#------------------------------------------------------------------------------
#$Date: 2024-07-05 17:58:07 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292890 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/14/1571421.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_1571421
loop_
_publ_author_name
'Philippi, Frederik'
'Middendorf, Maleen'
'Shigenobu, Keisuke'
'Matsuyama, Yuna'
'Palumbo, Oriele'
'Pugh, David'
'Sudoh, Taku'
'Dokko, Kaoru'
'Watanabe, Masayoshi'
'Schönhoff, Monika'
'Shinoda, Wataru'
'Ueno, Kazuhide'
_publ_section_title
;
 Evolving better solvate electrolytes for lithium secondary batteries.
;
_journal_issue                   19
_journal_name_full               'Chemical science'
_journal_page_first              7342
_journal_page_last               7358
_journal_paper_doi               10.1039/d4sc01492h
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C4 H4 N2 O2 S'
_chemical_formula_sum            'C4 H4 N2 O2 S'
_chemical_formula_weight         144.15
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-24
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-28 deposited with the CCDC.	2024-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                95.165(3)
_cell_angle_beta                 96.669(3)
_cell_angle_gamma                104.049(3)
_cell_formula_units_Z            2
_cell_length_a                   5.4317(2)
_cell_length_b                   7.1254(3)
_cell_length_c                   8.5194(3)
_cell_measurement_reflns_used    4826
_cell_measurement_temperature    223.15
_cell_measurement_theta_max      71.1740
_cell_measurement_theta_min      5.2600
_cell_volume                     315.30(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      223.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      6.00  43.00   0.50    0.50    --   45.50  49.00 -33.00   74
  2  ω     56.00 145.00   0.50    0.50    --   98.30 -49.00 178.00  178
  3  ω    124.00 173.00   0.50    0.50    --   98.30  49.00 -33.00   98
  4  ω     52.00 106.00   0.50    0.50    --   98.30  49.00 -33.00  108
  5  ω     17.00  68.00   0.50    0.50    --   45.50  57.00  60.00  102
  6  ω     12.00  88.00   0.50    0.50    --   45.50 -49.00 178.00  152
  7  ω    -41.00  66.00   0.50    0.50    --   45.50 -57.00 -60.00  214
  8  ω     95.00 121.00   0.50    0.50    --   45.50  49.00 -33.00   52
  9  ω     78.00 128.00   0.50    0.50    --   45.50  82.00 150.00  100
 10  ω      0.00  32.00   0.50    0.50    --   45.50  82.00 150.00   64
 11  ω    -27.00   1.00   0.50    0.50    --   45.50 -49.00 178.00   56
 12  ω     97.00 122.00   0.50    0.50    --   45.50  57.00  60.00   50
 13  ω      7.00  65.00   0.50    0.50    --   52.00  81.00-105.08  116
 14  ω     78.00 138.00   0.50    0.50    --   52.00  81.00-105.08  120
 15  ω    108.00 135.00   0.50    0.50    --   60.00  75.00-132.97   54
 16  ω     21.00  47.00   0.50    0.50    --   60.00  75.00-132.97   52
 17  ω     18.00  47.00   0.50    0.50    --   64.00  80.00  24.43   58
 18  ω     19.00  55.00   0.50    0.50    --   64.00  79.00 -62.68   72
 19  ω     25.00  67.00   0.50    0.50    --   72.00  82.00 -57.78   84
 20  ω     27.00  63.00   0.50    0.50    --   72.00  82.00 146.29   72
 21  ω     97.00 160.00   0.50    0.50    --   72.00  82.00 -57.78  126
 22  ω     90.00 116.00   0.50    0.50    --   76.00  81.00 114.28   52
 23  ω     29.00  55.00   0.50    0.50    --   76.00  82.00  66.19   52
 24  ω     30.00  55.00   0.50    0.50    --   76.00  81.00 114.28   50
 25  ω    155.00 188.00   0.50    0.50    --   98.30  30.00 150.00   66
 26  ω     19.00 145.00   0.50    0.50    --   98.30  30.00 150.00  252
 27  ω    100.00 126.00   0.50    0.50    --   98.30  82.00-120.00   52
 28  ω     10.00  65.00   0.50    0.50    --   98.30 -77.00  90.00  110
 29  ω    121.00 188.00   0.50    0.50    --   98.30  82.00   0.00  134
 30  ω     12.00 143.00   0.50    0.50    --   98.30 -77.00-150.00  262
 31  ω     85.00 110.00   0.50    0.50    --   98.30 -77.00  90.00   50
 32  ω     57.00 131.00   0.50    0.50    --   98.30  82.00  60.00  148
 33  ω    137.00 162.00   0.50    0.50    --   98.30  82.00  60.00   50
 34  ω     51.00  94.00   0.50    0.50    --   98.30  82.00   0.00   86
 35  ω    142.00 167.00   0.50    0.50    --   98.30  82.00  30.00   50
 36  ω     56.00  94.00   0.50    0.50    --   98.30  82.00  30.00   76
 37  ω    112.00 163.00   0.50    0.50    --   98.30  82.00 120.00  102
 38  ω     53.00  91.00   0.50    0.50    --   98.30  82.00-120.00   76
 39  ω     51.00  99.00   0.50    0.50    --   98.30  82.00 120.00   96
 40  ω     54.00  92.00   0.50    0.50    --   98.30  77.00 -30.00   76
 41  ω    163.00 188.00   0.50    0.50    --   98.30  61.00-120.00   50
 42  ω     58.00 126.00   0.50    0.50    --   98.30  61.00-120.00  136
