#------------------------------------------------------------------------------
#$Date: 2023-01-05 14:18:08 +0200 (Thu, 05 Jan 2023) $
#$Revision: 280124 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/21/7062198.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_7062198
loop_
_publ_author_name
'Hulushe, Siya T.'
'Malan, Frederick P.'
'Hosten, Eric C.'
'Lobb, Kevin A.'
'Khanye, Setshaba D.'
'Watkins, Gareth M.'
_publ_section_title
;
 Photo-and thermoresponsive N-salicylideneaniline derivatives: solid-state
 studies and structural aspects
;
_journal_issue                   43
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20940
_journal_page_last               20950
_journal_paper_doi               10.1039/D1NJ03056F
_journal_volume                  46
_journal_year                    2022
_chemical_compound_source        Synthesized
_chemical_formula_moiety         'C14 H9 F3 N2 O3'
_chemical_formula_sum            'C14 H9 F3 N2 O3'
_chemical_formula_weight         310.23
_chemical_melting_point          441
_chemical_name_common
2-((E)-(3-(trifluoromethyl)phenylimino)methyl)-4-nitrophenol
_chemical_name_systematic        Unk
_chemical_properties_physical    thermochromic
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-02-28
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2021-03-25 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.830(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3061(3)
_cell_length_b                   6.7681(2)
_cell_length_c                   14.2305(3)
_cell_measurement_reflns_used    6247
_cell_measurement_temperature    294.8(3)
_cell_measurement_theta_max      75.9850
_cell_measurement_theta_min      3.2670
_cell_volume                     1318.85(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.8(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00 120.00   0.50    0.10    --   47.20  77.00  30.00  190
  2  ω     32.00 120.00   0.50    0.10    --   47.20  57.00 120.00  176
  3  ω     32.00 122.00   0.50    0.10    --   47.20  13.00  79.00  180
  4  ω     25.00 120.00   0.50    0.10    --   47.20  77.00-120.00  190
  5  ω     25.00 120.00   0.50    0.10    --   47.20  77.00-180.00  190
  6  ω     92.00 177.00   0.50    0.80    --  104.75  45.00 -60.00  170
  7  ω    -26.00  42.00   0.50    0.10    --   47.20 -38.00 120.00  136
  8  ω     90.00 172.00   0.50    0.80    --  104.75  13.00  79.00  164
  9  ω    -27.00  12.00   0.50    0.10    --   47.20 -19.00 -60.00   78
 10  ω    -27.00  -1.00   0.50    0.10    --   47.20 -13.00 -91.00   52
 11  ω     32.00  80.00   0.50    0.80    --  104.75 -61.00-180.00   96
 12  ω     32.00  80.00   0.50    0.80    --  104.75 -61.00-150.00   96
 13  ω     32.00  80.00   0.50    0.80    --  104.75 -61.00 -30.00   96
 14  ω     32.00  80.00   0.50    0.80    --  104.75 -61.00  30.00   96
 15  ω     32.00  80.00   0.50    0.80    --  104.75 -61.00  90.00   96
 16  ω     32.00 112.00   0.50    0.80    --  104.75-125.00 150.00  160
 17  ω     32.00 106.00   0.50    0.80    --  104.75 -94.00  30.00  148
 18  ω     32.00 112.00   0.50    0.80    --  104.75-125.00-150.00  160
 19  ω     32.00 112.00   0.50    0.80    --  104.75-125.00-180.00  160
 20  ω     32.00 106.00   0.50    0.80    --  104.75 -94.00-180.00  148
 21  ω     -4.00  28.00   0.50    0.10    --  -47.20  19.00-150.00   64
 22  ω   -112.00 -29.00   0.50    0.80    -- -102.00 125.00-150.00  166
 23  ω   -112.00 -29.00   0.50    0.80    -- -102.00 125.00 -60.00  166
 24  ω    -72.00 -29.00   0.50    0.80    -- -102.00  61.00-180.00   86
 25  ω   -164.00 -87.00   0.50    0.80    -- -102.00 -13.00 -91.00  154
