# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_4.HBF4 _database_code_depnum_ccdc_archive 'CCDC 890293' #TrackingRef 'CrystallographicData.cif' _cell_length_a 11.9648(3) _cell_length_b 11.3421(4) _cell_length_c 12.6719(4) _cell_angle_alpha 90 _cell_angle_beta 117.4185(13) _cell_angle_gamma 90 _cell_volume 1526.48(8) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403 -0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C31 H37 B1 F4 N2 O3 # Dc = 1.25 Fooo = 604.00 Mu = 0.96 M = 572.45 # Found Formula = C31 H37 B1 F4 N2 O3 # Dc = 1.25 FOOO = 604.00 Mu = 0.96 M = 572.45 _chemical_formula_sum 'C31 H37 B1 F4 N2 O3' _chemical_formula_moiety 'C31 H37 B1 F4 N2 O3' _chemical_compound_source . _chemical_formula_weight 572.45 _cell_measurement_reflns_used 3487 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.060 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_max 0.240 _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 0.096 # Sheldrick geometric approximatio 0.98 0.99 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.99 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 6401 _reflns_number_total 3634 _diffrn_reflns_av_R_equivalents 0.031 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 3634 # Theoretical number of reflections is about 6987 _diffrn_reflns_theta_min 5.105 _diffrn_reflns_theta_max 27.462 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.913 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -15 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.32 _refine_diff_density_max 0.35 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 3634 _refine_ls_number_restraints 1 _refine_ls_number_parameters 370 _oxford_refine_ls_R_factor_ref 0.0599 _refine_ls_wR_factor_ref 0.1140 _refine_ls_goodness_of_fit_ref 0.9551 _refine_ls_shift/su_max 0.0001860 _refine_ls_shift/su_mean 0.0000177 # The values computed from all data _oxford_reflns_number_all 3634 _refine_ls_R_factor_all 0.0599 _refine_ls_wR_factor_all 0.1140 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2854 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_gt 0.0950 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration (4R,2'S) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 18.9 27.7 14.2 3.78 ; # Insert your own references if required - in alphabetical order 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens O6 O 0.8362(2) 0.5545(3) 0.82278(19) 0.0403 1.0000 Uani . . . . . . . C7 C 0.8692(3) 0.5484(3) 0.7457(2) 0.0282 1.0000 Uani . . . . . . . N8 N 0.9935(2) 0.5701(2) 0.7732(2) 0.0284 1.0000 Uani . . . . . . . C9 C 1.0467(3) 0.5619(3) 0.6952(3) 0.0303 1.0000 Uani . . . . . . . O10 O 0.9938(2) 0.5564(2) 0.58895(18) 0.0377 1.0000 Uani . . . . . . . O11 O 1.17247(19) 0.5622(2) 0.75969(18) 0.0339 1.0000 