# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2014 ####################################################################### # # 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_exp_1113 #TrackingRef 'BIC.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H15 B F2 N4 O2 S' _chemical_formula_weight 412.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' O O 0.0492 0.0322 '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' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8205(9) _cell_length_b 10.3904(11) _cell_length_c 12.6744(14) _cell_angle_alpha 111.822(10) _cell_angle_beta 97.397(9) _cell_angle_gamma 98.633(9) _cell_volume 925.97(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1473 _cell_measurement_theta_min 3.8319 _cell_measurement_theta_max 70.7343 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 1.949 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9438 _exptl_absorpt_correction_T_max 0.9621 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _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 5983 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.84 _diffrn_reflns_theta_max 67.25 _reflns_number_total 3323 _reflns_number_gt 2448 _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^)+(0.1589P)^2^+0.6772P] 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 3323 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1089 _refine_ls_R_factor_gt 0.0900 _refine_ls_wR_factor_ref 0.2804 _refine_ls_wR_factor_gt 0.2560 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 S1 S 0.41033(18) 0.70210(14) 0.04827(11) 0.0597(4) Uani 1 1 d . . . B1 B 0.1592(7) 0.7422(5) 0.4827(4) 0.0473(11) Uani 1 1 d . . . F1 F 0.2823(4) 0.8283(3) 0.4561(2) 0.0634(8) Uani 1 1 d . . . F2 F -0.0099(4) 0.7428(3) 0.4359(2) 0.0587(7) Uani 1 1 d . . . N1 N 0.3937(7) 0.4785(5) 0.7678(4) 0.0694(13) Uani 1 1 d . . . N2 N 0.1807(5) 0.7952(4) 0.6175(3) 0.0457(9) Uani 1 1 d . . . N3 N 0.2402(5) 0.7986(4) 0.7933(3) 0.0493(9) Uani 1 1 d . . . H3A H 0.2725 0.7733 0.8488 0.059 Uiso 1 1 calc R . . N4 N 0.1918(5) 0.5886(4) 0.4421(3) 0.0469(9) Uani 1 1 d . . . O1 O 0.1183(5) 0.5265(4) 0.2432(3) 0.0681(10) Uani 1 1 d . . . O2 O 0.3266(7) 0.7938(5) -0.0004(4) 0.0955(16) Uani 1 1 d . . . C1 C 0.1719(7) 0.4976(5) 0.3233(4) 0.0519(11) Uani 1 1 d . . . C2 C 0.2315(6) 0.3690(5) 0.3236(4) 0.0519(11) Uani 1 1 d . . . C3 C 0.2430(8) 0.2493(5) 0.2302(4) 0.0616(13) Uani 1 1 d . . . H3 H 0.2115 0.2410 0.1543 0.074 Uiso 1 1 calc R . . C4 C 0.3033(7) 0.1425(5) 0.2545(4) 0.0653(14) Uani 1 1 d . . . H4 H 0.3137 0.0610 0.1941 0.078 Uiso 1 1 calc R . . C5 C 0.3480(7) 0.1564(5) 0.3682(5) 0.0601(12) Uani 1 1 d . . . H5 H 0.3866 0.0828 0.3822 0.072 Uiso 1 1 calc R . . C6 C 0.3374(6) 0.2756(5) 0.4614(4) 0.0524(11) Uani 1 1 d . . . H6 H 0.3682 0.2834 0.5372 0.063 Uiso 1 1 calc R . . C7 C 0.2792(6) 0.3829(5) 0.4375(4) 0.0463(10) Uani 1 1 d . . . C8 C 0.2507(6) 0.5238(5) 0.5115(4) 0.0441(9) Uani 1 1 d . . . C9 C 0.2733(6) 0.5865(5) 0.6292(4) 0.0441(9) Uani 1 1 d . . . C10 C 0.3387(7) 0.5233(5) 0.7045(4) 0.0502(11) Uani 1 1 d . . . C11 C 0.2338(6) 0.7249(4) 0.6810(4) 0.0429(9) Uani 1 1 d . . . C12 C 0.1857(6) 0.9235(5) 0.8050(4) 0.0486(10) Uani 1 1 d . . . C13 C 0.1679(8) 1.0354(5) 0.9027(4) 0.0602(13) Uani 1 1 d . . . H13 H 0.1937 1.0362 0.9767 0.072 Uiso 1 1 calc R . . C14 C 0.1094(8) 1.1459(5) 0.8836(4) 0.0639(14) Uani 1 1 d . . . H14 H 0.0918 1.2218 0.9461 0.077 Uiso 1 1 calc R . . C15 C 0.0764(7) 1.1460(5) 0.7727(4) 0.0619(13) Uani 1 1 d . . . H15 H 0.0405 1.2234 0.7639 0.074 Uiso 1 1 calc R . . C16 C 0.0951(7) 1.0349(5) 0.6757(4) 0.0539(11) Uani 1 1 d . . . H16 H 0.0720 1.0350 0.6019 0.065 Uiso 1 1 calc R . . C17 C 0.1506(6) 0.9226(5) 0.6949(4) 0.0471(10) Uani 1 1 d . . . C18 C 0.4257(8) 0.7869(6) 0.2005(4) 0.0692(15) Uani 1 1 d . . . H18A H 0.5088 0.8763 0.2304 0.104 Uiso 1 1 calc R . . H18B H 0.4647 0.7277 0.2372 0.104 Uiso 1 1 calc R . . H18C H 0.3120 0.8027 0.2160 0.104 Uiso 1 1 calc R . . C19 C 0.2423(9) 0.5531(7) 0.0190(5) 0.0845(19) Uani 1 1 d . . . H19A H 0.1393 0.5840 0.0443 0.127 Uiso 1 1 calc R . . H19B H 0.2822 0.4981 0.0596 0.127 Uiso 1 1 calc R . . H19C H 0.2136 0.4960 -0.0629 0.127 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 S1 0.0726(9) 0.0573(8) 0.0524(7) 0.0249(6) 0.0133(6) 0.0147(6) B1 0.059(3) 0.047(3) 0.041(3) 0.023(2) 0.006(2) 0.016(2) F1 0.080(2) 0.0596(17) 0.0578(16) 0.0331(14) 0.0183(14) 0.0081(14) F2 0.0639(17) 0.0662(17) 0.0493(15) 0.0262(13) 0.0022(12) 0.0228(13) N1 0.104(4) 0.063(3) 0.053(2) 0.033(2) 0.011(2) 0.033(3) N2 0.055(2) 0.0440(19) 0.0393(19) 0.0183(16) 0.0051(15) 0.0144(16) N3 0.068(2) 0.048(2) 0.0363(18) 0.0209(16) 0.0073(16) 0.0173(18) N4 0.058(2) 0.049(2) 0.0359(18) 0.0188(16) 0.0067(15) 0.0151(16) O1 0.101(3) 0.072(2) 0.0376(17) 0.0267(17) 0.0092(17) 0.028(2) O2 0.170(5) 0.074(3) 0.052(2) 0.035(2) 0.007(3) 0.040(3) C1 0.060(3) 0.055(3) 0.041(2) 0.020(2) 0.0084(19) 0.011(2) C2 0.060(3) 0.048(2) 0.046(2) 0.018(2) 0.008(2) 0.013(2) C3 0.086(4) 0.054(3) 0.038(2) 0.013(2) 0.009(2) 0.016(2) C4 0.084(4) 0.050(3) 0.052(3) 0.010(2) 0.011(3) 0.018(3) C5 0.072(3) 0.049(3) 0.059(3) 0.019(2) 0.012(2) 0.019(2) C6 0.059(3) 0.051(3) 0.047(2) 0.020(2) 0.007(2) 0.015(2) C7 0.047(2) 0.044(2) 0.047(2) 0.0180(19) 0.0111(18) 0.0085(17) C8 