#------------------------------------------------------------------------------
#$Date: 2024-07-05 17:58:07 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292890 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/14/1571424.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_1571424
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         'C7 H9 Li N2 O3 S'
_chemical_formula_sum            'C7 H9 Li N2 O3 S'
_chemical_formula_weight         208.16
_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             2024-01-26
_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                98.120(3)
_cell_angle_beta                 97.915(4)
_cell_angle_gamma                113.035(4)
_cell_formula_units_Z            2
_cell_length_a                   6.7137(3)
_cell_length_b                   7.9569(3)
_cell_length_c                   11.1702(4)
_cell_measurement_reflns_used    3568
_cell_measurement_temperature    223.15
_cell_measurement_theta_max      71.3660
_cell_measurement_theta_min      6.1940
_cell_volume                     531.30(4)
_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_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    107.00 135.00   0.50    0.50    --   45.70  19.00-180.00   56
  2  ω    -43.00 103.00   0.50    0.50    --   45.70  19.00-180.00  292
  3  ω     45.00  90.00   0.50    0.50    --   45.70  57.00-120.00   90
  4  ω      3.00  60.00   0.50    0.50    --   45.70  82.00  30.00  114
  5  ω      3.00  48.00   0.50    0.50    --   45.70 -57.00-150.00   90
  6  ω     52.00  90.00   0.50    0.50    --   45.70 -57.00-150.00   76
  7  ω     60.00 142.00   0.50    0.50    --   98.30 -82.00  30.00  164
  8  ω     24.00  53.00   0.50    0.50    --   98.30 -82.00  30.00   58
  9  ω     32.00 141.00   0.50    0.50    --   98.30 -61.00  30.00  218
 10  ω      9.00  48.00   0.50    0.50    --   98.30  15.00 150.00   78
 11  ω     65.00 113.00   0.50    0.50    --   98.30  15.00 150.00   96
 12  ω    122.00 186.00   0.50    0.50    --   98.30  15.00 150.00  128
 13  ω     13.00  48.00   0.50    0.50    --   98.30 -82.00-120.00   70
 14  ω    100.00 145.00   0.50    0.50    --   98.30 -82.00-120.00   90
 15  ω     81.00 106.00   0.50    0.50    --   98.30 -77.00  90.00   50
 16  ω     74.00 188.00   0.50    0.50    --   98.30  15.00  60.00  228
 17  ω     63.00 108.00   0.50    0.50    --   98.30 -82.00 -30.00   90
 18  ω     11.00  54.00   0.50    0.50    --   98.30 -82.00 -30.00   86
 19  ω     11.00 107.00   0.50    0.50    --   98.30 -61.00-180.00  192
 20  ω     96.00 121.00   0.50    0.50    --   98.30  61.00-120.00   50
 21  ω     33.00 134.00   0.50    0.50    --   98.30 -82.00-180.00  202
 22  ω     89.00 137.00   0.50    0.50    --   98.30 -82.00-150.00   96
 23  ω      9.00  39.00   0.50    0.50    --   98.30  15.00  60.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4630
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.791
_diffrn_reflns_theta_min         6.187
_exptl_absorpt_coefficient_mu    2.586
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32755
_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    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.698
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         1993
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0530
_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)+(0.0831P)²+0.2210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1364
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1890
_reflns_number_total             1993
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc01492h3.cif
_cod_data_source_block           LiCMs(CN)2
_cod_depositor_comments
'Adding full bibliography for 1571419--1571424.cif.'
_cod_database_code               1571424
_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   0.698
_shelx_estimated_absorpt_t_min   0.600
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C7B) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.01
3. Others
 Fixed Sof: C5(0.35) C6(0.35) H6A(0.35) H6B(0.35) H6C(0.35) C7(0.35) H7A(0.35)
 H7B(0.35) H7C(0.35) C5A(0.35) C6A(0.35) H6AA(0.35) H6AB(0.35) H6AC(0.35)
 C7A(0.35) H7AA(0.35) H7AB(0.35) H7AC(0.35) C5B(0.3) C6B(0.3) H6BA(0.3)
 H6BB(0.3) H6BC(0.3) C7B(0.3) H7BA(0.3) H7BB(0.3) H7BC(0.3)
4.a Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C6A(H6AA,H6AB,H6AC),
 C7A(H7AA,H7AB,H7AC), C6B(H6BA,H6BB,H6BC), C7B(H7BA,H7BB,H7BC)
;
_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
;
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 0.42240(7) 0.69530(6) 0.85834(4) 0.0216(2) Uani 1 1 d . . . . .
O1 O 0.5049(2) 0.8674(2) 0.81293(15) 0.0298(4) Uani 1 1 d . . . . .
