Supplementary Material (ESI) for Journal of Materials Chemistry This journal is (c) The Royal Society of Chemistry 2004 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author 'Andrei S.Batsanov' _publ_contact_author_email a.s.batsanov@durham.ac.uk _journal_volume ? _journal_page_first ? _journal_page_last ? _publ_section_title ; Arene Perfluoroarene Interactions in Crystal Engineering 9: Structural Preferences in Polyfluorinated Tolans ; loop_ _publ_author_name C.E.Smith P.S.Smith R.L.Thomas E.G.Robins C.Dai A.J.Scott S.Borwick A.S.Batsanov S.W.Watt S.J.Clark C.Viney J.A.K.Howard W.Clegg T.B.Marder #====================================================================END data_1:2 _database_code_depnum_ccdc_archive 'CCDC 223639' _audit_creation_method SHELXL _chemical_name_systematic ; Tolan Perfluorotolan 1:1 molecular complex ; _chemical_name_common ? _chemical_formula_moiety 'C14 H10,C14 F10' _chemical_formula_sum 'C28 H10 F10' _chemical_formula_weight 536.36 _chemical_melting_point ? _chemical_compound_source ? 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' _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 6.0939(13) _cell_length_b 7.5286(15) _cell_length_c 12.491(3) _cell_angle_alpha 85.554(6) _cell_angle_beta 86.479(6) _cell_angle_gamma 84.095(6) _cell_volume 567.5(2) _cell_formula_units_Z 1 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 2140 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 28.01 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ;The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 3 sets of \w scans; each set at different \f and/or 2\q angles and each scan covering 0.3\% in \w. ; _diffrn_ambient_temperature 160(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 'Siemens SMART CCD area detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_reflns_number 3470 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0683 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 28.32 _reflns_number_total 2403 _reflns_number_gt 1486 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-96 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-96 (Sheldrick, 1996)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1017P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2403 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0961 _refine_ls_R_factor_gt 0.0675 _refine_ls_wR_factor_all 0.1782 _refine_ls_wR_factor_ref 0.1640 _refine_ls_goodness_of_fit_all 0.947 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 0.947 _refine_ls_restrained_S_obs 1.128 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.3279(5) 0.9286(3) 0.1353(2) 0.0402(7) Uani 1 d . . H1 H 0.2960 0.9177 0.0627 0.048 Uiso 1 calc R . C2 C 0.5366(5) 0.8708(3) 0.1707(2) 0.0393(7) Uani 1 d . . H2 H 0.6472 0.8193 0.1224 0.047 Uiso 1 calc R . C3 C 0.5840(4) 0.8875(3) 0.2755(2) 0.0355(6) Uani 1 d . . H3 H 0.7267 0.8461 0.2993 0.043 Uiso 1 calc R . C4 C 0.4238(4) 0.9649(3) 0.3473(2) 0.0313(6) Uani 1 d . . C5 C 0.2134(4) 1.0201(3) 0.3110(2) 0.0353(6) Uani 1 d . . H5 H 0.1014 1.0704 0.3591 0.042 Uiso 1 calc R . C6 C 0.1673(5) 1.0020(4) 0.2060(2) 0.0392(6) Uani 1 d . . H6 H 0.0239 1.0403 0.1821 0.047 Uiso 1 calc R . C7 C 0.4765(4) 0.9885(3) 0.4557(2) 0.0342(6) Uani 1 d . . C8 C 0.6660(4) 0.5801(3) 0.86430(19) 0.0315(6) Uani 1 d . . F1 F 0.7093(3) 0.6015(2) 0.96579(11) 0.0454(5) Uani 1 d . . C9 C 0.4622(4) 0.6444(3) 0.82617(19) 0.0293(6) Uani 1 d . . F2 F 0.3088(3) 0.72689(19) 0.89172(12) 0.0415(4) Uani 1 d . . C10 C 0.4189(4) 0.6235(3) 0.72202(19) 0.0277(6) Uani 1 d . . F3 F 0.2210(2) 0.68838(18) 0.68623(11) 0.0364(4) Uani 1 d . . C11 C 0.5742(4) 0.5375(3) 0.65203(19) 0.0265(5) Uani 1 d . . C12 C 0.7783(4) 0.4753(3) 0.69252(19) 0.0286(6) Uani 1 d . . F4 F 0.9336(2) 0.39162(19) 0.62882(12) 0.0386(4) Uani 1 d . . C13 C 0.8231(4) 0.4948(3) 0.7974(2) 0.0306(6) Uani 1 d . . F5 F 1.0196(2) 0.4297(2) 0.83496(12) 0.0428(4) Uani 1 d . . C14 C 0.5232(4) 0.5116(3) 0.54435(19) 0.0281(5) Uani 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 0.0497(18) 0.0335(14) 0.0394(15) -0.0018(12) -0.0031(13) -0.0135(12) C2 0.0371(16) 0.0335(14) 0.0471(17) -0.0064(12) 0.0088(13) -0.0061(11) C3 0.0275(14) 0.0279(13) 0.0504(17) -0.0007(11) 0.0015(12) -0.0031(10) C4 0.0287(14) 0.0248(12) 0.0402(15) -0.0001(10) 0.0031(11) -0.0062(10) C5 0.0301(14) 0.0307(13) 0.0436(15) -0.0020(11) 0.0070(12) -0.0022(10) C6 0.0313(15) 0.0376(14) 0.0494(17) -0.0003(12) -0.0065(13) -0.0068(11) C7 0.0295(14) 0.0284(12) 0.0443(14) -0.0012(11) 0.0027(12) -0.0047(10) C8 0.0361(15) 0.0319(13) 0.0287(13) -0.0001(10) -0.0034(11) -0.0142(11) F1 0.0536(11) 0.0515(10) 0.0336(9) -0.0039(7) -0.0076(7) -0.0146(8) C9 0.0307(14) 0.0259(12) 0.0314(13) -0.0049(10) 0.0080(11) -0.0072(10) F2 0.0418(10) 0.0406(9) 0.0414(9) -0.0117(7) 0.0107(7) -0.0018(7) C10 0.0211(13) 0.0240(12) 0.0383(14) -0.0003(10) -0.0023(11) -0.0047(9) F3 0.0213(8) 0.0401(8) 0.0468(9) -0.0025(7) -0.0027(6) 0.0020(6) C11 0.0238(13) 0.0228(11) 0.0337(13) -0.0018(10) -0.0011(10) -0.0070(9) C12 0.0231(13) 0.0262(12) 0.0365(14) -0.0034(10) 0.0042(11) -0.0049(9) F4 0.0245(8) 0.0424(9) 0.0477(9) -0.0093(7) 0.0032(7) 0.0041(6) C13 0.0249(13) 0.0282(12) 0.0397(14) 0.0026(10) -0.0077(11) -0.0078(10) F5 0.0264(9) 0.0497(9) 0.0527(10) 0.0039(7) -0.0144(7) -0.0047(7) C14 0.0216(12) 0.0254(11) 0.0372(13) -0.0020(10) 0.0005(11) -0.0031(9) _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 C6 1.379(4) . ? C1 C2 1.389(4) . ? C2 C3 1.376(4) . ? C3 C4 1.397(4) . ? C4 C5 1.398(3) . ? C4 C7 1.439(4) . ? C5 C6 1.379(4) . ? C7 C7 1.189(5) 2_676 ? C8 F1 1.336(3) . ? C8 C13 1.374(4) . ? C8 C9 1.384(4) . ? C9 F2 1.340(3) . ? C9 C10 1.367(3) . ? C10 F3 1.343(3) . ? C10 C11 1.393(3) . ? C11 C12 1.394(3) . ? C11 C14 1.431(3) . ? C12 F4 1.337(3) . ? C12 C13 1.377(3) . ? C13 F5 1.344(3) . ? C14 C14 1.190(5) 2_666 ? 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 119.6(3) . . ? C3 C2 C1 120.4(3) . . ? C2 C3 C4 120.5(2) . . ? C3 C4 C5 118.6(2) . . ? C3 C4 C7 120.3(2) . . ? C5 C4 C7 121.1(2) . . ? C6 C5 C4 120.5(2) . . ? C5 C6 C1 120.4(3) . . ? C7 C7 C4 178.2(4) 2_676 . ? F1 C8 C13 120.2(2) . . ? F1 C8 C9 120.0(2) . . ? C13 C8 C9 119.8(2) . . ? F2 C9 C10 120.5(2) . . ? F2 C9 C8 119.7(2) . . ? C10 C9 C8 119.9(2) . . ? F3 C10 C9 119.0(2) . . ? F3 C10 C11 119.1(2) . . ? C9 C10 C11 121.9(2) . . ? C10 C11 C12 116.9(2) . . ? C10 C11 C14 121.1(2) . . ? C12 C11 C14 122.0(2) . . ? F4 C12 C13 118.9(2) . . ? F4 C12 C11 119.4(2) . . ? C13 C12 C11 121.6(2) . . ? F5 C13 C8 119.8(2) . . ? F5 C13 C12 120.3(2) . . ? C8 C13 C12 119.9(2) . . ? C14 C14 C11 178.6(3) 2_666 . ? _refine_diff_density_max 0.442 _refine_diff_density_min -0.479 _refine_diff_density_rms 0.097 #========================================END data_3 _database_code_depnum_ccdc_archive 'CCDC 223640' _audit_creation_method SHELXL _chemical_name_systematic ; 1-(pentafluorophenyl)-2-phenylacetylene ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H5 F5' _chemical_formula_weight 268.18 _chemical_melting_point '104.0--105.0\% C' _chemical_compound_source ? 