[(Histamine)(18-crown-6)<sub>2</sub>][BF<sub>4</sub>]<sub>2</sub> is a high-temperature piezoelectric.
Li, Yi-Rong; Zhang, Yun-Fang; Tang, Yuan-Yuan; Zhang, Han-Yue; Chemical communications (Cambridge, England) 58 (2022) 5148–5151; doi:10.1039/d2cc00818a

data_7130006
_publ_section_title
;
 [(Histamine)(18-crown-6)<sub>2</sub>][BF<sub>4</sub>]<sub>2</sub> is a
 high-temperature piezoelectric.
;
_journal_issue                   33
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5148
_journal_page_last               5151
_journal_paper_doi               10.1039/d2cc00818a
_journal_volume                  58
_journal_year                    2022
_chemical_formula_moiety         '2(B F4), 2(C12 H24 O6), C5 H11 N3'
_chemical_formula_sum            'C29 H59 B2 F8 N3 O12'
_chemical_formula_weight         815.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-12-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-12-27 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.3886(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.9702(2)
_cell_length_b                   8.55111(17)
_cell_length_c                   19.0278(4)
_cell_measurement_reflns_used    6977
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.7520
_cell_measurement_theta_min      3.8790
_cell_volume                     2092.84(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.961
_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     64.00 103.00   0.50    0.41    --  107.00 -77.00-150.00   78
  2  \w     35.00  70.00   0.50    0.41    --  107.00 -61.00   0.00   70
  3  \w     41.00  71.00   0.50    0.41    --  107.00 -61.00 -90.00   60
  4  \w     44.00  71.00   0.50    0.41    --  107.00 -61.00  60.00   54
  5  \w     38.00  64.00   0.50    0.41    --  107.00 -61.00 150.00   52
  6  \w     90.00 177.00   0.50    0.41    --  107.00  95.00 114.00  174
  7  \w     91.00 170.00   0.50    0.41    --  107.00 125.00-120.00  158
  8  \w     40.00  66.00   0.50    0.41    --  107.00 -61.00-180.00   52
  9  \w     41.00  97.00   0.50    0.41    --  107.00-125.00 -90.00  112
 10  \w     66.00  99.00   0.50    0.41    --  107.00 -95.00   5.00   66
 11  \w     38.00  95.00   0.50    0.41    --  107.00 -94.00  60.00  114
 12  \w    -26.00  71.00   0.50    0.10    --   45.15 -95.00   5.00  194
 13  \w    -29.00  28.00   0.50    0.10    --  -45.15  95.00 114.00  114
 14  \w    -76.00 -41.00   0.50    0.10    --  -45.15  95.00 114.00   70
 15  \w   -105.00 -28.00   0.50    0.41    -- -102.00 125.00 150.00  154
 16  \w    -97.00 -71.00   0.50    0.41    -- -102.00  95.00 114.00   52
 17  \w    -66.00 -33.00   0.50    0.41    -- -102.00  61.00 -60.00   66
 18  \w    -66.00 -30.00   0.50    0.41    -- -102.00  61.00 -30.00   72
 19  \w    -22.00  32.00   0.50    0.10    --  -45.15  19.00-150.00  108
 20  \w    -23.00  18.00   0.50    0.10    --  -45.15  19.00  90.00   82
 21  \w    -16.00  20.00   0.50    0.10    --  -45.15  19.00 120.00   72
 22  \w   -158.00-116.00   0.50    0.41    -- -102.00 -95.00   5.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13258
_diffrn_reflns_point_group_measured_fraction_full 0.574
_diffrn_reflns_point_group_measured_fraction_max 0.549
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         26.543
_diffrn_reflns_theta_min         1.796
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.108a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 440 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.290
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         4808
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.291
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0958
_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^)+(0.2300P)^2^+0.0100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3067
_refine_ls_wR_factor_ref         0.3255
_reflns_Friedel_coverage         0.141
_reflns_Friedel_fraction_full    0.149
_reflns_Friedel_fraction_max     0.136
_reflns_number_gt                4030
_reflns_number_total             4808
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00818a2.cif
_cod_data_source_block           lyr-211017_auto
_cod_database_code               7130006
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
2. Rigid bond restraints
 F3, B1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C21, C22
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Others
 Sof(F4A)=1-FVAR(1)
 Sof(F4)=FVAR(1)
 Sof(F2A)=1-FVAR(2)
 Sof(F2)=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B),
 C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B),
  C18(H18A,H18B), C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B), C24(H24A,
 H24B), C25(H25A,H25B), C27(H27A,H27B), C28(H28A,H28B), C30(H30A,H30B),
 C31(H31A,H31B), C33(H33A,H33B), C34(H34A,H34B), C36(H36A,H36B), C47(H47A,H47B),
  C48(H48A,H48B)
4.b Aromatic/amide H refined with riding coordinates:
 C43(H43), C45(H45), N44(H44), N46(H46)
4.c Idealised Me refined as rotating group:
 N49(H49A,H49B,H49C)
;
_shelx_res_checksum              29231
_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
;