# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is © The Owner Societies 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_Adamantyl_mesityl_BODIPY _database_code_depnum_ccdc_archive 'CCDC 852756' #TrackingRef '8007_web_deposit_cif_file_0_PascalRetailleau_1320410039.IP-BDPY _todeposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,4-Difluoro-3,5-di-(adamantyl)-8-mesityl-4-bora-3a,4a-diaza-s-indacene ; _chemical_name_common 'Adamantyl mesityl BODIPY' _chemical_melting_point ? _chemical_formula_moiety 'C38 H45 B F2 N2' _chemical_formula_sum 'C38 H45 B F2 N2' _chemical_formula_weight 578.57 _chemical_absolute_configuration ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 14.0557(3) _cell_length_b 11.4779(3) _cell_length_c 19.3737(13) _cell_angle_alpha 90.00 _cell_angle_beta 98.905(7) _cell_angle_gamma 90.00 _cell_volume 3087.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 8387 _cell_measurement_theta_min 6.9 _cell_measurement_theta_max 72.0 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 0.626 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.833 _exptl_absorpt_process_details 'FS_ABSCOR (Rigaku, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku rapid II RAXIS conversion' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_type 'RAPID II large area curved imaging plate detector ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20448 _diffrn_reflns_av_R_equivalents 0.0586 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 7.14 _diffrn_reflns_theta_max 72.10 _reflns_number_total 5770 _reflns_number_gt 4394 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _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. 14 omitted reflections due to high Delta(F^^2)/esd (part of Rapid II detector shaded by the chi-partial arm). ; _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^)+(0.0756P)^2^+0.1698P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0019(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5756 _refine_ls_number_parameters 392 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1488 _refine_ls_wR_factor_gt 0.1383 _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_restrained_S_all 1.152 _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 F1 F 1.26208(6) 0.49098(9) 0.32372(4) 0.0433(3) Uani 1 1 d . . . F2 F 1.25747(7) 0.65974(9) 0.26253(5) 0.0450(3) Uani 1 1 d . . . N1 N 1.11884(8) 0.60941(13) 0.31541(6) 0.0296(3) Uani 1 1 d . . . N2 N 1.16334(8) 0.50084(12) 0.20916(6) 0.0290(3) Uani 1 1 d . . . C5 C 1.20784(10) 0.43720(15) 0.16374(7) 0.0275(4) Uani 1 1 d . . . C29 C 1.30663(10) 0.38003(15) 0.17834(7) 0.0257(4) Uani 1 1 d . . . C13 C 0.71448(11) 0.63049(17) 0.10184(7) 0.0362(4) Uani 1 1 d . . . C30 C 1.31005(11) 0.28533(16) 0.23551(7) 