#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/65/2236575.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_2236575
loop_
_publ_author_name
'Lu, Tao'
'Liao, Xiao-Jian'
'Liang, Yuan-Wei'
'Xu, Shi-Hai'
_publ_section_title
;
 2-Carbamoyl-3,4,5,6-tetrafluorobenzoic acid
;
_journal_coeditor_code           RK2367
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2864
_journal_paper_doi               10.1107/S1600536812036549
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C8 H3 F4 N O3'
_chemical_formula_moiety         'C8 H3 F4 N O3'
_chemical_formula_sum            'C8 H3 F4 N O3'
_chemical_formula_weight         237.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           Olex2
_cell_angle_alpha                90.00
_cell_angle_beta                 100.086(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.5872(6)
_cell_length_b                   6.9193(3)
_cell_length_c                   8.6129(4)
_cell_measurement_reflns_used    1702
_cell_measurement_temperature    268
_cell_measurement_theta_max      62.6002
_cell_measurement_theta_min      5.2118
_cell_volume                     855.89(7)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_molecular_graphics
'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material
'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      268
_diffrn_detector_area_resol_mean 16.0288
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type
'Agilent Xcalibur Gemini ultra Sapphire-3 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0127
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2346
_diffrn_reflns_theta_full        62.69
_diffrn_reflns_theta_max         62.69
_diffrn_reflns_theta_min         7.10
_exptl_absorpt_coefficient_mu    1.775
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2011)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0350
_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)+(0.0432P)²+0.5536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0913
_reflns_number_gt                1240
_reflns_number_total             1312
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2367.cif
_cod_data_source_block           I
_cod_database_code               2236575
_cod_database_fobs_code          2236575
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
F F1 0.27285(8) 0.04074(16) 0.69216(13) 0.0293(3) Uani d . 1 1
F F4 0.11543(8) 0.66145(18) 0.36824(14) 0.0328(3) Uani d . 1 1
F F2 0.09507(9) 0.02888(19) 0.54379(17) 0.0416(4) Uani d . 1 1
O O3 0.39455(9) 0.41810(19) 0.84775(14) 0.0219(3) Uani d . 1 1
F F3 0.01714(8) 0.3444(2) 0.38240(16) 0.0394(4) Uani d . 1 1
O O1 0.27710(9) 0.8186(2) 0.40108(15) 0.0253(4) Uani d . 1 1
H H1 0.3157 0.9023 0.3929 0.038 Uiso calc R 1 1
O O2 0.39129(9) 0.7021(2) 0.58320(16) 0.0280(4) Uani d . 1 1
