#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:15:48 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281436 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/59/7245952.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7245952
loop_
_publ_author_name
'Renier, Olivier'
'Bousrez, Guillaume'
'Smetana, Volodymyr'
'Mudring, Anja-Verena'
'Rogers, Robin D.'
_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         'C7 H5 N4 S, C8 H20 N'
_chemical_formula_sum            'C15 H25 N5 S'
_chemical_formula_weight         307.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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                   9.1606(16)
_cell_length_b                   17.221(3)
_cell_length_c                   21.778(4)
_cell_measurement_reflns_used    4741
_cell_measurement_temperature    100
_cell_measurement_theta_max      44.489
_cell_measurement_theta_min      4.060
_cell_volume                     3435.6(11)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6816
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        44.557
_diffrn_reflns_theta_max         44.557
_diffrn_reflns_theta_min         4.060
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.677
_exptl_absorpt_correction_T_max  0.7488
_exptl_absorpt_correction_T_min  0.5660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1275 before and 0.0987 after correction. The Ratio of minimum to maximum transmission is 0.7559. The λ/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    1.189
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         1349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0920P)²+7.3674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1574
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1210
_reflns_number_total             1349
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00961g2.cif
_cod_data_source_block           4_DBAHPhTzS
_cod_depositor_comments
'Adding full bibliography for 7245951--7245955.cif.'
_cod_original_cell_volume        3435.6(10)
_cod_database_code               7245952
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.633
_shelx_estimated_absorpt_t_min   0.488
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C11(H11), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C2(H2), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C12(H12A,H12B,
 H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.42552(13) 0.73579(7) 0.32769(5) 0.0247(7) Uani 1 1 d . . . . .
N5 N 0.4904(4) 0.6393(2) 0.42428(18) 0.0191(12) Uani 1 1 d . . . . .
N1 N 0.9591(4) 0.6919(2) 0.31895(16) 0.0207(12) Uani 1 1 d . . . . .
H1A H 0.861699 0.683535 0.323921 0.025 Uiso 1 1 calc R . . . .
H1B H 0.975915 0.700391 0.278317 0.025 Uiso 1 1 calc R . . . .
N2 N 0.6740(5) 0.6602(2) 0.36495(18) 0.0258(12) Uani 1 1 d . . . . .
N4 N 0.6063(5) 0.5992(2) 0.44841(19) 0.0278(12) Uani 1 1 d . . . . .
N3 N 0.7148(5) 0.6125(2) 0.4125(2) 0.0294(13) Uani 1 1 d . . . . .
C1 C 0.3526(6) 0.6359(3) 0.4557(2) 0.0175(13) Uani 1 1 d . . . . .
C7 C 0.5331(6) 0.6776(3) 0.3722(2) 0.0208(13) Uani 1 1 d . . . . .
C6 C 0.2768(5) 0.7035(3) 0.4681(2) 0.0193(13) Uani 1 1 d . . . . .
H6 H 0.312928 0.752083 0.454238 0.023 Uiso 1 1 calc R . . . .
C5 C 0.1479(6) 0.6996(3) 0.5010(2) 0.0230(14) Uani 1 1 d . . . . .
H5 H 0.094557 0.745725 0.509294 0.028 Uiso 1 1 calc R . . . .
C8 C 1.0409(5) 0.6215(3) 0.3389(2) 0.0242(14) Uani 1 1 d . . . . .
H8A H 1.033586 0.617274 0.384173 0.029 Uiso 1 1 calc R . . . .
H8B H 1.145286 0.628807 0.328659 0.029 Uiso 1 1 calc R . . . .
C2 C 0.3024(6) 0.5648(3) 0.4766(2) 0.0211(14) Uani 1 1 d . . . . .
H2 H 0.355739 0.518717 0.468249 0.025 Uiso 1 1 calc R . . . .
C9 C 1.0026(6) 0.7623(3) 0.3545(2) 0.0304(15) Uani 1 1 d . . . . .
H9A H 1.110392 0.763049 0.357774 0.036 Uiso 1 1 calc R . . . .
H9B H 0.963145 0.757399 0.396660 0.036 Uiso 1 1 calc R . . . .
C3 C 0.1741(6) 0.5615(3) 0.5097(2) 0.0257(14) Uani 1 1 d . . . . .
H3 H 0.138788 0.513032 0.524193 0.031 Uiso 1 1 calc R . . . .
C4 C 0.0966(5) 0.6292(3) 0.5218(2) 0.0276(15) Uani 1 1 d . . . . .
