Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'Chemical Communications' _publ_contact_author_name ; Dr. John F. Gallagher ; _publ_contact_author_address ; School of Chemical Sciences, Dublin City University, Dublin 9, Ireland ; _publ_contact_author_phone '353 1 7005114' _publ_contact_author_fax '353 1 7005503' _publ_contact_author_email 'john.gallagher@dcu.ie' _publ_requested_category FO _publ_requested_coeditor_name 'RSC then CSD review' _publ_contact_letter ; ; _publ_section_title ; Synthesis of BF~2~ chelates of tetra-aryl-azadipyrromethanes and spectroscopic evidence for their potential therapeutic behaviour. ; loop_ _publ_author_name _publ_author_address 'Killoran, John' ; Centre for Synthesis and Chemical Biology, Department of Chemistry, Conway Institute, University College Dublin, Belfield, Dublin 4, Ireland ; 'Allen, Lorcan' ; Department of Pharmacology, Conway Institute, University College Dublin, Belfield, Dublin 4, Ireland ; 'Duffy, Ruth' ; Department of Pharmacology, Conway Institute, University College Dublin, Belfield, Dublin 4, Ireland ; 'Gallagher, William M.' ; Department of Pharmacology, Conway Institute, University College Dublin, Belfield, Dublin 4, Ireland ; 'Gallagher, John F.' ; National Institute for Cellular Biotechnology, School of Chemical Sciences, Dublin City University, Dublin 9, Ireland ; 'O`Shea, Donal F.' ; Conway Institute of Biomolecular and Biomedical Research, Department of Chemistry, University College Dublin, Dublin 4, Ireland ; #====================================================================== # data_1-18 _database_code_CSD 184817 _audit_creation_method SHELXL97 _chemical_name_systematic ; BF~2~ chelate ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C37.50 H30 B F2 N3 O2' _chemical_formula_weight 603.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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 18.124(2) _cell_length_b 7.4096(7) _cell_length_c 23.634(3) _cell_angle_alpha 90 _cell_angle_beta 110.188(7) _cell_angle_gamma 90 _cell_volume 2978.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 81 _cell_measurement_theta_min 3.7 _cell_measurement_theta_max 17.7 _exptl_crystal_description red _exptl_crystal_colour block _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1260 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type '\p-scans' _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.991 _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'P4' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 4 _diffrn_standards_interval_count 