# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_compound1 _database_code_depnum_ccdc_archive 'CCDC 899844' #TrackingRef '13688_web_deposit_cif_file_0_AtsushiWakamiya_1346680845.compound1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H40 B Cl2 F5 N2' _chemical_formula_weight 749.47 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' 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 monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 12.5255(4) _cell_length_b 10.3779(3) _cell_length_c 29.0756(10) _cell_angle_alpha 90.00 _cell_angle_beta 95.2682(14) _cell_angle_gamma 90.00 _cell_volume 3763.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 6629 _cell_measurement_theta_min 2.0549 _cell_measurement_theta_max 30.9975 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1560 _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9554 _exptl_absorpt_correction_T_max 0.9663 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn70 CCD (4x4 bin mode) with MicroMax-007 ; _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30783 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6618 _reflns_number_gt 5925 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 for windows' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[?^2^(Fo^2^)+(0.0708P)^2^+4.5531P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef none _refine_ls_number_reflns 6618 _refine_ls_number_parameters 511 _refine_ls_number_restraints 146 _refine_ls_R_factor_all 0.0757 _refine_ls_R_factor_gt 0.0675 _refine_ls_wR_factor_ref 0.1687 _refine_ls_wR_factor_gt 0.1628 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.181 _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 N1 N -0.00444(17) -0.1993(2) 0.16548(7) 0.0206(5) Uani 1 1 d . . . C1 C -0.0814(2) -0.2421(3) 0.13364(9) 0.0222(6) Uani 1 1 d . . . C2 C -0.1126(2) -0.3685(3) 0.14607(9) 0.0262(6) Uani 1 1 d . . . H13 H -0.1647 -0.4210 0.1293 0.031 Uiso 1 1 calc R . . C3 C -0.0545(2) -0.4005(3) 0.18626(9) 0.0243(6) Uani 1 1 d . . . H14 H -0.0593 -0.4789 0.2028 0.029 Uiso 1 1 calc R . . C4 C 0.0150(2) -0.2953(3) 0.19903(9) 0.0199(5) Uani 1 1 d . . . C5 C 0.0927(2) -0.2804(3) 0.23583(9) 0.0198(5) Uani 1 1 d . . . C6 C 0.1568(2) -0.1671(3) 0.23995(9) 0.0219(6) Uani 1 1 d . . . N2 N 0.13385(17) -0.0661(2) 0.20924(8) 0.0220(5) Uani 1 1 d . . . C7 C 0.2451(2) -0.1342(3) 0.27182(9) 0.0221(6) Uani 1 1 d . . . C8 C 0.2728(2) -0.0054(3) 0.26073(9) 0.0238(6) Uani 1 1 d . . . C9 C 0.2042(2) 0.0323(3) 0.22169(9) 0.0244(6) Uani 1 1 d . . . C10 C 0.2156(2) 0.1523(3) 0.20030(10) 0.0284(6) Uani 1 1 d . . . H15 H 0.1690 0.1780 0.1743 0.034 Uiso 1 1 calc R . . C11 C 0.2973(2) 0.2311(3) 0.21857(11) 0.0327(7) Uani 1 1 d . . . H16 H 0.3075 0.3122 0.2045 0.039 Uiso 1 1 calc R . . C12 C 0.3662(2) 0.1952(3) 0.25758(11) 0.0321(7) Uani 1 1 d . . . H17 H 0.4212 0.2526 0.2692 0.039 Uiso 1 1 calc R . . C13 C 0.3551(2) 0.0789(3) 0.27897(10) 0.0278(6) Uani 1 1 d . . . H18 H 0.4014 0.0554 0.3054 0.033 Uiso 1 1 calc R . . B1 B 0.0434(2) -0.0604(3) 0.17025(11) 0.0244(7) Uani 1 1 d . . . F1 F -0.03736(13) 0.02368(16) 0.18192(6) 0.0362(4) Uani 1 1 d . . . F2 F 0.08124(14) -0.02111(17) 0.12942(5) 0.0341(4) Uani 1 1 d . . . C14 C -0.1251(2) -0.1658(3) 0.09316(9) 0.0221(6) Uani 1 1 d . . . C15 C -0.0743(2) -0.1674(3) 0.05235(9) 0.0242(6) Uani 1 1 d . . . C16 C -0.1190(2) -0.0957(3) 0.01479(9) 0.0277(6) Uani 1 1 d . . . H19 H -0.0844 -0.0952 -0.0129 0.033 Uiso 1 1 calc R . . C17 C -0.2126(2) -0.0252(3) 0.01674(10) 0.0279(6) Uani 1 1 d . . . C18 C -0.2629(2) -0.0287(3) 0.05725(10) 0.0264(6) Uani 1 1 d . . . H20 H -0.3282 0.0171 0.0586 0.032 Uiso 1 1 calc R . . C19 C -0.2209(2) -0.0973(3) 0.09599(9) 0.0238(6) Uani 1 1 d . . . C20 C 0.0248(2) -0.2470(3) 0.04870(11) 0.0351(7) Uani 1 1 d . . . H1 H 0.0828 -0.2148 0.0706 0.053 Uiso 1 1 calc R . . H2 H 0.0465 -0.2411 0.0172 0.053 Uiso 1 1 calc R . . H3 H 0.0097 -0.3371 0.0559 0.053 Uiso 1 1 calc R . . C21 C -0.2594(3) 0.0551(3) -0.02341(11) 0.0403(8) Uani 1 1 d . . . H4 H -0.2175 0.0420 -0.0499 0.060 Uiso 1 1 calc R . . H5 H -0.2572 0.1463 -0.0147 0.060 Uiso 1 1 calc R . . H6 H -0.3338 0.0291 -0.0318 0.060 Uiso 1 1 calc R . . C22 C -0.2766(2) -0.0972(3) 0.13961(10) 0.0342(7) Uani 1 1 d . . . H7 H -0.2937 -0.1859 0.1478 0.051 Uiso 1 1 calc R . . H8 H -0.3430 -0.0470 0.1348 0.051 Uiso 1 1 calc R . . H9 H -0.2296 -0.0585 0.1647 0.051 Uiso 1 1 calc R . . C23 C 0.1054(2) -0.3830(3) 0.27144(9) 0.0216(6) Uani 1 1 d . . . C24 C 0.1297(2) -0.5095(3) 0.25992(9) 0.0250(6) Uani 1 1 d . . . H21 H 0.1366 -0.5314 0.2286 0.030 Uiso 1 1 calc R . . C25 C 0.1440(2) -0.6032(3) 0.29377(10) 0.0293(6) Uani 1 1 d . . . H22 H 0.1611 -0.6890 0.2858 0.035 Uiso 1 1 calc R . . C26 C 0.1332(2) -0.5710(3) 0.33940(10) 0.0303(7) Uani 1 1 d . A . C27 C 0.1067(2) -0.4463(3) 0.35131(10) 0.0293(7) Uani 1 1 d . . . H23 H 0.0980 -0.4254 0.3826 0.035 Uiso 1 1 calc R . . C28 C 0.0931(2) -0.3526(3) 0.31740(9) 0.0243(6) Uani 1 1 d . . . H24 H 0.0753 -0.2671 0.3255 0.029 Uiso 1 1 calc R . . C29 C 0.1481(3) -0.6711(4) 0.37553(12) 0.0507(9) Uani 1 1 d DU . . F3A F 0.0514(5) -0.7313(7) 0.3801(3) 0.093(2) Uani 0.585(8) 1 d PDU A 1 F4A F 0.2044(8) -0.7729(6) 0.3641(2) 0.089(2) Uani 0.585(8) 1 d PDU A 1 F5A F 0.1841(8) -0.6330(7) 0.4157(2) 0.089(2) Uani 0.585(8) 1 d PU A 1 C30 C 0.3050(2) -0.2144(3) 0.30722(9) 0.0217(6) Uani 1 1 d . . . C31 C 0.3481(2) -0.3332(3) 0.29644(9) 0.0237(6) Uani 1 1 d . . . H25 H 0.3420 -0.3623 0.2653 0.028 Uiso 1 1 calc R . . C32 C 0.4002(2) -0.4093(3) 0.33091(10) 0.0264(6) Uani 1 1 d . . . H26 H 0.4284 -0.4905 0.3231 0.032 Uiso 1 1 calc R . . C33 C 0.4116(2) -0.3686(3) 0.37670(9) 0.0263(6) Uani 1 1 d . . . C34 C 0.3722(2) -0.2476(3) 0.38679(10) 0.0287(6) Uani 1 1 d . . . H27 H 0.3813 -0.2166 0.4176 0.034 Uiso 1 1 calc R . . C35 C 0.3199(2) -0.1716(3) 0.35276(9) 0.0267(6) Uani 1 1 d . . . H28 H 0.2939 -0.0892 0.3605 0.032 Uiso 1 1 calc R . . C36 C 0.4665(2) -0.4524(3) 0.41430(10) 0.0320(7) Uani 1 1 d . . . H29 H 0.4414 -0.5422 0.4094 0.038 Uiso 1 1 calc R . . H30 H 0.4441 -0.4235 0.4444 0.038 Uiso 1 1 calc R . . C37 C 0.5884(2) -0.4512(3) 0.41683(10) 0.0276(6) Uani 1 1 d . . . H31 H 0.6142 -0.3611 0.4195 0.033 Uiso 1 1 calc R . . H32 H 0.6119 -0.4878 0.3880 0.033 Uiso 1 1 calc R . . C38 C 0.6381(2) -0.5286(3) 0.45791(10) 0.0300(7) Uani 1 1 d . . . H33 H 0.6200 -0.4858 0.4866 0.036 Uiso 1 1 calc R . . H34 H 0.6047 -0.6151 0.4570 0.036 Uiso 1 1 calc R . . C39 C 0.7588(2) -0.5451(3) 0.46039(11) 0.0342(7) Uani 1 1 d . . . H35 H 0.7934 -0.4602 0.4663 0.041 Uiso 1 1 calc R . . H36 H 0.7787 -0.5765 0.4302 0.041 Uiso 1 1 calc R . . C40 C 0.8014(3) -0.6390(3) 0.49793(12) 0.0449(8) Uani 1 1 d . . . H37 H 0.7887 -0.6029 0.5285 0.054 Uiso 1 1 calc R . . H38 H 0.7610 -0.7209 0.4940 0.054 Uiso 1 1 calc R . . C41 C 0.9201(3) -0.6668(5) 0.4970(2) 0.0834(17) Uani 1 1 d . . . H10 H 0.9347 -0.6915 0.4657 0.125 Uiso 1 1 calc R . . H11 H 0.9407 -0.7373 0.5184 0.125 Uiso 1 1 calc R . . H12 H 0.9614 -0.5895 0.5064 0.125 Uiso 1 1 calc R . . Cl1A Cl 0.02376(10) -0.68508(13) 0.09441(6) 0.0664(6) Uani 0.889(6) 1 d PDU B 3 C43 C -0.0841(3) -0.7909(4) 0.09723(16) 0.0550(10) Uani 1 1 d D . . H39 H -0.0783 -0.8608 0.0744 0.066 Uiso 0.889(6) 1 calc PR B 3 H40 H -0.0795 -0.8307 0.1283 0.066 Uiso 0.889(6) 1 calc PR B 3 H41 H -0.0538 -0.8104 0.0677 0.066 Uiso 0.111(6) 1 calc PR B 4 H42 H -0.0919 -0.8729 0.1140 0.066 Uiso 0.111(6) 1 calc PR B 4 F3B F 0.1086(12) -0.7803(7) 0.3653(3) 0.085(3) Uani 0.415(8) 1 d PDU A 2 F4B F 0.2554(5) -0.6975(11) 0.3845(4) 0.093(3) Uani 0.415(8) 1 d PDU A 2 Cl2A Cl -0.20703(8) -0.71706(10) 0.08663(4) 0.0658(3) Uani 1 1 d . B . Cl1B Cl 0.0021(14) -0.6850(17) 0.1310(10) 0.147(7) Uani 0.111(6) 1 d PDU B 4 F5B F 0.1195(11) -0.6376(11) 0.4158(3) 0.088(3) Uani 0.415(8) 1 d PU A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0172(11) 0.0242(12) 0.0200(11) 0.0030(9) 0.0004(8) 0.0010(9) C1 0.0173(12) 0.0270(15) 0.0217(13) 0.0003(11) -0.0006(10) -0.0001(11) C2 0.0254(14) 0.0285(15) 0.0240(13) 0.0028(12) -0.0024(11) -0.0065(12) C3 0.0225(13) 0.0242(14) 0.0263(14) 0.0041(11) 0.0022(11) -0.0036(11) C4 0.0174(12) 0.0218(14) 0.0208(12) 0.0020(10) 0.0032(10) 0.0014(10) C5 0.0151(12) 0.0223(14) 0.0221(13) -0.0009(11) 0.0024(10) 0.0022(10) C6 0.0202(13) 0.0243(14) 0.0211(13) -0.0010(11) 0.0018(10) 0.0033(11) N2 0.0198(11) 0.0208(12) 0.0248(11) 0.0014(9) -0.0007(9) 0.0004(9) C7 0.0163(12) 0.0252(14) 0.0246(13) -0.0030(11) 0.0017(10) 0.0008(11) C8 0.0178(13) 0.0252(14) 0.0285(14) -0.0041(11) 0.0022(11) 0.0024(11) C9 0.0202(13) 0.0236(14) 0.0295(14) -0.0036(11) 0.0023(11) 0.0002(11) C10 0.0253(14) 0.0233(15) 0.0367(16) -0.0004(12) 0.0028(12) -0.0005(12) C11 0.0306(16) 0.0234(15) 0.0445(17) -0.0004(13) 0.0058(13) -0.0007(12) C12 0.0230(14) 0.0266(16) 0.0467(18) -0.0087(14) 0.0024(13) -0.0026(12) C13 0.0203(13) 0.0294(16) 0.0333(15) -0.0101(12) 0.0012(11) 0.0012(12) B1 0.0225(15) 0.0211(16) 0.0288(16) 0.0019(13) -0.0017(12) -0.0012(12) F1 0.0279(9) 0.0276(9) 0.0505(11) -0.0065(8) -0.0095(8) 0.0082(7) F2 0.0386(10) 0.0349(10) 0.0277(9) 0.0083(7) -0.0028(7) -0.0128(8) C14 0.0189(13) 0.0235(14) 0.0228(13) -0.0004(11) -0.0039(10) -0.0044(11) C15 0.0220(13) 0.0274(15) 0.0229(13) -0.0006(11) 0.0004(10) -0.0010(11) C16 0.0262(14) 0.0347(16) 0.0218(13) 0.0024(12) 0.0008(11) -0.0017(12) C17 0.0276(14) 0.0286(15) 0.0262(14) 0.0045(12) -0.0039(11) -0.0032(12) C18 0.0184(13) 0.0292(15) 0.0306(15) 0.0019(12) -0.0037(11) 0.0000(11) C19 0.0203(13) 0.0268(15) 0.0238(13) -0.0004(11) -0.0002(10) -0.0048(11) C20 0.0319(16) 0.0423(18) 