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_7133565
_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_absolute_configuration syn
_chemical_formula_moiety         'C9 H14 N O, C7 H4 F O2'
_chemical_formula_sum            'C16 H18 F N O3'
_chemical_formula_weight         291.31
_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   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2kfy10
_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                 99.161(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2750(8)
_cell_length_b                   6.2945(7)
_cell_length_c                   17.3045(18)
_cell_measurement_reflns_used    1292
_cell_measurement_temperature    339.99(12)
_cell_measurement_theta_max      67.5200
_cell_measurement_theta_min      2.6080
_cell_volume                     782.31(15)
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      339.99(12)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.912
_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  30.00   0.50    0.50    --  -44.83  19.00-180.00  108
  2  \w    -10.00  19.00   0.50    0.50    --  -44.83  19.00-120.00   58
  3  \w    -62.00 -29.00   0.50    1.20    -- -102.00  61.00 -30.00   66
  4  \w    -68.00 -41.00   0.50    1.20    -- -102.00  61.00 -60.00   54
  5  \w    -24.00   2.00   0.50    0.50    --  -44.83  19.00   0.00   52
  6  \w    -46.00 -19.00   0.50    0.50    --  -44.83 105.00 159.00   54
  7  \w   -101.00 -43.00   0.50    1.20    -- -102.00 105.00 159.00  116
  8  \w   -141.00 -85.00   0.50    1.20    -- -102.00-105.00  60.00  112
  9  \w      3.00  81.00   0.50    0.50    --   44.83-105.00  60.00  156
 10  \w     48.00  73.00   0.50    1.20    --  108.36-105.00  60.00   50
 11  \w     36.00  76.00   0.50    1.20    --  108.36 -94.00  60.00   80
 12  \w     77.00 105.00   0.50    1.20    --  108.36 -94.00  60.00   56
 13  \w     43.00  70.00   0.50    1.20    --  108.36 -61.00  90.00   54
 14  \w     39.00  66.00   0.50    1.20    --  108.36 -61.00 120.00   54
 15  \w     36.00  68.00   0.50    1.20    --  108.36 -61.00  60.00   64
 16  \w     37.00  70.00   0.50    1.20    --  108.36 -61.00  30.00   66
 17  \w     36.00  72.00   0.50    1.20    --  108.36 -61.00 -30.00   72
 18  \w    -28.00  44.00   0.50    0.50    --   44.83 -37.00 -60.00  144
 19  \w     35.00  73.00   0.50    1.20    --  108.36 -61.00-180.00   76
 20  \w     92.00 177.00   0.50    1.20    --  108.36  15.00 -90.00  170
 21  \w    138.00 171.00   0.50    1.20    --  108.36  61.00 120.00   66
 22  \w     90.00 136.00   0.50    1.20    --  108.36  61.00 120.00   92
 23  \w    117.00 143.00   0.50    1.20    --  108.36 105.00 159.00   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  0.0321
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3984
_diffrn_reflns_point_group_measured_fraction_full 0.827
_diffrn_reflns_point_group_measured_fraction_max 0.758
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.923
_diffrn_reflns_theta_min         2.586
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21829
_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    1.237
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 484 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2504
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0764
_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^)+(0.1570P)^2^+0.0173P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2153
_refine_ls_wR_factor_ref         0.2433
_reflns_Friedel_coverage         0.519
_reflns_Friedel_fraction_full    0.649
_reflns_Friedel_fraction_max     0.573
_reflns_number_gt                1664
_reflns_number_total             2504
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03343d2.cif
_cod_data_source_block           zn-240222-1r-340k--2_auto
_cod_depositor_comments
'Adding full bibliography for 7133559--7133566.cif.'
_cod_database_code               7133565
_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:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C16(H16), C7(H7), C12(H12), C3(H3), C15(H15), C4(H4), C13(H13)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C1(H1D,H1E,H1F)
;
_shelx_res_checksum              12187
_shelx_hkl_checksum              3286
_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
;