#------------------------------------------------------------------------------
#$Date: 2022-04-06 01:22:52 +0300 (Wed, 06 Apr 2022) $
#$Revision: 274360 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/67/1566749.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_1566749
loop_
_publ_author_name
'Peng, Hang'
'Qi, Jun-Chao'
'Song, Xian-Jiang'
'Xiong, Ren-Gen'
'Liao, Wei-Qiang'
_publ_section_title
;
 An Unprecedented Azobenzene-Based Organic Single-Component Ferroelectric
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00689H
_journal_year                    2022
_chemical_formula_moiety         'C12 H4 F6 N2'
_chemical_formula_sum            'C12 H4 F6 N2'
_chemical_formula_weight         290.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-01-24 deposited with the CCDC.	2022-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.270(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.4870(3)
_cell_length_b                   9.3652(6)
_cell_length_c                   13.1716(8)
_cell_measurement_reflns_used    1296
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.2210
_cell_measurement_theta_min      2.6600
_cell_volume                     549.04(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  43.00   0.50    2.00    --   20.00  54.00  60.00  144
  2  ω    -74.00  34.00   0.50    2.00    --   20.00  54.00  90.00  216
  3  ω     42.00  68.00   0.50    2.00    --   20.00  54.00  90.00   52
  4  ω    -72.00 -27.00   0.50    2.00    --   20.00  54.00   0.00   90
  5  ω     34.00 110.00   0.50    2.00    --   20.00  54.00   0.00  152
  6  ω    -30.00  -5.00   0.50    2.00    --   20.00  54.00-150.00   50
  7  ω     82.00 107.00   0.50    2.00    --   20.00  54.00-150.00   50
  8  ω    -69.00  44.00   0.50    2.00    --   20.00  54.00 -30.00  226
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0630564000
_diffrn_orient_matrix_UB_12      -0.0473783000
_diffrn_orient_matrix_UB_13      -0.0389106000
_diffrn_orient_matrix_UB_21      -0.0584879000
_diffrn_orient_matrix_UB_22      0.0590012000
_diffrn_orient_matrix_UB_23      -0.0299425000
_diffrn_orient_matrix_UB_31      0.1342088000
_diffrn_orient_matrix_UB_32      0.0034979000
_diffrn_orient_matrix_UB_33      -0.0231226000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4448
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.107
_diffrn_reflns_theta_min         2.676
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.60a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.755
_exptl_crystal_description       prism
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1540
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0485
_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)+(0.0612P)²+0.0396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1367
_reflns_Friedel_coverage         0.000
_reflns_number_gt                892
_reflns_number_total             1540
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc00689h2.cif
_cod_data_source_block           246_az_298k
_cod_database_code               1566749
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N F'
_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_max   0.991
_shelx_estimated_absorpt_t_min   0.986
_reflns_odcompleteness_completeness 99.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.151
_oxdiff_exptl_absorpt_empirical_full_min 0.720
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.3676(3) 0.31724(14) 0.62408(8) 0.0634(4) Uani 1 1 d . . . . .
F002 F 0.1650(3) 0.42580(13) 0.27048(9) 0.0650(4) Uani 1 1 d . . . . .
F003 F 0.8326(3) 0.05644(12) 0.38425(11) 0.0654(4) Uani 1 1 d . . . . .
N004 N 0.0426(4) 0.49321(18) 0.45692(12) 0.0437(4) Uani 1 1 d . . . . .
C005 C 0.2456(4) 0.37696(19) 0.44786(13) 0.0356(4) Uani 1 1 d . . . . .
C006 C 0.4004(4) 0.2923(2) 0.52480(14) 0.0399(5) Uani 1 1 d . . . . .
C007 C 0.3068(4) 0.3468(2) 0.34798(14) 0.0414(5) Uani 1 1 d . . . . .
C008 C 0.5981(4) 0.18471(19) 0.50590(15) 0.0438(5) Uani 1 1 d . . . . .
H008 H 0.698287 0.130414 0.558675 0.053 Uiso 1 1 calc R U . . .
C009 C 0.6394(4) 0.16181(19) 0.40491(16) 0.0443(5) Uani 1 1 d . . . . .
C00A C 0.4974(4) 0.2400(2) 0.32430(15) 0.0471(5) Uani 1 1 d . . . . .
H00A H 0.528766 0.221489 0.257094 0.057 Uiso 1 1 calc R U . . .
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'
F F 0.0171 0.0103 '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'
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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N004 N004 C005 115.1(2) 3_566 . ?
C006 C005 N004 129.18(17) . . ?
C006 C005 C007 115.19(16) . . ?
C007 C005 N004 115.58(15) . . ?
F001 C006 C005 119.78(17) . . ?
F001 C006 C008 116.68(17) . . ?
C008 C006 C005 123.50(17) . . ?
F002 C007 C005 117.83(16) . . ?
F002 C007 C00A 118.21(17) . . ?
C00A C007 C005 123.94(17) . . ?
C006 C008 H008 121.6 . . ?
C009 C008 C006 116.90(18) . . ?
C009 C008 H008 121.6 . . ?
F003 C009 C008 118.05(18) . . ?
F003 C009 C00A 118.32(19) . . ?
C00A C009 C008 123.63(18) . . ?
C007 C00A C009 116.82(18) . . ?
C007 C00A H00A 121.6 . . ?
C009 C00A H00A 121.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C006 1.355(2) . ?
F002 C007 1.353(2) . ?
F003 C009 1.364(2) . ?
N004 N004 1.249(3) 3_566 ?
N004 C005 1.434(2) . ?
C005 C006 1.400(2) . ?
C005 C007 1.406(2) . ?
C006 C008 1.386(2) . ?
C007 C00A 1.377(3) . ?
C008 H008 0.9300 . ?
C008 C009 1.383(3) . ?
C009 C00A 1.378(3) . ?
C00A H00A 0.9300 . ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F001 C006 C008 C009 -178.05(15) . . . . ?
F002 C007 C00A C009 179.72(16) . . . . ?
F003 C009 C00A C007 -179.18(16) . . . . ?
N004 N004 C005 C006 -12.0(3) 3_566 . . . ?
N004 N004 C005 C007 170.6(2) 3_566 . . . ?
N004 C005 C006 F001 -0.5(3) . . . . ?
N004 C005 C006 C008 -178.20(16) . . . . ?
N004 C005 C007 F002 -1.8(2) . . . . ?
N004 C005 C007 C00A 179.54(17) . . . . ?
C005 C006 C008 C009 -0.2(3) . . . . ?
C005 C007 C00A C009 -1.6(3) . . . . ?
C006 C005 C007 F002 -179.61(16) . . . . ?
C006 C005 C007 C00A 1.7(3) . . . . ?
C006 C008 C009 F003 -179.94(15) . . . . ?
C006 C008 C009 C00A 0.4(3) . . . . ?
C007 C005 C006 F001 177.00(15) . . . . ?
C007 C005 C006 C008 -0.7(3) . . . . ?
C008 C009 C00A C007 0.5(3) . . . . ?
