# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H12 F2 O3' _chemical_formula_sum 'C19 H12 F2 O3' _chemical_formula_weight 326.29 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' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 13.4533(5) _cell_length_b 9.8330(4) _cell_length_c 22.8428(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.222(5) _cell_angle_gamma 90.00 _cell_volume 3017.0(2) _cell_formula_units_Z 8 _cell_measurement_temperature 130(1) _cell_measurement_reflns_used 10084 _cell_measurement_theta_min 3.2875 _cell_measurement_theta_max 73.5346 _exptl_crystal_description prism _exptl_crystal_colour light-blue _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.961 _exptl_absorpt_correction_T_min 0.77401 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.43 (release 21-10-2010 CrysAlis171 .NET) (compiled Oct 21 2010,17:48:23) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(1) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset), Atlas' _diffrn_detector_area_resol_mean 10.5357 _diffrn_measurement_method \w-scan _diffrn_reflns_number 12858 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 73.69 _reflns_number_total 7066 _reflns_number_gt 6851 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis Pro (Agilent Technologies (2011))' _computing_cell_refinement 'CrysAlis Pro (Agilent Technologies (2011))' _computing_data_reduction 'CrysAlis Pro (Agilent Technologies (2011))' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0654P)^2^+0.1673P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.15(8) _refine_ls_number_reflns 7066 _refine_ls_number_parameters 900 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0341 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0922 _refine_ls_wR_factor_gt 0.0909 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 C1A C 1.14729(16) 0.6501(2) -0.03090(9) 0.0248(4) Uani 1 1 d . . . C2A C 1.08684(18) 0.7214(2) -0.07243(11) 0.0355(5) Uani 1 1 d . . . H2A H 1.0113 0.7053 -0.0752 0.053 Uiso 1 1 d R . . C3A C 1.1252(2) 0.8183(3) -0.10850(11) 0.0408(6) Uani 1 1 d . . . H3A H 1.0803 0.8634 -0.1341 0.047 Uiso 1 1 d R . . C4A C 1.22619(19) 0.8449(2) -0.10275(10) 0.0321(5) Uani 1 1 d . . . F4A F 1.26408(12) 0.94300(16) -0.13694(6) 0.0426(3) Uani 1 1 d . . . C5A C 1.28870(17) 0.7783(2) -0.06298(10) 0.0307(5) Uani 1 1 d . . . H5A H 1.3536 0.8021 -0.0611 0.031 Uiso 1 1 d R . . C6A C 1.24911(16) 0.6797(2) -0.02748(9) 0.0283(4) Uani 1 1 d . . . H6A H 1.2967 0.6298 0.0010 0.029 Uiso 1 1 d R . . C7A C 1.10371(16) 0.5471(2) 0.00733(9) 0.0254(4) Uani 1 1 d . . . C8A C 1.01157(16) 0.4882(2) -0.00775(10) 0.0315(5) Uani 1 1 d . . . H8A H 0.9788 0.5049 -0.0430 0.043 Uiso 1 1 d R . . C9A C 0.96936(17) 0.3934(2) 0.02807(11) 0.0331(5) Uani 1 1 d . . . O9A O 0.88021(13) 0.3432(2) 0.00800(9) 0.0460(5) Uani 1 1 d . . . H9A H 0.863(3) 0.286(4) 0.0370(19) 0.072(12) Uiso 1 1 d . . . C10A C 1.01806(15) 0.3516(2) 0.08134(9) 0.0253(4) Uani 1 1 d . . . C19A C 0.96662(16) 0.2570(2) 0.11891(9) 0.0262(4) Uani 1 1 d . . . O20A O 0.88155(12) 0.21343(18) 0.10460(8) 0.0351(4) Uani 1 1 d . . . O21A O 1.01192(12) 0.22050(19) 0.16844(8) 0.0376(4) Uani 1 1 d . . . H21A H 0.953(5) 0.136(7) 0.188(3) 0.17(3) Uiso 1 1 d . . . C11A C 1.11436(15) 0.4074(2) 0.09631(9) 0.0228(4) Uani 1 1 d . . . C12A C 1.15376(15) 0.5035(2) 0.06005(9) 0.0242(4) Uani 1 1 d . . . H12A H 1.2188 0.5370 0.0708 0.042 Uiso 1 1 d R . . C13A C 1.17771(14) 0.3676(2) 0.14937(9) 0.0222(4) Uani 1 1 d . . . C14A C 1.22266(16) 0.2393(2) 0.15293(10) 0.0320(4) Uani 1 1 d . . . H14A H 1.2184 0.1740 0.1200 0.030 Uiso 1 1 d R . . C15A C 1.28560(16) 0.2034(2) 0.20062(11) 0.0344(5) Uani 1 1 d . . . H15A H 1.3197 0.1148 0.2017 0.031 Uiso 1 1 d R . . C16A C 1.30271(16) 0.2965(3) 0.24445(10) 0.0320(5) Uani 1 1 d . . . F16A F 1.36637(12) 0.26397(19) 0.29047(7) 0.0473(4) Uani 1 1 d . . . C17A C 1.26139(16) 0.4250(3) 0.24277(9) 0.0340(5) Uani 1 1 d . . . H17A H 1.2760 0.4858 0.2744 0.048 Uiso 1 1 d R . . C18A C 1.19829(15) 0.4593(2) 0.19463(9) 0.0278(4) Uani 1 1 d . . . H18A H 1.1684 0.5454 0.1913 0.033 Uiso 1 1 d R . . C1B C 0.64043(16) -0.3891(2) 0.36260(9) 0.0256(4) Uani 1 1 d . . . C2B C 0.70066(17) -0.4628(2) 0.40342(10) 0.0312(5) Uani 1 1 d . . . H2B H 0.7679 -0.4476 0.4093 0.030 Uiso 1 1 d R . . C3B C 0.66095(19) -0.5627(2) 0.43806(10) 0.0354(5) Uani 1 1 d . . . H3B H 0.7000 -0.6146 0.4657 0.044 Uiso 1 1 d R . . C4B C 0.56088(19) -0.5885(2) 0.43149(9) 0.0318(5) Uani 1 1 d . . . F4B F 0.52168(12) -0.68726(17) 0.46430(6) 0.0440(4) Uani 1 1 d . . . C5B C 0.49764(17) -0.5176(2) 0.39270(10) 0.0308(4) Uani 1 1 d . . . H5B H 0.4271 -0.5387 0.3835 0.035 Uiso 1 1 d R . . C6B C 0.53889(17) -0.4180(2) 0.35850(9) 0.0284(4) Uani 1 1 d . . . H6B H 0.4947 -0.3648 0.3353 0.035 Uiso 1 1 d R . . C7B C 0.68411(16) -0.2854(2) 0.32448(9) 0.0253(4) Uani 1 1 d . . . C8B C 0.77416(16) -0.2244(2) 0.34043(10) 0.0299(4) Uani 1 1 d . . . H8B H 0.8148 -0.2430 0.3767 0.038 Uiso 1 1 d R . . C9B C 0.81680(15) -0.1306(2) 0.30385(10) 0.0297(4) Uani 1 1 d . . . O9B O 0.90623(13) -0.0793(2) 0.32325(8) 0.0429(4) Uani 1 1 d . . . H9B H 0.930(2) -0.028(3) 0.2976(14) 0.041(8) Uiso 1 1 d . . . C10B C 0.76821(16) -0.0919(2) 0.24940(9) 0.0256(4) Uani 1 1 d . . . O20B O 0.90517(12) 0.04572(18) 0.22586(8) 0.0366(4) Uani 1 1 d . . . O21B O 0.77644(12) 0.03420(18) 0.16133(7) 0.0344(4) Uani 1 1 d . . . H21B H 0.813(2) 0.094(3) 0.1425(14) 0.037(7) Uiso 1 1 d . . . C11B C 0.67419(15) -0.1517(2) 0.23431(9) 0.0229(4) Uani 1 1 d . . . C12B C 0.63541(15) -0.2466(2) 0.27107(9) 0.0238(4) Uani 1 1 d . . . H12B H 0.5696 -0.2898 0.2586 0.019 Uiso 1 1 d R . . C13B C 0.61099(15) -0.1176(2) 0.18004(9) 0.0227(4) Uani 1 1 d . . . C14B C 0.56657(15) 0.0099(2) 0.17301(9) 0.0275(4) Uani 1 1 d . . . H14B H 0.5856 0.0781 0.2034 0.031 Uiso 1 1 d R . . C15B C 0.50126(15) 0.0373(2) 0.12521(10) 0.0302(4) Uani 1 1 d . . . H15B H 0.4714 0.1236 0.1181 0.034 Uiso 1 1 d R . . C16B C 0.48264(16) -0.0646(3) 0.08496(9) 0.0291(4) Uani 1 1 d . . . F16B F 0.41579(11) -0.04005(16) 0.03874(6) 0.0408(3) Uani 1 1 d . . . C17B C 0.52446(16) -0.1915(2) 0.08985(9) 0.0294(4) Uani 1 1 d . . . H17B H 0.5094 -0.2588 0.0632 0.047 Uiso 1 1 d R . . C18B C 0.58959(14) -0.2180(2) 0.13826(9) 0.0255(4) Uani 1 1 d . . . H18B H 0.6199 -0.3055 0.1430 0.028 Uiso 1 1 d R . . C19B C 0.82074(16) 0.0008(2) 0.21145(10) 0.0258(4) Uani 1 1 d . . . C1C C 1.13419(16) -0.1358(2) 0.46906(9) 0.0257(4) Uani 1 1 d . . . C2C C 1.08013(18) -0.1852(3) 0.41965(10) 0.0341(5) Uani 1 1 d . . . H2C H 1.0107 -0.1568 0.4108 0.032 Uiso 1 1 d R . . C3C C 1.1198(2) -0.2825(3) 0.38391(10) 0.0401(6) Uani 1 1 d . . . H3C H 1.0794 -0.3132 0.3510 0.052 Uiso 1 1 d R . . C4C C 1.2142(2) -0.3299(3) 0.39778(10) 0.0357(5) Uani 1 1 d . . . F4C F 1.25303(13) -0.42758(19) 0.36366(7) 0.0506(4) Uani 1 1 d . . . C5C C 1.2711(2) -0.2825(3) 0.44508(11) 0.0379(5) Uani 1 1 d . . . H5C H 1.3361 -0.3098 0.4487 0.049 Uiso 1 1 d R . . C6C C 1.23020(19) -0.1859(3) 0.48092(11) 0.0359(5) Uani 1 1 d . . . H6C H 1.2725 -0.1490 0.5153 0.055 Uiso 1 1 d R . . C7C C 1.08894(16) -0.0365(2) 0.50885(9) 0.0248(4) Uani 1 1 d . . . C8C C 0.98744(17) -0.0096(2) 0.50542(10) 0.0303(4) Uani 1 1 d . . . H8C H 0.9424 -0.0424 0.4756 0.053 Uiso 1 1 d R . . C9C C 0.94522(15) 0.0786(2) 0.54489(10) 0.0304(4) Uani 1 1 d . . . O9C O 0.84573(12) 0.0985(2) 0.53682(8) 0.0434(4) Uani 1 1 d . . . H9C H 0.832(4) 0.163(6) 0.569(2) 0.099(15) Uiso 1 1 d . . . C10C C 1.00382(15) 0.1414(2) 0.59020(9) 0.0234(4) Uani 1 1 d . . . C19C C 0.95656(16) 0.2439(2) 0.62674(9) 0.0250(4) Uani 1 1 d . . . O20C O 0.86442(11) 0.25508(19) 0.62650(8) 0.0379(4) Uani 1 1 d . . . O21C O 1.01514(11) 0.32499(16) 0.65733(7) 0.0311(3) Uani 1 1 d . . . H21C H 0.975(3) 0.391(5) 0.682(2) 0.084(14) Uiso 1 1 d . . . C11C C 1.10719(15) 0.10906(19) 0.59580(8) 0.0217(4) Uani 1 1 d . . . C12C C 1.14728(15) 0.0264(2) 0.55427(9) 0.0222(4) Uani 1 1 d . . . H12C H 1.2145 0.0129 0.5573 0.027 Uiso 1 1 d R . . C13C C 1.17340(14) 0.14472(19) 0.64766(8) 0.0210(4) Uani 1 1 d . . . C14C C 1.14496(15) 0.1166(2) 0.70414(9) 0.0248(4) Uani 1 1 d . . . H14C H 1.0822 0.0830 0.7089 0.040 Uiso 1 1 d R . . C15C C 1.20951(16) 0.1371(2) 0.75289(9) 0.0301(4) Uani 1 1 d . . . H15C H 1.1904 0.1237 0.7918 0.038 Uiso 1 1 d R . . C16C C 1.30294(17) 0.1874(2) 0.74376(10) 0.0294(4) Uani 1 1 d . . . F16C F 1.36671(12) 0.20786(17) 0.79112(6) 0.0443(4) Uani 1 1 d . . . C17C C 1.33518(15) 0.2154(2) 0.68915(10) 0.0284(4) Uani 1 1 d . . . H17C H 1.4041 0.2509 0.6843 0.036 Uiso 1 1 d R . . C18C C 1.26951(14) 0.19434(19) 0.64082(8) 0.0236(4) Uani 1 1 d . . . H18C H 1.2897 0.2164 0.6029 0.032 Uiso 1 1 d R . . C1D C 0.64385(16) 