#------------------------------------------------------------------------------
#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/86/7118647.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_7118647
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            'C18 H12 F8 I2 N4'
_chemical_formula_weight         690.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 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                 108.999(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.390(4)
_cell_length_b                   6.3311(13)
_cell_length_c                   17.654(4)
_cell_measurement_temperature    150(2)
_cell_volume                     2154.8(8)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.876
_diffrn_reflns_theta_min         1.056
_exptl_absorpt_coefficient_mu    3.001
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADADBS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.127
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.074
_refine_diff_density_max         1.142
_refine_diff_density_min         -1.270
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0258P)²+2.4218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0700
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3882
_reflns_number_total             5121
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc08590j2.cif
_cod_data_source_block           Bushuyev4
_cod_database_code               7118647
#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.
;
_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, -y, -z'
'x, -y, 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
C1 C 0.7436(3) 0.4958(7) 0.5006(3) 0.0314(11) Uani 1 1 d . .
H4 H 0.7117 0.5980 0.4643 0.038 Uiso 1 1 calc R U
H1 H 0.7780 0.5767 0.5435 0.038 Uiso 1 1 calc R U
C2 C 0.7018(2) 0.3498(7) 0.5385(3) 0.0291(10) Uani 1 1 d . .
H3 H 0.7170 0.3718 0.5972 0.035 Uiso 1 1 calc R U
H12 H 0.6518 0.3848 0.5164 0.035 Uiso 1 1 calc R U
C3 C 0.6887(2) 0.0988(7) 0.4334(2) 0.0286(10) Uani 1 1 d . .
H11 H 0.6381 0.1250 0.4115 0.034 Uiso 1 1 calc R U
H2 H 0.6975 -0.0488 0.4208 0.034 Uiso 1 1 calc R U
C4 C 0.7273(3) 0.2521(8) 0.3945(3) 0.0338(11) Uani 1 1 d . .
H10 H 0.7500 0.1707 0.3620 0.041 Uiso 1 1 calc R U
H9 H 0.6935 0.3499 0.3582 0.041 Uiso 1 1 calc R U
C5 C 0.8272(2) 0.2273(8) 0.5107(3) 0.0328(11) Uani 1 1 d . .
H5 H 0.8631 0.3080 0.5520 0.039 Uiso 1 1 calc R U
H6 H 0.8508 0.1396 0.4810 0.039 Uiso 1 1 calc R U
C6 C 0.7878(2) 0.0831(7) 0.5517(3) 0.0317(11) Uani 1 1 d . .
H7 H 0.7959 -0.0667 0.5412 0.038 Uiso 1 1 calc R U
H8 H 0.8054 0.1061 0.6103 0.038 Uiso 1 1 calc R U
C7 C 0.5964(2) 0.3769(6) 0.1403(2) 0.0194(9) Uani 1 1 d . .
C8 C 0.5258(2) 0.4193(7) 0.1176(2) 0.0228(9) Uani 1 1 d . .
C9 C 0.5004(2) 0.5847(7) 0.1500(2) 0.0240(10) Uani 1 1 d . .
C10 C 0.5439(2) 0.7198(7) 0.2052(2) 0.0206(9) Uani 1 1 d . .
C11 C 0.6148(2) 0.6805(7) 0.2268(2) 0.0214(9) Uani 1 1 d . .
C12 C 0.6396(2) 0.5119(7) 0.1965(2) 0.0186(9) Uani 1 1 d . .
C13 C 0.8946(2) 1.0910(7) 0.8464(2) 0.0204(9) Uani 1 1 d . .
C14 C 0.9645(2) 1.0426(7) 0.8775(2) 0.0248(10) Uani 1 1 d . .
C15 C 0.9927(2) 0.8730(7) 0.8489(2) 0.0256(10) Uani 1 1 d . .
C16 C 0.9522(2) 0.7449(7) 0.7885(2) 0.0224(9) Uani 1 1 d . .
C17 C 0.8812(2) 0.7919(7) 0.7574(2) 0.0239(10) Uani 1 1 d . .
C18 C 0.8548(2) 0.9628(7) 0.7855(2) 0.0221(9) Uani 1 1 d . .
F1 F 0.43075(12) 0.6204(4) 0.12520(15) 0.0330(6) Uani 1 1 d . .
