#------------------------------------------------------------------------------ #$Date: 2014-07-15 22:48:18 +0300 (Tue, 15 Jul 2014) $ #$Revision: 120443 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/17/7151751.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7151751 loop_ _publ_author_name 'Ponce Gonz\'alez, Julia' 'Edgar, Mark' 'Elsegood, Mark R. J.' 'Weaver, George W.' _publ_section_title ; Synthesis of fluorinated fused benzofurans and benzothiophenes: Smiles-type rearrangement and cyclisation of perfluoro(het)aryl ethers and sulfides. ; _journal_issue 7 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 2294 _journal_page_last 2305 _journal_volume 9 _journal_year 2011 _chemical_formula_moiety 'C18 H8 F2 O2' _chemical_formula_sum 'C18 H8 F2 O2' _chemical_formula_weight 294.24 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 97.211(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 6.198(2) _cell_length_b 6.525(2) _cell_length_c 15.416(5) _cell_measurement_reflns_used 519 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 23.55 _cell_measurement_theta_min 3.32 _cell_volume 618.5(3) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX 2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device_type 'Bruker APEX 2 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_radiation_monochromator 'silicon 111' _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.6942 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0634 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 2656 _diffrn_reflns_theta_full 22.99 _diffrn_reflns_theta_max 22.99 _diffrn_reflns_theta_min 3.32 _diffrn_standards_decay_% 4 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_correction_T_min 0.992 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1, Sheldrick, G.M., (2008)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.580 _exptl_crystal_density_method 'not measured' _exptl_crystal_description lath _exptl_crystal_F_000 300 _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.974 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.094 _refine_ls_extinction_coef 0.8(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 101 _refine_ls_number_reflns 907 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.1365 _refine_ls_R_factor_gt 0.0949 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1905P)^2^+0.7738P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2480 _refine_ls_wR_factor_ref 0.2902 _reflns_number_gt 588 _reflns_number_total 907 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file c0ob00790k.txt _[local]_cod_data_source_block 22 _[local]_cod_cif_authors_sg_H-M P2(1)/n _cod_database_code 7151751 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' 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 O1 O 0.3000(7) 0.2143(7) 0.6197(3) 0.0524(15) Uani 1 1 d . . . C2 C 0.4431(10) 0.3776(10) 0.6368(4) 0.0476(18) Uani 1 1 d . . . C3 C 0.4151(11) 0.5308(11) 0.6944(4) 0.054(2) Uani 1 1 d . . . H3 H 0.2932 0.5348 0.7261 0.065 Uiso 1 1 calc R . . C4 C 0.5743(13) 0.6798(10) 0.7040(4) 0.060(2) Uani 1 1 d . . . H4 H 0.5616 