048(6) 0.0059(6) C14 0.0186(8) 0.0214(8) 0.0205(8) 0.0045(6) 0.0009(6) 0.0032(7) C15 0.0205(8) 0.0167(8) 0.0203(8) 0.0052(6) 0.0051(6) 0.0057(6) C16 0.0176(8) 0.0197(8) 0.0235(8) 0.0090(6) 0.0062(6) 0.0060(6) C17 0.0187(8) 0.0211(8) 0.0229(8) 0.0060(6) 0.0061(6) 0.0047(7) C18 0.0216(8) 0.0276(9) 0.0201(8) 0.0083(6) 0.0052(6) 0.0077(7) N3 0.0266(8) 0.0221(7) 0.0237(7) 0.0041(6) 0.0071(6) 0.0044(6) C20 0.0258(9) 0.0211(8) 0.0222(8) 0.0050(6) 0.0102(6) 0.0074(7) C21 0.0159(8) 0.0224(8) 0.0203(8) 0.0059(6) 0.0025(6) 0.0038(6) C22 0.0246(9) 0.0230(9) 0.0269(9) 0.0082(7) 0.0073(7) 0.0041(7) C23 0.0209(9) 0.0215(8) 0.0252(8) 0.0061(6) 0.0047(6) 0.0031(7) C24 0.0218(8) 0.0237(9) 0.0203(8) 0.0057(6) 0.0035(6) 0.0051(7) C25 0.0193(8) 0.0249(9) 0.0236(8) 0.0067(6) 0.0082(6) 0.0082(7) C26 0.0266(9) 0.0238(9) 0.0194(8) 0.0071(6) 0.0071(6) 0.0069(7) C27 0.0285(10) 0.0253(9) 0.0311(9) 0.0092(7) 0.0097(7) 0.0096(8) C28 0.0217(9) 0.0273(9) 0.0288(9) 0.0029(7) 0.0078(7) 0.0083(7) C29 0.0200(8) 0.0198(8) 0.0204(8) 0.0068(6) 0.0076(6) 0.0069(6) C30 0.0199(8) 0.0238(9) 0.0252(8) 0.0055(6) 0.0019(6) 0.0085(7) C31 0.0191(8) 0.0213(8) 0.0215(8) 0.0040(6) 0.0016(6) 0.0051(7) C32 0.0190(8) 0.0191(8) 0.0204(8) 0.0071(6) 0.0057(6) 0.0058(6) C33 0.0238(9) 0.0183(8) 0.0222(8) 0.0071(6) 0.0044(6) 0.0059(7) C34 0.0268(9) 0.0227(9) 0.0221(8) 0.0031(6) -0.0001(6) 0.0077(7) C35 0.0203(8) 0.0247(9) 0.0245(8) 0.0055(6) 0.0088(6) 0.0072(7) C36 0.0233(9) 0.0246(9) 0.0222(8) 0.0073(6) 0.0055(6) 0.0081(7) C37 0.0177(8) 0.0238(9) 0.0253(8) 0.0065(6) 0.0049(6) 0.0030(7) C38 0.0213(8) 0.0190(8) 0.0209(8) 0.0074(6) 0.0056(6) 0.0045(6) C39 0.0208(8) 0.0230(8) 0.0211(8) 0.0060(6) 0.0061(6) 0.0083(7) C40 0.0231(9) 0.0215(8) 0.0223(8) 0.0045(6) -0.0006(6) 0.0055(7) C41 0.0334(10) 0.0224(9) 0.0268(9) 0.0098(7) 0.0071(7) 0.0056(8) C42 0.0198(8) 0.0208(8) 0.0219(8) 0.0087(6) 0.0070(6) 0.0068(6) C43 0.0203(8) 0.0252(9) 0.0211(8) 0.0077(6) 0.0035(6) 0.0070(7) C44 0.0181(8) 0.0188(8) 0.0190(8) 0.0060(6) 0.0038(6) 0.0046(6) C45 0.0211(8) 0.0242(9) 0.0223(8) 0.0045(6) 0.0011(6) 0.0076(7) C46 0.0226(9) 0.0270(9) 0.0231(8) 0.0055(6) 0.0049(6) 0.0126(7) C47 0.0301(9) 0.0274(9) 0.0213(8) 0.0077(7) 0.0073(7) 0.0103(7) C49 0.0356(11) 0.0208(9) 0.0275(9) 0.0085(7) 0.0062(7) 0.0030(8) C50 0.0339(10) 0.0279(9) 0.0266(9) 0.0119(7) 0.0118(7) 0.0066(8) C51 0.0260(9) 0.0324(10) 0.0329(10) 0.0047(8) 0.0115(7) 0.0086(8) C52 0.0328(10) 0.0293(10) 0.0245(9) 0.0033(7) 0.0056(7) 0.0012(8) C53 0.0280(9) 0.0258(9) 0.0225(8) 0.0028(7) 0.0039(7) 0.0077(7) C54 0.0412(11) 0.0330(10) 0.0197(9) 0.0034(7) 0.0098(7) 0.0084(9) C55 0.0210(9) 0.0389(11) 0.0360(10) 0.0062(8) 0.0103(7) 0.0105(8) C56 0.0306(10) 0.0326(10) 0.0221(9) 0.0028(7) 0.0020(7) 0.0089(8) C57 0.0224(9) 0.0359(11) 0.0411(11) 0.0075(8) 0.0093(8) 0.0030(8) C58 0.0305(10) 0.0260(9) 0.0216(8) 0.0027(7) 0.0078(7) 0.0104(7) C59 0.0400(11) 0.0263(9) 0.0259(9) 0.0087(7) 0.0116(8) 0.0065(8) B1 0.0170(9) 0.0249(10) 0.0225(9) 0.0038(7) 0.0049(7) 0.0078(7) C61 0.0318(11) 0.0316(11) 0.0368(11) -0.0013(8) 0.0112(8) 0.0046(9) C62 0.0381(12) 0.0486(13) 0.0450(12) 0.0244(10) 0.0240(9) 0.0138(10) C70 0.0216(9) 0.0265(10) 0.0360(10) 0.0048(7) 0.0022(7) 0.0022(7) C69 0.0365(11) 0.0245(10) 0.0389(11) -0.0009(8) 0.0019(8) 0.0110(9) C65 0.0463(13) 0.0388(12) 0.0233(10) -0.0033(8) 0.0032(8) 0.0153(10) B2 0.0171(9) 0.0224(9) 0.0221(9) 0.0040(7) 0.0037(7) 0.0033(7) C67 0.0329(11) 0.0369(12) 0.0480(12) 0.0174(9) 0.0133(9) 0.0011(9) C68 0.0411(12) 0.0307(11) 0.0438(12) 0.0143(9) 0.0009(9) -0.0012(9) C72 0.0377(11) 0.0209(9) 0.0306(10) 0.0044(7) 0.0005(8) 0.0046(8) O4 0.0274(7) 0.0205(6) 0.0212(6) 0.0030(5) 0.0056(5) -0.0003(5) O5 0.0345(7) 0.0213(6) 0.0239(6) 0.0018(5) 0.0111(5) -0.0006(5) F5 0.0163(5) 0.0290(6) 0.0401(6) -0.0046(5) 0.0077(4) 0.0011(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F2 B1 1.371(2) . ? F1 B1 1.380(2) . ? F3 B2 1.373(2) . ? O2 C12 1.327(2) . ? O2 B1 1.483(2) . ? O3 C16 1.327(2) . ? O3 B1 1.488(2) . ? N4 C18 1.356(2) . ? N4 C31 1.377(2) . ? N4 H1 0.8800 . ? N2 C29 1.360(2) . ? N2 C44 1.379(2) . ? N2 H3 0.8800 . ? N1 C58 1.350(2) . ? N1 C39 1.380(2) . ? N1 H9 0.8800 . ? C12 C13 1.399(2) . ? C12 C39 1.418(2) . ? C13 C16 1.390(2) . ? C13 H63 0.9500 . ? C14 O5 1.320(2) . ? C14 C23 1.390(2) . ? C14 C24 1.420(2) . ? C15 C35 1.400(2) . ? C15 C17 1.403(2) . ? C15 C29 1.464(2) . ? C16 C44 1.430(2) . ? C17 C20 1.379(2) . ? C17 H4 0.9500 . ? C18 C36 1.405(3) . ? C18 C25 1.469(2) . ? N3 C53 1.348(2) . ? N3 C24 1.381(2) . ? N3 H5 0.8800 . ? C20 C33 1.393(3) . ? C20 H10 0.9500 . ? C21 O4 1.324(2) . ? C21 C23 1.389(2) . ? C21 C31 1.429(2) . ? C22 C52 1.187(3) . ? C22 C33 1.435(2) . ? C23 H6 0.9500 . ? C24 C40 1.409(3) . ? C25 C47 1.398(3) . ? C25 C59 1.395(3) . ? C26 C58 1.386(3) . ? C26 C38 1.406(2) . ? C26 C56 1.502(3) . ? C27 C47 1.386(3) . ? C27 C28 1.391(3) . ? C27 H11 0.9500 . ? C28 C54 1.390(3) . ? C28 C51 1.443(3) . ? C29 C42 1.398(2) . ? C30 C32 1.500(2) . ? C30 C70 1.525(3) . ? C30 H12 0.9900 . ? C30 H13 0.9900 . ? C31 C43 1.406(2) . ? C32 C44 1.403(2) . ? C32 C42 1.414(2) . ? C33 C37 1.399(2) . ? C34 C53 1.384(3) . ? C34 C40 1.406(2) . ? C34 C72 1.496(3) . ? C35 C37 1.382(2) . ? C35 H14 0.9500 . ? C36 C43 1.413(2) . ? C36 C50 1.506(2) . ? C37 H15 0.9500 . ? C38 C39 1.409(2) . ? C38 C45 1.495(2) . ? C40 C49 1.510(2) . ? C41 C43 1.501(3) . ? C41 C68 1.526(3) . ? C41 H16 0.9900 . ? C41 H17 0.9900 . ? C42 C46 1.501(2) . ? C45 C57 1.522(3) . ? C45 H18 0.9900 . ? C45 H19 0.9900 . ? C46 C55 1.530(3) . ? C46 H20 0.9900 . ? C46 H21 0.9900 . ? C47 H22 0.9500 . ? C49 C67 1.527(3) . ? C49 H25 0.9900 . ? C49 H26 0.9900 . ? C50 C62 1.516(3) . ? C50 H27 0.9900 . ? C50 H28 0.9900 . ? C51 C61 1.189(3) . ? C52 H29 0.9500 . ? C53 H30 0.9500 . ? C54 C59 1.382(3) . ? C54 H31 0.9500 . ? C55 H32 0.9800 . ? C55 H33 0.9800 . ? C55 H34 0.9800 . ? C56 C65 1.522(3) . ? C56 H35 0.9900 . ? C56 H36 0.9900 . ? C57 H37 0.9800 . ? C57 H38 0.9800 . ? C57 H39 0.9800 . ? C58 H40 0.9500 . ? C59 H41 0.9500 . ? C61 H42 0.9500 . ? C62 H43 0.9800 . ? C62 H44 0.9800 . ? C62 H45 0.9800 . ? C70 H46 0.9800 . ? C70 H47 0.9800 . ? C70 H48 0.9800 . ? C69 C72 1.520(3) . ? C69 H49 0.9800 . ? C69 H50 0.9800 . ? C69 H51 0.9800 . ? C65 H52 0.9800 . ? C65 H53 0.9800 . ? C65 H54 0.9800 . ? B2 F5 1.379(2) . ? B2 O5 1.479(2) . ? B2 O4 1.476(2) . ? C67 H55 0.9800 . ? C67 H56 0.9800 . ? C67 H57 0.9800 . ? C68 H58 0.9800 . ? C68 H59 0.9800 . ? C68 H60 0.9800 . ? C72 H66 0.9900 . ? C72 H77 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 C12 O2 B1 118.46(13) . . ? C16 O3 B1 117.97(13) . . ? C18 N4 C31 110.72(14) . . ? C18 N4 H1 124.6 . . ? C31 N4 H1 124.6 . . ? C29 N2 C44 110.36(14) . . ? C29 N2 H3 124.8 . . ? C44 N2 H3 124.8 . . ? C58 N1 C39 109.81(15) . . ? C58 N1 H9 125.1 . . ? C39 N1 H9 125.1 . . ? O2 C12 C13 119.88(15) . . ? O2 C12 C39 115.28(15) . . ? C13 C12 C39 124.84(16) . . ? C16 C13 C12 120.10(16) . . ? C16 C13 H63 119.9 . . ? C12 C13 H63 119.9 . . ? O5 C14 C23 120.65(16) . . ? O5 C14 C24 114.33(15) . . ? C23 C14 C24 125.02(16) . . ? C35 C15 C17 118.31(15) . . ? C35 C15 C29 120.51(15) . . ? C17 C15 C29 121.16(15) . . ? O3 C16 C13 120.17(15) . . ? O3 C16 C44 114.04(15) . . ? C13 C16 C44 125.75(16) . . ? C20 C17 C15 120.69(16) . . ? C20 C17 H4 119.7 . . ? C15 C17 H4 119.7 . . ? N4 C18 C36 107.50(15) . . ? N4 C18 C25 119.85(15) . . ? C36 C18 C25 132.59(15) . . ? C53 N3 C24 110.05(15) . . ? C53 N3 H5 125.0 . . ? C24 N3 H5 125.0 . . ? C17 C20 C33 120.78(16) . . ? C17 C20 H10 119.6 . . ? C33 C20 H10 119.6 . . ? O4 C21 C23 120.45(15) . . ? O4 C21 C31 113.72(15) . . ? C23 C21 C31 125.82(16) . . ? C52 C22 C33 175.45(19) . . ? C21 C23 C14 120.14(16) . . ? C21 C23 H6 119.9 . . ? C14 C23 H6 119.9 . . ? N3 C24 C40 106.52(15) . . ? N3 C24 C14 118.46(16) . . ? C40 C24 C14 135.00(16) . . ? C47 C25 C59 117.80(17) . . ? C47 C25 C18 120.33(15) . . ? C59 C25 C18 121.75(16) . . ? C58 C26 C38 107.10(15) . . ? C58 C26 C56 126.87(16) . . ? C38 C26 C56 126.00(17) . . ? C47 C27 C28 120.85(18) . . ? C47 C27 H11 119.6 . . ? C28 C27 H11 119.6 . . ? C54 C28 C27 118.54(17) . . ? C54 C28 C51 120.73(17) . . ? C27 C28 C51 120.70(18) . . ? N2 C29 C42 107.87(14) . . ? N2 C29 C15 120.72(15) . . ? C42 C29 C15 131.21(16) . . ? C32 C30 C70 112.65(15) . . ? C32 C30 H12 109.1 . . ? C70 C30 H12 109.1 . . ? C32 C30 H13 109.1 . . ? C70 C30 H13 109.1 . . ? H12 C30 H13 107.8 . . ? N4 C31 C43 107.18(14) . . ? N4 C31 C21 118.46(15) . . ? C43 C31 C21 134.28(16) . . ? C44 C32 C42 107.32(14) . . ? C44 C32 C30 128.39(15) . . ? C42 C32 C30 124.27(15) . . ? C20 C33 C37 118.90(16) . . ? C20 C33 C22 120.45(16) . . ? C37 C33 C22 120.51(16) . . ? C53 C34 C40 107.17(16) . . ? C53 C34 C72 126.29(17) . . ? C40 C34 C72 126.53(17) . . ? C37 C35 C15 120.89(15) . . ? C37 C35 H14 119.6 . . ? C15 C35 H14 119.6 . . ? C18 C36 C43 107.56(15) . . ? C18 C36 C50 127.30(16) . . ? C43 C36 C50 125.02(16) . . ? C35 C37 C33 120.36(16) . . ? C35 C37 H15 119.8 . . ? C33 C37 H15 119.8 . . ? C26 C38 C39 107.35(15) . . ? C26 C38 C45 124.59(15) . . ? C39 C38 C45 128.01(15) . . ? N1 C39 C38 106.76(14) . . ? N1 C39 C12 119.42(15) . . ? C38 C39 C12 133.77(16) . . ? C34 C40 C24 107.39(15) . . ? C34 C40 C49 123.85(16) . . ? C24 C40 C49 128.75(16) . . ? C43 C41 C68 113.39(17) . . ? C43 C41 H16 108.9 . . ? C68 C41 H16 108.9 . . ? C43 C41 H17 108.9 . . ? C68 C41 H17 108.9 . . ? H16 C41 H17 107.7 . . ? C29 C42 C32 107.37(15) . . ? C29 C42 C46 126.56(15) . . ? C32 C42 C46 125.99(15) . . ? C31 C43 C36 107.04(16) . . ? C31 C43 C41 127.94(16) . . ? C36 C43 C41 125.02(15) . . ? N2 C44 C32 107.08(14) . . ? N2 C44 C16 118.18(15) . . ? C32 C44 C16 134.73(15) . . ? C38 C45 C57 111.63(16) . . ? C38 C45 H18 109.3 . . ? C57 C45 H18 109.3 . . ? C38 C45 H19 109.3 . . ? C57 C45 H19 109.3 . . ? H18 C45 H19 108.0 . . ? C42 C46 C55 114.00(15) . . ? C42 C46 H20 108.8 . . ? C55 C46 H20 108.8 . . ? C42 C46 H21 108.8 . . ? C55 C46 H21 108.8 . . ? H20 C46 H21 107.6 . . ? C27 C47 C25 120.83(17) . . ? C27 C47 H22 119.6 . . ? C25 C47 H22 119.6 . . ? C40 C49 C67 113.33(16) . . ? C40 C49 H25 108.9 . . ? C67 C49 H25 108.9 . . ? C40 C49 H26 108.9 . . ? C67 C49 H26 108.9 . . ? H25 C49 H26 107.7 . . ? C36 C50 C62 113.68(16) . . ? C36 C50 H27 108.8 . . ? C62 C50 H27 108.8 . . ? C36 C50 H28 108.8 . . ? C62 C50 H28 108.8 . . ? H27 C50 H28 107.7 . . ? C61 C51 C28 178.2(2) . . ? C22 C52 H29 180.0 . . ? N3 C53 C34 108.86(16) . . ? N3 C53 H30 125.6 . . ? C34 C53 H30 125.6 . . ? C28 C54 C59 120.65(18) . . ? C28 C54 H31 119.7 . . ? C59 C54 H31 119.7 . . ? C46 C55 H32 109.5 . . ? C46 C55 H33 109.5 . . ? H32 C55 H33 109.5 . . ? C46 C55 H34 109.5 . . ? H32 C55 H34 109.5 . . ? H33 C55 H34 109.5 . . ? C26 C56 C65 113.92(17) . . ? C26 C56 H35 108.8 . . ? C65 C56 H35 108.8 . . ? C26 C56 H36 108.8 . . ? C65 C56 H36 108.8 . . ? H35 C56 H36 107.7 . . ? C45 C57 H37 109.5 . . ? C45 C57 H38 109.5 . . ? H37 C57 H38 109.5 . . ? C45 C57 H39 109.5 . . ? H37 C57 H39 109.5 . . ? H38 C57 H39 109.5 . . ? N1 C58 C26 108.95(15) . . ? N1 C58 H40 125.5 . . ? C26 C58 H40 125.5 . . ? C54 C59 C25 121.29(18) . . ? C54 C59 H41 119.4 . . ? C25 C59 H41 119.4 . . ? F2 B1 F1 111.68(15) . . ? F2 B1 O3 109.75(14) . . ? F1 B1 O3 107.56(15) . . ? F2 B1 O2 110.02(15) . . ? F1 B1 O2 107.94(14) . . ? O3 B1 O2 109.82(14) . . ? C51 C61 H42 180.0 . . ? C50 C62 H43 109.5 . . ? C50 C62 H44 109.5 . . ? H43 C62 H44 109.5 . . ? C50 C62 H45 109.5 . . ? H43 C62 H45 109.5 . . ? H44 C62 H45 109.5 . . ? C30 C70 H46 109.5 . . ? C30 C70 H47 109.5 . . ? H46 C70 H47 109.5 . . ? C30 C70 H48 109.5 . . ? H46 C70 H48 109.5 . . ? H47 C70 H48 109.5 . . ? C72 C69 H49 109.5 . . ? C72 C69 H50 109.5 . . ? H49 C69 H50 109.5 . . ? C72 C69 H51 109.5 . . ? H49 C69 H51 109.5 . . ? H50 C69 H51 109.5 . . ? C56 C65 H52 109.5 . . ? C56 C65 H53 109.5 . . ? H52 C65 H53 109.5 . . ? C56 C65 H54 109.5 . . ? H52 C65 H54 109.5 . . ? H53 C65 H54 109.5 . . ? F5 B2 F3 109.90(16) . . ? F5 B2 O5 107.69(15) . . ? F3 B2 O5 109.65(15) . . ? F5 B2 O4 108.02(14) . . ? F3 B2 O4 110.20(15) . . ? O5 B2 O4 111.32(14) . . ? C49 C67 H55 109.5 . . ? C49 C67 H56 109.5 . . ? H55 C67 H56 109.5 . . ? C49 C67 H57 109.5 . . ? H55 C67 H57 109.5 . . ? H56 C67 H57 109.5 . . ? C41 C68 H58 109.5 . . ? C41 C68 H59 109.5 . . ? H58 C68 H59 109.5 . . ? C41 C68 H60 109.5 . . ? H58 C68 H60 109.5 . . ? H59 C68 H60 109.5 . . ? C34 C72 C69 114.21(17) . . ? C34 C72 H66 108.7 . . ? C69 C72 H66 108.7 . . ? C34 C72 H77 108.7 . . ? C69 C72 H77 108.7 . . ? H66 C72 H77 107.6 . . ? C21 O4 B2 122.05(14) . . ? C14 O5 B2 121.92(14) . . ? 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 C12 C13 16.5(2) . . . . ? B1 O2 C12 C39 -163.92(15) . . . . ? O2 C12 C13 C16 8.2(2) . . . . ? C39 C12 C13 C16 -171.35(16) . . . . ? B1 O3 C16 C13 -18.6(2) . . . . ? B1 O3 C16 C44 163.68(14) . . . . ? C12 C13 C16 O3 -7.0(2) . . . . ? C12 C13 C16 C44 170.43(16) . . . . ? C35 C15 C17 C20 -1.3(3) . . . . ? C29 C15 C17 C20 179.79(16) . . . . ? C31 N4 C18 C36 0.90(19) . . . . ? C31 N4 C18 C25 -176.58(15) . . . . ? C15 C17 C20 C33 -0.6(3) . . . . ? O4 C21 C23 C14 -4.4(3) . . . . ? C31 C21 C23 C14 174.47(16) . . . . ? O5 C14 C23 C21 4.1(3) . . . . ? C24 C14 C23 C21 -175.22(16) . . . . ? C53 N3 C24 C40 -0.8(2) . . . . ? C53 N3 C24 C14 177.67(16) . . . . ? O5 C14 C24 N3 6.9(2) . . . . ? C23 C14 C24 N3 -173.74(16) . . . . ? O5 C14 C24 C40 -175.14(19) . . . . ? C23 C14 C24 C40 4.2(3) . . . . ? N4 C18 C25 C47 -25.0(2) . . . . ? C36 C18 C25 C47 158.32(19) . . . . ? N4 C18 C25 C59 150.95(18) . . . . ? C36 C18 C25 C59 -25.8(3) . . . . ? C47 C27 C28 C54 1.8(3) . . . . ? C47 C27 C28 C51 -176.46(17) . . . . ? C44 N2 C29 C42 0.15(18) . . . . ? C44 N2 C29 C15 -175.28(14) . . . . ? C35 C15 C29 N2 30.8(2) . . . . ? C17 C15 C29 N2 -150.31(16) . . . . ? C35 C15 C29 C42 -143.45(19) . . . . ? C17 C15 C29 C42 35.5(3) . . . . ? C18 N4 C31 C43 -0.48(19) . . . . ? C18 N4 C31 C21 176.77(15) . . . . ? O4 C21 C31 N4 -4.8(2) . . . . ? C23 C21 C31 N4 176.24(16) . . . . ? O4 C21 C31 C43 171.55(18) . . . . ? C23 C21 C31 C43 -7.4(3) . . . . ? C70 C30 C32 C44 81.4(2) . . . . ? C70 C30 C32 C42 -96.6(2) . . . . ? C17 C20 C33 C37 2.3(3) . . . . ? C17 C20 C33 C22 -173.56(16) . . . . ? C52 C22 C33 C20 76(3) . . . . ? C52 C22 C33 C37 -100(3) . . . . ? C17 C15 C35 C37 1.5(3) . . . . ? C29 C15 C35 C37 -179.57(16) . . . . ? N4 C18 C36 C43 -1.0(2) . . . . ? C25 C18 C36 C43 176.08(18) . . . . ? N4 C18 C36 C50 175.17(17) . . . . ? C25 C18 C36 C50 -7.8(3) . . . . ? C15 C35 C37 C33 0.2(3) . . . . ? C20 C33 C37 C35 -2.1(3) . . . . ? C22 C33 C37 C35 173.78(16) . . . . ? C58 C26 C38 C39 -1.28(19) . . . . ? C56 C26 C38 C39 177.23(17) . . . . ? C58 C26 C38 C45 -178.97(16) . . . . ? C56 C26 C38 C45 -0.5(3) . . . . ? C58 N1 C39 C38 -1.57(19) . . . . ? C58 N1 C39 C12 176.19(15) . . . . ? C26 C38 C39 N1 1.73(19) . . . . ? C45 C38 C39 N1 179.33(16) . . . . ? C26 C38 C39 C12 -175.57(18) . . . . ? C45 C38 C39 C12 2.0(3) . . . . ? O2 C12 C39 N1 6.6(2) . . . . ? C13 C12 C39 N1 -173.88(16) . . . . ? O2 C12 C39 C38 -176.38(18) . . . . ? C13 C12 C39 C38 3.2(3) . . . . ? C53 C34 C40 C24 -1.1(2) . . . . ? C72 C34 C40 C24 179.87(18) . . . . ? C53 C34 C40 C49 -179.83(17) . . . . ? C72 C34 C40 C49 1.1(3) . . . . ? N3 C24 C40 C34 1.2(2) . . . . ? C14 C24 C40 C34 -176.98(19) . . . . ? N3 C24 C40 C49 179.84(17) . . . . ? C14 C24 C40 C49 1.7(3) . . . . ? N2 C29 C42 C32 -0.29(18) . . . . ? C15 C29 C42 C32 174.49(16) . . . . ? N2 C29 C42 C46 -177.28(15) . . . . ? C15 C29 C42 C46 -2.5(3) . . . . ? C44 C32 C42 C29 0.32(18) . . . . ? C30 C32 C42 C29 178.61(15) . . . . ? C44 C32 C42 C46 177.33(15) . . . . ? C30 C32 C42 C46 -4.4(3) . . . . ? N4 C31 C43 C36 -0.13(19) . . . . ? C21 C31 C43 C36 -176.75(19) . . . . ? N4 C31 C43 C41 -179.64(17) . . . . ? C21 C31 C43 C41 3.7(3) . . . . ? C18 C36 C43 C31 0.66(19) . . . . ? C50 C36 C43 C31 -175.58(17) . . . . ? C18 C36 C43 C41 -179.81(17) . . . . ? C50 C36 C43 C41 4.0(3) . . . . ? C68 C41 C43 C31 89.1(2) . . . . ? C68 C41 C43 C36 -90.3(2) . . . . ? C29 N2 C44 C32 0.05(18) . . . . ? C29 N2 C44 C16 179.56(14) . . . . ? C42 C32 C44 N2 -0.23(18) . . . . ? C30 C32 C44 N2 -178.43(15) . . . . ? C42 C32 C44 C16 -179.62(18) . . . . ? C30 C32 C44 C16 2.2(3) . . . . ? O3 C16 C44 N2 0.2(2) . . . . ? C13 C16 C44 N2 -177.35(15) . . . . ? O3 C16 C44 C32 179.57(17) . . . . ? C13 C16 C44 C32 2.0(3) . . . . ? C26 C38 C45 C57 91.6(2) . . . . ? C39 C38 C45 C57 -85.6(2) . . . . ? C29 C42 C46 C55 -98.3(2) . . . . ? C32 C42 C46 C55 85.3(2) . . . . ? C28 C27 C47 C25 0.0(3) . . . . ? C59 C25 C47 C27 -1.6(3) . . . . ? C18 C25 C47 C27 174.46(17) . . . . ? C34 C40 C49 C67 88.9(2) . . . . ? C24 C40 C49 C67 -89.6(2) . . . . ? C18 C36 C50 C62 -63.1(3) . . . . ? C43 C36 C50 C62 112.4(2) . . . . ? C54 C28 C51 C61 -113(8) . . . . ? C27 C28 C51 C61 65(8) . . . . ? C24 N3 C53 C34 0.2(2) . . . . ? C40 C34 C53 N3 0.6(2) . . . . ? C72 C34 C53 N3 179.63(17) . . . . ? C27 C28 C54 C59 -2.1(3) . . . . ? C51 C28 C54 C59 176.18(19) . . . . ? C58 C26 C56 C65 -8.0(3) . . . . ? C38 C26 C56 C65 173.78(17) . . . . ? C39 N1 C58 C26 0.8(2) . . . . ? C38 C26 C58 N1 0.3(2) . . . . ? C56 C26 C58 N1 -178.16(17) . . . . ? C28 C54 C59 C25 0.5(3) . . . . ? C47 C25 C59 C54 1.3(3) . . . . ? C18 C25 C59 C54 -174.67(18) . . . . ? C16 O3 B1 F2 -81.30(18) . . . . ? C16 O3 B1 F1 157.01(13) . . . . ? C16 O3 B1 O2 39.8(2) . . . . ? C12 O2 B1 F2 82.15(18) . . . . ? C12 O2 B1 F1 -155.76(14) . . . . ? C12 O2 B1 O3 -38.8(2) . . . . ? C53 C34 C72 C69 3.9(3) . . . . ? C40 C34 C72 C69 -177.24(18) . . . . ? C23 C21 O4 B2 -8.7(2) . . . . ? C31 C21 O4 B2 172.24(15) . . . . ? F5 B2 O4 C21 137.95(16) . . . . ? F3 B2 O4 C21 -101.98(19) . . . . ? O5 B2 O4 C21 19.9(2) . . . . ? C23 C14 O5 B2 9.3(3) . . . . ? C24 C14 O5 B2 -171.26(15) . . . . ? F5 B2 O5 C14 -138.45(16) . . . . ? F3 B2 O5 C14 101.99(18) . . . . ? O4 B2 O5 C14 -20.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.648 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.068 # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.000 0.500 161.8 8.0 _platon_squeeze_details ; ; #============================================================================== # End of CIF #============================================================================== data_81006-3 _database_code_depnum_ccdc_archive 'CCDC 819393' #TrackingRef '- BF2_ethynyl_HMaeda_CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H33 B F2 N2 O2' _chemical_formula_weight 562.44 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' F F 0.0171 0.0103 '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 9.380(13) _cell_length_b 9.727(17) _cell_length_c 35.17(4) _cell_angle_alpha 89.33(6) _cell_angle_beta 84.28(4) _cell_angle_gamma 63.89(6) _cell_volume 2865(7) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 620 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 26.4 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9486 _exptl_absorpt_correction_T_max 0.9569 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _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 19716 _diffrn_reflns_av_R_equivalents 0.0669 _diffrn_reflns_av_sigmaI/netI 0.0892 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 9480 _reflns_number_gt 6403 _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. Poor Data Parameter/Ratio (6.69) was observed because the reflection intensity was low and 50% of molecule was disordered. