##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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data_global
_audit_creation_method     ?
_journal_data_validation_number     ?
_journal_date_recd_electronic     2001-05-15
_journal_date_accepted     2001-06-27
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2001
_journal_volume     57
_journal_issue     10
_journal_page_first     1184
_journal_page_last     1188
_journal_paper_category     FO
_publ_contact_author_name     'Professor Helen Stoeckli-Evans'
_publ_contact_author_address
;
Institut de Chimie
Universite de Neuchatel
Avenue de Bellevaux 51
Case Postale 2
CH-2007 Neuchatel
Switzerland
;
_publ_contact_author_email     'helen.stoeckli-evans@unine.ch'
_publ_contact_author_fax     '+41 32 718 25 11'
_publ_contact_author_phone     '+41 32 718 24 26'
_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
;
loop_
    _publ_author_name
    _publ_author_address
    'Alfonso, Montserrat'
;
Institut de Chimie
Université de Neuchâtel
Avenue de Bellevaux 51
Case Postale 2
CH-2007 Neuchâtel
Switzerland
;
    'Wang, Yi'
;
Institut de Chimie
Université de Neuchâtel
Avenue de Bellevaux 51
Case Postale 2
CH-2007 Neuchâtel
Switzerland
;
    'Stoeckli-Evans, Helen'
;
Institut de Chimie
Université de Neuchâtel
Avenue de Bellevaux 51
Case Postale 2
CH-2007 Neuchâtel
Switzerland
;
data_Ia
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
3-Carboxy-5-(2-pyridinio)-6-(2-pyridyl)pyrazine-2-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H10 N4 O4'
_chemical_formula_sum     'C16 H10 N4 O4'
_chemical_formula_weight     322.28
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
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'
_cell_length_a     10.4770(10)
_cell_length_b     13.523(2)
_cell_length_c     10.0580(10)
_cell_angle_alpha     90
_cell_angle_beta     110.070(10)
_cell_angle_gamma     90
_cell_volume     1338.5(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     20
_cell_measurement_theta_min     14
_cell_measurement_theta_max     19
_cell_measurement_temperature     293(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     pale_yellow
_exptl_crystal_size_max      .46
_exptl_crystal_size_mid      .30
_exptl_crystal_size_min      .11
_exptl_crystal_density_diffrn     1.599
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     664
_exptl_absorpt_coefficient_mu      .119
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
  ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Stoe four-circle'
_diffrn_measurement_method     2θ/ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2356
_diffrn_reflns_av_R_equivalents      .039
_diffrn_reflns_av_sigmaI/netI      .109
_diffrn_reflns_theta_min     2.07
_diffrn_reflns_theta_max     24.98
_diffrn_reflns_theta_full     24.98
_diffrn_measured_fraction_theta_max      .996
_diffrn_measured_fraction_theta_full      .996
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     0
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     60
_diffrn_standards_decay_%     <2
_refine_special_details
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and
  goodness of fit S are based on F², conventional R-factors R are based
  on F, with F set to zero for negative F². The threshold expression of
  F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
  not relevant to the choice of reflections for refinement.  R-factors based
  on F² are statistically about twice as large as those based on F, and R-
  factors based on ALL data will be even larger.
;
_reflns_number_total     2336
_reflns_number_gt     1227
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .120
_refine_ls_R_factor_gt      .049
_refine_ls_wR_factor_ref      .092
_refine_ls_goodness_of_fit_ref      .900
_refine_ls_restrained_S_all      .900
_refine_ls_number_reflns     2336
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                'calc w = 1/[σ²(Fo²)+(0.029P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .17
_refine_diff_density_min      -.20
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_extinction_coef      .014(2)
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'
_computing_data_collection     'STADI4 (Stoe & Cie, 1997)'
_computing_cell_refinement     'STADI4'
_computing_data_reduction     'X-RED in STADI4'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON99 (Spek, 1990)'
_computing_publication_material     'SHELXL97'
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
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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
    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_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
    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_
    _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)
data_II
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
6-Carboxy-5-carboxylatopyrazine-2,3-diyldi-2-pyridinium chloride 2.25 hydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H11 N4 O4 + , Cl - , 2.25H2 O'
_chemical_formula_sum     'C16 H15.5 Cl N4 O6.25'
_chemical_formula_weight     399.27
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'I 2/a'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y, -z'
    'x+1/2, y+1/2, z+1/2'
    '-x+1, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y, z'
    '-x+1/2, -y+1/2, -z+1/2'
    'x, -y+1/2, z+1/2'
_cell_length_a     19.5883(17)
_cell_length_b     8.0623(5)
_cell_length_c     22.936(2)
_cell_angle_alpha     90
_cell_angle_beta     90.559(11)
_cell_angle_gamma     90
_cell_volume     3622.0(5)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     5000
_cell_measurement_theta_min     2.08
_cell_measurement_theta_max     25.93
_cell_measurement_temperature     293(2)
_exptl_crystal_description     rod
_exptl_crystal_colour     colourless
_exptl_crystal_size_max      .5
_exptl_crystal_size_mid      .2
_exptl_crystal_size_min      .1
_exptl_crystal_density_diffrn     1.464
_exptl_crystal_density_meas     none
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1652
_exptl_absorpt_coefficient_mu      .255
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
  ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Stoe IPDS'
_diffrn_measurement_method     'φ oscillation'
_diffrn_detector_area_resol_mean     0.81\%A
_diffrn_reflns_number     13718
_diffrn_reflns_av_R_equivalents      .055
_diffrn_reflns_av_sigmaI/netI      .070
_diffrn_reflns_theta_min     2.08
_diffrn_reflns_theta_max     25.93
_diffrn_reflns_theta_full     25.93
_diffrn_measured_fraction_theta_max      .990
_diffrn_measured_fraction_theta_full      .990
_diffrn_reflns_limit_h_min     -24
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -28
_diffrn_reflns_limit_l_max     28
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and
  goodness of fit S are based on F², conventional R-factors R are based
  on F, with F set to zero for negative F². The threshold expression of
  F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
  not relevant to the choice of reflections for refinement.  R-factors based
  on F² are statistically about twice as large as those based on F, and R-
  factors based on ALL data will be even larger.
