data_chan91s_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H15 F O' _chemical_formula_sum 'C18 H15 F O' _chemical_formula_weight 266.30 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 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 5.6207(6) _cell_length_b 8.9814(9) _cell_length_c 13.4657(16) _cell_angle_alpha 90.00 _cell_angle_beta 98.176(6) _cell_angle_gamma 90.00 _cell_volume 672.86(13) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 3719 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 29.91 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9652 _exptl_absorpt_correction_T_max 0.9947 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10599 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 30.56 _reflns_number_total 2894 _reflns_number_gt 2398 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0855P)^2^+0.1807P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.4(11) _refine_ls_number_reflns 2894 _refine_ls_number_parameters 181 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1457 _refine_ls_wR_factor_gt 0.1228 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 C1 C 0.4626(4) 0.1765(3) 0.05653(19) 0.0201(5) Uani 1 1 d . . . H1 H 0.6193 0.1605 0.1006 0.024 Uiso 1 1 calc R . . C2 C 0.4706(6) 0.1255(3) -0.0495(2) 0.0339(6) Uani 1 1 d . . . H2A H 0.5933 0.0469 -0.0516 0.041 Uiso 1 1 calc R . . H2B H 0.5071 0.2096 -0.0924 0.041 Uiso 1 1 calc R . . C3 C 0.2198(6) 0.0652(4) -0.0834(2) 0.0371(7) Uani 1 1 d . . . H3A H 0.1399 0.1232 -0.1413 0.045 Uiso 1 1 calc R . . H3B H 0.2281 -0.0403 -0.1040 0.045 Uiso 1 1 calc R . . C4 C 0.2611(4) 0.0831(3) 0.08949(18) 0.0182(4) Uani 1 1 d . . . C5 C 0.3461(4) -0.0746(3) 0.12297(17) 0.0172(4) Uani 1 1 d . . . C6 C 0.1864(4) -0.1934(3) 0.1035(2) 0.0243(5) Uani 1 1 d . . . H6 H 0.0296 -0.1765 0.0686 0.029 Uiso 1 1 calc R . . C7 C 0.2558(5) -0.3367(3) 0.1348(2) 0.0283(6) Uani 1 1 d . . . H7 H 0.1465 -0.4172 0.1208 0.034 Uiso 1 1 calc R . . C8 C 0.4840(5) -0.3625(3) 0.18651(19) 0.0241(5) Uani 1 1 d . . . H8 H 0.5306 -0.4601 0.2086 0.029 Uiso 1 1 calc R . . C9 C 0.6420(5) -0.2454(3) 0.2055(2) 0.0248(5) Uani 1 1 d . . . H9 H 0.7982 -0.2628 0.2408 0.030 Uiso 1 1 calc R . . C10 C 0.5759(4) -0.1019(3) 0.1735(2) 0.0215(5) Uani 1 1 d . . . H10 H 0.6876 -0.0224 0.1862 0.026 Uiso 1 1 calc R . . C11 C 0.1478(4) 0.1569(3) 0.16772(19) 0.0194(5) Uani 1 1 d . . . C12 C 0.0562(4) 0.2216(3) 0.2308(2) 0.0211(5) Uani 1 1 d . . . C13 C -0.0535(4) 0.2996(3) 0.30644(19) 0.0206(5) Uani 1 1 d . . . C14 C 0.0349(5) 0.4370(3) 0.3420(2) 0.0241(5) Uani 1 1 d . . . H14 H 0.1685 0.4798 0.3166 0.029 Uiso 1 1 calc R . . C15 C -0.0710(5) 0.5122(3) 0.4146(2) 0.0267(5) Uani 1 1 d . . . H15 H -0.0099 0.6062 0.4383 0.032 Uiso 1 1 calc R . . C16 C -0.2661(5) 0.4502(3) 0.4526(2) 0.0272(6) Uani 1 1 d . . . H16 H -0.3370 0.5012 0.5028 0.033 Uiso 1 1 calc R . . C17 C -0.3571(5) 0.3132(3) 0.4169(2) 0.0271(6) Uani 1 1 d . . . H17 H -0.4911 0.2712 0.4424 0.032 Uiso 1 1 calc R . . C18 C -0.2525(5) 0.2378(3) 0.3440(2) 0.0262(5) Uani 1 1 d . . . H18 H -0.3154 0.1445 0.3196 0.031 Uiso 1 1 calc R . . F1 F 0.3914(3) 0.32689(17) 0.05367(14) 0.0326(4) Uani 1 1 d . . . O1 O 0.0871(3) 0.0783(2) 0.00087(15) 0.0283(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0200(11) 0.0164(11) 0.0247(12) 0.0008(9) 0.0060(9) 0.0021(9) C2 0.0459(17) 0.0323(15) 0.0270(14) 0.0053(12) 0.0177(12) 0.0053(13) C3 0.0558(19) 0.0355(16) 0.0183(13) -0.0031(11) -0.0009(12) 0.0059(14) C4 0.0179(11) 0.0196(11) 0.0174(11) 0.0007(8) 0.0033(8) -0.0004(8) C5 0.0182(10) 0.0178(10) 0.0161(10) -0.0016(8) 0.0041(8) -0.0013(8) C6 0.0187(11) 0.0235(12) 0.0304(14) 0.0013(10) 0.0021(9) -0.0045(9) C7 0.0300(14) 0.0202(12) 0.0347(15) 0.0009(10) 0.0040(11) -0.0081(10) C8 0.0316(13) 0.0196(12) 0.0224(12) 0.0027(9) 0.0085(10) 0.0023(10) C9 0.0230(12) 0.0265(13) 0.0240(12) 0.0011(10) 0.0006(9) 0.0038(9) C10 0.0195(11) 0.0200(11) 0.0243(12) -0.0004(9) 0.0004(9) 0.0006(9) C11 0.0174(10) 0.0197(11) 0.0214(11) 0.0038(9) 0.0040(8) 0.0003(8) C12 0.0190(10) 0.0216(11) 0.0234(12) 0.0027(9) 0.0056(9) 0.0027(9) C13 0.0181(11) 0.0224(11) 0.0221(12) 0.0035(9) 0.0058(9) 0.0069(9) C14 0.0228(12) 0.0240(13) 0.0265(13) 0.0016(10) 0.0067(9) -0.0006(9) C15 0.0310(14) 0.0207(12) 0.0286(13) -0.0019(10) 0.0048(11) 0.0021(10) C16 0.0327(14) 0.0250(13) 0.0257(13) 0.0009(10) 0.0103(11) 0.0108(10) C17 0.0231(12) 0.0299(14) 0.0305(14) 0.0036(11) 0.0117(10) 0.0055(10) C18 0.0276(13) 0.0233(12) 0.0299(14) -0.0004(10) 0.0117(11) 0.0010(10) F1 0.0389(9) 0.0202(8) 0.0410(10) 0.0033(7) 0.0140(7) -0.0005(7) O1 0.0284(10) 0.0285(10) 0.0261(10) 0.0010(8) -0.0027(7) -0.0010(8) _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 C1 F1 1.408(3) . ? C1 C2 1.507(4) . ? C1 C4 1.525(3) . ? C2 C3 1.518(5) . ? C3 O1 1.449(4) . ? C4 O1 1.432(3) . ? C4 C11 1.465(3) . ? C4 C5 1.541(3) . ? C5 C10 1.393(3) . ? C5 C6 1.395(3) . ? C6 C7 1.393(4) . ? C7 C8 1.389(4) . ? C8 C9 1.377(4) . ? C9 C10 1.393(4) . ? C11 C12 1.204(3) . ? C12 C13 1.444(3) . ? C13 C14 1.390(4) . ? C13 C18 1.406(3) . ? C14 C15 1.389(4) . ? C15 C16 1.390(4) . ? C16 C17 1.391(4) . ? C17 C18 1.390(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F1 C1 C2 108.2(2) . . ? F1 C1 C4 108.42(18) . . ? C2 C1 C4 103.4(2) . . ? C1 C2 C3 104.0(2) . . ? O1 C3 C2 107.1(2) . . ? O1 C4 C11 107.29(19) . . ? O1 C4 C1 102.79(19) . . ? C11 C4 C1 112.18(19) . . ? O1 C4 C5 111.27(19) . . ? C11 C4 C5 110.71(19) . . ? C1 C4 C5 112.24(18) . . ? C10 C5 C6 119.0(2) . . ? C10 C5 C4 122.1(2) . . ? C6 C5 C4 118.9(2) . . ? C7 C6 C5 120.3(2) . . ? C8 C7 C6 120.3(2) . . ? C9 C8 C7 119.4(2) . . ? C8 C9 C10 120.9(2) . . ? C9 C10 C5 120.1(2) . . ? C12 C11 C4 178.0(2) . . ? C11 C12 C13 179.9(3) . . ? C14 C13 C18 119.3(2) . . ? C14 C13 C12 120.4(2) . . ? C18 C13 C12 120.2(2) . . ? C15 C14 C13 120.4(2) . . ? C14 C15 C16 120.2(2) . . ? C15 C16 C17 119.8(2) . . ? C18 C17 C16 120.2(2) . . ? C17 C18 C13 120.0(2) . . ? C4 O1 C3 106.8(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.56 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.787 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.072