#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/26/8102687.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_8102687
loop_
_publ_author_name
'Jian-Ge Wang'
'Jian-Hua Qin'
_publ_section_title
;
 Crystal structure of dimethylamonium hydrogen
 2-propyl-4,5-imidazoledicarboxylate, [C2H8N][C8H9N2O4]
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              325
_journal_volume                  225
_journal_year                    2010
_chemical_formula_sum            'C10 H17 N3 O4'
_chemical_formula_weight         243.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 112.015(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1790(14)
_cell_length_b                   15.203(2)
_cell_length_c                   9.2891(14)
_cell_measurement_reflns_used    1510
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.39
_cell_measurement_theta_min      2.66
_cell_volume                     1201.8(3)
_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      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10454
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_correction_T_min  0.9728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2749
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0467
_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)+(0.0497P)²+0.1296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1194
_reflns_number_gt                1665
_reflns_number_total             2749
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2952.cff
_cod_data_source_block           bb
_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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        1201.7(3)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               8102687
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
O1 O 0.36617(15) 1.02223(9) 0.04975(16) 0.0526(4) Uani 1 1 d . . .
O2 O 0.14501(15) 1.09441(9) 0.00473(15) 0.0475(4) Uani 1 1 d . . .
H2 H 0.0812 1.1009 0.0464 0.071 Uiso 1 1 calc R . .
O3 O -0.04522(15) 1.11903(9) 0.12755(16) 0.0517(4) Uani 1 1 d . . .
O4 O -0.08178(18) 1.07398(11) 0.33847(18) 0.0706(5) Uani 1 1 d . . .
N1 N 0.35395(16) 0.94255(9) 0.31572(16) 0.0360(4) Uani 1 1 d . . .
N2 N 0.17872(16) 0.96398(9) 0.42134(16) 0.0376(4) Uani 1 1 d . . .
H2D H 0.1316 0.9595 0.4854 0.045 Uiso 1 1 calc R . .
N3 N 0.57305(18) 0.87988(11) 0.17314(18) 0.0463(4) Uani 1 1 d . . .
H3A H 0.5210 0.9017 0.2302 0.056 Uiso 1 1 calc R . .
H3B H 0.5901 0.9245 0.1177 0.056 Uiso 1 1 calc R . .
C1 C 0.6143(2) 0.75451(14) 0.6902(2) 0.0535(6) Uani 1 1 d . . .
H1A H 0.6501 0.7886 0.7841 0.080 Uiso 1 1 calc R . .
H1B H 0.7025 0.7266 0.6774 0.080 Uiso 1 1 calc R . .
H1C H 0.5418 0.7105 0.6960 0.080 Uiso 1 1 calc R . .
C2 C 0.5329(2) 0.81448(13) 0.5527(2) 0.0454(5) Uani 1 1 d . . .
H2A H 0.6076 0.8579 0.5460 0.054 Uiso 1 1 calc R . .
H2B H 0.4991 0.7799 0.4581 0.054 Uiso 1 1 calc R . .
C3 C 0.3935(2) 0.86087(13) 0.5636(2) 0.0454(5) Uani 1 1 d . . .
H3C H 0.3188 0.8171 0.5687 0.054 Uiso 1 1 calc R . .
H3D H 0.4277 0.8940 0.6599 0.054 Uiso 1 1 calc R . .
C4 C 0.3118(2) 0.92185(12) 0.4332(2) 0.0355(4) Uani 1 1 d . . .
C5 C -0.0090(2) 1.07264(13) 0.2509(2) 0.0434(5) Uani 1 1 d . . .
C6 C 0.13093(19) 1.01503(11) 0.29070(19) 0.0344(4) Uani 1 1 d . . .
C7 C 0.24112(19) 1.00121(11) 0.22556(19) 0.0336(4) Uani 1 1 d . . .
C8 C 0.2534(2) 1.04032(12) 0.0854(2) 0.0372(4) Uani 1 1 d . . .
C9 C 0.7253(3) 0.84541(18) 0.2782(3) 0.0715(7) Uani 1 1 d . . .
H9A H 0.7086 0.7943 0.3307 0.107 Uiso 1 1 calc R . .
H9B H 0.7787 0.8896 0.3533 0.107 Uiso 1 1 calc R . .
H9C H 0.7880 0.8299 0.2194 0.107 Uiso 1 1 calc R . .
C10 C 0.4738(3) 0.81377(16) 0.0656(3) 0.0733(7) Uani 1 1 d . . .