Uani . . . . . . . C12 C 1.2076(3) 0.5470(3) 0.8870(3) 0.0319 1.0000 Uani . . . . . . . C13 C 1.0912(3) 0.5955(3) 0.8962(3) 0.0304 1.0000 Uani . . . . . . . C14 C 1.0958(3) 0.7262(3) 0.9316(3) 0.0414 1.0000 Uani . . . . . . . C15 C 1.0086(4) 0.7522(4) 0.9859(4) 0.0524 1.0000 Uani . . . . . . . C16 C 1.0725(4) 0.8120(4) 0.8305(4) 0.0539 1.0000 Uani . . . . . . . C17 C 1.3312(3) 0.6121(3) 0.9561(3) 0.0412 1.0000 Uani . . . . . . . C18 C 1.2215(3) 0.4155(3) 0.9118(3) 0.0364 1.0000 Uani . . . . . . . C19 C 0.7771(3) 0.5146(3) 0.6181(2) 0.0260 1.0000 Uani . . . . . . . C20 C 0.6418(3) 0.5225(3) 0.6006(3) 0.0257 1.0000 Uani . . . . . . . N21 N 0.6001(2) 0.6434(2) 0.6175(2) 0.0263 1.0000 Uani . . . . . . . C22 C 0.5506(3) 0.7201(3) 0.5067(3) 0.0323 1.0000 Uani . . . . . . . C23 C 0.6388(3) 0.7307(3) 0.4526(3) 0.0341 1.0000 Uani . . . . . . . C24 C 0.7439(3) 0.8039(3) 0.5020(3) 0.0376 1.0000 Uani . . . . . . . C25 C 0.8260(4) 0.8087(4) 0.4526(4) 0.0459 1.0000 Uani . . . . . . . C26 C 0.8029(4) 0.7416(4) 0.3537(4) 0.0565 1.0000 Uani . . . . . . . C27 C 0.6975(5) 0.6709(4) 0.3020(3) 0.0541 1.0000 Uani . . . . . . . C28 C 0.6151(4) 0.6651(3) 0.3513(3) 0.0434 1.0000 Uani . . . . . . . C29 C 0.4978(3) 0.6356(3) 0.6568(3) 0.0318 1.0000 Uani . . . . . . . C30 C 0.5421(3) 0.5774(3) 0.7763(3) 0.0306 1.0000 Uani . . . . . . . C31 C 0.5033(3) 0.4638(3) 0.7847(3) 0.0344 1.0000 Uani . . . . . . . C32 C 0.5478(3) 0.4090(3) 0.8948(3) 0.0420 1.0000 Uani . . . . . . . C33 C 0.6302(3) 0.4680(4) 0.9965(3) 0.0429 1.0000 Uani . . . . . . . C34 C 0.6670(3) 0.5821(4) 0.9883(3) 0.0417 1.0000 Uani . . . . . . . C35 C 0.6231(3) 0.6368(3) 0.8797(3) 0.0360 1.0000 Uani . . . . . . . C36 C 0.8010(3) 0.3878(3) 0.5937(3) 0.0271 1.0000 Uani . . . . . . . C37 C 0.8221(3) 0.2996(3) 0.6759(3) 0.0361 1.0000 Uani . . . . . . . C38 C 0.8443(4) 0.1844(3) 0.6516(4) 0.0475 1.0000 Uani . . . . . . . C39 C 0.8431(4) 0.1582(3) 0.5448(4) 0.0473 1.0000 Uani . . . . . . . C40 C 0.8181(4) 0.2449(4) 0.4619(4) 0.0458 1.0000 Uani . . . . . . . C41 C 0.7970(3) 0.3598(3) 0.4852(3) 0.0360 1.0000 Uani . . . . . . . F1 F 0.26796(19) 0.34063(18) 0.24609(18) 0.0432 1.0000 Uani . . . . . . . B2 B 0.3322(4) 0.4485(3) 0.2565(3) 0.0372 1.0000 Uani . . . . . . . F3 F 0.2528(2) 0.5272(2) 0.17413(19) 0.0564 1.0000 Uani . . . . . . . F4 F 0.3716(2) 0.49185(19) 0.37062(17) 0.0457 1.0000 Uani . . . . . . . F5 F 0.4350(2) 0.4245(2) 0.2378(3) 0.0690 1.0000 Uani . . . . . . . H131 H 1.0736 0.5458 0.9485 0.0380 1.0000 Uiso R . . . . . . H141 H 1.1826 0.7400 0.9939 0.0513 1.0000 Uiso R . . . . . . H152 H 1.0203 0.8321 1.0150 0.0822 1.0000 Uiso R . . . . . . H153 H 1.0251 0.6963 1.0516 0.0815 1.0000 Uiso R . . . . . . H151 H 0.9236 0.7450 0.9250 0.0813 1.0000 Uiso R . . . . . . H163 H 1.0824 0.8925 0.8581 