data_crystal_004 _audit_creation_date 2013-08-19 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:59:47, GUI svn.r4466) ; _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_name '' _publ_contact_author_phone ? _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C24 H23 F O' _chemical_formula_sum 'C24 H23 F O' _chemical_formula_weight 346.42 _chemical_absolute_configuration syn _chemical_melting_point ? 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' 'F' 'F' 0.0171 0.0103 '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' _space_group_crystal_system 'monoclinic' _space_group_IT_number 5 _space_group_name_H-M_alt 'C 1 2 1' _space_group_name_Hall 'C 2y' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 16.777(6) _cell_length_b 15.082(5) _cell_length_c 15.600(6) _cell_angle_alpha 90 _cell_angle_beta 110.639(6) _cell_angle_gamma 90 _cell_volume 3694(2) _cell_formula_units_Z 8 _cell_measurement_reflns_used 5030 _cell_measurement_temperature 100 _cell_measurement_theta_max 24.86 _cell_measurement_theta_min 2.59 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type 'none' _exptl_absorpt_process_details ? _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 1472 _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_special_details ; ? ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.1056 _diffrn_reflns_av_unetI/netI 0.1027 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 25299 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.357 _diffrn_reflns_theta_min 1.395 _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_type 'MoK\a' _diffrn_radiation_wavelength 0.71073 _diffrn_source ? _diffrn_standards_number 0 _reflns_Friedel_coverage 0.923 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 5419 _reflns_number_total 7544 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.334 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.072 _refine_ls_abs_structure_details ; Flack x determined using 1982 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). The absolute stereochemistry cannot be determined from the diffraction data. The absolute stereochemistry was assigned by reference to the chiral center present in the starting material. ; _refine_ls_abs_structure_Flack -0.5(5) _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 471 _refine_ls_number_reflns 7544 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1120 _refine_ls_R_factor_gt 0.0797 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+11.5801P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1624 _refine_ls_wR_factor_ref 0.1746 _refine_special_details ; ? ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All O(H) groups 2.a Secondary CH2 refined with riding coordinates: C9(H9A,H9B), C12(H12A,H12B), C9B(H9BA,H9BB), C12B(H12C,H12D) 2.b Aromatic/amide H refined with riding coordinates: C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C4B(H4B), C5B(H5B), C6B(H6B), C7B(H7B), C8B(H8B), C10B(H10B), C14B(H14B), C15B(H15B), C16B(H16B), C17B(H17B), C18B(H18B), C20B(H20B), C21B(H21B), C22B(H22B), C23B(H23B), C24B(H24B) 2.c X=CH2 refined with riding coordinates: C11(H11A,H11B), C11B(H11C,H11D) 2.d Idealised tetrahedral OH refined as rotating group: O1(H1), O1B(H1B) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary ? 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.1016(2) 0.1283(2) 0.0191(2) 0.0229(9) Uani 1 1 d . . . . . O1 O 0.0459(3) -0.0295(3) -0.0636(3) 0.0223(11) Uani 1 1 d . . . . . H1 H 0.0195 0.0129 -0.0511 0.033 Uiso 1 1 calc R U . . . C1 C 0.1455(4) 0.0912(4) -0.0357(4) 0.0164(14) Uani 1 1 d . . . . . C2 C 0.1352(4) -0.0117(4) -0.0277(4) 0.0156(14) Uani 1 1 d . . . . . C3 C 0.1762(4) -0.0618(4) -0.0873(4) 0.0136(13) Uani 1 1 d . . . . . C4 C 0.2605(5) -0.0914(4) -0.0521(4) 0.0201(15) Uani 1 1 d . . . . . H4 H 0.2936 -0.0809 0.0104 0.024 Uiso 1 1 calc R U . . . C5 C 0.2962(5) -0.1357(4) -0.1074(4) 0.0199(14) Uani 1 1 d . . . . . H5 H 0.3537 -0.1551 -0.0826 0.024 Uiso 1 1 calc R U . . . C6 C 0.2495(5) -0.1518(4) -0.1975(4) 0.0242(16) Uani 1 1 d . . . . . H6 H 0.2745 -0.1829 -0.2346 0.029 Uiso 1 1 calc R U . . . C7 C 0.1667(5) -0.1233(4) -0.2346(4) 0.0207(15) Uani 1 1 d . . . . . H7 H 0.1349 -0.1331 -0.2976 0.025 Uiso 1 1 calc R U . . . C8 C 0.1294(5) -0.0801(4) -0.1793(4) 0.0160(14) Uani 1 1 d . . . . . H8 H 0.0713 -0.0628 -0.2045 0.019 Uiso 1 1 calc R U . . . C9 C 0.1698(5) -0.0412(4) 0.0728(4) 0.0199(15) Uani 1 1 d . . . . . H9A H 0.2315 -0.0278 0.0987 0.024 Uiso 1 1 calc R U . . . H9B H 0.1414 -0.0061 0.1075 0.024 Uiso 1 1 calc R U . . . C10 C 0.1571(4) -0.1379(4) 0.0866(4) 0.0209(15) Uani 1 1 d . . . . . H10 H 0.1846 -0.1797 0.0608 0.025 Uiso 1 1 calc R U . . . C11 C 0.1105(4) -0.1680(4) 0.1319(4) 0.0181(14) Uani 1 1 d . . . . . H11A H 0.0823 -0.1278 0.1585 0.022 Uiso 1 1 calc R U . . . H11B H 0.1049 -0.2301 0.1383 0.022 Uiso 1 1 calc R U . . . C12 C 0.0979(5) 0.1245(4) -0.1329(4) 0.0265(17) Uani 1 1 d . . . . . H12A H 0.1259 0.0994 -0.1737 0.032 Uiso 1 1 calc R U . . . H12B H 0.0392 0.1006 -0.1532 0.032 Uiso 1 1 calc R U . . . C13 C 0.0926(4) 0.2236(4) -0.1457(4) 0.0219(15) Uani 1 1 d . . . . . C14 C 0.0355(5) 0.2730(5) -0.1188(5) 0.0343(19) Uani 1 1 d . . . . . H14 H 0.0026 0.2439 -0.0886 0.041 Uiso 1 1 calc R U . . . C15 C 0.0250(5) 0.3644(5) -0.1350(5) 0.0316(18) Uani 1 1 d . . . . . H15 H -0.0133 0.3972 -0.1146 0.038 Uiso 1 1 calc R U . . . C16 C 0.0713(5) 0.4059(5) -0.1813(5) 0.0322(19) Uani 1 1 d . . . . . H16 H 0.0636 0.4676 -0.1941 0.039 Uiso 1 1 calc R U . . . C17 C 0.1290(5) 0.3585(5) -0.2094(4) 0.0288(17) Uani 