#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/71/2017115.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2017115
loop_
_publ_author_name
'Meng, Xiang-Gao'
'Cheng, Cui-Xia'
'Yan, Gang'
_publ_section_title
;
 A two-dimensional network in the molecular salt 2-methylimidazolium
 hydrogen glutarate, and three-dimensional networks in the salts
 2-methylimidazolium hydrogen succinate and 2-methylimidazolium
 hydrogen adipate monohydrate
;
_journal_coeditor_code           SK3296
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o217
_journal_page_last               o221
_journal_paper_doi               10.1107/S0108270109012530
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C4 H7 N2 + , C4 H5 O4 -'
_chemical_formula_sum            'C8 H12 N2 O4'
_chemical_formula_weight         200.20
_chemical_name_systematic
;
2-Methylimidazolium hydrogen succinate
;
_space_group_IT_number           36
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8017(10)
_cell_length_b                   8.1580(11)
_cell_length_c                   17.438(2)
_cell_measurement_reflns_used    2108
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.61
_cell_measurement_theta_min      2.34
_cell_volume                     967.6(2)
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '0.3° wide ω exposures'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed Siemens Mo tube'
_diffrn_radiation_type           'Mo k\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5389
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         654
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0344
_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/[σ²(Fo²)+(0.0665P)²+0.0213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0919
_reflns_number_gt                573
_reflns_number_total             654
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3296.cif
_cod_data_source_block           I
_cod_database_code               2017115
_cod_database_fobs_code          2017115
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5457(4) 0.0023(4) 0.7332(2) 0.0344(11) Uani d P 0.50 . -1
C C2 0.2982(7) 0.1668(6) 0.7569(3) 0.0504(11) Uani d P 0.50 . -1
H H6 0.2088 0.2323 0.7832 0.061 Uiso calc PR 0.50 . -1
C C3 0.3004(7) 0.1383(5) 0.6818(3) 0.0497(10) Uani d P 0.50 . -1
H H7 0.2133 0.1799 0.6455 0.060 Uiso calc PR 0.50 . -1
C C4 0.7232(7) -0.1032(4) 0.74288(13) 0.0603(12) Uani d P 0.50 A -1
H H4A 0.8296 -0.0385 0.7627 0.090 Uiso calc PR 0.50 A -1
H H4B 0.7601 -0.1484 0.6941 0.090 Uiso calc PR 0.50 A -1
H H4C 0.6942 -0.1905 0.7780 0.090 Uiso calc PR 0.50 A -1
C C5 0.5000(8) 0.67258(16) 0.96057(13) 0.0312(6) Uani d SR 1 . .
C C6 0.5000(8) 0.51001(15) 1.00107(11) 0.0329(6) Uani d SR 1 . .
H H6A 0.3848 0.5034 1.0337 0.040 Uiso calc PR 0.50 . .
H H6B 0.6152 0.5034 1.0337 0.040 Uiso calc PR 0.50 . .
C C7 0.5000(8) 0.36551(16) 0.94673(10) 0.0319(6) Uani d SR 1 . .
H H7A 0.6151 0.3729 0.9141 0.038 Uiso calc PR 0.50 . .
H H7B 0.3849 0.3729 0.9141 0.038 Uiso calc PR 0.50 . .
C C8 0.5000(8) 0.19911(18) 0.98588(10) 0.0269(5) Uani d SR 1 . .
N N1 0.4561(6) 0.0359(4) 0.66822(18) 0.0413(15) Uani d PD 0.50 . .
H H1 0.470(8) -0.013(5) 0.6247(16) 0.050 Uiso d PD 0.50 . .
N N2 0.4518(5) 0.0818(4) 0.78840(19) 0.0409(12) Uani d PD 0.50 . .
H H2 0.475(9) 0.079(4) 0.8376(13) 0.049 Uiso d PD 0.50 . .
O O1 0.5000 0.7967(2) 1.00811(13) 0.0503(6) Uani d SD 1 . .
H H1A 0.5000 0.878(4) 0.982(2) 0.075 Uiso d SD 1 . .
O O2 0.5000 0.6891(3) 0.89195(12) 0.0536(6) Uani d S 1 . .
O O3 0.5000 0.1882(2) 1.05627(11) 0.0442(5) Uani d S 1 . .