0.0828 1.0000 Uiso R . . . . . . H161 H 1.1299 0.7949 0.7978 0.0821 1.0000 Uiso R . . . . . . H162 H 0.9876 0.8028 0.7687 0.0826 1.0000 Uiso R . . . . . . H171 H 1.3561 0.6096 1.0407 0.0642 1.0000 Uiso R . . . . . . H172 H 1.3966 0.5772 0.9386 0.0634 1.0000 Uiso R . . . . . . H173 H 1.3183 0.6936 0.9290 0.0632 1.0000 Uiso R . . . . . . H182 H 1.2466 0.4007 0.9942 0.0571 1.0000 Uiso R . . . . . . H183 H 1.2816 0.3829 0.8904 0.0564 1.0000 Uiso R . . . . . . H181 H 1.1425 0.3748 0.8634 0.0564 1.0000 Uiso R . . . . . . H191 H 0.7881 0.5669 0.5630 0.0330 1.0000 Uiso R . . . . . . H201 H 0.6320 0.4688 0.6571 0.0334 1.0000 Uiso R . . . . . . H202 H 0.5888 0.4995 0.5206 0.0320 1.0000 Uiso R . . . . . . H221 H 0.5331 0.7986 0.5269 0.0404 1.0000 Uiso R . . . . . . H222 H 0.4742 0.6850 0.4491 0.0407 1.0000 Uiso R . . . . . . H241 H 0.7593 0.8486 0.5693 0.0473 1.0000 Uiso R . . . . . . H251 H 0.8974 0.8554 0.4879 0.0590 1.0000 Uiso R . . . . . . H261 H 0.8588 0.7446 0.3221 0.0691 1.0000 Uiso R . . . . . . H271 H 0.6821 0.6254 0.2337 0.0675 1.0000 Uiso R . . . . . . H281 H 0.5416 0.6172 0.3161 0.0536 1.0000 Uiso R . . . . . . H291 H 0.4691 0.7145 0.6609 0.0397 1.0000 Uiso R . . . . . . H292 H 0.4291 0.5911 0.5964 0.0398 1.0000 Uiso R . . . . . . H311 H 0.4500 0.4227 0.7166 0.0446 1.0000 Uiso R . . . . . . H321 H 0.5214 0.3320 0.8988 0.0497 1.0000 Uiso R . . . . . . H331 H 0.6600 0.4323 1.0706 0.0521 1.0000 Uiso R . . . . . . H341 H 0.7238 0.6208 1.0585 0.0512 1.0000 Uiso R . . . . . . H351 H 0.6492 0.7146 0.8742 0.0442 1.0000 Uiso R . . . . . . H371 H 0.8192 0.3177 0.7490 0.0432 1.0000 Uiso R . . . . . . H381 H 0.8605 0.1261 0.7079 0.0601 1.0000 Uiso R . . . . . . H391 H 0.8627 0.0816 0.5294 0.0596 1.0000 Uiso R . . . . . . H401 H 0.8151 0.2262 0.3893 0.0576 1.0000 Uiso R . . . . . . H411 H 0.7796 0.4203 0.4293 0.0467 1.0000 Uiso R . . . . . . H211 H 0.6689 0.6785 0.6780 0.0464 1.0000 Uiso 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 O6 0.0290(10) 0.0623(16) 0.0294(10) -0.0120(11) 0.0133(9) -0.0009(11) C7 0.0256(13) 0.0264(15) 0.0287(14) -0.0027(12) 0.0093(11) 0.0004(12) N8 0.0236(11) 0.0324(13) 0.0267(12) -0.0010(10) 0.0094(9) 0.0012(10) C9 0.0310(14) 0.0301(15) 0.0304(14) 0.0018(13) 0.0146(12) -0.0040(13) O10 0.0365(11) 0.0494(14) 0.0276(11) 0.0035(10) 0.0150(9) -0.0057(11) O11 0.0289(10) 0.0432(13) 0.0297(10) 0.0027(10) 0.0136(8) -0.0016(10) C12 0.0277(14) 0.0346(17) 0.0306(14) 0.0000(13) 0.0109(12) 0.0025(13) C13 0.0230(13) 0.0347(16) 0.0273(14) -0.0063(12) 0.0064(11) 0.0007(11) C14 0.0290(15) 0.0406(19) 0.0406(18) -0.0121(16) 0.0041(13) 0.0029(14) C15 0.0395(18) 0.056(2) 0.049(2) -0.0246(19) 0.0098(16) 0.0076(18) C16 0.052(2) 0.0293(18) 0.063(2) -0.0037(18) 0.0123(19) -0.0017(17) C17 0.0259(15) 0.045(2) 0.0441(19) -0.0041(16) 