0.046(2) 0.046(2) 0.044(2) 0.0217(19) 0.0072(18) 0.0087(17) C9 0.052(2) 0.043(2) 0.043(2) 0.0225(18) 0.0088(18) 0.0148(18) C10 0.067(3) 0.047(2) 0.043(2) 0.022(2) 0.012(2) 0.021(2) C11 0.050(2) 0.045(2) 0.037(2) 0.0198(18) 0.0057(17) 0.0128(18) C12 0.062(3) 0.041(2) 0.041(2) 0.0177(18) 0.0043(19) 0.0091(19) C13 0.089(4) 0.050(3) 0.039(2) 0.015(2) 0.007(2) 0.019(2) C14 0.088(4) 0.047(3) 0.050(3) 0.013(2) 0.007(3) 0.021(2) C15 0.081(3) 0.045(2) 0.058(3) 0.019(2) 0.006(3) 0.020(2) C16 0.068(3) 0.047(2) 0.047(2) 0.021(2) 0.002(2) 0.014(2) C17 0.054(2) 0.041(2) 0.045(2) 0.0176(19) 0.0050(19) 0.0108(18) C18 0.097(4) 0.058(3) 0.051(3) 0.022(2) 0.003(3) 0.023(3) C19 0.105(5) 0.075(4) 0.059(3) 0.019(3) 0.016(3) -0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.495(4) . ? S1 C19 1.760(6) . ? S1 C18 1.777(5) . ? B1 F1 1.375(6) . ? B1 F2 1.380(6) . ? B1 N4 1.556(6) . ? B1 N2 1.565(6) . ? N1 C10 1.138(6) . ? N2 C11 1.341(5) . ? N2 C17 1.399(6) . ? N3 C11 1.332(5) . ? N3 C12 1.388(6) . ? N4 C8 1.368(5) . ? N4 C1 1.422(6) . ? O1 C1 1.205(6) . ? C1 C2 1.481(7) . ? C2 C3 1.387(7) . ? C2 C7 1.391(6) . ? C3 C4 1.386(7) . ? C4 C5 1.386(7) . ? C5 C6 1.380(7) . ? C6 C7 1.381(6) . ? C7 C8 1.485(6) . ? C8 C9 1.362(6) . ? C9 C10 1.430(6) . ? C9 C11 1.441(6) . ? C12 C17 1.383(6) . ? C12 C13 1.389(6) . ? C13 C14 1.386(7) . ? C14 C15 1.395(7) . ? C15 C16 1.381(7) . ? C16 C17 1.395(6) . ? 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 O2 S1 C19 105.6(3) . . ? O2 S1 C18 104.6(3) . . ? C19 S1 C18 98.7(3) . . ? F1 B1 F2 110.8(4) . . ? F1 B1 N4 111.0(4) . . ? F2 B1 N4 111.2(4) . . ? F1 B1 N2 109.8(4) . . ? F2 B1 N2 109.0(4) . . ? N4 B1 N2 104.8(3) . . ? C11 N2 C17 106.8(3) . . ? C11 N2 B1 125.4(4) . . ? C17 N2 B1 127.8(4) . . ? C11 N3 C12 108.0(4) . . ? C8 N4 C1 110.2(4) . . ? C8 N4 B1 126.6(4) . . ? C1 N4 B1 123.1(4) . . ? O1 C1 N4 124.4(4) . . ? O1 C1 C2 130.1(5) . . ? N4 C1 C2 105.5(4) . . ? C3 C2 C7 121.8(5) . . ? C3 C2 C1 128.9(5) . . ? C7 C2 C1 109.4(4) . . ? C4 C3 C2 117.4(5) . . ? C5 C4 C3 120.4(5) . . ? C6 C5 C4 122.4(5) . . ? C5 C6 C7 117.4(4) . . ? C6 C7 C2 120.7(4) . . ? C6 C7 C8 133.4(4) . . ? C2 C7 C8 105.9(4) . . ? C9 C8 N4 121.7(4) . . ? C9 C8 C7 129.2(4) . . ? N4 C8 C7 109.0(4) . . ? C8 C9 C10 123.2(4) . . ? C8 C9 C11 118.7(4) . . ? C10 C9 C11 118.2(4) . . ? N1 C10 C9 177.2(5) . . ? N3 C11 N2 111.0(4) . . ? N3 C11 C9 126.8(4) . . ? N2 C11 C9 122.2(4) . . ? C17 C12 N3 106.8(4) . . ? C17 C12 C13 122.3(4) . . ? N3 C12 C13 130.9(4) . . ? C14 C13 C12 116.1(4) . . ? C13 C14 C15 121.6(5) . . ? C16 C15 C14 122.2(5) . . ? C15 C16 C17 116.0(4) . . ? C12 C17 C16 121.7(4) . . ? C12 C17 N2 107.4(4) . . ? C16 C17 N2 130.9(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 67.25 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.122 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.112 _database_code_depnum_ccdc_archive 'CCDC 923116' ####################################################################### # # 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_exp_1836 #TrackingRef 'BIN.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H15 B F2 N4 O2 S' _chemical_formula_weight 388.20 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9557(15) _cell_length_b 11.770(3) _cell_length_c 12.267(3) _cell_angle_alpha 62.48(3) _cell_angle_beta 87.54(2) _cell_angle_gamma 86.180(19) _cell_volume 888.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1167 _cell_measurement_theta_min 3.2643 _cell_measurement_theta_max 28.4637 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.451 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.223 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9162 _exptl_absorpt_correction_T_max 0.9568 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _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 5261 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3133 _reflns_number_gt 2121 _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^)+(0.0614P)^2^+0.0953P] 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 3133 _refine_ls_number_parameters 246 _refine_ls_number_restraints 762 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1415 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 0.989 _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 S1 S 0.16167(11) 0.84585(8) 0.48735(7) 0.0720(3) Uani 1 1 d U . . B1 B 0.2465(4) 0.8363(3) 0.8880(3) 0.0524(7) Uani 1 1 d U . . F1 F 0.4147(2) 0.79054(15) 0.85523(13) 0.0724(5) Uani 1 1 d U . . F2 F 0.0917(2) 0.81434(15) 0.83583(14) 0.0742(5) Uani 1 1 d U . . N1 N 0.2222(3) 0.76823(19) 1.03088(17) 0.0482(5) Uani 1 1 d U . . N2 N 0.1990(3) 0.7471(2) 1.21868(18) 0.0540(5) Uani 1 1 d U . . H2A H 0.1937 0.7661 1.2786 0.065 Uiso 1 1 calc R . . N3 N 0.2399(3) 0.9576(2) 1.05965(18) 0.0499(5) Uani 1 1 d U . . N4 N 0.2556(3) 0.97882(19) 0.85600(17) 0.0483(5) Uani 1 1 d U . . O1 O 0.2787(3) 1.06928(19) 0.64365(16) 0.0706(6) Uani 1 1 d U . . O2 O 0.1857(4) 0.7573(2) 0.43094(18) 0.0965(8) Uani 1 1 d U . . C1 C 0.2013(3) 0.6385(3) 1.1105(2) 0.0530(6) Uani 1 1 d U . . C2 C 0.1963(4) 0.5336(3) 1.0893(3) 0.0733(8) Uani 1 1 d U . . H2 H 0.2061 0.5417 1.0102 0.088 Uiso 1 1 calc R . . C3 C 0.1760(5) 0.4160(3) 1.1908(4) 0.0876(10) Uani 1 1 d U . . H3 H 0.1723 0.3430 1.1799 0.105 Uiso 1 1 calc R . . C4 