0.0313(15) -0.0002(14) 0.0049(12) 0.0081(14) C21 0.0442(19) 0.0412(19) 0.0340(17) 0.0105(15) -0.0040(14) 0.0045(15) C22 0.0235(14) 0.049(2) 0.0304(15) 0.0035(14) 0.0029(12) 0.0018(14) C23 0.0132(12) 0.0282(15) 0.0230(13) 0.0029(11) -0.0003(10) -0.0006(11) C24 0.0206(13) 0.0285(15) 0.0258(14) 0.0009(12) 0.0021(11) -0.0004(11) C25 0.0233(14) 0.0276(15) 0.0368(16) 0.0070(13) 0.0023(12) 0.0017(12) C26 0.0236(14) 0.0359(17) 0.0309(15) 0.0121(13) 0.0000(12) 0.0004(13) C27 0.0216(14) 0.0414(18) 0.0245(14) 0.0050(13) 0.0007(11) 0.0014(13) C28 0.0170(13) 0.0315(15) 0.0245(14) 0.0014(12) 0.0023(10) 0.0011(11) C29 0.060(2) 0.050(2) 0.0419(19) 0.0174(17) 0.0052(17) 0.0069(18) F3A 0.082(4) 0.089(4) 0.107(4) 0.072(3) 0.010(3) -0.011(3) F4A 0.136(5) 0.064(3) 0.072(3) 0.039(3) 0.033(3) 0.052(4) F5A 0.154(6) 0.060(3) 0.044(3) 0.024(2) -0.043(4) -0.007(4) C30 0.0149(12) 0.0272(15) 0.0224(13) -0.0010(11) -0.0015(10) -0.0012(11) C31 0.0172(13) 0.0285(15) 0.0252(14) -0.0032(11) 0.0006(10) -0.0005(11) C32 0.0213(13) 0.0253(15) 0.0322(15) -0.0012(12) 0.0000(11) 0.0013(11) C33 0.0186(13) 0.0330(16) 0.0270(14) 0.0057(12) 0.0012(11) -0.0022(12) C34 0.0231(14) 0.0393(17) 0.0230(14) -0.0030(12) -0.0016(11) -0.0020(13) C35 0.0213(13) 0.0299(16) 0.0290(14) -0.0035(12) 0.0026(11) 0.0022(12) C36 0.0295(16) 0.0386(18) 0.0280(15) 0.0068(13) 0.0028(12) -0.0006(13) C37 0.0280(15) 0.0281(15) 0.0265(14) 0.0036(12) 0.0020(11) 0.0016(12) C38 0.0356(16) 0.0301(16) 0.0236(14) 0.0034(12) -0.0017(12) 0.0008(13) C39 0.0347(16) 0.0283(16) 0.0374(17) 0.0068(13) -0.0085(13) -0.0032(13) C40 0.047(2) 0.0406(19) 0.0440(19) 0.0103(16) -0.0144(15) 0.0006(16) C41 0.044(2) 0.069(3) 0.130(4) 0.056(3) -0.031(3) -0.004(2) Cl1A 0.0427(7) 0.0538(8) 0.1032(13) 0.0065(7) 0.0082(6) -0.0180(5) C43 0.043(2) 0.046(2) 0.076(3) 0.011(2) 0.0060(19) -0.0074(17) F3B 0.134(7) 0.045(4) 0.070(4) 0.025(3) -0.025(5) -0.016(4) F4B 0.077(4) 0.094(5) 0.104(5) 0.072(4) -0.015(4) 0.015(4) Cl2A 0.0468(6) 0.0528(6) 0.0947(8) -0.0081(6) -0.0095(5) 0.0069(4) Cl1B 0.100(11) 0.097(10) 0.248(19) -0.008(13) 0.042(13) 0.005(9) F5B 0.148(7) 0.074(5) 0.046(4) 0.036(3) 0.030(5) 0.028(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 N1 C1 1.349(3) . ? N1 C4 1.400(3) . ? N1 B1 1.562(4) . ? C1 C2 1.425(4) . ? C1 C14 1.481(4) . ? C2 C3 1.360(4) . ? C3 C4 1.424(4) . ? C4 C5 1.388(4) . ? C5 C6 1.423(4) . ? C5 C23 1.484(4) . ? C6 N2 1.390(3) . ? C6 C7 1.417(4) . ? N2 C9 1.374(3) . ? N2 B1 1.528(4) . ? C7 C8 1.425(4) . ? C7 C30 1.474(4) . ? C8 C9 1.415(4) . ? C8 C13 1.417(4) . ? C9 C10 1.406(4) . ? C10 C11 1.377(4) . ? C11 C12 1.411(4) . ? C12 C13 1.371(4) . ? B1 F2 1.380(4) . ? B1 F1 1.401(4) . ? C14 C15 1.397(4) . ? C14 C19 1.403(4) . ? C15 C16 1.396(4) . ? C15 C20 1.503(4) . ? C16 C17 1.387(4) . ? C17 C18 1.387(4) . ? C17 C21 1.508(4) . ? C18 C19 1.394(4) . ? C19 C22 1.503(4) . ? C23 C24 1.395(4) . ? C23 C28 1.395(4) . ? C24 C25 1.384(4) . ? C25 C26 1.387(4) . ? C26 C27 1.387(4) . ? C26 C29 1.477(4) . ? C27 C28 1.384(4) . ? C29 F3B 1.261(6) . ? C29 F5A 1.275(7) . ? C29 F5B 1.304(10) . ? C29 F4A 1.329(5) . ? C29 F4B 1.373(6) . ? C29 F3A 1.380(6) . ? C30 C35 1.393(4) . ? C30 C31 1.393(4) . ? C31 C32 1.391(4) . ? C32 C33 1.392(4) . ? C33 C34 1.391(4) . ? C33 C36 1.511(4) . ? C34 C35 1.382(4) . ? C36 C37 1.523(4) . ? C37 C38 1.524(4) . ? C38 C39 1.517(4) . ? C39 C40 1.522(4) . ? C40 C41 1.517(6) . ? Cl1A C43 1.749(4) . ? C43 Cl2A 1.723(4) . ? C43 Cl1B 1.773(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 108.1(2) . . ? C1 N1 B1 127.5(2) . . ? C4 N1 B1 123.6(2) . . ? N1 C1 C2 109.0(2) . . ? N1 C1 C14 123.9(2) . . ? C2 C1 C14 127.1(2) . . ? C3 C2 C1 107.7(2) . . ? C2 C3 C4 107.6(2) . . ? C5 C4 N1 121.5(2) . . ? C5 C4 C3 130.9(2) . . ? N1 C4 C3 107.5(2) . . ? C4 C5 C6 120.5(2) . . ? C4 C5 C23 118.7(2) . . ? C6 C5 C23 120.8(2) . . ? N2 C6 C7 110.0(2) . . ? N2 C6 C5 119.2(2) . . ? C7 C6 C5 130.9(2) . . ? C9 N2 C6 107.5(2) . . ? C9 N2 B1 125.4(2) . . ? C6 N2 B1 127.0(2) . . ? C6 C7 C8 105.7(2) . . ? C6 C7 C30 129.6(2) . . ? C8 C7 C30 124.6(2) . . ? C9 C8 C13 119.8(3) . . ? C9 C8 C7 107.3(2) . . ? C13 C8 C7 132.7(3) . . ? N2 C9 C10 129.1(3) . . ? N2 C9 C8 109.5(2) . . ? C10 C9 C8 121.4(3) . . ? C11 C10 C9 117.2(3) . . ? C10 C11 C12 122.1(3) . . ? C13 C12 C11 121.2(3) . . ? C12 C13 C8 118.3(3) . . ? F2 B1 F1 109.7(2) . . ? F2 B1 N2 111.1(2) . . ? F1 B1 N2 110.3(2) . . ? F2 B1 N1 110.8(2) . . ? F1 B1 N1 108.4(2) . . ? N2 B1 N1 106.4(2) . . ? C15 C14 C19 121.0(2) . . ? C15 C14 C1 120.3(2) . . ? C19 C14 C1 118.7(2) . . ? C16 C15 C14 118.5(3) . . ? C16 C15 C20 120.8(2) . . ? C14 C15 C20 120.7(2) . . ? C17 C16 C15 122.0(3) . . ? C18 C17 C16 118.2(3) . . ? C18 C17 C21 119.8(3) . . ? C16 C17 C21 122.0(3) . . ? C17 C18 C19 122.2(3) . . ? C18 C19 C14 118.2(2) . . ? C18 C19 C22 120.8(3) . . ? C14 C19 C22 121.0(2) . . ? C24 C23 C28 119.2(2) . . ? C24 C23 C5 121.3(2) . . ? C28 C23 C5 119.5(2) . . ? C25 C24 C23 120.5(3) . . ? C24 C25 C26 119.6(3) . . ? C25 C26 C27 120.7(3) . . ? C25 C26 C29 119.6(3) . . ? C27 C26 C29 119.7(3) . . ? C28 C27 C26 119.6(3) . . ? C27 C28 C23 120.4(3) . . ? F3B C29 F5A 126.4(5) . . ? F3B C29 F5B 108.5(8) . . ? F5A C29 F5B 36.6(5) . . ? F3B C29 F4A 55.4(6) . . ? F5A C29 F4A 109.0(5) . . ? F5B C29 F4A 129.3(6) . . ? F3B C29 F4B 102.8(7) . . ? F5A C29 F4B 68.4(6) . . ? F5B C29 F4B 103.2(7) . . ? F4A C29 F4B 50.0(5) . . ? F3B C29 F3A 44.6(5) . . ? F5A C29 F3A 106.9(5) . . ? F5B C29 F3A 73.6(6) . . ? F4A C29 F3A 98.9(5) . . ? F4B C29 F3A 138.1(5) . . ? F3B C29 C26 116.3(4) . . ? F5A C29 C26 116.3(4) . . ? F5B C29 C26 115.1(5) . . ? F4A C29 C26 114.6(3) . . ? F4B C29 C26 109.4(4) . . ? F3A C29 C26 109.4(3) . . ? C35 C30 C31 118.3(2) . . ? C35 C30 C7 120.0(2) . . ? C31 C30 C7 121.7(2) . . ? C32 C31 C30 120.4(3) . . ? C31 C32 C33 121.2(3) . . ? C34 C33 C32 117.9(3) . . ? C34 C33 C36 120.9(3) . . ? C32 C33 C36 121.2(3) . . ? C35 C34 C33 121.2(3) . . ? C34 C35 C30 120.8(3) . . ? C33 C36 C37 114.7(2) . . ? C36 C37 C38 111.7(2) . . ? C39 C38 C37 115.5(2) . . ? C38 C39 C40 112.9(3) . . ? C41 C40 C39 112.8(3) . . ? Cl2A C43 Cl1A 113.2(2) . . ? Cl2A C43 Cl1B 108.2(6) . . ? Cl1A C43 Cl1B 37.1(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C2 -0.5(3) . . . . ? B1 N1 C1 C2 -171.1(2) . . . . ? C4 N1 C1 C14 178.6(2) . . . . ? B1 N1 C1 C14 8.1(4) . . . . ? N1 C1 C2 C3 0.9(3) . . . . ? C14 C1 C2 C3 -178.2(3) . . . . ? C1 C2 C3 C4 -0.9(3) . . . . ? C1 N1 C4 C5 178.2(2) . . . . ? B1 N1 C4 C5 -10.8(4) . . . . ? C1 N1 C4 C3 0.0(3) . . . . ? B1 N1 C4 C3 171.0(2) . . . . ? C2 C3 C4 C5 -177.4(3) . . . . ? C2 C3 C4 N1 0.6(3) . . . . ? N1 C4 C5 C6 -1.2(4) . . . . ? C3 C4 C5 C6 176.5(3) . . . . ? N1 C4 C5 C23 176.9(2) . . . . ? C3 C4 C5 C23 -5.3(4) . . . . ? C4 C5 C6 N2 6.2(4) . . . . ? C23 C5 C6 N2 -172.0(2) . . . . ? C4 C5 C6 C7 -174.6(3) . . . . ? C23 C5 C6 C7 7.2(4) . . . . ? C7 C6 N2 C9 -1.6(3) . . . . ? C5 C6 N2 C9 177.8(2) . . . . ? C7 C6 N2 B1 -178.4(2) . . . . ? C5 C6 N2 B1 0.9(4) . . . . ? N2 C6 C7 C8 2.6(3) . . . . ? C5 C6 C7 C8 -176.7(3) . . . . ? N2 C6 C7 C30 -172.8(2) . . . . ? C5 C6 C7 C30 7.9(5) . . . . ? C6 C7 C8 C9 -2.5(3) . . . . ? C30 C7 C8 C9 173.1(2) . . . . ? C6 C7 C8 C13 -177.9(3) . . . . ? C30 C7 C8 C13 -2.2(5) . . . . ? C6 N2 C9 C10 177.4(3) . . . . ? B1 N2 C9 C10 -5.7(4) . . . . ? C6 N2 C9 C8 -0.1(3) . . . . ? B1 N2 C9 C8 176.8(2) . . . . ? C13 C8 C9 N2 177.7(2) . . . . ? C7 C8 C9 N2 1.7(3) . . . . ? C13 C8 C9 C10 0.0(4) . . . . ? C7 C8 C9 C10 -176.0(2) . . . . ? N2 C9 C10 C11 -176.4(3) . . . . ? C8 C9 C10 C11 0.8(4) . . . . ? C9 C10 C11 C12 -1.0(4) . . . . ? C10 C11 C12 C13 0.4(5) . . . . ? C11 C12 C13 C8 0.4(4) . . . . ? C9 C8 C13 C12 -0.6(4) . . . . ? C7 C8 C13 C12 174.2(3) . . . . ? C9 N2 B1 F2 52.4(4) . . . . ? C6 N2 B1 F2 -131.3(3) . . . . ? C9 N2 B1 F1 -69.5(3) . . . . ? C6 N2 B1 F1 106.8(3) . . . . ? C9 N2 B1 N1 173.1(2) . . . . ? C6 N2 B1 N1 -10.6(4) . . . . ? C1 N1 B1 F2 -54.6(3) . . . . ? C4 N1 B1 F2 136.2(2) . . . . ? C1 N1 B1 F1 65.9(3) . . . . ? C4 N1 B1 F1 -103.3(3) . . . . ? C1 N1 B1 N2 -175.5(2) . . . . ? C4 N1 B1 N2 15.3(3) . . . . ? N1 C1 C14 C15 86.2(3) . . . . ? C2 C1 C14 C15 -94.8(3) . . . . ? N1 C1 C14 C19 -96.7(3) . . . . ? C2 C1 C14 C19 82.3(4) . . . . ? C19 C14 C15 C16 2.0(4) . . . . ? C1 C14 C15 C16 179.0(2) . . . . ? C19 C14 C15 C20 -176.5(3) . . . . ? C1 C14 C15 C20 0.6(4) . . . . ? C14 C15 C16 C17 -0.9(4) . . . . ? C20 C15 C16 C17 177.6(3) . . . . ? C15 C16 C17 C18 -1.0(4) . . . . ? C15 C16 C17 C21 178.4(3) . . . . ? C16 C17 C18 C19 1.9(4) . . . . ? C21 C17 C18 C19 -177.5(3) . . . . ? C17 C18 C19 C14 -0.9(4) . . . . ? C17 C18 C19 C22 178.9(3) . . . . ? C15 C14 C19 C18 -1.1(4) . . . . ? C1 C14 C19 C18 -178.3(2) . . . . ? C15 C14 C19 C22 179.1(3) . . . . ? C1 C14 C19 C22 1.9(4) . . . . ? C4 C5 C23 C24 59.0(3) . . . . ? C6 C5 C23 C24 -122.8(3) . . . . ? C4 C5 C23 C28 -121.2(3) . . . . ? C6 C5 C23 C28 56.9(3) . . . . ? C28 C23 C24 C25 -1.5(4) . . . . ? C5 C23 C24 C25 178.3(2) . . . . ? C23 C24 C25 C26 0.4(4) . . . . ? C24 C25 C26 C27 1.0(4) . . . . ? C24 C25 C26 C29 179.8(3) . . . . ? C25 C26 C27 C28 -1.3(4) . . . . ? C29 C26 C27 C28 179.8(3) . . . . ? C26 C27 C28 C23 0.3(4) . . . . ? C24 C23 C28 C27 1.1(4) . . . . ? C5 C23 C28 C27 -178.7(2) . . . . ? C25 C26 C29 F3B -40.8(9) . . . . ? C27 C26 C29 F3B 138.1(9) . . . . ? C25 C26 C29 F5A 149.9(6) . . . . ? C27 C26 C29 F5A -31.2(7) . . . . ? C25 C26 C29 F5B -169.3(8) . . . . ? C27 C26 C29 F5B 9.6(9) . . . . ? C25 C26 C29 F4A 21.2(7) . . . . ? C27 C26 C29 F4A -160.0(6) . . . . ? C25 C26 C29 F4B 75.1(8) . . . . ? C27 C26 C29 F4B -106.0(7) . . . . ? C25 C26 C29 F3A -88.8(6) . . . . ? C27 C26 C29 F3A 90.1(6) . . . . ? C6 C7 C30 C35 -127.8(3) . . . . ? C8 C7 C30 C35 57.6(4) . . . . ? C6 C7 C30 C31 52.5(4) . . . . ? C8 C7 C30 C31 -122.1(3) . . . . ? C35 C30 C31 C32 3.1(4) . . . . ? C7 C30 C31 C32 -177.2(2) . . . . ? C30 C31 C32 C33 -0.7(4) . . . . ? C31 C32 C33 C34 -1.9(4) . . . . ? C31 C32 C33 C36 178.9(3) . . . . ? C32 C33 C34 C35 2.2(4) . . . . ? C36 C33 C34 C35 -178.7(3) . . . . ? C33 C34 C35 C30 0.2(4) . . . . ? C31 C30 C35 C34 -2.8(4) . . . . ? C7 C30 C35 C34 177.4(3) . . . . ? C34 C33 C36 C37 -100.5(3) . . . . ? C32 C33 C36 C37 78.6(4) . . . . ? C33 C36 C37 C38 175.2(3) . . . . ? C36 C37 C38 C39 173.6(3) . . . . ? C37 C38 C39 C40 -171.6(3) . . . . ? C38 C39 C40 C41 173.