[(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_7130008
_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 H10 N3, C5 H11 N3'
_chemical_formula_sum            'C34 H69 B2 F8 N6 O12'
_chemical_formula_weight         927.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-01-02 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.244(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6823(2)
_cell_length_b                   28.9209(7)
_cell_length_c                   15.9356(3)
_cell_measurement_reflns_used    8639
_cell_measurement_temperature    280.9(9)
_cell_measurement_theta_max      68.1500
_cell_measurement_theta_min      3.0610
_cell_volume                     4792.23(18)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      280.9(9)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.958
_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     34.00  66.00   0.50    0.50    --  107.00 -61.00-180.00   64
  2  \w     37.00  65.00   0.50    0.50    --  107.00 -61.00-120.00   56
  3  \w     88.00 173.00   0.50    0.50    --  107.00  30.00 -90.00  170
  4  \w    133.00 158.00   0.50    0.50    --  107.00  90.00 -46.00   50
  5  \w     36.00  61.00   0.50    0.50    --  107.00 -61.00  90.00   50
  6  \w     38.00 102.00   0.50    0.50    --  107.00 -77.00  30.00  128
  7  \w    -72.00 -19.00   0.50    0.50    --  -45.28  90.00 -46.00  106
  8  \w   -112.00 -28.00   0.50    0.50    -- -102.00 125.00  90.00  168
  9  \w    -15.00  28.00   0.50    0.50    --  -45.28  90.00 -46.00   86
 10  \w    -97.00 -46.00   0.50    0.50    -- -102.00  90.00 -46.00  102
 11  \w   -104.00 -64.00   0.50    0.50    -- -102.00  77.00 -60.00   80
 12  \w    -63.00 -37.00   0.50    0.50    -- -102.00  61.00 -60.00   52
 13  \w    -55.00 -28.00   0.50    0.50    -- -102.00  77.00 -60.00   54
 14  \w    -69.00 -44.00   0.50    0.50    -- -102.00  61.00  90.00   50
 15  \w    -69.00 -38.00   0.50    0.50    -- -102.00  61.00 150.00   62
 16  \w    -69.00 -33.00   0.50    0.50    -- -102.00  61.00 120.00   72
 17  \w   -175.00 -84.00   0.50    0.50    -- -102.00 -94.00-120.00  182
 18  \w   -161.00 -80.00   0.50    0.50    -- -102.00 -90.00-161.00  162
 19  \w   -117.00 -27.00   0.50    0.50    --  -45.28 -57.00-150.00  180
 20  \w    -40.00  20.00   0.50    0.50    --  -45.28  37.00-180.00  120
 21  \w    -17.00  33.00   0.50    0.50    --  -45.28  19.00  90.00  100
 22  \w    -24.00  26.00   0.50    0.50    --   45.28 -90.00-161.00  100
 23  \w     50.00  97.00   0.50    0.50    --  107.00 -90.00-161.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1129239000
_diffrn_orient_matrix_UB_12      0.0114514000
_diffrn_orient_matrix_UB_13      -0.0764035000
_diffrn_orient_matrix_UB_21      -0.0152930000
_diffrn_orient_matrix_UB_22      0.0474598000
_diffrn_orient_matrix_UB_23      0.0403881000
_diffrn_orient_matrix_UB_31      0.0947618000
_diffrn_orient_matrix_UB_32      0.0212618000
_diffrn_orient_matrix_UB_33      -0.0489376000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34798
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.870
_diffrn_reflns_theta_min         3.056
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.990
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_correction_T_min  0.888
_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_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             1972
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.836
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     761
_refine_ls_number_reflns         9564
_refine_ls_number_restraints     149
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.0922
_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^)+(0.1827P)^2^+1.4056P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2916
_refine_ls_wR_factor_ref         0.3248
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5954
_reflns_number_total             9564
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00818a2.cif
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7130008
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N B F'
_shelx_estimated_absorpt_t_max   0.908
_shelx_estimated_absorpt_t_min   0.890