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' _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 6.1305(10) _cell_length_b 7.2444(12) _cell_length_c 12.754(2) _cell_angle_alpha 85.229(4) _cell_angle_beta 84.793(4) _cell_angle_gamma 85.766(4) _cell_volume 560.88(16) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 1891 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 28.19 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.588 _exptl_crystal_density_method ? _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.150 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ;The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 3 sets of \w scans; each set at different \f and/or 2\q angles and each scan covering 0.3\% in \w. ; _diffrn_ambient_temperature 160(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 'Siemens SMART CCD area detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_reflns_number 3479 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0635 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 28.25 _reflns_number_total 2409 _reflns_number_gt 1527 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-96 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-96 (Sheldrick, 1996)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0890P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.005(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2409 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0971 _refine_ls_R_factor_gt 0.0623 _refine_ls_wR_factor_all 0.1767 _refine_ls_wR_factor_ref 0.1584 _refine_ls_goodness_of_fit_all 1.059 _refine_ls_goodness_of_fit_ref 1.213 _refine_ls_restrained_S_all 1.059 _refine_ls_restrained_S_obs 1.213 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C -0.2189(4) 0.2141(4) 0.8436(2) 0.0293(6) Uani 1 d . . F1 F -0.2852(3) 0.2038(2) 0.94653(12) 0.0416(5) Uani 1 d . . C2 C -0.3600(4) 0.2936(4) 0.7711(2) 0.0282(6) Uani 1 d . . F2 F -0.5624(2) 0.3579(2) 0.80578(13) 0.0387(5) Uani 1 d . . C3 C -0.2922(4) 0.3044(4) 0.6658(2) 0.0291(6) Uani 1 d . . F3 F -0.4309(3) 0.3839(2) 0.59732(13) 0.0388(5) Uani 1 d . . C4 C -0.0833(4) 0.2370(3) 0.6280(2) 0.0264(6) Uani 1 d . . C5 C 0.0529(4) 0.1568(4) 0.7037(2) 0.0270(6) Uani 1 d . . F4 F 0.2554(2) 0.0881(2) 0.67211(13) 0.0369(5) Uani 1 d . . C6 C -0.0118(4) 0.1468(4) 0.8094(2) 0.0290(6) Uani 1 d . . F5 F 0.1254(3) 0.0712(2) 0.87990(13) 0.0394(5) Uani 1 d . . C7 C -0.0125(4) 0.2485(4) 0.5183(2) 0.0282(6) Uani 1 d . . C8 C 0.0460(4) 0.2591(4) 0.4265(2) 0.0290(6) Uani 1 d . . C9 C 0.1137(4) 0.2715(3) 0.3157(2) 0.0254(6) Uani 1 d . . C10 C 0.3282(4) 0.2164(4) 0.2790(2) 0.0314(7) Uani 1 d . . H10 H 0.4319 0.1722 0.3278 0.038 Uiso 1 calc R . C11 C 0.3899(5) 0.2259(4) 0.1724(2) 0.0345(7) Uani 1 d . . H11 H 0.5355 0.1863 0.1479 0.041 Uiso 1 calc R . C12 C 0.2413(5) 0.2928(4) 0.1005(2) 0.0368(7) Uani 1 d . . H12 H 0.2847 0.3001 0.0269 0.044 Uiso 1 calc R . C13 C 0.0302(5) 0.3487(4) 0.1365(2) 0.0346(7) Uani 1 d . . H13 H -0.0717 0.3946 0.0871 0.042 Uiso 1 calc R . C14 C -0.0356(4) 0.3393(4) 0.2426(2) 0.0307(6) Uani 1 d . . H14 H -0.1817 0.3787 0.2663 0.037 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0330(15) 0.0268(14) 0.0287(15) -0.0020(12) -0.0011(11) -0.0071(12) F1 0.0484(10) 0.0473(11) 0.0277(9) -0.0009(8) 0.0028(7) -0.0036(8) C2 0.0243(13) 0.0213(14) 0.0382(16) -0.0011(12) 0.0007(11) -0.0010(11) F2 0.0292(9) 0.0378(10) 0.0470(11) -0.0021(8) 0.0045(7) 0.0008(7) C3 0.0314(15) 0.0219(14) 0.0347(16) 0.0029(12) -0.0085(12) -0.0048(11) F3 0.0359(9) 0.0395(10) 0.0402(10) 0.0078(8) -0.0127(7) 0.0032(7) C4 0.0310(14) 0.0170(13) 0.0315(15) 0.0007(11) -0.0024(11) -0.0069(11) C5 0.0247(13) 0.0201(13) 0.0359(16) -0.0036(12) -0.0004(11) -0.0014(11) F4 0.0269(9) 0.0365(10) 0.0462(10) -0.0048(8) 0.0000(7) 0.0034(7) C6 0.0302(14) 0.0245(14) 0.0330(15) 0.0015(12) -0.0096(12) -0.0030(11) F5 0.0393(10) 0.0405(10) 0.0388(10) 0.0031(8) -0.0143(8) 0.0006(8) C7 0.0316(14) 0.0198(13) 0.0334(16) -0.0026(11) -0.0019(12) -0.0042(11) C8 0.0286(14) 0.0180(13) 0.0402(18) -0.0009(12) -0.0034(12) -0.0021(11) C9 0.0288(14) 0.0176(13) 0.0301(15) -0.0020(11) -0.0010(11) -0.0044(10) C10 0.0332(15) 0.0249(15) 0.0365(16) -0.0012(13) -0.0066(12) -0.0024(12) C11 0.0330(15) 0.0312(16) 0.0384(17) -0.0061(13) 0.0043(13) -0.0013(12) C12 0.0469(18) 0.0357(17) 0.0276(15) -0.0027(13) 0.0033(13) -0.0097(14) C13 0.0402(16) 0.0324(16) 0.0322(16) 0.0025(13) -0.0102(12) -0.0050(13) C14 0.0262(14) 0.0257(14) 0.0392(16) -0.0002(13) -0.0004(12) -0.0019(11) _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 1.336(3) . ? C1 C6 1.372(4) . ? C1 C2 1.385(4) . ? C2 F2 1.342(3) . ? C2 C3 1.367(4) . ? C3 F3 1.340(3) . ? C3 C4 1.395(4) . ? C4 C5 1.396(4) . ? C4 C7 1.425(4) . ? C5 F4 1.343(3) . ? C5 C6 1.368(4) . ? C6 F5 1.343(3) . ? C7 C8 1.191(4) . ? C8 C9 1.433(4) . ? C9 C10 1.397(4) . ? C9 C14 1.400(4) . ? C10 C11 1.375(4) . ? C11 C12 1.386(4) . ? C12 C13 1.377(4) . ? C13 C14 1.375(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 C6 120.4(2) . . ? F1 C1 C2 119.8(2) . . ? C6 C1 C2 119.9(3) . . ? F2 C2 C3 121.1(2) . . ? F2 C2 C1 119.1(2) . . ? C3 C2 C1 119.8(2) . . ? F3 C3 C2 118.6(2) . . ? F3 C3 C4 119.4(2) . . ? C2 C3 C4 122.0(3) . . ? C3 C4 C5 116.3(2) . . ? C3 C4 C7 122.0(2) . . ? C5 C4 C7 121.7(2) . . ? F4 C5 C6 118.6(2) . . ? F4 C5 C4 119.1(2) . . ? C6 C5 C4 122.3(2) . . ? F5 C6 C5 120.5(2) . . ? F5 C6 C1 119.8(2) . . ? C5 C6 C1 119.7(3) . . ? C8 C7 C4 179.6(3) . . ? C7 C8 C9 179.2(3) . . ? C10 C9 C14 119.0(2) . . ? C10 C9 C8 120.8(2) . . ? C14 C9 C8 120.2(2) . . ? C11 C10 C9 120.2(3) . . ? C10 C11 C12 120.4(3) . . ? C13 C12 C11 119.5(3) . . ? C14 C13 C12 121.1(3) . . ? C13 C14 C9 119.7(3) . . ? _refine_diff_density_max 0.344 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.092 #======================================================END data_4a _database_code_depnum_ccdc_archive 'CCDC 223641' _chemical_name_systematic ; 1-(4-methoxytetrafluorophenyl)-2-phenylacetylene ; _chemical_name_common ? _chemical_melting_point '76.5--78.0\% C' _chemical_formula_moiety 'C15 H8 F4 O' _chemical_formula_sum 'C15 H8 F4 O' _chemical_formula_weight 280.21 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 P2(1)/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 7.413(2) _cell_length_b 12.941(5) _cell_length_c 12.868(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.85(2) _cell_angle_gamma 90.00 _cell_volume 1212.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 14 _cell_measurement_theta_min 24.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas 'Not measured' _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_method ? _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 1.204 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7262 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'from 108 \y-scans of 3 reflections' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku AFC6S Diffractometer' _diffrn_measurement_method \w/2\q-scans _diffrn_standards_number 3 _diffrn_standards_interval_count 147 _diffrn_standards_interval_time . _diffrn_standards_decay_% 0.7 _diffrn_reflns_number 3146 _diffrn_reflns_av_R_equivalents 0.0721 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.89 _diffrn_reflns_theta_max 74.99 _reflns_number_total 2300 _reflns_number_gt 2035 _reflns_threshold_expression I>2\s(I) _computing_data_collection MSC/AFC _computing_cell_refinement MSC/AFC _computing_data_reduction TEXSAN _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL _computing_publication_material 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. ; _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^)+(0.0862P)^2^+0.4574P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2300 