0.8987(2) 0.87074(9) 0.0257(4) Uani 1 1 d . . . C2D C 0.69055(17) 0.9325(2) 0.92489(9) 0.0302(4) Uani 1 1 d . . . H2D H 0.7481 0.8899 0.9374 0.036 Uiso 1 1 d R . . C3D C 0.64933(18) 1.0260(2) 0.96217(10) 0.0336(5) Uani 1 1 d . . . H3D H 0.6773 1.0486 1.0020 0.035 Uiso 1 1 d R . . C4D C 0.55993(18) 1.0849(2) 0.94472(9) 0.0297(4) Uani 1 1 d . . . F4D F 0.52004(11) 1.17778(15) 0.98038(6) 0.0381(3) Uani 1 1 d . . . C5D C 0.50913(17) 1.0531(2) 0.89254(10) 0.0300(4) Uani 1 1 d . . . H5D H 0.4457 1.0936 0.8803 0.028 Uiso 1 1 d R . . C6D C 0.55185(16) 0.9603(2) 0.85556(9) 0.0272(4) Uani 1 1 d . . . H6D H 0.5164 0.9435 0.8167 0.032 Uiso 1 1 d R . . C7D C 0.69069(16) 0.8025(2) 0.83046(9) 0.0252(4) Uani 1 1 d . . . C8D C 0.79229(17) 0.7767(2) 0.83544(10) 0.0321(5) Uani 1 1 d . . . H8D H 0.8345 0.8193 0.8630 0.031 Uiso 1 1 d R . . C9D C 0.83642(16) 0.6873(2) 0.79747(10) 0.0315(4) Uani 1 1 d . . . O9D O 0.93571(12) 0.6679(2) 0.80754(9) 0.0459(5) Uani 1 1 d . . . H9D H 0.960(3) 0.609(5) 0.7776(18) 0.072(11) Uiso 1 1 d . . . C10D C 0.78008(16) 0.6226(2) 0.75135(10) 0.0266(4) Uani 1 1 d . . . C19D C 0.82870(16) 0.5169(2) 0.71755(10) 0.0265(4) Uani 1 1 d . . . O20D O 0.92067(12) 0.5046(2) 0.71858(9) 0.0411(4) Uani 1 1 d . . . O21D O 0.77069(11) 0.43440(15) 0.68711(8) 0.0306(3) Uani 1 1 d . . . H21D H 0.807(2) 0.380(3) 0.6663(12) 0.031(7) Uiso 1 1 d . . . C11D C 0.67727(15) 0.6554(2) 0.74374(9) 0.0223(4) Uani 1 1 d . . . C12D C 0.63491(15) 0.7397(2) 0.78402(9) 0.0225(4) Uani 1 1 d . . . H12D H 0.5612 0.7652 0.7776 0.032 Uiso 1 1 d R . . C13D C 0.61364(15) 0.61531(19) 0.69105(9) 0.0225(4) Uani 1 1 d . . . C14D C 0.64588(15) 0.6377(2) 0.63435(9) 0.0257(4) Uani 1 1 d . . . H14D H 0.7120 0.6775 0.6316 0.028 Uiso 1 1 d R . . C15D C 0.58479(17) 0.6110(2) 0.58496(9) 0.0293(4) Uani 1 1 d . . . H15D H 0.6052(18) 0.631(3) 0.5472(12) 0.028 Uiso 1 1 d . . . C16D C 0.49041(17) 0.5634(2) 0.59290(10) 0.0296(5) Uani 1 1 d . . . F16D F 0.42862(11) 0.53679(17) 0.54450(6) 0.0417(3) Uani 1 1 d . . . C17D C 0.45448(15) 0.5407(2) 0.64724(9) 0.0277(4) Uani 1 1 d . . . H17D H 0.3877 0.5074 0.6511 0.039 Uiso 1 1 d R . . C18D C 0.51723(14) 0.56684(19) 0.69662(9) 0.0244(4) Uani 1 1 d . . . H18D H 0.4957 0.5545 0.7344 0.018 Uiso 1 1 d 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 C1A 0.0285(10) 0.0245(9) 0.0211(9) -0.0023(8) -0.0009(7) 0.0006(8) C2A 0.0315(11) 0.0376(11) 0.0364(12) 0.0089(10) -0.0071(9) -0.0036(9) C3A 0.0403(13) 0.0430(13) 0.0374(12) 0.0151(11) -0.0109(10) -0.0021(10) C4A 0.0431(13) 0.0272(10) 0.0263(10) 0.0050(8) 0.0037(9) -0.0031(9) F4A 0.0495(8) 0.0396(7) 0.0390(8) 0.0169(6) 0.0044(6) -0.0058(6) C5A 0.0304(11) 0.0308(10) 0.0310(10) 0.0025(9) 0.0035(9) -0.0022(8) C6A 0.0290(10) 0.0299(10) 0.0257(9) 0.0034(8) 0.0001(8) 0.0007(8) C7A 0.0274(11) 0.0264(9) 0.0220(9) -0.0015(8) -0.0019(8) 0.0008(8) C8A 0.0297(11) 0.0372(11) 0.0264(10) 0.0062(8) -0.0072(8) -0.0038(9) C9A 0.0272(11) 0.0382(11) 0.0332(11) 0.0027(9) -0.0041(8) -0.0067(9) O9A 0.0303(8) 0.0618(11) 0.0441(9) 0.0203(9) -0.0149(7) -0.0201(8) C10A 0.0234(10) 0.0260(9) 0.0262(10) 0.0004(8) -0.0010(7) -0.0006(8) C19A 0.0251(10) 0.0240(9) 0.0295(10) 0.0006(8) 0.0006(8) -0.0003(7) O20A 0.0237(7) 0.0442(9) 0.0367(8) 0.0101(7) -0.0025(6) -0.0094(6) O21A 0.0292(8) 0.0452(9) 0.0377(9) 0.0148(7) -0.0051(7) -0.0122(7) C11A 0.0238(10) 0.0225(8) 0.0222(9) -0.0024(7) 0.0008(7) -0.0004(7) C12A 0.0225(9) 0.0253(9) 0.0244(9) -0.0012(8) -0.0033(7) -0.0024(7) C13A 0.0199(9) 0.0238(9) 0.0227(9) 0.0023(7) 0.0007(7) -0.0034(7) C14A 0.0331(11) 0.0233(9) 0.0387(11) -0.0015(8) -0.0062(9) -0.0032(8) C15A 0.0307(10) 0.0268(9) 0.0450(12) 0.0111(9) -0.0043(9) -0.0020(8) C16A 0.0224(10) 0.0467(12) 0.0268(10) 0.0135(9) -0.0004(8) -0.0012(9) F16A 0.0379(7) 0.0691(10) 0.0339(7) 0.0187(7) -0.0078(6) 0.0028(7) C17A 0.0328(11) 0.0479(12) 0.0209(9) -0.0052(9) -0.0013(8) 0.0031(9) C18A 0.0261(9) 0.0319(10) 0.0255(9) -0.0019(8) 0.0030(7) 0.0046(8) C1B 0.0309(10) 0.0241(9) 0.0216(9) 0.0010(8) -0.0001(8) 0.0003(8) C2B 0.0327(11) 0.0325(10) 0.0278(10) 0.0059(8) -0.0048(8) -0.0025(8) C3B 0.0433(13) 0.0347(11) 0.0275(11) 0.0088(9) -0.0040(9) 0.0000(9) C4B 0.0436(13) 0.0300(10) 0.0220(9) 0.0059(8) 0.0052(8) -0.0037(9) F4B 0.0514(8) 0.0457(8) 0.0352(7) 0.0182(6) 0.0061(6) -0.0061(7) C5B 0.0291(10) 0.0348(11) 0.0290(10) 0.0038(9) 0.0043(8) -0.0008(9) C6B 0.0293(10) 0.0302(10) 0.0254(10) 0.0050(8) -0.0006(8) 0.0017(8) C7B 0.0257(10) 0.0241(9) 0.0259(10) 0.0021(8) 0.0002(8) 0.0015(7) C8B 0.0290(10) 0.0311(10) 0.0286(10) 0.0062(8) -0.0068(8) -0.0002(8) C9B 0.0223(10) 0.0320(10) 0.0339(11) 0.0055(8) -0.0057(8) -0.0040(8) O9B 0.0293(8) 0.0536(10) 0.0440(9) 0.0197(9) -0.0143(7) -0.0164(8) C10B 0.0242(10) 0.0256(9) 0.0266(9) 0.0033(8) -0.0013(8) 0.0001(7) O20B 0.0243(8) 0.0450(9) 0.0397(9) 0.0136(7) -0.0048(6) -0.0102(6) O21B 0.0289(8) 0.0415(8) 0.0322(8) 0.0126(7) -0.0039(6) -0.0114(7) C11B 0.0227(9) 0.0223(8) 0.0234(10) -0.0007(7) 0.0000(7) 0.0013(7) C12B 0.0233(10) 0.0242(9) 0.0237(9) 0.0009(7) -0.0015(7) -0.0019(7) C13B 0.0198(9) 0.0263(9) 0.0220(9) 0.0018(7) 0.0006(7) -0.0035(7) C14B 0.0286(10) 0.0232(9) 0.0304(10) 0.0003(8) -0.0024(8) -0.0035(7) C15B 0.0282(10) 0.0270(9) 0.0348(10) 0.0113(8) -0.0020(8) -0.0017(8) C16B 0.0249(10) 0.0413(11) 0.0202(9) 0.0093(8) -0.0065(8) -0.0074(8) F16B 0.0364(7) 0.0532(8) 0.0308(7) 0.0135(6) -0.0155(6) -0.0068(6) C17B 0.0317(10) 0.0361(10) 0.0201(9) -0.0026(8) -0.0003(7) -0.0046(8) C18B 0.0242(9) 0.0281(9) 0.0241(9) -0.0023(7) 0.0007(7) 0.0007(7) C19B 0.0202(9) 0.0266(9) 0.0303(10) 0.0023(8) -0.0013(8) 0.0004(8) C1C 0.0302(10) 0.0271(9) 0.0198(9) 0.0004(8) 0.0006(8) -0.0018(8) C2C 0.0331(11) 0.0441(12) 0.0246(10) -0.0054(9) -0.0023(8) 0.0015(9) C3C 0.0455(13) 0.0494(14) 0.0249(10) -0.0137(10) -0.0027(9) -0.0013(10) C4C 0.0500(14) 0.0327(11) 0.0252(10) -0.0058(9) 0.0093(9) 0.0030(10) F4C 0.0644(10) 0.0531(9) 0.0350(8) -0.0202(7) 0.0097(7) 0.0118(8) C5C 0.0384(13) 0.0446(13) 0.0305(11) -0.0079(10) 0.0007(9) 0.0123(10) C6C 0.0366(12) 0.0390(12) 0.0315(11) -0.0118(9) -0.0044(9) 0.0069(9) C7C 0.0279(10) 0.0259(9) 0.0203(9) 0.0005(7) -0.0025(7) 0.0012(8) C8C 0.0261(10) 0.0379(11) 0.0261(10) -0.0086(8) -0.0058(8) 0.0006(8) C9C 0.0218(10) 0.0369(11) 0.0318(11) -0.0046(9) -0.0049(8) 0.0022(8) O9C 0.0237(8) 0.0601(11) 0.0452(9) -0.0233(9) -0.0091(7) 0.0082(7) C10C 0.0190(9) 0.0249(9) 0.0261(10) -0.0023(7) -0.0011(7) 0.0006(7) C19C 0.0225(10) 0.0266(9) 0.0256(9) -0.0002(8) -0.0004(7) -0.0005(8) O20C 0.0204(7) 0.0441(9) 0.0488(10) -0.0206(8) -0.0009(6) 0.0022(6) O21C 0.0205(7) 0.0316(7) 0.0411(9) -0.0120(6) 0.0005(6) 0.0010(6) C11C 0.0229(9) 0.0209(8) 0.0212(9) 0.0012(7) -0.0010(7) -0.0012(7) C12C 0.0207(9) 0.0229(9) 0.0227(9) 0.0018(7) -0.0009(7) 0.0018(7) C13C 0.0209(9) 0.0199(8) 0.0219(9) -0.0026(7) -0.0015(7) 0.0023(7) C14C 0.0239(9) 0.0270(9) 0.0233(9) -0.0009(7) -0.0001(7) -0.0016(7) C15C 0.0359(11) 0.0323(10) 0.0216(9) 0.0000(8) -0.0022(8) -0.0001(8) C16C 0.0303(11) 0.0284(10) 0.0280(10) -0.0046(8) -0.0106(8) 0.0005(8) F16C 0.0423(8) 0.0572(9) 0.0315(7) -0.0055(6) -0.0169(6) -0.0055(7) C17C 0.0215(9) 0.0271(9) 0.0359(10) -0.0044(8) -0.0045(8) 0.0007(7) C18C 0.0221(9) 0.0245(8) 0.0240(9) -0.0013(7) 0.0006(7) 0.0026(7) C1D 0.0303(10) 0.0258(9) 0.0207(9) -0.0006(8) -0.0019(7) 0.0004(8) C2D 0.0319(11) 0.0346(10) 0.0231(9) -0.0034(8) -0.0065(8) 0.0059(8) C3D 0.0391(12) 0.0378(11) 0.0232(10) -0.0062(8) -0.0044(8) 0.0007(9) C4D 0.0375(11) 0.0280(10) 0.0239(10) -0.0042(8) 0.0050(8) 0.0008(8) F4D 0.0460(8) 0.0371(7) 0.0312(7) -0.0109(6) 0.0021(6) 0.0078(6) C5D 0.0316(11) 0.0308(10) 0.0274(10) -0.0024(8) -0.0009(8) 0.0042(8) C6D 0.0300(10) 0.0291(10) 0.0221(9) -0.0023(7) -0.0033(8) 0.0019(8) C7D 0.0284(10) 0.0257(9) 0.0212(9) 0.0004(8) -0.0011(8) 0.0017(8) C8D 0.0305(11) 0.0357(11) 0.0292(10) -0.0095(9) -0.0063(8) 0.0000(8) C9D 0.0226(10) 0.0372(11) 0.0339(11) -0.0060(9) -0.0048(8) 0.0031(8) O9D 0.0229(8) 0.0606(11) 0.0529(11) -0.0286(9) -0.0105(7) 0.0086(7) C10D 0.0269(10) 0.0255(9) 0.0273(10) -0.0027(8) -0.0005(8) 0.0011(8) C19D 0.0201(10) 0.0296(10) 0.0297(10) -0.0030(8) -0.0003(7) -0.0006(8) O20D 0.0216(7) 0.0501(10) 0.0511(10) -0.0228(8) -0.0029(7) 0.0025(7) O21D 0.0209(7) 0.0267(7) 0.0443(9) -0.0116(6) 0.0013(6) -0.0005(6) C11D 0.0219(9) 0.0203(8) 0.0245(9) 0.0015(7) -0.0004(7) -0.0029(7) C12D 0.0226(9) 0.0227(8) 0.0218(9) 0.0016(7) -0.0008(7) 0.0018(7) C13D 0.0228(9) 0.0198(8) 0.0248(9) -0.0024(7) -0.0008(7) 0.0026(7) C14D 0.0276(10) 0.0238(8) 0.0255(9) -0.0008(7) 0.0007(7) -0.0008(7) C15D 0.0364(11) 0.0285(9) 0.0227(9) -0.0010(8) -0.0001(8) 0.0020(8) C16D 0.0331(11) 0.0279(10) 0.0264(10) -0.0072(8) -0.0115(8) 0.0054(8) F16D 0.0408(8) 0.0513(8) 