#------------------------------------------------------------------------------
#$Date: 2022-05-18 12:24:14 +0300 (Wed, 18 May 2022) $
#$Revision: 275516 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105293.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_8105293
loop_
_publ_author_name
'Wu, Wen-Neng'
'Fei, Qiang'
'Ge, Yong-Hui'
'Gan, Xiu-Hai'
_publ_section_title
;
 Crystal structure of
 4-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)oxy)benzoic acid,
 C13H9F3N2O3
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              805
_journal_page_last               806
_journal_paper_doi               10.1515/ncrs-2020-0020
_journal_volume                  235
_journal_year                    2020
_chemical_formula_sum            'C13 H9 F3 N2 O3'
_chemical_formula_weight         298.22
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 110.691(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6952(7)
_cell_length_b                   19.6715(18)
_cell_length_c                   8.0995(8)
_cell_measurement_reflns_used    1240
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.67
_cell_measurement_theta_min      2.504
_cell_volume                     1296.0(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0664
_diffrn_reflns_av_sigmaI/netI    0.0588
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6503
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_correction_T_min  0.9598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0558
_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)+(0.0476P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1358
_reflns_number_gt                1237
_reflns_number_total             2290
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2020-0020_suppl.cif
_cod_data_source_block           190801d
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               8105293
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.0828(2) 0.81901(13) 1.3721(3) 0.1159(9) Uani 1 1 d . . .
F2 F -0.0740(2) 0.83549(12) 1.1076(3) 0.1119(8) Uani 1 1 d . . .
F3 F 0.0187(2) 0.73781(13) 1.1919(3) 0.1068(8) Uani 1 1 d . . .
N1 N 0.4796(3) 0.83773(12) 1.0814(3) 0.0539(6) Uani 1 1 d . . .
N2 N 0.3434(3) 0.78537(13) 1.2559(3) 0.0606(7) Uani 1 1 d . . .
O1 O 0.8158(2) 0.95736(13) 0.4385(3) 0.0912(8) Uani 1 1 d . . .
H1 H 0.8943 0.9705 0.4133 0.137 Uiso 1 1 calc R . .
O2 O 0.9716(3) 0.99741(13) 0.7010(3) 0.0903(8) Uani 1 1 d . . .
O3 O 0.3322(2) 0.90623(11) 0.8472(2) 0.0673(6) Uani 1 1 d . . .
C1 C 0.8430(4) 0.96901(17) 0.6009(4) 0.0653(9) Uani 1 1 d . . .
C2 C 0.7139(3) 0.94836(14) 0.6706(4) 0.0557(8) Uani 1 1 d . . .
C3 C 0.7361(3) 0.95991(15) 0.8464(4) 0.0600(8) Uani 1 1 d . . .
H3 H 0.8344 0.9784 0.9215 0.072 Uiso 1 1 calc R . .
C4 C 0.6131(3) 0.94408(15) 0.9102(4) 0.0606(8) Uani 1 1 d . . .
H4 H 0.6274 0.9519 1.0279 0.073 Uiso 1 1 calc R . .
C5 C 0.4690(3) 0.91658(14) 0.7975(4) 0.0571(8) Uani 1 1 d . . .
C6 C 0.4459(3) 0.90429(16) 0.6236(4) 0.0659(9) Uani 1 1 d . . .
H6 H 0.3481 0.8852 0.5490 0.079 Uiso 1 1 calc R . .
C7 C 0.5691(3) 0.92053(15) 0.5612(4) 0.0661(9) Uani 1 1 d . . .
H7 H 0.5542 0.9125 0.4434 0.079 Uiso 1 1 calc R . .
C8 C 0.3410(3) 0.86677(15) 0.9872(4) 0.0552(8) Uani 1 1 d . . .
C9 C 0.4763(3) 0.79749(15) 1.2135(4) 0.0546(8) Uani 1 1 d . . .
C10 C 0.2060(3) 0.81714(16) 1.1579(4) 0.0558(8) Uani 1 1 d . . .
C11 C 0.1957(3) 0.85940(16) 1.0215(4) 0.0607(8) Uani 1 1 d . . .
H11 H 0.0990 0.8817 0.9560 0.073 Uiso 1 1 calc R . .
C12 C 0.6342(3) 0.76481(16) 1.3207(4) 0.0727(9) Uani 1 1 d . . .
H12A H 0.6190 0.7391 1.4146 0.109 Uiso 1 1 calc R . .
H12B H 0.7160 0.7992 1.3695 0.109 Uiso 1 1 calc R . .
H12C H 0.6694 0.7350 1.2472 0.109 Uiso 1 1 calc R . .
C13 C 0.0579(4) 0.8031(2) 1.2070(5) 0.0748(10) Uani 1 1 d . . .
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C8 N1 C9 116.6(2) . .
C10 N2 C9 115.9(2) . .
