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_7133559
_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         '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           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.cc2kfxvs
_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                 100.127(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2717(9)
_cell_length_b                   6.1735(9)
_cell_length_c                   17.314(2)
_cell_measurement_reflns_used    3839
_cell_measurement_temperature    289(13)
_cell_measurement_theta_max      75.9000
_cell_measurement_theta_min      2.5910
_cell_volume                     765.15(17)
_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      289.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.892
_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     60.00 103.00   0.50    1.08    --  108.36-125.00-180.00   86
  2  \w     37.00 105.00   0.50    1.08    --  108.36 -94.00 -60.00  136
  3  \w     74.00 102.00   0.50    1.08    --  108.36 -77.00  30.00   56
  4  \w     38.00  69.00   0.50    1.08    --  108.36 -77.00  30.00   62
  5  \w     41.00  85.00   0.50    1.08    --  108.36 -94.00  30.00   88
  6  \w    -12.00  19.00   0.50    0.27    --   45.08 -29.00-122.00   62
  7  \w     47.00  72.00   0.50    1.08    --  108.36 -61.00-180.00   50
  8  \w     42.00  67.00   0.50    1.08    --  108.36 -61.00 -60.00   50
  9  \w     35.00  66.00   0.50    1.08    --  108.36 -61.00 -30.00   62
 10  \w    -30.00  27.00   0.50    0.27    --   45.08 -19.00  60.00  114
 11  \w     27.00 123.00   0.50    0.27    --   45.08  29.00  38.00  192
 12  \w     54.00  90.00   0.50    0.27    --   45.08  37.00  90.00   72
 13  \w     21.00  89.00   0.50    0.27    --   45.08  77.00  90.00  136
 14  \w     92.00 153.00   0.50    1.08    --  108.36  29.00  38.00  122
 15  \w     27.00  78.00   0.50    0.27    --   45.08  57.00-180.00  102
 16  \w    -16.00  12.00   0.50    0.27    --  -45.08  19.00 -60.00   56
 17  \w    -23.00  26.00   0.50    0.27    --  -45.08  19.00-180.00   98
 18  \w    -66.00 -40.00   0.50    1.08    -- -102.00  61.00-180.00   52
 19  \w    -64.00 -38.00   0.50    1.08    -- -102.00  61.00-150.00   52
 20  \w   -104.00 -41.00   0.50    1.08    -- -102.00  77.00 -60.00  126
 21  \w    -63.00 -37.00   0.50    1.08    -- -102.00  61.00 150.00   52
 22  \w      0.00  25.00   0.50    0.27    --  -45.08  29.00  38.00   50
 23  \w    -74.00 -49.00   0.50    0.27    --  -45.08 -29.00-122.00   50
 24  \w   -101.00 -76.00   0.50    1.08    -- -102.00 -77.00-150.00   50
 25  \w   -104.00 -78.00   0.50    1.08    -- -102.00 -77.00 120.00   52
 26  \w   -101.00 -76.00   0.50    1.08    -- -102.00 -76.00 125.56   50
 27  \w   -102.00 -77.00   0.50    1.08    -- -102.00 -74.00 152.03   50
 28  \w   -104.00 -79.00   0.50    1.08    -- -102.00 -69.00 156.40   50
 29  \w   -103.00 -78.00   0.50    1.08    -- -102.00 -73.00 140.67   50
 30  \w   -108.00 -82.00   0.50    1.08    -- -102.00 -64.00 134.87   52
 31  \w   -175.00-111.00   0.50    1.08    -- -102.00 -76.00 125.56  128
 32  \w   -116.00 -87.00   0.50    1.08    -- -102.00 -61.00 120.00   58
 33  \w   -107.00 -81.00   0.50    1.08    -- -102.00 -64.00-165.15   52
 34  \w   -107.00 -82.00   0.50    1.08    -- -102.00 -61.00-180.00   50
 35  \w   -127.00 -84.00   0.50    1.08    -- -102.00 -61.00-150.00   86
 36  \w   -170.00-122.00   0.50    1.08    -- -102.00 -61.00-180.00   96
 37  \w   -169.00-143.00   0.50    1.08    -- -102.00 -61.00-150.00   52
 38  \w   -155.00-129.00   0.50    1.08    -- -102.00 -58.00  77.92   52
 39  \w   -114.00 -83.00   0.50    1.08    -- -102.00 -58.00  77.92   62
 40  \w   -108.00 -83.00   0.50    1.08    -- -102.00 -61.00  90.00   50
 41  \w   -113.00 -86.00   0.50    1.08    -- -102.00 -52.00 102.95   54
 42  \w   -167.00 -83.00   0.50    1.08    -- -102.00 -50.00  71.84  168
 43  \w   -175.00-134.00   0.50    1.08    -- -102.00 -60.00 172.10   82
 44  \w   -120.00 -84.00   0.50    1.08    -- -102.00 -52.00 153.77   72
 45  \w   -108.00 -83.00   0.50    1.08    -- -102.00 -60.00 172.10   50
 46  \w   -112.00 -84.00   0.50    1.08    -- -102.00 -51.00 141.35   56
 47  \w   -113.00 -87.00   0.50    1.08    -- -102.00 -30.00 150.00   52
 48  \w   -165.00-139.00   0.50    1.08    -- -102.00 -30.00 150.00   52
 49  \w   -126.00 -86.00   0.50    1.08    -- -102.00 -47.00  76.13   80
 50  \w   -129.00 -84.00   0.50    1.08    -- -102.00 -29.00-122.00   90
 51  \w   -130.00 -86.00   0.50    1.08    -- -102.00 -45.00-180.00   88
;
_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  0.0797
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_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            8494
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         88.491
_diffrn_reflns_theta_min         2.592
_exptl_absorpt_coefficient_mu    0.793
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70348
_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_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Flack x determined using 683 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.22(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2874
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0780
_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^)+(0.1461P)^2^+0.0859P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2212
_refine_ls_wR_factor_ref         0.2520
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.885
_reflns_Friedel_fraction_max     0.741
_reflns_number_gt                2191
_reflns_number_total             2874
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03343d2.cif
_cod_data_source_block           zn-240130-1r-296k_auto
_cod_depositor_comments
'Adding full bibliography for 7133559--7133566.cif.'
_cod_original_cell_volume        765.17(18)
_cod_database_code               7133559
_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:
 C4(H4), C6(H6), C7(H7), C11(H11), C14(H14), C3(H3), C12(H12), C15(H15)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C1(H1D,H1E,H1F)
;
_shelx_res_checksum              82861
_shelx_hkl_checksum              62905
_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
;