0.0082(13) -0.0019(14) C18 0.0380(17) 0.0310(17) 0.0376(17) 0.0002(14) 0.0153(14) 0.0062(14) C19 0.0269(13) 0.0266(14) 0.0227(12) -0.0013(11) 0.0100(11) -0.0010(11) C20 0.0276(13) 0.0218(13) 0.0267(13) -0.0013(11) 0.0117(11) 0.0018(11) N21 0.0243(11) 0.0259(12) 0.0254(11) -0.0007(10) 0.0086(9) 0.0021(10) C22 0.0310(14) 0.0271(15) 0.0288(14) 0.0031(12) 0.0052(12) 0.0053(12) C23 0.0390(16) 0.0311(16) 0.0265(15) 0.0062(13) 0.0101(12) 0.0042(13) C24 0.0443(18) 0.0289(16) 0.0385(17) 0.0060(14) 0.0181(14) 0.0030(15) C25 0.049(2) 0.042(2) 0.051(2) 0.0119(18) 0.0260(18) 0.0023(17) C26 0.074(3) 0.055(3) 0.057(2) 0.021(2) 0.044(2) 0.015(2) C27 0.086(3) 0.049(2) 0.0341(18) 0.0051(17) 0.033(2) 0.007(2) C28 0.057(2) 0.0381(19) 0.0291(16) 0.0004(14) 0.0143(15) -0.0006(17) C29 0.0263(14) 0.0344(16) 0.0354(16) -0.0015(13) 0.0147(12) 0.0038(13) C30 0.0260(14) 0.0338(16) 0.0326(15) -0.0028(13) 0.0140(12) 0.0011(13) C31 0.0324(15) 0.0309(16) 0.0385(16) -0.0045(14) 0.0151(13) 0.0009(13) C32 0.0433(19) 0.0362(18) 0.047(2) 0.0051(16) 0.0217(16) 0.0044(15) C33 0.0376(17) 0.055(2) 0.0345(17) 0.0093(16) 0.0151(14) 0.0088(16) C34 0.0350(16) 0.058(2) 0.0308(16) -0.0041(16) 0.0138(13) -0.0060(16) C35 0.0382(16) 0.0355(17) 0.0348(16) -0.0088(14) 0.0173(13) -0.0084(14) C36 0.0237(13) 0.0246(14) 0.0305(14) -0.0029(11) 0.0103(11) -0.0005(11) C37 0.0359(17) 0.0345(17) 0.0384(17) 0.0029(14) 0.0176(14) 0.0027(14) C38 0.046(2) 0.0309(18) 0.065(2) 0.0081(17) 0.0245(18) 0.0041(16) C39 0.0447(19) 0.0307(18) 0.073(3) -0.0094(18) 0.0328(19) 0.0002(15) C40 0.049(2) 0.047(2) 0.050(2) -0.0168(17) 0.0298(18) -0.0025(17) C41 0.0389(17) 0.0348(17) 0.0389(17) -0.0031(14) 0.0218(14) -0.0010(14) F1 0.0416(11) 0.0361(11) 0.0391(10) -0.0031(8) 0.0077(9) -0.0056(9) B2 0.0371(19) 0.0306(19) 0.0367(18) -0.0007(15) 0.0108(15) -0.0003(15) F3 0.0808(16) 0.0424(13) 0.0384(11) 0.0117(10) 0.0209(11) 0.0166(12) F4 0.0493(12) 0.0366(11) 0.0347(10) -0.0021(8) 0.0053(9) -0.0037(9) F5 0.0611(15) 0.0544(15) 0.107(2) -0.0144(15) 0.0523(16) -0.0059(13) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.6656(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O6 . C7 . 1.213(4) yes C7 . N8 . 1.384(4) yes C7 . C19 . 1.528(4) yes N8 . C9 . 1.404(4) yes N8 . C13 . 1.484(4) yes C9 . O10 . 1.197(4) yes C9 . O11 . 1.342(4) yes O11 . C12 . 1.478(4) yes C12 . C13 . 1.551(4) yes C12 . C17 . 1.519(4) yes C12 . C18 . 1.518(5) yes C13 . C14 . 1.542(5) yes C13 . H131 . 0.964 no C14 . C15 . 1.521(5) yes C14 . C16 . 1.529(6) yes C14 . H141 . 0.985 no C15 . H152 . 0.963 no C15 . H153 . 0.991 no C15 . H151 . 0.956 no C16 . H163 . 0.965 no C16 . H161 . 0.972 no C16 . H162 . 0.961 no C17 . H171 . 0.972 no C17 . H172 . 0.989 no C17 . H173 . 0.974 no C18 . H182 . 0.960 no C18 . H183 . 0.952 no C18 . H181 . 