O O4 0.5000 0.0755(2) 0.94090(11) 0.0418(5) Uani d S 1 . .
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N1 3_655 3_655 132.4(4) no
N2 C1 N1 3_655 . 127.2(4) no
N1 C1 N2 3_655 . 125.9(4) no
N1 C1 N2 . . 107.5(3) no
N2 C1 C4 3_655 . 102.5(3) no
N1 C1 C4 3_655 . 104.7(3) no
N1 C1 C4 . . 126.3(3) no
N2 C1 C4 . . 126.2(3) no
C3 C2 N2 . . 107.3(4) no
C3 C2 N2 . 3_655 102.1(3) no
C3 C2 H6 . . 126.3 no
N2 C2 H6 . . 126.3 no
N2 C2 H6 3_655 . 130.3 no
C2 C3 N1 . . 106.6(4) no
C2 C3 N1 . 3_655 102.3(3) no
C2 C3 H7 . . 126.7 no
N1 C3 H7 . . 126.7 no
N1 C3 H7 3_655 . 129.9 no
O2 C5 O1 . . 122.89(17) no
O2 C5 C6 . . 124.44(13) no
O1 C5 C6 . . 112.66(12) no
C5 C6 C7 . . 113.17(16) no
C5 C6 H6A . . 108.9 no
C7 C6 H6A . . 108.9 no
C5 C6 H6B . . 108.9 no
C7 C6 H6B . . 108.9 no
H6A C6 H6B . . 107.8 no
C6 C7 C8 . . 114.51(14) no
C6 C7 H7A . . 108.6 no
C8 C7 H7A . . 108.6 no
C6 C7 H7B . . 108.6 no
C8 C7 H7B . . 108.6 no
H7A C7 H7B . . 107.6 no
O3 C8 O4 . . 123.73(16) no
O3 C8 C7 . . 120.83(13) no
O4 C8 C7 . . 115.43(12) no
N1 N1 C3 3_655 . 140.6(3) no
C1 N1 C3 . . 109.7(3) no
C3 N1 C3 . 3_655 113.0(4) no
C1 N1 H1 3_655 . 138(3) no
C1 N1 H1 . . 127(3) no
C3 N1 H1 . . 121(3) no
C3 N1 H1 3_655 . 103(3) no
N2 N2 C2 3_655 . 139.8(3) no
C1 N2 C2 . . 108.9(3) no
C2 N2 C2 . 3_655 112.3(4) no
C1 N2 H2 3_655 . 143(3) no
C1 N2 H2 . . 128(3) no
C2 N2 H2 . . 123(4) no
C2 N2 H2 3_655 . 97(4) no
C5 O1 H1A . . 106(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 3_655 1.160(5) no
C1 N1 3_655 1.166(5) no
C1 N1 . 1.316(5) no
C1 N2 . 1.324(5) no
C1 C4 . 1.492(5) no
C2 C3 . 1.331(6) no
C2 N2 . 1.369(5) no
C2 N2 3_655 1.917(5) no
C2 H6 . 0.9300 no
C3 N1 . 1.370(6) no
C3 N1 3_655 1.871(6) no
C3 H7 . 0.9300 no
C4 H4A . 0.9600 no
C4 H4B . 0.9600 no
C4 H4C . 0.9600 no
C5 O2 . 1.204(3) no
C5 O1 . 1.309(3) no
C5 C6 . 1.503(2) no
C6 C7 . 1.513(2) no
C6 H6A . 0.9700 no
C6 H6B . 0.9700 no
C7 C8 . 1.520(2) no
C7 H7A . 0.9700 no
C7 H7B . 0.9700 no
C8 O3 . 1.231(3) no
C8 O4 . 1.278(2) no
N1 N1 3_655 0.598(8) no
N1 C1 3_655 1.166(5) no
N1 C3 3_655 1.871(6) no
N1 H1 . 0.86(2) no
N2 N2 3_655 0.655(6) no
N2 C1 3_655 1.160(5) no
N2 C2 3_655 1.917(5) no
N2 H2 . 0.87(2) no
O1 H1A . 0.81(2) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O3 2_654 0.86(2) 1.87(2) 2.691(4) 158(4) yes