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[_s^2^(Fo^2^)+(0.0601P)^2^+3.7946P] 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 ref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9480 _refine_ls_number_parameters 1416 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1089 _refine_ls_R_factor_gt 0.0699 _refine_ls_wR_factor_ref 0.1833 _refine_ls_wR_factor_gt 0.1593 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.0923(4) 0.8997(4) 0.04918(10) 0.022 Uani 1 1 d . . . B2 B 0.0898(11) 0.4299(11) 0.4503(2) 0.030 Uani 0.52 1 d P A 1 B2B B 0.1159(12) 0.3558(14) 0.4481(3) 0.042 Uani 0.48 1 d P B 2 C1 C 0.1018(5) 0.5558(5) 0.34833(12) 0.042 Uani 1 1 d . . . H32 H 0.056(5) 0.557(5) 0.3758(12) 0.050 Uiso 1 1 d . . . C2 C 0.1550(4) 0.5465(4) 0.31598(10) 0.033 Uani 1 1 d . . . C3 C 0.2170(4) 0.5367(4) 0.27653(9) 0.027 Uani 1 1 d . . . C4 C 0.3783(4) 0.4970(4) 0.26640(10) 0.028 Uani 1 1 d . . . H1 H 0.453(4) 0.476(4) 0.2856(10) 0.034 Uiso 1 1 d . . . C5 C 0.4377(4) 0.4849(4) 0.22829(10) 0.028 Uani 1 1 d . . . H2 H 0.552(4) 0.460(4) 0.2213(9) 0.033 Uiso 1 1 d . . . C6 C 0.3379(4) 0.5127(4) 0.19946(9) 0.024 Uani 1 1 d . . . C7 C 0.1772(4) 0.5530(4) 0.20996(10) 0.028 Uani 1 1 d . . . H3 H 0.112(4) 0.569(4) 0.1917(10) 0.033 Uiso 1 1 d . . . C8 C 0.1179(4) 0.5644(4) 0.24768(10) 0.031 Uani 1 1 d . . . H4 H 0.010(5) 0.596(4) 0.2530(10) 0.037 Uiso 1 1 d . . . C9 C 0.3992(4) 0.5053(4) 0.15923(9) 0.024 Uani 1 1 d . . . C10 C 0.5391(4) 0.4032(4) 0.13828(9) 0.024 Uani 1 1 d . . . C11 C 0.5380(4) 0.4555(4) 0.10074(9) 0.023 Uani 1 1 d . . . C12 C 0.3964(4) 0.5895(4) 0.09948(9) 0.022 Uani 1 1 d . . . C13 C 0.3329(4) 0.7001(4) 0.07109(9) 0.021 Uani 1 1 d . . . C14 C 0.4192(4) 0.7149(4) 0.03836(9) 0.021 Uani 1 1 d . . . H5 H 0.535(4) 0.642(4) 0.0330(9) 0.025 Uiso 1 1 d . . . C15 C 0.3512(4) 0.8392(4) 0.01509(9) 0.020 Uani 1 1 d . . . C16 C 0.4336(4) 0.8737(3) -0.01673(9) 0.019 Uani 1 1 d . . . C17 C 0.5959(4) 0.8158(4) -0.03073(9) 0.021 Uani 1 1 d . . . C18 C 0.6046(4) 0.8897(4) -0.06489(9) 0.021 Uani 1 1 d . . . C19 C 0.4476(4) 0.9954(4) -0.07101(9) 0.020 Uani 1 1 d . . . C20 C 0.3856(4) 1.1063(4) -0.10064(9) 0.022 Uani 1 1 d . . . C21 C 0.2218(4) 1.1981(4) -0.10065(10) 0.030 Uani 1 1 d . . . H6 H 0.144(4) 1.183(4) -0.0821(10) 0.036 Uiso 1 1 d . . . C22 C 0.1619(4) 1.3040(4) -0.12836(10) 0.032 Uani 1 1 d . . . H7 H 0.052(5) 1.362(4) -0.1275(10) 0.038 Uiso 1 1 d . . . C23 C 0.2624(4) 1.3247(4) -0.15731(9) 0.025 Uani 1 1 d . . . C24 C 0.4262(4) 1.2341(4) -0.15779(10) 0.028 Uani 1 1 d . . . H8 H 0.500(4) 1.248(4) -0.1809(10) 0.034 Uiso 1 1 d . . . C25 C 0.4851(4) 1.1277(4) -0.13004(10) 0.029 Uani 1 1 d . . . H9 H 0.597(4) 1.065(4) -0.1313(10) 0.034 Uiso 1 1 d . . . C26 C 0.2023(4) 1.4388(4) -0.18560(10) 0.028 Uani 1 1 d . . . C27 C 0.1560(5) 1.5327(5) -0.20854(11) 0.036 Uani 1 1 d . . . H33 H 0.119(5) 1.605(5) -0.2249(11) 0.043 Uiso 1 1 d . . . C28 C 0.6704(4) 0.2597(4) 0.15170(11) 0.030 Uani 1 1 d . . . H12 H 0.735(4) 0.285(4) 0.1679(10) 0.036 Uiso 1 1 d . . . H13 H 0.745(4) 0.194(4) 0.1298(10) 0.036 Uiso 1 1 d . . . C29 C 0.6181(5) 0.1525(5) 0.17403(13) 0.036 Uani 1 1 d . . . H14 H 0.551(5) 0.207(5) 0.1989(12) 0.055 Uiso 1 1 d . . . H15 H 0.713(5) 0.055(5) 0.1806(11) 0.055 Uiso 1 1 d . . . H16 H 0.555(5) 0.127(5) 0.1605(12) 0.055 Uiso 1 1 d . . . C30 C 0.6634(4) 0.3770(4) 0.06838(10) 0.026 Uani 1 1 d . . . H17 H 0.620(4) 0.405(4) 0.0425(10) 0.031 Uiso 1 1 d . . . H18 H 0.694(4) 0.266(4) 0.0708(9) 0.031 Uiso 1 1 d . . . C31 C 0.8094(4) 0.4081(5) 0.06879(12) 0.034 Uani 1 1 d . . . H19 H 0.768(5) 0.530(5) 0.0663(11) 0.051 Uiso 1 1 d . . . H20 H 0.899(5) 0.352(5) 0.0450(11) 0.051 Uiso 1 1 d . . . H21 H 0.853(5) 0.373(5) 0.0948(12) 0.051 Uiso 1 1 d . . . C32 C 0.7384(4) 0.7043(4) -0.01234(10) 0.022 Uani 1 1 d . . . H22 H 0.707(4) 0.709(4) 0.0155(9) 0.026 Uiso 1 1 d . . . H23 H 0.830(4) 0.735(4) -0.0173(9) 0.026 Uiso 1 1 d . . . C33 C 0.8027(5) 0.5397(4) -0.02782(11) 0.029 Uani 1 1 d . . . H24 H 0.727(5) 0.504(5) -0.0240(11) 0.044 Uiso 1 1 d . . . H25 H 0.903(5) 0.468(5) -0.0150(10) 0.044 Uiso 1 1 d . . . H26 H 0.825(4) 0.539(4) -0.0555(11) 0.044 Uiso 1 1 d . . . C34 C 0.7580(4) 0.8508(4) -0.08936(10) 0.025 Uani 1 1 d . . . H27 H 0.848(4) 0.795(4) -0.0722(9) 0.030 Uiso 1 1 d . . . H28 H 0.770(4) 0.941(4) -0.0980(9) 0.030 Uiso 1 1 d . . . C35 C 0.7827(4) 0.7443(4) -0.12363(10) 0.031 Uani 1 1 d . . . H29 H 0.767(4) 0.646(5) -0.1137(11) 0.046 Uiso 1 1 d . . . H30 H 0.893(5) 0.713(4) -0.1396(11) 0.046 Uiso 1 1 d . . . H31 H 0.703(5) 0.808(5) -0.1449(11) 0.046 Uiso 1 1 d . . . C36 C 0.1805(17) 0.888(2) 0.7212(5) 0.083 Uani 0.52 1 d P A 1 H36 H 0.132(14) 0.959(14) 0.740(4) 0.100 Uiso 0.52 1 d P C 1 C37 C 0.2159(15) 0.8233(15) 0.6949(4) 0.065 Uani 0.52 1 d P A 1 C38 C 0.2596(13) 0.7413(12) 0.6657(4) 0.054 Uani 0.52 1 d P A 1 C39 C 0.4122(10) 0.6882(9) 0.6509(2) 0.036 Uani 0.52 1 d P A 1 H63 H 0.4844 0.7084 0.6643 0.043 Uiso 0.52 1 calc PR A 1 C40 C 0.4673(10) 0.6048(8) 0.6166(2) 0.033 Uani 0.52 1 d P A 1 H64 H 0.5741 0.5756 0.6059 0.039 Uiso 0.52 1 calc PR A 1 C41 C 0.3692(10) 0.5634(9) 0.5976(2) 0.036 Uani 0.52 1 d P A 1 C42 C 0.2109(12) 0.6291(11) 0.6124(3) 0.057 Uani 0.52 1 d P A 1 H65 H 0.1373 0.6062 0.6003 0.069 Uiso 0.52 1 calc PR A 1 C43 C 0.1627(12) 0.7151(12) 0.6405(3) 0.059 Uani 0.52 1 d P A 1 H66 H 0.0502 0.7701 0.6462 0.070 Uiso 0.52 1 calc PR A 1 C44 C 0.4311(9) 0.4677(8) 0.5625(2) 0.029 Uani 0.52 1 d P A 1 C45 C 0.5880(9) 0.3580(9) 0.5493(2) 0.035 Uani 0.52 1 d P A 1 C46 C 0.5834(9) 0.2930(8) 0.5140(2) 0.033 Uani 0.52 1 d P A 1 C47 C 0.4214(9) 0.3616(8) 0.5062(2) 0.027 Uani 0.52 1 d P A 1 C48 C 0.3438(8) 0.3406(8) 0.4765(2) 0.027 Uani 0.52 1 d P A 1 C49 C 0.4087(10) 0.2220(9) 0.4488(3) 0.035 Uani 0.52 1 d P A 1 H115 H 0.5108 0.1395 0.4508 0.042 Uiso 0.52 1 calc PR A 1 C50 C 0.3281(10) 0.2233(9) 0.4191(2) 0.035 Uani 0.52 1 d P A 1 C51 C 0.3873(10) 0.1131(10) 0.3876(2) 0.040 Uani 0.52 1 d P A 1 C61 C 0.1231(12) 0.0050(11) 0.1914(2) 0.025 Uani 0.52 1 d P A 1 C57 C 0.2061(10) 0.1366(10) 0.2354(2) 0.032 Uani 0.52 1 d P A 1 H119 H 0.1789 0.2198 0.2187 0.039 Uiso 0.52 1 calc PR A 1 C58 C 0.1842(13) 0.0073(12) 0.2261(2) 0.028 Uani 0.52 1 d P A 1 C60 C 0.2598(9) -0.0906(9) 0.2867(2) 0.032 Uani 0.52 1 d P A 1 H68 H 0.2736 -0.1675 0.3048 0.039 Uiso 0.52 1 calc PR A 1 C62 C 0.0511(12) -0.0124(12) 0.1581(3) 0.027 Uani 0.52 1 d P A 1 H62 H -0.003(11) -0.020(10) 0.137(3) 0.032 Uiso 0.52 1 d P D 1 C59 C 0.1988(9) -0.0981(9) 0.2532(2) 0.032 Uani 0.52 1 d P A 1 H69 H 0.1671 -0.1764 0.2489 0.039 Uiso 0.52 1 calc PR A 1 C56 C 0.2672(10) 0.1409(10) 0.2691(2) 0.034 Uani 0.52 1 d P A 1 H120 H 0.2866 0.2260 0.2749 0.041 Uiso 0.52 1 calc PR A 1 C55 C 0.3016(10) 0.0238(9) 0.2950(2) 0.034 Uani 0.52 1 d P A 1 C54 C 0.3707(10) 0.0278(10) 0.3305(2) 0.038 Uani 0.52 1 d P A 1 C52 C 0.5163(12) -0.0314(11) 0.3813(3) 0.056 Uani 0.52 1 d P A 1 C53 C 0.5055(12) -0.0843(11) 0.3461(3) 0.061 Uani 0.52 1 d P A 1 C63 C 0.7357(11) 0.3040(10) 0.5708(3) 0.055 Uani 0.52 1 d P A 1 H71 H 0.8283 0.2734 0.5511 0.066 Uiso 0.52 1 calc PR A 1 H72 H 0.7278 0.3954 0.5847 0.066 Uiso 0.52 1 calc PR A 1 C64 C 0.7800(13) 0.1776(15) 0.5990(3) 0.080 Uani 0.52 1 d P A 1 H73 H 0.7003 0.2105 0.6214 0.120 Uiso 0.52 1 calc PR A 1 H74 H 0.8852 0.1545 0.6070 0.120 Uiso 0.52 1 calc PR A 1 H75 H 0.7834 0.0857 0.5870 0.120 Uiso 0.52 1 calc PR A 1 C65 C 0.7223(9) 0.1722(9) 0.4902(2) 0.038 Uani 0.52 1 d P A 1 H76 H 0.8186 0.1876 0.4927 0.046 Uiso 0.52 1 calc PR A 1 H77 H 0.7015 0.1838 0.4631 0.046 Uiso 0.52 1 calc PR A 1 C66 C 0.7568(14) 0.0021(11) 0.5023(3) 0.064 Uani 0.52 1 d P A 1 H78 H 0.7832 -0.0120 0.5288 0.097 Uiso 0.52 1 calc PR A 1 H79 H 0.8467 -0.0721 0.4853 0.097 Uiso 0.52 1 calc PR A 1 H80 H 0.6618 -0.0138 0.5001 0.097 Uiso 0.52 1 calc PR A 1 C67 C 0.6451(14) -0.1187(14) 0.4083(4) 0.078 Uani 0.52 1 d P A 1 H81 H 0.6787 -0.2303 0.4062 0.094 Uiso 0.52 1 calc PR A 1 H82 H 0.6049 -0.0829 0.4352 0.094 Uiso 0.52 1 calc PR A 1 C68 C 0.8050(14) -0.0752(12) 0.3924(4) 0.086 Uani 0.52 1 d P A 1 H83 H 0.8336 -0.0993 0.3649 0.129 Uiso 0.52 1 calc PR A 1 H84 H 0.8974 -0.1363 0.4061 0.129 Uiso 0.52 1 calc PR A 1 H85 H 0.7727 0.0340 0.3973 0.129 Uiso 0.52 1 calc PR A 1 C69 C 0.6070(13) -0.2365(13) 0.3285(3) 0.077 Uani 0.52 1 d P A 1 H86 H 0.6852 -0.2986 0.3461 0.092 Uiso 0.52 1 calc PR A 1 H87 H 0.5404 -0.2890 0.3238 0.092 Uiso 0.52 1 calc PR A 1 C70 C 0.6863(15) -0.2253(15) 0.2946(3) 0.074 Uani 0.52 1 d P A 1 H88 H 0.6096 -0.1542 0.2783 0.111 Uiso 0.52 1 calc PR A 1 H89 H 0.7425 -0.3265 0.2817 0.111 Uiso 0.52 1 calc PR A 1 H90 H 0.7637 -0.1872 0.2997 0.111 Uiso 0.52 1 calc PR A 1 C68B C 0.7242(15) -0.1866(13) 0.4124(4) 0.072 Uani 0.48 1 d P B 2 H91 H 0.6298 -0.1395 0.4311 0.108 Uiso 0.48 1 calc PR B 2 H92 H 0.8207 -0.2144 0.4252 0.108 Uiso 0.48 1 calc PR B 2 H93 H 0.7269 -0.2788 0.4007 0.108 Uiso 0.48 1 calc PR B 2 C67B C 0.7177(10) -0.0864(13) 0.3850(3) 0.053 Uani 0.48 1 d P B 2 H94 H 0.8124 -0.1378 0.3662 0.063 Uiso 0.48 1 calc PR B 2 H95 H 0.7275 0.0001 0.3971 0.063 Uiso 0.48 1 calc PR B 2 C69B C 0.6853(12) -0.1916(11) 0.3041(2) 0.037 Uani 0.48 1 d P B 2 H96 H 0.7882 -0.1932 0.3090 0.044 Uiso 0.48 1 calc PR B 2 H97 H 0.6708 -0.1680 0.2769 0.044 Uiso 0.48 1 calc PR B 2 C70B C 0.6965(10) -0.3536(10) 0.3106(2) 0.042 Uani 0.48 1 d P B 2 H98 H 0.7140 -0.3800 0.3373 0.064 Uiso 0.48 1 calc PR B 2 H99 H 0.7857 -0.4285 0.2937 0.064 Uiso 0.48 1 calc PR B 2 H100 H 0.5968 -0.3550 0.3051 0.064 Uiso 0.48 1 calc PR B 2 C63B C 0.7692(13) 0.2385(13) 0.5671(3) 0.061 Uani 0.48 1 d P B 2 H101 H 0.8027 0.3219 0.5661 0.074 Uiso 0.48 1 calc PR B 2 H102 H 0.8572 0.1438 0.5550 0.074 Uiso 0.48 1 calc PR B 2 C65B C 0.7493(13) 0.0566(12) 0.4964(3) 0.052 Uani 0.48 1 d P B 2 H103 H 0.8193 -0.0052 0.5156 0.062 Uiso 0.48 1 calc PR B 2 H104 H 0.7094 -0.0072 0.4834 0.062 Uiso 0.48 1 calc PR B 2 C64B C 0.7101(13) 0.2112(14) 0.6114(3) 0.062 Uani 0.48 1 d P B 2 H105 H 0.6228 0.3069 0.6223 0.094 Uiso 0.48 1 calc PR B 2 H106 H 0.7997 0.1789 0.6269 0.094 Uiso 0.48 1 calc PR B 2 H107 H 0.6730 0.1315 0.6110 0.094 Uiso 0.48 1 calc PR B 2 C66B C 0.8334(15) 0.1143(15) 0.4692(4) 0.078 Uani 0.48 1 d P B 2 H108 H 0.7674 0.1622 0.4484 0.117 Uiso 0.48 1 calc PR B 2 H109 H 0.9339 0.0294 0.4586 0.117 Uiso 0.48 1 calc PR B 2 H110 H 0.8562 0.1903 0.4820 0.117 Uiso 0.48 1 calc PR B 2 C36B C 0.1894(14) 0.8457(16) 0.7344(4) 0.057 Uani 0.48 1 d P B 2 H36B H 0.177(13) 0.892(14) 0.755(3) 0.068 Uiso 0.48 1 d P E 2 C37B C 0.2222(15) 0.7782(14) 0.7029(4) 0.060 Uani 0.48 1 d P B 2 C38B C 0.2822(15) 0.6973(12) 0.6607(4) 0.051 Uani 0.48 1 d P B 2 C39B C 0.4455(11) 0.6375(10) 0.6452(3) 0.040 Uani 0.48 1 d P B 2 H111 H 0.5162 0.6656 0.6570 0.048 Uiso 0.48 1 calc PR B 2 C40B C 0.5016(11) 0.5410(10) 0.6138(3) 0.040 Uani 0.48 1 d P B 2 H112 H 0.6132 0.4919 0.6063 0.048 Uiso 0.48 1 calc PR B 2 C41B C 0.3995(11) 0.5117(10) 0.5922(3) 0.035 Uani 0.48 1 d P B 2 C42B C 0.2390(11) 0.5706(11) 0.6077(3) 0.045 Uani 0.48 1 d P B 2 H113 H 0.1648 0.5600 0.5929 0.055 Uiso 0.48 1 calc PR B 2 C43B C 0.1789(13) 0.6499(12) 0.6467(3) 0.055 Uani 0.48 1 d P B 2 H114 H 0.0798 0.6654 0.6602 0.066 Uiso 0.48 1 calc PR B 2 C44B C 0.4628(11) 0.4021(10) 0.5593(2) 0.038 Uani 0.48 1 d P B 2 C45B C 0.6140(11) 0.2834(12) 0.5485(3) 0.052 Uani 0.48 1 d P B 2 C46B C 0.6077(12) 0.2042(13) 0.5155(3) 0.055 Uani 0.48 1 d P B 2 C47B C 0.4492(10) 0.2821(12) 0.5063(3) 0.044 Uani 0.48 1 d P B 2 C48B C 0.3721(10) 0.2605(12) 0.4744(3) 0.040 Uani 0.48 1 d P B 2 C49B C 0.4459(11) 0.1637(11) 0.4439(3) 0.043 Uani 0.48 1 d P B 2 H116 H 0.5537 0.0894 0.4441 0.051 Uiso 0.48 1 calc PR B 2 C50B C 0.3618(10) 0.1727(11) 0.4112(3) 0.041 Uani 0.48 1 d P B 2 C51B C 0.4289(10) 0.0882(12) 0.3770(2) 0.037 Uani 0.48 1 d P B 2 C52B C 0.5732(9) -0.0212(10) 0.3637(2) 0.034 Uani 0.48 1 d P B 2 C53B C 0.5597(8) -0.0706(9) 0.3273(2) 0.026 Uani 0.48 1 d P B 2 C54B C 0.4113(9) 0.0188(9) 0.3175(2) 0.028 Uani 0.48 1 d P B 2 C55B C 0.3346(10) 0.0189(10) 0.2831(2) 0.028 Uani 0.48 1 d P B 2 C56B C 0.2950(10) 0.1329(10) 0.2571(2) 0.031 Uani 0.48 1 d P B 2 H121 H 0.3143 0.2189 0.2618 0.037 Uiso 0.48 1 calc PR B 2 C57B C 0.2288(11) 0.1263(11) 0.2247(2) 0.031 Uani 0.48 1 d P B 2 H122 H 0.2100 0.2039 0.2065 0.037 Uiso 0.48 1 calc PR B 2 C58B C 0.1885(14) 0.0088(13) 0.2178(2) 0.030 Uani 0.48 1 d P B 2 C59B C 0.2417(10) -0.1152(10) 0.2428(2) 0.031 Uani 0.48 1 d P B 2 H59B H 0.214(9) -0.205(9) 0.238(2) 0.038 Uiso 0.48 1 d P F 2 C60B C 0.3111(11) -0.1095(10) 0.2748(2) 0.035 Uani 0.48 1 d P B 2 H60B H 0.348(10) -0.193(10) 0.293(2) 0.042 Uiso 0.48 1 d P G 2 C61B C 0.1095(13) -0.0030(13) 0.1847(3) 0.027 Uani 0.48 1 d P B 2 C62B C 0.0622(14) 0.0040(13) 0.1634(3) 0.031 Uani 0.48 1 d P B 2 H62B H 0.014(13) 0.013(12) 0.138(3) 0.037 Uiso 0.48 1 d P H 2 F1 F 0.0204(2) 0.8274(2) 0.02983(5) 0.027 Uani 1 1 d . . . F2 F -0.0234(2) 1.0318(2) 0.06745(5) 0.027 Uani 1 1 d . . . F3 F -0.0064(5) 0.3687(5) 0.46859(13) 0.038 Uani 0.52 1 d P A 1 F4 F -0.0072(5) 0.5735(4) 0.43727(12) 0.032 Uani 0.52 1 d P A 1 F3B F 0.0240(6) 0.2910(7) 0.46360(14) 0.051 Uani 0.48 1 d P B 2 F4B F 0.0191(6) 0.5038(6) 0.43806(14) 0.042 Uani 0.48 1 d P B 2 N1 N 0.3118(3) 0.6125(3) 0.13513(8) 0.023 Uani 1 1 d . . . H10 H 0.232(4) 0.698(4) 0.1409(9) 0.028 Uiso 1 1 d . . . N2 N 0.3489(3) 0.9828(3) -0.04155(7) 0.020 Uani 1 1 d . . . H11 H 0.243(4) 1.034(4) -0.0377(9) 0.024 Uiso 1 1 d . . . N3 N 0.3359(7) 0.4672(7) 0.53627(18) 0.027 Uani 0.52 1 d P A 1 H3A H 0.259(9) 0.504(8) 0.537(2) 0.032 Uiso 0.52 1 d P I 1 N4 N 0.3000(9) 0.1406(9) 0.3574(2) 0.037 Uani 0.52 1 d P A 1 H4A H 0.218(9) 0.208(9) 0.359(2) 0.045 Uiso 0.52 1 d P J 1 N3B N 0.3665(8) 0.3952(9) 0.5331(2) 0.036 Uani 0.48 1 d P B 2 H117 H 0.2638 0.4567 0.5336 0.043 Uiso 0.48 1 calc PR B 2 N4B N 0.3306(9) 0.1178(10) 0.34810(19) 0.032 Uani 0.48 1 d P B 2 H118 H 0.2314 0.1893 0.3492 0.038 Uiso 0.48 1 calc PR B 2 O1 O 0.1804(2) 0.7976(2) 0.07911(6) 0.024 Uani 1 1 d . . . O2 O 0.1984(2) 0.9355(2) 0.02195(6) 0.023 Uani 1 1 d . . . O3 O 0.1930(6) 0.4470(6) 0.47578(13) 0.029 Uani 0.52 1 d P A 1 O4 O 0.1819(6) 0.3348(5) 0.41581(15) 0.033 Uani 0.52 1 d P A 1 O3B O 0.2195(7) 0.3638(8) 0.47685(16) 0.046 Uani 0.48 1 d P B 2 O4B O 0.2103(7) 0.2713(7) 0.41348(17) 0.042 Uani 0.48 1 d P B 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 B1 0.014 0.022 0.024 0.006 -0.003 -0.004 B2 0.030 0.028 0.037 0.009 -0.016 -0.015 B2B 0.031 0.049 0.045 -0.004 -0.016 -0.014 C1 0.037 0.052 0.032 -0.001 -0.002 -0.015 C2 0.032 0.033 0.032 -0.001 -0.006 -0.013 C3 0.031 0.023 0.026 0.002 -0.002 -0.011 C4 0.028 0.028 0.029 0.006 -0.011 -0.011 C5 0.022 0.026 0.032 0.005 -0.007 -0.008 C6 0.020 0.018 0.030 0.003 -0.004 -0.005 C7 0.023 0.030 0.029 0.002 -0.008 -0.010 C8 0.025 0.032 0.036 -0.001 -0.005 -0.012 C9 0.022 0.022 0.028 0.006 -0.010 -0.008 C10 0.021 0.020 0.027 0.005 -0.009 -0.006 C11 0.019 0.021 0.030 0.001 -0.010 -0.007 C12 0.016 0.021 0.026 0.002 -0.006 -0.007 C13 0.016 0.019 0.026 -0.002 -0.005 -0.004 C14 0.015 0.020 0.025 0.002 -0.005 -0.004 C15 0.014 0.019 0.027 -0.001 -0.007 -0.006 C16 0.015 0.016 0.025 0.001 -0.005 -0.005 C17 0.017 0.017 0.028 -0.002 -0.004 -0.006 C18 0.020 0.019 0.027 -0.001 -0.004 -0.009 C19 0.018 0.019 0.022 -0.002 -0.002 -0.007 C20 0.021 0.021 0.026 0.001 -0.005 -0.009 C21 0.019 0.037 0.030 0.008 -0.003 -0.009 C22 0.019 0.035 0.036 0.009 -0.006 -0.006 C23 0.024 0.025 0.028 0.001 -0.006 -0.011 C24 0.024 0.030 0.028 0.005 -0.001 -0.010 C25 0.020 0.029 0.033 0.006 -0.002 -0.007 C26 0.021 0.030 0.035 0.004 -0.007 -0.012 C27 0.030 0.037 0.043 0.013 -0.014 -0.015 C28 0.025 0.027 0.032 0.007 -0.009 -0.005 C29 0.033 0.022 0.051 0.003 -0.013 -0.007 C30 0.023 0.017 0.032 -0.001 -0.007 -0.002 C31 0.021 0.038 0.037 0.003 -0.002 -0.008 C32 0.016 0.018 0.027 0.002 -0.004 -0.005 C33 0.027 0.020 0.034 0.001 -0.008 -0.003 C34 0.016 0.024 0.032 0.001 -0.005 -0.005 C35 0.028 0.032 0.028 -0.002 0.001 -0.010 C36 0.064 0.090 0.100 0.017 -0.019 -0.038 C37 0.052 0.072 0.081 0.016 -0.023 -0.034 C38 0.043 0.063 0.063 0.012 -0.019 -0.026 C39 0.037 0.041 0.038 0.015 -0.017 -0.022 C40 0.033 0.030 0.042 0.016 -0.014 -0.018 C41 0.034 0.042 0.038 0.017 -0.018 -0.020 C42 0.038 0.067 0.071 0.010 -0.029 -0.022 C43 0.044 0.060 0.080 0.009 -0.024 -0.027 C44 0.028 0.029 0.038 0.014 -0.018 -0.017 C45 0.035 0.022 0.058 0.004 -0.026 -0.017 C46 0.035 0.020 0.049 0.010 -0.024 -0.014 C47 0.033 0.019 0.037 0.015 -0.014 -0.016 C48 0.025 0.024 0.044 0.012 -0.017 -0.018 C49 0.034 0.026 0.046 0.002 -0.017 -0.012 C50 0.033 0.030 0.046 -0.005 -0.018 -0.015 C51 0.039 0.038 0.044 -0.002 -0.018 -0.015 C61 0.024 0.021 0.028 -0.001 -0.004 -0.007 C57 0.031 0.026 0.036 0.004 0.000 -0.010 C58 0.027 0.028 0.027 0.002 -0.006 -0.010 C60 0.039 0.028 0.031 0.000 -0.009 -0.015 C62 0.021 0.023 0.032 -0.008 -0.001 -0.005 C59 0.039 0.026 0.032 0.002 -0.004 -0.014 C56 0.035 0.031 0.037 -0.004 -0.004 -0.015 C55 0.037 0.027 0.036 -0.002 -0.008 -0.011 C54 0.041 0.031 0.040 -0.004 -0.019 -0.012 C52 0.058 0.054 0.061 0.001 -0.025 -0.025 C53 0.058 0.051 0.060 -0.006 -0.019 -0.009 C63 0.044 0.043 0.072 -0.010 -0.034 -0.007 C64 0.050 0.107 0.067 -0.019 -0.022 -0.017 C65 0.030 0.032 0.056 0.001 -0.022 -0.013 C66 0.075 0.041 0.076 0.013 -0.041 -0.018 C67 0.078 0.064 0.090 0.005 -0.042 -0.023 C68 0.086 0.050 0.122 -0.003 -0.065 -0.019 C69 0.064 0.074 0.073 0.000 -0.015 -0.011 C70 0.051 0.072 0.076 -0.017 0.000 -0.007 C68B 0.070 0.050 0.096 0.009 -0.032 -0.021 C67B 0.022 0.087 0.041 -0.001 -0.007 -0.016 C69B 0.030 0.053 0.030 -0.005 -0.002 -0.020 C70B 0.039 0.039 0.039 -0.009 0.008 -0.010 C63B 0.051 0.063 0.073 -0.005 -0.029 -0.023 C65B 0.051 0.058 0.056 0.010 -0.027 -0.028 C64B 0.056 0.071 0.063 0.004 -0.028 -0.026 C66B 0.076 0.074 0.090 0.006 -0.022 -0.036 C36B 0.047 0.087 0.047 0.014 -0.023 -0.034 C37B 0.051 0.066 0.068 0.016 -0.024 -0.028 C38B 0.046 0.052 0.063 0.001 -0.023 -0.025 C39B 0.038 0.046 0.043 0.013 -0.018 -0.023 C40B 0.035 0.049 0.039 0.012 -0.013 -0.019 C41B 0.032 0.039 0.040 0.009 -0.015 -0.019 C42B 0.036 0.048 0.059 -0.008 -0.026 -0.020 C43B 0.044 0.060 0.063 0.009 -0.020 -0.023 C44B 0.034 0.044 0.038 0.005 -0.019 -0.016 C45B 0.042 0.055 0.057 0.001 -0.020 -0.017 C46B 0.045 0.059 0.060 0.000 -0.022 -0.018 C47B 0.034 0.048 0.046 0.006 -0.014 -0.013 C48B 0.028 0.048 0.047 0.001 -0.012 -0.018 C49B 0.031 0.047 0.045 -0.006 -0.009 -0.011 C50B 0.029 0.045 0.045 -0.004 -0.011 -0.011 C51B 0.030 0.049 0.033 -0.005 -0.008 -0.016 C52B 0.018 0.064 0.023 0.002 0.004 -0.021 C53B 0.018 0.044 0.019 0.002 0.004 -0.019 C54B 0.032 0.030 0.024 -0.001 0.001 -0.017 C55B 0.033 0.029 0.023 0.001 -0.005 -0.015 C56B 0.039 0.029 0.026 0.002 0.002 -0.018 C57B 0.035 0.030 0.026 0.003 -0.004 -0.013 C58B 0.028 0.024 0.030 0.001 -0.006 -0.004 C59B 0.032 0.026 0.032 -0.001 -0.010 -0.010 C60B 0.039 0.026 0.035 0.005 -0.007 -0.009 C61B 0.024 0.026 0.026 -0.006 -0.009 -0.006 C62B 0.030 0.029 0.033 -0.002 -0.011 -0.010 F1 0.022 0.028 0.030 0.004 -0.007 -0.010 F2 0.019 0.021 0.031 0.004 -0.001 -0.002 F3 0.036 0.035 0.052 0.009 -0.015 -0.021 F4 0.034 0.025 0.040 0.008 -0.020 -0.013 F3B 0.038 0.065 0.046 0.003 -0.010 -0.018 F4B 0.038 0.053 0.036 -0.010 -0.006 -0.020 N1 0.015 0.022 0.028 0.005 -0.006 -0.003 N2 0.013 0.016 0.027 0.002 -0.004 -0.002 N3 0.027 0.024 0.037 0.015 -0.017 -0.014 N4 0.039 0.031 0.040 0.001 -0.010 -0.014 N3B 0.026 0.042 0.042 0.010 -0.018 -0.014 N4B 0.032 0.035 0.028 -0.002 -0.012 -0.013 O1 0.016 0.024 0.026 0.003 -0.004 -0.004 O2 0.015 0.022 0.027 0.004 -0.003 -0.004 O3 0.027 0.025 0.039 0.011 -0.019 -0.012 O4 0.030 0.025 0.043 0.005 -0.020 -0.008 O3B 0.033 0.057 0.040 -0.006 -0.014 -0.010 O4B 0.030 0.048 0.043 -0.007 -0.012 -0.011 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 F2 1.377(4) . ? B1 F1 1.390(4) . ? B1 O2 1.461(4) . ? B1 O1 1.484(4) . ? B2 F3 1.390(9) . ? B2 F4 1.392(11) . ? B2 O3 1.446(10) . ? B2 O4 1.478(11) . ? B2B F3B 1.347(13) . ? B2B F4B 1.387(13) . ? B2B O4B 1.453(12) . ? B2B O3B 1.496(11) . ? C1 C2 1.184(5) . ? C1 H32 1.01(4) . ? C2 C3 1.437(5) . ? C3 C8 1.388(5) . ? C3 C4 1.396(5) . ? C4 C5 1.385(5) . ? C4 H1 0.97(4) . ? C5 C6 1.392(5) . ? C5 H2 1.00(3) . ? C6 C7 1.391(5) . ? C6 C9 1.463(5) . ? C7 C8 1.373(5) . ? C7 H3 0.90(4) . ? C8 H4 0.92(4) . ? C9 N1 1.357(4) . ? C9 C10 1.389(5) . ? C10 C11 1.409(5) . ? C10 C28 1.509(5) . ? C11 C12 1.397(5) . ? C11 C30 1.492(5) . ? C12 N1 1.380(4) . ? C12 C13 1.428(5) . ? C13 O1 1.326(4) . ? C13 C14 1.383(5) . ? C14 C15 1.393(5) . ? C14 H5 1.00(3) . ? C15 O2 1.321(4) . ? C15 C16 1.418(5) . ? C16 N2 1.376(4) . ? C16 C17 1.406(5) . ? C17 C18 1.407(5) . ? C17 C32 1.504(5) . ? C18 C19 1.413(5) . ? C18 C34 1.495(5) . ? C19 N2 1.361(4) . ? C19 C20 1.460(5) . ? C20 C21 1.396(5) . ? C20 C25 1.399(5) . ? C21 C22 1.379(5) . ? C21 H6 0.98(4) . ? C22 C23 1.392(5) . ? C22 H7 0.93(4) . ? C23 C24 1.393(5) . ? C23 C26 1.441(5) . ? C24 C25 1.382(5) . ? C24 H8 1.06(3) . ? C25 H9 0.95(4) . ? C26 C27 1.173(5) . ? C27 H33 0.87(4) . ? C28 C29 1.517(6) . ? C28 H12 0.98(4) . ? C28 H13 1.00(4) . ? C29 H14 1.03(4) . ? C29 H15 1.02(4) . ? C29 H16 0.91(4) . ? C30 C31 1.528(5) . ? C30 H17 1.02(3) . ? C30 H18 0.99(4) . ? C31 H19 1.08(4) . ? C31 H20 1.08(4) . ? C31 H21 1.03(4) . ? C32 C33 1.526(5) . ? C32 H22 0.99(3) . ? C32 H23 1.03(3) . ? C33 H24 0.92(4) . ? C33 H25 1.04(4) . ? C33 H26 0.97(4) . ? C34 C35 1.530(5) . ? C34 H27 1.03(4) . ? C34 H28 0.98(4) . ? C35 