data_2003671 _journal_name_full 'Acta Crystallographica' _journal_year 1995 _journal_volume C51 _journal_page_first 1427 _journal_page_last 1429 _publ_section_title ; 2,3,4,5-Tetrafluoro-N-(4-fluorophenyl)-6-hydroxybenzamide: an Example of a Combined Inter- and Intramolecular O...H...O Bifurcated Hydrogen Bond ; _chemical_formula_moiety 'C13 H6 F5 N1 O2' _chemical_formula_sum 'C13 H6 F5 N1 O2' _chemical_formula_structural 'C13 H6 F5 N1 O2' _chemical_formula_weight 303.19 loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' -x,-y,-z _symmetry_space_group_name_H-M 'P -1' _cell_length_a 5.842(1) _cell_length_b 10.309(1) _cell_length_c 11.062(1) _cell_angle_alpha 66.53(1) _cell_angle_beta 76.15(1) _cell_angle_gamma 73.03(1) _cell_volume 578.7(3) _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.740 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method ? _diffrn_radiation_type 'MoK\a' _diffrn_radiation_wavelength 0.71069 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.50 _cell_measurement_theta_max 12.50 _exptl_absorpt_coefficient_mu 0.1630 _cell_measurement_temperature 296 _exptl_crystal_description 'plate' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.05 _exptl_crystal_size_rad ? _exptl_crystal_colour 'colourless' _chemical_compound_source ? _diffrn_measurement_device 'CAD4' _diffrn_measurement_method '\w/2\q' _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_t_min ? _exptl_absorpt_correction_t_max ? _diffrn_reflns_number 2071 _reflns_number_total 2019 _reflns_number_observed 1303 _reflns_observed_criterion 'I>3\s(I)' _diffrn_reflns_av_R_equivalents 0.029 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'insignificant' _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.0528 _refine_ls_wR_factor_obs 0.0530 _refine_ls_wR_factor_all ? _refine_ls_goodness_of_fit_obs 1.390 _refine_ls_goodness_of_fit_all ? _refine_ls_number_reflns 1303 _refine_ls_number_parameters 214 _refine_ls_hydrogen_treatment refall _refine_ls_weighting_scheme sigma _refine_ls_shift/esd_max 0.0818 _refine_diff_density_max 0.25235 _refine_diff_density_min -0.19193 _refine_ls_extinction_method 'none' _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C 'International Tables' 0.002 0.002 H 'International Tables' 0.000 0.000 F 'International Tables' 0.014 0.010 N 'International Tables' 0.004 0.003 O 'International Tables' 0.008 0.006 _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? ;PROCESS TEXSAN (Molecular Structure Corporation, 1985) ; ; FINISH TEXSAN. Literature Survey: CSSR (1984) ; loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv C1 0.4903(5) 0.3711(3) 0.6878(3) 0.050(2) C2 0.2789(6) 0.3306(3) 0.7636(3) 0.058(3) C3 0.1906(6) 0.2262(3) 0.7560(3) 0.063(3) C4 0.3123(7) 0.1556(3) 0.6684(3) 0.063(3) C5 0.5211(7) 0.1921(3) 0.5922(3) 0.060(3) C6 0.6123(6) 0.2969(3) 0.5993(3) 0.052(3) C7 0.5979(6) 0.4830(3) 0.6917(3) 0.049(2) C11 0.5603(6) 0.6597(3) 0.8006(3) 0.052(2) C12 0.7621(6) 0.7168(3) 0.7310(3) 0.061(3) C13 0.8193(7) 0.8174(4) 0.7645(4) 0.065(3) C14 0.6774(7) 0.8613(3) 0.8636(3) 0.067(3) C15 0.4746(7) 0.8090(4) 0.9323(3) 0.068(3) C16 0.4168(7) 0.7074(3) 0.9004(3) 0.061(3) O6 0.8170(4) 0.3240(2) 0.5177(2) 0.065(2) O7 0.7885(4) 0.5078(2) 0.6190(2) 0.065(2) N7 0.4866(6) 0.5548(3) 0.7752(3) 0.061(3) F2 0.1467(3) 0.3965(2) 0.8510(2) 0.072(2) F3 -0.0141(4) 0.1927(2) 0.8318(2) 0.089(2) F4 0.2253(4) 0.0552(2) 0.6602(3) 0.089(2) F5 0.6380(4) 0.1236(2) 0.5064(2) 0.082(2) F14 0.7374(5) 0.9589(2) 0.8962(2) 0.097(2) H6 0.849(7) 0.392(4) 0.536(4) 0.09(1) H7 0.363(7) 0.536(4) 0.813(4) 0.08(1) H12 0.857(7) 0.685(4) 0.656(4) 0.09(1) H13 0.951(8) 0.849(4) 0.726(4) 0.09(1) H15 0.384(8) 0.842(4) 1.001(4) 0.11(1) H16 0.280(6) 0.671(3) 0.945(3) 0.06(1) loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 C1 0.051(2) -0.018(1) -0.003(2) 0.047(1) -0.018(1) 0.053(2) C2 0.055(2) -0.017(2) 0.006(2) 0.054(2) -0.026(2) 0.064(2) C3 0.053(2) -0.028(2) -0.002(2) 0.062(2) -0.020(2) 0.076(2) C4 0.071(3) -0.023(2) -0.011(2) 0.048(2) -0.024(2) 0.080(2) C5 0.071(2) -0.018(2) -0.004(2) 0.052(2) -0.024(2) 0.062(2) C6 0.057(2) -0.019(1) -0.002(2) 0.047(2) -0.018(1) 0.054(2) C7 0.052(2) -0.018(1) 0.000(2) 0.048(2) -0.019(1) 0.050(2) C11 0.058(2) -0.020(1) 0.004(2) 0.048(2) -0.021(1) 0.052(2) C12 0.065(2) -0.030(2) 0.010(2) 0.064(2) -0.034(2) 0.064(2) C13 0.067(2) -0.035(2) 0.012(2) 0.064(2) -0.032(2) 0.074(2) C14 0.085(3) -0.030(2) 0.004(2) 0.061(2) -0.036(2) 0.070(2) C15 0.079(3) -0.030(2) 0.008(2) 0.074(2) -0.039(2) 0.063(2) C16 0.065(2) -0.028(2) 0.017(2) 0.065(2) -0.032(2) 0.059(2) O6 0.068(1) -0.035(1) 0.020(1) 0.070(1) -0.039(1) 0.069(1) O7 0.067(1) -0.039(1) 0.020(1) 0.069(1) -0.041(1) 0.073(1) N7 0.059(2) -0.033(2) 0.017(2) 0.065(2) -0.037(1) 0.069(2) F2 0.062(1) -0.0313(9) 0.0205(10) 0.076(1) -0.044(1) 0.087(1) F3 0.070(1) -0.050(1) 0.022(1) 0.089(1) -0.043(1) 0.116(2) F4 0.100(2) -0.046(1) -0.003(1) 0.069(1) -0.045(1) 0.119(2) F5 0.105(2) -0.035(1) 0.009(1) 0.070(1) -0.048(1) 0.088(1) F14 0.116(2) -0.061(1) 0.017(1) 0.107(1) -0.074(1) 0.111(2)