;
_reflns_number_total     3488
_reflns_number_gt     1943
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .081
_refine_ls_R_factor_gt      .039
_refine_ls_wR_factor_ref      .093
_refine_ls_goodness_of_fit_ref      .823
_refine_ls_restrained_S_all      .823
_refine_ls_number_reflns     3488
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w = 1/[σ²(Fo²)+(0.05P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max      .027
_refine_ls_shift/su_mean      .001
_refine_diff_density_max      .63
_refine_diff_density_min      -.26
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'Cl' 'Cl'  .1484  .1585
                         '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'
_computing_data_collection     'EXPOSE (Stoe & Cie, 2000)'
_computing_cell_refinement     'CELL (Stoe & Cie, 2000)'
_computing_data_reduction     'INTEGRATE (Stoe & Cie, 2000)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON99 (Spek, 1990)'
_computing_publication_material     'SHELXL97'
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  .00022(9)  .1926(2)  .33297(7)  .0504(5) Uani d . 1 . . O
    O2  -.04931(9)  .4384(2)  .31389(8)  .0468(4) Uani d . 1 . . O
    H2O  -.0711(17)  .427(4)  .3513(16)  .098(11) Uiso d . 1 . . H
    O3  -.12559(9)  .1414(3)  .14811(8)  .0677(6) Uani d . 1 . . O
    O4  -.12505(7)  .1999(2)  .24294(7)  .0445(4) Uani d . 1 . . O
    N1  .07729(9)  .3448(2)  .23364(8)  .0335(5) Uani d . 1 . . N
    N2  -.00305(9)  .2937(2)  .13643(8)  .0332(4) Uani d . 1 . . N
    N3  .20722(9)  .4782(3)  .21689(8)  .0362(5) Uani d . 1 . . N
    H3N  .1784(14)  .552(4)  .2371(11)  .059(8) Uiso d . 1 . . H
    N4  .04464(11)  .2977(3)  .02828(8)  .0419(5) Uani d . 1 . . N
    H4N  .0143(14)  .218(4)  .0390(11)  .056(9) Uiso d . 1 . . H
    C1  .01098(10)  .3102(3)  .23847(9)  .0299(5) Uani d . 1 . . C
    C2  -.02847(10)  .2726(3)  .18944(9)  .0315(5) Uani d . 1 . . C
    C3  .06192(11)  .3391(3)  .13071(9)  .0327(5) Uani d . 1 . . C
    C4  .10405(10)  .3533(3)  .17995(9)  .0316(5) Uani d . 1 . . C
    C5  .17977(11)  .3684(3)  .17965(10)  .0347(5) Uani d . 1 . . C
    C6  .22210(13)  .2671(4)  .14841(12)  .0462(7) Uani d . 1 . . C
    H6  .2041(12)  .194(3)  .1250(11)  .043(8) Uiso d . 1 . . H
    C7  .29176(13)  .2780(4)  .15607(13)  .0529(7) Uani d . 1 . . C
    H7  .3200(15)  .208(4)  .1362(12)  .068(9) Uiso d . 1 . . H
    C8  .31845(13)  .3931(4)  .19409(12)  .0492(7) Uani d . 1 . . C
    H8  .3652(14)  .403(3)  .2006(10)  .051(7) Uiso d . 1 . . H
    C9  .27469(12)  .4937(4)  .22394(12)  .0438(7) Uani d . 1 . . C
    H9  .2894(12)  .575(3)  .2516(11)  .043(7) Uiso d . 1 . . H
    C10  .08151(12)  .3768(3)  .06990(10)  .0367(6) Uani d . 1 . . C
    C11  .12867(14)  .4934(4)  .05341(12)  .0500(7) Uani d . 1 . . C
    H11  .1562(14)  .547(4)  .0826(12)  .060(8) Uiso d . 1 . . H
    C12  .13715(17)  .5273(5)  -.00524(13)  .0633(9) Uani d . 1 . . C
    H12  .1709(15)  .608(4)  -.0163(12)  .063(8) Uiso d . 1 . . H
    C13  .09857(17)  .4461(4)  -.04616(13)  .0629(9) Uani d . 1 . . C
    H14  .0993(16)  .469(4)  -.0863(15)  .089(10) Uiso d . 1 . . H
    C14  .05233(17)  .3294(4)  -.02876(12)  .0562(8) Uani d . 1 . . C
    H13  .0220(14)  .270(4)  -.0548(12)  .064(9) Uiso d . 1 . . H
    C15  -.01420(11)  .3048(3)  .30038(10)  .0357(6) Uani d . 1 . . C
    C16  -.09956(11)  .1984(3)  .19289(11)  .0389(6) Uani d . 1 . . C
    Cl1  .12673(3)  .94713(9)  .07395(3)  .0540(2) Uani d . 1 . . Cl
    O1W  .44735(11)  .9286(3)  .04654(11)  .0664(6) Uani d . 1 . . O
    H1A  .4215(18)  .931(4)  .0177(16)  .084(12) Uiso d . 1 . . H
    H1B  .4188(19)  .899(5)  .0784(18)  .106(13) Uiso d . 1 . . H
    O2W  .2565(4)  .7120(7)  .1020(5)  .089(3) Uani d P  .62(2) A 1 O
    H21  .228(4)  .789(11)  .088(3)  .09(2) Uiso d P  .62(2) A 1 H
    H22  .288(4)  .774(10)  .107(4)  .11(3) Uiso d P  .62(2) A 1 H
    O3W  .2358(5)  .770(2)  .1446(9)  .115(8) Uani d P  .38(2) A 2 O
    H31  .286(5)  .786(10)  .145(4)  .06(2) Uiso d P  .38(2) A 2 H
    H32  .210(6)  .846(15)  .115(7)  .11(4) Uiso d P  .38(2) A 2 H
    O4W  .2500  .1391(9)  .0000  .137(4) Uani d SP  .50 B 2 O
    H41  .2187  .0920  .0189  .100 Uiso d P  .50 C 2 H
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 . 1.205(3) ?