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.544 _refine_diff_density_min -0.890 _refine_diff_density_rms 0.060 #------------------------------------------------------------------------------ # TEXT data_compound2 _database_code_depnum_ccdc_archive 'CCDC 899845' #TrackingRef '13689_web_deposit_cif_file_1_AtsushiWakamiya_1346680845.compound2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C77.50 H65 B2 Cl4.50 F10 N4' _chemical_formula_weight 1423.48 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 22.654(4) _cell_length_b 23.390(4) _cell_length_c 13.523(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7165(2) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 15702 _cell_measurement_theta_min 2.6977 _cell_measurement_theta_max 31.5050 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2938 _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9505 _exptl_absorpt_correction_T_max 0.9974 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn70 CCD (4x4 bin mode) with MicroMax-007 ; _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44733 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_sigmaI/netI 0.0326 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 24.99 _reflns_number_total 6277 _reflns_number_gt 5261 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 for windows' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[?^2^(Fo^2^)+(0.1544P)^2^+7.9346P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef none _refine_ls_number_reflns 6277 _refine_ls_number_parameters 526 _refine_ls_number_restraints 139 _refine_ls_R_factor_all 0.1011 _refine_ls_R_factor_gt 0.0899 _refine_ls_wR_factor_ref 0.2610 _refine_ls_wR_factor_gt 0.2464 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.101 _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 N1 N 0.35278(12) 0.18731(12) 0.0408(2) 0.0369(6) Uani 1 1 d . . . C1 C 0.32535(16) 0.23400(15) 0.0064(2) 0.0408(8) Uani 1 1 d . . . C2 C 0.28578(18) 0.21798(17) -0.0701(3) 0.0494(9) Uani 1 1 d . . . H1 H 0.2610 0.2431 -0.1066 0.059 Uiso 1 1 calc R . . C3 C 0.28953(17) 0.16007(16) -0.0819(3) 0.0461(9) Uani 1 1 d . . . H2 H 0.2682 0.1376 -0.1282 0.055 Uiso 1 1 calc R . . C4 C 0.33156(15) 0.13976(15) -0.0113(2) 0.0375(7) Uani 1 1 d . . . C5 C 0.35055(14) 0.08459(15) 0.0074(2) 0.0351(7) Uani 1 1 d . . . C6 C 0.39450(14) 0.07454(14) 0.0799(2) 0.0335(7) Uani 1 1 d . . . N2 N 0.42024(12) 0.12162(12) 0.1271(2) 0.0373(7) Uani 1 1 d . . . C7 C 0.41970(13) 0.02334(14) 0.1163(2) 0.0324(7) Uani 1 1 d . . . C8 C 0.46304(13) 0.04005(13) 0.1880(2) 0.0316(7) Uani 1 1 d . . . C9 C 0.46215(13) 0.10172(13) 0.1913(2) 0.0341(7) Uani 1 1 d . . . C10 C 0.5000 0.1337(2) 0.2500 0.0379(10) Uani 1 2 d S . . H3 H 0.5000 0.1743 0.2500 0.045 Uiso 1 2 calc SR . . C11 C 0.5000 0.0086(2) 0.2500 0.0325(9) Uani 1 2 d S . . H4 H 0.5000 -0.0320 0.2500 0.039 Uiso 1 2 calc SR . . B1 B 0.40342(19) 0.18491(17) 0.1175(3) 0.0449(10) Uani 1 1 d . . . F1 F 0.45071(10) 0.21663(10) 0.0842(3) 0.0770(9) Uani 1 1 d . . . F2 F 0.38455(12) 0.20597(11) 0.20775(18) 0.0683(8) Uani 1 1 d . . . C12 C 0.33362(17) 0.29218(15) 0.0479(2) 0.0430(8) Uani 1 1 d . . . C13 C 0.37263(18) 0.33054(17) 0.0024(3) 0.0517(9) Uani 1 1 d . . . C14 C 0.3770(2) 0.38552(18) 0.0403(4) 0.0611(11) Uani 1 1 d . . . H5 H 0.4031 0.4118 0.0095 0.073 Uiso 1 1 calc R . . C15 C 0.3448(2) 0.40323(18) 0.1211(3) 0.0593(11) Uani 1 1 d . . . C16 C 0.3074(2) 0.36519(18) 0.1641(3) 0.0552(10) Uani 1 1 d . . . H6 H 0.2849 0.3771 0.2198 0.066 Uiso 1 1 calc R . . C17 C 0.30067(18) 0.30861(17) 0.1292(3) 0.0483(9) Uani 1 1 d . . . C18 C 0.4091(2) 0.3125(2) -0.0854(4) 0.0721(14) Uani 1 1 d . . . H7 H 0.4355 0.3437 -0.1046 0.108 Uiso 1 1 calc R . . H8 H 0.3829 0.3031 -0.1408 0.108 Uiso 1 1 calc R . . H9 H 0.4326 0.2788 -0.0679 0.108 Uiso 1 1 calc R . . C19 C 0.3509(3) 0.4639(2) 0.1599(4) 0.0791(15) Uani 1 1 d . . . H10 H 0.3642 0.4890 0.1064 0.119 Uiso 1 1 calc R . . H11 H 0.3798 0.4646 0.2138 0.119 Uiso 1 1 calc R . . H12 H 0.3126 0.4772 0.1846 0.119 Uiso 1 1 calc R . . C20 C 0.2586(2) 0.26827(19) 0.1784(3) 0.0631(12) Uani 1 1 d . . . H13 H 0.2396 0.2442 0.1282 0.095 Uiso 1 1 calc R . . H14 H 0.2284 0.2901 0.2139 0.095 Uiso 1 1 calc R . . H15 H 0.2801 0.2440 0.2252 0.095 Uiso 1 1 calc R . . C21 C 0.32296(14) 0.03745(15) -0.0508(2) 0.0360(7) Uani 1 1 d . . . C22 C 0.26245(15) 0.02738(16) -0.0410(3) 0.0404(8) Uani 1 1 d . . . H23 H 0.2394 0.0506 0.0017 0.048 Uiso 1 1 calc R . . C23 C 0.23606(16) -0.01672(16) -0.0941(3) 0.0434(8) Uani 1 1 d . . . H16 H 0.1950 -0.0240 -0.0870 0.052 Uiso 1 1 calc R . . C24 C 0.26984(15) -0.05000(15) -0.1576(2) 0.0401(8) Uani 1 1 d . A . C25 C 0.32977(16) -0.03977(15) -0.1676(3) 0.0415(8) Uani 1 1 d . . . H17 H 0.3528 -0.0628 -0.2108 0.050 Uiso 1 1 calc R . . C26 C 0.35612(15) 0.00410(15) -0.1146(2) 0.0373(7) Uani 1 1 d . . . H18 H 0.3971 0.0113 -0.1221 0.045 Uiso 1 1 calc R . . C27 C 0.24180(18) -0.09838(16) -0.2127(3) 0.0470(9) Uani 1 1 d D . . F3A F 0.24859(16) -0.14854(11) -0.1673(2) 0.0703(10) Uani 0.916(6) 1 d P A 1 F4A F 0.18247(12) -0.09230(13) -0.2203(2) 0.0677(10) Uani 0.916(6) 1 d P A 1 F5A F 0.26165(16) -0.10378(15) -0.3033(2) 0.0781(13) Uani 0.916(6) 1 d P A 1 C28 C 0.40656(13) -0.03581(13) 0.0872(2) 0.0329(7) Uani 1 1 d . . . C29 C 0.35053(15) -0.05956(15) 0.0989(3) 0.0380(7) Uani 1 1 d . . . H19 H 0.3206 -0.0385 0.1319 0.046 Uiso 1 1 calc R . . C30 C 0.33841(15) -0.11358(15) 0.0628(3) 0.0425(8) Uani 1 1 d . . . H20 H 0.3000 -0.1290 0.0712 0.051 Uiso 1 1 calc R . . C31 C 0.38096(17) -0.14574(16) 0.0146(3) 0.0476(9) Uani 1 1 d . C . C32 C 0.43770(16) -0.12291(16) 0.0065(3) 0.0431(8) Uani 1 1 d . . . H21 H 0.4680 -0.1446 -0.0243 0.052 Uiso 1 1 calc R . . C33 C 0.45020(15) -0.06912(14) 0.0428(3) 0.0383(8) Uani 1 1 d . . . H22 H 0.4892 -0.0545 0.0374 0.046 Uiso 1 1 calc R . . Cl1 Cl 0.5589(2) -0.1444(3) 0.2101(3) 0.0473(11) Uani 0.50 1 d P . 3 C34 C 0.4935(5) -0.1825(4) 0.2174(5) 0.058(2) Uani 0.50 1 d P . . Cl2 Cl 0.5074(10) -0.25208(11) 0.2578(11) 0.095(4) Uani 0.50 1 d P . . C35 C 0.3666(2) -0.20355(18) -0.0288(4) 0.0688(13) Uani 1 1 d DU . . H41 H 0.3817 -0.2057 -0.0974 0.083 Uiso 0.50 1 calc PR B 3 H42 H 0.3232 -0.2088 -0.0308 0.083 Uiso 0.50 1 calc PR B 3 H43 H 0.3279 -0.2151 -0.0012 0.083 Uiso 0.50 1 calc PR B 4 H44 H 0.3606 -0.1977 -0.1006 0.083 Uiso 0.50 1 calc PR B 4 C36B C 0.4060(4) -0.2530(3) -0.0183(8) 0.066(2) Uani 0.50 1 d PDU C 4 H24 H 0.4085 -0.2624 0.0530 0.079 Uiso 0.50 1 calc PR C 4 H25 H 0.4459 -0.2410 -0.0396 0.079 Uiso 0.50 1 calc PR C 4 C36A C 0.3955(4) -0.2526(3) 0.0355(7) 0.056(2) Uiso 0.50 1 d PDU C 3 H26 H 0.4390 -0.2482 0.0329 0.068 Uiso 0.50 1 calc PR C 3 H27 H 0.3832 -0.2474 0.1052 0.068 Uiso 0.50 1 calc PR C 3 Cl3 Cl 0.5593(4) -0.1490(5) 0.2060(7) 0.102(3) Uani 0.50 1 d P . 4 F3B F 0.2856(11) -0.1333(13) -0.245(3) 0.075(11) Uiso 0.084(6) 1 d PD A 2 F4B F 0.2123(15) -0.0847(14) -0.2961(17) 0.068(10) Uiso 0.084(6) 1 d PD A 2 F5B F 0.1974(14) -0.1278(16) -0.172(3) 0.084(12) Uiso 0.084(6) 1 d PD A 2 C37B C 0.3900(4) -0.3107(4) -0.0763(8) 0.076(3) Uani 0.50 1 d PDU C 4 H28 H 0.3747 -0.3407 -0.0315 0.091 Uiso 0.50 1 calc PR C 4 H29 H 0.3616 -0.3040 -0.1307 0.091 Uiso 0.50 1 calc PR C 4 C38A C 0.4237(4) -0.3554(3) -0.0406(9) 0.072(2) Uani 0.50 1 d PDU C 3 H32 H 0.4496 -0.3682 0.0141 0.086 Uiso 0.50 1 calc PR C 3 H33 H 0.4489 -0.3330 -0.0863 0.086 Uiso 0.50 1 calc PR C 3 C37A C 0.3798(4) -0.3141(3) 0.0035(10) 0.075(3) Uani 0.50 1 d PDU C 3 H30 H 0.3631 -0.3332 0.0626 0.091 Uiso 0.50 1 calc PR C 3 H31 H 0.3472 -0.3107 -0.0448 0.091 Uiso 0.50 1 calc PR C 3 C39A C 0.4046(4) -0.4088(3) -0.0963(10) 0.082(3) Uani 0.50 1 d PDU C 3 H36 H 0.3641 -0.4191 -0.0754 0.098 Uiso 0.50 1 calc PR C 3 H37 H 0.4034 -0.4001 -0.1679 0.098 Uiso 0.50 1 calc PR C 3 C40A C 0.4448(5) -0.4600(4) -0.0797(13) 0.099(4) Uani 0.50 1 d PDU C 3 H38 H 0.4803 -0.4559 -0.1204 0.149 Uiso 0.50 1 calc PR C 3 H39 H 0.4239 -0.4951 -0.0982 0.149 Uiso 0.50 1 calc PR C 3 H40 H 0.4560 -0.4619 -0.0098 0.149 Uiso 0.50 1 calc PR C 3 C39B C 0.4757(8) -0.3514(8) -0.2127(11) 0.132(4) Uani 0.50 1 d PDU . 4 C38B C 0.4533(5) -0.3250(8) -0.1155(11) 0.121(4) Uani 0.50 1 d PDU C 4 H34 H 0.4748 -0.2882 -0.1107 0.146 Uiso 0.50 1 calc PR C 4 H35 H 0.4704 -0.3497 -0.0635 0.146 Uiso 0.50 1 calc PR C 4 C40B C 0.5000 -0.2960(10) -0.2500 0.148(6) Uani 0.50 2 d SPDU . 4 C40C C 0.5000 -0.4084(9) -0.2500 0.152(6) Uani 0.50 2 d SPDU D 5 C41 C 0.4965(10) -0.4363(15) 0.2156(18) 0.136(13) Uiso 0.25 1 d PD . 5 Cl4 Cl 0.5005(13) -0.4667(12) 0.100(2) 0.349(14) Uiso 0.25 1 d PD . 5 Cl5 Cl 0.5445(6) -0.4136(6) 0.3049(10) 0.169(4) Uiso 0.25 1 d PD . 5 Cl6 Cl 0.5694(8) -0.4229(10) 0.2453(19) 0.259(9) Uiso 0.25 1 d PD . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0370(14) 0.0350(15) 0.0387(15) 0.0004(11) -0.0010(12) 0.0056(11) C1 0.0457(19) 0.0407(19) 0.0359(17) 0.0032(14) 0.0031(14) 0.0106(15) C2 0.063(2) 0.047(2) 0.0381(18) 0.0019(16) -0.0091(17) 0.0196(18) C3 0.055(2) 0.046(2) 0.0368(18) -0.0033(15) -0.0076(15) 0.0127(17) C4 0.0378(17) 0.0395(18) 0.0352(17) -0.0016(14) 0.0007(14) 0.0064(14) C5 0.0323(16) 0.0394(18) 0.0336(16) 0.0008(14) 0.0015(13) 0.0029(13) C6 0.0300(15) 0.0342(17) 0.0364(16) -0.0014(13) 0.0005(13) -0.0016(12) N2 0.0349(14) 0.0330(15) 0.0440(15) 0.0014(12) -0.0045(12) 0.0021(11) C7 0.0284(15) 0.0346(16) 0.0342(16) -0.0015(13) 0.0003(12) -0.0012(12) C8 0.0259(14) 0.0311(16) 0.0379(16) 0.0012(13) 0.0024(13) 0.0004(12) C9 0.0288(15) 0.0320(16) 0.0414(17) -0.0014(13) -0.0024(13) 0.0018(12) C10 0.033(2) 0.031(2) 0.050(3) 0.000 -0.003(2) 0.000 C11 0.026(2) 0.034(2) 0.038(2) 0.000 0.0007(18) 0.000 B1 0.042(2) 0.0311(19) 0.062(3) -0.0011(18) -0.0142(19) 0.0059(16) F1 0.0444(13) 0.0413(13) 0.145(3) 0.0277(15) -0.0192(14) -0.0047(10) F2 0.0867(18) 0.0563(14) 0.0620(15) -0.0224(12) -0.0372(13) 0.0339(13) C12 0.053(2) 0.0401(19) 0.0359(17) 0.0024(14) -0.0060(15) 0.0152(16) C13 0.059(2) 0.041(2) 0.056(2) 0.0033(17) 0.0033(19) 0.0089(17) C14 0.074(3) 0.038(2) 0.071(3) 0.0002(19) 0.002(2) 0.007(2) C15 0.078(3) 0.047(2) 0.053(2) -0.0046(19) -0.011(2) 0.009(2) C16 0.076(3) 0.050(2) 0.040(2) -0.0051(17) -0.0030(19) 0.015(2) C17 0.060(2) 0.049(2) 0.0362(18) 0.0003(15) -0.0026(16) 0.0168(18) C18 0.085(3) 0.052(3) 0.079(3) 0.002(2) 0.032(3) 0.008(2) C19 0.114(4) 0.048(3) 0.076(3) -0.012(2) -0.009(3) 0.007(3) C20 0.085(3) 0.054(2) 0.051(2) -0.0048(19) 0.023(2) 0.012(2) C21 0.0331(16) 0.0426(18) 0.0321(16) 0.0029(14) -0.0020(13) 0.0031(13) C22 0.0317(17) 0.048(2) 0.0412(18) -0.0033(15) 0.0015(14) 0.0022(14) C23 0.0370(18) 0.050(2) 0.0436(19) -0.0017(16) -0.0022(15) 0.0015(15) C24 0.0433(19) 0.0417(18) 0.0352(17) 0.0024(14) -0.0069(14) -0.0049(15) C25 0.0452(19) 0.0433(19) 0.0359(17) -0.0026(15) 0.0020(15) 0.0013(15) C26 0.0337(16) 0.0424(18) 0.0359(17) 0.0000(14) 0.0027(13) 0.0006(14) C27 0.053(2) 0.047(2) 0.0409(19) 0.0003(16) -0.0050(16) -0.0069(17) F3A 0.102(2) 0.0397(14) 0.0692(18) 0.0018(12) -0.0197(16) -0.0092(14) F4A 0.0491(16) 0.0649(18) 0.089(2) -0.0139(16) -0.0139(14) -0.0094(13) F5A 0.097(3) 0.094(2) 0.0426(15) -0.0215(15) 0.0126(15) -0.047(2) C28 0.0296(15) 0.0324(16) 0.0368(16) 0.0025(13) 0.0009(12) -0.0032(12) C29 0.0342(17) 0.0371(18) 0.0428(18) 0.0012(14) -0.0009(14) -0.0010(13) C30 0.0358(17) 0.0374(18) 0.054(2) -0.0023(15) -0.0012(15) -0.0043(14) C31 0.051(2) 0.0372(19) 0.055(2) -0.0048(16) -0.0076(17) -0.0040(16) C32 0.0437(19) 0.0387(19) 0.047(2) -0.0083(15) 0.0013(15) 0.0023(15) C33 0.0336(16) 0.0389(18) 0.0423(18) 0.0022(14) 0.0011(14) -0.0008(13) Cl1 0.039(2) 0.050(2) 0.053(2) 0.0029(16) 0.0073(16) 0.0019(17) C34 0.083(6) 0.049(4) 0.043(4) -0.003(3) 0.015(5) -0.011(4) Cl2 0.128(9) 0.0541(11) 0.103(5) 0.027(4) 0.065(6) 0.014(3) C35 0.059(3) 0.047(2) 0.100(3) -0.027(2) -0.012(2) -0.002(2) C36B 0.061(5) 0.063(5) 0.074(6) 0.010(4) -0.004(5) -0.001(4) Cl3 0.091(5) 0.069(4) 0.145(7) 0.010(4) 0.019(4) 0.003(3) C37B 0.041(4) 0.104(7) 0.082(6) 0.036(5) -0.025(4) -0.025(4) C38A 0.054(4) 0.035(4) 0.126(7) -0.007(4) 0.003(5) -0.007(3) C37A 0.059(5) 0.036(4) 0.131(7) -0.017(5) -0.010(5) 0.004(4) C39A 0.060(5) 0.049(5) 0.136(8) -0.014(5) -0.012(5) -0.006(4) C40A 0.085(7) 0.044(5) 0.169(10) -0.014(6) -0.011(7) 0.005(5) C39B 0.120(9) 0.148(10) 0.129(9) -0.023(7) -0.012(7) -0.010(7) C38B 0.107(7) 0.132(9) 0.125(8) -0.008(7) -0.005(7) 0.004(7) C40B 0.141(12) 0.156(12) 0.148(12) 0.000 -0.012(11) 0.000 C40C 0.135(12) 0.160(13) 0.160(12) 0.000 -0.022(11) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.340(4) . ? N1 C4 1.401(4) . ? N1 B1 1.548(5) . ? C1 C2 1.419(5) . ? C1 C12 1.484(5) . ? C2 C3 1.367(5) . ? C3 C4 1.430(5) . ? C4 C5 1.383(5) . ? C5 C6 1.417(5) . ? C5 C21 1.492(5) . ? C6 N2 1.400(4) . ? C6 C7 1.415(4) . ? N2 C9 1.368(4) . ? N2 B1 1.534(5) . ? C7 C8 1.434(4) . ? C7 C28 1.469(4) . ? C8 C11 1.395(4) . ? C8 C9 1.443(4) . ? C9 C10 1.387(4) . ? C10 C9 1.387(4) 4_655 ? C11 C8 1.395(4) 4_655 ? B1 F1 1.379(5) . ? B1 F2 1.384(5) . ? C12 C17 1.383(5) . ? C12 C13 1.401(6) . ? C13 C14 1.388(6) . ? C13 C18 1.507(6) . ? C14 C15 1.377(7) . ? C15 C16 1.360(7) . ? C15 C19 1.519(6) . ? C16 C17 1.414(6) . ? C17 C20 1.498(6) . ? C21 C26 1.385(5) . ? C21 C22 1.397(5) . ? C22 C23 1.392(5) . ? C23 C24 1.389(5) . ? C24 C25 1.385(5) . ? C24 C27 1.496(5) . ? C25 C26 1.387(5) . ? C27 F5A 1.311(5) . ? C27 F3A 1.333(5) . ? C27 F5B 1.337(10) . ? C27 F4B 1.350(10) . ? C27 F4A 1.355(5) . ? C27 F3B 1.356(10) . ? C28 C33 1.394(5) . ? C28 C29 1.395(4) . ? C29 C30 1.382(5) . ? C30 C31 1.385(5) . ? C31 C32 1.396(5) . ? C31 C35 1.510(5) . ? C32 C33 1.380(5) . ? Cl1 C34 1.732(11) . ? Cl1 C34 1.779(11) 4_655 ? C34 C34 0.930(16) 4_655 ? C34 Cl2 1.662(10) 4_655 ? C34 Cl3 1.690(14) . ? C34 Cl2 1.745(11) . ? C34 Cl3 1.764(14) 4_655 ? C34 Cl1 1.779(11) 4_655 ? Cl2 Cl2 0.40(5) 4_655 ? Cl2 C34 1.662(10) 4_655 ? C35 C36B 1.468(7) . ? C35 C36A 1.582(8) . ? C36B C37B 1.601(9) . ? C36A C37A 1.544(8) . ? Cl3 C34 1.764(14) 4_655 ? C37B C38B 1.564(9) . ? C38A C37A 1.509(8) . ? C38A C39A 1.523(8) . ? C39A C40A 1.520(9) . ? C39B C39B 1.49(3) 4_654 ? C39B C40B 1.495(10) . ? C39B C38B 1.540(10) . ? C40B C39B 1.495(10) 4_654 ? C41 C41 0.94(5) 4_655 ? C41 Cl5 1.11(3) 4_655 ? C41 Cl6 1.61(4) 4_655 ? C41 Cl5 1.710(10) . ? C41 Cl4 1.717(10) . ? C41 Cl6 1.729(10) . ? Cl4 Cl5 2.06(3) 4_655 ? Cl5 Cl6 1.01(2) . ? Cl5 C41 1.11(3) 4_655 ? Cl5 Cl4 2.06(3) 4_655 ? Cl6 C41 1.61(4) 4_655 ? 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 C1 N1 C4 108.3(3) . . ? C1 N1 B1 127.3(3) . . ? C4 N1 B1 124.2(3) . . ? N1 C1 C2 109.3(3) . . ? N1 C1 C12 123.9(3) . . ? C2 C1 C12 126.7(3) . . ? C3 C2 C1 107.9(3) . . ? C2 C3 C4 107.0(3) . . ? C5 C4 N1 122.8(3) . . ? C5 C4 C3 129.7(3) . . ? N1 C4 C3 107.5(3) . . ? C4 C5 C6 120.0(3) . . ? C4 C5 C21 117.6(3) . . ? C6 C5 C21 122.5(3) . . ? N2 C6 C7 109.8(3) . . ? N2 C6 C5 118.5(3) . . ? C7 C6 C5 131.7(3) . . ? C9 N2 C6 108.1(3) . . ? C9 N2 B1 123.7(3) . . ? C6 N2 B1 128.1(3) . . ? C6 C7 C8 106.3(3) . . ? C6 C7 C28 128.5(3) . . ? C8 C7 C28 125.2(3) . . ? C11 C8 C7 132.4(3) . . ? C11 C8 C9 121.1(3) . . ? C7 C8 C9 106.5(3) . . ? N2 C9 C10 127.5(3) . . ? N2 C9 C8 109.3(3) . . ? C10 C9 C8 123.3(3) . . ? C9 C10 C9 114.7(4) 4_655 . ? C8 C11 C8 116.4(4) 4_655 . ? F1 B1 F2 109.7(3) . . ? F1 B1 N2 110.7(3) . . ? F2 B1 N2 110.2(3) . . ? F1 B1 N1 109.7(3) . . ? F2 B1 N1 110.4(3) . . ? N2 B1 N1 106.0(3) . . ? C17 C12 C13 120.7(4) . . ? C17 C12 C1 119.2(3) . . ? C13 C12 C1 120.1(3) . . ? C14 C13 C12 118.4(4) . . ? C14 C13 C18 120.8(4) . . ? C12 C13 C18 120.8(4) . . ? C15 C14 C13 122.3(4) . . ? C16 C15 C14 118.2(4) . . ? C16 C15 C19 121.3(4) . . ? C14 C15 C19 120.5(5) . . ? C15 C16 C17 122.4(4) . . ? C12 C17 C16 117.9(4) . . ? C12 C17 C20 121.4(4) . . ? C16 C17 C20 120.6(4) . . ? C26 C21 C22 119.7(3) . . ? C26 C21 C5 121.2(3) . . ? C22 C21 C5 119.1(3) . . ? C23 C22 C21 119.9(3) . . ? C24 C23 C22 119.8(3) . . ? C25 C24 C23 120.2(3) . . ? C25 C24 C27 119.9(3) . . ? C23 C24 C27 119.8(3) . . ? C24 C25 C26 119.9(3) . . ? C21 C26 C25 120.4(3) . . ? F5A C27 F3A 107.8(4) . . ? F5A C27 F5B 126.4(17) . . ? F3A C27 F5B 56(2) . . ? F5A C27 F4B 54.0(16) . . ? F3A C27 F4B 130.6(15) . . ? F5B C27 F4B 95(2) . . ? F5A C27 F4A 106.2(3) . . ? F3A C27 F4A 104.0(3) . . ? F5B C27 F4A 49(2) . . ? F4B C27 F4A 54.6(16) . . ? F5A C27 F3B 52.5(17) . . ? F3A C27 F3B 62.2(17) . . ? F5B C27 F3B 112(2) . . ? F4B C27 F3B 104(2) . . ? F4A C27 F3B 139.8(16) . . ? F5A C27 C24 113.1(3) . . ? F3A C27 C24 112.8(3) . . ? F5B C27 C24 120.2(17) . . ? F4B C27 C24 116.5(15) . . ? F4A C27 C24 112.3(3) . . ? F3B C27 C24 107.7(16) . . ? C33 C28 C29 118.1(3) . . ? C33 C28 C7 119.9(3) . . ? C29 C28 C7 121.9(3) . . ? C30 C29 C28 120.3(3) . . ? C29 C30 C31 121.6(3) . . ? C30 C31 C32 118.0(3) . . ? C30 C31 C35 121.3(4) . . ? C32 C31 C35 120.7(4) . . ? C33 C32 C31 120.6(3) . . ? C32 C33 C28 121.1(3) . . ? C34 Cl1 C34 30.7(5) . 4_655 ? C34 C34 Cl2 79.2(7) 4_655 4_655 ? C34 C34 Cl3 78.8(12) 4_655 . ? Cl2 C34 Cl3 118.8(10) 4_655 . ? C34 C34 Cl1 77.4(11) 4_655 . ? Cl2 C34 Cl1 121.7(10) 4_655 . ? Cl3 C34 Cl1 3.8(6) . . ? C34 C34 Cl2 69.2(6) 4_655 . ? Cl2 C34 Cl2 13.0(15) 4_655 . ? Cl3 C34 Cl2 107.6(10) . . ? Cl1 C34 Cl2 110.1(9) . . ? C34 C34 Cl3 70.0(10) 4_655 4_655 ? Cl2 C34 Cl3 108.0(8) 4_655 4_655 ? Cl3 C34 Cl3 116.4(8) . 4_655 ? Cl1 C34 Cl3 112.6(5) . 4_655 ? Cl2 C34 Cl3 110.6(7) . 4_655 ? C34 C34 Cl1 71.9(9) 4_655 4_655 ? Cl2 C34 Cl1 111.8(7) 4_655 4_655 ? Cl3 C34 Cl1 114.0(5) . 4_655 ? Cl1 C34 Cl1 110.2(6) . 4_655 ? Cl2 C34 Cl1 114.5(7) . 4_655 ? Cl3 C34 Cl1 3.9(5) 4_655 4_655 ? Cl2 Cl2 C34 95.6(12) 4_655 4_655 ? Cl2 Cl2 C34 71.3(10) 4_655 . ? C34 Cl2 C34 31.6(5) 4_655 . ? C36B C35 C31 122.5(5) . . ? C36B C35 C36A 28.8(4) . . ? C31 C35 C36A 110.2(4) . . ? C35 C36B C37B 118.6(7) . . ? C37A C36A C35 115.2(7) . . ? C34 Cl3 C34 31.1(6) . 4_655 ? C38B C37B C36B 98.0(8) . . ? C37A C38A C39A 122.2(8) . . ? C38A C37A C36A 123.6(8) . . ? C40A C39A C38A 113.7(8) . . ? C39B C39B C40B 60.1(7) 4_654 . ? C39B C39B C38B 145.2(16) 4_654 . ? C40B C39B C38B 93.5(10) . . ? C39B C38B C37B 132.7(13) . . ? C39B C40B C39B 59.8(14) . 4_654 ? C41 C41 Cl5 113(4) 4_655 4_655 ? C41 C41 Cl6 80(3) 4_655 4_655 ? Cl5 C41 Cl6 38.0(15) 4_655 4_655 ? C41 C41 Cl5 36.5(19) 4_655 . ? Cl5 C41 Cl5 124(3) 4_655 . ? Cl6 C41 Cl5 107.3(16) 4_655 . ? C41 C41 Cl4 152(2) 4_655 . ? Cl5 C41 Cl4 90.9(18) 4_655 . ? Cl6 C41 Cl4 115.3(16) 4_655 . ? Cl5 C41 Cl4 137(2) . . ? C41 C41 Cl6 67(2) 4_655 . ? Cl5 C41 Cl6 141(3) 4_655 . ? Cl6 C41 Cl6 140.6(18) 4_655 . ? Cl5 C41 Cl6 34.1(8) . . ? Cl4 C41 Cl6 104(2) . . ? C41 Cl4 Cl5 32.5(10) . 