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#$Date: 2024-10-08 21:26:17 +0300 (Tue, 08 Oct 2024) $
#$Revision: 295359 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/19/7061994.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_7061994
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_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
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2022-07-18 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.249(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3244(3)
_cell_length_b                   6.58850(10)
_cell_length_c                   14.1537(3)
_cell_measurement_temperature    141(2)
_cell_volume                     1275.70(4)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      141(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6765
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.918
_diffrn_reflns_theta_min         3.270
_exptl_absorpt_coefficient_mu    1.259
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_F_000             628
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0403
_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)+(0.0528P)²+1.3485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1195
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1288
_reflns_number_total             1456
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj03056f3.cif
_cod_data_source_block           SH01_133_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_units_Z            8
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_original_formula_sum        'C7 H4 F1.50 N O1.50'
_cod_database_code               7061994
_shelx_shelxl_version_number     2016/6
_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
F6 F 0.96283(7) 0.66176(17) 0.11002(8) 0.0437(3) Uani 1 1 d . . . . .
F20 F 0.87995(11) 0.500000 -0.01923(10) 0.0487(4) Uani 1 2 d S T P . .
O16 O 0.91302(11) 0.500000 0.53855(12) 0.0397(5) Uani 1 2 d S T P . .
O5 O 0.63008(13) 0.500000 0.79801(11) 0.0393(4) Uani 1 2 d S T P . .
N11 N 0.78166(13) 0.500000 0.36460(12) 0.0253(4) Uani 1 2 d S T P . .
N4 N 0.60956(14) 0.500000 0.70782(13) 0.0317(4) Uani 1 2 d S T P . .
O21 O 0.52546(13) 0.500000 0.65424(14) 0.0694(8) Uani 1 2 d S T P . .
C10 C 0.75717(15) 0.500000 0.25968(14) 0.0242(4) Uani 1 2 d S T P . .
C2 C 0.66521(16) 0.500000 0.56023(15) 0.0263(5) Uani 1 2 d S T P . .
H2 H 0.598809 0.500000 0.520659 0.032 Uiso 1 2 calc R U P . .
C8 C 0.81886(16) 0.500000 0.11859(15) 0.0265(5) Uani 1 2 d S T P . .
C3 C 0.68810(16) 0.500000 0.66218(15) 0.0261(5) Uani 1 2 d S T P . .
C12 C 0.71490(15) 0.500000 0.40834(15) 0.0254(4) Uani 1 2 d S T P . .
H12 H 0.648111 0.500000 0.369933 0.030 Uiso 1 2 calc R U P . .
C1 C 0.73985(15) 0.500000 0.51565(14) 0.0245(4) Uani 1 2 d S T P . .
H1 H 0.885(3) 0.500000 0.474(3) 0.070(11) Uiso 1 2 d S . P . .
C15 C 0.83826(16) 0.500000 0.57671(16) 0.0293(5) Uani 1 2 d S T P . .
C9 C 0.83527(15) 0.500000 0.22066(15) 0.0253(4) Uani 1 2 d S T P . .
H9 H 0.900286 0.500000 0.263749 0.030 Uiso 1 2 calc R U P . .
C14 C 0.85853(17) 0.500000 0.67943(16) 0.0347(5) Uani 1 2 d S T P . .
H14 H 0.924539 0.500000 0.720076 0.042 Uiso 1 2 calc R U P . .
C7 C 0.90517(16) 0.500000 0.07926(15) 0.0299(5) Uani 1 2 d S T P . .
C13 C 0.78420(17) 0.500000 0.72266(15) 0.0300(5) Uani 1 2 d S T P . .
H13 H 0.798380 0.500000 0.792617 0.036 Uiso 1 2 calc R U P . .
C18 C 0.64663(17) 0.500000 0.09420(16) 0.0354(5) Uani 1 2 d S T P . .
H18 H 0.581703 0.500000 0.050914 0.042 Uiso 1 2 calc R U P . .
C17 C 0.66156(16) 0.500000 0.19499(15) 0.0306(5) Uani 1 2 d S T P . .
H17 H 0.607301 0.500000 0.220602 0.037 Uiso 1 2 calc R U P . .
C19 C 0.72446(17) 0.500000 0.05458(15) 0.0312(5) Uani 1 2 d S T P . .
H19 H 0.713252 0.500000 -0.015022 0.037 Uiso 1 2 calc R U 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 121.03(18) . . ?
O21 N4 O5 122.5(2) . . ?
O21 N4 C3 118.42(18) . . ?
O5 N4 C3 119.08(19) . . ?
C9 C10 C17 119.12(18) . . ?
C9 C10 N11 115.97(18) . . ?
C17 C10 N11 124.92(19) . . ?