C 0.1611(5) 0.4042(3) 1.3079(3) 0.0856(10) Uani 1 1 d U . . H4 H 0.1488 0.3231 1.3739 0.103 Uiso 1 1 calc R . . C5 C 0.1638(4) 0.5078(3) 1.3309(3) 0.0704(8) Uani 1 1 d U . . H5 H 0.1515 0.4993 1.4101 0.084 Uiso 1 1 calc R . . C6 C 0.1861(3) 0.6262(3) 1.2288(2) 0.0542(6) Uani 1 1 d U . . C7 C 0.2213(3) 0.8296(2) 1.1001(2) 0.0464(6) Uani 1 1 d U . . C8 C 0.2557(3) 1.0245(2) 0.9415(2) 0.0488(6) Uani 1 1 d U . . C9 C 0.2788(3) 1.1644(2) 0.8745(2) 0.0508(6) Uani 1 1 d U . . C10 C 0.2894(4) 1.2548(3) 0.9161(3) 0.0645(7) Uani 1 1 d U . . H10 H 0.2801 1.2327 0.9993 0.077 Uiso 1 1 calc R . . C11 C 0.3146(4) 1.3803(3) 0.8271(3) 0.0758(9) Uani 1 1 d U . . H11 H 0.3217 1.4438 0.8516 0.091 Uiso 1 1 calc R . . C12 C 0.3292(4) 1.4132(3) 0.7043(3) 0.0778(9) Uani 1 1 d U . . H12 H 0.3453 1.4984 0.6476 0.093 Uiso 1 1 calc R . . C13 C 0.3207(4) 1.3224(3) 0.6631(3) 0.0678(8) Uani 1 1 d U . . H13 H 0.3324 1.3443 0.5800 0.081 Uiso 1 1 calc R . . C14 C 0.2938(3) 1.1976(2) 0.7511(2) 0.0535(6) Uani 1 1 d U . . C15 C 0.2761(3) 1.0808(3) 0.7369(2) 0.0541(6) Uani 1 1 d U . . C16 C 0.3603(5) 0.8080(3) 0.5843(3) 0.0886(10) Uani 1 1 d U . . H16A H 0.3496 0.7236 0.6517 0.133 Uiso 1 1 calc R . . H16B H 0.3627 0.8693 0.6153 0.133 Uiso 1 1 calc R . . H16C H 0.4771 0.8105 0.5387 0.133 Uiso 1 1 calc R . . C17 C 0.2267(5) 0.9986(3) 0.3742(3) 0.0875(10) Uani 1 1 d U . . H17A H 0.3561 0.9926 0.3461 0.131 Uiso 1 1 calc R . . H17B H 0.2191 1.0572 0.4087 0.131 Uiso 1 1 calc R . . H17C H 0.1403 1.0289 0.3063 0.131 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 S1 0.0793(5) 0.0840(6) 0.0659(5) -0.0452(4) 0.0138(4) -0.0182(4) B1 0.0569(17) 0.0612(17) 0.0438(16) -0.0279(14) -0.0056(13) -0.0023(14) F1 0.0891(12) 0.0805(11) 0.0534(9) -0.0388(8) 0.0051(8) 0.0141(9) F2 0.0917(12) 0.0768(10) 0.0615(10) -0.0349(9) -0.0224(8) -0.0143(9) N1 0.0490(11) 0.0570(13) 0.0434(11) -0.0269(10) -0.0007(9) -0.0045(9) N2 0.0510(12) 0.0704(15) 0.0425(12) -0.0279(11) -0.0009(9) -0.0007(10) N3 0.0519(12) 0.0597(13) 0.0446(12) -0.0299(10) -0.0028(9) 0.0010(10) N4 0.0498(12) 0.0586(12) 0.0406(11) -0.0263(10) -0.0001(9) -0.0035(9) O1 0.0861(14) 0.0817(14) 0.0451(11) -0.0303(10) 0.0017(10) -0.0052(11) O2 0.165(2) 0.0877(15) 0.0575(13) -0.0481(12) 0.0042(13) -0.0312(15) C1 0.0496(14) 0.0605(16) 0.0506(15) -0.0265(13) -0.0033(11) -0.0051(12) C2 0.090(2) 0.0654(18) 0.0688(19) -0.0332(16) 0.0007(16) -0.0141(15) C3 0.097(2) 0.066(2) 0.100(3) -0.0371(19) -0.005(2) -0.0163(17) C4 0.078(2) 0.071(2) 0.081(2) -0.0108(18) -0.0043(18) -0.0136(17) C5 0.0597(17) 0.078(2) 0.0597(18) -0.0196(16) -0.0002(13) -0.0045(14) C6 0.0433(14) 0.0656(17) 0.0491(15) -0.0221(13) -0.0040(11) -0.0035(12) C7 0.0424(13) 0.0631(16) 0.0385(13) -0.0277(12) -0.0013(10) -0.0008(11) C8 0.0373(13) 0.0651(16) 0.0527(15) -0.0347(13) -0.0029(11) 0.0016(11) C9 0.0395(13) 0.0568(15) 0.0608(16) -0.0314(13) -0.0047(11) 0.0022(11) C10 0.0539(16) 0.0697(18) 0.0795(19) -0.0428(16) -0.0101(14) 0.0056(13) C11 0.0619(18) 0.0606(19) 0.112(3) -0.0462(19) -0.0075(17) 0.0019(14) C12 0.067(2) 0.0580(18) 0.095(2) -0.0243(18) -0.0019(17) -0.0019(14) C13 0.0576(17) 0.0631(18) 0.0717(19) -0.0223(16) -0.0027(14) 0.0034(13) C14 0.0398(13) 0.0565(15) 0.0598(17) -0.0235(13) -0.0032(11) 0.0025(11) C15 0.0486(14) 0.0642(16) 0.0485(15) -0.0256(13) -0.0007(12) 0.0003(12) C16 0.124(3) 0.092(2) 0.062(2) -0.0439(18) -0.0143(19) -0.005(2) C17 0.083(2) 0.072(2) 0.093(3) -0.0258(19) -0.0048(19) -0.0006(17) _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 S1 O2 1.492(2) . ? S1 C16 1.758(3) . ? S1 C17 1.764(3) . ? B1 F2 1.373(3) . ? B1 F1 1.377(3) . ? B1 N4 1.541(4) . ? B1 N1 1.561(3) . ? N1 C7 1.345(3) . ? N1 C1 1.395(3) . ? N2 C7 1.333(3) . ? N2 C6 1.379(3) . ? N3 C8 1.295(3) . ? N3 C7 1.364(3) . ? N4 C8 1.382(3) . ? N4 C15 1.407(3) . ? O1 C15 1.212(3) . ? C1 C2 1.377(4) . ? C1 C6 1.390(4) . ? C2 C3 1.380(4) . ? C3 C4 1.379(5) . ? C4 C5 1.374(4) . ? C5 C6 1.391(4) . ? C8 C9 1.479(4) . ? C9 C14 1.378(4) . ? C9 C10 1.382(4) . ? C10 C11 1.390(4) . ? C11 C12 1.372(4) . ? C12 C13 1.383(4) . ? C13 C14 1.383(4) . ? C14 C15 1.477(4) . ? 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 O2 S1 C16 105.29(16) . . ? O2 S1 C17 107.22(15) . . ? C16 S1 C17 98.52(16) . . ? F2 B1 F1 110.1(2) . . ? F2 B1 N4 112.3(2) . . ? F1 B1 N4 111.5(2) . . ? F2 B1 N1 109.6(2) . . ? F1 B1 N1 109.7(2) . . ? N4 B1 N1 103.3(2) . . ? C7 N1 C1 107.3(2) . . ? C7 N1 B1 123.8(2) . . ? C1 N1 B1 129.0(2) . . ? C7 N2 C6 108.3(2) . . ? C8 N3 C7 114.7(2) . . ? C8 N4 C15 109.7(2) . . ? C8 N4 B1 124.6(2) . . ? C15 N4 B1 125.5(2) . . ? C2 C1 C6 121.4(3) . . ? C2 C1 N1 131.7(2) . . ? C6 C1 N1 106.9(2) . . ? C1 C2 C3 117.0(3) . . ? C4 C3 C2 121.4(3) . . ? C5 C4 C3 122.5(3) . . ? C4 C5 C6 116.0(3) . . ? N2 C6 C1 107.0(2) . . ? N2 C6 C5 131.3(3) . . ? C1 C6 C5 121.7(3) . . ? N2 C7 N1 110.4(2) . . ? N2 C7 N3 122.7(2) . . ? N1 C7 N3 126.9(2) . . ? N3 C8 N4 126.5(2) . . ? N3 C8 C9 125.4(2) . . ? N4 C8 C9 108.0(2) . . ? C14 C9 C10 121.4(3) . . ? C14 C9 C8 107.2(2) . . ? C10 C9 C8 131.3(3) . . ? C9 C10 C11 116.6(3) . . ? C12 C11 C10 121.9(3) . . ? C11 C12 C13 121.4(3) . . ? C12 C13 C14 116.9(3) . . ? C9 C14 C13 121.8(3) . . ? C9 C14 C15 108.3(2) . . ? C13 C14 C15 129.9(3) . . ? O1 C15 N4 124.3(2) . . ? O1 C15 C14 129.0(3) . . ? N4 C15 C14 106.7(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.253 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 923117' ####################################################################### # # 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_liu20120706a #TrackingRef 'BT.