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1488 _refine_ls_wR_factor_gt 0.1430 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 O O 0.0662(2) 0.57393(15) 0.87657(12) 0.0432(4) Uani 1 1 d . . . F2 F -0.00662(16) 0.77575(10) 0.83697(9) 0.0352(3) Uani 1 1 d . . . F3 F -0.01559(16) 0.85780(9) 0.64566(9) 0.0333(3) Uani 1 1 d . . . F5 F 0.17839(15) 0.53996(9) 0.52492(9) 0.0328(3) Uani 1 1 d . . . F6 F 0.17459(17) 0.45520(9) 0.71313(10) 0.0390(3) Uani 1 1 d . . . C1 C 0.0836(2) 0.61343(16) 0.78114(14) 0.0277(4) Uani 1 1 d . . . C2 C 0.0385(2) 0.71643(15) 0.76027(13) 0.0251(4) Uani 1 1 d . . . C3 C 0.0353(2) 0.75871(14) 0.66185(14) 0.0234(4) Uani 1 1 d . . . C4 C 0.0819(2) 0.70144(14) 0.57855(13) 0.0222(4) Uani 1 1 d . . . C5 C 0.1316(2) 0.59909(14) 0.60099(14) 0.0239(4) Uani 1 1 d . . . C6 C 0.1310(2) 0.55544(14) 0.69868(15) 0.0271(4) Uani 1 1 d . . . C7 C 0.0781(2) 0.74427(15) 0.47580(14) 0.0260(4) Uani 1 1 d . . . C8 C 0.0790(2) 0.77449(15) 0.38795(14) 0.0273(4) Uani 1 1 d . . . C9 C 0.0830(2) 0.80823(15) 0.28208(14) 0.0245(4) Uani 1 1 d . . . C10 C 0.1122(2) 0.91200(15) 0.26037(15) 0.0277(4) Uani 1 1 d . . . H10 H 0.135(3) 0.9638(19) 0.3162(18) 0.029(6) Uiso 1 1 d . . . C11 C 0.1214(3) 0.94312(15) 0.15838(16) 0.0293(4) Uani 1 1 d . . . H11 H 0.143(3) 1.012(2) 0.1448(19) 0.032(6) Uiso 1 1 d . . . C12 C 0.0991(2) 0.87130(16) 0.07670(14) 0.0280(4) Uani 1 1 d . . . H12 H 0.104(3) 0.8942(18) 0.0078(19) 0.027(5) Uiso 1 1 d . . . C13 C 0.0685(3) 0.76824(16) 0.09754(15) 0.0287(4) Uani 1 1 d . . . H13 H 0.047(3) 0.7165(19) 0.0396(19) 0.034(6) Uiso 1 1 d . . . C14 C 0.0610(2) 0.73601(15) 0.19958(15) 0.0272(4) Uani 1 1 d . . . H14 H 0.030(3) 0.6660(19) 0.2131(19) 0.034(6) Uiso 1 1 d . . . C15 C 0.2172(3) 0.5202(2) 0.93643(17) 0.0386(5) Uani 1 1 d . . . H151 H 0.328(5) 0.560(3) 0.945(3) 0.085(11) Uiso 1 1 d . . . H152 H 0.239(7) 0.458(4) 0.909(4) 0.117(16) Uiso 1 1 d . . . H153 H 0.188(4) 0.507(2) 1.007(2) 0.055(8) 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 O 0.0362(8) 0.0674(11) 0.0290(8) 0.0248(7) 0.0141(6) 0.0136(7) F2 0.0392(6) 0.0477(8) 0.0199(6) -0.0088(5) 0.0089(4) 0.0036(5) F3 0.0425(6) 0.0255(6) 0.0328(7) -0.0003(4) 0.0090(5) 0.0027(4) F5 0.0325(6) 0.0361(6) 0.0315(6) -0.0114(5) 0.0107(4) 0.0006(4) F6 0.0434(7) 0.0281(6) 0.0468(8) 0.0084(5) 0.0119(6) 0.0051(5) C1 0.0208(8) 0.0420(11) 0.0209(9) 0.0071(8) 0.0056(6) 0.0004(7) C2 0.0221(8) 0.0363(10) 0.0175(8) -0.0039(7) 0.0054(6) -0.0006(7) C3 0.0235(8) 0.0250(8) 0.0217(9) -0.0007(7) 0.0041(6) -0.0021(6) C4 0.0208(7) 0.0299(9) 0.0166(8) -0.0001(6) 0.0048(6) -0.0034(6) C5 0.0192(7) 0.0292(9) 0.0241(9) -0.0061(7) 0.0067(6) -0.0027(6) C6 0.0225(8) 0.0267(9) 0.0322(10) 0.0046(7) 0.0055(7) 0.0002(6) C7 0.0267(8) 0.0327(9) 0.0193(9) -0.0010(7) 0.0063(6) -0.0027(7) C8 0.0253(8) 0.0354(10) 0.0222(9) 0.0014(7) 0.0068(7) 0.0010(7) C9 0.0212(8) 0.0326(9) 0.0203(9) 0.0034(7) 0.0056(6) 0.0015(6) C10 0.0284(8) 0.0300(9) 0.0244(9) -0.0003(7) 0.0042(7) 0.0029(7) C11 0.0296(9) 0.0283(9) 0.0291(10) 0.0074(8) 0.0036(7) 0.0007(7) C12 0.0268(8) 0.0385(10) 0.0186(9) 0.0075(7) 0.0041(7) 0.0001(7) C13 0.0298(9) 0.0367(10) 0.0198(9) -0.0015(8) 0.0051(7) -0.0041(7) C14 0.0301(9) 0.0289(9) 0.0231(9) 0.0031(7) 0.0060(7) -0.0038(7) C15 0.0367(10) 0.0523(13) 0.0252(10) 0.0108(9) 0.0016(8) 0.0057(10) _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 O C1 1.359(2) . ? O C15 1.416(2) . ? F2 C2 1.342(2) . ? F3 C3 1.342(2) . ? F5 C5 1.339(2) . ? F6 C6 1.341(2) . ? C1 C2 1.388(3) . ? C1 C6 1.397(3) . ? C2 C3 1.376(3) . ? C3 C4 1.399(3) . ? C4 C5 1.391(3) . ? C4 C7 1.429(2) . ? C5 C6 1.379(3) . ? C7 C8 1.197(3) . ? C8 C9 1.436(3) . ? C9 C10 1.397(3) . ? C9 C14 1.401(3) . ? C10 C11 1.387(3) . ? C11 C12 1.389(3) . ? C12 C13 1.387(3) . ? C13 C14 1.389(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O C15 118.47(15) . . ? O C1 C2 118.41(18) . . ? O C1 C6 124.37(19) . . ? C2 C1 C6 117.04(16) . . ? F2 C2 C3 119.09(17) . . ? F2 C2 C1 119.44(16) . . ? C3 C2 C1 121.46(17) . . ? F3 C3 C2 118.60(16) . . ? F3 C3 C4 119.35(16) . . ? C2 C3 C4 122.05(17) . . ? C5 C4 C3 116.08(16) . . ? C5 C4 C7 121.32(16) . . ? C3 C4 C7 122.60(17) . . ? F5 C5 C6 118.58(17) . . ? F5 C5 C4 119.19(16) . . ? C6 C5 C4 122.22(16) . . ? F6 C6 C5 118.72(17) . . ? F6 C6 C1 120.17(17) . . ? C5 C6 C1 121.11(17) . . ? C8 C7 C4 176.0(2) . . ? C7 C8 C9 178.4(2) . . ? C10 C9 C14 119.37(17) . . ? C10 C9 C8 120.90(17) . . ? C14 C9 C8 119.72(18) . . ? C11 C10 C9 120.36(17) . . ? C10 C11 C12 120.11(18) . . ? C13 C12 C11 119.83(17) . . ? C12 C13 C14 120.56(18) . . ? C13 C14 C9 119.76(18) . . ? 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 O C15 56.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.921 _diffrn_reflns_theta_full 74.99 _diffrn_measured_fraction_theta_full 0.921 _refine_diff_density_max 0.338 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.069 #========================================END data_4c _database_code_depnum_ccdc_archive 'CCDC 223642' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(4-n-propoxytetrafluorophenyl)-2-phenylacetylene ; _chemical_name_common ? _chemical_melting_point '75.0--75.5\% C' _chemical_formula_moiety ? _chemical_formula_sum 'C17 H12 F4 O' _chemical_formula_weight 308.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 7.752(2) _cell_length_b 8.652(2) _cell_length_c 11.119(3) _cell_angle_alpha 98.57(1) _cell_angle_beta 108.81(1) _cell_angle_gamma 92.06(1) _cell_volume 695.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 1.20 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.473 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 5 sets of \w scans; each set at different \f and/or 2\q angles and each scan covering 0.3\% in \w. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 120(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 8542 _diffrn_reflns_av_R_equivalents 0.0646 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 29.00 _reflns_number_total 3638 _reflns_number_gt 3232 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _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^)+(0.0606P)^2^+0.1926P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3638 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1154 _refine_ls_wR_factor_gt 0.1101 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 F2 F 0.29543(9) 0.50606(8) 0.41046(6) 0.02601(17) Uani 1 1 d . . . F3 F 0.41871(10) 0.66869(8) 0.65192(7) 0.02957(17) Uani 1 1 d . . . F5 F 0.05548(10) 0.31720(9) 0.77906(6) 0.02889(17) Uani 1 1 d . . . F6 F -0.06828(10) 0.15590(8) 0.53723(7) 0.02796(17) Uani 1 1 d . . . O O 0.04153(10) 0.24823(9) 0.34439(7) 0.02159(17) Uani 1 1 d . . . C1 C 0.11436(13) 0.32404(12) 0.46851(9) 0.01721(19) Uani 1 1 d . . . C2 C 0.24012(14) 0.45571(12) 0.50227(9) 0.0183(2) Uani 1 1 d . . . C3 C 0.30316(14) 0.53926(12) 0.62644(10) 0.0199(2) Uani 1 1 d . . . C4 C 0.24588(14) 0.49568(13) 0.72496(9) 0.0196(2) Uani 1 1 d . . . C5 C 0.11941(14) 0.36406(13) 0.69029(9) 0.0200(2) Uani 1 1 d . . . C6 C 0.05577(14) 0.28023(12) 0.56575(9) 0.0189(2) Uani 1 1 d . . . C7 C 0.31146(15) 0.58412(14) 0.85269(10) 0.0237(2) Uani 1 1 d . . . C8 C 0.36800(15) 0.65966(13) 0.95937(10) 0.0235(2) Uani 1 1 d . . . C9 C 0.43455(14) 0.75132(13) 1.08695(9) 0.0203(2) Uani 1 1 d . . . C10 C 0.57100(15) 0.87567(13) 1.11695(10) 0.0227(2) Uani 1 1 d . . . C11 C 0.63410(15) 0.96555(13) 1.24005(11) 0.0240(2) Uani 1 1 d . . . C12 C 0.56281(15) 0.93124(13) 1.33411(10) 0.0229(2) Uani 1 1 d . . . C13 C 0.42830(16) 0.80730(13) 1.30547(10) 0.0237(2) Uani 1 1 d . . . C14 C 0.36330(15) 0.71723(13) 1.18229(10) 0.0229(2) Uani 1 1 d . . . C15 C 0.15988(15) 0.14077(13) 0.30194(10) 0.0218(2) Uani 1 1 d . . . C16 C 0.09674(17) 0.11575(14) 0.15601(10) 0.0266(2) Uani 1 1 d . . . C17 C 0.12927(18) 0.26303(17) 0.10302(11) 0.0309(3) Uani 1 1 d . . . H10 H 0.622(2) 0.897(2) 1.0517(16) 0.037(4) Uiso 1 1 d . . . H11 H 0.729(2) 1.051(2) 1.2599(16) 0.037(4) Uiso 1 1 d . . . H12 H 0.608(2) 0.9953(19) 1.4194(15) 0.032(4) Uiso 1 1 d . . . H13 H 0.379(2) 0.7811(19) 1.3710(15) 0.032(4) Uiso 1 1 d . . . H14 H 0.270(2) 0.6323(19) 1.1617(15) 0.029(4) Uiso 1 1 d . . . H15A H 0.148(2) 0.0439(19) 0.3340(14) 0.028(4) Uiso 1 1 d . . . H15B H 0.288(2) 0.1857(17) 0.3396(13) 0.022(3) Uiso 1 1 d . . . H16A H 0.166(2) 0.032(2) 0.1297(16) 0.036(4) Uiso 1 1 d . . . H16B H -0.032(2) 0.077(2) 0.1236(15) 0.034(4) Uiso 1 1 d . . . H17A H 0.086(3) 0.241(2) 0.0055(19) 0.050(5) Uiso 1 1 d . . . H17B H 0.258(3) 0.298(2) 0.1321(16) 0.042(5) Uiso 1 1 d . . . H17C H 0.065(2) 0.352(2) 0.1302(16) 0.037(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 F2 0.0306(3) 0.0288(3) 0.0237(3) 0.0069(3) 0.0152(3) -0.0017(3) F3 0.0275(3) 0.0238(3) 0.0341(4) -0.0036(3) 0.0107(3) -0.0083(3) F5 0.0335(4) 0.0384(4) 0.0196(3) 0.0080(3) 0.0143(3) 0.0009(3) F6 0.0293(3) 0.0268(4) 0.0267(3) 0.0009(3) 0.0106(3) -0.0100(3) O 0.0197(3) 0.0283(4) 0.0141(3) -0.0021(3) 0.0045(3) 0.0024(3) C1 0.0166(4) 0.0199(5) 0.0140(4) 0.0010(3) 0.0043(3) 0.0029(3) C2 0.0187(4) 0.0215(5) 0.0169(4) 0.0048(4) 0.0080(3) 0.0023(4) C3 0.0169(4) 0.0187(5) 0.0225(5) 0.0004(4) 0.0058(4) -0.0002(3) C4 0.0179(4) 0.0231(5) 0.0157(4) 0.0002(3) 0.0037(3) 0.0049(4) C5 0.0204(5) 0.0257(5) 0.0155(4) 0.0050(4) 0.0071(3) 0.0040(4) C6 0.0185(4) 0.0192(5) 0.0187(4) 0.0026(4) 0.0064(4) -0.0009(4) C7 0.0208(5) 0.0280(5) 0.0194(5) -0.0004(4) 0.0041(4) 0.0049(4) C8 0.0216(5) 0.0267(5) 0.0201(5) 0.0013(4) 0.0051(4) 0.0048(4) C9 0.0204(5) 0.0219(5) 0.0163(4) 0.0002(4) 0.0039(3) 0.0040(4) C10 0.0237(5) 0.0262(5) 0.0192(5) 0.0039(4) 0.0083(4) 0.0017(4) C11 0.0222(5) 0.0228(5) 0.0244(5) 0.0000(4) 0.0065(4) -0.0021(4) C12 0.0255(5) 0.0226(5) 0.0174(4) -0.0016(4) 0.0049(4) 0.0018(4) C13 0.0284(5) 0.0243(5) 0.0200(5) 0.0026(4) 0.0107(4) 0.0017(4) C14 0.0238(5) 0.0201(5) 0.0234(5) 0.0003(4) 0.0080(4) -0.0015(4) C15 0.0275(5) 0.0207(5) 0.0179(4) 0.0002(4) 0.0096(4) 0.0029(4) C16 0.0324(6) 0.0293(6) 0.0171(5) -0.0025(4) 0.0100(4) -0.0004(4) C17 0.0323(6) 0.0420(7) 0.0221(5) 0.0094(5) 0.0124(4) 0.0034(5) _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 F2 C2 1.3479(11) . ? F3 C3 1.3440(12) . ? F5 C5 1.3434(12) . ? F6 C6 1.3453(12) . ? O C1 1.3619(12) . ? O C15 1.4625(13) . ? C1 C6 1.3947(13) . ? C1 C2 1.3950(14) . ? C2 C3 1.3820(14) . ? C3 C4 1.4014(14) . ? C4 C5 1.3970(15) . ? C4 C7 1.4295(14) . ? C5 C6 1.3861(14) . ? C7 C8 1.1998(16) . ? C8 C9 1.4390(14) . ? C9 C10 1.4041(15) . ? C9 C14 1.4052(15) . ? C10 C11 1.3932(15) . ? C11 C12 1.3931(16) . ? C12 C13 1.3936(16) . ? C13 C14 1.3949(15) . ? C15 C16 1.5148(15) . ? C16 C17 1.5268(18) . ? 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 C1 O C15 114.66(8) . . ? O C1 C6 121.17(9) . . ? O C1 C2 121.63(9) . . ? C6 C1 C2 117.03(9) . . ? F2 C2 C3 119.36(9) . . ? F2 C2 C1 119.16(9) . . ? C3 C2 C1 121.42(9) . . ? F3 C3 C2 118.67(9) . . ? F3 C3 C4 119.32(9) . . ? C2 C3 C4 121.98(9) . . ? C5 C4 C3 116.26(9) . . ? C5 C4 C7 122.48(9) . . ? C3 C4 C7 121.25(10) . . ? F5 C5 C6 118.54(9) . . ? F5 C5 C4 119.61(9) . . ? C6 C5 C4 121.86(9) . . ? F6 C6 C5 119.34(9) . . ? F6 C6 C1 119.19(9) . . ? C5 C6 C1 121.46(9) . . ? C8 C7 C4 179.10(13) . . ? C7 C8 C9 179.46(12) . . ? C10 C9 C14 119.54(9) . . ? C10 C9 C8 120.18(10) . . ? C14 C9 C8 120.28(10) . . ? C11 C10 C9 120.22(10) . . ? C12 C11 C10 119.96(10) . . ? C11 C12 C13 120.21(10) . . ? C12 C13 C14 120.29(10) . . ? C13 C14 C9 119.77(10) . . ? O C15 C16 107.72(9) . . ? C15 C16 C17 113.15(10) . . ? 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 C2 C1 O C15 80.2(1) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.387 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.055 #=============================================END data_4d _database_code_depnum_ccdc_archive 'CCDC 223643' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(4-iso-propoxytetrafluorophenyl)-2-phenylacetylene ; _chemical_name_common ? _chemical_melting_point '64.2--64.7\% C' _chemical_formula_moiety 'C17 H12 F4 O' _chemical_formula_sum 'C17 H12 F4 O' _chemical_formula_weight 308.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.1278(15) _cell_length_b 15.444(4) _cell_length_c 15.382(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.35(2) _cell_angle_gamma 90.00 _cell_volume 1443.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 22.3 _cell_measurement_theta_max 27.2 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method ? _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 1.062 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8899 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'T_max,min from 108 \y-scans of 3 reflections' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku AFC6S 4-circle diffractometer' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 147 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.8 _diffrn_reflns_number 3919 _diffrn_reflns_av_R_equivalents 0.0137 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.07 _diffrn_reflns_theta_max 75.07 _reflns_number_total 2840 _reflns_number_gt 2399 _reflns_observed_criterion I>2\s(I) _computing_data_collection MSC/AFC _computing_cell_refinement MSC/AFC _computing_data_reduction TEXSAN _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL _computing_publication_material 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. ; _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^)+(0.0755P)^2^+0.3384P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2840 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1303 _refine_ls_wR_factor_gt 0.1219 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 O O 0.7552(2) 0.88336(7) 0.05455(7) 0.0311(3) Uani 1 1 d . . . F2 F 1.05649(17) 0.77312(6) 0.14480(7) 0.0369(3) Uani 1 1 d . . . F3 F 0.95817(18) 0.60649(6) 0.17042(7) 0.0391(3) Uani 1 1 d . . . F5 F 0.24391(17) 0.65202(7) 0.02159(7) 0.0372(3) Uani 1 1 d . . . F6 F 0.34306(17) 0.81796(6) -0.00402(7) 0.0361(3) Uani 1 1 d . . . C1 C 0.7020(3) 0.79977(10) 0.07013(10) 0.0280(4) Uani 1 1 d . . . C2 C 0.8553(3) 0.74347(11) 0.11393(10) 0.0286(3) Uani 1 1 d . . . C3 C 0.8044(3) 0.65791(10) 0.12690(10) 0.0292(4) Uani 1 1 d . . . C4 C 0.5968(3) 0.62407(10) 0.09739(10) 0.0285(4) Uani 1 1 d . . . C5 C 0.4454(3) 0.68087(10) 0.05253(10) 0.0283(3) Uani 1 1 d . . . C6 C 0.4958(3) 0.76658(10) 0.03935(10) 0.0287(4) Uani 1 1 d . . . C7 C 0.5395(3) 0.53639(11) 0.11374(11) 0.0312(4) Uani 1 1 d . . . C8 C 0.4871(3) 0.46392(11) 0.12828(10) 0.0310(4) Uani 1 1 d . . . C9 C 0.4257(3) 0.37635(10) 0.14483(10) 0.0284(3) Uani 1 1 d . . . C10 C 0.5815(3) 0.31882(11) 0.18636(11) 0.0312(4) Uani 1 1 d . . . H10 H 0.724(4) 0.3388(13) 0.2046(14) 0.032(5) Uiso 1 1 d . . . C11 C 0.5237(3) 0.23341(11) 0.20017(12) 0.0340(4) Uani 1 1 d . . . H11 H 0.637(4) 