#------------------------------------------------------------------------------
#$Date: 2020-10-17 08:07:23 +0300 (Sat, 17 Oct 2020) $
#$Revision: 258450 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/36/2243629.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_2243629
loop_
_publ_author_name
'Ye, Naike'
'Tanski, Joseph M.'
_publ_section_title
;
 The crystal structure of 5-(trifluoromethyl)picolinic acid monohydrate
 reveals a water-bridged hydrogen-bonding network
;
_journal_coeditor_code           DJ2015
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1752
_journal_page_last               1756
_journal_paper_doi               10.1107/S2056989020013523
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C7 H4 F3 N O2, H2 O'
_chemical_formula_moiety         'C7 H4 F3 N O2, H2 O'
_chemical_formula_sum            'C7 H6 F3 N O3'
_chemical_formula_weight         209.13
_chemical_name_common
;
5-(Trifluoromethyl)picolinic acid monohydrate
;
_chemical_name_systematic
;
5-(Trifluoromethyl)pyridine-2-carboxylic acid monohydrate
;
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 99.983(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9213(10)
_cell_length_b                   10.0759(12)
_cell_length_c                   9.1010(11)
_cell_measurement_reflns_used    7786
_cell_measurement_temperature    125.(2)
_cell_measurement_theta_max      30.1946
_cell_measurement_theta_min      3.0418
_cell_volume                     805.70(16)
_computing_cell_refinement
;
SAINT (Bruker, 2017)
;
_computing_data_collection
;
APEX2 (Bruker, 2017)
;
_computing_data_reduction
;
SAINT (Bruker, 2017)
;
_computing_molecular_graphics
;
SHELXTL2014 (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL2014 (Sheldrick, 2008), OLEX2 (Dolomanov et al.,
2009), and
Mercury (Macrae et al.,  2020)
;
_computing_structure_refinement
;
SHELXL2017/1 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      125(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0255
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19282
_diffrn_reflns_theta_full        30.52
_diffrn_reflns_theta_max         30.52
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2017)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0402
_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
'w=1/[σ²(Fo²)+(0.0559P)²+0.2301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1025
_reflns_number_gt                2126
_reflns_number_total             2463
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dj2015sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243629
loop_
_space_group_symop_operation_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
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 1.02797(8) 0.44945(10) 0.19056(8) 0.0387(2) Uani d 1 . .
F F2 0.91945(11) 0.63911(8) 0.13936(9) 0.0398(2) Uani d 1 . .
F F3 0.80545(8) 0.45876(7) 0.06062(7) 0.02763(17) Uani d 1 . .
O O1 0.62864(9) 0.36976(7) 0.76271(8) 0.02126(17) Uani d 1 . .
H H1 0.572(2) 0.365(2) 0.838(2) 0.056(6) Uiso d 1 . .
O O2 0.57174(9) 0.58725(7) 0.74769(8) 0.02259(17) Uani d 1 . .
N N 0.69746(10) 0.60686(8) 0.49521(9) 0.01815(18) Uani d 1 . .
C C1 0.62637(11) 0.48809(9) 0.70248(10) 0.01643(18) Uani d 1 . .
C C2 0.70005(11) 0.48977(9) 0.56536(10) 0.01547(18) Uani d 1 . .
C C3 0.76396(12) 0.37599(9) 0.51689(11) 0.01936(19) Uani d 1 . .
H H3A 0.762813 0.29467 0.569519 0.023 Uiso calc 1 . .
C C4 0.82968(12) 0.38369(10) 0.38964(11) 0.0205(2) Uani d 1 . .
H H4A 0.87462 0.307748 0.353174 0.025 Uiso calc 1 . .
C C5 0.82825(11) 0.50451(10) 0.31708(11) 0.01741(19) Uani d 1 . .
C C6 0.76044(12) 0.61375(10) 0.37220(11) 0.01917(19) Uani d 1 . .
H H6A 0.758767 0.695976 0.32085 0.023 Uiso calc 1 . .
C C7 0.89493(12) 0.51403(10) 0.17683(11) 0.0210(2) Uani d 1 . .
O O1W 0.46520(10) 0.34230(8) 0.96069(9) 0.02433(18) Uani d 1 . .
H H2W 0.469(2) 0.3734(17) 1.043(2) 0.040(5) Uiso d 1 . .
H H1W 0.4241(19) 0.2651(19) 0.9607(19) 0.043(5) Uiso d 1 . .
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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 H1 . . 113.0(13) ?
C6 N C2 . . 117.98(8) ?
O2 C1 O1 . . 125.78(9) ?
O2 C1 C2 . . 121.95(8) ?
O1 C1 C2 . . 112.26(8) ?
N C2 C3 . . 123.42(9) ?
N C2 C1 . . 115.48(8) ?
C3 C2 C1 . . 121.09(8) ?
C2 C3 C4 . . 118.41(9) ?
C2 C3 H3A . . 120.8 ?
C4 C3 H3A . . 120.8 ?
C5 C4 C3 . . 118.49(9) ?
C5 C4 H4A . . 120.8 ?
C3 C4 H4A . . 120.8 ?
C4 C5 C6 . . 119.52(9) ?
C4 C5 C7 . . 119.30(9) ?
C6 C5 C7 . . 121.14(9) ?
N C6 C5 . . 122.17(9) ?
N C6 H6A . . 118.9 ?
C5 C6 H6A . . 118.9 ?
F3 C7 F2 . . 107.12(9) ?
F3 C7 F1 . . 105.68(8) ?
F2 C7 F1 . . 107.51(9) ?
F3 C7 C5 . . 112.15(8) ?
F2 C7 C5 . . 112.61(8) ?
F1 C7 C5 . . 111.38(9) ?
H2W O1W H1W . . 107.4(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C7 . 1.3402(13) ?
F2 C7 . 1.3335(13) ?
F3 C7 . 1.3317(12) ?
O1 C1 . 1.3109(11) ?
O1 H1 . 0.92(2) ?
O2 C1 . 1.2143(12) ?
N C6 . 1.3387(12) ?
N C2 . 1.3397(12) ?
C1 C2 . 1.5081(13) ?
C2 C3 . 1.3861(13) ?
C3 C4 . 1.3879(13) ?
C3 H3A . 0.95 ?
C4 C5 . 1.3840(14) ?
C4 H4A . 0.95 ?
C5 C6 . 1.3908(13) ?
C5 C7 . 1.5019(13) ?
C6 H6A . 0.95 ?
O1W H2W . 0.808(19) ?
O1W H1W . 0.859(19) ?
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 H1 O1W . 0.92(2) 1.60(2) 2.5219(11) 174.(2) y
O1W H2W O2 3_667 0.808(19) 2.038(19) 2.8213(11) 163.2(17) y
O1W H1W O2 2_646 0.859(19) 2.615(18) 3.1769(11) 124.1(13) y
O1W H1W N 2_646 0.859(19) 2.008(18) 2.8455(11) 164.5(16) y

_cod_database_fobs_code 2243629
