Helical ammonium halide framework constituting polar conglomerate crystals of 2-ethylanilinium chloride
Tashiro, Shohei; CrystEngComm 27 (2025) 729–735; doi:10.1039/D4CE01084A

data_7249722
_publ_section_title
;
 Helical ammonium halide framework constituting polar conglomerate
 crystals of 2-ethylanilinium chloride
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              729
_journal_page_last               735
_journal_paper_doi               10.1039/D4CE01084A
_journal_volume                  27
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'Cl, C8 H12 N'
_chemical_formula_sum            'C8 H12 Cl N'
_chemical_formula_weight         157.64
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-30
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-09-25 deposited with the CCDC.	2024-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   21.7201(11)
_cell_length_b                   21.7201(11)
_cell_length_c                   4.8629(3)
_cell_measurement_reflns_used    2483
_cell_measurement_temperature    93
_cell_measurement_theta_max      72.1780
_cell_measurement_theta_min      4.0760
_cell_volume                     1986.78(19)
_computing_cell_refinement       'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.111a 64-bit (release 27-02-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      93
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -22.00  11.00   0.50   31.92    --   47.04 -30.00  59.00   66
  2  \w     15.00  84.00   0.50   31.92    --   47.04 -30.00  59.00  138
  3  \w     14.00 135.00   0.50   47.00    --  103.80 -59.00  74.00  242
  4  \w     16.00 135.00   0.50   47.00    --  103.80 -76.00 -92.00  238
  5  \w     77.00 134.00   0.50   31.92    --   47.04  77.00  60.00  114
  6  \w     86.00 136.00   0.50   31.92    --   47.04  82.00-180.00  100
  7  \w     82.00 126.00   0.50   31.92    --   47.04  82.00   0.00   88
  8  \w     69.00 152.00   0.50   47.00    --  103.80  30.00   0.00  166
  9  \w    163.00 189.00   0.50   47.00    --  103.80  82.00 -90.00   52
 10  \w    100.00 145.00   0.50   47.00    --  103.80  82.00 -90.00   90
 11  \w    163.00 192.00   0.50   47.00    --  103.80  30.00   0.00   58
 12  \w     27.00 185.00   0.50   47.00    --  103.80   7.00-168.00  316
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0611591000
_diffrn_orient_matrix_UB_12      -0.0017189000
_diffrn_orient_matrix_UB_13      -0.1666366000
_diffrn_orient_matrix_UB_21      0.0405855000
_diffrn_orient_matrix_UB_22      0.0069568000
_diffrn_orient_matrix_UB_23      -0.2687799000
_diffrn_orient_matrix_UB_31      -0.0362729000
_diffrn_orient_matrix_UB_32      -0.0815570000
_diffrn_orient_matrix_UB_33      -0.0193043000
_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  0.0793
_diffrn_reflns_av_unetI/netI     0.1103
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            10699
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        66.549
_diffrn_reflns_theta_max         66.549
_diffrn_reflns_theta_min         2.349
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    3.234
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.111a (Rigaku Oxford Diffraction, 2024)
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    1.186
_exptl_crystal_description       needle
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.029
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1407 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4608
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0554P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1310
_reflns_Friedel_coverage         0.971
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3842
_reflns_number_total             4608
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01084a2.cif
_cod_data_source_block           2EAC
_cod_depositor_comments          'Adding full bibliography for 7249722.cif.'
_cod_original_cell_volume        1986.8(2)
_cod_database_code               7249722
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNClO
_shelx_estimated_absorpt_t_max   0.912
_shelx_estimated_absorpt_t_min   0.600
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.620(3)
 0.380(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C7(H7A,H7B), C23(H23A,H23B)
3.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C18(H18), C10(H10), C21(H21), C2(H2), C4(H4), C3(H3), C19(H19),
 C5(H5), C11(H11), C20(H20), C12(H12)
3.c Idealised Me refined as rotating group:
 N3(H3A,H3B,H3C), N2(H2A,H2B,H2C), N1(H1A,H1B,H1C), C24(H24A,H24B,H24C),
 C8(H8A,H8B,H8C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              83431
_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 2.006
_oxdiff_exptl_absorpt_empirical_full_min 0.386