#------------------------------------------------------------------------------
#$Date: 2024-10-08 21:26:17 +0300 (Tue, 08 Oct 2024) $
#$Revision: 295359 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/20/7062001.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_7062001
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_name_full               'New Journal of Chemistry'
_journal_paper_doi               10.1039/D1NJ03056F
_journal_year                    2022
_chemical_formula_moiety         'C14 H8 F3 N2 O3'
_chemical_formula_sum            'C14 H8 F3 N2 O3'
_chemical_formula_weight         309.22
_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     dual
_audit_creation_date             2021-04-07
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_audit_update_record
;
2022-07-18 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.790(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3168(6)
_cell_length_b                   6.7716(3)
_cell_length_c                   14.2320(5)
_cell_measurement_reflns_used    4246
_cell_measurement_temperature    299.97(12)
_cell_measurement_theta_max      77.4950
_cell_measurement_theta_min      3.2120
_cell_volume                     1320.94(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.97a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.97a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.97a (Rigaku OD, 2021)'
_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      299.97(12)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00 119.00   0.50    0.28    --   46.82  42.00  32.00  168
  2  ω     24.00 120.00   0.50    0.28    --   46.82  77.00  90.00  192
  3  ω     24.00 118.00   0.50    0.28    --   46.82  77.00 -60.00  188
  4  ω     79.00 178.00   0.50    1.13    --  110.25 125.00-120.00  198
  5  ω     98.00 178.00   0.50    1.13    --  110.25  42.00  32.00  160
  6  ω    -27.00  13.00   0.50    0.28    --   46.82 -19.00  60.00   80
  7  ω    -25.00  48.00   0.50    0.28    --   46.82 -42.00-119.00  146
  8  ω     38.00  80.00   0.50    1.13    --  110.25 -61.00 -60.00   84
  9  ω     38.00  80.00   0.50    1.13    --  110.25 -61.00-120.00   84
 10  ω     38.00  80.00   0.50    1.13    --  110.25 -61.00-180.00   84
 11  ω     38.00 106.00   0.50    1.13    --  110.25 -94.00-180.00  136
 12  ω     38.00 111.00   0.50    1.13    --  110.25-125.00-180.00  146
 13  ω     38.00 106.00   0.50    1.13    --  110.25 -94.00-120.00  136
 14  ω     38.00 106.00   0.50    1.13    --  110.25 -94.00 -60.00  136
 15  ω     38.00 111.00   0.50    1.13    --  110.25-125.00  30.00  146
 16  ω    -40.00  25.00   0.50    0.28    --  -46.82  42.00  32.00  130
 17  ω     -5.00  29.00   0.50    0.28    --  -46.82  19.00 150.00   68
 18  ω     -5.00  29.00   0.50    0.28    --  -46.82  19.00-150.00   68
 19  ω     -5.00  29.00   0.50    0.28    --  -46.82  19.00-180.00   68
 20  ω   -119.00 -24.00   0.50    0.28    --  -46.82 -77.00-180.00  190
 21  ω   -174.00 -89.00   0.50    1.13    -- -102.00 -42.00-119.00  170
 22  ω   -119.00 -34.00   0.50    0.28    --  -46.82 -42.00-119.00  170
 23  ω   -174.00 -89.00   0.50    1.13    -- -102.00 -45.00 150.00  170
 24  ω    -72.00 -29.00   0.50    1.13    -- -102.00  61.00  60.00   86
 25  ω    -72.00 -29.00   0.50    1.13    -- -102.00  61.00 120.00   86
 26  ω    -72.00 -29.00   0.50    1.13    -- -102.00  61.00 150.00   86
 27  ω   -125.00 -29.00   0.50    1.13    -- -102.00  77.00  60.00  192
 28  ω    -72.00 -29.00   0.50    1.13    -- -102.00  61.00-150.00   86
;
_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      -0.0597759000
_diffrn_orient_matrix_UB_12      -0.0795797000
_diffrn_orient_matrix_UB_13      -0.1008986000
_diffrn_orient_matrix_UB_21      -0.0944711000
_diffrn_orient_matrix_UB_22      0.0748930000
_diffrn_orient_matrix_UB_23      0.0191172000
_diffrn_orient_matrix_UB_31      0.0117094000
_diffrn_orient_matrix_UB_32      0.1995032000
_diffrn_orient_matrix_UB_33      -0.0473329000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6419
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         83.762
_diffrn_reflns_theta_min         3.244
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.97a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_description       platelets
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.212
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.183
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0655
_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)+(0.1432P)²+0.2926P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2135
_refine_ls_wR_factor_ref         0.2377
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1180
_reflns_number_total             1460
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj03056f3.cif
_cod_data_source_block           sh01_300_auto
_cod_depositor_comments
;

2024-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         154.61
_cod_original_formula_moiety         'C7 H4.5 F1.5 N O1.5'
_cod_original_formula_units_Z            8
_cod_original_formula_sum        'C7 H4 F1.50 N O1.50'
_cod_database_code               7062001
_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.
;
_diffrn_oxdiff_digest_frames
;
01f203b30d18f3ebd198937fdf4ca71d820005189e0
;
_diffrn_oxdiff_digest_hkl
;
0146843d9690de31a3e2cd2921f9e33b6824e5
;
_reflns_odcompleteness_completeness 98.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C18(H18), C9(H9), C2(H2), C14(H14), C13(H13), C17(H17), C19(H19)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.388
_oxdiff_exptl_absorpt_empirical_full_min 0.571
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
F6 F 0.04059(13) 0.3457(3) 0.89104(13) 0.1085(7) Uani 1 1 d . . . . .
N11 N 0.21877(16) 0.500000 0.63409(15) 0.0576(6) Uani 1 2 d S T P . .
