####################################################################### # # 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_bt1303 _database_code_depnum_ccdc_archive 'CCDC 715296' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'C16 H12 F N O3' _chemical_melting_point ? _chemical_formula_moiety 'C16 H12 F N O3' _chemical_formula_sum 'C16 H12 F N O3' _chemical_formula_weight 285.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna2(1) _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 27.274(3) _cell_length_b 5.7146(7) _cell_length_c 16.204(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2525.5(5) _cell_formula_units_Z 8 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 8452 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 29.31 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.862 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details 'SADABS-2007/4 (Bruker, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker/Siemens SMART APEX' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37390 _diffrn_reflns_av_R_equivalents 0.0655 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 30.06 _reflns_number_total 3771 _reflns_number_gt 3083 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART v. 5.632 (Bruker, 2006)' _computing_cell_refinement 'SAINT+ v. 7.23a (Bruker, 2006)' _computing_data_reduction 'SAINT+ v. 7.23a (Bruker, 2006)' _computing_structure_solution 'XS, SHELXTL v. 6.14 (Bruker, 2003)' _computing_structure_refinement 'XL, SHELXTL v. 6.14 (Bruker, 2003)' _computing_molecular_graphics 'XP, SHELXTL v. 6.14 (Bruker, 2003)' _computing_publication_material 'XCIF, SHELXTL, v. 6.14 (Bruker, 2003)' _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^)+(0.0669P)^2^+0.2842P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 3771 _refine_ls_number_parameters 379 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1150 _refine_ls_wR_factor_gt 0.1052 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 C2 C 0.42577(9) 0.6092(5) 0.23408(16) 0.0195(5) Uani 1 1 d . . . C3 C 0.40714(10) 0.4272(4) 0.28104(17) 0.0208(5) Uani 1 1 d . . . H3 H 0.4277 0.3038 0.2998 0.025 Uiso 1 1 calc R . . C4 C 0.35738(9) 0.4312(4) 0.29982(17) 0.0192(5) Uani 1 1 d . . . H4 H 0.3435 0.3077 0.3314 0.023 Uiso 1 1 calc R . . C5 C 0.32763(9) 0.6138(4) 0.27296(15) 0.0168(5) Uani 1 1 d . . . C6 C 0.34759(9) 0.7935(4) 0.22584(18) 0.0206(5) Uani 1 1 d . . . H6 H 0.3273 0.9177 0.2072 0.025 Uiso 1 1 calc R . . C7 C 0.39723(9) 0.7921(4) 0.20588(17) 0.0205(5) Uani 1 1 d . . . H7 H 0.4111 0.9141 0.1737 0.025 Uiso 1 1 calc R . . C8 C 0.27302(9) 0.6075(4) 0.29170(16) 0.0170(5) Uani 1 1 d . . . C9 C 0.24598(9) 0.4432(4) 0.23085(17) 0.0181(5) Uani 1 1 d . . . C10 C 0.19201(9) 0.4613(4) 0.22917(16) 0.0173(5) Uani 1 1 d . . . C11 C 0.16591(10) 