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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/7/06/19/7061997.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_7061997
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
_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                 107.166(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3145(4)
_cell_length_b                   6.6220(2)
_cell_length_c                   14.1681(4)
_cell_measurement_temperature    180(2)
_cell_volume                     1283.18(7)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.957
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6866
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.250
_diffrn_reflns_theta_min         3.265
_exptl_absorpt_coefficient_mu    1.252
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'Not measured'
_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         0.235
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0438
_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)+(0.0492P)²+1.2761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1241
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1303
_reflns_number_total             1447
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj03056f3.cif
_cod_data_source_block           SH01_180_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 F1.50 N O1.50'
_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               7061997
_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 0.03797(8) 0.3397(2) 0.89031(8) 0.0551(4) Uani 1 1 d . . . . .
F20 F 0.12096(12) 0.500000 1.01876(10) 0.0610(5) Uani 1 2 d S T P . .
O16 O 0.08710(12) 0.500000 0.46160(13) 0.0491(5) Uani 1 2 d S T P . .
O5 O 0.36994(15) 0.500000 0.20228(12) 0.0487(5) Uani 1 2 d S T P . .
N11 N 0.21831(13) 0.500000 0.63499(13) 0.0308(4) Uani 1 2 d S T P . .
N4 N 0.39030(15) 0.500000 0.29199(14) 0.0390(5) Uani 1 2 d S T P . .
O21 O 0.47428(14) 0.500000 0.34536(15) 0.0834(10) Uani 1 2 d S T P . .
C1 C 0.26007(16) 0.500000 0.48407(15) 0.0302(5) Uani 1 2 d S T P . .
H1 H 0.113(3) 0.500000 0.523(3) 0.069(11) Uiso 1 2 d S . P . .
C3 C 0.31181(17) 0.500000 0.33775(16) 0.0321(5) Uani 1 2 d S T P . .
C8 C 0.18164(16) 0.500000 0.88107(15) 0.0317(5) Uani 1 2 d S T P . .
C9 C 0.16510(16) 0.500000 0.77914(15) 0.0303(5) Uani 1 2 d S T P . .
H9 H 0.100023 0.500000 0.736296 0.036 Uiso 1 2 calc R U P . .
C7 C 0.09562(18) 0.500000 0.92066(16) 0.0375(6) Uani 1 2 d S T P . .
C10 C 0.24307(16) 0.500000 0.73983(15) 0.0295(5) Uani 1 2 d S T P . .
C2 C 0.33463(16) 0.500000 0.43950(16) 0.0321(5) Uani 1 2 d S T P . .
H2 H 0.401041 0.500000 0.478943 0.039 Uiso 1 2 calc R U P . .
C14 C 0.14164(18) 0.500000 0.32075(17) 0.0429(6) Uani 1 2 d S T P . .
H14 H 0.075614 0.500000 0.280234 0.051 Uiso 1 2 calc R U P . .
C12 C 0.28504(16) 0.500000 0.59121(15) 0.0313(5) Uani 1 2 d S T P . .
H12 H 0.351855 0.500000 0.629471 0.038 Uiso 1 2 calc R U P . .
C15 C 0.16186(17) 0.500000 0.42341(17) 0.0356(5) Uani 1 2 d S T P . .
C17 C 0.33851(17) 0.500000 0.80396(17) 0.0377(6) Uani 1 2 d S T P . .
H17 H 0.392679 0.500000 0.778141 0.045 Uiso 1 2 calc R U P . .
C13 C 0.21574(18) 0.500000 0.27757(16) 0.0372(5) Uani 1 2 d S T P . .
H13 H 0.201538 0.500000 0.207702 0.045 Uiso 1 2 calc R U P . .
C18 C 0.35372(18) 0.500000 0.90473(17) 0.0436(6) Uani 1 2 d S T P . .
H18 H 0.418703 0.500000 0.947796 0.052 Uiso 1 2 calc R U P . .
C19 C 0.27592(18) 0.500000 0.94441(16) 0.0383(6) Uani 1 2 d S T P . .
H19 H 0.287251 0.500000 1.013943 0.046 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 120.89(19) . . ?
O21 N4 O5 122.5(2) . . ?
O21 N4 C3 118.35(19) . . ?
O5 N4 C3 119.2(2) . . ?
C2 C1 C15 118.82(19) . . ?
C2 C1 C12 119.3(2) . . ?
C15 C1 C12 121.9(2) . . ?
C2 C3 C13 121.8(2) . . ?
C2 C3 N4 119.3(2) . . ?