0.0316(4) Uani 1 1 d . . . H30A H 1.2969 0.3212 0.2795 0.038 Uiso 1 1 calc R . . H30B H 1.2597 0.2261 0.2209 0.038 Uiso 1 1 calc R . . C8 C 1.07098(10) 0.52833(15) 0.17461(7) 0.0299(4) Uani 1 1 d . . . C10 C 0.90318(10) 0.60263(16) 0.17010(7) 0.0303(4) Uani 1 1 d . . . C31 C 1.40943(11) 0.22656(16) 0.24786(8) 0.0337(4) Uani 1 1 d . . . H31 H 1.4110 0.1671 0.2858 0.040 Uiso 1 1 calc R . . C4 C 1.11485(11) 0.65291(16) 0.38057(8) 0.0343(4) Uani 1 1 d . . . C38 C 1.42817(11) 0.16692(16) 0.18107(8) 0.0360(4) Uani 1 1 d . . . H38A H 1.4920 0.1285 0.1891 0.043 Uiso 1 1 calc R . . H38B H 1.3786 0.1066 0.1671 0.043 Uiso 1 1 calc R . . C7 C 1.06011(11) 0.48221(16) 0.10682(8) 0.0354(4) Uani 1 1 d . . . H7 H 1.0046 0.4882 0.0722 0.043 Uiso 1 1 calc R . . C11 C 0.83285(11) 0.52125(16) 0.18123(8) 0.0327(4) Uani 1 1 d . . . C3 C 1.02122(11) 0.69384(19) 0.38279(9) 0.0475(5) Uani 1 1 d . . . H3 H 0.9991 0.7273 0.4223 0.057 Uiso 1 1 calc R . . C6 C 1.14442(11) 0.42686(17) 0.09987(8) 0.0355(4) Uani 1 1 d . . . H6 H 1.1580 0.3882 0.0591 0.043 Uiso 1 1 calc R . . C12 C 0.73934(11) 0.53781(17) 0.14642(8) 0.0367(4) Uani 1 1 d . . . H12 H 0.6910 0.4833 0.1536 0.044 Uiso 1 1 calc R . . C19 C 1.19515(10) 0.65646(15) 0.44334(7) 0.0301(4) Uani 1 1 d . . . C32 C 1.48773(11) 0.31777(17) 0.26973(8) 0.0401(5) Uani 1 1 d . . . H32A H 1.4762 0.3567 0.3133 0.048 Uiso 1 1 calc R . . H32B H 1.5516 0.2795 0.2787 0.048 Uiso 1 1 calc R . . C1 C 1.02704(11) 0.62422(16) 0.27625(8) 0.0332(4) Uani 1 1 d . . . C9 C 1.00406(10) 0.58634(15) 0.20771(7) 0.0304(4) Uani 1 1 d . . . C34 C 1.38785(10) 0.46947(16) 0.19960(8) 0.0339(4) Uani 1 1 d . . . H34A H 1.3869 0.5287 0.1624 0.041 Uiso 1 1 calc R . . H34B H 1.3774 0.5097 0.2430 0.041 Uiso 1 1 calc R . . C33 C 1.48612(11) 0.40773(17) 0.21147(9) 0.0377(4) Uani 1 1 d . . . H33 H 1.5379 0.4666 0.2256 0.045 Uiso 1 1 calc R . . C37 C 1.32704(11) 0.31785(17) 0.11137(7) 0.0338(4) Uani 1 1 d . . . H37A H 1.2760 0.2595 0.0968 0.041 Uiso 1 1 calc R . . H37B H 1.3255 0.3756 0.0733 0.041 Uiso 1 1 calc R . . C36 C 1.42532(11) 0.25719(16) 0.12336(8) 0.0336(4) Uani 1 1 d . . . H36 H 1.4366 0.2180 0.0792 0.040 Uiso 1 1 calc R . . B1 B 1.20512(12) 0.56431(18) 0.27939(9) 0.0303(5) Uani 1 1 d . . . C35 C 1.50409(11) 0.34777(17) 0.14464(9) 0.0399(5) Uani 1 1 d . . . H35A H 1.5679 0.3094 0.1523 0.048 Uiso 1 1 calc R . . H35B H 1.5037 0.4061 0.1069 0.048 Uiso 1 1 calc R . . C27 C 1.28895(12) 0.70759(19) 0.42600(8) 0.0425(5) Uani 1 1 d . . . H27A H 1.2774 0.7878 0.4079 0.051 Uiso 1 1 calc R . . H27B H 1.3120 0.6601 0.3893 0.051 Uiso 1 1 calc R . . C2 C 0.96727(11) 0.67733(18) 0.31842(9) 0.0461(5) Uani 1 1 d . . . H2 H 0.9016 0.6980 0.3049 0.055 Uiso 1 1 calc R . . C17 C 0.61136(12) 0.6468(2) 0.06641(9) 0.0541(6) Uani 