H29 1.08(4) . ? C35 H30 1.04(4) . ? C35 H31 1.09(4) . ? C36 C37 1.062(18) . ? C36 H36 0.88(13) . ? C36 H36B 1.19(11) . ? C37 C38 1.226(17) . ? C38 C39 1.339(14) . ? C38 C43 1.432(15) . ? C39 C40 1.383(12) . ? C39 H63 0.9500 . ? C40 C41 1.382(12) . ? C40 H64 0.9500 . ? C41 C42 1.380(13) . ? C41 C44 1.461(12) . ? C42 C43 1.214(14) . ? C42 H65 0.9500 . ? C43 H66 0.9500 . ? C44 N3 1.347(9) . ? C44 C45 1.419(11) . ? C45 C46 1.413(11) . ? C45 C63 1.525(11) . ? C46 C47 1.420(10) . ? C46 C65 1.495(11) . ? C47 C48 1.395(10) . ? C47 N3 1.395(10) . ? C48 O3 1.338(9) . ? C48 C49 1.395(11) . ? C49 C50 1.345(11) . ? C49 H115 0.9500 . ? C50 O4 1.338(10) . ? C50 C51 1.436(11) . ? C51 N4 1.358(12) . ? C51 C52 1.395(14) . ? C61 C58 1.404(11) . ? C61 C62 1.456(11) . ? C57 C56 1.374(12) . ? C57 C58 1.407(14) . ? C57 H119 0.9500 . ? C58 C59 1.361(12) . ? C60 C55 1.375(11) . ? C60 C59 1.378(11) . ? C60 H68 0.9500 . ? C60 H60B 1.01(8) . ? C62 H62 0.97(9) . ? C62 H62B 0.79(12) . ? C59 H69 0.9500 . ? C59 H59B 1.12(8) . ? C56 C55 1.392(12) . ? C56 H120 0.9500 . ? C55 C54 1.474(11) . ? C54 N4 1.341(10) . ? C54 C53 1.413(12) . ? C52 C53 1.378(13) . ? C52 C67 1.545(14) . ? C53 C69 1.465(14) . ? C63 C64 1.508(17) . ? C63 H71 0.9900 . ? C63 H72 0.9900 . ? C64 H73 0.9800 . ? C64 H74 0.9800 . ? C64 H75 0.9800 . ? C65 C66 1.600(12) . ? C65 H76 0.9900 . ? C65 H77 0.9900 . ? C66 H78 0.9800 . ? C66 H79 0.9800 . ? C66 H80 0.9800 . ? C67 C68 1.769(18) . ? C67 H81 0.9900 . ? C67 H82 0.9900 . ? C68 H83 0.9800 . ? C68 H84 0.9800 . ? C68 H85 0.9800 . ? C69 C70 1.369(16) . ? C69 H86 0.9900 . ? C69 H87 0.9900 . ? C70 H88 0.9800 . ? C70 H89 0.9800 . ? C70 H90 0.9800 . ? C68B C67B 1.347(15) . ? C68B H91 0.9800 . ? C68B H92 0.9800 . ? C68B H93 0.9800 . ? C67B C52B 1.496(11) . ? C67B H94 0.9900 . ? C67B H95 0.9900 . ? C69B C53B 1.431(11) . ? C69B C70B 1.549(14) . ? C69B H96 0.9900 . ? C69B H97 0.9900 . ? C70B H98 0.9800 . ? C70B H99 0.9800 . ? C70B H100 0.9800 . ? C63B C45B 1.536(14) . ? C63B C64B 1.659(16) . ? C63B H101 0.9900 . ? C63B H102 0.9900 . ? C65B C66B 1.442(15) . ? C65B C46B 1.563(15) . ? C65B H103 0.9900 . ? C65B H104 0.9900 . ? C64B H105 0.9800 . ? C64B H106 0.9800 . ? C64B H107 0.9800 . ? C66B H108 0.9800 . ? C66B H109 0.9800 . ? C66B H110 0.9800 . ? C36B C37B 1.233(19) . ? C36B H36 1.00(13) . ? C36B H36B 0.83(12) . ? C37B C38B 1.618(18) . ? C38B C43B 1.374(15) . ? C38B C39B 1.428(16) . ? C39B C40B 1.360(13) . ? C39B H111 0.9500 . ? C40B C41B 1.401(13) . ? C40B H112 0.9500 . ? C41B C42B 1.406(13) . ? C41B C44B 1.471(12) . ? C42B C43B 1.511(15) . ? C42B H113 0.9500 . ? C43B H114 0.9500 . ? C44B N3B 1.376(11) . ? C44B C45B 1.397(13) . ? C45B C46B 1.420(14) . ? C46B C47B 1.411(13) . ? C47B N3B 1.352(12) . ? C47B C48B 1.458(12) . ? C48B O3B 1.334(10) . ? C48B C49B 1.347(13) . ? C49B C50B 1.441(13) . ? C49B H116 0.9500 . ? C50B O4B 1.313(11) . ? C50B C51B 1.391(12) . ? C51B C52B 1.343(12) . ? C51B N4B 1.382(12) . ? C52B C53B 1.409(10) . ? C53B C54B 1.355(11) . ? C54B N4B 1.371(10) . ? C54B C55B 1.467(11) . ? C55B C56B 1.373(12) . ? C55B C60B 1.400(12) . ? C56B C57B 1.366(13) . ? C56B H121 0.9500 . ? C57B C58B 1.383(15) . ? C57B H122 0.9500 . ? C58B C59B 1.418(14) . ? C58B C61B 1.474(13) . ? C59B C60B 1.365(12) . ? C59B H59B 1.03(8) . ? C60B H60B 0.98(8) . ? C61B C62B 0.895(10) . ? C62B H62 1.24(9) . ? C62B H62B 1.01(12) . ? N1 H10 0.85(4) . ? N2 H11 0.89(3) . ? N3 H3A 0.65(7) . ? N4 H4A 0.76(8) . ? N3B H3A 1.09(7) . ? N3B H117 0.8800 . ? N4B H4A 1.07(8) . ? N4B H118 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 F2 B1 F1 109.5(3) . . ? F2 B1 O2 110.2(3) . . ? F1 B1 O2 109.4(3) . . ? F2 B1 O1 107.3(3) . . ? F1 B1 O1 108.8(3) . . ? O2 B1 O1 111.6(3) . . ? F3 B2 F4 108.9(7) . . ? F3 B2 O3 111.5(6) . . ? F4 B2 O3 108.6(6) . . ? F3 B2 O4 110.0(7) . . ? F4 B2 O4 106.0(6) . . ? O3 B2 O4 111.6(7) . . ? F3B B2B F4B 109.3(8) . . ? F3B B2B O4B 110.5(9) . . ? F4B B2B O4B 107.5(8) . . ? F3B B2B O3B 109.6(8) . . ? F4B B2B O3B 108.3(9) . . ? O4B B2B O3B 111.5(7) . . ? C2 C1 H32 176(2) . . ? C1 C2 C3 179.1(4) . . ? C8 C3 C4 118.6(3) . . ? C8 C3 C2 120.6(3) . . ? C4 C3 C2 120.7(3) . . ? C5 C4 C3 120.4(3) . . ? C5 C4 H1 118(2) . . ? C3 C4 H1 122(2) . . ? C4 C5 C6 120.8(3) . . ? C4 C5 H2 120(2) . . ? C6 C5 H2 119(2) . . ? C7 C6 C5 118.3(3) . . ? C7 C6 C9 120.8(3) . . ? C5 C6 C9 120.9(3) . . ? C8 C7 C6 121.2(3) . . ? C8 C7 H3 120(2) . . ? C6 C7 H3 119(2) . . ? C7 C8 C3 120.7(3) . . ? C7 C8 H4 118(2) . . ? C3 C8 H4 122(2) . . ? N1 C9 C10 107.8(3) . . ? N1 C9 C6 120.0(3) . . ? C10 C9 C6 132.2(3) . . ? C9 C10 C11 107.6(3) . . ? C9 C10 C28 128.0(3) . . ? C11 C10 C28 124.4(3) . . ? C12 C11 C10 107.3(3) . . ? C12 C11 C30 127.1(3) . . ? C10 C11 C30 125.5(3) . . ? N1 C12 C11 106.9(3) . . ? N1 C12 C13 119.0(3) . . ? C11 C12 C13 134.0(3) . . ? O1 C13 C14 120.3(3) . . ? O1 C13 C12 114.4(3) . . ? C14 C13 C12 125.3(3) . . ? C13 C14 C15 120.6(3) . . ? C13 C14 H5 119.4(19) . . ? C15 C14 H5 119.7(19) . . ? O2 C15 C14 120.0(3) . . ? O2 C15 C16 115.0(3) . . ? C14 C15 C16 125.1(3) . . ? N2 C16 C17 106.9(3) . . ? N2 C16 C15 119.7(3) . . ? C17 C16 C15 133.4(3) . . ? C16 C17 C18 107.3(3) . . ? C16 C17 C32 128.1(3) . . ? C18 C17 C32 124.5(3) . . ? C17 C18 C19 107.7(3) . . ? C17 C18 C34 122.8(3) . . ? C19 C18 C34 129.4(3) . . ? N2 C19 C18 106.8(3) . . ? N2 C19 C20 121.3(3) . . ? C18 C19 C20 131.9(3) . . ? C21 C20 C25 116.6(3) . . ? C21 C20 C19 121.0(3) . . ? C25 C20 C19 122.4(3) . . ? C22 C21 C20 121.5(3) . . ? C22 C21 H6 117(2) . . ? C20 C21 H6 121(2) . . ? C21 C22 C23 121.3(3) . . ? C21 C22 H7 119(2) . . ? C23 C22 H7 120(2) . . ? C22 C23 C24 118.0(3) . . ? C22 C23 C26 122.0(3) . . ? C24 C23 C26 119.9(3) . . ? C25 C24 C23 120.2(3) . . ? C25 C24 H8 123(2) . . ? C23 C24 H8 117(2) . . ? C24 C25 C20 122.3(3) . . ? C24 C25 H9 119(2) . . ? C20 C25 H9 119(2) . . ? C27 C26 C23 178.5(4) . . ? C26 C27 H33 178(3) . . ? C10 C28 C29 116.2(3) . . ? C10 C28 H12 111(2) . . ? C29 C28 H12 107(2) . . ? C10 C28 H13 112(2) . . ? C29 C28 H13 104(2) . . ? H12 C28 H13 107(3) . . ? C28 C29 H14 110(2) . . ? C28 C29 H15 112(2) . . ? H14 C29 H15 109(3) . . ? C28 C29 H16 110(3) . . ? H14 C29 H16 107(3) . . ? H15 C29 H16 109(4) . . ? C11 C30 C31 113.3(3) . . ? C11 C30 H17 111.9(19) . . ? C31 C30 H17 108.8(19) . . ? C11 C30 H18 105.8(19) . . ? C31 C30 H18 110(2) . . ? H17 C30 H18 106(3) . . ? C30 C31 H19 107(2) . . ? C30 C31 H20 113(2) . . ? H19 C31 H20 108(3) . . ? C30 C31 H21 106(2) . . ? H19 C31 H21 111(3) . . ? H20 C31 H21 112(3) . . ? C17 C32 C33 113.7(3) . . ? C17 C32 H22 107.9(19) . . ? C33 C32 H22 109.8(19) . . ? C17 C32 H23 109.4(19) . . ? C33 C32 H23 106.6(19) . . ? H22 C32 H23 109(3) . . ? C32 C33 H24 111(2) . . ? C32 C33 H25 111(2) . . ? H24 C33 H25 109(3) . . ? C32 C33 H26 108(2) . . ? H24 C33 H26 105(3) . . ? H25 C33 H26 112(3) . . ? C18 C34 C35 113.0(3) . . ? C18 C34 H27 106.5(18) . . ? C35 C34 H27 108.3(19) . . ? C18 C34 H28 113(2) . . ? C35 C34 H28 110(2) . . ? H27 C34 H28 106(3) . . ? C34 C35 H29 109(2) . . ? C34 C35 H30 112(2) . . ? H29 C35 H30 112(3) . . ? C34 C35 H31 110(2) . . ? H29 C35 H31 114(3) . . ? H30 C35 H31 100(3) . . ? C37 C36 H36 165(9) . . ? C37 C36 H36B 150(7) . . ? H36 C36 H36B 44(8) . . ? C36 C37 C38 176.2(16) . . ? C37 C38 C39 118.4(11) . . ? C37 C38 C43 128.0(12) . . ? C39 C38 C43 112.4(10) . . ? C38 C39 C40 121.7(9) . . ? C38 C39 H63 119.1 . . ? C40 C39 H63 119.1 . . ? C41 C40 C39 120.9(8) . . ? C41 C40 H64 119.5 . . ? C39 C40 H64 119.5 . . ? C42 C41 C40 115.1(8) . . ? C42 C41 C44 124.2(8) . . ? C40 C41 C44 120.5(7) . . ? C43 C42 C41 122.1(10) . . ? C43 C42 H65 119.0 . . ? C41 C42 H65 119.0 . . ? C42 C43 C38 126.0(11) . . ? C42 C43 H66 117.0 . . ? C38 C43 H66 117.0 . . ? N3 C44 C45 106.6(7) . . ? N3 C44 C41 122.4(7) . . ? C45 C44 C41 130.9(7) . . ? C46 C45 C44 108.5(7) . . ? C46 C45 C63 124.3(7) . . ? C44 C45 C63 126.8(7) . . ? C45 C46 C47 106.7(7) . . ? C45 C46 C65 126.2(7) . . ? C47 C46 C65 127.1(7) . . ? C48 C47 N3 120.7(7) . . ? C48 C47 C46 132.9(7) . . ? N3 C47 C46 106.4(6) . . ? O3 C48 C47 114.7(7) . . ? O3 C48 C49 119.1(6) . . ? C47 C48 C49 126.2(7) . . ? C50 C49 C48 120.6(7) . . ? C50 C49 H115 119.7 . . ? C48 C49 H115 119.7 . . ? O4 C50 C49 121.6(7) . . ? O4 C50 C51 113.0(7) . . ? C49 C50 C51 125.4(8) . . ? N4 C51 C52 107.6(7) . . ? N4 C51 C50 118.4(7) . . ? C52 C51 C50 133.8(9) . . ? C58 C61 C62 171.6(10) . . ? C56 C57 C58 119.1(8) . . ? C56 C57 H119 120.5 . . ? C58 C57 H119 120.5 . . ? C59 C58 C61 122.1(9) . . ? C59 C58 C57 119.1(7) . . ? C61 C58 C57 118.0(8) . . ? C55 C60 C59 122.5(8) . . ? C55 C60 H68 118.8 . . ? C59 C60 H68 118.8 . . ? C55 C60 H60B 109(5) . . ? C59 C60 H60B 112(5) . . ? H68 C60 H60B 43.1 . . ? C61 C62 H62 176(6) . . ? C61 C62 H62B 154(6) . . ? H62 C62 H62B 26(9) . . ? C58 C59 C60 119.7(8) . . ? C58 C59 H69 120.2 . . ? C60 C59 H69 120.2 . . ? C58 C59 H59B 107(4) . . ? C60 C59 H59B 126(4) . . ? H69 C59 H59B 28.1 . . ? C57 C56 C55 121.7(8) . . ? C57 C56 H120 119.1 . . ? C55 C56 H120 119.1 . . ? C60 C55 C56 116.8(7) . . ? C60 C55 C54 121.8(7) . . ? C56 C55 C54 121.3(7) . . ? N4 C54 C53 105.7(7) . . ? N4 C54 C55 123.6(7) . . ? C53 C54 C55 130.4(8) . . ? C53 C52 C51 106.3(8) . . ? C53 C52 C67 126.0(9) . . ? C51 C52 C67 127.7(9) . . ? C52 C53 C54 108.9(8) . . ? C52 C53 C69 126.3(9) . . ? C54 C53 C69 124.5(8) . . ? C64 C63 C45 123.8(9) . . ? C64 C63 H71 106.4 . . ? C45 C63 H71 106.4 . . ? C64 C63 H72 106.4 . . ? C45 C63 H72 106.4 . . ? H71 C63 H72 106.5 . . ? C46 C65 C66 113.0(7) . . ? C46 C65 H76 109.0 . . ? C66 C65 H76 109.0 . . ? C46 C65 H77 109.0 . . ? C66 C65 H77 109.0 . . ? H76 C65 H77 107.8 . . ? C52 C67 C68 104.2(9) . . ? C52 C67 H81 110.9 . . ? C68 C67 H81 110.9 . . ? C52 C67 H82 110.9 . . ? C68 C67 H82 110.9 . . ? H81 C67 H82 108.9 . . ? C70 C69 C53 110.6(11) . . ? C70 C69 H86 109.5 . . ? C53 C69 H86 109.5 . . ? C70 C69 H87 109.5 . . ? C53 C69 H87 109.5 . . ? H86 C69 H87 108.1 . . ? C67B C68B H91 109.5 . . ? C67B C68B H92 109.5 . . ? H91 C68B H92 109.5 . . ? C67B C68B H93 109.5 . . ? H91 C68B H93 109.5 . . ? H92 C68B H93 109.5 . . ? C68B C67B C52B 117.9(9) . . ? C68B C67B H94 107.8 . . ? C52B C67B H94 107.8 . . ? C68B C67B H95 107.8 . . ? C52B C67B H95 107.8 . . ? H94 C67B H95 107.2 . . ? C53B C69B C70B 115.4(7) . . ? C53B C69B H96 108.4 . . ? C70B C69B H96 108.4 . . ? C53B C69B H97 108.4 . . ? C70B C69B H97 108.4 . . ? H96 C69B H97 107.5 . . ? C69B C70B H98 109.5 . . ? C69B C70B H99 109.5 . . ? H98 C70B H99 109.5 . . ? C69B C70B H100 109.5 . . ? H98 C70B H100 109.5 . . ? H99 C70B H100 109.5 . . ? C45B C63B C64B 100.0(8) . . ? C45B C63B H101 111.8 . . ? C64B C63B H101 111.8 . . ? C45B C63B H102 111.8 . . ? C64B C63B H102 111.8 . . ? H101 C63B H102 109.5 . . ? C66B C65B C46B 104.1(9) . . ? C66B C65B H103 110.9 . . ? C46B C65B H103 110.9 . . ? C66B C65B H104 110.9 . . ? C46B C65B H104 110.9 . . ? H103 C65B H104 109.0 . . ? C63B C64B H105 109.5 . . ? C63B C64B H106 109.5 . . ? H105 C64B H106 109.5 . . ? C63B C64B H107 109.5 . . ? H105 C64B H107 109.5 . . ? H106 C64B H107 109.5 . . ? C65B C66B H108 109.5 . . ? C65B C66B H109 109.5 . . ? H108 C66B H109 109.5 . . ? C65B C66B H110 109.5 . . ? H108 C66B H110 109.5 . . ? H109 C66B H110 109.5 . . ? C37B C36B H36 127(9) . . ? C37B C36B H36B 173(8) . . ? H36 C36B H36B 53(9) . . ? C36B C37B C38B 172.8(12) . . ? C43B C38B C39B 121.6(10) . . ? C43B C38B C37B 113.8(11) . . ? C39B C38B C37B 121.7(10) . . ? C40B C39B C38B 121.0(9) . . ? C40B C39B H111 119.5 . . ? C38B C39B H111 119.5 . . ? C39B C40B C41B 122.0(9) . . ? C39B C40B H112 119.0 . . ? C41B C40B H112 119.0 . . ? C40B C41B C42B 116.2(8) . . ? C40B C41B C44B 121.2(8) . . ? C42B C41B C44B 121.6(8) . . ? C41B C42B C43B 123.1(8) . . ? C41B C42B H113 118.4 . . ? C43B C42B H113 118.4 . . ? C38B C43B C42B 113.1(10) . . ? C38B C43B H114 123.4 . . ? C42B C43B H114 123.4 . . ? N3B C44B C45B 105.7(8) . . ? N3B C44B C41B 122.0(8) . . ? C45B C44B C41B 132.2(8) . . ? C44B C45B C46B 109.2(8) . . ? C44B C45B C63B 128.6(9) . . ? C46B C45B C63B 122.1(9) . . ? C47B C46B C45B 105.4(9) . . ? C47B C46B C65B 129.6(9) . . ? C45B C46B C65B 125.0(9) . . ? N3B C47B C46B 108.1(8) . . ? N3B C47B C48B 120.6(8) . . ? C46B C47B C48B 131.3(9) . . ? O3B C48B C49B 123.3(8) . . ? O3B C48B C47B 110.5(8) . . ? C49B C48B C47B 125.8(8) . . ? C48B C49B C50B 120.2(8) . . ? C48B C49B H116 119.9 . . ? C50B C49B H116 119.9 . . ? O4B C50B C51B 117.3(9) . . ? O4B C50B C49B 117.3(8) . . ? C51B C50B C49B 125.3(8) . . ? C52B C51B N4B 107.5(7) . . ? C52B C51B C50B 135.5(9) . . ? N4B C51B C50B 116.9(8) . . ? C51B C52B C53B 107.3(7) . . ? C51B C52B C67B 125.9(8) . . ? C53B C52B C67B 126.6(7) . . ? C54B C53B C52B 108.8(7) . . ? C54B C53B C69B 126.1(7) . . ? C52B C53B C69B 125.0(7) . . ? C53B C54B N4B 106.4(7) . . ? C53B C54B C55B 131.7(7) . . ? N4B C54B C55B 121.9(7) . . ? C56B C55B C60B 117.8(7) . . ? C56B C55B C54B 123.7(8) . . ? C60B C55B C54B 118.3(7) . . ? C57B C56B C55B 122.0(8) . . ? C57B C56B H121 119.0 . . ? C55B C56B H121 119.0 . . ? C56B C57B C58B 121.2(8) . . ? C56B C57B H122 119.4 . . ? C58B C57B H122 119.4 . . ? C57B C58B C59B 116.5(9) . . ? C57B C58B C61B 124.7(9) . . ? C59B C58B C61B 118.5(10) . . ? C60B C59B C58B 121.4(9) . . ? C60B C59B H59B 121(4) . . ? C58B C59B H59B 118(4) . . ? C59B C60B C55B 120.4(8) . . ? C59B C60B H60B 123(5) . . ? C55B C60B H60B 116(5) . . ? C62B C61B C58B 170.7(15) . . ? C61B C62B H62 164(4) . . ? C61B C62B H62B 176(6) . . ? H62 C62B H62B 18(8) . . ? C9 N1 C12 110.2(3) . . ? C9 N1 H10 128(2) . . ? C12 N1 H10 119(2) . . ? C19 N2 C16 111.2(3) . . ? C19 N2 H11 128(2) . . ? C16 N2 H11 121(2) . . ? C44 N3 C47 111.8(6) . . ? C44 N3 H3A 127(7) . . ? C47 N3 H3A 121(7) . . ? C54 N4 C51 111.2(7) . . ? C54 N4 H4A 130(6) . . ? C51 N4 H4A 119(6) . . ? C47B N3B C44B 111.5(7) . . ? C47B N3B H3A 141(4) . . ? C44B N3B H3A 104(4) . . ? C47B N3B H117 124.2 . . ? C44B N3B H117 124.2 . . ? H3A N3B H117 24.1 . . ? C54B N4B C51B 109.6(7) . . ? C54B N4B H4A 144(4) . . ? C51B N4B H4A 106(4) . . ? C54B N4B H118 125.2 . . ? C51B N4B H118 125.2 . . ? H4A N4B H118 19.1 . . ? C13 O1 B1 119.7(3) . . ? C15 O2 B1 120.9(3) . . ? C48 O3 B2 121.2(6) . . ? C50 O4 B2 118.2(6) . . ? C48B O3B B2B 119.0(7) . . ? C50B O4B B2B 124.9(8) . . ? 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 C1 C2 C3 C8 -20(26) . . . . ? C1 C2 C3 C4 161(26) . . . . ? C8 C3 C4 C5 -0.3(5) . . . . ? C2 C3 C4 C5 178.7(3) . . . . ? C3 C4 C5 C6 0.3(5) . . . . ? C4 C5 C6 C7 0.0(5) . . . . ? C4 C5 C6 C9 177.8(3) . . . . ? C5 C6 C7 C8 -0.4(5) . . . . ? C9 C6 C7 C8 -178.2(3) . . . . ? C6 C7 C8 C3 0.4(5) . . . . ? C4 C3 C8 C7 -0.1(5) . . . . ? C2 C3 C8 C7 -179.1(3) . . . . ? C7 C6 C9 N1 39.7(5) . . . . ? C5 C6 C9 N1 -138.0(3) . . . . ? C7 C6 C9 C10 -139.8(4) . . . . ? C5 C6 C9 C10 42.6(5) . . . . ? N1 C9 C10 C11 2.7(4) . . . . ? C6 C9 C10 C11 -177.8(3) . . . . ? N1 C9 C10 C28 -176.4(3) . . . . ? C6 C9 C10 C28 3.1(6) . . . . ? C9 C10 C11 C12 0.0(4) . . . . ? C28 C10 C11 C12 179.1(3) . . . . ? C9 C10 C11 C30 -177.9(3) . . . . ? C28 C10 C11 C30 1.2(5) . . . . ? C10 C11 C12 N1 -2.6(4) . . . . ? C30 C11 C12 N1 175.2(3) . . . . ? C10 C11 C12 C13 174.3(3) . . . . ? C30 C11 C12 C13 -7.9(6) . . . . ? N1 C12 C13 O1 -14.6(4) . . . . ? C11 C12 C13 O1 168.8(3) . . . . ? N1 C12 C13 C14 162.3(3) . . . . ? C11 C12 C13 C14 -14.3(6) . . . . ? O1 C13 C14 C15 5.3(5) . . . . ? C12 C13 C14 C15 -171.4(3) . . . . ? C13 C14 C15 O2 -7.1(5) . . . . ? C13 C14 C15 C16 173.2(3) . . . . ? O2 C15 C16 N2 -11.3(4) . . . . ? C14 C15 C16 N2 168.5(3) . . . . ? O2 C15 C16 C17 170.4(3) . . . . ? C14 C15 C16 C17 -9.9(6) . . . . ? N2 C16 C17 C18 -1.7(3) . . . . ? C15 C16 C17 C18 176.8(3) . . . . ? N2 C16 C17 C32 174.3(3) . . . . ? C15 C16 C17 C32 -7.2(6) . . . . ? C16 C17 C18 C19 1.5(3) . . . . ? C32 C17 C18 C19 -174.6(3) . . . . ? C16 C17 C18 C34 -176.2(3) . . . . ? C32 C17 C18 C34 7.7(5) . . . . ? C17 C18 C19 N2 -0.7(3) . . . . ? C34 C18 C19 N2 176.8(3) . . . . ? C17 C18 C19 C20 177.3(3) . . . . ? C34 C18 C19 C20 -5.2(6) . . . . ? N2 C19 C20 C21 -3.0(5) . . . . ? C18 C19 C20 C21 179.2(3) . . . . ? N2 C19 C20 C25 176.3(3) . . . . ? C18 C19 C20 C25 -1.5(5) . . . . ? C25 C20 C21 C22 0.2(5) . . . . ? C19 C20 C21 C22 179.6(3) . . . . ? C20 C21 C22 C23 -0.6(6) . . . . ? C21 C22 C23 C24 0.6(5) . . . . ? C21 C22 C23 C26 -177.5(3) . . . . ? C22 C23 C24 C25 -0.2(5) . . . . ? C26 C23 C24 C25 178.0(3) . . . . ? C23 C24 C25 C20 -0.2(5) . . . . ? C21 C20 C25 C24 0.2(5) . . . . ? C19 C20 C25 C24 -179.2(3) . . . . ? C22 C23 C26 C27 136(16) . . . . ? C24 C23 C26 C27 -42(16) . . . . ? C9 C10 C28 C29 47.3(5) . . . . ? C11 C10 C28 C29 -131.6(4) . . . . ? C12 C11 C30 C31 101.6(4) . . . . ? C10 C11 C30 C31 -81.0(4) . . . . ? C16 C17 C32 C33 98.8(4) . . . . ? C18 C17 C32 C33 -85.9(4) . . . . ? C17 C18 C34 C35 99.3(4) . . . . ? C19 C18 C34 C35 -77.8(5) . . . . ? C36 C37 C38 C39 -87(24) . . . . ? C36 C37 C38 C43 106(23) . . . . ? C37 C38 C39 C40 -175.0(10) . . . . ? C43 C38 C39 C40 -5.9(14) . . . . ? C38 C39 C40 C41 -4.8(13) . . . . ? C39 C40 C41 C42 8.7(12) . . . . ? C39 C40 C41 C44 -176.4(7) . . . . ? C40 C41 C42 C43 -1.0(15) . . . . ? C44 C41 C42 C43 -175.6(10) . . . . ? C41 C42 C43 C38 -11.3(19) . . . . ? C37 C38 C43 C42 -177.6(13) . . . . ? C39 C38 C43 C42 14.6(17) . . . . ? C42 C41 C44 N3 17.9(13) . . . . ? C40 C41 C44 N3 -156.4(7) . . . . ? C42 C41 C44 C45 -159.0(9) . . . . ? C40 C41 C44 C45 26.7(13) . . . . ? N3 C44 C45 C46 0.7(8) . . . . ? C41 C44 C45 C46 177.9(8) . . . . ? N3 C44 C45 C63 -173.2(8) . . . . ? C41 C44 C45 C63 4.1(13) . . . . ? C44 C45 C46 C47 -1.3(8) . . . . ? C63 C45 C46 C47 172.7(7) . . . . ? C44 C45 C46 C65 -179.8(7) . . . . ? C63 C45 C46 C65 -5.7(13) . . . . ? C45 C46 C47 C48 -177.9(7) . . . . ? C65 C46 C47 C48 0.6(13) . . . . ? C45 C46 C47 N3 1.5(8) . . . . ? C65 C46 C47 N3 179.9(7) . . . . ? N3 C47 C48 O3 12.1(9) . . . . ? C46 C47 C48 O3 -168.6(7) . . . . ? N3 C47 C48 C49 -167.9(7) . . . . ? C46 C47 C48 C49 11.4(13) . . . . ? O3 C48 C49 C50 7.5(12) . . . . ? C47 C48 C49 C50 -172.5(7) . . . . ? C48 C49 C50 O4 -2.2(13) . . . . ? C48 C49 C50 C51 175.7(8) . . . . ? O4 C50 C51 N4 6.3(12) . . . . ? C49 C50 C51 N4 -171.7(9) . . . . ? O4 C50 C51 C52 -167.6(10) . . . . ? C49 C50 C51 C52 14.4(17) . . . . ? C62 C61 C58 C59 16(7) . . . . ? C62 C61 C58 C57 -154(6) . . . . ? C56 C57 C58 C59 10.7(13) . . . . ? C56 C57 C58 C61 -179.3(8) . . . . ? C61 C58 C59 C60 179.9(9) . . . . ? C57 C58 C59 C60 -10.6(13) . . . . ? C55 C60 C59 C58 2.7(12) . . . . ? C58 C57 C56 C55 -2.8(12) . . . . ? C59 C60 C55 C56 5.1(11) . . . . ? C59 C60 C55 C54 -178.3(7) . . . . ? C57 C56 C55 C60 -4.9(11) . . . . ? C57 C56 C55 C54 178.5(7) . . . . ? C60 C55 C54 N4 -117.3(10) . . . . ? C56 C55 C54 N4 59.1(12) . . . . ? C60 C55 C54 C53 54.5(13) . . . . ? C56 C55 C54 C53 -129.1(11) . . . . ? N4 C51 C52 C53 2.5(12) . . . . ? C50 C51 C52 C53 176.8(10) . . . . ? N4 C51 C52 C67 -176.4(10) . . . . ? C50 C51 C52 C67 -2.1(18) . . . . ? C51 C52 C53 C54 0.3(12) . . . . ? C67 C52 C53 C54 179.3(10) . . . . ? C51 C52 C53 C69 -174.6(11) . . . . ? C67 C52 C53 C69 4.4(19) . . . . ? N4 C54 C53 C52 -3.0(12) . . . . ? C55 C54 C53 C52 -175.9(9) . . . . ? N4 C54 C53 C69 172.0(11) . . . . ? C55 C54 C53 C69 -0.9(18) . . . . ? C46 C45 C63 C64 -87.8(12) . . . . ? C44 C45 C63 C64 85.2(11) . . . . ? C45 C46 C65 C66 86.7(9) . . . . ? C47 C46 C65 C66 -91.4(9) . . . . ? C53 C52 C67 C68 85.9(13) . . . . ? C51 C52 C67 C68 -95.4(12) . . . . ? C52 C53 C69 C70 -119.7(13) . . . . ? C54 C53 C69 C70 66.2(15) . . . . ? C36B C37B C38B C43B -165(9) . . . . ? C36B C37B C38B C39B 34(10) . . . . ? C43B C38B C39B C40B 5.7(18) . . . . ? C37B C38B C39B C40B 165.3(10) . . . . ? C38B C39B C40B C41B 8.7(16) . . . . ? C39B C40B C41B C42B -8.5(14) . . . . ? C39B C40B C41B C44B -177.4(9) . . . . ? C40B C41B C42B C43B -4.9(14) . . . . ? C44B C41B C42B C43B 164.0(9) . . . . ? C39B C38B C43B C42B -17.3(16) . . . . ? C37B C38B C43B C42B -178.3(9) . . . . ? C41B C42B C43B C38B 17.4(15) . . . . ? C40B C41B C44B N3B -165.9(8) . . . . ? C42B C41B C44B N3B 25.7(14) . . . . ? C40B C41B C44B C45B 19.0(17) . . . . ? C42B C41B C44B C45B -149.3(11) . . . . ? N3B C44B C45B C46B -0.3(12) . . . . ? C41B C44B C45B C46B 175.4(10) . . . . ? N3B C44B C45B C63B 178.8(10) . . . . ? C41B C44B C45B C63B -5.6(19) . . . . ? C64B C63B C45B C44B 56.5(14) . . . . ? C64B C63B C45B C46B -124.5(11) . . . . ? C44B