#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/55/2225543.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_2225543
loop_
_publ_author_name
'Kaluderović, Goran N.'
'Mohamad Eshkourfu, Rabia O.'
'Gómez-Ruiz, Santiago'
'Mitić, Dragana'
'Andelković, Katarina K.'
_publ_section_title
;
 2,2'-{1,1'-[2,2'-Oxalylbis(hydrazin-2-yl-1-ylidene)]diethylidyne}dipyridinium
 bis(perchlorate) dihydrate
;
_journal_coeditor_code           GK2261
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o904
_journal_page_last               o905
_journal_paper_doi               10.1107/S1600536810010238
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H18 N6 O2 2+, 2Cl O4 -, 2H2 O'
_chemical_formula_moiety         'C16 H18 N6 O2 2+, 2(Cl O4 -), 2(H2 O)'
_chemical_formula_sum            'C16 H22 Cl2 N6 O12'
_chemical_formula_weight         561.3
_chemical_name_systematic
;
2,2'-{1,1'-[2,2'-Oxalylbis(hydrazin-2-yl-1-ylidene)]diethylidyne}dipyridinium
bis(perchlorate) dihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90.240(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0166(3)
_cell_length_b                   15.6855(5)
_cell_length_c                   10.1152(4)
_cell_measurement_reflns_used    4422
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      32.22
_cell_measurement_theta_min      2.89
_cell_volume                     1113.26(7)
_computing_cell_refinement
;
CrysAlis Pro  (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis Pro  (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis Pro  (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 16.356
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction XcaliburS CCD'
_diffrn_measurement_method       'ω scans and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12596
_diffrn_reflns_theta_full        30.5
_diffrn_reflns_theta_max         30.5
_diffrn_reflns_theta_min         2.9
_exptl_absorpt_coefficient_mu    0.37
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis Pro; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.483
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3402
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0575P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1054
_reflns_number_gt                2504
_reflns_number_total             3402
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gk2261.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225543
_cod_database_fobs_code          2225543
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
Cl Cl1 -0.06740(7) 0.17109(3) 0.03091(5) 0.02258(12) Uani d . 1 . .
O O1 0.5097(2) -0.08816(8) 0.10597(12) 0.0239(3) Uani d . 1 . .
O O2 -0.0958(2) 0.23504(9) -0.06811(15) 0.0357(4) Uani d . 1 . .
O O3 -0.2032(3) 0.18404(10) 0.13518(17) 0.0553(6) Uani d . 1 . .
O O4 -0.0935(2) 0.08764(8) -0.02205(14) 0.0331(3) Uani d . 1 . .
O O5 0.1188(3) 0.17823(11) 0.0853(3) 0.0705(7) Uani d . 1 . .
O O6 0.3496(2) -0.14953(9) 0.35088(15) 0.0285(3) Uani d D 1 . .
N N1 0.2466(2) -0.01871(9) 0.50693(15) 0.0167(3) Uani d . 1 . .
N N2 0.3686(2) 0.03179(9) 0.27403(15) 0.0190(2) Uani d . 1 . .
N N3 0.4253(2) 0.05006(10) 0.14877(14) 0.0190(2) Uani d . 1 . .
C C1 0.2678(2) 0.06619(11) 0.48485(17) 0.0168(3) Uani d . 1 . .
C C2 0.2139(3) 0.12184(11) 0.58310(18) 0.0206(4) Uani d . 1 . .
H H2 0.2278 0.1815 0.5705 0.025 Uiso calc R 1 . .
C C3 0.1395(3) 0.09094(12) 0.70044(18) 0.0226(4) Uani d . 1 . .
H H3 0.1008 0.1295 0.7675 0.027 Uiso calc R 1 . .
C C4 0.1214(2) 0.00423(12) 0.72004(18) 0.0214(4) Uani d . 1 . .
H H4 0.0714 -0.0176 0.8004 0.026 Uiso calc R 1 . .
C C5 0.1775(2) -0.05004(11) 0.62031(17) 0.0193(4) Uani d . 1 . .
H H5 0.1672 -0.11 0.632 0.023 Uiso calc R 1 . .
C C6 0.3414(2) 0.09391(11) 0.35522(17) 0.0174(3) Uani d . 1 . .
C C7 0.3775(3) 0.18669(11) 0.3335(2) 0.0271(4) Uani d . 1 . .
H H7A 0.4424 0.1947 0.2488 0.041 Uiso calc R 1 . .
H H7B 0.4579 0.2088 0.4052 0.041 Uiso calc R 1 . .
H H7C 0.2559 0.2174 0.3323 0.041 Uiso calc R 1 . .
C C8 0.4826(2) -0.01508(11) 0.07098(18) 0.0188(3) Uani d . 1 . .
H H1N 0.279(3) -0.0545(14) 0.449(2) 0.026(4) Uiso d . 1 . .
H H3N 0.401(3) 0.0985(14) 0.118(2) 0.026(4) Uiso d . 1 . .
H H6A 0.388(4) -0.1348(17) 0.2784(19) 0.049(6) Uiso d D 1 . .