1 1 d . . . H17A H 0.6035 0.7253 0.0464 0.081 Uiso 1 1 calc R . . H17B H 0.5677 0.6368 0.1008 0.081 Uiso 1 1 calc R . . H17C H 0.5962 0.5889 0.0291 0.081 Uiso 1 1 calc R . . C15 C 0.88028(11) 0.69747(17) 0.12570(8) 0.0358(4) Uani 1 1 d . . . C23 C 1.24063(13) 0.7351(2) 0.56652(9) 0.0555(6) Uani 1 1 d . . . H23 H 1.2181 0.7848 0.6032 0.067 Uiso 1 1 calc R . . C18 C 0.95440(13) 0.7890(2) 0.11577(12) 0.0603(6) Uani 1 1 d . . . H18A H 0.9489 0.8547 0.1472 0.091 Uiso 1 1 calc R . . H18B H 0.9433 0.8162 0.0673 0.091 Uiso 1 1 calc R . . H18C H 1.0191 0.7552 0.1264 0.091 Uiso 1 1 calc R . . C16 C 0.85552(13) 0.41860(18) 0.22923(10) 0.0481(5) Uani 1 1 d . . . H16A H 0.8740 0.4463 0.2773 0.072 Uiso 1 1 calc R . . H16B H 0.9088 0.3741 0.2151 0.072 Uiso 1 1 calc R . . H16C H 0.7986 0.3686 0.2266 0.072 Uiso 1 1 calc R . . C25 C 1.33298(14) 0.7851(2) 0.54774(9) 0.0541(6) Uani 1 1 d . . . H25A H 1.3832 0.7870 0.5896 0.065 Uiso 1 1 calc R . . H25B H 1.3219 0.8658 0.5303 0.065 Uiso 1 1 calc R . . C20 C 1.21345(15) 0.53349(18) 0.47298(9) 0.0533(6) Uani 1 1 d . . . H20A H 1.2343 0.4821 0.4371 0.064 Uiso 1 1 calc R . . H20B H 1.1532 0.5013 0.4858 0.064 Uiso 1 1 calc R . . C26 C 1.36590(12) 0.7094(2) 0.49171(9) 0.0516(6) Uani 1 1 d . . . H26 H 1.4271 0.7418 0.4793 0.062 Uiso 1 1 calc R . . C14 C 0.78561(11) 0.70876(17) 0.09177(8) 0.0376(4) Uani 1 1 d . . . H14 H 0.7696 0.7724 0.0608 0.045 Uiso 1 1 calc R . . C24 C 1.16322(13) 0.7333(2) 0.50090(9) 0.0579(6) Uani 1 1 d . . . H24A H 1.1515 0.8137 0.4831 0.070 Uiso 1 1 calc R . . H24B H 1.1022 0.7028 0.5133 0.070 Uiso 1 1 calc R . . C22 C 1.25791(16) 0.6121(2) 0.59395(9) 0.0702(8) Uani 1 1 d . . . H22A H 1.1976 0.5798 0.6066 0.084 Uiso 1 1 calc R . . H22B H 1.3073 0.6126 0.6364 0.084 Uiso 1 1 calc R . . C28 C 1.38355(15) 0.5870(2) 0.51854(11) 0.0714(8) Uani 1 1 d . . . H28A H 1.4345 0.5873 0.5600 0.086 Uiso 1 1 calc R . . H28B H 1.4058 0.5380 0.4821 0.086 Uiso 1 1 calc R . . C21 C 1.29182(18) 0.5370(2) 0.53795(10) 0.0687(7) Uani 1 1 d . . . H21 H 1.3044 0.4561 0.5563 0.082 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 F1 0.0385(5) 0.0569(8) 0.0299(5) -0.0091(4) -0.0089(4) 0.0214(5) F2 0.0394(6) 0.0496(8) 0.0478(6) -0.0141(5) 0.0127(4) -0.0108(5) N1 0.0218(6) 0.0373(10) 0.0279(6) -0.0051(6) -0.0019(5) 0.0051(6) N2 0.0213(6) 0.0384(10) 0.0255(6) -0.0003(6) -0.0017(5) 0.0035(6) C5 0.0250(7) 0.0318(11) 0.0250(7) -0.0020(7) 0.0017(6) 0.0014(7) C29 0.0239(7) 0.0282(11) 0.0239(6) 0.0005(6) 0.0006(5) 0.0008(6) C13 0.0243(8) 0.0564(13) 0.0258(7) -0.0037(8) -0.0025(6) 0.0075(8) C30 0.0304(8) 0.0360(12) 0.0283(7) 0.0014(7) 0.0043(6) 0.0002(7) C8 0.0222(7) 0.0357(11) 0.0293(7) 0.0004(7) -0.0034(6) 0.0028(7) C10 0.0218(7) 0.0396(12) 0.0275(7) -0.0027(7) -0.0021(6) 