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H9 B F2 N2 O S' _chemical_formula_weight 326.12 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 8.6511(7) _cell_length_b 11.6621(9) _cell_length_c 13.9426(8) _cell_angle_alpha 90.00 _cell_angle_beta 100.040(7) _cell_angle_gamma 90.00 _cell_volume 1385.13(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1300 _cell_measurement_theta_min 2.5795 _cell_measurement_theta_max 28.3052 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.261 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9922 _exptl_absorpt_correction_T_max 0.9974 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'multiwire proportional' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8306 _diffrn_reflns_av_R_equivalents 0.0593 _diffrn_reflns_av_sigmaI/netI 0.0655 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2440 _reflns_number_gt 1390 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0835P)^2^+0.2470P] 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 constru _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2440 _refine_ls_number_parameters 208 _refine_ls_number_restraints 666 _refine_ls_R_factor_all 0.1154 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1853 _refine_ls_wR_factor_gt 0.1504 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.071 _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 S1 S 1.02223(15) 0.33602(11) 1.09253(7) 0.0625(4) Uani 1 1 d U . . F1 F 0.7105(4) 0.3580(2) 0.77016(18) 0.0834(9) Uani 1 1 d U . . F2 F 0.8232(3) 0.1837(3) 0.77412(18) 0.0821(8) Uani 1 1 d U . . N1 N 0.6192(5) 0.2126(3) 0.8685(2) 0.0586(8) Uani 1 1 d U . . N2 N 0.8824(4) 0.3008(3) 0.9174(2) 0.0575(7) Uani 1 1 d U . . O1 O 0.4582(4) 0.1616(3) 0.7237(2) 0.0817(10) Uani 1 1 d U . . B1 B 0.7555(7) 0.2633(5) 0.8276(3) 0.0599(9) Uani 1 1 d U . . C1 C 1.1200(6) 0.3736(4) 0.9985(3) 0.0596(9) Uani 1 1 d U . . C2 C 1.2658(6) 0.4229(4) 1.0049(3) 0.0675(10) Uani 1 1 d U . . H2 H 1.3269 0.4392 1.0651 0.081 Uiso 1 1 calc R . . C3 C 1.3189(6) 0.4477(4) 0.9192(3) 0.0700(10) Uani 1 1 d U . . H3 H 1.4168 0.4816 0.9215 0.084 Uiso 1 1 calc R . . C4 C 1.2273(6) 0.4225(4) 0.8299(3) 0.0658(10) Uani 1 1 d U . . H4 H 1.2657 0.4394 0.7733 0.079 Uiso 1 1 calc R . . C5 C 1.0817(6) 0.3732(4) 0.8227(3) 0.0635(9) Uani 1 1 d U . . H5 H 1.0210 0.3571 0.7623 0.076 Uiso 1 1 calc R . . C6 C 1.0277(6) 0.3481(4) 0.9088(3) 0.0581(8) Uani 1 1 d U . . C7 C 0.8642(6) 0.2898(4) 1.0102(3) 0.0559(8) Uani 1 1 d U . . C8 C 0.7245(5) 0.2449(4) 1.0364(3) 0.0571(8) Uani 1 1 d U . . H8 H 0.7133 0.2415 1.1015 0.069 Uiso 1 1 calc R . . C9 C 0.6091(6) 0.2075(4) 0.9666(3) 0.0580(8) Uani 1 1 d U . . C10 C 0.4585(6) 0.1538(4) 0.9759(3) 0.0584(8) Uani 1 1 d U . . C11 C 0.3933(6) 0.1265(4) 1.0557(3) 0.0624(9) Uani 1 1 d U . . H11 H 0.4447 0.1427 1.1186 0.075 Uiso 1 1 calc R . . C12 C 0.2488(6) 0.0741(4) 1.0391(3) 0.0668(10) Uani 1 1 d U . . H12 H 0.2022 0.0540 1.0920 0.080 Uiso 1 1 calc R . . C13 C 0.1696(6) 0.0500(4) 0.9450(3) 0.0689(10) Uani 1 1 d U . . H13 H 0.0716 0.0149 0.9364 0.083 Uiso 1 1 calc R . . C14 C 0.2358(6) 0.0777(4) 0.8648(3) 0.0666(9) Uani 1 1 d U . . H14 H 0.1845 0.0618 0.8019 0.080 Uiso 1 1 calc R . . C15 C 0.3810(6) 0.1300(4) 0.8816(3) 0.0608(9) Uani 1 1 d U . . C16 C 0.4813(6) 0.1673(4) 0.8126(3) 0.0636(9) Uani 1 1 d U . . 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 S1 0.0767(8) 0.0719(8) 0.0374(6) 0.0019(5) 0.0059(5) -0.0087(6) F1 0.1035(19) 0.0856(18) 0.0555(14) 0.0217(13) -0.0021(14) -0.0201(15) F2 0.0996(19) 0.0922(19) 0.0580(14) -0.0264(13) 0.0237(14) -0.0169(15) N1 0.0781(15) 0.0593(15) 0.0378(13) -0.0005(12) 0.0083(12) -0.0121(13) N2 0.0757(15) 0.0590(14) 0.0388(13) 0.0012(12) 0.0130(12) -0.0069(13) O1 0.107(2) 0.094(2) 0.0404(15) -0.0012(15) 0.0034(16) -0.0264(18) B1 0.0801(17) 0.0601(16) 0.0396(15) 0.0013(14) 0.0111(14) -0.0093(15) C1 0.0740(18) 0.0629(18) 0.0425(15) 0.0040(15) 0.0114(15) -0.0051(16) C2 0.0776(19) 0.0723(19) 0.0510(17) 0.0026(16) 0.0068(16) -0.0069(17) C3 0.078(2) 0.074(2) 0.0579(19) 0.0044(18) 0.0114(18) -0.0089(19) C4 0.078(2) 0.070(2) 0.0510(17) 0.0037(16) 0.0153(17) -0.0049(18) C5 0.0796(18) 0.0651(17) 0.0456(15) 0.0014(15) 0.0106(15) -0.0060(16) C6 0.0750(16) 0.0595(16) 0.0409(14) 0.0005(13) 0.0127(14) -0.0066(14) C7 0.0751(16) 0.0566(16) 0.0364(14) 0.0001(13) 0.0108(14) -0.0060(15) C8 0.0768(16) 0.0580(15) 0.0366(14) 0.0005(13) 0.0101(13) -0.0074(14) C9 0.0776(16) 0.0572(15) 0.0397(14) -0.0013(13) 0.0116(13) -0.0072(14) C10 0.0763(17) 0.0566(16) 0.0426(14) -0.0006(14) 0.0112(14) -0.0065(15) C11 0.0781(18) 0.0629(17) 0.0462(15) -0.0017(15) 0.0111(15) -0.0069(16) C12 0.080(2) 0.067(2) 0.0533(18) -0.0002(17) 0.0134(17) -0.0100(18) C13 0.079(2) 0.069(2) 0.0584(18) -0.0020(17) 0.0113(17) -0.0118(18) C14 0.0807(18) 0.0665(18) 0.0504(16) -0.0011(15) 0.0052(16) -0.0103(16) C15 0.0779(17) 0.0596(16) 0.0447(15) 0.0004(14) 0.0095(14) -0.0080(15) C16 0.0817(17) 0.0630(17) 0.0449(15) 0.0004(14) 0.0080(15) -0.0110(15) _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 S1 C7 1.712(5) . ? S1 C1 1.736(4) . ? F1 B1 1.380(6) . ? F2 B1 1.383(6) . ? N1 C9 1.387(5) . ? N1 C16 1.409(6) . ? N1 B1 1.516(6) . ? N2 C7 1.336(5) . ? N2 C6 1.397(6) . ? N2 B1 1.577(6) . ? O1 C16 1.222(5) . ? C1 C2 1.375(6) . ? C1 C6 1.393(6) . ? C2 C3 1.384(6) . ? C3 C4 1.385(6) . ? C4 C5 1.373(6) . ? C5 C6 1.393(5) . ? C7 C8 1.422(6) . ? C8 C9 1.339(6) . ? C9 C10 1.471(6) . ? C10 C11 1.370(6) . ? C10 C15 1.396(6) . ? C11 C12 1.375(6) . ? C12 C13 1.398(6) . ? C13 C14 1.381(6) . ? C14 C15 1.379(6) . ? C15 C16 1.470(6) . ? 