#------------------------------------------------------------------------------
#$Date: 2022-10-25 03:50:47 +0300 (Tue, 25 Oct 2022) $
#$Revision: 278763 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/19/7061996.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_7061996
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         'C7 H4 F1.50 N O1.50'
_chemical_formula_sum            'C7 H4 F1.5 N O1.5'
_chemical_formula_weight         154.61
_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                 107.224(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.3165(4)
_cell_length_b                   6.5939(2)
_cell_length_c                   14.1523(4)
_cell_measurement_temperature    150(2)
_cell_volume                     1276.09(7)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.960
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.960
_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            6528
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.129
_diffrn_reflns_theta_min         3.269
_exptl_absorpt_coefficient_mu    1.259
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.610
_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         0.273
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.208
_refine_ls_R_factor_all          0.0460
_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)+(0.0416P)²+1.6317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1311
_reflns_number_total             1442
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj03056f3.cif
_cod_data_source_block           SH01_150_auto
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_original_formula_sum        'C7 H4 F1.50 N O1.50'
_cod_database_code               7061996
_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 0.96270(8) 0.66148(19) 0.10991(8) 0.0448(3) Uani 1 1 d . . . . .
F20 F 0.87981(12) 0.500000 -0.01915(11) 0.0502(5) Uani 1 2 d S T P . .
O16 O 0.91294(13) 0.500000 0.53844(13) 0.0404(5) Uani 1 2 d S T P . .
O5 O 0.63011(15) 0.500000 0.79793(13) 0.0401(5) Uani 1 2 d S T P . .
N11 N 0.78179(14) 0.500000 0.36473(14) 0.0251(4) Uani 1 2 d S T P . .
N4 N 0.60955(16) 0.500000 0.70797(15) 0.0322(5) Uani 1 2 d S T P . .
O21 O 0.52550(15) 0.500000 0.65428(15) 0.0703(9) Uani 1 2 d S T P . .
C1 C 0.73978(17) 0.500000 0.51572(16) 0.0253(5) Uani 1 2 d S T P . .
H1 H 0.887(3) 0.500000 0.474(3) 0.061(11) Uiso 1 2 d S . P . .
C10 C 0.75722(17) 0.500000 0.25975(16) 0.0245(5) Uani 1 2 d S T P . .
C8 C 0.81890(17) 0.500000 0.11869(16) 0.0265(5) Uani 1 2 d S T P . .
C12 C 0.71497(17) 0.500000 0.40843(16) 0.0258(5) Uani 1 2 d S T P . .
H12 H 0.648170 0.500000 0.369989 0.031 Uiso 1 2 calc R U P . .
C3 C 0.68815(18) 0.500000 0.66220(17) 0.0270(5) Uani 1 2 d S T P . .
C9 C 0.83521(17) 0.500000 0.22077(16) 0.0252(5) Uani 1 2 d S T P . .
H9 H 0.900242 0.500000 0.263861 0.030 Uiso 1 2 calc R U P . .
C13 C 0.78430(19) 0.500000 0.72251(17) 0.0306(5) Uani 1 2 d S T P . .
H13 H 0.798528 0.500000 0.792474 0.037 Uiso 1 2 calc R U P . .
C2 C 0.66537(17) 0.500000 0.56039(17) 0.0269(5) Uani 1 2 d S T P . .
H2 H 0.598934 0.500000 0.520862 0.032 Uiso 1 2 calc R U P . .
C14 C 0.85838(18) 0.500000 0.67939(18) 0.0358(6) Uani 1 2 d S T P . .
H14 H 0.924418 0.500000 0.720026 0.043 Uiso 1 2 calc R U P . .
C18 C 0.64664(19) 0.500000 0.09434(18) 0.0365(6) Uani 1 2 d S T P . .
H18 H 0.581701 0.500000 0.051036 0.044 Uiso 1 2 calc R U P . .
C15 C 0.83816(18) 0.500000 0.57662(18) 0.0302(5) Uani 1 2 d S T P . .
C7 C 0.90501(18) 0.500000 0.07936(17) 0.0306(5) Uani 1 2 d S T P . .
C17 C 0.66162(18) 0.500000 0.19539(17) 0.0314(6) Uani 1 2 d S T P . .
H17 H 0.607399 0.500000 0.221106 0.038 Uiso 1 2 calc R U P . .
