#------------------------------------------------------------------------------ #$Date: 2015-02-25 15:01:53 +0200 (Wed, 25 Feb 2015) $ #$Revision: 132410 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/51/61/1516193.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_1516193 loop_ _publ_author_name 'Hathwar, Venkatesha R.' 'Thakur, Tejender S.' 'Dubey, Ritesh' 'Pavan, Mysore S.' 'Row, Tayur N Guru' 'Desiraju, Gautam R.' _publ_section_title ; Extending the supramolecular synthon based fragment approach (SBFA) for transferability of multipole charge density parameters to monofluorobenzoic acids and their cocrystals with isonicotinamide: importance of C-H···O, C-H···F, and F···F intermolecular regions. ; _journal_issue 45 _journal_name_full 'The journal of physical chemistry. A' _journal_page_first 12852 _journal_page_last 12863 _journal_paper_doi 10.1021/jp2039866 _journal_volume 115 _journal_year 2011 _chemical_compound_source 'see text' _chemical_formula_moiety 'C7 H5 F O2' _chemical_formula_sum 'C7 H5 F O2' _chemical_formula_weight 140.11 _chemical_name_common '2-fluorobenzoic acid' _chemical_name_systematic ? _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _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 difmap _cell_angle_alpha 90 _cell_angle_beta 92.82(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.5525(13) _cell_length_b 3.7524(8) _cell_length_c 25.021(5) _cell_measurement_reflns_used 1291 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.4 _cell_volume 614.5(2) _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 13.6612 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_orient_matrix_type d*Trek _diffrn_orient_matrix_UB_11 0.021235 _diffrn_orient_matrix_UB_12 -0.002683 _diffrn_orient_matrix_UB_13 -0.151292 _diffrn_orient_matrix_UB_21 0.008321 _diffrn_orient_matrix_UB_22 -0.266301 _diffrn_orient_matrix_UB_23 0.005891 _diffrn_orient_matrix_UB_31 -0.039286 _diffrn_orient_matrix_UB_32 -0.001393 _diffrn_orient_matrix_UB_33 -0.007477 _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_probe x-ray _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1278 _diffrn_reflns_av_sigmaI/netI 0.0933 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 5097 _diffrn_reflns_reduction_process ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.8556 2theta: 29.3264 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.8556 2theta: 29.3264 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.8556 2theta: 29.3264 ; _diffrn_reflns_theta_full 27.25 _diffrn_reflns_theta_max 27.25 _diffrn_reflns_theta_min 1.63 _exptl_absorpt_coefficient_mu 0.130 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_correction_T_min 0.903 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.515 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description Needle _exptl_crystal_F_000 288 _exptl_crystal_size_max 0.800 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.313 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.111 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 111 _refine_ls_number_reflns 1360 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.141 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0556 _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^)+(0.0884P)^2^+0.0917P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1552 _refine_ls_wR_factor_ref 0.1831 _reflns_number_gt 1125 _reflns_number_total 1360 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file 2FBzAplaton.cif _[local]_cod_data_source_block shelxl _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius ; _cod_database_code 1516193 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z 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 F1 0.0203(7) 0.0509(8) 0.0209(6) 0.0052(5) 0.0042(5) -0.0057(5) O1 