C45B C46B C47B 1.7(13) . . . . ? C63B C45B C46B C47B -177.4(10) . . . . ? C44B C45B C46B C65B -175.3(10) . . . . ? C63B C45B C46B C65B 5.6(18) . . . . ? C66B C65B C46B C47B 94.5(13) . . . . ? C66B C65B C46B C45B -89.3(13) . . . . ? C45B C46B C47B N3B -2.6(12) . . . . ? C65B C46B C47B N3B 174.3(10) . . . . ? C45B C46B C47B C48B 176.2(10) . . . . ? C65B C46B C47B C48B -6.9(19) . . . . ? N3B C47B C48B O3B -0.1(13) . . . . ? C46B C47B C48B O3B -178.7(10) . . . . ? N3B C47B C48B C49B 172.2(10) . . . . ? C46B C47B C48B C49B -6.5(18) . . . . ? O3B C48B C49B C50B 2.5(15) . . . . ? C47B C48B C49B C50B -168.8(10) . . . . ? C48B C49B C50B O4B -4.0(15) . . . . ? C48B C49B C50B C51B 174.3(10) . . . . ? O4B C50B C51B C52B -179.0(11) . . . . ? C49B C50B C51B C52B 3(2) . . . . ? O4B C50B C51B N4B 1.2(14) . . . . ? C49B C50B C51B N4B -177.0(10) . . . . ? N4B C51B C52B C53B -5.7(11) . . . . ? C50B C51B C52B C53B 174.5(11) . . . . ? N4B C51B C52B C67B 178.6(9) . . . . ? C50B C51B C52B C67B -1.2(19) . . . . ? C68B C67B C52B C51B 75.9(14) . . . . ? C68B C67B C52B C53B -98.9(11) . . . . ? C51B C52B C53B C54B 5.4(10) . . . . ? C67B C52B C53B C54B -178.9(8) . . . . ? C51B C52B C53B C69B -176.9(9) . . . . ? C67B C52B C53B C69B -1.2(14) . . . . ? C70B C69B C53B C54B -93.2(10) . . . . ? C70B C69B C53B C52B 89.5(10) . . . . ? C52B C53B C54B N4B -2.9(9) . . . . ? C69B C53B C54B N4B 179.5(8) . . . . ? C52B C53B C54B C55B 179.4(8) . . . . ? C69B C53B C54B C55B 1.7(14) . . . . ? C53B C54B C55B C56B -111.0(11) . . . . ? N4B C54B C55B C56B 71.5(11) . . . . ? C53B C54B C55B C60B 64.1(12) . . . . ? N4B C54B C55B C60B -113.4(9) . . . . ? C60B C55B C56B C57B 2.6(12) . . . . ? C54B C55B C56B C57B 177.7(7) . . . . ? C55B C56B C57B C58B 4.4(13) . . . . ? C56B C57B C58B C59B -9.5(13) . . . . ? C56B C57B C58B C61B 176.9(9) . . . . ? C57B C58B C59B C60B 8.0(13) . . . . ? C61B C58B C59B C60B -177.9(9) . . . . ? C58B C59B C60B C55B -1.4(13) . . . . ? C56B C55B C60B C59B -4.0(12) . . . . ? C54B C55B C60B C59B -179.3(7) . . . . ? C57B C58B C61B C62B 1(10) . . . . ? C59B C58B C61B C62B -173(9) . . . . ? C10 C9 N1 C12 -4.4(4) . . . . ? C6 C9 N1 C12 176.0(3) . . . . ? C11 C12 N1 C9 4.4(4) . . . . ? C13 C12 N1 C9 -173.1(3) . . . . ? C18 C19 N2 C16 -0.4(3) . . . . ? C20 C19 N2 C16 -178.6(3) . . . . ? C17 C16 N2 C19 1.3(3) . . . . ? C15 C16 N2 C19 -177.5(3) . . . . ? C45 C44 N3 C47 0.3(8) . . . . ? C41 C44 N3 C47 -177.3(7) . . . . ? C48 C47 N3 C44 178.3(6) . . . . ? C46 C47 N3 C44 -1.1(8) . . . . ? C53 C54 N4 C51 4.7(11) . . . . ? C55 C54 N4 C51 178.2(8) . . . . ? C52 C51 N4 C54 -4.6(11) . . . . ? C50 C51 N4 C54 -180.0(8) . . . . ? C46B C47B N3B C44B 2.5(11) . . . . ? C48B C47B N3B C44B -176.4(8) . . . . ? C45B C44B N3B C47B -1.4(11) . . . . ? C41B C44B N3B C47B -177.6(9) . . . . ? C53B C54B N4B C51B -0.7(10) . . . . ? C55B C54B N4B C51B 177.4(8) . . . . ? C52B C51B N4B C54B 4.1(11) . . . . ? C50B C51B N4B C54B -176.1(8) . . . . ? C14 C13 O1 B1 13.9(4) . . . . ? C12 C13 O1 B1 -169.0(3) . . . . ? F2 B1 O1 C13 -150.0(3) . . . . ? F1 B1 O1 C13 91.6(3) . . . . ? O2 B1 O1 C13 -29.1(4) . . . . ? C14 C15 O2 B1 -10.9(4) . . . . ? C16 C15 O2 B1 168.8(3) . . . . ? F2 B1 O2 C15 146.8(3) . . . . ? F1 B1 O2 C15 -92.7(3) . . . . ? O1 B1 O2 C15 27.7(4) . . . . ? C47 C48 O3 B2 -171.3(6) . . . . ? C49 C48 O3 B2 8.8(10) . . . . ? F3 B2 O3 C48 96.5(8) . . . . ? F4 B2 O3 C48 -143.5(6) . . . . ? O4 B2 O3 C48 -27.0(9) . . . . ? C49 C50 O4 B2 -18.4(11) . . . . ? C51 C50 O4 B2 163.5(7) . . . . ? F3 B2 O4 C50 -92.9(8) . . . . ? F4 B2 O4 C50 149.6(6) . . . . ? O3 B2 O4 C50 31.5(9) . . . . ? C49B C48B O3B B2B 11.1(14) . . . . ? C47B C48B O3B B2B -176.4(8) . . . . ? F3B B2B O3B C48B 101.4(10) . . . . ? F4B B2B O3B C48B -139.4(8) . . . . ? O4B B2B O3B C48B -21.3(13) . . . . ? C51B C50B O4B B2B 172.4(9) . . . . ? C49B C50B O4B B2B -9.2(14) . . . . ? F3B B2B O4B C50B -101.1(10) . . . . ? F4B B2B O4B C50B 139.7(9) . . . . ? O3B B2B O4B C50B 21.1(14) . . . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 0.593 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.056 #============================================================================== # End of CIF #============================================================================== data_90206ma _database_code_depnum_ccdc_archive 'CCDC 819394' #TrackingRef '- BF2_ethynyl_HMaeda_CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H56 B2 F4 N4 O4' _chemical_formula_weight 922.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21 /c' _symmetry_space_group_name_Hall '-P 2ybc' _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 29.692(5) _cell_length_b 23.863(4) _cell_length_c 16.660(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.025(3) _cell_angle_gamma 90.00 _cell_volume 11787(4) _cell_formula_units_Z 8 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 158 _cell_measurement_theta_min 3 _cell_measurement_theta_max 26.38 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.040 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3888 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9642 _exptl_absorpt_correction_T_max 0.9891 _exptl_absorpt_process_details ; SADABS (Sheldrick, 1997) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK_a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 60126 _diffrn_reflns_av_R_equivalents 0.0731 _diffrn_reflns_av_sigmaI/netI 0.1129 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.10 _diffrn_reflns_theta_max 25.00 _reflns_number_total 20747 _reflns_number_gt 11132 _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. ISOR was applied for carbons C56, C55, C106, and C54. ; _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^)+(0.0984P)^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 20747 _refine_ls_number_parameters 1261 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.1232 _refine_ls_R_factor_gt 0.0663 _refine_ls_wR_factor_ref 0.1829 _refine_ls_wR_factor_gt 0.1642 _refine_ls_goodness_of_fit_ref 0.916 _refine_ls_restrained_S_all 0.936 _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 1.43981(11) 0.39124(16) 0.6933(3) 0.0478(10) Uani 1 1 d . . . H1 H 1.4291 0.4249 0.6645 0.072 Uiso 1 1 calc R . . H2 H 1.4623 0.3722 0.6621 0.072 Uiso 1 1 calc R . . H3 H 1.4535 0.4019 0.7459 0.072 Uiso 1 1 calc R . . C2 C 1.40031(10) 0.35201(14) 0.7048(2) 0.0385(9) Uani 1 1 d . . . H4 H 1.3890 0.3379 0.6517 0.046 Uiso 1 1 calc R . . H5 H 1.4110 0.3194 0.7373 0.046 Uiso 1 1 calc R . . C3 C 1.36249(10) 0.37948(13) 0.7452(2) 0.0283(8) Uani 1 1 d . . . C4 C 1.36384(10) 0.43091(13) 0.7828(2) 0.0297(8) Uani 1 1 d . . . H6 H 1.3894 0.4548 0.7881 0.036 Uiso 1 1 calc R . . C5 C 1.29505(9) 0.39778(12) 0.7934(2) 0.0253(8) Uani 1 1 d . . . C6 C 1.31906(9) 0.35817(13) 0.7525(2) 0.0266(8) Uani 1 1 d . . . C7 C 1.30312(10) 0.30222(13) 0.7226(2) 0.0311(8) Uani 1 1 d . . . H7 H 1.3208 0.2910 0.6765 0.037 Uiso 1 1 calc R . . H8 H 1.2711 0.3051 0.7033 0.037 Uiso 1 1 calc R . . C8 C 1.30772(11) 0.25762(14) 0.7871(2) 0.0392(9) Uani 1 1 d . . . H9 H 1.3394 0.2542 0.8058 0.059 Uiso 1 1 calc R . . H10 H 1.2971 0.2217 0.7650 0.059 Uiso 1 1 calc R . . H11 H 1.2896 0.2681 0.8323 0.059 Uiso 1 1 calc R . . C9 C 1.24983(10) 0.40189(13) 0.8170(2) 0.0280(8) Uani 1 1 d . . . C10 C 1.21808(9) 0.35932(13) 0.8140(2) 0.0269(8) Uani 1 1 d . . . H12 H 1.2243 0.3250 0.7878 0.032 Uiso 1 1 calc R . . C11 C 1.17766(10) 0.36671(12) 0.8487(2) 0.0288(8) Uani 1 1 d . . . C12 C 1.14298(9) 0.32613(12) 0.8581(2) 0.0254(8) Uani 1 1 d . . . C13 C 1.13664(10) 0.27006(12) 0.8369(2) 0.0261(8) Uani 1 1 d . . . C14 C 1.16992(10) 0.23140(13) 0.8022(2) 0.0295(8) Uani 1 1 d . . . H13 H 1.1875 0.2521 0.7630 0.035 Uiso 1 1 calc R . . H14 H 1.1536 0.2007 0.7731 0.035 Uiso 1 1 calc R . . C15 C 1.20191(10) 0.20654(14) 0.8666(2) 0.0376(9) Uani 1 1 d . . . H15 H 1.2176 0.2368 0.8963 0.056 Uiso 1 1 calc R . . H16 H 1.2240 0.1827 0.8414 0.056 Uiso 1 1 calc R . . H17 H 1.1848 0.1841 0.9036 0.056 Uiso 1 1 calc R . . C16 C 1.09383(10) 0.25484(12) 0.8620(2) 0.0265(8) Uani 1 1 d . . . C17 C 1.07351(10) 0.19750(12) 0.8519(2) 0.0311(8) Uani 1 1 d . . . H18 H 1.0512 0.1920 0.8932 0.037 Uiso 1 1 calc R . . H19 H 1.0976 0.1692 0.8613 0.037 Uiso 1 1 calc R . . C18 C 1.05065(12) 0.18764(15) 0.7697(2) 0.0432(10) Uani 1 1 d . . . H20 H 1.0265 0.2152 0.7601 0.065 Uiso 1 1 calc R . . H21 H 1.0378 0.1498 0.7674 0.065 Uiso 1 1 calc R . . H22 H 1.0728 0.1915 0.7285 0.065 Uiso 1 1 calc R . . C19 C 1.07568(10) 0.30121(12) 0.8989(2) 0.0257(8) Uani 1 1 d . . . C20 C 1.03457(10) 0.30967(12) 0.9415(2) 0.0282(8) Uani 1 1 d . . . C21 C 1.03529(10) 0.34709(13) 1.0060(2) 0.0316(8) Uani 1 1 d . . . H23 H 1.0630 0.3641 1.0236 0.038 Uiso 1 1 calc R . . C22 C 0.99666(10) 0.35981(13) 1.0444(2) 0.0338(9) Uani 1 1 d . . . H24 H 0.9977 0.3854 1.0882 0.041 Uiso 1 1 calc R . . C23 C 0.95643(11) 0.33518(13) 1.0190(2) 0.0359(9) Uani 1 1 d . . . H25 H 0.9294 0.3448 1.0439 0.043 Uiso 1 1 calc R . . C24 C 0.95546(10) 0.29646(14) 0.9574(2) 0.0340(9) Uani 1 1 d . . . C25 C 0.99423(10) 0.28442(13) 0.9178(2) 0.0299(8) Uani 1 1 d . . . H26 H 0.9930 0.2587 0.8741 0.036 Uiso 1 1 calc R . . C26 C 0.91400(11) 0.27030(14) 0.9316(2) 0.0377(9) Uani 1 1 d . . . C27 C 0.87993(11) 0.24732(15) 0.9094(2) 0.0436(10) Uani 1 1 d . . . C28 C 0.84193(11) 0.21960(15) 0.8812(2) 0.0413(10) Uani 1 1 d . . . C29 C 0.80969(11) 0.19423(15) 0.8557(2) 0.0409(9) Uani 1 1 d . . . C30 C 0.77462(10) 0.15729(14) 0.8273(2) 0.0362(9) Uani 1 1 d . . . C31 C 0.73023(10) 0.17571(15) 0.8175(2) 0.0362(9) Uani 1 1 d . . . H27 H 0.7232 0.2138 0.8279 0.043 Uiso 1 1 calc R . . C32 C 0.69622(10) 0.13874(14) 0.7925(2) 0.0309(8) Uani 1 1 d . . . C33 C 0.70779(11) 0.08351(14) 0.7793(2) 0.0394(9) Uani 1 1 d . . . H28 H 0.6848 0.0573 0.7641 0.047 Uiso 1 1 calc R . . C34 C 0.75167(11) 0.06582(15) 0.7875(3) 0.0456(10) Uani 1 1 d . . . H29 H 0.7589 0.0279 0.7769 0.055 Uiso 1 1 calc R . . C35 C 0.78499(11) 0.10250(15) 0.8110(2) 0.0415(10) Uani 1 1 d . . . H30 H 0.8154 0.0902 0.8161 0.050 Uiso 1 1 calc R . . C36 C 0.64929(10) 0.15587(13) 0.7793(2) 0.0286(8) Uani 1 1 d . . . C37 C 0.62310(10) 0.19795(14) 0.8107(2) 0.0328(8) Uani 1 1 d . . . C38 C 0.63802(11) 0.24080(14) 0.8719(2) 0.0391(9) Uani 1 1 d . . . H31 H 0.6641 0.2257 0.9046 0.047 Uiso 1 1 calc R . . H32 H 0.6133 0.2472 0.9084 0.047 Uiso 1 1 calc R . . C39 C 0.65121(13) 0.29583(15) 0.8370(3) 0.0502(11) Uani 1 1 d . . . H33 H 0.6759 0.2901 0.8011 0.075 Uiso 1 1 calc R . . H34 H 0.6612 0.3214 0.8805 0.075 Uiso 1 1 calc R . . H35 H 0.6252 0.3121 0.8066 0.075 Uiso 1 1 calc R . . C40 C 0.57860(10) 0.19059(13) 0.7777(2) 0.0311(8) Uani 1 1 d . . . C41 C 0.53814(10) 0.22394(14) 0.7989(2) 0.0359(9) Uani 1 1 d . . . H36 H 0.5439 0.2399 0.8533 0.043 Uiso 1 1 calc R . . H37 H 0.5121 0.1982 0.8011 0.043 Uiso 1 1 calc R . . C42 C 0.52569(11) 0.27079(14) 0.7419(2) 0.0424(10) Uani 1 1 d . . . H38 H 0.5510 0.2971 0.7400 0.064 Uiso 1 1 calc R . . H39 H 0.4992 0.2905 0.7604 0.064 Uiso 1 1 calc R . . H40 H 0.5188 0.2555 0.6881 0.064 Uiso 1 1 calc R . . C43 C 0.57886(9) 0.14463(13) 0.7270(2) 0.0273(8) Uani 1 1 d . . . C44 C 0.54665(9) 0.11497(12) 0.6786(2) 0.0250(7) Uani 1 1 d . . . C45 C 0.50258(9) 0.13050(12) 0.6601(2) 0.0262(8) Uani 1 1 d . . . H41 H 0.4917 0.1656 0.6777 0.031 Uiso 1 1 calc R . . C46 C 0.47406(10) 0.09477(12) 0.6156(2) 0.0251(7) Uani 1 1 d . . . C47 C 0.42710(10) 0.10300(13) 0.5991(2) 0.0266(8) Uani 1 1 d . . . C48 C 0.39589(9) 0.14274(12) 0.6233(2) 0.0267(8) Uani 1 1 d . . . C49 C 0.40435(10) 0.18980(13) 0.6798(2) 0.0289(8) Uani 1 1 d . . . H42 H 0.3790 0.2167 0.6737 0.035 Uiso 1 1 calc R . . H43 H 0.4321 0.2096 0.6654 0.035 Uiso 1 1 calc R . . C50 C 0.40963(11) 0.17161(15) 0.7669(2) 0.0388(9) Uani 1 1 d . . . H44 H 0.3818 0.1534 0.7824 0.058 Uiso 1 1 calc R . . H45 H 0.4157 0.2045 0.8011 0.058 Uiso 1 1 calc R . . H46 H 0.4348 0.1451 0.7736 0.058 Uiso 1 1 calc R . . C51 C 0.35438(10) 0.12869(13) 0.5840(2) 0.0293(8) Uani 1 1 d . . . C52 C 0.36133(10) 0.08164(14) 0.5392(2) 0.0343(9) Uani 1 1 d . . . H47 H 0.3388 0.0629 0.5066 0.041 Uiso 1 1 calc R . . C53 C 0.31065(10) 0.15894(15) 0.5900(2) 0.0395(9) Uani 1 1 d . . . H48 H 0.3168 0.1992 0.5993 0.047 Uiso 1 1 calc R . . H49 H 0.2952 0.1444 0.6369 0.047 Uiso 1 1 calc R . . C54 C 0.27963(14) 0.1526(2) 0.5154(3) 0.0754(15) Uani 1 1 d U . . H50 H 0.2954 0.1647 0.4682 0.113 Uiso 1 1 calc R . . H51 H 0.2527 0.1758 0.5207 0.113 Uiso 1 1 calc R . . H52 H 0.2707 0.1133 0.5091 0.113 Uiso 1 1 calc R . . C55 C 0.92367(14) 0.1945(2) 0.7219(3) 0.0897(17) Uani 1 1 d U . . H53 H 0.9100 0.1789 0.7693 0.135 Uiso 1 1 calc R . . H54 H 0.9475 0.2209 0.7390 0.135 Uiso 1 1 calc R . . H55 H 0.9366 0.1641 0.6909 0.135 Uiso 1 1 calc R . . C56 C 0.88783(13) 0.22474(19) 0.6698(3) 0.0751(14) Uani 1 1 d U . . H56 H 0.8768 0.2573 0.7000 0.090 Uiso 1 1 calc R . . H57 H 0.9017 0.2392 0.6213 0.090 Uiso 1 1 calc R . . C57 C 0.84827(11) 0.18835(16) 0.6443(3) 0.0516(12) Uani 1 1 d . A . C58 C 0.84895(10) 0.13144(15) 0.6356(2) 0.0380(9) Uani 1 1 d . A . H58 H 0.8746 0.1080 0.6448 0.046 Uiso 1 1 calc R . . C59 C 0.77879(10) 0.15902(13) 0.6062(2) 0.0340(9) Uani 1 1 d . A . C60 C 0.80425(11) 0.20624(15) 0.6269(3) 0.0573(13) Uani 1 1 d . . . C63 C 0.73306(10) 0.14912(13) 0.5843(2) 0.0306(8) Uani 1 1 d . . . C64 C 0.69881(10) 0.18845(13) 0.5834(2) 0.0310(8) Uani 1 1 d . A . H59 H 0.7053 0.2260 0.5992 0.037 Uiso 1 1 calc R . . C65 C 0.65568(10) 0.17359(13) 0.5598(2) 0.0275(8) Uani 1 1 d . . . C66 C 0.61740(9) 0.20983(13) 0.5557(2) 0.0256(7) Uani 1 1 d . A . C67 C 0.61040(10) 0.26586(13) 0.5740(2) 0.0334(8) Uani 1 1 d . . . C68 C 0.64286(11) 0.30658(15) 0.6133(3) 0.0451(10) Uani 1 1 d . A . H60 H 0.6652 0.2855 0.6477 0.054 Uiso 1 1 calc R . . H61 H 0.6261 0.3315 0.6487 0.054 Uiso 1 1 calc R . . C69 C 0.66752(13) 0.34193(16) 0.5557(3) 0.0613(13) Uani 1 1 d . . . H62 H 0.6859 0.3178 0.5228 0.092 Uiso 1 1 calc R A . H63 H 0.6871 0.3685 0.5858 0.092 Uiso 1 1 calc R . . H64 H 0.6457 0.3626 0.5209 0.092 Uiso 1 1 calc R . . C70 C 0.56535(10) 0.27819(14) 0.5498(2) 0.0361(9) Uani 1 1 d . A . C71 C 0.54401(11) 0.33510(14) 0.5553(3) 0.0440(10) Uani 1 1 d . . . H65 H 0.5157 0.3316 0.5836 0.053 Uiso 1 1 calc R A . H66 H 0.5645 0.3599 0.5878 0.053 Uiso 1 1 calc R . . C72 C 0.53380(12) 0.36168(15) 0.4752(3) 0.0512(11) Uani 1 1 d . A . H67 H 0.5613 0.3630 0.4452 0.077 Uiso 1 1 calc R . . H68 H 0.5226 0.3998 0.4828 0.077 Uiso 1 1 calc R . . H69 H 0.5108 0.3396 0.4450 0.077 Uiso 1 1 calc R . . C73 C 0.54555(10) 0.22906(13) 0.5190(2) 0.0299(8) Uani 1 1 d . . . C74 C 0.49990(10) 0.21496(13) 0.4867(2) 0.0300(8) Uani 1 1 d . A . C75 C 0.49262(10) 0.16661(13) 0.4422(2) 0.0323(8) Uani 1 1 d . . . H70 H 0.5174 0.1429 0.4320 0.039 Uiso 1 1 calc R A . C76 C 0.45001(11) 0.15221(14) 0.4122(2) 0.0352(9) Uani 1 1 d . A . H71 H 0.4458 0.1187 0.3820 0.042 Uiso 1 1 calc R . . C77 C 0.41380(10) 0.18580(14) 0.4255(2) 0.0337(8) Uani 1 1 d . . . H72 H 0.3845 0.1756 0.4048 0.040 Uiso 1 1 calc R A . C78 C 0.42005(10) 0.23455(14) 0.4692(2) 0.0298(8) Uani 1 1 d . A . C79 C 0.46311(9) 0.24874(13) 0.5000(2) 0.0281(8) Uani 1 1 d . . . H73 H 0.4673 0.2821 0.5306 0.034 Uiso 1 1 calc R A . C80 C 0.38243(10) 0.26945(14) 0.4837(2) 0.0328(8) Uani 1 1 d . . . C81 C 0.34996(11) 0.29749(15) 0.4946(2) 0.0369(9) Uani 1 1 d . A . C82 C 0.31336(11) 0.33000(15) 0.5086(2) 0.0381(9) Uani 1 1 d . . . C83 C 0.28192(11) 0.35839(15) 0.5237(2) 0.0423(10) Uani 1 1 d . A . C84 C 0.24611(11) 0.39513(16) 0.5431(2) 0.0430(10) Uani 1 1 d . . . C85 C 0.20833(10) 0.37390(15) 0.5796(2) 0.0337(8) Uani 1 1 d . A . H74 H 0.2056 0.3349 0.5894 0.040 Uiso 1 1 calc R . . C86 C 0.17498(11) 0.41062(15) 0.6010(2) 0.0388(9) Uani 1 1 d . . . C87 C 0.17880(13) 0.46767(17) 0.5854(3) 0.0569(12) Uani 1 1 d . A . H75 H 0.1558 0.4926 0.6007 0.068 Uiso 1 1 calc R . . C88 C 0.21552(14) 0.48810(17) 0.5482(3) 0.0626(13) Uani 1 1 d . . . H76 H 0.2177 0.5271 0.5374 0.075 Uiso 1 1 calc R A . C89 C 0.24915(13) 0.45242(17) 0.5265(3) 0.0606(13) Uani 1 1 d . A . H77 H 0.2744 0.4667 0.5002 0.073 Uiso 1 1 calc R . . C90 C 0.13367(10) 0.38990(14) 0.6358(2) 0.0338(8) Uani 1 1 d . A . C91 C 0.10567(10) 0.34569(13) 0.6137(2) 0.0288(8) Uani 1 1 d . . . C92 C 0.11371(10) 0.30265(13) 0.5507(2) 0.0332(8) Uani 1 1 d . A . H78 H 0.1332 0.3193 0.5107 0.040 Uiso 1 1 calc R . . H79 H 0.0845 0.2933 0.5226 0.040 Uiso 1 1 calc R . . C93 C 0.13530(11) 0.24909(14) 0.5818(2) 0.0381(9) Uani 1 1 d . . . H80 H 0.1645 0.2576 0.6092 0.057 Uiso 1 1 calc R A . H81 H 0.1397 0.2236 0.5368 0.057 Uiso 1 1 calc R . . H82 H 0.1156 0.2312 0.6198 0.057 Uiso 1 1 calc R . . C94 C 0.06699(10) 0.34993(13) 0.6580(2) 0.0286(8) Uani 1 1 d . A . C95 C 0.02668(10) 0.31286(13) 0.6479(2) 0.0339(8) Uani 1 1 d . . . H83 H 0.0131 0.3084 0.7005 0.041 Uiso 1 1 calc R A . H84 H 0.0363 0.2754 0.6301 0.041 Uiso 1 1 calc R . . C96 C -0.00876(11) 0.33581(17) 0.5871(3) 0.0513(11) Uani 1 1 d . A . H85 H -0.0175 0.3736 0.6031 0.077 Uiso 1 1 calc R . . H86 H -0.0353 0.3114 0.5852 0.077 Uiso 1 1 calc R . . H87 H 0.0037 0.3372 0.5338 0.077 Uiso 1 1 calc R . . C97 C 0.07222(9) 0.39658(13) 0.7080(2) 0.0294(8) Uani 1 1 d . . . C98 C 0.04616(10) 0.42297(13) 0.7656(2) 0.0304(8) Uani 1 1 d . A . C99 C 0.00344(10) 0.40945(13) 0.7848(2) 0.0291(8) Uani 1 1 d . . . H88 H -0.0113 0.3783 0.7594 0.035 Uiso 1 1 calc R A . C100 C -0.01873(10) 0.44043(12) 0.8407(2) 0.0297(8) Uani 1 1 d . A . C101 C -0.06346(10) 0.43186(13) 0.8637(2) 0.0321(8) Uani 1 1 d . . . C102 C -0.09906(10) 0.39632(14) 0.8374(2) 0.0364(9) Uani 1 1 d . A . C103 C -0.10078(11) 0.35860(15) 0.7668(3) 0.0458(11) Uani 1 1 d . . . H89 H -0.1247 0.3303 0.7730 0.055 Uiso 1 1 calc R A . H90 H -0.0717 0.3385 0.7648 0.055 Uiso 1 1 calc R . . C104 C -0.10996(13) 0.38961(18) 0.6885(3) 0.0583(12) Uani 1 1 d . A . H91 H -0.1388 0.4095 0.6900 0.087 Uiso 1 1 calc R . . H92 H -0.1113 0.3628 0.6439 0.087 Uiso 1 1 calc R . . H93 H -0.0857 0.4167 0.6810 0.087 Uiso 1 1 calc R . . C105 C -0.17922(11) 0.37739(16) 0.8870(3) 0.0566(12) Uani 1 1 d . A . H94 H -0.1789 0.3452 0.8495 0.068 Uiso 1 1 calc R . . H95 H -0.1839 0.3623 0.9413 0.068 Uiso 1 1 calc R . . C106 C -0.21705(17) 0.4127(2) 0.8635(4) 0.108(2) Uani 1 1 d U . . H96 H -0.2165 0.4463 0.8972 0.162 Uiso 1 1 calc R . . H97 H -0.2452 0.3921 0.8702 0.162 Uiso 1 1 calc R . . H98 H -0.2152 0.4235 0.8070 0.162 Uiso 1 1 calc R . . C107 C -0.13399(11) 0.40537(14) 0.8884(3) 0.0418(10) Uani 1 1 d . . . C108 C -0.11980(11) 0.44515(14) 0.9433(2) 0.0390(9) Uani 1 1 d . A . H99 H -0.1370 0.4592 0.9854 0.047 Uiso 1 1 calc R . . N1 N 1.32334(8) 0.44188(10) 0.81049(17) 0.0279(7) Uani 1 1 d . . . H100 H 1.3160 0.4727 0.8358 0.034 Uiso 1 1 calc R . . N2 N 1.10575(8) 0.34309(10) 0.89580(17) 0.0277(7) Uani 1 1 d . . . H101 H 1.1019 0.3769 0.9154 0.033 Uiso 1 1 calc R . . N3 N 0.62193(7) 0.12443(10) 0.72932(17) 0.0276(6) Uani 1 1 d . . . H102 H 0.6307 0.0951 0.7022 0.033 Uiso 1 1 calc R . . N4 N 0.40448(8) 0.06612(10) 0.54831(17) 0.0317(7) Uani 1 1 d . . . H103 H 0.4165 0.0369 0.5254 0.038 Uiso 1 1 calc R . . N5 N 0.80780(8) 0.11440(11) 0.61202(18) 0.0346(7) Uani 1 1 d . . . H104 H 0.8002 0.0794 0.6016 0.042 Uiso 1 1 calc R A . N6 N 0.57770(8) 0.18880(10) 0.52344(17) 0.0274(6) Uani 1 1 d . A . H105 H 0.5736 0.1539 0.5077 0.033 Uiso 1 1 calc R . . N7 N 0.11326(8) 0.41963(11) 0.69293(18) 0.0341(7) Uani 1 1 d . A . H106 H 0.1247 0.4496 0.7170 0.041 Uiso 1 1 calc R . . N8 N -0.07814(8) 0.46089(11) 0.92836(18) 0.0345(7) Uani 1 1 d . A . H107 H -0.0623 0.4862 0.9559 0.041 Uiso 1 1 calc R . . O1 O 1.24012(6) 0.45065(8) 0.84914(15) 0.0333(6) Uani 1 1 d . . . O2 O 1.16749(7) 0.41534(9) 0.88033(16) 0.0390(6) Uani 1 1 d . . . O3 O 0.56237(6) 0.06782(8) 0.65017(14) 0.0290(5) Uani 1 1 d . . . O4 O 0.48992(6) 0.04861(8) 0.58511(14) 0.0286(5) Uani 1 1 d . . . O5 O 0.72432(6) 0.09706(8) 0.56361(15) 0.0341(6) Uani 1 1 d . A . O6 O 0.64621(6) 0.12247(8) 0.53567(14) 0.0310(6) Uani 1 1 d . A . O7 O 0.06752(7) 0.46570(9) 0.80142(15) 0.0366(6) Uani 1 1 d . . . O8 O 0.00229(7) 0.48224(9) 0.87877(15) 0.0351(6) Uani 1 1 d . . . B1 B 1.19332(12) 0.46538(16) 0.8634(3) 0.0355(11) Uani 1 1 d . . . B2 B 0.53877(12) 0.03929(15) 0.5840(3) 0.0284(9) Uani 1 1 d . . . B3 B 0.67837(11) 0.07682(15) 0.5459(3) 0.0290(9) Uani 1 1 d . . . B4 B 0.05104(12) 0.48914(16) 0.8749(3) 0.0344(10) Uani 1 1 d . A . F1 F 1.17419(6) 0.49165(7) 0.79619(14) 