    O2 C15 . 1.317(3) ?
    O2 H2O .  .97(4) ?
    O3 C16 . 1.231(3) ?
    O4 C16 . 1.256(3) ?
    N1 C1 . 1.334(3) ?
    N1 C4 . 1.345(3) ?
    N2 C2 . 1.329(3) ?
    N2 C3 . 1.332(3) ?
    N3 C9 . 1.336(3) ?
    N3 C5 . 1.339(3) ?
    N3 H3N .  .94(3) ?
    N4 C14 . 1.343(3) ?
    N4 C10 . 1.351(3) ?
    N4 H4N .  .91(3) ?
    C1 C2 . 1.392(3) ?
    C1 C15 . 1.508(3) ?
    C2 C16 . 1.518(3) ?
    C3 C4 . 1.397(3) ?
    C3 C10 . 1.482(3) ?
    C4 C5 . 1.488(3) ?
    C5 C6 . 1.371(3) ?
    C6 C7 . 1.377(4) ?
    C6 H6 .  .87(3) ?
    C7 C8 . 1.373(4) ?
    C7 H7 .  .92(3) ?
    C8 C9 . 1.369(4) ?
    C8 H8 .  .93(3) ?
    C9 H9 .  .95(3) ?
    C10 C11 . 1.373(4) ?
    C11 C12 . 1.384(4) ?
    C11 H11 .  .96(3) ?
    C12 C13 . 1.366(5) ?
    C12 H12 .  .96(3) ?
    C13 C14 . 1.368(5) ?
    C13 H14 .  .94(3) ?
    C14 H13 .  .96(3) ?
    O1W H1A .  .83(4) ?
    O1W H1B .  .95(4) ?
    O2W H21 .  .89(9) ?
    O2W H22 .  .81(9) ?
    O2W H31 . 1.29(8) ?
    O2W H32 . 1.45(12) ?
    O3W H21 . 1.32(6) ?
    O3W H22 . 1.34(7) ?
    O3W H31 . 1.00(10) ?
    O3W H32 . 1.05(14) ?
    O4W H41 .  .8444 ?
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
    C15 O2 H2O . . 112(2) ?
    C1 N1 C4 . . 118.39(18) ?
    C2 N2 C3 . . 119.48(18) ?
    C9 N3 C5 . . 122.0(2) ?
    C9 N3 H3N . . 118.5(16) ?
    C5 N3 H3N . . 119.4(16) ?
    C14 N4 C10 . . 122.3(3) ?
    C14 N4 H4N . . 118.5(17) ?
    C10 N4 H4N . . 119.2(17) ?
    N1 C1 C2 . . 120.78(19) ?
    N1 C1 C15 . . 114.33(18) ?
    C2 C1 C15 . . 124.77(19) ?
    N2 C2 C1 . . 120.09(19) ?
    N2 C2 C16 . . 116.74(19) ?
    C1 C2 C16 . . 123.09(19) ?
    N2 C3 C4 . . 120.02(19) ?
    N2 C3 C10 . . 113.93(19) ?
    C4 C3 C10 . . 126.0(2) ?
    N1 C4 C3 . . 120.24(19) ?
    N1 C4 C5 . . 113.94(19) ?
    C3 C4 C5 . . 125.7(2) ?
    N3 C5 C6 . . 119.1(2) ?
    N3 C5 C4 . . 116.4(2) ?
    C6 C5 C4 . . 124.2(2) ?
    C5 C6 C7 . . 119.9(3) ?
    C5 C6 H6 . . 118.9(16) ?
    C7 C6 H6 . . 121.2(16) ?
    C8 C7 C6 . . 119.7(3) ?
    C8 C7 H7 . . 120.3(19) ?
    C6 C7 H7 . . 120.0(19) ?
    C9 C8 C7 . . 118.8(3) ?
    C9 C8 H8 . . 119.1(16) ?
    C7 C8 H8 . . 122.1(16) ?