296 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1 _diffrn_reflns_number 9803 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.1447 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.8 _diffrn_reflns_theta_max 26.0 _reflns_number_total 5871 _reflns_number_gt 2130 _reflns_threshold_expression >2\s(I) _computing_data_collection 'XSCANS (Bruker, 1996)' _computing_cell_refinement 'XSCANS (Bruker, 1996)' _computing_data_reduction 'XSCANS (Bruker, 1996)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1998)' _computing_publication_material 'PLATON (Spek, 1998)' _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 'w=1/[\s^2^(Fo^2^)+(0.0657P)^2^] 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 SHELXL _refine_ls_extinction_coef 0.0026(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5871 _refine_ls_number_parameters 446 _refine_ls_number_restraints 61 _refine_ls_R_factor_all 0.2409 _refine_ls_R_factor_gt 0.0790 _refine_ls_wR_factor_ref 0.1750 _refine_ls_wR_factor_gt 0.1265 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.986 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.45296(17) 0.5666(4) 0.23997(14) 0.0516(9) Uani 1 d . . . C1 C 0.4188(2) 0.5584(5) 0.18100(18) 0.0504(10) Uani 1 d . . . N2 N 0.33708(16) 0.5466(4) 0.15044(13) 0.0484(9) Uani 1 d . . . B1 B 0.2775(3) 0.5609(8) 0.1848(2) 0.0573(14) Uani 1 d . . . F1 F 0.23168(14) 0.7095(4) 0.16396(9) 0.0980(10) Uani 1 d . . . F2 F 0.23120(14) 0.4092(4) 0.17691(9) 0.0927(9) Uani 1 d . . . C2 C 0.4093(2) 0.5715(5) 0.27486(17) 0.0502(11) Uani 1 d . . . N3 N 0.32728(17) 0.5765(4) 0.25329(12) 0.0495(9) Uani 1 d . . . C3 C 0.4575(2) 0.5642(5) 0.13729(17) 0.0497(10) Uani 1 d . . . C4 C 0.3981(2) 0.5603(5) 0.08206(17) 0.0547(11) Uani 1 d . . . H4 H 0.4052 0.5646 0.0449 0.066 Uiso 1 calc R . . C5 C 0.3255(2) 0.5489(5) 0.09043(16) 0.0493(11) Uani 1 d . . . C11A C 0.5424(2) 0.5660(5) 0.14841(18) 0.0511(10) Uani 1 d . . . C12A C 0.5986(3) 0.5818(7) 0.2048(2) 0.0929(17) Uani 1 d . . . H12A H 0.5829 0.5959 0.2381 0.112 Uiso 1 calc R . . C13A C 0.6783(3) 0.5773(8) 0.2132(2) 0.0984(18) Uani 1 d . . . H13A H 0.7150 0.5866 0.2519 0.118 Uiso 1 calc R . . C14A C 0.7031(3) 0.5597(6) 0.1662(2) 0.0718(13) Uani 1 d . . . H14A H 0.7565 0.5532 0.1721 0.086 Uiso 1 calc R . . C15A C 0.6484(3) 0.5516(6) 0.1094(2) 0.0802(14) Uani 1 d . . . H15A H 0.6647 0.5433 0.0762 0.096 Uiso 1 calc R . . C16A C 0.5695(2) 0.5556(6) 0.10103(19) 0.0773(14) Uani 1 d . . . H16A H 0.5333 0.5511 0.0620 0.093 Uiso 1 calc R . . C21A C 0.2501(2) 0.5358(5) 0.04017(16) 