0.0426(5) Uani 1 1 d . . . F2 F 1.19334(6) 0.50002(7) 0.92870(13) 0.0426(5) Uani 1 1 d . . . F3 F 0.54773(6) -0.01632(7) 0.58911(12) 0.0391(5) Uani 1 1 d . . . F4 F 0.55360(6) 0.06095(8) 0.51195(12) 0.0376(5) Uani 1 1 d . . . F5 F 0.67749(6) 0.04488(8) 0.47874(13) 0.0450(5) Uani 1 1 d . A . F6 F 0.66575(6) 0.04479(7) 0.61076(13) 0.0395(5) Uani 1 1 d . A . F7 F 0.07172(6) 0.46095(7) 0.94047(12) 0.0368(5) Uani 1 1 d . . . F8 F 0.06133(6) 0.54477(7) 0.87827(12) 0.0368(5) Uani 1 1 d . . . C132 C 0.7894(3) 0.2688(6) 0.6062(9) 0.035(3) Uani 0.496(15) 1 d P A 2 H108 H 0.8152 0.2901 0.5863 0.043 Uiso 0.496(15) 1 calc PR A 2 H109 H 0.7646 0.2691 0.5641 0.043 Uiso 0.496(15) 1 calc PR A 2 C133 C 0.7739(3) 0.2949(5) 0.6827(6) 0.052(3) Uani 0.496(15) 1 d P A 2 H110 H 0.7472 0.2748 0.6999 0.078 Uiso 0.496(15) 1 calc PR A 2 H111 H 0.7662 0.3343 0.6729 0.078 Uiso 0.496(15) 1 calc PR A 2 H112 H 0.7981 0.2923 0.7248 0.078 Uiso 0.496(15) 1 calc PR A 2 C134 C 0.7892(4) 0.2611(6) 0.6547(8) 0.048(4) Uani 0.504(15) 1 d P A 1 H113 H 0.8101 0.2764 0.6977 0.057 Uiso 0.504(15) 1 calc PR A 1 H114 H 0.7583 0.2594 0.6742 0.057 Uiso 0.504(15) 1 calc PR A 1 C135 C 0.7909(4) 0.2955(5) 0.5764(9) 0.063(4) Uani 0.504(15) 1 d P A 1 H115 H 0.8218 0.2962 0.5589 0.095 Uiso 0.504(15) 1 calc PR A 1 H116 H 0.7808 0.3339 0.5862 0.095 Uiso 0.504(15) 1 calc PR A 1 H117 H 0.7710 0.2782 0.5346 0.095 Uiso 0.504(15) 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 C1 0.0267(19) 0.057(2) 0.061(3) 0.000(2) 0.0108(17) 0.0094(17) C2 0.0215(18) 0.040(2) 0.054(3) -0.0083(18) 0.0024(16) 0.0027(15) C3 0.0172(16) 0.0318(19) 0.036(2) -0.0025(16) -0.0002(14) 0.0047(13) C4 0.0122(16) 0.0295(18) 0.047(2) 0.0001(17) 0.0009(14) 0.0005(13) C5 0.0124(15) 0.0238(17) 0.040(2) -0.0035(15) 0.0011(13) 0.0028(12) C6 0.0168(16) 0.0293(18) 0.033(2) 0.0011(15) -0.0026(13) 0.0054(13) C7 0.0206(17) 0.0272(18) 0.046(2) -0.0078(16) 0.0028(15) 0.0033(13) C8 0.0269(18) 0.034(2) 0.057(3) -0.0073(18) 0.0046(17) 0.0015(15) C9 0.0227(17) 0.0241(18) 0.037(2) -0.0035(15) 0.0014(14) 0.0016(13) C10 0.0156(16) 0.0220(17) 0.043(2) -0.0034(15) 0.0040(14) 0.0031(12) C11 0.0208(17) 0.0218(18) 0.044(2) -0.0059(16) -0.0009(14) 0.0010(13) C12 0.0134(15) 0.0240(17) 0.039(2) -0.0018(15) 0.0009(13) 0.0025(12) C13 0.0206(16) 0.0204(17) 0.037(2) -0.0039(15) -0.0029(14) 0.0010(13) C14 0.0235(17) 0.0235(17) 0.042(2) -0.0060(16) 0.0048(15) -0.0027(13) C15 0.0257(18) 0.0320(19) 0.056(3) -0.0013(18) 0.0071(16) 0.0062(14) C16 0.0189(16) 0.0220(17) 0.038(2) -0.0019(15) -0.0051(14) -0.0007(13) C17 0.0233(17) 0.0235(17) 0.046(2) -0.0022(16) -0.0018(15) -0.0015(13) C18 0.039(2) 0.041(2) 0.049(3) -0.0104(19) -0.0013(18) -0.0130(17) C19 0.0187(16) 0.0217(17) 0.036(2) 0.0026(15) -0.0018(14) -0.0044(13) C20 0.0194(16) 0.0221(17) 0.043(2) -0.0014(16) -0.0008(14) 0.0017(13) C21 0.0187(17) 0.0251(18) 0.051(3) -0.0012(17) 0.0000(15) -0.0030(13) C22 0.0174(17) 0.0318(19) 0.052(3) -0.0075(17) 0.0003(15) 0.0013(14) C23 0.0236(18) 0.0305(19) 0.054(3) -0.0064(18) 0.0067(16) 0.0042(14) C24 0.0201(17) 0.0319(19) 0.050(3) 0.0016(18) 0.0010(15) -0.0023(14) C25 0.0168(16) 0.0288(18) 0.044(2) 0.0008(16) -0.0003(14) -0.0003(13) C26 0.0197(18) 0.038(2) 0.056(3) -0.0099(18) 0.0052(16) -0.0025(15) C27 0.0211(19) 0.049(2) 0.062(3) -0.010(2) 0.0070(17) -0.0001(16) C28 0.0173(18) 0.046(2) 0.061(3) -0.010(2) 0.0031(16) -0.0013(16) C29 0.0199(18) 0.048(2) 0.055(3) -0.0065(19) 0.0009(16) 0.0006(16) C30 0.0178(17) 0.043(2) 0.048(3) -0.0096(18) -0.0001(15) -0.0056(15) C31 0.0201(17) 0.040(2) 0.048(3) -0.0097(18) 0.0014(15) -0.0014(15) C32 0.0205(17) 0.036(2) 0.036(2) -0.0074(16) -0.0010(14) 0.0004(14) C33 0.0244(18) 0.038(2) 0.055(3) -0.0121(19) -0.0030(16) -0.0036(15) C34 0.030(2) 0.036(2) 0.070(3) -0.012(2) -0.0060(18) 0.0080(16) C35 0.0191(17) 0.050(2) 0.055(3) -0.007(2) -0.0027(16) 0.0043(16) C36 0.0187(16) 0.0279(18) 0.039(2) -0.0070(16) 0.0022(14) -0.0038(13) C37 0.0229(17) 0.035(2) 0.041(2) -0.0075(17) 0.0062(15) -0.0023(14) C38 0.0319(19) 0.046(2) 0.040(2) -0.0168(18) 0.0015(16) 0.0005(16) C39 0.045(2) 0.043(2) 0.062(3) -0.020(2) -0.005(2) 0.0068(18) C40 0.0230(17) 0.0335(19) 0.037(2) -0.0064(17) 0.0063(14) -0.0010(14) C41 0.0245(18) 0.044(2) 0.040(2) -0.0131(18) 0.0018(15) 0.0016(15) C42 0.0293(19) 0.038(2) 0.060(3) -0.0132(19) 0.0016(17) 0.0043(15) C43 0.0137(15) 0.0272(18) 0.041(2) -0.0028(16) 0.0041(14) -0.0013(13) C44 0.0206(16) 0.0205(17) 0.034(2) -0.0013(15) 0.0066(14) -0.0011(13) C45 0.0209(16) 0.0202(16) 0.038(2) -0.0025(15) 0.0064(14) 0.0007(13) C46 0.0221(16) 0.0240(17) 0.030(2) -0.0020(15) 0.0045(14) 0.0005(13) C47 0.0213(16) 0.0279(18) 0.031(2) -0.0027(15) 0.0026(14) -0.0015(13) C48 0.0176(16) 0.0264(17) 0.036(2) -0.0001(15) 0.0028(14) -0.0011(13) C49 0.0162(16) 0.0309(18) 0.040(2) -0.0062(16) 0.0024(14) 0.0031(13) C50 0.0246(18) 0.045(2) 0.047(3) -0.0100(18) 0.0042(16) 0.0036(15) C51 0.0181(16) 0.0282(18) 0.042(2) 0.0007(16) 0.0034(14) -0.0006(13) C52 0.0167(17) 0.041(2) 0.044(2) -0.0030(18) -0.0049(15) -0.0058(14) C53 0.0200(17) 0.047(2) 0.051(3) -0.0094(19) -0.0017(16) -0.0008(15) C54 0.052(2) 0.091(3) 0.080(3) -0.022(3) -0.021(2) 0.026(2) C55 0.041(2) 0.122(3) 0.106(4) -0.063(3) -0.005(2) -0.002(2) C56 0.034(2) 0.067(3) 0.123(4) -0.052(3) 0.003(2) -0.0041(19) C57 0.0174(18) 0.048(2) 0.089(3) -0.031(2) 0.0046(18) -0.0023(16) C58 0.0159(17) 0.043(2) 0.056(3) -0.0054(19) 0.0036(15) 0.0027(15) C59 0.0142(16) 0.0290(19) 0.059(3) -0.0076(17) 0.0047(15) 0.0033(13) C60 0.0196(19) 0.031(2) 0.122(4) -0.030(2) 0.007(2) 0.0001(15) C63 0.0250(17) 0.0227(18) 0.044(2) 0.0002(16) 0.0048(15) -0.0015(13) C64 0.0177(16) 0.0216(17) 0.054(2) -0.0067(16) 0.0011(15) 0.0013(13) C65 0.0262(17) 0.0229(18) 0.034(2) 0.0013(15) 0.0057(14) -0.0006(13) C66 0.0169(16) 0.0270(18) 0.033(2) 0.0014(15) 0.0009(13) -0.0006(13) C67 0.0192(17) 0.033(2) 0.049(2) -0.0053(17) 0.0040(15) 0.0034(14) C68 0.0264(19) 0.039(2) 0.070(3) -0.016(2) 0.0027(18) 0.0032(16) C69 0.049(3) 0.039(2) 0.096(4) -0.013(2) 0.002(2) -0.0051(19) C70 0.0253(18) 0.0293(19) 0.054(3) -0.0019(17) 0.0064(16) 0.0027(14) C71 0.0253(19) 0.037(2) 0.070(3) -0.011(2) 0.0026(18) 0.0000(15) C72 0.041(2) 0.034(2) 0.078(3) -0.002(2) 0.005(2) 0.0076(17) C73 0.0194(16) 0.0297(18) 0.041(2) 0.0022(16) 0.0057(14) 0.0049(14) C74 0.0238(17) 0.0321(19) 0.035(2) 0.0069(16) 0.0048(14) 0.0008(14) C75 0.0256(18) 0.0284(19) 0.043(2) 0.0067(17) 0.0026(15) 0.0049(14) C76 0.0297(19) 0.034(2) 0.042(2) 0.0046(17) -0.0023(16) -0.0006(15) C77 0.0218(17) 0.042(2) 0.037(2) 0.0088(18) 0.0000(15) -0.0024(15) C78 0.0207(17) 0.036(2) 0.032(2) 0.0052(16) 0.0029(14) 0.0017(14) C79 0.0187(16) 0.0297(18) 0.036(2) -0.0021(15) 0.0066(14) 0.0016(13) C80 0.0194(17) 0.045(2) 0.033(2) -0.0014(17) -0.0007(14) -0.0011(16) C81 0.0207(18) 0.052(2) 0.038(2) -0.0001(18) -0.0009(15) 0.0009(17) C82 0.0235(19) 0.050(2) 0.041(2) -0.0039(18) 0.0029(16) -0.0013(17) C83 0.0217(19) 0.050(2) 0.056(3) -0.009(2) 0.0040(17) 0.0001(17) C84 0.0274(19) 0.048(2) 0.054(3) -0.018(2) 0.0117(17) 0.0023(16) C85 0.0213(17) 0.040(2) 0.040(2) -0.0087(17) 0.0024(15) 0.0002(15) C86 0.0269(19) 0.036(2) 0.054(3) -0.0131(18) 0.0090(16) -0.0019(15) C87 0.040(2) 0.047(3) 0.086(4) -0.017(2) 0.025(2) 0.0008(18) C88 0.052(3) 0.041(2) 0.098(4) -0.006(2) 0.033(2) -0.004(2) C89 0.040(2) 0.049(3) 0.096(4) -0.014(2) 0.030(2) -0.0085(19) C90 0.0210(17) 0.036(2) 0.045(2) -0.0071(18) 0.0061(15) 0.0069(15) C91 0.0222(17) 0.0294(18) 0.035(2) -0.0046(16) 0.0010(14) 0.0072(14) C92 0.0227(17) 0.037(2) 0.040(2) -0.0056(17) -0.0009(15) 0.0025(14) C93 0.034(2) 0.036(2) 0.045(3) -0.0114(18) 0.0037(16) 0.0064(15) C94 0.0205(17) 0.0308(18) 0.034(2) -0.0026(16) 0.0016(14) 0.0069(13) C95 0.0276(18) 0.0304(19) 0.044(2) -0.0110(17) 0.0042(16) -0.0009(14) C96 0.027(2) 0.062(3) 0.064(3) -0.021(2) -0.0030(18) -0.0002(18) C97 0.0162(16) 0.0293(18) 0.043(2) -0.0094(16) 0.0041(14) 0.0016(13) C98 0.0220(17) 0.0284(18) 0.041(2) -0.0049(16) -0.0017(15) 0.0058(14) C99 0.0182(16) 0.0257(18) 0.043(2) -0.0093(16) 0.0016(15) -0.0009(13) C100 0.0194(16) 0.0212(17) 0.048(2) -0.0035(16) -0.0007(15) 0.0002(13) C101 0.0209(17) 0.0273(18) 0.048(3) -0.0086(17) 0.0051(15) 0.0010(14) C102 0.0195(17) 0.0317(19) 0.058(3) -0.0084(18) 0.0042(16) 0.0036(14) C103 0.0186(18) 0.043(2) 0.076(3) -0.023(2) 0.0021(18) -0.0043(15) C104 0.048(2) 0.059(3) 0.067(3) -0.024(2) -0.004(2) 0.000(2) C105 0.024(2) 0.050(2) 0.097(4) -0.018(2) 0.008(2) -0.0046(17) C106 0.060(3) 0.100(3) 0.162(4) 0.009(3) -0.009(3) -0.003(3) C107 0.0240(18) 0.035(2) 0.067(3) -0.0053(19) 0.0066(18) -0.0019(15) C108 0.0231(18) 0.036(2) 0.059(3) -0.0069(19) 0.0158(16) 0.0007(15) N1 0.0166(13) 0.0223(14) 0.0449(19) -0.0077(13) 0.0012(12) 0.0015(10) N2 0.0148(13) 0.0176(14) 0.051(2) -0.0059(13) 0.0031(12) -0.0020(10) N3 0.0129(13) 0.0263(14) 0.0437(19) -0.0082(13) 0.0035(11) 0.0012(10) N4 0.0210(14) 0.0256(15) 0.049(2) -0.0141(14) 0.0028(12) -0.0029(11) N5 0.0170(14) 0.0256(15) 0.062(2) 0.0006(14) 0.0045(13) -0.0007(11) N6 0.0203(14) 0.0225(14) 0.0394(18) -0.0010(13) 0.0015(12) 0.0000(11) N7 0.0212(14) 0.0289(15) 0.053(2) -0.0120(14) 0.0061(13) 0.0012(11) N8 0.0180(14) 0.0329(16) 0.053(2) -0.0120(15) 0.0092(13) -0.0028(12) O1 0.0167(11) 0.0220(12) 0.0621(18) -0.0111(11) 0.0118(10) -0.0011(9) O2 0.0206(12) 0.0216(12) 0.076(2) -0.0141(12) 0.0167(11) -0.0008(9) O3 0.0195(11) 0.0257(12) 0.0415(15) -0.0076(11) -0.0012(10) 0.0035(9) O4 0.0197(11) 0.0228(12) 0.0434(16) -0.0102(10) 0.0018(10) 0.0021(9) O5 0.0186(11) 0.0227(12) 0.0607(18) 0.0000(11) -0.0003(10) -0.0003(9) O6 0.0175(11) 0.0220(12) 0.0534(17) -0.0002(11) 0.0000(10) -0.0015(9) O7 0.0213(12) 0.0355(13) 0.0539(17) -0.0219(12) 0.0100(11) -0.0056(10) O8 0.0210(12) 0.0319(13) 0.0528(17) -0.0179(12) 0.0079(10) -0.0033(10) B1 0.019(2) 0.026(2) 0.062(3) -0.015(2) 0.0076(19) -0.0033(16) B2 0.0227(19) 0.021(2) 0.041(3) -0.0035(18) -0.0005(17) 0.0025(15) B3 0.0208(19) 0.0195(19) 0.046(3) 0.0000(19) 0.0007(17) 0.0001(15) B4 0.021(2) 0.025(2) 0.058(3) -0.017(2) 0.0083(19) -0.0010(16) F1 0.0221(10) 0.0280(10) 0.0779(17) -0.0056(11) 0.0057(10) -0.0011(8) F2 0.0265(10) 0.0261(10) 0.0770(17) -0.0150(11) 0.0201(10) -0.0038(8) F3 0.0296(10) 0.0261(10) 0.0609(15) -0.0113(10) -0.0062(9) 0.0046(8) F4 0.0207(10) 0.0481(12) 0.0439(14) -0.0064(10) 0.0013(8) -0.0013(8) F5 0.0260(10) 0.0471(12) 0.0617(16) -0.0186(11) 0.0002(9) 0.0016(9) F6 0.0225(10) 0.0332(11) 0.0629(15) 0.0161(10) 0.0033(9) 0.0048(8) F7 0.0257(10) 0.0297(10) 0.0553(14) -0.0125(10) 0.0046(9) -0.0003(8) F8 0.0259(10) 0.0266(10) 0.0591(14) -0.0150(9) 0.0123(9) -0.0032(8) C132 0.012(4) 0.026(7) 0.068(10) -0.005(7) -0.001(6) 0.004(4) C133 0.032(5) 0.050(6) 0.073(7) -0.032(5) 0.003(4) 0.007(4) C134 0.026(5) 0.043(8) 0.075(9) -0.010(8) 0.011(6) -0.007(4) C135 0.049(6) 0.033(7) 0.108(11) 0.011(6) 0.012(6) 0.004(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 C2 1.521(5) . ? C1 H1 0.9800 . ? C1 H2 0.9800 . ? C1 H3 0.9800 . ? C2 C3 1.491(4) . ? C2 H4 0.9900 . ? C2 H5 0.9900 . ? C3 C4 1.377(4) . ? C3 C6 1.397(4) . ? C4 N1 1.337(4) . ? C4 H6 0.9500 . ? C5 N1 1.367(4) . ? C5 C6 1.385(4) . ? C5 C9 1.422(4) . ? C6 C7 1.493(4) . ? C7 C8 1.513(5) . ? C7 H7 0.9900 . ? C7 H8 0.9900 . ? C8 H9 0.9800 . ? C8 H10 0.9800 . ? C8 H11 0.9800 . ? C9 O1 1.319(4) . ? C9 C10 1.385(4) . ? C10 C11 1.371(4) . ? C10 H12 0.9500 . ? C11 O2 1.316(4) . ? C11 C12 1.428(4) . ? C12 N2 1.362(4) . ? C12 C13 1.394(4) . ? C13 C16 1.407(4) . ? C13 C14 1.491(4) . ? C14 C15 1.516(4) . ? C14 H13 0.9900 . ? C14 H14 0.9900 . ? C15 H15 0.9800 . ? C15 H16 0.9800 . ? C15 H17 0.9800 . ? C16 C19 1.388(4) . ? C16 C17 1.501(4) . ? C17 C18 1.514(5) . ? C17 H18 0.9900 . ? C17 H19 0.9900 . ? C18 H20 0.9800 . ? C18 H21 0.9800 . ? C18 H22 0.9800 . ? C19 N2 1.343(4) . ? C19 C20 1.458(4) . ? C20 C25 1.380(4) . ? C20 C21 1.396(5) . ? C21 C22 1.377(5) . ? C21 H23 0.9500 . ? C22 C23 1.378(4) . ? C22 H24 0.9500 . ? C23 C24 1.381(5) . ? C23 H25 0.9500 . ? C24 C25 1.387(5) . ? C24 C26 1.426(4) . ? C25 H26 0.9500 . ? C26 C27 1.192(4) . ? C27 C28 1.369(5) . ? C28 C29 1.192(4) . ? C29 C30 1.426(4) . ? C30 C35 1.374(5) . ? C30 C31 1.391(4) . ? C31 C32 1.388(4) . ? C31 H27 0.9500 . ? C32 C33 1.383(5) . ? C32 C36 1.458(4) . ? C33 C34 1.370(4) . ? C33 H28 0.9500 . ? C34 C35 1.363(5) . ? C34 H29 0.9500 . ? C35 H30 0.9500 . ? C36 N3 1.359(4) . ? C36 C37 1.389(4) . ? C37 C40 1.415(4) . ? C37 C38 1.495(4) . ? C38 C39 1.497(5) . ? C38 H31 0.9900 . ? C38 H32 0.9900 . ? C39 H33 0.9800 . ? C39 H34 0.9800 . ? C39 H35 0.9800 . ? C40 C43 1.385(4) . ? C40 C41 1.498(4) . ? C41 C42 1.500(5) . ? C41 H36 0.9900 . ? C41 H37 0.9900 . ? C42 H38 0.9800 . ? C42 H39 0.9800 . ? C42 H40 0.9800 . ? C43 N3 1.365(4) . ? C43 C44 1.409(4) . ? C44 O3 1.316(4) . ? C44 C45 1.379(4) . ? C45 C46 1.388(4) . ? C45 H41 0.9500 . ? C46 O4 1.310(4) . ? C46 C47 1.420(4) . ? C47 N4 1.372(4) . ? C47 C48 1.400(4) . ? C48 C51 1.406(4) . ? C48 C49 1.478(4) . ? C49 C50 1.515(5) . ? C49 H42 0.9900 . ? C49 H43 0.9900 . ? C50 H44 0.9800 . ? C50 H45 0.9800 . ? C50 H46 0.9800 . ? C51 C52 1.369(5) . ? C51 C53 1.494(4) . ? C52 N4 1.334(4) . ? C52 H47 0.9500 . ? C53 C54 1.515(5) . ? C53 H48 0.9900 . ? C53 H49 0.9900 . ? C54 H50 0.9800 . ? C54 H51 0.9800 . ? C54 H52 0.9800 . ? C55 C56 1.520(7) . ? C55 H53 0.9800 . ? C55 H54 0.9800 . ? C55 H55 0.9800 . ? C56 C57 1.504(5) . ? C56 H56 0.9900 . ? C56 H57 0.9900 . ? C57 C58 1.366(5) . ? C57 C60 1.391(5) . ? C58 N5 1.327(4) . ? C58 H58 0.9500 . ? C59 N5 1.370(4) . ? C59 C60 1.390(4) . ? C59 C63 1.407(4) . ? C60 C134 1.466(15) . ? C60 C132 1.589(14) . ? C63 O5 1.311(4) . ? C63 C64 1.383(4) . ? C64 C65 1.366(4) . ? C64 H59 0.9500 . ? C65 O6 1.310(4) . ? C65 C66 1.427(4) . ? C66 N6 1.365(4) . ? C66 C67 1.389(4) . ? C67 C70 1.407(4) . ? C67 C68 1.495(4) . ? C68 C69 1.497(6) . ? C68 H60 0.9900 . ? C68 H61 0.9900 . ? C69 H62 0.9800 . ? C69 H63 0.9800 . ? C69 H64 0.9800 . ? C70 C73 1.397(4) . ? C70 C71 1.503(5) . ? C71 C72 1.495(5) . ? C71 H65 0.9900 . ? C71 H66 0.9900 . ? C72 H67 0.9800 . ? C72 H68 0.9800 . ? C72 H69 0.9800 . ? C73 N6 1.354(4) . ? C73 C74 1.471(4) . ? C74 C75 1.383(5) . ? C74 C79 1.385(4) . ? C75 C76 1.379(4) . ? C75 H70 0.9500 . ? C76 C77 1.369(5) . ? C76 H71 0.9500 . ? C77 C78 1.379(5) . ? C77 H72 0.9500 . ? C78 C79 1.394(4) . ? C78 C80 1.424(4) . ? C79 H73 0.9500 . ? C80 C81 1.195(4) . ? C81 C82 1.365(5) . ? C82 C83 1.191(5) . ? C83 C84 1.428(5) . ? C84 C85 1.399(5) . ? C84 C89 1.399(5) . ? C85 C86 1.384(5) . ? C85 H74 0.9500 . ? C86 C87 1.392(5) . ? C86 C90 1.470(5) . ? C87 C88 1.372(5) . ? C87 H75 0.9500 . ? C88 C89 1.375(5) . ? C88 H76 0.9500 . ? C89 H77 0.9500 . ? C90 N7 1.355(4) . ? C90 C91 1.381(4) . ? C91 C94 1.402(5) . ? C91 C92 1.496(4) . ? C92 C93 1.509(4) . ? C92 H78 0.9900 . ? C92 H79 0.9900 . ? C93 H80 0.9800 . ? C93 H81 0.9800 . ? C93 H82 0.9800 . ? C94 C97 1.393(4) . ? C94 C95 1.491(4) . ? C95 C96 1.523(5) . ? C95 H83 0.9900 . ? C95 H84 0.9900 . ? C96 H85 0.9800 . ? C96 H86 0.9800 . ? C96 H87 0.9800 . ? C97 N7 1.372(4) . ? C97 C98 1.412(5) . ? C98 O7 1.326(4) . ? C98 C99 1.363(4) . ? C99 C100 1.383(5) . ? C99 H88 0.9500 . ? C100 O8 1.321(3) . ? C100 C101 1.417(4) . ? C101 N8 1.370(4) . ? C101 C102 1.408(4) . ? C102 C107 1.393(5) . ? C102 C103 1.480(5) . ? C103 C104 1.511(6) . ? C103 H89 0.9900 . ? C103 H90 0.9900 . ? C104 H91 0.9800 . ? C104 H92 0.9800 . ? C104 H93 0.9800 . ? C105 C106 1.441(6) . ? C105 C107 1.499(5) . ? C105 H94 0.9900 . ? C105 H95 0.9900 . ? C106 H96 0.9800 . ? C106 H97 0.9800 . ? C106 H98 0.9800 . ? C107 C108 1.369(5) . ? C108 N8 1.329(4) . ? C108 H99 0.9500 . ? N1 H100 0.8800 . ? N2 H101 0.8800 . ? N3 H102 0.8800 . ? N4 H103 0.8800 . ? N5 H104 0.8800 . ? N6 H105 0.8800 . ? N7 H106 0.8800 . ? N8 H107 0.8800 . ? O1 B1 1.465(4) . ? O2 B1 1.455(4) . ? O3 B2 1.445(4) . ? O4 B2 1.469(4) . ? O5 B3 1.462(4) . ? O6 B3 1.453(4) . ? O7 B4 1.455(5) . ? O8 B4 1.462(4) . ? B1 F2 1.366(4) . ? B1 F1 1.380(5) . ? B2 F3 1.355(4) . ? B2 F4 1.399(5) . ? B3 F5 1.354(4) . ? B3 F6 1.391(4) . ? B4 F8 1.363(4) . ? B4 F7 1.397(5) . ? C132 C133 1.511(16) . ? C132 H108 0.9900 . ? C132 H109 0.9900 . ? C133 H110 0.9800 . ? C133 H111 0.9800 . ? C133 H112 0.9800 . ? C134 C135 1.544(18) . ? C134 H113 0.9900 . ? C134 H114 0.9900 . ? C135 H115 0.9800 . ? C135 H116 0.9800 . ? C135 H117 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 C2 C1 H1 109.5 . . ? C2 C1 H2 109.5 . . ? H1 C1 H2 109.5 . . ? C2 C1 H3 109.5 . . ? H1 C1 H3 109.5 . . ? H2 C1 H3 109.5 . . ? C3 C2 C1 113.0(3) . . ? C3 C2 H4 109.0 . . ? C1 C2 H4 109.0 . . ? C3 C2 H5 109.0 . . ? C1 C2 H5 109.0 . . ? H4 C2 H5 107.8 . . ? C4 C3 C6 106.9(3) . . ? C4 C3 C2 126.3(3) . . ? C6 C3 C2 126.8(3) . . ? N1 C4 C3 109.0(3) . . ? N1 C4 H6 125.5 . . ? C3 C4 H6 125.5 . . ? N1 C5 C6 107.5(3) . . ? N1 C5 C9 117.9(3) . . ? C6 C5 C9 134.5(3) . . ? C5 C6 C3 107.2(3) . . ? C5 C6 C7 127.7(3) . . ? C3 C6 C7 125.1(3) . . ? C6 C7 C8 112.2(3) . . ? C6 C7 H7 109.2 . . ? C8 C7 H7 109.2 . . ? C6 C7 H8 109.2 . . ? C8 C7 H8 109.2 . . ? H7 C7 H8 107.9 . . ? C7 C8 H9 109.5 . . ? C7 C8 H10 109.5 . . ? H9 C8 H10 109.5 . . ? C7 C8 H11 109.5 . . ? H9 C8 H11 109.5 . . ? H10 C8 H11 109.5 . . ? O1 C9 C10 119.9(3) . . ? O1 C9 C5 113.8(3) . . ? C10 C9 C5 126.2(3) . . ? C11 C10 C9 120.0(3) . . ? C11 C10 H12 120.0 . . ? C9 C10 H12 120.0 . . ? O2 C11 C10 120.5(3) . . ? O2 C11 C12 111.8(3) . . ? C10 C11 C12 127.7(3) . . ? N2 C12 C13 107.5(3) . . ? N2 C12 C11 117.2(3) . . ? C13 C12 C11 135.4(3) . . ? C12 C13 C16 106.5(3) . . ? C12 C13 C14 127.5(3) . . ? C16 C13 C14 125.7(3) . . ? C13 C14 C15 111.8(3) . . ? C13 C14 H13 109.3 . . ? C15 C14 H13 109.3 . . ? C13 C14 H14 109.3 . . ? C15 C14 H14 109.3 . . ? H13 C14 H14 107.9 . . ? C14 C15 H15 109.5 . . ? C14 C15 H16 109.5 . . ? H15 C15 H16 109.5 . . ? C14 C15 H17 109.5 . . ? H15 C15 H17 109.5 . . ? H16 C15 H17 109.5 . . ? C19 C16 C13 107.7(3) . . ? C19 C16 C17 127.8(3) . . ? C13 C16 C17 124.5(3) . . ? C16 C17 C18 113.7(3) . . ? C16 C17 H18 108.8 . . ? C18 C17 H18 108.8 . . ? C16 C17 H19 108.8 . . ? C18 C17 H19 108.8 . . ? H18 C17 H19 107.7 . . ? C17 C18 H20 109.5 . . ? C17 C18 H21 109.5 . . ? H20 C18 H21 109.5 . . ? C17 C18 H22 109.5 . . ? H20 C18 H22 109.5 . . ? H21 C18 H22 109.5 . . ? N2 C19 C16 107.6(3) . . ? N2 C19 C20 119.4(3) . . ? C16 C19 C20 132.9(3) . . ? C25 C20 C21 118.6(3) . . ? C25 C20 C19 122.4(3) . . ? C21 C20 C19 118.9(3) . . ? C22 C21 C20 121.3(3) . . ? C22 C21 H23 119.3 . . ? C20 C21 H23 119.3 . . ? C21 C22 C23 119.5(3) . . ? C21 C22 H24 120.2 . . ? C23 C22 H24 120.2 . . ? C22 C23 C24 119.9(3) . . ? C22 C23 H25 120.1 . . ? C24 C23 H25 120.1 . . ? C23 C24 C25 120.5(3) . . ? C23 C24 C26 120.0(3) . . ? C25 C24 C26 119.4(3) . . ? C20 C25 C24 120.2(3) . . ? C20 C25 H26 119.9 . . ? C24 C25 H26 119.9 . . ? C27 C26 C24 178.3(4) . . ? C26 C27 C28 177.3(4) . . ? C29 C28 C27 178.0(4) . . ? C28 C29 C30 172.3(4) . . ? C35 C30 C31 119.9(3) . . ? C35 C30 C29 119.1(3) . . ? C31 C30 C29 121.0(3) . . ? C32 C31 C30 120.3(3) . . ? C32 C31 H27 119.9 . . ? C30 C31 H27 119.9 . . ? C33 C32 C31 118.1(3) . . ? C33 C32 C36 119.1(3) . . ? C31 C32 C36 122.8(3) . . ? C34 C33 C32 121.4(3) . . ? C34 C33 H28 119.3 . . ? C32 C33 H28 119.3 . . ? C35 C34 C33 120.2(3) . . ? C35 C34 H29 119.9 . . ? C33 C34 H29 119.9 . . ? C34 C35 C30 120.1(3) . . ? C34 C35 H30 120.0 . . ? C30 C35 H30 120.0 . . ? N3 C36 C37 107.6(3) . . ? N3 C36 C32 118.3(3) . . ? C37 C36 C32 134.1(3) . . ? C36 C37 C40 107.1(3) . . ? C36 C37 C38 126.8(3) . . ? C40 C37 C38 125.9(3) . . ? C37 C38 C39 114.2(3) . . ? C37 C38 H31 108.7 . . ? C39 C38 H31 108.7 . . ? C37 C38 H32 108.7 . . ? C39 C38 H32 108.7 . . ? H31 C38 H32 107.6 . . ? C38 C39 H33 109.5 . . ? C38 C39 H34 109.5 . . ? H33 C39 H34 109.5 . . ? C38 C39 H35 109.5 . . ? H33 C39 H35 109.5 . . ? H34 C39 H35 109.5 . . ? C43 C40 C37 107.5(3) . . ? C43 C40 C41 126.5(3) . . ? C37 C40 C41 125.9(3) . . ? C40 C41 C42 114.9(3) . . ? C40 C41 H36 108.5 . . ? C42 C41 H36 108.5 . . ? C40 C41 H37 108.5 . . ? C42 C41 H37 108.5 . . ? H36 C41 H37 107.5 . . ? C41 C42 H38 109.5 . . ? C41 C42 H39 109.5 . . ? H38 C42 H39 109.5 . . ? C41 C42 H40 109.5 . . ? H38 C42 H40 109.5 . . ? H39 C42 H40 109.5 . . ? N3 C43 C40 107.3(3) . . ? N3 C43 C44 116.4(3) . . ? C40 C43 C44 136.2(3) . . ? O3 C44 C45 120.0(3) . . ? O3 C44 C43 113.1(3) . . ? C45 C44 C43 126.9(3) . . ? C44 C45 C46 119.9(3) . . ? C44 C45 H41 120.0 . . ? C46 C45 H41 120.0 . . ? O4 