#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/31/1573175.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_1573175
loop_
_publ_author_name
'Xantini, Zizipho'
'Muller, Alfred'
'Lammertsma, Koop'
_publ_section_title
;
 2,4-Dichloro-6-{N-[2-(trifluoromethyl)phenyl]carboximidoyl}phenol
;
_journal_coeditor_code           PK4045
_journal_issue                   11
_journal_name_full               IUCrData
_journal_page_first              x241074
_journal_paper_doi               10.1107/S2414314624010745
_journal_volume                  9
_journal_year                    2024
_chemical_formula_iupac          'C14 H8 Cl2 F3 N O'
_chemical_formula_moiety         'C14 H8 Cl2 F3 N O'
_chemical_formula_sum            'C14 H8 Cl2 F3 N O'
_chemical_formula_weight         334.11
_chemical_name_systematic
;
2,4-Dichloro-6-{N-[2-(trifluoromethyl)phenyl]carboximidoyl}phenol
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.8436(3)
_cell_length_b                   13.8612(4)
_cell_length_c                   25.8433(7)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.69
_cell_measurement_theta_min      3.04
_cell_volume                     2809.73(15)
_computing_cell_refinement
;
APEX2 (Bruker, 2010)
;
_computing_data_collection
;
APEX2 (Bruker, 2010)
;
_computing_data_reduction
;
APEX2 (Bruker, 2010)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL (Sheldrick, 2015b) and publCIF (Westrip,
2010)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            27956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.882
_diffrn_reflns_theta_min         1.576
_exptl_absorpt_coefficient_mu    0.492
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.135
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.357
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0542P)²+0.6574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                2679
_reflns_number_total             3353
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            pk4045.cif
_cod_data_source_block           I
_cod_database_code               1573175
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.834
_shelx_estimated_absorpt_t_max   0.937
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
Cl Cl1 0.22744(7) 0.45151(3) 0.52669(2) 0.07023(17) Uani d 1 . .
Cl Cl2 0.51694(7) 0.71474(4) 0.65169(2) 0.07656(18) Uani d 1 . .
O O1 0.30841(17) 0.58814(9) 0.44463(5) 0.0565(3) Uani d 1 . .
N N1 0.43077(18) 0.75064(9) 0.40953(5) 0.0490(3) Uani d 1 . .
F F1 0.6420(3) 0.65886(12) 0.27056(5) 0.1294(7) Uani d 1 . .
C C1 0.5703(3) 0.67847(16) 0.31575(7) 0.0737(6) Uani d 1 . .
C C2 0.5393(3) 0.78362(13) 0.32338(7) 0.0587(4) Uani d 1 . .
C C3 0.4678(2) 0.81737(11) 0.36918(6) 0.0508(4) Uani d 1 . .
C C4 0.4317(3) 0.91504(13) 0.37471(8) 0.0655(5) Uani d 1 . .
H H4 0.380492 0.937641 0.404823 0.079 Uiso calc 1 . .
C C5 0.4722(3) 0.97866(16) 0.33510(10) 0.0846(7) Uani d 1 . .
H H5 0.447098 1.043908 0.338600 0.101 Uiso calc 1 . .
C C6 0.5491(4) 0.94580(17) 0.29087(9) 0.0917(8) Uani d 1 . .
H H6 0.578551 0.989010 0.264838 0.110 Uiso calc 1 . .
C C7 0.5829(3) 0.84888(17) 0.28488(8) 0.0796(6) Uani d 1 . .
H H7 0.635311 0.827058 0.254796 0.096 Uiso calc 1 . .
C C8 0.4679(2) 0.77357(11) 0.45590(6) 0.0476(3) Uani d 1 . .
H H8 0.518662 0.833044 0.462209 0.057 Uiso calc 1 . .
C C9 0.43343(19) 0.70977(10) 0.49926(6) 0.0448(3) Uani d 1 . .
C C10 0.35574(19) 0.61936(10) 0.49151(6) 0.0459(3) Uani d 1 . .
C C11 0.3277(2) 0.56153(11) 0.53473(7) 0.0509(4) Uani d 1 . .
C C12 0.3767(2) 0.58980(12) 0.58379(7) 0.0556(4) Uani d 1 . .
H H12 0.357636 0.549712 0.612062 0.067 Uiso calc 1 . .
F F2 0.4265(2) 0.62654(10) 0.31795(6) 0.1064(5) Uani d 1 . .
F F3 0.6717(2) 0.63993(9) 0.35177(5) 0.0902(4) Uani d 1 . .
C C14 0.4823(2) 0.73832(12) 0.54898(6) 0.0494(4) Uani d 1 . .
H H14 0.533728 0.798015 0.554050 0.059 Uiso calc 1 . .
C C13 0.4542(2) 0.67828(13) 0.59027(6) 0.0535(4) Uani d 1 . .
H H1 0.340(3) 0.6303(17) 0.4244(9) 0.076(7) 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'
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 O1 H1 . . 105.2(16) ?
C8 N1 C3 . . 118.70(14) ?
F1 C1 F3 . . 106.3(2) ?
F1 C1 F2 . . 106.53(19) ?
F3 C1 F2 . . 104.88(18) ?
F1 C1 C2 . . 112.73(18) ?
F3 C1 C2 . . 113.33(17) ?
F2 C1 C2 . . 112.5(2) ?
C7 C2 C3 . . 119.36(18) ?
C7 C2 C1 . . 120.17(18) ?
C3 C2 C1 . . 120.47(16) ?