    N3 C9 C8 . . 120.5(3) ?
    N3 C9 H9 . . 116.0(14) ?
    C8 C9 H9 . . 123.5(14) ?
    N4 C10 C11 . . 119.0(2) ?
    N4 C10 C3 . . 115.2(2) ?
    C11 C10 C3 . . 125.5(2) ?
    C10 C11 C12 . . 119.4(3) ?
    C10 C11 H11 . . 119.4(16) ?
    C12 C11 H11 . . 121.2(16) ?
    C13 C12 C11 . . 120.1(3) ?
    C13 C12 H12 . . 121.3(17) ?
    C11 C12 H12 . . 118.6(17) ?
    C12 C13 C14 . . 119.5(3) ?
    C12 C13 H14 . . 125(2) ?
    C14 C13 H14 . . 116(2) ?
    N4 C14 C13 . . 119.7(3) ?
    N4 C14 H13 . . 115.7(17) ?
    C13 C14 H13 . . 124.5(17) ?
    O1 C15 O2 . . 126.0(2) ?
    O1 C15 C1 . . 121.9(2) ?
    O2 C15 C1 . . 112.0(2) ?
    O3 C16 O4 . . 126.9(2) ?
    O3 C16 C2 . . 118.4(2) ?
    O4 C16 C2 . . 114.6(2) ?
    H1A O1W H1B . . 105(3) ?
    H21 O2W H22 . . 95(7) ?
    H21 O2W H31 . . 103(6) ?
    H22 O2W H31 . . 42(6) ?
    H21 O2W H32 . . 33(6) ?
    H22 O2W H32 . . 90(7) ?
    H31 O2W H32 . . 78(7) ?
    H21 O3W H22 . . 57(5) ?
    H21 O3W H31 . . 96(6) ?
    H22 O3W H31 . . 41(5) ?
    H21 O3W H32 . . 40(6) ?
    H22 O3W H32 . . 87(7) ?
    H31 O3W H32 . . 114(8) ?
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
    C4 N1 C1 C2 . . . . 4.4(3) ?
    C4 N1 C1 C15 . . . . -179.5(2) ?
    C3 N2 C2 C1 . . . . 4.9(3) ?
    C3 N2 C2 C16 . . . . -171.9(2) ?
    N1 C1 C2 N2 . . . . -9.6(3) ?
    C15 C1 C2 N2 . . . . 174.7(2) ?
    N1 C1 C2 C16 . . . . 167.0(2) ?
    C15 C1 C2 C16 . . . . -8.7(4) ?
    C2 N2 C3 C4 . . . . 4.3(3) ?
    C2 N2 C3 C10 . . . . -173.4(2) ?
    C1 N1 C4 C3 . . . . 4.9(3) ?
    C1 N1 C4 C5 . . . . -171.7(2) ?
    N2 C3 C4 N1 . . . . -9.5(3) ?
    C10 C3 C4 N1 . . . . 167.9(2) ?
    N2 C3 C4 C5 . . . . 166.7(2) ?
    C10 C3 C4 C5 . . . . -15.9(4) ?
    C9 N3 C5 C6 . . . . 1.0(4) ?
    C9 N3 C5 C4 . . . . 174.7(2) ?
    N1 C4 C5 N3 . . . . -45.6(3) ?
    C3 C4 C5 N3 . . . . 138.0(2) ?
    N1 C4 C5 C6 . . . . 127.8(3) ?
    C3 C4 C5 C6 . . . . -48.6(4) ?
    N3 C5 C6 C7 . . . .  .7(4) ?
    C4 C5 C6 C7 . . . . -172.5(2) ?
    C5 C6 C7 C8 . . . . -1.4(4) ?
    C6 C7 C8 C9 . . . .  .5(4) ?
    C5 N3 C9 C8 . . . . -1.9(4) ?
    C7 C8 C9 N3 . . . . 1.1(4) ?
    C14 N4 C10 C11 . . . .  -.2(4) ?
    C14 N4 C10 C3 . . . . 174.3(2) ?
    N2 C3 C10 N4 . . . . -26.8(3) ?
    C4 C3 C10 N4 . . . . 155.6(2) ?
    N2 C3 C10 C11 . . . . 147.2(2) ?
    C4 C3 C10 C11 . . . . -30.3(4) ?
    N4 C10 C11 C12 . . . .  .2(4) ?
    C3 C10 C11 C12 . . . . -173.6(2) ?
    C10 C11 C12 C13 . . . .  .4(4) ?
    C11 C12 C13 C14 . . . . -1.0(5) ?
    C10 N4 C14 C13 . . . .  -.4(4) ?
    C12 C13 C14 N4 . . . . 1.0(4) ?
    N1 C1 C15 O1 . . . . -72.5(3) ?
    C2 C1 C15 O1 . . . . 103.4(3) ?
    N1 C1 C15 O2 . . . . 104.1(2) ?
    C2 C1 C15 O2 . . . . -80.0(3) ?
    N2 C2 C16 O3 . . . . 9.8(3) ?
    C1 C2 C16 O3 . . . . -166.9(2) ?
    N2 C2 C16 O4 . . . . -171.5(2) ?