0.7901 0.7432 0.072 Uiso 1 1 calc R . . C5 C 0.7529(11) 0.6731(11) 0.6577(5) 0.057(2) Uani 1 1 d . . . H5 H 0.8597 0.7781 0.6661 0.068 Uiso 1 1 calc R . . C6 C 0.7772(10) 0.5174(10) 0.6002(4) 0.0504(19) Uani 1 1 d . . . H6 H 0.8990 0.5124 0.5685 0.061 Uiso 1 1 calc R . . C7 C 0.6180(10) 0.3677(9) 0.5899(4) 0.0480(19) Uani 1 1 d . . . C8 C 0.5862(9) 0.1777(9) 0.5372(4) 0.0428(17) Uani 1 1 d . . . C9 C 0.6941(9) 0.0819(10) 0.4779(4) 0.0454(18) Uani 1 1 d . . . F1 F 0.8815(5) 0.1611(6) 0.4546(2) 0.0546(14) Uani 1 1 d . . . C10 C 0.3932(10) 0.0946(9) 0.5589(4) 0.0442(18) 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 O1 0.056(3) 0.044(3) 0.059(3) -0.006(2) 0.012(2) -0.004(2) C2 0.048(4) 0.036(4) 0.056(4) 0.007(3) -0.009(3) -0.007(3) C3 0.056(4) 0.056(5) 0.048(4) 0.008(3) 0.002(3) 0.009(3) C4 0.091(5) 0.042(4) 0.041(4) -0.008(3) -0.016(4) 0.016(4) C5 0.054(4) 0.040(4) 0.069(5) 0.008(3) -0.019(3) -0.012(3) C6 0.051(4) 0.050(4) 0.048(4) 0.013(3) 0.000(3) 0.003(3) C7 0.062(4) 0.035(4) 0.042(4) 0.002(3) -0.010(3) 0.010(3) C8 0.042(3) 0.035(4) 0.047(4) 0.004(3) -0.009(3) -0.003(3) C9 0.032(3) 0.042(4) 0.062(4) 0.016(3) 0.006(3) -0.008(3) F1 0.046(2) 0.045(2) 0.074(3) 0.0042(18) 0.0130(17) -0.0054(16) C10 0.054(4) 0.040(4) 0.040(3) 0.003(3) 0.006(3) 0.017(3) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C10 104.3(5) . . ? C3 C2 C7 123.3(6) . . ? C3 C2 O1 123.8(6) . . ? C7 C2 O1 112.9(6) . . ? C2 C3 C4 116.0(6) . . ? C3 C4 C5 121.8(6) . . ? C6 C5 C4 121.0(6) . . ? C5 C6 C7 117.6(6) . . ? C2 C7 C6 120.2(6) . . ? C2 C7 C8 105.5(6) . . ? C6 C7 C8 134.3(6) . . ? C9 C8 C10 119.7(5) . . ? C9 C8 C7 135.6(6) . . ? C10 C8 C7 104.7(5) . . ? C8 C9 F1 121.0(6) . . ? C8 C9 C10 117.8(5) . 3_656 ? F1 C9 C10 121.2(6) . 3_656 ? C9 C10 C8 122.5(5) 3_656 . ? C9 C10 O1 125.0(5) 3_656 . ? C8 C10 O1 112.5(5) . . ? 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 O1 C2 1.391(7) . ? O1 C10 1.400(7) . ? C2 C3 1.362(9) . ? C2 C7 1.378(9) . ? C3 C4 1.380(10) . ? C4 C5 1.391(11) . ? C5 C6 1.368(10) . ? C6 C7 1.384(9) . ? C7 C8 1.481(9) . ? C8 C9 1.352(8) . ? C8 C10 1.391(8) . ? C9 F1 1.360(6) . ? C9 C10 1.366(9) 3_656 ? C10 C9 1.366(9) 3_656 ? 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 C10 O1 C2 C3 -179.0(5) . . . . ? C10 O1 C2 C7 0.6(6) . . . . ? C7 C2 C3 C4 -0.1(9) . . . . ? O1 C2 C3 C4 179.4(6) . . . . ? C2 C3 C4 C5 -0.2(9) . . . . ? C3 C4 C5 C6 0.2(9) . . . . ? C4 C5 C6 C7 0.0(9) . . . . ? C3 C2 C7 C6 0.4(9) . . . . ? O1 C2 C7 C6 -179.2(5) . . . . ? C3 C2 C7 C8 179.1(5) . . . . ? O1 C2 C7 C8 -0.4(7) . . . . ? C5 C6 C7 C2 -0.3(9) . . . . ? C5 C6 C7 C8 -178.6(6) . . . . ? C2 C7 C8 C9 178.9(7) . . . . ? C6 C7 C8 C9 -2.6(12) . . . . ? C2 C7 C8 C10 0.1(6) . . . . ? C6 C7 C8 C10 178.6(6) . . . . ? C10 C8 C9 F1 179.0(5) . . . . ? C7 C8 C9 F1 0.4(10) . . . . ? C10 C8 C9 C10 0.2(9) . . . 3_656 ? C7 C8 C9 C10 -178.4(6) . . . 3_656 ? C9 C8 C10 C9 -0.2(10) . . . 3_656 ? C7 C8 C10 C9 178.8(5) . . . 3_656 ? C9 C8 C10 O1 -178.8(5) . . . . ? C7 C8 C10 O1 0.2(6) . . . . ? C2 O1 C10 C9 -179.0(6) . . . 3_656 ? C2 O1 C10 C8 -0.5(6) . . . . ? _journal_paper_doi 10.1039/c0ob00790k