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_7133563
_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 H5 O2, C9 H14 N O'
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_weight         273.32
_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.cc2kfy0z
_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                 90.471(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0189(3)
_cell_length_b                   6.0835(2)
_cell_length_c                   20.7340(6)
_cell_measurement_reflns_used    4690
_cell_measurement_temperature    299.98(10)
_cell_measurement_theta_max      76.3130
_cell_measurement_theta_min      3.6680
_cell_volume                     1515.96(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_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      299.98(10)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.953
_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     39.00  65.00   0.50    0.56    --  108.36 -61.00-150.00   52
  2  \w     40.00  73.00   0.50    0.56    --  108.36 -61.00-120.00   66
  3  \w     36.00  73.00   0.50    0.56    --  108.36 -61.00 -60.00   74
  4  \w     41.00  67.00   0.50    0.56    --  108.36 -61.00 -90.00   52
  5  \w     36.00  71.00   0.50    0.56    --  108.36 -61.00  30.00   70
  6  \w     36.00 107.00   0.50    0.56    --  108.36 -77.00  90.00  142
  7  \w    -30.00  43.00   0.50    0.14    --   45.20 -37.00 120.00  146
  8  \w    107.00 154.00   0.50    0.56    --  108.36  30.00 -60.00   94
  9  \w     85.00 164.00   0.50    0.56    --  108.36  85.00  -9.00  158
 10  \w    122.00 159.00   0.50    0.56    --  108.36  30.00 -30.00   74
 11  \w     61.00 127.00   0.50    0.56    --  108.36 -85.00-129.00  132
 12  \w    -21.00  75.00   0.50    0.14    --   45.20 -85.00-129.00  192
 13  \w     -3.00  33.00   0.50    0.14    --  -45.20  19.00-180.00   72
 14  \w    -17.00  19.00   0.50    0.14    --  -45.20  19.00-120.00   72
 15  \w    -68.00 -39.00   0.50    0.56    -- -102.00  61.00-180.00   58
 16  \w    -69.00 -32.00   0.50    0.56    -- -102.00  61.00-150.00   74
 17  \w    -22.00  27.00   0.50    0.14    --  -45.20  19.00   0.00   98
 18  \w    -24.00   1.00   0.50    0.14    --  -45.20  85.00  -9.00   50
 19  \w   -104.00 -79.00   0.50    0.56    -- -102.00  85.00  -9.00   50
 20  \w   -124.00 -99.00   0.50    0.56    -- -102.00 -61.00 -90.00   50
 21  \w   -171.00-133.00   0.50    0.56    -- -102.00 -61.00 -90.00   76
 22  \w   -172.00-126.00   0.50    0.56    -- -102.00 -85.00-129.00   92
;
_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  0.0270
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8593
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.689
_diffrn_reflns_theta_min         3.678
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0663P)^2^+0.1546P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1275
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2440
_reflns_number_total             3036
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03343d2.cif
_cod_data_source_block           zn-240312-h-300k_auto
_cod_depositor_comments
'Adding full bibliography for 7133559--7133566.cif.'
_cod_database_code               7133563
_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:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C15(H15), C12(H12), C3(H3), C5(H5), C2(H2), C1(H1), C6(H6)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              46822
_shelx_hkl_checksum              81624
_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
;