0.0045(7) C31 0.0330(8) 0.0386(12) 0.0286(7) 0.0047(7) 0.0016(6) 0.0070(7) C4 0.0263(8) 0.0453(13) 0.0303(7) -0.0070(7) 0.0013(6) 0.0044(7) C38 0.0334(8) 0.0351(12) 0.0373(8) -0.0027(8) -0.0008(7) 0.0044(7) C7 0.0282(8) 0.0462(13) 0.0287(7) -0.0018(7) -0.0059(6) 0.0036(7) C11 0.0281(8) 0.0389(12) 0.0299(7) -0.0016(7) 0.0005(6) 0.0025(7) C3 0.0281(8) 0.0748(16) 0.0388(9) -0.0181(9) 0.0023(7) 0.0107(9) C6 0.0315(8) 0.0468(13) 0.0260(7) -0.0068(7) -0.0030(6) 0.0051(8) C12 0.0252(8) 0.0497(13) 0.0338(8) -0.0041(8) 0.0001(6) -0.0036(8) C19 0.0258(7) 0.0366(12) 0.0267(7) -0.0041(7) 0.0002(6) 0.0018(7) C32 0.0293(8) 0.0511(14) 0.0357(8) -0.0104(8) -0.0080(7) 0.0095(8) C1 0.0214(7) 0.0425(12) 0.0339(8) -0.0047(7) -0.0016(6) 0.0065(7) C9 0.0234(8) 0.0343(11) 0.0316(7) -0.0005(7) -0.0011(6) 0.0016(7) C34 0.0269(8) 0.0332(12) 0.0417(8) -0.0030(7) 0.0060(6) -0.0002(7) C33 0.0235(8) 0.0386(12) 0.0503(10) -0.0093(8) 0.0034(7) -0.0037(7) C37 0.0314(8) 0.0442(12) 0.0247(7) -0.0031(7) 0.0011(6) 0.0086(8) C36 0.0323(8) 0.0404(12) 0.0282(7) -0.0025(7) 0.0047(6) 0.0079(7) B1 0.0211(8) 0.0383(14) 0.0295(8) -0.0064(8) -0.0023(6) 0.0027(8) C35 0.0294(8) 0.0449(13) 0.0478(9) -0.0015(9) 0.0136(7) 0.0030(8) C27 0.0362(9) 0.0603(14) 0.0294(8) -0.0032(8) 0.0000(7) -0.0107(9) C2 0.0239(8) 0.0696(16) 0.0426(9) -0.0137(9) -0.0016(7) 0.0118(8) C17 0.0272(9) 0.0968(19) 0.0348(8) 0.0078(10) -0.0058(7) 0.0066(10) C15 0.0280(8) 0.0410(12) 0.0369(8) 0.0046(8) 0.0006(6) 0.0030(7) C23 0.0442(10) 0.0849(19) 0.0349(9) -0.0259(10) -0.0017(8) 0.0105(11) C18 0.0385(10) 0.0598(16) 0.0793(14) 0.0233(12) -0.0017(9) -0.0060(10) C16 0.0394(10) 0.0487(14) 0.0539(11) 0.0110(10) -0.0001(8) 0.0032(9) C25 0.0609(12) 0.0555(15) 0.0401(9) -0.0120(9) -0.0101(8) -0.0117(11) C20 0.0680(13) 0.0476(15) 0.0386(9) 0.0026(9) -0.0100(9) -0.0116(11) C26 0.0319(9) 0.0865(18) 0.0348(9) -0.0126(10) 0.0002(7) -0.0136(10) C14 0.0318(8) 0.0454(13) 0.0335(8) 0.0092(8) -0.0014(6) 0.0084(8) C24 0.0387(10) 0.0921(19) 0.0403(10) -0.0250(11) -0.0024(8) 0.0150(11) C22 0.0706(15) 0.107(2) 0.0293(9) 0.0064(11) -0.0028(9) -0.0236(14) C28 0.0520(13) 0.100(2) 0.0518(11) -0.0264(13) -0.0243(10) 0.0337(13) C21 0.0988(18) 0.0518(16) 0.0438(11) 0.0095(10) -0.0254(11) 0.0013(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 F1 B1 1.3689(19) . ? F2 B1 1.386(2) . ? N1 C4 1.3667(19) . ? N1 C1 1.4022(17) . ? N1 B1 1.577(2) . ? N2 C5 1.3673(19) . ? N2 C8 1.4014(16) . ? N2 B1 1.575(2) . ? C5 C6 1.4137(18) . ? C5 C29 1.5222(19) . ? C29 C34 1.543(2) . ? C29 C37 1.546(2) . ? C29 C30 1.547(2) . ? C13 C14 1.380(2) . ? C13 C12 1.381(2) . ? C13 C17 1.5162(19) . ? C30 C31 1.536(2) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C8 C9 1.388(2) . ? C8 C7 1.402(2) . ? C10 C15 1.394(2) . ? C10 C11 