#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/87/2228785.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_2228785
loop_
_publ_author_name
'Gao, Zhu-Qing'
'Gu, Jin-Zhong'
_publ_section_title
;
 Piperazine-1,4-diium bis(hydrogen
 2-propyl-1H-imidazole-4,5-dicarboxylate) monohydrate
;
_journal_coeditor_code           JH2238
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o31
_journal_paper_doi               10.1107/S1600536810049822
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C4 H12 N2 2+, 2C8 H9 N2 O4 -, H2 O1'
_chemical_formula_moiety         'C4 H12 N2 2+, 2(C8 H9 N2 O4 -), H2 O1'
_chemical_formula_sum            'C20 H32 N6 O9'
_chemical_formula_weight         500.52
_chemical_name_systematic
;
Piperazine-1,4-diium bis(hydrogen
2-propyl-1H-imidazole-4,5-dicarboxylate) monohydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 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                 101.296(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.288(2)
_cell_length_b                   15.965(3)
_cell_length_c                   14.449(4)
_cell_measurement_reflns_used    1047
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     2553.5(10)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6239
_diffrn_reflns_theta_full        24.27
_diffrn_reflns_theta_max         24.27
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2066
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0619P)²+1.5738P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1358
_reflns_number_gt                1499
_reflns_number_total             2066
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jh2238.cif
_cod_data_source_block           I
_cod_original_cell_volume        2553.6(10)
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               2228785
_cod_database_fobs_code          2228785
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -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 0.0849(2) 0.71261(16) 0.09103(17) 0.0422(6) Uani d . 1 . .
C C2 0.1935(2) 0.67934(14) 0.15314(16) 0.0364(6) Uani d . 1 . .
C C3 0.2144(2) 0.64165(14) 0.24013(16) 0.0363(6) Uani d . 1 . .
C C4 0.1292(2) 0.62027(16) 0.30292(18) 0.0424(6) Uani d . 1 . .
C C5 0.5184(2) 0.6485(2) 0.1969(2) 0.0611(8) Uani d . 1 . .
H H5A 0.5649 0.6478 0.2609 0.073 Uiso calc R 1 . .
H H5B 0.5409 0.6984 0.1661 0.073 Uiso calc R 1 . .
C C6 0.5505(3) 0.5713(3) 0.1446(4) 0.1233(18) Uani d U 1 . .
H H6A 0.5028 0.5710 0.0810 0.148 Uiso calc R 1 . .
H H6B 0.5308 0.5212 0.1765 0.148 Uiso calc R 1 . .
C C7 0.6847(4) 0.5704(3) 0.1403(5) 0.171(3) Uani d U 1 . .
H H7A 0.7039 0.6195 0.1078 0.205 Uiso calc R 1 . .
H H7B 0.7024 0.5213 0.1072 0.205 Uiso calc R 1 . .
H H7C 0.7320 0.5699 0.2032 0.205 Uiso calc R 1 . .
C C8 0.5499(2) 0.57768(16) 0.47554(19) 0.0483(7) Uani d . 1 . .
H H8A 0.5643 0.6370 0.4872 0.058 Uiso calc R 1 . .
H H8B 0.5864 0.5617 0.4227 0.058 Uiso calc R 1 . .
C C9 0.3930(2) 0.47110(16) 0.43879(17) 0.0456(7) Uani d . 1 . .
H H9A 0.4231 0.4509 0.3845 0.055 Uiso calc R 1 . .
H H9B 0.3062 0.4627 0.4267 0.055 Uiso calc R 1 . .
C C12 0.3877(2) 0.65313(16) 0.20022(17) 0.0429(6) Uani d . 1 . .
H H2 -0.004(2) 0.6647(18) 0.195(2) 0.103(11) Uiso d . 1 . .
H H1W 0.8140 0.7443 0.0209 0.31(5) Uiso d RD 1 . .
N N1 0.30493(17) 0.68560(13) 0.12993(13) 0.0410(5) Uani d . 1 . .
H H1 0.3196 0.7069 0.0787 0.049 Uiso calc R 1 . .
N N2 0.33568(18) 0.62552(13) 0.26903(14) 0.0426(5) Uani d . 1 . .
N N3 0.42026(17) 0.56200(13) 0.45216(14) 0.0426(5) Uani d . 1 . .
H H3A 0.3883 0.5897 0.3989 0.051 Uiso calc R 1 . .
H H3B 0.3856 0.5818 0.4988 0.051 Uiso calc R 1 . .