    C1 C2 C16 O4 . . . . 11.8(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 Cl1 4_445  .97(4) 2.05(4) 2.9996(18) 168(3)
    N3 H3N O4 4_455  .94(3) 1.65(3) 2.582(3) 167(2)
    N4 H4N O1W 6_565  .91(3) 1.78(3) 2.674(3) 169(3)
    O1W H1A Cl1 2  .83(4) 2.30(4) 3.112(3) 167(3)
    O1W H1B O3 6_665  .95(4) 1.86(4) 2.802(3) 170(3)
    O2W H21 Cl1 .  .89(9) 2.38(10) 3.230(6) 160(6)
    O2W H22 O3 6_665  .81(9) 2.04(10) 2.794(6) 155(8)
    O3W H31 O3 6_665 1.00(10) 1.82(10) 2.809(9) 168(7)
    O3W H32 Cl1 . 1.05(14) 2.04(14) 3.028(9) 157(9)
    O4W H41 Cl1 1_545  .84 2.50 3.344(3) 179
data_IIIa
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
6-carboxy-5-carboxylatopyrazine-2,3-diyldi-2-pyridinium perchlorate trihydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H11 N4 O4 + , Cl O4 - , 3H2 O'
_chemical_formula_sum     'C16 H17 Cl N4 O11'
_chemical_formula_weight     476.79
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 2/c'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
_cell_length_a     6.1401(7)
_cell_length_b     15.6358(12)
_cell_length_c     10.7154(8)
_cell_angle_alpha     90
_cell_angle_beta     106.934(8)
_cell_angle_gamma     90
_cell_volume     984.13(15)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5000
_cell_measurement_theta_min     1.65
_cell_measurement_theta_max     26.05
_cell_measurement_temperature     223(2)
_exptl_crystal_description     block
_exptl_crystal_colour     'pale yellow'
_exptl_crystal_size_max      .36
_exptl_crystal_size_mid      .35
_exptl_crystal_size_min      .26
_exptl_crystal_density_diffrn     1.609
_exptl_crystal_density_meas     none
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     492
_exptl_absorpt_coefficient_mu      .266
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
  ?
;
_diffrn_ambient_temperature     223(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Stoe IPDS'
_diffrn_measurement_method     'φ oscillation'
_diffrn_detector_area_resol_mean     0.82\%A
_diffrn_reflns_number     7650
_diffrn_reflns_av_R_equivalents      .033
_diffrn_reflns_av_sigmaI/netI      .028
_diffrn_reflns_theta_min     2.38
_diffrn_reflns_theta_max     25.94
_diffrn_reflns_theta_full     25.94
_diffrn_measured_fraction_theta_max      .990
_diffrn_measured_fraction_theta_full      .990
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and
  goodness of fit S are based on F², conventional R-factors R are based
  on F, with F set to zero for negative F². The threshold expression of
  F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
  not relevant to the choice of reflections for refinement.  R-factors based
  on F² are statistically about twice as large as those based on F, and R-
  factors based on ALL data will be even larger.
;
_reflns_number_total     1914
_reflns_number_gt     1419
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .057
_refine_ls_R_factor_gt      .040
_refine_ls_wR_factor_ref      .115
_refine_ls_goodness_of_fit_ref     1.017
_refine_ls_restrained_S_all     1.017
_refine_ls_number_reflns     1914
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0786P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .18
_refine_diff_density_min      -.58
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'Cl' 'Cl'  .1484  .1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'EXPOSE (Stoe & Cie, 2000)'
_computing_cell_refinement     'CELL (Stoe & Cie, 2000)'
_computing_data_reduction     'X-RED in STADI4 (Stoe & Cie, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON99 (Spek, 1990)'
_computing_publication_material     'SHELXL97'
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  .3233(3)  -.03491(9)  .10493(15)  .0487(4) Uani d . 1 . . O
    O2  .1347(3)  -.12771(9)  .18880(15)  .0464(4) Uani d . 1 . . O
    H2O  .0000  -.130(3)  .2500  .080(12) Uiso d S 1 . . H
    N1  .0965(3)  .09766(9)  .15109(14)  .0297(4) Uani d . 1 . . N
    N2  .1821(3)  .24553(10)  .03765(14)  .0321(4) Uani d . 1 . . N
    H2N  .285(4)  .2022(15)  .051(2)  .047(6) Uiso d . 1 . . H
    C1  .0643(3)  .02366(11)  .20518(16)  .0298(4) Uani d . 1 . . C
    C2  .0346(3)  .17086(11)  .19261(16)  .0276(4) Uani d . 1 . . C
    C3  .0324(3)  .24614(11)  .10802(16)  .0291(4) Uani d . 1 . . C
    C4  -.1222(4)  .31173(12)  .09105(19)  .0362(5) Uani d . 1 . . C
    H4  -.229(4)  .3116(13)  .1394(19)  .035(5) Uiso d . 1 . . H
    C5  -.1203(4)  .37640(13)  .0023(2)  .0447(5) Uani d . 1 . . C
    H5  -.224(5)  .4201(16)  -.010(2)  .054(7) Uiso d . 1 . . H
    C6  .0372(4)  .37459(14)  -.0665(2)  .0456(5) Uani d . 1 . . C
    H6  .045(4)  .4182(16)  -.125(2)  .053(6) Uiso d . 1 . . H
    C7  .1876(4)  .30819(13)  -.04735(19)  .0402(5) Uani d . 1 . . C
    H7  .299(4)  .3010(14)  -.096(2)  .045(6) Uiso d . 1 . . H
    C8  .1833(4)  -.05126(12)  .16216(18)  .0351(4) Uani d . 1 . . C
    Cl1  .5000  .44850(5)  .2500  .0616(3) Uani d S 1 . . Cl
    O11  .5000  .35788(14)  .2500  .0530(6) Uani d S 1 . . O
    O12  .5187(7)  .4638(2)  .4036(3)  .0658(10) Uani d P  .50 . . O
    O13  .2741(12)  .4793(5)  .2005(7)  .100(3) Uani d P  .50 . . O
    O14  .3338(13)  .4887(5)  .2673(6)  .093(2) Uani d P  .50 . . O
    O1W  .5044(3)  .12538(10)  .06311(16)  .0441(4) Uani d . 1 . . O
    H1A  .552(5)  .1116(17)  .000(3)  .072(9) Uiso d . 1 . . H
    H1B  .442(5)  .0793(18)  .080(2)  .054(7) Uiso d . 1 . . H
    O2W  .5000  .25145(16)  .7500  .0713(8) Uani d S 1 . . O
    H2WA  .3585  .2104  .7136  .100 Uiso d . 1 . . H
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C8 . 1.219(2) ?
