#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/71/2017117.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_2017117
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 + , C6 H9 O4 -, H2 O'
_chemical_formula_sum            'C10 H18 N2 O5'
_chemical_formula_weight         246.26
_chemical_name_systematic
;
2-methylimidazolium hydrogen adipate monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL97
_cell_angle_alpha                96.8800(10)
_cell_angle_beta                 92.7940(10)
_cell_angle_gamma                106.6110(10)
_cell_formula_units_Z            2
_cell_length_a                   4.9383(4)
_cell_length_b                   8.0682(6)
_cell_length_c                   16.6840(13)
_cell_measurement_reflns_used    2128
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.47
_cell_volume                     630.00(8)
_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      297(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6477
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.212
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2421
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0495
_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)+(0.0972P)²+0.0502P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1592
_reflns_number_gt                1905
_reflns_number_total             2421
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3296.cif
_cod_data_source_block           III
_cod_database_code               2017117
_cod_database_fobs_code          2017117
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.2664(4) 0.9849(2) 0.26207(12) 0.0407(5) Uani d . 1 . .
C C2 0.2364(4) 0.8946(2) 0.38189(13) 0.0486(5) Uani d . 1 . .
H H2 0.1930 0.8843 0.4350 0.058 Uiso calc R 1 . .
C C3 0.3761(5) 0.8038(3) 0.33743(14) 0.0530(5) Uani d . 1 . .
H H3 0.4482 0.7174 0.3537 0.064 Uiso calc R 1 . .
C C4 0.2385(5) 1.0795(3) 0.19338(13) 0.0579(6) Uani d . 1 . .
H H4A 0.0583 1.0243 0.1630 0.087 Uiso calc R 1 . .
H H4B 0.3880 1.0775 0.1589 0.087 Uiso calc R 1 . .
H H4C 0.2510 1.1983 0.2134 0.087 Uiso calc R 1 . .
C C5 0.7289(4) 0.5974(2) 0.16367(10) 0.0371(4) Uani d . 1 . .
C C6 0.8623(5) 0.4902(3) 0.10637(11) 0.0445(5) Uani d . 1 . .
H H6A 1.0337 0.4815 0.1342 0.053 Uiso calc R 1 . .
H H6B 0.7327 0.3730 0.0939 0.053 Uiso calc R 1 . .
C C7 0.9369(4) 0.5593(2) 0.02766(11) 0.0400(5) Uani d . 1 . .
H H7A 1.0723 0.6748 0.0393 0.048 Uiso calc R 1 . .
H H7B 0.7674 0.5703 -0.0004 0.048 Uiso calc R 1 . .
C C8 0.8109(3) 0.3255(2) 0.36414(11) 0.0341(4) Uani d . 1 . .
C C9 0.6488(4) 0.4454(2) 0.39884(10) 0.0333(4) Uani d . 1 . .
H H9A 0.4761 0.4240 0.3639 0.040 Uiso calc R 1 . .
H H9B 0.7616 0.5648 0.3970 0.040 Uiso calc R 1 . .
C C10 0.5691(4) 0.4305(2) 0.48431(10) 0.0326(4) Uani d . 1 . .
H H10A 0.7378 0.4424 0.5195 0.039 Uiso calc R 1 . .
H H10B 0.4386 0.3156 0.4859 0.039 Uiso calc R 1 . .
N N1 0.3944(4) 0.8610(2) 0.26335(11) 0.0463(4) Uani d D 1 . .
H H1 0.472(4) 0.821(3) 0.2210(11) 0.056 Uiso d D 1 . .
N N2 0.1689(3) 1.0066(2) 0.33376(10) 0.0428(4) Uani d D 1 . .
H H2A 0.076(4) 1.086(2) 0.3508(12) 0.051 Uiso d D 1 . .
O O1 0.6446(3) 0.71668(17) 0.14081(8) 0.0495(4) Uani d . 1 . .
O O2 0.7027(3) 0.5613(2) 0.23510(8) 0.0565(4) Uani d . 1 . .
H H2B 0.795(5) 0.453(3) 0.2611(15) 0.085 Uiso d . 1 . .
O O3 0.8821(3) 0.33834(18) 0.29100(8) 0.0516(4) Uani d . 1 . .
O O4 0.8761(3) 0.22082(16) 0.40353(8) 0.0445(4) Uani d . 1 . .
O O5 0.7220(4) 0.9398(4) 0.01894(16) 0.0995(8) Uani d D 1 . .
H H5D 0.699(9) 0.876(5) 0.053(2) 0.149 Uiso d D 1 . .
H H5E 0.610(13) 0.998(8) 0.018(4) 0.149 Uiso d PD 0.50 . .
H H5F 0.870(9) 0.964(11) 0.001(4) 0.149 Uiso d PD 0.50 . .