0.0312(7) -0.0088(6) -0.0159(6) 0.0002(6) C17D 0.0225(9) 0.0271(9) 0.0328(10) -0.0049(8) -0.0036(8) -0.0004(8) C18D 0.0219(9) 0.0250(9) 0.0261(9) -0.0039(7) -0.0004(7) 0.0013(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1A C6A 1.398(3) . ? C1A C2A 1.402(3) . ? C1A C7A 1.480(3) . ? C2A C3A 1.379(3) . ? C2A H2A 1.0264 . ? C3A C4A 1.383(4) . ? C3A H3A 0.9294 . ? C4A F4A 1.358(3) . ? C4A C5A 1.370(3) . ? C5A C6A 1.389(3) . ? C5A H5A 0.9032 . ? C6A H6A 1.0139 . ? C7A C8A 1.393(3) . ? C7A C12A 1.413(3) . ? C8A C9A 1.383(3) . ? C8A H8A 0.9097 . ? C9A O9A 1.353(3) . ? C9A C10A 1.410(3) . ? O9A H9A 0.91(4) . ? C10A C11A 1.431(3) . ? C10A C19A 1.465(3) . ? C19A O20A 1.248(3) . ? C19A O21A 1.305(3) . ? O21A H21A 1.25(7) . ? C11A C12A 1.382(3) . ? C11A C13A 1.494(3) . ? C12A H12A 0.9533 . ? C13A C18A 1.388(3) . ? C13A C14A 1.400(3) . ? C14A C15A 1.387(3) . ? C14A H14A 0.9890 . ? C15A C16A 1.367(4) . ? C15A H15A 0.9845 . ? C16A F16A 1.356(3) . ? C16A C17A 1.380(4) . ? C17A C18A 1.392(3) . ? C17A H17A 0.9496 . ? C18A H18A 0.9381 . ? C1B C6B 1.393(3) . ? C1B C2B 1.402(3) . ? C1B C7B 1.483(3) . ? C2B C3B 1.387(3) . ? C2B H2B 0.9197 . ? C3B C4B 1.370(4) . ? C3B H3B 0.9469 . ? C4B F4B 1.352(3) . ? C4B C5B 1.382(3) . ? C5B C6B 1.388(3) . ? C5B H5B 0.9821 . ? C6B H6B 0.9345 . ? C7B C8B 1.382(3) . ? C7B C12B 1.405(3) . ? C8B C9B 1.390(3) . ? C8B H8B 0.9843 . ? C9B O9B 1.356(3) . ? C9B C10B 1.424(3) . ? O9B H9B 0.85(3) . ? C10B C11B 1.419(3) . ? C10B C19B 1.467(3) . ? O20B C19B 1.246(3) . ? O20B H21A 1.42(7) . ? O21B C19B 1.303(3) . ? O21B H21B 0.89(3) . ? C11B C12B 1.378(3) . ? C11B C13B 1.501(3) . ? C12B H12B 1.0083 . ? C13B C18B 1.392(3) . ? C13B C14B 1.394(3) . ? C14B C15B 1.389(3) . ? C14B H14B 0.9897 . ? C15B C16B 1.373(3) . ? C15B H15B 0.9488 . ? C16B F16B 1.369(2) . ? C16B C17B 1.371(3) . ? C17B C18B 1.396(3) . ? C17B H17B 0.9135 . ? C18B H18B 0.9556 . ? C1C C6C 1.395(3) . ? C1C C2C 1.395(3) . ? C1C C7C 1.487(3) . ? C2C C3C 1.385(3) . ? C2C H2C 0.9846 . ? C3C C4C 1.373(4) . ? C3C H3C 0.9529 . ? C4C F4C 1.360(3) . ? C4C C5C 1.370(4) . ? C5C C6C 1.388(3) . ? C5C H5C 0.9136 . ? C6C H6C 1.0110 . ? C7C C8C 1.389(3) . ? C7C C12C 1.408(3) . ? C8C C9C 1.394(3) . ? C8C H8C 0.9436 . ? C9C O9C 1.355(3) . ? C9C C10C 1.408(3) . ? O9C H9C 0.99(5) . ? C10C C11C 1.425(3) . ? C10C C19C 1.475(3) . ? C19C O20C 1.244(3) . ? C19C O21C 1.297(3) . ? O21C H21C 1.03(5) . ? C11C C12C 1.382(3) . ? C11C C13C 1.484(3) . ? C12C H12C 0.9123 . ? C13C C14C 1.394(3) . ? C13C C18C 1.399(3) . ? C14C C15C 1.388(3) . ? C14C H14C 0.9187 . ? C15C C16C 1.377(3) . ? C15C H15C 0.9472 . ? C16C F16C 1.357(3) . ? C16C C17C 1.372(3) . ? C17C C18C 1.390(3) . ? C17C H17C 1.0022 . ? C18C H18C 0.9475 . ? C1D C2D 1.396(3) . ? C1D C6D 1.404(3) . ? C1D C7D 1.485(3) . ? C2D C3D 1.389(3) . ? C2D H2D 0.9127 . ? C3D C4D 1.374(3) . ? C3D H3D 0.9892 . ? C4D F4D 1.354(3) . ? C4D C5D 1.376(3) . ? C5D C6D 1.389(3) . ? C5D H5D 0.9688 . ? C6D H6D 0.9982 . ? C7D C8D 1.389(3) . ? C7D C12D 1.407(3) . ? C8D C9D 1.391(3) . ? C8D H8D 0.9232 . ? C9D O9D 1.356(3) . ? C9D C10D 1.414(3) . ? O9D H9D 0.96(4) . ? C10D C11D 1.421(3) . ? C10D C19D 1.470(3) . ? C19D O20D 1.242(3) . ? C19D O21D 1.300(3) . ? O21D H21D 0.88(3) . ? C11D C12D 1.384(3) . ? C11D C13D 1.490(3) . ? C12D H12D 1.0254 . ? C13D C18D 1.394(3) . ? C13D C14D 1.406(3) . ? C14D C15D 1.383(3) . ? C14D H14D 0.9768 . ? C15D C16D 1.375(3) . ? C15D H15D 0.94(3) . ? C16D F16D 1.371(2) . ? C16D C17D 1.375(3) . ? C17D C18D 1.394(3) . ? C17D H17D 0.9644 . ? C18D H18D 0.9342 . ? 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 C6A C1A C2A 117.6(2) . . ? C6A C1A C7A 121.93(19) . . ? C2A C1A C7A 120.5(2) . . ? C3A C2A C1A 121.9(2) . . ? C3A C2A H2A 118.1 . . ? C1A C2A H2A 120.0 . . ? C2A C3A C4A 118.2(2) . . ? C2A C3A H3A 117.0 . . ? C4A C3A H3A 124.8 . . ? F4A C4A C5A 119.0(2) . . ? F4A C4A C3A 118.6(2) . . ? C5A C4A C3A 122.4(2) . . ? C4A C5A C6A 118.7(2) . . ? C4A C5A H5A 117.6 . . ? C6A C5A H5A 123.7 . . ? C5A C6A C1A 121.3(2) . . ? C5A C6A H6A 117.6 . . ? C1A C6A H6A 121.1 . . ? C8A C7A C12A 117.37(19) . . ? C8A C7A C1A 120.97(19) . . ? C12A C7A C1A 121.66(19) . . ? C9A C8A C7A 121.5(2) . . ? C9A C8A H8A 116.7 . . ? C7A C8A H8A 121.6 . . ? O9A C9A C8A 115.5(2) . . ? O9A C9A C10A 123.1(2) . . ? C8A C9A C10A 121.4(2) . . ? C9A O9A H9A 103(3) . . ? C9A C10A C11A 117.71(19) . . ? C9A C10A C19A 118.59(19) . . ? C11A C10A C19A 123.68(19) . . ? O20A C19A O21A 120.63(19) . . ? O20A C19A C10A 121.4(2) . . ? O21A C19A C10A 118.00(19) . . ? C19A O21A H21A 103(3) . . ? C12A C11A C10A 119.46(19) . . ? C12A C11A C13A 116.41(18) . . ? C10A C11A C13A 124.13(18) . . ? C11A C12A C7A 122.53(19) . . ? C11A C12A H12A 117.3 . . ? C7A C12A H12A 120.1 . . ? C18A C13A C14A 118.35(19) . . ? C18A C13A C11A 121.01(18) . . ? C14A C13A C11A 120.53(18) . . ? C15A C14A C13A 121.2(2) . . ? C15A C14A H14A 116.0 . . ? C13A C14A H14A 122.4 . . ? C16A C15A C14A 118.4(2) . . ? C16A C15A H15A 121.0 . . ? C14A C15A H15A 120.5 . . ? F16A C16A C15A 118.9(2) . . ? F16A C16A C17A 118.3(2) . . ? C15A C16A C17A 122.8(2) . . ? C16A C17A C18A 118.1(2) . . ? C16A C17A H17A 119.3 . . ? C18A C17A H17A 122.6 . . ? C13A C18A C17A 121.2(2) . . ? C13A C18A H18A 117.3 . . ? C17A C18A H18A 121.5 . . ? C6B C1B C2B 117.86(19) . . ? C6B C1B C7B 121.32(19) . . ? C2B C1B C7B 120.8(2) . . ? C3B C2B C1B 121.2(2) . . ? C3B C2B H2B 116.1 . . ? C1B C2B H2B 122.7 . . ? C4B C3B C2B 118.4(2) . . ? C4B C3B H3B 118.5 . . ? C2B C3B H3B 123.0 . . ? F4B C4B C3B 118.9(2) . . ? F4B C4B C5B 118.2(2) . . ? C3B C4B C5B 122.9(2) . . ? C4B C5B C6B 117.7(2) . . ? C4B C5B H5B 125.7 . . ? C6B C5B H5B 116.2 . . ? C5B C6B C1B 121.8(2) . . ? C5B C6B H6B 117.0 . . ? C1B C6B H6B 120.9 . . ? C8B C7B C12B 118.04(19) . . ? C8B C7B C1B 120.93(19) . . ? C12B C7B C1B 121.04(19) . . ? C7B C8B C9B 120.98(19) . . ? C7B C8B H8B 125.4 . . ? C9B C8B H8B 113.6 . . ? O9B C9B C8B 116.04(19) . . ? O9B C9B C10B 122.79(19) . . ? C8B C9B C10B 121.17(19) . . ? C9B O9B H9B 111(2) . . ? C11B C10B C9B 117.44(19) . . ? C11B C10B C19B 124.48(19) . . ? C9B C10B C19B 118.00(19) . . ? C19B O20B H21A 120(3) . . ? C19B O21B H21B 110.7(19) . . ? C12B C11B C10B 119.69(19) . . ? C12B C11B C13B 116.00(18) . . ? C10B C11B C13B 124.31(18) . . ? C11B C12B C7B 122.63(19) . . ? C11B C12B H12B 118.0 . . ? C7B C12B H12B 119.4 . . ? C18B C13B C14B 119.21(19) . . ? C18B C13B C11B 119.56(18) . . ? C14B C13B C11B 121.01(18) . . ? C15B C14B C13B 120.88(19) . . ? C15B C14B H14B 123.2 . . ? C13B C14B H14B 115.9 . . ? C16B C15B C14B 117.9(2) . . ? C16B C15B H15B 118.6 . . ? C14B C15B H15B 123.4 . . ? F16B C16B C17B 118.2(2) . . ? F16B C16B C15B 118.3(2) . . ? C17B C16B C15B 123.45(19) . . ? C16B C17B C18B 118.06(19) . . ? C16B C17B H17B 122.0 . . ? C18B C17B H17B 119.9 . . ? C13B C18B C17B 120.48(19) . . ? C13B C18B H18B 119.3 . . ? C17B C18B H18B 120.2 . . ? O20B C19B O21B 120.5(2) . . ? O20B C19B C10B 121.8(2) . . ? O21B C19B C10B 117.68(19) . . ? C6C C1C C2C 118.0(2) . . ? C6C C1C C7C 121.30(19) . . ? C2C C1C C7C 120.7(2) . . ? C3C C2C C1C 121.1(2) . . ? C3C C2C H2C 117.9 . . ? C1C C2C H2C 120.9 . . ? C4C C3C C2C 118.7(2) . . ? C4C C3C H3C 123.7 . . ? C2C C3C H3C 117.6 . . ? F4C C4C C5C 118.5(2) . . ? F4C C4C C3C 119.2(2) . . ? C5C C4C C3C 122.4(2) . . ? C4C C5C C6C 118.4(2) . . ? C4C C5C H5C 117.4 . . ? C6C C5C H5C 123.9 . . ? C5C C6C C1C 121.4(2) . . ? C5C C6C H6C 118.7 . . ? C1C C6C H6C 119.9 . . ? C8C C7C C12C 117.59(19) . . ? C8C C7C C1C 121.72(19) . . ? C12C C7C C1C 120.54(19) . . ? C7C C8C C9C 121.15(19) . . ? C7C C8C H8C 124.4 . . ? C9C C8C H8C 114.3 . . ? O9C C9C C8C 115.91(19) . . ? O9C C9C C10C 123.00(19) . . ? C8C C9C C10C 121.08(19) . . ? C9C O9C H9C 102(3) . . ? C9C C10C C11C 118.12(18) . . ? C9C C10C C19C 118.31(19) . . ? C11C C10C C19C 123.44(19) . . ? O20C C19C O21C 121.53(19) . . ? O20C C19C C10C 121.3(2) . . ? O21C C19C C10C 117.17(19) . . ? C19C O21C H21C 111(2) . . ? C12C C11C C10C 119.09(18) . . ? C12C C11C C13C 116.57(17) . . ? C10C C11C C13C 123.91(18) . . ? C11C C12C C7C 122.77(19) . . ? C11C C12C H12C 117.1 . . ? C7C C12C H12C 120.1 . . ? C14C C13C C18C 118.43(18) . . ? C14C C13C C11C 120.56(17) . . ? C18C C13C C11C 120.69(17) . . ? C15C C14C C13C 121.45(18) . . ? C15C C14C H14C 119.8 . . ? C13C C14C H14C 118.8 . . ? C16C C15C C14C 117.77(19) . . ? C16C C15C H15C 119.3 . . ? C14C C15C H15C 122.8 . . ? F16C C16C C17C 118.5(2) . . ? F16C C16C C15C 118.3(2) . . ? C17C C16C C15C 123.2(2) . . ? C16C C17C C18C 118.21(19) . . ? C16C C17C H17C 120.8 . . ? C18C C17C H17C 121.0 . . ? C17C C18C C13C 120.90(18) . . ? C17C C18C H18C 119.4 . . ? C13C C18C H18C 119.7 . . ? C2D C1D C6D 