# Electronic Supplementary Material (ESI) for Chemical Communications # 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_mo_20130521a_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H8 B F2 N3 O' _chemical_formula_weight 271.03 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P 21/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 7.1416(9) _cell_length_b 8.4969(11) _cell_length_c 19.655(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.473(2) _cell_angle_gamma 90.00 _cell_volume 1176.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _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 8411 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2679 _reflns_number_gt 2053 _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^)+(0.0505P)^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 2679 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.1110 _refine_ls_wR_factor_gt 0.1030 _refine_ls_goodness_of_fit_ref 1.326 _refine_ls_restrained_S_all 1.326 _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 F1 F 0.57694(13) 0.76101(9) 0.21590(4) 0.0616(3) Uani 1 1 d . . . O1 O 0.19645(15) 0.84781(14) 0.10597(5) 0.0658(3) Uani 1 1 d . . . F2 F 0.38343(11) 0.55257(10) 0.19064(4) 0.0630(3) Uani 1 1 d . . . N1 N 0.70313(14) 0.53427(11) 0.16741(5) 0.0394(3) Uani 1 1 d . . . C1 C 0.7690(2) 0.45291(15) 0.22591(7) 0.0477(3) Uani 1 1 d . . . H1 H 0.7029 0.4584 0.2628 0.057 Uiso 1 1 calc R . . N2 N 0.72910(15) 0.59886(13) 0.05050(6) 0.0440(3) Uani 1 1 d . . . C9 C 0.4252(2) 0.87025(18) -0.12907(7) 0.0569(4) Uani 1 1 d . . . H9 H 0.4558 0.8808 -0.1730 0.068 Uiso 1 1 calc R . . C8 C 0.5366(2) 0.77573(16) -0.08123(7) 0.0505(3) Uani 1 1 d . . . H8 H 0.6415 0.7224 -0.0921 0.061 Uiso 1 1 calc R . . N3 N 0.46631(15) 0.70306(12) 0.09627(5) 0.0401(3) Uani 1 1 d . . . C2 C 0.9288(2) 0.36364(18) 0.23212(8) 0.0564(4) Uani 1 1 d . . . H2 H 0.9705 0.3077 0.2724 0.068 Uiso 1 1 calc R . . C10 C 0.2699(2) 0.94904(17) -0.11276(8) 0.0593(4) Uani 1 1 d . . . H10 H 0.1985 1.0126 -0.1458 0.071 Uiso 1 1 calc R . . C3 C 1.0282(2) 0.3573(2) 0.17755(8) 0.0605(4) Uani 1 1 d . . . H3 H 1.1398 0.2993 0.1813 0.073 Uiso 1 1 calc R . . C4 C 0.96174(19) 0.43686(17) 0.11797(8) 0.0552(4) Uani 1 1 d . . . H4 H 1.0279 0.4323 0.0810 0.066 Uiso 1 1 calc R . . C11 C 0.2179(2) 0.93576(17) -0.04843(7) 0.0549(4) Uani 1 1 d . . . H11 H 0.1128 0.9888 -0.0376 0.066 Uiso 1 1 calc R . . C12 C 0.32770(18) 0.84080(15) -0.00085(6) 0.0434(3) Uani 1 1 d . . . C13 C 0.31260(19) 0.80345(15) 0.07198(7) 0.0456(3) Uani 1 1 d . . . C7 C 0.48516(18) 0.76403(14) -0.01660(6) 0.0402(3) Uani 1 1 d . . . C6 C 0.57421(17) 0.67913(14) 0.04563(6) 0.0376(3) Uani 1 1 d . . . B1 B 0.5215(2) 0.64197(17) 0.16933(7) 0.0403(3) Uani 1 1 d . . . C5 C 0.79547(17) 0.52452(14) 0.11251(7) 0.0411(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 F1 0.0821(6) 0.0634(5) 0.0364(5) -0.0148(4) 0.0012(4) 0.0061(4) O1 0.0652(7) 0.0919(8) 0.0448(6) 0.0087(5) 0.0224(5) 0.0242(6) F2 0.0527(5) 0.0799(6) 0.0595(6) 0.0245(4) 0.0179(4) -0.0055(4) N1 0.0442(6) 0.0437(6) 0.0293(6) -0.0008(4) 0.0028(4) -0.0078(4) C1 0.0552(8) 0.0538(8) 0.0317(7) 0.0029(6) 0.0002(6) -0.0064(6) N2 0.0485(6) 0.0501(6) 0.0351(6) 0.0026(5) 0.0118(5) -0.0008(5) C9 0.0787(11) 0.0640(9) 0.0280(7) 0.0038(6) 0.0088(7) -0.0162(8) C8 0.0644(9) 0.0556(8) 0.0338(7) -0.0021(6) 0.0150(6) -0.0053(7) N3 0.0454(6) 0.0486(6) 0.0273(5) 0.0007(4) 0.0086(4) 0.0008(5) C2 0.0557(9) 0.0618(9) 0.0462(8) 0.0076(7) -0.0083(7) -0.0039(7) C10 0.0747(10) 0.0614(9) 0.0374(8) 0.0097(7) -0.0040(7) -0.0055(8) C3 0.0451(8) 0.0712(10) 0.0625(10) 0.0108(8) 0.0011(7) 0.0043(7) C4 0.0445(7) 0.0679(9) 0.0543(9) 0.0065(7) 0.0116(7) 0.0009(7) C11 0.0596(8) 0.0620(8) 0.0416(8) 0.0056(6) 0.0036(7) 0.0067(7) C12 0.0517(7) 0.0483(7) 0.0296(7) 0.0003(5) 0.0046(6) -0.0024(6) C13 0.0485(7) 0.0547(7) 0.0339(7) 0.0003(6) 0.0078(6) 0.0017(6) C7 0.0497(7) 0.0426(6) 0.0284(7) -0.0018(5) 0.0072(5) -0.0067(5) C6 0.0451(7) 0.0412(6) 0.0271(6) -0.0027(5) 0.0079(5) -0.0065(5) B1 0.0474(8) 0.0473(8) 0.0263(7) 0.0009(6) 0.0069(6) -0.0042(6) C5 0.0419(7) 0.0454(7) 0.0359(7) -0.0001(5) 0.0058(5) -0.0082(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 F1 B1 1.3777(16) . ? O1 C13 1.2077(15) . ? F2 B1 1.3642(15) . ? N1 C1 1.3577(16) . ? N1 C5 1.3566(16) . ? N1 B1 1.5928(18) . ? C1 C2 1.359(2) . ? C1 H1 0.9300 . ? N2 C6 1.2896(16) . ? N2 C5 1.3853(16) . ? C9 C10 1.378(2) . ? C9 C8 1.384(2) . ? C9 H9 0.9300 . ? C8 C7 1.3826(18) . ? C8 H8 0.9300 . ? N3 C6 1.3705(15) . ? N3 C13 1.4099(17) . ? N3 B1 1.5169(17) . ? C2 C3 1.381(2) . ? C2 H2 0.9300 . ? C10 C11 1.380(2) . ? C10 H10 0.9300 . ? C3 C4 1.368(2) . ? C3 H3 0.9300 . ? C4 C5 1.3909(19) . ? C4 H4 0.9300 . ? C11 C12 1.3782(19) . ? C11 H11 0.9300 . ? C12 C7 1.3786(18) . ? C12 C13 1.4873(17) . ? C7 C6 1.4715(17) . ? 