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 C7 S1 C1 90.6(2) . . ? C9 N1 C16 109.7(4) . . ? C9 N1 B1 125.1(4) . . ? C16 N1 B1 125.2(3) . . ? C7 N2 C6 112.4(4) . . ? C7 N2 B1 124.0(4) . . ? C6 N2 B1 123.7(3) . . ? F1 B1 F2 109.1(4) . . ? F1 B1 N1 111.8(4) . . ? F2 B1 N1 111.8(4) . . ? F1 B1 N2 109.0(4) . . ? F2 B1 N2 108.2(4) . . ? N1 B1 N2 106.8(3) . . ? C2 C1 C6 121.5(4) . . ? C2 C1 S1 128.3(4) . . ? C6 C1 S1 110.2(4) . . ? C1 C2 C3 118.1(4) . . ? C2 C3 C4 120.5(5) . . ? C5 C4 C3 121.9(4) . . ? C4 C5 C6 117.8(4) . . ? C5 C6 C1 120.2(4) . . ? C5 C6 N2 126.8(4) . . ? C1 C6 N2 113.0(4) . . ? N2 C7 C8 122.2(4) . . ? N2 C7 S1 113.8(3) . . ? C8 C7 S1 124.0(3) . . ? C9 C8 C7 119.5(4) . . ? C8 C9 N1 122.4(4) . . ? C8 C9 C10 129.3(4) . . ? N1 C9 C10 108.3(4) . . ? C11 C10 C15 121.4(4) . . ? C11 C10 C9 131.8(4) . . ? C15 C10 C9 106.8(4) . . ? C10 C11 C12 117.2(4) . . ? C11 C12 C13 122.0(4) . . ? C14 C13 C12 120.5(5) . . ? C15 C14 C13 117.4(4) . . ? C14 C15 C10 121.4(4) . . ? C14 C15 C16 130.1(4) . . ? C10 C15 C16 108.4(4) . . ? O1 C16 N1 123.7(4) . . ? O1 C16 C15 129.5(5) . . ? N1 C16 C15 106.7(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.357 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 923118' ####################################################################### # # 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_exp_974 #TrackingRef 'BTC.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H8 B F2 N3 O S' _chemical_formula_weight 351.13 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' O O 0.0106 0.0060 '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' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 13.6330(14) _cell_length_b 9.7606(11) _cell_length_c 21.294(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2833.5(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.646 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.264 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9921 _exptl_absorpt_correction_T_max 0.9947 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 15867 _diffrn_reflns_av_R_equivalents 0.1290 _diffrn_reflns_av_sigmaI/netI 0.0828 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2495 _reflns_number_gt 1657 _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^)+(0.0927P)^2^+0.6489P] 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 2495 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1004 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1821 _refine_ls_wR_factor_gt 0.1515 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 S1 S 0.10931(7) 0.28708(10) 0.45407(5) 0.0249(3) Uani 1 1 d . . . B1 B 0.3901(3) 0.1809(5) 0.4043(2) 0.0233(10) Uani 1 1 d . . . F1 F 0.44579(15) 0.1211(2) 0.45189(11) 0.0284(6) Uani 1 1 d . . . F2 F 0.44225(17) 0.2864(2) 0.37765(11) 0.0292(6) Uani 1 1 d . . . N1 N 0.2924(2) 0.2400(3) 0.43310(16) 0.0225(8) Uani 1 1 d . . . N2 N 0.3578(2) 0.0731(3) 0.35543(16) 0.0227(8) Uani 1 1 d . . . N3 N 0.0051(3) 0.0818(4) 0.33051(18) 0.0295(9) Uani 1 1 d . . . O1 O 0.5130(2) -0.0034(3) 0.32623(14) 0.0285(7) Uani 1 1 d . . . C1 C 0.2906(3) 0.3383(4) 0.48190(19) 0.0232(9) Uani 1 1 d . . . C2 C 0.3711(3) 0.3995(4) 0.5101(2) 0.0278(10) Uani 1 1 d . . . H2 H 0.4347 0.3770 0.4981 0.033 Uiso 1 1 calc R . . C3 C 0.3534(3) 0.4948(4) 0.5564(2) 0.0302(10) Uani 1 1 d . . . H3 H 0.4061 0.5376 0.5760 0.036 Uiso 1 1 calc R . . C4 C 0.2576(3) 0.5287(4) 0.5748(2) 0.0301(10) Uani 1 1 d . . . H4 H 0.2479 0.5928 0.6065 0.036 Uiso 1 1 calc R . . C5 C 0.1782(3) 0.4689(4) 0.5467(2) 0.0286(10) Uani 1 1 d . . . H5 H 0.1147 0.4909 0.5591 0.034 Uiso 1 1 calc R . . C6 C 0.1953(3) 0.3741(4) 0.49913(19) 0.0244(9) Uani 1 1 d . . . C7 C 0.2027(3) 0.2068(4) 0.4148(2) 0.0247(10) Uani 1 1 d . . . C8 C 0.1854(3) 0.1081(4) 0.36524(19) 0.0222(9) Uani 1 1 d . . . C9 C 0.2640(3) 0.0438(4) 0.33830(19) 0.0218(9) Uani 1 1 d . . . C10 C 0.2656(3) -0.0640(4) 0.28910(18) 0.0218(9) Uani 1 1 d . . . C11 C 0.3635(3) -0.0950(4) 0.2784(2) 0.0263(10) Uani 1 1 d . . . C12 C 0.4257(3) -0.0081(4) 0.32041(19) 0.0232(9) Uani 1 1 d . . . C13 C 0.3913(3) -0.1943(4) 0.2351(2) 0.0272(10) Uani 1 1 d . . . H13 H 0.4569 -0.2130 0.2268 0.033 Uiso 1 1 calc R . . C16 C 0.1914(3) -0.1318(4) 0.25855(19) 0.0231(9) Uani 1 1 d . . . H16 H 0.1258 -0.1106 0.2658 0.028 Uiso 1 1 calc R . . C14 C 0.3165(3) -0.2637(4) 0.2048(2) 0.0269(10) Uani 1 1 d . . . H14 H 0.3324 -0.3322 0.1762 0.032 Uiso 1 1 calc R . . C15 C 0.2186(3) -0.2344(4) 0.2159(2) 0.0266(10) Uani 1 1 d . . . H15 H 0.1703 -0.2834 0.1948 0.032 Uiso 1 1 calc R . . C17 C 0.0858(3) 0.0885(4) 0.34556(19) 0.0241(9) 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 S1 0.0258(6) 0.0290(6) 0.0199(6) -0.0015(4) 0.0010(4) 