1 1 d . . . . . H17 H 0.1617 0.3876 -0.2399 0.035 Uiso 1 1 calc R U . . . C18 C 0.1380(5) 0.2673(4) -0.1921(4) 0.0276(17) Uani 1 1 d . . . . . H18 H 0.1762 0.2345 -0.2127 0.033 Uiso 1 1 calc R U . . . C19 C 0.2370(4) 0.1211(4) 0.0060(4) 0.0155(14) Uani 1 1 d . . . . . C20 C 0.2704(5) 0.1510(4) 0.0962(4) 0.0221(15) Uani 1 1 d . . . . . H20 H 0.2345 0.1553 0.1314 0.027 Uiso 1 1 calc R U . . . C21 C 0.3555(5) 0.1745(5) 0.1350(4) 0.0304(18) Uani 1 1 d . . . . . H21 H 0.3774 0.1950 0.1965 0.036 Uiso 1 1 calc R U . . . C22 C 0.4088(5) 0.1683(4) 0.0848(5) 0.0278(16) Uani 1 1 d . . . . . H22 H 0.4671 0.1845 0.1114 0.033 Uiso 1 1 calc R U . . . C23 C 0.3764(4) 0.1384(4) -0.0043(4) 0.0220(15) Uani 1 1 d . . . . . H23 H 0.4128 0.1333 -0.0388 0.026 Uiso 1 1 calc R U . . . C24 C 0.2919(5) 0.1156(4) -0.0439(4) 0.0242(16) Uani 1 1 d . . . . . H24 H 0.2705 0.0960 -0.1057 0.029 Uiso 1 1 calc R U . . . F1B F -0.1077(2) -0.1387(2) -0.5179(2) 0.0209(9) Uani 1 1 d . . . . . O1B O -0.0359(3) -0.2912(3) -0.4322(3) 0.0221(11) Uani 1 1 d . . . . . H1B H -0.0163 -0.2568 -0.4622 0.033 Uiso 1 1 calc R U . . . C1B C -0.1411(4) -0.1774(4) -0.4552(4) 0.0150(13) Uani 1 1 d . . . . . C2B C -0.1270(4) -0.2804(4) -0.4616(4) 0.0166(14) Uani 1 1 d . . . . . C3B C -0.1590(4) -0.3340(4) -0.3988(4) 0.0149(13) Uani 1 1 d . . . . . C4B C -0.2425(4) -0.3634(4) -0.4252(4) 0.0186(14) Uani 1 1 d . . . . . H4B H -0.2812 -0.3486 -0.4844 0.022 Uiso 1 1 calc R U . . . C5B C -0.2708(5) -0.4135(4) -0.3680(4) 0.0233(16) Uani 1 1 d . . . . . H5B H -0.3281 -0.4337 -0.3887 0.028 Uiso 1 1 calc R U . . . C6B C -0.2166(5) -0.4346(4) -0.2807(5) 0.0281(17) Uani 1 1 d . . . . . H6B H -0.2367 -0.4680 -0.2408 0.034 Uiso 1 1 calc R U . . . C7B C -0.1331(5) -0.4069(4) -0.2522(4) 0.0225(15) Uani 1 1 d . . . . . H7B H -0.0954 -0.4218 -0.1925 0.027 Uiso 1 1 calc R U . . . C8B C -0.1034(4) -0.3573(4) -0.3096(4) 0.0181(14) Uani 1 1 d . . . . . H8B H -0.0455 -0.3388 -0.2891 0.022 Uiso 1 1 calc R U . . . C9B C -0.1665(4) -0.3114(4) -0.5627(4) 0.0171(14) Uani 1 1 d . . . . . H9BA H -0.2287 -0.3010 -0.5848 0.021 Uiso 1 1 calc R U . . . H9BB H -0.1426 -0.2751 -0.6008 0.021 Uiso 1 1 calc R U . . . C10B C -0.1501(4) -0.4077(4) -0.5750(4) 0.0206(15) Uani 1 1 d . . . . . H10B H -0.1681 -0.4499 -0.5404 0.025 Uiso 1 1 calc R U . . . C11B C -0.1125(6) -0.4372(5) -0.6301(6) 0.047(3) Uani 1 1 d . . . . . H11C H -0.0937 -0.3967 -0.6656 0.057 Uiso 1 1 calc R U . . . H11D H -0.1041 -0.4991 -0.6346 0.057 Uiso 1 1 calc R U . . . C12B C -0.0884(5) -0.1389(4) -0.3617(4) 0.0236(16) Uani 1 1 d . . . . . H12C H -0.1117 -0.1617 -0.3157 0.028 Uiso 1 1 calc R U . . . H12D H -0.0293 -0.1612 -0.3445 0.028 Uiso 1 1 calc R U . . . C13B C -0.0857(5) -0.0392(4) -0.3562(4) 0.0222(16) Uani 1 1 d . . . . . C14B C -0.0328(5) 