0.974 no C19 . C20 . 1.532(4) yes C19 . C36 . 1.525(4) yes C19 . H191 . 0.971 no C20 . N21 . 1.508(4) yes C20 . H201 . 0.987 no C20 . H202 . 0.952 no N21 . C22 . 1.521(4) yes N21 . C29 . 1.522(4) yes N21 . H211 . 0.917 no C22 . C23 . 1.504(5) yes C22 . H221 . 0.975 no C22 . H222 . 0.955 no C23 . C24 . 1.392(5) yes C23 . C28 . 1.396(5) yes C24 . C25 . 1.387(5) yes C24 . H241 . 0.935 no C25 . C26 . 1.381(6) yes C25 . H251 . 0.927 no C26 . C27 . 1.379(7) yes C26 . H261 . 0.925 no C27 . C28 . 1.391(6) yes C27 . H271 . 0.950 no C28 . H281 . 0.952 no C29 . C30 . 1.506(4) yes C29 . H291 . 0.968 no C29 . H292 . 0.969 no C30 . C31 . 1.390(5) yes C30 . C35 . 1.393(4) yes C31 . C32 . 1.391(5) yes C31 . H311 . 0.929 no C32 . C33 . 1.383(5) yes C32 . H321 . 0.938 no C33 . C34 . 1.385(6) yes C33 . H331 . 0.931 no C34 . C35 . 1.375(5) yes C34 . H341 . 0.943 no C35 . H351 . 0.949 no C36 . C37 . 1.381(4) yes C36 . C41 . 1.390(4) yes C37 . C38 . 1.396(5) yes C37 . H371 . 0.964 no C38 . C39 . 1.379(6) yes C38 . H381 . 0.926 no C39 . C40 . 1.369(6) yes C39 . H391 . 0.943 no C40 . C41 . 1.384(5) yes C40 . H401 . 0.928 no C41 . H411 . 0.939 no F1 . B2 . 1.419(4) yes B2 . F3 . 1.369(4) yes B2 . F4 . 1.388(4) yes B2 . F5 . 1.383(5) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O6 . C7 . N8 . 119.8(3) yes O6 . C7 . C19 . 121.5(3) yes N8 . C7 . C19 . 118.6(2) yes C7 . N8 . C9 . 126.4(2) yes C7 . N8 . C13 . 122.4(2) yes C9 . N8 . C13 . 111.0(2) yes N8 . C9 . O10 . 128.3(3) yes N8 . C9 . O11 . 108.4(2) yes O10 . C9 . O11 . 123.3(3) yes C9 . O11 . C12 . 109.9(2) yes O11 . C12 . C13 . 103.1(2) yes O11 . C12 . C17 . 106.5(3) yes C13 . C12 . C17 . 117.0(3) yes O11 . C12 . C18 . 106.8(3) yes C13 . C12 . C18 . 110.5(3) yes C17 . C12 . C18 . 111.9(3) yes C12 . C13 . N8 . 98.8(2) yes C12 . C13 . C14 . 116.7(3) yes N8 . C13 . C14 . 113.4(3) yes C12 . C13 . H131 . 109.4 no N8 . C13 . H131 . 106.9 no C14 . C13 . H131 . 110.6 no C13 . C14 . C15 . 112.2(3) yes C13 . C14 . C16 . 113.6(3) yes C15 . C14 . C16 . 110.9(3) yes C13 . C14 . H141 . 105.6 no C15 . C14 . H141 . 107.2 no C16 . C14 . H141 . 106.8 no C14 . C15 . H152 . 110.3 no C14 . C15 . H153 . 110.0 no H152 . C15 . H153 . 110.1 no C14 . C15 . H151 . 108.3 no H152 . C15 . H151 . 107.6 no H153 . C15 . H151 . 110.5 no C14 . C16 . H163 . 110.8 no C14 . C16 . H161 . 109.8 no H163 . C16 . H161 . 110.5 no C14 . C16 . H162 . 109.3 no H163 . C16 . H162 . 107.8 no H161 . C16 . H162 . 108.6 no C12 . C17 . H171 . 110.1 no C12 . C17 . H172 . 109.7 no H171 . C17 . H172 . 111.3 no C12 . C17 . H173 . 107.7 no H171 . C17 . H173 . 109.6 no H172 . C17 . H173 . 108.4 no C12 . C18 . H182 . 110.3 no C12 . C18 . H183 . 110.3 no H182 . C18 . H183 . 110.1 no C12 . C18 . H181 . 110.7 no H182 . C18 . H181 . 109.2 no H183 . C18 . H181 . 