1.401(2) . ? C10 C9 1.5021(18) . ? C31 C38 1.523(2) . ? C31 C32 1.530(2) . ? C31 H31 1.0000 . ? C4 C3 1.404(2) . ? C4 C19 1.5264(19) . ? C38 C36 1.520(2) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C7 C6 1.369(2) . ? C7 H7 0.9500 . ? C11 C12 1.3944(19) . ? C11 C16 1.504(2) . ? C3 C2 1.369(2) . ? C3 H3 0.9500 . ? C6 H6 0.9500 . ? C12 H12 0.9500 . ? C19 C27 1.527(2) . ? C19 C20 1.531(3) . ? C19 C24 1.542(2) . ? C32 C33 1.527(2) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C1 C9 1.387(2) . ? C1 C2 1.399(2) . ? C34 C33 1.538(2) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C33 C35 1.522(2) . ? C33 H33 1.0000 . ? C37 C36 1.532(2) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C36 C35 1.528(2) . ? C36 H36 1.0000 . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C27 C26 1.538(2) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C2 H2 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C15 C14 1.396(2) . ? C15 C18 1.512(3) . ? C23 C25 1.514(3) . ? C23 C22 1.515(3) . ? C23 C24 1.540(2) . ? C23 H23 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C25 C26 1.518(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C20 C21 1.540(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C26 C28 1.505(3) . ? C26 H26 1.0000 . ? C14 H14 0.9500 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C22 C21 1.519(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C28 C21 1.511(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C21 H21 1.0000 . ? 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 C4 N1 C1 106.83(12) . . ? C4 N1 B1 132.29(11) . . ? C1 N1 B1 120.44(12) . . ? C5 N2 C8 107.17(11) . . ? C5 N2 B1 131.05(12) . . ? C8 N2 B1 120.17(13) . . ? N2 C5 C6 108.59(13) . . ? N2 C5 C29 127.28(12) . . ? C6 C5 C29 124.06(14) . . ? C5 C29 C34 112.26(13) . . ? C5 C29 C37 108.99(11) . . ? C34 C29 C37 107.79(12) . . ? C5 C29 C30 111.24(12) . . ? C34 C29 C30 109.67(11) . . ? C37 C29 C30 106.69(14) . . ? C14 C13 C12 118.11(14) . . ? C14 C13 C17 121.22(16) . . ? C12 C13 C17 120.66(16) . . ? C31 C30 C29 110.29(12) . . ? C31 C30 H30A 109.6 . . ? C29 C30 H30A 109.6 . . ? C31 C30 H30B 109.6 . . ? C29 C30 H30B 109.6 . . ? H30A C30 H30B 108.1 . . ? C9 C8 N2 122.09(13) . . ? C9 C8 C7 129.08(13) . . ? N2 C8 C7 108.72(13) . . ? C15 C10 C11 120.98(14) . . ? C15 C10 C9 120.46(15) . . ? C11 C10 C9 118.56(14) . . ? C38 C31 C32 109.35(14) . . ? C38 C31 C30 109.75(12) . . ? C32 C31 C30 109.90(14) . . ? C38 C31 H31 109.3 . . ? C32 C31 H31 109.3 . . ? C30 C31 H31 109.3 . . ? N1 C4 C3 108.86(13) . . ? N1 C4 C19 127.93(13) . . ? C3 C4 C19 123.20(14) . . ? C36 C38 C31 109.28(14) . . ? C36 C38 H38A 109.8 . . ? C31 C38 H38A 109.8 . . ? C36 C38 H38B 109.8 . . ? C31 C38 H38B 109.8 . . ? H38A C38 H38B 108.3 . . ? C6 