0.0456(10) Uani 1 d . . . C22A C 0.2433(2) 0.6180(5) -0.01435(17) 0.0501(11) Uani 1 d . . . H22A H 0.2849 0.6868 -0.0171 0.060 Uiso 1 calc R . . C23A C 0.1766(2) 0.5997(5) -0.06423(17) 0.0531(11) Uani 1 d . . . H23A H 0.1733 0.6548 -0.1004 0.064 Uiso 1 calc R . . C24A C 0.1142(2) 0.4990(5) -0.06049(16) 0.0475(11) Uani 1 d . . . C25A C 0.1190(2) 0.4142(5) -0.00814(17) 0.0541(11) Uani 1 d . . . H25A H 0.0775 0.3438 -0.0061 0.065 Uiso 1 calc R . . C26A C 0.1867(2) 0.4341(5) 0.04213(16) 0.0552(11) Uani 1 d . . . H26A H 0.1896 0.3779 0.0780 0.066 Uiso 1 calc R . . O1A O 0.04961(16) 0.4937(4) -0.11242(10) 0.0635(8) Uani 1 d . . . C27A C -0.0202(2) 0.4149(6) -0.10770(17) 0.0796(14) Uani 1 d . . . H27A H -0.0132 0.2868 -0.1025 0.119 Uiso 1 calc R . . H27B H -0.0639 0.4395 -0.1438 0.119 Uiso 1 calc R . . H27C H -0.0302 0.4656 -0.0737 0.119 Uiso 1 calc R . . C6 C 0.3040(2) 0.5732(5) 0.30218(16) 0.0485(10) Uani 1 d . . . C7 C 0.3711(2) 0.5694(5) 0.35481(16) 0.0563(11) Uani 1 d . . . H7 H 0.3706 0.5671 0.3940 0.068 Uiso 1 calc R . . C8 C 0.4374(2) 0.5695(5) 0.33915(16) 0.0498(10) Uani 1 d . . . C11B C 0.5192(2) 0.5696(6) 0.38093(17) 0.0533(11) Uani 1 d . . . C12B C 0.5363(3) 0.6056(6) 0.44094(18) 0.0727(14) Uani 1 d . . . H12B H 0.4953 0.6306 0.4550 0.087 Uiso 1 calc R . . C13B C 0.6127(3) 0.6059(7) 0.4813(2) 0.0882(16) Uani 1 d . . . H13B H 0.6224 0.6274 0.5220 0.106 Uiso 1 calc R . . C14B C 0.6734(3) 0.5746(6) 0.4615(2) 0.0764(14) Uani 1 d . . . H14B H 0.7249 0.5797 0.4882 0.092 Uiso 1 calc R . . C15B C 0.6587(3) 0.5361(7) 0.4028(2) 0.0924(17) Uani 1 d . . . H15B H 0.7002 0.5119 0.3893 0.111 Uiso 1 calc R . . C16B C 0.5822(3) 0.5326(7) 0.36253(19) 0.0825(15) Uani 1 d . . . H16B H 0.5730 0.5047 0.3223 0.099 Uiso 1 calc R . . C21B C 0.2227(2) 0.5745(6) 0.30254(17) 0.0498(11) Uani 1 d . . . C22B C 0.1629(2) 0.6765(6) 0.26287(16) 0.0542(11) Uani 1 d . . . H22B H 0.1732 0.7460 0.2337 0.065 Uiso 1 calc R . . C23B C 0.0879(2) 0.6760(6) 0.26619(17) 0.0538(11) Uani 1 d . . . H23B H 0.0486 0.7476 0.2401 0.065 Uiso 1 calc R . . C24B C 0.0718(2) 0.5701(6) 0.30794(18) 0.0504(11) Uani 1 d . . . C25B C 0.1312(2) 0.4705(6) 0.34880(17) 0.0576(12) Uani 1 d . . . H25B H 0.1209 0.4015 0.3781 0.069 Uiso 1 calc R . . C26B C 0.2054(2) 0.4743(5) 0.34585(17) 0.0523(11) Uani 1 d . . . H26B H 0.2451 0.4080 0.3736 0.063 Uiso 1 calc R . . O1B O -0.00110(16) 0.5544(4) 0.31284(11) 0.0677(8) Uani 1 d . . . C27B C -0.0639(2) 0.6570(6) 0.27229(19) 0.0867(15) Uani 1 d . . . H27D H -0.0514 0.7832 0.2775 0.130 Uiso 1 calc R . . H27E H -0.1114 0.6343 0.2806 