0.0097(5) -0.3902(4) 0.0246(16) Uani 1 1 d . . . . . H14B H 0.0014 -0.0198 -0.4187 0.030 Uiso 1 1 calc R U . . . C15B C -0.0299(5) 0.1010(5) -0.3825(5) 0.0313(18) Uani 1 1 d . . . . . H15B H 0.0055 0.1333 -0.4074 0.038 Uiso 1 1 calc R U . . . C16B C -0.0765(5) 0.1464(4) -0.3402(4) 0.0268(17) Uani 1 1 d . . . . . H16B H -0.0724 0.2091 -0.3342 0.032 Uiso 1 1 calc R U . . . C17B C -0.1292(5) 0.0992(4) -0.3069(4) 0.0243(16) Uani 1 1 d . . . . . H17B H -0.1625 0.1295 -0.2780 0.029 Uiso 1 1 calc R U . . . C18B C -0.1342(5) 0.0067(4) -0.3149(4) 0.0238(16) Uani 1 1 d . . . . . H18B H -0.1713 -0.0249 -0.2919 0.029 Uiso 1 1 calc R U . . . C19B C -0.2339(4) -0.1537(4) -0.4850(4) 0.0120(12) Uani 1 1 d . . . . . C20B C -0.2771(4) -0.1204(4) -0.5730(4) 0.0153(13) Uani 1 1 d . . . . . H20B H -0.2466 -0.1094 -0.6129 0.018 Uiso 1 1 calc R U . . . C21B C -0.3633(4) -0.1034(4) -0.6025(4) 0.0196(15) Uani 1 1 d . . . . . H21B H -0.3913 -0.0800 -0.6622 0.023 Uiso 1 1 calc R U . . . C22B C -0.4087(5) -0.1199(4) -0.5467(5) 0.0286(17) Uani 1 1 d . . . . . H22B H -0.4683 -0.1093 -0.5678 0.034 Uiso 1 1 calc R U . . . C23B C -0.3672(5) -0.1520(4) -0.4597(5) 0.0268(16) Uani 1 1 d . . . . . H23B H -0.3984 -0.1633 -0.4204 0.032 Uiso 1 1 calc R U . . . C24B C -0.2806(5) -0.1678(4) -0.4290(4) 0.0193(15) Uani 1 1 d . . . . . H24B H -0.2527 -0.1887 -0.3683 0.023 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.031(2) 0.0190(19) 0.0175(18) -0.0068(15) 0.0073(17) -0.0015(17) O1 0.017(3) 0.020(2) 0.030(3) -0.009(2) 0.008(2) -0.007(2) C1 0.020(4) 0.017(3) 0.010(3) -0.007(2) 0.003(3) 0.002(3) C2 0.015(4) 0.014(3) 0.018(3) -0.007(2) 0.006(3) -0.008(3) C3 0.023(4) 0.007(3) 0.012(3) -0.003(2) 0.006(3) -0.003(3) C4 0.028(4) 0.015(3) 0.014(3) -0.001(2) 0.003(3) -0.001(3) C5 0.028(4) 0.012(3) 0.022(3) 0.002(3) 0.012(3) 0.004(3) C6 0.044(5) 0.018(3) 0.016(3) 0.002(3) 0.017(3) 0.005(3) C7 0.032(4) 0.018(3) 0.012(3) -0.002(2) 0.008(3) -0.002(3) C8 0.025(4) 0.012(3) 0.012(3) -0.001(2) 0.007(3) -0.003(3) C9 0.030(4) 0.016(3) 0.014(3) -0.001(2) 0.008(3) -0.008(3) C10 0.037(4) 0.010(3) 0.019(3) 0.000(2) 0.013(3) -0.003(3) C11 0.031(4) 0.009(3) 0.018(3) 0.002(2) 0.012(3) -0.002(3) C12 0.033(5) 0.019(3) 0.016(3) 0.000(3) -0.006(3) 0.001(3) C13 0.022(4) 0.019(3) 0.015(3) -0.004(3) -0.005(3) -0.003(3) C14 0.038(5) 0.034(4) 0.022(4) 0.001(3) -0.001(3) -0.003(4) C15 0.033(5) 0.031(4) 0.026(4) 0.000(3) 0.004(3) 0.007(3) C16 0.046(5) 0.017(3) 0.022(3) 0.005(3) -0.003(4) 0.004(3) C17 0.041(5) 0.026(4) 0.017(3) 0.004(3) 0.007(3) 0.003(3) C18 0.035(5) 0.024(4) 0.015(3) 0.008(3) -0.001(3) 0.007(3) C19 0.027(4) 0.005(3) 0.008(3) 0.003(2) -0.001(3) 0.001(3) C20 0.026(4) 0.019(3) 0.017(3) -0.002(2) 0.002(3) 0.003(3) C21 0.029(5) 0.037(4) 0.019(3) -0.014(3) 0.001(3) 0.005(3) C22 0.026(4) 0.023(4) 