H H6B 0.295(4) -0.1971(13) 0.351(3) 0.049(6) Uiso d D 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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
O5 Cl1 O4 . . 109.55(10) ?
O5 Cl1 O2 . . 109.96(11) ?
O4 Cl1 O2 . . 111.30(9) ?
O5 Cl1 O3 . . 108.40(14) ?
O4 Cl1 O3 . . 108.69(10) ?
O2 Cl1 O3 . . 108.87(9) ?
H6A O6 H6B . . 114(3) ?
C5 N1 C1 . . 122.70(15) ?
C5 N1 H1N . . 116.7(15) ?
C1 N1 H1N . . 120.6(15) ?
C6 N2 N3 . . 118.61(14) ?
C8 N3 N2 . . 118.15(15) ?
C8 N3 H3N . . 122.0(14) ?
N2 N3 H3N . . 118.4(15) ?
N1 C1 C2 . . 118.18(16) ?
N1 C1 C6 . . 118.26(15) ?
C2 C1 C6 . . 123.53(16) ?
C1 C2 C3 . . 120.13(17) ?
C1 C2 H2 . . 119.9 ?
C3 C2 H2 . . 119.9 ?
C4 C3 C2 . . 120.17(17) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C5 C4 C3 . . 118.46(17) ?
C5 C4 H4 . . 120.8 ?
C3 C4 H4 . . 120.8 ?
N1 C5 C4 . . 120.35(16) ?
N1 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
N2 C6 C1 . . 113.35(15) ?
N2 C6 C7 . . 128.13(17) ?
C1 C6 C7 . . 118.52(15) ?
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 ?
O1 C8 N3 . . 126.18(17) ?
O1 C8 C8 . 3_655 122.6(2) ?
N3 C8 C8 . 3_655 111.16(18) ?
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
Cl1 O5 . 1.4198(17) ?
Cl1 O4 . 1.4259(14) ?
Cl1 O2 . 1.4309(14) ?
Cl1 O3 . 1.4386(17) ?
O1 C8 . 1.214(2) ?
O6 H6A . 0.815(17) ?
O6 H6B . 0.839(17) ?
N1 C5 . 1.340(2) ?
N1 C1 . 1.359(2) ?
N1 H1N . 0.84(2) ?
N2 C6 . 1.289(2) ?
N2 N3 . 1.360(2) ?
N3 C8 . 1.352(2) ?
N3 H3N . 0.84(2) ?
C1 C2 . 1.377(2) ?
C1 C6 . 1.477(2) ?
C2 C3 . 1.386(3) ?
C2 H2 . 0.95 ?
C3 C4 . 1.381(3) ?
C3 H3 . 0.95 ?
C4 C5 . 1.379(3) ?
C4 H4 . 0.95 ?
C5 H5 . 0.95 ?
C6 C7 . 1.493(2) ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
C8 C8 3_655 1.532(4) ?
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 H1N O6 . 0.84(2) 1.86(2) 2.690(2) 168(2) yes
N1 H1N N2 . 0.84(2) 2.32(2) 2.632(2) 102(2) yes
N3 H3N O5 . 0.84(2) 2.36(2) 3.011(2) 134(2) yes
N3 H3N O1 3_655 0.84(2) 2.36(2) 2.686(2) 104(2) yes
O6 H6A O1 . 0.82(2) 2.08(2) 2.889(2) 173(2) yes
O6 H6A N2 . 0.82(2) 2.62(3) 2.952(2) 106(2) no
O6 H6B O3 2_545 0.84(2) 1.98(2) 2.809(2) 171(2) yes
C2 H2 O5 5_555 0.95 2.33 3.206(2) 152 no
C4 H4 O4 3_556 0.95 2.50 3.384(2) 155 no
C5 H5 O2 2_545 0.95 2.56 3.460(2) 157 no
C7 H7A N3 . 0.98 2.49 2.864(2) 103 no
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 N2 N3 C8 . . . . 169.62(16) ?
C5 N1 C1 C2 . . . . -0.7(2) ?
C5 N1 C1 C6 . . . . -178.72(16) ?
N1 C1 C2 C3 . . . . -0.3(3) ?
C6 C1 C2 C3 . . . . 177.63(16) ?
C1 C2 C3 C4 . . . . 0.9(3) ?
C2 C3 C4 C5 . . . . -0.5(3) ?
C1 N1 C5 C4 . . . . 1.1(3) ?
C3 C4 C5 N1 . . . . -0.5(3) ?
N3 N2 C6 C1 . . . . 176.07(14) ?
N3 N2 C6 C7 . . . . -4.8(3) ?
N1 C1 C6 N2 . . . . 3.3(2) ?
C2 C1 C6 N2 . . . . -174.65(17) ?
N1 C1 C6 C7 . . . . -175.92(16) ?
C2 C1 C6 C7 . . . . 6.1(3) ?
N2 N3 C8 O1 . . . . -9.0(3) ?
N2 N3 C8 C8 . . . 3_655 172.93(16) ?