4_655 ? Cl6 Cl5 C41 100(3) . 4_655 ? Cl6 Cl5 C41 74.0(8) . . ? C41 Cl5 C41 31(2) 4_655 . ? Cl6 Cl5 Cl4 130(2) . 4_655 ? C41 Cl5 Cl4 56.6(13) 4_655 4_655 ? C41 Cl5 Cl4 86.3(16) . 4_655 ? Cl5 Cl6 C41 42.5(15) . 4_655 ? Cl5 Cl6 C41 71.9(9) . . ? C41 Cl6 C41 32.5(15) 4_655 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C2 -0.6(4) . . . . ? B1 N1 C1 C2 174.2(3) . . . . ? C4 N1 C1 C12 176.1(3) . . . . ? B1 N1 C1 C12 -9.2(6) . . . . ? N1 C1 C2 C3 0.0(4) . . . . ? C12 C1 C2 C3 -176.5(4) . . . . ? C1 C2 C3 C4 0.5(4) . . . . ? C1 N1 C4 C5 -179.2(3) . . . . ? B1 N1 C4 C5 5.9(5) . . . . ? C1 N1 C4 C3 0.9(4) . . . . ? B1 N1 C4 C3 -174.0(3) . . . . ? C2 C3 C4 C5 179.2(4) . . . . ? C2 C3 C4 N1 -0.9(4) . . . . ? N1 C4 C5 C6 -1.8(5) . . . . ? C3 C4 C5 C6 178.1(3) . . . . ? N1 C4 C5 C21 177.9(3) . . . . ? C3 C4 C5 C21 -2.2(5) . . . . ? C4 C5 C6 N2 -3.7(5) . . . . ? C21 C5 C6 N2 176.6(3) . . . . ? C4 C5 C6 C7 176.9(3) . . . . ? C21 C5 C6 C7 -2.9(5) . . . . ? C7 C6 N2 C9 1.2(4) . . . . ? C5 C6 N2 C9 -178.3(3) . . . . ? C7 C6 N2 B1 -174.6(3) . . . . ? C5 C6 N2 B1 5.8(5) . . . . ? N2 C6 C7 C8 -0.6(4) . . . . ? C5 C6 C7 C8 178.8(3) . . . . ? N2 C6 C7 C28 -179.3(3) . . . . ? C5 C6 C7 C28 0.2(6) . . . . ? C6 C7 C8 C11 177.4(3) . . . . ? C28 C7 C8 C11 -3.9(5) . . . . ? C6 C7 C8 C9 -0.2(3) . . . . ? C28 C7 C8 C9 178.5(3) . . . . ? C6 N2 C9 C10 177.0(3) . . . . ? B1 N2 C9 C10 -6.9(5) . . . . ? C6 N2 C9 C8 -1.4(4) . . . . ? B1 N2 C9 C8 174.7(3) . . . . ? C11 C8 C9 N2 -176.9(2) . . . . ? C7 C8 C9 N2 1.0(4) . . . . ? C11 C8 C9 C10 4.6(4) . . . . ? C7 C8 C9 C10 -177.5(3) . . . . ? N2 C9 C10 C9 179.6(4) . . . 4_655 ? C8 C9 C10 C9 -2.2(2) . . . 4_655 ? C7 C8 C11 C8 -179.4(4) . . . 4_655 ? C9 C8 C11 C8 -2.2(2) . . . 4_655 ? C9 N2 B1 F1 63.7(5) . . . . ? C6 N2 B1 F1 -121.0(4) . . . . ? C9 N2 B1 F2 -57.8(4) . . . . ? C6 N2 B1 F2 117.4(4) . . . . ? C9 N2 B1 N1 -177.4(3) . . . . ? C6 N2 B1 N1 -2.1(5) . . . . ? C1 N1 B1 F1 -58.1(5) . . . . ? C4 N1 B1 F1 115.9(4) . . . . ? C1 N1 B1 F2 63.0(5) . . . . ? C4 N1 B1 F2 -123.1(3) . . . . ? C1 N1 B1 N2 -177.7(3) . . . . ? C4 N1 B1 N2 -3.7(5) . . . . ? N1 C1 C12 C17 -84.4(5) . . . . ? C2 C1 C12 C17 91.7(5) . . . . ? N1 C1 C12 C13 98.2(4) . . . . ? C2 C1 C12 C13 -85.8(5) . . . . ? C17 C12 C13 C14 -0.6(6) . . . . ? C1 C12 C13 C14 176.8(4) . . . . ? C17 C12 C13 C18 179.2(4) . . . . ? C1 C12 C13 C18 -3.4(6) . . . . ? C12 C13 C14 C15 0.6(7) . . . . ? C18 C13 C14 C15 -179.3(4) . . . . ? C13 C14 C15 C16 -0.4(7) . . . . ? C13 C14 C15 C19 -179.9(4) . . . . ? C14 C15 C16 C17 0.2(7) . . . . ? C19 C15 C16 C17 179.7(4) . . . . ? C13 C12 C17 C16 0.4(5) . . . . ? C1 C12 C17 C16 -177.0(3) . . . . ? C13 C12 C17 C20 179.7(4) . . . . ? C1 C12 C17 C20 2.3(5) . . . . ? C15 C16 C17 C12 -0.2(6) . . . . ? C15 C16 C17 C20 -179.5(4) . . . . ? C4 C5 C21 C26 116.7(4) . . . . ? C6 C5 C21 C26 -63.6(4) . . . . ? C4 C5 C21 C22 -62.7(4) . . . . ? C6 C5 C21 C22 117.0(4) . . . . ? C26 C21 C22 C23 1.1(5) . . . . ? C5 C21 C22 C23 -179.5(3) . . . . ? C21 C22 C23 C24 -0.9(5) . . . . ? C22 C23 C24 C25 0.5(5) . . . . ? C22 C23 C24 C27 178.4(3) . . . . ? C23 C24 C25 C26 -0.4(5) . . . . ? C27 C24 C25 C26 -178.3(3) . . . . ? C22 C21 C26 C25 -1.0(5) . . . . ? C5 C21 C26 C25 179.6(3) . . . . ? C24 C25 C26 C21 0.7(5) . . . . ? C25 C24 C27 F5A -40.5(5) . . . . ? C23 C24 C27 F5A 141.6(4) . . . . ? C25 C24 C27 F3A 82.2(4) . . . . ? C23 C24 C27 F3A -95.7(4) . . . . ? C25 C24 C27 F5B 145(2) . . . . ? C23 C24 C27 F5B -33(2) . . . . ? C25 C24 C27 F4B -100.4(18) . . . . ? C23 C24 C27 F4B 81.7(18) . . . . ? C25 C24 C27 F4A -160.7(3) . . . . ? C23 C24 C27 F4A 21.4(5) . . . . ? C25 C24 C27 F3B 15.6(18) . . . . ? C23 C24 C27 F3B -162.3(18) . . . . ? C6 C7 C28 C33 116.1(4) . . . . ? C8 C7 C28 C33 -62.3(4) . . . . ? C6 C7 C28 C29 -61.3(5) . . . . ? C8 C7 C28 C29 120.3(4) . . . . ? C33 C28 C29 C30 -3.1(5) . . . . ? C7 C28 C29 C30 174.3(3) . . . . ? C28 C29 C30 C31 0.3(5) . . . . ? C29 C30 C31 C32 2.3(6) . . . . ? C29 C30 C31 C35 -177.1(4) . . . . ? C30 C31 C32 C33 -2.0(6) . . . . ? C35 C31 C32 C33 177.4(4) . . . . ? C31 C32 C33 C28 -0.9(5) . . . . ? C29 C28 C33 C32 3.5(5) . . . . ? C7 C28 C33 C32 -174.1(3) . . . . ? C34 Cl1 C34 Cl2 -68.7(9) 4_655 . . 4_655 ? C34 Cl1 C34 Cl3 -112(8) 4_655 . . . ? C34 Cl1 C34 Cl2 -62.1(8) 4_655 . . . ? C34 Cl1 C34 Cl3 61.8(7) 4_655 . . 4_655 ? C34 Cl1 C34 Cl1 65.1(7) 4_655 . . 4_655 ? C34 C34 Cl2 Cl2 138(4) 4_655 . . 4_655 ? Cl3 C34 Cl2 Cl2 -151(4) . . . 4_655 ? Cl1 C34 Cl2 Cl2 -154(4) . . . 4_655 ? Cl3 C34 Cl2 Cl2 81(4) 4_655 . . 4_655 ? Cl1 C34 Cl2 Cl2 81(4) 4_655 . . 4_655 ? Cl2 C34 Cl2 C34 -138(4) 4_655 . . 4_655 ? Cl3 C34 Cl2 C34 70.3(13) . . . 4_655 ? Cl1 C34 Cl2 C34 67.3(12) . . . 4_655 ? Cl3 C34 Cl2 C34 -57.8(11) 4_655 . . 4_655 ? Cl1 C34 Cl2 C34 -57.5(11) 4_655 . . 4_655 ? C30 C31 C35 C36B -136.9(7) . . . . ? C32 C31 C35 C36B 43.7(8) . . . . ? C30 C31 C35 C36A -107.7(6) . . . . ? C32 C31 C35 C36A 72.9(7) . . . . ? C31 C35 C36B C37B -173.9(7) . . . . ? C36A C35 C36B C37B 114.0(15) . . . . ? C36B C35 C36A C37A -63.7(11) . . . . ? C31 C35 C36A C37A 175.2(7) . . . . ? Cl2 C34 Cl3 C34 -70.9(9) 4_655 . . 4_655 ? Cl1 C34 Cl3 C34 68(8) . . . 4_655 ? Cl2 C34 Cl3 C34 -63.8(8) . . . 4_655 ? Cl3 C34 Cl3 C34 60.9(7) 4_655 . . 4_655 ? Cl1 C34 Cl3 C34 64.3(6) 4_655 . . 4_655 ? C35 C36B C37B C38B 136.1(10) . . . . ? C39A C38A C37A C36A -163.1(11) . . . . ? C35 C36A C37A C38A 112.1(12) . . . . ? C37A C38A C39A C40A -143.8(13) . . . . ? C39B C39B C38B C37B 146(3) 4_654 . . . ? C40B C39B C38B C37B 107.8(19) . . . . ? C36B C37B C38B C39B -143.8(19) . . . . ? C38B C39B C40B C39B 156(2) . . . 4_654 ? C41 C41 Cl4 Cl5 151(8) 4_655 . . 4_655 ? Cl6 C41 Cl4 Cl5 30.2(15) 4_655 . . 4_655 ? Cl5 C41 Cl4 Cl5 -148(5) . . . 4_655 ? Cl6 C41 Cl4 Cl5 -143(3) . . . 4_655 ? C41 C41 Cl5 Cl6 146(3) 4_655 . . . ? Cl5 C41 Cl5 Cl6 -132(4) 4_655 . . . ? Cl6 C41 Cl5 Cl6 -170(3) 4_655 . . . ? Cl4 C41 Cl5 Cl6 9(4) . . . . ? Cl5 C41 Cl5 C41 83(5) 4_655 . . 4_655 ? Cl6 C41 Cl5 C41 45(4) 4_655 . . 4_655 ? Cl4 C41 Cl5 C41 -137(3) . . . 4_655 ? Cl6 C41 Cl5 C41 -146(3) . . . 4_655 ? C41 C41 Cl5 Cl4 12(2) 4_655 . . 4_655 ? Cl5 C41 Cl5 Cl4 95(3) 4_655 . . 4_655 ? Cl6 C41 Cl5 Cl4 56(2) 4_655 . . 4_655 ? Cl4 C41 Cl5 Cl4 -125(4) . . . 4_655 ? Cl6 C41 Cl5 Cl4 -134(2) . . . 4_655 ? C41 Cl5 Cl6 C41 -16.9(12) . . . 4_655 ? Cl4 Cl5 Cl6 C41 53.9(18) 4_655 . . 4_655 ? C41 Cl5 Cl6 C41 16.9(12) 4_655 . . . ? Cl4 Cl5 Cl6 C41 71(2) 4_655 . . . ? C41 C41 Cl6 Cl5 -21.5(17) 4_655 . . . ? Cl5 C41 Cl6 Cl5 77(4) 4_655 . . . ? Cl6 C41 Cl6 Cl5 15(5) 4_655 . . . ? Cl4 C41 Cl6 Cl5 -174(3) . . . . ? Cl5 C41 Cl6 C41 99(4) 4_655 . . 4_655 ? Cl6 C41 Cl6 C41 37(5) 4_655 . . 4_655 ? Cl5 C41 Cl6 C41 21.5(17) . . . 4_655 ? Cl4 C41 Cl6 C41 -152.6(17) . . . 4_655 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.833 _refine_diff_density_min -0.621 _refine_diff_density_rms 0.075 #------------------------------------------------------------------------------ # TEXT data_compound3 _database_code_depnum_ccdc_archive 'CCDC 899846' #TrackingRef '13690_web_deposit_cif_file_2_AtsushiWakamiya_1346680845.compound3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H30 B F5 N2' _chemical_formula_weight 572.41 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' 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.2815(2) _cell_length_b 20.19380(10) _cell_length_c 30.6952(4) _cell_angle_alpha 90.02 _cell_angle_beta 90.0000(6) _cell_angle_gamma 90.00 _cell_volume 5753.16(15) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 8342 _cell_measurement_theta_min 2.2934 _cell_measurement_theta_max 27.8764 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2384 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9804 _exptl_absorpt_correction_T_max 0.9853 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn70 CCD (4x4 bin mode) with MicroMax-007 ; _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 58752 _diffrn_reflns_av_R_equivalents 0.0604 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.50 _reflns_number_total 10608 _reflns_number_gt 9175 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 for windows' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[?