O2 O 0.4709(3) 0.5434(2) 0.80544(15) 0.0312(4) Uani 1 1 d . . . . .
O3 O 0.7303(4) 0.9382(3) 0.58465(17) 0.0501(5) Uani 1 1 d . . . . .
N1 N -0.0774(3) 0.2699(3) 0.8249(2) 0.0399(5) Uani 1 1 d . . . . .
N2 N -0.0273(3) 0.8530(3) 0.8245(2) 0.0404(5) Uani 1 1 d . . . . .
C1 C 0.5326(4) 0.7556(3) 1.0180(2) 0.0344(5) Uani 1 1 d . . . . .
H1A H 0.692202 0.798668 1.032392 0.052 Uiso 1 1 calc R U . . .
H1B H 0.469914 0.646985 1.053640 0.052 Uiso 1 1 calc R U . . .
H1C H 0.496671 0.854370 1.056252 0.052 Uiso 1 1 calc R U . . .
C2 C 0.1403(3) 0.6172(3) 0.8368(2) 0.0267(5) Uani 1 1 d . . . . .
C3 C 0.0171(4) 0.4274(3) 0.8305(2) 0.0290(5) Uani 1 1 d . . . . .
C4 C 0.0466(4) 0.7457(3) 0.8312(2) 0.0291(5) Uani 1 1 d . . . . .
C5 C 0.7513(13) 1.0033(12) 0.4907(7) 0.0422(17) Uani 0.35 1 d . . P A 1
C6 C 0.8486(16) 1.2068(13) 0.4880(9) 0.054(2) Uani 0.35 1 d . . P A 1
H6A H 0.911529 1.280398 0.571841 0.081 Uiso 0.35 1 calc R U P A 1
H6B H 0.733631 1.239308 0.449907 0.081 Uiso 0.35 1 calc R U P A 1
H6C H 0.963755 1.232558 0.440486 0.081 Uiso 0.35 1 calc R U P A 1
C7 C 0.636(8) 0.869(8) 0.370(5) 0.053(9) Uani 0.35 1 d . . P A 1
H7A H 0.744520 0.851103 0.327302 0.079 Uiso 0.35 1 calc R U P A 1
H7B H 0.550248 0.917484 0.320479 0.079 Uiso 0.35 1 calc R U P A 1
H7C H 0.537959 0.749908 0.385154 0.079 Uiso 0.35 1 calc R U P A 1
C5A C 0.6026(17) 0.8299(12) 0.4832(8) 0.0352(19) Uani 0.35 1 d . . P A 2
C6A C 0.3924(18) 0.6641(13) 0.4732(9) 0.065(3) Uani 0.35 1 d . . P A 2
H6AA H 0.399801 0.553858 0.428277 0.098 Uiso 0.35 1 calc R U P A 2
H6AB H 0.270052 0.682738 0.429349 0.098 Uiso 0.35 1 calc R U P A 2
H6AC H 0.369836 0.647480 0.555406 0.098 Uiso 0.35 1 calc R U P A 2
C7A C 0.677(7) 0.864(3) 0.367(3) 0.042(9) Uani 0.35 1 d . . P A 2
H7AA H 0.691234 0.986450 0.355953 0.063 Uiso 0.35 1 calc R U P A 2
H7AB H 0.569302 0.769219 0.297759 0.063 Uiso 0.35 1 calc R U P A 2
H7AC H 0.819201 0.857803 0.370491 0.063 Uiso 0.35 1 calc R U P A 2
C5B C 0.712(3) 0.8324(15) 0.4962(10) 0.047(3) Uani 0.3 1 d . . P A 3
C6B C 0.683(10) 0.880(8) 0.367(4) 0.046(13) Uani 0.3 1 d . . P A 3
H6BA H 0.530136 0.860073 0.339008 0.070 Uiso 0.3 1 calc R U P A 3
H6BB H 0.719525 0.800023 0.308588 0.070 Uiso 0.3 1 calc R U P A 3
H6BC H 0.779895 1.009775 0.372000 0.070 Uiso 0.3 1 calc R U P A 3
C7B C 0.765(4) 0.668(2) 0.5000(18) 0.106(5) Uani 0.3 1 d . U P A 3
H7BA H 0.921672 0.704783 0.501513 0.159 Uiso 0.3 1 calc R U P A 3
H7BB H 0.678513 0.570056 0.427207 0.159 Uiso 0.3 1 calc R U P A 3
H7BC H 0.730446 0.621284 0.573713 0.159 Uiso 0.3 1 calc R U P A 3
Li1 Li 0.7876(6) 0.9859(5) 0.7650(4) 0.0291(8) Uani 1 1 d . . . . .
