#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/55/2005550.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_2005550
loop_
_publ_author_name
'Mrvos-Sermek, D.'
'Popovic, Z.'
'Matkovic-Calogovic, D.'
_publ_contact_author
;
      Dr Draginja Mrvoš-Sermek
      Laboratory of General and Inorganic Chemistry
      Faculty of Science, University of Zagreb
      P.O.B. 153
      Ul. kralja Zvonimira 8
      10000 Zagreb, Croatia
;
_publ_section_title
;
 Hydrogen Bonding in the 2,2'-Bipyridinium Salt of
 1,2,4,5-Benzenetetracarboxylic Acid (Pyromellitic Acid)
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2538
_journal_page_last               2541
_journal_paper_doi               10.1107/S0108270196003940
_journal_volume                  52
_journal_year                    1996
_chemical_formula_iupac
'C10 H9 N2 + , 1/2C10 H4 O8 2- , 1/2C10 H6 O8'
_chemical_formula_moiety         'C20 H14 N2 O8'
_chemical_formula_structural
'(C10 H8 N2 H) 1/2(C6 H2 (COO)4 H2) 1/2(C6 H2 (COO)4 H4)'
_chemical_formula_sum            'C20 H14 N2 O8'
_chemical_formula_weight         410.33
_chemical_name_systematic
;
2,2'-Bipyridinium salt of benzene-1,2,4,5-tetracarboxylic acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                69.09(4)
_cell_angle_beta                 87.72(3)
_cell_angle_gamma                84.06(6)
_cell_formula_units_Z            2
_cell_length_a                   7.912(4)
_cell_length_b                   10.307(5)
_cell_length_c                   11.533(9)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16.83
_cell_measurement_theta_min      8.60
_cell_volume                     873.8(10)
_computing_cell_refinement       DIF4
_computing_data_collection       'DIF4 (Stoe & Cie, 1992a)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1992b)'
_computing_molecular_graphics
'ORTEP92 (Vicković, 1994), PLUTON (Spek, 1993)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Philips PW1100 updated by Stoe'
_diffrn_measurement_method       ω/θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'x-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8255
_diffrn_reflns_theta_max         30.09
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        5
_diffrn_standards_interval_time  100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Transparent
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.008
_refine_ls_goodness_of_fit_obs   1.140
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_restrained_S_obs      1.140
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_obs          0.0434
_refine_ls_shift/esd_max         0.124