0.130 Uiso 1 calc R . . H27F H -0.0713 0.6224 0.2316 0.130 Uiso 1 calc R . . C1T C 0.042(3) 0.908(4) -0.015(2) 0.124(13) Uani 0.50 d PDU . . H1T H 0.0883 0.8525 -0.0144 0.149 Uiso 0.50 calc PR . . C2T C -0.025(2) 0.898(3) -0.0624(13) 0.124(7) Uani 0.50 d PDU . . H2T H -0.0189 0.8266 -0.0931 0.149 Uiso 0.50 calc PR . . C3T C -0.092(2) 0.960(4) -0.0759(16) 0.106(9) Uani 0.50 d PDU . . H3T H -0.1327 0.9387 -0.1123 0.127 Uiso 0.50 calc PR . . C4T C -0.1013(13) 1.082(2) -0.0230(11) 0.084(4) Uani 0.50 d PDU . . H4T H -0.1473 1.1421 -0.0255 0.100 Uiso 0.50 calc PR . . C5T C -0.0276(14) 1.089(4) 0.0313(16) 0.084(9) Uani 0.50 d PDU . . H5T H -0.0266 1.1531 0.0653 0.100 Uiso 0.50 calc PR . . C6T C 0.0384(12) 0.999(3) 0.0304(12) 0.095(4) Uani 0.50 d PDU . . C7T C 0.1143(17) 0.996(5) 0.0769(19) 0.147(17) Uani 0.50 d PDU . . H7T1 H 0.1087 1.0195 0.1152 0.220 Uiso 0.50 calc PR . . H7T2 H 0.1472 1.0862 0.0689 0.220 Uiso 0.50 calc PR . . H7T3 H 0.1377 0.8790 0.0779 0.220 Uiso 0.50 calc PR . . 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 0.0457(19) 0.061(2) 0.043(2) 0.0066(19) 0.0083(18) 0.0017(19) C1 0.047(3) 0.051(3) 0.049(3) 0.006(2) 0.012(2) 0.005(2) N2 0.038(2) 0.055(2) 0.047(2) 0.0049(18) 0.0084(16) 0.0038(18) B1 0.043(3) 0.074(4) 0.050(3) 0.015(3) 0.010(3) 0.002(4) F1 0.0839(18) 0.150(3) 0.0629(15) 0.0328(17) 0.0285(13) 0.065(2) F2 0.0732(18) 0.144(3) 0.0573(15) -0.0104(15) 0.0185(13) -0.0505(19) C2 0.040(3) 0.054(3) 0.051(3) 0.006(2) 0.009(2) 0.002(2) N3 0.042(2) 0.059(2) 0.044(2) 0.0025(18) 0.0120(17) 0.0019(19) C3 0.041(2) 0.055(3) 0.048(2) 0.001(2) 0.009(2) 0.002(2) C4 0.050(3) 0.065(3) 0.051(3) -0.002(2) 0.022(2) -0.001(3) C5 0.049(3) 0.050(3) 0.046(3) -0.001(2) 0.013(2) 0.001(2) C11A 0.047(3) 0.052(3) 0.056(3) -0.003(2) 0.020(2) 0.000(2) C12A 0.047(3) 0.161(5) 0.066(3) 0.008(3) 0.013(3) -0.008(3) C13A 0.046(3) 0.155(6) 0.083(4) 0.009(4) 0.008(3) -0.006(4) C14A 0.046(3) 0.073(3) 0.100(4) 0.012(3) 0.030(3) 0.004(3) C15A 0.057(3) 0.104(4) 0.083(4) -0.008(3) 0.030(3) -0.008(3) C16A 0.046(3) 0.115(4) 0.068(3) -0.009(3) 0.016(2) -0.003(3) C21A 0.043(2) 0.048(3) 0.043(2) -0.002(2) 0.011(2) 0.006(2) C22A 0.041(2) 0.060(3) 0.049(2) 0.005(2) 0.015(2) -0.005(2) C23A 0.055(3) 0.062(3) 0.047(3) 0.009(2) 0.024(2) 0.007(2) C24A 0.041(2) 0.059(3) 0.038(2) 0.000(2) 0.009(2) 0.004(2) C25A 0.048(3) 0.060(3) 0.048(2) 0.007(2) 0.009(2) -0.007(2) C26A 0.056(3) 0.061(3) 0.047(2) 0.004(2) 0.016(2) -0.004(3) O1A 0.0539(18) 0.083(2) 0.0468(17) 0.0021(15) 0.0089(15) -0.0032(17) C27A 0.057(3) 0.108(4) 0.061(3) -0.003(3) 