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_7054488
_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, Cl'
_chemical_formula_sum            'C8 H15 Cl N2'
_chemical_formula_weight         174.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-05-02
_audit_creation_method
;
  Olex2 1.2
  (compiled 2013.04.25 svn.r2679, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.572(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.77997(17)
_cell_length_b                   14.4971(4)
_cell_length_c                   9.8785(3)
_cell_measurement_reflns_used    2253
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.9330
_cell_measurement_theta_min      5.5000
_cell_volume                     954.47(5)
_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 0.9994
_diffrn_measured_fraction_theta_max 0.9994
_diffrn_measurement_details
;
  1 omega -116.00  -90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -54.0000 -157.0000 26

  2 omega  -71.00  -31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -54.0000 -157.0000 40

  3 omega   61.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -54.0000   22.0000 50

  4 omega   75.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -54.0000 -166.0000 30

  5 omega   82.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   54.0000  157.0000 29

  6 omega  120.00  164.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   54.0000  157.0000 44

  7 omega   37.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -54.0000 -166.0000 34

  8 omega -125.00  -84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000    0.0000 41

  9 omega  -60.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   54.0000  166.0000 49

 10 omega -113.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000  -90.0000 31

 11 omega -122.00  -81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000  -94.0000 -180.0000 41

 12 omega  -56.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.5000   54.0000  -22.0000 38

 13 omega   36.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -45.0000  120.0000 60

 14 omega   71.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -45.0000  -90.0000 28

 15 omega   41.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316  -45.0000  -90.0000 26

 16 omega  150.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000  -90.0000 26

 17 omega   86.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   45.0000  -90.0000 25

 18 omega   81.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   30.0000   90.0000 96

 19 omega  106.00  131.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.1316   54.0000  -13.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.2163932000
_diffrn_orient_matrix_UB_12      0.0054178000
_diffrn_orient_matrix_UB_13      0.0273276000
_diffrn_orient_matrix_UB_21      -0.0689612000
_diffrn_orient_matrix_UB_22      -0.0684779000
_diffrn_orient_matrix_UB_23      -0.1186976000
_diffrn_orient_matrix_UB_31      0.0437572000
_diffrn_orient_matrix_UB_32      -0.0810651000
_diffrn_orient_matrix_UB_33      0.1014973000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4198
_diffrn_reflns_theta_full        70.07
_diffrn_reflns_theta_max         70.07
_diffrn_reflns_theta_min         5.48
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.066
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.953
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.3009
_exptl_crystal_size_mid          0.1526
_exptl_crystal_size_min          0.1152
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0284(19)
_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   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0628P)^2^+0.0806P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1064
_reflns_number_gt                1593
_reflns_number_total             1807
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4nj01301h2.cif
_cod_data_source_block           cs007
_cod_depositor_comments
'Adding full bibliography for 7054487--7054489.cif.'
_cod_original_cell_volume        954.48(5)
_cod_database_code               7054488
_chemical_oxdiff_formula         'C8 H15 Cl N2'
_reflns_odcompleteness_completeness 99.94
_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
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)
;