_refine_ls_shift/esd_mean        0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0680P)²+0.0338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1250
_refine_ls_wR_factor_obs         0.1032
_reflns_number_observed          3010
_reflns_number_total             5135
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            sk1020.cif
_cod_data_source_block           BPYPMA
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.0338P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.0338P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        873.8(9)
_cod_database_code               2005550
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_type_symbol
C1 1 0.0276(2) 0.62280(12) 0.40103(12) 0.0255(3) Uani d C
C2 1 0.1299(2) 0.49917(13) 0.41489(12) 0.0255(3) Uani d C
C3 1 -0.1015(2) 0.62203(13) 0.48657(13) 0.0284(3) Uani d C
C4 1 0.0551(2) 0.75264(13) 0.29338(13) 0.0290(3) Uani d C
C5 1 0.2758(2) 0.48896(13) 0.32964(13) 0.0292(3) Uani d C
O1 1 -0.0287(2) 0.86506(10) 0.30435(11) 0.0424(3) Uani d O
O2 1 0.1459(2) 0.75279(11) 0.20732(10) 0.0455(3) Uani d O
O3 1 0.41073(14) 0.53972(11) 0.35046(11) 0.0397(3) Uani d O
O4 1 0.2677(2) 0.43037(12) 0.25633(11) 0.0469(3) Uani d O
C6 1 0.8823(2) 0.55003(13) 0.07401(12) 0.0248(3) Uani d C
C7 1 0.9622(2) 0.64554(12) -0.02758(13) 0.0248(3) Uani d C
C8 1 0.9239(2) 0.40887(13) 0.09747(13) 0.0279(3) Uani d C
C9 1 0.7521(2) 0.58270(14) 0.16282(13) 0.0301(3) Uani d C
C10 1 0.9376(2) 0.80409(13) -0.07402(14) 0.0314(3) Uani d C
O5 1 0.66599(15) 0.48694(11) 0.22418(11) 0.0477(3) Uani d O
O6 1 0.7345(2) 0.70153(11) 0.17194(11) 0.0443(3) Uani d O
O7 1 1.0042(2) 0.86988(10) -0.17144(11) 0.0499(3) Uani d O
O8 1 0.8470(2) 0.86584(11) -0.01146(13) 0.0527(4) Uani d O
C11 1 0.4017(2) -0.0148(2) 0.34354(14) 0.0343(3) Uani d C
N1 1 0.3085(2) 0.05731(14) 0.40365(13) 0.0431(4) Uani d N
C12 1 0.2344(3) -0.0162(2) 0.5088(2) 0.0535(5) Uani d C
C13 1 0.2501(3) -0.1596(2) 0.5568(2) 0.0559(5) Uani d C
C14 1 0.3468(3) -0.2318(2) 0.4951(2) 0.0499(5) Uani d C
C15 1 0.4251(2) -0.1589(2) 0.3858(2) 0.0422(4) Uani d C
C16 1 0.4782(2) 0.07304(14) 0.22683(14) 0.0311(3) Uani d C
N2 1 0.4422(2) 0.21122(12) 0.19672(12) 0.0339(3) Uani d N
C17 1 0.5000(2) 0.3058(2) 0.09424(15) 0.0381(4) Uani d C
C18 1 0.6020(2) 0.2631(2) 0.0134(2) 0.0391(4) Uani d C
C19 1 0.6441(2) 0.1220(2) 0.0411(2) 0.0422(4) Uani d C
C20 1 0.5822(2) 0.0269(2) 0.1473(2) 0.0410(4) Uani d C
H3 1 -0.1755(19) 0.7080(16) 0.4772(14) 0.028(4) Uiso d H
H1O 1 -0.0089(26) 0.9493(22) 0.2441(19) 0.061(6) Uiso d H
H3O 1 0.5079(28) 0.5258(21) 0.2976(20) 0.064(6) Uiso d H
H8 1 0.8694(19) 0.3450(16) 0.1668(14) 0.027(4) Uiso d H
H8O 1 0.8112(29) 0.7900(24) 0.0742(22) 0.070(7) Uiso d H
