Synthesis and physical properties of tris(dialkylamino)cyclopropenium dicyanamide ionic liquids
Curnow, Owen J.; Polson, Matthew I. J.; Walst, Kelvin J.; Yunis, Ruhamah; RSC Advances 8 (2018) 28313–; doi:10.1039/C8RA05558K

data_7231323
_publ_section_title
;
 Synthesis and physical properties of tris(dialkylamino)cyclopropenium
 dicyanamide ionic liquids
;
_journal_issue                   50
_journal_name_full               'RSC Advances'
_journal_page_first              28313
_journal_paper_doi               10.1039/C8RA05558K
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'H2 O, C9 H18 N3, C2 N3'
_chemical_formula_sum            'C11 H20 N6 O'
_chemical_formula_weight         252.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-06-22 deposited with the CCDC.
2018-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.386(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.2120(4)
_cell_length_b                   9.00560(10)
_cell_length_c                   13.5409(2)
_cell_measurement_reflns_used    15377
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.6250
_cell_measurement_theta_min      3.8980
_cell_volume                     2741.81(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_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
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     63.00 115.00   1.00    4.00    --  111.00-125.00 120.00   52
  2  \w     47.00  79.00   1.00    4.00    --  111.00 -94.00   0.00   32
  3  \w     44.00  73.00   1.00    4.00    --  111.00 -94.00  60.00   29
  4  \w     44.00  81.00   1.00    4.00    --  111.00 -94.00 120.00   37
  5  \w     44.00 119.00   1.00    4.00    --  111.00-125.00  60.00   75
  6  \w     84.00 109.00   1.00    4.00    --  111.00 -94.00 -60.00   25
  7  \w     68.00 118.00   1.00    4.00    --  111.00-125.00 -60.00   50
  8  \w    101.00 141.00   1.00    4.00    --  111.00 -77.00-150.00   40
  9  \w     70.00  99.00   1.00    4.00    --  111.00-125.00-180.00   29
 10  \w     56.00  96.00   1.00    4.00    --  111.00 -94.00-180.00   40
 11  \w     47.00  83.00   1.00    4.00    --  111.00 -77.00-150.00   36
 12  \w     31.00  66.00   1.00    4.00    --  111.00 -94.00 -60.00   35
 13  \w     24.00  94.00   1.00    1.00    --   42.50-125.00-120.00   70
 14  \w     23.00  89.00   1.00    1.00    --   42.50-125.00 120.00   66
 15  \w     64.00 121.00   1.00    4.00    --   86.00  64.00 -89.72   57
 16  \w    128.00 153.00   1.00    4.00    --   86.00  64.00 -89.72   25
 17  \w    141.00 167.00   1.00    4.00    --  111.00  61.00-141.98   26
 18  \w    120.00 174.00   1.00    4.00    --  111.00  77.00 -60.00   54
 19  \w    116.00 177.00   1.00    4.00    --  111.00  77.00-150.00   61
 20  \w    122.00 174.00   1.00    4.00    --  111.00  77.00-180.00   52
 21  \w    105.00 135.00   1.00    1.00    --   66.00  76.00-167.58   30
 22  \w     99.00 125.00   1.00    1.00    --   54.00  77.00-133.48   26
 23  \w    102.00 129.00   1.00    1.00    --   70.00  76.00 -59.59   27
 24  \w     89.00 124.00   1.00    1.00    --   62.00  77.00  -4.20   35
 25  \w    109.00 135.00   1.00    1.00    --   66.00  77.00  46.04   26
 26  \w    113.00 139.00   1.00    4.00    --   82.00  68.00  60.82   26
 27  \w    112.00 159.00   1.00    4.00    --  111.00  77.00  60.00   47
 28  \w    124.00 157.00   1.00    4.00    --  111.00  61.00 120.00   33
 29  \w    143.00 169.00   1.00    4.00    --  111.00  77.00 120.00   26
 30  \w    127.00 177.00   1.00    4.00    --  111.00  77.00  90.00   50
 31  \w     85.00 115.00   1.00    4.00    --  111.00  61.00 120.00   30
 32  \w     87.00 165.00   1.00    4.00    --  111.00  61.00 150.00   78
 33  \w     86.00 136.00   1.00    4.00    --  111.00  61.00  60.00   50
 34  \w     83.00 161.00   1.00    4.00    --  111.00  72.00  80.92   78
 35  \w     85.00 134.00   1.00    4.00    --  111.00  61.00 -30.00   49
 36  \w     91.00 178.00   1.00    4.00    --  111.00  61.00-120.00   87
 37  \w     86.00 119.00   1.00    4.00    --  111.00  61.00-141.98   33
 38  \w     85.00 143.00   1.00    4.00    --  111.00  61.00-180.00   58
 39  \w     85.00 148.00   1.00    4.00    --  111.00  61.00 -90.00   63
 40  \w     81.00 115.00   1.00    4.00    --  111.00  77.00 -60.00   34
 41  \w     81.00 178.00   1.00    4.00    --  111.00  77.00   0.00   97
 42  \w     81.00 106.00   1.00    4.00    --  111.00  77.00  60.00   25
 43  \w     81.00 176.00   1.00    4.00    --  111.00  77.00  30.00   95
 44  \w     84.00 178.00   1.00    4.00    --  111.00  77.00 -90.00   94