0.029(4) -0.005(3) 0.003(3) 0.003(3) C23 0.026(4) 0.016(3) 0.025(3) 0.001(3) 0.010(3) 0.005(3) C24 0.037(5) 0.025(4) 0.008(3) 0.001(2) 0.004(3) -0.008(3) F1B 0.020(2) 0.031(2) 0.0140(17) 0.0071(15) 0.0084(15) -0.0059(17) O1B 0.013(3) 0.034(3) 0.017(2) 0.0110(19) 0.0032(19) 0.001(2) C1B 0.018(4) 0.019(3) 0.008(3) 0.001(2) 0.005(3) -0.009(3) C2B 0.013(4) 0.026(3) 0.011(3) 0.006(2) 0.005(3) -0.001(3) C3B 0.015(3) 0.017(3) 0.015(3) 0.002(2) 0.008(3) 0.000(3) C4B 0.023(4) 0.020(3) 0.019(3) 0.001(3) 0.014(3) -0.001(3) C5B 0.037(4) 0.015(3) 0.029(4) -0.013(3) 0.024(3) -0.009(3) C6B 0.045(5) 0.019(3) 0.026(4) -0.004(3) 0.020(4) -0.012(3) C7B 0.038(5) 0.017(3) 0.013(3) 0.004(3) 0.010(3) 0.003(3) C8B 0.027(4) 0.017(3) 0.013(3) -0.002(2) 0.011(3) -0.003(3) C9B 0.020(4) 0.020(3) 0.011(3) 0.003(2) 0.006(3) 0.000(3) C10B 0.028(4) 0.022(3) 0.012(3) 0.004(3) 0.007(3) -0.001(3) C11B 0.073(7) 0.030(4) 0.064(5) -0.031(4) 0.055(5) -0.032(4) C12B 0.028(4) 0.026(4) 0.014(3) 0.009(3) 0.003(3) -0.008(3) C13B 0.031(4) 0.022(3) 0.009(3) 0.005(2) 0.001(3) -0.009(3) C14B 0.021(4) 0.029(4) 0.019(3) 0.010(3) 0.000(3) -0.007(3) C15B 0.030(5) 0.032(4) 0.023(4) 0.009(3) -0.002(3) -0.014(3) C16B 0.035(4) 0.017(3) 0.022(3) 0.008(3) 0.001(3) 0.001(3) C17B 0.028(4) 0.022(3) 0.018(3) 0.003(3) 0.002(3) 0.005(3) C18B 0.033(4) 0.020(3) 0.015(3) 0.005(3) 0.004(3) -0.004(3) C19B 0.016(3) 0.011(3) 0.011(3) -0.001(2) 0.006(2) -0.004(2) C20B 0.023(4) 0.012(3) 0.010(3) 0.001(2) 0.005(3) 0.002(3) C21B 0.020(4) 0.012(3) 0.020(3) 0.004(2) -0.001(3) 0.003(3) C22B 0.023(4) 0.019(3) 0.045(4) 0.006(3) 0.012(4) 0.007(3) C23B 0.027(4) 0.020(4) 0.043(4) 0.003(3) 0.024(4) 0.006(3) C24B 0.033(4) 0.012(3) 0.015(3) -0.004(2) 0.010(3) 0.000(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C1 1.426(7) . ? O1 C2 1.428(8) . ? C1 C2 1.572(8) . ? C1 C12 1.527(8) . ? C1 C19 1.509(9) . ? C2 C3 1.534(8) . ? C2 C9 1.534(8) . ? C3 C4 1.398(9) . ? C3 C8 1.400(8) . ? C4 C5 1.383(9) . ? C5 C6 1.368(9) . ? C6 C7 1.372(10) . ? C7 C8 1.393(9) . ? C9 C10 1.500(8) . ? C10 C11 1.307(9) . ? C12 C13 1.507(9) . ? C13 C14 1.390(11) . ? C13 C18 1.389(10) . ? C14 C15 1.402(10) . ? C15 C16 1.384(11) . ? C16 C17 1.393(10) . ? C17 C18 1.399(9) . ? C19 C20 1.393(8) . ? C19 C24 1.403(9) . ? C20 C21 1.386(10) . ? C21 C22 1.384(11) . ? C22 C23 1.378(9) . ? C23 C24 1.374(10) . ? F1B C1B 1.414(6) . ? O1B C2B 1.440(8) . ? C1B C2B 1.579(9) . ? C1B C12B 1.529(8) . ? C1B C19B 1.502(9) . ? C2B C3B 1.508(8) . ? C2B C9B 1.553(8) . ? C3B C4B 1.386(9) . ? C3B C8B 1.419(8) . ? C4B C5B 1.374(8) . ? C5B C6B 1.383(10) . ? C6B C7B 1.377(10) . ? C7B C8B 1.388(8) . ? C9B C10B 1.503(8) . ? C10B C11B 1.311(10) . ? C12B C13B 1.507(9) . ? C13B C14B 1.396(9) . ? C13B C18B 1.387(10) . ? C14B C15B 1.380(10) . ? C15B C16B 1.371(10) . ? C16B C17B 1.373(10) . ? C17B C18B 1.400(9) . ? C19B C20B 1.400(8) . ? C19B C24B 1.380(8) . ? C20B C21B 1.378(9) . ? C21B C22B 1.367(10) . ? C22B C23B 1.377(10) . ? C23B C24B 1.381(10) . ? 