Bridging the crystal and solution structure of a series of lipid-inspired ionic liquids.
Bellia, Sophia A.; Metzler, Matthew; Huynh, Marissa; Zeller, Matthias; Mirjafari, Arsalan; Cohn, Pamela; Hillesheim, Patrick C.; Soft matter 19 (2023) 749–765; doi:10.1039/d2sm01478e

data_1568262
_publ_section_title
;
 Bridging the crystal and solution structure of a series of lipid-inspired
 ionic liquids.
;
_journal_issue                   4
_journal_name_full               'Soft matter'
_journal_page_first              749
_journal_page_last               765
_journal_paper_doi               10.1039/d2sm01478e
_journal_volume                  19
_journal_year                    2023
_chemical_formula_moiety         'C21 H41 N2, C2 F6 N O4 S2'
_chemical_formula_sum            'C23 H41 F6 N3 O4 S2'
_chemical_formula_weight         601.71
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-11-07
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-09 deposited with the CCDC.	2022-12-28 downloaded from the CCDC.
;
_cell_angle_alpha                96.4858(18)
_cell_angle_beta                 95.9509(17)
_cell_angle_gamma                98.1327(17)
_cell_formula_units_Z            4
_cell_length_a                   7.0531(2)
_cell_length_b                   15.7762(5)
_cell_length_c                   27.1070(9)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      78.9869
_cell_measurement_theta_min      5.3969
_cell_volume                     2944.75(16)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Apex3 v2019.11-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics
;
SHELXLE Rev1183 (H\"ubschle et al., 2011)
Olex2 1.5 (Dolomanov et al., 2009)
;
_computing_publication_material
;
SHELXLE Rev1183 (H\"ubschle et al., 2011)
Olex2 1.5 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1183 (H\"ubschle et al., 2011)
Olex2 1.5 (Dolomanov et al., 2009)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type
;
Bruker AXS D8 Quest diffractometer with PhotonIII_C14 charge-integrating and 
photon counting pixel array detector
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            28387
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.610
_diffrn_reflns_theta_min         2.853
_exptl_absorpt_coefficient_mu    2.276
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.5947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       plate
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1385
_refine_ls_number_reflns         12039
_refine_ls_number_restraints     2748
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0890
_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^)+(0.0683P)^2^+10.5612P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2519
_refine_ls_wR_factor_ref         0.2612
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9026
_reflns_number_total             12039
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sm01478e2.cif