 26  ω   -168.00 -88.00   0.50    0.80    -- -102.00 -15.00-150.00  160
 27  ω   -122.00 -32.00   0.50    0.10    --  -47.20 -13.00 -91.00  180
 28  ω   -175.00 -79.00   0.50    0.80    -- -102.00 -77.00-180.00  192
 29  ω   -168.00 -88.00   0.50    0.80    -- -102.00 -15.00   0.00  160
 30  ω   -175.00 -96.00   0.50    0.80    -- -102.00 -77.00 150.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1049165000
_diffrn_orient_matrix_UB_12      -0.0376430000
_diffrn_orient_matrix_UB_13      -0.0653580000
_diffrn_orient_matrix_UB_21      -0.0369736000
_diffrn_orient_matrix_UB_22      0.0037298000
_diffrn_orient_matrix_UB_23      0.0914719000
_diffrn_orient_matrix_UB_31      -0.0169314000
_diffrn_orient_matrix_UB_32      0.2244124000
_diffrn_orient_matrix_UB_33      -0.0124666000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0106
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8627
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.016
_diffrn_reflns_theta_min         3.245
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.218
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_recrystallization_method Methanol
_exptl_crystal_size_max          0.731
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.166
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0017(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1415
_refine_ls_number_restraints     44
_refine_ls_restrained_S_all      1.265
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0510
_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)+(0.0662P)²+0.7550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1470
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1262
_reflns_number_total             1415
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj03056f2.cif
_cod_data_source_block           sh01b_rt
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               7062198
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.78125(14) 0.500000 0.36601(13) 0.0511(5) Uani 1 2 d S T P . .
O3 O 0.62984(18) 0.500000 0.79707(14) 0.0862(7) Uani 1 2 d S T P . .
O1 O 0.91216(13) 0.500000 0.53797(15) 0.0857(8) Uani 1 2 d S T P . .
N2 N 0.60994(18) 0.500000 0.70844(16) 0.0668(6) Uani 1 2 d S T P . .
F1 F 0.95934(10) 0.6551(3) 0.10894(11) 0.0974(6) Uani 0.974(2) 1 d D U . A 1
C1 C 0.71542(17) 0.500000 0.41028(16) 0.0521(6) Uani 1 2 d S T P . .
H1A H 0.650043 0.500000 0.373542 0.062 Uiso 1 2 calc RS T P . .
C22 C 0.83341(17) 0.500000 0.22173(16) 0.0509(6) Uani 1 2 d S T P . .
H22 H 0.897143 0.500000 0.262869 0.061 Uiso 1 2 calc RS T P . .
C21 C 0.75635(16) 0.500000 0.26184(15) 0.0485(6) Uani 1 2 d S T P . .
C11 C 0.74021(17) 0.500000 0.51679(16) 0.0494(6) Uani 1 2 d S T P . .
C16 C 0.66604(17) 0.500000 0.56173(16) 0.0534(6) Uani 1 2 d S T P . .
H16 H 0.601125 0.500000 0.523635 0.064 Uiso 1 2 calc RS T P . .
C14 C 0.7835(2) 0.500000 0.72148(17) 0.0639(7) Uani 1 2 d S T P . .
H14 H 0.797344 0.500000 0.789493 0.077 Uiso 1 2 calc RS T P . .
C23 C 0.81682(17) 0.500000 0.12057(16) 0.0536(6) Uani 1 2 d DS TU P A .
C13 C 0.8573(2) 0.500000 0.67815(19) 0.0746(9) Uani 1 2 d S T P . .
H13 H 0.921782 0.500000 0.717359 0.090 Uiso 1 2 calc RS T P . .
C26 C 0.66120(18) 0.500000 0.19902(17) 0.0639(7) Uani 1 2 d S T P . .
H26 H 0.608415 0.500000 0.224783 0.077 Uiso 1 2 calc RS T P . .
C25 C 0.6455(2) 0.500000 0.09907(18) 0.0747(9) Uani 1 2 d S T P A .
H25 H 0.581886 0.500000 0.057725 0.090 Uiso 1 2 calc RS T P . .
O2 O 0.52675(17) 0.500000 0.65627(17) 0.1316(15) Uani 1 2 d S T P . .
C15 C 0.68841(18) 0.500000 0.66261(17) 0.0533(6) Uani 1 2 d S T P . .