0.004(2) -0.013(3) C6 0.043(2) 0.055(3) 0.045(2) 0.003(2) 0.012(2) 0.007(2) C7 0.058(3) 0.064(3) 0.045(2) 0.000(2) 0.015(2) 0.002(3) C8 0.051(3) 0.052(3) 0.043(2) -0.003(2) 0.011(2) -0.001(2) C11B 0.049(3) 0.058(3) 0.042(2) 0.004(2) 0.002(2) -0.003(2) C12B 0.060(3) 0.099(4) 0.048(3) 0.006(3) 0.006(2) -0.006(3) C13B 0.080(4) 0.116(5) 0.052(3) 0.013(3) 0.000(3) -0.009(4) C14B 0.057(3) 0.082(4) 0.071(4) 0.017(3) -0.002(3) -0.012(3) C15B 0.052(3) 0.139(5) 0.074(3) 0.003(4) 0.006(3) 0.012(3) C16B 0.057(3) 0.125(5) 0.058(3) 0.002(3) 0.011(3) 0.012(3) C21B 0.048(3) 0.053(3) 0.044(2) -0.004(2) 0.011(2) 0.002(3) C22B 0.055(3) 0.057(3) 0.047(2) 0.005(2) 0.013(2) -0.001(3) C23B 0.048(3) 0.057(3) 0.052(3) 0.002(2) 0.012(2) 0.008(2) C24B 0.044(3) 0.056(3) 0.050(3) -0.010(2) 0.016(2) -0.006(3) C25B 0.055(3) 0.064(3) 0.051(3) 0.006(2) 0.015(2) 0.001(3) C26B 0.052(3) 0.056(3) 0.045(2) 0.005(2) 0.012(2) 0.007(2) O1B 0.0498(18) 0.076(2) 0.076(2) 0.0107(17) 0.0199(16) 0.0041(18) C27B 0.045(3) 0.101(4) 0.107(4) 0.019(3) 0.018(3) 0.012(3) C1T 0.18(3) 0.046(15) 0.15(3) 0.011(16) 0.068(19) 0.034(18) C2T 0.18(2) 0.082(13) 0.164(18) 0.031(14) 0.130(17) 0.023(17) C3T 0.11(2) 0.10(2) 0.117(16) 0.029(13) 0.052(17) -0.010(18) C4T 0.092(11) 0.069(10) 0.107(12) 0.007(10) 0.056(9) 0.021(10) C5T 0.061(12) 0.087(17) 0.13(2) 0.008(13) 0.071(14) 0.010(12) C6T 0.097(12) 0.050(10) 0.143(16) 0.020(10) 0.047(12) -0.003(10) C7T 0.084(15) 0.058(14) 0.24(3) 0.064(16) -0.019(17) -0.004(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 N1 C1 1.317(4) . ? N1 C2 1.326(4) . ? C1 N2 1.409(4) . ? C1 C3 1.435(5) . ? N2 C5 1.360(4) . ? N2 B1 1.562(5) . ? B1 F1 1.365(5) . ? B1 F2 1.377(5) . ? B1 N3 1.561(5) . ? C2 N3 1.395(4) . ? C2 C8 1.426(5) . ? N3 C6 1.360(4) . ? C3 C4 1.376(4) . ? C3 C11A 1.470(5) . ? C4 C5 1.400(5) . ? C4 H4 0.9300 . ? C5 C21A 1.472(5) . ? C11A C16A 1.370(5) . ? C11A C12A 1.375(5) . ? C12A C13A 1.390(6) . ? C12A H12A 0.9300 . ? C13A C14A 1.340(6) . ? C13A H13A 0.9300 . ? C14A C15A 1.367(5) . ? C14A H14A 0.9300 . ? C15A C16A 1.376(5) . ? C15A H15A 0.9300 . ? C16A H16A 0.9300 . ? C21A C26A 1.388(5) . ? C21A C22A 1.392(5) . ? C22A C23A 1.374(5) . ? C22A H22A 0.9300 . ? C23A C24A 1.382(5) . ? C23A H23A 0.9300 . ? C24A C25A 1.363(5) . ? C24A O1A 1.374(4) . ? C25A C26A 1.390(4) . ? C25A H25A 0.9300 . ? C26A H26A 0.9300 . ? O1A C27A 1.432(4) . ? C27A H27A 0.9600 . ? C27A H27B 0.9600 . ? C27A H27C 0.9600 . ? C6 C7 1.408(4) . ? C6 C21B 1.476(5) . ? C7 C8 1.374(5) . ? C7 H7 0.9300 . ? C8 C11B 1.471(5) . ? C11B C12B 1.370(5) . ? C11B C16B 1.382(5) . ? C12B