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_7245951
_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         'C2 H3 N4 S, C8 H20 N'
_chemical_formula_sum            'C10 H23 N5 S'
_chemical_formula_weight         245.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 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            4
_cell_length_a                   9.089(3)
_cell_length_b                   11.287(3)
_cell_length_c                   13.926(4)
_cell_measurement_reflns_used    1214
_cell_measurement_temperature    100
_cell_measurement_theta_max      36.273
_cell_measurement_theta_min      5.04
_cell_volume                     1428.6(7)
_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
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0673
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1739
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        36.369
_diffrn_reflns_theta_max         36.369
_diffrn_reflns_theta_min         5.044
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.890
_exptl_absorpt_correction_T_max  0.7472
_exptl_absorpt_correction_T_min  0.4839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1201 before and 0.0916 after correction. The Ratio of minimum to maximum transmission is 0.6476. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.35(8)
_refine_ls_extinction_coef       0.0035(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0586P)^2^+0.2328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1061
_reflns_Friedel_coverage         0.612
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                591
_reflns_number_total             665
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00961g2.cif
_cod_data_source_block           2_DBAHMeTzS
_cod_depositor_comments
'Adding full bibliography for 7245951--7245955.cif.'
_cod_original_cell_volume        1428.6(8)
_cod_database_code               7245951
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.601
_shelx_estimated_absorpt_t_min   0.452
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.65(8)
 0.35(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(N5) = Uanis(C1)
Uanis(N1) = Uanis(C2)
Uanis(C8) = Uanis(C7)
4.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6)
4.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C4(H4A,H4B), C3(H3A,H3B)
4.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C1(H1C,H1D,H1E), C8(H8A,H8B,H8C), C7(H7A,H7B,H7C), C10(H10A,
 H10B,H10C)
;
_shelx_res_checksum              94055
_shelx_hkl_checksum              12708
_olex2_submission_special_instructions 'No special instructions were received'