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_7713518
_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 F3 O3 S, C2 H7 Cl N, 0.5(C12 H24 O6), 0.5(C12 H23 O6)'
_chemical_formula_sum            'C15 H30.5 Cl F3 N O9 S'
_chemical_formula_weight         493.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-01
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_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            8
_cell_length_a                   17.3300(6)
_cell_length_b                   11.3842(5)
_cell_length_c                   23.0199(11)
_cell_measurement_reflns_used    7112
_cell_measurement_temperature    200.01(10)
_cell_measurement_theta_max      29.8000
_cell_measurement_theta_min      1.9940
_cell_volume                     4541.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.814
_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  12.00   0.50    4.89    --    5.00 -31.00 -37.00  162
  2  \w      0.00  57.00   0.50    4.89    --    5.00  37.00-180.00  114
  3  \w    -16.00  27.00   0.50    4.89    --   -5.46 -99.00 -30.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0121603000
_diffrn_orient_matrix_UB_12      0.0230090000
_diffrn_orient_matrix_UB_13      0.0370310000
_diffrn_orient_matrix_UB_21      0.0111415000
_diffrn_orient_matrix_UB_22      0.0163683000
_diffrn_orient_matrix_UB_23      -0.0500322000
_diffrn_orient_matrix_UB_31      -0.0374490000
_diffrn_orient_matrix_UB_32      0.0123447000
_diffrn_orient_matrix_UB_33      -0.0028037000
_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  0.0496
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.814
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            28185
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.690
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.936
_diffrn_reflns_theta_min         1.996
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.329
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       plate
_exptl_crystal_F_000             2076
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         2.051
_refine_diff_density_min         -1.365
_refine_diff_density_rms         0.178
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.6(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         9927
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.1521
_refine_ls_R_factor_gt           0.1179
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.003
_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          0.2916
_refine_ls_wR_factor_ref         0.3191
_reflns_Friedel_coverage         0.657
_reflns_Friedel_fraction_full    0.806
_reflns_Friedel_fraction_max     0.560
_reflns_number_gt                6793
_reflns_number_total             9927
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt01426f2.cif
_cod_data_source_block           10_200k_auto
_cod_original_formula_sum        'C15 H30.50 Cl F3 N O9 S'
_cod_database_code               7713518
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.993
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.4(2)
 0.6(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
3. Restrained distances
 C01F-C01I
 1.54 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C01F) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C01E) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O00M) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Secondary CH2 refined with riding coordinates:
 C00O(H00A,H00B), C00R(H00C,H00D), C00W(H00E,H00F), C00X(H00G,H00H), C00Y(H00I,
 H00J), C00Z(H00K,H00L), C010(H01A,H01B), C011(H01M,H01N), C012(H01O,H01P),
 C013(H01C,H01D), C015(H01Q,H01R), C017(H01S,H01T), C018(H01E,H01F), C019(H01U,
 H01V), C01A(H01G,H01H), C01B(H01W,H01X), C01C(H01Y,H), C01D(H01I,H01J),
 C01E(H01K,H01L), C01F(H6,HA), C01G(H01Z,HB), C01I(H7,HC), C01K(H1,HD), C01L(H2,
 HE), C01M(H4,HF), C01N(H3,HG), C01O(H5,HH)
5.b Aromatic/amide H refined with riding coordinates:
 C01J(H01)
5.c Idealised Me refined as rotating group:
 N00I(H00P,H00Q,H00R), N00S(H00M,H00N,H00O)
;
_shelx_res_checksum              15181
_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 1.623
_oxdiff_exptl_absorpt_empirical_full_min 0.580