C7 C8 107.26(12) . . ? C6 C7 H7 126.4 . . ? C8 C7 H7 126.4 . . ? C12 C11 C10 118.00(15) . . ? C12 C11 C16 119.96(16) . . ? C10 C11 C16 122.04(14) . . ? C2 C3 C4 108.38(15) . . ? C2 C3 H3 125.8 . . ? C4 C3 H3 125.8 . . ? C7 C6 C5 108.24(14) . . ? C7 C6 H6 125.9 . . ? C5 C6 H6 125.9 . . ? C13 C12 C11 122.41(16) . . ? C13 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? C4 C19 C27 113.09(13) . . ? C4 C19 C20 109.56(14) . . ? C27 C19 C20 109.65(15) . . ? C4 C19 C24 109.23(13) . . ? C27 C19 C24 107.28(15) . . ? C20 C19 C24 107.88(15) . . ? C33 C32 C31 109.28(12) . . ? C33 C32 H32A 109.8 . . ? C31 C32 H32A 109.8 . . ? C33 C32 H32B 109.8 . . ? C31 C32 H32B 109.8 . . ? H32A C32 H32B 108.3 . . ? C9 C1 C2 128.58(14) . . ? C9 C1 N1 122.58(14) . . ? C2 C1 N1 108.80(13) . . ? C1 C9 C8 121.24(13) . . ? C1 C9 C10 119.20(14) . . ? C8 C9 C10 119.47(13) . . ? C33 C34 C29 110.09(14) . . ? C33 C34 H34A 109.6 . . ? C29 C34 H34A 109.6 . . ? C33 C34 H34B 109.6 . . ? C29 C34 H34B 109.6 . . ? H34A C34 H34B 108.2 . . ? C35 C33 C32 109.73(15) . . ? C35 C33 C34 110.17(13) . . ? C32 C33 C34 109.41(13) . . ? C35 C33 H33 109.2 . . ? C32 C33 H33 109.2 . . ? C34 C33 H33 109.2 . . ? C36 C37 C29 111.26(11) . . ? C36 C37 H37A 109.4 . . ? C29 C37 H37A 109.4 . . ? C36 C37 H37B 109.4 . . ? C29 C37 H37B 109.4 . . ? H37A C37 H37B 108.0 . . ? C38 C36 C35 109.26(13) . . ? C38 C36 C37 109.98(13) . . ? C35 C36 C37 109.29(14) . . ? C38 C36 H36 109.4 . . ? C35 C36 H36 109.4 . . ? C37 C36 H36 109.4 . . ? F1 B1 F2 110.70(13) . . ? F1 B1 N2 111.18(15) . . ? F2 B1 N2 107.60(13) . . ? F1 B1 N1 109.84(13) . . ? F2 B1 N1 108.50(14) . . ? N2 B1 N1 108.94(11) . . ? C33 C35 C36 109.17(13) . . ? C33 C35 H35A 109.8 . . ? C36 C35 H35A 109.8 . . ? C33 C35 H35B 109.8 . . ? C36 C35 H35B 109.8 . . ? H35A C35 H35B 108.3 . . ? C19 C27 C26 110.10(14) . . ? C19 C27 H27A 109.6 . . ? C26 C27 H27A 109.6 . . ? C19 C27 H27B 109.6 . . ? C26 C27 H27B 109.6 . . ? H27A C27 H27B 108.2 . . ? C3 C2 C1 107.12(14) . . ? C3 C2 H2 126.4 . . ? C1 C2 H2 126.4 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C10 C15 C14 118.38(16) . . ? C10 C15 C18 121.53(14) . . ? C14 C15 C18 120.05(16) . . ? C25 C23 C22 109.90(18) . . ? C25 C23 C24 109.22(17) . . ? C22 C23 C24 109.34(18) . . ? C25 C23 H23 109.5 . . ? C22 C23 H23 109.5 . . ? C24 C23 H23 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C23 C25 C26 108.82(16) . . ? C23 C25 H25A 109.9 . . ? C26 C25 H25A 109.9 . . ? C23 C25 H25B 109.9 . . ? C26 C25 H25B 109.9 . . ? H25A C25 H25B 108.3 . . ? C19 C20 C21 109.87(16) . . ? C19 C20 H20A 109.7 . . ? C21 C20 H20A 109.7 . . ? C19 C20 H20B 109.7 . . ? C21 C20 H20B 109.7 . . ? H20A C20 H20B 108.2 . . ? C28 C26 C25 109.85(17) . . ? C28 C26 C27 109.30(16) . . ? C25 C26 C27 