#------------------------------------------------------------------------------ #$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/2/2204471.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2204471 _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M P21/c loop_ _publ_author_name 'Song, Xiu-Yan' 'Dong, Xiao-Hong' 'Zhang, Shu-Sheng' 'Li, Xue-Mei' 'Wen, Yong-Hong' 'Zhong, Hui-Min' _publ_section_title ; 2-Fluoro-4-hydroxybenzonitrile ; _journal_issue 11 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o1919 _journal_page_last o1920 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C7 H4 F N O' _chemical_formula_moiety 'C7 H4 F N O' _chemical_formula_sum 'C7 H4 F N O' _chemical_formula_weight 137.11 _chemical_name_systematic ; 2-Fluoro-4-hydroxybenzonitrile ; _symmetry_cell_setting Monoclinic _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 95.035(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 3.8051(17) _cell_length_b 11.852(5) _cell_length_c 13.903(6) _cell_measurement_reflns_used 1352 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.0 _cell_measurement_theta_min 2.26 _cell_volume 624.5(5) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.962 _diffrn_measured_fraction_theta_max 0.962 _diffrn_measurement_device_type 'Siemens SMART 1000 CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0094 _diffrn_reflns_av_sigmaI/netI 0.0119 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 2477 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.26 _diffrn_standards_decay_% negligible _diffrn_standards_interval_count none _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_T_max 0.9893 _exptl_absorpt_correction_T_min 0.9707 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 280 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.136 _refine_diff_density_min -0.167 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 91 _refine_ls_number_reflns 1065 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.080 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0342 _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^)+(0.0517P)^2^+0.0925P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0940 _refine_ls_wR_factor_ref 0.0985 _reflns_number_gt 919 _reflns_number_total 1065 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cv6381.cif 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' 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' N N 0.0061 0.0033 '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_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol C1 0.4517(4) 0.74745(11) -0.11348(10) 0.0480(4) Uani d . 1 C C2 0.3287(4) 0.64315(12) -0.08612(10) 0.0533(4) Uani d . 1 C C3 0.1802(4) 0.56630(12) -0.15008(11) 0.0540(4) Uani d . 1 C H3A 0.1018 0.4970 -0.1290 0.065 Uiso calc R 1 H C4 0.1486(4) 0.59386(11) -0.24790(10) 0.0483(4) Uani d . 1 C C5 0.2662(4) 0.69813(12) -0.27815(10) 0.0513(4) Uani d . 1 C H5A 0.2425 0.7168 -0.3434 0.062 Uiso calc R 1 H C6 0.4173(4) 0.77343(12) -0.21164(10) 0.0511(4) Uani d . 1 C H6A 0.4976 0.8426 -0.2324 0.061 Uiso calc R 1 H C7 0.6166(4) 0.82215(13) -0.04236(11) 0.0555(4) Uani d . 1 C N1 0.7527(4) 0.87913(12) 0.01558(10) 0.0707(4) Uani d . 1 N O1 0.0011(3) 0.51595(9) -0.30928(8) 0.0645(4) Uani d . 1 O H1A -0.0052 0.5400 -0.3647 0.097 Uiso calc R 1 H F1 0.3558(3) 0.61821(8) 0.00932(6) 0.0826(4) Uani d . 1 F loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0462(8) 0.0486(8) 0.0487(8) 0.0078(6) 0.0015(6) -0.0013(6) C2 0.0628(9) 0.0545(8) 0.0423(8) 0.0107(7) 0.0018(7) 0.0061(6) C3 0.0631(9) 0.0437(8) 0.0551(9) 0.0028(6) 0.0043(7) 0.0101(6) C4 0.0493(8) 0.0442(7) 0.0504(8) 0.0065(6) -0.0006(6) -0.0003(6) C5 0.0572(9) 0.0519(8) 0.0443(8) 0.0020(6) 0.0023(6) 0.0065(6) C6 0.0520(8) 0.0474(8) 0.0541(8) -0.0009(6) 0.0047(7) 0.0051(6) C7 0.0553(9) 0.0582(9) 0.0524(9) 0.0068(7) 0.0013(7) 0.0004(7) N1 0.0804(10) 0.0705(9) 0.0587(8) -0.0034(8) -0.0079(7) -0.0067(7) O1 0.0843(8) 0.0502(6) 0.0566(7) -0.0047(5) -0.0080(6) -0.0001(5) F1 0.1280(10) 0.0727(7) 0.0455(6) -0.0014(6) -0.0014(6) 0.0111(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 1.387(2) ? C1 C6 1.394(2) ? C1 C7 1.430(2) yes C2 F1 1.3544(17) yes C2 C3 1.361(2) ? C3 C4 1.393(2) ? C3 H3A 0.9300 ? C4 O1 1.3460(17) yes C4 C5 1.392(2) ? C5 C6 1.374(2) ? C5 H5A 0.9300 ? C6 H6A 0.9300 ? C7 N1 1.1402(19) yes O1 H1A 0.8200 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 C1 C6 117.42(13) C2 C1 C7 120.01(13) C6 C1 C7 122.54(14) F1 C2 C3 119.06(14) F1 C2 C1 117.70(13) C3 C2 C1 123.24(13) C2 C3 C4 118.44(14) C2 C3 H3A 120.8 C4 C3 H3A 120.8 O1 C4 C5 123.00(13) O1 C4 C3 116.96(13) C5 C4 C3 120.03(13) C6 C5 C4 119.99(14) C6 C5 H5A 120.0 C4 C5 H5A 120.0 C5 C6 C1 120.87(14) C5 C6 H6A 119.6 C1 C6 H6A 119.6 N1 C7 C1 178.07(16) C4 O1 H1A 109.5 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 C6 C1 C2 F1 -178.88(13) C7 C1 C2 F1 3.1(2) C6 C1 C2 C3 0.4(2) C7 C1 C2 C3 -177.67(14) F1 C2 C3 C4 178.92(13) C1 C2 C3 C4 -0.3(2) C2 C3 C4 O1 179.91(13) C2 C3 C4 C5 -0.2(2) O1 C4 C5 C6 -179.42(14) C3 C4 C5 C6 0.8(2) C4 C5 C6 C1 -0.7(2) C2 C1 C6 C5 0.1(2) C7 C1 C6 C5 178.14(13) C2 C1 C7 N1 40(5) C6 C1 C7 N1 -138(5) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O1 H1A N1 4_475 0.82 2.07 2.822(2) 153 yes _cod_database_code 2204471