^2^(Fo^2^)+(0.0646P)^2^+0.8106P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef none _refine_ls_number_reflns 10608 _refine_ls_number_parameters 802 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1170 _refine_ls_wR_factor_gt 0.1030 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 0.0575(3) 0.27966(11) 0.24355(8) 0.0261(5) Uani 1 1 d . . . F1 F 0.18694(13) 0.28395(6) 0.22142(5) 0.0366(3) Uani 1 1 d . . . F2 F 0.08107(14) 0.27848(5) 0.28798(4) 0.0333(3) Uani 1 1 d . . . N1 N -0.02582(19) 0.21635(8) 0.22904(5) 0.0255(4) Uani 1 1 d . . . C1 C 0.0106(2) 0.15261(10) 0.23694(7) 0.0296(5) Uani 1 1 d . . . C2 C -0.0924(3) 0.11033(11) 0.21739(7) 0.0354(5) Uani 1 1 d . . . H1 H -0.0937 0.0633 0.2187 0.043 Uiso 1 1 calc R . . C3 C -0.1904(2) 0.14988(11) 0.19608(7) 0.0329(5) Uani 1 1 d . . . H2 H -0.2709 0.1352 0.1796 0.039 Uiso 1 1 calc R . . C4 C -0.1493(2) 0.21657(10) 0.20328(7) 0.0267(5) Uani 1 1 d . . . C5 C -0.2163(2) 0.27539(10) 0.19098(7) 0.0263(5) Uani 1 1 d . . . C6 C -0.1670(2) 0.33600(10) 0.20645(7) 0.0257(4) Uani 1 1 d . . . C7 C -0.2212(2) 0.40078(10) 0.20162(7) 0.0299(5) Uani 1 1 d . . . H3 H -0.3054 0.4132 0.1860 0.036 Uiso 1 1 calc R . . C8 C -0.1298(2) 0.44296(11) 0.22372(7) 0.0327(5) Uani 1 1 d . . . H4 H -0.1406 0.4895 0.2266 0.039 Uiso 1 1 calc R . . C9 C -0.0173(2) 0.40420(10) 0.24118(7) 0.0281(5) Uani 1 1 d . . . N2 N -0.04127(18) 0.33955(8) 0.23134(5) 0.0237(4) Uani 1 1 d . . . C10 C 0.1460(2) 0.13326(10) 0.25946(7) 0.0305(5) Uani 1 1 d . . . C11 C 0.2708(3) 0.12593(11) 0.23446(7) 0.0335(5) Uani 1 1 d . . . C12 C 0.3987(3) 0.10950(12) 0.25536(8) 0.0405(6) Uani 1 1 d . . . H5 H 0.4842 0.1051 0.2386 0.049 Uiso 1 1 calc R . . C13 C 0.4051(3) 0.09936(12) 0.30017(8) 0.0424(6) Uani 1 1 d . . . C14 C 0.2790(3) 0.10535(11) 0.32381(8) 0.0428(6) Uani 1 1 d . . . H6 H 0.2816 0.0974 0.3543 0.051 Uiso 1 1 calc R . . C15 C 0.1482(3) 0.12257(11) 0.30470(7) 0.0355(5) Uani 1 1 d . . . C16 C 0.2674(3) 0.13439(13) 0.18549(7) 0.0424(6) Uani 1 1 d . . . H7 H 0.3661 0.1374 0.1744 0.064 Uiso 1 1 calc R . . H8 H 0.2149 0.1750 0.1782 0.064 Uiso 1 1 calc R . . H9 H 0.2189 0.0963 0.1722 0.064 Uiso 1 1 calc R . . C17 C 0.5461(3) 0.08326(15) 0.32227(9) 0.0607(9) Uani 1 1 d . . . H10 H 0.5643 0.1155 0.3455 0.091 Uiso 1 1 calc R . . H11 H 0.6244 0.0853 0.3009 0.091 Uiso 1 1 calc R . . H12 H 0.5413 0.0386 0.3347 0.091 Uiso 1 1 calc R . . C18 C 0.0143(3) 0.12976(13) 0.33167(8) 0.0487(7) Uani 1 1 d . . . H13 H 0.0335 0.1145 0.3614 0.073 Uiso 1 1 calc R . . H14 H -0.0631 0.1031 0.3189 0.073 Uiso 1 1 calc R . . H15 H -0.0149 0.1764 0.3323 0.073 Uiso 1 1 calc R . . C19 C -0.3366(2) 0.27193(10) 0.15897(7) 0.0269(5) Uani 1 1 d . . . C20 C -0.4790(2) 0.28703(11) 0.16967(8) 0.0332(5) Uani 1 1 d . . . H16 H -0.5031 0.3005 0.1984 0.040 Uiso 1 1 calc R . . C21 C -0.5845(3) 0.28220(11) 0.13816(8) 0.0360(5) Uani 1 1 d . . . H17 H -0.6817 0.2921 0.1453 0.043 Uiso 1 1 calc R . . C22 C -0.5488(3) 0.26283(11) 0.09596(8) 0.0329(5) Uani 1 1 d . . . C23 C -0.4073(3) 0.24905(12) 0.08514(8) 0.0361(6) Uani 1 1 d . . . H18 H -0.3828 0.2370 0.0562 0.043 Uiso 1 1 calc R . . C24 C -0.3022(3) 0.25292(11) 0.11673(8) 0.0337(5) Uani 1 1 d . . . H19 H -0.2052 0.2425 0.1096 0.040 Uiso 1 1 calc R . . C25 C -0.6636(3) 0.25874(13) 0.06236(9) 0.0437(6) Uani 1 1 d . . . F3 F -0.78661(19) 0.23444(11) 0.07750(7) 0.0761(6) Uani 1 1 d . . . F4 F -0.6982(2) 0.31841(8) 0.04597(5) 0.0667(5) Uani 1 1 d . . . F5 F -0.6272(2) 0.22192(9) 0.02810(6) 0.0700(6) Uani 1 1 d . . . C26 C 0.1171(2) 0.42587(10) 0.26299(7) 0.0288(5) Uani 1 1 d . . . C27 C 0.2400(2) 0.43673(11) 0.23744(7) 0.0323(5) Uani 1 1 d . . . C28 C 0.3688(3) 0.45301(11) 0.25821(8) 0.0375(5) Uani 1 1 d . . . H20 H 0.4530 0.4595 0.2412 0.045 Uiso 1 1 calc R . . C29 C 0.3772(3) 0.46001(12) 0.30324(8) 0.0403(6) Uani 1 1 d . . . C30 C 0.2520(3) 0.45162(11) 0.32748(8) 0.0389(6) Uani 1 1 d . . . H21 H 0.2559 0.4579 0.3581 0.047 Uiso 1 1 calc R . . C31 C 0.1214(3) 0.43433(10) 0.30840(7) 0.0317(5) Uani 1 1 d . . . C32 C 0.2340(3) 0.43128(12) 0.18844(7) 0.0393(6) Uani 1 1 d . . . H22 H 0.1861 0.4705 0.1764 0.059 Uiso 1 1 calc R . . H23 H 0.1800 0.3915 0.1803 0.059 Uiso 1 1 calc R . . H24 H 0.3322 0.4284 0.1768 0.059 Uiso 1 1 calc R . . C33 C 0.5187(3) 0.47550(15) 0.32497(9) 0.0583(8) Uani 1 1 d . . . H25 H 0.5140 0.5196 0.3382 0.087 Uiso 1 1 calc R . . H26 H 0.5961 0.4745 0.3032 0.087 Uiso 1 1 calc R . . H27 H 0.5382 0.4425 0.3476 0.087 Uiso 1 1 calc R . . C34 C -0.0109(3) 0.42411(12) 0.33583(8) 0.0425(6) Uani 1 1 d . . . H28 H 0.0127 0.4321 0.3665 0.064 Uiso 1 1 calc R . . H29 H -0.0453 0.3785 0.3323 0.064 Uiso 1 1 calc R . . H30 H -0.0863 0.4550 0.3266 0.064 Uiso 1 1 calc R . . B2 B -0.0675(3) 0.25027(11) -0.00630(8) 0.0260(5) Uani 1 1 d . . . F6 F -0.19830(13) 0.25502(6) -0.02829(5) 0.0370(3) Uani 1 1 d . . . F7 F -0.08993(14) 0.24922(6) 0.03797(4) 0.0340(3) Uani 1 1 d . . . N3 N 0.01386(18) 0.18663(8) -0.02106(6) 0.0261(4) Uani 1 1 d . . . C35 C -0.0236(2) 0.12296(10) -0.01312(7) 0.0296(5) Uani 1 1 d . . . C36 C 0.0796(2) 0.08082(10) -0.03210(7) 0.0327(5) Uani 1 1 d . . . H31 H 0.0798 0.0338 -0.0309 0.039 Uiso 1 1 calc R . . C37 C 0.1800(2) 0.11967(10) -0.05272(7) 0.0308(5) Uani 1 1 d . . . H32 H 0.2617 0.1045 -0.0685 0.037 Uiso 1 1 calc R . . C38 C 0.1392(2) 0.18631(10) -0.04616(7) 0.0268(5) Uani 1 1 d . . . C39 C 0.2062(2) 0.24494(10) -0.05905(7) 0.0259(5) Uani 1 1 d . . . C40 C 0.1563(2) 0.30604(10) -0.04431(7) 0.0266(5) Uani 1 1 d . . . C41 C 0.2101(2) 0.37113(10) -0.04990(7) 0.0306(5) Uani 1 1 d . . . H33 H 0.2941 0.3833 -0.0657 0.037 Uiso 1 1 calc R . . C42 C 0.1186(2) 0.41341(11) -0.02833(7) 0.0324(5) Uani 1 1 d . . . H34 H 0.1283 0.4601 -0.0263 0.039 Uiso 1 1 calc R . . C43 C 0.0075(2) 0.37484(10) -0.00978(7) 0.0271(5) Uani 1 1 d . . . N4 N 0.03097(19) 0.31016(8) -0.01899(6) 0.0264(4) Uani 1 1 d . . . C44 C -0.1622(2) 0.10542(10) 0.00809(7) 0.0292(5) Uani 1 1 d . . . C45 C -0.1715(2) 0.09528(10) 0.05315(7) 0.0313(5) Uani 1 1 d . . . C46 C -0.3059(3) 0.08170(11) 0.07118(8) 0.0367(5) Uani 1 1 d . . . H35 H -0.3129 0.0746 0.1017 0.044 Uiso 1 1 calc R . . C47 C -0.4306(3) 0.07817(11) 0.04597(8) 0.0366(5) Uani 1 1 d . . . C48 C -0.4172(3) 0.08626(11) 0.00135(8) 0.0377(5) Uani 1 1 d . . . H36 H -0.5006 0.0827 -0.0164 0.045 Uiso 1 1 calc R . . C49 C -0.2845(2) 0.09952(11) -0.01833(7) 0.0332(5) Uani 1 1 d . . . C50 C -0.0392(3) 0.10037(12) 0.08186(8) 0.0395(6) Uani 1 1 d . . . H37 H -0.0648 0.0887 0.1119 0.059 Uiso 1 1 calc R . . H38 H -0.0021 0.1458 0.0811 0.059 Uiso 1 1 calc R . . H39 H 0.0350 0.0699 0.0712 0.059 Uiso 1 1 calc R . . C51 C -0.5771(3) 0.06678(14) 0.06614(9) 0.0493(7) Uani 1 1 d . . . H40 H -0.5807 0.0223 0.0789 0.074 Uiso 1 1 calc R . . H41 H -0.6516 0.0708 0.0437 0.074 Uiso 1 1 calc R . . H42 H -0.5940 0.0998 0.0890 0.074 Uiso 1 1 calc R . . C52 C -0.2747(3) 0.10743(12) -0.06699(7) 0.0399(6) Uani 1 1 d . . . H43 H -0.2249 0.1489 -0.0739 0.060 Uiso 1 1 calc R . . H44 H -0.3720 0.1084 -0.0794 0.060 Uiso 1 1 calc R . . H45 H -0.2210 0.0701 -0.0794 0.060 Uiso 1 1 calc R . . C53 C -0.1251(2) 0.39730(10) 0.01275(7) 0.0287(5) Uani 1 1 d . . . C54 C -0.1271(3) 0.40638(11) 0.05792(7) 0.0350(5) Uani 1 1 d . . . C55 C -0.2559(3) 0.42557(11) 0.07774(8) 0.0401(6) Uani 1 1 d . . . H46 H -0.2576 0.4329 0.1083 0.048 Uiso 1 1 calc R . . C56 C -0.3814(3) 0.43425(11) 0.05396(8) 0.0400(6) Uani 1 1 d . . . C57 C -0.3766(3) 0.42594(11) 0.00915(8) 0.0367(5) Uani 1 1 d . . . H47 H -0.4621 0.4323 -0.0074 0.044 Uiso 1 1 calc R . . C58 C -0.2498(2) 0.40857(10) -0.01226(7) 0.0328(5) Uani 1 1 d . . . C59 C 0.0046(3) 0.39488(14) 0.08538(8) 0.0478(6) Uani 1 1 d . . . H48 H -0.0139 0.4100 0.1152 0.072 Uiso 1 1 calc R . . H49 H 0.0860 0.4197 0.0732 0.072 Uiso 1 1 calc R . . H50 H 0.0277 0.3475 0.0856 0.072 Uiso 1 1 calc R . . C60 C -0.5221(3) 0.45194(13) 0.07673(10) 0.0567(8) Uani 1 1 d . . . H51 H -0.5999 0.4543 0.0552 0.085 Uiso 1 1 calc R . . H52 H -0.5119 0.4949 0.0912 0.085 Uiso 1 1 calc R . . H53 H -0.5450 0.4179 0.0984 0.085 Uiso 1 1 calc R . . C61 C -0.2467(3) 0.40245(12) -0.06120(7) 0.0387(6) Uani 1 1 d . . . H54 H -0.2018 0.4420 -0.0738 0.058 Uiso 1 1 calc R . . H55 H -0.3454 0.3982 -0.0722 0.058 Uiso 1 1 calc R . . H56 H -0.1910 0.3632 -0.0694 0.058 Uiso 1 1 calc R . . C62 C 0.3265(2) 0.24143(10) -0.09101(7) 0.0281(5) Uani 1 1 d . A . C63 C 0.2940(3) 0.22027(11) -0.13297(7) 0.0321(5) Uani 1 1 d . . . H57 H 0.1978 0.2086 -0.1402 0.039 Uiso 1 1 calc R . . C64 C 0.4005(3) 0.21607(12) -0.16428(8) 0.0372(6) Uani 1 1 d . A . H58 H 0.3777 0.2021 -0.1930 0.045 Uiso 1 1 calc R . . C65 C 0.5406(3) 0.23250(11) -0.15336(8) 0.0343(5) Uani 1 1 d . . . C66 C 0.5741(3) 0.25395(11) -0.11179(8) 0.0366(6) Uani 1 1 d . A . H59 H 0.6706 0.2653 -0.1047 0.044 Uiso 1 1 calc R . . C67 C 0.4669(2) 0.25889(11) -0.08054(8) 0.0332(5) Uani 1 1 d . . . H60 H 0.4894 0.2742 -0.0521 0.040 Uiso 1 1 calc R A . C68B C 0.6687(15) 0.2271(6) -0.1826(4) 0.037(3) Uiso 0.48(2) 1 d P A 2 F8B F 0.6352(18) 0.1796(9) -0.2146(6) 0.127(6) Uani 0.48(2) 1 d P A 2 F9B F 0.6797(13) 0.2821(5) -0.2086(4) 0.081(3) Uani 0.48(2) 1 d P A 2 F10B F 0.7880(10) 0.2212(5) -0.1690(4) 0.086(3) Uani 0.48(2) 1 d P A 2 F9A F 0.6140(13) 0.2568(6) -0.2249(2) 0.075(3) Uani 0.52(2) 1 d P A 1 F10A F 0.7777(10) 0.2482(9) -0.1765(4) 0.115(5) Uani 0.52(2) 1 d P A 1 C68A C 0.6447(11) 0.2261(5) -0.1913(4) 0.039(2) Uani 0.52(2) 1 d P A 1 F8A F 0.6780(9) 0.1642(4) -0.1996(3) 0.072(2) Uani 0.52(2) 1 d P 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 B1 0.0291(12) 0.0242(13) 0.0248(13) -0.0005(9) -0.0018(11) 0.0026(9) F1 0.0289(7) 0.0307(7) 0.0501(8) -0.0016(6) 0.0056(6) -0.0003(5) F2 0.0440(8) 0.0250(7) 0.0307(7) -0.0008(5) -0.0119(6) 0.0015(5) N1 0.0296(9) 0.0235(9) 0.0235(9) 0.0004(7) -0.0015(8) -0.0002(7) C1 0.0371(12) 0.0258(11) 0.0259(11) 0.0005(9) 0.0003(10) 0.0007(9) C2 0.0451(13) 0.0227(11) 0.0386(13) -0.0012(9) -0.0049(11) -0.0033(9) C3 0.0361(12) 0.0330(12) 0.0295(12) -0.0043(9) -0.0041(10) -0.0051(10) C4 0.0278(11) 0.0282(11) 0.0242(11) -0.0025(8) -0.0013(9) -0.0020(8) C5 0.0270(11) 0.0294(12) 0.0226(11) 0.0004(8) 0.0018(9) -0.0001(8) C6 0.0259(10) 0.0278(11) 0.0235(11) 0.0009(8) -0.0008(8) 0.0006(8) C7 0.0326(11) 0.0305(11) 0.0266(11) 0.0011(9) -0.0019(9) 0.0053(9) C8 0.0408(12) 0.0262(11) 0.0312(12) 0.0014(9) -0.0012(10) 0.0046(9) C9 0.0342(11) 0.0248(11) 0.0253(11) -0.0004(8) -0.0009(9) -0.0012(9) N2 0.0256(8) 0.0219(8) 0.0238(9) -0.0005(7) -0.0021(7) -0.0001(7) C10 0.0421(12) 0.0207(10) 0.0287(11) -0.0011(8) -0.0052(10) 0.0034(9) C11 0.0426(13) 0.0259(11) 0.0321(12) -0.0014(9) -0.0055(10) 0.0068(9) C12 0.0436(13) 0.0347(13) 0.0431(15) -0.0066(11) -0.0080(11) 0.0125(11) C13 0.0540(15) 0.0317(12) 0.0414(15) -0.0093(10) -0.0159(12) 0.0141(11) C14 0.0662(17) 0.0300(12) 