C13B 1.385(5) . ? C12B H12B 0.9300 . ? C13B C14B 1.356(6) . ? C13B H13B 0.9300 . ? C14B C15B 1.351(5) . ? C14B H14B 0.9300 . ? C15B C16B 1.385(5) . ? C15B H15B 0.9300 . ? C16B H16B 0.9300 . ? C21B C26B 1.385(5) . ? C21B C22B 1.387(5) . ? C22B C23B 1.389(5) . ? C22B H22B 0.9300 . ? C23B C24B 1.369(5) . ? C23B H23B 0.9300 . ? C24B O1B 1.370(4) . ? C24B C25B 1.386(5) . ? C25B C26B 1.370(5) . ? C25B H25B 0.9300 . ? C26B H26B 0.9300 . ? O1B C27B 1.428(4) . ? C27B H27D 0.9600 . ? C27B H27E 0.9600 . ? C27B H27F 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 119.7(3) . . ? N1 C1 N2 124.9(3) . . ? N1 C1 C3 126.3(4) . . ? N2 C1 C3 108.7(3) . . ? C5 N2 C1 106.9(3) . . ? C5 N2 B1 130.9(3) . . ? C1 N2 B1 121.5(3) . . ? F1 B1 F2 110.1(4) . . ? F1 B1 N3 112.1(4) . . ? F2 B1 N3 107.9(4) . . ? F1 B1 N2 108.1(4) . . ? F2 B1 N2 111.9(4) . . ? N3 B1 N2 106.8(3) . . ? N1 C2 N3 124.2(3) . . ? N1 C2 C8 126.3(4) . . ? N3 C2 C8 109.5(3) . . ? C6 N3 C2 107.0(3) . . ? C6 N3 B1 129.9(3) . . ? C2 N3 B1 122.5(3) . . ? C4 C3 C1 105.4(3) . . ? C4 C3 C11A 126.7(4) . . ? C1 C3 C11A 127.8(3) . . ? C3 C4 C5 109.4(3) . . ? C3 C4 H4 125.3 . . ? C5 C4 H4 125.3 . . ? N2 C5 C4 109.5(3) . . ? N2 C5 C21A 127.4(3) . . ? C4 C5 C21A 123.1(3) . . ? C16A C11A C12A 116.3(4) . . ? C16A C11A C3 120.1(4) . . ? C12A C11A C3 123.6(4) . . ? C11A C12A C13A 121.4(4) . . ? C11A C12A H12A 119.3 . . ? C13A C12A H12A 119.3 . . ? C14A C13A C12A 120.9(4) . . ? C14A C13A H13A 119.5 . . ? C12A C13A H13A 119.5 . . ? C13A C14A C15A 118.7(4) . . ? C13A C14A H14A 120.6 . . ? C15A C14A H14A 120.6 . . ? C14A C15A C16A 120.4(4) . . ? C14A C15A H15A 119.8 . . ? C16A C15A H15A 119.8 . . ? C11A C16A C15A 122.1(4) . . ? C11A C16A H16A 119.0 . . ? C15A C16A H16A 119.0 . . ? C26A C21A C22A 117.3(3) . . ? C26A C21A C5 123.9(4) . . ? C22A C21A C5 118.6(4) . . ? C23A C22A C21A 121.4(4) . . ? C23A C22A H22A 119.3 . . ? C21A C22A H22A 119.3 . . ? C22A C23A C24A 119.7(3) . . ? C22A C23A H23A 120.1 . . ? C24A C23A H23A 120.1 . . ? C25A C24A O1A 124.4(4) . . ? C25A C24A C23A 120.6(3) . . ? O1A C24A C23A 115.0(4) . . ? C24A C25A C26A 119.2(4) . . ? C24A C25A H25A 120.4 . . ? C26A C25A H25A 120.4 . . ? C21A C26A C25A 121.7(4) . . ? C21A C26A H26A 119.1 . . ? C25A C26A H26A 119.1 . . ? C24A O1A C27A 116.5(3) . . ? O1A C27A H27A 109.5 . . ? O1A C27A H27B 109.5 . . ? H27A C27A H27B 109.5 . . ? O1A C27A H27C 109.5 . . ? H27A C27A H27C 109.5 . . ? H27B C27A H27C 109.5 . . ? N3 C6 C7 109.0(3) . . ? N3 C6 C21B 127.4(3) . . ? C7 C6 C21B 123.7(3) . . ? C8 C7 C6 109.3(3) . . ? C8 C7 H7 