#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/78/2227801.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_2227801
loop_
_publ_author_name
'Liu, Ping-xian'
'Li, Zhi-an'
'Chen, Dao-yong'
_publ_section_title
;
 Tetraimidazolium piperazinediium bis(benzene-1,3,5-tricarboxylate)
 dihydrate
;
_journal_coeditor_code           LH5148
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2900
_journal_paper_doi               10.1107/S1600536810041310
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac
'4C3 H5 N2 +, C4 H12 N2 +, 2C9 H3 O6 3-, 2H2 O'
_chemical_formula_moiety
'4(C3 H5 N2) +, (C4 H12 N2)+, 2(C9 H3 O6 3-), 2H2 O'
_chemical_formula_sum            'C34 H42 N10 O14'
_chemical_formula_weight         814.78
_chemical_name_systematic
;
Tetraimidazolium piperazinediium bis(benzene-1,3,5-tricarboxylate) dihydrate
;
_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           SHELXL-97
_cell_angle_alpha                96.8950(10)
_cell_angle_beta                 95.2010(10)
_cell_angle_gamma                101.439(2)
_cell_formula_units_Z            1
_cell_length_a                   7.1548(4)
_cell_length_b                   9.9424(5)
_cell_length_c                   13.3567(7)
_cell_measurement_reflns_used    2102
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.22
_cell_measurement_theta_min      2.43
_cell_volume                     918.11(8)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '0.3° wide ω scans'
_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  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10341
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_correction_T_min  0.9671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0453
_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)+(0.0631P)²+0.0369P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1218
_reflns_number_gt                2757
_reflns_number_total             3925
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5148.cif
_cod_data_source_block           I
_cod_database_code               2227801
_cod_database_fobs_code          2227801
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 0.2128(2) -0.05764(17) 0.89657(11) 0.0263(4) Uani d . 1 . .
C C2 0.1004(2) -0.17749(17) 0.84080(11) 0.0263(4) Uani d . 1 . .
H H2 0.0409 -0.2481 0.8743 0.032 Uiso calc R 1 . .
C C3 0.0756(2) -0.19338(17) 0.73487(11) 0.0274(4) Uani d . 1 . .
C C4 0.1609(2) -0.08588(18) 0.68651(12) 0.0295(4) Uani d . 1 . .
H H4 0.1465 -0.0964 0.6159 0.035 Uiso calc R 1 . .
C C5 0.2676(2) 0.03761(17) 0.74101(12) 0.0267(4) Uani d . 1 . .
C C6 0.2947(2) 0.04896(17) 0.84640(12) 0.0274(4) Uani d . 1 . .
H H6 0.3694 0.1297 0.8838 0.033 Uiso calc R 1 . .
C C7 0.2458(2) -0.04026(18) 1.01134(12) 0.0297(4) Uani d . 1 . .
C C8 -0.0459(2) -0.32408(19) 0.67241(12) 0.0332(4) Uani d . 1 . .
C C9 0.3502(2) 0.15651(19) 0.68720(13) 0.0310(4) Uani d . 1 . .
C C10 0.2728(3) -0.0067(2) 1.32738(13) 0.0391(5) Uani d . 1 . .
H H10 0.3430 0.0790 1.3175 0.047 Uiso calc R 1 . .
C C11 0.1114(3) -0.2190(2) 1.29964(14) 0.0432(5) Uani d . 1 . .
H H11 0.0505 -0.3063 1.2661 0.052 Uiso calc R 1 . .
C C12 0.1222(3) -0.1753(2) 1.39965(13) 0.0421(5) Uani d . 1 . .
H H12 0.0702 -0.2261 1.4484 0.051 Uiso calc R 1 . .
C C13 0.2479(3) 0.3752(2) 0.99158(14) 0.0401(5) Uani d . 1 . .
H H13 0.2379 0.2876 1.0111 0.048 Uiso calc R 1 . .
C C14 0.2247(3) 0.4896(2) 1.04845(14) 0.0396(5) Uani d . 1 . .
H H14 0.1949 0.4961 1.1150 0.048 Uiso calc R 1 . .
C C15 0.2920(3) 0.5449(2) 0.90127(14) 0.0400(5) Uani d . 1 . .
