#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/02/2210221.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_2210221
loop_
_publ_author_name
'Aghabozorg, Hossein'
'Ghasemikhah, Pouya'
'Ghadermazi, Mohammad'
'Attar Gharamaleki, Jafar'
'Sheshmani, Shabnam'
_publ_section_title
;
 Piperazinium bis(pyridine-2,6-dicarboxylato)mercurate(II) hexahydrate
;
_journal_coeditor_code           FI2005
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2269
_journal_page_last               m2271
_journal_paper_doi               10.1107/S1600536806032211
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '(C4 H12 N2) [Hg (C7 H3 N1 O4)2], 6H2 O'
_chemical_formula_moiety         'C4 H12 N2 2+ C14 H6 Hg N2 O8 2-, 6H2 O'
_chemical_formula_sum            'C18 H30 Hg N4 O14'
_chemical_formula_weight         727.05
_chemical_name_systematic
;
Piperazinium bis(pyridine-2,6-dicarboxylato)mercurate(II) hexahydrate
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.444(7)
_cell_length_b                   8.377(4)
_cell_length_c                   22.512(13)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3
_cell_volume                     2535(2)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1998)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART 1000 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  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16680
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.36
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.146
_exptl_absorpt_correction_T_max  0.427
_exptl_absorpt_correction_T_min  0.303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         2.657
_refine_diff_density_min         -1.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2731
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0240
_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)+(0.0328P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0617
_reflns_number_gt                1739
_reflns_number_total             2731
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fi2005.cif
_cod_data_source_block           I
_cod_database_code               2210221
_cod_database_fobs_code          2210221
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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
Hg Hg1 0.5000 0.72351(2) 0.2500 0.02021(8) Uani d S 1
O O1 0.34504(19) 0.4607(3) 0.39279(11) 0.0265(6) Uani d . 1
O O2 0.4688(2) 0.5437(3) 0.33497(12) 0.0296(7) Uani d . 1
O O3 0.4172(2) 0.9091(3) 0.18068(12) 0.0309(7) Uani d . 1
O O4 0.2664(2) 0.9466(3) 0.14124(11) 0.0310(7) Uani d . 1
N N1 0.3387(3) 0.7123(4) 0.26561(14) 0.0202(7) Uani d . 1
C C1 0.3031(3) 0.6258(4) 0.31094(15) 0.0205(8) Uani d . 1
C C2 0.2013(3) 0.6166(5) 0.32082(16) 0.0245(8) Uani d . 1
H H2A 0.1763 0.5583 0.3538 0.029 Uiso calc R 1
C C3 0.1367(3) 0.6925(5) 0.28248(17) 0.0276(9) Uani d . 1
H H3A 0.0669 0.6849 0.2881 0.033 Uiso calc R 1
C C4 0.1760(3) 0.7809(5) 0.23513(18) 0.0269(10) Uani d . 1
H H4A 0.1328 0.8339 0.2082 0.032 Uiso calc R 1
C C5 0.2770(3) 0.7904(4) 0.22783(17) 0.0215(9) Uani d . 1
C C6 0.3786(3) 0.5369(5) 0.34932(16) 0.0253(9) Uani d . 1
C C7 0.3248(3) 0.8894(4) 0.17902(16) 0.0253(9) Uani d . 1
N N1S 0.4947(2) 0.6331(3) 0.53959(12) 0.0200(6) Uani d . 1
H H1SC 0.5441 0.6072 0.5661 0.024 Uiso d R 1
H H1SD 0.4670 0.7283 0.5514 0.024 Uiso d R 1
C C1S 0.4169(3) 0.5063(4) 0.54052(17) 0.0239(8) Uani d . 1
H H1SE 0.3617 0.5362 0.5136 0.029 Uiso calc R 1
H H1SF 0.3896 0.4957 0.5812 0.029 Uiso calc R 1
C C2S 0.5387(3) 0.6523(5) 0.47921(16) 0.0244(8) Uani d . 1
H H2SC 0.5911 0.7353 0.4801 0.029 Uiso calc R 1
H H2SD 0.4866 0.6863 0.4508 0.029 Uiso calc R 1
O O1S 0.2943(2) 1.1970(3) 0.06515(12) 0.0361(7) Uani d . 1
H H1SB 0.2697 1.2685 0.0853 0.043 Uiso d R 1
H H1SA 0.2935 1.1143 0.0846 0.043 Uiso d R 1
O O2S 0.3325(2) 1.1386(3) -0.05314(12) 0.0400(8) Uani d . 1
H H2SB 0.3320 1.1593 -0.0175 0.048 Uiso d R 1
H H2SA 0.2824 1.1028 -0.0690 0.048 Uiso d R 1
O O3S 0.4956(2) 0.9449(3) -0.07949(13) 0.0357(7) Uani d . 1
H H3SB 0.5095 0.9881 -0.1111 0.043 Uiso d R 1
H H3SA 0.4491 1.0019 -0.0692 0.043 Uiso d R 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'
Hg Hg -2.3894 9.2266 '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
N1 Hg1 N1 . 3_655 175.08(16) yes
N1 Hg1 O3 . 3_655 111.75(10) ?