_cod_data_source_block           c16_dime_tf2n_0m
_cod_depositor_comments
'Adding full bibliography for 1568260--1568262.cif.'
_cod_database_code               1568262
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.895
_shelx_estimated_absorpt_t_min   0.672
_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. Uiso/Uaniso restraints and constraints
N1A \\sim N2A \\sim C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim C6A \\sim
C7A \\sim C8A \\sim C9A \\sim C10A \\sim C11A \\sim C12A \\sim C13A \\sim C14A
\\sim C15A \\sim C16A \\sim C17A \\sim C18A \\sim C19A \\sim C20A \\sim C21A
\\sim N1C \\sim N2C \\sim C1C \\sim C2C \\sim C3C \\sim C4C \\sim C5C \\sim C6C
\\sim C7C \\sim C8C \\sim C9C \\sim C10C \\sim C11C \\sim C12C \\sim C13C \\sim
C14C \\sim C15C \\sim C16C \\sim C17C \\sim C18C \\sim C19C \\sim C20C \\sim
C21C: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04 within
2A
N1B \\sim N2B \\sim C1B \\sim C2B \\sim C3B \\sim C4B \\sim C5B \\sim C6B \\sim
C7B \\sim C8B \\sim C9B \\sim C10B \\sim C11B \\sim C12B \\sim C13B \\sim C14B
\\sim C15B \\sim C16B \\sim C17B \\sim C18B \\sim C19B \\sim C20B \\sim C21B
\\sim N1D \\sim N2D \\sim C1D \\sim C2D \\sim C3D \\sim C4D \\sim C5D \\sim C6D
\\sim C7D \\sim C8D \\sim C9D \\sim C10D \\sim C11D \\sim C12D \\sim C13D \\sim
C14D \\sim C15D \\sim C16D \\sim C17D \\sim C18D \\sim C19D \\sim C20D \\sim
C21D: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04 within
2A
F1A \\sim F2A \\sim F3A \\sim C22A \\sim S1A \\sim O1A \\sim O2A \\sim N3A
\\sim S2A \\sim O3A \\sim O4A \\sim C23A \\sim F4A \\sim F5A \\sim F6A \\sim
F1C \\sim F2C \\sim F3C \\sim C22C \\sim S1C \\sim O1C \\sim O2C \\sim N3C
\\sim S2C \\sim O3C \\sim O4C \\sim C23C \\sim F4C \\sim F5C \\sim F6C: within
2A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 2A
F4A \\sim F5A \\sim F6A \\sim F4C \\sim F5C \\sim F6C: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
F1B \\sim F2B \\sim F3B \\sim C22B \\sim S1B \\sim O1B \\sim O2B \\sim N3B
\\sim S2B \\sim O3B \\sim O4B \\sim C23B \\sim F4B \\sim F5B \\sim F6B \\sim
F1D \\sim F2D \\sim F3D \\sim C22D \\sim S1D \\sim O1D \\sim O2D \\sim N3D
\\sim S2D \\sim O3D \\sim O4D \\sim C23D \\sim F4D \\sim F5D \\sim F6D: within
2A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 2A
F4B \\sim F5B \\sim F6B \\sim F4D \\sim F5D \\sim F6D: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
3. Same fragment restrains
{N1A, N2A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, C10A, C11A, C12A, C13A,
C14A, C15A, C16A, C17A, C18A, C19A, C20A, C21A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{N1C, N2C, C1C, C2C, C3C, C4C, C5C, C6C, C7C, C8C, C9C, C10C, C11C, C12C, C13C,
C14C, C15C, C16C, C17C, C18C, C19C, C20C, C21C}
{N1A, N2A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, C10A, C11A, C12A, C13A,