H H15 0.3176 0.5954 0.8480 0.048 Uiso calc R 1 . .
C C16 0.3894(3) 0.4987(2) 0.58396(13) 0.0422(5) Uani d . 1 . .
H H16A 0.3773 0.5318 0.6539 0.051 Uiso calc R 1 . .
H H16B 0.2710 0.4341 0.5557 0.051 Uiso calc R 1 . .
C C17 0.5803(3) 0.3814(2) 0.47501(14) 0.0462(5) Uani d . 1 . .
H H17A 0.4688 0.3126 0.4428 0.055 Uiso calc R 1 . .
H H17B 0.6910 0.3387 0.4747 0.055 Uiso calc R 1 . .
N N1 0.2057(2) -0.11215(17) 1.25638(11) 0.0396(4) Uani d . 1 . .
H H1A 0.217(3) -0.111(2) 1.1923(16) 0.048 Uiso d . 1 . .
N N2 0.2245(2) -0.04171(17) 1.41557(11) 0.0389(4) Uani d . 1 . .
H H2A 0.265(3) 0.014(2) 1.4745(16) 0.047 Uiso d . 1 . .
N N3 0.2891(2) 0.41179(16) 0.89917(12) 0.0374(4) Uani d . 1 . .
H H3A 0.320(3) 0.355(2) 0.8468(14) 0.045 Uiso d . 1 . .
N N4 0.2528(2) 0.59528(17) 0.99092(11) 0.0361(4) Uani d . 1 . .
H H4A 0.240(3) 0.686(2) 1.0107(14) 0.043 Uiso d . 1 . .
N N5 0.5516(2) 0.42669(17) 0.58090(11) 0.0388(4) Uani d . 1 . .
H H5A 0.667(3) 0.486(2) 0.6204(14) 0.047 Uiso d . 1 . .
H H5B 0.520(3) 0.350(2) 0.6120(15) 0.047 Uiso d . 1 . .
O O1 0.3047(2) 0.07841(13) 1.05718(9) 0.0488(4) Uani d . 1 . .
O O2 0.21058(18) -0.14867(12) 1.05409(8) 0.0379(3) Uani d . 1 . .
O O3 -0.15144(18) -0.40803(13) 0.71833(9) 0.0450(4) Uani d . 1 . .
O O4 -0.0363(2) -0.34118(16) 0.58017(9) 0.0617(5) Uani d . 1 . .
O O5 0.3573(2) 0.13542(13) 0.59351(9) 0.0436(3) Uani d . 1 . .
O O6 0.41142(19) 0.27435(12) 0.73950(9) 0.0415(3) Uani d . 1 . .
O O7 0.4407(2) 0.26393(16) 1.22724(10) 0.0498(4) Uani d . 1 . .
H H7A 0.407(3) 0.201(3) 1.1749(19) 0.075 Uiso d . 1 . .
H H7B 0.342(3) 0.306(3) 1.2364(18) 0.075 Uiso d . 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
C6 C1 C2 . . 119.32(14) ?
C6 C1 C7 . . 119.29(14) ?
C2 C1 C7 . . 121.39(15) ?
C1 C2 C3 . . 120.66(15) ?
C1 C2 H2 . . 119.7 ?
C3 C2 H2 . . 119.7 ?
C4 C3 C2 . . 118.85(14) ?
C4 C3 C8 . . 119.66(14) ?
C2 C3 C8 . . 121.48(15) ?
C3 C4 C5 . . 121.49(14) ?
C3 C4 H4 . . 119.3 ?
C5 C4 H4 . . 119.3 ?
C4 C5 C6 . . 118.38(15) ?
C4 C5 C9 . . 120.74(14) ?
C6 C5 C9 . . 120.88(15) ?
C1 C6 C5 . . 121.22(15) ?
C1 C6 H6 . . 119.4 ?
C5 C6 H6 . . 119.4 ?
O1 C7 O2 . . 124.44(15) ?
O1 C7 C1 . . 117.75(16) ?
O2 C7 C1 . . 117.81(14) ?
O4 C8 O3 . . 124.28(16) ?
O4 C8 C3 . . 117.93(16) ?