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 C5 119.77(11) . . ? C1 N1 B1 116.27(10) . . ? C5 N1 B1 123.93(10) . . ? N1 C1 C2 121.95(13) . . ? N1 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? C6 N2 C5 118.12(10) . . ? C10 C9 C8 121.23(13) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C7 C8 C9 117.14(13) . . ? C7 C8 H8 121.4 . . ? C9 C8 H8 121.4 . . ? C6 N3 C13 110.09(10) . . ? C6 N3 B1 123.17(10) . . ? C13 N3 B1 126.45(10) . . ? C1 C2 C3 118.89(13) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C9 C10 C11 121.45(14) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C4 C3 C2 119.72(14) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.14(14) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C12 C11 C10 117.45(14) . . ? C12 C11 H11 121.3 . . ? C10 C11 H11 121.3 . . ? C7 C12 C11 121.24(12) . . ? C7 C12 C13 107.84(11) . . ? C11 C12 C13 130.90(13) . . ? O1 C13 N3 124.67(12) . . ? O1 C13 C12 129.12(13) . . ? N3 C13 C12 106.21(11) . . ? C12 C7 C8 121.48(12) . . ? C12 C7 C6 107.58(10) . . ? C8 C7 C6 130.93(12) . . ? N2 C6 N3 127.06(11) . . ? N2 C6 C7 124.68(11) . . ? N3 C6 C7 108.25(10) . . ? F2 B1 F1 110.36(11) . . ? F2 B1 N3 113.12(11) . . ? F1 B1 N3 112.28(11) . . ? F2 B1 N1 108.66(10) . . ? F1 B1 N1 106.95(11) . . ? N3 B1 N1 105.07(9) . . ? N1 C5 N2 122.10(11) . . ? N1 C5 C4 119.47(12) . . ? N2 C5 C4 118.44(12) . . ? 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 C5 N1 C1 C2 1.54(18) . . . . ? B1 N1 C1 C2 -176.40(12) . . . . ? C10 C9 C8 C7 0.0(2) . . . . ? N1 C1 C2 C3 0.9(2) . . . . ? C8 C9 C10 C11 -0.7(2) . . . . ? C1 C2 C3 C4 -1.8(2) . . . . ? C2 C3 C4 C5 0.4(2) . . . . ? C9 C10 C11 C12 0.2(2) . . . . ? C10 C11 C12 C7 1.0(2) . . . . ? C10 C11 C12 C13 179.05(14) . . . . ? C6 N3 C13 O1 -178.26(13) . . . . ? B1 N3 C13 O1 -4.4(2) . . . . ? C6 N3 C13 C12 1.22(13) . . . . ? B1 N3 C13 C12 175.12(11) . . . . ? C7 C12 C13 O1 179.28(15) . . . . ? C11 C12 C13 O1 1.0(2) . . . . ? C7 C12 C13 N3 -0.17(14) . . . . ? C11 C12 C13 N3 -178.41(14) . . . . ? C11 C12 C7 C8 -1.7(2) . . . . ? C13 C12 C7 C8 179.83(12) . . . . ? C11 C12 C7 C6 177.59(12) . . . . ? C13 C12 C7 C6 -0.86(13) . . . . ? C9 C8 C7 C12 1.19(19) . . . . ? C9 C8 C7 C6 -177.94(12) . . . . ? C5 N2 C6 N3 1.46(18) . . . . ? C5 N2 C6 C7 -179.72(11) . . . . ? C13 N3 C6 N2 177.22(12) . . . . ? B1 N3 C6 N2 3.07(19) . . . . ? C13 N3 C6 C7 -1.76(13) . . . . ? B1 N3 C6 C7 -175.91(10) . . . . ? C12 C7 C6 N2 -177.38(12) . . . . ? C8 C7 C6 N2 1.8(2) . . . . ? C12 C7 C6 N3 1.63(13) . . . . ? C8 C7 C6 N3 -179.14(13) . . . . ? C6 N3 B1 F2 -125.47(12) . . . . ? C13 N3 B1 F2 61.37(16) . . . . ? C6 N3 B1 F1 108.80(13) . . . . ? C13 N3 B1 F1 -64.36(16) . . . . ? C6 N3 B1 N1 -7.09(15) . . . . ? C13 N3 B1 N1 179.75(11) . . . . ? C1 N1 B1 F2 -52.45(14) . . . . ? C5 N1 B1 F2 129.71(11) . . . . ? C1 N1 B1 F1 66.69(13) . . . . ? C5 N1 B1 F1 -111.16(12) . . . . ? C1 N1 B1 N3 -173.80(10) . . . . ? C5 N1 B1 N3 8.36(15) . . . . ? C1 N1 C5 N2 176.77(11) . . . . ? B1 N1 C5 N2 -5.46(17) . . . . ? C1 N1 C5 C4 -2.94(17) . . . . ? B1 N1 C5 C4 174.83(12) . . . . ? C6 N2 C5 N1 -0.15(17) . . . . ? C6 N2 C5 C4 179.57(12) . . . . ? C3 C4 C5 N1 2.0(2) . . . . ? C3 C4 C5 N2 -177.74(13) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.140 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 968011' ####################################################################### # # 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_mo_20130701b_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H10 B F2 N3 O' _chemical_formula_weight 321.09 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' 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' 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P 21/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 8.575(2) _cell_length_b 12.611(3) _cell_length_c 13.588(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.164(4) _cell_angle_gamma 90.00 _cell_volume 1411.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _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 9279 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3203 _reflns_number_gt 2456 _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^)+(0.0563P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3203 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1150 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 1.256 _refine_ls_restrained_S_all 1.256 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.94713(13) 0.05929(9) 0.24701(7) 0.0540(3) Uani 1 1 d . . . F1 F 0.63491(12) 0.19760(6) 0.21962(6) 0.0516(3) Uani 1 1 d . . . F2 F 0.81343(11) 0.28878(7) 0.15502(6) 0.0515(3) Uani 1 1 d . . . C2 C 0.49396(18) 0.39702(11) 0.15125(10) 0.0401(3) Uani 1 1 d . . . H2 H 0.5786 0.3732 0.2057 0.048 Uiso 1 1 calc R . . C7 C 0.30185(17) 0.33509(12) -0.12344(10) 0.0423(3) Uani 1 1 d . . . H7 H 0.2218 0.3616 -0.1790 0.051 Uiso 1 1 calc R . . C8 C 0.38540(17) 0.24743(12) -0.13478(9) 0.0406(3) Uani 1 1 d . . . H8 H 0.3626 0.2140 -0.1982 0.049 Uiso 1 1 calc R . . N2 N 0.57824(13) 0.11248(9) -0.07057(7) 0.0360(3) Uani 1 1 d . . . C12 C 0.76183(18) -0.10024(11) -0.08456(11) 0.0433(3) Uani 1 1 d . . . H12 H 0.6865 -0.0894 -0.1478 0.052 Uiso 1 1 calc R . . N1 N 0.54729(12) 0.25538(8) 0.04112(7) 0.0301(2) Uani 