0.0013(4) B1 0.024(3) 0.026(2) 0.020(2) 0.001(2) -0.001(2) -0.004(2) F1 0.0274(13) 0.0363(13) 0.0216(13) -0.0008(11) -0.0013(10) 0.0022(10) F2 0.0325(14) 0.0307(14) 0.0243(13) -0.0006(11) 0.0031(11) -0.0055(10) N1 0.026(2) 0.0240(18) 0.0177(18) 0.0002(14) 0.0006(15) -0.0016(14) N2 0.0235(18) 0.0282(18) 0.0165(18) -0.0012(15) -0.0010(14) 0.0009(15) N3 0.028(2) 0.034(2) 0.026(2) 0.0008(16) -0.0003(17) 0.0010(16) O1 0.0223(17) 0.0362(18) 0.0269(17) -0.0041(14) 0.0009(13) -0.0003(12) C1 0.029(2) 0.024(2) 0.017(2) 0.0043(18) -0.0022(18) 0.0011(17) C2 0.030(2) 0.031(2) 0.022(2) 0.0009(19) -0.0034(19) -0.0005(18) C3 0.040(3) 0.030(2) 0.021(2) -0.0003(19) -0.006(2) -0.005(2) C4 0.040(3) 0.029(2) 0.022(2) -0.0040(19) 0.001(2) 0.005(2) C5 0.034(2) 0.032(2) 0.019(2) -0.0023(19) 0.000(2) 0.0071(19) C6 0.031(2) 0.024(2) 0.018(2) 0.0041(18) -0.0021(18) 0.0001(18) C7 0.031(3) 0.023(2) 0.020(2) 0.0038(18) -0.0017(18) -0.0001(18) C8 0.024(2) 0.023(2) 0.020(2) 0.0007(17) -0.0028(17) -0.0013(17) C9 0.024(2) 0.022(2) 0.019(2) 0.0063(17) 0.0013(17) 0.0008(17) C10 0.028(2) 0.023(2) 0.014(2) 0.0053(17) 0.0009(17) 0.0005(17) C11 0.033(2) 0.027(2) 0.020(2) 0.0048(18) -0.0023(18) -0.0013(18) C12 0.028(2) 0.023(2) 0.019(2) 0.0030(17) 0.0017(19) 0.0012(17) C13 0.026(2) 0.032(2) 0.023(2) 0.0032(19) 0.0041(19) 0.0001(18) C16 0.024(2) 0.026(2) 0.020(2) 0.0047(18) 0.0028(18) 0.0031(17) C14 0.035(3) 0.029(2) 0.016(2) -0.0025(18) -0.0006(19) 0.0030(19) C15 0.031(2) 0.031(2) 0.018(2) 0.0020(19) -0.0020(19) -0.0011(18) C17 0.028(2) 0.022(2) 0.023(2) 0.0016(17) 0.0092(19) 0.0007(18) _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 S1 C7 1.712(4) . ? S1 C6 1.737(4) . ? B1 F2 1.374(5) . ? B1 F1 1.394(5) . ? B1 N2 1.544(6) . ? B1 N1 1.576(6) . ? N1 C7 1.324(5) . ? N1 C1 1.415(5) . ? N2 C9 1.361(5) . ? N2 C12 1.428(5) . ? N3 C17 1.148(5) . ? O1 C12 1.197(4) . ? C1 C2 1.386(5) . ? C1 C6 1.394(6) . ? C2 C3 1.378(6) . ? C2 H2 0.9300 . ? C3 C4 1.402(6) . ? C3 H3 0.9300 . ? C4 C5 1.367(6) . ? C4 H4 0.9300 . ? C5 C6 1.392(6) . ? C5 H5 0.9300 . ? C7 C8 1.449(6) . ? C8 C9 1.368(5) . ? C8 C17 1.434(6) . ? C9 C10 1.485(6) . ? C10 C16 1.374(5) . ? C10 C11 1.386(6) . ? C11 C13 1.391(6) . ? C11 C12 1.496(6) . ? C13 C14 1.383(6) . ? C13 H13 0.9300 . ? C16 C15 1.401(6) . ? C16 H16 0.9300 . ? C14 C15 1.385(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? 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 C7 S1 C6 89.5(2) . . ? F2 B1 F1 109.4(3) . . ? F2 B1 N2 112.3(4) . . ? F1 B1 N2 111.1(3) . . ? F2 B1 N1 108.9(3) . . ? F1 B1 N1 109.3(3) . . ? N2 B1 N1 105.7(3) . . ? C7 N1 C1 111.5(3) . . ? C7 N1 B1 125.3(3) . . ? C1 N1 B1 123.3(3) . . ? C9 N2 C12 110.6(3) . . ? C9 N2 B1 126.3(3) . . ? C12 N2 B1 123.1(3) . . ? C2 C1 C6 121.0(4) . . ? C2 C1 N1 126.6(4) . . ? C6 C1 N1 112.3(3) . . ? C3 C2 C1 117.5(4) . . ? C3 C2 H2 121.2 . . ? C1 C2 H2 121.2 . . ? C2 C3 C4 121.4(4) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 121.0(4) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 118.0(4) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C5 C6 C1 121.0(4) . . ? C5 C6 S1 127.9(3) . . ? C1 C6 S1 111.1(3) . . ? N1 C7 C8 121.8(4) . . ? N1 C7 S1 115.6(3) . . ? C8 C7 S1 122.7(3) . . ? C9 C8 C17 123.9(4) . . ? C9 C8 C7 119.0(4) . . ? C17 C8 C7 117.1(4) . . ? N2 C9 C8 121.8(4) . . ? N2 C9 C10 108.9(3) . . ? C8 C9 C10 129.3(4) . . ? C16 C10 C11 121.7(4) . . ? C16 C10 C9 131.7(4) . . ? C11 C10 C9 106.6(3) . . ? C10 C11 C13 121.6(4) . . ? C10 C11 C12 108.9(4) . . ? C13 C11 C12 129.6(4) . . ? O1 C12 N2 124.6(4) . . ? O1 C12 C11 130.4(4) . . ? N2 C12 C11 105.0(3) . . ? C14 C13 C11 116.7(4) . . ? C14 C13 H13 121.6 . . ? C11 C13 H13 121.6 . . ? C10 C16 C15 117.1(4) . . ? C10 C16 H16 121.4 . . ? C15 C16 H16 121.4 . . ? C13 C14 C15 121.9(4) . . ? C13 C14 H14 119.0 . . ? C15 C14 H14 119.0 . . ? C14 C15 C16 120.9(4) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? N3 C17 C8 175.5(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.642 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.094 _database_code_depnum_ccdc_archive 'CCDC 923119' ####################################################################### # # 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_exp_1851 #TrackingRef 'BTN.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H16 B2 F4 N6 O2 S2' _chemical_formula_weight 654.23 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' O O 0.0106 0.0060 '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' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3276(6) _cell_length_b 9.7084(6) _cell_length_c 19.6254(12) _cell_angle_alpha 103.803(5) _cell_angle_beta 90.192(6) _cell_angle_gamma 115.396(7) _cell_volume 1381.81(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2956 _cell_measurement_theta_min 2.7219 _cell_measurement_theta_max 28.3750 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.572 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.264 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9492 _exptl_absorpt_correction_T_max 0.9741 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _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 9147 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4880 _reflns_number_gt 4016 _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^)+(0.0000P)^2^+25.7410P] 