0.1939(15) 0.2300(16) 0.046(6) Uiso 1 1 d . . . C12 C 0.3115(3) 0.20517(11) 0.17232(11) 0.0339(4) Uani 1 1 d . . . H12 H 0.277(4) 0.1455(14) 0.1824(14) 0.038(5) Uiso 1 1 d . . . C13 C 0.1549(3) 0.26194(12) 0.13187(12) 0.0354(4) Uani 1 1 d . . . H13 H 0.000(4) 0.2425(15) 0.1111(15) 0.045(6) Uiso 1 1 d . . . C14 C 0.2108(3) 0.34755(11) 0.11838(11) 0.0335(4) Uani 1 1 d . . . H14 H 0.105(4) 0.3877(13) 0.0924(14) 0.037(5) Uiso 1 1 d . . . C15 C 0.7598(3) 0.94103(10) 0.13113(11) 0.0324(4) Uani 1 1 d . . . H15 H 0.819(4) 0.9082(14) 0.1843(15) 0.043(6) Uiso 1 1 d . . . C16 C 0.5292(4) 0.97148(13) 0.13802(13) 0.0402(4) Uani 1 1 d . . . H161 H 0.426(5) 0.9219(18) 0.1465(18) 0.064(7) Uiso 1 1 d . . . H162 H 0.535(4) 1.0084(15) 0.1892(16) 0.046(6) Uiso 1 1 d . . . H163 H 0.469(4) 1.0069(15) 0.0849(16) 0.046(6) Uiso 1 1 d . . . C17 C 0.9131(4) 1.01404(14) 0.11539(17) 0.0493(5) Uani 1 1 d . . . H171 H 0.927(5) 1.0538(18) 0.1654(19) 0.070(8) Uiso 1 1 d . . . H172 H 0.864(5) 1.0440(17) 0.0572(19) 0.063(8) Uiso 1 1 d . . . H173 H 1.062(5) 0.9898(18) 0.1192(18) 0.060(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 O 0.0435(7) 0.0236(5) 0.0268(5) -0.0004(4) 0.0063(5) -0.0021(5) F2 0.0299(6) 0.0360(5) 0.0431(6) -0.0023(4) -0.0017(4) -0.0015(4) F3 0.0402(6) 0.0344(5) 0.0403(5) 0.0065(4) -0.0038(4) 0.0104(4) F5 0.0321(6) 0.0356(5) 0.0426(6) -0.0031(4) 0.0001(4) -0.0033(4) F6 0.0351(6) 0.0309(5) 0.0393(5) 0.0033(4) -0.0063(4) 0.0079(4) C1 0.0372(10) 0.0235(7) 0.0240(7) -0.0002(6) 0.0074(6) 0.0009(6) C2 0.0293(9) 0.0294(8) 0.0270(7) -0.0031(6) 0.0034(6) -0.0007(6) C3 0.0340(9) 0.0288(7) 0.0247(7) 0.0018(6) 0.0033(6) 0.0066(6) C4 0.0381(10) 0.0248(7) 0.0236(7) -0.0012(6) 0.0073(6) 0.0012(6) C5 0.0276(9) 0.0293(8) 0.0277(7) -0.0034(6) 0.0030(6) -0.0021(6) C6 0.0330(9) 0.0268(7) 0.0260(7) 0.0011(6) 0.0026(6) 0.0068(6) C7 0.0391(10) 0.0277(8) 0.0271(7) 0.0007(6) 0.0053(7) 0.0020(7) C8 0.0369(10) 0.0299(8) 0.0260(7) -0.0001(6) 0.0034(6) 0.0022(7) C9 0.0358(9) 0.0268(7) 0.0232(7) -0.0014(6) 0.0055(6) -0.0006(6) C10 0.0317(10) 0.0304(8) 0.0313(8) 0.0000(6) 0.0036(7) -0.0020(7) C11 0.0382(10) 0.0293(8) 0.0339(8) 0.0026(6) 0.0029(7) 0.0021(7) C12 0.0410(10) 0.0275(8) 0.0339(8) -0.0012(6) 0.0070(7) -0.0066(7) C13 0.0314(10) 0.0389(9) 0.0361(9) -0.0050(7) 0.0048(7) -0.0069(7) C14 0.0350(10) 0.0338(8) 0.0314(8) -0.0007(7) 0.0033(7) 0.0038(7) C15 0.0414(10) 0.0266(7) 0.0273(8) -0.0030(6) -0.0025(7) 0.0019(7) C16 0.0473(12) 0.0383(9) 0.0364(9) 0.0002(8) 0.0109(8) 0.0080(8) C17 0.0448(13) 0.0384(10) 0.0627(14) -0.0110(10) -0.0009(10) -0.0092(9) _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 O C1 1.3603(19) . ? O C15 1.4741(19) . ? F2 C2 1.344(2) . ? F3 C3 1.3435(19) . ? F5 C5 1.3411(19) . ? F6 C6 1.3384(18) . ? C1 C6 1.389(2) . ? C1 C2 1.390(2) . ? C2 C3 1.378(2) . ? C3 C4 1.396(2) . ? C4 C5 1.394(2) . ? C4 C7 1.429(2) . ? C5 C6 1.380(2) . ? C7 C8 1.193(2) . ? C8 C9 1.435(2) . ? C9 C10 1.398(2) . ? C9 C14 1.400(3) . ? C10 C11 1.389(2) . ? C10 H10 0.93(2) . ? C11 C12 1.387(3) . ? C11 H11 0.99(2) . ? C12 C13 1.387(3) . ? C12 H12 0.96(2) . ? C13 C14 1.388(3) . ? C13 H13 1.01(2) . ? C14 H14 0.95(2) . ? C15 C16 1.506(3) . ? C15 C17 1.507(3) . ? C15 H15 0.99(2) . ? C16 H161 1.01(3) . ? C16 H162 0.97(2) . ? C16 H163 1.01(2) . ? C17 H171 0.98(3) . ? C17 H172 1.02(3) . ? C17 H173 0.98(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O C15 114.40(12) . . ? O C1 C6 121.23(15) . . ? O C1 C2 121.12(16) . . ? C6 C1 C2 117.59(15) . . ? F2 C2 C3 119.34(15) . . ? F2 C2 C1 119.41(15) . . ? C3 C2 C1 121.26(16) . . ? F3 C3 C2 118.80(15) . . ? F3 C3 C4 119.49(14) . . ? C2 C3 C4 121.70(15) . . ? C5 C4 C3 116.52(14) . . ? C5 C4 C7 121.35(16) . . ? C3 C4 C7 122.11(15) . . ? F5 C5 C6 118.68(15) . . ? F5 C5 C4 119.41(14) . . ? C6 C5 C4 121.92(16) . . ? F6 C6 C5 119.09(15) . . ? F6 C6 C1 119.91(14) . . ? C5 C6 C1 121.00(15) . . ? C8 C7 C4 178.34(19) . . ? C7 C8 C9 179.23(18) . . ? C10 C9 C14 119.55(15) . . ? C10 C9 C8 120.03(16) . . ? C14 C9 C8 120.41(16) . . ? C11 C10 C9 120.04(17) . . ? C11 C10 H10 121.0(13) . . ? C9 C10 H10 119.0(13) . . ? C12 C11 C10 119.94(17) . . ? C12 C11 H11 121.4(14) . . ? C10 C11 H11 118.6(14) . . ? C11 C12 C13 120.49(16) . . ? C11 C12 H12 117.8(14) . . ? C13 C12 H12 121.7(14) . . ? C12 C13 C14 119.97(17) . . ? C12 C13 H13 121.6(13) . . ? C14 C13 H13 118.5(13) . . ? C13 C14 C9 120.00(16) . . ? C13 C14 H14 121.1(13) . . ? C9 C14 H14 118.8(13) . . ? O C15 C16 108.82(14) . . ? O C15 C17 105.81(15) . . ? C16 C15 C17 112.80(16) . . ? O C15 H15 108.5(13) . . ? C16 C15 H15 110.4(13) . . ? C17 C15 H15 110.3(13) . . ? C15 C16 H161 112.4(16) . . ? C15 C16 H162 107.5(14) . . ? H161 C16 H162 108(2) . . ? C15 C16 H163 111.0(14) . . ? H161 C16 H163 110(2) . . ? H162 C16 H163 108.1(18) . . ? C15 C17 H171 109.7(17) . . ? C15 C17 H172 111.0(16) . . ? H171 C17 H172 113(2) . . ? C15 C17 H173 107.3(16) . . ? H171 C17 H173 102(2) . . ? H172 C17 H173 113(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C1 O C15 -77.75(19) . . . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 75.07 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.259 _refine_diff_density_min -0.410 _refine_diff_density_rms 0.064 #===============================================END data_4f _database_code_depnum_ccdc_archive 'CCDC 223644' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(4-n-pentoxytetrafluorophenyl)-2-phenylacetylene ; _chemical_name_common ? _chemical_melting_point '27.0--27.5\% C' _chemical_formula_moiety 'C19 H16 F4 O' _chemical_formula_sum 'C19 H16 F4 O' _chemical_formula_weight 336.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 8.514(1) _cell_length_b 10.454(2) _cell_length_c 10.600(2) _cell_angle_alpha 63.225(2) _cell_angle_beta 76.621(3) _cell_angle_gamma 85.017(3) _cell_volume 819.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3572 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 26.34 _exptl_crystal_description 'irregular shape' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 5 sets of \w scans; each set at different \f and/or 2\q angles and each scan covering 0.3\% in \w. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 120(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 'SMART 1K CCD area detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 6775 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 26.38 _reflns_number_total 3315 _reflns_number_gt 2605 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _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^)+(0.0565P)^2^+0.5500P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3315 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1275 _refine_ls_wR_factor_gt 0.1155 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 O O 0.51465(17) 0.81398(14) 0.40293(15) 0.0294(3) Uani 1 1 d . . . F2 F 0.45636(13) 0.62315(12) 0.67385(12) 0.0288(3) Uani 1 1 d . . . F3 F 0.62099(15) 0.37910(12) 0.77183(12) 0.0333(3) Uani 1 1 d . . . F5 F 0.92822(14) 0.51008(13) 0.29639(13) 0.0331(3) Uani 1 1 d . . . F6 F 0.76814(15) 0.75225(13) 0.19751(12) 0.0338(3) Uani 1 1 d . . . C1 C 0.6070(2) 0.69674(19) 0.4345(2) 0.0216(4) Uani 1 1 d . . . C2 C 0.5758(2) 0.59659(19) 0.5800(2) 0.0217(4) Uani 1 1 d . . . C3 C 0.6600(2) 0.47147(19) 0.6300(2) 0.0233(4) Uani 1 1 d . . . C4 C 0.7820(2) 0.43635(19) 0.5376(2) 0.0229(4) Uani 1 1 d . . . C5 C 0.8122(2) 0.5360(2) 0.3924(2) 0.0240(4) Uani 