1 1 d . . . C16 C 0.88690(16) -0.04673(10) 0.09062(10) 0.0378(3) Uani 1 1 d . . . C14 C 0.9779(2) -0.20270(12) 0.02737(14) 0.0535(4) Uani 1 1 d . . . H14 H 1.0467 -0.2611 0.0367 0.064 Uiso 1 1 calc R . . C5 C 0.2444(2) 0.47506(12) -0.01119(12) 0.0484(4) Uani 1 1 d . . . H5 H 0.1626 0.5024 -0.0653 0.058 Uiso 1 1 calc R . . C11 C 0.77517(16) -0.03029(10) -0.00389(10) 0.0351(3) Uani 1 1 d . . . C4 C 0.2756(2) 0.52060(13) 0.08357(12) 0.0531(4) Uani 1 1 d . . . H4 H 0.2134 0.5776 0.0942 0.064 Uiso 1 1 calc R . . C3 C 0.4011(2) 0.48135(12) 0.16444(11) 0.0485(4) Uani 1 1 d . . . H3 H 0.4221 0.5132 0.2286 0.058 Uiso 1 1 calc R . . N3 N 0.74767(13) 0.10926(9) 0.10017(7) 0.0339(3) Uani 1 1 d . . . C15 C 0.99036(19) -0.13306(12) 0.10844(12) 0.0490(4) Uani 1 1 d . . . H15 H 1.0650 -0.1440 0.1719 0.059 Uiso 1 1 calc R . . C9 C 0.50715(15) 0.20604(10) -0.05119(9) 0.0325(3) Uani 1 1 d . . . C13 C 0.8658(2) -0.18734(12) -0.06698(13) 0.0509(4) Uani 1 1 d . . . H13 H 0.8599 -0.2359 -0.1194 0.061 Uiso 1 1 calc R . . C1 C 0.46113(16) 0.34617(10) 0.05507(9) 0.0323(3) Uani 1 1 d . . . B1 B 0.69222(19) 0.21388(12) 0.13547(10) 0.0341(3) Uani 1 1 d . . . C17 C 0.87192(16) 0.04267(11) 0.15931(10) 0.0380(3) Uani 1 1 d . . . C6 C 0.33546(16) 0.38674(10) -0.02749(10) 0.0368(3) Uani 1 1 d . . . C10 C 0.68928(15) 0.06958(10) 0.00350(9) 0.0322(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 O1 0.0484(6) 0.0661(8) 0.0377(5) 0.0022(4) -0.0044(4) 0.0060(5) F1 0.0750(7) 0.0499(5) 0.0335(4) 0.0094(3) 0.0209(4) 0.0149(4) F2 0.0450(5) 0.0434(5) 0.0554(5) -0.0079(4) -0.0037(4) -0.0092(4) C2 0.0485(8) 0.0334(7) 0.0377(6) -0.0007(5) 0.0111(6) 0.0007(6) C7 0.0399(8) 0.0488(8) 0.0343(6) 0.0084(6) 0.0040(5) 0.0099(6) C8 0.0421(8) 0.0474(8) 0.0289(6) -0.0008(5) 0.0040(5) 0.0064(6) N2 0.0365(6) 0.0371(6) 0.0310(5) -0.0031(4) 0.0038(4) 0.0039(5) C12 0.0424(8) 0.0380(8) 0.0486(7) -0.0048(6) 0.0113(6) -0.0002(6) N1 0.0320(6) 0.0289(6) 0.0284(5) 0.0013(4) 0.0068(4) -0.0010(4) C16 0.0335(7) 0.0353(7) 0.0434(7) 0.0077(5) 0.0088(6) -0.0011(5) C14 0.0511(10) 0.0337(8) 0.0790(11) 0.0088(7) 0.0237(8) 0.0089(7) C5 0.0522(9) 0.0417(8) 0.0529(8) 0.0107(6) 0.0170(7) 0.0127(7) C11 0.0319(7) 0.0307(7) 0.0425(7) 0.0025(5) 0.0098(5) -0.0022(5) C4 0.0641(11) 0.0395(8) 0.0602(9) 0.0019(7) 0.0247(8) 0.0147(7) C3 0.0644(10) 0.0379(8) 0.0468(7) -0.0058(6) 0.0215(7) 0.0023(7) N3 0.0322(6) 0.0347(6) 0.0306(5) 0.0013(4) 0.0018(4) 0.0014(4) C15 0.0417(8) 0.0441(9) 0.0588(8) 0.0147(7) 0.0099(7) 0.0066(6) C9 0.0335(7) 0.0338(7) 0.0298(6) 0.0002(5) 0.0079(5) -0.0004(5) C13 0.0515(9) 0.0354(8) 0.0696(10) -0.0066(7) 0.0230(8) -0.0007(7) C1 0.0364(7) 0.0284(6) 0.0336(6) 0.0029(5) 0.0120(5) -0.0006(5) B1 0.0387(8) 0.0328(8) 0.0274(6) 0.0002(5) 0.0035(5) -0.0005(6) C17 0.0328(7) 0.0414(8) 0.0365(6) 0.0066(5) 0.0041(5) 0.0003(5) C6 0.0389(7) 0.0348(7) 0.0380(6) 0.0066(5) 0.0128(5) 0.0029(6) C10 0.0310(6) 0.0322(7) 0.0323(6) -0.0007(5) 0.0069(5) -0.0028(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 O1 C17 1.2051(15) . ? F1 B1 1.3799(17) . ? F2 B1 1.3745(17) . ? C2 C3 1.370(2) . ? C2 C1 1.4119(17) . ? C2 H2 0.9300 . ? C7 C8 1.349(2) . ? C7 C6 1.4134(19) . ? C7 H7 0.9300 . ? C8 C9 1.4115(17) . ? C8 H8 0.9300 . ? N2 C10 1.2957(15) . ? N2 C9 1.3865(16) . ? C12 C11 1.3867(19) . ? C12 C13 1.393(2) . ? C12 H12 0.9300 . ? N1 C9 1.3560(15) . ? N1 C1 1.4038(17) . ? N1 B1 1.6047(16) . ? C16 C15 1.383(2) . ? C16 C11 1.3876(18) . ? C16 C17 1.492(2) . ? C14 C13 1.385(2) . ? C14 C15 1.390(2) . ? C14 H14 0.9300 . ? C5 C4 1.367(2) . ? C5 C6 1.413(2) . ? C5 H5 0.9300 . ? C11 C10 1.4764(18) . ? C4 C3 1.398(2) . ? C4 H4 0.9300 . ? C3 H3 0.9300 . ? N3 C10 1.3640(15) . ? N3 C17 1.4176(16) . ? N3 B1 1.5244(19) . ? C15 H15 0.9300 . ? C13 H13 0.9300 . ? C1 C6 1.4172(17) . ? 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 C3 C2 C1 120.02(12) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C8 C7 C6 120.30(11) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 120.56(12) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 N2 C9 118.35(10) . . ? C11 C12 C13 117.26(13) . . ? C11 C12 H12 121.4 . . ? C13 C12 H12 121.4 . . ? C9 N1 C1 119.45(10) . . ? C9 N1 B1 122.01(10) . . ? C1 N1 B1 118.54(10) . . ? C15 C16 C11 121.59(13) . . ? C15 C16 C17 130.42(12) . . ? C11 C16 C17 107.98(11) . . ? C13 C14 C15 121.70(14) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C4 C5 C6 120.49(13) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C12 C11 C16 121.36(13) . . ? C12 C11 C10 131.56(12) . . ? C16 C11 C10 107.07(11) . . ? C5 C4 C3 119.85(14) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C2 C3 C4 121.38(13) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C10 N3 C17 110.18(11) . . ? C10 N3 B1 123.89(10) . . ? C17 N3 B1 125.83(10) . . ? C16 C15 C14 117.07(14) . . ? C16 C15 H15 121.5 . . ? C14 C15 H15 121.5 . . ? N1 C9 N2 123.66(10) . . ? N1 C9 C8 121.01(12) . . ? N2 C9 C8 115.32(10) . . ? C14 C13 C12 121.02(15) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? N1 C1 C2 121.24(11) . . ? N1 C1 C6 120.02(11) . . ? C2 