N1 Hg1 O3 3_655 3_655 71.55(10) ?
N1 Hg1 O3 . . 71.55(10) yes
N1 Hg1 O3 3_655 . 111.75(10) yes
O3 Hg1 O3 3_655 . 101.90(14) yes
N1 Hg1 O2 . . 71.51(10) yes
N1 Hg1 O2 3_655 . 105.36(10) yes
O3 Hg1 O2 3_655 . 88.33(10) ?
O3 Hg1 O2 . . 142.87(9) yes
N1 Hg1 O2 . 3_655 105.36(10) ?
N1 Hg1 O2 3_655 3_655 71.51(10) ?
O3 Hg1 O2 3_655 3_655 142.87(9) ?
O3 Hg1 O2 . 3_655 88.33(10) yes
O2 Hg1 O2 . 3_655 104.86(14) yes
C6 O2 Hg1 . . 113.0(2) ?
C7 O3 Hg1 . . 112.5(2) ?
C1 N1 C5 . . 121.3(4) ?
C1 N1 Hg1 . . 119.8(3) ?
C5 N1 Hg1 . . 118.8(3) ?
N1 C1 C2 . . 120.3(3) ?
N1 C1 C6 . . 117.2(3) ?
C2 C1 C6 . . 122.5(3) ?
C3 C2 C1 . . 119.6(4) ?
C3 C2 H2A . . 120.2 ?
C1 C2 H2A . . 120.2 ?
C2 C3 C4 . . 118.8(4) ?
C2 C3 H3A . . 120.6 ?
C4 C3 H3A . . 120.6 ?
C5 C4 C3 . . 119.7(4) ?
C5 C4 H4A . . 120.1 ?
C3 C4 H4A . . 120.1 ?
N1 C5 C4 . . 120.2(4) ?
N1 C5 C7 . . 117.3(4) ?
C4 C5 C7 . . 122.5(4) ?
O1 C6 O2 . . 124.9(4) yes
O1 C6 C1 . . 116.8(4) yes
O2 C6 C1 . . 118.3(3) yes
O4 C7 O3 . . 126.2(4) yes
O4 C7 C5 . . 115.8(4) yes
O3 C7 C5 . . 118.0(3) yes
C1S N1S C2S . . 111.6(3) ?
C1S N1S H1SC . . 109.3 ?
C2S N1S H1SC . . 109.3 ?
C1S N1S H1SD . . 109.3 ?
C2S N1S H1SD . . 109.3 ?
H1SC N1S H1SD . . 108.0 ?
N1S C1S C2S . 5_666 110.0(3) ?
N1S C1S H1SE . . 109.7 ?
C2S C1S H1SE 5_666 . 109.7 ?
N1S C1S H1SF . . 109.7 ?
C2S C1S H1SF 5_666 . 109.7 ?
H1SE C1S H1SF . . 108.2 ?
N1S C2S C1S . 5_666 109.1(3) ?
N1S C2S H2SC . . 109.9 ?
C1S C2S H2SC 5_666 . 109.9 ?
N1S C2S H2SD . . 109.9 ?
C1S C2S H2SD 5_666 . 109.9 ?
H2SC C2S H2SD . . 108.3 ?
H1SB O1S H1SA . . 108.5 ?
H2SB O2S H2SA . . 119.7 ?
H3SB O3S H3SA . . 99.4 ?
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
Hg1 N1 . 2.198(4) yes
Hg1 N1 3_655 2.198(4) ?
Hg1 O3 3_655 2.468(3) ?
Hg1 O2 . 2.471(3) yes
Hg1 O3 . 2.468(3) yes
Hg1 O2 3_655 2.471(3) ?
O1 C6 . 1.252(4) yes
O2 C6 . 1.257(5) yes
O3 C7 . 1.254(5) yes
O4 C7 . 1.253(4) yes
N1 C1 . 1.340(4) ?
N1 C5 . 1.356(5) ?
C1 C2 . 1.388(5) ?
C1 C6 . 1.527(5) ?
