Synthesis and physical properties of tris(dialkylamino)cyclopropenium bistriflamide ionic liquids
Walst, Kelvin J.; Yunis, Ruhamah; Bayley, Paul; MacFarlane, Doug; Ward, Callum J.; Wang, Ruomeng; Curnow, Owen John; RSC Adv.  (2015) –; doi:10.1039/C5RA05254H

data_7220231
_publ_section_title
;
 Synthesis and physical properties of tris(dialkylamino)cyclopropenium
 bistriflamide ionic liquids
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA05254H
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C2 F6 N O4 S2, C21 H42 N3'
_chemical_formula_sum            'C23 H42 F6 N4 O4 S2'
_chemical_formula_weight         616.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-03-24 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.887(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.2495(4)
_cell_length_b                   10.09683(17)
_cell_length_c                   34.2770(7)
_cell_measurement_reflns_used    12841
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.5050
_cell_measurement_theta_min      3.0320
_cell_volume                     6407.6(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6501
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -21.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000  -90.0000 42

  2 omega  -61.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   77.0000   90.0000 56

  3 omega -109.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000    0.0000 -120.0000 152

  4 omega   31.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.3755 -125.0000   30.0000 57

  5 omega   32.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  -90.0000 77

  6 omega   47.00  135.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000  -30.0000 88

  7 omega   90.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   30.0000   60.0000 88

  8 omega   50.00  122.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -61.0000  120.0000 72

  9 omega   40.00  151.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -15.0000   30.0000 111

 10 omega   41.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  -30.0000 57

 11 omega   38.00   89.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  -90.0000 51

 12 omega   41.00   87.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000 -120.0000 46

 13 omega   45.00  112.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000 -180.0000 67

 14 omega   29.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.3755 -125.0000 -150.0000 67

 15 omega   42.00   88.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000   30.0000 46

 16 omega   38.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000  150.0000 53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0494840000
_diffrn_orient_matrix_UB_12      0.1007885000
_diffrn_orient_matrix_UB_13      0.0130037000
_diffrn_orient_matrix_UB_21      0.0578729000
_diffrn_orient_matrix_UB_22      0.0207712000
_diffrn_orient_matrix_UB_23      0.0405896000
_diffrn_orient_matrix_UB_31      0.0335352500
_diffrn_orient_matrix_UB_32      0.1127271500
_diffrn_orient_matrix_UB_33      -0.0191247500
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            22160
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.473
_diffrn_reflns_theta_min         2.681
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.114
_exptl_absorpt_correction_T_max  0.735
_exptl_absorpt_correction_T_min  0.635
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             2608
_exptl_crystal_size_max          0.3354
_exptl_crystal_size_mid          0.2735
_exptl_crystal_size_min          0.1846
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 4535 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.496(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     715
_refine_ls_number_reflns         11920
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0713P)^2^+1.9568P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1111
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.839
_reflns_Friedel_fraction_max     0.788
_reflns_number_gt                11444
_reflns_number_total             11920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra05254h2.cif
_cod_data_source_block           cham17ai
_cod_database_code               7220231
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         C23H42N4O4F6S2
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C45(H45A,H45B), C15(H15A,H15B), C52(H52A,H52B), C47(H47A,H47B),
 C13(H13A,H13B), C61(H61A,H61B), C22(H22A,H22B), C51(H51A,H51B), C44(H44A,H44B),
  C54(H54A,H54B), C20(H20A,H20B), C55(H55A,H55B), C9(H9A,H9B), C6(H6A,H6B),
 C19(H19A,H19B), C59(H59A,H59B), C58(H58A,H58B), C62(H62A,H62B), C12(H12A,H12B),
  C48(H48A,H48B), C5(H5A,H5B), C16(H16A,H16B), C23(H23A,H23B)
2.b Idealised Me refined as rotating group:
 C57(H57A,H57B,H57C), C43(H43A,H43B,H43C), C18(H18A,H18B,H18C), C24(H24A,H24B,
 H24C), C10(H10A,H10B,H10C), C56(H56A,H56B,H56C), C50(H50A,H50B,H50C), C63(H63A,
 H63B,H63C), C49(H49A,H49B,H49C), C11(H11A,H11B,H11C), C4(H4A,H4B,H4C),
 C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'