C3 C2 C1 119.78(19) . . ?
C19 C8 C9 120.63(19) . . ?
C19 C8 C7 120.62(18) . . ?
C9 C8 C7 118.75(18) . . ?
C2 C3 C13 121.9(2) . . ?
C2 C3 N4 119.26(19) . . ?
C13 C3 N4 118.83(18) . . ?
N11 C12 C1 121.09(19) . . ?
C2 C1 C15 118.78(18) . . ?
C2 C1 C12 119.30(19) . . ?
C15 C1 C12 121.92(19) . . ?
O16 C15 C14 118.53(19) . . ?
O16 C15 C1 121.68(19) . . ?
C14 C15 C1 119.8(2) . . ?
C10 C9 C8 120.33(19) . . ?
C13 C14 C15 120.9(2) . . ?
F20 C7 F6 106.85(12) . . ?
F20 C7 F6 106.85(12) . 6_565 ?
F6 C7 F6 105.44(18) . 6_565 ?
F20 C7 C8 113.01(18) . . ?
F6 C7 C8 112.10(12) . . ?
F6 C7 C8 112.10(12) 6_565 . ?
C14 C13 C3 118.82(19) . . ?
C17 C18 C19 121.4(2) . . ?
C18 C17 C10 119.8(2) . . ?
C8 C19 C18 118.71(19) . . ?
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 1.3395(17) . ?
F20 C7 1.332(2) . ?
O16 C15 1.335(3) . ?
O5 N4 1.222(2) . ?
N11 C12 1.284(3) . ?
N11 C10 1.421(3) . ?
N4 O21 1.218(3) . ?
N4 C3 1.454(3) . ?
C10 C9 1.387(3) . ?
C10 C17 1.404(3) . ?
C2 C3 1.382(3) . ?
C2 C1 1.393(3) . ?
C8 C19 1.387(3) . ?
C8 C9 1.393(3) . ?
C8 C7 1.499(3) . ?
C3 C13 1.389(3) . ?
C12 C1 1.453(3) . ?
C1 C15 1.418(3) . ?
C15 C14 1.396(3) . ?
C14 C13 1.376(3) . ?
C18 C17 1.378(3) . ?
C18 C19 1.389(3) . ?
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
_geom_torsion_publ_flag
C12 N11 C10 C9 180.000(0) . . . . ?
C12 N11 C10 C17 0.000(0) . . . . ?
C1 C2 C3 C13 0.000(1) . . . . ?
C1 C2 C3 N4 180.000(1) . . . . ?
O21 N4 C3 C2 0.000(1) . . . . ?
O5 N4 C3 C2 180.000(1) . . . . ?
O21 N4 C3 C13 180.000(1) . . . . ?
O5 N4 C3 C13 0.000(1) . . . . ?
C10 N11 C12 C1 180.000(0) . . . . ?
C3 C2 C1 C15 0.000(1) . . . . ?
C3 C2 C1 C12 180.000(1) . . . . ?
N11 C12 C1 C2 180.000(0) . . . . ?
N11 C12 C1 C15 0.000(1) . . . . ?
C2 C1 C15 O16 180.000(1) . . . . ?
C12 C1 C15 O16 0.000(1) . . . . ?
C2 C1 C15 C14 0.000(1) . . . . ?
C12 C1 C15 C14 180.000(1) . . . . ?
C17 C10 C9 C8 0.000(0) . . . . ?
N11 C10 C9 C8 180.000(0) . . . . ?
C19 C8 C9 C10 0.000(0) . . . . ?
C7 C8 C9 C10 180.000(0) . . . . ?
O16 C15 C14 C13 180.000(1) . . . . ?
C1 C15 C14 C13 0.000(1) . . . . ?
C19 C8 C7 F20 0.000(0) . . . . ?
C9 C8 C7 F20 180.000(0) . . . . ?
C19 C8 C7 F6 120.82(13) . . . . ?
C9 C8 C7 F6 -59.18(13) . . . . ?
C19 C8 C7 F6 -120.82(13) . . . 6_565 ?
C9 C8 C7 F6 59.18(13) . . . 6_565 ?
C15 C14 C13 C3 0.000(1) . . . . ?
C2 C3 C13 C14 0.000(1) . . . . ?
N4 C3 C13 C14 180.000(1) . . . . ?
C19 C18 C17 C10 0.000(0) . . . . ?
C9 C10 C17 C18 0.000(0) . . . . ?
N11 C10 C17 C18 180.000(0) . . . . ?
C9 C8 C19 C18 0.000(0) . . . . ?
C7 C8 C19 C18 180.0 . . . . ?
C17 C18 C19 C8 0.000(0) . . . . ?