0.0320(13) -0.0038(10) -0.0130(13) 0.0101(12) C15 0.0503(14) 0.0253(11) 0.0307(12) 0.0009(9) -0.0054(11) 0.0043(10) C16 0.0489(15) 0.0443(14) 0.0340(13) 0.0017(11) 0.0004(11) 0.0122(11) C17 0.0687(19) 0.0580(17) 0.0554(18) -0.0166(14) -0.0283(16) 0.0282(15) C18 0.0612(17) 0.0478(16) 0.0370(14) 0.0067(11) 0.0015(13) 0.0033(13) C19 0.0284(11) 0.0281(11) 0.0242(11) -0.0006(9) -0.0002(9) -0.0011(8) C20 0.0289(12) 0.0427(13) 0.0279(12) -0.0040(10) -0.0013(10) 0.0028(9) C21 0.0264(12) 0.0422(14) 0.0394(14) -0.0014(10) -0.0011(11) 0.0029(9) C22 0.0336(12) 0.0358(11) 0.0293(13) 0.0001(10) -0.0065(10) 0.0015(10) C23 0.0353(13) 0.0475(15) 0.0254(13) -0.0040(10) -0.0032(10) 0.0040(10) C24 0.0291(12) 0.0432(14) 0.0287(13) -0.0023(9) -0.0001(10) 0.0026(10) C25 0.0400(15) 0.0499(15) 0.0413(16) -0.0077(12) -0.0106(12) 0.0056(12) F3 0.0445(10) 0.1140(15) 0.0698(13) 0.0069(11) -0.0214(10) -0.0271(10) F4 0.0743(11) 0.0619(10) 0.0641(11) 0.0038(8) -0.0376(9) 0.0150(9) F5 0.0683(11) 0.0868(13) 0.0549(11) -0.0303(9) -0.0332(10) 0.0253(9) C26 0.0368(12) 0.0225(10) 0.0272(11) 0.0008(8) -0.0042(10) -0.0008(9) C27 0.0388(12) 0.0275(11) 0.0308(12) 0.0015(9) -0.0058(10) -0.0062(9) C28 0.0394(12) 0.0344(12) 0.0388(13) 0.0045(10) -0.0038(11) -0.0083(10) C29 0.0464(14) 0.0329(12) 0.0415(14) 0.0064(10) -0.0128(12) -0.0094(10) C30 0.0589(16) 0.0282(12) 0.0294(12) 0.0014(9) -0.0127(11) -0.0072(11) C31 0.0428(13) 0.0220(10) 0.0302(12) -0.0001(9) -0.0048(10) -0.0001(9) C32 0.0455(14) 0.0402(13) 0.0322(13) 0.0009(10) -0.0003(11) -0.0125(11) C33 0.0609(18) 0.0611(18) 0.0530(17) 0.0114(14) -0.0229(14) -0.0243(15) C34 0.0537(16) 0.0430(14) 0.0308(13) -0.0036(10) 0.0008(11) -0.0031(11) B2 0.0245(11) 0.0267(13) 0.0269(14) 0.0004(9) 0.0002(11) 0.0002(9) F6 0.0281(6) 0.0316(7) 0.0513(9) -0.0027(6) -0.0077(6) 0.0013(5) F7 0.0413(7) 0.0321(7) 0.0285(7) -0.0007(5) 0.0110(6) 0.0000(6) N3 0.0269(9) 0.0264(9) 0.0250(9) -0.0001(7) 0.0031(7) -0.0002(7) C35 0.0382(12) 0.0238(11) 0.0268(11) -0.0009(8) -0.0002(10) -0.0007(9) C36 0.0413(13) 0.0236(11) 0.0331(12) -0.0017(9) 0.0017(10) 0.0024(9) C37 0.0336(11) 0.0298(11) 0.0289(11) -0.0029(9) 0.0029(9) 0.0045(9) C38 0.0260(10) 0.0297(11) 0.0247(11) -0.0017(8) 0.0019(9) 0.0005(8) C39 0.0241(10) 0.0333(12) 0.0203(11) -0.0019(8) -0.0022(9) 0.0017(9) C40 0.0264(10) 0.0315(11) 0.0219(11) 0.0016(8) 0.0003(9) -0.0016(9) C41 0.0322(11) 0.0297(11) 0.0300(12) 0.0018(9) 0.0006(9) -0.0033(9) C42 0.0390(12) 0.0248(11) 0.0333(12) 0.0006(9) 0.0009(10) -0.0008(9) C43 0.0315(11) 0.0245(10) 0.0255(11) 0.0002(8) -0.0021(9) 0.0021(9) N4 0.0283(9) 0.0251(9) 0.0259(9) -0.0011(7) 0.0007(8) 0.0016(7) C44 0.0353(12) 0.0217(10) 0.0307(12) -0.0001(8) 0.0043(10) -0.0030(9) C45 0.0401(12) 0.0245(10) 0.0292(12) 0.0000(9) 0.0014(10) -0.0007(9) C46 0.0486(14) 0.0315(12) 0.0301(12) 0.0012(9) 0.0093(11) -0.0047(10) C47 0.0401(13) 0.0332(12) 0.0366(13) -0.0013(10) 0.0059(11) -0.0058(10) C48 0.0370(13) 0.0376(13) 0.0385(13) -0.0025(10) 0.0007(11) -0.0083(10) C49 0.0381(12) 0.0271(11) 0.0344(13) -0.0015(9) 0.0014(10) -0.0055(9) C50 0.0439(13) 0.0419(13) 0.0327(13) 0.0021(10) -0.0007(11) 0.0001(11) C51 0.0432(15) 0.0589(16) 0.0458(15) -0.0007(13) 0.0107(12) -0.0135(12) C52 0.0451(14) 0.0426(13) 0.0318(13) -0.0011(10) 0.0000(11) -0.0094(11) C53 0.0361(12) 0.0203(10) 0.0298(12) -0.0015(8) 0.0036(10) 0.0030(9) C54 0.0464(13) 0.0287(11) 0.0299(12) 0.0025(9) 0.0020(11) 0.0044(10) C55 0.0591(16) 0.0316(12) 0.0295(13) 0.0026(10) 0.0109(11) 0.0085(11) C56 0.0477(14) 0.0286(12) 0.0437(14) 0.0063(10) 0.0140(12) 0.0099(10) C57 0.0371(12) 0.0328(12) 0.0403(14) 0.0052(10) 0.0034(11) 0.0077(10) C58 0.0395(13) 0.0258(11) 0.0331(13) 0.0008(9) -0.0003(10) 0.0050(9) C59 0.0547(16) 0.0571(16) 0.0315(13) -0.0067(12) -0.0099(12) 0.0099(13) C60 0.0613(18) 0.0474(15) 0.0614(18) 0.0119(13) 0.0294(15) 0.0187(13) C61 0.0435(14) 0.0400(13) 0.0327(13) -0.0017(10) -0.0024(11) 0.0107(11) C62 0.0292(11) 0.0286(11) 0.0265(12) 0.0016(9) 0.0021(10) 0.0012(9) C63 0.0302(12) 0.0413(14) 0.0247(12) -0.0033(9) 0.0008(10) -0.0012(9) C64 0.0403(14) 0.0464(15) 0.0247(12) -0.0051(10) 0.0013(11) 0.0000(10) C65 0.0327(12) 0.0361(12) 0.0341(14) 0.0005(10) 0.0087(11) 0.0008(10) C66 0.0294(12) 0.0437(14) 0.0367(14) 0.0008(10) 0.0017(11) -0.0022(10) C67 0.0301(12) 0.0435(12) 0.0259(12) -0.0032(9) -0.0006(10) -0.0027(10) F8B 0.108(8) 0.159(12) 0.113(9) -0.103(8) 0.078(7) -0.076(7) F9B 0.070(5) 0.097(5) 0.075(6) 0.036(4) 0.039(5) 0.014(4) F10B 0.046(4) 0.123(6) 0.089(4) 0.022(5) 0.035(3) 0.037(5) F9A 0.076(5) 0.105(5) 0.044(3) 0.025(3) 0.030(3) 0.034(4) F10A 0.062(5) 0.190(12) 0.095(7) -0.072(7) 0.047(5) -0.070(6) C68A 0.028(4) 0.067(6) 0.022(4) -0.001(3) -0.002(3) 0.000(3) F8A 0.074(4) 0.052(3) 0.090(5) -0.003(3) 0.047(3) 0.020(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 F2 1.381(3) . ? B1 F1 1.382(3) . ? B1 N1 1.559(3) . ? B1 N2 1.564(3) . ? N1 C1 1.353(3) . ? N1 C4 1.392(3) . ? C1 C2 1.415(3) . ? C1 C10 1.486(3) . ? C2 C3 1.376(3) . ? C3 C4 1.417(3) . ? C4 C5 1.393(3) . ? C5 C6 1.390(3) . ? C5 C19 1.489(3) . ? C6 N2 1.397(3) . ? C6 C7 1.410(3) . ? C7 C8 1.381(3) . ? C8 C9 1.411(3) . ? C9 N2 1.358(3) . ? C9 C26 1.481(3) . ? C10 C11 1.397(3) . ? C10 C15 1.406(3) . ? C11 C12 1.390(3) . ? C11 C16 1.513(3) . ? C12 C13 1.392(3) . ? C13 C14 1.382(4) . ? C13 C17 1.510(4) . ? C14 C15 1.392(3) . ? C15 C18 1.500(3) . ? C19 C24 1.389(3) . ? C19 C20 1.396(3) . ? C20 C21 1.379(3) . ? C21 C22 1.393(3) . ? C22 C23 1.383(3) . ? C22 C25 1.485(3) . ? C23 C24 1.378(3) . ? C25 F3 1.327(3) . ? C25 F5 1.331(3) . ? C25 F4 1.345(3) . ? C26 C27 1.402(3) . ? C26 C31 1.405(3) . ? C27 C28 1.394(3) . ? C27 C32 1.509(3) . ? C28 C29 1.392(3) . ? C29 C30 1.390(4) . ? C29 C33 1.507(3) . ? C30 C31 1.391(3) . ? C31 C34 1.503(3) . ? B2 F7 1.375(3) . ? B2 F6 1.392(3) . ? B2 N3 1.558(3) . ? B2 N4 1.565(3) . ? N3 C35 1.354(3) . ? N3 C38 1.395(3) . ? C35 C36 1.407(3) . ? C35 C44 1.485(3) . ? C36 C37 1.373(3) . ? C37 C38 1.412(3) . ? C38 C39 1.395(3) . ? C39 C40 1.393(3) . ? C39 C62 1.488(3) . ? C40 N4 1.401(3) . ? C40 C41 1.417(3) . ? C41 C42 1.374(3) . ? C42 C43 1.412(3) . ? C43 N4 1.354(3) . ? C43 C53 1.483(3) . ? C44 C49 1.400(3) . ? C44 C45 1.401(3) . ? C45 C46 1.392(3) . ? C45 C50 1.515(3) . ? C46 C47 1.394(3) . ? C47 C48 1.385(3) . ? C47 C51 1.511(3) . ? C48 C49 1.398(3) . ? C49 C52 1.505(3) . ? C53 C54 1.399(3) . ? C53 C58 1.408(3) . ? C54 C55 1.396(3) . ? C54 C59 1.503(3) . ? C55 C56 1.386(4) . ? C56 C57 1.386(3) . ? C56 C60 1.523(3) . ? C57 C58 1.393(3) . ? C58 C61 1.508(3) . ? C62 C67 1.388(3) . ? C62 C63 1.390(3) . ? C63 C64 1.381(3) . ? C64 C65 1.383(3) . ? C65 C66 1.383(3) . ? C65 C68B 1.495(14) . ? C65 C68A 1.519(10) . ? C66 C67 1.386(3) . ? C68B F10B 1.190(17) . ? C68B F9B 1.370(16) . ? C68B F8B 1.406(15) . ? F9A C68A 1.237(12) . ? F10A C68A 1.389(13) . ? C68A F8A 1.312(13) . ? 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 110.41(19) . . ? F2 B1 N1 110.25(17) . . ? F1 B1 N1 110.02(17) . . ? F2 B1 N2 110.06(17) . . ? F1 B1 N2 110.07(17) . . ? N1 B1 N2 105.94(18) . . ? C1 N1 C4 108.10(16) . . ? C1 N1 B1 127.21(18) . . ? C4 N1 B1 124.61(16) . . ? N1 C1 C2 109.20(19) . . ? N1 C1 C10 123.02(19) . . ? C2 C1 C10 127.57(19) . . ? C3 C2 C1 107.34(19) . . ? C2 C3 C4 107.4(2) . . ? N1 C4 C5 121.62(18) . . ? N1 C4 C3 107.89(18) . . ? C5 C4 C3 130.4(2) . . ? C6 C5 C4 120.7(2) . . ? C6 C5 C19 120.89(18) . . ? C4 C5 C19 118.29(19) . . ? C5 C6 N2 120.46(18) . . ? C5 C6 C7 131.6(2) . . ? N2 C6 C7 107.95(18) . . ? C8 C7 C6 107.53(19) . . ? C7 C8 C9 107.43(19) . . ? N2 C9 C8 109.12(18) . . ? N2 C9 C26 121.48(18) . . ? C8 C9 C26 129.11(19) . . ? C9 N2 C6 107.93(16) . . ? C9 N2 B1 126.44(18) . . ? C6 N2 B1 125.57(16) . . ? C11 C10 C15 120.9(2) . . ? C11 C10 C1 118.25(18) . . ? C15 C10 C1 120.8(2) . . ? C12 C11 C10 118.7(2) . . ? C12 C11 C16 120.2(2) . . ? C10 C11 C16 121.1(2) . . ? C11 C12 C13 121.8(2) . . ? C14 C13 C12 118.0(2) . . ? C14 C13 C17 121.1(2) . . ? C12 C13 C17 120.8(3) . . ? C13 C14 C15 122.6(2) . . ? C14 C15 C10 117.9(2) . . ? C14 C15 C18 120.9(2) . . ? C10 C15 C18 121.2(2) . . ? C24 C19 C20 119.9(2) . . ? C24 C19 C5 117.1(2) . . ? C20 C19 C5 123.0(2) . . ? C21 C20 C19 119.4(2) . . ? C20 C21 C22 120.2(2) . . ? C23 C22 C21 120.4(2) . . ? C23 C22 C25 120.2(2) . . ? C21 C22 C25 119.4(2) . . ? C24 C23 C22 119.5(2) . . ? C23 C24 C19 120.6(2) . . ? F3 C25 F5 106.8(2) . . ? F3 C25 F4 104.9(2) . . ? F5 C25 F4 105.4(2) . . ? F3 C25 C22 113.2(2) . . ? F5 C25 C22 113.4(2) . . ? F4 C25 C22 112.4(2) . . ? C27 C26 C31 120.9(2) . . ? C27 C26 C9 118.57(18) . . ? C31 C26 C9 120.5(2) . . ? C28 C27 C26 118.6(2) . . ? C28 C27 C32 120.3(2) . . ? C26 C27 C32 121.1(2) . . ? C29 C28 C27 121.8(2) . . ? C30 C29 C28 118.2(2) . . ? C30 C29 C33 121.1(2) . . ? C28 C29 C33 120.6(2) . . ? C29 C30 C31 122.3(2) . . ? C30 C31 C26 118.2(2) . . ? C30 C31 C34 120.72(19) . . ? C26 C31 C34 121.1(2) . . ? F7 B2 F6 110.39(19) . . ? F7 B2 N3 110.35(17) . . ? F6 B2 N3 109.81(17) . . ? F7 B2 N4 110.27(18) . . ? F6 B2 N4 109.58(17) . . ? N3 B2 N4 106.37(17) . . ? C35 N3 C38 108.01(17) . . ? C35 N3 B2 127.33(18) . . ? C38 N3 B2 124.65(17) . . ? N3 C35 C36 108.96(19) . . ? N3 C35 C44 121.88(19) . . ? C36 C35 C44 128.81(19) . . ? C37 C36 C35 107.88(19) . . ? C36 C37 C38 107.29(19) . . ? C39 C38 N3 121.64(19) . . ? C39 C38 C37 130.5(2) . . ? N3 C38 C37 107.83(18) . . ? C40 C39 C38 120.7(2) . . ? C40 C39 C62 120.39(19) . . ? C38 C39 C62 118.77(19) . . ? C39 C40 N4 120.58(19) . . ? C39 C40 C41 131.7(2) . . ? N4 C40 C41 107.76(18) . . ? C42 C41 C40 107.46(19) . . ? C41 