#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/79/2217960.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_2217960
loop_
_publ_author_name
'Wang, Zhong-Long'
'Jia, Li-Hui'
_publ_section_title
;
 Three-dimensional network in piperazine-1,4-diium--picrate--piperazine
 (1/2/1)
;
_journal_coeditor_code           LH2598
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o665
_journal_page_last               o666
_journal_paper_doi               10.1107/S1600536808005710
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C4 H12 N2 2+, 2C6 H2 N3 O7 -, C4 H10 N2'
_chemical_formula_moiety         'C4 H12 N2 2+, 2C6 H2 N3 O7 -, C4 H10 N2'
_chemical_formula_sum            'C20 H26 N10 O14'
_chemical_formula_weight         630.50
_chemical_name_systematic
;
piperazine-1,4-diium--picrate--piperazine (1/2/1)
;
_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                98.1400(10)
_cell_angle_beta                 98.9740(10)
_cell_angle_gamma                109.2500(10)
_cell_formula_units_Z            1
_cell_length_a                   7.7150(6)
_cell_length_b                   8.1658(6)
_cell_length_c                   11.3024(8)
_cell_measurement_reflns_used    2518
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      26.15
_cell_measurement_theta_min      2.70
_cell_volume                     649.62(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, 2003)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6131
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_correction_T_min  0.9629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.274
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0680
_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)+(0.0397P)²+1.3400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1653
_refine_ls_wR_factor_ref         0.1689
_reflns_number_gt                1917
_reflns_number_total             2258
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2598.cif
_cod_data_source_block           I
_cod_database_code               2217960
_cod_database_fobs_code          2217960
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
C C1 0.1576(5) 0.8052(4) 0.9002(3) 0.0332(8) Uani d . 1
C C2 0.2353(5) 0.7965(5) 1.0152(3) 0.0378(9) Uani d . 1
H H2 0.2296 0.6883 1.0348 0.045 Uiso calc R 1
C C3 0.3230(5) 0.9530(5) 1.1019(3) 0.0348(8) Uani d . 1
C C4 0.3317(5) 1.1141(5) 1.0738(3) 0.0380(9) Uani d . 1
H H4 0.3912 1.2181 1.1329 0.046 Uiso calc R 1
C C5 0.2518(5) 1.1200(5) 0.9578(3) 0.0371(8) Uani d . 1
C C6 0.1526(5) 0.9660(5) 0.8609(3) 0.0333(8) Uani d . 1
C C7 0.1883(5) 1.0168(5) 0.4896(3) 0.0392(9) Uani d . 1