H4 H 0.008047 0.626825 0.544435 0.033 Uiso 1 1 calc R . . . .
C13 C 0.7922(5) 0.8438(3) 0.3153(3) 0.0352(16) Uani 1 1 d . . . . .
H13A H 0.769398 0.895186 0.298570 0.053 Uiso 1 1 calc GR . . . .
H13B H 0.736936 0.835587 0.353273 0.053 Uiso 1 1 calc GR . . . .
H13C H 0.765469 0.803819 0.285266 0.053 Uiso 1 1 calc GR . . . .
C15 C 1.0031(6) 0.9020(3) 0.3738(3) 0.0495(17) Uani 1 1 d . . . . .
H15A H 1.108893 0.898518 0.379884 0.074 Uiso 1 1 calc GR . . . .
H15B H 0.953375 0.894841 0.413234 0.074 Uiso 1 1 calc GR . . . .
H15C H 0.978490 0.953178 0.357017 0.074 Uiso 1 1 calc GR . . . .
C11 C 0.9538(6) 0.8387(3) 0.3288(2) 0.0335(15) Uani 1 1 d . . . . .
H11 H 1.007200 0.847038 0.289272 0.040 Uiso 1 1 calc R . . . .
C14 C 1.0814(7) 0.4801(3) 0.3380(3) 0.0543(19) Uani 1 1 d . . . . .
H14A H 1.182529 0.484790 0.323794 0.081 Uiso 1 1 calc GR . . . .
H14B H 1.041010 0.430311 0.324438 0.081 Uiso 1 1 calc GR . . . .
H14C H 1.078935 0.482798 0.382944 0.081 Uiso 1 1 calc GR . . . .
C12 C 0.9520(13) 0.5389(4) 0.2512(5) 0.120(4) Uani 1 1 d . . . . .
H12A H 0.875215 0.576520 0.241470 0.144 Uiso 1 1 calc GR . . . .
H12B H 0.915730 0.486173 0.243775 0.144 Uiso 1 1 calc GR . . . .
H12C H 1.037261 0.548624 0.225125 0.48(18) Uiso 1 1 calc GR . . . .
C10 C 0.9908(9) 0.5462(4) 0.3113(3) 0.079(3) Uani 1 1 d . . . . .
H10 H 0.895002 0.538371 0.332450 0.095 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 N5 C1 118.5(4) . . ?
C7 N5 N4 109.8(4) . . ?
C7 N5 C1 131.7(4) . . ?
C8 N1 C9 112.0(4) . . ?
C7 N2 N3 108.0(4) . . ?
N3 N4 N5 106.0(4) . . ?
N4 N3 N2 110.8(4) . . ?
C6 C1 N5 120.1(4) . . ?
C6 C1 C2 120.8(5) . . ?
C2 C1 N5 119.0(4) . . ?
N5 C7 S1 126.0(4) . . ?
N2 C7 S1 128.6(4) . . ?
N2 C7 N5 105.4(4) . . ?
C1 C6 C5 119.4(4) . . ?
C4 C5 C6 120.3(5) . . ?
N1 C8 C10 115.6(4) . . ?
C3 C2 C1 119.4(4) . . ?
N1 C9 C11 116.0(4) . . ?
C2 C3 C4 120.0(5) . . ?
C5 C4 C3 120.1(5) . . ?
C9 C11 C13 114.6(4) . . ?
C9 C11 C15 107.3(4) . . ?
C13 C11 C15 111.8(4) . . ?
C8 C10 C14 109.0(5) . . ?
C12 C10 C8 123.1(6) . . ?
C12 C10 C14 116.0(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.707(5) . ?
N5 N4 1.371(5) . ?
N5 C1 1.437(6) . ?
N5 C7 1.371(6) . ?
N1 C8 1.491(6) . ?
N1 C9 1.493(6) . ?
N2 N3 1.373(5) . ?
N2 C7 1.334(6) . ?
N4 N3 1.286(5) . ?
C1 C6 1.381(6) . ?
C1 C2 1.385(6) . ?
C6 C5 1.382(7) . ?
C5 C4 1.378(6) . ?
C8 C10 1.500(8) . ?
C2 C3 1.379(6) . ?
C9 C11 1.497(7) . ?
C3 C4 1.389(7) . ?
C13 C11 1.512(7) . ?
C15 C11 1.535(7) . ?
C14 C10 1.524(8) . ?
C12 C10 1.362(10) . ?