F2 F 0.48054(13) 0.2966(4) 0.06273(15) 0.0365(7) Uani 1 1 d . .
F3 F 0.65889(13) 0.8104(4) 0.27992(14) 0.0319(6) Uani 1 1 d . .
F4 F 0.70874(11) 0.4807(4) 0.22128(13) 0.0276(6) Uani 1 1 d . .
F5 F 0.78604(12) 1.0045(4) 0.75167(14) 0.0310(6) Uani 1 1 d . .
F6 F 0.84003(13) 0.6701(4) 0.69944(15) 0.0335(6) Uani 1 1 d . .
F7 F 1.00665(13) 1.1591(4) 0.93744(15) 0.0376(7) Uani 1 1 d . .
F8 F 1.06091(12) 0.8293(4) 0.88213(16) 0.0366(7) Uani 1 1 d . .
I1 I 0.63960(2) 0.13699(4) 0.08787(2) 0.02077(8) Uani 1 1 d . .
I2 I 0.84916(2) 1.33838(4) 0.89291(2) 0.02330(8) Uani 1 1 d . .
N1 N 0.71267(17) 0.1291(5) 0.52087(19) 0.0199(7) Uani 1 1 d . .
N2 N 0.77972(18) 0.3741(5) 0.4555(2) 0.0230(8) Uani 1 1 d . .
N3 N 0.52134(19) 0.9157(6) 0.2310(2) 0.0279(9) Uani 1 1 d . .
N4 N 0.97639(19) 0.5486(6) 0.7656(2) 0.0300(9) 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
N2 C1 C2 111.4(3) .
N1 C2 C1 109.6(3) .
N1 C3 C4 110.0(3) .
N2 C4 C3 111.0(3) .
N2 C5 C6 110.8(4) .
N1 C6 C5 110.3(3) .
C12 C7 C8 116.5(4) .
C12 C7 I1 119.8(3) .
C8 C7 I1 123.6(3) .
F2 C8 C9 118.4(4) .
F2 C8 C7 120.0(4) .
C9 C8 C7 121.6(4) .
F1 C9 C8 119.3(4) .
F1 C9 C10 119.1(4) .
C8 C9 C10 121.6(4) .
C9 C10 C11 117.0(4) .
C9 C10 N3 123.8(4) .
C11 C10 N3 118.3(4) .
F3 C11 C12 120.1(4) .
F3 C11 C10 118.7(4) .
C12 C11 C10 121.2(4) .
F4 C12 C11 118.0(4) .
F4 C12 C7 119.8(4) .
C11 C12 C7 122.2(4) .
C18 C13 C14 116.6(4) .
C18 C13 I2 121.1(3) .
C14 C13 I2 122.3(3) .
F7 C14 C13 120.2(4) .
F7 C14 C15 118.4(4) .
C13 C14 C15 121.4(4) .
F8 C15 C16 119.2(4) .
F8 C15 C14 119.3(4) .
C16 C15 C14 121.4(4) .
C15 C16 C17 117.3(4) .
C15 C16 N4 123.4(4) .
C17 C16 N4 118.4(4) .
F6 C17 C18 120.6(4) .
F6 C17 C16 119.2(4) .
C18 C17 C16 120.2(4) .
F5 C18 C17 117.7(4) .
F5 C18 C13 119.3(4) .
C17 C18 C13 123.0(4) .
C2 N1 C3 109.0(3) .
C2 N1 C6 108.7(3) .
C3 N1 C6 108.1(3) .
C5 N2 C4 108.8(4) .
C5 N2 C1 108.2(3) .
C4 N2 C1 107.5(4) .
N3 N3 C10 120.9(2) 2_655
N4 N4 C16 120.3(2) 2_756
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.467(5) .
C1 C2 1.549(6) .
C2 N1 1.464(5) .
C3 N1 1.472(5) .
C3 C4 1.545(6) .
C4 N2 1.466(6) .
C5 N2 1.462(5) .
C5 C6 1.543(6) .
C6 N1 1.478(5) .
C7 C12 1.387(5) .
C7 C8 1.388(6) .
C7 I1 2.115(4) .
C8 F2 1.346(5) .
C8 C9 1.373(6) .
C9 F1 1.361(5) .
