Biomimetic design of protic lipidic ionic liquids with enhanced fluidity
O'Brien, Richard A.; Zayas, Manuel Sanchez; Nestor, Stephen T.; Gaitor, Jamie C.; Paul, Lauran M.; Edhegard, Forrest A.; Minkowicz, Samuel; Sykora, Richard E.; Sheng, Yinghong; Michael, Scott F.; Isern, Sharon; Mirjafari, Arsalan; New J. Chem. 40 (2016) 7795–; doi:10.1039/C6NJ00657D

data_7055692
_publ_section_title
;
 Biomimetic design of protic lipidic ionic liquids with enhanced fluidity
;
_journal_issue                   9
_journal_name_full               'New J. Chem.'
_journal_page_first              7795
_journal_paper_doi               10.1039/C6NJ00657D
_journal_volume                  40
_journal_year                    2016
_chemical_formula_moiety         'C20 H39 N2 S, C2 F6 N O4 S2'
_chemical_formula_sum            'C22 H39 F6 N3 O4 S3'
_chemical_formula_weight         619.74
_chemical_melting_point          299.28
_chemical_name_common            '[minSstearyl][NTf2]'
_chemical_name_systematic
'2-(hexadecylthio)-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-08-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-01-28 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                88.524(3)
_cell_angle_beta                 81.396(3)
_cell_angle_gamma                87.366(4)
_cell_formula_units_Z            4
_cell_length_a                   8.5670(4)
_cell_length_b                   14.0926(7)
_cell_length_c                   25.1175(9)
_cell_measurement_reflns_used    4180
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      25.0400
_cell_measurement_theta_min      2.7570
_cell_volume                     2994.6(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.31a (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,12:40:55)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.31a (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,12:40:55)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.31a (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,12:40:55)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 16.0514
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -38.00    8.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1508   57.0000    0.0000 46

  2 omega  -85.00  -20.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1508  -57.0000   30.0000 65

  3 omega  -24.00   25.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1508  -99.0000  150.0000 49

  4 omega  -85.00   -3.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1508  -57.0000 -120.0000 82

  5 omega  -17.00   53.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1508   57.0000 -180.0000 70

  6 omega  -29.00   47.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1508   77.0000   90.0000 76
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0561298000
_diffrn_orient_matrix_UB_12      0.0295060000
_diffrn_orient_matrix_UB_13      0.0084813000
_diffrn_orient_matrix_UB_21      -0.0395815000
_diffrn_orient_matrix_UB_22      -0.0030509000
_diffrn_orient_matrix_UB_23      0.0268509000
_diffrn_orient_matrix_UB_31      0.0480343000
_diffrn_orient_matrix_UB_32      -0.0407387000
_diffrn_orient_matrix_UB_33      0.0048071000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            20923
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.41
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.31a (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,12:40:55)
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    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1304
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     695
_refine_ls_number_reflns         10642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.7683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1237
_reflns_number_gt                6863
_reflns_number_total             10642
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6nj00657d2.cif
_cod_data_source_block           2
_cod_depositor_comments          'Adding full bibliography for 7055692.cif.'
_cod_database_code               7055692
_chemical_oxdiff_formula         'S3 C22 F6 N3 O4 H39'
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.04
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C32(H32A,H32B), C14(H14A,H14B), C10(H10A,H10B), C17(H17A,H17B),
 C31(H31A,H31B), C36(H36A,H36B), C37(H37A,H37B), C18(H18A,H18B), C34(H34A,H34B),
  C30(H30A,H30B), C8(H8A,H8B), C33(H33A,H33B), C11(H11A,H11B), C35(H35A,H35B),
 C6(H6A,H6B), C12(H12A,H12B), C28(H28A,H28B), C13(H13A,H13B), C15(H15A,H15B),
 C26(H26A,H26B), C39(H39A,H39B), C16(H16A,H16B), C7(H7A,H7B), C25(H25A,H25B),
 C27(H27A,H27B), C19(H19A,H19B), C5(H5A,H5B), C29(H29A,H29B), C38(H38A,H38B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C23(H23), C22(H22)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C20(H20A,H20B,H20C), C40(H40A,H40B,H40C), C24(H24A,H24B,H24C)
;
_olex2_date_sample_data_collection 2015-08-12
_olex2_submission_special_instructions 'No special instructions were received'