 43  ω      9.00 142.00   0.50    0.50    --   98.30 -82.00  30.00  266
 44  ω    156.00 186.00   0.50    0.50    --   98.30   0.00   0.00   60
 45  ω     95.00 150.00   0.50    0.50    --   98.30   0.00   0.00  110
 46  ω    118.00 144.00   0.50    0.50    --   98.30  82.00 -60.00   52
 47  ω     66.00  91.00   0.50    0.50    --   98.30   0.00   0.00   50
 48  ω     39.00  96.00   0.50    0.50    --   98.30 -82.00-180.00  114
 49  ω     10.00  51.00   0.50    0.50    --   98.30   0.00   0.00   82
 50  ω     88.00 142.00   0.50    0.50    --   98.30 -77.00 -60.00  108
 51  ω     51.00  76.00   0.50    0.50    --   98.30  82.00 -60.00   50
 52  ω    119.00 146.00   0.50    0.50    --   98.30  45.00  60.00   54
 53  ω     58.00 164.00   0.50    0.50    --   98.30  61.00-180.00  212
 54  ω     51.00 104.00   0.50    0.50    --   98.30  82.00-180.00  106
 55  ω     91.00 116.00   0.50    0.50    --   98.30 -82.00-120.00   50
 56  ω     48.00  81.00   0.50    0.50    --   98.30  45.00  60.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2908751000
_diffrn_orient_matrix_UB_12      -0.0203450000
_diffrn_orient_matrix_UB_13      -0.0320902000
_diffrn_orient_matrix_UB_21      0.0464114000
_diffrn_orient_matrix_UB_22      0.1667407000
_diffrn_orient_matrix_UB_23      -0.1049831000
_diffrn_orient_matrix_UB_31      -0.0223000000
_diffrn_orient_matrix_UB_32      -0.1490482000
_diffrn_orient_matrix_UB_33      -0.1469751000
_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  0.0423
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5481
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.550
_diffrn_reflns_theta_min         5.267
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.987
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.66a (Rigaku Oxford Diffraction, 2019)
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    1.518
_exptl_crystal_description       block
_exptl_crystal_F_000             148
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.130(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0308
_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)+(0.0418P)²+0.1672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0799
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1182
_reflns_number_total             1207
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc01492h3.cif
_cod_data_source_block           537-HCMs(CN)2
_cod_depositor_comments
'Adding full bibliography for 1571419--1571424.cif.'
_cod_database_code               1571421
_shelx_shelxl_version_number     2019/3
_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   0.586
_shelx_estimated_absorpt_t_min   0.503
_reflns_odcompleteness_completeness 99.12
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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 2.011
_oxdiff_exptl_absorpt_empirical_full_min 0.528
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.61943(7) 0.30253(5) 0.62636(4) 0.0195(2) Uani 1 1 d . . . . .
O1 O 0.6924(3) 0.21378(19) 0.48829(14) 0.0319(3) Uani 1 1 d . . . . .
O2 O 0.3769(2) 0.3479(2) 0.61813(16) 0.0340(4) Uani 1 1 d . . . . .
N1 N 1.0145(3) -0.0081(2) 0.7890(2) 0.0382(4) Uani 1 1 d . . . . .
N2 N 0.5433(4) 0.2801(3) 1.04751(19) 0.0378(4) Uani 1 1 d . . . . .
C1 C 0.8360(3) 0.0492(2) 0.7819(2) 0.0235(4) Uani 1 1 d . . . . .
C2 C 0.5708(3) 0.2103(2) 0.9276(2) 0.0232(4) Uani 1 1 d . . . . .
C3 C 0.6076(3) 0.1242(2) 0.77230(18) 0.0185(3) Uani 1 1 d . . . . .
H3 H 0.457101 0.012994 0.734026 0.022 Uiso 1 1 calc R U . . .
C4 C 0.8657(3) 0.5044(2) 0.7142(2) 0.0261(4) Uani 1 1 d . . . . .
H4A H 1.022882 0.464249 0.738214 0.039 Uiso 1 1 calc R U . . .
H4B H 0.819741 0.558695 0.811837 0.039 Uiso 1 1 calc R U . . .
H4C H 0.891109 0.602156 0.641357 0.039 Uiso 1 1 calc R U . . .
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'
O O 0.0492 0.0322 '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
O1 S1 C3 105.40(8) . . ?
O1 S1 C4 109.90(8) . . ?
O2 S1 O1 120.21(8) . . ?
O2 S1 C3 104.68(7) . . ?
O2 S1 C4 110.72(9) . . ?
C4 S1 C3 104.49(8) . . ?
N1 C1 C3 179.53(18) . . ?
N2 C2 C3 178.86(18) . . ?
S1 C3 H3 107.7 . . ?
C1 C3 S1 110.92(11) . . ?
C1 C3 C2 112.20(14) . . ?
C1 C3 H3 107.7 . . ?
C2 C3 S1 110.49(11) . . ?
C2 C3 H3 107.7 . . ?
S1 C4 H4A 109.5 . . ?
S1 C4 H4B 109.5 . . ?
S1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
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 O1 1.4272(13) . ?
S1 O2 1.4261(13) . ?
S1 C3 1.8513(15) . ?
S1 C4 1.7487(17) . ?
N1 C1 1.137(2) . ?
N2 C2 1.137(2) . ?
C1 C3 1.462(2) . ?
C2 C3 1.464(2) . ?
C3 H3 0.9900 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 C3 C1 46.74(13) . . . . ?
O1 S1 C3 C2 171.82(11) . . . . ?
O2 S1 C3 C1 174.46(12) . . . . ?
O2 S1 C3 C2 -60.46(13) . . . . ?
C4 S1 C3 C1 -69.09(13) . . . . ?
C4 S1 C3 C2 55.98(13) . . . . ?