C1 O1 H1 109.5 . .
C8 O3 C5 121.5(2) . .
O2 C1 O1 123.1(3) . .
O2 C1 C2 119.8(3) . .
O1 C1 C2 117.1(3) . .
C7 C2 C3 119.5(2) . .
C7 C2 C1 120.6(3) . .
C3 C2 C1 119.8(3) . .
C4 C3 C2 120.2(3) . .
C4 C3 H3 119.9 . .
C2 C3 H3 119.9 . .
C5 C4 C3 119.1(3) . .
C5 C4 H4 120.4 . .
C3 C4 H4 120.4 . .
C6 C5 C4 121.3(3) . .
C6 C5 O3 116.0(3) . .
C4 C5 O3 122.4(3) . .
C5 C6 C7 119.1(3) . .
C5 C6 H6 120.4 . .
C7 C6 H6 120.4 . .
C2 C7 C6 120.8(3) . .
C2 C7 H7 119.6 . .
C6 C7 H7 119.6 . .
N1 C8 O3 120.4(2) . .
N1 C8 C11 123.5(3) . .
O3 C8 C11 116.1(3) . .
N2 C9 N1 125.1(3) . .
N2 C9 C12 118.5(3) . .
N1 C9 C12 116.5(2) . .
N2 C10 C11 123.9(2) . .
N2 C10 C13 115.4(3) . .
C11 C10 C13 120.7(3) . .
C10 C11 C8 114.9(3) . .
C10 C11 H11 122.5 . .
C8 C11 H11 122.5 . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
F2 C13 F1 107.7(3) . .
F2 C13 F3 105.9(3) . .
F1 C13 F3 105.6(3) . .
F2 C13 C10 113.3(3) . .
F1 C13 C10 112.2(3) . .
F3 C13 C10 111.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C13 1.315(4) .
F2 C13 1.310(3) .
F3 C13 1.324(4) .
N1 C8 1.308(3) .
N1 C9 1.340(3) .
N2 C10 1.333(3) .
N2 C9 1.337(3) .
O1 C1 1.272(3) .
O1 H1 0.8200 .
O2 C1 1.257(3) .
O3 C8 1.354(3) .
O3 C5 1.398(3) .
C1 C2 1.480(4) .
C2 C7 1.372(4) .
C2 C3 1.386(4) .
C3 C4 1.378(3) .
C3 H3 0.9300 .
C4 C5 1.374(4) .
C4 H4 0.9300 .
C5 C6 1.372(4) .
C6 C7 1.375(4) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 C11 1.394(3) .
C9 C12 1.486(4) .
C10 C11 1.360(4) .
C10 C13 1.501(4) .
C11 H11 0.9300 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O2 C1 C2 C7 176.6(3) . . . .
O1 C1 C2 C7 -2.6(4) . . . .
O2 C1 C2 C3 -0.6(5) . . . .
O1 C1 C2 C3 -179.8(3) . . . .
C7 C2 C3 C4 -0.6(5) . . . .
C1 C2 C3 C4 176.6(3) . . . .
C2 C3 C4 C5 0.2(5) . . . .
C3 C4 C5 C6 0.4(5) . . . .
C3 C4 C5 O3 -172.7(2) . . . .
C8 O3 C5 C6 128.2(3) . . . .
C8 O3 C5 C4 -58.3(4) . . . .
C4 C5 C6 C7 -0.6(5) . . . .
O3 C5 C6 C7 172.9(3) . . . .
C3 C2 C7 C6 0.3(5) . . . .
C1 C2 C7 C6 -176.9(3) . . . .
C5 C6 C7 C2 0.3(5) . . . .
C9 N1 C8 O3 -177.6(2) . . . .
C9 N1 C8 C11 2.1(4) . . . .
C5 O3 C8 N1 0.8(4) . . . .
C5 O3 C8 C11 -178.9(3) . . . .
C10 N2 C9 N1 -0.8(4) . . . .
C10 N2 C9 C12 178.6(3) . . . .
C8 N1 C9 N2 -0.4(4) . . . .
C8 N1 C9 C12 -179.8(3) . . . .
C9 N2 C10 C11 0.4(4) . . . .
C9 N2 C10 C13 -179.9(3) . . . .
N2 C10 C11 C8 1.1(4) . . . .
C13 C10 C11 C8 -178.6(3) . . . .
N1 C8 C11 C10 -2.4(4) . . . .
O3 C8 C11 C10 177.2(2) . . . .
N2 C10 C13 F2 179.9(3) . . . .
C11 C10 C13 F2 -0.4(5) . . . .
N2 C10 C13 F1 57.7(4) . . . .
C11 C10 C13 F1 -122.6(3) . . . .
N2 C10 C13 F3 -60.6(4) . . . .
C11 C10 C13 F3 119.1(3) . . . .