117.6(2) . . ? C2D C1D C7D 121.0(2) . . ? C6D C1D C7D 121.38(19) . . ? C3D C2D C1D 121.7(2) . . ? C3D C2D H2D 118.2 . . ? C1D C2D H2D 120.0 . . ? C4D C3D C2D 118.3(2) . . ? C4D C3D H3D 116.9 . . ? C2D C3D H3D 124.6 . . ? F4D C4D C3D 118.7(2) . . ? F4D C4D C5D 118.7(2) . . ? C3D C4D C5D 122.6(2) . . ? C4D C5D C6D 118.3(2) . . ? C4D C5D H5D 122.8 . . ? C6D C5D H5D 118.9 . . ? C5D C6D C1D 121.5(2) . . ? C5D C6D H6D 117.1 . . ? C1D C6D H6D 121.3 . . ? C8D C7D C12D 117.55(19) . . ? C8D C7D C1D 121.0(2) . . ? C12D C7D C1D 121.33(19) . . ? C7D C8D C9D 121.1(2) . . ? C7D C8D H8D 122.5 . . ? C9D C8D H8D 116.3 . . ? O9D C9D C8D 115.7(2) . . ? O9D C9D C10D 123.0(2) . . ? C8D C9D C10D 121.3(2) . . ? C9D O9D H9D 109(2) . . ? C9D C10D C11D 117.77(19) . . ? C9D C10D C19D 118.3(2) . . ? C11D C10D C19D 123.72(19) . . ? O20D C19D O21D 121.1(2) . . ? O20D C19D C10D 122.1(2) . . ? O21D C19D C10D 116.79(19) . . ? C19D O21D H21D 109.0(18) . . ? C12D C11D C10D 119.26(19) . . ? C12D C11D C13D 117.13(18) . . ? C10D C11D C13D 123.31(18) . . ? C11D C12D C7D 122.79(19) . . ? C11D C12D H12D 118.8 . . ? C7D C12D H12D 118.1 . . ? C18D C13D C14D 118.31(18) . . ? C18D C13D C11D 120.77(18) . . ? C14D C13D C11D 120.64(18) . . ? C15D C14D C13D 121.44(19) . . ? C15D C14D H14D 121.7 . . ? C13D C14D H14D 116.8 . . ? C16D C15D C14D 117.90(19) . . ? C16D C15D H15D 120.8(15) . . ? C14D C15D H15D 121.1(15) . . ? F16D C16D C15D 118.8(2) . . ? F16D C16D C17D 118.0(2) . . ? C15D C16D C17D 123.3(2) . . ? C16D C17D C18D 118.21(19) . . ? C16D C17D H17D 120.9 . . ? C18D C17D H17D 120.9 . . ? C17D C18D C13D 120.88(18) . . ? C17D C18D H18D 121.3 . . ? C13D C18D H18D 117.8 . . ? 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 C6A C1A C2A C3A -0.6(4) . . . . ? C7A C1A C2A C3A 179.7(2) . . . . ? C1A C2A C3A C4A -0.3(4) . . . . ? C2A C3A C4A F4A -178.1(2) . . . . ? C2A C3A C4A C5A 0.3(4) . . . . ? F4A C4A C5A C6A 178.9(2) . . . . ? C3A C4A C5A C6A 0.5(4) . . . . ? C4A C5A C6A C1A -1.4(3) . . . . ? C2A C1A C6A C5A 1.4(3) . . . . ? C7A C1A C6A C5A -178.92(19) . . . . ? C6A C1A C7A C8A -159.8(2) . . . . ? C2A C1A C7A C8A 19.8(3) . . . . ? C6A C1A C7A C12A 19.6(3) . . . . ? C2A C1A C7A C12A -160.8(2) . . . . ? C12A C7A C8A C9A 1.6(3) . . . . ? C1A C7A C8A C9A -179.0(2) . . . . ? C7A C8A C9A O9A -179.3(2) . . . . ? C7A C8A C9A C10A -0.3(4) . . . . ? O9A C9A C10A C11A 177.0(2) . . . . ? C8A C9A C10A C11A -2.0(3) . . . . ? O9A C9A C10A C19A -4.7(3) . . . . ? C8A C9A C10A C19A 176.4(2) . . . . ? C9A C10A C19A O20A 0.1(3) . . . . ? C11A C10A C19A O20A 178.3(2) . . . . ? C9A C10A C19A O21A -179.1(2) . . . . ? C11A C10A C19A O21A -0.9(3) . . . . ? C9A C10A C11A C12A 2.9(3) . . . . ? C19A C10A C11A C12A -175.30(19) . . . . ? C9A C10A C11A C13A -176.46(19) . . . . ? C19A C10A C11A C13A 5.3(3) . . . . ? C10A C11A C12A C7A -1.7(3) . . . . ? C13A C11A C12A C7A 177.70(18) . . . . ? C8A C7A C12A C11A -0.5(3) . . . . ? C1A C7A C12A C11A -179.97(19) . . . . ? C12A C11A C13A C18A 67.5(2) . . . . ? C10A C11A C13A C18A -113.1(2) . . . . ? C12A C11A C13A C14A -108.6(2) . . . . ? C10A C11A C13A C14A 70.8(3) . . . . ? C18A C13A C14A C15A 0.6(3) . . . . ? C11A C13A C14A C15A 176.78(19) . . . . ? C13A C14A C15A C16A 0.2(3) . . . . ? C14A C15A C16A F16A -178.12(19) . . . . ? C14A C15A C16A C17A -1.1(3) . . . . ? F16A C16A C17A C18A 178.21(19) . . . . ? C15A C16A C17A C18A 1.1(3) . . . . ? C14A C13A C18A C17A -0.5(3) . . . . ? C11A C13A C18A C17A -176.68(19) . . . . ? C16A C17A C18A C13A -0.3(3) . . . . ? C6B C1B C2B C3B 1.0(3) . . . . ? C7B C1B C2B C3B -178.1(2) . . . . ? C1B C2B C3B C4B 0.1(4) . . . . ? C2B C3B C4B F4B 178.9(2) . . . . ? C2B C3B C4B C5B -1.2(4) . . . . ? F4B C4B C5B C6B -178.9(2) . . . . ? C3B C4B C5B C6B 1.2(4) . . . . ? C4B C5B C6B C1B 0.0(3) . . . . ? C2B C1B C6B C5B -1.0(3) . . . . ? C7B C1B C6B C5B 178.0(2) . . . . ? C6B C1B C7B C8B 158.2(2) . . . . ? C2B C1B C7B C8B -22.8(3) . . . . ? C6B C1B C7B C12B -22.0(3) . . . . ? C2B C1B C7B C12B 157.1(2) . . . . ? C12B C7B C8B C9B -2.0(3) . . . . ? C1B C7B C8B C9B 177.8(2) . . . . ? C7B C8B C9B O9B -178.6(2) . . . . ? C7B C8B C9B C10B 1.4(4) . . . . ? O9B C9B C10B C11B -179.3(2) . . . . ? C8B C9B C10B C11B 0.7(3) . . . . ? O9B C9B C10B C19B 4.0(3) . . . . ? C8B C9B C10B C19B -176.1(2) . . . . ? C9B C10B C11B C12B -2.2(3) . . . . ? C19B C10B C11B C12B 174.4(2) . . . . ? C9B C10B C11B C13B 177.11(19) . . . . ? C19B C10B C11B C13B -6.3(3) . . . . ? C10B C11B C12B C7B 1.7(3) . . . . ? C13B C11B C12B C7B -177.68(18) . . . . ? C8B C7B C12B C11B 0.5(3) . . . . ? C1B C7B C12B C11B -179.38(19) . . . . ? C12B C11B C13B C18B -63.4(2) . . . . ? C10B C11B C13B C18B 117.3(2) . . . . ? C12B C11B C13B C14B 111.2(2) . . . . ? C10B C11B C13B C14B -68.1(3) . . . . ? C18B C13B C14B C15B 0.3(3) . . . . ? C11B C13B C14B C15B -174.37(18) . . . . ? C13B C14B C15B C16B -0.6(3) . . . . ? C14B C15B C16B F16B 177.83(18) . . . . ? C14B C15B C16B C17B 0.5(3) . . . . ? F16B C16B C17B C18B -177.52(18) . . . . ? C15B C16B C17B C18B -0.2(3) . . . . ? C14B C13B C18B C17B 0.0(3) . . . . ? C11B C13B C18B C17B 174.77(17) . . . . ? C16B C17B C18B C13B -0.1(3) . . . . ? C11B C10B C19B O20B -176.9(2) . . . . ? C9B C10B C19B O20B -0.3(3) . . . . ? C11B C10B C19B O21B 2.5(3) . . . . ? C9B C10B C19B O21B 179.1(2) . . . . ? C6C C1C C2C C3C 1.0(4) . . . . ? C7C C1C C2C C3C -176.8(2) . . . . ? C1C C2C C3C C4C -0.3(4) . . . . ? C2C C3C C4C F4C 178.6(2) . . . . ? C2C C3C C4C C5C -1.2(4) . . . . ? F4C C4C C5C C6C -178.0(2) . . . . ? C3C C4C C5C C6C 1.8(4) . . . . ? C4C C5C C6C C1C -1.0(4) . . . . ? C2C C1C C6C C5C -0.3(4) . . . . ? C7C C1C C6C C5C 177.5(2) . . . . ? C6C C1C C7C C8C -165.0(2) . . . . ? C2C C1C C7C C8C 12.7(3) . . . . ? C6C C1C C7C C12C 10.4(3) . . . . ? C2C C1C C7C C12C -171.8(2) . . . . ? C12C C7C C8C C9C 1.1(3) . . . . ? C1C C7C C8C C9C 176.7(2) . . . . ? C7C C8C C9C O9C 179.2(2) . . . . ? C7C C8C C9C C10C -1.1(4) . . . . ? O9C C9C C10C C11C 177.7(2) . . . . ? C8C C9C C10C C11C -2.0(3) . . . . ? O9C C9C C10C C19C -6.3(3) . . . . ? C8C C9C C10C C19C 174.0(2) . . . . ? C9C C10C C19C O20C 15.0(3) . . . . ? C11C C10C C19C O20C -169.3(2) . . . . ? C9C C10C C19C O21C -162.5(2) . . . . ? C11C C10C C19C O21C 13.2(3) . . . . ? C9C C10C C11C C12C 4.9(3) . . . . ? C19C C10C C11C C12C -170.76(18) . . . . ? C9C C10C C11C C13C -167.25(19) . . . . ? C19C C10C C11C C13C 17.0(3) . . . . ? C10C C11C C12C C7C -5.1(3) . . . . ? C13C C11C C12C C7C 167.65(18) . . . . ? C8C C7C C12C C11C 2.0(3) . . . . ? C1C C7C C12C C11C -173.61(18) . . . . ? C12C C11C C13C C14C -123.9(2) . . . . ? C10C C11C C13C C14C 48.5(3) . . . . ? C12C C11C C13C C18C 49.6(3) . . . . ? C10C C11C C13C C18C -138.0(2) . . . . ? C18C C13C C14C C15C 0.2(3) . . . . ? C11C C13C C14C C15C 173.78(18) . . . . ? C13C C14C C15C C16C 0.4(3) . . . . ? C14C C15C C16C F16C 180.00(19) . . . . ? C14C C15C C16C C17C -1.2(3) . . . . ? F16C C16C C17C C18C -179.95(19) . . . . ? C15C C16C C17C C18C 1.2(3) . . . . ? C16C C17C C18C C13C -0.5(3) . . . . ? C14C C13C C18C C17C -0.1(3) . . . . ? C11C C13C C18C C17C -173.72(18) . . . . ? C6D C1D C2D C3D -1.5(3) . . . . ? C7D C1D C2D C3D 177.7(2) . . . . ? C1D C2D C3D C4D 0.5(4) . . . . ? C2D C3D C4D F4D -178.9(2) . . . . ? C2D C3D C4D C5D 1.3(4) . . . . ? F4D C4D C5D C6D 178.4(2) . . . . ? C3D C4D C5D C6D -1.8(4) . . . . ? C4D C5D C6D C1D 0.7(3) . . . . ? C2D C1D C6D C5D 0.9(3) . . . . ? C7D C1D C6D C5D -178.3(2) . . . . ? C2D C1D C7D C8D -20.7(3) . . . . ? C6D C1D C7D C8D 158.5(2) . . . . ? C2D C1D C7D C12D 162.7(2) . . . . ? C6D C1D C7D C12D -18.1(3) . . . . ? C12D C7D C8D C9D -2.8(3) . . . . ? C1D C7D C8D C9D -179.5(2) . . . . ? C7D C8D C9D O9D -178.5(2) . . . . ? C7D C8D C9D C10D 1.9(4) . . . . ? O9D C9D C10D C11D -177.5(2) . . . . ? C8D C9D C10D C11D 2.1(3) . . . . ? O9D C9D C10D C19D 7.9(3) . . . . ? C8D C9D C10D C19D -172.5(2) . . . . ? C9D C10D C19D O20D -17.0(3) . . . . ? C11D C10D C19D O20D 168.7(2) . . . . ? C9D C10D C19D O21D 161.7(2) . . . . ? C11D C10D C19D O21D -12.6(3) . . . . ? C9D C10D C11D C12D -5.2(3) . . . . ? C19D C10D C11D C12D 169.17(19) . . . . ? C9D C10D C11D C13D 168.4(2) . . . . ? C19D C10D C11D C13D -17.2(3) . . . . ? C10D C11D C12D C7D 4.5(3) . . . . ? C13D C11D C12D C7D -169.54(18) . . . . ? C8D C7D C12D C11D -0.4(3) . . . . ? C1D C7D C12D C11D 176.30(19) . . . . ? C12D C11D C13D C18D -48.2(3) . . . . ? C10D C11D C13D C18D 138.0(2) . . . . ? C12D C11D C13D C14D 125.6(2) . . . . ? C10D C11D C13D C14D -48.1(3) . . . . ? C18D C13D C14D C15D -0.9(3) . . . . ? C11D C13D C14D C15D -174.89(18) . . . . ? C13D C14D C15D C16D 0.9(3) . . . . ? C14D C15D C16D F16D 179.74(19) . . . . ? C14D C15D C16D C17D -0.3(3) . . . . ? F16D