0.2924(4) 0.18433(18) 0.0208(5) Uani 1 1 d . . . H11 H 0.1831 0.1697 0.1573 0.025 Uiso 1 1 calc R . . C12 C 0.11538(10) 0.3032(5) 0.17918(19) 0.0236(6) Uani 1 1 d . . . H12 H 0.0977 0.1870 0.1496 0.028 Uiso 1 1 calc R . . C13 C 0.09070(10) 0.4849(5) 0.21751(18) 0.0245(6) Uani 1 1 d . . . H13 H 0.0560 0.4947 0.2131 0.029 Uiso 1 1 calc R . . C14 C 0.11599(9) 0.6527(5) 0.26226(18) 0.0237(6) Uani 1 1 d . . . H14 H 0.0985 0.7763 0.2881 0.028 Uiso 1 1 calc R . . C15 C 0.16721(9) 0.6419(4) 0.26977(16) 0.0188(5) Uani 1 1 d . . . C16 C 0.19450(9) 0.8197(4) 0.32066(18) 0.0217(5) Uani 1 1 d . . . H16A H 0.1930 0.7734 0.3795 0.026 Uiso 1 1 calc R . . H16B H 0.1781 0.9736 0.3151 0.026 Uiso 1 1 calc R . . C17 C 0.24805(9) 0.8439(4) 0.29489(17) 0.0194(5) Uani 1 1 d . . . H17A H 0.2498 0.9187 0.2399 0.023 Uiso 1 1 calc R . . H17B H 0.2654 0.9458 0.3347 0.023 Uiso 1 1 calc R . . C19 C 0.33006(9) 0.1220(5) 0.50833(16) 0.0187(5) Uani 1 1 d . . . C20 C 0.34638(9) -0.0698(5) 0.46376(16) 0.0185(5) Uani 1 1 d . . . H20 H 0.3242 -0.1889 0.4469 0.022 Uiso 1 1 calc R . . C21 C 0.39578(9) -0.0837(4) 0.44440(16) 0.0189(5) Uani 1 1 d . . . H21 H 0.4077 -0.2140 0.4140 0.023 Uiso 1 1 calc R . . C22 C 0.42830(9) 0.0927(4) 0.46919(16) 0.0167(5) Uani 1 1 d . . . C23 C 0.41045(9) 0.2814(5) 0.51463(18) 0.0207(5) Uani 1 1 d . . . H23 H 0.4324 0.4004 0.5324 0.025 Uiso 1 1 calc R . . C24 C 0.36114(9) 0.2973(5) 0.53421(18) 0.0223(6) Uani 1 1 d . . . H24 H 0.3490 0.4265 0.5649 0.027 Uiso 1 1 calc R . . C25 C 0.48237(9) 0.0710(4) 0.44969(16) 0.0176(5) Uani 1 1 d . . . C26 C 0.50822(9) -0.1005(4) 0.50978(17) 0.0168(5) Uani 1 1 d . . . C27 C 0.56280(9) -0.0939(4) 0.51028(16) 0.0173(5) Uani 1 1 d . . . C28 C 0.58745(9) -0.2673(4) 0.55484(18) 0.0197(5) Uani 1 1 d . . . H28 H 0.5693 -0.3884 0.5810 0.024 Uiso 1 1 calc R . . C29 C 0.63805(9) -0.2641(5) 0.56122(18) 0.0218(6) Uani 1 1 d . . . H29 H 0.6548 -0.3841 0.5903 0.026 Uiso 1 1 calc R . . C30 C 0.66388(9) -0.0826(5) 0.52443(17) 0.0234(6) Uani 1 1 d . . . H30 H 0.6985 -0.0756 0.5304 0.028 Uiso 1 1 calc R . . C31 C 0.63994(10) 0.0885(5) 0.47916(18) 0.0221(5) Uani 1 1 d . . . H31 H 0.6584 0.2097 0.4537 0.027 Uiso 1 1 calc R . . C32 C 0.58901(9) 0.0846(4) 0.47056(16) 0.0179(5) Uani 1 1 d . . . C33 C 0.56303(9) 0.2654(4) 0.41894(17) 0.0194(5) Uani 1 1 d . . . H33A H 0.5639 0.2165 0.3603 0.023 Uiso 1 1 calc R . . H33B H 0.5806 0.4163 0.4236 0.023 Uiso 1 1 calc R . . C34 C 0.50968(9) 0.3002(4) 0.44517(17) 0.0178(5) Uani 1 1 d . . . H34A H 0.5088 0.3771 0.4999 0.021 Uiso 1 1 calc R . . H34B H 0.4931 0.4046 0.4051 0.021 Uiso 1 1 calc R . . F1 F 0.26703(5) 0.4961(3) 0.36940(9) 0.0215(3) Uani 1 1 d . . . F2 F 0.48635(5) -0.0432(3) 0.37149(10) 0.0220(3) Uani 1 1 d . . . N1 N 0.47816(8) 0.6053(4) 0.21146(14) 0.0220(5) Uani 1 1 d . . . N18 N 0.27760(8) 0.1389(4) 