O3 C8 C3 . . 117.79(14) ?
O5 C9 O6 . . 122.58(16) ?
O5 C9 C5 . . 119.37(16) ?
O6 C9 C5 . . 118.05(14) ?
N1 C10 N2 . . 108.95(18) ?
N1 C10 H10 . . 125.5 ?
N2 C10 H10 . . 125.5 ?
C12 C11 N1 . . 107.52(17) ?
C12 C11 H11 . . 126.2 ?
N1 C11 H11 . . 126.2 ?
C11 C12 N2 . . 106.45(17) ?
C11 C12 H12 . . 126.8 ?
N2 C12 H12 . . 126.8 ?
C14 C13 N3 . . 106.88(17) ?
C14 C13 H13 . . 126.6 ?
N3 C13 H13 . . 126.6 ?
C13 C14 N4 . . 107.51(16) ?
C13 C14 H14 . . 126.2 ?
N4 C14 H14 . . 126.2 ?
N3 C15 N4 . . 109.13(17) ?
N3 C15 H15 . . 125.4 ?
N4 C15 H15 . . 125.4 ?
N5 C16 C17 . 2_666 110.90(16) ?
N5 C16 H16A . . 109.5 ?
C17 C16 H16A 2_666 . 109.5 ?
N5 C16 H16B . . 109.5 ?
C17 C16 H16B 2_666 . 109.5 ?
H16A C16 H16B . . 108.0 ?
N5 C17 C16 . 2_666 111.07(16) ?
N5 C17 H17A . . 109.4 ?
C16 C17 H17A 2_666 . 109.4 ?
N5 C17 H17B . . 109.4 ?
C16 C17 H17B 2_666 . 109.4 ?
H17A C17 H17B . . 108.0 ?
C10 N1 C11 . . 108.59(15) ?
C10 N1 H1A . . 124.3(14) ?
C11 N1 H1A . . 127.1(14) ?
C10 N2 C12 . . 108.49(16) ?
C10 N2 H2A . . 122.6(13) ?
C12 N2 H2A . . 128.7(13) ?
C15 N3 C13 . . 108.45(16) ?
C15 N3 H3A . . 125.6(13) ?
C13 N3 H3A . . 125.7(12) ?
C15 N4 C14 . . 108.03(16) ?
C15 N4 H4A . . 126.1(12) ?
C14 N4 H4A . . 125.8(12) ?
C17 N5 C16 . . 110.82(14) ?
C17 N5 H5A . . 113.0(11) ?
C16 N5 H5A . . 110.0(11) ?
C17 N5 H5B . . 108.4(13) ?
C16 N5 H5B . . 107.1(13) ?
H5A N5 H5B . . 107.3(16) ?
H7A O7 H7B . . 108(2) ?
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 C6 . 1.382(2) ?
C1 C2 . 1.385(2) ?
C1 C7 . 1.513(2) ?
C2 C3 . 1.396(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.382(2) ?
C3 C8 . 1.517(2) ?
C4 C5 . 1.390(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.391(2) ?
C5 C9 . 1.506(2) ?
C6 H6 . 0.9300 ?
C7 O1 . 1.236(2) ?
C7 O2 . 1.272(2) ?
C8 O4 . 1.233(2) ?
C8 O3 . 1.265(2) ?
C9 O5 . 1.251(2) ?
C9 O6 . 1.264(2) ?
C10 N1 . 1.307(2) ?
C10 N2 . 1.324(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.345(3) ?
C11 N1 . 1.361(2) ?
C11 H11 . 0.9300 ?
C12 N2 . 1.365(2) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.337(3) ?
C13 N3 . 1.369(2) ?
C13 H13 . 0.9300 ?
C14 N4 . 1.369(2) ?
C14 H14 . 0.9300 ?
C15 N3 . 1.317(2) ?
C15 N4 . 1.318(2) ?
C15 H15 . 0.9300 ?
C16 N5 . 1.481(3) ?
C16 C17 2_666 1.497(3) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 N5 . 1.477(2) ?
C17 C16 2_666 1.497(3) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
N1 H1A . 0.87(2) ?
N2 H2A . 0.90(2) ?
N3 H3A . 0.915(19) ?
N4 H4A . 0.93(2) ?