C14A, C15A, C16A, C17A, C18A, C19A, C20A, C21A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{N1B, N2B, C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B, C9B, C10B, C11B, C12B, C13B,
C14B, C15B, C16B, C17B, C18B, C19B, C20B, C21B}
{N1A, N2A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, C10A, C11A, C12A, C13A,
C14A, C15A, C16A, C17A, C18A, C19A, C20A, C21A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{N1D, N2D, C1D, C2D, C3D, C4D, C5D, C6D, C7D, C8D, C9D, C10D, C11D, C12D, C13D,
C14D, C15D, C16D, C17D, C18D, C19D, C20D, C21D}
{F1A, F2A, F3A, C22A, S1A, O1A, O2A, N3A, S2A, O3A, O4A, C23A, F4A, F5A, F6A}
sigma for 1-2: 0.02, 1-3: 0.04
as in
{F1C, F2C, F3C, C22C, S1C, O1C, O2C, N3C, S2C, O3C, O4C, C23C, F4C, F5C, F6C}
{F1B, F2B, F3B, C22B, S1B, O1B, O2B, N3B, S2B, O3B, O4B, C23B, F4B, F5B, F6B}
sigma for 1-2: 0.02, 1-3: 0.04
as in
{F1D, F2D, F3D, C22D, S1D, O1D, O2D, N3D, S2D, O3D, O4D, C23D, F4D, F5D, F6D}
4. Others
 Sof(N1C)=Sof(N2C)=Sof(C1C)=Sof(C2C)=Sof(H2C)=Sof(C3C)=Sof(H3C)=Sof(C4C)=
 Sof(H4CA)=Sof(H4CB)=Sof(H4CC)=Sof(C5C)=Sof(H5CA)=Sof(H5CB)=Sof(H5CC)=Sof(C6C)=
 Sof(H6CA)=Sof(H6CB)=Sof(C7C)=Sof(H7CA)=Sof(H7CB)=Sof(C8C)=Sof(H8CA)=Sof(H8CB)=
 Sof(C9C)=Sof(H9CA)=Sof(H9CB)=Sof(C10C)=Sof(H10C)=Sof(H10D)=Sof(C11C)=Sof(H11C)=
 Sof(H11D)=Sof(C12C)=Sof(H12C)=Sof(H12D)=Sof(C13C)=Sof(H13C)=Sof(H13D)=
 Sof(C14C)=Sof(H14C)=Sof(H14D)=Sof(C15C)=Sof(H15C)=Sof(H15D)=Sof(C16C)=
 Sof(H16C)=Sof(H16D)=Sof(C17C)=Sof(H17C)=Sof(H17D)=Sof(C18C)=Sof(H18C)=
 Sof(H18D)=Sof(C19C)=Sof(H19C)=Sof(H19D)=Sof(C20C)=Sof(H20C)=Sof(H20D)=
 Sof(C21C)=Sof(H21D)=Sof(H21E)=Sof(H21F)=1-FVAR(1)
 Sof(N1A)=Sof(N2A)=Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=
 Sof(H4AA)=Sof(H4AB)=Sof(H4AC)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(H5AC)=Sof(C6A)=
 Sof(H6AA)=Sof(H6AB)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C10A)=Sof(H10A)=Sof(H10B)=Sof(C11A)=Sof(H11A)=
 Sof(H11B)=Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(C13A)=Sof(H13A)=Sof(H13B)=
 Sof(C14A)=Sof(H14A)=Sof(H14B)=Sof(C15A)=Sof(H15A)=Sof(H15B)=Sof(C16A)=
 Sof(H16A)=Sof(H16B)=Sof(C17A)=Sof(H17A)=Sof(H17B)=Sof(C18A)=Sof(H18A)=
 Sof(H18B)=Sof(C19A)=Sof(H19A)=Sof(H19B)=Sof(C20A)=Sof(H20A)=Sof(H20B)=
 Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(1)
 Sof(N1D)=Sof(N2D)=Sof(C1D)=Sof(C2D)=Sof(H2D)=Sof(C3D)=Sof(H3D)=Sof(C4D)=
 Sof(H4DA)=Sof(H4DB)=Sof(H4DC)=Sof(C5D)=Sof(H5DA)=Sof(H5DB)=Sof(H5DC)=Sof(C6D)=
 Sof(H6DA)=Sof(H6DB)=Sof(C7D)=Sof(H7DA)=Sof(H7DB)=Sof(C8D)=Sof(H8DA)=Sof(H8DB)=
 Sof(C9D)=Sof(H9DA)=Sof(H9DB)=Sof(C10D)=Sof(H10G)=Sof(H10H)=Sof(C11D)=Sof(H11G)=
 Sof(H11H)=Sof(C12D)=Sof(H12G)=Sof(H12H)=Sof(C13D)=Sof(H13G)=Sof(H13H)=
 Sof(C14D)=Sof(H14G)=Sof(H14H)=Sof(C15D)=Sof(H15G)=Sof(H15H)=Sof(C16D)=
 Sof(H16G)=Sof(H16H)=Sof(C17D)=Sof(H17G)=Sof(H17H)=Sof(C18D)=Sof(H18G)=
 Sof(H18H)=Sof(C19D)=Sof(H19G)=Sof(H19H)=Sof(C20D)=Sof(H20G)=Sof(H20H)=
 Sof(C21D)=Sof(H21J)=Sof(H21K)=Sof(H21L)=1-FVAR(2)
 Sof(N1B)=Sof(N2B)=Sof(C1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=
