H/F substitution achieves high piezoelectricity in enantiomeric molecular crystals.
Mao, Wei-Xin; Zhou, Long-Xing; Deng, Xin; Lan, Jin-Fei; Song, Xian-Jiang; Zhang, Han-Yue; Chemical communications (Cambridge, England) 60 (2024) 10172–10175; doi:10.1039/d4cc03343d

data_7133566
_publ_section_title
;
 H/F substitution achieves high piezoelectricity in enantiomeric molecular
 crystals.
;
_journal_issue                   74
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10172
_journal_page_last               10175
_journal_paper_doi               10.1039/d4cc03343d
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C7 H4 F O2, C9 H14 N O'
_chemical_formula_sum            'C16 H18 F N O3'
_chemical_formula_weight         291.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2kfxzx
_audit_creation_date             2024-07-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-07-01 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.293(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2351(3)
_cell_length_b                   6.07500(10)
_cell_length_c                   20.6390(4)
_cell_measurement_reflns_used    5457
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      76.3930
_cell_measurement_theta_min      3.5890
_cell_volume                     1533.67(5)
_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      300(2)
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.950
_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     -5.00  20.00   0.50    0.24    --   45.45 -15.00-100.00   50
  2  \w     36.00  70.00   0.50    0.98    --  108.36 -61.00  60.00   68
  3  \w     35.00  69.00   0.50    0.98    --  108.36 -61.00  90.00   68
  4  \w     22.00 123.00   0.50    0.24    --   45.45  15.00  70.00  202
  5  \w    104.00 178.00   0.50    0.98    --  108.36  30.00 150.00  148
  6  \w     85.00 134.00   0.50    0.98    --  108.36  15.00  70.00   98
  7  \w    107.00 137.00   0.50    0.98    --  108.36  61.00 -30.00   60
  8  \w    152.00 178.00   0.50    0.98    --  108.36  61.00 -30.00   52
  9  \w     72.00  97.00   0.50    0.98    --  108.36 -94.00-120.00   50
 10  \w     78.00 109.00   0.50    0.98    --  108.36-125.00-180.00   62
 11  \w     35.00  61.00   0.50    0.98    --  108.36 -94.00-120.00   52
 12  \w     30.00  92.00   0.50    0.24    --   45.45-125.00-150.00  124
 13  \w   -166.00 -79.00   0.50    0.98    -- -102.00 -15.00-100.00  174
 14  \w   -119.00 -21.00   0.50    0.24    --  -45.45 -15.00-100.00  196
 15  \w    -63.00 -38.00   0.50    0.98    -- -102.00 125.00  60.00   50
 16  \w   -111.00 -69.00   0.50    0.98    -- -102.00 125.00  60.00   84
 17  \w    -22.00   3.00   0.50    0.24    --  -45.45  15.00  70.00   50
 18  \w    -69.00 -44.00   0.50    0.98    -- -102.00  61.00  30.00   50
 19  \w   -103.00 -76.00   0.50    0.98    -- -102.00  77.00-150.00   54
 20  \w    -68.00 -30.00   0.50    0.98    -- -102.00  61.00-150.00   76
 21  \w    -66.00 -35.00   0.50    0.98    -- -102.00  61.00-180.00   62
 22  \w    -16.00  10.00   0.50    0.24    --  -45.45  19.00-180.00   52
 23  \w    -64.00 -34.00   0.50    0.98    -- -102.00  77.00-150.00   60
 24  \w    -69.00 -31.00   0.50    0.98    -- -102.00  61.00-120.00   76
 25  \w    -54.00 -28.00   0.50    0.98    -- -102.00  61.00  90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9684
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.520
_diffrn_reflns_theta_min         3.613
_exptl_absorpt_coefficient_mu    0.791
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0518P)^2^+0.1867P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1130
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2523
_reflns_number_total             3067
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03343d2.cif
_cod_data_source_block           zn-240312-f_auto
_cod_depositor_comments
'Adding full bibliography for 7133559--7133566.cif.'
_cod_database_code               7133566
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C13(H13), C5(H5), C4(H4), C8(H8), C12(H12), C15(H15), C10(H10)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C1(H1D,H1E,H1F)
;
_shelx_res_checksum              71505
_shelx_hkl_checksum              61729
_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
;