1 1 d . . . C6 C 0.7287(2) 0.6628(2) 0.3407(2) 0.0230(4) Uani 1 1 d . . . C7 C 0.8680(2) 0.3051(2) 0.5911(2) 0.0249(4) Uani 1 1 d . . . C8 C 0.9367(2) 0.1943(2) 0.6414(2) 0.0246(4) Uani 1 1 d . . . C9 C 1.0170(2) 0.0591(2) 0.6987(2) 0.0219(4) Uani 1 1 d . . . C10 C 0.9882(2) -0.0302(2) 0.8480(2) 0.0256(4) Uani 1 1 d . . . H10 H 0.910(3) -0.003(2) 0.912(2) 0.028(6) Uiso 1 1 d . . . C11 C 1.0640(2) -0.1613(2) 0.9007(2) 0.0279(4) Uani 1 1 d . . . H11 H 1.047(3) -0.222(2) 1.000(3) 0.032(6) Uiso 1 1 d . . . C12 C 1.1680(2) -0.2052(2) 0.8057(2) 0.0266(4) Uani 1 1 d . . . H12 H 1.218(3) -0.299(2) 0.845(2) 0.026(5) Uiso 1 1 d . . . C13 C 1.1977(2) -0.1170(2) 0.6577(2) 0.0267(4) Uani 1 1 d . . . H13 H 1.271(3) -0.148(3) 0.591(3) 0.037(6) Uiso 1 1 d . . . C14 C 1.1244(2) 0.0150(2) 0.6036(2) 0.0257(4) Uani 1 1 d . . . H14 H 1.141(3) 0.074(2) 0.502(3) 0.030(6) Uiso 1 1 d . . . C15 C 0.5300(2) 0.9312(2) 0.2572(2) 0.0238(4) Uani 1 1 d . . . H151 H 0.641(3) 0.968(2) 0.221(2) 0.029(6) Uiso 1 1 d . . . H152 H 0.496(3) 0.897(2) 0.197(2) 0.022(5) Uiso 1 1 d . . . C16 C 0.4142(2) 1.0427(2) 0.2775(2) 0.0240(4) Uani 1 1 d . . . H161 H 0.304(3) 0.993(2) 0.325(2) 0.028(6) Uiso 1 1 d . . . H162 H 0.443(2) 1.068(2) 0.347(2) 0.021(5) Uiso 1 1 d . . . C17 C 0.4035(3) 1.1767(2) 0.1374(2) 0.0270(4) Uani 1 1 d . . . H171 H 0.512(3) 1.228(3) 0.091(3) 0.041(7) Uiso 1 1 d . . . H172 H 0.369(3) 1.151(2) 0.067(3) 0.033(6) Uiso 1 1 d . . . C18 C 0.2807(3) 1.2803(2) 0.1704(2) 0.0282(4) Uani 1 1 d . . . H181 H 0.172(3) 1.223(3) 0.222(3) 0.044(7) Uiso 1 1 d . . . H182 H 0.314(3) 1.301(2) 0.243(2) 0.029(6) Uiso 1 1 d . . . C19 C 0.2614(3) 1.4176(2) 0.0367(3) 0.0380(5) Uani 1 1 d . . . H191 H 0.367(4) 1.474(3) -0.011(3) 0.056(8) Uiso 1 1 d . . . H192 H 0.220(3) 1.396(3) -0.034(3) 0.045(7) Uiso 1 1 d . . . H193 H 0.185(4) 1.479(3) 0.063(3) 0.055(8) 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 O 0.0288(7) 0.0250(7) 0.0253(7) -0.0084(6) 0.0004(6) 0.0128(6) F2 0.0275(6) 0.0295(6) 0.0252(6) -0.0136(5) 0.0017(5) 0.0104(5) F3 0.0391(7) 0.0289(6) 0.0237(6) -0.0082(5) -0.0035(5) 0.0120(5) F5 0.0275(6) 0.0362(7) 0.0347(7) -0.0212(5) 0.0023(5) 0.0118(5) F6 0.0356(7) 0.0320(6) 0.0242(6) -0.0104(5) 0.0028(5) 0.0108(5) C1 0.0189(9) 0.0204(9) 0.0262(10) -0.0120(8) -0.0045(7) 0.0053(7) C2 0.0187(9) 0.0243(9) 0.0253(9) -0.0163(8) -0.0013(7) 0.0051(7) C3 0.0242(9) 0.0214(9) 0.0229(9) -0.0090(8) -0.0052(7) 0.0032(7) C4 0.0192(9) 0.0220(9) 0.0320(10) -0.0158(8) -0.0071(8) 0.0047(7) C5 0.0168(9) 0.0289(10) 0.0321(10) -0.0210(8) -0.0012(7) 0.0038(7) C6 0.0222(9) 0.0233(9) 0.0215(9) -0.0106(8) -0.0002(7) 0.0023(7) C7 0.0221(9) 0.0255(10) 0.0312(10) -0.0167(8) -0.0060(8) 0.0043(8) C8 0.0213(9) 0.0274(10) 0.0295(10) -0.0175(8) -0.0046(8) 0.0052(8) C9 0.0170(9) 0.0237(9) 0.0284(10) -0.0150(8) -0.0056(7) 0.0044(7) C10 0.0219(9) 0.0318(10) 0.0266(10) -0.0179(8) -0.0028(8) 0.0051(8) C11 0.0267(10) 0.0299(10) 0.0209(10) -0.0075(8) -0.0029(8) 0.0037(8) C12 0.0241(10) 0.0227(10) 0.0303(10) -0.0111(8) -0.0055(8) 0.0080(8) C13 0.0244(10) 0.0283(10) 0.0275(10) -0.0151(8) -0.0032(8) 0.0088(8) C14 0.0266(10) 0.0265(10) 0.0227(10) -0.0115(8) -0.0041(8) 0.0073(8) C15 0.0237(10) 0.0217(9) 0.0240(10) -0.0100(8) -0.0040(8) 0.0060(7) C16 0.0226(9) 0.0230(9) 0.0256(10) -0.0109(8) -0.0056(8) 0.0066(7) C17 0.0268(10) 0.0234(10) 0.0270(10) -0.0091(8) -0.0051(8) 0.0057(8) C18 0.0339(11) 0.0219(10) 0.0292(10) -0.0112(8) -0.0105(9) 0.0080(8) C19 0.0411(13) 0.0262(11) 0.0386(13) -0.0081(10) -0.0105(10) 0.0097(10) _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 O C1 1.348(2) . ? O C15 1.460(2) . ? F2 C2 1.354(2) . ? F3 C3 1.349(2) . ? F5 C5 1.349(2) . ? F6 C6 1.353(2) . ? C1 C2 1.397(3) . ? C1 C6 1.402(2) . ? C2 C3 1.376(3) . ? C3 C4 1.400(3) . ? C4 C5 1.393(3) . ? C4 C7 1.434(3) . ? C5 C6 1.387(3) . ? C7 C8 1.199(3) . ? C8 C9 1.444(3) . ? C9 C10 1.401(3) . ? C9 C14 1.408(3) . ? C10 C11 1.389(3) . ? C10 H10 0.96(2) . ? C11 C12 1.394(3) . ? C11 H11 0.94(2) . ? C12 C13 1.390(3) . ? C12 H12 0.98(2) . ? C13 C14 1.387(3) . ? C13 H13 0.98(2) . ? C14 H14 0.95(2) . ? C15 C16 1.518(3) . ? C15 H151 0.97(2) . ? C15 H152 0.96(2) . ? C16 C17 1.530(3) . ? C16 H161 1.01(2) . ? C16 H162 0.98(2) . ? C17 C18 1.537(3) . ? C17 H171 1.01(3) . ? C17 H172 1.01(2) . ? C18 C19 1.527(3) . ? C18 H181 1.04(3) . ? C18 H182 0.99(2) . ? C19 H191 1.01(3) . ? C19 H192 1.01(3) . ? C19 H193 0.96(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O C15 123.23(14) . . ? O C1 C2 115.06(15) . . ? O C1 C6 128.57(17) . . ? C2 C1 C6 116.37(16) . . ? F2 C2 C3 119.28(16) . . ? F2 C2 C1 118.42(15) . . ? C3 C2 C1 122.29(16) . . ? F3 C3 C2 118.74(16) . . ? F3 C3 C4 119.32(16) . . ? C2 C3 C4 121.92(17) . . ? C5 C4 C3 115.68(16) . . ? C5 C4 C7 122.98(17) . . ? C3 C4 C7 121.34(17) . . ? F5 C5 C6 117.76(17) . . ? F5 C5 C4 119.29(16) . . ? C6 C5 C4 122.95(17) . . ? F6 C6 C5 118.09(16) . . ? F6 C6 C1 121.12(16) . . ? C5 C6 C1 120.79(17) . . ? C8 C7 C4 177.3(2) . . ? C7 C8 C9 177.9(2) . . ? C10 C9 C14 119.30(17) . . ? C10 C9 C8 120.95(17) . . ? C14 C9 C8 119.75(18) . . ? C11 C10 C9 120.07(17) . . ? C11 C10 H10 120.7(13) . . ? C9 C10 H10 119.1(13) . . ? C10 C11 C12 120.29(18) . . ? C10 C11 H11 121.3(14) . . ? C12 C11 H11 118.4(14) . . ? C13 C12 C11 119.96(18) . . ? C13 C12 H12 121.0(13) . . ? C11 C12 H12 119.0(13) . . ? C14 C13 C12 120.37(18) . . ? C14 C13 H13 119.9(14) . . ? C12 C13 H13 119.7(14) . . ? C13 C14 C9 120.00(18) . . ? C13 C14 H14 120.6(14) . . ? C9 C14 H14 119.3(14) . . ? O C15 C16 104.17(15) . . ? O C15 H151 109.1(13) . . ? C16 C15 H151 111.4(13) . . ? O C15 H152 108.9(12) . . ? C16 C15 H152 110.4(12) . . ? H151 C15 H152 112.5(18) . . ? C15 C16 C17 114.58(16) . . ? C15 C16 H161 106.2(12) . . ? C17 C16 H161 109.6(12) . . ? C15 C16 H162 109.1(12) . . ? C17 C16 H162 110.8(12) . . ? H161 C16 H162 106.1(17) . . ? C16 C17 C18 110.04(16) . . ? C16 C17 H171 110.0(14) . . ? C18 C17 H171 108.2(14) . . ? C16 C17 H172 111.1(13) . . ? C18 C17 H172 108.7(13) . . ? H171 C17 H172 108.7(19) . . ? C19 C18 C17 113.86(18) . . ? C19 C18 H181 111.0(14) . . ? C17 C18 H181 106.0(14) . . ? C19 C18 H182 111.5(13) . . ? C17 C18 H182 107.9(13) . . ? H181 C18 H182 106.2(19) . . ? C18 C19 H191 110.4(16) . . ? C18 C19 H192 111.2(15) . . ? H191 C19 H192 111(2) . . ? C18 C19 H193 110.9(17) . . ? H191 C19 H193 106(2) . . ? H192 C19 H193 107(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 O C1 C2 179.49(17) . . . . ? C15 O C1 C6 -0.7(3) . . . . ? C5 C4 C7 C8 175(4) . . . . ? C3 C4 C7 C8 -6(5) . . . . ? C4 C7 C8 C9 123(6) . . . . ? C7 C8 C9 C10 -124(6) . . . . ? C7 C8 C9 C14 56(6) . . . . ? C1 O C15 C16 -174.96(17) . . . . ? O C15 C16 C17 -178.12(17) . . . . ? C15 C16 C17 C18 178.82(18) . . . . ? C16 C17 C18 C19 -179.89(19) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.274 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.055 #===============================================END data_4i _database_code_depnum_ccdc_archive 'CCDC 223645' _chemical_name_systematic ; 1-(4-tolyloxytetrafluorophenyl)-2-phenylacetylene ; _chemical_name_common ? _chemical_melting_point '85.0--86.5\% C' _chemical_formula_moiety 'C21 H12 F4 O' _chemical_formula_sum 'C21 H12 F4 O' _chemical_formula_weight 356.31 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.918(2) _cell_length_b 5.777(2) _cell_length_c 35.872(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.32(1) _cell_angle_gamma 90.00 _cell_volume 1636.