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 F7-B2 = F6A-B2
 1.3 with sigma of 0.01
 O6-C33 \\sim O6A-C33A
 with sigma of 0.04
 O1-C25 \\sim O1A-C25A
 with sigma of 0.02
 O1-C24 \\sim O1A-C24A
 with sigma of 0.02
 O4-C32 \\sim O4A-C32A
 with sigma of 0.04
 O2-C26 \\sim O2A-C26A
 with sigma of 0.02
 O2-C27 \\sim O2A-C27A
 with sigma of 0.02
 O3-C30 \\sim O3A-C30A
 with sigma of 0.04
 O4-C30 \\sim O4A-C30A
 with sigma of 0.02
 O4-C31 \\sim O4A-C31A
 with sigma of 0.02
 O5-C32 \\sim O5A-C32A
 with sigma of 0.02
 O3-C28 \\sim O3A-C28A
 with sigma of 0.02
 O5-C33 \\sim O5A-C33A
 with sigma of 0.02
 O3-C29 \\sim O3A-C29A
 with sigma of 0.02
 O5-C31 \\sim O5A-C31A
 with sigma of 0.04
 O6-C23 \\sim O6A-C23A
 with sigma of 0.02
 O6-C34 \\sim O6A-C34A
 with sigma of 0.02
 C23-C24 \\sim C23A-C24A
 with sigma of 0.02
 C25-C26 \\sim C25A-C26A
 with sigma of 0.02
 O3-C27 \\sim O3A-C27A
 with sigma of 0.04
 O4-C29 \\sim O4A-C29A
 with sigma of 0.04
 C27-C28 \\sim C27A-C28A
 with sigma of 0.02
 O5-C34 \\sim O5A-C34A
 with sigma of 0.04
 O6-C24 \\sim O6A-C24A
 with sigma of 0.04
 C29-C30 \\sim C29A-C30A
 with sigma of 0.02
 C31-C32 \\sim C31A-C32A
 with sigma of 0.02
 C23-C34 \\sim C23A-C34A
 with sigma of 0.04
 C33-C34 \\sim C33A-C34A
 with sigma of 0.02
 C24-C25 \\sim C24A-C25A
 with sigma of 0.04
 C26-C27 \\sim C26A-C27A
 with sigma of 0.04
 C28-C29 \\sim C28A-C29A
 with sigma of 0.04
 O1-C23 \\sim O1A-C23A
 with sigma of 0.04
 O1-C26 \\sim O1A-C26A
 with sigma of 0.04
 C30-C31 \\sim C30A-C31A
 with sigma of 0.04
 C32-C33 \\sim C32A-C33A
 with sigma of 0.04
 O2-C25 \\sim O2A-C25A
 with sigma of 0.04
 O2-C28 \\sim O2A-C28A
 with sigma of 0.04
3. Rigid bond restraints
 C24, C26, C27, C5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 O8, C12, O8, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C32A) \\sim Ueq, Uanis(C29A) \\sim Ueq, Uanis(C26A) \\sim Ueq,
Uanis(C24A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C30A) \\sim Ueq, Uanis(C34A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C27A) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C28) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C26) \\sim Ueq, Uanis(F7) \\sim Ueq, Uanis(F6A) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(F8A) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F5A) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(F5A)=Sof(F7A)=Sof(F6A)=Sof(F8A)=1-FVAR(1)
 Sof(F5)=Sof(F6)=Sof(F7)=Sof(F8)=FVAR(1)
 Sof(C31A)=Sof(H31C)=Sof(H31D)=Sof(O1A)=Sof(C24A)=Sof(H24C)=Sof(H24D)=
 Sof(C25A)=Sof(H25C)=Sof(H25D)=Sof(C23A)=Sof(H23C)=Sof(H23D)=Sof(C26A)=
 Sof(H26C)=Sof(H26D)=Sof(O6A)=Sof(O2A)=Sof(C34A)=Sof(H34C)=Sof(H34D)=Sof(C27A)=
 Sof(H27C)=Sof(H27D)=Sof(C33A)=Sof(H33C)=Sof(H33D)=Sof(C28A)=Sof(H28C)=
 Sof(H28D)=Sof(O5A)=Sof(O3A)=Sof(C32A)=Sof(H32C)=Sof(H32D)=Sof(C29A)=Sof(H29C)=
 Sof(H29D)=Sof(C30A)=Sof(H30C)=Sof(H30D)=Sof(O4A)=1-FVAR(2)
 Sof(O1)=Sof(O2)=Sof(O3)=Sof(O4)=Sof(O5)=Sof(O6)=Sof(C23)=Sof(H23A)=Sof(H23B)=
 Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=
 Sof(H26B)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(C29)=
 Sof(H29A)=Sof(H29B)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(H31A)=Sof(H31B)=
 Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(C34)=Sof(H34A)=
 Sof(H34B)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,
 H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B),
 C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C1(H1A,H1B), C2(H2A,H2B),
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B),
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C16(H16A,H16B),
 C17(H17A,H17B), C21(H21A,H21B), C22(H22A,H22B), C31A(H31C,H31D), C24A(H24C,
 H24D), C25A(H25C,H25D), C23A(H23C,H23D), C26A(H26C,H26D), C34A(H34C,H34D),
 C27A(H27C,H27D), C33A(H33C,H33D), C28A(H28C,H28D), C32A(H32C,H32D), C29A(H29C,
 H29D), C30A(H30C,H30D)
6.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C14(H14), N4(H4), N5(H5), C18(H18), C19(H19)
6.c Idealised Me refined as rotating group:
 N3(H3C,H3D,H3E), N6(H6C,H6D,H6E)
;
_shelx_res_checksum              38804
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.475
_oxdiff_exptl_absorpt_empirical_full_min 0.667