C16D C17D C18D 179.66(18) . . . . ? C15D C16D C17D C18D -0.3(3) . . . . ? C16D C17D C18D C13D 0.3(3) . . . . ? C14D C13D C18D C17D 0.3(3) . . . . ? C11D C13D C18D C17D 174.26(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O9A H9A O20A 0.91(4) 1.71(4) 2.548(2) 153(4) . O9B H9B O20B 0.85(3) 1.80(3) 2.541(2) 144(3) . O9C H9C O20C 0.99(5) 1.64(5) 2.564(2) 154(4) . O9D H9D O20D 0.96(4) 1.75(4) 2.589(2) 143(3) . O21A H21A O20B 1.25(7) 1.42(7) 2.636(2) 163(6) . O21B H21B O20A 0.89(3) 1.75(3) 2.644(2) 178(3) . O21C H21C O20D 1.03(5) 1.60(5) 2.625(2) 174(4) . O21D H21D O20C 0.88(3) 1.73(3) 2.610(2) 171(3) . C5A H5A F4B 0.90 2.56 3.285(3) 137.2 2_654 C6A H6A F16D 1.01 2.57 3.553(3) 162.4 2_664 C18A H18A O21C 0.94 2.51 3.325(2) 145.5 2_564 C17A H17A F4C 0.95 2.25 3.126(3) 153.6 1_565 C5B H5B F4C 0.98 2.60 3.436(3) 143.0 1_455 C6B H6B F16C 0.93 2.48 3.406(3) 169.3 2_454 C17B H17B F4B 0.91 2.34 3.104(2) 141.6 2_544 C2C H2C O9B 0.98 2.50 3.291(3) 137.4 . C15C H15C F4A 0.95 2.57 3.211(3) 125.1 1_546 C2D H2D O9C 0.91 2.56 3.223(3) 129.9 2_565 C5D H5D F16C 0.97 2.51 3.295(3) 138.0 1_465 C12D H12D F16A 1.03 2.67 3.624(3) 154.9 2_465 C14D H14D O20A 0.98 2.63 3.592(3) 170.0 2_565 C15D H15D F4D 0.94(3) 2.64(3) 3.248(2) 122.8(19) 2_574 _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 70.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.221 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 933612' ####################################################################### # # 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_2A _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 F2 O3' _chemical_formula_sum 'C21 H16 F2 O3' _chemical_formula_weight 354.34 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' F F 0.0171 0.0103 '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 7.3019(6) _cell_length_b 10.2526(9) _cell_length_c 13.0430(10) _cell_angle_alpha 94.613(7) _cell_angle_beta 103.996(7) _cell_angle_gamma 110.709(8) _cell_volume 871.30(14) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2341 _cell_measurement_theta_min 2.1557 _cell_measurement_theta_max 26.9494 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_T_min 0.92005 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.43 (release 21-10-2010 CrysAlis171 .NET) (compiled Oct 21 2010,17:48:23) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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, Sapphire2, large Be window' _diffrn_detector_area_resol_mean 8.1929 _diffrn_measurement_method \w-scan _diffrn_reflns_number 5343 _diffrn_reflns_av_R_equivalents 0.0139 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 27.01 _reflns_number_total 3409 _reflns_number_gt 2401 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis Pro (Agilent Technologies (2011))' _computing_cell_refinement 'CrysAlis Pro (Agilent Technologies (2011))' _computing_data_reduction 'CrysAlis Pro (Agilent Technologies (2011))' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0554P)^2^+0.1029P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.013(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3409 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1323 _refine_ls_wR_factor_gt 0.1161 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.004 _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 C1 C 0.7360(3) 0.57723(18) 0.25080(15) 0.0580(5) Uani 1 1 d . . . C2 C 0.8637(3) 0.5297(2) 0.3209(2) 0.0707(6) Uani 1 1 d . . . H2 H 0.877(3) 0.549(2) 0.3946(17) 0.074(6) Uiso 1 1 d . . . C3 C 0.9780(4) 0.4638(2) 0.2852(2) 0.0821(7) Uani 1 1 d . . . H3 H 1.066(4) 0.434(3) 0.3392(19) 0.097(8) Uiso 1 1 d . . . C4 C 0.9626(4) 0.4452(2) 0.1790(2) 0.0813(7) Uani 1 1 d . . . F4 F 1.0756(2) 0.38080(17) 0.14340(14) 0.1191(6) Uani 1 1 d . . . C5 C 0.8395(4) 0.4890(2) 0.1067(2) 0.0799(6) Uani 1 1 d . . . H5 H 0.826(3) 0.472(2) 0.031(2) 0.093(7) Uiso 1 1 d . . . C6 C 0.7262(4) 0.5540(2) 0.14299(18) 0.0695(6) Uani 1 1 d . . . H6 H 0.641(3) 0.583(2) 0.0948(16) 0.073(6) Uiso 1 1 d . . . C7 C 0.6162(3) 0.64993(18) 0.28889(14) 0.0548(5) Uani 1 1 d . . . C8 C 0.5590(3) 0.6273(2) 0.38184(15) 0.0627(5) Uani 1 1 d . . . H8 H 0.594(3) 0.561(2) 0.4223(16) 0.076(6) Uiso 1 1 d . . . C9 C 0.4518(3) 0.6987(2) 0.41778(14) 0.0614(5) Uani 1 1 d . . . O9 O 0.4009(3) 0.66753(18) 0.50870(11) 0.0865(5) Uani 1 1 d . . . H9 H 0.332(4) 0.727(3) 0.519(2) 0.119(10) Uiso 1 1 d . . . C10 C 0.3930(3) 0.79584(18) 0.36116(13) 0.0528(4) Uani 1 1 d . . . C19 C 0.2714(3) 0.86217(19) 0.40301(14) 0.0583(5) Uani 1 1 d . . . O20 O 0.2331(3) 0.84609(17) 0.48843(11) 0.0868(5) Uani 1 1 d . . . O21 O 0.2028(2) 0.93927(16) 0.34216(11) 0.0719(4) Uani 1 1 d . . . C22 C 0.0875(4) 1.0123(3) 0.3817(2) 0.0774(6) Uani 1 1 d . . . H22A H 0.173(4) 1.067(3) 0.458(2) 0.102(8) Uiso 1 1 d . . . H22B H -0.039(4) 0.942(2) 0.3857(16) 0.082(7) Uiso 1 1 d . . . C23 C 0.0570(5) 1.1084(4) 0.3086(3) 0.1298(12) Uani 1 1 d . . . H23A H 0.1874 1.1767 0.3092 0.195 Uiso 1 1 calc R . . H23B H -0.0215 1.1566 0.3315 0.195 Uiso 1 1 calc R . . H23C H -0.0149 1.0551 0.2372 0.195 Uiso 1 1 calc R . . C11 C 0.4508(3) 0.81923(17) 0.26626(13) 0.0496(4) Uani 1 1 d . . . C12 C 0.5593(3) 0.74659(18) 0.23249(14) 0.0553(5) Uani 1 1 d . . . H12 H 0.606(3) 0.7690(19) 0.1678(14) 0.058(5) Uiso 1 1 d . . . C13 C 0.4064(3) 0.92106(18) 0.19825(12) 0.0486(4) Uani 1 1 d . . . C14 C 0.5059(3) 1.0657(2) 0.23178(16) 0.0590(5) Uani 1 1 d . . . H14 H 0.602(3) 1.104(2) 0.3049(17) 0.080(6) Uiso 1 1 d . . . C15 C 0.4700(3) 1.1581(2) 0.16592(19) 0.0699(6) Uani 1 1 d . . . H15 H 0.539(4) 1.258(3) 0.1913(17) 0.094(7) Uiso 1 1 d . . . C16 C 0.3357(4) 1.1038(3) 0.06726(17) 0.0709(6) Uani 1 1 d . . . F16 F 0.2976(3) 1.19395(17) 0.00194(12) 0.1117(5) Uani 1 1 d . . . C17 C 0.2341(4) 0.9624(3) 0.03001(18) 0.0824(7) Uani 1 1 d . . . H17 H 0.130(4) 0.924(3) -0.039(2) 0.108(8) Uiso 1 1 d . . . C18 C 0.2707(4) 0.8704(2) 0.09708(16) 0.0712(6) Uani 1 1 d . . . H18 H 0.194(3) 0.766(3) 0.0713(16) 0.090(7) Uiso 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 C1 0.0700(12) 0.0397(9) 0.0647(11) 0.0191(8) 0.0205(9) 0.0190(9) C2 0.0819(14) 0.0538(12) 0.0735(14) 0.0146(10) 0.0147(11) 0.0272(11) C3 0.0754(15) 0.0637(14) 0.1025(19) 0.0152(13) 0.0118(14) 0.0304(12) C4 0.0799(15) 0.0583(13) 0.116(2) 0.0169(13) 0.0423(14) 0.0292(12) F4 0.1167(12) 0.1119(12) 0.1604(14) 0.0217(10) 0.0607(10) 0.0683(10) C5 0.1023(18) 0.0656(14) 0.0889(17) 0.0262(12) 0.0467(14) 0.0372(13) C6 0.0913(15) 0.0589(12) 0.0719(14) 0.0264(10) 0.0316(12) 0.0364(11) C7 0.0701(11) 0.0391(9) 0.0532(10) 0.0168(7) 0.0162(8) 0.0182(8) C8 0.0903(14) 0.0496(11) 0.0530(11) 0.0256(8) 0.0196(10) 0.0299(10) C9 0.0886(14) 0.0512(11) 0.0452(10) 0.0206(8) 0.0216(9) 0.0238(10) O9 0.1443(15) 0.0891(11) 0.0592(9) 0.0443(8) 0.0506(9) 0.0632(11) C10 0.0693(11) 0.0445(9) 0.0436(9) 0.0147(7) 0.0181(8) 0.0183(9) C19 0.0730(12) 0.0504(10) 0.0477(10) 0.0138(8) 0.0186(9) 0.0177(9) O20 0.1348(14) 0.0974(12) 0.0541(8) 0.0285(8) 0.0452(8) 0.0603(11) O21 0.0904(10) 0.0852(10) 0.0708(9) 0.0377(7) 0.0430(7) 0.0516(8) C22 0.0755(15) 0.0881(17) 0.0875(17) 0.0256(14) 0.0414(13) 0.0397(14) C23 0.141(3) 0.159(3) 0.171(3) 0.095(2) 0.088(2) 0.112(2) C11 0.0628(10) 0.0398(9) 0.0429(9) 0.0141(7) 0.0134(8) 0.0157(8) C12 0.0761(12) 0.0466(10) 0.0481(10) 0.0199(8) 0.0236(9) 0.0234(9) C13 0.0614(10) 0.0466(9) 0.0438(9) 0.0173(7) 0.0200(8) 0.0227(8) C14 0.0662(12) 0.0493(11) 0.0592(11) 0.0205(9) 0.0171(9) 0.0181(9) C15 0.0794(14) 0.0525(12) 0.0867(15) 0.0337(11) 0.0339(12) 0.0247(11) C16 0.0931(15) 0.0816(15) 0.0705(14) 0.0510(12) 0.0400(12) 0.0529(13) F16 0.1498(13) 0.1257(12) 0.1117(10) 0.0885(9) 0.0566(9) 0.0869(11) C17 0.1081(18) 0.0949(19) 0.0516(12) 0.0241(11) 0.0095(12) 0.0544(16) C18 0.0940(15) 0.0578(13) 0.0543(11) 0.0123(9) 0.0061(10) 0.0303(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 C2 1.387(3) . ? C1 C6 1.387(3) . ? C1 C7 1.476(3) . ? C2 C3 1.380(3) . ? C2 H2 0.94(2) . ? C3 C4 1.355(3) . ? C3 H3 0.98(2) . ? C4 C5 1.357(3) . ? C4 F4 1.361(3) . ? C5 C6 1.372(3) . ? C5 H5 0.97(2) . ? C6 H6 0.92(2) . ? C7 C8 1.386(3) . ? C7 C12 1.399(2) . ? C8 C9 1.376(3) . ? C8 H8 0.96(2) . ? C9 O9 1.355(2) . ? C9 C10 1.410(2) . ? O9 H9 0.94(3) . ? C10 C11 1.413(2) . ? C10 C19 1.467(3) . ? C19 O20 1.222(2) . ? C19 O21 1.302(2) . ? O21 C22 1.459(3) . ? C22 C23 1.460(3) . ? C22 H22A 1.03(2) . ? C22 H22B 0.97(2) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C11 C12 1.382(2) . ? C11 C13 1.494(2) . ? C12 H12 0.998(18) . ? C13 C18 1.373(2) . ? C13 C14 1.378(2) . ? C14 C15 1.379(3) . ? C14 H14 0.99(2) . ? C15 C16 1.348(3) . ? C15 H15 0.95(2) . ? C16 C17 1.357(3) . ? C16 F16 1.361(2) . ? C17 C18 1.387(3) . ? C17 H17 0.97(2) . ? C18 H18 1.00(2) . ? 