#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/58/2235805.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_2235805
loop_
_publ_author_name
'Ying, Yi-Mei'
'Zhang, Tong'
'Yang, Guang-Rui'
'Ma, Ning'
_publ_section_title
;
 Ethane-1,2-diaminium
 bis(4-carboxy-2-propyl-1H-imidazole-5-carboxyate) monohydrate
;
_journal_coeditor_code           GG2081
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2327
_journal_paper_doi               10.1107/S1600536812029406
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C2 H10 N2 2+, 2C8 H9 N2 O4 -, H2 O'
_chemical_formula_moiety         'C2 H10 N2 2+, 2(C8 H9 N2 O4 -), H2 O'
_chemical_formula_sum            'C18 H30 N6 O9'
_chemical_formula_weight         474.48
_chemical_name_systematic
;
Ethane-1,2-diaminium bis(4-carboxy-2-propyl-1H-imidazole-5-carboxyate)
monohydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 112.991(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.234(4)
_cell_length_b                   16.859(4)
_cell_length_c                   9.699(3)
_cell_measurement_reflns_used    356
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      14.77
_cell_measurement_theta_min      2.48
_cell_volume                     2293.1(11)
_computing_cell_refinement       'SAINT-Plus (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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART 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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0645
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5444
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_correction_T_min  0.9612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.447
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2011
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1098P)²+0.4118P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1678
_refine_ls_wR_factor_ref         0.1824
_reflns_number_gt                1500
_reflns_number_total             2011
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg2081.cif
_cod_data_source_block           I
_cod_original_cell_volume        2293.1(10)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2235805
_cod_database_fobs_code          2235805
loop_
_symmetry_equiv_pos_as_xyz
'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, -y, -z'
'x, -y, 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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.21377(15) 0.37000(13) 0.0929(2) 0.0456(6) Uani d . 1 1 . .
N N2 0.35960(14) 0.32244(13) 0.1911(2) 0.0433(6) Uani d . 1 1 . .
H H2A 0.4125 0.3057 0.2578 0.052 Uiso calc R 1 1 . .
N N3 0.00885(15) 0.38982(11) 0.0087(2) 0.0402(5) Uani d . 1 1 . .
H H3A 0.0712 0.3859 0.0313 0.048 Uiso calc R 1 1 . .
H H3B -0.0229 0.3808 -0.0887 0.048 Uiso calc R 1 1 . .
H H3C -0.0083 0.3542 0.0613 0.048 Uiso calc R 1 1 . .
O O1 0.10537(13) 0.39974(12) -0.2035(2) 0.0555(6) Uani d . 1 1 . .
O O2 0.21678(14) 0.35742(13) -0.2760(2) 0.0566(6) Uani d . 1 1 . .
H H2 0.2714 0.3404 -0.2372 0.068 Uiso calc R 1 1 . .
O O3 0.37886(14) 0.30257(13) -0.1635(2) 0.0578(6) Uani d . 1 1 . .
O O4 0.48440(12) 0.27422(11) 0.0614(2) 0.0509(5) Uani d . 1 1 . .
O O1W 0.5000 0.20888(16) -0.2500 0.0544(7) Uani d SD 1 2 . .
H H1W 0.460(2) 0.2394(18) -0.236(4) 0.082 Uiso d D 1 1 . .
C C1 0.18526(18) 0.37268(15) -0.1732(3) 0.0420(6) Uani d . 1 1 . .
C C2 0.24741(17) 0.35651(13) -0.0175(3) 0.0381(6) Uani d . 1 1 . .
C C3 0.33827(17) 0.32705(13) 0.0420(3) 0.0383(6) Uani d . 1 1 . .
C C4 0.40669(18) 0.29940(14) -0.0224(3) 0.0427(6) Uani d . 1 1 . .
C C5 0.28372(19) 0.34863(17) 0.2174(3) 0.0483(7) Uani d . 1 1 . .
C C6 0.2826(3) 0.3534(2) 0.3692(4) 0.0794(11) Uani d DU 1 1 A .
H H6A 0.2221 0.3324 0.3638 0.095 Uiso calc R 1 1 . .
H H6B 0.3321 0.3185 0.4343 0.095 Uiso calc R 1 1 . .
C C7 0.2958(4) 0.4296(3) 0.4395(5) 0.1099(14) Uani d DU 1 1 . .
H H7A 0.2500 0.4671 0.3743 0.132 Uiso calc PR 0.716(9) 1 A 1
H H7B 0.2863 0.4261 0.5325 0.132 Uiso calc PR 0.716(9) 1 A 1
H H7C 0.2345 0.4451 0.4399 0.132 Uiso d PR 0.284(9) 1 A 2
H H7D 0.3065 0.4642 0.3676 0.132 Uiso d PR 0.284(9) 1 A 2
C C8 0.3826(5) 0.4534(3) 0.4659(8) 0.095(2) Uani d PU 0.716(9) 1 A 1
H H8A 0.3969 0.4436 0.3794 0.142 Uiso calc PR 0.716(9) 1 A 1
H H8B 0.4268 0.4248 0.5500 0.142 Uiso calc PR 0.716(9) 1 A 1
H H8C 0.3879 0.5091 0.4877 0.142 Uiso calc PR 0.716(9) 1 A 1
C C8' 0.3712(10) 0.4585(7) 0.5926(14) 0.074(4) Uani d PU 0.284(9) 1 A 2
H H8'A 0.4097 0.4994 0.5756 0.111 Uiso calc PR 0.284(9) 1 A 2
H H8'B 0.4110 0.4147 0.6435 0.111 Uiso calc PR 0.284(9) 1 A 2
H H8'C 0.3393 0.4791 0.6529 0.111 Uiso calc PR 0.284(9) 1 A 2
C C9 -0.0132(2) 0.46962(15) 0.0454(3) 0.0439(6) Uani d . 1 1 . .