125.3 . . ? C6 C7 H7 125.3 . . ? C7 C8 C2 105.2(3) . . ? C7 C8 C11B 126.3(3) . . ? C2 C8 C11B 128.4(4) . . ? C12B C11B C16B 116.7(4) . . ? C12B C11B C8 120.6(4) . . ? C16B C11B C8 122.7(4) . . ? C11B C12B C13B 121.9(4) . . ? C11B C12B H12B 119.1 . . ? C13B C12B H12B 119.1 . . ? C14B C13B C12B 120.0(4) . . ? C14B C13B H13B 120.0 . . ? C12B C13B H13B 120.0 . . ? C15B C14B C13B 119.7(4) . . ? C15B C14B H14B 120.2 . . ? C13B C14B H14B 120.2 . . ? C14B C15B C16B 120.4(5) . . ? C14B C15B H15B 119.8 . . ? C16B C15B H15B 119.8 . . ? C11B C16B C15B 121.3(4) . . ? C11B C16B H16B 119.3 . . ? C15B C16B H16B 119.3 . . ? C26B C21B C22B 117.9(4) . . ? C26B C21B C6 118.8(4) . . ? C22B C21B C6 123.3(4) . . ? C21B C22B C23B 120.9(4) . . ? C21B C22B H22B 119.6 . . ? C23B C22B H22B 119.6 . . ? C24B C23B C22B 119.9(4) . . ? C24B C23B H23B 120.0 . . ? C22B C23B H23B 120.0 . . ? C23B C24B O1B 124.2(4) . . ? C23B C24B C25B 119.9(4) . . ? O1B C24B C25B 115.9(4) . . ? C26B C25B C24B 119.6(4) . . ? C26B C25B H25B 120.2 . . ? C24B C25B H25B 120.2 . . ? C25B C26B C21B 121.7(4) . . ? C25B C26B H26B 119.2 . . ? C21B C26B H26B 119.2 . . ? C24B O1B C27B 117.8(3) . . ? O1B C27B H27D 109.5 . . ? O1B C27B H27E 109.5 . . ? H27D C27B H27E 109.5 . . ? O1B C27B H27F 109.5 . . ? H27D C27B H27F 109.5 . . ? H27E C27B H27F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 N2 -2.8(6) . . . . ? C2 N1 C1 C3 175.6(4) . . . . ? N1 C1 N2 C5 177.4(4) . . . . ? C3 C1 N2 C5 -1.2(4) . . . . ? N1 C1 N2 B1 6.0(6) . . . . ? C3 C1 N2 B1 -172.7(4) . . . . ? C5 N2 B1 F1 -51.6(6) . . . . ? C1 N2 B1 F1 117.5(4) . . . . ? C5 N2 B1 F2 69.7(6) . . . . ? C1 N2 B1 F2 -121.2(4) . . . . ? C5 N2 B1 N3 -172.4(4) . . . . ? C1 N2 B1 N3 -3.3(6) . . . . ? C1 N1 C2 N3 -2.9(6) . . . . ? C1 N1 C2 C8 176.0(4) . . . . ? N1 C2 N3 C6 177.6(4) . . . . ? C8 C2 N3 C6 -1.4(4) . . . . ? N1 C2 N3 B1 5.1(6) . . . . ? C8 C2 N3 B1 -173.9(4) . . . . ? F1 B1 N3 C6 69.5(6) . . . . ? F2 B1 N3 C6 -51.9(6) . . . . ? N2 B1 N3 C6 -172.3(4) . . . . ? F1 B1 N3 C2 -119.9(4) . . . . ? F2 B1 N3 C2 118.7(4) . . . . ? N2 B1 N3 C2 -1.7(6) . . . . ? N1 C1 C3 C4 -177.2(4) . . . . ? N2 C1 C3 C4 1.5(4) . . . . ? N1 C1 C3 C11A 5.2(7) . . . . ? N2 C1 C3 C11A -176.2(4) . . . . ? C1 C3 C4 C5 -1.1(5) . . . . ? C11A C3 C4 C5 176.5(4) . . . . ? C1 N2 C5 C4 0.5(4) . . . . ? B1 N2 C5 C4 170.8(4) . . . . ? C1 N2 C5 C21A 178.6(4) . . . . ? B1 N2 C5 C21A -11.1(7) . . . . ? C3 C4 C5 N2 0.4(5) . . . . ? C3 C4 C5 C21A -177.8(4) . . . . ? C4 C3 C11A C16A -2.9(7) . . . . ? C1 C3 C11A C16A 174.2(4) . . . . ? C4 C3 C11A C12A 