C27 C 0.9016(2) 0.500000 0.07979(18) 0.0651(7) Uani 1 2 d DS TU P . .
C12 C 0.83752(18) 0.500000 0.57629(18) 0.0601(7) Uani 1 2 d S T P . .
C24 C 0.72276(19) 0.500000 0.05886(17) 0.0647(7) Uani 1 2 d S T P . .
H24 H 0.711329 0.500000 -0.008887 0.078 Uiso 1 2 calc RS T P A .
H1 H 0.890(3) 0.500000 0.479(3) 0.093(12) Uiso 1 2 d S T P . .
F3 F 0.87658(15) 0.500000 -0.01694(12) 0.1078(9) Uani 0.974(2) 2 d DS TU P A 1
F1A F 0.9936(14) 0.500000 0.140(2) 0.0974(6) Uani 0.052(5) 2 d DS TU P A 2
F3A F 0.897(5) 0.663(9) 0.022(5) 0.1078(9) Uani 0.0130(12) 1 d D U . A 2
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'
F F 0.0727 0.0534 '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'
O O 0.0492 0.0322 '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
_geom_angle_publ_flag
C1 N1 C21 121.2(2) . . ?
O3 N2 C15 119.3(2) . . ?
O2 N2 O3 122.3(2) . . ?
O2 N2 C15 118.5(2) . . ?
N1 C1 C11 121.5(2) . . ?
C21 C22 C23 120.7(2) . . ?
C22 C21 N1 116.26(19) . . ?
C22 C21 C26 118.9(2) . . ?
C26 C21 N1 124.9(2) . . ?
C16 C11 C1 119.5(2) . . ?
C16 C11 C12 118.6(2) . . ?
C12 C11 C1 121.9(2) . . ?
C15 C16 C11 120.1(2) . . ?
C13 C14 C15 118.8(2) . . ?
C22 C23 C27 119.3(2) . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 C27 120.5(2) . . ?
C14 C13 C12 121.2(2) . . ?
C25 C26 C21 120.0(2) . . ?
C26 C25 C24 121.2(2) . . ?
C16 C15 N2 119.4(2) . . ?
C14 C15 N2 118.9(2) . . ?
C14 C15 C16 121.7(2) . . ?
F1 C27 F1 104.7(2) . 6_565 ?
F1 C27 C23 112.48(14) . . ?
F1 C27 C23 112.48(14) 6_565 . ?
F1 C27 F3A 58(3) 6_565 6_565 ?
F1 C27 F3A 138(3) . 6_565 ?
F3 C27 F1 106.42(15) . 6_565 ?
F3 C27 F1 106.42(15) . . ?
F3 C27 C23 113.7(2) . . ?
F3 C27 F3A 54(4) . 6_565 ?
F1A C27 C23 120.7(16) . . ?
F1A C27 F3A 105(3) . . ?
F1A C27 F3A 105(3) . 6_565 ?
F3A C27 C23 109(3) 6_565 . ?
F3A C27 C23 109(3) . . ?
F3A C27 F3A 108(8) . 6_565 ?
O1 C12 C11 121.7(2) . . ?
O1 C12 C13 118.7(2) . . ?
C13 C12 C11 119.6(2) . . ?
C23 C24 C25 119.1(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.276(3) . ?
N1 C21 1.421(3) . ?
O3 N2 1.210(3) . ?
O1 C12 1.332(3) . ?
N2 O2 1.207(3) . ?
N2 C15 1.452(3) . ?
F1 C27 1.326(2) . ?
C1 C11 1.453(3) . ?
C22 C21 1.380(3) . ?
C22 C23 1.389(3) . ?
C21 C26 1.396(3) . ?
C11 C16 1.388(3) . ?
C11 C12 1.404(3) . ?
C16 C15 1.377(3) . ?
C14 C13 1.368(4) . ?
C14 C15 1.375(4) . ?
C23 C27 1.488(3) . ?
C23 C24 1.378(3) . ?
C13 C12 1.394(3) . ?
C26 C25 1.374(3) . ?
C25 C24 1.384(4) . ?
C27 F3 1.318(3) . ?
C27 F1A 1.346(16) . ?
C27 F3A 1.365(17) 6_565 ?
C27 F3A 1.365(17) . ?
