#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/22/2012254.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_2012254
loop_
_publ_author_name
'Alfonso, Montserrat'
'Wang, Yi'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 Hydrogen bonding in the inner-salt zwitterion and in two different
 charged forms of 5,6-bis(2-pyridyl)pyrazine-2,3-dicarboxylic acid
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1184
_journal_page_last               1188
_journal_paper_doi               10.1107/S0108270101010757
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C16 H10 N4 O4'
_chemical_formula_sum            'C16 H10 N4 O4'
_chemical_formula_weight         322.28
_chemical_name_systematic
;
3-Carboxy-5-(2-pyridinio)-6-(2-pyridyl)pyrazine-2-carboxylate
;
_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'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 110.070(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4770(10)
_cell_length_b                   13.523(2)
_cell_length_c                   10.0580(10)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19
_cell_measurement_theta_min      14
_cell_volume                     1338.5(3)
_computing_cell_refinement       STADI4
_computing_data_collection       'STADI4 (Stoe & Cie, 1997)'
_computing_data_reduction        'X-RED in STADI4'
_computing_molecular_graphics    'PLATON99 (Spek, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .996
_diffrn_measured_fraction_theta_max .996
_diffrn_measurement_device_type  'Stoe four-circle'
_diffrn_measurement_method       2θ/ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .039
_diffrn_reflns_av_sigmaI/netI    .109
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2356
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .119
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            pale_yellow
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          .46
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .11
_refine_diff_density_max         .17
_refine_diff_density_min         -.20
_refine_ls_extinction_coef       .014(2)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   .900
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         2336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .900
_refine_ls_R_factor_all          .120
_refine_ls_R_factor_gt           .049
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.029P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .092
_reflns_number_gt                1227
_reflns_number_total             2336
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd1159.cif
_cod_data_source_block           Ia
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2012254
_cod_database_fobs_code          2012254
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_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
_atom_site_type_symbol
O1 -.0606(2) .16027(19) .7237(2) .0590(7) Uani d . 1 . . O
O2 -.1543(2) .26898(18) .5480(2) .0416(6) Uani d . 1 . . O
O3 -.2703(2) .07332(17) .3870(2) .0471(7) Uani d . 1 . . O
O4 -.26759(19) .13092(17) .1812(2) .0417(6) Uani d . 1 . . O
N1 .1355(2) .16093(19) .5751(2) .0360(7) Uani d . 1 . . N
N2 .0163(2) .10376(19) .2992(2) .0350(7) Uani d . 1 . . N
N3 .4589(2) .12789(19) .5341(2) .0374(7) Uani d . 1 . . N
N4 .3489(2) .09486(19) .2720(3) .0355(7) Uani d . 1 . . N
C1 .0013(3) .1570(2) .5164(3) .0334(8) Uani d . 1 . . C
C2 -.0600(3) .1244(2) .3771(3) .0319(8) Uani d . 1 . . C
C3 .1531(3) .1131(2) .3540(3) .0291(8) Uani d . 1 . . C
C4 .2148(3) .1377(2) .4983(3) .0309(8) Uani d . 1 . . C
C5 .3616(3) .1443(2) .5897(3) .0312(7) Uani d . 1 . . C
C6 .3982(3) .1669(3) .7323(3) .0415(9) Uani d . 1 . . C
C7 .5345(3) .1726(3) .8139(4) .0449(9) Uani d . 1 . . C
C8 .6322(3) .1562(3) .7545(3) .0415(9) Uani d . 1 . . C
C9 .5914(3) .1339(3) .6132(3) .0396(9) Uani d . 1 . . C
C10 .2126(3) .0967(2) .2395(3) .0328(8) Uani d . 1 . . C
C11 .1310(3) .0839(3) .0996(3) .0427(9) Uani d . 1 . . C
