#------------------------------------------------------------------------------
#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/86/7118650.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_7118650
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            'C12 H2 Br2 F6 N2'
_chemical_formula_weight         447.96
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-10-13 deposited with the CCDC.
2015-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.917(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.630(2)
_cell_length_b                   4.7239(9)
_cell_length_c                   12.695(2)
_cell_measurement_temperature    100(2)
_cell_volume                     623.74(19)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6895
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.933
_diffrn_reflns_theta_min         1.958
_exptl_absorpt_coefficient_mu    6.569
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.385
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.361
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.151
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0178
_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)+(0.0175P)²+0.5553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0403
_refine_ls_wR_factor_ref         0.0416
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1314
_reflns_number_total             1462
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc08590j2.cif
_cod_data_source_block           AB120_0m
_cod_original_cell_volume        623.7(2)
_cod_database_code               7118650
#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   0.200
_shelx_estimated_absorpt_t_max   0.437
_exptl_absorpt_special_details   SADABS
_shelxl_version_number           2014/6
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Br1 Br 0.69165(2) 0.16088(4) 0.43148(2) 0.01668(7) Uani 1 1 d . .
C1 C 0.86333(18) 0.5578(4) 0.55624(14) 0.0135(4) Uani 1 1 d . .
C2 C 0.74343(18) 0.4258(4) 0.54136(15) 0.0136(4) Uani 1 1 d . .
C3 C 0.66069(17) 0.4864(4) 0.60871(15) 0.0161(4) Uani 1 1 d . .
C4 C 0.69330(19) 0.6879(4) 0.68770(15) 0.0170(4) Uani 1 1 d . .
C5 C 0.80903(19) 0.8276(4) 0.70360(15) 0.0177(4) Uani 1 1 d . .
H1 H 0.8309 0.9676 0.7580 0.021 Uiso 1 1 calc R U
C6 C 0.89203(18) 0.7575(4) 0.63797(16) 0.0162(4) Uani 1 1 d . .
F1 F 0.54870(11) 0.3496(2) 0.59837(10) 0.0217(3) Uani 1 1 d . .
F2 F 0.60991(11) 0.7473(3) 0.75060(9) 0.0230(3) Uani 1 1 d . .
F3 F 1.00342(11) 0.9010(3) 0.65229(10) 0.0233(3) Uani 1 1 d . .
N1 N 0.94071(14) 0.4956(3) 0.48021(12) 0.0149(3) 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'
Br Br -0.2901 2.4595 '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
C6 C1 C2 117.26(17) .
C6 C1 N1 125.36(17) .
C2 C1 N1 117.10(16) .
C3 C2 C1 120.34(17) .
C3 C2 Br1 118.34(14) .
C1 C2 Br1 121.31(14) .
F1 C3 C4 119.46(16) .
F1 C3 C2 120.55(17) .
C4 C3 C2 119.98(17) .
F2 C4 C5 119.64(18) .
F2 C4 C3 118.80(17) .
C5 C4 C3 121.56(17) .
C6 C5 C4 117.59(18) .
C6 C5 H1 121.2 .
C4 C5 H1 121.2 .
F3 C6 C5 117.07(17) .
F3 C6 C1 119.68(17) .
C5 C6 C1 123.19(18) .
N1 N1 C1 113.25(19) 3_766
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C2 1.8701(19) .
C1 C6 1.389(3) .
C1 C2 1.396(3) .
C1 N1 1.422(2) .
C2 C3 1.377(3) .
C3 F1 1.337(2) .
C3 C4 1.374(3) .
C4 F2 1.340(2) .
C4 C5 1.374(3) .
C5 C6 1.373(3) .
C5 H1 0.9500 .
C6 F3 1.344(2) .
N1 N1 1.257(3) 3_766
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_4
C6 C1 C2 C3 -2.5(3) .
N1 C1 C2 C3 -176.84(17) .
C6 C1 C2 Br1 178.23(14) .
N1 C1 C2 Br1 3.9(2) .
C1 C2 C3 F1 -176.44(17) .
Br1 C2 C3 F1 2.9(2) .
C1 C2 C3 C4 3.2(3) .
Br1 C2 C3 C4 -177.47(14) .
F1 C3 C4 F2 -1.8(3) .
C2 C3 C4 F2 178.55(17) .
F1 C3 C4 C5 177.92(17) .
C2 C3 C4 C5 -1.7(3) .
F2 C4 C5 C6 179.30(17) .
C3 C4 C5 C6 -0.4(3) .
C4 C5 C6 F3 178.22(17) .
C4 C5 C6 C1 1.1(3) .
C2 C1 C6 F3 -176.72(17) .
N1 C1 C6 F3 -2.9(3) .
C2 C1 C6 C5 0.3(3) .
N1 C1 C6 C5 174.14(18) .
C6 C1 N1 N1 37.2(3) 3_766
C2 C1 N1 N1 -148.9(2) 3_766
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132934272
