#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/76/2217606.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_2217606
loop_
_publ_author_name
'Aleksandra A. Knapik'
'Wladek Minor'
'Maksymilian Chruszcz'
_publ_section_title
;
 2,3-Difluorobenzoic acid
;
_journal_coeditor_code           OM2199
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o466
_journal_page_last               o466
_journal_paper_doi               10.1107/S1600536808001232
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C7 H4 F2 O2'
_chemical_formula_moiety         'C7 H4 F2 O2'
_chemical_formula_sum            'C7 H4 F2 O2'
_chemical_formula_weight         158.10
_chemical_name_common            '2,3-difluorobenzoic acid'
_chemical_name_systematic        '2,3-difluorobenzoic acid'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.270(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.7610(10)
_cell_length_b                   6.5200(10)
_cell_length_c                   26.521(2)
_cell_measurement_reflns_used    25713
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      3.1
_cell_volume                     649.8(2)
_computing_cell_refinement       'HKL-2000 (Otwinowski & Minor, 1997)'
_computing_data_collection       'HKL-2000 (Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL-2000 (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
HKL-3000SM (Minor et al.,  2006),
Mercury (Macrae et al.,  2006),
ORTEPIII (Burnett & Johnson, 1996) and
ORTEP-3 (Farrugia, 1997)
;
_computing_publication_material  'HKL-3000SM (Minor et al.,  2006)'
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) and
HKL-3000SM (Minor et al.,  2006)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
and HKL-3000SM (Minor et al.,  2006)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans with χ offset'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71074
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_sigmaI/netI    0.0142
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            25713
_diffrn_reflns_theta_full        30.0
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         3.1
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Otwinowski et al.,  2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1881
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0435
_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/[σ²(Fo²)+(0.0665P)²+0.0891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1331
_reflns_number_gt                1371
_reflns_number_total             1881
_reflns_observed_criterion       >-3sigma(I)
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om2199.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2217606
_cod_database_fobs_code          2217606
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_site_type_symbol
_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_occupancy
C C1 0.3028(3) 0.18896(18) 0.09787(4) 0.0453(3) Uani d 1
C C2 0.3710(3) 0.2435(2) 0.14793(5) 0.0507(3) Uani d 1
C C3 0.2895(4) 0.1088(2) 0.18600(5) 0.0580(3) Uani d 1
C C4 0.1428(4) -0.0797(2) 0.17592(6) 0.0607(4) Uani d 1
C C5 0.0737(4) -0.1357(2) 0.12626(6) 0.0587(3) Uani d 1
C C6 0.1521(3) -0.0033(2) 0.08785(5) 0.0517(3) Uani d 1
C C7 0.3892(3) 0.32666(19) 0.05550(5) 0.0485(3) Uani d 1
F F1 0.5159(3) 0.42443(14) 0.16134(3) 0.0748(3) Uani d 1
F F2 0.3611(3) 0.16829(19) 0.23412(3) 0.0893(4) Uani d 1
O O1 0.5592(3) 0.48801(16) 0.06313(4) 0.0673(3) Uani d 1
O O2 0.2818(3) 0.26822(19) 0.01143(4) 0.0742(4) Uani d 1
H H2 0.330(8) 0.372(4) -0.0169(13) 0.158(11) Uiso d 1
H H4 0.090(5) -0.174(3) 0.2020(8) 0.087(6) Uiso d 1
H H5 -0.026(5) -0.264(3) 0.1183(7) 0.079(5) Uiso d 1
H H6 0.104(4) -0.037(3) 0.0534(6) 0.057(4) Uiso d 1
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 0.0441(6) 0.0446(6) 0.0472(6) 0.0012(5) 0.0014(4) -0.0005(5)
C2 0.0550(7) 0.0465(6) 0.0503(6) 0.0009(5) 0.0003(5) -0.0037(5)
C3 0.0635(8) 0.0653(8) 0.0451(6) 0.0066(6) 0.0024(5) 0.0018(6)
C4 0.0593(7) 0.0625(8) 0.0607(8) 0.0018(6) 0.0074(6) 0.0151(6)
C5 0.0565(7) 0.0494(7) 0.0699(9) -0.0047(6) 0.0003(6) 0.0058(6)
C6 0.0524(7) 0.0495(7) 0.0529(7) -0.0036(5) -0.0017(5) -0.0021(5)
C7 0.0503(6) 0.0481(6) 0.0471(6) -0.0027(5) 0.0001(5) -0.0024(5)
F1 0.1091(7) 0.0572(5) 0.0576(5) -0.0162(5) -0.0039(5) -0.0095(4)
F2 0.1270(9) 0.0956(8) 0.0449(5) -0.0067(7) 0.0015(5) -0.0011(5)
O1 0.0901(7) 0.0569(6) 0.0544(5) -0.0240(5) -0.0021(5) 0.0016(4)
O2 0.1028(9) 0.0728(7) 0.0461(5) -0.0317(6) -0.0058(5) 0.0013(5)
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
C2 C1 C6 118.03(12)
C2 C1 C7 122.09(11)
C6 C1 C7 119.88(11)
F1 C2 C3 117.71(12)
F1 C2 C1 122.43(12)
C3 C2 C1 119.86(12)
F2 C3 C4 120.41(13)
F2 C3 C2 117.76(14)
C4 C3 C2 121.82(13)
C3 C4 C5 118.84(13)
C3 C4 H4 122.2(12)
C5 C4 H4 119.0(12)
C6 C5 C4 120.17(14)
C6 C5 H5 119.2(12)
C4 C5 H5 120.6(11)
C5 C6 C1 121.28(13)
C5 C6 H6 122.0(10)
C1 C6 H6 116.8(10)
O1 C7 O2 122.84(12)
O1 C7 C1 121.00(11)
O2 C7 C1 116.15(11)
C7 O2 H2 114.3(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3885(17)
C1 C6 1.3968(17)
C1 C7 1.4842(17)
C2 F1 1.3415(16)
C2 C3 1.3819(19)
C3 F2 1.3508(16)
C3 C4 1.369(2)
C4 C5 1.381(2)
C4 H4 0.95(2)
C5 C6 1.376(2)
C5 H5 0.94(2)
C6 H6 0.950(16)
C7 O1 1.2435(16)
C7 O2 1.2796(15)
O2 H2 1.03(3)
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
C5 H5 O1 1_445 0.94(2) 2.65(2) 3.509(2) 153(2)
O2 H2 O1 3_665 1.03(3) 1.60(3) 2.625(2) 173(3)
C6 H6 O2 3_555 0.95(2) 2.67(2) 3.498(2) 146.0(10)
C4 H4 F2 2_545 0.95(2) 2.65(2) 3.513(2) 151(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
C6 C1 C2 F1 179.84(11)
C7 C1 C2 F1 0.6(2)
C6 C1 C2 C3 -0.03(19)
C7 C1 C2 C3 -179.23(12)
F1 C2 C3 F2 0.0(2)
C1 C2 C3 F2 179.88(12)
F1 C2 C3 C4 -179.64(13)
C1 C2 C3 C4 0.2(2)
F2 C3 C4 C5 -179.87(13)
C2 C3 C4 C5 -0.2(2)
C3 C4 C5 C6 0.0(2)
C4 C5 C6 C1 0.2(2)
C2 C1 C6 C5 -0.17(19)
C7 C1 C6 C5 179.05(12)
C2 C1 C7 O1 7.3(2)
C6 C1 C7 O1 -171.85(12)
C2 C1 C7 O2 -173.28(12)
C6 C1 C7 O2 7.53(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 328957