C42 C43 107.63(19) . . ? N4 C43 C42 109.31(18) . . ? N4 C43 C53 121.71(19) . . ? C42 C43 C53 128.72(19) . . ? C43 N4 C40 107.83(17) . . ? C43 N4 B2 126.85(18) . . ? C40 N4 B2 125.23(17) . . ? C49 C44 C45 120.6(2) . . ? C49 C44 C35 117.94(18) . . ? C45 C44 C35 121.4(2) . . ? C46 C45 C44 118.5(2) . . ? C46 C45 C50 120.6(2) . . ? C44 C45 C50 120.9(2) . . ? C45 C46 C47 122.2(2) . . ? C48 C47 C46 117.9(2) . . ? C48 C47 C51 120.3(2) . . ? C46 C47 C51 121.8(2) . . ? C47 C48 C49 122.0(2) . . ? C48 C49 C44 118.7(2) . . ? C48 C49 C52 120.2(2) . . ? C44 C49 C52 121.2(2) . . ? C54 C53 C58 120.6(2) . . ? C54 C53 C43 120.9(2) . . ? C58 C53 C43 118.54(18) . . ? C55 C54 C53 118.7(2) . . ? C55 C54 C59 119.7(2) . . ? C53 C54 C59 121.6(2) . . ? C56 C55 C54 121.7(2) . . ? C55 C56 C57 118.7(2) . . ? C55 C56 C60 120.5(2) . . ? C57 C56 C60 120.8(2) . . ? C56 C57 C58 121.7(2) . . ? C57 C58 C53 118.6(2) . . ? C57 C58 C61 120.5(2) . . ? C53 C58 C61 121.0(2) . . ? C67 C62 C63 119.8(2) . . ? C67 C62 C39 122.7(2) . . ? C63 C62 C39 117.6(2) . . ? C64 C63 C62 120.6(2) . . ? C63 C64 C65 119.3(2) . . ? C66 C65 C64 120.7(2) . . ? C66 C65 C68B 113.5(5) . . ? C64 C65 C68B 125.8(5) . . ? C66 C65 C68A 126.2(5) . . ? C64 C65 C68A 113.1(5) . . ? C68B C65 C68A 13.2(5) . . ? C65 C66 C67 119.9(2) . . ? C66 C67 C62 119.7(2) . . ? F10B C68B F9B 102.5(11) . . ? F10B C68B F8B 112.5(14) . . ? F9B C68B F8B 99.5(11) . . ? F10B C68B C65 122.4(11) . . ? F9B C68B C65 110.5(9) . . ? F8B C68B C65 107.0(10) . . ? F9A C68A F8A 111.8(9) . . ? F9A C68A F10A 108.4(9) . . ? F8A C68A F10A 99.2(9) . . ? F9A C68A C65 116.7(7) . . ? F8A C68A C65 112.3(8) . . ? F10A C68A C65 106.7(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 F2 B1 N1 C1 -53.7(3) . . . . ? F1 B1 N1 C1 68.3(3) . . . . ? N2 B1 N1 C1 -172.73(18) . . . . ? F2 B1 N1 C4 129.8(2) . . . . ? F1 B1 N1 C4 -108.2(2) . . . . ? N2 B1 N1 C4 10.7(3) . . . . ? C4 N1 C1 C2 -1.9(2) . . . . ? B1 N1 C1 C2 -178.9(2) . . . . ? C4 N1 C1 C10 173.25(19) . . . . ? B1 N1 C1 C10 -3.7(3) . . . . ? N1 C1 C2 C3 1.9(3) . . . . ? C10 C1 C2 C3 -172.9(2) . . . . ? C1 C2 C3 C4 -1.2(3) . . . . ? C1 N1 C4 C5 177.6(2) . . . . ? B1 N1 C4 C5 -5.3(3) . . . . ? C1 N1 C4 C3 1.1(2) . . . . ? B1 N1 C4 C3 178.24(19) . . . . ? C2 C3 C4 N1 0.1(2) . . . . ? C2 C3 C4 C5 -176.0(2) . . . . ? N1 C4 C5 C6 -4.2(3) . . . . ? C3 C4 C5 C6 171.4(2) . . . . ? N1 C4 C5 C19 172.45(18) . . . . ? C3 C4 C5 C19 -12.0(4) . . . . ? C4 C5 C6 N2 6.0(3) . . . . ? C19 C5 C6 N2 -170.54(18) . . . . ? C4 C5 C6 C7 -174.7(2) . . . . ? C19 C5 C6 C7 8.8(4) . . . . ? C5 C6 C7 C8 -179.9(2) . . . . ? N2 C6 C7 C8 -0.5(2) . . . . ? C6 C7 C8 C9 1.5(2) . . . . ? C7 C8 C9 N2 -2.0(2) . . . . ? C7 C8 C9 C26 171.9(2) . . . . ? C8 C9 N2 C6 1.6(2) . . . . ? C26 C9 N2 C6 -172.78(18) . . . . ? C8 C9 N2 B1 178.87(19) . . . . ? C26 C9 N2 B1 4.5(3) . . . . ? C5 C6 N2 C9 178.78(19) . . . . ? C7 C6 N2 C9 -0.7(2) . . . . ? C5 C6 N2 B1 1.5(3) . . . . ? C7 C6 N2 B1 -177.96(19) . . . . ? F2 B1 N2 C9 55.1(3) . . . . ? F1 B1 N2 C9 -66.8(3) . . . . ? N1 B1 N2 C9 174.28(18) . . . . ? F2 B1 N2 C6 -128.1(2) . . . . ? F1 B1 N2 C6 110.0(2) . . . . ? N1 B1 N2 C6 -8.9(3) . . . . ? N1 C1 C10 C11 -86.2(3) . . . . ? C2 C1 C10 C11 88.0(3) . . . . ? N1 C1 C10 C15 93.8(3) . . . . ? C2 C1 C10 C15 -92.0(3) . . . . ? C15 C10 C11 C12 -1.7(3) . . . . ? C1 C10 C11 C12 178.4(2) . . . . ? C15 C10 C11 C16 177.2(2) . . . . ? C1 C10 C11 C16 -2.7(3) . . . . ? C10 C11 C12 C13 0.9(4) . . . . ? C16 C11 C12 C13 -178.0(2) . . . . ? C11 C12 C13 C14 0.7(4) . . . . ? C11 C12 C13 C17 -178.4(2) . . . . ? C12 C13 C14 C15 -1.6(4) . . . . ? C17 C13 C14 C15 177.5(2) . . . . ? C13 C14 C15 C10 0.9(4) . . . . ? C13 C14 C15 C18 -178.9(2) . . . . ? C11 C10 C15 C14 0.8(3) . . . . ? C1 C10 C15 C14 -179.2(2) . . . . ? C11 C10 C15 C18 -179.4(2) . . . . ? C1 C10 C15 C18 0.5(3) . . . . ? C6 C5 C19 C24 109.2(2) . . . . ? C4 C5 C19 C24 -67.4(3) . . . . ? C6 C5 C19 C20 -70.5(3) . . . . ? C4 C5 C19 C20 112.9(2) . . . . ? C24 C19 C20 C21 0.7(3) . . . . ? C5 C19 C20 C21 -179.6(2) . . . . ? C19 C20 C21 C22 -0.4(3) . . . . ? C20 C21 C22 C23 -0.8(4) . . . . ? C20 C21 C22 C25 -179.2(2) . . . . ? C21 C22 C23 C24 1.7(4) . . . . ? C25 C22 C23 C24 -179.8(2) . . . . ? C22 C23 C24 C19 -1.4(4) . . . . ? C20 C19 C24 C23 0.2(3) . . . . ? C5 C19 C24 C23 -179.5(2) . . . . ? C23 C22 C25 F3 142.3(2) . . . . ? C21 C22 C25 F3 -39.2(3) . . . . ? C23 C22 C25 F5 20.4(3) . . . . ? C21 C22 C25 F5 -161.1(2) . . . . ? C23 C22 C25 F4 -99.0(3) . . . . ? C21 C22 C25 F4 79.4(3) . . . . ? N2 C9 C26 C27 83.1(3) . . . . ? C8 C9 C26 C27 -90.1(3) . . . . ? N2 C9 C26 C31 -96.0(3) . . . . ? C8 C9 C26 C31 90.9(3) . . . . ? C31 C26 C27 C28 3.1(3) . . . . ? C9 C26 C27 C28 -175.97(19) . . . . ? C31 C26 C27 C32 -176.7(2) . . . . ? C9 C26 C27 C32 4.2(3) . . . . ? C26 C27 C28 C29 -1.4(3) . . . . ? C32 C27 C28 C29 178.4(2) . . . . ? C27 C28 C29 C30 -1.3(4) . . . . ? C27 C28 C29 C33 178.0(2) . . . . ? C28 C29 C30 C31 2.3(4) . . . . ? C33 C29 C30 C31 -177.0(2) . . . . ? C29 C30 C31 C26 -0.6(3) . . . . ? C29 C30 C31 C34 178.5(2) . . . . ? C27 C26 C31 C30 -2.1(3) . . . . ? C9 C26 C31 C30 176.93(19) . . . . ? C27 C26 C31 C34 178.7(2) . . . . ? C9 C26 C31 C34 -2.2(3) . . . . ? F7 B2 N3 C35 53.6(3) . . . . ? F6 B2 N3 C35 -68.3(3) . . . . ? N4 B2 N3 C35 173.19(18) . . . . ? F7 B2 N3 C38 -127.9(2) . . . . ? F6 B2 N3 C38 110.2(2) . . . . ? N4 B2 N3 C38 -8.3(3) . . . . ? C38 N3 C35 C36 1.5(2) . . . . ? B2 N3 C35 C36 -179.76(19) . . . . ? C38 N3 C35 C44 -172.23(18) . . . . ? B2 N3 C35 C44 6.5(3) . . . . ? N3 C35 C36 C37 -1.3(3) . . . . ? C44 C35 C36 C37 171.9(2) . . . . ? C35 C36 C37 C38 0.5(2) . . . . ? C35 N3 C38 C39 -178.85(19) . . . . ? B2 N3 C38 C39 2.4(3) . . . . ? C35 N3 C38 C37 -1.2(2) . . . . ? B2 N3 C38 C37 -179.98(19) . . . . ? C36 C37 C38 C39 177.8(2) . . . . ? C36 C37 C38 N3 0.5(2) . . . . ? N3 C38 C39 C40 5.1(3) . . . . ? C37 C38 C39 C40 -171.9(2) . . . . ? N3 C38 C39 C62 -171.13(18) . . . . ? C37 C38 C39 C62 11.8(3) . . . . ? C38 C39 C40 N4 -5.0(3) . . . . ? C62 C39 C40 N4 171.21(18) . . . . ? C38 C39 C40 C41 174.9(2) . . . . ? C62 C39 C40 C41 -8.9(4) . . . . ? C39 C40 C41 C42 -179.9(2) . . . . ? N4 C40 C41 C42 0.0(2) . . . . ? C40 C41 C42 C43 -0.6(2) . . . . ? C41 C42 C43 N4 1.0(3) . . . . ? C41 C42 C43 C53 -173.1(2) . . . . ? C42 C43 N4 C40 -1.0(2) . . . . ? C53 C43 N4 C40 173.58(18) . . . . ? C42 C43 N4 B2 -177.77(19) . . . . ? C53 C43 N4 B2 -3.2(3) . . . . ? C39 C40 N4 C43 -179.41(19) . . . . ? C41 C40 N4 C43 0.7(2) . . . . ? C39 C40 N4 B2 -2.6(3) . . . . ? C41 C40 N4 B2 177.46(19) . . . . ? F7 B2 N4 C43 -55.7(3) . . . . ? F6 B2 N4 C43 66.0(3) . . . . ? N3 B2 N4 C43 -175.35(18) . . . . ? F7 B2 N4 C40 128.1(2) . . . . ? F6 B2 N4 C40 -110.2(2) . . . . ? N3 B2 N4 C40 8.5(3) . . . . ? N3 C35 C44 C49 85.2(3) . . . . ? C36 C35 C44 C49 -87.2(3) . . . . ? N3 C35 C44 C45 -94.5(3) . . . . ? C36 C35 C44 C45 93.0(3) . . . . ? C49 C44 C45 C46 -2.4(3) . . . . ? C35 C44 C45 C46 177.33(19) . . . . ? C49 C44 C45 C50 178.9(2) . . . . ? C35 C44 C45 C50 -1.4(3) . . . . ? C44 C45 C46 C47 -0.3(3) . . . . ? C50 C45 C46 C47 178.5(2) . . . . ? C45 C46 C47 C48 2.3(3) . . . . ? C45 C46 C47 C51 -176.9(2) . . . . ? C46 C47 C48 C49 -1.9(3) . . . . ? C51 C47 C48 C49 177.4(2) . . . . ? C47 C48 C49 C44 -0.7(3) . . . . ? C47 C48 C49 C52 179.5(2) . . . . ? C45 C44 C49 C48 2.8(3) . . . . ? C35 C44 C49 C48 -176.9(2) . . . . ? C45 C44 C49 C52 -177.4(2) . . . . ? C35 C44 C49 C52 2.9(3) . . . . ? N4 C43 C53 C54 95.1(3) . . . . ? C42 C43 C53 C54 -91.4(3) . . . . ? N4 C43 C53 C58 -84.1(3) . . . . ? C42 C43 C53 C58 89.4(3) . . . . ? C58 C53 C54 C55 1.2(3) . . . . ? C43 C53 C54 C55 -178.0(2) . . . . ? C58 C53 C54 C59 -179.8(2) . . . . ? C43 C53 C54 C59 0.9(3) . . . . ? C53 C54 C55 C56 1.5(4) . . . . ? C59 C54 C55 C56 -177.5(2) . . . . ? C54 C55 C56 C57 -2.4(4) . . . . ? C54 C55 C56 C60 177.0(2) . . . . ? C55 C56 C57 C58 0.6(4) . . . . ? C60 C56 C57 C58 -178.8(2) . . . . ? C56 C57 C58 C53 2.0(3) . . . . ? C56 C57 C58 C61 -177.7(2) . . . . ? C54 C53 C58 C57 -2.9(3) . . . . ? C43 C53 C58 C57 176.3(2) . . . . ? C54 C53 C58 C61 176.7(2) . . . . ? C43 C53 C58 C61 -4.0(3) . . . . ? C40 C39 C62 C67 69.0(3) . . . . ? C38 C39 C62 C67 -114.8(2) . . . . ? C40 C39 C62 C63 -110.4(2) . . . . ? C38 C39 C62 C63 65.9(3) . . . . ? C67 C62 C63 C64 0.4(3) . . . . ? C39 C62 C63 C64 179.8(2) . . . . ? C62 C63 C64 C65 0.7(4) . . . . ? C63 C64 C65 C66 -1.0(4) . . . . ? C63 C64 C65 C68B 176.5(7) . . . . ? C63 C64 C65 C68A -179.4(5) . . . . ? C64 C65 C66 C67 0.3(4) . . . . ? C68B C65 C66 C67 -177.5(6) . . . . ? C68A C65 C66 C67 178.4(5) . . . . ? C65 C66 C67 C62 0.8(4) . . . . ? C63 C62 C67 C66 -1.2(3) . . . . ? C39 C62 C67 C66 179.5(2) . . . . ? C66 C65 C68B F10B 22.2(14) . . . . ? C64 C65 C68B F10B -155.4(10) . . . . ? C68A C65 C68B F10B -172(5) . . . . ? C66 C65 C68B F9B -98.4(8) . . . . ? C64 C65 C68B F9B 83.9(10) . . . . ? C68A C65 C68B F9B 67(4) . . . . ? C66 C65 C68B F8B 154.2(15) . . . . ? C64 C65 C68B F8B -23.4(18) . . . . ? C68A C65 C68B F8B -40(3) . . . . ? C66 C65 C68A F9A -123.6(8) . . . . ? C64 C65 C68A F9A 54.7(10) . . . . ? C68B C65 C68A F9A -140(4) . . . . ? C66 C65 C68A F8A 105.5(10) . . . . ? C64 C65 C68A F8A -76.3(10) . . . . ? C68B C65 C68A F8A 89(4) . . . . ? C66 C65 C68A F10A -2.2(13) . . . . ? C64 C65 C68A F10A 176.1(10) . . . . ? C68B C65 C68A F10A -19(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.242 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.078 #------------------------------------------------------------------------------ # TEXT