H H7A 0.3073 1.0068 0.5226 0.047 Uiso calc R 1
H H7B 0.1971 1.0570 0.4132 0.047 Uiso calc R 1
C C8 0.0332(5) 0.8378(5) 0.4654(3) 0.0381(9) Uani d . 1
H H8A 0.0549 0.7561 0.4034 0.046 Uiso calc R 1
H H8B 0.0337 0.7912 0.5397 0.046 Uiso calc R 1
C C9 0.3474(5) 1.5596(5) 0.4793(4) 0.0405(9) Uani d . 1
H H9A 0.4124 1.6869 0.4938 0.049 Uiso calc R 1
H H9B 0.2133 1.5352 0.4581 0.049 Uiso calc R 1
C C10 0.5940(5) 1.5299(5) 0.6247(3) 0.0386(9) Uani d . 1
H H10A 0.6210 1.4848 0.6976 0.046 Uiso calc R 1
H H10B 0.6639 1.6566 0.6425 0.046 Uiso calc R 1
N N1 0.0732(4) 0.6390(4) 0.8092(3) 0.0405(8) Uani d . 1
N N2 0.4143(5) 0.9504(4) 1.2226(3) 0.0443(8) Uani d . 1
N N3 0.2705(6) 1.2965(4) 0.9349(3) 0.0528(9) Uani d . 1
N N4 0.1521(4) 1.1476(4) 0.5768(3) 0.0364(7) Uani d . 1
H H4A 0.157(6) 1.118(5) 0.647(4) 0.044 Uiso d . 1
H H4B 0.228(6) 1.255(6) 0.584(4) 0.044 Uiso d . 1
N N5 0.3922(5) 1.4953(4) 0.5905(3) 0.0383(7) Uani d . 1
H H5A 0.359(6) 1.548(5) 0.649(4) 0.046 Uiso d . 1
O O1 0.0655(4) 0.9638(4) 0.7581(2) 0.0471(7) Uani d . 1
O O2 0.1103(5) 0.6367(4) 0.7077(3) 0.0579(8) Uani d . 1
O O3 -0.0265(5) 0.5088(4) 0.8379(3) 0.0720(10) Uani d . 1
O O4 0.4179(6) 0.8106(4) 1.2447(3) 0.0925(14) Uani d . 1
O O5 0.4870(5) 1.0892(4) 1.2985(3) 0.0599(9) Uani d . 1
O O6 0.3035(6) 1.4152(4) 1.0227(3) 0.0831(12) Uani d . 1
O O7 0.2583(6) 1.3203(4) 0.8304(3) 0.0799(12) Uani 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
C2 C1 C6 . . 125.4(3) no
C2 C1 N1 . . 117.1(3) no
C6 C1 N1 . . 117.5(3) no
C1 C2 C3 . . 118.3(3) no
C1 C2 H2 . . 120.8 no
C3 C2 H2 . . 120.8 no
C4 C3 C2 . . 121.2(3) no
C4 C3 N2 . . 118.7(3) no
C2 C3 N2 . . 120.0(3) no
C5 C4 C3 . . 119.5(3) no
C5 C4 H4 . . 120.2 no
C3 C4 H4 . . 120.2 no
C4 C5 C6 . . 124.3(3) no
C4 C5 N3 . . 116.0(3) no
C6 C5 N3 . . 119.7(3) no
O1 C6 C5 . . 126.4(3) no
O1 C6 C1 . . 122.4(3) no
C5 C6 C1 . . 111.1(3) no
N4 C7 C8 . . 110.9(3) no
N4 C7 H7A . . 109.5 no
C8 C7 H7A . . 109.5 no
N4 C7 H7B . . 109.5 no
C8 C7 H7B . . 109.5 no
H7A C7 H7B . . 108.0 no
N4 C8 C7 2_576 . 110.4(3) no
N4 C8 H8A 2_576 . 109.6 no
C7 C8 H8A . . 109.6 no
N4 C8 H8B 2_576 . 109.6 no
C7 C8 H8B . . 109.6 no
H8A C8 H8B . . 108.1 no
N5 C9 C10 . 2_686 110.2(3) no
N5 C9 H9A . . 109.6 no
C10 C9 H9A 2_686 . 109.6 no
N5 C9 H9B . . 109.6 no
C10 C9 H9B 2_686 . 109.6 no
H9A C9 H9B . . 108.1 no
N5 C10 C9 . 2_686 109.1(3) no
N5 C10 H10A . . 109.9 no
C9 C10 H10A 2_686 . 109.9 no
N5 C10 H10B . . 109.9 no
C9 C10 H10B 2_686 . 109.9 no
H10A C10 H10B . . 108.3 no
O3 N1 O2 . . 122.7(3) no
O3 N1 C1 . . 118.9(3) no
O2 N1 C1 . . 118.3(3) no
O4 N2 O5 . . 122.3(3) no
O4 N2 C3 . . 118.7(3) no