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 F1 C1 C2 104.2(5) . . ? F1 C1 C12 105.4(5) . . ? F1 C1 C19 106.7(4) . . ? C12 C1 C2 111.7(5) . . ? C19 C1 C2 112.6(5) . . ? C19 C1 C12 115.2(5) . . ? O1 C2 C1 106.5(5) . . ? O1 C2 C3 107.5(5) . . ? O1 C2 C9 108.3(5) . . ? C3 C2 C1 110.6(5) . . ? C9 C2 C1 110.8(4) . . ? C9 C2 C3 112.8(5) . . ? C4 C3 C2 121.8(5) . . ? C4 C3 C8 117.6(6) . . ? C8 C3 C2 120.6(6) . . ? C5 C4 C3 120.7(6) . . ? C6 C5 C4 120.6(7) . . ? C5 C6 C7 120.4(6) . . ? C6 C7 C8 119.6(6) . . ? C7 C8 C3 121.0(6) . . ? C10 C9 C2 114.0(5) . . ? C11 C10 C9 123.9(6) . . ? C13 C12 C1 116.3(5) . . ? C14 C13 C12 120.4(7) . . ? C18 C13 C12 121.5(6) . . ? C18 C13 C14 117.8(6) . . ? C13 C14 C15 121.9(7) . . ? C16 C15 C14 118.8(7) . . ? C15 C16 C17 120.8(7) . . ? C16 C17 C18 118.9(7) . . ? C13 C18 C17 121.7(7) . . ? C20 C19 C1 121.2(6) . . ? C20 C19 C24 118.1(6) . . ? C24 C19 C1 120.7(5) . . ? C21 C20 C19 120.6(7) . . ? C22 C21 C20 120.4(6) . . ? C23 C22 C21 119.3(7) . . ? C24 C23 C22 120.9(7) . . ? C23 C24 C19 120.7(6) . . ? F1B C1B C2B 105.0(5) . . ? F1B C1B C12B 105.4(5) . . ? F1B C1B C19B 107.9(5) . . ? C12B C1B C2B 112.6(5) . . ? C19B C1B C2B 112.2(5) . . ? C19B C1B C12B 113.1(5) . . ? O1B C2B C1B 104.9(5) . . ? O1B C2B C3B 108.3(5) . . ? O1B C2B C9B 108.3(5) . . ? C3B C2B C1B 113.0(5) . . ? C3B C2B C9B 112.1(5) . . ? C9B C2B C1B 109.9(4) . . ? C4B C3B C2B 122.2(5) . . ? C4B C3B C8B 117.3(5) . . ? C8B C3B C2B 120.5(6) . . ? C5B C4B C3B 121.8(6) . . ? C4B C5B C6B 120.5(7) . . ? C7B C6B C5B 119.3(6) . . ? C6B C7B C8B 120.7(6) . . ? C7B C8B C3B 120.3(6) . . ? C10B C9B C2B 112.8(5) . . ? C11B C10B C9B 124.3(6) . . ? C13B C12B C1B 115.4(5) . . ? C14B C13B C12B 121.1(7) . . ? C18B C13B C12B 120.9(6) . . ? C18B C13B C14B 118.0(6) . . ? C15B C14B C13B 120.1(7) . . ? C16B C15B C14B 122.1(7) . . ? C15B C16B C17B 118.4(6) . . ? C16B C17B C18B 120.6(7) . . ? C13B C18B C17B 120.8(7) . . ? C20B C19B C1B 120.7(5) . . ? C24B C19B C1B 121.7(5) . . ? C24B C19B C20B 117.6(6) . . ? C21B C20B C19B 121.0(6) . . ? C22B C21B C20B 120.5(6) . . ? C21B C22B C23B 119.4(7) . . ? C22B C23B C24B 120.4(6) . . ? C19B C24B C23B 121.1(6) . . ? _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelxl_version_number 2013-2 # start Validation Reply Form _vrf_PLAT417_crystal_004 ; PROBLEM: Short Inter D-H..H-D H1B .. H1B .. 1.46 Ang. RESPONSE: This alert results from hydrogen-bonding disorder between symmetry generated hydrogen-bonded pairs. ; # end Validation Reply Form #============================================================================== # Schley, Caltech 8/19/2013