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 964 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 27.45 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan covering 0.3\% in \w. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 120(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 SMART CCD 1K area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 11617 _diffrn_reflns_av_R_equivalents 0.0469 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 27.45 _reflns_number_total 3421 _reflns_number_gt 2962 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SMART-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _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^)+(0.0311P)^2^+1.0639P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3421 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.0990 _refine_ls_wR_factor_gt 0.0934 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 O O 0.47009(15) 0.2958(2) 0.17127(3) 0.0316(3) Uani 1 1 d . . . C1 C 0.4158(2) 0.2185(3) 0.13614(4) 0.0263(3) Uani 1 1 d . . . F2 F 0.57217(13) -0.12887(18) 0.14441(3) 0.0352(2) Uani 1 1 d . . . C2 C 0.4739(2) 0.0109(3) 0.12208(4) 0.0262(3) Uani 1 1 d . . . F3 F 0.49088(13) -0.25300(17) 0.07299(3) 0.0328(2) Uani 1 1 d . . . C3 C 0.4316(2) -0.0510(3) 0.08549(4) 0.0253(3) Uani 1 1 d . . . C4 C 0.3302(2) 0.0877(3) 0.06124(4) 0.0250(3) Uani 1 1 d . . . F5 F 0.17455(13) 0.43657(18) 0.05393(3) 0.0362(3) Uani 1 1 d . . . C5 C 0.2726(2) 0.2953(3) 0.07581(4) 0.0263(3) Uani 1 1 d . . . F6 F 0.25455(13) 0.55770(17) 0.12573(3) 0.0356(2) Uani 1 1 d . . . C6 C 0.3137(2) 0.3573(3) 0.11253(4) 0.0263(3) Uani 1 1 d . . . C7 C 0.2837(2) 0.0210(3) 0.02345(4) 0.0283(3) Uani 1 1 d . . . C8 C 0.2414(2) -0.0320(3) -0.00814(4) 0.0285(4) Uani 1 1 d . . . C9 C 0.1911(2) -0.0875(3) -0.04650(4) 0.0259(3) Uani 1 1 d . . . C10 C 0.2393(2) -0.2968(3) -0.06214(5) 0.0292(4) Uani 1 1 d . . . H10 H 0.303(3) -0.409(4) -0.0475(5) 0.036(5) Uiso 1 1 d . . . C11 C 0.1927(2) -0.3445(3) -0.09952(5) 0.0314(4) Uani 1 1 d . . . H11 H 0.225(2) -0.495(4) -0.1105(5) 0.037(5) Uiso 1 1 d . . . C12 C 0.0978(2) -0.1854(3) -0.12124(5) 0.0309(4) Uani 1 1 d . . . H12 H 0.066(2) -0.218(4) -0.1482(6) 0.038(5) Uiso 1 1 d . . . C13 C 0.0490(2) 0.0228(3) -0.10567(5) 0.0311(4) Uani 1 1 d . . . H13 H -0.014(3) 0.132(4) -0.1209(5) 0.036(5) Uiso 1 1 d . . . C14 C 0.0952(2) 0.0724(3) -0.06848(5) 0.0285(4) Uani 1 1 d . . . H14 H 0.063(2) 0.212(4) -0.0575(5) 0.031(5) Uiso 1 1 d . . . C15 C 0.36774(19) 0.2501(3) 0.20081(4) 0.0238(3) Uani 1 1 d . . . C16 C 0.3736(2) 0.4132(3) 0.22903(4) 0.0249(3) Uani 1 1 d . . . H16 H 0.435(2) 0.550(3) 0.2261(5) 0.028(5) Uiso 1 1 d . . . C17 C 0.2896(2) 0.3695(3) 0.26106(4) 0.0263(3) Uani 1 1 d . . . H17 H 0.297(2) 0.480(4) 0.2816(5) 0.036(5) Uiso 1 1 d . . . C18 C 0.20071(19) 0.1639(3) 0.26503(4) 0.0259(3) Uani 1 1 d . . . C19 C 0.1928(2) 0.0067(3) 0.23542(5) 0.0277(3) Uani 1 1 d . . . H19 H 0.131(2) -0.137(4) 0.2371(5) 0.031(5) Uiso 1 1 d . . . C20 C 0.2759(2) 0.0469(3) 0.20318(4) 0.0270(3) Uani 1 1 d . . . H20 H 0.274(2) -0.062(3) 0.1841(5) 0.031(5) Uiso 1 1 d . . . C21 C 0.1232(2) 0.1053(4) 0.30104(5) 0.0347(4) Uani 1 1 d . . . H21C H 0.095(3) 0.249(4) 0.3148(7) 0.057(7) Uiso 1 1 d . . . H21B H 0.019(3) 0.012(4) 0.2959(6) 0.043(6) Uiso 1 1 d . . . H21A H 0.201(3) 0.019(4) 0.3171(6) 0.040(5) 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 O 0.0328(6) 0.0389(7) 0.0237(5) -0.0047(5) 0.0051(5) -0.0144(5) C1 0.0264(8) 0.0291(8) 0.0239(7) -0.0003(6) 0.0057(6) -0.0094(7) F2 0.0363(6) 0.0367(6) 0.0320(5) 0.0080(4) -0.0011(4) 0.0027(4) C2 0.0257(8) 0.0266(8) 0.0265(8) 0.0057(6) 0.0034(6) -0.0024(7) F3 0.0380(6) 0.0248(5) 0.0364(5) -0.0030(4) 0.0088(4) 0.0034(4) C3 0.0271(8) 0.0210(8) 0.0287(8) -0.0002(6) 0.0083(6) -0.0022(6) C4 0.0251(8) 0.0266(8) 0.0238(7) 0.0005(6) 0.0052(6) -0.0059(6) F5 0.0377(6) 0.0330(6) 0.0372(5) 0.0053(4) -0.0018(4) 0.0057(5) C5 0.0253(8) 0.0252(8) 0.0284(8) 0.0045(6) 0.0022(6) -0.0023(6) F6 0.0409(6) 0.0253(5) 0.0416(6) -0.0071(4) 0.0098(4) 0.0007(4) C6 0.0282(8) 0.0210(8) 0.0309(8) -0.0030(6) 0.0095(6) -0.0032(6) C7 0.0286(8) 0.0285(8) 0.0283(8) 0.0006(7) 0.0059(6) -0.0038(7) C8 0.0289(8) 0.0283(9) 0.0289(8) 0.0002(7) 0.0066(6) -0.0037(7) C9 0.0257(8) 0.0286(8) 0.0242(7) -0.0010(6) 0.0067(6) -0.0065(7) C10 0.0310(9) 0.0272(9) 0.0299(8) 0.0015(7) 0.0055(7) -0.0016(7) C11 0.0355(9) 0.0278(9) 0.0318(8) -0.0047(7) 0.0088(7) -0.0046(7) C12 0.0329(9) 0.0362(9) 0.0241(8) -0.0039(7) 0.0049(7) -0.0073(8) C13 0.0310(9) 0.0332(9) 0.0293(8) 0.0038(7) 0.0036(7) -0.0004(7) C14 0.0307(9) 0.0268(9) 0.0288(8) -0.0021(7) 0.0074(7) -0.0025(7) C15 0.0222(7) 0.0275(8) 0.0216(7) 0.0016(6) 0.0009(6) -0.0014(6) C16 0.0259(8) 0.0215(8) 0.0267(7) 0.0011(6) -0.0022(6) -0.0017(6) C17 0.0273(8) 0.0276(8) 0.0235(7) -0.0035(6) -0.0017(6) 0.0035(7) C18 0.0221(8) 0.0315(9) 0.0238(7) 0.0045(6) 0.0002(6) 0.0030(6) C19 0.0264(8) 0.0258(8) 0.0309(8) 0.0027(7) 0.0014(6) -0.0039(7) C20 0.0286(8) 0.0259(8) 0.0262(8) -0.0039(7) 0.0010(6) -0.0049(7) C21 0.0317(9) 0.0458(11) 0.0265(8) 0.0058(8) 0.0027(7) -0.0004(9) _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 O C1 1.3752(19) . ? O C15 1.4064(18) . ? C1 C6 1.383(2) . ? C1 C2 1.393(2) . ? F2 C2 1.3434(18) . ? C2 C3 1.377(2) . ? F3 C3 1.3474(18) . ? C3 C4 1.392(2) . ? C4 C5 1.398(2) . ? C4 C7 1.431(2) . ? F5 C5 1.3389(18) . ? C5 C6 1.380(2) . ? F6 C6 1.3481(18) . ? C7 C8 1.197(2) . ? C8 C9 1.440(2) . ? C9 C10 1.399(2) . ? C9 C14 1.400(2) . ? C10 C11 1.391(2) . ? C11 C12 1.389(3) . ? C12 C13 1.393(3) . ? C13 C14 1.386(2) . ? C15 C16 1.381(2) . ? C15 C20 1.387(2) . ? C16 C17 1.393(2) . ? C17 C18 1.393(2) . ? C18 C19 1.395(2) . ? C18 C21 1.510(2) . ? C19 C20 1.393(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 C1 O C15 118.13(12) . . ? O C1 C6 120.06(15) . . ? O C1 C2 121.53(15) . . ? C6 C1 C2 118.14(14) . . ? F2 C2 C3 120.07(15) . . ? F2 C2 C1 119.58(14) . . ? C3 C2 C1 120.35(15) . . ? F3 C3 C2 118.43(14) . . ? F3 C3 C4 119.32(14) . . ? C2 C3 C4 122.25(15) . . ? C3 C4 C5 116.69(14) . . ? C3 C4 C7 122.13(15) . . ? C5 C4 C7 121.17(15) . . ? F5 C5 C6 119.08(15) . . ? F5 C5 C4 119.64(14) . . ? C6 C5 C4 121.28(15) . . ? F6 C6 C5 119.66(15) . . ? F6 C6 C1 119.06(14) . . ? C5 C6 C1 121.28(15) . . ? C8 C7 C4 178.48(18) . . ? C7 C8 C9 177.99(18) . . ? C10 C9 C14 119.84(15) . . ? C10 C9 C8 120.75(15) . . ? C14 C9 C8 119.39(15) . . ? C11 C10 C9 119.80(16) . . ? C12 C11 C10 120.19(16) . . ? C11 C12 C13 120.08(15) . . ? C14 C13 C12 120.23(17) . . ? C13 C14 C9 119.85(16) . . ? C16 C15 C20 121.42(14) . . ? C16 C15 O 115.74(14) . . ? C20 C15 O 122.67(14) . . ? C15 C16 C17 119.27(15) . . ? C18 C17 C16 120.99(15) . . ? C17 C18 C19 118.12(14) . . ? C17 C18 C21 121.30(15) . . ? C19 C18 C21 120.49(16) . . ? C20 C19 C18 121.76(15) . . ? C15 C20 C19 118.37(15) . . ? _diffrn_measured_fraction_theta_max 0.913 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.913 _refine_diff_density_max 0.238 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.047 #===============================================END #===============================================END data_4i _database_code_depnum_ccdc_archive 'CCDC 223646' _chemical_name_systematic ; 1-(4-tolyloxytetrafluorophenyl)-2-phenylacetylene ; _chemical_name_common ? _chemical_melting_point '85.0--86.5\% C' _chemical_formula_moiety 'C21 H12 F4 O' _chemical_formula_sum 'C21 H12 F4 O' _chemical_formula_weight 356.31 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.918(2) _cell_length_b 5.777(2) _cell_length_c 35.872(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.32(1) _cell_angle_gamma 90.00 _cell_volume 1636.