H10A H 0.5253 0.7929 -0.0007 0.110 Uiso 1 1 calc R . .
H10B H 0.3748 0.8397 0.0036 0.110 Uiso 1 1 calc R . .
H10C H 0.4565 0.7654 0.1237 0.110 Uiso 1 1 calc R . .
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'
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
C8 O2 H2 109.5 . . ?
C4 N1 C7 105.55(14) . . ?
C4 N2 C6 108.77(14) . . ?
C4 N2 H2D 125.6 . . ?
C6 N2 H2D 125.6 . . ?
C10 N3 C9 113.63(18) . . ?
C10 N3 H3A 108.8 . . ?
C9 N3 H3A 108.8 . . ?
C10 N3 H3B 108.8 . . ?
C9 N3 H3B 108.8 . . ?
H3A N3 H3B 107.7 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 112.89(17) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 114.91(15) . . ?
C4 C3 H3C 108.5 . . ?
C2 C3 H3C 108.5 . . ?
C4 C3 H3D 108.5 . . ?
C2 C3 H3D 108.5 . . ?
H3C C3 H3D 107.5 . . ?
N1 C4 N2 110.83(15) . . ?
N1 C4 C3 127.29(16) . . ?
N2 C4 C3 121.88(15) . . ?
O4 C5 O3 124.02(17) . . ?
O4 C5 C6 118.64(17) . . ?
O3 C5 C6 117.33(16) . . ?
N2 C6 C7 105.05(14) . . ?
N2 C6 C5 121.09(15) . . ?
C7 C6 C5 133.78(16) . . ?
C6 C7 N1 109.80(15) . . ?
C6 C7 C8 129.76(16) . . ?
N1 C7 C8 120.42(15) . . ?
O1 C8 O2 121.95(16) . . ?
O1 C8 C7 119.90(16) . . ?
O2 C8 C7 118.13(15) . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
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
O1 C8 1.230(2) . ?
O2 C8 1.292(2) . ?
O2 H2 0.8200 . ?
O3 C5 1.279(2) . ?
O4 C5 1.231(2) . ?
N1 C4 1.325(2) . ?
N1 C7 1.385(2) . ?
N2 C4 1.347(2) . ?
N2 C6 1.367(2) . ?
N2 H2D 0.8600 . ?
N3 C10 1.468(3) . ?
N3 C9 1.469(2) . ?
N3 H3A 0.9000 . ?
N3 H3B 0.9000 . ?
C1 C2 1.518(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.498(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.486(2) . ?
C3 H3C 0.9700 . ?
C3 H3D 0.9700 . ?
C5 C6 1.482(2) . ?
C6 C7 1.376(2) . ?
C7 C8 1.474(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
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
O2 H2 O3 0.82 1.63 2.4463(18) 177.1 .
N2 H2D O4 0.86 1.92 2.755(2) 162.0 3_576
N3 H3A N1 0.90 2.07 2.950(2) 166.1 .
N3 H3B O1 0.90 1.92 2.771(2) 156.0 3_675
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 178.77(17) . . . . ?
C7 N1 C4 N2 0.2(2) . . . . ?
C7 N1 C4 C3 179.92(18) . . . . ?
C6 N2 C4 N1 -0.2(2) . . . . ?
C6 N2 C4 C3 -179.94(16) . . . . ?
C2 C3 C4 N1 -4.0(3) . . . . ?
C2 C3 C4 N2 175.64(17) . . . . ?
C4 N2 C6 C7 0.1(2) . . . . ?
C4 N2 C6 C5 -177.08(16) . . . . ?
O4 C5 C6 N2 0.2(3) . . . . ?
O3 C5 C6 N2 179.33(17) . . . . ?
O4 C5 C6 C7 -176.0(2) . . . . ?
O3 C5 C6 C7 3.1(3) . . . . ?
N2 C6 C7 N1 0.02(19) . . . . ?
C5 C6 C7 N1 176.70(19) . . . . ?
N2 C6 C7 C8 -178.26(17) . . . . ?
C5 C6 C7 C8 -1.6(3) . . . . ?
C4 N1 C7 C6 -0.15(19) . . . . ?
C4 N1 C7 C8 178.32(16) . . . . ?
C6 C7 C8 O1 176.65(18) . . . . ?
N1 C7 C8 O1 -1.5(3) . . . . ?
C6 C7 C8 O2 -2.1(3) . . . . ?
N1 C7 C8 O2 179.73(16) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653984
