#------------------------------------------------------------------------------
#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/86/7118649.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_7118649
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_moiety         'C12 F10 N2'
_chemical_formula_sum            'C12 F10 N2'
_chemical_formula_weight         362.14
_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'
_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                 95.3090(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.098(2)
_cell_length_b                   7.5871(9)
_cell_length_c                   8.8151(10)
_cell_measurement_reflns_used    3070
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.39
_cell_volume                     1138.6(2)
_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    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_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  0.0183
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6339
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.393
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.113
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.760
_exptl_crystal_size_mid          0.606
_exptl_crystal_size_min          0.172
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0284
_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)+(0.0519P)²+0.5272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0864
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1137
_reflns_number_total             1289
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc08590j2.cif
_cod_data_source_block           AB113_0m
_cod_database_code               7118649
#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   0.837
_shelx_estimated_absorpt_t_max   0.959
_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+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
C1 C 0.18156(7) 0.73149(15) 0.13883(12) 0.0152(3) Uani 1 1 d
C2 C 0.14773(7) 0.58814(15) 0.20870(13) 0.0159(3) Uani 1 1 d
C3 C 0.09716(7) 0.61005(16) 0.32123(13) 0.0171(3) Uani 1 1 d
C4 C 0.07895(7) 0.77880(17) 0.36633(12) 0.0182(3) Uani 1 1 d
C5 C 0.11010(7) 0.92339(15) 0.29805(13) 0.0171(3) Uani 1 1 d
C6 C 0.16089(7) 0.90041(15) 0.18602(13) 0.0149(2) Uani 1 1 d
F1 F 0.16501(4) 0.42364(9) 0.16824(8) 0.0217(2) Uani 1 1 d
F2 F 0.06584(4) 0.47013(10) 0.38527(8) 0.0237(2) Uani 1 1 d
F3 F 0.03069(4) 0.80182(10) 0.47564(8) 0.0258(2) Uani 1 1 d
F4 F 0.09114(4) 1.08595(9) 0.34065(8) 0.0238(2) Uani 1 1 d
F5 F 0.18872(4) 1.04670(9) 0.12487(7) 0.0200(2) Uani 1 1 d
N1 N 0.23264(6) 0.68595(13) 0.02724(11) 0.0181(2) 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
C2 C1 C6 116.95(10) .
C2 C1 N1 114.96(10) .
C6 C1 N1 128.09(11) .
F1 C2 C3 118.07(10) .
F1 C2 C1 119.76(10) .
C3 C2 C1 122.16(10) .
F2 C3 C4 120.23(11) .
F2 C3 C2 120.53(11) .
C4 C3 C2 119.24(10) .
F3 C4 C5 119.93(11) .
F3 C4 C3 119.86(11) .
C5 C4 C3 120.21(10) .
F4 C5 C4 119.77(10) .
F4 C5 C6 120.02(10) .
C4 C5 C6 120.21(10) .
F5 C6 C5 116.86(10) .
F5 C6 C1 121.92(10) .
C5 C6 C1 121.22(10) .
N1 N1 C1 114.82(12) 7_565
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.4010(16) .
C1 C6 1.4028(15) .
C1 N1 1.4173(14) .
C2 F1 1.3386(13) .
C2 C3 1.3850(16) .
C3 F2 1.3372(13) .
C3 C4 1.3846(16) .
C4 F3 1.3368(13) .
C4 C5 1.3815(17) .
C5 F4 1.3378(13) .
C5 C6 1.3851(17) .
C6 F5 1.3403(13) .
N1 N1 1.2570(19) 7_565
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 137522