C2 C3 . 1.380(5) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.401(6) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.370(6) ?
C4 H4A . 0.9500 ?
C5 C7 . 1.519(5) ?
N1S C1S . 1.491(4) ?
N1S C2S . 1.491(5) ?
N1S H1SC . 0.9200 ?
N1S H1SD . 0.9200 ?
C1S C2S 5_666 1.523(5) ?
C1S H1SE . 0.9900 ?
C1S H1SF . 0.9900 ?
C2S C1S 5_666 1.523(5) ?
C2S H2SC . 0.9900 ?
C2S H2SD . 0.9900 ?
O1S H1SB . 0.8201 ?
O1S H1SA . 0.8198 ?
O2S H2SB . 0.8199 ?
O2S H2SA . 0.8200 ?
O3S H3SB . 0.8200 ?
O3S H3SA . 0.8200 ?
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
N1S H1SC O1 5_666 0.92 1.84 2.753(4) 169 yes
N1S H1SD O3S 3_655 0.92 1.99 2.765(4) 141 yes
O1S H1SB O4 8_665 0.82 2.01 2.823(4) 170 yes
O1S H1SA O4 1_555 0.82 1.93 2.734(4) 166 yes
O2S H2SB O1S 1_555 0.82 1.95 2.756(4) 165 yes
O2S H2SA O1 2_564 0.82 1.99 2.805(4) 174 yes
O3S H3SB O3 5_675 0.82 2.04 2.839(4) 164 yes
O3S H3SA O2S 1_555 0.82 1.97 2.792(4) 174 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
N1 Hg1 O2 C6 . . -3.7(3) yes
N1 Hg1 O2 C6 3_655 . -179.8(3) ?
O3 Hg1 O2 C6 3_655 . 109.9(3) ?
O3 Hg1 O2 C6 . . 2.2(3) ?
O2 Hg1 O2 C6 3_655 . -105.3(3) ?
N1 Hg1 O3 C7 . . -12.1(3) yes
N1 Hg1 O3 C7 3_655 . 164.0(3) ?
O3 Hg1 O3 C7 3_655 . -121.3(3) ?
O2 Hg1 O3 C7 . . -18.0(3) ?
O2 Hg1 O3 C7 3_655 . 94.7(3) ?
O3 Hg1 N1 C1 3_655 . -78.2(3) ?
O3 Hg1 N1 C1 . . -174.0(3) ?
O2 Hg1 N1 C1 . . 2.2(2) ?
O2 Hg1 N1 C1 3_655 . 103.1(3) ?
O3 Hg1 N1 C5 3_655 . 103.5(3) ?
O3 Hg1 N1 C5 . . 7.7(3) ?
O2 Hg1 N1 C5 . . -176.1(3) ?
O2 Hg1 N1 C5 3_655 . -75.2(3) ?
C5 N1 C1 C2 . . -1.1(5) ?
Hg1 N1 C1 C2 . . -179.3(3) ?
C5 N1 C1 C6 . . 177.5(3) ?
Hg1 N1 C1 C6 . . -0.8(4) ?
N1 C1 C2 C3 . . 2.2(6) ?
C6 C1 C2 C3 . . -176.3(3) ?
C1 C2 C3 C4 . . -1.6(6) ?
C2 C3 C4 C5 . . -0.1(6) ?
C1 N1 C5 C4 . . -0.6(6) ?
Hg1 N1 C5 C4 . . 177.6(3) ?
C1 N1 C5 C7 . . 178.1(3) ?
Hg1 N1 C5 C7 . . -3.6(4) ?
C3 C4 C5 N1 . . 1.2(6) ?
C3 C4 C5 C7 . . -177.5(3) ?
Hg1 O2 C6 O1 . . -176.1(3) yes
Hg1 O2 C6 C1 . . 4.7(4) ?
N1 C1 C6 O1 . . 177.7(3) ?
C2 C1 C6 O1 . . -3.8(5) ?
N1 C1 C6 O2 . . -3.0(5) ?
C2 C1 C6 O2 . . 175.5(4) ?
Hg1 O3 C7 O4 . . -167.1(3) yes
Hg1 O3 C7 C5 . . 14.4(4) ?
N1 C5 C7 O4 . . 172.9(3) ?
C4 C5 C7 O4 . . -8.4(5) ?
N1 C5 C7 O3 . . -8.5(5) ?
C4 C5 C7 O3 . . 170.3(4) ?
C2S N1S C1S C2S . 5_666 58.7(4) ?
C1S N1S C2S C1S . 5_666 -58.2(4) ?