    O2 C8 . 1.284(2) ?
    O2 H2O . 1.1965(19) ?
    N1 C2 . 1.323(2) ?
    N1 C1 . 1.334(2) ?
    N2 C7 . 1.345(2) ?
    N2 C3 . 1.348(2) ?
    N2 H2N .  .91(2) ?
    C1 C1 2 1.410(4) ?
    C1 C8 . 1.522(3) ?
    C2 C2 2 1.413(3) ?
    C2 C3 . 1.483(2) ?
    C3 C4 . 1.373(3) ?
    C4 C5 . 1.391(3) ?
    C4 H4 .  .95(2) ?
    C5 C6 . 1.376(3) ?
    C5 H5 .  .92(3) ?
    C6 C7 . 1.365(3) ?
    C6 H6 .  .94(2) ?
    C7 H7 .  .98(2) ?
    Cl1 O14 . 1.258(6) ?
    Cl1 O14 2_655 1.258(6) ?
    Cl1 O11 . 1.417(2) ?
    Cl1 O13 2_655 1.418(6) ?
    Cl1 O13 . 1.418(6) ?
    Cl1 O12 . 1.634(3) ?
    Cl1 O12 2_655 1.634(3) ?
    O12 O14 . 1.615(8) ?
    O13 O14 .  .718(7) ?
    O1W H1A .  .84(3) ?
    O1W H1B .  .86(3) ?
    O2W H2WA . 1.0590 ?
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
    C8 O2 H2O . . 113(2) ?
    C2 N1 C1 . . 120.69(15) ?
    C7 N2 C3 . . 121.96(18) ?
    C7 N2 H2N . . 119.7(14) ?
    C3 N2 H2N . . 118.3(14) ?
    N1 C1 C1 . 2 118.63(10) ?
    N1 C1 C8 . . 113.01(16) ?
    C1 C1 C8 2 . 128.32(11) ?
    N1 C2 C2 . 2 118.77(10) ?
    N1 C2 C3 . . 115.67(15) ?
    C2 C2 C3 2 . 125.48(10) ?
    N2 C3 C4 . . 119.27(17) ?
    N2 C3 C2 . . 116.75(16) ?
    C4 C3 C2 . . 123.80(16) ?
    C3 C4 C5 . . 119.36(19) ?
    C3 C4 H4 . . 119.3(12) ?
    C5 C4 H4 . . 121.4(12) ?
    C6 C5 C4 . . 119.9(2) ?
    C6 C5 H5 . . 120.4(16) ?
    C4 C5 H5 . . 119.7(16) ?
    C7 C6 C5 . . 119.05(19) ?
    C7 C6 H6 . . 119.3(15) ?
    C5 C6 H6 . . 121.6(15) ?
    N2 C7 C6 . . 120.44(19) ?
    N2 C7 H7 . . 115.9(13) ?
    C6 C7 H7 . . 123.6(13) ?
    O1 C8 O2 . . 123.39(17) ?
    O1 C8 C1 . . 117.52(17) ?
    O2 C8 C1 . . 119.08(17) ?
    O14 Cl1 O14 . 2_655 120.0(8) ?
    O14 Cl1 O11 . . 120.0(4) ?
    O14 Cl1 O11 2_655 . 120.0(4) ?
    O14 Cl1 O13 . 2_655 121.5(4) ?
    O14 Cl1 O13 2_655 2_655 30.4(4) ?
    O11 Cl1 O13 . 2_655 109.9(3) ?
    O14 Cl1 O13 . . 30.4(4) ?
    O14 Cl1 O13 2_655 . 121.5(4) ?
    O11 Cl1 O13 . . 109.9(3) ?
    O13 Cl1 O13 2_655 . 140.3(6) ?
    O14 Cl1 O12 . . 66.4(3) ?
    O14 Cl1 O12 2_655 . 104.7(3) ?
    O11 Cl1 O12 . . 98.43(13) ?
    O13 Cl1 O12 2_655 . 78.5(4) ?
    O13 Cl1 O12 . . 95.8(4) ?
    O14 Cl1 O12 . 2_655 104.7(3) ?
    O14 Cl1 O12 2_655 2_655 66.4(3) ?
    O11 Cl1 O12 . 2_655 98.43(13) ?
    O13 Cl1 O12 2_655 2_655 95.8(4) ?
