#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:16:01 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180069 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/15/7051515.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7051515
loop_
_publ_author_name
'Katritzky, Alan R.'
'Yang, Hongfang'
'Zhang, Dazhi'
'Kirichenko, Kostyantyn'
'Smiglak, Marcin'
'Holbrey, John D.'
'Reichert, W. Matthew'
'Rogers, Robin D.'
_publ_section_title
;
 Strategies toward the design of energetic ionic liquids: nitro- and
 nitrile-substituted N,N′-dialkylimidazolium salts
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              349
_journal_paper_doi               10.1039/b509260d
_journal_volume                  30
_journal_year                    2006
_chemical_formula_sum            'C8 H10 N4 O4 S'
_chemical_formula_weight         258.26
_chemical_name_common
'1,3-dimethyl-4,5-dicyanoimidazolium methylsulfate'
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.568(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.4703(14)
_cell_length_b                   7.9000(13)
_cell_length_c                   8.9145(15)
_cell_measurement_reflns_used    822
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.28
_cell_measurement_theta_min      2.59
_cell_volume                     554.75(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2579
_diffrn_reflns_theta_full        23.29
_diffrn_reflns_theta_max         23.29
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8358
_exptl_absorpt_correction_type   sphere
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.21(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1552
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0717P)²+0.0628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0986
_reflns_number_gt                1438
_reflns_number_total             1552
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b509260d.txt
_cod_data_source_block           13b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7051515
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.26141(8) 1.37136(11) 0.35585(9) 0.0307(3) Uani 1 1 d . . .
O1 O 0.3120(6) 1.5210(6) 0.4298(6) 0.0348(12) Uani 0.50 1 d P A 1
O2 O 0.2197(7) 1.2348(6) 0.4506(6) 0.0382(13) Uani 0.50 1 d P A 1
O3 O 0.4300(6) 1.2779(6) 0.3394(6) 0.0329(12) Uani 0.50 1 d P A 1
O1A O 0.2200(6) 1.5283(7) 0.4345(6) 0.0339(12) Uani 0.50 1 d P A 2
O2A O 0.3303(7) 1.2451(6) 0.4715(6) 0.0370(13) Uani 0.50 1 d P A 2
O3A O 0.4213(6) 1.4594(6) 0.3223(5) 0.0265(10) Uani 0.50 1 d P A 2
O4 O 0.1395(3) 1.3553(5) 0.1968(3) 0.0516(8) Uani 1 1 d . A .
N1 N 0.1415(3) 0.8615(4) 0.3195(3) 0.0236(6) Uani 1 1 d . . .
N3 N 0.3299(3) 0.8523(4) 0.2099(3) 0.0226(6) Uani 1 1 d . . .
N4 N 0.2039(5) 0.6009(5) -0.1347(5) 0.0505(11) Uani 1 1 d . . .
N5 N -0.2140(5) 0.6174(5) 0.1078(4) 0.0391(9) Uani 1 1 d . . .
C2 C 0.2965(4) 0.9100(4) 0.3335(4) 0.0225(8) Uani 1 1 d . . .
H2A H 0.376(4) 0.982(4) 0.418(4) 0.008(7) Uiso 1 1 d . . .
C4 C 0.1918(4) 0.7600(4) 0.1118(4) 0.0245(8) Uani 1 1 d . . .
C5 C 0.0746(4) 0.7653(4) 0.1817(4) 0.0231(7) Uani 1 1 d . . .
C6 C 0.0653(6) 0.8886(8) 0.4412(5) 0.0395(10) Uani 1 1 d . . .
H6A H -0.032(5) 0.909(5) 0.395(5) 0.040(13) Uiso 1 1 d . . .
H6B H 0.114(6) 0.805(6) 0.520(6) 0.055(15) Uiso 1 1 d . . .
H6C H 0.138(8) 0.986(10) 0.495(8) 0.11(2) Uiso 1 1 d . . .
C7 C 0.4892(4) 0.8792(8) 0.1823(5) 0.0386(9) Uani 1 1 d . . .
H7A H 0.564(5) 0.938(5) 0.265(5) 0.037(11) Uiso 1 1 d . . .
H7B H 0.534(7) 0.767(7) 0.175(6) 0.070(16) Uiso 1 1 d . . .
H7C H 0.462(5) 0.936(5) 0.080(6) 0.045(12) Uiso 1 1 d . . .