C9 C10 1.381(6) .
C10 C11 1.393(6) .
C10 N3 1.447(5) .
C11 F3 1.347(4) .
C11 C12 1.364(6) .
C12 F4 1.347(4) .
C13 C18 1.380(6) .
C13 C14 1.384(6) .
C13 I2 2.117(4) .
C14 F7 1.346(5) .
C14 C15 1.389(6) .
C15 F8 1.351(5) .
C15 C16 1.379(6) .
C16 C17 1.404(6) .
C16 N4 1.442(5) .
C17 F6 1.337(5) .
C17 C18 1.371(6) .
C18 F5 1.359(5) .
N3 N3 1.259(7) 2_655
N4 N4 1.255(7) 2_756
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
N2 C1 C2 N1 2.3(5) .
N1 C3 C4 N2 3.6(5) .
N2 C5 C6 N1 2.2(5) .
C12 C7 C8 F2 179.3(4) .
I1 C7 C8 F2 4.1(6) .
C12 C7 C8 C9 -0.8(6) .
I1 C7 C8 C9 -176.1(3) .
F2 C8 C9 F1 -0.6(6) .
C7 C8 C9 F1 179.5(4) .
F2 C8 C9 C10 -178.6(4) .
C7 C8 C9 C10 1.6(7) .
F1 C9 C10 C11 -178.1(4) .
C8 C9 C10 C11 -0.1(6) .
F1 C9 C10 N3 -8.8(6) .
C8 C9 C10 N3 169.2(4) .
C9 C10 C11 F3 179.3(4) .
N3 C10 C11 F3 9.4(5) .
C9 C10 C11 C12 -2.1(6) .
N3 C10 C11 C12 -172.0(4) .
F3 C11 C12 F4 0.0(5) .
C10 C11 C12 F4 -178.6(3) .
F3 C11 C12 C7 -178.4(4) .
C10 C11 C12 C7 3.0(6) .
C8 C7 C12 F4 -179.9(3) .
I1 C7 C12 F4 -4.4(5) .
C8 C7 C12 C11 -1.5(6) .
I1 C7 C12 C11 174.0(3) .
C18 C13 C14 F7 -179.5(4) .
I2 C13 C14 F7 -2.5(6) .
C18 C13 C14 C15 -0.3(6) .
I2 C13 C14 C15 176.7(3) .
F7 C14 C15 F8 0.5(6) .
C13 C14 C15 F8 -178.7(4) .
F7 C14 C15 C16 178.9(4) .
C13 C14 C15 C16 -0.3(7) .
F8 C15 C16 C17 178.0(4) .
C14 C15 C16 C17 -0.4(6) .
F8 C15 C16 N4 8.7(6) .
C14 C15 C16 N4 -169.7(4) .
C15 C16 C17 F6 -179.3(4) .
N4 C16 C17 F6 -9.4(6) .
C15 C16 C17 C18 1.8(6) .
N4 C16 C17 C18 171.7(4) .
F6 C17 C18 F5 -0.8(6) .
C16 C17 C18 F5 178.2(4) .
F6 C17 C18 C13 178.5(4) .
C16 C17 C18 C13 -2.5(6) .
C14 C13 C18 F5 -179.0(4) .
I2 C13 C18 F5 4.0(5) .
C14 C13 C18 C17 1.8(6) .
I2 C13 C18 C17 -175.3(3) .
C1 C2 N1 C3 -60.3(5) .
C1 C2 N1 C6 57.3(5) .
C4 C3 N1 C2 57.2(5) .
C4 C3 N1 C6 -60.8(5) .
C5 C6 N1 C2 -60.4(4) .
C5 C6 N1 C3 57.8(5) .
C6 C5 N2 C4 -59.6(5) .
C6 C5 N2 C1 56.9(5) .
C3 C4 N2 C5 56.5(5) .
C3 C4 N2 C1 -60.5(5) .
C2 C1 N2 C5 -60.0(5) .
C2 C1 N2 C4 57.3(5) .
C9 C10 N3 N3 64.6(7) 2_655
C11 C10 N3 N3 -126.3(5) 2_655
C15 C16 N4 N4 -66.3(7) 2_756
C17 C16 N4 N4 124.4(5) 2_756
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139186905