    O13 Cl1 O12 . 2_655 78.5(4) ?
    O12 Cl1 O12 . 2_655 163.1(3) ?
    O14 O12 Cl1 . . 45.6(2) ?
    O14 O13 Cl1 . . 62.4(8) ?
    O13 O14 Cl1 . . 87.2(9) ?
    O13 O14 O12 . . 150.7(12) ?
    Cl1 O14 O12 . . 68.0(4) ?
    H1A O1W H1B . . 104(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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C2 N1 C1 C1 . . . 2 8.5(3) ?
    C2 N1 C1 C8 . . . . -169.67(16) ?
    C1 N1 C2 C2 . . . 2 9.4(3) ?
    C1 N1 C2 C3 . . . . -167.37(16) ?
    C7 N2 C3 C4 . . . . 1.2(3) ?
    C7 N2 C3 C2 . . . . 176.52(16) ?
    N1 C2 C3 N2 . . . . -29.8(2) ?
    C2 C2 C3 N2 2 . . . 153.7(2) ?
    N1 C2 C3 C4 . . . . 145.31(18) ?
    C2 C2 C3 C4 2 . . . -31.2(3) ?
    N2 C3 C4 C5 . . . .  -.4(3) ?
    C2 C3 C4 C5 . . . . -175.34(18) ?
    C3 C4 C5 C6 . . . .  -.7(3) ?
    C4 C5 C6 C7 . . . .  .9(3) ?
    C3 N2 C7 C6 . . . . -1.0(3) ?
    C5 C6 C7 N2 . . . .  -.1(3) ?
    N1 C1 C8 O1 . . . . 12.7(2) ?
    C1 C1 C8 O1 2 . . . -165.2(2) ?
    N1 C1 C8 O2 . . . . -168.12(16) ?
    C1 C1 C8 O2 2 . . . 14.0(3) ?
    O14 Cl1 O12 O14 2_655 . . . 116.7(8) ?
    O11 Cl1 O12 O14 . . . . -119.1(4) ?
    O13 Cl1 O12 O14 2_655 . . . 132.2(4) ?
    O13 Cl1 O12 O14 . . . . -8.0(7) ?
    O12 Cl1 O12 O14 2_655 . . . 60.9(4) ?
    O14 Cl1 O13 O14 2_655 . . . -96.5(14) ?
    O11 Cl1 O13 O14 . . . . 115.8(11) ?
    O13 Cl1 O13 O14 2_655 . . . -64.2(11) ?
    O12 Cl1 O13 O14 . . . . 14.6(12) ?
    O12 Cl1 O13 O14 2_655 . . . -149.3(12) ?
    Cl1 O13 O14 O12 . . . . -31(2) ?
    O14 Cl1 O14 O13 2_655 . . . 102.1(12) ?
    O11 Cl1 O14 O13 . . . . -77.9(12) ?
    O13 Cl1 O14 O13 2_655 . . . 137.5(11) ?
    O12 Cl1 O14 O13 . . . . -164.1(13) ?
    O12 Cl1 O14 O13 2_655 . . . 31.1(13) ?
    O14 Cl1 O14 O12 2_655 . . . -93.9(3) ?
    O11 Cl1 O14 O12 . . . . 86.1(3) ?
    O13 Cl1 O14 O12 2_655 . . . -58.4(5) ?
    O13 Cl1 O14 O12 . . . . 164.1(13) ?
    O12 Cl1 O14 O12 2_655 . . . -164.8(2) ?
    Cl1 O12 O14 O13 . . . . 34(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 O2 2 1.1965(19) 1.1965(19) 2.392(3) 177(4)
    N2 H2N O1W .  .91(2) 1.78(3) 2.684(2) 172(2)
    O1W H1A O1 3_655  .84(3) 1.94(3) 2.734(2) 156(3)
    O1W H1B O1 .  .86(3) 1.98(3) 2.830(2) 172(3)
    O2W H2WA O2 4_556 1.06 1.85 2.889(2) 167
data_IIIb
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
6-carboxy-5-carboxylatopyrazine-2,3-diyldi-2-pyridinium hexafluorophosphate
trihydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H11 N4 O4 + , P F6 - , 3H2 O'
_chemical_formula_sum     'C16 H17 F6 N4 O7 P'
_chemical_formula_weight     522.31
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 2/c'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
_cell_length_a     6.1910(6)
_cell_length_b     15.6564(11)
_cell_length_c     10.8349(10)
_cell_angle_alpha     90
_cell_angle_beta     106.400(11)
_cell_angle_gamma     90
_cell_volume     1007.48(15)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5000
_cell_measurement_theta_min     1.65
_cell_measurement_theta_max     26.05
_cell_measurement_temperature     293(2)
_exptl_crystal_description     rod
_exptl_crystal_colour     pale_yellow
_exptl_crystal_size_max      .70
_exptl_crystal_size_mid      .20
_exptl_crystal_size_min      .15
_exptl_crystal_density_diffrn     1.722
_exptl_crystal_density_meas     none
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     532
_exptl_absorpt_coefficient_mu      .242
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
  ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Stoe IPDS'
_diffrn_measurement_method     'φ oscillation'
_diffrn_detector_area_resol_mean     0.81\%A
_diffrn_reflns_number     7713
_diffrn_reflns_av_R_equivalents      .029
_diffrn_reflns_av_sigmaI/netI      .019
_diffrn_reflns_theta_min     3.26
_diffrn_reflns_theta_max     25.87
_diffrn_reflns_theta_full     25.87
_diffrn_measured_fraction_theta_max      .987
_diffrn_measured_fraction_theta_full      .987
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and
  goodness of fit S are based on F², conventional R-factors R are based
  on F, with F set to zero for negative F². The threshold expression of
  F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
  not relevant to the choice of reflections for refinement.  R-factors based
  on F² are statistically about twice as large as those based on F, and R-
  factors based on ALL data will be even larger.
