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_7133562
_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.cc2kfy21
_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                 99.245(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2717(9)
_cell_length_b                   6.3005(13)
_cell_length_c                   17.295(2)
_cell_measurement_reflns_used    2179
_cell_measurement_temperature    339.97(11)
_cell_measurement_theta_max      74.2770
_cell_measurement_theta_min      2.5690
_cell_volume                     782.1(2)
_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      340.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.839
_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    -69.00 -28.00   0.50    1.20    -- -102.00  61.00 -60.00   82
  2  \w    -66.00 -28.00   0.50    1.20    -- -102.00  61.00   0.00   76
  3  \w   -104.00 -52.00   0.50    1.20    -- -102.00  77.00  60.00  104
  4  \w    -60.00 -28.00   0.50    1.20    -- -102.00  61.00 120.00   64
  5  \w    -64.00 -37.00   0.50    1.20    -- -102.00  61.00 150.00   54
  6  \w    -23.00  33.00   0.50    0.40    --  -44.95  19.00 150.00  112
  7  \w    -26.00  31.00   0.50    0.40    --  -44.95  40.00   2.00  114
  8  \w    -66.00 -41.00   0.50    1.20    -- -102.00  61.00 -30.00   50
  9  \w   -120.00 -31.00   0.50    0.40    --  -44.95 -40.00-151.00  178
 10  \w   -169.00 -84.00   0.50    1.20    -- -102.00 -40.00-151.00  170
 11  \w     57.00  96.00   0.50    0.40    --   44.95  40.00   2.00   78
 12  \w    102.00 127.00   0.50    1.20    --  108.36  40.00   2.00   50
 13  \w    142.00 178.00   0.50    1.20    --  108.36  30.00  90.00   72
 14  \w    100.00 136.00   0.50    1.20    --  108.36  30.00  90.00   72
 15  \w     51.00 108.00   0.50    1.20    --  108.36 -77.00  90.00  114
 16  \w     37.00  63.00   0.50    1.20    --  108.36 -61.00 150.00   52
 17  \w     35.00  70.00   0.50    1.20    --  108.36 -61.00 -30.00   70
 18  \w      8.00  47.00   0.50    0.40    --   44.95 -40.00-151.00   78
 19  \w     36.00  73.00   0.50    1.20    --  108.36 -61.00-150.00   74
 20  \w     38.00  74.00   0.50    1.20    --  108.36 -94.00-150.00   72
 21  \w     39.00  65.00   0.50    1.20    --  108.36-125.00-180.00   52
 22  \w     81.00 107.00   0.50    1.20    --  108.36-125.00-180.00   52
 23  \w     78.00 105.00   0.50    1.20    --  108.36 -94.00-150.00   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  0.0374
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3788
_diffrn_reflns_point_group_measured_fraction_full 0.700
_diffrn_reflns_point_group_measured_fraction_max 0.599
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         85.012
_diffrn_reflns_theta_min         2.588
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09176
_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    1.237
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 399 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.012(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   1.177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2123
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.190
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0878
_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^)+(0.1318P)^2^+0.3701P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2715
_refine_ls_wR_factor_ref         0.2987
_reflns_Friedel_coverage         0.306
_reflns_Friedel_fraction_full    0.383
_reflns_Friedel_fraction_max     0.309
_reflns_number_gt                1573
_reflns_number_total             2123
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03343d2.cif
_cod_data_source_block           zn-240130-1-340k_auto
_cod_depositor_comments
'Adding full bibliography for 7133559--7133566.cif.'
_cod_database_code               7133562
_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. Restrained distances
 C15-C10
 1.39 with sigma of 0.001
 C14-C13
 1.39 with sigma of 0.001
 C15-C14
 1.39 with sigma of 0.001
 C13-C12
 1.39 with sigma of 0.001
 C11-C12
 1.39 with sigma of 0.001
 C2-C1
 1.47 with sigma of 0.001
 C6-C7
 1.39 with sigma of 0.001
 C5-C4
 1.39 with sigma of 0.001
 C3-C4
 1.39 with sigma of 0.001
 C7-C8
 1.39 with sigma of 0.001
 C5-C6
 1.39 with sigma of 0.001
 C8-C3
 1.39 with sigma of 0.001
 C13-C16
 1.47 with sigma of 0.001
 C2-C3
 1.47 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C2(H2)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C14(H14), C7(H7), C8(H8), C15(H15), C11(H11), C12(H12)
4.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              32769
_shelx_hkl_checksum              47829
_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
;