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 C2 C1 C6 117.1(2) . . ? C2 C1 C7 121.65(18) . . ? C6 C1 C7 121.26(17) . . ? C3 C2 C1 121.4(2) . . ? C3 C2 H2 120.6(13) . . ? C1 C2 H2 117.8(13) . . ? C4 C3 C2 118.6(2) . . ? C4 C3 H3 124.3(14) . . ? C2 C3 H3 117.1(14) . . ? C3 C4 C5 122.4(2) . . ? C3 C4 F4 118.8(2) . . ? C5 C4 F4 118.7(2) . . ? C4 C5 C6 118.5(2) . . ? C4 C5 H5 121.6(14) . . ? C6 C5 H5 119.9(14) . . ? C5 C6 C1 121.9(2) . . ? C5 C6 H6 119.3(13) . . ? C1 C6 H6 118.7(13) . . ? C8 C7 C12 117.62(18) . . ? C8 C7 C1 121.76(16) . . ? C12 C7 C1 120.62(16) . . ? C9 C8 C7 121.04(17) . . ? C9 C8 H8 118.8(12) . . ? C7 C8 H8 120.1(12) . . ? O9 C9 C8 116.40(17) . . ? O9 C9 C10 121.86(19) . . ? C8 C9 C10 121.71(16) . . ? C9 O9 H9 102.9(17) . . ? C9 C10 C11 117.50(17) . . ? C9 C10 C19 117.86(15) . . ? C11 C10 C19 124.62(16) . . ? O20 C19 O21 121.25(19) . . ? O20 C19 C10 123.22(18) . . ? O21 C19 C10 115.52(15) . . ? C19 O21 C22 117.90(16) . . ? C23 C22 O21 107.38(19) . . ? C23 C22 H22A 111.2(14) . . ? O21 C22 H22A 107.5(13) . . ? C23 C22 H22B 113.5(13) . . ? O21 C22 H22B 108.3(13) . . ? H22A C22 H22B 108.8(19) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C12 C11 C10 119.48(15) . . ? C12 C11 C13 115.92(14) . . ? C10 C11 C13 124.59(16) . . ? C11 C12 C7 122.64(17) . . ? C11 C12 H12 118.1(10) . . ? C7 C12 H12 119.1(10) . . ? C18 C13 C14 118.48(17) . . ? C18 C13 C11 119.59(16) . . ? C14 C13 C11 121.84(15) . . ? C15 C14 C13 121.06(19) . . ? C15 C14 H14 119.6(12) . . ? C13 C14 H14 119.3(12) . . ? C16 C15 C14 118.5(2) . . ? C16 C15 H15 121.9(14) . . ? C14 C15 H15 119.6(14) . . ? C15 C16 C17 122.90(18) . . ? C15 C16 F16 119.0(2) . . ? C17 C16 F16 118.1(2) . . ? C16 C17 C18 118.1(2) . . ? C16 C17 H17 122.7(15) . . ? C18 C17 H17 119.0(16) . . ? C13 C18 C17 120.9(2) . . ? C13 C18 H18 120.2(12) . . ? C17 C18 H18 118.9(12) . . ? 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 C6 C1 C2 C3 0.8(3) . . . . ? C7 C1 C2 C3 -178.92(18) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? C2 C3 C4 F4 179.75(19) . . . . ? C3 C4 C5 C6 -0.3(4) . . . . ? F4 C4 C5 C6 -179.90(19) . . . . ? C4 C5 C6 C1 0.7(3) . . . . ? C2 C1 C6 C5 -1.0(3) . . . . ? C7 C1 C6 C5 178.75(19) . . . . ? C2 C1 C7 C8 -25.9(3) . . . . ? C6 C1 C7 C8 154.38(19) . . . . ? C2 C1 C7 C12 153.06(18) . . . . ? C6 C1 C7 C12 -26.7(3) . . . . ? C12 C7 C8 C9 -0.7(3) . . . . ? C1 C7 C8 C9 178.30(17) . . . . ? C7 C8 C9 O9 179.15(18) . . . . ? C7 C8 C9 C10 1.0(3) . . . . ? O9 C9 C10 C11 -178.94(17) . . . . ? C8 C9 C10 C11 -0.9(3) . . . . ? O9 C9 C10 C19 -0.7(3) . . . . ? C8 C9 C10 C19 177.35(17) . . . . ? C9 C10 C19 O20 6.0(3) . . . . ? C11 C10 C19 O20 -175.85(18) . . . . ? C9 C10 C19 O21 -173.08(16) . . . . ? C11 C10 C19 O21 5.0(3) . . . . ? O20 C19 O21 C22 3.2(3) . . . . ? C10 C19 O21 C22 -177.67(18) . . . . ? C19 O21 C22 C23 170.9(2) . . . . ? C9 C10 C11 C12 0.5(2) . . . . ? C19 C10 C11 C12 -177.60(16) . . . . ? C9 C10 C11 C13 -178.26(16) . . . . ? C19 C10 C11 C13 3.6(3) . . . . ? C10 C11 C12 C7 -0.2(3) . . . . ? C13 C11 C12 C7 178.64(16) . . . . ? C8 C7 C12 C11 0.3(3) . . . . ? C1 C7 C12 C11 -178.68(16) . . . . ? C12 C11 C13 C18 69.2(2) . . . . ? C10 C11 C13 C18 -112.0(2) . . . . ? C12 C11 C13 C14 -107.3(2) . . . . ? C10 C11 C13 C14 71.5(2) . . . . ? C18 C13 C14 C15 0.4(3) . . . . ? C11 C13 C14 C15 176.93(18) . . . . ? C13 C14 C15 C16 -0.4(3) . . . . ? C14 C15 C16 C17 0.1(3) . . . . ? C14 C15 C16 F16 179.39(18) . . . . ? C15 C16 C17 C18 0.2(4) . . . . ? F16 C16 C17 C18 -179.1(2) . . . . ? C14 C13 C18 C17 -0.1(3) . . . . ? C11 C13 C18 C17 -176.7(2) . . . . ? C16 C17 C18 C13 -0.2(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O9 H9 O20 0.94(3) 1.65(3) 2.536(2) 155(3) . C6 H6 F16 0.92(2) 2.65(2) 3.350(2) 133.4(16) 2_675 C12 H12 F16 0.998(18) 2.499(19) 3.494(2) 175.4(14) 2_675 C8 H8 O9 0.96(2) 2.58(2) 3.518(2) 164.2(16) 2_666 _diffrn_measured_fraction_theta_max 0.897 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.146 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 933613' ####################################################################### # # 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_2B _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 F2 O3' _chemical_formula_sum 'C21 H16 F2 O3' _chemical_formula_weight 354.34 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' F F 0.0171 0.0103 '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 6.9778(3) _cell_length_b 11.1289(5) _cell_length_c 11.5383(5) _cell_angle_alpha 96.213(3) _cell_angle_beta 98.252(4) _cell_angle_gamma 93.542(4) _cell_volume 878.80(7) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2961 _cell_measurement_theta_min 2.9530 _cell_measurement_theta_max 28.1370 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_T_min 0.99613 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.43 (release 21-10-2010 CrysAlis171 .NET) (compiled Oct 21 2010,17:48:23) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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' _diffrn_detector_area_resol_mean 16.1544 _diffrn_measurement_method \w-scan _diffrn_reflns_number 9504 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3080 _reflns_number_gt 1988 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis Pro (Agilent Technologies (2011))' _computing_cell_refinement 'CrysAlis Pro (Agilent Technologies (2011))' _computing_data_reduction 'CrysAlis Pro (Agilent Technologies (2011))' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0459P)^2^+0.1470P] 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 3080 _refine_ls_number_parameters 288 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0853 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1134 _refine_ls_wR_factor_gt 0.1007 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 C1 C 0.8604(3) 0.74124(17) 0.73871(18) 0.0560(5) Uani 1 1 d . . . C2 C 0.6776(4) 0.7287(2) 0.7728(2) 0.0652(6) Uani 1 1 d . . . H2 H 0.567(3) 0.6974(19) 0.7142(19) 0.074(7) Uiso 1 1 d . . . C3 C 0.6499(5) 0.7651(2) 0.8868(2) 0.0809(8) Uani 1 1 d . . . H3 H 0.520(4) 0.758(2) 0.911(2) 0.109(9) Uiso 1 1 d . . . C4 C 0.8050(5) 0.8125(2) 0.9664(2) 0.0855(8) Uani 1 1 d . . . F4 F 0.7796(3) 0.84952(18) 1.07871(14) 0.1340(7) Uani 1 1 d . . . C5 C 0.9866(5) 0.8271(3) 0.9375(3) 0.0878(8) Uani 1 1 d . . . H5 H 1.082(4) 0.860(2) 0.992(2) 0.087(8) Uiso 1 1 d . . . C6 C 1.0133(4) 0.7912(2) 0.8235(2) 0.0727(7) Uani 1 1 d . . . H6 H 1.138(3) 0.7970(19) 0.8044(19) 0.074(7) Uiso 1 1 d . . . C7 C 0.8885(3) 0.70332(17) 0.61536(18) 0.0524(5) Uani 1 1 d . . . C8 C 0.7746(3) 0.60792(18) 0.5473(2) 0.0563(6) Uani 1 1 d . . . H8 H 0.676(3) 0.5629(18) 0.5797(17) 0.067(6) Uiso 1 1 d . . . C9 C 0.7997(3) 0.57471(17) 0.4323(2) 0.0563(5) Uani 1 1 d . . . O9 O 0.6808(2) 0.48025(14) 0.37133(17) 0.0785(5) Uani 1 1 d . . . H9 H 0.723(4) 0.474(2) 0.298(2) 0.103(10) Uiso 1 1 d . . . C10 C 0.9457(3) 0.63328(17) 0.38166(18) 0.0514(5) Uani 1 1 d . . . C19 C 0.9761(3) 0.58338(19) 0.2628(2) 0.0609(6) Uani 1 1 d . . . O20 O 0.8578(2) 0.51346(16) 0.19579(15) 0.0892(6) Uani 1 1 d . . . O21 O 1.1467(2) 0.61512(13) 0.23552(13) 0.0723(5) Uani 1 1 d . . . C22 C 1.1861(5) 0.5719(3) 0.1182(2) 0.0809(8) Uani 1 1 d . . . H22A H 1.164(3) 0.480(2) 0.108(2) 0.099(8) Uiso 1 1 d . . . H22B H 1.080(4) 0.606(3) 0.053(3) 0.137(12) Uiso 1 1 d . . . C23 C 1.3803(5) 0.6217(3) 0.1100(3) 0.1199(11) Uani 1 1 d . . . H23A H 1.3863 0.7085 0.1237 0.180 Uiso 1 1 calc R . . H23B H 1.4107 0.5974 0.0327 0.180 Uiso 1 1 calc R . . H23C H 1.4724 0.5920 0.1680 0.180 Uiso 1 1 calc R . . C11 C 1.0596(3) 0.73293(17) 0.45013(18) 0.0491(5) Uani 1 1 d . . . C12 C 1.0286(3) 0.76552(19) 0.56417(19) 0.0541(5) Uani 1 1 d . . . H12 H 1.099(3) 0.8349(17) 0.6052(16) 0.054(5) Uiso 1 1 d . . . C13 C 1.2094(3) 0.80749(16) 0.40289(17) 0.0483(5) Uani 1 1 d . . . C14 C 1.1582(3) 0.88407(19) 0.3199(2) 0.0622(6) Uani 1 1 d . . . H14 H 1.030(3) 0.8886(17) 0.2929(17) 0.061(6) Uiso 1 1 d . . . C15 C 1.2970(4) 0.9532(2) 0.2769(2) 0.0680(7) Uani 1 1 d . . . H15 H 1.263(3) 1.0035(19) 0.2188(19) 0.070(7) Uiso 1 1 d . . . C16 C 1.4872(3) 0.9434(2) 0.3191(2) 0.0662(6) Uani 1 1 d . . . F16 F 1.6246(2) 1.01107(13) 0.27606(13) 0.1004(5) Uani 1 1 d . . . C17 C 1.5440(4) 0.8708(2) 0.4021(2) 0.0724(7) Uani 1 1 d . . . H17 H 1.674(4) 0.864(2) 0.430(2) 0.086(8) Uiso 1 1 d . . . C18 C 1.4035(3) 0.8025(2) 0.4441(2) 0.0642(6) Uani 1 1 d . . . H18 H 1.437(3) 0.7468(19) 0.4996(19) 0.074(7) Uiso 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 C1 0.0611(14) 0.0500(12) 0.0569(14) 0.0106(10) 0.0076(11) -0.0016(10) C2 0.0697(16) 0.0667(15) 0.0595(16) 0.0143(12) 