C1 C6 118.72(12) . . ? F2 B1 F1 111.51(11) . . ? F2 B1 N3 111.73(12) . . ? F1 B1 N3 110.25(11) . . ? F2 B1 N1 107.83(10) . . ? F1 B1 N1 109.59(12) . . ? N3 B1 N1 105.72(9) . . ? O1 C17 N3 124.64(13) . . ? O1 C17 C16 129.39(13) . . ? N3 C17 C16 105.97(10) . . ? C5 C6 C7 121.89(12) . . ? C5 C6 C1 119.48(12) . . ? C7 C6 C1 118.60(12) . . ? N2 C10 N3 126.03(12) . . ? N2 C10 C11 125.17(11) . . ? N3 C10 C11 108.79(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 C6 C7 C8 C9 0.1(2) . . . . ? C13 C12 C11 C16 -0.4(2) . . . . ? C13 C12 C11 C10 178.17(14) . . . . ? C15 C16 C11 C12 0.4(2) . . . . ? C17 C16 C11 C12 179.23(13) . . . . ? C15 C16 C11 C10 -178.48(13) . . . . ? C17 C16 C11 C10 0.38(15) . . . . ? C6 C5 C4 C3 1.6(3) . . . . ? C1 C2 C3 C4 -1.6(2) . . . . ? C5 C4 C3 C2 -0.5(3) . . . . ? C11 C16 C15 C14 0.2(2) . . . . ? C17 C16 C15 C14 -178.41(14) . . . . ? C13 C14 C15 C16 -0.7(2) . . . . ? C1 N1 C9 N2 -175.90(12) . . . . ? B1 N1 C9 N2 4.69(19) . . . . ? C1 N1 C9 C8 3.06(19) . . . . ? B1 N1 C9 C8 -176.35(12) . . . . ? C10 N2 C9 N1 -0.01(19) . . . . ? C10 N2 C9 C8 -179.02(13) . . . . ? C7 C8 C9 N1 -2.5(2) . . . . ? C7 C8 C9 N2 176.51(13) . . . . ? C15 C14 C13 C12 0.7(3) . . . . ? C11 C12 C13 C14 -0.2(2) . . . . ? C9 N1 C1 C2 177.01(12) . . . . ? B1 N1 C1 C2 -3.56(18) . . . . ? C9 N1 C1 C6 -1.22(18) . . . . ? B1 N1 C1 C6 178.21(12) . . . . ? C3 C2 C1 N1 -175.80(13) . . . . ? C3 C2 C1 C6 2.5(2) . . . . ? C10 N3 B1 F2 -111.84(13) . . . . ? C17 N3 B1 F2 64.19(17) . . . . ? C10 N3 B1 F1 123.56(13) . . . . ? C17 N3 B1 F1 -60.41(17) . . . . ? C10 N3 B1 N1 5.19(17) . . . . ? C17 N3 B1 N1 -178.77(11) . . . . ? C9 N1 B1 F2 113.00(13) . . . . ? C1 N1 B1 F2 -66.41(15) . . . . ? C9 N1 B1 F1 -125.44(12) . . . . ? C1 N1 B1 F1 55.14(14) . . . . ? C9 N1 B1 N3 -6.64(17) . . . . ? C1 N1 B1 N3 173.95(11) . . . . ? C10 N3 C17 O1 178.68(14) . . . . ? B1 N3 C17 O1 2.2(2) . . . . ? C10 N3 C17 C16 -0.87(14) . . . . ? B1 N3 C17 C16 -177.36(12) . . . . ? C15 C16 C17 O1 -0.5(3) . . . . ? C11 C16 C17 O1 -179.25(15) . . . . ? C15 C16 C17 N3 178.99(14) . . . . ? C11 C16 C17 N3 0.27(15) . . . . ? C4 C5 C6 C7 177.31(15) . . . . ? C4 C5 C6 C1 -0.7(2) . . . . ? C8 C7 C6 C5 -176.34(14) . . . . ? C8 C7 C6 C1 1.7(2) . . . . ? N1 C1 C6 C5 176.94(12) . . . . ? C2 C1 C6 C5 -1.3(2) . . . . ? N1 C1 C6 C7 -1.1(2) . . . . ? C2 C1 C6 C7 -179.42(13) . . . . ? C9 N2 C10 N3 -1.8(2) . . . . ? C9 N2 C10 C11 179.16(12) . . . . ? C17 N3 C10 N2 -178.09(13) . . . . ? B1 N3 C10 N2 -1.5(2) . . . . ? C17 N3 C10 C11 1.12(15) . . . . ? B1 N3 C10 C11 177.70(12) . . . . ? C12 C11 C10 N2 -0.4(2) . . . . ? C16 C11 C10 N2 178.29(13) . . . . ? C12 C11 C10 N3 -179.62(14) . . . . ? C16 C11 C10 N3 -0.93(15) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.146 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 968012' ####################################################################### # # 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_20130918aa_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43 H26 B2 Cl2 F4 N6 O2' _chemical_formula_weight 827.22 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 Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.7070(17) _cell_length_b 15.0371(16) _cell_length_c 16.4939(18) _cell_angle_alpha 90.00 _cell_angle_beta 112.855(2) _cell_angle_gamma 90.00 _cell_volume 3589.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6392 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 27.74 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1688 _exptl_absorpt_coefficient_mu 0.253 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9372 _exptl_absorpt_correction_T_max 0.9559 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16605 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0230 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.01 _reflns_number_total 6325 _reflns_number_gt 5130 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0628P)^2^+1.6684P] 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 6325 _refine_ls_number_parameters 532 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1221 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 Cl1 Cl 0.29879(5) 0.45224(5) 0.29827(5) 0.0719(2) Uani 1 1 d . . . Cl2 Cl 0.19159(7) 0.58608(6) 0.34483(6) 0.0928(3) Uani 1 1 d . . . F1 F 1.08318(9) 0.32552(8) 0.18140(7) 0.0495(3) Uani 1 1 d . . . F2 F 0.94267(9) 0.26379(8) 0.15436(8) 0.0505(3) Uani 1 1 d . . . N1 N 0.91515(11) 0.40392(11) -0.05462(10) 0.0340(4) Uani 1 1 d . . . N2 N 0.99196(11) 0.27692(10) 0.03153(10) 0.0331(4) Uani 1 1 d . . . N3 N 0.94747(11) 0.40918(11) 0.09823(10) 0.0357(4) Uani 1 1 d . . . O1 O 0.95756(13) 0.45741(11) 0.23511(9) 0.0580(5) Uani 1 1 d . . . C4 C 0.78833(13) 0.66701(13) -0.02849(13) 0.0361(4) Uani 1 1 d . . . C2 C 0.86863(13) 0.52872(12) 0.01547(12) 0.0323(4) Uani 1 1 d . . . C1 C 0.91193(13) 0.44250(13) 0.01463(12) 0.0323(4) Uani 1 1 d . . . C13 C 0.95575(13) 0.32138(13) -0.04564(12) 0.0328(4) Uani 1 1 d . . . C14 C 0.95684(14) 0.28419(14) -0.12359(12) 0.0379(5) Uani 1 1 d . . . H14 H 0.9306 