[(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_7130007
_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(C12 H24 O6), 2(B F4), 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           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-11-10
_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                 99.57(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.926(3)
_cell_length_b                   8.7447(16)
_cell_length_c                   19.506(5)
_cell_measurement_reflns_used    1759
_cell_measurement_temperature    402(10)
_cell_measurement_theta_max      31.2530
_cell_measurement_theta_min      1.8810
_cell_volume                     2174.2(9)
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      402(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -16.00  24.00   0.50    2.45    --   -5.21  53.00   2.00   80
  2  \w     41.00  67.00   0.50    2.45    --   -5.21  53.00   2.00   52
  3  \w    -18.00  39.00   0.50    2.45    --    5.05 -99.00 -60.00  114
  4  \w    -18.00  28.00   0.50    2.45    --   -5.21 -99.00-150.00   92
  5  \w    -36.00 -10.00   0.50    2.45    --   -5.21 -53.00-142.00   52
  6  \w    -77.00 -47.00   0.50    2.45    --   -5.21 -53.00-142.00   60
  7  \w    -77.00   3.00   0.50    2.45    --   -5.21 -37.00 120.00  160
;
_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      -0.0525474000
_diffrn_orient_matrix_UB_12      0.0190801000
_diffrn_orient_matrix_UB_13      -0.0141818000
_diffrn_orient_matrix_UB_21      0.0022079000
_diffrn_orient_matrix_UB_22      -0.0494865000
_diffrn_orient_matrix_UB_23      -0.0285855000
_diffrn_orient_matrix_UB_31      -0.0181691000
_diffrn_orient_matrix_UB_32      -0.0611961000
_diffrn_orient_matrix_UB_33      0.0186222000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17941
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.500
_diffrn_reflns_theta_max         24.500
_diffrn_reflns_theta_min         1.764
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43746
_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    1.246
_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         0.281
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.289
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     481
_refine_ls_number_reflns         3612
_refine_ls_number_restraints     1070
_refine_ls_restrained_S_all      1.288
_refine_ls_R_factor_all          0.1991
_refine_ls_R_factor_gt           0.1259
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3768
_refine_ls_wR_factor_ref         0.4455
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1479
_reflns_number_total             3612
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00818a2.cif
_cod_data_source_block           lyr-1017-409_auto
_cod_original_cell_volume        2174.1(8)
_cod_database_code               7130007
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N B F'
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.986
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
 O2-C8 = O2-C19 = O3-C9 = O3-C10 = O4-C11 = O5-C13 = O5-C14 = O6-C16 = O6-C15 =
  O7-C18
 1.43 with sigma of 0.02
 C1-N5 = C1-C1A = N5-C6 = C6-N7 = N7-C1A
 1.42 with sigma of 0.02
 O4-C12 = O7-C17
 1.42 with sigma of 0.02
 C8-C9 = C10-C11 = C12-C13 = C14-C15 = C16-C17 = C18-C19
 1.49 with sigma of 0.02
 C1-C6 = C1-N7 = N5-N7 = C6-C1A
 2.29 with sigma of 0.04
 N2-C4
 2.54 with sigma of 0.04
 O4-C10 = O4-C13 = O5-C15
 2.38 with sigma of 0.04
 O2-C9 = O2-C18 = O3-C8 = O3-C11 = O5-C12 = O6-C17 = O7-C19 = O7-C16
 2.37 with sigma of 0.04
 O6-C14
 2.36 with sigma of 0.04
 O2-C8 \\sim O2-C19 \\sim O3-C9 \\sim O3-C10 \\sim O4-C11 \\sim O4-C12 \\sim
O5-C13 \\sim O5-C14 \\sim O6-C15
 \\sim O6-C16 \\sim O7-C17 \\sim O7-C18
 with sigma of 0.02
 C8-C9 \\sim C10-C11 \\sim C12-C13 \\sim C14-C15 \\sim C16-C17 \\sim C18-C19
 with sigma of 0.02
 C9-C10 \\sim C11-C12 \\sim C13-C14 \\sim C15-C16 \\sim C17-C18 \\sim C19-C8
 with sigma of 0.04
 O2-C9 \\sim O3-C11 \\sim O4-C13 \\sim O5-C15 \\sim O6-C17 \\sim O7-C19 \\sim
O3-C8 \\sim O4-C10 \\sim O5-C12
 \\sim O6-C14 \\sim O7-C16 \\sim O2-C18
 with sigma of 0.04
 O5-C13 \\sim O5A-C13A
 with sigma of 0.02
 O6-C15 \\sim O6A-C15A
 with sigma of 0.02
 O5-C14 \\sim O5A-C14A