C13 C3 N4 118.8(2) . . ?
C19 C8 C9 120.5(2) . . ?
C19 C8 C7 120.69(19) . . ?
C9 C8 C7 118.81(19) . . ?
C10 C9 C8 120.4(2) . . ?
F20 C7 F6 106.78(13) . . ?
F20 C7 F6 106.78(13) . 6_565 ?
F6 C7 F6 105.3(2) . 6_565 ?
F20 C7 C8 113.04(19) . . ?
F6 C7 C8 112.21(12) . . ?
F6 C7 C8 112.21(12) 6_565 . ?
C9 C10 C17 119.10(19) . . ?
C9 C10 N11 115.95(19) . . ?
C17 C10 N11 124.9(2) . . ?
C3 C2 C1 119.8(2) . . ?
C13 C14 C15 121.0(2) . . ?
N11 C12 C1 121.1(2) . . ?
O16 C15 C14 118.5(2) . . ?
O16 C15 C1 121.7(2) . . ?
C14 C15 C1 119.7(2) . . ?
C18 C17 C10 119.8(2) . . ?
C14 C13 C3 118.8(2) . . ?
C17 C18 C19 121.3(2) . . ?
C8 C19 C18 118.9(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 1.3355(19) . ?
F20 C7 1.329(3) . ?
O16 C15 1.334(3) . ?
O5 N4 1.217(3) . ?
N11 C12 1.283(3) . ?
N11 C10 1.422(3) . ?
N4 O21 1.217(3) . ?
N4 C3 1.454(3) . ?
C1 C2 1.391(3) . ?
C1 C15 1.415(3) . ?
C1 C12 1.453(3) . ?
C3 C2 1.381(3) . ?
C3 C13 1.388(3) . ?
C8 C19 1.383(3) . ?
C8 C9 1.393(3) . ?
C8 C7 1.496(3) . ?
C9 C10 1.387(3) . ?
C10 C17 1.400(3) . ?
C14 C13 1.372(3) . ?
C14 C15 1.397(3) . ?
C17 C18 1.379(3) . ?
C18 C19 1.388(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
O21 N4 C3 C2 0.000(1) . . . . ?
O5 N4 C3 C2 180.000(0) . . . . ?
O21 N4 C3 C13 180.000(0) . . . . ?
O5 N4 C3 C13 0.000(0) . . . . ?
C19 C8 C9 C10 0.000(1) . . . . ?
C7 C8 C9 C10 180.000(1) . . . . ?
C19 C8 C7 F20 0.000(1) . . . . ?
C9 C8 C7 F20 180.000(1) . . . . ?
C19 C8 C7 F6 -120.83(14) . . . . ?
C9 C8 C7 F6 59.17(14) . . . . ?
C19 C8 C7 F6 120.83(14) . . . 6_565 ?
C9 C8 C7 F6 -59.17(14) . . . 6_565 ?
C8 C9 C10 C17 0.000(1) . . . . ?
C8 C9 C10 N11 180.000(1) . . . . ?
C12 N11 C10 C9 180.000(1) . . . . ?
C12 N11 C10 C17 0.000(1) . . . . ?
C13 C3 C2 C1 0.000(1) . . . . ?
N4 C3 C2 C1 180.000(0) . . . . ?
C15 C1 C2 C3 0.000(1) . . . . ?
C12 C1 C2 C3 180.000(0) . . . . ?
C10 N11 C12 C1 180.000(1) . . . . ?
C2 C1 C12 N11 180.000(1) . . . . ?
C15 C1 C12 N11 0.000(1) . . . . ?
C13 C14 C15 O16 180.000(0) . . . . ?
C13 C14 C15 C1 0.000(1) . . . . ?
C2 C1 C15 O16 180.000(0) . . . . ?
C12 C1 C15 O16 0.000(1) . . . . ?
C2 C1 C15 C14 0.000(1) . . . . ?
C12 C1 C15 C14 180.000(0) . . . . ?
C9 C10 C17 C18 0.000(1) . . . . ?
N11 C10 C17 C18 180.000(1) . . . . ?
C15 C14 C13 C3 0.000(0) . . . . ?
C2 C3 C13 C14 0.000(1) . . . . ?
N4 C3 C13 C14 180.000(0) . . . . ?
C10 C17 C18 C19 0.000(1) . . . . ?
C9 C8 C19 C18 0.000(1) . . . . ?
C7 C8 C19 C18 180.000(1) . . . . ?
C17 C18 C19 C8 0.000(1) . . . . ?