0.3154 -0.1762 0.045 Uiso 1 1 calc R . . C11 C 0.87867(14) 0.54453(13) 0.10314(12) 0.0341(4) Uani 1 1 d . . . C21 C 1.03166(14) 0.19317(13) 0.03390(13) 0.0358(4) Uani 1 1 d . . . C10 C 0.84397(14) 0.61867(13) 0.12605(13) 0.0373(5) Uani 1 1 d . . . H10 H 0.8505 0.6276 0.1840 0.045 Uiso 1 1 calc R . . C9 C 0.79758(13) 0.68245(13) 0.06013(13) 0.0357(4) Uani 1 1 d . . . C3 C 0.82455(14) 0.58796(13) -0.04984(13) 0.0364(4) Uani 1 1 d . . . H3 H 0.8183 0.5768 -0.1074 0.044 Uiso 1 1 calc R . . C12 C 0.93109(15) 0.46874(13) 0.15672(13) 0.0392(5) Uani 1 1 d . . . C15 C 0.99553(15) 0.20384(14) -0.12298(14) 0.0408(5) Uani 1 1 d . . . H15 H 0.9963 0.1802 -0.1748 0.049 Uiso 1 1 calc R . . C16 C 1.03481(14) 0.15583(13) -0.04364(13) 0.0377(4) Uani 1 1 d . . . C20 C 1.06992(16) 0.14455(14) 0.11287(14) 0.0471(5) Uani 1 1 d . . . H20 H 1.0667 0.1668 0.1642 0.057 Uiso 1 1 calc R . . C8 C 0.76128(15) 0.76193(14) 0.07936(15) 0.0432(5) Uani 1 1 d . . . H8 H 0.7670 0.7733 0.1367 0.052 Uiso 1 1 calc R . . C17 C 1.07781(16) 0.07308(14) -0.03958(15) 0.0472(5) Uani 1 1 d . . . H17 H 1.0795 0.0483 -0.0906 0.057 Uiso 1 1 calc R . . C5 C 0.74353(15) 0.73112(15) -0.09306(14) 0.0448(5) Uani 1 1 d . . . H5 H 0.7373 0.7217 -0.1508 0.054 Uiso 1 1 calc R . . B1 B 0.99258(17) 0.31811(15) 0.12147(14) 0.0362(5) Uani 1 1 d . . . C6 C 0.70909(16) 0.80701(15) -0.07194(16) 0.0507(6) Uani 1 1 d . . . H6 H 0.6796 0.8488 -0.1153 0.061 Uiso 1 1 calc R . . C18 C 1.11686(18) 0.02898(15) 0.03787(16) 0.0540(6) Uani 1 1 d . . . H18 H 1.1469 -0.0248 0.0402 0.065 Uiso 1 1 calc R . . C7 C 0.71800(16) 0.82215(15) 0.01467(16) 0.0488(5) Uani 1 1 d . . . H7 H 0.6941 0.8740 0.0283 0.059 Uiso 1 1 calc R . . C19 C 1.11186(18) 0.06437(15) 0.11398(16) 0.0549(6) Uani 1 1 d . . . H19 H 1.1375 0.0330 0.1665 0.066 Uiso 1 1 calc R . . F3 F 0.31658(9) 0.17577(9) 0.28815(8) 0.0558(4) Uani 1 1 d . . . F4 F 0.44790(9) 0.10725(9) 0.29611(8) 0.0553(3) Uani 1 1 d . . . N6 N 0.45682(11) 0.20874(11) 0.41598(10) 0.0361(4) Uani 1 1 d . . . N4 N 0.44646(12) 0.12576(11) 0.53618(10) 0.0382(4) Uani 1 1 d . . . C23 C 0.36651(13) -0.01736(13) 0.51073(13) 0.0361(4) Uani 1 1 d . . . C34 C 0.47339(13) 0.19876(13) 0.50210(13) 0.0368(4) Uani 1 1 d . . . C22 C 0.40095(13) 0.06236(13) 0.48307(13) 0.0359(4) Uani 1 1 d . . . N5 N 0.37816(12) 0.05926(11) 0.39464(10) 0.0387(4) Uani 1 1 d . . . C25 C 0.32929(14) -0.12472(13) 0.59886(14) 0.0388(5) Uani 1 1 d . . . C42 C 0.48736(14) 0.28622(14) 0.38852(14) 0.0393(5) Uani 1 1 d . . . C33 C 0.33007(15) -0.02090(15) 0.35968(14) 0.0430(5) Uani 1 1 d . . . C31 C 0.28213(15) -0.14862(14) 0.43956(15) 0.0447(5) Uani 1 1 d . . . H31 H 0.2528 -0.1824 0.3891 0.054 Uiso 1 1 calc R . . O2 O 0.30185(13) -0.04177(12) 0.28314(10) 0.0609(5) Uani 1 1 d . . . C24 C 0.36960(14) -0.04235(14) 0.59131(13) 0.0394(5) Uani 1 1 d . . . H24 H 0.3975 -0.0062 0.6402 0.047 Uiso 1 1 calc R . . C32 C 0.32290(14) -0.06965(14) 0.43539(13) 0.0391(5) Uani 1 1 d . . . C41 C 0.47371(17) 0.29890(16) 0.29948(15) 0.0490(5) Uani 1 1 d . . . H41 H 0.4433 0.2557 0.2579 0.059 Uiso 1 1 calc R . . C30 C 0.28536(14) -0.17840(14) 0.52270(14) 0.0413(5) Uani 1 1 d . . . C35 C 0.51981(15) 0.26503(14) 0.56428(14) 0.0447(5) Uani 1 1 d . . . H35 H 0.5310 0.2562 0.6234 0.054 Uiso 1 1 calc R . . C37 C 0.53270(15) 0.35359(14) 0.44929(15) 0.0450(5) Uani 1 1 d . . . C40 C 0.50501(19) 0.37434(17) 0.27426(17) 0.0583(7) Uani 1 1 d . . . H40 H 0.4958 0.3816 0.2155 0.070 Uiso 1 1 calc R . . C28 C 0.25158(17) -0.28784(16) 0.61352(18) 0.0560(6) Uani 1 1 d . . . H28 H 0.2261 -0.3422 0.6188 0.067 Uiso 1 1 calc R . . C26 C 0.33206(16) -0.15518(15) 0.68082(15) 0.0486(5) Uani 1 1 d . . . H26 H 0.3601 -0.1202 0.7307 0.058 Uiso 1 1 calc R . . C29 C 0.24702(16) -0.26055(15) 0.53365(17) 0.0525(6) Uani 1 1 d . . . H29 H 0.2180 -0.2966 0.4849 0.063 Uiso 1 1 calc R . . C36 C 0.54795(16) 0.34069(15) 0.53901(15) 0.0499(6) Uani 1 1 d . . . H36 H 0.5773 0.3844 0.5803 0.060 Uiso 1 1 calc R . . C39 C 0.5503(2) 0.44075(17) 0.33430(18) 0.0637(7) Uani 1 1 d . . . H39 H 0.5715 0.4915 0.3158 0.076 Uiso 1 1 calc R . . C27 C 0.29440(17) -0.23483(16) 0.68813(17) 0.0550(6) Uani 1 1 d . . . H27 H 0.2971 -0.2540 0.7427 0.066 Uiso 1 1 calc R . . B2 B 0.39738(17) 0.13587(18) 0.34346(15) 0.0432(6) Uani 1 1 d . . . C38 C 0.56329(19) 0.43086(16) 0.42029(18) 0.0598(6) Uani 1 1 d . . . H38 H 0.5927 0.4756 0.4604 0.072 Uiso 1 1 calc R . . C43 C 0.19025(19) 0.50142(19) 0.27299(18) 0.0654(7) Uani 1 1 d . . . H43A H 0.1685 0.5252 0.2137 0.078 Uiso 1 1 calc R . . H43B H 0.1469 0.4560 0.2742 0.078 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0669(4) 0.0758(5) 0.0720(4) 0.0159(4) 0.0258(4) 0.0132(3) Cl2 0.1351(8) 0.0732(5) 0.0801(5) -0.0296(4) 0.0527(5) -0.0053(5) F1 0.0516(8) 0.0483(7) 0.0352(6) -0.0028(5) 0.0024(6) 0.0043(6) F2 0.0726(9) 0.0427(7) 0.0449(7) 0.0066(5) 0.0323(7) -0.0027(6) N1 0.0392(9) 0.0352(9) 0.0269(8) 0.0016(7) 0.0119(7) 0.0015(7) N2 0.0370(9) 0.0317(9) 0.0286(8) 0.0011(7) 0.0105(7) -0.0018(7) N3 0.0449(10) 0.0341(9) 0.0271(8) 0.0007(7) 0.0130(7) 0.0006(7) O1 