2-Chloroethylamine·Trifluoromethanesulfonate Combined with 18-Crown-6: a Ferroelectric with Excellent Dielectric Switching Properties
Song, Ning; Ying, Ting-Ting; Tan, Yu-Hui; Tang, Yun Zhi; Liao, Juan; Wang, Li Juan; Wang, Fang Xin; Wan, Ming-Yang; Dalton Transactions  (2023) –; doi:10.1039/D3DT01426F

data_7713519
_publ_section_title
;
 2-Chloroethylamine&#x00B7;Trifluoromethanesulfonate Combined with
 18-Crown-6: a Ferroelectric with Excellent Dielectric Switching
 Properties
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT01426F
_journal_year                    2023
_chemical_formula_moiety         'C H F3 O3 S, C12 H24 O6, C2 Cl N'
_chemical_formula_sum            'C15 H25 Cl F3 N O9 S'
_chemical_formula_weight         487.87
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-02-16 deposited with the CCDC.	2023-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8615(11)
_cell_length_b                   11.5618(18)
_cell_length_c                   23.392(3)
_cell_measurement_reflns_used    2247
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.6420
_cell_measurement_theta_min      1.9780
_cell_volume                     2396.6(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_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_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_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    -48.00 -21.00   0.50    6.44    --   20.00  54.00-120.00   54
  2  \w    -12.00  22.00   0.50    6.44    --   20.00  54.00-120.00   68
  3  \w    -70.00 110.00   0.50    6.44    --   20.00  54.00  60.00  360
  4  \w    -60.00 -35.00   0.50    6.44    --   20.00  54.00 -60.00   50
  5  \w     23.00  99.00   0.50    6.44    --   20.00  54.00 -60.00  152
  6  \w    -68.00 -43.00   0.50    6.44    --   20.00  54.00 -30.00   50
  7  \w    -19.00   6.00   0.50    6.44    --   20.00  54.00 -30.00   50
  8  \w     30.00  89.00   0.50    6.44    --   20.00  54.00 -30.00  118
  9  \w     32.00  57.00   0.50    6.44    --   20.00  54.00-150.00   50
 10  \w    -52.00  -9.00   0.50    6.44    --   20.00  54.00 120.00   86
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0679208000
_diffrn_orient_matrix_UB_12      0.0085582000
_diffrn_orient_matrix_UB_13      0.0154590000
_diffrn_orient_matrix_UB_21      0.0287715000
_diffrn_orient_matrix_UB_22      -0.0528636000
_diffrn_orient_matrix_UB_23      -0.0108865000
_diffrn_orient_matrix_UB_31      0.0311044000
_diffrn_orient_matrix_UB_32      0.0298617000
_diffrn_orient_matrix_UB_33      -0.0237214000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15297
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         1.741
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.60a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2237
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0722
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1688P)^2^+0.2857P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2304
_refine_ls_wR_factor_ref         0.2800
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1256
_reflns_number_total             2237
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt01426f2.cif
_cod_data_source_block           lyk_zj2
_cod_original_cell_volume        2396.7(6)
_cod_database_code               7713519
_shelx_shelxl_version_number     2018/3
_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,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 Cl1A-C2A = Cl1-C2
 1.6 with sigma of 0.02
 C2A-C00N \\sim C2-C00M
 with sigma of 0.02
 Cl1-C2 \\sim Cl1A-C2A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N1 \\sim C00M \\sim Cl1 \\sim C2 \\sim C00N \\sim Cl1A \\sim C2A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 Cl1A, C2A, C00N
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 N1, C00M, C2, Cl1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Others
 Sof(C00N)=Sof(Cl1A)=Sof(C2A)=0.5*(1-FVAR(2))
 Sof(C00M)=Sof(Cl1)=Sof(C2)=0.5*FVAR(2)
 Fixed Sof: S001(0.5) F007(0.5) F008(0.5) O009(0.5) H009(0.5) O00B(0.5)
 C00H(0.5) F1(0.5) O1(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00C(H00C,H00D), C00D(H00E,H00F), C00E(H00G,H00H), C00F(H00I,
 H00J), C00G(H00K,H00L)
6.b Idealised tetrahedral OH refined as rotating group:
 O009(H009)
;
_shelx_res_checksum              23073
_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 1.384
_oxdiff_exptl_absorpt_empirical_full_min 0.799