Peralkylated imidazolium carbonate ionic liquids: synthesis using dimethyl carbonate, reactivity and structure
Maton, C.; Van Hecke, K.; Stevens, C. V.; New J. Chem. 39 (2015) 461–; doi:10.1039/C4NJ01301H

data_7054487
_publ_section_title
;
 Peralkylated imidazolium carbonate ionic liquids: synthesis using
 dimethyl carbonate, reactivity and structure
;
_journal_issue                   1
_journal_name_full               'New J. Chem.'
_journal_page_first              461
_journal_paper_doi               10.1039/C4NJ01301H
_journal_volume                  39
_journal_year                    2015
_chemical_formula_moiety         'C8 H15 N2, C H O3'
_chemical_formula_sum            'C9 H16 N2 O3'
_chemical_formula_weight         200.24
_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             2013-05-01
_audit_creation_method
;
  Olex2 1.2
  (compiled 2013.04.25 svn.r2679, GUI svn.r4466)
;
_cell_angle_alpha                74.586(4)
_cell_angle_beta                 80.157(4)
_cell_angle_gamma                83.657(3)
_cell_formula_units_Z            2
_cell_length_a                   6.9516(3)
_cell_length_b                   8.1294(3)
_cell_length_c                   9.6234(4)
_cell_measurement_reflns_used    5019
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.9680
_cell_measurement_theta_min      4.7940
_cell_volume                     515.35(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.4839
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.9973
_diffrn_measurement_details
;
  1 omega  -63.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048  -45.0000  -33.0000 47

  2 omega  -54.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048   45.0000  -63.0000 84

  3 omega   65.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048   45.0000  116.0000 25

  4 omega  -31.00   -4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048  -45.0000   63.0000 27

  5 omega   -1.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048  -45.0000   63.0000 43

  6 omega  -57.00  -25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -45.0000 -116.0000 32

  7 omega -115.00  -63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -45.0000 -116.0000 52

  8 omega   84.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000  116.0000 25

  9 omega   36.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -45.0000  146.0000 62

 10 omega  127.00  154.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000  116.0000 27

 11 omega  106.00  131.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000   33.0000 25

 12 omega   52.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -45.0000   63.0000 26

 13 omega -113.00  -81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048  -57.0000  150.0000 32

 14 omega  -55.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8048  -57.0000  150.0000 41

 15 omega   24.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048 -125.0000   30.0000 73

 16 omega   41.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8048   45.0000   33.0000 25

 17 omega    6.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   88.0000   34.1948 25

 18 omega  -92.00  -67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -45.0000  -33.0000 25

 19 omega  -55.00   20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   45.0000 -146.0000 75

 20 omega   21.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000 -124.9277 25

 21 omega   22.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000  -65.5444 27

 22 omega   21.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000 -159.5750 25

 23 omega   20.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000  124.1860 25

 24 omega   29.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000   58.0167 27

 25 omega   30.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000  -18.6978 26

 26 omega   30.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   75.0000  153.4449 103

 27 omega   34.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000 -121.9961 26

 28 omega   37.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000  -93.8165 29

 29 omega   40.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000   72.7692 26

 30 omega  115.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000   72.7692 26

 31 omega   47.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   64.0000   21.9531 27

 32 omega   43.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   67.0000  -52.8924 27

 33 omega   44.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   69.0000  -13.4032 26

 34 omega   47.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   52.0000 -155.7302 36

 35 omega   49.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   61.0000   53.6754 25

 36 omega   53.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   70.0000   77.3764 38

 37 omega  118.00  143.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   46.0000  -17.3513 25

 38 omega   75.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   46.0000  -17.3513 26

 39 omega   79.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000 -120.0000 95

 40 omega   83.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000  120.0000 40

 41 omega   38.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000  -90.0000 65

 42 omega   81.00  136.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000    0.0000 55

 43 omega   90.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000 -120.0000 26

 44 omega   87.00  134.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -61.0000 -120.0000 47

 45 omega  126.00  172.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000 -150.0000 46

 46 omega   86.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000  -60.0000 91

 47 omega   32.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000 -180.0000 63

 48 omega   85.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000    0.0000 26

 49 omega  118.00  166.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000  150.0000 48

 50 omega   78.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000  150.0000 34

 51 omega   81.00  154.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000  120.0000 73

 52 omega   81.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000 -150.0000 35

 53 omega   81.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000  -60.0000 27

 54 omega   81.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000 -150.0000 25

 55 omega   37.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -94.0000   90.0000 69

 56 omega   83.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000 -150.0000 27

 57 omega   79.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   77.0000   60.0000 99

 58 omega   82.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000   60.0000 26

 59 omega   82.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   61.0000   30.0000 81

 60 omega   37.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316 -125.0000   90.0000 76
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1531496000
_diffrn_orient_matrix_UB_12      0.0600133000
_diffrn_orient_matrix_UB_13      0.0707049000
_diffrn_orient_matrix_UB_21      0.1590084000
_diffrn_orient_matrix_UB_22      -0.1187326000
_diffrn_orient_matrix_UB_23      -0.0634686000
_diffrn_orient_matrix_UB_31      0.0457268000
_diffrn_orient_matrix_UB_32      0.1453458000
_diffrn_orient_matrix_UB_33      -0.1384308000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8198
_diffrn_reflns_theta_full        72.06
_diffrn_reflns_theta_max         72.06
_diffrn_reflns_theta_min         4.82
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.806
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
   model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.2834
_exptl_crystal_size_mid          0.1519
_exptl_crystal_size_min          0.1137
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.0911P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1125
_reflns_number_gt                1822
_reflns_number_total             2005
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4nj01301h2.cif
_cod_data_source_block           cs006
_cod_depositor_comments
'Adding full bibliography for 7054487--7054489.cif.'
_cod_database_code               7054487
_chemical_oxdiff_formula         'C9 H16 N2 O3'
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates and stretchable bonds:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates and stretchable bonds:
 C1(H1)
2.c Idealised Me refined as rotating group with stretchable bonds:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C)
2.d Idealised tetrahedral OH refined as rotating group with stretchable bonds:
 O1(H1A)
;