0.0130(13) -0.0112(12) C3 0.088(2) 0.0895(19) 0.070(2) 0.0160(15) 0.0268(16) -0.0039(15) C4 0.112(2) 0.0935(19) 0.0530(17) 0.0079(14) 0.0233(16) 0.0033(17) F4 0.1612(17) 0.1760(18) 0.0632(11) -0.0066(11) 0.0319(10) 0.0010(13) C5 0.094(2) 0.100(2) 0.0601(19) -0.0009(15) -0.0074(17) 0.0005(17) C6 0.0686(18) 0.0824(17) 0.0640(18) 0.0038(13) 0.0048(13) 0.0017(13) C7 0.0503(12) 0.0496(12) 0.0571(14) 0.0098(10) 0.0059(10) 0.0010(9) C8 0.0509(13) 0.0486(12) 0.0696(16) 0.0111(11) 0.0097(11) -0.0033(10) C9 0.0520(13) 0.0473(12) 0.0655(15) 0.0023(10) 0.0027(10) -0.0056(10) O9 0.0785(11) 0.0661(10) 0.0828(13) -0.0099(9) 0.0127(9) -0.0280(8) C10 0.0496(12) 0.0454(11) 0.0571(14) 0.0037(10) 0.0037(9) 0.0020(9) C19 0.0620(14) 0.0558(13) 0.0635(15) 0.0070(11) 0.0070(12) -0.0007(11) O20 0.0872(12) 0.0924(12) 0.0756(12) -0.0213(9) 0.0062(9) -0.0208(10) O21 0.0819(11) 0.0699(10) 0.0631(10) -0.0056(8) 0.0200(8) -0.0080(8) C22 0.113(2) 0.0674(17) 0.0647(18) -0.0040(13) 0.0323(16) -0.0026(16) C23 0.126(3) 0.132(3) 0.110(3) 0.000(2) 0.058(2) 0.006(2) C11 0.0429(11) 0.0469(11) 0.0568(14) 0.0080(10) 0.0037(9) 0.0033(9) C12 0.0526(13) 0.0466(12) 0.0592(15) 0.0003(10) 0.0037(10) -0.0061(10) C13 0.0453(12) 0.0451(11) 0.0520(13) 0.0001(9) 0.0044(9) -0.0005(9) C14 0.0524(14) 0.0571(13) 0.0750(17) 0.0123(12) 0.0024(12) -0.0024(11) C15 0.0777(18) 0.0543(13) 0.0723(17) 0.0149(12) 0.0115(13) -0.0061(12) C16 0.0644(16) 0.0626(14) 0.0695(16) -0.0069(12) 0.0250(13) -0.0206(12) F16 0.0942(11) 0.1004(11) 0.1070(12) 0.0027(9) 0.0424(9) -0.0365(9) C17 0.0441(14) 0.0985(19) 0.0718(17) 0.0032(14) 0.0083(12) -0.0024(13) C18 0.0513(14) 0.0780(16) 0.0652(16) 0.0169(13) 0.0089(11) 0.0048(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 C6 1.384(3) . ? C1 C2 1.391(3) . ? C1 C7 1.484(3) . ? C2 C3 1.378(3) . ? C2 H2 0.97(2) . ? C3 C4 1.354(4) . ? C3 H3 0.99(3) . ? C4 F4 1.357(3) . ? C4 C5 1.360(4) . ? C5 C6 1.375(4) . ? C5 H5 0.88(2) . ? C6 H6 0.93(2) . ? C7 C8 1.382(3) . ? C7 C12 1.398(3) . ? C8 C9 1.378(3) . ? C8 H8 0.97(2) . ? C9 O9 1.361(2) . ? C9 C10 1.405(3) . ? O9 H9 0.93(3) . ? C10 C11 1.417(3) . ? C10 C19 1.472(3) . ? C19 O20 1.222(2) . ? C19 O21 1.312(2) . ? O21 C22 1.456(3) . ? C22 C23 1.452(4) . ? C22 H22A 1.02(3) . ? C22 H22B 1.09(3) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C11 C12 1.378(3) . ? C11 C13 1.494(3) . ? C12 H12 0.932(19) . ? C13 C14 1.374(3) . ? C13 C18 1.376(3) . ? C14 C15 1.381(3) . ? C14 H14 0.91(2) . ? C15 C16 1.362(3) . ? C15 H15 0.93(2) . ? C16 C17 1.352(3) . ? C16 F16 1.364(2) . ? C17 C18 1.377(3) . ? C17 H17 0.93(2) . ? C18 H18 0.95(2) . ? 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 C6 C1 C2 117.6(2) . . ? C6 C1 C7 121.6(2) . . ? C2 C1 C7 120.81(19) . . ? C3 C2 C1 121.2(2) . . ? C3 C2 H2 119.4(13) . . ? C1 C2 H2 119.3(13) . . ? C4 C3 C2 118.8(3) . . ? C4 C3 H3 119.8(15) . . ? C2 C3 H3 121.5(16) . . ? C3 C4 F4 119.4(3) . . ? C3 C4 C5 122.4(3) . . ? F4 C4 C5 118.2(3) . . ? C4 C5 C6 118.6(3) . . ? C4 C5 H5 118.8(17) . . ? C6 C5 H5 122.6(17) . . ? C5 C6 C1 121.5(3) . . ? C5 C6 H6 119.0(14) . . ? C1 C6 H6 119.5(14) . . ? C8 C7 C12 118.3(2) . . ? C8 C7 C1 121.16(18) . . ? C12 C7 C1 120.51(18) . . ? C9 C8 C7 120.73(19) . . ? C9 C8 H8 118.6(12) . . ? C7 C8 H8 120.7(12) . . ? O9 C9 C8 116.95(18) . . ? O9 C9 C10 121.7(2) . . ? C8 C9 C10 121.36(18) . . ? C9 O9 H9 102.3(16) . . ? C9 C10 C11 118.02(19) . . ? C9 C10 C19 117.68(18) . . ? C11 C10 C19 124.24(18) . . ? O20 C19 O21 121.7(2) . . ? O20 C19 C10 123.7(2) . . ? O21 C19 C10 114.53(18) . . ? C19 O21 C22 117.84(18) . . ? C23 C22 O21 106.8(2) . . ? C23 C22 H22A 116.5(14) . . ? O21 C22 H22A 107.4(14) . . ? C23 C22 H22B 110.0(15) . . ? O21 C22 H22B 108.5(17) . . ? H22A C22 H22B 107(2) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C12 C11 C10 119.19(18) . . ? C12 C11 C13 117.99(17) . . ? C10 C11 C13 122.79(18) . . ? C11 C12 C7 122.30(19) . . ? C11 C12 H12 117.2(11) . . ? C7 C12 H12 120.3(11) . . ? C14 C13 C18 118.36(19) . . ? C14 C13 C11 121.47(18) . . ? C18 C13 C11 120.16(19) . . ? C13 C14 C15 121.3(2) . . ? C13 C14 H14 118.9(12) . . ? C15 C14 H14 119.9(12) . . ? C16 C15 C14 118.0(2) . . ? C16 C15 H15 120.4(13) . . ? C14 C15 H15 121.5(13) . . ? C17 C16 C15 122.7(2) . . ? C17 C16 F16 119.2(2) . . ? C15 C16 F16 118.1(2) . . ? C16 C17 C18 118.5(2) . . ? C16 C17 H17 122.2(14) . . ? C18 C17 H17 119.3(14) . . ? C13 C18 C17 121.2(2) . . ? C13 C18 H18 117.5(12) . . ? C17 C18 H18 121.2(12) . . ? 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 C6 C1 C2 C3 0.2(3) . . . . ? C7 C1 C2 C3 -179.2(2) . . . . ? C1 C2 C3 C4 -0.7(4) . . . . ? C2 C3 C4 F4 179.5(2) . . . . ? C2 C3 C4 C5 0.9(4) . . . . ? C3 C4 C5 C6 -0.6(4) . . . . ? F4 C4 C5 C6 -179.2(2) . . . . ? C4 C5 C6 C1 0.1(4) . . . . ? C2 C1 C6 C5 0.1(4) . . . . ? C7 C1 C6 C5 179.5(2) . . . . ? C6 C1 C7 C8 149.3(2) . . . . ? C2 C1 C7 C8 -31.3(3) . . . . ? C6 C1 C7 C12 -32.2(3) . . . . ? C2 C1 C7 C12 147.1(2) . . . . ? C12 C7 C8 C9 0.4(3) . . . . ? C1 C7 C8 C9 178.90(19) . . . . ? C7 C8 C9 O9 -179.65(18) . . . . ? C7 C8 C9 C10 2.4(3) . . . . ? O9 C9 C10 C11 178.34(18) . . . . ? C8 C9 C10 C11 -3.8(3) . . . . ? O9 C9 C10 C19 -4.4(3) . . . . ? C8 C9 C10 C19 173.43(19) . . . . ? C9 C10 C19 O20 17.1(3) . . . . ? C11 C10 C19 O20 -165.8(2) . . . . ? C9 C10 C19 O21 -159.57(18) . . . . ? C11 C10 C19 O21 17.5(3) . . . . ? O20 C19 O21 C22 4.8(3) . . . . ? C10 C19 O21 C22 -178.5(2) . . . . ? C19 O21 C22 C23 178.7(2) . . . . ? C9 C10 C11 C12 2.5(3) . . . . ? C19 C10 C11 C12 -174.58(19) . . . . ? C9 C10 C11 C13 -175.60(18) . . . . ? C19 C10 C11 C13 7.3(3) . . . . ? C10 C11 C12 C7 0.2(3) . . . . ? C13 C11 C12 C7 178.41(18) . . . . ? C8 C7 C12 C11 -1.7(3) . . . . ? C1 C7 C12 C11 179.76(18) . . . . ? C12 C11 C13 C14 -107.8(2) . . . . ? C10 C11 C13 C14 70.3(3) . . . . ? C12 C11 C13 C18 70.8(3) . . . . ? C10 C11 C13 C18 -111.1(2) . . . . ? C18 C13 C14 C15 1.0(3) . . . . ? C11 C13 C14 C15 179.7(2) . . . . ? C13 C14 C15 C16 0.1(3) . . . . ? C14 C15 C16 C17 -1.1(4) . . . . ? C14 C15 C16 F16 179.5(2) . . . . ? C15 C16 C17 C18 1.1(4) . . . . ? F16 C16 C17 C18 -179.6(2) . . . . ? C14 C13 C18 C17 -1.1(3) . . . . ? C11 C13 C18 C17 -179.8(2) . . . . ? C16 C17 C18 C13 0.1(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2 O9 0.97(2) 2.56(2) 3.417(3) 147.9(16) 2_666 C8 H8 O9 0.97(2) 2.66(2) 3.551(3) 153.7(16) 2_666 C12 H12 F16 0.932(19) 2.618(19) 3.524(2) 164.0(15) 2_876 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.113 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.028 _database_code_depnum_ccdc_archive 'CCDC 933614' ####################################################################### # # 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_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H14 F2 N2 O2' _chemical_formula_sum 'C19 H14 F2 N2 O2' _chemical_formula_weight 340.32 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' N N 0.0311 0.0180 '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' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.6775(3) _cell_length_b 30.6798(9) _cell_length_c 9.5451(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.898(4) _cell_angle_gamma 90.00 _cell_volume 1599.02(12) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 6967 _cell_measurement_theta_min 2.8783 _cell_measurement_theta_max 73.6368 _exptl_crystal_description block _exptl_crystal_colour pale-blue _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.917 _exptl_absorpt_correction_T_min 0.90416 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.43 (release 21-10-2010 CrysAlis171 .NET) (compiled Oct 21 2010,17:48:23) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset), Atlas' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 10.5357 _diffrn_reflns_number 9401 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0146 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 73.79 _reflns_number_total 3108 _reflns_number_gt 2879 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis Pro (Agilent Technologies (2011))' _computing_cell_refinement 'CrysAlis Pro (Agilent Technologies (2011))' _computing_data_reduction 'CrysAlis Pro (Agilent Technologies (2011))' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0530P)^2^+0.3829P] 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 3108 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1084 _refine_ls_wR_factor_gt 0.1058 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 C1 C 0.8271(3) 0.06883(5) -0.13316(15) 0.0464(3) Uani 1 1 d . . . C2 C 1.0106(3) 0.07027(6) -0.20355(18) 0.0578(4) Uani 1 1 d . . . H2 H 1.098(3) 0.0958(7) -0.202(2) 0.065(5) Uiso 1 1 d . . . C3 C 1.0665(4) 0.03395(6) -0.2750(2) 