An Unprecedented Azobenzene-Based Organic Single-Component Ferroelectric
Peng, Hang; Qi, Jun-Chao; Song, Xian-Jiang; Xiong, Ren-Gen; Liao, Wei-Qiang; Chemical Science  (2022) –; doi:10.1039/D2SC00689H

data_1566750
_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 H6 F5 N3'
_chemical_formula_sum            'C12 H6 F5 N3'
_chemical_formula_weight         287.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-11-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-01-25 deposited with the CCDC.	2022-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.008(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.76719(12)
_cell_length_b                   6.2632(2)
_cell_length_c                   24.1516(7)
_cell_measurement_reflns_used    2232
_cell_measurement_temperature    298(17)
_cell_measurement_theta_max      75.8620
_cell_measurement_theta_min      3.5740
_cell_volume                     569.50(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.96(17)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     24.00 111.00   0.50    0.80    --   45.15  72.00 -81.00  174
  2  \w     84.00 171.00   0.50    0.80    --  107.00  72.00 -81.00  174
  3  \w    131.00 157.00   0.50    0.80    --  107.00  15.00-150.00   52
  4  \w     83.00 125.00   0.50    0.80    --  107.00  15.00-150.00   84
  5  \w     38.00 105.00   0.50    0.80    --  107.00 -94.00   0.00  134
  6  \w    -21.00   4.00   0.50    0.80    --  -45.15  72.00 -81.00   50
  7  \w    -22.00  33.00   0.50    0.80    --  -45.15  19.00 -90.00  110
  8  \w    -20.00   5.00   0.50    0.80    --   45.15 -72.00 148.00   50
  9  \w     11.00  48.00   0.50    0.80    --   45.15 -72.00 148.00   74
 10  \w     42.00  85.00   0.50    0.80    --  107.00 -72.00 148.00   86
 11  \w     34.00  59.00   0.50    0.80    --  107.00 -61.00   0.00   50
 12  \w     42.00  67.00   0.50    0.80    --  107.00 -61.00-180.00   50
 13  \w    -89.00 -34.00   0.50    0.80    -- -102.00  72.00 -81.00  110
 14  \w    -62.00 -28.00   0.50    0.80    -- -102.00  61.00 -90.00   68
 15  \w    -69.00 -31.00   0.50    0.80    -- -102.00  61.00   0.00   76
 16  \w    -68.00 -29.00   0.50    0.80    -- -102.00  61.00 120.00   78
 17  \w   -151.00-126.00   0.50    0.80    -- -102.00 -72.00 148.00   50
 18  \w   -173.00-129.00   0.50    0.80    -- -102.00 -45.00-150.00   88
 19  \w   -113.00 -88.00   0.50    0.80    -- -102.00 -45.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0641814000
_diffrn_orient_matrix_UB_12      0.1662481000
_diffrn_orient_matrix_UB_13      0.0463100000
_diffrn_orient_matrix_UB_21      0.2850799000
_diffrn_orient_matrix_UB_22      0.1084277000
_diffrn_orient_matrix_UB_23      -0.0344727000
_diffrn_orient_matrix_UB_31      -0.2862742000
_diffrn_orient_matrix_UB_32      0.1454129000
_diffrn_orient_matrix_UB_33      -0.0272166000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0115
_diffrn_reflns_av_unetI/netI     0.0071
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            2826
_diffrn_reflns_point_group_measured_fraction_full 0.741
_diffrn_reflns_point_group_measured_fraction_max 0.689
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.045
_diffrn_reflns_theta_min         1.830
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.437
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.108a (Rigaku Oxford Diffraction, 2021)
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    1.675
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 390 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.35(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1645
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.176
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0539
_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/[\s^2^(Fo^2^)+(0.0932P)^2^+0.1617P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1575
_reflns_Friedel_coverage         0.349
_reflns_Friedel_fraction_full    0.442
_reflns_Friedel_fraction_max     0.394
_reflns_number_gt                1503
_reflns_number_total             1645
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00689h2.cif
_cod_data_source_block           P21
_cod_database_code               1566750
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N F'
_reflns_odcompleteness_completeness 98.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 N3-C12
 1.48 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F1 \\sim C2: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.01
within 2A
4.a Rotating group:
 N3(H3A,H3B)
4.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C5(H5), C9(H9), C3(H3)
;
_shelx_res_checksum              70019
_shelx_hkl_checksum              18748
_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 2.729
_oxdiff_exptl_absorpt_empirical_full_min 0.663