O5 N2 C3 . . 119.0(3) no
O6 N3 O7 . . 122.6(4) no
O6 N3 C5 . . 117.9(3) no
O7 N3 C5 . . 119.5(3) no
C7 N4 C8 . 2_576 112.2(3) no
C7 N4 H4A . . 109(3) no
C8 N4 H4A 2_576 . 109(3) no
C7 N4 H4B . . 114(3) no
C8 N4 H4B 2_576 . 102(3) no
H4A N4 H4B . . 110(4) no
C10 N5 C9 . . 110.9(3) no
C10 N5 H5A . . 109(3) no
C9 N5 H5A . . 109(3) 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 C2 . 1.366(5) no
C1 C6 . 1.454(5) no
C1 N1 . 1.461(5) no
C2 C3 . 1.385(5) no
C2 H2 . 0.9300 no
C3 C4 . 1.380(5) no
C3 N2 . 1.441(5) no
C4 C5 . 1.373(5) no
C4 H4 . 0.9300 no
C5 C6 . 1.442(5) no
C5 N3 . 1.464(5) no
C6 O1 . 1.243(4) no
C7 N4 . 1.475(5) no
C7 C8 . 1.508(5) no
C7 H7A . 0.9700 no
C7 H7B . 0.9700 no
C8 N4 2_576 1.484(5) no
C8 H8A . 0.9700 no
C8 H8B . 0.9700 no
C9 N5 . 1.465(5) no
C9 C10 2_686 1.504(5) no
C9 H9A . 0.9700 no
C9 H9B . 0.9700 no
C10 N5 . 1.465(5) no
C10 C9 2_686 1.504(5) no
C10 H10A . 0.9700 no
C10 H10B . 0.9700 no
N1 O3 . 1.210(4) no
N1 O2 . 1.224(4) no
N2 O4 . 1.210(4) no
N2 O5 . 1.221(4) no
N3 O6 . 1.215(4) no
N3 O7 . 1.219(4) no
N4 C8 2_576 1.484(5) no
N4 H4A . 0.86(4) no
N4 H4B . 0.86(4) no
N5 H5A . 0.86(4) 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
N4 H4A O1 . 0.86(4) 1.95(4) 2.745(4) 153(4) yes
N4 H4A O7 . 0.86(4) 2.31(4) 2.870(5) 123(3) yes
N4 H4B N5 . 0.86(4) 1.94(4) 2.799(4) 176(4) yes
N5 H5A O2 1_565 0.86(4) 2.41(4) 3.153(5) 145(4) yes
C2 H2 O6 1_545 0.93 2.47 3.335(5) 155 yes
C7 H7B O1 2_576 0.97 2.52 3.211(5) 128 yes
C8 H8B O1 . 0.97 2.60 3.267(5) 127 yes
C8 H8B O2 . 0.97 2.52 3.458(5) 162 yes
C9 H9A O5 2_687 0.97 2.60 3.272(5) 127 yes
C10 H10A O4 2_677 0.97 2.52 3.310(5) 138 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_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . -2.3(6) no
N1 C1 C2 C3 . . 177.5(3) no
C1 C2 C3 C4 . . 0.2(6) no
C1 C2 C3 N2 . . -177.1(3) no
C2 C3 C4 C5 . . 0.2(6) no
N2 C3 C4 C5 . . 177.5(3) no
C3 C4 C5 C6 . . 1.6(6) no
C3 C4 C5 N3 . . -178.8(3) no
C4 C5 C6 O1 . . 173.8(4) no
N3 C5 C6 O1 . . -5.7(6) no
C4 C5 C6 C1 . . -3.2(5) no
N3 C5 C6 C1 . . 177.2(3) no
C2 C1 C6 O1 . . -173.5(4) no
N1 C1 C6 O1 . . 6.7(5) no
C2 C1 C6 C5 . . 3.7(5) no
N1 C1 C6 C5 . . -176.1(3) no
N4 C7 C8 N4 . 2_576 55.1(4) no
C2 C1 N1 O3 . . 44.6(5) no
C6 C1 N1 O3 . . -135.6(4) no
C2 C1 N1 O2 . . -133.7(4) no
C6 C1 N1 O2 . . 46.1(5) no
C4 C3 N2 O4 . . -175.0(4) no
C2 C3 N2 O4 . . 2.4(6) no
C4 C3 N2 O5 . . 4.3(5) no
C2 C3 N2 O5 . . -178.4(4) no
C4 C5 N3 O6 . . -20.6(6) no
C6 C5 N3 O6 . . 159.0(4) no
C4 C5 N3 O7 . . 157.2(4) no
C6 C5 N3 O7 . . -23.2(6) no
C8 C7 N4 C8 . 2_576 -56.1(4) no
C9 C10 N5 C9 2_686 . -58.5(4) no
C10 C9 N5 C10 2_686 . 59.1(4) no