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 964 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 27.45 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan covering 0.3\% in \w. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 120(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 SMART CCD 1K area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 11617 _diffrn_reflns_av_R_equivalents 0.0469 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 27.45 _reflns_number_total 3421 _reflns_number_gt 2962 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SMART-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _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^)+(0.0311P)^2^+1.0639P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3421 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.0990 _refine_ls_wR_factor_gt 0.0934 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 O O 0.47009(15) 0.2958(2) 0.17127(3) 0.0316(3) Uani 1 1 d . . . C1 C 0.4158(2) 0.2185(3) 0.13614(4) 0.0263(3) Uani 1 1 d . . . F2 F 0.57217(13) -0.12887(18) 0.14441(3) 0.0352(2) Uani 1 1 d . . . C2 C 0.4739(2) 0.0109(3) 0.12208(4) 0.0262(3) Uani 1 1 d . . . F3 F 0.49088(13) -0.25300(17) 0.07299(3) 0.0328(2) Uani 1 1 d . . . C3 C 0.4316(2) -0.0510(3) 0.08549(4) 0.0253(3) Uani 1 1 d . . . C4 C 0.3302(2) 0.0877(3) 0.06124(4) 0.0250(3) Uani 1 1 d . . . F5 F 0.17455(13) 0.43657(18) 0.05393(3) 0.0362(3) Uani 1 1 d . . . C5 C 0.2726(2) 0.2953(3) 0.07581(4) 0.0263(3) Uani 1 1 d . . . F6 F 0.25455(13) 0.55770(17) 0.12573(3) 0.0356(2) Uani 1 1 d . . . C6 C 0.3137(2) 0.3573(3) 0.11253(4) 0.0263(3) Uani 1 1 d . . . C7 C 0.2837(2) 0.0210(3) 0.02345(4) 0.0283(3) Uani 1 1 d . . . C8 C 0.2414(2) -0.0320(3) -0.00814(4) 0.0285(4) Uani 1 1 d . . . C9 C 0.1911(2) -0.0875(3) -0.04650(4) 0.0259(3) Uani 1 1 d . . . C10 C 0.2393(2) -0.2968(3) -0.06214(5) 0.0292(4) Uani 1 1 d . . . H10 H 0.303(3) -0.409(4) -0.0475(5) 0.036(5) Uiso 1 1 d . . . C11 C 0.1927(2) -0.3445(3) -0.09952(5) 0.0314(4) Uani 1 1 d . . . H11 H 0.225(2) -0.495(4) -0.1105(5) 0.037(5) Uiso 1 1 d . . . C12 C 0.0978(2) -0.1854(3) -0.12124(5) 0.0309(4) Uani 1 1 d . . . H12 H 0.066(2) -0.218(4) -0.1482(6) 0.038(5) Uiso 1 1 d . . . C13 C 0.0490(2) 0.0228(3) -0.10567(5) 0.0311(4) Uani 1 1 d . . . H13 H -0.014(3) 0.132(4) -0.1209(5) 0.036(5) Uiso 1 1 d . . . C14 C 0.0952(2) 0.0724(3) -0.06848(5) 0.0285(4) Uani 1 1 d . . . H14 H 0.063(2) 0.212(4) -0.0575(5) 0.031(5) Uiso 1 1 d . . . C15 C 0.36774(19) 0.2501(3) 0.20081(4) 0.0238(3) Uani 1 1 d . . . C16 C 0.3736(2) 0.4132(3) 0.22903(4) 0.0249(3) Uani 1 1 d . . . H16 H 0.435(2) 0.550(3) 0.2261(5) 0.028(5) Uiso 1 1 d . . . C17 C 0.2896(2) 0.3695(3) 0.26106(4) 0.0263(3) Uani 1 1 d . . . H17 H 0.297(2) 0.480(4) 0.2816(5) 0.036(5) Uiso 1 1 d . . . C18 C 0.20071(19) 0.1639(3) 0.26503(4) 0.0259(3) Uani 1 1 d . . . C19 C 0.1928(2) 0.0067(3) 0.23542(5) 0.0277(3) Uani 1 1 d . . . H19 H 0.131(2) -0.137(4) 0.2371(5) 0.031(5) Uiso 1 1 d . . . C20 C 0.2759(2) 0.0469(3) 0.20318(4) 0.0270(3) Uani 1 1 d . . . H20 H 0.274(2) -0.062(3) 0.1841(5) 0.031(5) Uiso 1 1 d . . . C21 C 0.1232(2) 0.1053(4) 0.30104(5) 0.0347(4) Uani 1 1 d . . . H21C H 0.095(3) 0.249(4) 0.3148(7) 0.057(7) Uiso 1 1 d . . . H21B H 0.019(3) 0.012(4) 0.2959(6) 0.043(6) Uiso 1 1 d . . . H21A H 0.201(3) 0.019(4) 0.3171(6) 0.040(5) 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 O 0.0328(6) 0.0389(7) 0.0237(5) -0.0047(5) 0.0051(5) -0.0144(5) C1 0.0264(8) 0.0291(8) 0.0239(7) -0.0003(6) 0.0057(6) -0.0094(7) F2 0.0363(6) 0.0367(6) 0.0320(5) 0.0080(4) -0.0011(4) 0.0027(4) C2 0.0257(8) 0.0266(8) 0.0265(8) 0.0057(6) 0.0034(6) -0.0024(7) F3 0.0380(6) 0.0248(5) 0.0364(5) -0.0030(4) 0.0088(4) 0.0034(4) C3 0.0271(8) 0.0210(8) 0.0287(8) -0.0002(6) 0.0083(6) -0.0022(6) C4 0.0251(8) 0.0266(8) 0.0238(7) 0.0005(6) 0.0052(6) -0.0059(6) F5 0.0377(6) 0.0330(6) 0.0372(5) 0.0053(4) -0.0018(4) 0.0057(5) C5 0.0253(8) 0.0252(8) 0.0284(8) 0.0045(6) 0.0022(6) -0.0023(6) F6 0.0409(6) 0.0253(5) 0.0416(6) -0.0071(4) 0.0098(4) 0.0007(4) C6 0.0282(8) 0.0210(8) 0.0309(8) -0.0030(6) 0.0095(6) -0.0032(6) C7 0.0286(8) 0.0285(8) 0.0283(8) 0.0006(7) 0.0059(6) -0.0038(7) C8 0.0289(8) 0.0283(9) 0.0289(8) 0.0002(7) 0.0066(6) -0.0037(7) C9 0.0257(8) 0.0286(8) 0.0242(7) -0.0010(6) 0.0067(6) -0.0065(7) C10 0.0310(9) 0.0272(9) 0.0299(8) 0.0015(7) 0.0055(7) -0.0016(7) C11 0.0355(9) 0.0278(9) 0.0318(8) -0.0047(7) 0.0088(7) -0.0046(7) C12 0.0329(9) 0.0362(9) 0.0241(8) -0.0039(7) 0.0049(7) -0.0073(8) C13 0.0310(9) 0.0332(9) 0.0293(8) 0.0038(7) 0.0036(7) -0.0004(7) C14 0.0307(9) 0.0268(9) 0.0288(8) -0.0021(7) 0.0074(7) -0.0025(7) C15 0.0222(7) 0.0275(8) 0.0216(7) 0.0016(6) 0.0009(6) -0.0014(6) C16 0.0259(8) 0.0215(8) 0.0267(7) 0.0011(6) -0.0022(6) -0.0017(6) C17 0.0273(8) 0.0276(8) 0.0235(7) -0.0035(6) -0.0017(6) 0.0035(7) C18 0.0221(8) 0.0315(9) 0.0238(7) 0.0045(6) 0.0002(6) 0.0030(6) C19 0.0264(8) 0.0258(8) 0.0309(8) 0.0027(7) 0.0014(6) -0.0039(7) C20 0.0286(8) 0.0259(8) 0.0262(8) -0.0039(7) 0.0010(6) -0.0049(7) C21 0.0317(9) 0.0458(11) 0.0265(8) 0.0058(8) 0.0027(7) -0.0004(9) _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 O C1 1.3752(19) . ? O C15 1.4064(18) . ? C1 C6 1.383(2) . ? C1 C2 1.393(2) . ? F2 C2 1.3434(18) . ? C2 C3 1.377(2) . ? F3 C3 1.3474(18) . ? C3 C4 1.392(2) . ? C4 C5 1.398(2) . ? C4 C7 1.431(2) . ? F5 C5 1.3389(18) . ? C5 C6 1.380(2) . ? F6 C6 1.3481(18) . ? C7 C8 1.197(2) . ? C8 C9 1.440(2) . ? C9 C10 1.399(2) . ? C9 C14 1.400(2) . ? C10 C11 1.391(2) . ? C11 C12 1.389(3) . ? C12 C13 1.393(3) . ? C13 C14 1.386(2) . ? C15 C16 1.381(2) . ? C15 C20 1.387(2) . ? C16 C17 1.393(2) . ? C17 C18 1.393(2) . ? C18 C19 1.395(2) . ? C18 C21 1.510(2) . ? C19 C20 1.393(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 C1 O C15 118.13(12) . . ? O C1 C6 120.06(15) . . ? O C1 C2 121.53(15) . . ? C6 C1 C2 118.14(14) . . ? F2 C2 C3 120.07(15) . . ? F2 C2 C1 119.58(14) . . ? C3 C2 C1 120.35(15) . . ? F3 C3 C2 118.43(14) . . ? F3 C3 C4 119.32(14) . . ? C2 C3 C4 122.25(15) . . ? C3 C4 C5 116.69(14) . . ? C3 C4 C7 122.13(15) . . ? C5 C4 C7 121.17(15) . . ? F5 C5 C6 119.08(15) . . ? F5 C5 C4 119.64(14) . . ? C6 C5 C4 121.28(15) . . ? F6 C6 C5 119.66(15) . . ? F6 C6 C1 119.06(14) . . ? C5 C6 C1 121.28(15) . . ? C8 C7 C4 178.48(18) . . ? C7 C8 C9 177.99(18) . . ? C10 C9 C14 119.84(15) . . ? C10 C9 C8 120.75(15) . . ? C14 C9 C8 119.39(15) . . ? C11 C10 C9 119.80(16) . . ? C12 C11 C10 120.19(16) . . ? C11 C12 C13 120.08(15) . . ? C14 C13 C12 120.23(17) . . ? C13 C14 C9 119.85(16) . . ? C16 C15 C20 121.42(14) . . ? C16 C15 O 115.74(14) . . ? C20 C15 O 122.67(14) . . ? C15 C16 C17 119.27(15) . . ? C18 C17 C16 120.99(15) . . ? C17 C18 C19 118.12(14) . . ? C17 C18 C21 121.30(15) . . ? C19 C18 C21 120.49(16) . . ? C20 C19 C18 121.76(15) . . ? C15 C20 C19 118.37(15) . . ? _diffrn_measured_fraction_theta_max 0.913 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.913 _refine_diff_density_max 0.238 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.047 #===============================================END