110.28(16) . . ? C28 C26 H26 109.1 . . ? C25 C26 H26 109.1 . . ? C27 C26 H26 109.1 . . ? C13 C14 C15 122.11(16) . . ? C13 C14 H14 118.9 . . ? C15 C14 H14 118.9 . . ? C23 C24 C19 110.92(14) . . ? C23 C24 H24A 109.5 . . ? C19 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? C19 C24 H24B 109.5 . . ? H24A C24 H24B 108.0 . . ? C23 C22 C21 109.23(17) . . ? C23 C22 H22A 109.8 . . ? C21 C22 H22A 109.8 . . ? C23 C22 H22B 109.8 . . ? C21 C22 H22B 109.8 . . ? H22A C22 H22B 108.3 . . ? C26 C28 C21 109.82(17) . . ? C26 C28 H28A 109.7 . . ? C21 C28 H28A 109.7 . . ? C26 C28 H28B 109.7 . . ? C21 C28 H28B 109.7 . . ? H28A C28 H28B 108.2 . . ? C28 C21 C22 109.66(19) . . ? C28 C21 C20 109.67(17) . . ? C22 C21 C20 109.57(19) . . ? C28 C21 H21 109.3 . . ? C22 C21 H21 109.3 . . ? C20 C21 H21 109.3 . . ? 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 C8 N2 C5 C6 1.40(19) . . . . ? B1 N2 C5 C6 -163.72(17) . . . . ? C8 N2 C5 C29 -175.60(15) . . . . ? B1 N2 C5 C29 19.3(3) . . . . ? N2 C5 C29 C34 -60.4(2) . . . . ? C6 C5 C29 C34 123.00(17) . . . . ? N2 C5 C29 C37 -179.76(16) . . . . ? C6 C5 C29 C37 3.7(2) . . . . ? N2 C5 C29 C30 62.9(2) . . . . ? C6 C5 C29 C30 -113.69(17) . . . . ? C5 C29 C30 C31 178.41(12) . . . . ? C34 C29 C30 C31 -56.82(17) . . . . ? C37 C29 C30 C31 59.66(15) . . . . ? C5 N2 C8 C9 175.70(16) . . . . ? B1 N2 C8 C9 -17.2(2) . . . . ? C5 N2 C8 C7 -1.00(19) . . . . ? B1 N2 C8 C7 166.06(15) . . . . ? C29 C30 C31 C38 -61.64(18) . . . . ? C29 C30 C31 C32 58.64(16) . . . . ? C1 N1 C4 C3 0.5(2) . . . . ? B1 N1 C4 C3 172.65(18) . . . . ? C1 N1 C4 C19 179.13(17) . . . . ? B1 N1 C4 C19 -8.7(3) . . . . ? C32 C31 C38 C36 -60.68(16) . . . . ? C30 C31 C38 C36 59.93(17) . . . . ? C9 C8 C7 C6 -176.21(18) . . . . ? N2 C8 C7 C6 0.2(2) . . . . ? C15 C10 C11 C12 0.2(2) . . . . ? C9 C10 C11 C12 179.54(14) . . . . ? C15 C10 C11 C16 -179.59(16) . . . . ? C9 C10 C11 C16 -0.2(2) . . . . ? N1 C4 C3 C2 -0.9(2) . . . . ? C19 C4 C3 C2 -179.61(18) . . . . ? C8 C7 C6 C5 0.7(2) . . . . ? N2 C5 C6 C7 -1.3(2) . . . . ? C29 C5 C6 C7 175.81(16) . . . . ? C14 C13 C12 C11 0.1(2) . . . . ? C17 C13 C12 C11 -178.49(16) . . . . ? C10 C11 C12 C13 0.2(2) . . . . ? C16 C11 C12 C13 179.94(16) . . . . ? N1 C4 C19 C27 50.2(3) . . . . ? C3 C4 C19 C27 -131.3(2) . . . . ? N1 C4 C19 C20 -72.4(2) . . . . ? C3 C4 C19 C20 106.0(2) . . . . ? N1 C4 C19 C24 169.62(19) . . . . ? C3 C4 C19 C24 -12.0(3) . . . . ? C38 C31 C32 C33 59.75(17) . . . . ? C30 C31 C32 C33 -60.77(17) . . . . ? C4 N1 C1 C9 -178.00(17) . . . . ? B1 N1 C1 C9 8.7(3) . . . . ? C4 N1 C1 C2 0.0(2) . . . . ? B1 N1 C1 C2 -173.20(16) . . . . ? C2 C1 C9 C8 -175.88(19) . . . . ? N1 C1 C9 C8 1.8(3) . . . . ? C2 C1 C9 C10 0.7(3) . . . . ? N1 C1 C9 C10 178.30(15) . . . . ? N2 C8 C9 C1 2.6(3) . . . . ? C7 