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'
Li Li 0.0008 0.0003 '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 C1 106.70(11) . . ?
O1 S1 C2 107.25(9) . . ?
O2 S1 O1 118.22(9) . . ?
O2 S1 C1 107.96(10) . . ?
O2 S1 C2 108.30(10) . . ?
C2 S1 C1 108.04(12) . . ?
S1 O1 Li1 127.76(14) . . ?
C5 O3 Li1 147.7(4) . . ?
C5A O3 Li1 146.3(4) . . ?
C5B O3 Li1 144.0(7) . . ?
C3 N1 Li1 162.3(2) . 1_445 ?
C4 N2 Li1 162.7(2) . 1_455 ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 S1 117.31(16) . . ?
C3 C2 C4 123.52(19) . . ?
C4 C2 S1 119.12(16) . . ?
N1 C3 C2 177.4(2) . . ?
N2 C4 C2 178.3(2) . . ?
O3 C5 C6 125.7(7) . . ?
O3 C5 C7 116(2) . . ?
C7 C5 C6 117(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 C5A C6A 125.2(7) . . ?
O3 C5A C7A 117.8(13) . . ?
C7A C5A C6A 116.9(13) . . ?
C5A C6A H6AA 109.5 . . ?
C5A C6A H6AB 109.5 . . ?
C5A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
C5A C7A H7AA 109.5 . . ?
C5A C7A H7AB 109.5 . . ?
C5A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
O3 C5B C6B 121(2) . . ?
O3 C5B C7B 122.9(12) . . ?
C7B C5B C6B 115(2) . . ?
C5B C6B H6BA 109.5 . . ?
C5B C6B H6BB 109.5 . . ?
C5B C6B H6BC 109.5 . . ?
H6BA C6B H6BB 109.5 . . ?
H6BA C6B H6BC 109.5 . . ?
H6BB C6B H6BC 109.5 . . ?
C5B C7B H7BA 109.5 . . ?
C5B C7B H7BB 109.5 . . ?
C5B C7B H7BC 109.5 . . ?
H7BA C7B H7BB 109.5 . . ?
H7BA C7B H7BC 109.5 . . ?
H7BB C7B H7BC 109.5 . . ?
O1 Li1 O3 107.6(2) . . ?
O1 Li1 N1 111.40(19) . 1_665 ?
O1 Li1 N2 105.89(18) . 1_655 ?
O3 Li1 N1 106.23(19) . 1_665 ?
O3 Li1 N2 108.83(19) . 1_655 ?
N2 Li1 N1 116.6(2) 1_655 1_665 ?
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 1.4557(15) . ?
S1 O2 1.4403(14) . ?
S1 C1 1.754(2) . ?
S1 C2 1.715(2) . ?
O1 Li1 1.949(4) . ?
O3 C5 1.235(8) . ?
O3 C5A 1.281(9) . ?
O3 C5B 1.162(11) . ?
O3 Li1 1.951(4) . ?
N1 C3 1.150(3) . ?
N1 Li1 2.044(4) 1_445 ?
N2 C4 1.149(3) . ?
N2 Li1 2.026(4) 1_455 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.395(3) . ?
C2 C4 1.398(3) . ?
C5 C6 1.497(12) . ?
C5 C7 1.49(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C5A C6A 1.484(14) . ?
C5A C7A 1.48(4) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C6A H6AC 0.9700 . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C7A H7AC 0.9700 . ?
C5B C6B 1.55(4) . ?
C5B C7B 1.49(2) . ?
C6B H6BA 0.9700 . ?
C6B H6BB 0.9700 . ?
C6B H6BC 0.9700 . ?
C7B H7BA 0.9700 . ?
C7B H7BB 0.9700 . ?
C7B H7BC 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 C2 C3 157.40(18) . . . . ?
O1 S1 C2 C4 -25.0(2) . . . . ?
O2 S1 O1 Li1 -37.6(2) . . . . ?
O2 S1 C2 C3 28.8(2) . . . . ?
O2 S1 C2 C4 -153.65(19) . . . . ?
C1 S1 O1 Li1 84.2(2) . . . . ?
C1 S1 C2 C3 -87.9(2) . . . . ?
C1 S1 C2 C4 89.6(2) . . . . ?
C2 S1 O1 Li1 -160.2(2) . . . . ?
Li1 O3 C5 C6 -5.5(12) . . . . ?
Li1 O3 C5 C7 -175(2) . . . . ?
Li1 O3 C5A C6A 4.3(15) . . . . ?
Li1 O3 C5A C7A -171.2(17) . . . . ?
Li1 O3 C5B C6B -175(3) . . . . ?
Li1 O3 C5B C7B -9(3) . . . . ?