 45  \w     81.00 177.00   1.00    4.00    --  111.00  77.00 -30.00   96
 46  \w     78.00 103.00   1.00    4.00    --  106.00  69.00 -59.77   25
 47  \w     77.00 103.00   1.00    4.00    --  106.00  71.00  -2.37   26
 48  \w     66.00  92.00   1.00    4.00    --   94.00  67.00  27.61   26
 49  \w     65.00  92.00   1.00    4.00    --   94.00  72.00  -9.00   27
 50  \w     55.00  81.00   1.00    4.00    --   82.00  68.00  60.82   26
 51  \w     60.00  92.00   1.00    4.00    --   90.00  77.00 105.51   32
 52  \w     81.00 111.00   1.00    4.00    --  111.00  77.00 120.00   30
 53  \w     82.00 108.00   1.00    4.00    --  111.00  77.00  90.00   26
 54  \w     61.00  92.00   1.00    4.00    --   90.00  73.00 156.98   31
 55  \w     57.00  83.00   1.00    4.00    --   82.00  75.00 149.36   26
 56  \w     48.00  74.00   1.00    4.00    --   78.00  76.00 100.71   26
 57  \w     44.00  70.00   1.00    1.00    --   74.00  75.00  85.66   26
 58  \w     36.00  73.00   1.00    1.00    --   66.00  77.00  46.04   37
 59  \w     48.00  74.00   1.00    4.00    --   78.00  76.00  10.82   26
 60  \w     54.00  80.00   1.00    4.00    --   82.00  67.00 -44.77   26
 61  \w     49.00  84.00   1.00    4.00    --   78.00  74.00 -96.39   35
 62  \w     65.00  91.00   1.00    4.00    --   90.00  61.00-145.44   26
 63  \w     85.00 107.00   1.00    4.00    --  111.00  77.00-150.00   22
 64  \w     81.00 107.00   1.00    4.00    --  111.00  77.00-120.00   26
 65  \w     91.00 108.00   1.00    4.00    --  111.00  77.00-180.00   17
 66  \w     48.00  63.00   1.00    4.00    --   78.00  77.00-170.82   15
 67  \w     44.00  69.00   1.00    1.00    --   74.00  75.00-126.63   25
 68  \w     38.00  82.00   1.00    1.00    --   66.00  76.00-167.58   44
 69  \w     37.00  68.00   1.00    1.00    --   66.00  77.00 -93.88   31
 70  \w     40.00  66.00   1.00    1.00    --   70.00  76.00 -59.59   26
 71  \w     44.00  70.00   1.00    1.00    --   74.00  76.00  -5.53   26
 72  \w     32.00  58.00   1.00    1.00    --   62.00  77.00  -4.20   26
 73  \w     19.00  44.00   1.00    1.00    --   50.00  81.00  21.30   25
 74  \w     19.00  44.00   1.00    1.00    --   50.00  80.00 -31.34   25
 75  \w     14.00  39.00   1.00    1.00    --   46.00  83.00 -66.37   25
 76  \w     25.00  51.00   1.00    1.00    --   54.00  77.00-133.48   26
 77  \w     -1.00  24.00   1.00    1.00    --   34.00  89.00  78.40   25
 78  \w     19.00  44.00   1.00    1.00    --   50.00  81.00  79.19   25
 79  \w     32.00  58.00   1.00    1.00    --   62.00  77.00 115.03   26
 80  \w     36.00  62.00   1.00    1.00    --   66.00  77.00 166.57   26
 81  \w     18.00  43.00   1.00    1.00    --   50.00  82.00 154.89   25
 82  \w    -64.00  29.00   1.00    1.00    --  -38.50  57.00   0.00   93
 83  \w    -54.00  -8.00   1.00    1.00    --  -38.50 -77.00 -30.00   46
 84  \w   -108.00 -19.00   1.00    1.00    --  -38.50 -37.00  30.00   89
 85  \w   -110.00 -57.00   1.00    1.00    --  -38.50 -77.00 -30.00   53
 86  \w    -99.00 -18.00   1.00    1.00    --  -38.50 -37.00-180.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0377159000
_diffrn_orient_matrix_UB_12      -0.1208544000
_diffrn_orient_matrix_UB_13      -0.0668428000
_diffrn_orient_matrix_UB_21      -0.0482207000
_diffrn_orient_matrix_UB_22      0.0181131000
_diffrn_orient_matrix_UB_23      0.0593419000
_diffrn_orient_matrix_UB_31      -0.0307108000
_diffrn_orient_matrix_UB_32      0.1197276000
_diffrn_orient_matrix_UB_33      -0.0762724000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29797
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.824
_diffrn_reflns_theta_min         3.932
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2881
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0654P)^2^+1.0121P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1103
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2635
_reflns_number_total             2881
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra05558k2.cif
_cod_data_source_block           mry2767a
_cod_database_code               7231323
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C11H20N6O
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.818
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H) groups
2. Restrained distances
 O1-H1B = O1-H1A
 0.86 with sigma of 0.02
3.a Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C9(H9A,H9B,H9C), C7(H7A,
 H7B,H7C), C8(H8A,H8B,H8C)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.880
_oxdiff_exptl_absorpt_empirical_full_min 0.711