0.52954(14) 0.0212(5) Uani 1 1 d . . . O1 O 0.50531(7) 0.4693(4) 0.24808(14) 0.0340(5) Uani 1 1 d . . . O2 O 0.49183(7) 0.7387(4) 0.15692(13) 0.0283(5) Uani 1 1 d . . . O3 O 0.26872(7) 0.3056(3) 0.18848(13) 0.0220(4) Uani 1 1 d . . . O4 O 0.26493(7) 0.2919(4) 0.57837(13) 0.0260(5) Uani 1 1 d . . . O5 O 0.24913(7) 0.0003(4) 0.49764(14) 0.0312(5) Uani 1 1 d . . . O6 O 0.48471(6) -0.2334(3) 0.55212(14) 0.0220(4) 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 C2 0.0159(11) 0.0251(13) 0.0175(13) -0.0025(10) -0.0021(10) -0.0042(9) C3 0.0214(12) 0.0215(12) 0.0194(13) 0.0025(10) -0.0032(10) 0.0005(10) C4 0.0221(12) 0.0172(11) 0.0183(12) 0.0035(10) -0.0013(10) -0.0042(9) C5 0.0169(11) 0.0200(11) 0.0135(12) -0.0016(9) -0.0007(9) -0.0021(9) C6 0.0217(12) 0.0188(12) 0.0214(14) 0.0001(10) -0.0016(10) 0.0006(10) C7 0.0227(12) 0.0178(12) 0.0210(14) 0.0022(10) 0.0006(11) -0.0042(10) C8 0.0177(11) 0.0176(11) 0.0157(12) 0.0017(9) 0.0005(9) -0.0011(9) C9 0.0216(12) 0.0131(11) 0.0196(12) 0.0026(9) -0.0011(10) -0.0023(9) C10 0.0158(11) 0.0186(11) 0.0175(12) 0.0021(9) -0.0012(10) -0.0015(9) C11 0.0230(13) 0.0188(12) 0.0208(14) 0.0000(10) -0.0002(11) -0.0002(10) C12 0.0188(13) 0.0287(14) 0.0231(15) 0.0006(11) -0.0030(11) -0.0065(11) C13 0.0198(12) 0.0287(14) 0.0250(14) 0.0071(12) -0.0021(11) 0.0010(10) C14 0.0207(12) 0.0254(13) 0.0250(14) 0.0027(11) 0.0028(11) 0.0025(10) C15 0.0217(12) 0.0182(12) 0.0164(12) 0.0035(10) 0.0009(10) -0.0010(10) C16 0.0243(13) 0.0173(12) 0.0236(14) -0.0022(10) 0.0026(11) 0.0023(10) C17 0.0207(12) 0.0162(11) 0.0214(13) 0.0007(11) 0.0003(10) -0.0009(10) C19 0.0157(11) 0.0220(12) 0.0184(13) 0.0018(10) -0.0002(10) 0.0032(9) C20 0.0200(12) 0.0189(12) 0.0167(13) 0.0001(10) -0.0030(10) -0.0020(9) C21 0.0223(12) 0.0154(11) 0.0190(12) -0.0017(10) -0.0020(10) 0.0023(9) C22 0.0174(11) 0.0155(11) 0.0172(12) 0.0016(9) -0.0014(10) 0.0007(9) C23 0.0196(12) 0.0197(12) 0.0229(14) -0.0049(10) -0.0004(10) -0.0040(9) C24 0.0228(13) 0.0191(12) 0.0248(15) -0.0050(10) 0.0007(11) 0.0030(10) C25 0.0202(12) 0.0183(12) 0.0143(12) -0.0041(9) 0.0003(10) 0.0014(9) C26 0.0185(12) 0.0136(10) 0.0182(12) -0.0049(9) -0.0005(10) 0.0008(9) C27 0.0176(11) 0.0160(11) 0.0182(12) -0.0044(9) -0.0009(10) 0.0011(9) C28 0.0194(12) 0.0194(12) 0.0204(14) -0.0025(10) -0.0016(11) 0.0009(9) C29 0.0227(13) 0.0228(13) 0.0199(15) -0.0018(10) -0.0051(11) 0.0034(10) C30 0.0158(11) 0.0281(14) 0.0263(15) -0.0059(11) -0.0013(10) 0.0007(10) C31 0.0192(12) 0.0218(12) 0.0254(14) -0.0031(10) 0.0024(11) -0.0033(10) C32 0.0195(12) 0.0176(12) 0.0166(12) -0.0034(9) 0.0005(10) 0.0000(9) C33 0.0198(12) 0.0185(12) 0.0200(13) 0.0014(10) 0.0032(10) -0.0001(9) C34 0.0178(12) 0.0163(11) 0.0194(12) 0.0012(10) 0.0005(10) 0.0002(9) F1 0.0242(7) 0.0243(7) 0.0158(7) 0.0059(6) 0.0012(6) -0.0009(6) F2 0.0226(8) 