C12 .1874(3) .0685(3) -.0032(4) .0474(10) Uani d . 1 . . C
C13 .3273(3) .0655(3) .0342(3) .0429(9) Uani d . 1 . . C
C14 .4054(3) .0804(3) .1723(3) .0420(9) Uani d . 1 . . C
C15 -.0765(3) .1949(3) .6078(3) .0383(9) Uani d . 1 . . C
C16 -.2119(3) .1083(2) .3103(3) .0335(8) Uani d . 1 . . C
H2O -.200(4) .315(3) .623(4) .095(13) Uiso d . 1 . . H
H3N .419(3) .112(2) .407(3) .071(11) Uiso d . 1 . . H
H6 .326(3) .171(2) .768(3) .044(9) Uiso d . 1 . . H
H7 .561(2) .1891(19) .912(3) .028(8) Uiso d . 1 . . H
H8 .723(3) .1572(19) .805(3) .025(8) Uiso d . 1 . . H
H9 .659(3) .120(2) .560(3) .059(10) Uiso d . 1 . . H
H11 .034(3) .087(2) .074(3) .056(10) Uiso d . 1 . . H
H12 .127(3) .059(2) -.104(3) .063(10) Uiso d . 1 . . H
H13 .368(3) .052(2) -.035(3) .039(9) Uiso d . 1 . . H
H14 .515(3) .076(2) .207(3) .065(10) Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
C15 O2 H2O 115.4(17)
C1 N1 C4 120.2(2)
C2 N2 C3 120.6(2)
C5 N3 C9 121.5(3)
C5 N3 H3N 115.7(14)
C9 N3 H3N 122.7(14)
C14 N4 C10 121.5(3)
C14 N4 H3N 123.8(13)
C10 N4 H3N 114.6(13)
N1 C1 C2 120.7(3)
N1 C1 C15 115.3(3)
C2 C1 C15 123.9(3)
N2 C2 C1 119.7(3)
N2 C2 C16 117.5(3)
C1 C2 C16 122.8(3)
N2 C3 C4 119.2(3)
N2 C3 C10 109.5(2)
C4 C3 C10 131.2(2)
N1 C4 C3 119.2(2)
N1 C4 C5 109.8(2)
C3 C4 C5 131.0(3)
N3 C5 C6 119.3(3)
N3 C5 C4 120.1(2)
C6 C5 C4 120.6(3)
C7 C6 C5 119.2(3)
C7 C6 H6 125.0(17)
C5 C6 H6 115.5(17)
C8 C7 C6 120.5(3)
C8 C7 H7 119.7(15)
C6 C7 H7 119.8(15)
C7 C8 C9 118.4(3)
C7 C8 H8 123.2(16)
C9 C8 H8 118.4(16)
N3 C9 C8 121.2(3)
N3 C9 H9 115.6(16)
C8 C9 H9 123.2(16)
N4 C10 C11 118.5(3)
N4 C10 C3 120.0(2)
C11 C10 C3 121.6(3)
C12 C11 C10 120.6(3)
C12 C11 H11 119.6(17)
C10 C11 H11 119.8(17)
C11 C12 C13 119.4(3)
C11 C12 H12 119.6(17)
C13 C12 H12 121.1(17)
C14 C13 C12 118.8(3)
C14 C13 H13 120.6(16)
C12 C13 H13 120.6(16)
N4 C14 C13 121.2(3)
N4 C14 H14 117.3(15)
C13 C14 H14 121.4(15)
O1 C15 O2 126.8(3)
O1 C15 C1 121.9(3)
O2 C15 C1 111.3(3)
O3 C16 O4 125.7(3)
O3 C16 C2 116.6(3)
O4 C16 C2 117.7(3)
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
O1 C15 . 1.214(3) ?
O2 C15 . 1.301(4) ?
O2 H2O . 1.20(4) ?
O3 C16 . 1.231(3) ?
O4 C16 . 1.265(3) ?
N1 C1 . 1.326(4) ?
N1 C4 . 1.352(3) ?
N2 C2 . 1.327(3) ?
N2 C3 . 1.354(3) ?
N3 C5 . 1.338(3) ?
N3 C9 . 1.345(3) ?
N3 H3N . 1.22(3) ?
N4 C14 . 1.342(3) ?
N4 C10 . 1.351(3) ?
N4 H3N . 1.32(3) ?
C1 C2 . 1.398(4) ?
C1 C15 . 1.512(4) ?
C2 C16 . 1.516(4) ?
C3 C4 . 1.411(4) ?
C3 C10 . 1.502(4) ?
C4 C5 . 1.499(4) ?
C5 C6 . 1.386(4) ?
C6 C7 . 1.383(4) ?
C6 H6 . .94(3) ?
C7 C8 . 1.368(4) ?
C7 H7 . .96(2) ?
C8 C9 . 1.370(4) ?
C8 H8 . .91(2) ?
C9 H9 . 1.03(3) ?
C10 C11 . 1.384(4) ?
C11 C12 . 1.372(4) ?
C11 H11 . .95(3) ?
C12 C13 . 1.383(4) ?
C12 H12 . 1.00(3) ?
C13 C14 . 1.364(4) ?
C13 H13 . .95(3) ?
C14 H14 . 1.08(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
O2 H2O O4 4_566 1.20(4) 1.29(4) 2.475(3) 169(3)
N3 H3N N4 . 1.22(3) 1.32(3) 2.528(3) 167(3)
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
C4 N1 C1 C2 3.1(5)
C4 N1 C1 C15 -173.8(3)
C3 N2 C2 C1 .7(4)
C3 N2 C2 C16 -177.6(3)
N1 C1 C2 N2 -4.8(5)
C15 C1 C2 N2 171.8(3)
N1 C1 C2 C16 173.4(3)
C15 C1 C2 C16 -10.0(5)
C2 N2 C3 C4 4.9(4)
C2 N2 C3 C10 -173.5(3)
C1 N1 C4 C3 2.5(4)
C1 N1 C4 C5 -178.0(3)
N2 C3 C4 N1 -6.5(4)
C10 C3 C4 N1 171.4(3)
N2 C3 C4 C5 174.1(3)
C10 C3 C4 C5 -8.0(6)
C9 N3 C5 C6 -.7(5)
C9 N3 C5 C4 179.6(3)
N1 C4 C5 N3 -177.5(3)
C3 C4 C5 N3 2.0(5)
N1 C4 C5 C6 2.8(4)
C3 C4 C5 C6 -177.7(3)
N3 C5 C6 C7 .4(5)
C4 C5 C6 C7 -179.9(3)
C5 C6 C7 C8 .0(6)
C6 C7 C8 C9 -.1(6)
C5 N3 C9 C8 .6(5)
C7 C8 C9 N3 -.2(5)
C14 N4 C10 C11 -.5(5)
C14 N4 C10 C3 180.0(3)
N2 C3 C10 N4 -174.9(3)
C4 C3 C10 N4 7.0(5)
N2 C3 C10 C11 5.6(4)
C4 C3 C10 C11 -172.5(3)
N4 C10 C11 C12 .8(5)
C3 C10 C11 C12 -179.6(3)
C10 C11 C12 C13 .2(6)
C11 C12 C13 C14 -1.5(6)
C10 N4 C14 C13 -.9(5)
C12 C13 C14 N4 1.9(5)
N1 C1 C15 O1 -57.6(4)
C2 C1 C15 O1 125.6(4)
N1 C1 C15 O2 119.9(3)
C2 C1 C15 O2 -56.8(4)
N2 C2 C16 O3 140.5(3)
C1 C2 C16 O3 -37.8(5)
N2 C2 C16 O4 -39.0(4)
C1 C2 C16 O4 142.8(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 352318