C8 C 0.1938(4) 0.6727(5) -0.0277(4) 0.0324(8) Uani 1 1 d . . .
C9 C -0.0871(5) 0.6837(5) 0.1371(4) 0.0310(8) Uani 1 1 d . . .
C10 C 0.5035(4) 1.3554(8) 0.2468(4) 0.0468(10) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2A 107.1(2) . . ?
O1 S1 O4 123.5(3) . . ?
O2A S1 O4 128.7(3) . . ?
O1 S1 O2 117.2(3) . . ?
O2A S1 O2 35.7(2) . . ?
O4 S1 O2 105.3(3) . . ?
O1 S1 O1A 31.4(2) . . ?
O2A S1 O1A 110.2(3) . . ?
O4 S1 O1A 109.0(2) . . ?
O2 S1 O1A 100.70(19) . . ?
O1 S1 O3A 65.3(2) . . ?
O2A S1 O3A 106.7(3) . . ?
O4 S1 O3A 101.6(2) . . ?
O2 S1 O3A 142.3(2) . . ?
O1A S1 O3A 94.8(2) . . ?
O1 S1 O3 107.8(3) . . ?
O2A S1 O3 67.0(2) . . ?
O4 S1 O3 101.8(2) . . ?
O2 S1 O3 96.8(3) . . ?
O1A S1 O3 138.69(19) . . ?
O3A S1 O3 51.69(16) . . ?
C10 O3 S1 117.2(4) . . ?
C10 O3A S1 115.3(3) . . ?
C2 N1 C5 108.2(2) . . ?
C2 N1 C6 125.2(3) . . ?
C5 N1 C6 126.2(3) . . ?
C2 N3 C4 108.7(2) . . ?
C2 N3 C7 125.6(3) . . ?
C4 N3 C7 125.7(3) . . ?
N3 C2 N1 109.3(3) . . ?
C5 C4 N3 106.6(3) . . ?
C5 C4 C8 131.4(3) . . ?
N3 C4 C8 121.9(3) . . ?
C4 C5 N1 107.3(3) . . ?
C4 C5 C9 130.3(3) . . ?
N1 C5 C9 122.3(3) . . ?
N4 C8 C4 176.4(4) . . ?
N5 C9 C5 177.3(4) . . ?
O3 C10 O3A 63.2(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.345(5) . ?
S1 O2A 1.399(5) . ?
S1 O4 1.420(3) . ?
S1 O2 1.490(5) . ?
S1 O1A 1.527(5) . ?
S1 O3A 1.645(4) . ?
S1 O3 1.661(5) . ?
O3 C10 1.350(6) . ?
O3A C10 1.399(6) . ?
N1 C2 1.329(4) . ?
N1 C5 1.377(4) . ?
N1 C6 1.468(4) . ?
N3 C2 1.315(4) . ?
N3 C4 1.383(4) . ?
N3 C7 1.474(4) . ?
N4 C8 1.140(5) . ?
N5 C9 1.137(5) . ?
C4 C5 1.353(4) . ?
C4 C8 1.427(5) . ?
C5 C9 1.432(5) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2A O2A 0.98(3) 2.20(3) 2.888(6) 126(2) .
C2 H2A O1 0.98(3) 2.51(3) 3.328(6) 141(2) 2_646
C2 H2A O3 0.98(3) 2.53(3) 3.112(6) 118(2) .
C2 H2A O3A 0.98(3) 2.33(3) 3.144(6) 140(2) 2_646
C2 H2A O2 0.98(3) 2.47(3) 2.931(6) 108.2(19) .
C6 H6C O2 0.99(7) 2.17(8) 3.019(8) 143(6) .
C6 H6A N4 0.79(4) 2.70(4) 3.301(7) 134(4) 2
C7 H7A O1 0.91(4) 2.61(4) 3.430(7) 150(3) 2_646
C7 H7C N5 0.96(5) 2.59(4) 3.351(6) 136(3) 2
C7 H7B N5 0.97(6) 2.69(6) 3.502(6) 141(4) 1_655
C2 H2A O2A 0.98(3) 2.20(3) 2.888(6) 126(2) .
C6 H6B O1A 0.94(5) 2.59(5) 3.144(8) 118(4) 1_545
C7 H7A O2A 0.91(4) 2.67(4) 3.084(7) 109(3) 2_646
C6 H6C O2A 0.99(7) 2.67(7) 3.549(8) 147(5) .
