#------------------------------------------------------------------------------
#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/86/7118646.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_7118646
loop_
_publ_author_name
'Bushuyev, Oleksandr S.'
'Tomberg, Anna'
'Vinden, Joanna R.'
'Moitessier, Nicolas'
'Barrett, Christopher J.'
'Friščić, Tomislav'
_publ_section_title
;
 Azo⋯phenyl stacking: a persistent self-assembly motif guides the
 assembly of fluorinated cis-azobenzenes into photo-mechanical needle crystals
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   10
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2103
_journal_page_last               2106
_journal_paper_doi               10.1039/c5cc08590j
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C26 H14 F8 I2 N4'
_chemical_formula_weight         788.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-10-13 deposited with the CCDC.
2015-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.287(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.300(4)
_cell_length_b                   5.4157(7)
_cell_length_c                   17.841(2)
_cell_measurement_temperature    151(2)
_cell_volume                     2717.9(6)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      151(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8190
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         1.448
_exptl_absorpt_coefficient_mu    2.393
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_description       needle
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.664
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0226
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0167P)²+2.5118P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0475
_refine_ls_wR_factor_ref         0.0500
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2590
_reflns_number_total             2982
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc08590j2.cif
_cod_data_source_block           mo_Bushuyev5_0m
_cod_original_cell_volume        2718.0(6)
_cod_database_code               7118646
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelx_estimated_absorpt_t_min   0.299
_shelx_estimated_absorpt_t_max   0.839
_shelxl_version_number           2014-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
I1 I 0.39909(2) 0.21790(3) 0.96134(2) 0.02820(6) Uani 1 1 d . .
F1 F 0.50758(5) 0.3523(3) 0.93226(8) 0.0331(3) Uani 1 1 d . .
F2 F 0.54375(5) 0.7094(3) 0.85148(8) 0.0336(3) Uani 1 1 d . .
F3 F 0.35185(5) 0.6086(3) 0.84063(9) 0.0397(4) Uani 1 1 d . .
F4 F 0.38830(6) 0.9668(3) 0.76052(9) 0.0413(4) Uani 1 1 d . .
N1 N 0.14710(8) 0.5815(4) 0.94319(13) 0.0363(5) Uani 1 1 d . .
N2 N 0.48388(8) 1.0679(4) 0.77107(12) 0.0323(5) Uani 1 1 d . .
C1 C 0.12733(10) 0.7704(5) 0.90297(17) 0.0366(6) Uani 1 1 d . .
H1 H 0.0940 0.7937 0.9014 0.044 Uiso 1 1 calc R U
C2 C 0.15295(10) 0.9337(5) 0.86354(15) 0.0344(6) Uani 1 1 d . .
H3 H 0.1372 1.0660 0.8363 0.041 Uiso 1 1 calc R U
C3 C 0.20170(9) 0.9045(5) 0.86373(14) 0.0281(6) Uani 1 1 d . .
C4 C 0.22955(10) 1.0819(5) 0.82341(15) 0.0342(6) Uani 1 1 d . .
H4 H 0.2121 1.2001 0.7923 0.041 Uiso 1 1 calc R U
C5 C 0.27583(11) 1.0920(5) 0.82643(17) 0.0421(7) Uani 1 1 d . .
H5 H 0.2949 0.9778 0.8568 0.050 Uiso 1 1 calc R U
H2 H 0.2905 1.2135 0.7983 0.050 Uiso 1 1 calc R U
C6 C 0.19396(11) 0.5506(5) 0.94287(17) 0.0421(7) Uani 1 1 d . .
H7 H 0.2086 0.4158 0.9704 0.050 Uiso 1 1 calc R U
C7 C 0.22231(10) 0.7037(5) 0.90471(17) 0.0384(7) Uani 1 1 d . .
H6 H 0.2555 0.6729 0.9063 0.046 Uiso 1 1 calc R U
C8 C 0.42880(9) 0.4725(4) 0.88971(13) 0.0249(5) Uani 1 1 d . .
C9 C 0.47732(9) 0.5026(4) 0.89010(13) 0.0240(5) Uani 1 1 d . .
C10 C 0.49613(9) 0.6829(4) 0.84724(13) 0.0246(5) Uani 1 1 d . .