C46 C45 120.1(3) . . ? O4 C46 C47 114.3(3) . . ? C45 C46 C47 125.6(3) . . ? N4 C47 C48 107.6(2) . . ? N4 C47 C46 118.3(3) . . ? C48 C47 C46 134.1(3) . . ? C47 C48 C51 106.4(3) . . ? C47 C48 C49 127.2(3) . . ? C51 C48 C49 126.4(3) . . ? C48 C49 C50 113.4(3) . . ? C48 C49 H42 108.9 . . ? C50 C49 H42 108.9 . . ? C48 C49 H43 108.9 . . ? C50 C49 H43 108.9 . . ? H42 C49 H43 107.7 . . ? C49 C50 H44 109.5 . . ? C49 C50 H45 109.5 . . ? H44 C50 H45 109.5 . . ? C49 C50 H46 109.5 . . ? H44 C50 H46 109.5 . . ? H45 C50 H46 109.5 . . ? C52 C51 C48 107.2(3) . . ? C52 C51 C53 126.1(3) . . ? C48 C51 C53 126.7(3) . . ? N4 C52 C51 109.7(3) . . ? N4 C52 H47 125.2 . . ? C51 C52 H47 125.2 . . ? C51 C53 C54 113.0(3) . . ? C51 C53 H48 109.0 . . ? C54 C53 H48 109.0 . . ? C51 C53 H49 109.0 . . ? C54 C53 H49 109.0 . . ? H48 C53 H49 107.8 . . ? C53 C54 H50 109.5 . . ? C53 C54 H51 109.5 . . ? H50 C54 H51 109.5 . . ? C53 C54 H52 109.5 . . ? H50 C54 H52 109.5 . . ? H51 C54 H52 109.5 . . ? C56 C55 H53 109.5 . . ? C56 C55 H54 109.5 . . ? H53 C55 H54 109.5 . . ? C56 C55 H55 109.5 . . ? H53 C55 H55 109.5 . . ? H54 C55 H55 109.5 . . ? C57 C56 C55 113.6(4) . . ? C57 C56 H56 108.8 . . ? C55 C56 H56 108.8 . . ? C57 C56 H57 108.8 . . ? C55 C56 H57 108.8 . . ? H56 C56 H57 107.7 . . ? C58 C57 C60 107.6(3) . . ? C58 C57 C56 126.0(3) . . ? C60 C57 C56 126.4(3) . . ? N5 C58 C57 108.5(3) . . ? N5 C58 H58 125.7 . . ? C57 C58 H58 125.7 . . ? N5 C59 C60 106.3(3) . . ? N5 C59 C63 118.8(3) . . ? C60 C59 C63 134.8(3) . . ? C59 C60 C57 107.2(3) . . ? C59 C60 C134 129.2(5) . . ? C57 C60 C134 120.4(5) . . ? C59 C60 C132 124.5(5) . . ? C57 C60 C132 125.4(5) . . ? C134 C60 C132 31.2(5) . . ? O5 C63 C64 120.3(3) . . ? O5 C63 C59 113.7(3) . . ? C64 C63 C59 126.0(3) . . ? C65 C64 C63 120.3(3) . . ? C65 C64 H59 119.9 . . ? C63 C64 H59 119.9 . . ? O6 C65 C64 120.8(3) . . ? O6 C65 C66 113.1(3) . . ? C64 C65 C66 126.1(3) . . ? N6 C66 C67 107.7(3) . . ? N6 C66 C65 117.7(3) . . ? C67 C66 C65 134.5(3) . . ? C66 C67 C70 106.8(3) . . ? C66 C67 C68 128.4(3) . . ? C70 C67 C68 124.8(3) . . ? C67 C68 C69 114.3(3) . . ? C67 C68 H60 108.7 . . ? C69 C68 H60 108.7 . . ? C67 C68 H61 108.7 . . ? C69 C68 H61 108.7 . . ? H60 C68 H61 107.6 . . ? C68 C69 H62 109.5 . . ? C68 C69 H63 109.5 . . ? H62 C69 H63 109.5 . . ? C68 C69 H64 109.5 . . ? H62 C69 H64 109.5 . . ? H63 C69 H64 109.5 . . ? C73 C70 C67 107.7(3) . . ? C73 C70 C71 127.6(3) . . ? C67 C70 C71 124.7(3) . . ? C72 C71 C70 113.3(3) . . ? C72 C71 H65 108.9 . . ? C70 C71 H65 108.9 . . ? C72 C71 H66 108.9 . . ? C70 C71 H66 108.9 . . ? H65 C71 H66 107.7 . . ? C71 C72 H67 109.5 . . ? C71 C72 H68 109.5 . . ? H67 C72 H68 109.5 . . ? C71 C72 H69 109.5 . . ? H67 C72 H69 109.5 . . ? H68 C72 H69 109.5 . . ? N6 C73 C70 107.1(3) . . ? N6 C73 C74 119.4(3) . . ? C70 C73 C74 133.5(3) . . ? C75 C74 C79 118.0(3) . . ? C75 C74 C73 120.1(3) . . ? C79 C74 C73 121.9(3) . . ? C76 C75 C74 121.1(3) . . ? C76 C75 H70 119.4 . . ? C74 C75 H70 119.4 . . ? C77 C76 C75 120.6(3) . . ? C77 C76 H71 119.7 . . ? C75 C76 H71 119.7 . . ? C76 C77 C78 119.6(3) . . ? C76 C77 H72 120.2 . . ? C78 C77 H72 120.2 . . ? C77 C78 C79 119.6(3) . . ? C77 C78 C80 119.8(3) . . ? C79 C78 C80 120.5(3) . . ? C74 C79 C78 121.0(3) . . ? C74 C79 H73 119.5 . . ? C78 C79 H73 119.5 . . ? C81 C80 C78 177.9(4) . . ? C80 C81 C82 178.7(4) . . ? C83 C82 C81 177.6(4) . . ? C82 C83 C84 176.5(4) . . ? C85 C84 C89 120.1(3) . . ? C85 C84 C83 120.0(3) . . ? C89 C84 C83 119.9(3) . . ? C86 C85 C84 119.0(3) . . ? C86 C85 H74 120.5 . . ? C84 C85 H74 120.5 . . ? C85 C86 C87 120.3(3) . . ? C85 C86 C90 120.8(3) . . ? C87 C86 C90 118.7(3) . . ? C88 C87 C86 120.4(4) . . ? C88 C87 H75 119.8 . . ? C86 C87 H75 119.8 . . ? C87 C88 C89 120.3(4) . . ? C87 C88 H76 119.9 . . ? C89 C88 H76 119.9 . . ? C88 C89 C84 119.9(4) . . ? C88 C89 H77 120.1 . . ? C84 C89 H77 120.1 . . ? N7 C90 C91 107.6(3) . . ? N7 C90 C86 121.0(3) . . ? C91 C90 C86 130.9(3) . . ? C90 C91 C94 107.6(3) . . ? C90 C91 C92 126.6(3) . . ? C94 C91 C92 125.8(3) . . ? C91 C92 C93 114.9(3) . . ? C91 C92 H78 108.5 . . ? C93 C92 H78 108.5 . . ? C91 C92 H79 108.5 . . ? C93 C92 H79 108.5 . . ? H78 C92 H79 107.5 . . ? C92 C93 H80 109.5 . . ? C92 C93 H81 109.5 . . ? H80 C93 H81 109.5 . . ? C92 C93 H82 109.5 . . ? H80 C93 H82 109.5 . . ? H81 C93 H82 109.5 . . ? C97 C94 C91 107.7(3) . . ? C97 C94 C95 127.3(3) . . ? C91 C94 C95 124.9(3) . . ? C94 C95 C96 112.6(3) . . ? C94 C95 H83 109.1 . . ? C96 C95 H83 109.1 . . ? C94 C95 H84 109.1 . . ? C96 C95 H84 109.1 . . ? H83 C95 H84 107.8 . . ? C95 C96 H85 109.5 . . ? C95 C96 H86 109.5 . . ? H85 C96 H86 109.5 . . ? C95 C96 H87 109.5 . . ? H85 C96 H87 109.5 . . ? H86 C96 H87 109.5 . . ? N7 C97 C94 106.5(3) . . ? N7 C97 C98 118.0(3) . . ? C94 C97 C98 135.6(3) . . ? O7 C98 C99 120.3(3) . . ? O7 C98 C97 112.5(3) . . ? C99 C98 C97 127.1(3) . . ? C98 C99 C100 120.9(3) . . ? C98 C99 H88 119.6 . . ? C100 C99 H88 119.6 . . ? O8 C100 C99 119.8(3) . . ? O8 C100 C101 113.9(3) . . ? C99 C100 C101 126.3(3) . . ? N8 C101 C102 106.6(3) . . ? N8 C101 C100 118.8(3) . . ? C102 C101 C100 134.6(3) . . ? C107 C102 C101 106.7(3) . . ? C107 C102 C103 125.8(3) . . ? C101 C102 C103 127.5(3) . . ? C102 C103 C104 112.6(3) . . ? C102 C103 H89 109.1 . . ? C104 C103 H89 109.1 . . ? C102 C103 H90 109.1 . . ? C104 C103 H90 109.1 . . ? H89 C103 H90 107.8 . . ? C103 C104 H91 109.5 . . ? C103 C104 H92 109.5 . . ? H91 C104 H92 109.5 . . ? C103 C104 H93 109.5 . . ? H91 C104 H93 109.5 . . ? H92 C104 H93 109.5 . . ? C106 C105 C107 115.4(4) . . ? C106 C105 H94 108.4 . . ? C107 C105 H94 108.4 . . ? C106 C105 H95 108.4 . . ? C107 C105 H95 108.4 . . ? H94 C105 H95 107.5 . . ? C105 C106 H96 109.5 . . ? C105 C106 H97 109.5 . . ? H96 C106 H97 109.5 . . ? C105 C106 H98 109.5 . . ? H96 C106 H98 109.5 . . ? H97 C106 H98 109.5 . . ? C108 C107 C102 107.6(3) . . ? C108 C107 C105 124.3(4) . . ? C102 C107 C105 128.1(3) . . ? N8 C108 C107 109.1(3) . . ? N8 C108 H99 125.4 . . ? C107 C108 H99 125.4 . . ? C4 N1 C5 109.3(3) . . ? C4 N1 H100 125.3 . . ? C5 N1 H100 125.3 . . ? C19 N2 C12 110.7(3) . . ? C19 N2 H101 124.6 . . ? C12 N2 H101 124.6 . . ? C36 N3 C43 110.6(3) . . ? C36 N3 H102 124.7 . . ? C43 N3 H102 124.7 . . ? C52 N4 C47 109.1(3) . . ? C52 N4 H103 125.4 . . ? C47 N4 H103 125.4 . . ? C58 N5 C59 110.4(3) . . ? C58 N5 H104 124.8 . . ? C59 N5 H104 124.8 . . ? C73 N6 C66 110.6(3) . . ? C73 N6 H105 124.7 . . ? C66 N6 H105 124.7 . . ? C90 N7 C97 110.6(3) . . ? C90 N7 H106 124.7 . . ? C97 N7 H106 124.7 . . ? C108 N8 C101 110.0(3) . . ? C108 N8 H107 125.0 . . ? C101 N8 H107 125.0 . . ? C9 O1 B1 120.5(2) . . ? C11 O2 B1 120.8(3) . . ? C44 O3 B2 120.7(2) . . ? C46 O4 B2 120.5(2) . . ? C63 O5 B3 122.4(2) . . ? C65 O6 B3 122.2(2) . . ? C98 O7 B4 120.1(3) . . ? C100 O8 B4 120.5(3) . . ? F2 B1 F1 110.7(3) . . ? F2 B1 O2 108.7(3) . . ? F1 B1 O2 109.4(3) . . ? F2 B1 O1 108.3(3) . . ? F1 B1 O1 109.3(3) . . ? O2 B1 O1 110.4(3) . . ? F3 B2 F4 110.3(3) . . ? F3 B2 O3 109.1(3) . . ? F4 B2 O3 108.6(3) . . ? F3 B2 O4 109.8(3) . . ? F4 B2 O4 108.1(3) . . ? O3 B2 O4 111.0(3) . . ? F5 B3 F6 109.8(3) . . ? F5 B3 O6 109.9(3) . . ? F6 B3 O6 107.5(3) . . ? F5 B3 O5 109.2(3) . . ? F6 B3 O5 108.2(3) . . ? O6 B3 O5 112.1(3) . . ? F8 B4 F7 110.4(3) . . ? F8 B4 O7 108.9(3) . . ? F7 B4 O7 108.6(3) . . ? F8 B4 O8 109.2(3) . . ? F7 B4 O8 107.9(3) . . ? O7 B4 O8 111.8(3) . . ? C133 C132 C60 107.3(11) . . ? C133 C132 H108 110.3 . . ? C60 C132 H108 110.3 . . ? C133 C132 H109 110.3 . . ? C60 C132 H109 110.3 . . ? H108 C132 H109 108.5 . . ? C132 C133 H110 109.5 . . ? C132 C133 H111 109.5 . . ? H110 C133 H111 109.5 . . ? C132 C133 H112 109.5 . . ? H110 C133 H112 109.5 . . ? H111 C133 H112 109.5 . . ? C60 C134 C135 100.6(10) . . ? C60 C134 H113 111.6 . . ? C135 C134 H113 111.6 . . ? C60 C134 H114 111.6 . . ? C135 C134 H114 111.6 . . ? H113 C134 H114 109.4 . . ? 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 C1 C2 C3 C4 -11.5(5) . . . . ? C1 C2 C3 C6 168.6(3) . . . . ? C6 C3 C4 N1 -1.3(4) . . . . ? C2 C3 C4 N1 178.8(3) . . . . ? N1 C5 C6 C3 -0.1(4) . . . . ? C9 C5 C6 C3 177.7(4) . . . . ? N1 C5 C6 C7 178.5(3) . . . . ? C9 C5 C6 C7 -3.6(6) . . . . ? C4 C3 C6 C5 0.8(4) . . . . ? C2 C3 C6 C5 -179.3(3) . . . . ? C4 C3 C6 C7 -177.8(3) . . . . ? C2 C3 C6 C7 2.1(5) . . . . ? C5 C6 C7 C8 -84.5(4) . . . . ? C3 C6 C7 C8 93.9(4) . . . . ? N1 C5 C9 O1 3.9(4) . . . . ? C6 C5 C9 O1 -173.8(4) . . . . ? N1 C5 C9 C10 -171.5(3) . . . . ? C6 C5 C9 C10 10.8(6) . . . . ? O1 C9 C10 C11 -4.0(5) . . . . ? C5 C9 C10 C11 171.2(3) . . . . ? C9 C10 C11 O2 4.5(5) . . . . ? C9 C10 C11 C12 -173.6(3) . . . . ? O2 C11 C12 N2 0.9(4) . . . . ? C10 C11 C12 N2 179.1(3) . . . . ? O2 C11 C12 C13 -179.7(4) . . . . ? C10 C11 C12 C13 -1.5(6) . . . . ? N2 C12 C13 C16 1.2(4) . . . . ? C11 C12 C13 C16 -178.2(4) . . . . ? N2 C12 C13 C14 -173.0(3) . . . . ? C11 C12 C13 C14 7.5(6) . . . . ? C12 C13 C14 C15 82.1(4) . . . . ? C16 C13 C14 C15 -91.1(4) . . . . ? C12 C13 C16 C19 -1.1(4) . . . . ? C14 C13 C16 C19 173.2(3) . . . . ? C12 C13 C16 C17 -179.2(3) . . . . ? C14 C13 C16 C17 -4.9(5) . . . . ? C19 C16 C17 C18 98.9(4) . . . . ? C13 C16 C17 C18 -83.4(4) . . . . ? C13 C16 C19 N2 0.6(4) . . . . ? C17 C16 C19 N2 178.6(3) . . . . ? C13 C16 C19 C20 -174.6(3) . . . . ? C17 C16 C19 C20 3.4(6) . . . . ? N2 C19 C20 C25 147.3(3) . . . . ? C16 C19 C20 C25 -37.8(5) . . . . ? N2 C19 C20 C21 -28.9(4) . . . . ? C16 C19 C20 C21 145.9(4) . . . . ? C25 C20 C21 C22 -1.3(5) . . . . ? C19 C20 C21 C22 175.1(3) . . . . ? C20 C21 C22 C23 0.0(5) . . . . ? C21 C22 C23 C24 2.4(5) . . . . ? C22 C23 C24 C25 -3.6(5) . . . . ? C22 C23 C24 C26 179.1(3) . . . . ? C21 C20 C25 C24 0.2(5) . . . . ? C19 C20 C25 C24 -176.1(3) . . . . ? C23 C24 C25 C20 2.3(5) . . . . ? C26 C24 C25 C20 179.6(3) . . . . ? C23 C24 C26 C27 -157(16) . . . . ? C25 C24 C26 C27 26(16) . . . . ? C24 C26 C27 C28 -23(23) . . . . ? C26 C27 C28 C29 20(20) . . . . ? C27 C28 C29 C30 34(16) . . . . ? C28 C29 C30 C35 -15(3) . . . . ? C28 C29 C30 C31 164(3) . . . . ? C35 C30 C31 C32 1.1(6) . . . . ? C29 C30 C31 C32 -177.7(4) . . . . ? C30 C31 C32 C33 1.0(5) . . . . ? C30 C31 C32 C36 -178.5(3) . . . . ? C31 C32 C33 C34 -2.3(6) . . . . ? C36 C32 C33 C34 177.2(4) . . . . ? C32 C33 C34 C35 1.5(6) . . . . ? C33 C34 C35 C30 0.7(6) . . . . ? C31 C30 C35 C34 -2.0(6) . . . . ? C29 C30 C35 C34 176.8(4) . . . . ? C33 C32 C36 N3 -22.8(5) . . . . ? C31 C32 C36 N3 156.8(3) . . . . ? C33 C32 C36 C37 153.0(4) . . . . ? C31 C32 C36 C37 -27.5(6) . . . . ? N3 C36 C37 C40 0.1(4) . . . . ? C32 C36 C37 C40 -176.0(4) . . . . ? N3 C36 C37 C38 176.5(3) . . . . ? C32 C36 C37 C38 0.4(7) . . . . ? C36 C37 C38 C39 96.2(4) . . . . ? C40 C37 C38 C39 -88.1(4) . . . . ? C36 C37 C40 C43 -0.3(4) . . . . ? C38 C37 C40 C43 -176.7(3) . . . . ? C36 C37 C40 C41 175.5(3) . . . . ? C38 C37 C40 C41 -0.8(6) . . . . ? C43 C40 C41 C42 -87.1(4) . . . . ? C37 C40 C41 C42 97.8(4) . . . . ? C37 C40 C43 N3 0.4(4) . . . . ? C41 C40 C43 N3 -175.5(3) . . . . ? C37 C40 C43 C44 178.2(4) . . . . ? C41 C40 C43 C44 2.4(7) . . . . ? N3 C43 C44 O3 7.7(4) . . . . ? C40 C43 C44 O3 -170.0(4) . . . . ? N3 C43 C44 C45 -172.6(3) . . . . ? C40 C43 C44 C45 9.7(7) . . . . ? O3 C44 C45 C46 3.9(5) . . . . ? C43 C44 C45 C46 -175.8(3) . . . . ? C44 C45 C46 O4 -6.0(5) . . . . ? C44 C45 C46 C47 173.4(3) . . . . ? O4 C46 C47 N4 -6.1(4) . . . . ? C45 C46 C47 N4 174.5(3) . . . . ? O4 C46 C47 C48 174.6(4) . . . . ? C45 C46 C47 C48 -4.8(6) . . . . ? N4 C47 C48 C51 -1.1(4) . . . . ? C46 C47 C48 C51 178.3(4) . . . . ? N4 C47 C48 C49 178.2(3) . . . . ? C46 C47 C48 C49 -2.5(6) . . . . ? C47 C48 C49 C50 -74.4(4) . . . . ? C51 C48 C49 C50 104.6(4) . . . . ? C47 C48 C51 C52 0.8(4) . . . . ? C49 C48 C51 C52 -178.4(3) . . . . ? C47 C48 C51 C53 -179.6(3) . . . . ? C49 C48 C51 C53 1.2(6) . . . . ? C48 C51 C52 N4 -0.3(4) . . . . ? C53 C51 C52 N4 -179.9(3) . . . . ? C52 C51 C53 C54 -28.2(5) . . . . ? C48 C51 C53 C54 152.3(4) . . . . ? C55 C56 C57 C58 -26.8(7) . . . . ? C55 C56 C57 C60 151.7(5) . . . . ? C60 C57 C58 N5 1.5(5) . . . . ? C56 C57 C58 N5 -179.8(4) . . . . ? N5 C59 C60 C57 0.3(5) . . . . ? C63 C59 C60 C57 178.7(4) . . . . ? N5 C59 C60 C134 -159.1(8) . . . . ? C63 C59 C60 C134 19.3(11) . . . . ? N5 C59 C60 C132 162.1(7) . . . . ? C63 C59 C60 C132 -19.5(10) . . . . ? C58 C57 C60 C59 -1.1(5) . . . . ? C56 C57 C60 C59 -179.8(5) . . . . ? C58 C57 C60 C134 160.5(7) . . . . ? C56 C57 C60 C134 -18.2(9) . . . . ? C58 C57 C60 C132 -162.6(7) . . . . ? C56 C57 C60 C132 18.6(10) . . . . ? N5 C59 C63 O5 -6.6(5) . . . . ? C60 C59 C63 O5 175.2(4) . . . . ? N5 C59 C63 C64 173.3(4) . . . . ? C60 C59 C63 C64 -5.0(7) . . . . ? O5 C63 C64 C65 -1.0(5) . . . . ? C59 C63 C64 C65 179.2(4) . . . . ? C63 C64 C65 O6 -1.8(5) . . . . ? C63 C64 C65 C66 -179.7(3) . . . . ? O6 C65 C66 N6 -4.1(4) . . . . ? C64 C65 C66 N6 173.9(3) . . . . ? O6 C65 C66 C67 179.9(4) . . . . ? C64 C65 C66 C67 -2.0(6) . . . . ? N6 C66 C67 C70 -1.4(4) . . . . ? C65 C66 C67 C70 174.9(4) . . . . ? N6 C66 C67 C68 177.3(4) . . . . ? C65 C66 C67 C68 -6.4(7) . . . . ? C66 C67 C68 C69 95.0(5) . . . . ? C70 C67 C68 C69 -86.5(5) . . . . ? C66 C67 C70 C73 1.4(4) . . . . ? C68 C67 C70 C73 -177.4(3) . . . . ? C66 C67 C70 C71 -177.2(4) . . . . ? C68 C67 C70 C71 4.0(6) . . . . ? C73 C70 C71 C72 -67.8(5) . . . . ? C67 C70 C71 C72 110.5(4) . . . . ? C67 C70 C73 N6 -0.8(4) . . . . ? C71 C70 C73 N6 177.7(4) . . . . ? C67 C70 C73 C74 178.3(4) . . . . ? C71 C70 C73 C74 -3.2(7) . . . . ? N6 C73 C74 C75 -17.1(5) . . . . ? C70 C73 C74 C75 163.8(4) . . . . ? N6 C73 C74 C79 162.4(3) . . . . ? C70 C73 C74 C79 -16.6(6) . . . . ? C79 C74 C75 C76 -0.4(5) . . . . ? C73 C74 C75 C76 179.2(3) . . . . ? C74 C75 C76 C77 0.4(5) . . . . ? C75 C76 C77 C78 0.2(5) . . . . ? C76 C77 C78 C79 -0.7(5) . . . . ? C76 C77 C78 C80 -179.6(3) . . . . ? C75 C74 C79 C78 -0.2(5) . . . . ? C73 C74 C79 C78 -179.7(3) . . . . ? C77 C78 C79 C74 0.7(5) . . . . ? C80 C78 C79 C74 179.6(3) . . . . ? C77 C78 C80 C81 2(11) . . . . ? C79 C78 C80 C81 -177(100) . . . . ? C78 C80 C81 C82 152(15) . . . . ? C80 C81 C82 C83 -23(26) . . . . ? C81 C82 C83 C84 67(14) . . . . ? C82 C83 C84 C85 -145(7) . . . . ? C82 C83 C84 C89 34(8) . . . . ? C89 C84 C85 C86 -2.0(6) . . . . ? C83 C84 C85 C86 177.1(3) . . . . ? C84 C85 C86 C87 0.9(6) . . . . ? C84 C85 C86 C90 177.0(3) . . . . ? C85 C86 C87 C88 0.4(6) . . . . ? C90 C86 C87 C88 -175.8(4) . . . . ? C86 C87 C88 C89 -0.5(7) . . . . ? C87 C88 C89 C84 -0.6(7) . . . . ? C85 C84 C89 C88 1.9(7) . . . . ? C83 C84 C89 C88 -177.2(4) . . . . ? C85 C86 C90 N7 144.9(3) . . . . ? C87 C86 C90 N7 -39.0(5) . . . . ? C85 C86 C90 C91 -45.0(6) . . . . ? C87 C86 C90 C91 131.2(4) . . . . ? N7 C90 C91 C94 1.1(4) . . . . ? C86 C90 C91 C94 -170.0(4) . . . . ? N7 C90 C91 C92 178.1(3) . . . . ? C86 C90 C91 C92 7.0(6) . . . . ? C90 C91 C92 C93 95.1(4) . . . . ? C94 C91 C92 C93 -88.3(4) . . . . ? C90 C91 C94 C97 -0.9(4) . . . . ? C92 C91 C94 C97 -177.9(3) . . . . ? C90 C91 C94 C95 175.2(3) . . . . ? C92 C91 C94 C95 -1.8(5) . . . . ? C97 C94 C95 C96 84.4(4) . . . . ? C91 C94 C95 C96 -90.9(4) . . . . ? C91 C94 C97 N7 0.3(4) . . . . ? C95 C94 C97 N7 -175.7(3) . . . . ? C91 C94 C97 C98 179.9(4) . . . . ? C95 C94 C97 C98 3.9(6) . . . . ? N7 C97 C98 O7 -4.2(4) . . . . ? C94 C97 C98 O7 176.3(4) . . . . ? N7 C97 C98 C99 174.6(3) . . . . ? C94 C97 C98 C99 -4.9(7) . . . . ? O7 C98 C99 C100 1.1(5) . . . . ? C97 C98 C99 C100 -177.6(3) . . . . ? C98 C99 C100 O8 -2.9(5) . . . . ? C98 C99 C100 C101 177.7(3) . . . . ? O8 C100 C101 N8 -8.8(4) . . . . ? C99 C100 C101 N8 170.5(3) . . . . ? O8 C100 C101 C102 175.0(4) . . . . ? C99 C100 C101 C102 -5.7(6) . . . . ? N8 C101 C102 C107 -0.4(4) . . . . ? C100 C101 C102 C107 176.1(4) . . . . ? N8 C101 C102 C103 176.6(3) . . . . ? C100 C101 C102 C103 -6.9(6) . . . . ? C107 C102 C103 C104 99.2(4) . . . . ? C101 C102 C103 C104 -77.3(4) . . . . ? C101 C102 C107 C108 0.2(4) . . . . ? C103 C102 C107 C108 -176.9(3) . . . . ? C101 C102 C107 C105 -179.0(4) . . . . ? C103 C102 C107 C105 3.9(6) . . . . ? C106 C105 C107 C108 69.9(6) . . . . ? C106 C105 C107 C102 -111.0(5) . . . . ? C102 C107 C108 N8 0.1(4) . . . . ? C105 C107 C108 N8 179.4(3) . . . . ? C3 C4 N1 C5 1.3(4) . . . . ? C6 C5 N1 C4 -0.7(4) . . . . ? C9 C5 N1 C4 -179.0(3) . . . . ? C16 C19 N2 C12 0.1(4) . . . . ? C20 C19 N2 C12 176.1(3) . . . . ? C13 C12 N2 C19 -0.9(4) . . . . ? C11 C12 N2 C19 178.7(3) . . . . ? C37 C36 N3 C43 0.1(4) . . . . ? C32 C36 N3 C43 176.9(3) . . . . ? C40 C43 N3 C36 -0.3(4) . . . . ? C44 C43 N3 C36 -178.6(3) . . . . ? C51 C52 N4 C47 -0.4(4) . . . . ? C48 C47 N4 C52 0.9(4) . . . . ? C46 C47 N4 C52 -178.6(3) . . . . ? C57 C58 N5 C59 -1.3(5) . . . . ? C60 C59 N5 C58 0.6(4) . . . . ? C63 C59 N5 C58 -178.1(3) . . . . ? C70 C73 N6 C66 -0.1(4) . . . . ? C74 C73 N6 C66 -179.3(3) . . . . ? C67 C66 N6 C73 0.9(4) . . . . ? C65 C66 N6 C73 -176.1(3) . . . . ? C91 C90 N7 C97 -0.9(4) . . . . ? C86 C90 N7 C97 171.3(3) . . . . ? C94 C97 N7 C90 0.4(4) . . . . ? C98 C97 N7 C90 -179.3(3) . . . . ? C107 C108 N8 C101 -0.4(4) . . . . ? C102 C101 N8 C108 0.5(4) . . . . ? C100 C101 N8 C108 -176.6(3) . . . . ? C10 C9 O1 B1 -15.2(5) . . . . ? C5 C9 O1 B1 169.1(3) . . . . ? C10 C11 O2 B1 14.3(5) . . . . ? C12 C11 O2 B1 -167.3(3) . . . . ? C45 C44 O3 B2 16.2(5) . . . . ? C43 C44 O3 B2 -164.0(3) . . . . ? C45 C46 O4 B2 -11.8(5) . . . . ? C47 C46 O4 B2 168.7(3) . . . . ? C64 C63 O5 B3 -5.6(5) . . . . ? C59 C63 O5 B3 174.2(3) . . . . ? C64 C65 O6 B3 11.2(5) . . . . ? C66 C65 O6 B3 -170.6(3) . . . . ? C99 C98 O7 B4 16.0(5) . . . . ? C97 C98 O7 B4 -165.1(3) . . . . ? C99 C100 O8 B4 -12.5(5) . . . . ? C101 C100 O8 B4 166.9(3) . . . . ? C11 O2 B1 F2 -149.1(3) . . . . ? C11 O2 B1 F1 89.9(4) . . . . ? C11 O2 B1 O1 -30.4(5) . . . . ? C9 O1 B1 F2 149.7(3) . . . . ? C9 O1 B1 F1 -89.5(4) . . . . ? C9 O1 B1 O2 30.8(5) . . . . ? C44 O3 B2 F3 -152.3(3) . . . . ? C44 O3 B2 F4 87.4(3) . . . . ? C44 O3 B2 O4 -31.3(4) . . . . ? C46 O4 B2 F3 149.7(3) . . . . ? C46 O4 B2 F4 -90.0(3) . . . . ? C46 O4 B2 O3 29.0(4) . . . . ? C65 O6 B3 F5 -137.9(3) . . . . ? C65 O6 B3 F6 102.6(3) . . . . ? C65 O6 B3 O5 -16.2(5) . . . . ? C63 O5 B3 F5 135.5(3) . . . . ? C63 O5 B3 F6 -105.0(3) . . . . ? C63 O5 B3 O6 13.4(5) . . . . ? C98 O7 B4 F8 -149.5(3) . . . . ? C98 O7 B4 F7 90.1(3) . . . . ? C98 O7 B4 O8 -28.8(4) . . . . ? C100 O8 B4 F8 147.7(3) . . . . ? C100 O8 B4 F7 -92.3(4) . . . . ? C100 O8 B4 O7 27.1(5) . . . . ? C59 C60 C132 C133 103.8(8) . . . . ? C57 C60 C132 C133 -97.7(8) . . . . ? C134 C60 C132 C133 -6.3(9) . . . . ? C59 C60 C134 C135 -101.0(9) . . . . ? C57 C60 C134 C135 101.9(9) . . . . ? C132 C60 C134 C135 -7.3(9) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.463 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.061 # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.003 0.000 0.000 1545.4 107.7 2 0.195 0.500 0.500 1545.3 107.7 3 0.251 0.707 0.075 9.9 0.6 4 0.749 0.207 0.424 9.9 0.7 5 0.251 0.793 0.575 9.9 0.6 6 0.749 0.293 0.924 9.9 0.7 _platon_squeeze_details ; ; #============================================================================== # End of CIF #============================================================================== data_81005-3 _database_code_depnum_ccdc_archive 'CCDC 819395' #TrackingRef '- BF2_ethynyl_HMaeda_CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C86 H128 B2 Cl2 F4 N6 O4.75' _chemical_formula_weight 1490.