Molecular design principles of ionic liquids with a sulfonyl fluoride moiety
Siegel, David J.; Anderson, Grace I.; Cyr, Noah; Lambrecht, Daniel S.; Zeller, Matthias; Hillesheim, Patrick C.; Mirjafari, Arsalan; New Journal of Chemistry 45 (2021) 2443–2452; doi:10.1039/D0NJ05603K

data_7060309
_publ_section_title
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 Molecular design principles of ionic liquids with a sulfonyl fluoride
 moiety
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_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2443
_journal_page_last               2452
_journal_paper_doi               10.1039/D0NJ05603K
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C6 H10 F N2 O2 S, C4 F10 N1 O4 S2'
_chemical_formula_sum            'C10 H10 F11 N3 O6 S3'
_chemical_formula_weight         573.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-08-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
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_audit_update_record
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2020-09-18 deposited with the CCDC.	2021-01-15 downloaded from the CCDC.
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_cell_angle_alpha                90
_cell_angle_beta                 97.2610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8011(3)
_cell_length_b                   11.0925(3)
_cell_length_c                   18.3728(6)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      36.33
_cell_measurement_theta_min      2.50
_cell_volume                     1981.45(10)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Apex3 v2018.1-0 (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker AXS D8 Quest ECO diffractometer with a Photon II 
charge-integrating pixel array detector (CPAD)
;
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            83794
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.346
_diffrn_reflns_theta_min         2.149
_diffrn_source                   '1 kW fine focus sealed tube X-ray source'
_exptl_absorpt_coefficient_mu    0.512
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0784 before and 0.0558 after correction.
The Ratio of minimum to maximum transmission is 0.8944.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.922
_exptl_crystal_description       plate
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.081
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         9618
_refine_ls_number_restraints     1223
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0490
_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/[\s^2^(Fo^2^)+(0.0461P)^2^+1.9361P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1340
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7876
_reflns_number_total             9618
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj05603k2.cif
_cod_data_source_block           siegel10_so3f_mimso2fbeti_0113
_cod_depositor_comments
'Adding full bibliography for 7060306--7060309.cif.'
_cod_database_code               7060309
_plat230_alert_2_b
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PROBLEM: Hirshfeld Test Diff for    S1       --O1       .       10.1 s.u. 
RESPONSE: There is likely some rotational disorder in the functional group. This disorder, however, could not be modeled in a meaningful manner. 
;
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.821
_shelx_estimated_absorpt_t_min   0.821
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{N4A, N4B}
3. Restrained distances
 N4A-S2A \\sim N4B-S2B \\sim N4C-S2C \\sim N4A-S3A \\sim N4C-S3C
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
S2A \\sim S3A \\sim F2A \\sim F3A \\sim F4A \\sim F5A \\sim F6A \\sim F7A \\sim
F8A \\sim F9A \\sim F10A \\sim F11A \\sim O3A \\sim O4A \\sim O5A \\sim O6A
\\sim N4A \\sim C9A \\sim C10A \\sim C11A \\sim C12A \\sim S2B \\sim F2B \\sim
F3B \\sim F4B \\sim F5B \\sim F6B \\sim O3B \\sim O4B \\sim N4B \\sim C9B \\sim
C10B \\sim S2C \\sim S3C \\sim F2C \\sim F3C \\sim F4C \\sim F5C \\sim F6C
\\sim F7C \\sim F8C \\sim F9C \\sim F10C \\sim F11C \\sim O3C \\sim O4C \\sim
O5C \\sim O6C \\sim N4C \\sim C9C \\sim C10C \\sim C11B \\sim C12B: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.01 within 2A
Uanis(N4A) = Uanis(N4B)
5. Same fragment restrains
{S2A, F2A, F3A, F4A, F5A, F6A, O3A, O4A, N4A, C9A, C10A} sigma for 1-2: 0.02,
1-3: 0.04
as in
{S2B, F2B, F3B, F4B, F5B, F6B, O3B, O4B, N4B, C9B, C10B}
{S2A, F2A, F3A, F4A, F5A, F6A, O3A, O4A, N4A, C9A, C10A} sigma for 1-2: 0.02,
1-3: 0.04
as in
{S2C, F2C, F3C, F4C, F5C, F6C, O3C, O4C, N4C, C9C, C10C}
{S3A, F7A, F8A, F9A, F10A, F11A, O5A, O6A, C11A, C12A} sigma for 1-2: 0.02,
1-3: 0.04
as in
{S3C, F7C, F8C, F9C, F10C, F11C, O5C, O6C, C11B, C12B}
6. Others
 1*[Sof(S2A)+Sof(F2A)+Sof(F3A)+Sof(F4A)+Sof(F5A)+Sof(F6A)+Sof(O3A)+Sof(O4A)+
 Sof(N4A)+Sof(C9A)+Sof(C10A)]+1*[Sof(S2B)+Sof(F2B)+Sof(F3B)+Sof(F4B)+Sof(F5B)+
 Sof(F6B)+Sof(O3B)+Sof(O4B)+Sof(N4B)+Sof(C9B)+Sof(C10B)]+1*[Sof(S3A)+Sof(F7A)+
 Sof(F8A)+Sof(F9A)+Sof(F10A)+Sof(F11A)+Sof(O5A)+Sof(O6A)+Sof(C11A)+Sof(C12A)+
 Sof(S2C)+Sof(F2C)+Sof(F3C)+Sof(F4C)+Sof(F5C)+Sof(F6C)+Sof(O3C)+Sof(O4C)+
 Sof(N4C)+Sof(C9C)+Sof(C10C)+Sof(S3C)+Sof(F7C)+Sof(F8C)+Sof(F9C)+Sof(F10C)+
 Sof(F11C)+Sof(O5C)+Sof(O6C)+Sof(C11B)+Sof(C12B)]=1 with esd of 0
 Sof(S2A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=Sof(O3A)=Sof(O4A)=
 Sof(N4A)=Sof(C9A)=Sof(C10A)=FVAR(1)
 Sof(S2B)=Sof(F2B)=Sof(F3B)=Sof(F4B)=Sof(F5B)=Sof(F6B)=Sof(O3B)=Sof(O4B)=
 Sof(N4B)=Sof(C9B)=Sof(C10B)=FVAR(2)
 Sof(S3A)=Sof(F7A)=Sof(F8A)=Sof(F9A)=Sof(F10A)=Sof(F11A)=Sof(O5A)=Sof(O6A)=
 Sof(C11A)=Sof(C12A)=1-FVAR(3)
 Sof(S2C)=Sof(F2C)=Sof(F3C)=Sof(F4C)=Sof(F5C)=Sof(F6C)=Sof(O3C)=Sof(O4C)=
 Sof(N4C)=Sof(C9C)=Sof(C10C)=Sof(S3C)=Sof(F7C)=Sof(F8C)=Sof(F9C)=Sof(F10C)=
 Sof(F11C)=Sof(O5C)=Sof(O6C)=Sof(C11B)=Sof(C12B)=FVAR(3)
7.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5)
7.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
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_shelx_res_checksum              96311
_shelx_hkl_checksum              98419
_olex2_submission_special_instructions 'No special instructions were received'