0.0246(7) 0.0189(8) -0.0065(7) 0.0000(6) 0.0020(6) N1 0.0192(11) 0.0277(11) 0.0192(11) -0.0017(9) 0.0002(9) -0.0031(9) N18 0.0168(10) 0.0261(11) 0.0207(12) 0.0007(9) 0.0003(8) 0.0023(9) O1 0.0220(10) 0.0475(13) 0.0326(12) 0.0112(10) -0.0004(9) 0.0064(9) O2 0.0256(10) 0.0324(11) 0.0269(12) 0.0037(9) 0.0036(9) -0.0061(8) O3 0.0205(9) 0.0193(9) 0.0261(10) -0.0057(8) 0.0025(8) -0.0003(7) O4 0.0211(9) 0.0288(11) 0.0281(11) -0.0044(9) 0.0024(8) 0.0061(8) O5 0.0206(9) 0.0407(12) 0.0322(12) -0.0094(10) 0.0011(9) -0.0077(9) O6 0.0202(9) 0.0176(9) 0.0283(11) 0.0021(8) 0.0024(8) -0.0019(7) _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 C2 C7 1.381(4) . ? C2 C3 1.385(4) . ? C2 N1 1.475(3) . ? C3 C4 1.391(4) . ? C3 H3 0.9500 . ? C4 C5 1.392(3) . ? C4 H4 0.9500 . ? C5 C6 1.390(4) . ? C5 C8 1.521(3) . ? C6 C7 1.392(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 F1 1.420(3) . ? C8 C17 1.514(3) . ? C8 C9 1.548(3) . ? C9 O3 1.214(3) . ? C9 C10 1.476(3) . ? C10 C15 1.398(3) . ? C10 C11 1.402(4) . ? C11 C12 1.382(4) . ? C11 H11 0.9500 . ? C12 C13 1.385(4) . ? C12 H12 0.9500 . ? C13 C14 1.386(4) . ? C13 H13 0.9500 . ? C14 C15 1.404(4) . ? C14 H14 0.9500 . ? C15 C16 1.505(4) . ? C16 C17 1.525(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C19 C24 1.378(4) . ? C19 C20 1.386(4) . ? C19 N18 1.475(3) . ? C20 C21 1.385(4) . ? C20 H20 0.9500 . ? C21 C22 1.401(3) . ? C21 H21 0.9500 . ? C22 C23 1.394(4) . ? C22 C25 1.513(3) . ? C23 C24 1.385(4) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 F2 1.429(3) . ? C25 C34 1.509(3) . ? C25 C26 1.551(3) . ? C26 O6 1.208(3) . ? C26 C27 1.489(3) . ? C27 C28 1.398(4) . ? C27 C32 1.402(4) . ? C28 C29 1.384(3) . ? C28 H28 0.9500 . ? C29 C30 1.388(4) . ? C29 H29 0.9500 . ? C30 C31 1.386(4) . ? C30 H30 0.9500 . ? C31 C32 1.396(3) . ? C31 H31 0.9500 . ? C32 C33 1.506(4) . ? C33 C34 1.529(3) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? N1 O2 1.225(3) . ? N1 O1 1.226(3) . ? N18 O5 1.224(3) . ? N18 O4 1.229(3) . ? 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 C2 C3 122.9(2) . . ? C7 C2 N1 118.4(2) . . ? C3 C2 N1 118.7(2) . . ? C2 C3 C4 117.7(2) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 121.1 . . ? C3 C4 C5 120.9(2) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 119.8(2) . . ? C6 C5 C8 120.7(2) . . ? C4 C5 C8 119.4(2) . . ? C5 C6 C7 120.3(2) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C2 C7 C6 118.4(2) . . ? C2 C7 H7 120.8 . . ? C6 C7 H7 120.8 . . ? F1 C8 C17 108.5(2) . . ? F1 C8 C5 107.48(19) . . ? C17 C8 C5 115.2(2) . . ? F1 C8 C9 103.77(18) . . ? C17 C8 C9 110.4(2) . . ? C5 C8 C9 110.7(2) . . ? O3 C9 C10 123.0(2) . . ? O3 C9 C8 120.6(2) . . ? C10 C9 C8 116.4(2) . . ? C15 C10 C11 120.4(2) . . ? C15 C10 C9 121.7(2) . . ? C11 C10 C9 117.9(2) . . ? C12 C11 C10 