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 9.681(7) _cell_length_b 9.695(7) _cell_length_c 22.899(14) _cell_angle_alpha 95.21(2) _cell_angle_beta 91.74(2) _cell_angle_gamma 92.92(3) _cell_volume 2136(3) _cell_formula_units_Z 1 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 9555 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.6 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.159 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 0.137 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9349 _exptl_absorpt_correction_T_max 0.9865 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _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 16858 _diffrn_reflns_av_R_equivalents 0.0727 _diffrn_reflns_av_sigmaI/netI 0.1138 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.48 _reflns_number_total 9234 _reflns_number_gt 4766 _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. ISOR was applied for carbon C32 and C32B. ; _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^)+(0.1221P)^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 9234 _refine_ls_number_parameters 525 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1354 _refine_ls_R_factor_gt 0.0698 _refine_ls_wR_factor_ref 0.2345 _refine_ls_wR_factor_gt 0.1809 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.958 _refine_ls_shift/su_max 0.009 _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 -0.2234(4) 0.5744(3) 0.58509(15) 0.0404(8) Uani 1 1 d . . . H1 H -0.3203 0.5534 0.5855 0.048 Uiso 1 1 calc R . . C2 C -0.1551(4) 0.6340(3) 0.54031(14) 0.0371(7) Uani 1 1 d . . . C3 C -0.0131(4) 0.6475(3) 0.55682(13) 0.0374(7) Uani 1 1 d . . . C4 C 0.0008(3) 0.5958(3) 0.61194(14) 0.0350(7) Uani 1 1 d . . . C5 C 0.1173(3) 0.5873(3) 0.65007(14) 0.0356(7) Uani 1 1 d . . . C6 C 0.1086(3) 0.5372(3) 0.70535(13) 0.0347(7) Uani 1 1 d . . . H2 H 0.0204 0.5230 0.7216 0.042 Uiso 1 1 calc R . . C7 C 0.2247(3) 0.5084(3) 0.73630(14) 0.0349(7) Uani 1 1 d . . . C8 C 0.2205(3) 0.4377(3) 0.78894(14) 0.0348(7) Uani 1 1 d . . . C9 C 0.3250(3) 0.4091(3) 0.82928(15) 0.0375(7) Uani 1 1 d . . . C10 C 0.2631(3) 0.3421(3) 0.87406(14) 0.0366(7) Uani 1 1 d . . . C11 C 0.1203(3) 0.3292(3) 0.86036(13) 0.0329(7) Uani 1 1 d . . . C12 C 0.0043(3) 0.2701(3) 0.89164(13) 0.0328(7) Uani 1 1 d . . . C13 C -0.1223(3) 0.3323(3) 0.89250(14) 0.0366(7) Uani 1 1 d . . . H3 H -0.1323 0.4148 0.8737 0.044 Uiso 1 1 calc R . . C14 C -0.2342(4) 0.2756(3) 0.92038(14) 0.0389(7) Uani 1 1 d . . . H4 H -0.3189 0.3209 0.9215 0.047 Uiso 1 1 calc R . . C15 C -0.2228(3) 0.1527(3) 0.94674(13) 0.0356(7) Uani 1 1 d . . . C16 C -0.0961(3) 0.0905(3) 0.94653(14) 0.0371(7) Uani 1 1 d . . . H5 H -0.0867 0.0075 0.9650 0.044 Uiso 1 1 calc R . . C17 C 0.0153(3) 0.1481(3) 0.91980(13) 0.0354(7) Uani 1 1 d . . . H6 H 0.1011 0.1048 0.9204 0.042 Uiso 1 1 calc R . . C18 C -0.3415(4) 0.0875(4) 0.97153(14) 0.0405(8) Uani 1 1 d . . . C19 C -0.4425(4) 0.0315(4) 0.98995(15) 0.0416(8) Uani 1 1 d . . . C20 C -0.2185(4) 0.6751(4) 0.48403(15) 0.0457(8) Uani 1 1 d . . . H7 H -0.1670 0.6337 0.4507 0.055 Uiso 1 1 calc R . . H8 H -0.2079 0.7772 0.4840 0.055 Uiso 1 1 calc R . . C21 C -0.3706(4) 0.6303(4) 0.47464(17) 0.0550(10) Uani 1 1 d . . . H9 H -0.3823 0.5293 0.4748 0.082 Uiso 1 1 calc R . . H10 H -0.4045 0.6576 0.4368 0.082 Uiso 1 1 calc R . . H11 H -0.4234 0.6750 0.5062 0.082 Uiso 1 1 calc R . . C22 C 0.0984(4) 0.7083(3) 0.52136(14) 0.0418(8) Uani 1 1 d . . . H12 H 0.0690 0.6965 0.4793 0.050 Uiso 1 1 calc R . . H13 H 0.1836 0.6576 0.5261 0.050 Uiso 1 1 calc R . . C23 C 0.1297(5) 0.8616(4) 0.53997(19) 0.0573(11) Uani 1 1 d . . . H14 H 0.0442 0.9112 0.5379 0.086 Uiso 1 1 calc R . . H15 H 0.1970 0.8995 0.5137 0.086 Uiso 1 1 calc R . . H16 H 0.1681 0.8729 0.5803 0.086 Uiso 1 1 calc R . . C24 C 0.4774(4) 0.4478(4) 0.82574(18) 0.0502(9) Uani 1 1 d . . . H17 H 0.5045 0.4332 0.7844 0.060 Uiso 1 1 calc R . . H18 H 0.5311 0.3860 0.8488 0.060 Uiso 1 1 calc R . . C25 C 0.5135(5) 0.5972(5) 0.8487(2) 0.0685(13) Uani 1 1 d . . . H19 H 0.4680 0.6591 0.8235 0.103 Uiso 1 1 calc R . . H20 H 0.6140 0.6153 0.8486 0.103 Uiso 1 1 calc R . . H21 H 0.4818 0.6137 0.8888 0.103 Uiso 1 1 calc R . . C26 C 0.3316(4) 0.3085(4) 0.93039(15) 0.0449(8) Uani 1 1 d . . . H22 H 0.4329 0.3082 0.9255 0.054 Uiso 1 1 calc R . . H23 H 0.2990 0.2140 0.9387 0.054 Uiso 1 1 calc R . . C27 C 0.3023(5) 0.4105(5) 0.98255(17) 0.0706(13) Uani 1 1 d . . . H24 H 0.3390 0.5035 0.9756 0.106 Uiso 1 1 calc R . . H25 H 0.3468 0.3817 1.0181 0.106 Uiso 1 1 calc R . . H26 H 0.2021 0.4121 0.9874 0.106 Uiso 1 1 calc R . . N1 N -0.1308(3) 0.5510(3) 0.62784(12) 0.0378(6) Uani 1 1 d . . . H27 H -0.1502 0.5136 0.6604 0.045 Uiso 1 1 calc R . . N2 N 0.0975(3) 0.3874(3) 0.80938(11) 0.0328(6) Uani 1 1 d . . . H28 H 0.0158 0.3922 0.7920 0.039 Uiso 1 1 calc R . . O1 O 0.2394(2) 0.6250(2) 0.63070(10) 0.0401(5) Uani 1 1 d . . . O2 O 0.3485(2) 0.5446(2) 0.71815(10) 0.0397(5) Uani 1 1 d . . . B1 B 0.3589(4) 0.6450(4) 0.67323(18) 0.0407(9) Uani 1 1 d . . . F1 F 0.4772(2) 0.6265(2) 0.64349(9) 0.0520(5) Uani 1 1 d . . . F2 F 0.3578(2) 0.7776(2) 0.70146(9) 0.0521(5) Uani 1 1 d . . . Cl1 Cl -0.20180(9) 0.38760(9) 0.74298(4) 0.0429(2) Uani 1 1 d . . . N3 N -0.1822(3) -0.0546(3) 0.74241(12) 0.0385(6) Uani 1 1 d . . . C28 C -0.0539(4) 0.0401(3) 0.73849(15) 0.0394(8) Uani 1 1 d . A . H29 H -0.0210 0.0743 0.7788 0.047 Uiso 1 1 calc R . . H30 H -0.0803 0.1215 0.7184 0.047 Uiso 1 1 calc R . . C29 C 0.0665(4) -0.0252(4) 0.70639(17) 0.0465(9) Uani 1 1 d . . . H31 H 0.1020 -0.0996 0.7286 0.056 Uiso 1 1 calc R A . H32 H 0.0336 -0.0672 0.6671 0.056 Uiso 1 1 calc R . . C30 C 0.1824(4) 0.0842(4) 0.69998(18) 0.0522(9) Uani 1 1 d . A . H33 H 0.2673 0.0372 0.6887 0.063 Uiso 1 1 calc R . . H34 H 0.2019 0.1381 0.7384 0.063 Uiso 1 1 calc R . . C31 C 0.1483(5) 0.1840(4) 0.65448(17) 0.0595(11) Uani 1 1 d . . . H35 H 0.1212 0.1310 0.6170 0.089 Uiso 1 1 calc R A . H36 H 0.2299 0.2451 0.6493 0.089 Uiso 1 1 calc R . . H37 H 0.0718 0.2399 0.6679 0.089 Uiso 1 1 calc R . . C32 C -0.2567(19) -0.1005(19) 0.6865(8) 0.041(3) Uani 0.566(13) 1 d PU A 2 H56 H -0.3286 -0.1724 0.6939 0.049 Uiso 0.566(13) 1 calc PR A 2 H57 H -0.1906 -0.1447 0.6595 0.049 Uiso 0.566(13) 1 calc PR A 2 C33 C -0.3253(11) 0.0114(8) 0.6558(4) 0.053(2) Uani 0.566(13) 1 d P A 2 H58 H -0.4004 0.0477 0.6802 0.063 Uiso 0.566(13) 1 calc PR A 2 H59 H -0.2564 0.0889 0.6522 0.063 Uiso 0.566(13) 1 calc PR A 2 C34 C -0.3847(15) -0.0392(18) 0.5958(8) 0.068(4) Uani 0.566(13) 1 d P A 2 H60 H -0.3085 -0.0678 0.5704 0.082 Uiso 0.566(13) 1 calc PR A 2 H61 H -0.4474 -0.1219 0.5990 0.082 Uiso 0.566(13) 1 calc PR A 2 C35 C -0.4622(13) 0.0665(15) 0.5679(5) 0.111(5) Uani 0.566(13) 1 d P A 2 H62 H -0.5439 0.0879 0.5906 0.166 Uiso 0.566(13) 1 calc PR A 2 H63 H -0.4914 0.0306 0.5278 0.166 Uiso 0.566(13) 1 calc PR A 2 H64 H -0.4025 0.1509 0.5668 0.166 Uiso 0.566(13) 1 calc PR A 2 C32B C -0.236(3) -0.086(3) 0.6756(9) 0.039(4) Uani 0.434(13) 1 d PU A 1 H65 H -0.1728 -0.1490 0.6551 0.046 Uiso 0.434(13) 1 calc PR A 1 H66 H -0.3283 -0.1356 0.6751 0.046 Uiso 0.434(13) 1 calc PR A 1 C33B C -0.2491(14) 0.0391(10) 0.6412(5) 0.048(3) Uani 0.434(13) 1 d P A 1 H67 H -0.2821 0.1173 0.6670 0.058 Uiso 0.434(13) 1 calc PR A 1 H68 H -0.1569 0.0678 0.6274 0.058 Uiso 0.434(13) 1 calc PR A 1 C34B C -0.347(2) 0.007(3) 0.5896(10) 0.069(6) Uani 0.434(13) 1 d P A 1 H69 H -0.3285 -0.0842 0.5693 0.082 Uiso 0.434(13) 1 calc PR A 1 H70 H -0.3336 0.0782 0.5616 0.082 Uiso 0.434(13) 1 calc PR A 1 C35B C -0.5001(18) 0.005(2) 0.6095(7) 0.125(8) Uani 0.434(13) 1 d P A 1 H71 H -0.5093 -0.0517 0.6427 0.187 Uiso 0.434(13) 1 calc PR A 1 H72 H -0.5616 -0.0354 0.5769 0.187 Uiso 0.434(13) 1 calc PR A 1 H73 H -0.5253 0.0995 0.6214 0.187 Uiso 0.434(13) 1 calc PR A 1 C36 C -0.2795(4) 0.0270(3) 0.78162(15) 0.0416(8) Uani 1 1 d . A . H38 H -0.2287 0.0600 0.8188 0.050 Uiso 1 1 calc R . . H39 H -0.3047 0.1098 0.7622 0.050 Uiso 1 1 calc R . . C37 C -0.4118(4) -0.0517(3) 0.79613(17) 0.0451(8) Uani 1 1 d . . . H40 H -0.3907 -0.1157 0.8261 0.054 Uiso 1 1 calc R A . H41 H -0.4498 -0.1080 0.7605 0.054 Uiso 1 1 calc R . . C38 C -0.5197(4) 0.0468(4) 0.81902(16) 0.0450(8) Uani 1 1 d . A . H42 H -0.4793 0.1071 0.8531 0.054 Uiso 1 1 calc R . . H43 H -0.5446 0.1069 0.7880 0.054 Uiso 1 1 calc R . . C39 C -0.6490(4) -0.0294(4) 0.83719(18) 0.0542(10) Uani 1 1 d . . . H44 H -0.6839 -0.0966 0.8049 0.081 Uiso 1 1 calc R A . H45 H -0.7196 0.0372 0.8467 0.081 Uiso 1 1 calc R . . H46 H -0.6275 -0.0782 0.8717 0.081 Uiso 1 1 calc R . . C40 C -0.1458(4) -0.1873(3) 0.76775(15) 0.0424(8) Uani 1 1 d . A . H47 H -0.0809 -0.2358 0.7414 0.051 Uiso 1 1 calc R . . H48 H -0.2310 -0.2480 0.7682 0.051 Uiso 1 1 calc R . . C41 C -0.0809(4) -0.1683(3) 0.82912(15) 0.0444(8) Uani 1 1 d . . . H49 H -0.0062 -0.0943 0.8311 0.053 Uiso 1 1 calc R A . H50 H -0.1516 -0.1388 0.8573 0.053 Uiso 1 1 calc R . . C42 C -0.0224(5) -0.3005(4) 0.84607(18) 0.0619(12) Uani 1 1 d . A . H51 H 0.0504 -0.3273 0.8185 0.074 Uiso 1 1 calc R . . H52 H -0.0967 -0.3751 0.8418 0.074 Uiso 1 1 calc R . . C43 C 0.0385(6) -0.2906(4) 0.90789(18) 0.0701(13) Uani 1 1 d . . . H53 H 0.1145 -0.2193 0.9122 0.105 Uiso 1 1 calc R A . H54 H 0.0737 -0.3803 0.9159 0.105 Uiso 1 1 calc R . . H55 H -0.0332 -0.2659 0.9357 0.105 Uiso 1 1 calc R . . O3 O 0.4859(11) 0.6996(11) 0.3225(5) 0.113(6) Uani 0.373(13) 1 d P . . 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 0.0406(19) 0.0337(16) 0.0474(18) 0.0028(15) -0.0028(15) 0.0115(14) C2 0.0402(19) 0.0324(15) 0.0399(16) 0.0058(14) 0.0011(14) 0.0114(13) C3 0.046(2) 0.0308(15) 0.0365(16) 0.0050(13) -0.0005(14) 0.0111(14) C4 0.0326(17) 0.0315(15) 0.0426(16) 0.0078(13) 0.0057(14) 0.0101(13) C5 0.0369(18) 0.0287(14) 0.0428(16) 0.0049(13) 0.0083(14) 0.0118(13) C6 0.0342(18) 0.0320(15) 0.0402(16) 0.0097(13) 0.0079(14) 0.0106(13) C7 0.0333(17) 0.0283(14) 0.0447(17) 0.0067(13) 0.0047(14) 0.0088(12) C8 0.0312(17) 0.0268(14) 0.0480(17) 0.0071(13) 0.0047(14) 0.0093(12) C9 0.0305(17) 0.0330(16) 0.0511(19) 0.0109(14) 0.0009(14) 0.0094(13) C10 0.0358(18) 0.0288(15) 0.0476(18) 0.0116(14) 0.0014(14) 0.0117(13) C11 0.0309(17) 0.0284(14) 0.0409(16) 0.0059(13) -0.0003(13) 0.0135(12) C12 0.0329(17) 0.0288(14) 0.0378(15) 0.0049(13) 0.0012(13) 0.0099(12) C13 0.0372(18) 0.0284(15) 0.0462(17) 0.0098(13) -0.0016(14) 0.0105(13) C14 0.0324(18) 0.0378(17) 0.0487(18) 0.0094(15) 0.0008(15) 0.0128(13) C15 0.0343(18) 0.0348(16) 0.0387(16) 0.0076(14) 0.0023(13) 0.0050(13) C16 0.0403(19) 0.0327(16) 0.0407(16) 0.0127(14) -0.0007(14) 0.0109(13) C17 0.0338(18) 0.0323(15) 0.0420(16) 0.0060(14) 0.0042(14) 0.0136(13) C18 0.0360(19) 0.0436(18) 0.0441(18) 0.0108(15) 0.0012(15) 0.0130(15) C19 0.0336(19) 0.0452(19) 0.0490(19) 0.0173(16) 0.0016(15) 0.0096(15) C20 0.044(2) 0.050(2) 0.0447(18) 0.0100(16) -0.0001(16) 0.0149(16) C21 0.050(2) 0.067(3) 0.048(2) 0.0069(19) -0.0091(18) 0.0114(19) C22 0.048(2) 0.0406(18) 0.0383(16) 0.0068(15) 0.0020(15) 0.0093(15) C23 0.065(3) 0.043(2) 0.066(2) 0.0113(18) 0.018(2) 0.0014(19) C24 0.0318(19) 0.055(2) 0.070(2) 0.0338(19) -0.0014(17) 0.0080(16) C25 0.054(3) 0.067(3) 0.084(3) 0.020(2) -0.010(2) -0.017(2) C26 0.0344(19) 0.0458(19) 0.057(2) 0.0190(17) -0.0016(16) 0.0066(15) C27 0.075(3) 0.090(3) 0.048(2) 0.004(2) -0.010(2) 0.027(3) N1 0.0393(16) 0.0333(13) 0.0429(14) 0.0094(12) 0.0028(12) 0.0113(11) N2 0.0310(14) 0.0291(12) 0.0404(13) 0.0099(11) 0.0017(11) 0.0110(10) O1 0.0349(13) 0.0434(13) 0.0444(12) 0.0128(10) 0.0053(10) 0.0080(10) O2 0.0336(13) 0.0423(12) 0.0460(12) 0.0142(10) 0.0056(10) 0.0089(10) B1 0.035(2) 0.041(2) 0.049(2) 0.0128(17) 0.0045(17) 0.0067(16) F1 0.0368(12) 0.0652(14) 0.0572(12) 0.0185(10) 0.0093(9) 0.0081(10) F2 0.0604(14) 0.0390(11) 0.0572(12) 0.0071(9) -0.0070(10) 0.0053(10) Cl1 0.0356(5) 0.0431(4) 0.0529(5) 0.0170(4) 0.0003(4) 0.0080(3) N3 0.0394(16) 0.0318(13) 0.0445(15) -0.0001(12) -0.0027(12) 0.0131(11) C28 0.042(2) 0.0312(15) 0.0461(18) 0.0070(14) 0.0035(15) 0.0089(14) C29 0.045(2) 0.0384(18) 0.057(2) 0.0068(16) 0.0029(17) 0.0126(15) C30 0.044(2) 0.051(2) 0.064(2) 0.0127(19) 0.0083(18) 0.0104(17) C31 0.079(3) 0.042(2) 0.059(2) 0.0102(18) 0.012(2) 0.005(2) C32 0.043(6) 0.038(5) 0.044(7) 0.007(4) 0.006(4) 0.020(4) C33 0.051(6) 0.048(4) 0.059(5) -0.001(4) -0.016(4) 0.019(4) C34 0.056(10) 0.091(11) 0.060(8) 0.015(6) -0.019(7) 0.020(7) C35 0.100(9) 0.155(12) 0.086(7) 0.041(7) -0.032(6) 0.055(8) C32B 0.046(7) 0.048(7) 0.022(5) -0.002(5) -0.005(5) 0.004(5) C33B 0.047(7) 0.049(5) 0.051(5) 0.008(4) -0.003(5) 0.008(5) C34B 0.050(9) 0.112(17) 0.044(6) 0.014(9) 0.007(6) -0.009(8) C35B 0.091(13) 0.187(19) 0.109(12) 0.099(12) -0.012(9) -0.012(12) C36 0.046(2) 0.0293(15) 0.0508(19) 0.0005(14) 0.0051(16) 0.0140(14) C37 0.038(2) 0.0362(17) 0.062(2) 0.0024(16) 0.0012(17) 0.0107(14) C38 0.039(2) 0.0438(19) 0.054(2) 0.0042(16) 0.0048(16) 0.0144(15) C39 0.045(2) 0.058(2) 0.060(2) 0.0022(19) 0.0025(18) 0.0115(18) C40 0.051(2) 0.0268(15) 0.0511(19) 0.0058(14) 0.0030(16) 0.0150(14) C41 0.055(2) 0.0335(16) 0.0457(18) 0.0062(15) 0.0015(17) 0.0116(15) C42 0.095(3) 0.0308(18) 0.061(2) 0.0058(17) -0.011(2) 0.0225(19) C43 0.102(4) 0.047(2) 0.064(3) 0.011(2) -0.014(3) 0.025(2) O3 0.082(8) 0.099(8) 0.146(11) -0.051(7) -0.056(7) 0.043(6) _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 1.350(4) . ? C1 C2 1.390(5) . ? C1 H1 0.9500 . ? C2 C3 1.411(5) . ? C2 C20 1.505(5) . ? C3 C4 1.405(5) . ? C3 C22 1.499(5) . ? C4 N1 1.394(4) . ? C4 C5 1.415(5) . ? C5 O1 1.321(4) . ? C5 C6 1.400(5) . ? C6 C7 1.365(5) . ? C6 H2 0.9500 . ? C7 O2 1.321(4) . ? C7 C8 1.441(5) . ? C8 N2 1.375(4) . ? C8 C9 1.404(5) . ? C9 C10 1.397(5) . ? C9 C24 1.511(5) . ? C10 C11 1.405(5) . ? C10 C26 1.502(5) . ? C11 N2 1.359(4) . ? C11 C12 1.470(4) . ? C12 C13 1.393(5) . ? C12 C17 1.405(4) . ? C13 C14 1.388(5) . ? C13 H3 0.9500 . ? C14 C15 1.391(5) . ? C14 H4 0.9500 . ? C15 C16 1.394(5) . ? C15 C18 1.439(5) . ? C16 C17 1.375(5) . ? C16 H5 0.9500 . ? C17 H6 0.9500 . ? C18 C19 1.201(5) . ? C19 C19 1.356(7) 2_457 ? C20 C21 1.518(5) . ? C20 H7 0.9900 . ? C20 H8 0.9900 . ? C21 H9 0.9800 . ? C21 H10 0.9800 . ? C21 H11 0.9800 . ? C22 C23 1.521(5) . ? C22 H12 0.9900 . ? C22 H13 0.9900 . ? C23 H14 0.9800 . ? C23 H15 0.9800 . ? C23 H16 0.9800 . ? C24 C25 1.514(6) . ? C24 H17 0.9900 . ? C24 H18 0.9900 . ? C25 H19 0.9800 . ? C25 H20 0.9800 . ? C25 H21 0.9800 . ? C26 C27 1.524(6) . ? C26 H22 0.9900 . ? C26 H23 0.9900 . ? C27 H24 0.9800 . ? C27 H25 0.9800 . ? C27 H26 0.9800 . ? N1 H27 0.8800 . ? N2 H28 0.8800 . ? O1 B1 1.483(5) . ? O2 B1 1.481(5) . ? B1 F1 1.362(5) . ? B1 F2 1.386(4) . ? N3 C32 1.471(18) . ? N3 C40 1.511(4) . ? N3 C28 1.516(4) . ? N3 C36 1.522(4) . ? N3 C32B 1.60(2) . ? C28 C29 1.530(5) . ? C28 H29 0.9900 . ? C28 H30 0.9900 . ? C29 C30 1.524(5) . ? C29 H31 0.9900 . ? C29 H32 0.9900 . ? C30 C31 1.524(6) . ? C30 H33 0.9900 . ? C30 H34 0.9900 . ? C31 H35 0.9800 . ? C31 H36 0.9800 . ? C31 H37 0.9800 . ? C32 C33 1.51(2) . ? C32 H56 0.9900 . ? C32 H57 0.9900 . ? C33 C34 1.502(19) . ? C33 H58 0.9900 . ? C33 H59 0.9900 . ? C34 C35 1.479(19) . ? C34 H60 0.9900 . ? C34 H61 0.9900 . ? C35 H62 0.9800 . ? C35 H63 0.9800 . ? C35 H64 0.9800 . ? C32B C33B 1.51(3) . ? C32B H65 0.9900 . ? C32B H66 0.9900 . ? C33B C34B 1.49(3) . ? C33B H67 0.9900 . ? C33B H68 0.9900 . ? C34B C35B 1.56(3) . ? C34B H69 0.9900 . ? C34B H70 0.9900 . ? C35B H71 0.9800 . ? C35B H72 0.9800 . ? C35B H73 0.9800 . ? C36 C37 1.519(5) . ? C36 H38 0.9900 . ? C36 H39 0.9900 . ? C37 C38 1.523(5) . ? C37 H40 0.9900 . ? C37 H41 0.9900 . ? C38 C39 1.509(5) . ? C38 H42 0.9900 . ? C38 H43 0.9900 . ? C39 H44 0.9800 . ? C39 H45 0.9800 . ? C39 H46 0.9800 . ? C40 C41 1.513(5) . ? C40 H47 0.9900 . ? C40 H48 0.9900 . ? C41 C42 1.506(5) . ? C41 H49 0.9900 . ? C41 H50 0.9900 . ? C42 C43 1.510(6) . ? C42 H51 0.9900 . ? C42 H52 0.9900 . ? C43 H53 0.9800 . ? C43 H54 0.9800 . ? C43 H55 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 109.5(3) . . ? N1 C1 H1 125.3 . . ? C2 C1 H1 125.3 . . ? C1 C2 C3 107.2(3) . . ? C1 C2 C20 127.1(3) . . ? C3 C2 C20 125.7(3) . . ? C4 C3 C2 107.0(3) . . ? C4 C3 C22 127.9(3) . . ? C2 C3 C22 125.1(3) . . ? N1 C4 C3 107.5(3) . . ? N1 C4 C5 120.6(3) . . ? C3 C4 C5 131.9(3) . . ? O1 C5 C6 119.7(3) . . ? O1 C5 C4 117.1(3) . . ? C6 C5 C4 123.2(3) . . ? C7 C6 C5 121.1(3) . . ? C7 C6 H2 119.5 . . ? C5 C6 H2 119.5 . . ? O2 C7 C6 120.2(3) . . ? O2 C7 C8 116.7(3) . . ? C6 C7 C8 123.1(3) . . ? N2 C8 C9 106.8(3) . . ? N2 C8 C7 121.4(3) . . ? C9 C8 C7 131.8(3) . . ? C10 C9 C8 108.2(3) . . ? C10 C9 C24 125.9(3) . . ? C8 C9 C24 125.9(3) . . ? C9 C10 C11 106.8(3) . . ? C9 C10 C26 126.9(3) . . ? C11 C10 C26 125.8(3) . . ? N2 C11 C10 108.0(3) . . ? N2 C11 C12 120.6(3) . . ? C10 C11 C12 131.3(3) . . ? C13 C12 C17 117.9(3) . . ? C13 C12 C11 120.3(3) . . ? C17 C12 C11 121.7(3) . . ? C14 C13 C12 121.0(3) . . ? C14 C13 H3 119.5 . . ? C12 C13 H3 119.5 . . ? C13 C14 C15 120.4(3) . . ? C13 C14 H4 119.8 . . ? C15 C14 H4 119.8 . . ? C14 C15 C16 118.9(3) . . ? C14 C15 C18 120.6(3) . . ? C16 C15 C18 120.5(3) . . ? C17 C16 C15 120.7(3) . . ? C17 C16 H5 119.7 . . ? C15 C16 H5 119.7 . . ? C16 C17 C12 121.0(3) . . ? C16 C17 H6 119.5 . . ? C12 C17 H6 119.5 . . ? C19 C18 C15 177.3(4) . . ? C18 C19 C19 179.2(5) . 2_457 ? C2 C20 C21 113.7(3) . . ? C2 C20 H7 108.8 . . ? C21 C20 H7 108.8 . . ? C2 C20 H8 108.8 . . ? C21 C20 H8 108.8 . . ? H7 C20 H8 107.7 . . ? C20 C21 H9 109.5 . . ? C20 C21 H10 109.5 . . ? H9 C21 H10 109.5 . . ? C20 C21 H11 109.5 . . ? H9 C21 H11 109.5 . . ? H10 C21 H11 109.5 . . ? C3 C22 C23 111.8(3) . . ? C3 C22 H12 109.3 . . ? C23 C22 H12 109.3 . . ? C3 C22 H13 109.3 . . ? C23 C22 H13 109.3 . . ? H12 C22 H13 107.9 . . ? C22 C23 H14 109.5 . . ? C22 C23 H15 109.5 . . ? H14 C23 H15 109.5 . . ? C22 C23 H16 109.5 . . ? H14 C23 H16 109.5 . . ? H15 C23 H16 109.5 . . ? C9 C24 C25 112.4(3) . . ? C9 C24 H17 109.1 . . ? C25 C24 H17 109.1 . . ? C9 C24 H18 109.1 . . ? C25 C24 H18 109.1 . . ? H17 C24 H18 107.9 . . ? C24 C25 H19 109.5 . . ? C24 C25 H20 109.5 . . ? H19 C25 H20 109.5 . . ? C24 C25 H21 109.5 . . ? H19 C25 H21 109.5 . . ? H20 C25 H21 109.5 . . ? C10 C26 C27 113.1(3) . . ? C10 C26 H22 109.0 . . ? C27 C26 H22 109.0 . . ? C10 C26 H23 109.0 . . ? C27 C26 H23 109.0 . . ? H22 C26 H23 107.8 . . ? C26 C27 H24 109.5 . . ? C26 C27 H25 109.5 . . ? H24 C27 H25 109.5 . . ? C26 C27 H26 109.5 . . ? H24 C27 H26 109.5 . . ? H25 C27 H26 109.5 . . ? C1 N1 C4 108.9(3) . . ? C1 N1 H27 125.6 . . ? C4 N1 H27 125.6 . . ? C11 N2 C8 110.2(3) . . ? C11 N2 H28 124.9 . . ? C8 N2 H28 124.9 . . ? C5 O1 B1 118.3(3) . . ? C7 O2 B1 118.6(3) . . ? F1 B1 F2 111.5(3) . . ? F1 B1 O2 109.3(3) . . ? F2 B1 O2 108.2(3) . . ? F1 B1 O1 108.6(3) . . ? F2 B1 O1 108.2(3) . . ? O2 B1 O1 111.1(3) . . ? C32 N3 C40 104.7(7) . . ? C32 N3 C28 116.0(8) . . ? C40 N3 C28 110.7(3) . . ? C32 N3 C36 108.3(7) . . ? C40 N3 C36 111.2(3) . . ? C28 N3 C36 106.0(2) . . ? C32 N3 C32B 12.5(14) . . ? C40 N3 C32B 110.6(9) . . ? C28 N3 C32B 103.5(9) . . ? C36 N3 C32B 114.4(10) . . ? N3 C28 C29 115.7(3) . . ? N3 C28 H29 108.4 . . ? C29 C28 H29 108.4 . . ? N3 C28 H30 108.4 . . ? C29 C28 H30 108.4 . . ? H29 C28 H30 107.4 . . ? C30 C29 C28 110.4(3) . . ? C30 C29 H31 109.6 . . ? C28 C29 H31 109.6 . . ? C30 C29 H32 109.6 . . ? C28 C29 H32 109.6 . . ? H31 C29 H32 108.1 . . ? C29 C30 C31 113.3(4) . . ? C29 C30 H33 108.9 . . ? C31 C30 H33 108.9 . . ? C29 C30 H34 108.9 . . ? C31 C30 H34 108.9 . . ? H33 C30 H34 107.7 . . ? C30 C31 H35 109.5 . . ? C30 C31 H36 109.5 . . ? H35 C31 H36 109.5 . . ? C30 C31 H37 109.5 . . ? H35 C31 H37 109.5 . . ? H36 C31 H37 109.5 . . ? N3 C32 C33 116.1(12) . . ? N3 C32 H56 108.3 . . ? C33 C32 H56 108.3 . . ? N3 C32 H57 108.3 . . ? C33 C32 H57 108.3 . . ? H56 C32 H57 107.4 . . ? C34 C33 C32 113.2(11) . . ? C34 C33 H58 108.9 . . ? C32 C33 H58 108.9 . . ? C34 C33 H59 108.9 . . ? C32 C33 H59 108.9 . . ? H58 C33 H59 107.8 . . ? C35 C34 C33 113.2(14) . . ? C35 C34 H60 108.9 . . ? C33 C34 H60 108.9 . . ? C35 C34 H61 108.9 . . ? C33 C34 H61 108.9 . . ? H60 C34 H61 107.7 . . ? C34 C35 H62 109.5 . . ? C34 C35 H63 109.5 . . ? H62 C35 H63 109.5 . . ? C34 C35 H64 109.5 . . ? H62 C35 H64 109.5 . . ? H63 C35 H64 109.5 . . ? C33B C32B N3 116.1(15) . . ? C33B C32B H65 108.3 . . ? N3 C32B H65 108.3 . . ? C33B C32B H66 108.3 . . ? N3 C32B H66 108.3 . . ? H65 C32B H66 107.4 . . ? C34B C33B C32B 111.0(13) . . ? C34B C33B H67 109.4 . . ? C32B C33B H67 109.4 . . ? C34B C33B H68 109.4 . . ? C32B C33B H68 109.4 . . ? H67 C33B H68 108.0 . . ? C33B C34B C35B 110.7(17) . . ? C33B C34B H69 109.5 . . ? C35B C34B H69 109.5 . . ? C33B C34B H70 109.5 . . ? C35B C34B H70 109.5 . . ? H69 C34B H70 108.1 . . ? C37 C36 N3 115.6(3) . . ? C37 C36 H38 108.4 . . ? N3 C36 H38 108.4 . . ? C37 C36 H39 108.4 . . ? N3 C36 H39 108.4 . . ? H38 C36 H39 107.4 . . ? C36 C37 C38 111.4(3) . . ? C36 C37 H40 109.3 . . ? C38 C37 H40 109.3 . . ? C36 C37 H41 109.3 . . ? C38 C37 H41 109.3 . . ? H40 C37 H41 108.0 . . ? C39 C38 C37 112.4(3) . . ? C39 C38 H42 109.1 . . ? C37 C38 H42 109.1 . . ? C39 C38 H43 109.1 . . ? C37 C38 H43 109.1 . . ? H42 C38 H43 107.9 . . ? C38 C39 H44 109.5 . . ? C38 C39 H45 109.5 . . ? H44 C39 H45 109.5 . . ? C38 C39 H46 109.5 . . ? H44 C39 H46 109.5 . . ? H45 C39 H46 109.5 . . ? N3 C40 C41 115.0(3) . . ? N3 C40 H47 108.5 . . ? C41 C40 H47 108.5 . . ? N3 C40 H48 108.5 . . ? C41 C40 H48 108.5 . . ? H47 C40 H48 107.5 . . ? C42 C41 C40 111.3(3) . . ? C42 C41 H49 109.4 . . ? C40 C41 H49 109.4 . . ? C42 C41 H50 109.4 . . ? C40 C41 H50 109.4 . . ? H49 C41 H50 108.0 . . ? C41 C42 C43 114.0(3) . . ? C41 C42 H51 108.7 . . ? C43 C42 H51 108.7 . . ? C41 C42 H52 108.7 . . ? C43 C42 H52 108.7 . . ? H51 C42 H52 107.6 . . ? C42 C43 H53 109.5 . . ? C42 C43 H54 109.5 . . ? H53 C43 H54 109.5 . . ? C42 C43 H55 109.5 . . ? H53 C43 H55 109.5 . . ? H54 C43 H55 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 0.0(4) . . . . ? N1 C1 C2 C20 179.1(3) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C20 C2 C3 C4 -179.4(3) . . . . ? C1 C2 C3 C22 -179.4(3) . . . . ? C20 C2 C3 C22 1.5(5) . . . . ? C2 C3 C4 N1 0.5(3) . . . . ? C22 C3 C4 N1 179.5(3) . . . . ? C2 C3 C4 C5 -177.7(3) . . . . ? C22 C3 C4 C5 1.3(6) . . . . ? N1 C4 C5 O1 176.6(3) . . . . ? C3 C4 C5 O1 -5.3(5) . . . . ? N1 C4 C5 C6 -1.2(5) . . . . ? C3 C4 C5 C6 176.9(3) . . . . ? O1 C5 C6 C7 -9.1(5) . . . . ? C4 C5 C6 C7 168.6(3) . . . . ? C5 C6 C7 O2 9.0(5) . . . . ? C5 C6 C7 C8 -170.4(3) . . . . ? O2 C7 C8 N2 -175.6(3) . . . . ? C6 C7 C8 N2 3.8(5) . . . . ? O2 C7 C8 C9 6.8(5) . . . . ? C6 C7 C8 C9 -173.8(3) . . . . ? N2 C8 C9 C10 -0.3(3) . . . . ? C7 C8 C9 C10 177.5(3) . . . . ? N2 C8 C9 C24 -178.7(3) . . . . ? C7 C8 C9 C24 -0.9(6) . . . . ? C8 C9 C10 C11 0.4(4) . . . . ? C24 C9 C10 C11 178.9(3) . . . . ? C8 C9 C10 C26 -171.5(3) . . . . ? C24 C9 C10 C26 6.9(6) . . . . ? C9 C10 C11 N2 -0.4(3) . . . . ? C26 C10 C11 N2 171.7(3) . . . . ? C9 C10 C11 C12 -178.8(3) . . . . ? C26 C10 C11 C12 -6.7(5) . . . . ? N2 C11 C12 C13 -36.1(4) . . . . ? C10 C11 C12 C13 142.1(3) . . . . ? N2 C11 C12 C17 141.9(3) . . . . ? C10 C11 C12 C17 -39.9(5) . . . . ? C17 C12 C13 C14 0.1(5) . . . . ? C11 C12 C13 C14 178.1(3) . . . . ? C12 C13 C14 C15 -1.8(5) . . . . ? C13 C14 C15 C16 2.4(5) . . . . ? C13 C14 C15 C18 -175.0(3) . . . . ? C14 C15 C16 C17 -1.2(5) . . . . ? C18 C15 C16 C17 176.1(3) . . . . ? C15 C16 C17 C12 -0.5(5) . . . . ? C13 C12 C17 C16 1.1(4) . . . . ? C11 C12 C17 C16 -176.9(3) . . . . ? C14 C15 C18 C19 75(8) . . . . ? C16 C15 C18 C19 -102(8) . . . . ? C15 C18 C19 C19 -33(44) . . . 