 with sigma of 0.02
 O6-C16 \\sim O6A-C16A
 with sigma of 0.02
 C13-C14 \\sim C13A-C14A
 with sigma of 0.04
 O7-C17 \\sim O7A-C17A
 with sigma of 0.02
 O7-C18 \\sim O7A-C18A
 with sigma of 0.02
 O4-C11 \\sim O4A-C11A
 with sigma of 0.02
 O6-C17 \\sim O6A-C17A
 with sigma of 0.04
 C8-C9 \\sim C8A-C9A
 with sigma of 0.02
 O7-C19 \\sim O7A-C19A
 with sigma of 0.04
 O3-C10 \\sim O3A-C10A
 with sigma of 0.02
 C9-C10 \\sim C9A-C10A
 with sigma of 0.04
 C10-C11 \\sim C10A-C11A
 with sigma of 0.02
 C11-C12 \\sim C11A-C12A
 with sigma of 0.04
 C12-C13 \\sim C12A-C13A
 with sigma of 0.02
 C17-C18 \\sim C17A-C18A
 with sigma of 0.04
 O4-C12 \\sim O4A-C12A
 with sigma of 0.02
 O2-C8 \\sim O2A-C8A
 with sigma of 0.02
 O3-C9 \\sim O3A-C9A
 with sigma of 0.02
 O6-C14 \\sim O6A-C14A
 with sigma of 0.04
 C14-C15 \\sim C14A-C15A
 with sigma of 0.02
 O7-C16 \\sim O7A-C16A
 with sigma of 0.04
 C16-C17 \\sim C16A-C17A
 with sigma of 0.02
 C8-C19 \\sim C8A-C19A
 with sigma of 0.04
 C18-C19 \\sim C18A-C19A
 with sigma of 0.02
 O2-C9 \\sim O2A-C9A
 with sigma of 0.04
 O2-C18 \\sim O2A-C18A
 with sigma of 0.04
 O3-C8 \\sim O3A-C8A
 with sigma of 0.04
 C15-C16 \\sim C15A-C16A
 with sigma of 0.04
 O3-C11 \\sim O3A-C11A
 with sigma of 0.04
 O4-C10 \\sim O4A-C10A
 with sigma of 0.04
 O4-C13 \\sim O4A-C13A
 with sigma of 0.04
 O5-C12 \\sim O5A-C12A
 with sigma of 0.04
 O5-C15 \\sim O5A-C15A
 with sigma of 0.04
 O2-C19 \\sim O2A-C19A
 with sigma of 0.02
3. Rigid bond restraints
 F6A, B2, F4, B2, F3, B2, F4A, B2, F5A, B2, F5, B2, F3A, B2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O2 \\sim O3 \\sim O4 \\sim O5 \\sim O6 \\sim O7 \\sim C8 \\sim C9 \\sim C10
\\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18
\\sim C19: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
Uanis(C8A) \\sim Ueq: with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C9A) \\sim Ueq, Uanis(C8A) \\sim Ueq, Uanis(O2A) \\sim Ueq, Uanis(C19A)
\\sim Ueq, Uanis(O3A) \\sim Ueq, Uanis(C18A) \\sim Ueq, Uanis(C10A) \\sim Ueq,
Uanis(O7A) \\sim Ueq, Uanis(C11A) \\sim Ueq, Uanis(C17A) \\sim Ueq, Uanis(O4A)
\\sim Ueq, Uanis(C16A) \\sim Ueq, Uanis(C12A) \\sim Ueq, Uanis(O6A) \\sim Ueq,
Uanis(C13A) \\sim Ueq, Uanis(C15A) \\sim Ueq, Uanis(O5A) \\sim Ueq, Uanis(C14A)
\\sim Ueq: with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(F3) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 O2, O3, O4, O5, O6, O7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18,
 C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(F3A)=Sof(F5A)=Sof(F6A)=Sof(F4A)=1-FVAR(1)
 Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
 Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(O2A)=Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(C9A)=
 Sof(H9AA)=Sof(H9AB)=Sof(C18A)=Sof(H18C)=Sof(H18D)=Sof(O3A)=Sof(O7A)=Sof(C10A)=
 Sof(H10C)=Sof(H10D)=Sof(C17A)=Sof(H17C)=Sof(H17D)=Sof(C11A)=Sof(H11C)=
 Sof(H11D)=Sof(C16A)=Sof(H16C)=Sof(H16D)=Sof(O4A)=Sof(O6A)=Sof(C12A)=Sof(H12C)=
 Sof(H12D)=Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C13A)=Sof(H13C)=Sof(H13D)=
 Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(O5A)=1-FVAR(2)
 Sof(O2)=Sof(O3)=Sof(O4)=Sof(O5)=Sof(O6)=Sof(O7)=Sof(C8)=Sof(H8A)=Sof(H8B)=
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11A)=
 Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=
 Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=
 Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(C19)=Sof(H19A)=
 Sof(H19B)=FVAR(2)
 Fixed Sof: N2(0.5) H2A(0.5) H2B(0.5) H2C(0.5) C3(0.5) H3A(0.5) H3B(0.5)
 C4(0.5) H4A(0.5) H4B(0.5) C1(0.5) N5(0.5) H5(0.5) C6(0.5) H6(0.5) N7(0.5)
 H7(0.5) C1A(0.5) H1A(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B),
  C18(H18A,H18B), C19(H19A,H19B), C3(H3A,H3B), C4(H4A,H4B), C8A(H8AA,H8AB),
 C19A(H19C,H19D), C9A(H9AA,H9AB), C18A(H18C,H18D), C10A(H10C,H10D), C17A(H17C,
 H17D), C11A(H11C,H11D), C16A(H16C,H16D), C12A(H12C,H12D), C15A(H15C,H15D),
 C13A(H13C,H13D), C14A(H14C,H14D)
7.b Aromatic/amide H refined with riding coordinates:
 N5(H5), C6(H6), N7(H7), C1A(H1A)
7.c Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C)
;
_shelx_res_checksum              25893
_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 2.396
_oxdiff_exptl_absorpt_empirical_full_min 0.499