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'
O O 0.0106 0.0060 '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'
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 . . 107.10(18) no
N2 C1 C4 . . 126.71(18) no
N1 C1 C4 . . 126.18(18) no
C3 C2 N2 . . 106.48(18) no
C3 C2 H2 . . 126.8 no
N2 C2 H2 . . 126.8 no
C2 C3 N1 . . 107.48(19) no
C2 C3 H3 . . 126.3 no
N1 C3 H3 . . 126.3 no
C1 C4 H4A . . 109.5 no
C1 C4 H4B . . 109.5 no
H4A C4 H4B . . 109.5 no
C1 C4 H4C . . 109.5 no
H4A C4 H4C . . 109.5 no
H4B C4 H4C . . 109.5 no
O1 C5 O2 . . 120.97(16) no
O1 C5 C6 . . 120.80(15) no
O2 C5 C6 . . 118.23(16) no
C7 C6 C5 . . 115.71(15) no
C7 C6 H6A . . 108.4 no
C5 C6 H6A . . 108.4 no
C7 C6 H6B . . 108.4 no
C5 C6 H6B . . 108.4 no
H6A C6 H6B . . 107.4 no
C6 C7 C7 . 2_765 112.34(18) no
C6 C7 H7A . . 109.1 no
C7 C7 H7A 2_765 . 109.1 no
C6 C7 H7B . . 109.1 no
C7 C7 H7B 2_765 . 109.1 no
H7A C7 H7B . . 107.9 no
O4 C8 O3 . . 121.13(15) no
O4 C8 C9 . . 121.84(16) no
O3 C8 C9 . . 117.03(14) no
C8 C9 C10 . . 116.58(14) no
C8 C9 H9A . . 108.1 no
C10 C9 H9A . . 108.1 no
C8 C9 H9B . . 108.1 no
C10 C9 H9B . . 108.2 no
H9A C9 H9B . . 107.3 no
C9 C10 C10 . 2_666 111.84(17) no
C9 C10 H10A . . 109.2 no
C10 C10 H10A 2_666 . 109.2 no
C9 C10 H10B . . 109.3 no
C10 C10 H10B 2_666 . 109.2 no
H10A C10 H10B . . 107.9 no
C1 N1 C3 . . 109.24(17) no
C1 N1 H1 . . 123.6(14) no
C3 N1 H1 . . 127.1(14) no
C1 N2 C2 . . 109.70(16) no
C1 N2 H2A . . 126.5(13) no
C2 N2 H2A . . 123.8(13) no
C5 O2 H2B . . 123.0(13) no
C8 O3 H2B . . 111.4(12) no
H5D O5 H5E . . 114(3) no
H5D O5 H5F . . 118(4) no
H5E O5 H5F . . 125(6) 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 . 1.322(2) no
C1 N1 . 1.329(2) no
C1 C4 . 1.472(3) no
C2 C3 . 1.331(3) no
C2 N2 . 1.376(3) no
C2 H2 . 0.9300 no
C3 N1 . 1.368(3) no
C3 H3 . 0.9300 no
C4 H4A . 0.9600 no
C4 H4B . 0.9600 no
C4 H4C . 0.9600 no
C5 O1 . 1.244(2) no
C5 O2 . 1.264(2) no
C5 C6 . 1.511(2) no
C6 C7 . 1.509(3) no
C6 H6A . 0.9700 no
C6 H6B . 0.9700 no
C7 C7 2_765 1.530(3) no
C7 H7A . 0.9700 no
C7 H7B . 0.9700 no
C8 O4 . 1.232(2) no
C8 O3 . 1.294(2) no
C8 C9 . 1.505(2) no
C9 C10 . 1.507(2) no
C9 H9A . 0.9700 no
C9 H9B . 0.9700 no
C10 C10 2_666 1.526(3) no
C10 H10A . 0.9700 no
C10 H10B . 0.9700 no
N1 H1 . 0.890(15) no
N2 H2A . 0.915(15) no
O2 H2B . 1.21(3) no
O3 H2B . 1.26(3) no
O5 H5D . 0.80(4) no
O5 H5E . 0.82(2) no
O5 H5F . 0.785(19) 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 O1 . 0.889(15) 1.867(16) 2.751(2) 172(2) yes
N2 H2A O4 1_465 0.913(15) 1.846(16) 2.7464(19) 168.4(19) yes
O2 H2B O3 . 1.22(2) 1.25(2) 2.4747(19) 177(2) yes
O5 H5D O1 . 0.80(4) 2.04(4) 2.843(2) 178(4) yes
O5 H5F O5 2_775 0.785(19) 2.01(3) 2.770(4) 162(7) yes
O5 H5E O5 2_675 0.825(19) 1.93(3) 2.715(4) 157(7) 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 . . . . 0.3(2) no
O1 C5 C6 C7 . . . . 11.5(3) no
O2 C5 C6 C7 . . . . -169.22(17) no
C5 C6 C7 C7 . . . 2_765 -178.4(2) no
O4 C8 C9 C10 . . . . -0.2(2) no
O3 C8 C9 C10 . . . . -179.49(14) no
C8 C9 C10 C10 . . . 2_666 174.59(17) no
N2 C1 N1 C3 . . . . 0.1(2) no
C4 C1 N1 C3 . . . . -179.76(19) no
C2 C3 N1 C1 . . . . -0.3(2) no
N1 C1 N2 C2 . . . . 0.1(2) no
C4 C1 N2 C2 . . . . 179.98(18) no
C3 C2 N2 C1 . . . . -0.3(2) no
