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_7133560
_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 H5 O2'
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_weight         273.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2kfxyw
_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
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1046(2)
_cell_length_b                   7.3469(2)
_cell_length_c                   33.6375(9)
_cell_measurement_reflns_used    2632
_cell_measurement_temperature    298.7(9)
_cell_measurement_theta_max      73.4180
_cell_measurement_theta_min      2.6110
_cell_volume                     1508.64(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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      299.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.956
_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    -84.00 -31.00   0.50    0.45    -- -102.00 107.00-133.00  106
  2  \w    -69.00 -28.00   0.50    0.45    -- -102.00  61.00  30.00   82
  3  \w   -120.00 -32.00   0.50    0.20    --  -45.08 -18.00 -96.00  176
  4  \w     47.00  88.00   0.50    0.20    --   45.08-125.00 -30.00   82
  5  \w     76.00 102.00   0.50    0.45    --  108.36-129.00  50.00   52
  6  \w     76.00 103.00   0.50    0.45    --  108.36 -94.00 120.00   54
  7  \w     92.00 162.00   0.50    0.45    --  108.36  18.00  71.00  140
  8  \w     92.00 142.00   0.50    0.45    --  108.36  30.00 150.00  100
  9  \w    -18.00  27.00   0.50    0.20    --   45.08 -19.00 120.00   90
 10  \w     39.00  64.00   0.50    0.45    --  108.36 -61.00-150.00   50
 11  \w     43.00  70.00   0.50    0.45    --  108.36 -61.00-180.00   54
;
_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  0.0169
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            4665
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.359
_diffrn_reflns_theta_min         2.627
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67085
_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    1.203
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 728 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(13)
_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         2684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0873P)^2^+0.1292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1471
_reflns_Friedel_coverage         0.499
_reflns_Friedel_fraction_full    0.778
_reflns_Friedel_fraction_max     0.697
_reflns_number_gt                2359
_reflns_number_total             2684
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03343d2.cif
_cod_data_source_block           zn-240130-6hs_auto
_cod_depositor_comments
'Adding full bibliography for 7133559--7133566.cif.'
_cod_database_code               7133560
_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:
 C8(H8), C4(H4), C5(H5), C7(H7), C16(H16), C12(H12), C15(H15), C13(H13),
 C14(H14)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              32468
_shelx_hkl_checksum              2330
_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
;