175.6(4) . . . . ? C1 C3 C11A C12A -7.3(7) . . . . ? C16A C11A C12A C13A -3.5(7) . . . . ? C3 C11A C12A C13A 178.0(4) . . . . ? C11A C12A C13A C14A 0.9(9) . . . . ? C12A C13A C14A C15A 1.9(8) . . . . ? C13A C14A C15A C16A -2.1(8) . . . . ? C12A C11A C16A C15A 3.3(7) . . . . ? C3 C11A C16A C15A -178.1(4) . . . . ? C14A C15A C16A C11A -0.6(8) . . . . ? N2 C5 C21A C26A -33.8(6) . . . . ? C4 C5 C21A C26A 144.0(4) . . . . ? N2 C5 C21A C22A 151.4(4) . . . . ? C4 C5 C21A C22A -30.7(6) . . . . ? C26A C21A C22A C23A 0.1(5) . . . . ? C5 C21A C22A C23A 175.2(3) . . . . ? C21A C22A C23A C24A 0.5(6) . . . . ? C22A C23A C24A C25A -1.5(6) . . . . ? C22A C23A C24A O1A 178.2(3) . . . . ? O1A C24A C25A C26A -178.0(3) . . . . ? C23A C24A C25A C26A 1.8(6) . . . . ? C22A C21A C26A C25A 0.1(5) . . . . ? C5 C21A C26A C25A -174.7(4) . . . . ? C24A C25A C26A C21A -1.1(6) . . . . ? C25A C24A O1A C27A 9.2(5) . . . . ? C23A C24A O1A C27A -170.6(3) . . . . ? C2 N3 C6 C7 1.0(4) . . . . ? B1 N3 C6 C7 172.7(4) . . . . ? C2 N3 C6 C21B -179.3(4) . . . . ? B1 N3 C6 C21B -7.6(7) . . . . ? N3 C6 C7 C8 -0.2(5) . . . . ? C21B C6 C7 C8 -179.9(4) . . . . ? C6 C7 C8 C2 -0.7(5) . . . . ? C6 C7 C8 C11B 178.8(4) . . . . ? N1 C2 C8 C7 -177.7(4) . . . . ? N3 C2 C8 C7 1.3(5) . . . . ? N1 C2 C8 C11B 2.9(7) . . . . ? N3 C2 C8 C11B -178.1(4) . . . . ? C7 C8 C11B C12B -13.1(7) . . . . ? C2 C8 C11B C12B 166.1(4) . . . . ? C7 C8 C11B C16B 166.3(4) . . . . ? C2 C8 C11B C16B -14.4(7) . . . . ? C16B C11B C12B C13B 0.3(7) . . . . ? C8 C11B C12B C13B 179.7(4) . . . . ? C11B C12B C13B C14B 1.8(8) . . . . ? C12B C13B C14B C15B -2.7(8) . . . . ? C13B C14B C15B C16B 1.5(8) . . . . ? C12B C11B C16B C15B -1.5(7) . . . . ? C8 C11B C16B C15B 179.1(4) . . . . ? C14B C15B C16B C11B 0.6(8) . . . . ? N3 C6 C21B C26B 143.6(4) . . . . ? C7 C6 C21B C26B -36.8(6) . . . . ? N3 C6 C21B C22B -38.8(6) . . . . ? C7 C6 C21B C22B 140.8(4) . . . . ? C26B C21B C22B C23B -0.8(5) . . . . ? C6 C21B C22B C23B -178.4(4) . . . . ? C21B C22B C23B C24B -1.8(6) . . . . ? C22B C23B C24B O1B -176.9(3) . . . . ? C22B C23B C24B C25B 3.2(6) . . . . ? C23B C24B C25B C26B -2.1(6) . . . . ? O1B C24B C25B C26B 178.1(3) . . . . ? C24B C25B C26B C21B -0.6(6) . . . . ? C22B C21B C26B C25B 1.9(6) . . . . ? C6 C21B C26B C25B 179.7(4) . . . . ? C23B C24B O1B C27B -0.9(6) . . . . ? C25B C24B O1B C27B 179.0(3) . . . . ? _diffrn_measured_fraction_theta_max 1.00 _diffrn_reflns_theta_full 26.0 _diffrn_measured_fraction_theta_full 1.00 _refine_diff_density_max 0.25 _refine_diff_density_min -0.21 _refine_diff_density_rms 0.05