H H9A 0.0219 0.4798 0.1513 0.053 Uiso calc R 1 1 . .
H H9B -0.0807 0.4735 0.0245 0.053 Uiso calc R 1 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 0.0016 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C5 N1 C2 . . 104.8(2)
C5 N2 C3 . . 108.4(2)
C5 N2 H2A . . 125.8
C3 N2 H2A . . 125.8
C9 N3 H3A . . 109.5
C9 N3 H3B . . 109.5
H3A N3 H3B . . 109.5
C9 N3 H3C . . 109.5
H3A N3 H3C . . 109.5
H3B N3 H3C . . 109.5
C1 O2 H2 . . 109.5
O1 C1 O2 . . 121.7(2)
O1 C1 C2 . . 120.0(2)
O2 C1 C2 . . 118.4(2)
C3 C2 N1 . . 110.8(2)
C3 C2 C1 . . 130.1(2)
N1 C2 C1 . . 119.1(2)
N2 C3 C2 . . 104.6(2)
N2 C3 C4 . . 121.1(2)
C2 C3 C4 . . 134.3(2)
O4 C4 O3 . . 124.2(2)
O4 C4 C3 . . 119.2(2)
O3 C4 C3 . . 116.6(2)
N1 C5 N2 . . 111.3(2)
N1 C5 C6 . . 125.5(3)
N2 C5 C6 . . 123.2(3)
C7 C6 C5 . . 117.9(4)
C7 C6 H6A . . 107.8
C5 C6 H6A . . 107.8
C7 C6 H6B . . 107.8
C5 C6 H6B . . 107.8
H6A C6 H6B . . 107.2
C8 C7 C6 . . 108.1(5)
C8 C7 C8' . . 53.5(6)
C6 C7 C8' . . 130.3(6)
C8 C7 H7A . . 110.1
C6 C7 H7A . . 110.1
C8' C7 H7A . . 119.5
C8 C7 H7B . . 110.1
C6 C7 H7B . . 110.1
C8' C7 H7B . . 57.0
H7A C7 H7B . . 108.4
C8 C7 H7C . . 144.9
C6 C7 H7C . . 106.7
C8' C7 H7C . . 105.3
H7A C7 H7C . . 51.7
H7B C7 H7C . . 61.3
C8 C7 H7D . . 61.0
C6 C7 H7D . . 103.2
C8' C7 H7D . . 103.3
H7A C7 H7D . . 54.6
H7B C7 H7D . . 146.5
H7C C7 H7D . . 105.9
C7 C8 H7D . . 45.3
C7 C8 H8A . . 109.5
H7D C8 H8A . . 79.0
C7 C8 H8B . . 109.5
H7D C8 H8B . . 153.6
C7 C8 H8C . . 109.5
H7D C8 H8C . . 89.9
C7 C8' H8'A . . 109.5
C7 C8' H8'B . . 109.5
H8'A C8' H8'B . . 109.5
C7 C8' H8'C . . 109.5
H8'A C8' H8'C . . 109.5
H8'B C8' H8'C . . 109.5
N3 C9 C9 . 5_565 110.1(2)
N3 C9 H9A . . 109.6
C9 C9 H9A 5_565 . 109.6
N3 C9 H9B . . 109.6
C9 C9 H9B 5_565 . 109.6
H9A C9 H9B . . 108.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C5 . 1.311(3)
N1 C2 . 1.375(3)
N2 C5 . 1.351(3)
N2 C3 . 1.355(3)
N2 H2A . 0.8600
N3 C9 . 1.464(3)
N3 H3A . 0.8900
N3 H3B . 0.8900
N3 H3C . 0.8900
O1 C1 . 1.223(3)
O2 C1 . 1.289(3)
O2 H2 . 0.8200
O3 C4 . 1.266(3)
O4 C4 . 1.221(3)
O1W H1W . 0.849(10)
C1 C2 . 1.461(4)
C2 C3 . 1.368(3)
C3 C4 . 1.484(4)
C5 C6 . 1.481(4)
C6 C7 . 1.433(6)
C6 H6A . 0.9700
C6 H6B . 0.9700
C7 C8 . 1.309(7)
C7 C8' . 1.558(13)
C7 H7A . 0.9700
C7 H7B . 0.9700
C7 H7C . 0.9699
C7 H7D . 0.9698
C8 H7D . 1.1934
C8 H8A . 0.9600
C8 H8B . 0.9600
C8 H8C . 0.9600
C8' H8'A . 0.9600
C8' H8'B . 0.9600
C8' H8'C . 0.9600
C9 C9 5_565 1.505(5)
C9 H9A . 0.9700
C9 H9B . 0.9700
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
N2 H2A O4 2_655 0.86 1.92 2.759(3) 166.2
N3 H3A N1 . 0.89 2.03 2.921(3) 175.7
N3 H3A O1 . 0.89 2.54 2.964(3) 110.2
N3 H3B O1 2_554 0.89 1.94 2.792(3) 159.6
N3 H3C O1W 7 0.89 2.08 2.917(3) 156.8
O2 H2 O3 . 0.82 1.64 2.457(3) 177.4
O1W H1W O3 . 0.849(10) 1.957(13) 2.795(2) 169(4)