C8 C9 C1 178.61(19) . . . . ? N2 C8 C9 C10 -173.90(15) . . . . ? C7 C8 C9 C10 2.1(3) . . . . ? C15 C10 C9 C1 97.3(2) . . . . ? C11 C10 C9 C1 -82.0(2) . . . . ? C15 C10 C9 C8 -86.1(2) . . . . ? C11 C10 C9 C8 94.58(19) . . . . ? C5 C29 C34 C33 -178.23(12) . . . . ? C37 C29 C34 C33 -58.20(16) . . . . ? C30 C29 C34 C33 57.58(16) . . . . ? C31 C32 C33 C35 -59.61(17) . . . . ? C31 C32 C33 C34 61.37(18) . . . . ? C29 C34 C33 C35 60.57(18) . . . . ? C29 C34 C33 C32 -60.15(16) . . . . ? C5 C29 C37 C36 -179.24(13) . . . . ? C34 C29 C37 C36 58.68(18) . . . . ? C30 C29 C37 C36 -59.04(17) . . . . ? C31 C38 C36 C35 61.11(16) . . . . ? C31 C38 C36 C37 -58.85(17) . . . . ? C29 C37 C36 C38 59.91(19) . . . . ? C29 C37 C36 C35 -60.03(18) . . . . ? C5 N2 B1 F1 -50.9(2) . . . . ? C8 N2 B1 F1 145.58(14) . . . . ? C5 N2 B1 F2 70.5(2) . . . . ? C8 N2 B1 F2 -93.05(16) . . . . ? C5 N2 B1 N1 -172.09(15) . . . . ? C8 N2 B1 N1 24.4(2) . . . . ? C4 N1 B1 F1 46.4(2) . . . . ? C1 N1 B1 F1 -142.31(15) . . . . ? C4 N1 B1 F2 -74.7(2) . . . . ? C1 N1 B1 F2 96.57(16) . . . . ? C4 N1 B1 N2 168.44(17) . . . . ? C1 N1 B1 N2 -20.3(2) . . . . ? C32 C33 C35 C36 60.02(17) . . . . ? C34 C33 C35 C36 -60.50(19) . . . . ? C38 C36 C35 C33 -60.67(17) . . . . ? C37 C36 C35 C33 59.72(17) . . . . ? C4 C19 C27 C26 179.47(16) . . . . ? C20 C19 C27 C26 -57.9(2) . . . . ? C24 C19 C27 C26 59.0(2) . . . . ? C4 C3 C2 C1 0.9(2) . . . . ? C9 C1 C2 C3 177.3(2) . . . . ? N1 C1 C2 C3 -0.6(2) . . . . ? C11 C10 C15 C14 -0.8(2) . . . . ? C9 C10 C15 C14 179.85(15) . . . . ? C11 C10 C15 C18 177.16(17) . . . . ? C9 C10 C15 C18 -2.2(3) . . . . ? C22 C23 C25 C26 60.2(2) . . . . ? C24 C23 C25 C26 -59.8(2) . . . . ? C4 C19 C20 C21 -177.95(16) . . . . ? C27 C19 C20 C21 57.4(2) . . . . ? C24 C19 C20 C21 -59.1(2) . . . . ? C23 C25 C26 C28 -60.1(2) . . . . ? C23 C25 C26 C27 60.5(2) . . . . ? C19 C27 C26 C28 59.8(2) . . . . ? C19 C27 C26 C25 -61.1(2) . . . . ? C12 C13 C14 C15 -0.8(3) . . . . ? C17 C13 C14 C15 177.82(17) . . . . ? C10 C15 C14 C13 1.1(3) . . . . ? C18 C15 C14 C13 -176.85(17) . . . . ? C25 C23 C24 C19 60.7(2) . . . . ? C22 C23 C24 C19 -59.5(2) . . . . ? C4 C19 C24 C23 177.63(17) . . . . ? C27 C19 C24 C23 -59.4(2) . . . . ? C20 C19 C24 C23 58.6(2) . . . . ? C25 C23 C22 C21 -60.0(2) . . . . ? C24 C23 C22 C21 59.9(2) . . . . ? C25 C26 C28 C21 60.03(19) . . . . ? C27 C26 C28 C21 -61.1(2) . . . . ? C26 C28 C21 C22 -59.5(2) . . . . ? C26 C28 C21 C20 60.9(2) . . . . ? C23 C22 C21 C28 59.2(2) . . . . ? C23 C22 C21 C20 -61.2(2) . . . . ? C19 C20 C21 C28 -58.9(2) . . . . ? C19 C20 C21 C22 61.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 72.10 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.238 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.044