N N1 0.45248(11) 0.2650(2) 0.65574(18) 0.0234(4) Uani d . 1 1
H H1A 0.5059 0.2493 0.7150 0.028 Uiso calc R 1 1
H H1B 0.4431 0.2227 0.5604 0.028 Uiso calc R 1 1
C C1 0.25134(12) 0.5238(3) 0.5229(2) 0.0182(4) Uani d . 1 1
C C5 0.23637(13) 0.1978(3) 0.6119(2) 0.0213(4) Uani d . 1 1
C C6 0.29012(12) 0.3598(3) 0.6086(2) 0.0173(4) Uani d . 1 1
C C4 0.14478(14) 0.1886(3) 0.5367(2) 0.0266(5) Uani d . 1 1
C C3 0.10574(13) 0.3486(3) 0.4559(2) 0.0259(5) Uani d . 1 1
C C8 0.31341(12) 0.6916(3) 0.5074(2) 0.0182(4) Uani d . 1 1
C C2 0.15862(13) 0.5134(3) 0.4498(2) 0.0223(4) Uani d . 1 1
C C7 0.38555(12) 0.3533(3) 0.7106(2) 0.0174(4) Uani d . 1 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
F1 0.0368(7) 0.0204(6) 0.0312(6) 0.0008(5) 0.0074(5) 0.0066(5)
F4 0.0216(6) 0.0325(7) 0.0399(7) 0.0031(5) -0.0069(5) 0.0090(5)
F2 0.0326(7) 0.0308(7) 0.0608(9) -0.0166(6) 0.0066(6) 0.0017(6)
O3 0.0257(7) 0.0245(7) 0.0145(7) 0.0056(6) 0.0007(5) -0.0019(5)
F3 0.0163(6) 0.0463(8) 0.0514(8) -0.0076(5) -0.0056(5) -0.0016(6)
O1 0.0235(7) 0.0248(8) 0.0254(7) -0.0043(6) -0.0017(6) 0.0084(6)
O2 0.0205(7) 0.0282(8) 0.0318(8) -0.0053(6) -0.0053(6) 0.0070(6)
N1 0.0191(8) 0.0329(10) 0.0168(8) 0.0069(7) -0.0009(6) -0.0051(7)
C1 0.0191(9) 0.0204(10) 0.0153(9) 0.0009(7) 0.0036(7) -0.0015(7)
C5 0.0257(10) 0.0190(10) 0.0203(9) 0.0030(8) 0.0068(8) 0.0016(7)
C6 0.0186(9) 0.0200(10) 0.0140(8) 0.0013(7) 0.0052(7) -0.0020(7)
C4 0.0237(10) 0.0265(11) 0.0312(11) -0.0084(8) 0.0090(8) -0.0043(9)
C3 0.0153(9) 0.0326(12) 0.0288(10) -0.0020(8) 0.0013(8) -0.0046(9)
C8 0.0191(9) 0.0198(10) 0.0150(9) 0.0012(7) 0.0015(7) -0.0004(7)
C2 0.0187(9) 0.0262(11) 0.0208(9) 0.0036(8) 0.0004(7) 0.0014(8)
C7 0.0213(9) 0.0157(9) 0.0153(9) 0.0004(7) 0.0032(7) 0.0023(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
C8 O1 H1 109.5
H1A N1 H1B 120.0
C7 N1 H1A 120.0
C7 N1 H1B 120.0
C6 C1 C8 118.48(16)
C2 C1 C6 117.56(17)
C2 C1 C8 123.83(17)
F1 C5 C6 119.64(16)
F1 C5 C4 117.84(17)
C6 C5 C4 122.52(18)
C1 C6 C7 124.76(16)
C5 C6 C1 119.22(16)
C5 C6 C7 115.81(16)
F2 C4 C5 120.50(18)
F2 C4 C3 120.74(17)
C3 C4 C5 118.76(18)
F3 C3 C4 120.14(18)
F3 C3 C2 119.97(18)
C4 C3 C2 119.88(17)
O1 C8 C1 113.98(15)
O2 C8 O1 124.27(17)
O2 C8 C1 121.69(16)
F4 C2 C1 122.02(17)
F4 C2 C3 115.95(16)
C3 C2 C1 122.02(18)
O3 C7 N1 123.22(17)
O3 C7 C6 118.21(15)
N1 C7 C6 118.29(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C5 1.346(2)
F4 C2 1.336(2)
F2 C4 1.329(2)
O3 C7 1.249(2)
F3 C3 1.336(2)
O1 H1 0.8200
O1 C8 1.312(2)
O2 C8 1.209(2)
N1 H1A 0.8600
N1 H1B 0.8600
N1 C7 1.308(2)
C1 C6 1.416(3)
C1 C8 1.493(3)
C1 C2 1.390(3)
C5 C6 1.371(3)
C5 C4 1.380(3)
C6 C7 1.511(2)
C4 C3 1.377(3)
C3 C2 1.383(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
O1 H1 O3 4_575 0.82 1.78 2.5965(18) 172.4
N1 H1A O3 2_646 0.86 2.82 3.281(2) 115.6
N1 H1A O2 2_646 0.86 2.11 2.940(2) 161.2