N2 H2 O4 . 0.87(2) 1.81(2) 2.680(4) 175(6) yes
O1 H1A O4 1_565 0.81(2) 1.76(2) 2.558(3) 169(5) yes
C2 H6 O2 5_445 0.93 2.40 3.113(5) 133.8 yes
C3 H7 O3 6_554 0.93 2.38 3.311(5) 174.5 yes
C4 H4C O2 1_545 0.96 2.58 3.455(5) 151.5 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N2 C2 C3 N1 . . . . 0.0(5) no
N2 C2 C3 N1 3_655 . . . 12.0(5) no
N2 C2 C3 N1 . . . 3_655 -11.2(5) no
N2 C2 C3 N1 3_655 . . 3_655 0.8(4) no
O2 C5 C6 C7 . . . . 0.0(3) no
O1 C5 C6 C7 . . . . 180.0(3) no
C5 C6 C7 C8 . . . . 180.0 no
C6 C7 C8 O3 . . . . 0.0(3) no
C6 C7 C8 O4 . . . . 180.0(3) no
N2 C1 N1 N1 3_655 . . 3_655 112.1(4) no
N2 C1 N1 N1 . . . 3_655 137.3(3) no
C4 C1 N1 N1 . . . 3_655 -41.5(3) no
N2 C1 N1 C1 3_655 . . 3_655 -67.9(4) no
N1 C1 N1 C1 3_655 . . 3_655 179.999(4) no
N2 C1 N1 C1 . . . 3_655 -42.7(3) no
C4 C1 N1 C1 . . . 3_655 138.5(3) no
N2 C1 N1 C3 3_655 . . . -25.6(6) no
N1 C1 N1 C3 3_655 . . . -137.7(3) no
N2 C1 N1 C3 . . . . -0.4(4) no
C4 C1 N1 C3 . . . . -179.2(4) no
N2 C1 N1 C3 3_655 . . 3_655 81.2(4) no
N1 C1 N1 C3 3_655 . . 3_655 -30.9(2) no
N2 C1 N1 C3 . . . 3_655 106.5(3) no
C4 C1 N1 C3 . . . 3_655 -72.4(4) no
C2 C3 N1 N1 . . . 3_655 -69.9(5) no
C2 C3 N1 C1 . . . 3_655 18.8(4) no
N1 C3 N1 C1 3_655 . . 3_655 88.7(4) no
C2 C3 N1 C1 . . . . 0.2(5) no
N1 C3 N1 C1 3_655 . . . 70.1(4) no
C2 C3 N1 C3 . . . 3_655 -69.9(5) no
N1 C3 N1 C3 3_655 . . 3_655 0.001(2) no
N1 C1 N2 N2 3_655 . . 3_655 -114.4(4) no
N1 C1 N2 N2 . . . 3_655 -136.7(3) no
C4 C1 N2 N2 . . . 3_655 42.1(3) no
N2 C1 N2 C1 3_655 . . 3_655 180.001(3) no
N1 C1 N2 C1 3_655 . . 3_655 65.6(4) no
N1 C1 N2 C1 . . . 3_655 43.3(3) no
C4 C1 N2 C1 . . . 3_655 -137.9(3) no
N2 C1 N2 C2 3_655 . . . 137.1(3) no
N1 C1 N2 C2 3_655 . . . 22.7(6) no
N1 C1 N2 C2 . . . . 0.4(4) no
C4 C1 N2 C2 . . . . 179.2(4) no
N2 C1 N2 C2 3_655 . . 3_655 31.2(2) no
N1 C1 N2 C2 3_655 . . 3_655 -83.2(4) no
N1 C1 N2 C2 . . . 3_655 -105.5(3) no
C4 C1 N2 C2 . . . 3_655 73.3(4) no
C3 C2 N2 N2 . . . 3_655 67.2(5) no
C3 C2 N2 C1 . . . 3_655 -18.9(5) no
N2 C2 N2 C1 3_655 . . 3_655 -86.1(3) no
C3 C2 N2 C1 . . . . -0.2(5) no
N2 C2 N2 C1 3_655 . . . -67.5(3) no
C3 C2 N2 C2 . . . 3_655 67.2(5) no
N2 C2 N2 C2 3_655 . . 3_655 -0.003(4) no