106.1 no C7 . C19 . C20 . 109.7(2) yes C7 . C19 . C36 . 109.9(2) yes C20 . C19 . C36 . 108.1(2) yes C7 . C19 . H191 . 109.7 no C20 . C19 . H191 . 110.2 no C36 . C19 . H191 . 109.3 no C19 . C20 . N21 . 115.4(2) yes C19 . C20 . H201 . 109.2 no N21 . C20 . H201 . 107.5 no C19 . C20 . H202 . 106.2 no N21 . C20 . H202 . 107.4 no H201 . C20 . H202 . 111.1 no C20 . N21 . C22 . 113.7(2) yes C20 . N21 . C29 . 111.2(2) yes C22 . N21 . C29 . 107.8(2) yes C20 . N21 . H211 . 106.6 no C22 . N21 . H211 . 109.9 no C29 . N21 . H211 . 107.4 no N21 . C22 . C23 . 114.2(2) yes N21 . C22 . H221 . 108.6 no C23 . C22 . H221 . 109.1 no N21 . C22 . H222 . 107.2 no C23 . C22 . H222 . 108.1 no H221 . C22 . H222 . 109.6 no C22 . C23 . C24 . 121.4(3) yes C22 . C23 . C28 . 119.2(3) yes C24 . C23 . C28 . 119.3(3) yes C23 . C24 . C25 . 120.1(3) yes C23 . C24 . H241 . 119.4 no C25 . C24 . H241 . 120.5 no C24 . C25 . C26 . 120.0(4) yes C24 . C25 . H251 . 119.4 no C26 . C25 . H251 . 120.5 no C25 . C26 . C27 . 120.6(4) yes C25 . C26 . H261 . 119.3 no C27 . C26 . H261 . 120.1 no C26 . C27 . C28 . 119.8(4) yes C26 . C27 . H271 . 120.0 no C28 . C27 . H271 . 120.2 no C23 . C28 . C27 . 120.2(4) yes C23 . C28 . H281 . 119.2 no C27 . C28 . H281 . 120.7 no N21 . C29 . C30 . 113.0(2) yes N21 . C29 . H291 . 108.9 no C30 . C29 . H291 . 108.7 no N21 . C29 . H292 . 106.8 no C30 . C29 . H292 . 110.1 no H291 . C29 . H292 . 109.4 no C29 . C30 . C31 . 120.5(3) yes C29 . C30 . C35 . 120.3(3) yes C31 . C30 . C35 . 119.2(3) yes C30 . C31 . C32 . 120.3(3) yes C30 . C31 . H311 . 120.4 no C32 . C31 . H311 . 119.3 no C31 . C32 . C33 . 119.8(3) yes C31 . C32 . H321 . 119.3 no C33 . C32 . H321 . 120.9 no C32 . C33 . C34 . 119.8(3) yes C32 . C33 . H331 . 120.5 no C34 . C33 . H331 . 119.7 no C33 . C34 . C35 . 120.5(3) yes C33 . C34 . H341 . 118.7 no C35 . C34 . H341 . 120.7 no C30 . C35 . C34 . 120.2(3) yes C30 . C35 . H351 . 119.3 no C34 . C35 . H351 . 120.4 no C19 . C36 . C37 . 121.1(3) yes C19 . C36 . C41 . 119.5(3) yes C37 . C36 . C41 . 119.4(3) yes C36 . C37 . C38 . 119.9(3) yes C36 . C37 . H371 . 119.7 no C38 . C37 . H371 . 120.4 no C37 . C38 . C39 . 120.1(4) yes C37 . C38 . H381 . 119.5 no C39 . C38 . H381 . 120.3 no C38 . C39 . C40 . 119.9(3) yes C38 . C39 . H391 . 120.7 no C40 . C39 . H391 . 119.4 no C39 . C40 . C41 . 120.6(4) yes C39 . C40 . H401 . 119.4 no C41 . C40 . H401 . 120.0 no C36 . C41 . C40 . 120.0(3) yes C36 . C41 . H411 . 118.3 no C40 . C41 . H411 . 121.7 no F1 . B2 . F3 . 109.6(3) yes F1 . B2 . F4 . 108.1(3) yes F3 . B2 . F4 . 110.3(3) yes F1 . B2 . F5 . 107.5(3) yes F3 . B2 . F5 . 110.9(3) yes F4 . B2 . F5 . 110.3(3) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C15 . H151 . O6 . 122 0.96 2.49 3.103(5) yes C19 . H191 . C23 . 124 0.97 2.51 3.154(5) yes