N5 H5A . 0.98(2) ?
N5 H5B . 0.91(2) ?
O7 H7A . 0.86(3) ?
O7 H7B . 0.90(3) ?
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 H1A O2 . 0.87(2) 1.83(2) 2.6870(18) 166.9(19) y
N2 H2A O5 1_556 0.90(2) 1.86(2) 2.7522(19) 177.4(19) y
N3 H3A O6 . 0.915(19) 1.80(2) 2.701(2) 168.8(18) y
N4 H4A O2 1_565 0.93(2) 1.74(2) 2.668(2) 176.6(18) y
N5 H5A O3 1_665 0.98(2) 1.83(2) 2.7872(19) 166.7(17) y
N5 H5A O4 1_665 0.98(2) 2.60(2) 3.366(2) 135.7(14) y
N5 H5B O5 . 0.91(2) 2.19(2) 2.985(2) 145.2(16) y
N5 H5B O6 . 0.91(2) 2.10(2) 2.888(2) 145.1(18) y
O7 H7A O1 . 0.86(3) 1.86(3) 2.7184(17) 171(2) y
O7 H7B O3 2_557 0.90(3) 1.95(3) 2.840(2) 169(2) y
C10 H10 O7 . 0.93 2.35 3.217(3) 155.9 y
C12 H12 O4 1_556 0.93 2.32 3.244(2) 174.8 y
C13 H13 O1 . 0.93 2.36 3.267(2) 164.1 y
C14 H14 O3 2_557 0.93 2.51 3.372(2) 154.0 y
C15 H15 O7 2_667 0.93 2.38 3.186(2) 145.4 y
C16 H16B O4 2_556 0.97 2.32 3.200(2) 150.1 y
C16 H16A O7 2_667 0.97 2.48 3.207(2) 131.7 y
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
C6 C1 C2 C3 . . . . 2.5(2) ?
C7 C1 C2 C3 . . . . -178.26(15) ?
C1 C2 C3 C4 . . . . -1.7(3) ?
C1 C2 C3 C8 . . . . 179.66(15) ?
C2 C3 C4 C5 . . . . -1.0(3) ?
C8 C3 C4 C5 . . . . 177.65(15) ?
C3 C4 C5 C6 . . . . 2.9(3) ?
C3 C4 C5 C9 . . . . -176.58(15) ?
C2 C1 C6 C5 . . . . -0.5(2) ?
C7 C1 C6 C5 . . . . -179.78(15) ?
C4 C5 C6 C1 . . . . -2.1(2) ?
C9 C5 C6 C1 . . . . 177.32(15) ?
C6 C1 C7 O1 . . . . 17.1(2) ?
C2 C1 C7 O1 . . . . -162.20(16) ?
C6 C1 C7 O2 . . . . -163.16(15) ?
C2 C1 C7 O2 . . . . 17.6(2) ?
C4 C3 C8 O4 . . . . 13.2(3) ?
C2 C3 C8 O4 . . . . -168.22(17) ?
C4 C3 C8 O3 . . . . -166.35(16) ?
C2 C3 C8 O3 . . . . 12.2(3) ?
C4 C5 C9 O5 . . . . -14.7(3) ?
C6 C5 C9 O5 . . . . 165.86(16) ?
C4 C5 C9 O6 . . . . 165.85(16) ?
C6 C5 C9 O6 . . . . -13.6(2) ?
N1 C11 C12 N2 . . . . -0.3(2) ?
N3 C13 C14 N4 . . . . -0.3(2) ?
N2 C10 N1 C11 . . . . -0.1(2) ?
C12 C11 N1 C10 . . . . 0.3(2) ?
N1 C10 N2 C12 . . . . 0.0(2) ?
C11 C12 N2 C10 . . . . 0.2(2) ?
N4 C15 N3 C13 . . . . -0.5(2) ?
C14 C13 N3 C15 . . . . 0.5(2) ?
N3 C15 N4 C14 . . . . 0.3(2) ?
C13 C14 N4 C15 . . . . 0.0(2) ?
C16 C17 N5 C16 2_666 . . . 56.2(2) ?
C17 C16 N5 C17 2_666 . . . -56.1(2) ?