H12 1 0.1569(27) 0.0409(21) 0.5462(20) 0.060(6) Uiso d H
H13 1 0.1958(26) -0.2076(21) 0.6361(20) 0.062(6) Uiso d H
H14 1 0.3563(25) -0.3344(21) 0.5241(18) 0.056(6) Uiso d H
H15 1 0.4893(25) -0.2054(21) 0.3402(19) 0.052(5) Uiso d H
H17 1 0.4598(24) 0.4003(20) 0.0856(17) 0.053(6) Uiso d H
H18 1 0.6431(25) 0.3326(21) -0.0594(19) 0.055(6) Uiso d H
H19 1 0.7163(24) 0.0878(19) -0.0169(17) 0.047(5) Uiso d H
H20 1 0.6014(23) -0.0717(20) 0.1665(17) 0.051(5) Uiso d H
HN2 1 0.3749(25) 0.2426(20) 0.2496(18) 0.056(6) Uiso d H
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'
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
5 0 -6
1 -3 -5
-5 3 2
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
C3 C1 C2 . . 119.21(12) yes
C3 C1 C4 . . 120.85(12) yes
C2 C1 C4 . . 119.92(11) yes
C3 C2 C1 2_566 . 119.76(11) yes
C3 C2 C5 2_566 . 116.57(12) yes
C1 C2 C5 . . 123.64(12) yes
C2 C3 C1 2_566 . 121.02(12) yes
C2 C3 H3 2_566 . 119.0(9) no
C1 C3 H3 . . 120.0(9) no
O2 C4 O1 . . 124.39(13) yes
O2 C4 C1 . . 122.75(13) yes
O1 C4 C1 . . 112.86(12) yes
O4 C5 O3 . . 125.04(13) yes
O4 C5 C2 . . 121.71(15) yes
O3 C5 C2 . . 113.06(13) yes
C4 O1 H1O . . 116.6(13) no
C5 O3 H3O . . 111.8(12) no
C8 C6 C7 . . 117.64(11) yes
C8 C6 C9 . . 114.71(12) yes
C7 C6 C9 . . 127.65(12) yes
C8 C7 C6 2_765 . 117.51(12) yes
C8 C7 C10 2_765 . 114.35(12) yes
C6 C7 C10 . . 128.13(12) yes
C6 C8 C7 . 2_765 124.85(12) yes
C6 C8 H8 . . 117.0(9) no
C7 C8 H8 2_765 . 118.2(9) no
O5 C9 O6 . . 122.78(13) yes
O5 C9 C6 . . 116.52(13) yes
O6 C9 C6 . . 120.70(13) yes
O7 C10 O8 . . 121.20(14) yes
O7 C10 C7 . . 118.91(13) yes
O8 C10 C7 . . 119.89(13) yes
C9 O6 H8O . . 108.2(10) no
C10 O8 H8O . . 109.0(12) no
N1 C11 C15 . . 123.56(15) yes
N1 C11 C16 . . 114.07(14) yes
C15 C11 C16 . . 122.37(14) yes
C12 N1 C11 . . 116.9(2) yes
N1 C12 C13 . . 123.2(2) yes
N1 C12 H12 . . 114.4(12) no
C13 C12 H12 . . 122.1(12) no
C14 C13 C12 . . 119.3(2) yes
C14 C13 H13 . . 121.4(13) no
C12 C13 H13 . . 119.3(13) no
C13 C14 C15 . . 119.0(2) yes
C13 C14 H14 . . 121.7(12) no
C15 C14 H14 . . 119.2(12) no
C14 C15 C11 . . 118.0(2) yes
C14 C15 H15 . . 121.0(12) no
C11 C15 H15 . . 120.9(12) no
N2 C16 C20 . . 117.82(14) yes
N2 C16 C11 . . 115.69(13) yes
C20 C16 C11 . . 126.49(14) yes
C17 N2 C16 . . 123.64(13) yes
C17 N2 HN2 . . 118.0(12) no
C16 N2 HN2 . . 118.3(12) no
N2 C17 C18 . . 119.83(15) yes
N2 C17 H17 . . 113.0(11) no
C18 C17 H17 . . 127.1(11) no
C17 C18 C19 . . 118.65(15) yes
C17 C18 H18 . . 118.7(12) no
C19 C18 H18 . . 122.6(12) no
C20 C19 C18 . . 120.21(14) yes
C20 C19 H19 . . 119.3(11) no
C18 C19 H19 . . 120.5(11) no
C19 C20 C16 . . 119.84(15) yes
C19 C20 H20 . . 122.6(11) no