0.0292(9) 0.0447(10) 0.0183(8) 0.0036(6) -0.0001(6) -0.0122(7) O2 0.0223(8) 0.0386(9) 0.0213(7) 0.0012(6) 0.0004(6) -0.0101(6) C1 0.0167(10) 0.0194(9) 0.0205(10) 0.0008(7) 0.0016(7) 0.0002(7) C2 0.0185(10) 0.0229(9) 0.0237(10) 0.0007(7) 0.0026(7) 0.0011(7) C3 0.0270(11) 0.0270(10) 0.0189(10) -0.0005(7) -0.0004(7) 0.0027(8) C4 0.0249(11) 0.0242(10) 0.0247(10) -0.0014(7) -0.0061(8) 0.0011(8) C5 0.0187(10) 0.0217(9) 0.0334(11) 0.0002(8) -0.0005(8) -0.0018(8) C6 0.0226(11) 0.0236(9) 0.0217(10) 0.0031(7) 0.0025(8) -0.0015(8) C7 0.0208(10) 0.0223(9) 0.0191(9) 0.0012(7) 0.0015(7) -0.0004(7) loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv F1 F Uani 0.11453(17) 0.5249(4) 0.17152(5) 1.000 0.0306(4) O1 O Uani 0.2371(2) 0.7306(4) 0.01172(5) 1.000 0.0308(5) O2 O Uani 0.0297(2) 0.4438(4) 0.06627(6) 1.000 0.0274(5) C1 C Uani 0.3374(3) 0.7117(5) 0.10359(7) 1.000 0.0188(6) C2 C Uani 0.2972(3) 0.6600(5) 0.15754(8) 1.000 0.0217(6) C3 C Uani 0.4392(3) 0.7438(5) 0.19879(8) 1.000 0.0244(6) C4 C Uani 0.6281(3) 0.8841(5) 0.18599(8) 1.000 0.0248(6) C5 C Uani 0.6738(3) 0.9411(5) 0.13285(9) 1.000 0.0247(6) C6 C Uani 0.5299(3) 0.8562(5) 0.09203(8) 1.000 0.0226(6) C7 C Uani 0.1868(3) 0.6179(5) 0.05906(7) 1.000 0.0207(5) H1 H Uiso 0.121(7) 0.666(11) -0.026(2) 1.000 0.108(15) H3 H Uiso 0.406(4) 0.710(6) 0.2371(11) 1.000 0.036(6) H4 H Uiso 0.731(4) 0.941(6) 0.2169(11) 1.000 0.035(7) H5 H Uiso 0.789(4) 1.031(7) 0.1267(11) 1.000 0.034(7) H6 H Uiso 0.568(3) 0.897(6) 0.0556(9) 1.000 0.022(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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_publ_flag C7 O1 H1 118(2) no C2 C1 C7 122.50(18) no C6 C1 C7 120.03(16) no C2 C1 C6 117.47(17) no F1 C2 C3 117.26(17) yes C1 C2 C3 122.19(18) no F1 C2 C1 120.55(17) yes C2 C3 C4 118.88(18) no C3 C4 C5 120.73(19) no C4 C5 C6 119.68(18) no C1 C6 C5 121.04(18) no O1 C7 C1 114.24(17) yes O2 C7 C1 122.58(17) yes O1 C7 O2 123.18(17) yes C2 C3 H3 120.8(15) no C4 C3 H3 120.3(15) no C3 C4 H4 117.6(15) no C5 C4 H4 121.6(15) no C4 C5 H5 118.0(19) no C6 C5 H5 122.3(19) no C1 C6 H6 121.7(12) no C5 C6 H6 117.2(12) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag F1 C2 1.361(2) yes O1 C7 1.315(2) yes O2 C7 1.240(2) yes O1 H1 1.21(5) no C1 C6 1.416(3) no C1 C7 1.494(3) no C1 C2 1.402(3) no C2 C3 1.391(3) no C3 C4 1.397(3) no C4 C5 1.394(3) no C5 C6 1.393(3) no C3 H3 1.00(3) no C4 H4 1.02(3) no C5 H5 0.85(3) no C6 H6 0.97(2) no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag F1 O2 2.682(2) . no F1 H3 2.58(3) 2_545 no O1 O2 2.638(2) 3_565 no O2 O1 2.638(2) 3_565 no O2 C7 3.273(2) 1_545 no O2 F1 2.682(2) . no O2 C7 3.386(2) 3_565 no O1 H6 2.58(2) 3_675 no O1 H6 2.46(2) . no O1 H1 2.82(4) 3_565 no O2 H5 2.72(3) 1_445 no O2 H1 1.44(5) 3_565 no C1 C6 3.466(3) 1_545 no C3 C4 3.476(3) 1_545 no C4 C3 3.476(3) 1_565 no C6 C1 3.466(3) 1_565 no C7 O2 3.386(2) 3_565 no C7 O2 3.273(2) 1_565 no C4 H4 3.05(3) 2_645 no C7 H1 2.39(5) 3_565 no H1 O1 2.82(4) 3_565 no H1 O2 1.44(5) 3_565 no H1 C7 2.39(5) 3_565 no H1 H1 2.44(7) 3_565 no H3 F1 2.58(3) 2_555 no H4 C4 3.05(3) 2_655 no H4 H4 2.51(4) 2_645 no H4 H4 2.51(4) 2_655 no H5 O2 2.72(3) 1_665 no H6 O1 2.46(2) . no H6 O1 2.58(2) 3_675 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O1 H1 O2 1.21(5) 1.44(5) 2.638(2) 172(4) 3_565 yes C6 H6 O1 0.97(2) 2.58(2) 3.444(2) 149.3(17) 3_675 yes 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_publ_flag C6 C1 C2 F1 179.45(17) no C6 C1 C2 C3 -0.3(3) no C7 C1 C2 F1 -1.1(3) no C7 C1 C2 C3 179.17(18) no C2 C1 C6 C5 0.4(3) no C7 C1 C6 C5 -179.11(18) no C2 C1 C7 O1 170.70(18) no C2 C1 C7 O2 -10.4(3) no C6 C1 C7 O1 -9.8(3) no C6 C1 C7 O2 169.12(19) no F1 C2 C3 C4 -179.79(17) no C1 C2 C3 C4 0.0(3) no C2 C3 C4 C5 0.3(3) no C3 C4 C5 C6 -0.2(3) no C4 C5 C6 C1 -0.1(3) no