Investigation of the role of hydrogen bonding in ionic liquid-like salts with both N- and S-soft donors
Renier, Olivier; Bousrez, Guillaume; Smetana, Volodymyr; Mudring, Anja-Verena; Rogers, Robin D.; CrystEngComm 25 (2023) 530–540; doi:10.1039/D2CE00961G

data_7245954
_publ_section_title
;
 Investigation of the role of hydrogen bonding in ionic liquid-like salts
 with both N- and S-soft donors
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              530
_journal_page_last               540
_journal_paper_doi               10.1039/D2CE00961G
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C3 H3 N2 S2, 0.5(C8 H20.463 N), 0.5(C8 H20 N)'
_chemical_formula_sum            'C11 H23.23 N3 S2'
_chemical_formula_weight         261.68
_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
_audit_creation_date             2021-05-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-05-17 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.8848(14)
_cell_length_b                   6.9574(4)
_cell_length_c                   23.6250(17)
_cell_measurement_reflns_used    9214
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.57
_cell_measurement_theta_min      2.44
_cell_volume                     2939.7(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            27448
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.583
_diffrn_reflns_theta_min         2.066
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1056 before and 0.0784 after correction. The Ratio of minimum to maximum transmission is 0.8526. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       plate
_exptl_crystal_F_000             1138
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.984
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details
;
 Flack x determined using 2366 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         8128
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0589
_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^)+(0.0131P)^2^+4.8729P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1276
_reflns_Friedel_coverage         0.957
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                6754
_reflns_number_total             8128
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00961g2.cif
_cod_data_source_block           6_DBAHMeDiTS
_cod_depositor_comments
'Adding full bibliography for 7245951--7245955.cif.'
_cod_database_code               7245954
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.73(13)
 0.27(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
3. Others
 Sof(H12A)=Sof(H12B)=Sof(H12C)=Sof(H8AA)=Sof(H8AB)=Sof(H13A)=Sof(H13B)=
 Sof(H13C)=Sof(C11)=Sof(H11)=1-FVAR(1)
 Sof(H12D)=Sof(H12E)=Sof(H12F)=Sof(C10)=Sof(H8BC)=Sof(H8BD)=Sof(H13D)=
 Sof(H13E)=Sof(H13F)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C10(H10), C9(H9), C19(H19), C18(H18), C11(H11)
4.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N1'(H1'A,H1'B), C8(H8BC,H8BD), C8(H8AA,H8AB), C7(H7A,H7B),
 C17(H17A,H17B), C16(H16A,H16B)
4.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C12(H12D,H12E,H12F), C12(H12A,H12B,H12C), C15(H15A,H15B,
 H15C), C13(H13D,H13E,H13F), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C3(H3A,
 H3B,H3C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C),
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              69533
_shelx_hkl_checksum              68694
_olex2_submission_special_instructions 'No special instructions were received'