120.5(2) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 119.4(3) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C12 C13 C14 120.8(2) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C13 C14 C15 120.7(3) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C10 C15 C14 118.2(2) . . ? C10 C15 C16 121.1(2) . . ? C14 C15 C16 120.7(2) . . ? C15 C16 C17 112.6(2) . . ? C15 C16 H16A 109.1 . . ? C17 C16 H16A 109.1 . . ? C15 C16 H16B 109.1 . . ? C17 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? C8 C17 C16 111.1(2) . . ? C8 C17 H17A 109.4 . . ? C16 C17 H17A 109.4 . . ? C8 C17 H17B 109.4 . . ? C16 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? C24 C19 C20 122.4(2) . . ? C24 C19 N18 118.6(2) . . ? C20 C19 N18 119.0(2) . . ? C21 C20 C19 118.4(2) . . ? C21 C20 H20 120.8 . . ? C19 C20 H20 120.8 . . ? C20 C21 C22 120.6(2) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C23 C22 C21 119.1(2) . . ? C23 C22 C25 120.9(2) . . ? C21 C22 C25 119.9(2) . . ? C24 C23 C22 120.7(2) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C19 C24 C23 118.7(2) . . ? C19 C24 H24 120.6 . . ? C23 C24 H24 120.6 . . ? F2 C25 C34 108.4(2) . . ? F2 C25 C22 107.25(19) . . ? C34 C25 C22 114.9(2) . . ? F2 C25 C26 103.50(18) . . ? C34 C25 C26 110.8(2) . . ? C22 C25 C26 111.3(2) . . ? O6 C26 C27 122.9(2) . . ? O6 C26 C25 120.8(2) . . ? C27 C26 C25 116.2(2) . . ? C28 C27 C32 120.5(2) . . ? C28 C27 C26 117.7(2) . . ? C32 C27 C26 121.7(2) . . ? C29 C28 C27 120.6(2) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C28 C29 C30 118.9(2) . . ? C28 C29 H29 120.5 . . ? C30 C29 H29 120.5 . . ? C31 C30 C29 121.0(2) . . ? C31 C30 H30 119.5 . . ? C29 C30 H30 119.5 . . ? C30 C31 C32 120.7(2) . . ? C30 C31 H31 119.7 . . ? C32 C31 H31 119.7 . . ? C31 C32 C27 118.2(2) . . ? C31 C32 C33 120.8(2) . . ? C27 C32 C33 120.9(2) . . ? C32 C33 C34 112.5(2) . . ? C32 C33 H33A 109.1 . . ? C34 C33 H33A 109.1 . . ? C32 C33 H33B 109.1 . . ? C34 C33 H33B 109.1 . . ? H33A C33 H33B 107.8 . . ? C25 C34 C33 111.7(2) . . ? C25 C34 H34A 109.3 . . ? C33 C34 H34A 109.3 . . ? C25 C34 H34B 109.3 . . ? C33 C34 H34B 109.3 . . ? H34A C34 H34B 107.9 . . ? O2 N1 O1 124.0(2) . . ? O2 N1 C2 117.7(2) . . ? O1 N1 C2 118.3(2) . . ? O5 N18 O4 123.7(2) . . ? O5 N18 C19 118.3(2) . . ? O4 N18 C19 118.0(2) . . ? 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 C7 C2 C3 C4 0.2(4) . . . . ? N1 C2 C3 C4 -178.3(2) . . . . ? C2 C3 C4 C5 -0.7(4) . . . . ? C3 C4 C5 C6 0.8(4) . . . . ? C3 C4 C5 C8 177.6(2) . . . . ? C4 C5 C6 C7 -0.4(4) . . . . ? C8 C5 C6 C7 -177.1(2) . . . . ? C3 C2 C7 C6 0.2(4) . . . . ? N1 C2 C7 C6 178.8(2) . . . . ? C5 C6 C7 C2 -0.1(4) . . . . ? C6 C5 C8 F1 -149.9(2) . . . . ? C4 C5 C8 F1 33.4(3) . . . . ? C6 C5 C8 C17 -28.8(3) . . . . ? C4 C5 C8 C17 154.5(2) . . . . ? C6 C5 C8 C9 97.4(3) . . . . ? C4 C5 C8 C9 -79.3(3) . . . . ? F1 