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 4880 _refine_ls_number_parameters 415 _refine_ls_number_restraints 1338 _refine_ls_R_factor_all 0.1632 _refine_ls_R_factor_gt 0.1487 _refine_ls_wR_factor_ref 0.3225 _refine_ls_wR_factor_gt 0.3165 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.017 _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 S2 S 0.2393(4) 0.2006(3) 0.50251(14) 0.0473(6) Uani 1 1 d U . . F3 F 0.3047(8) 0.5927(7) 0.3821(3) 0.0558(15) Uani 1 1 d U . . F4 F 0.0263(8) 0.5299(7) 0.4138(3) 0.0603(16) Uani 1 1 d U . . C30 C 0.3004(11) 0.8266(10) 0.5220(4) 0.0312(16) Uani 1 1 d U . . N5 N 0.3406(11) 0.5042(9) 0.5645(4) 0.0423(16) Uani 1 1 d U . . C22 C 0.2587(12) 0.3855(10) 0.5040(5) 0.0362(17) Uani 1 1 d U . . N4 N 0.1836(10) 0.3899(9) 0.4458(4) 0.0383(15) Uani 1 1 d U . . N6 N 0.2785(10) 0.6721(9) 0.5062(4) 0.0373(15) Uani 1 1 d U . . C29 C 0.3974(13) 0.8998(11) 0.5982(5) 0.0399(18) Uani 1 1 d U . . C24 C 0.4186(12) 0.7815(11) 0.6201(5) 0.0376(17) Uani 1 1 d U . . O2 O 0.2590(11) 0.8905(9) 0.4881(4) 0.0618(19) Uani 1 1 d U . . C21 C 0.1115(12) 0.2451(11) 0.3943(5) 0.0394(18) Uani 1 1 d U . . C23 C 0.3401(12) 0.6365(11) 0.5622(5) 0.0373(17) Uani 1 1 d U . . C25 C 0.4988(13) 0.8128(12) 0.6872(5) 0.046(2) Uani 1 1 d U . . H25 H 0.5127 0.7340 0.7019 0.055 Uiso 1 1 calc R . . C16 C 0.1288(12) 0.1249(11) 0.4166(5) 0.0404(19) Uani 1 1 d U . . C17 C 0.0620(13) -0.0294(11) 0.3729(5) 0.043(2) Uani 1 1 d U . . H17 H 0.0706 -0.1101 0.3880 0.052 Uiso 1 1 calc R . . C20 C 0.0239(13) 0.2152(11) 0.3273(5) 0.044(2) Uani 1 1 d U . . H20 H 0.0085 0.2933 0.3124 0.053 Uiso 1 1 calc R . . C26 C 0.5562(14) 0.9576(13) 0.7307(6) 0.054(2) Uani 1 1 d U . . H26 H 0.6089 0.9773 0.7760 0.065 Uiso 1 1 calc R . . B2 B 0.1933(15) 0.5499(13) 0.4353(6) 0.040(2) Uani 1 1 d U . . C18 C -0.0165(14) -0.0552(12) 0.3071(6) 0.053(2) Uani 1 1 d U . . H18 H -0.0568 -0.1555 0.2762 0.063 Uiso 1 1 calc R . . C28 C 0.4573(14) 1.0491(13) 0.6436(6) 0.053(2) Uani 1 1 d U . . H28 H 0.4422 1.1279 0.6293 0.064 Uiso 1 1 calc R . . C19 C -0.0394(14) 0.0590(13) 0.2839(6) 0.053(2) Uani 1 1 d U . . H19 H -0.0976 0.0329 0.2389 0.063 Uiso 1 1 calc R . . C27 C 0.5403(14) 1.0811(13) 0.7109(6) 0.054(2) Uani 1 1 d U . . H27 H 0.5841 1.1815 0.7419 0.065 Uiso 1 1 calc R . . S1 S 1.0375(3) 1.3076(3) 0.00325(14) 0.0493(7) Uani 1 1 d U . . F1 F 0.4997(8) 0.9759(7) 0.0910(3) 0.0582(16) Uani 1 1 d U . . F2 F 0.7147(8) 0.9123(7) 0.1232(3) 0.0579(15) Uani 1 1 d U . . N2 N 0.8386(10) 1.0030(10) -0.0569(4) 0.0440(17) Uani 1 1 d U . . N1 N 0.7957(10) 1.1163(9) 0.0604(4) 0.0403(16) Uani 1 1 d U . . C7 C 0.8784(12) 1.1248(11) 0.0034(5) 0.0388(18) Uani 1 1 d U . . N3 N 0.6089(10) 0.8348(9) 0.0002(4) 0.0400(16) Uani 1 1 d U . . C6 C 0.8650(12) 1.2605(11) 0.1115(5) 0.0387(18) Uani 1 1 d U . . O1 O 0.3665(10) 0.6173(9) 0.0175(4) 0.061(2) Uani 1 1 d U . . C8 C 0.7053(12) 0.8706(11) -0.0553(5) 0.0394(18) Uani 1 1 d U . . B1 B 0.6443(14) 0.9577(13) 0.0717(6) 0.042(2) Uani 1 1 d U . . C10 C 0.6875(14) 0.6898(13) -0.1816(5) 0.053(2) Uani 1 1 d U . . H10 H 0.7821 0.7668 -0.1965 0.063 Uiso 1 1 calc R . . C5 C 0.8128(13) 1.2905(11) 0.1782(5) 0.0419(19) Uani 1 1 d U . . H5 H 0.7215 1.2103 0.1928 0.050 Uiso 1 1 calc R . . C14 C 0.4970(12) 0.6115(11) -0.0918(5) 0.0402(18) Uani 1 1 d U . . C9 C 0.6350(12) 0.7216(11) -0.1150(5) 0.0416(18) Uani 1 1 d U . . C1 C 1.0034(13) 1.3851(12) 0.0892(6) 0.047(2) Uani 1 1 d U . . C15 C 0.4717(12) 0.6818(11) -0.0173(5) 0.0424(19) Uani 1 1 d U . . C13 C 0.4026(14) 0.4558(13) -0.1379(6) 0.054(2) Uani 1 1 d U . . H13 H 0.3073 0.3769 -0.1244 0.065 Uiso 1 1 calc R . . C2 C 1.0869(14) 1.5328(11) 0.1315(6) 0.048(2) Uani 1 1 d U . . H2 H 1.1749 1.6129 0.1158 0.058 Uiso 1 1 calc R . . C11 C 0.5954(15) 0.5424(13) -0.2237(6) 0.057(2) Uani 1 1 d U . . H11 H 0.6259 0.5171 -0.2690 0.068 Uiso 1 1 calc R . . C3 C 1.0381(15) 1.5643(12) 0.2009(6) 0.056(2) Uani 1 1 d U . . H3 H 1.0979 1.6650 0.2315 0.068 Uiso 1 1 calc R . . C4 C 0.9000(14) 1.4442(12) 0.2237(6) 0.050(2) Uani 1 1 d U . . H4 H 0.8665 1.4664 0.2686 0.060 Uiso 1 1 calc R . . C12 C 0.4581(14) 0.4291(14) -0.2014(6) 0.057(2) Uani 1 1 d U . . H12 H 0.4001 0.3282 -0.2320 0.069 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 S2 0.0594(16) 0.0402(13) 0.0500(14) 0.0174(11) 0.0056(12) 0.0261(12) F3 0.073(4) 0.046(3) 0.051(3) 0.016(3) 0.016(3) 0.026(3) F4 0.063(4) 0.061(4) 0.067(4) 0.015(3) -0.007(3) 0.038(3) C30 0.038(4) 0.035(4) 0.035(4) 0.020(3) 0.021(3) 0.024(3) N5 0.051(3) 0.041(3) 0.036(3) 0.008(3) 0.005(3) 0.023(3) C22 0.045(4) 0.038(4) 0.035(4) 0.014(3) 0.006(3) 0.024(3) N4 0.041(3) 0.041(3) 0.035(3) 0.013(3) 0.004(3) 0.019(3) N6 0.041(3) 0.042(3) 0.037(3) 0.017(3) 0.008(3) 0.023(3) C29 0.045(4) 0.040(4) 0.038(4) 0.016(3) 0.011(3) 0.019(3) C24 0.041(4) 0.039(4) 0.036(4) 0.012(3) 0.009(3) 0.020(3) O2 0.084(5) 0.053(4) 0.060(4) 0.020(4) 0.004(4) 0.038(4) C21 0.043(4) 0.038(4) 0.039(4) 0.012(3) 0.009(3) 0.018(3) C23 0.043(4) 0.039(4) 0.036(4) 0.010(3) 0.008(3) 0.025(3) C25 0.051(4) 0.046(4) 0.042(4) 0.010(3) 0.009(4) 0.023(3) C16 0.036(4) 0.040(4) 0.042(4) 0.006(3) 0.009(3) 0.017(3) C17 0.048(4) 0.032(4) 0.047(4) 0.010(3) 0.005(4) 0.016(3) C20 0.047(4) 0.040(4) 0.043(4) 0.010(3) 0.006(3) 0.018(3) C26 0.051(5) 