 Sof(H4BA)=Sof(H4BB)=Sof(H4BC)=Sof(C5B)=Sof(H5BA)=Sof(H5BB)=Sof(H5BC)=Sof(C6B)=
 Sof(H6BA)=Sof(H6BB)=Sof(C7B)=Sof(H7BA)=Sof(H7BB)=Sof(C8B)=Sof(H8BA)=Sof(H8BB)=
 Sof(C9B)=Sof(H9BA)=Sof(H9BB)=Sof(C10B)=Sof(H10E)=Sof(H10F)=Sof(C11B)=Sof(H11E)=
 Sof(H11F)=Sof(C12B)=Sof(H12E)=Sof(H12F)=Sof(C13B)=Sof(H13E)=Sof(H13F)=
 Sof(C14B)=Sof(H14E)=Sof(H14F)=Sof(C15B)=Sof(H15E)=Sof(H15F)=Sof(C16B)=
 Sof(H16E)=Sof(H16F)=Sof(C17B)=Sof(H17E)=Sof(H17F)=Sof(C18B)=Sof(H18E)=
 Sof(H18F)=Sof(C19B)=Sof(H19E)=Sof(H19F)=Sof(C20B)=Sof(H20E)=Sof(H20F)=
 Sof(C21B)=Sof(H21G)=Sof(H21H)=Sof(H21I)=FVAR(2)
 Sof(F1C)=Sof(F2C)=Sof(F3C)=Sof(C22C)=Sof(S1C)=Sof(O1C)=Sof(O2C)=Sof(N3C)=
 Sof(S2C)=Sof(O3C)=Sof(O4C)=Sof(C23C)=Sof(F4C)=Sof(F5C)=Sof(F6C)=1-FVAR(3)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(C22A)=Sof(S1A)=Sof(O1A)=Sof(O2A)=Sof(N3A)=
 Sof(S2A)=Sof(O3A)=Sof(O4A)=Sof(C23A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=FVAR(3)
 Sof(F1D)=Sof(F2D)=Sof(F3D)=Sof(C22D)=Sof(S1D)=Sof(O1D)=Sof(O2D)=Sof(N3D)=
 Sof(S2D)=Sof(O3D)=Sof(O4D)=Sof(C23D)=Sof(F4D)=Sof(F5D)=Sof(F6D)=1-FVAR(4)
 Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(C22B)=Sof(S1B)=Sof(O1B)=Sof(O2B)=Sof(N3B)=
 Sof(S2B)=Sof(O3B)=Sof(O4B)=Sof(C23B)=Sof(F4B)=Sof(F5B)=Sof(F6B)=FVAR(4)
5.a Secondary CH2 refined with riding coordinates:
 C6A(H6AA,H6AB), C7A(H7AA,H7AB), C8A(H8AA,H8AB), C9A(H9AA,H9AB), C10A(H10A,
 H10B), C11A(H11A,H11B), C12A(H12A,H12B), C13A(H13A,H13B), C14A(H14A,H14B),
 C15A(H15A,H15B), C16A(H16A,H16B), C17A(H17A,H17B), C18A(H18A,H18B), C19A(H19A,
 H19B), C20A(H20A,H20B), C6C(H6CA,H6CB), C7C(H7CA,H7CB), C8C(H8CA,H8CB),
 C9C(H9CA,H9CB), C10C(H10C,H10D), C11C(H11C,H11D), C12C(H12C,H12D), C13C(H13C,
 H13D), C14C(H14C,H14D), C15C(H15C,H15D), C16C(H16C,H16D), C17C(H17C,H17D),
 C18C(H18C,H18D), C19C(H19C,H19D), C20C(H20C,H20D), C6B(H6BA,H6BB), C7B(H7BA,
 H7BB), C8B(H8BA,H8BB), C9B(H9BA,H9BB), C10B(H10E,H10F), C11B(H11E,H11F),
 C12B(H12E,H12F), C13B(H13E,H13F), C14B(H14E,H14F), C15B(H15E,H15F), C16B(H16E,
 H16F), C17B(H17E,H17F), C18B(H18E,H18F), C19B(H19E,H19F), C20B(H20E,H20F),
 C6D(H6DA,H6DB), C7D(H7DA,H7DB), C8D(H8DA,H8DB), C9D(H9DA,H9DB), C10D(H10G,
 H10H), C11D(H11G,H11H), C12D(H12G,H12H), C13D(H13G,H13H), C14D(H14G,H14H),
 C15D(H15G,H15H), C16D(H16G,H16H), C17D(H17G,H17H), C18D(H18G,H18H), C19D(H19G,
 H19H), C20D(H20G,H20H)
5.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C2C(H2C), C3C(H3C), C2B(H2B), C3B(H3B), C2D(H2D), C3D(H3D)
5.c Idealised Me refined as rotating group:
 C4A(H4AA,H4AB,H4AC), C5A(H5AA,H5AB,H5AC), C21A(H21A,H21B,H21C), C4C(H4CA,H4CB,
 H4CC), C5C(H5CA,H5CB,H5CC), C21C(H21D,H21E,H21F), C4B(H4BA,H4BB,H4BC),
 C5B(H5BA,H5BB,H5BC), C21B(H21G,H21H,H21I), C4D(H4DA,H4DB,H4DC), C5D(H5DA,H5DB,
 H5DC), C21D(H21J,H21K,H21L)
;
_shelx_res_checksum              96802
_shelx_hkl_checksum              27946
_olex2_submission_special_instructions 'No special instructions were received'