C8 C9 O3 -100.2(3) . . . . ? C17 C8 C9 O3 143.6(2) . . . . ? C5 C8 C9 O3 14.8(3) . . . . ? F1 C8 C9 C10 78.6(2) . . . . ? C17 C8 C9 C10 -37.6(3) . . . . ? C5 C8 C9 C10 -166.4(2) . . . . ? O3 C9 C10 C15 -171.0(3) . . . . ? C8 C9 C10 C15 10.2(4) . . . . ? O3 C9 C10 C11 8.1(4) . . . . ? C8 C9 C10 C11 -170.6(2) . . . . ? C15 C10 C11 C12 0.5(4) . . . . ? C9 C10 C11 C12 -178.7(3) . . . . ? C10 C11 C12 C13 1.1(4) . . . . ? C11 C12 C13 C14 -1.4(4) . . . . ? C12 C13 C14 C15 -0.1(4) . . . . ? C11 C10 C15 C14 -1.9(4) . . . . ? C9 C10 C15 C14 177.3(2) . . . . ? C11 C10 C15 C16 177.8(2) . . . . ? C9 C10 C15 C16 -3.1(4) . . . . ? C13 C14 C15 C10 1.6(4) . . . . ? C13 C14 C15 C16 -178.0(2) . . . . ? C10 C15 C16 C17 23.7(3) . . . . ? C14 C15 C16 C17 -156.7(2) . . . . ? F1 C8 C17 C16 -55.0(3) . . . . ? C5 C8 C17 C16 -175.5(2) . . . . ? C9 C8 C17 C16 58.1(3) . . . . ? C15 C16 C17 C8 -51.4(3) . . . . ? C24 C19 C20 C21 -0.4(4) . . . . ? N18 C19 C20 C21 -179.9(2) . . . . ? C19 C20 C21 C22 -0.2(4) . . . . ? C20 C21 C22 C23 0.8(4) . . . . ? C20 C21 C22 C25 178.2(2) . . . . ? C21 C22 C23 C24 -1.0(4) . . . . ? C25 C22 C23 C24 -178.3(2) . . . . ? C20 C19 C24 C23 0.3(4) . . . . ? N18 C19 C24 C23 179.8(2) . . . . ? C22 C23 C24 C19 0.4(4) . . . . ? C23 C22 C25 F2 -148.1(2) . . . . ? C21 C22 C25 F2 34.6(3) . . . . ? C23 C22 C25 C34 -27.6(4) . . . . ? C21 C22 C25 C34 155.1(2) . . . . ? C23 C22 C25 C26 99.3(3) . . . . ? C21 C22 C25 C26 -78.0(3) . . . . ? F2 C25 C26 O6 -99.5(3) . . . . ? C34 C25 C26 O6 144.6(2) . . . . ? C22 C25 C26 O6 15.5(3) . . . . ? F2 C25 C26 C27 79.2(2) . . . . ? C34 C25 C26 C27 -36.8(3) . . . . ? C22 C25 C26 C27 -165.8(2) . . . . ? O6 C26 C27 C28 7.4(4) . . . . ? C25 C26 C27 C28 -171.3(2) . . . . ? O6 C26 C27 C32 -170.0(3) . . . . ? C25 C26 C27 C32 11.3(3) . . . . ? C32 C27 C28 C29 0.7(4) . . . . ? C26 C27 C28 C29 -176.7(2) . . . . ? C27 C28 C29 C30 1.6(4) . . . . ? C28 C29 C30 C31 -2.5(4) . . . . ? C29 C30 C31 C32 1.1(4) . . . . ? C30 C31 C32 C27 1.3(4) . . . . ? C30 C31 C32 C33 -177.8(3) . . . . ? C28 C27 C32 C31 -2.2(4) . . . . ? C26 C27 C32 C31 175.2(2) . . . . ? C28 C27 C32 C33 177.0(2) . . . . ? C26 C27 C32 C33 -5.7(4) . . . . ? C31 C32 C33 C34 -155.3(2) . . . . ? C27 C32 C33 C34 25.6(3) . . . . ? F2 C25 C34 C33 -55.8(3) . . . . ? C22 C25 C34 C33 -175.7(2) . . . . ? C26 C25 C34 C33 57.1(3) . . . . ? C32 C33 C34 C25 -51.7(3) . . . . ? C7 C2 N1 O2 -13.2(3) . . . . ? C3 C2 N1 O2 165.5(2) . . . . ? C7 C2 N1 O1 166.9(3) . . . . ? C3 C2 N1 O1 -14.5(4) . . . . ? C24 C19 N18 O5 170.6(3) . . . . ? C20 C19 N18 O5 -9.8(4) . . . . ? C24 C19 N18 O4 -9.4(4) . . . . ? C20 C19 N18 O4 170.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 30.06 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.456 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.066