C11 C 0.46695(9) 0.8446(4) 0.80301(13) 0.0253(5) Uani 1 1 d . .
C12 C 0.39975(9) 0.6293(5) 0.84388(14) 0.0269(5) Uani 1 1 d . .
C13 C 0.41807(9) 0.8132(5) 0.80224(14) 0.0284(5) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C1 N1 C6 116.8(2) .
N2 N2 C11 122.45(13) 2_656
N1 C1 C2 123.4(3) .
C1 C2 C3 120.1(3) .
C2 C3 C7 116.5(2) .
C2 C3 C4 120.5(2) .
C7 C3 C4 123.0(2) .
C5 C4 C3 126.3(3) .
N1 C6 C7 123.8(3) .
C6 C7 C3 119.4(3) .
C9 C8 C12 117.1(2) .
C9 C8 I1 122.28(18) .
C12 C8 I1 120.44(19) .
F1 C9 C8 120.1(2) .
F1 C9 C10 118.4(2) .
C8 C9 C10 121.5(2) .
F2 C10 C9 119.1(2) .
F2 C10 C11 119.5(2) .
C9 C10 C11 121.2(2) .
C10 C11 C13 117.2(2) .
C10 C11 N2 123.4(2) .
C13 C11 N2 118.1(2) .
F3 C12 C13 118.1(2) .
F3 C12 C8 120.1(2) .
C13 C12 C8 121.8(2) .
F4 C13 C12 119.6(2) .
F4 C13 C11 119.4(2) .
C12 C13 C11 121.0(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C8 2.116(2) .
F1 C9 1.349(3) .
F2 C10 1.349(3) .
F3 C12 1.355(3) .
F4 C13 1.349(3) .
N1 C1 1.337(4) .
N1 C6 1.337(4) .
N2 N2 1.244(4) 2_656
N2 C11 1.441(3) .
C1 C2 1.384(4) .
C2 C3 1.388(4) .
C3 C7 1.402(4) .
C3 C4 1.478(4) .
C4 C5 1.306(4) .
C6 C7 1.383(4) .
C8 C9 1.382(3) .
C8 C12 1.385(3) .
C9 C10 1.382(3) .
C10 C11 1.389(4) .
C11 C13 1.392(4) .
C12 C13 1.378(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
C6 N1 C1 C2 -1.5(4) .
N1 C1 C2 C3 0.7(4) .
C1 C2 C3 C7 0.5(4) .
C1 C2 C3 C4 -178.4(3) .
C2 C3 C4 C5 171.5(3) .
C7 C3 C4 C5 -7.4(4) .
C1 N1 C6 C7 1.0(4) .
N1 C6 C7 C3 0.2(5) .
C2 C3 C7 C6 -1.0(4) .
C4 C3 C7 C6 178.0(3) .
C12 C8 C9 F1 -178.5(2) .
I1 C8 C9 F1 5.9(3) .
C12 C8 C9 C10 0.6(3) .
I1 C8 C9 C10 -174.92(18) .
F1 C9 C10 F2 -2.9(3) .
C8 C9 C10 F2 177.9(2) .
F1 C9 C10 C11 -179.6(2) .
C8 C9 C10 C11 1.2(4) .
F2 C10 C11 C13 -178.3(2) .
C9 C10 C11 C13 -1.6(3) .
F2 C10 C11 N2 -11.2(3) .
C9 C10 C11 N2 165.5(2) .
N2 N2 C11 C10 57.1(4) 2_656
N2 N2 C11 C13 -135.9(3) 2_656
C9 C8 C12 F3 179.7(2) .
I1 C8 C12 F3 -4.7(3) .
C9 C8 C12 C13 -2.2(4) .
I1 C8 C12 C13 173.50(18) .
F3 C12 C13 F4 0.6(3) .
C8 C12 C13 F4 -177.6(2) .
F3 C12 C13 C11 -180.0(2) .
C8 C12 C13 C11 1.8(4) .
C10 C11 C13 F4 179.6(2) .
N2 C11 C13 F4 11.8(3) .
C10 C11 C13 C12 0.1(4) .
N2 C11 C13 C12 -167.7(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139186904
