#------------------------------------------------------------------------------
#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/86/7118643.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_7118643
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            'C6 F5 N'
_chemical_formula_weight         181.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_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                 127.333(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.770(6)
_cell_length_b                   5.569(3)
_cell_length_c                   9.822(4)
_cell_measurement_temperature    100(2)
_cell_volume                     598.9(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3440
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.164
_diffrn_reflns_theta_min         2.608
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.008
_exptl_crystal_description       needle
_exptl_crystal_F_000             352
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.896
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 464 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1370
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0360
_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)+(0.0390P)²+0.2217P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0842
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.892
_reflns_number_gt                1206
_reflns_number_total             1370
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc08590j2.cif
_cod_data_source_block           AB112_0m
_cod_database_code               7118643
#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.
;
_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, -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
F1 F 0.64026(17) 0.4344(4) 0.0758(2) 0.0395(5) Uani 1 1 d
F2 F 0.57796(17) 0.0999(4) 0.2123(2) 0.0426(6) Uani 1 1 d
F3 F 0.73241(18) -0.2683(4) 0.3985(2) 0.0411(5) Uani 1 1 d
F4 F 1.00818(15) 0.0301(3) 0.3041(2) 0.0319(5) Uani 1 1 d
F5 F 0.85335(16) 0.3933(4) 0.1196(2) 0.0366(5) Uani 1 1 d
N1 N 0.9431(2) -0.3411(5) 0.4410(3) 0.0308(6) Uani 1 1 d
C1 C 0.7161(3) 0.2514(6) 0.1676(4) 0.0283(7) Uani 1 1 d
C2 C 0.6843(3) 0.0832(6) 0.2373(4) 0.0288(7) Uani 1 1 d
C3 C 0.7636(3) -0.1032(6) 0.3311(3) 0.0283(7) Uani 1 1 d
C4 C 0.8755(3) -0.1248(5) 0.3611(3) 0.0246(6) Uani 1 1 d
C5 C 0.9043(3) 0.0473(6) 0.2872(3) 0.0243(6) Uani 1 1 d
C6 C 0.8252(3) 0.2329(6) 0.1915(3) 0.0266(7) 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'
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'
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
N1 N1 C4 122.38(16) 2_756
F1 C1 C6 119.7(3) .
F1 C1 C2 119.9(3) .
C6 C1 C2 120.4(3) .
F2 C2 C3 120.8(3) .
F2 C2 C1 120.3(3) .
C3 C2 C1 118.8(3) .
F3 C3 C2 118.9(3) .
F3 C3 C4 118.8(3) .
C2 C3 C4 122.3(3) .
C3 C4 C5 117.3(3) .
C3 C4 N1 117.3(3) .
C5 C4 N1 124.6(3) .
F4 C5 C6 118.8(3) .
F4 C5 C4 120.3(3) .
C6 C5 C4 120.9(3) .
F5 C6 C5 120.0(3) .
F5 C6 C1 119.8(3) .
C5 C6 C1 120.2(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C1 1.341(4) .
F2 C2 1.333(3) .
F3 C3 1.346(3) .
F4 C5 1.340(3) .
F5 C6 1.334(3) .
N1 N1 1.263(5) 2_756
N1 C4 1.431(4) .
C1 C6 1.377(4) .
C1 C2 1.379(5) .
C2 C3 1.378(5) .
C3 C4 1.388(4) .
C4 C5 1.397(4) .
C5 C6 1.377(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
F1 C1 C2 F2 0.8(4) .
C6 C1 C2 F2 -179.2(3) .
F1 C1 C2 C3 180.0(3) .
C6 C1 C2 C3 0.0(4) .
F2 C2 C3 F3 -0.4(4) .
C1 C2 C3 F3 -179.6(3) .
F2 C2 C3 C4 -179.3(3) .
C1 C2 C3 C4 1.5(4) .
F3 C3 C4 C5 179.0(2) .
C2 C3 C4 C5 -2.1(4) .
F3 C3 C4 N1 8.9(4) .
C2 C3 C4 N1 -172.2(3) .
N1 N1 C4 C3 -137.1(4) 2_756
N1 N1 C4 C5 53.6(5) 2_756
C3 C4 C5 F4 -176.7(2) .
N1 C4 C5 F4 -7.4(4) .
C3 C4 C5 C6 1.3(4) .
N1 C4 C5 C6 170.6(3) .
F4 C5 C6 F5 -0.9(4) .
C4 C5 C6 F5 -178.9(3) .
F4 C5 C6 C1 178.1(2) .
C4 C5 C6 C1 0.1(4) .
F1 C1 C6 F5 -1.7(4) .
C2 C1 C6 F5 178.2(3) .
F1 C1 C6 C5 179.2(3) .
C2 C1 C6 C5 -0.8(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 137522