C16 C20 H20 . . 117.4(11) 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 C3 . 1.390(2) yes
C1 C2 . 1.399(2) yes
C1 C4 . 1.494(2) yes
C2 C3 2_566 1.388(2) yes
C2 C5 . 1.506(2) yes
C3 C2 2_566 1.388(2) no
C3 H3 . 0.98(2) no
C4 O2 . 1.201(2) yes
C4 O1 . 1.318(2) yes
C5 O4 . 1.208(2) yes
C5 O3 . 1.302(2) yes
O1 H1O . 0.92(2) no
O3 H3O . 0.99(2) no
C6 C8 . 1.388(2) yes
C6 C7 . 1.410(2) yes
C6 C9 . 1.521(2) yes
C7 C8 2_765 1.391(2) yes
C7 C10 . 1.521(2) yes
C8 C7 2_765 1.391(2) no
C8 H8 . 0.96(2) no
C9 O5 . 1.241(2) yes
C9 O6 . 1.259(2) yes
C10 O7 . 1.218(2) yes
C10 O8 . 1.277(2) yes
O6 H8O . 1.34(2) no
O8 H8O . 1.07(2) no
C11 N1 . 1.339(2) yes
C11 C15 . 1.382(2) yes
C11 C16 . 1.475(2) yes
N1 C12 . 1.329(2) yes
C12 C13 . 1.374(3) yes
C12 H12 . 1.00(2) no
C13 C14 . 1.365(3) yes
C13 H13 . 0.98(2) no
C14 C15 . 1.377(3) yes
C14 H14 . 0.98(2) no
C15 H15 . 0.93(2) no
C16 N2 . 1.342(2) yes
C16 C20 . 1.384(2) yes
N2 C17 . 1.335(2) yes
N2 HN2 . 0.92(2) no
C17 C18 . 1.369(2) yes
C17 H17 . 0.96(2) no
C18 C19 . 1.380(2) yes
C18 H18 . 0.96(2) no
C19 C20 . 1.377(2) yes
C19 H19 . 1.00(2) no
C20 H20 . 0.96(2) 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_4
_geom_torsion
_geom_torsion_publ_flag
C3 C1 C2 C3 . 2_566 -0.1(3) no
C4 C1 C2 C3 . 2_566 -178.53(14) no
C3 C1 C2 C5 . . -178.45(15) no
C4 C1 C2 C5 . . 3.1(2) no
C2 C1 C3 C2 . 2_566 0.1(3) no
C4 C1 C3 C2 . 2_566 178.51(14) no
C3 C1 C4 O2 . . -167.7(2) no
C2 C1 C4 O2 . . 10.7(2) no
C3 C1 C4 O1 . . 13.0(2) no
C2 C1 C4 O1 . . -168.54(14) no
C3 C2 C5 O4 2_566 . 73.6(2) no
C1 C2 C5 O4 . . -108.0(2) no
C3 C2 C5 O3 2_566 . -101.7(2) no
C1 C2 C5 O3 . . 76.7(2) no
C8 C6 C7 C8 . 2_765 0.5(2) no
C9 C6 C7 C8 . 2_765 -178.99(15) no
C8 C6 C7 C10 . . 179.06(15) no
C9 C6 C7 C10 . . -0.4(3) no
C7 C6 C8 C7 . 2_765 -0.5(3) no
C9 C6 C8 C7 . 2_765 179.01(15) no
C8 C6 C9 O5 . . -17.8(2) no
C7 C6 C9 O5 . . 161.6(2) no
C8 C6 C9 O6 . . 162.26(15) no
C7 C6 C9 O6 . . -18.2(3) no
C8 C7 C10 O7 2_765 . 6.3(2) no
C6 C7 C10 O7 . . -172.3(2) no
C8 C7 C10 O8 2_765 . -174.2(2) no
C6 C7 C10 O8 . . 7.2(3) no
C15 C11 N1 C12 . . -0.6(3) no
C16 C11 N1 C12 . . 179.2(2) no
C11 N1 C12 C13 . . 0.2(3) no
N1 C12 C13 C14 . . 0.4(4) no
C12 C13 C14 C15 . . -0.5(3) no
C13 C14 C15 C11 . . 0.0(3) no
N1 C11 C15 C14 . . 0.6(3) no
C16 C11 C15 C14 . . -179.3(2) no
N1 C11 C16 N2 . . -0.9(2) no
C15 C11 C16 N2 . . 179.0(2) no
N1 C11 C16 C20 . . 178.9(2) no
C15 C11 C16 C20 . . -1.3(3) no
C20 C16 N2 C17 . . 0.6(3) no
C11 C16 N2 C17 . . -179.7(2) no
C16 N2 C17 C18 . . -0.1(3) no
N2 C17 C18 C19 . . -0.6(3) no
C17 C18 C19 C20 . . 0.8(3) no
C18 C19 C20 C16 . . -0.3(3) no
N2 C16 C20 C19 . . -0.4(3) no
C11 C16 C20 C19 . . 179.9(2) no