O O1 -0.01641(15) 0.70340(13) 0.11795(13) 0.0582(6) Uani d . 1 . .
O O2 0.09473(15) 0.74761(12) 0.01667(12) 0.0510(5) Uani d . 1 . .
O O3 0.01637(15) 0.63600(13) 0.27299(13) 0.0566(5) Uani d . 1 . .
O O4 0.16861(16) 0.58907(12) 0.38055(12) 0.0537(5) Uani d . 1 . .
O O5 0.7500 0.7747(3) 0.0000 0.170(3) Uani d SD 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
_geom_angle_publ_flag
O2 C1 O1 . . 123.5(2) ?
O2 C1 C2 . . 119.2(2) ?
O1 C1 C2 . . 117.3(2) ?
N1 C2 C3 . . 104.8(2) ?
N1 C2 C1 . . 121.4(2) ?
C3 C2 C1 . . 133.8(2) ?
C2 C3 N2 . . 110.1(2) ?
C2 C3 C4 . . 130.1(2) ?
N2 C3 C4 . . 119.8(2) ?
O4 C4 O3 . . 122.9(2) ?
O4 C4 C3 . . 119.3(2) ?
O3 C4 C3 . . 117.8(2) ?
C12 C5 C6 . . 112.9(3) ?
C12 C5 H5A . . 109.0 ?
C6 C5 H5A . . 109.0 ?
C12 C5 H5B . . 109.0 ?
C6 C5 H5B . . 109.0 ?
H5A C5 H5B . . 107.8 ?
C5 C6 C7 . . 111.2(4) ?
C5 C6 H6A . . 109.4 ?
C7 C6 H6A . . 109.4 ?
C5 C6 H6B . . 109.4 ?
C7 C6 H6B . . 109.4 ?
H6A C6 H6B . . 108.0 ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N3 C8 C9 . 5_666 110.6(2) ?
N3 C8 H8A . . 109.5 ?
C9 C8 H8A 5_666 . 109.5 ?
N3 C8 H8B . . 109.5 ?
C9 C8 H8B 5_666 . 109.5 ?
H8A C8 H8B . . 108.1 ?
N3 C9 C8 . 5_666 110.8(2) ?
N3 C9 H9A . . 109.5 ?
C8 C9 H9A 5_666 . 109.5 ?
N3 C9 H9B . . 109.5 ?
C8 C9 H9B 5_666 . 109.5 ?
H9A C9 H9B . . 108.1 ?
N2 C12 N1 . . 110.5(2) ?
N2 C12 C5 . . 126.6(2) ?
N1 C12 C5 . . 122.9(2) ?
C12 N1 C2 . . 108.89(19) ?
C12 N1 H1 . . 125.6 ?
C2 N1 H1 . . 125.6 ?
C12 N2 C3 . . 105.7(2) ?
C8 N3 C9 . . 111.74(18) ?
C8 N3 H3A . . 109.3 ?
C9 N3 H3A . . 109.3 ?
C8 N3 H3B . . 109.3 ?
C9 N3 H3B . . 109.3 ?
H3A N3 H3B . . 107.9 ?
C1 O1 H2 . . 112.1(11) ?
C4 O3 H2 . . 112.9(12) ?
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 O2 . 1.235(3) ?
C1 O1 . 1.286(3) ?
C1 C2 . 1.469(3) ?
C2 N1 . 1.368(3) ?
C2 C3 . 1.372(3) ?
C3 N2 . 1.375(3) ?
C3 C4 . 1.486(3) ?
C4 O4 . 1.228(3) ?
C4 O3 . 1.287(3) ?
C5 C12 . 1.487(3) ?
C5 C6 . 1.526(5) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C7 . 1.528(5) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 N3 . 1.458(3) ?
C8 C9 5_666 1.497(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 N3 . 1.488(3) ?
C9 C8 5_666 1.497(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C12 N2 . 1.325(3) ?
C12 N1 . 1.342(3) ?
N1 H1 . 0.8600 ?
N3 H3A . 0.9000 ?
N3 H3B . 0.9000 ?
O1 H2 . 1.26(3) ?
O3 H2 . 1.19(3) ?
O5 H1W . 0.8739 ?
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
O3 H2 O1 . 1.19(3) 1.26(3) 2.447(3) 172(3)
O5 H1W O1 1_655 0.87 2.24 3.065(3) 158.0
N1 H1 O2 2 0.86 1.94 2.773(3) 161.6
N3 H3A N2 . 0.90 1.94 2.820(3) 165.4
N3 H3B O4 2_556 0.90 1.96 2.826(3) 160.7