0.0685(5) Uani 1 1 d . . . H3 H 1.194(4) 0.0357(7) -0.323(2) 0.085(6) Uiso 1 1 d . . . C4 C 0.9422(4) -0.00382(6) -0.2710(2) 0.0699(5) Uani 1 1 d . . . F4 F 0.9957(3) -0.03916(4) -0.34235(17) 0.1067(5) Uani 1 1 d . . . C5 C 0.7673(4) -0.00734(7) -0.1991(3) 0.0784(6) Uani 1 1 d . . . H5 H 0.685(5) -0.0356(9) -0.198(3) 0.116(9) Uiso 1 1 d . . . C6 C 0.7094(4) 0.02931(6) -0.1306(2) 0.0637(4) Uani 1 1 d . . . H6 H 0.577(4) 0.0286(7) -0.085(2) 0.080(6) Uiso 1 1 d . . . C7 C 0.7517(3) 0.10893(4) -0.06881(14) 0.0434(3) Uani 1 1 d . . . C8 C 0.7751(3) 0.14951(5) -0.12871(15) 0.0453(3) Uani 1 1 d . . . H8 H 0.848(3) 0.1528(5) -0.2079(18) 0.051(4) Uiso 1 1 d . . . C9 C 0.6973(3) 0.18714(4) -0.07368(14) 0.0418(3) Uani 1 1 d . . . O9 O 0.7240(2) 0.22740(3) -0.12701(12) 0.0550(3) Uani 1 1 d . . . H9 H 0.754(4) 0.2258(8) -0.212(3) 0.093(7) Uiso 1 1 d . . . C10 C 0.5936(2) 0.18485(4) 0.04322(13) 0.0384(3) Uani 1 1 d . . . C19 C 0.5188(2) 0.22582(4) 0.10602(13) 0.0395(3) Uani 1 1 d . . . O20 O 0.6170(2) 0.23730(4) 0.23061(11) 0.0588(3) Uani 1 1 d . . . N21 N 0.3302(2) 0.24646(4) 0.01872(12) 0.0487(3) Uani 1 1 d . . . H21 H 0.279(3) 0.2413(6) -0.077(2) 0.059(5) Uiso 1 1 d . . . N22 N 0.2269(3) 0.28294(5) 0.06972(15) 0.0591(4) Uani 1 1 d . . . H22B H 0.287(5) 0.3058(9) 0.040(3) 0.098(8) Uiso 1 1 d . . . H22A H 0.063(6) 0.2825(9) 0.032(3) 0.116(10) Uiso 1 1 d . . . C11 C 0.5706(2) 0.14408(4) 0.10547(14) 0.0402(3) Uani 1 1 d . . . C12 C 0.6509(3) 0.10686(5) 0.04912(15) 0.0448(3) Uani 1 1 d . . . H12 H 0.636(3) 0.0779(6) 0.0935(18) 0.056(4) Uiso 1 1 d . . . C13 C 0.4621(2) 0.14017(4) 0.23105(14) 0.0406(3) Uani 1 1 d . . . C14 C 0.2477(3) 0.16212(5) 0.23167(16) 0.0471(3) Uani 1 1 d . . . H14 H 0.160(3) 0.1784(6) 0.148(2) 0.055(4) Uiso 1 1 d . . . C15 C 0.1531(3) 0.16057(6) 0.35018(17) 0.0535(4) Uani 1 1 d . . . H15 H 0.003(4) 0.1759(6) 0.346(2) 0.070(5) Uiso 1 1 d . . . C16 C 0.2734(3) 0.13597(5) 0.46747(17) 0.0555(4) Uani 1 1 d . . . F16 F 0.1815(2) 0.13466(4) 0.58477(12) 0.0868(4) Uani 1 1 d . . . C17 C 0.4811(3) 0.11266(5) 0.47116(16) 0.0538(4) Uani 1 1 d . . . H17 H 0.562(4) 0.0962(6) 0.554(2) 0.069(5) Uiso 1 1 d . . . C18 C 0.5763(3) 0.11505(5) 0.35204(15) 0.0459(3) Uani 1 1 d . . . H18 H 0.730(3) 0.0997(5) 0.3543(17) 0.049(4) Uiso 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 C1 0.0529(8) 0.0477(7) 0.0396(7) 0.0012(5) 0.0142(6) 0.0073(6) C2 0.0681(10) 0.0536(9) 0.0592(9) 0.0032(7) 0.0300(8) 0.0087(8) C3 0.0774(12) 0.0719(11) 0.0655(10) -0.0003(8) 0.0352(9) 0.0217(9) C4 0.0841(12) 0.0558(10) 0.0698(11) -0.0126(8) 0.0208(9) 0.0194(9) F4 0.1343(12) 0.0745(8) 0.1198(11) -0.0333(7) 0.0489(9) 0.0258(7) C5 0.0919(14) 0.0535(10) 0.0957(15) -0.0171(10) 0.0359(12) -0.0054(9) C6 0.0714(11) 0.0534(9) 0.0740(11) -0.0082(8) 0.0327(9) -0.0037(8) C7 0.0482(7) 0.0447(7) 0.0388(7) 0.0012(5) 0.0146(5) 0.0034(5) C8 0.0551(8) 0.0494(8) 0.0362(7) 0.0040(5) 0.0206(6) 0.0055(6) C9 0.0499(7) 0.0425(7) 0.0349(6) 0.0055(5) 0.0148(5) 0.0034(5) O9 0.0831(8) 0.0445(5) 0.0487(6) 0.0092(4) 0.0369(6) 0.0058(5) C10 0.0410(6) 0.0442(7) 0.0300(6) 0.0025(5) 0.0097(5) 0.0030(5) C19 0.0469(7) 0.0443(7) 0.0286(6) 0.0016(5) 0.0125(5) -0.0011(5) O20 0.0688(7) 0.0650(7) 0.0349(5) -0.0104(4) 0.0015(5) 0.0020(5) N21 0.0643(7) 0.0522(7) 0.0293(6) -0.0015(5) 0.0125(5) 0.0178(6) N22 0.0826(11) 0.0531(8) 0.0476(7) 0.0022(6) 0.0282(7) 0.0232(7) C11 0.0414(7) 0.0465(7) 0.0339(6) 0.0027(5) 0.0123(5) 0.0007(5) C12 0.0531(8) 0.0423(7) 0.0424(7) 0.0041(5) 0.0187(6) 0.0010(6) C13 0.0452(7) 0.0425(7) 0.0364(6) 0.0009(5) 0.0150(5) -0.0051(5) C14 0.0443(7) 0.0550(8) 0.0442(7) 0.0047(6) 0.0158(6) -0.0020(6) C15 0.0489(8) 0.0623(9) 0.0562(9) -0.0010(7) 0.0263(7) -0.0059(7) C16 0.0639(9) 0.0660(9) 0.0456(8) -0.0024(7) 0.0304(7) -0.0167(7) F16 0.0999(8) 0.1180(10) 0.0615(6) 0.0091(6) 0.0540(6) -0.0083(7) C17 0.0668(9) 0.0556(9) 0.0401(7) 0.0095(6) 0.0165(7) -0.0092(7) C18 0.0527(8) 0.0432(7) 0.0439(7) 0.0044(5) 0.0166(6) -0.0026(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 C2 1.387(2) . ? C1 C6 1.388(2) . ? C1 C7 1.4892(19) . ? C2 C3 1.388(2) . ? C2 H2 0.92(2) . ? C3 C4 1.363(3) . ? C3 H3 0.96(2) . ? C4 C5 1.358(3) . ? C4 F4 1.3581(19) . ? C5 C6 1.384(2) . ? C5 H5 0.99(3) . ? C6 H6 0.97(2) . ? C7 C8 1.3915(19) . ? C7 C12 1.3970(18) . ? C8 C9 1.3896(19) . ? C8 H8 0.961(17) . ? C9 O9 1.3602(16) . ? C9 C10 1.3985(17) . ? O9 H9 0.87(3) . ? C10 C11 1.4062(18) . ? C10 C19 1.5032(18) . ? C19 O20 1.2190(16) . ? C19 N21 1.3239(18) . ? N21 N22 1.4108(17) . ? N21 H21 0.90(2) . ? N22 H22B 0.86(3) . ? N22 H22A 0.90(3) . ? C11 C12 1.3912(19) . ? C11 C13 1.4948(17) . ? C12 H12 0.997(18) . ? C13 C18 1.3920(19) . ? C13 C14 1.393(2) . ? C14 C15 1.3795(19) . ? C14 H14 0.956(18) . ? C15 C16 1.368(2) . ? C15 H15 0.96(2) . ? C16 F16 1.3590(16) . ? C16 C17 1.371(2) . ? C17 C18 1.388(2) . ? C17 H17 0.94(2) . ? C18 H18 0.989(17) . ? 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 C2 C1 C6 117.75(14) . . ? C2 C1 C7 120.83(14) . . ? C6 C1 C7 121.36(13) . . ? C1 C2 C3 121.06(17) . . ? C1 C2 H2 119.3(12) . . ? C3 C2 H2 119.6(12) . . ? C4 C3 C2 118.63(17) . . ? C4 C3 H3 121.7(13) . . ? C2 C3 H3 119.7(13) . . ? C5 C4 F4 119.02(18) . . ? C5 C4 C3 122.54(16) . . ? F4 C4 C3 118.44(18) . . ? C4 C5 C6 118.39(19) . . ? C4 C5 H5 119.3(16) . . ? C6 C5 H5 122.3(16) . . ? C5 C6 C1 121.57(17) . . ? C5 C6 H6 120.7(13) . . ? C1 C6 H6 117.6(13) . . ? C8 C7 C12 118.55(12) . . ? C8 C7 C1 119.94(12) . . ? C12 C7 C1 121.49(12) . . ? C9 C8 C7 120.80(12) . . ? C9 C8 H8 117.4(10) . . ? C7 C8 H8 121.8(10) . . ? O9 C9 C8 122.23(11) . . ? O9 C9 C10 117.30(11) . . ? C8 C9 C10 120.44(12) . . ? C9 O9 H9 111.6(16) . . ? C9 C10 C11 119.34(11) . . ? C9 C10 C19 120.19(11) . . ? C11 C10 C19 120.41(11) . . ? O20 C19 N21 123.43(13) . . ? O20 C19 C10 121.78(12) . . ? N21 C19 C10 114.66(11) . . ? C19 N21 N22 120.21(12) . . ? C19 N21 H21 122.5(11) . . ? N22 N21 H21 116.5(11) . . ? N21 N22 H22B 106.9(17) . . ? N21 N22 H22A 109.4(19) . . ? H22B N22 H22A 110(2) . . ? C12 C11 C10 119.24(11) . . ? C12 C11 C13 119.66(12) . . ? C10 C11 C13 121.11(11) . . ? C11 C12 C7 121.62(12) . . ? C11 C12 H12 119.5(10) . . ? C7 C12 H12 118.9(10) . . ? C18 C13 C14 118.23(12) . . ? C18 C13 C11 120.62(12) . . ? C14 C13 C11 121.14(12) . . ? C15 C14 C13 121.60(14) . . ? C15 C14 H14 118.2(10) . . ? C13 C14 H14 120.2(10) . . ? C16 C15 C14 118.09(15) . . ? C16 C15 H15 122.8(12) . . ? C14 C15 H15 119.1(12) . . ? F16 C16 C15 118.18(15) . . ? F16 C16 C17 119.00(15) . . ? C15 C16 C17 122.82(13) . . ? C16 C17 C18 118.45(14) . . ? C16 C17 H17 121.0(12) . . ? C18 C17 H17 120.5(12) . . ? C17 C18 C13 120.77(14) . . ? C17 C18 H18 119.8(9) . . ? C13 C18 H18 119.3(9) . . ? 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 C6 C1 C2 C3 3.0(3) . . . . ? C7 C1 C2 C3 -174.16(15) . . . . ? C1 C2 C3 C4 -2.0(3) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C2 C3 C4 F4 179.33(17) . . . . ? F4 C4 C5 C6 -178.05(19) . . . . ? C3 C4 C5 C6 1.8(3) . . . . ? C4 C5 C6 C1 -0.6(3) . . . . ? C2 C1 C6 C5 -1.7(3) . . . . ? C7 C1 C6 C5 175.45(18) . . . . ? C2 C1 C7 C8 28.8(2) . . . . ? C6 C1 C7 C8 -148.32(16) . . . . ? C2 C1 C7 C12 -152.97(15) . . . . ? C6 C1 C7 C12 29.9(2) . . . . ? C12 C7 C8 C9 -0.7(2) . . . . ? C1 C7 C8 C9 177.58(13) . . . . ? C7 C8 C9 O9 178.06(13) . . . . ? C7 C8 C9 C10 0.0(2) . . . . ? O9 C9 C10 C11 -177.70(12) . . . . ? C8 C9 C10 C11 0.5(2) . . . . ? O9 C9 C10 C19 -0.56(19) . . . . ? C8 C9 C10 C19 177.64(13) . . . . ? C9 C10 C19 O20 -115.72(15) . . . . ? C11 C10 C19 O20 61.39(19) . . . . ? C9 C10 C19 N21 68.22(17) . . . . ? C11 C10 C19 N21 -114.67(14) . . . . ? O20 C19 N21 N22 -2.2(2) . . . . ? C10 C19 N21 N22 173.83(13) . . . . ? C9 C10 C11 C12 -0.15(19) . . . . ? C19 C10 C11 C12 -177.28(12) . . . . ? C9 C10 C11 C13 179.67(12) . . . . ? C19 C10 C11 C13 2.53(19) . . . . ? C10 C11 C12 C7 -0.7(2) . . . . ? C13 C11 C12 C7 179.52(12) . . . . ? C8 C7 C12 C11 1.1(2) . . . . ? C1 C7 C12 C11 -177.19(13) . . . . ? C12 C11 C13 C18 46.68(18) . . . . ? C10 C11 C13 C18 -133.14(14) . . . . ? C12 C11 C13 C14 -134.58(14) . . . . ? C10 C11 C13 C14 45.60(19) . . . . ? C18 C13 C14 C15 2.2(2) . . . . ? C11 C13 C14 C15 -176.55(13) . . . . ? C13 C14 C15 C16 -1.3(2) . . . . ? C14 C15 C16 F16 179.52(14) . . . . ? C14 C15 C16 C17 -0.7(2) . . . . ? F16 C16 C17 C18 -178.55(14) . . . . ? C15 C16 C17 C18 1.6(2) . . . . ? C16 C17 C18 C13 -0.6(2) . . . . ? C14 C13 C18 C17 -1.2(2) . . . . ? C11 C13 C18 C17 177.57(13) . . . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 70.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.181 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.035 _database_code_depnum_ccdc_archive 'CCDC 933615'