C19 C 0.72435(19) 0.500000 0.05497(17) 0.0318(6) Uani 1 2 d S T P . .
H19 H 0.713091 0.500000 -0.014640 0.038 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 121.0(2) . . ?
O21 N4 O5 122.7(2) . . ?
O21 N4 C3 118.3(2) . . ?
O5 N4 C3 119.1(2) . . ?
C2 C1 C15 118.7(2) . . ?
C2 C1 C12 119.5(2) . . ?
C15 C1 C12 121.8(2) . . ?
C9 C10 C17 119.2(2) . . ?
C9 C10 N11 115.9(2) . . ?
C17 C10 N11 124.8(2) . . ?
C19 C8 C9 120.4(2) . . ?
C19 C8 C7 120.8(2) . . ?
C9 C8 C7 118.8(2) . . ?
N11 C12 C1 121.1(2) . . ?
C2 C3 C13 121.8(2) . . ?
C2 C3 N4 119.3(2) . . ?
C13 C3 N4 118.9(2) . . ?
C10 C9 C8 120.4(2) . . ?
C14 C13 C3 118.9(2) . . ?
C3 C2 C1 119.9(2) . . ?
C13 C14 C15 121.0(2) . . ?
C17 C18 C19 121.3(2) . . ?
O16 C15 C14 118.6(2) . . ?
O16 C15 C1 121.7(2) . . ?
C14 C15 C1 119.7(2) . . ?
F20 C7 F6 106.74(14) . 6_565 ?
F20 C7 F6 106.73(14) . . ?
F6 C7 F6 105.4(2) 6_565 . ?
F20 C7 C8 113.1(2) . . ?
F6 C7 C8 112.19(13) 6_565 . ?
F6 C7 C8 112.19(13) . . ?
C18 C17 C10 119.7(2) . . ?
C18 C19 C8 119.0(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 1.3384(19) . ?
F20 C7 1.333(3) . ?
O16 C15 1.334(3) . ?
O5 N4 1.219(3) . ?
N11 C12 1.284(3) . ?
N11 C10 1.422(3) . ?
N4 O21 1.218(3) . ?
N4 C3 1.455(3) . ?
C1 C2 1.390(3) . ?
C1 C15 1.417(3) . ?
C1 C12 1.453(3) . ?
C10 C9 1.384(3) . ?
C10 C17 1.402(3) . ?
C8 C19 1.387(3) . ?
C8 C9 1.393(3) . ?
C8 C7 1.495(3) . ?
C3 C2 1.380(3) . ?
C3 C13 1.388(3) . ?
C13 C14 1.371(4) . ?
C14 C15 1.396(3) . ?
C18 C17 1.382(3) . ?
C18 C19 1.384(4) . ?
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) . . . . ?
C10 N11 C12 C1 180.000(0) . . . . ?
C2 C1 C12 N11 180.000(1) . . . . ?
C15 C1 C12 N11 0.000(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) . . . . ?
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) . . . . ?
C2 C3 C13 C14 0.000(1) . . . . ?
N4 C3 C13 C14 180.000(1) . . . . ?
C13 C3 C2 C1 0.000(1) . . . . ?
N4 C3 C2 C1 180.000(1) . . . . ?
C15 C1 C2 C3 0.000(1) . . . . ?
C12 C1 C2 C3 180.000(1) . . . . ?
C3 C13 C14 C15 0.000(1) . . . . ?
C13 C14 C15 O16 180.000(1) . . . . ?
C13 C14 C15 C1 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) . . . . ?
C19 C8 C7 F20 0.000(0) . . . . ?
C9 C8 C7 F20 180.000(0) . . . . ?
C19 C8 C7 F6 -120.78(14) . . . 6_565 ?
C9 C8 C7 F6 59.22(14) . . . 6_565 ?
C19 C8 C7 F6 120.78(14) . . . . ?
C9 C8 C7 F6 -59.22(14) . . . . ?
C19 C18 C17 C10 0.000(0) . . . . ?
C9 C10 C17 C18 0.000(0) . . . . ?
N11 C10 C17 C18 180.000(0) . . . . ?
C17 C18 C19 C8 0.000(0) . . . . ?
C9 C8 C19 C18 0.000(0) . . . . ?
C7 C8 C19 C18 180.0 . . . . ?