0.057(5) 0.042(5) 0.004(4) 0.005(4) 0.017(4) B2 0.043(4) 0.040(4) 0.042(4) 0.007(4) 0.004(4) 0.024(3) C18 0.051(5) 0.039(5) 0.049(5) 0.001(4) 0.004(4) 0.009(4) C28 0.052(4) 0.051(4) 0.050(4) 0.009(4) 0.011(4) 0.020(4) C19 0.049(5) 0.052(5) 0.049(5) 0.009(4) 0.006(4) 0.017(4) C27 0.051(5) 0.047(5) 0.052(5) -0.003(4) 0.007(4) 0.018(4) S1 0.0446(14) 0.0423(14) 0.0527(15) 0.0187(11) 0.0096(11) 0.0087(11) F1 0.046(3) 0.059(4) 0.059(4) 0.011(3) 0.019(3) 0.016(3) F2 0.062(4) 0.055(3) 0.048(3) 0.021(3) 0.001(3) 0.015(3) N2 0.038(3) 0.049(4) 0.040(3) 0.015(3) 0.007(3) 0.013(3) N1 0.037(3) 0.046(3) 0.039(3) 0.016(3) 0.006(3) 0.018(3) C7 0.036(4) 0.042(4) 0.039(4) 0.019(3) 0.010(3) 0.014(3) N3 0.038(3) 0.049(4) 0.038(3) 0.023(3) 0.006(3) 0.019(3) C6 0.039(4) 0.037(4) 0.044(4) 0.015(3) 0.002(3) 0.017(3) O1 0.059(4) 0.055(4) 0.049(4) 0.012(3) 0.013(3) 0.008(4) C8 0.037(4) 0.042(4) 0.040(4) 0.014(3) 0.002(3) 0.016(3) B1 0.037(4) 0.048(4) 0.042(4) 0.018(4) 0.006(4) 0.018(3) C10 0.053(4) 0.056(4) 0.046(4) 0.018(4) 0.004(4) 0.018(4) C5 0.043(4) 0.040(4) 0.046(4) 0.014(3) 0.008(3) 0.020(3) C14 0.042(4) 0.042(4) 0.038(4) 0.018(3) 0.002(3) 0.016(3) C9 0.041(4) 0.046(4) 0.041(4) 0.014(3) 0.001(3) 0.022(3) C1 0.041(4) 0.047(4) 0.055(4) 0.015(4) 0.001(4) 0.021(3) C15 0.037(4) 0.040(4) 0.052(4) 0.030(3) -0.009(3) 0.009(3) C13 0.048(4) 0.052(4) 0.053(4) 0.008(4) -0.004(4) 0.016(4) C2 0.049(4) 0.036(4) 0.060(5) 0.018(4) 0.004(4) 0.017(3) C11 0.055(5) 0.062(5) 0.049(5) 0.006(4) -0.001(4) 0.027(4) C3 0.063(5) 0.037(4) 0.064(5) 0.008(4) -0.005(5) 0.019(4) C4 0.052(5) 0.046(4) 0.055(5) 0.010(4) 0.004(4) 0.025(4) C12 0.049(5) 0.057(5) 0.059(5) -0.002(4) -0.005(4) 0.025(4) _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 S2 C22 1.725(9) . ? S2 C16 1.745(10) . ? F3 B2 1.418(12) . ? F4 B2 1.370(12) . ? C30 O2 1.151(10) . ? C30 N6 1.387(11) . ? C30 C29 1.546(13) . ? N5 C23 1.297(11) . ? N5 C22 1.369(11) . ? C22 N4 1.318(11) . ? N4 C21 1.397(11) . ? N4 B2 1.583(13) . ? N6 C23 1.387(11) . ? N6 B2 1.526(13) . ? C29 C28 1.380(14) . ? C29 C24 1.394(12) . ? C24 C25 1.378(13) . ? C24 C23 1.463(12) . ? C21 C16 1.401(13) . ? C21 C20 1.406(13) . ? C25 C26 1.334(14) . ? C16 C17 1.399(13) . ? C17 C18 1.363(14) . ? C20 C19 1.413(14) . ? C26 C27 1.402(15) . ? C18 C19 1.377(15) . ? C28 C27 1.390(15) . ? S1 C7 1.700(9) . ? S1 C1 1.753(11) . ? F1 B1 1.333(12) . ? F2 B1 1.410(12) . ? N2 C8 1.297(12) . ? N2 C7 1.379(12) . ? N1 C7 1.317(11) . ? N1 C6 1.390(12) . ? N1 B1 1.584(13) . ? N3 C8 1.378(11) . ? N3 C15 1.389(11) . ? N3 B1 1.542(14) . ? C6 C5 1.385(13) . ? C6 C1 1.430(13) . ? O1 C15 1.168(11) . ? C8 C9 1.506(13) . ? C10 C11 1.345(15) . ? C10 C9 1.387(14) . ? C5 C4 1.408(14) . ? C14 C9 1.361(13) . ? C14 C13 1.431(14) . ? C14 C15 1.516(14) . ? C1 C2 1.342(14) . ? C13 C12 1.337(15) . ? C2 C3 1.423(15) . ? C11 C12 1.365(16) . ? C3 C4 1.409(15) . ? 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 C22 S2 C16 90.6(4) . . ? O2 C30 N6 130.1(9) . . ? O2 C30 C29 126.1(8) . . ? N6 C30 C29 103.8(7) . . ? C23 N5 C22 113.2(8) . . ? N4 C22 N5 128.8(8) . . ? N4 C22 S2 113.6(7) . . ? N5 C22 S2 117.5(6) . . ? C22 N4 C21 113.2(8) . . ? C22 N4 B2 121.5(8) . . ? C21 N4 B2 125.0(7) . . ? C23 N6 C30 113.1(7) . . ? C23 N6 B2 122.2(7) . . ? C30 N6 B2 124.7(7) . . ? C28 C29 C24 120.1(9) . . ? C28 C29 C30 132.4(9) . . ? C24 C29 C30 107.5(8) . . ? C25 C24 C29 120.2(9) . . ? C25 C24 C23 131.7(9) . . ? C29 C24 C23 108.1(8) . . ? N4 C21 C16 113.0(8) . . ? N4 C21 C20 125.7(8) . . ? C16 C21 C20 121.3(9) . . ? N5 C23 N6 128.5(8) . . ? N5 C23 C24 124.1(8) . . ? N6 C23 C24 107.4(7) . . ? C26 C25 C24 119.3(10) . . ? C17 C16 C21 121.5(9) . . ? C17 C16 S2 128.9(8) . . ? C21 C16 S2 109.6(7) . . ? C18 C17 C16 116.5(9) . . ? C21 C20 C19 115.8(9) . . ? C25 C26 C27 122.7(10) . . ? F4 B2 F3 108.4(8) . . ? F4 B2 N6 113.9(8) . . ? F3 B2 N6 110.1(8) . . ? F4 B2 N4 110.3(8) . . ? F3 B2 N4 108.5(7) . . ? N6 B2 N4 105.5(7) . . ? C17 C18 C19 123.6(10) . . ? C29 C28 C27 119.6(10) . . ? C18 C19 C20 121.2(10) . . ? C28 C27 C26 118.1(10) . . ? C7 S1 C1 90.5(5) . . ? C8 N2 C7 114.6(8) . . ? C7 N1 C6 112.1(8) . . ? C7 N1 B1 124.0(8) . . ? C6 N1 B1 123.8(8) . . ? N1 C7 N2 126.1(8) . . ? N1 C7 S1 115.6(7) . . ? N2 C7 S1 118.1(6) . . ? C8 N3 C15 112.7(8) . . ? C8 N3 B1 122.5(8) . . ? C15 N3 B1 124.7(8) . . ? C5 C6 N1 126.7(8) . . ? C5 C6 C1 120.1(9) . . ? N1 C6 C1 113.2(8) . . ? N2 C8 N3 128.2(9) . . ? N2 C8 C9 124.5(8) . . ? N3 C8 C9 107.1(8) . . ? F1 B1 F2 111.0(8) . . ? F1 B1 N3 113.5(8) . . ? F2 B1 N3 108.1(8) . . ? F1 B1 N1 111.2(8) . . ? F2 B1 N1 108.5(8) . . ? N3 B1 N1 104.2(7) . . ? C11 C10 C9 116.9(10) . . ? C6 C5 C4 119.0(9) . . ? C9 C14 C13 118.6(9) . . ? C9 C14 C15 110.5(8) . . ? C13 C14 C15 130.9(9) . . ? C14 C9 C10 122.9(9) . . ? C14 C9 C8 105.8(8) . . ? C10 C9 C8 131.3(9) . . ? C2 C1 C6 121.8(10) . . ? C2 C1 S1 129.7(8) . . ? C6 C1 S1 108.5(7) . . ? O1 C15 N3 129.2(10) . . ? O1 C15 C14 127.1(9) . . ? N3 C15 C14 103.6(8) . . ? C12 C13 C14 116.8(10) . . ? C1 C2 C3 118.7(10) . . ? C10 C11 C12 121.4(11) . . ? C4 C3 C2 120.6(10) . . ? C5 C4 C3 119.8(10) . . ? C13 C12 C11 123.4(11) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.919 _refine_diff_density_min -0.644 _refine_diff_density_rms 0.133 _database_code_depnum_ccdc_archive 'CCDC 923120'