C4 C3 C2 . . 119.81(16) ?
C4 C3 N1 . . 121.04(16) ?
C2 C3 N1 . . 119.14(15) ?
C5 C4 C3 . . 119.7(2) ?
C5 C4 H4 . . 120.1 ?
C3 C4 H4 . . 120.1 ?
C6 C5 C4 . . 120.3(2) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C7 . . 120.2(2) ?
C5 C6 H6 . . 119.9 ?
C7 C6 H6 . . 119.9 ?
C6 C7 C2 . . 120.5(2) ?
C6 C7 H7 . . 119.7 ?
C2 C7 H7 . . 119.7 ?
N1 C8 C9 . . 122.10(14) ?
N1 C8 H8 . . 119.0 ?
C9 C8 H8 . . 119.0 ?
C14 C9 C10 . . 120.08(14) ?
C14 C9 C8 . . 119.06(14) ?
C10 C9 C8 . . 120.84(14) ?
O1 C10 C11 . . 119.74(14) ?
O1 C10 C9 . . 122.44(14) ?
C11 C10 C9 . . 117.82(14) ?
C12 C11 C10 . . 121.95(15) ?
C12 C11 Cl1 . . 119.14(13) ?
C10 C11 Cl1 . . 118.90(13) ?
C13 C12 C11 . . 119.09(15) ?
C13 C12 H12 . . 120.5 ?
C11 C12 H12 . . 120.5 ?
C13 C14 C9 . . 119.98(15) ?
C13 C14 H14 . . 120.0 ?
C9 C14 H14 . . 120.0 ?
C14 C13 C12 . . 121.07(16) ?
C14 C13 Cl2 . . 119.29(14) ?
C12 C13 Cl2 . . 119.64(13) ?
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
Cl1 C11 . 1.7286(16) ?
Cl2 C13 . 1.7369(18) ?
O1 C10 . 1.3389(19) ?
O1 H1 . 0.82(2) ?
N1 C8 . 1.274(2) ?
N1 C3 . 1.424(2) ?
F1 C1 . 1.324(2) ?
C1 F3 . 1.336(3) ?
C1 F2 . 1.339(3) ?
C1 C2 . 1.491(3) ?
C2 C7 . 1.388(3) ?
C2 C3 . 1.391(3) ?
C3 C4 . 1.391(2) ?
C4 C5 . 1.388(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.370(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.378(3) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.453(2) ?
C8 H8 . 0.9300 ?
C9 C14 . 1.398(2) ?
C9 C10 . 1.408(2) ?
C10 C11 . 1.392(2) ?
C11 C12 . 1.382(3) ?
C12 C13 . 1.379(3) ?
C12 H12 . 0.9300 ?
C14 C13 . 1.371(2) ?
C14 H14 . 0.9300 ?
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 N1 . 0.82(2) 1.86(2) 2.6111(18) 152(2) yes
C14 H14 O1 3_566 0.93 2.67 3.515(2) 151.4 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
F1 C1 C2 C7 . . . . 0.8(3) ?
F3 C1 C2 C7 . . . . 121.5(2) ?
F2 C1 C2 C7 . . . . -119.7(2) ?
F1 C1 C2 C3 . . . . -178.7(2) ?
F3 C1 C2 C3 . . . . -58.0(3) ?
F2 C1 C2 C3 . . . . 60.8(2) ?
C7 C2 C3 C4 . . . . 3.8(3) ?
C1 C2 C3 C4 . . . . -176.72(19) ?
C7 C2 C3 N1 . . . . -177.07(18) ?
C1 C2 C3 N1 . . . . 2.5(3) ?
C8 N1 C3 C4 . . . . -44.0(2) ?
C8 N1 C3 C2 . . . . 136.83(17) ?
C2 C3 C4 C5 . . . . -2.1(3) ?
N1 C3 C4 C5 . . . . 178.77(18) ?
C3 C4 C5 C6 . . . . -0.6(4) ?
C4 C5 C6 C7 . . . . 1.6(4) ?
C5 C6 C7 C2 . . . . 0.1(4) ?
C3 C2 C7 C6 . . . . -2.8(3) ?
C1 C2 C7 C6 . . . . 177.7(2) ?
C3 N1 C8 C9 . . . . 179.68(14) ?
N1 C8 C9 C14 . . . . 178.07(15) ?
N1 C8 C9 C10 . . . . -0.4(2) ?
C14 C9 C10 O1 . . . . -179.21(14) ?
C8 C9 C10 O1 . . . . -0.7(2) ?
C14 C9 C10 C11 . . . . 1.0(2) ?
C8 C9 C10 C11 . . . . 179.47(14) ?
O1 C10 C11 C12 . . . . 178.95(15) ?
C9 C10 C11 C12 . . . . -1.3(2) ?
O1 C10 C11 Cl1 . . . . -1.5(2) ?
C9 C10 C11 Cl1 . . . . 178.29(12) ?
C10 C11 C12 C13 . . . . 0.6(2) ?
Cl1 C11 C12 C13 . . . . -178.95(13) ?
C10 C9 C14 C13 . . . . -0.1(2) ?
C8 C9 C14 C13 . . . . -178.60(15) ?
C9 C14 C13 C12 . . . . -0.6(3) ?
C9 C14 C13 Cl2 . . . . 179.61(12) ?
C11 C12 C13 C14 . . . . 0.4(3) ?
C11 C12 C13 Cl2 . . . . -179.85(13) ?