0.0916(13) 0.0520(10) 0.0282(8) 0.0051(7) 0.0208(8) 0.0176(9) C4 0.0349(10) 0.0371(11) 0.0357(10) 0.0014(8) 0.0131(8) -0.0020(8) C2 0.0336(10) 0.0332(10) 0.0304(10) 0.0003(8) 0.0129(8) -0.0032(8) C1 0.0335(10) 0.0351(10) 0.0276(9) 0.0024(8) 0.0112(8) -0.0028(8) C13 0.0325(10) 0.0350(10) 0.0286(9) 0.0010(8) 0.0094(8) -0.0026(8) C14 0.0437(11) 0.0411(11) 0.0265(10) 0.0018(8) 0.0111(9) 0.0001(9) C11 0.0395(11) 0.0340(10) 0.0286(9) 0.0010(8) 0.0129(8) -0.0036(8) C21 0.0383(11) 0.0313(10) 0.0363(10) 0.0003(8) 0.0128(9) -0.0032(8) C10 0.0450(12) 0.0372(11) 0.0308(10) -0.0029(8) 0.0162(9) -0.0050(9) C9 0.0363(10) 0.0341(10) 0.0383(11) -0.0007(8) 0.0162(9) -0.0042(8) C3 0.0405(11) 0.0393(11) 0.0300(10) 0.0002(8) 0.0143(8) 0.0006(9) C12 0.0506(12) 0.0371(11) 0.0299(10) -0.0009(8) 0.0157(9) -0.0024(9) C15 0.0480(12) 0.0411(12) 0.0343(11) -0.0045(9) 0.0171(9) -0.0034(10) C16 0.0418(11) 0.0343(11) 0.0371(11) -0.0018(8) 0.0153(9) -0.0043(9) C20 0.0624(14) 0.0406(12) 0.0355(11) 0.0058(9) 0.0158(10) 0.0053(11) C8 0.0488(12) 0.0394(12) 0.0453(12) -0.0048(9) 0.0225(10) -0.0026(10) C17 0.0574(14) 0.0373(12) 0.0506(13) -0.0027(10) 0.0252(11) 0.0011(10) C5 0.0493(13) 0.0450(12) 0.0370(11) 0.0051(9) 0.0133(10) 0.0063(10) B1 0.0456(13) 0.0347(12) 0.0266(11) 0.0011(9) 0.0119(10) -0.0010(10) C6 0.0528(14) 0.0445(13) 0.0501(13) 0.0103(10) 0.0149(11) 0.0096(11) C18 0.0664(16) 0.0378(12) 0.0608(15) 0.0066(11) 0.0280(13) 0.0109(11) C7 0.0510(13) 0.0371(11) 0.0604(14) -0.0013(10) 0.0238(11) 0.0061(10) C19 0.0684(16) 0.0417(13) 0.0503(14) 0.0130(10) 0.0184(12) 0.0092(11) F3 0.0503(8) 0.0679(9) 0.0416(7) 0.0073(6) 0.0097(6) 0.0106(7) F4 0.0616(8) 0.0616(8) 0.0494(7) -0.0081(6) 0.0288(7) 0.0046(7) N6 0.0375(9) 0.0387(9) 0.0320(9) 0.0026(7) 0.0133(7) 0.0066(7) N4 0.0426(10) 0.0380(9) 0.0312(8) 0.0001(7) 0.0113(7) -0.0034(8) C23 0.0329(10) 0.0355(10) 0.0366(10) -0.0026(8) 0.0098(8) 0.0029(8) C34 0.0357(10) 0.0394(11) 0.0325(10) 0.0032(8) 0.0101(8) 0.0041(9) C22 0.0328(10) 0.0385(11) 0.0340(10) 0.0000(8) 0.0102(8) 0.0052(8) N5 0.0416(10) 0.0403(10) 0.0324(9) -0.0034(7) 0.0124(7) 0.0025(8) C25 0.0356(11) 0.0338(11) 0.0448(11) 0.0003(9) 0.0130(9) 0.0043(8) C42 0.0391(11) 0.0389(11) 0.0414(11) 0.0081(9) 0.0175(9) 0.0108(9) C33 0.0426(12) 0.0447(12) 0.0399(12) -0.0076(9) 0.0139(9) 0.0020(10) C31 0.0432(12) 0.0414(12) 0.0472(12) -0.0142(10) 0.0149(10) -0.0004(10) O2 0.0748(12) 0.0653(11) 0.0392(9) -0.0151(8) 0.0184(8) -0.0105(9) C24 0.0395(11) 0.0363(11) 0.0380(11) -0.0026(9) 0.0101(9) 0.0006(9) C32 0.0371(11) 0.0387(11) 0.0400(11) -0.0047(9) 0.0132(9) 0.0049(9) C41 0.0597(14) 0.0480(13) 0.0447(12) 0.0092(10) 0.0261(11) 0.0141(11) C30 0.0359(11) 0.0357(11) 0.0522(13) -0.0047(9) 0.0169(10) 0.0043(9) C35 0.0508(13) 0.0442(12) 0.0341(11) 0.0007(9) 0.0110(9) -0.0055(10) C37 0.0461(12) 0.0412(12) 0.0472(12) 0.0071(10) 0.0178(10) 0.0058(10) C40 0.0751(17) 0.0557(15) 0.0529(14) 0.0197(12) 0.0346(13) 0.0184(13) C28 0.0568(15) 0.0377(12) 0.0754(17) 0.0028(12) 0.0279(13) -0.0044(11) C26 0.0509(13) 0.0448(13) 0.0468(13) 0.0012(10) 0.0154(10) -0.0012(10) C29 0.0513(14) 0.0383(12) 0.0663(16) -0.0116(11) 0.0212(12) -0.0046(10) C36 0.0537(14) 0.0440(13) 0.0458(13) -0.0023(10) 0.0126(11) -0.0068(10) C39 0.0795(19) 0.0488(15) 0.0714(18) 0.0202(13) 0.0387(15) 0.0053(13) C27 0.0561(14) 0.0495(14) 0.0589(15) 0.0102(11) 0.0217(12) -0.0008(11) B2 0.0424(13) 0.0510(15) 0.0353(12) -0.0002(11) 0.0139(11) 0.0065(11) C38 0.0697(17) 0.0444(14) 0.0640(16) 0.0084(12) 0.0247(13) -0.0020(12) C43 0.0660(17) 0.0653(17) 0.0571(15) -0.0178(13) 0.0156(13) 0.0058(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C43 1.754(3) . ? Cl2 C43 1.734(3) . ? F1 B1 1.386(3) . ? F2 B1 1.381(3) . ? N1 C1 1.299(2) . ? N1 C13 1.377(3) . ? N2 C13 1.352(2) . ? N2 C21 1.399(2) . ? N2 B1 1.604(3) . ? N3 C1 1.366(2) . ? N3 C12 1.411(3) . ? N3 B1 1.521(3) . ? O1 C12 1.207(2) . ? C4 C5 1.406(3) . ? C4 C3 1.420(3) . ? C4 C9 1.431(3) . ? C2 C3 1.362(3) . ? C2 C11 1.412(3) . ? C2 C1 1.467(3) . ? C13 C14 1.408(3) . ? C14 C15 1.351(3) . ? C14 H14 0.9300 . ? C11 C10 1.358(3) . ? C11 C12 1.481(3) . ? C21 C20 1.409(3) . ? C21 C16 1.415(3) . ? C10 C9 1.420(3) . ? C10 H10 0.9300 . ? C9 C8 1.412(3) . ? C3 H3 0.9300 . ? C15 C16 1.410(3) . ? C15 H15 0.9300 . ? C16 C17 1.405(3) . ? C20 C19 1.371(3) . ? C20 H20 0.9300 . ? C8 C7 1.363(3) . ? C8 H8 0.9300 . ? C17 C18 1.356(3) . ? C17 H17 0.9300 . ? C5 C6 1.365(3) . ? C5 H5 0.9300 . ? C6 C7 1.399(3) . ? C6 H6 0.9300 . ? C18 C19 1.394(3) . ? C18 H18 0.9300 . ? C7 H7 0.9300 . ? C19 H19 0.9300 . ? F3 B2 1.380(3) . ? F4 B2 1.381(3) . ? N6 C34 1.349(3) . ? N6 C42 1.401(3) . ? N6 B2 1.623(3) . ? N4 C22 1.304(3) . ? N4 C34 1.373(3) . ? C23 C24 1.364(3) . ? C23 C32 1.404(3) . ? C23 C22 1.459(3) . ? C34 C35 1.413(3) . ? C22 N5 1.361(2) . ? N5 C33 1.420(3) . ? N5 B2 1.526(3) . ? C25 C26 1.412(3) . ? C25 C24 1.418(3) . ? C25 C30 1.426(3) . ? C42 C37 1.408(3) . ? C42 C41 1.412(3) . ? C33 O2 1.206(3) . ? C33 C32 1.489(3) . ? C31 C32 1.363(3) . ? C31 C30 1.425(3) . ? C31 H31 0.9300 . ? C24 H24 0.9300 . ? C41 C40 1.364(3) . ? C41 H41 0.9300 . ? C30 C29 1.416(3) . ? C35 C36 1.344(3) . ? C35 H35 0.9300 . ? C37 C38 1.410(3) . ? C37 C36 1.418(3) . ? C40 C39 1.392(4) . ? C40 H40 0.9300 . ? C28 C29 1.355(4) . ? C28 C27 1.400(4) . ? C28 H28 0.9300 . ? C26 C27 1.362(3) . ? C26 H26 0.9300 . ? C29 H29 0.9300 . ? C36 H36 0.9300 . ? C39 C38 1.360(4) . ? C39 H39 0.9300 . ? C27 H27 0.9300 . ? C38 H38 0.9300 . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? 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 C13 118.84(16) . . ? C13 N2 C21 119.42(16) . . ? C13 N2 B1 121.93(16) . . ? C21 N2 B1 118.64(15) . . ? C1 N3 C12 110.23(16) . . ? C1 N3 B1 123.53(16) . . ? C12 N3 B1 126.14(16) . . ? C5 C4 C3 121.13(18) . . ? C5 C4 C9 119.01(19) . . ? C3 C4 C9 119.85(18) . . ? C3 C2 C11 121.34(18) . . ? C3 C2 C1 131.76(17) . . ? C11 C2 C1 106.90(16) . . ? N1 C1 N3 125.69(18) . . ? N1 C1 C2 125.41(17) . . ? N3 C1 C2 108.89(16) . . ? N2 C13 N1 123.70(17) . . ? N2 C13 C14 120.88(18) . . ? N1 C13 C14 115.41(16) . . ? C15 C14 C13 120.89(18) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C10 C11 C2 121.74(18) . . ? C10 C11 C12 131.01(17) . . ? C2 C11 C12 107.25(17) . . ? N2 C21 C20 121.22(18) . . ? N2 C21 C16 120.25(17) . . ? C20 C21 C16 118.53(18) . . ? C11 C10 C9 118.91(17) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C8 C9 C10 122.09(18) . . ? C8 C9 C4 118.50(18) . . ? C10 C9 C4 119.40(18) . . ? C2 C3 C4 118.76(17) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? O1 C12 N3 124.37(19) . . ? O1 C12 C11 128.94(19) . . ? N3 C12 C11 106.68(16) . . ? C14 C15 C16 119.89(19) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C17 C16 C15 121.79(19) . . ? C17 C16 C21 119.56(19) . . ? C15 C16 C21 118.65(18) . . ? C19 C20 C21 119.9(2) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C7 C8 C9 120.6(2) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C18 C17 C16 120.7(2) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C6 C5 C4 120.8(2) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? F2 B1 F1 110.47(17) . . ? F2 B1 N3 110.59(18) . . ? F1 B1 N3 110.86(17) . . ? F2 B1 N2 109.54(16) . . ? F1 B1 N2 109.05(17) . . ? N3 B1 N2 106.24(15) . . ? C5 C6 C7 120.3(2) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C17 C18 C19 119.9(2) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C8 C7 C6 120.9(2) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C20 C19 C18 121.3(2) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C34 N6 C42 118.86(17) . . ? C34 N6 B2 121.41(17) . . ? C42 N6 B2 119.63(16) . . ? C22 N4 C34 119.02(17) . . ? C24 C23 C32 121.93(19) . . ? C24 C23 C22 130.83(18) . . ? C32 C23 C22 107.22(17) . . ? N6 C34 N4 123.76(18) . . ? N6 C34 C35 121.32(19) . . ? N4 C34 C35 114.91(17) . . ? N4 C22 N5 126.32(19) . . ? N4 C22 C23 124.30(18) . . ? N5 C22 C23 109.38(17) . . ? C22 N5 C33 109.95(17) . . ? C22 N5 B2 122.74(17) . . ? C33 N5 B2 127.18(17) . . ? C26 C25 C24 121.23(19) . . ? C26 C25 C30 118.97(19) . . ? C24 C25 C30 119.79(19) . . ? N6 C42 C37 120.68(18) . . ? N6 C42 C41 121.1(2) . . ? C37 C42 C41 118.3(2) . . ? O2 C33 N5 124.5(2) . . ? O2 C33 C32 129.3(2) . . ? N5 C33 C32 106.19(17) . . ? C32 C31 C30 118.71(19) . . ? C32 C31 H31 120.6 . . ? C30 C31 H31 120.6 . . ? C23 C24 C25 118.55(19) . . ? C23 C24 H24 120.7 . . ? C25 C24 H24 120.7 . . ? C31 C32 C23 121.4(2) . . ? C31 C32 C33 131.36(19) . . ? C23 C32 C33 107.26(18) . . ? C40 C41 C42 120.2(2) . . ? C40 C41 H41 119.9 . . ? C42 C41 H41 119.9 . . ? C29 C30 C31 122.6(2) . . ? C29 C30 C25 117.8(2) . . ? C31 C30 C25 119.63(19) . . ? C36 C35 C34 120.7(2) . . ? C36 C35 H35 119.6 . . ? C34 C35 H35 119.6 . . ? C42 C37 C38 119.7(2) . . ? C42 C37 C36 118.6(2) . . ? C38 C37 C36 121.7(2) . . ? C41 C40 C39 121.7(2) . . ? C41 C40 H40 119.2 . . ? C39 C40 H40 119.2 . . ? C29 C28 C27 120.6(2) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C27 C26 C25 121.1(2) . . ? C27 C26 H26 119.4 . . ? C25 C26 H26 119.4 . . ? C28 C29 C30 121.6(2) . . ? C28 C29 H29 119.2 . . ? C30 C29 H29 119.2 . . ? C35 C36 C37 119.8(2) . . ? C35 C36 H36 120.1 . . ? C37 C36 H36 120.1 . . ? C38 C39 C40 119.5(2) . . ? C38 C39 H39 120.3 . . ? C40 C39 H39 120.3 . . ? C26 C27 C28 120.0(2) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? F3 B2 F4 110.17(18) . . ? F3 B2 N5 111.42(19) . . ? F4 B2 N5 110.99(19) . . ? F3 B2 N6 108.16(18) . . ? F4 B2 N6 109.56(18) . . ? N5 B2 N6 106.41(16) . . ? C39 C38 C37 120.7(2) . . ? C39 C38 H38 119.6 . . ? C37 C38 H38 119.6 . . ? Cl2 C43 Cl1 113.24(15) . . ? Cl2 C43 H43A 108.9 . . ? Cl1 C43 H43A 108.9 . . ? Cl2 C43 H43B 108.9 . . ? Cl1 C43 H43B 108.9 . . ? H43A C43 H43B 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C13 N1 C1 N3 1.4(3) . . . . ? C13 N1 C1 C2 -177.95(17) . . . . ? C12 N3 C1 N1 -179.79(18) . . . . ? B1 N3 C1 N1 -3.2(3) . . . . ? C12 N3 C1 C2 -0.3(2) . . . . ? B1 N3 C1 C2 176.26(17) . . . . ? C3 C2 C1 N1 -0.9(3) . . . . ? C11 C2 C1 N1 178.52(18) . . . . ? C3 C2 C1 N3 179.7(2) . . . . ? C11 C2 C1 N3 -0.9(2) . . . . ? C21 N2 C13 N1 179.90(17) . . . . ? B1 N2 C13 N1 -1.3(3) . . . . ? C21 N2 C13 C14 0.5(3) . . . . ? B1 N2 C13 C14 179.36(18) . . . . ? C1 N1 C13 N2 0.8(3) . . . . ? C1 N1 C13 C14 -179.76(18) . . . . ? N2 C13 C14 C15 -1.2(3) . . . . ? N1 C13 C14 C15 179.39(19) . . . . ? C3 C2 C11 C10 0.8(3) . . . . ? C1 C2 C11 C10 -178.62(18) . . . . ? C3 C2 C11 C12 -178.77(18) . . . . ? C1 C2 C11 C12 1.8(2) . . . . ? C13 N2 C21 C20 -179.84(19) . . . . ? B1 N2 C21 C20 1.3(3) . . . . ? C13 N2 C21 C16 0.7(3) . . . . ? B1 N2 C21 C16 -178.16(18) . . . . ? C2 C11 C10 C9 -0.9(3) . . . . ? C12 C11 C10 C9 178.6(2) . . . . ? C11 C10 C9 C8 -178.75(19) . . . . ? C11 C10 C9 C4 0.2(3) . . . . ? C5 C4 C9 C8 -0.1(3) . . . . ? C3 C4 C9 C8 179.66(18) . . . . ? C5 C4 C9 C10 -179.06(19) . . . . ? C3 C4 C9 C10 0.7(3) . . . . ? C11 C2 C3 C4 0.1(3) . . . . ? C1 C2 C3 C4 179.37(19) . . . . ? C5 C4 C3 C2 178.94(19) . . . . ? C9 C4 C3 C2 -0.8(3) . . . . ? C1 N3 C12 O1 -177.6(2) . . . . ? B1 N3 C12 O1 5.9(3) . . . . ? C1 N3 C12 C11 1.4(2) . . . . ? B1 N3 C12 C11 -175.07(18) . . . . ? C10 C11 C12 O1 -2.6(4) . . . . ? C2 C11 C12 O1 177.0(2) . . . . ? C10 C11 C12 N3 178.5(2) . . . . ? C2 C11 C12 N3 -2.0(2) . . . . ? C13 C14 C15 C16 0.5(3) . . . . ? C14 C15 C16 C17 -178.4(2) . . . . ? C14 C15 C16 C21 0.7(3) . . . . ? N2 C21 C16 C17 177.77(19) . . . . ? C20 C21 C16 C17 -1.7(3) . . . . ? N2 C21 C16 C15 -1.3(3) . . . . ? C20 C21 C16 C15 179.2(2) . . . . ? N2 C21 C20 C19 -177.2(2) . . . . ? C16 C21 C20 C19 2.2(3) . . . . ? C10 C9 C8 C7 179.3(2) . . . . ? C4 C9 C8 C7 0.4(3) . . . . ? C15 C16 C17 C18 178.6(2) . . . . ? C21 C16 C17 C18 -0.5(3) . . . . ? C3 C4 C5 C6 -179.9(2) . . . . ? C9 C4 C5 C6 -0.1(3) . . . . ? C1 N3 B1 F2 -116.5(2) . . . . ? C12 N3 B1 F2 59.6(3) . . . . ? C1 N3 B1 F1 120.67(19) . . . . ? C12 N3 B1 F1 -63.3(3) . . . . ? C1 N3 B1 N2 2.3(3) . . . . ? C12 N3 B1 N2 178.38(17) . . . . ? C13 N2 B1 F2 119.19(19) . . . . ? C21 N2 B1 F2 -62.0(2) . . . . ? C13 N2 B1 F1 -119.80(19) . . . . ? C21 N2 B1 F1 59.0(2) . . . . ? C13 N2 B1 N3 -0.3(2) . . . . ? C21 N2 B1 N3 178.56(16) . . . . ? C4 C5 C6 C7 0.0(4) . . . . ? C16 C17 C18 C19 2.1(4) . . . . ? C9 C8 C7 C6 -0.5(3) . . . . ? C5 C6 C7 C8 0.2(4) . . . . ? C21 C20 C19 C18 -0.6(4) . . . . ? C17 C18 C19 C20 -1.6(4) . . . . ? C42 N6 C34 N4 179.87(18) . . . . ? B2 N6 C34 N4 3.5(3) . . . . ? C42 N6 C34 C35 0.6(3) . . . . ? B2 N6 C34 C35 -175.74(19) . . . . ? C22 N4 C34 N6 -1.1(3) . . . . ? C22 N4 C34 C35 178.18(19) . . . . ? C34 N4 C22 N5 1.7(3) . . . . ? C34 N4 C22 C23 -178.37(18) . . . . ? C24 C23 C22 N4 2.6(3) . . . . ? C32 C23 C22 N4 -179.10(19) . . . . ? C24 C23 C22 N5 -177.5(2) . . . . ? C32 C23 C22 N5 0.8(2) . . . . ? N4 C22 N5 C33 178.97(19) . . . . ? C23 C22 N5 C33 -0.9(2) . . . . ? N4 C22 N5 B2 -5.0(3) . . . . ? C23 C22 N5 B2 175.13(17) . . . . ? C34 N6 C42 C37 -1.5(3) . . . . ? B2 N6 C42 C37 174.99(18) . . . . ? C34 N6 C42 C41 178.45(19) . . . . ? B2 N6 C42 C41 -5.1(3) . . . . ? C22 N5 C33 O2 -179.6(2) . . . . ? B2 N5 C33 O2 4.6(3) . . . . ? C22 N5 C33 C32 0.7(2) . . . . ? B2 N5 C33 C32 -175.15(18) . . . . ? C32 C23 C24 C25 1.5(3) . . . . ? C22 C23 C24 C25 179.58(19) . . . . ? C26 C25 C24 C23 178.6(2) . . . . ? C30 C25 C24 C23 -1.1(3) . . . . ? C30 C31 C32 C23 -0.8(3) . . . . ? C30 C31 C32 C33 -179.1(2) . . . . ? C24 C23 C32 C31 -0.6(3) . . . . ? C22 C23 C32 C31 -179.04(19) . . . . ? C24 C23 C32 C33 178.09(18) . . . . ? C22 C23 C32 C33 -0.4(2) . . . . ? O2 C33 C32 C31 -1.4(4) . . . . ? N5 C33 C32 C31 178.3(2) . . . . ? O2 C33 C32 C23 -179.9(2) . . . . ? N5 C33 C32 C23 -0.2(2) . . . . ? N6 C42 C41 C40 -179.2(2) . . . . ? C37 C42 C41 C40 0.7(3) . . . . ? C32 C31 C30 C29 -178.3(2) . . . . ? C32 C31 C30 C25 1.1(3) . . . . ? C26 C25 C30 C29 -0.4(3) . . . . ? C24 C25 C30 C29 179.30(19) . . . . ? C26 C25 C30 C31 -179.91(19) . . . . ? C24 C25 C30 C31 -0.2(3) . . . . ? N6 C34 C35 C36 0.8(3) . . . . ? N4 C34 C35 C36 -178.5(2) . . . . ? N6 C42 C37 C38 179.7(2) . . . . ? C41 C42 C37 C38 -0.2(3) . . . . ? N6 C42 C37 C36 0.9(3) . . . . ? C41 C42 C37 C36 -179.0(2) . . . . ? C42 C41 C40 C39 -0.4(4) . . . . ? C24 C25 C26 C27 -179.1(2) . . . . ? C30 C25 C26 C27 0.6(3) . . . . ? C27 C28 C29 C30 0.3(4) . . . . ? C31 C30 C29 C28 179.5(2) . . . . ? C25 C30 C29 C28 0.0(3) . . . . ? C34 C35 C36 C37 -1.3(4) . . . . ? C42 C37 C36 C35 0.5(3) . . . . ? C38 C37 C36 C35 -178.3(2) . . . . ? C41 C40 C39 C38 -0.5(4) . . . . ? C25 C26 C27 C28 -0.3(4) . . . . ? C29 C28 C27 C26 -0.1(4) . . . . ? C22 N5 B2 F3 -111.6(2) . . . . ? C33 N5 B2 F3 63.8(3) . . . . ? C22 N5 B2 F4 125.3(2) . . . . ? C33 N5 B2 F4 -59.4(3) . . . . ? C22 N5 B2 N6 6.1(3) . . . . ? C33 N5 B2 N6 -178.52(17) . . . . ? C34 N6 B2 F3 114.3(2) . . . . ? C42 N6 B2 F3 -62.1(2) . . . . ? C34 N6 B2 F4 -125.59(19) . . . . ? C42 N6 B2 F4 58.1(2) . . . . ? C34 N6 B2 N5 -5.5(2) . . . . ? C42 N6 B2 N5 178.12(16) . . . . ? C40 C39 C38 C37 1.0(4) . . . . ? C42 C37 C38 C39 -0.6(4) . . . . ? C36 C37 C38 C39 178.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.521 _refine_diff_density_min -0.562 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 968013'