F20 F 0.12362(18) 0.500000 1.01708(14) 0.1178(10) Uani 1 2 d S T P . .
O16 O 0.08802(16) 0.500000 0.46218(17) 0.0921(9) Uani 1 2 d S T P . .
O5 O 0.3701(2) 0.500000 0.20307(16) 0.0925(8) Uani 1 2 d S T P . .
N4 N 0.3897(2) 0.500000 0.29117(19) 0.0744(8) Uani 1 2 d S T P . .
C3 C 0.3112(2) 0.500000 0.3374(2) 0.0602(7) Uani 1 2 d S T P . .
C10 C 0.24382(19) 0.500000 0.73792(18) 0.0553(6) Uani 1 2 d S T P . .
C8 C 0.1835(2) 0.500000 0.87916(18) 0.0608(7) Uani 1 2 d S T P . .
C1 C 0.2595(2) 0.500000 0.48330(18) 0.0558(7) Uani 1 2 d S T P . .
C12 C 0.2843(2) 0.500000 0.58921(19) 0.0584(7) Uani 1 2 d S T P . .
H12 H 0.349695 0.500000 0.625683 0.070 Uiso 1 2 calc RS T P . .
C15 C 0.1628(2) 0.500000 0.4236(2) 0.0675(8) Uani 1 2 d S T P . .
C18 C 0.3551(2) 0.500000 0.9012(2) 0.0818(10) Uani 1 2 d S T P . .
H18 H 0.418767 0.500000 0.942384 0.098 Uiso 1 2 calc RS T P . .
O21 O 0.4736(2) 0.500000 0.3439(2) 0.1394(17) Uani 1 2 d S T P . .
C9 C 0.1666(2) 0.500000 0.77810(18) 0.0571(7) Uani 1 2 d S T P . .
H9 H 0.102849 0.500000 0.737097 0.069 Uiso 1 2 calc RS T P . .
C2 C 0.3338(2) 0.500000 0.43782(19) 0.0605(7) Uani 1 2 d S T P . .
H2 H 0.398744 0.500000 0.475690 0.073 Uiso 1 2 calc RS T P . .
C14 C 0.1426(2) 0.500000 0.3218(2) 0.0813(10) Uani 1 2 d S T P . .
H14 H 0.078113 0.500000 0.282805 0.098 Uiso 1 2 calc RS T P . .
C13 C 0.2168(2) 0.500000 0.27821(19) 0.0703(8) Uani 1 2 d S T P . .
H13 H 0.203148 0.500000 0.210234 0.084 Uiso 1 2 calc RS T P . .
C7 C 0.0979(2) 0.500000 0.9200(2) 0.0706(8) Uani 1 2 d S T P . .
C17 C 0.3386(2) 0.500000 0.8008(2) 0.0702(8) Uani 1 2 d S T P . .
H17 H 0.391275 0.500000 0.774864 0.084 Uiso 1 2 calc RS T P . .
C19 C 0.2771(2) 0.500000 0.9414(2) 0.0712(8) Uani 1 2 d S T P . .
H19 H 0.288159 0.500000 1.009077 0.085 Uiso 1 2 calc RS T P . .
H20 H 0.110(3) 0.500000 0.528(3) 0.096(12) Uiso 1 2 d S T P . .
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
C12 N11 C10 121.3(2) . . ?
O5 N4 C3 119.5(3) . . ?
O5 N4 O21 122.3(3) . . ?
O21 N4 C3 118.2(2) . . ?
C2 C3 N4 119.4(3) . . ?
C2 C3 C13 122.3(3) . . ?
C13 C3 N4 118.3(2) . . ?
C9 C10 N11 116.1(2) . . ?
C9 C10 C17 118.8(2) . . ?
C17 C10 N11 125.2(2) . . ?
C9 C8 C7 118.9(3) . . ?
C19 C8 C9 120.9(2) . . ?
C19 C8 C7 120.2(2) . . ?
C15 C1 C12 122.4(2) . . ?
C2 C1 C12 119.5(2) . . ?
C2 C1 C15 118.1(2) . . ?
N11 C12 C1 121.8(3) . . ?
O16 C15 C1 121.3(3) . . ?
O16 C15 C14 118.5(3) . . ?
C14 C15 C1 120.2(3) . . ?
C17 C18 C19 120.5(3) . . ?
C10 C9 C8 120.4(2) . . ?
C3 C2 C1 120.1(3) . . ?
C13 C14 C15 120.9(3) . . ?
C3 C13 C14 118.4(2) . . ?
F6 C7 F6 104.8(3) 6_565 . ?
F6 C7 F20 106.64(17) . . ?
F6 C7 F20 106.64(17) 6_565 . ?
F6 C7 C8 112.54(15) . . ?
F6 C7 C8 112.54(15) 6_565 . ?
F20 C7 C8 113.1(3) . . ?
C18 C17 C10 120.6(3) . . ?
C8 C19 C18 118.8(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
F6 C7 1.319(3) . ?
N11 C10 1.416(3) . ?
N11 C12 1.279(4) . ?
F20 C7 1.324(3) . ?
O16 C15 1.337(4) . ?
O5 N4 1.203(3) . ?
N4 C3 1.457(4) . ?
N4 O21 1.218(4) . ?
C3 C2 1.371(4) . ?
C3 C13 1.372(4) . ?
C10 C9 1.384(4) . ?
C10 C17 1.394(4) . ?
C8 C9 1.388(3) . ?
C8 C7 1.501(4) . ?
C8 C19 1.376(4) . ?
C1 C12 1.445(3) . ?
C1 C15 1.400(4) . ?
C1 C2 1.396(4) . ?
C15 C14 1.392(4) . ?
C18 C17 1.379(4) . ?
C18 C19 1.394(5) . ?
C14 C13 1.376(4) . ?