2_457 ? C1 C2 C20 C21 -6.9(5) . . . . ? C3 C2 C20 C21 172.0(3) . . . . ? C4 C3 C22 C23 -84.3(4) . . . . ? C2 C3 C22 C23 94.6(4) . . . . ? C10 C9 C24 C25 -96.8(4) . . . . ? C8 C9 C24 C25 81.3(5) . . . . ? C9 C10 C26 C27 100.4(4) . . . . ? C11 C10 C26 C27 -70.2(4) . . . . ? C2 C1 N1 C4 0.3(4) . . . . ? C3 C4 N1 C1 -0.5(3) . . . . ? C5 C4 N1 C1 178.0(3) . . . . ? C10 C11 N2 C8 0.3(3) . . . . ? C12 C11 N2 C8 178.9(3) . . . . ? C9 C8 N2 C11 0.0(3) . . . . ? C7 C8 N2 C11 -178.1(3) . . . . ? C6 C5 O1 B1 -14.5(4) . . . . ? C4 C5 O1 B1 167.7(3) . . . . ? C6 C7 O2 B1 14.7(4) . . . . ? C8 C7 O2 B1 -165.8(3) . . . . ? C7 O2 B1 F1 -155.1(3) . . . . ? C7 O2 B1 F2 83.3(3) . . . . ? C7 O2 B1 O1 -35.3(4) . . . . ? C5 O1 B1 F1 155.3(3) . . . . ? C5 O1 B1 F2 -83.6(3) . . . . ? C5 O1 B1 O2 35.0(4) . . . . ? C32 N3 C28 C29 -66.1(9) . . . . ? C40 N3 C28 C29 53.0(4) . . . . ? C36 N3 C28 C29 173.7(3) . . . . ? C32B N3 C28 C29 -65.6(10) . . . . ? N3 C28 C29 C30 174.1(3) . . . . ? C28 C29 C30 C31 -73.1(4) . . . . ? C40 N3 C32 C33 170.8(10) . . . . ? C28 N3 C32 C33 -66.8(13) . . . . ? C36 N3 C32 C33 52.1(14) . . . . ? C32B N3 C32 C33 -69(7) . . . . ? N3 C32 C33 C34 173.1(11) . . . . ? C32 C33 C34 C35 175.1(13) . . . . ? C32 N3 C32B C33B 128(8) . . . . ? C40 N3 C32B C33B -168.1(13) . . . . ? C28 N3 C32B C33B -49.5(17) . . . . ? C36 N3 C32B C33B 65.3(17) . . . . ? N3 C32B C33B C34B -158.3(16) . . . . ? C32B C33B C34B C35B 76(2) . . . . ? C32 N3 C36 C37 59.7(8) . . . . ? C40 N3 C36 C37 -54.9(4) . . . . ? C28 N3 C36 C37 -175.3(3) . . . . ? C32B N3 C36 C37 71.4(10) . . . . ? N3 C36 C37 C38 -162.8(3) . . . . ? C36 C37 C38 C39 -176.5(3) . . . . ? C32 N3 C40 C41 -173.8(8) . . . . ? C28 N3 C40 C41 60.5(4) . . . . ? C36 N3 C40 C41 -57.0(4) . . . . ? C32B N3 C40 C41 174.7(9) . . . . ? N3 C40 C41 C42 -168.6(3) . . . . ? C40 C41 C42 C43 -177.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 0.308 _refine_diff_density_min -0.548 _refine_diff_density_rms 0.067 #============================================================================== # End of CIF #============================================================================== #============================================================================== # End of CIF #============================================================================== data_81202mae _database_code_depnum_ccdc_archive 'CCDC 819396' #TrackingRef '- BF2_ethynyl_HMaeda_CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C54 H56 B2 F4 N4 O4, 2(C3 H6 O)' _chemical_formula_sum 'C60 H68 B2 Cl0 F4 N4 O6' _chemical_formula_weight 1038.80 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' F F 0.0171 0.0103 '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 b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 14.226(2) _cell_length_b 19.130(3) _cell_length_c 19.557(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5322.4(16) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 30131 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2200 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9729 _exptl_absorpt_correction_T_max 0.9818 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _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 46570 _diffrn_reflns_av_R_equivalents 0.0957 _diffrn_reflns_av_sigmaI/netI 0.0540 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6093 _reflns_number_gt 4027 _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^)+(0.0558P)^2^+1.4978P] 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 6093 _refine_ls_number_parameters 349 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0871 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1290 _refine_ls_wR_factor_gt 0.1131 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.62517(12) 0.29300(10) 0.61568(10) 0.0248(4) Uani 1 1 d . . . H1 H 0.6768 0.2654 0.6009 0.030 Uiso 1 1 calc R . . C2 C 0.62750(12) 0.34159(10) 0.66781(10) 0.0240(4) Uani 1 1 d . . . C3 C 0.53673(12) 0.37121(10) 0.67279(9) 0.0210(4) Uani 1 1 d . . . C4 C 0.48151(12) 0.33898(9) 0.62262(9) 0.0201(4) Uani 1 1 d . . . C5 C 0.38515(12) 0.34319(9) 0.60296(9) 0.0202(4) Uani 1 1 d . . . C6 C 0.32467(12) 0.39812(10) 0.61734(10) 0.0219(4) Uani 1 1 d . . . H2 H 0.3470 0.4377 0.6418 0.026 Uiso 1 1 calc R . . C7 C 0.23168(12) 0.39548(9) 0.59604(9) 0.0204(4) Uani 1 1 d . . . C8 C 0.16260(12) 0.44870(9) 0.60580(9) 0.0198(4) Uani 1 1 d . . . C9 C 0.16762(12) 0.52011(10) 0.62255(9) 0.0213(4) Uani 1 1 d . . . C10 C 0.07616(12) 0.54774(10) 0.61520(9) 0.0211(4) Uani 1 1 d . . . C11 C 0.01652(12) 0.49270(9) 0.59657(9) 0.0197(4) Uani 1 1 d . . . C12 C -0.08516(12) 0.49007(9) 0.58345(9) 0.0200(4) Uani 1 1 d . . . C13 C -0.14443(13) 0.54545(10) 0.60164(11) 0.0273(4) Uani 1 1 d . . . H3 H -0.1193 0.5842 0.6259 0.033 Uiso 1 1 calc R . . C14 C -0.23856(13) 0.54469(10) 0.58495(10) 0.0270(4) Uani 1 1 d . . . H4 H -0.2771 0.5834 0.5968 0.032 Uiso 1 1 calc R . . C15 C -0.27792(12) 0.48786(10) 0.55092(10) 0.0231(4) Uani 1 1 d . . . C16 C -0.22127(13) 0.43038(10) 0.53656(10) 0.0260(4) Uani 1 1 d . . . H5 H -0.2478 0.3900 0.5160 0.031 Uiso 1 1 calc R . . C17 C -0.12658(13) 0.43190(10) 0.55214(10) 0.0241(4) Uani 1 1 d . . . H6 H -0.0887 0.3925 0.5413 0.029 Uiso 1 1 calc R . . C18 C -0.37422(13) 0.49036(10) 0.52955(10) 0.0247(4) Uani 1 1 d . . . C19 C -0.45424(13) 0.49638(10) 0.51047(10) 0.0245(4) Uani 1 1 d . . . C20 C 0.71204(13) 0.35934(12) 0.71061(11) 0.0323(5) Uani 1 1 d . . . H7 H 0.6911 0.3693 0.7579 0.039 Uiso 1 1 calc R . . H8 H 0.7414 0.4024 0.6923 0.039 Uiso 1 1 calc R . . C21 C 0.78501(17) 0.30207(15) 0.71258(16) 0.0579(8) Uani 1 1 d . . . H9 H 0.7565 0.2590 0.7301 0.087 Uiso 1 1 calc R . . H10 H 0.8369 0.3162 0.7426 0.087 Uiso 1 1 calc R . . H11 H 0.8091 0.2938 0.6663 0.087 Uiso 1 1 calc R . . C22 C 0.50787(13) 0.42676(10) 0.72246(10) 0.0245(4) Uani 1 1 d . . . H12 H 0.5440 0.4208 0.7654 0.029 Uiso 1 1 calc R . . H13 H 0.4404 0.4209 0.7334 0.029 Uiso 1 1 calc R . . C23 C 0.52392(15) 0.50029(10) 0.69501(11) 0.0337(5) Uani 1 1 d . . . H14 H 0.5904 0.5062 0.6833 0.051 Uiso 1 1 calc R . . H15 H 0.5063 0.5346 0.7300 0.051 Uiso 1 1 calc R . . H16 H 0.4854 0.5075 0.6541 0.051 Uiso 1 1 calc R . . C24 C 0.25377(13) 0.56147(10) 0.64081(10) 0.0251(4) Uani 1 1 d . . . H17 H 0.2441 0.6108 0.6271 0.030 Uiso 1 1 calc R . . H18 H 0.3079 0.5431 0.6146 0.030 Uiso 1 1 calc R . . C25 C 0.27731(15) 0.55899(11) 0.71704(11) 0.0337(5) Uani 1 1 d . . . H19 H 0.2240 0.5770 0.7434 0.050 Uiso 1 1 calc R . . H20 H 0.3329 0.5878 0.7260 0.050 Uiso 1 1 calc R . . H21 H 0.2901 0.5106 0.7306 0.050 Uiso 1 1 calc R . . C26 C 0.05477(13) 0.62500(10) 0.61685(10) 0.0237(4) Uani 1 1 d . . . H22 H -0.0010 0.6338 0.5878 0.028 Uiso 1 1 calc R . . H23 H 0.1084 0.6503 0.5961 0.028 Uiso 1 1 calc R . . C27 C 0.03621(15) 0.65570(10) 0.68725(10) 0.0314(5) Uani 1 1 d . . . H24 H -0.0220 0.6359 0.7058 0.047 Uiso 1 1 calc R . . H25 H 0.0299 0.7066 0.6836 0.047 Uiso 1 1 calc R . . H26 H 0.0887 0.6444 0.7177 0.047 Uiso 1 1 calc R . . N1 N 0.53792(10) 0.29099(8) 0.58921(8) 0.0232(3) Uani 1 1 d . . . H27 H 0.5196 0.2634 0.5558 0.028 Uiso 1 1 calc R . . N2 N 0.07033(10) 0.43411(8) 0.58951(8) 0.0200(3) Uani 1 1 d . . . H28 H 0.0492 0.3930 0.5765 0.024 Uiso 1 1 calc R . . O1 O 0.35629(9) 0.28884(7) 0.56739(8) 0.0303(3) Uani 1 1 d . . . O2 O 0.19982(9) 0.33969(7) 0.56396(8) 0.0317(3) Uani 1 1 d . . . B1 B 0.26286(15) 0.28587(11) 0.53611(13) 0.0278(5) Uani 1 1 d . . . F1 F 0.27331(8) 0.29641(7) 0.46624(6) 0.0381(3) Uani 1 1 d . . . F2 F 0.22370(8) 0.22136(6) 0.54841(7) 0.0371(3) Uani 1 1 d . . . C28 C 0.50286(17) 0.33555(11) 0.41908(13) 0.0407(6) Uani 1 1 d . . . H29 H 0.4570 0.3425 0.4559 0.061 Uiso 1 1 calc R . . H30 H 0.4801 0.3581 0.3772 0.061 Uiso 1 1 calc R . . H31 H 0.5632 0.3562 0.4324 0.061 Uiso 1 1 calc R . . C29 C 0.51550(13) 0.25943(10) 0.40659(11) 0.0269(4) Uani 1 1 d . . . C30 C 0.5435(2) 0.23850(13) 0.33601(12) 0.0535(7) Uani 1 1 d . . . H32 H 0.5460 0.1874 0.3330 0.080 Uiso 1 1 calc R . . H33 H 0.6055 0.2580 0.3255 0.080 Uiso 1 1 calc R . . H34 H 0.4973 0.2564 0.3032 0.080 Uiso 1 1 calc R . . O3 O 0.50583(9) 0.21615(7) 0.45223(7) 0.0286(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 0.0177(9) 0.0289(10) 0.0279(10) -0.0020(8) 0.0001(8) 0.0022(8) C2 0.0190(8) 0.0284(10) 0.0245(10) -0.0004(8) -0.0012(7) -0.0009(8) C3 0.0210(8) 0.0226(9) 0.0193(9) 0.0024(7) 0.0003(7) -0.0014(8) C4 0.0204(9) 0.0187(9) 0.0212(9) -0.0003(7) 0.0022(7) 0.0025(7) C5 0.0223(9) 0.0196(9) 0.0188(9) -0.0017(7) 0.0007(7) -0.0008(8) C6 0.0224(9) 0.0199(9) 0.0234(10) -0.0027(8) -0.0009(8) -0.0008(8) C7 0.0221(9) 0.0188(9) 0.0204(9) 0.0010(7) 0.0005(7) -0.0007(8) C8 0.0185(8) 0.0204(9) 0.0206(9) 0.0013(7) 0.0001(7) 0.0009(7) C9 0.0228(9) 0.0210(9) 0.0200(9) 0.0018(7) 0.0020(7) 0.0000(8) C10 0.0224(9) 0.0210(9) 0.0198(9) -0.0001(8) 0.0003(7) 0.0008(7) C11 0.0222(9) 0.0199(9) 0.0171(9) 0.0020(7) 0.0006(7) 0.0031(7) C12 0.0214(8) 0.0209(9) 0.0175(9) 0.0015(7) 0.0017(7) 0.0021(8) C13 0.0246(9) 0.0229(10) 0.0343(11) -0.0070(9) -0.0009(8) 0.0008(8) C14 0.0233(9) 0.0233(10) 0.0345(11) -0.0026(9) 0.0011(8) 0.0036(8) C15 0.0198(8) 0.0277(10) 0.0218(10) 0.0047(8) 0.0006(7) 0.0020(8) C16 0.0244(9) 0.0258(10) 0.0277(10) -0.0039(8) -0.0014(8) -0.0004(8) C17 0.0234(9) 0.0214(9) 0.0275(10) -0.0008(8) -0.0001(8) 0.0047(8) C18 0.0254(9) 0.0257(10) 0.0232(10) -0.0019(8) 0.0009(8) 0.0014(8) C19 0.0240(9) 0.0252(10) 0.0243(10) -0.0022(8) 0.0003(8) 0.0026(8) C20 0.0237(9) 0.0417(12) 0.0314(11) -0.0072(10) -0.0048(8) 0.0020(9) C21 0.0367(13) 0.0647(18) 0.072(2) -0.0230(15) -0.0264(13) 0.0163(13) C22 0.0241(9) 0.0270(10) 0.0223(10) -0.0048(8) -0.0003(8) 0.0009(8) C23 0.0373(11) 0.0262(11) 0.0375(12) -0.0079(9) -0.0004(9) 0.0001(9) C24 0.0230(9) 0.0212(9) 0.0311(11) -0.0020(8) -0.0004(8) -0.0010(8) C25 0.0300(10) 0.0353(12) 0.0356(12) -0.0070(10) -0.0054(9) -0.0025(9) C26 0.0236(9) 0.0194(9) 0.0282(10) 0.0009(8) 0.0009(8) 0.0016(8) C27 0.0422(11) 0.0212(10) 0.0306(11) 0.0003(8) -0.0022(9) 0.0040(9) N1 0.0210(7) 0.0242(8) 0.0244(8) -0.0062(7) -0.0018(7) 0.0010(7) N2 0.0188(7) 0.0185(8) 0.0226(8) -0.0017(6) -0.0016(6) -0.0004(6) O1 0.0241(7) 0.0255(7) 0.0413(9) -0.0134(6) -0.0088(6) 0.0067(6) O2 0.0222(7) 0.0241(7) 0.0487(9) -0.0136(7) -0.0082(6) 0.0024(6) B1 0.0226(11) 0.0209(11) 0.0400(14) -0.0084(10) -0.0094(10) 0.0018(9) F1 0.0346(6) 0.0428(7) 0.0371(7) -0.0040(6) -0.0076(5) -0.0008(6) F2 0.0295(6) 0.0224(6) 0.0593(9) -0.0050(6) -0.0016(6) 0.0011(5) C28 0.0528(14) 0.0239(11) 0.0452(14) 0.0035(10) 0.0055(11) 0.0027(10) C29 0.0228(9) 0.0251(10) 0.0329(11) 0.0011(9) -0.0038(8) 0.0016(8) C30 0.091(2) 0.0403(14) 0.0291(13) 0.0023(11) -0.0054(13) 0.0134(14) O3 0.0260(7) 0.0253(7) 0.0347(8) 0.0021(6) 0.0024(6) -0.0002(6) _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 1.345(2) . ? C1 C2 1.380(3) . ? C1 H1 0.9500 . ? C2 C3 1.413(2) . ? C2 C20 1.504(3) . ? C3 C4 1.400(2) . ? C3 C22 1.497(3) . ? C4 N1 1.383(2) . ? C4 C5 1.426(2) . ? C5 O1 1.317(2) . ? C5 C6 1.387(3) . ? C6 C7 1.388(2) . ? C6 H2 0.9500 . ? C7 O2 1.318(2) . ? C7 C8 1.428(2) . ? C8 N2 1.379(2) . ? C8 C9 1.407(3) . ? C9 C10 1.412(2) . ? C9 C24 1.502(3) . ? C10 C11 1.401(3) . ? C10 C26 1.509(3) . ? C11 N2 1.364(2) . ? C11 C12 1.470(2) . ? C12 C13 1.400(3) . ? C12 C17 1.400(3) . ? C13 C14 1.378(3) . ? C13 H3 0.9500 . ? C14 C15 1.392(3) . ? C14 H4 0.9500 . ? C15 C16 1.392(3) . ? C15 C18 1.433(3) . ? C16 C17 1.381(3) . ? C16 H5 0.9500 . ? C17 H6 0.9500 . ? C18 C19 1.203(3) . ? C19 C19 1.372(4) 5_466 ? C20 C21 1.510(3) . ? C20 H7 0.9900 . ? C20 H8 0.9900 . ? C21 H9 0.9800 . ? C21 H10 0.9800 . ? C21 H11 0.9800 . ? C22 C23 1.523(3) . ? C22 H12 0.9900 . ? C22 H13 0.9900 . ? C23 H14 0.9800 . ? C23 H15 0.9800 . ? C23 H16 0.9800 . ? C24 C25 1.529(3) . ? C24 H17 0.9900 . ? C24 H18 0.9900 . ? C25 H19 0.9800 . ? C25 H20 0.9800 . ? C25 H21 0.9800 . ? C26 C27 1.520(3) . ? C26 H22 0.9900 . ? C26 H23 0.9900 . ? C27 H24 0.9800 . ? C27 H25 0.9800 . ? C27 H26 0.9800 . ? N1 H27 0.8800 . ? N2 H28 0.8800 . ? O1 B1 1.464(2) . ? O2 B1 1.470(3) . ? B1 F2 1.375(3) . ? B1 F1 1.389(3) . ? C28 C29 1.487(3) . ? C28 H29 0.9800 . ? C28 H30 0.9800 . ? C28 H31 0.9800 . ? C29 O3 1.225(2) . ? C29 C30 1.492(3) . ? C30 H32 0.9800 . ? C30 H33 0.9800 . ? C30 H34 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 109.00(16) . . ? N1 C1 H1 125.5 . . ? C2 C1 H1 125.5 . . ? C1 C2 C3 107.40(16) . . ? C1 C2 C20 125.62(17) . . ? C3 C2 C20 126.98(17) . . ? C4 C3 C2 106.72(16) . . ? C4 C3 C22 127.84(16) . . ? C2 C3 C22 125.44(16) . . ? N1 C4 C3 107.33(15) . . ? N1 C4 C5 117.89(16) . . ? C3 C4 C5 134.70(17) . . ? O1 C5 C6 120.79(16) . . ? O1 C5 C4 113.43(15) . . ? C6 C5 C4 125.77(16) . . ? C5 C6 C7 120.19(17) . . ? C5 C6 H2 119.9 . . ? C7 C6 H2 119.9 . . ? O2 C7 C6 120.00(16) . . ? O2 C7 C8 113.85(15) . . ? C6 C7 C8 126.15(17) . . ? N2 C8 C9 107.38(15) . . ? N2 C8 C7 118.67(16) . . ? C9 C8 C7 133.53(17) . . ? C8 C9 C10 107.05(16) . . ? C8 C9 C24 127.48(16) . . ? C10 C9 C24 125.38(17) . . ? C11 C10 C9 107.65(16) . . ? C11 C10 C26 128.29(16) . . ? C9 C10 C26 123.39(16) . . ? N2 C11 C10 107.70(15) . . ? N2 C11 C12 120.43(16) . . ? C10 C11 C12 131.85(16) . . ? C13 C12 C17 117.33(16) . . ? C13 C12 C11 121.50(17) . . ? C17 C12 C11 121.17(16) . . ? C14 C13 C12 121.12(18) . . ? C14 C13 H3 119.4 . . ? C12 C13 H3 119.4 . . ? C13 C14 C15 120.81(18) . . ? C13 C14 H4 119.6 . . ? C15 C14 H4 119.6 . . ? C16 C15 C14 118.72(16) . . ? C16 C15 C18 121.39(17) . . ? C14 C15 C18 119.86(17) . . ? C17 C16 C15 120.22(18) . . ? C17 C16 H5 119.9 . . ? C15 C16 H5 119.9 . . ? C16 C17 C12 121.57(17) . . ? C16 C17 H6 119.2 . . ? C12 C17 H6 119.2 . . ? C19 C18 C15 176.2(2) . . ? C18 C19 C19 179.3(3) . 5_466 ? C2 C20 C21 113.58(18) . . ? C2 C20 H7 108.8 . . ? C21 C20 H7 108.8 . . ? C2 C20 H8 108.8 . . ? C21 C20 H8 108.8 . . ? H7 C20 H8 107.7 . . ? C20 C21 H9 109.5 . . ? C20 C21 H10 109.5 . . ? H9 C21 H10 109.5 . . ? C20 C21 H11 109.5 . . ? H9 C21 H11 109.5 . . ? H10 C21 H11 109.5 . . ? C3 C22 C23 112.69(16) . . ? C3 C22 H12 109.1 . . ? C23 C22 H12 109.1 . . ? C3 C22 H13 109.1 . . ? C23 C22 H13 109.1 . . ? H12 C22 H13 107.8 . . ? C22 C23 H14 109.5 . . ? C22 C23 H15 109.5 . . ? H14 C23 H15 109.5 . . ? C22 C23 H16 109.5 . . ? H14 C23 H16 109.5 . . ? H15 C23 H16 109.5 . . ? C9 C24 C25 113.22(16) . . ? C9 C24 H17 108.9 . . ? C25 C24 H17 108.9 . . ? C9 C24 H18 108.9 . . ? C25 C24 H18 108.9 . . ? H17 C24 H18 107.7 . . ? C24 C25 H19 109.5 . . ? C24 C25 H20 109.5 . . ? H19 C25 H20 109.5 . . ? C24 C25 H21 109.5 . . ? H19 C25 H21 109.5 . . ? H20 C25 H21 109.5 . . ? C10 C26 C27 115.64(16) . . ? C10 C26 H22 108.4 . . ? C27 C26 H22 108.4 . . ? C10 C26 H23 108.4 . . ? C27 C26 H23 108.4 . . ? H22 C26 H23 107.4 . . ? C26 C27 H24 109.5 . . ? C26 C27 H25 109.5 . . ? H24 C27 H25 109.5 . . ? C26 C27 H26 109.5 . . ? H24 C27 H26 109.5 . . ? H25 C27 H26 109.5 . . ? C1 N1 C4 109.54(16) . . ? C1 N1 H27 125.2 . . ? C4 N1 H27 125.2 . . ? C11 N2 C8 110.15(15) . . ? C11 N2 H28 124.9 . . ? C8 N2 H28 124.9 . . ? C5 O1 B1 122.32(15) . . ? C7 O2 B1 122.25(14) . . ? F2 B1 F1 110.23(17) . . ? F2 B1 O1 109.24(17) . . ? F1 B1 O1 107.94(17) . . ? F2 B1 O2 108.45(17) . . ? F1 B1 O2 109.15(17) . . ? O1 B1 O2 111.82(16) . . ? C29 C28 H29 109.5 . . ? C29 C28 H30 109.5 . . ? H29 C28 H30 109.5 . . ? C29 C28 H31 109.5 . . ? H29 C28 H31 109.5 . . ? H30 C28 H31 109.5 . . ? O3 C29 C28 121.90(19) . . ? O3 C29 C30 121.52(19) . . ? C28 C29 C30 116.55(19) . . ? C29 C30 H32 109.5 . . ? C29 C30 H33 109.5 . . ? H32 C30 H33 109.5 . . ? C29 C30 H34 109.5 . . ? H32 C30 H34 109.5 . . ? H33 C30 H34 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 -0.6(2) . . . . ? N1 C1 C2 C20 179.74(19) . . . . ? C1 C2 C3 C4 0.0(2) . . . . ? C20 C2 C3 C4 179.66(19) . . . . ? C1 C2 C3 C22 -179.55(18) . . . . ? C20 C2 C3 C22 0.1(3) . . . . ? C2 C3 C4 N1 0.6(2) . . . . ? C22 C3 C4 N1 -179.90(17) . . . . ? C2 C3 C4 C5 177.2(2) . . . . ? C22 C3 C4 C5 -3.3(3) . . . . ? N1 C4 C5 O1 16.2(2) . . . . ? C3 C4 C5 O1 -160.2(2) . . . . ? N1 C4 C5 C6 -162.79(18) . . . . ? C3 C4 C5 C6 20.9(3) . . . . ? O1 C5 C6 C7 2.0(3) . . . . ? C4 C5 C6 C7 -179.12(18) . . . . ? C5 C6 C7 O2 2.2(3) . . . . ? C5 C6 C7 C8 -178.39(18) . . . . ? O2 C7 C8 N2 7.9(2) . . . . ? C6 C7 C8 N2 -171.57(18) . . . . ? O2 C7 C8 C9 -163.6(2) . . . . ? C6 C7 C8 C9 17.0(3) . . . . ? N2 C8 C9 C10 -0.5(2) . . . . ? C7 C8 C9 C10 171.6(2) . . . . ? N2 C8 C9 C24 -177.14(17) . . . . ? C7 C8 C9 C24 -5.0(3) . . . . ? C8 C9 C10 C11 2.0(2) . . . . ? C24 C9 C10 C11 178.75(17) . . . . ? C8 C9 C10 C26 -169.31(17) . . . . ? C24 C9 C10 C26 7.4(3) . . . . ? C9 C10 C11 N2 -2.8(2) . . . . ? C26 C10 C11 N2 167.99(17) . . . . ? C9 C10 C11 C12 178.65(18) . . . . ? C26 C10 C11 C12 -10.6(3) . . . . ? N2 C11 C12 C13 168.61(17) . . . . ? C10 C11 C12 C13 -13.0(3) . . . . ? N2 C11 C12 C17 -11.4(3) . . . . ? C10 C11 C12 C17 166.98(19) . . . . ? C17 C12 C13 C14 -4.5(3) . . . . ? C11 C12 C13 C14 175.47(18) . . . . ? C12 C13 C14 C15 1.6(3) . . . . ? C13 C14 C15 C16 2.7(3) . . . . ? C13 C14 C15 C18 -175.35(19) . . . . ? C14 C15 C16 C17 -4.0(3) . . . . ? C18 C15 C16 C17 174.04(18) . . . . ? C15 C16 C17 C12 1.0(3) . . . . ? C13 C12 C17 C16 3.2(3) . . . . ? C11 C12 C17 C16 -176.77(18) . . . . ? C16 C15 C18 C19 -137(3) . . . . ? C14 C15 C18 C19 41(3) . . . . ? C15 C18 C19 C19 -84(26) . . . 5_466 ? C1 C2 C20 C21 -22.9(3) . . . . ? C3 C2 C20 C21 157.5(2) . . . . ? C4 C3 C22 C23 -90.6(2) . . . . ? C2 C3 C22 C23 88.9(2) . . . . ? C8 C9 C24 C25 -87.5(2) . . . . ? C10 C9 C24 C25 96.5(2) . . . . ? C11 C10 C26 C27 102.5(2) . . . . ? C9 C10 C26 C27 -88.1(2) . . . . ? C2 C1 N1 C4 1.0(2) . . . . ? C3 C4 N1 C1 -0.9(2) . . . . ? C5 C4 N1 C1 -178.24(16) . . . . ? C10 C11 N2 C8 2.5(2) . . . . ? C12 C11 N2 C8 -178.72(16) . . . . ? C9 C8 N2 C11 -1.2(2) . . . . ? C7 C8 N2 C11 -174.76(16) . . . . ? C6 C5 O1 B1 5.5(3) . . . . ? C4 C5 O1 B1 -173.51(18) . . . . ? C6 C7 O2 B1 -13.7(3) . . . . ? C8 C7 O2 B1 166.80(18) . . . . ? C5 O1 B1 F2 -135.21(18) . . . . ? C5 O1 B1 F1 104.9(2) . . . . ? C5 O1 B1 O2 -15.2(3) . . . . ? C7 O2 B1 F2 139.88(18) . . . . ? C7 O2 B1 F1 -100.0(2) . . . . ? C7 O2 B1 O1 19.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.268 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.050