;
_reflns_number_total     1944
_reflns_number_gt     1628
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .050
_refine_ls_R_factor_gt      .044
_refine_ls_wR_factor_ref      .152
_refine_ls_goodness_of_fit_ref     1.197
_refine_ls_restrained_S_all     1.197
_refine_ls_number_reflns     1944
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.1018P)²+0.1313P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .25
_refine_diff_density_min      -.83
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'P' 'P'  .1023  .0942
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F'  .0171  .0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'EXPOSE (Stoe & Cie, 2000)'
_computing_cell_refinement     'CELL (Stoe & Cie, 2000)'
_computing_data_reduction     'INTEGRATE (Stoe & Cie, 2000)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON99 (Spek, 1990)'
_computing_publication_material     'SHELXL97'
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
    N1  .4040(3)  .09425(10)  .34843(16)  .0286(4) Uani d . 1 . . N
    N2  .3208(3)  .24229(11)  .46196(15)  .0302(4) Uani d . 1 . . N
    H2N  .214(6)  .2008(19)  .451(3)  .049(7) Uiso d . 1 . . H
    O1  .1776(3)  -.03754(11)  .39442(18)  .0473(5) Uani d . 1 . . O
    O2  .3656(3)  -.13016(10)  .31136(18)  .0478(5) Uani d . 1 . . O
    H2O  .5000  -.124(4)  .2500  .101(19) Uiso d S 1 . . H
    C1  .4356(3)  .02054(13)  .29450(18)  .0293(4) Uani d . 1 . . C
    C2  .4658(3)  .16771(12)  .30675(17)  .0263(4) Uani d . 1 . . C
    C3  .4688(3)  .24235(13)  .39136(17)  .0265(4) Uani d . 1 . . C
    C4  .6261(4)  .30703(14)  .40890(19)  .0334(5) Uani d . 1 . . C
    H4  .747(5)  .3146(17)  .359(3)  .045(7) Uiso d . 1 . . H
    C5  .6266(4)  .37137(15)  .4977(2)  .0407(5) Uani d . 1 . . C
    H5  .725(5)  .4157(19)  .508(3)  .048(8) Uiso d . 1 . . H
    C6  .4718(4)  .36946(15)  .5673(2)  .0411(6) Uani d . 1 . . C
    H6  .474(5)  .413(2)  .634(3)  .053(8) Uiso d . 1 . . H
    C7  .3190(4)  .30384(14)  .54757(19)  .0363(5) Uani d . 1 . . C
    H7  .215(5)  .2940(17)  .592(3)  .042(7) Uiso d . 1 . . H
    C8  .3177(4)  -.05412(14)  .3380(2)  .0361(5) Uani d . 1 . . C
    O1W  -.0014(3)  .12351(12)  .43619(18)  .0434(5) Uani d . 1 . . O
    H1WA  -.047(6)  .110(2)  .495(4)  .069(11) Uiso d . 1 . . H
    H1WB  .059(7)  .076(2)  .416(4)  .074(11) Uiso d . 1 . . H
    O2W  .0000  -.2445(3)  .2500  .1238(18) Uani d S 1 . . O
    H2WA  -.1451  -.2321  .2136  .100 Uiso d . 1 . . H
    P1  .0000  .45753(5)  .2500  .0331(3) Uani d S 1 . . P
    F1  .0000  .35438(12)  .2500  .0437(5) Uani d S 1 . . F
    F2  .0000  .55917(14)  .2500  .0610(6) Uani d S 1 . . F
    F3  .0436(3)  .45621(10)  .40178(13)  .0532(5) Uani d . 1 . . F
    F4  .2650(2)  .45701(10)  .26905(15)  .0523(4) Uani d . 1 . . F
_geom_special_details
;
  All esds (except the esd in the dihedral angle between two l.s. planes)
  are estimated using the full covariance matrix.  The cell esds are taken
  into account individually in the estimation of esds in distances, angles
  and torsion angles; correlations between esds in cell parameters are only
  used when they are defined by crystal symmetry.  An approximate (isotropic)
  treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    N1 C2 . 1.331(3) ?
    N1 C1 . 1.333(3) ?
    N2 C7 . 1.340(3) ?
    N2 C3 . 1.349(3) ?
    N2 H2N .  .91(3) ?
    O1 C8 . 1.222(3) ?
    O2 C8 . 1.279(3) ?
    O2 H2O . 1.206(5) ?
    C1 C1 2_655 1.414(4) ?
    C1 C8 . 1.522(3) ?
    C2 C2 2_655 1.409(4) ?
    C2 C3 . 1.482(3) ?
    C3 C4 . 1.380(3) ?
    C4 C5 . 1.393(3) ?
    C4 H4 . 1.05(3) ?
    C5 C6 . 1.377(4) ?
    C5 H5 .  .91(3) ?
    C6 C7 . 1.372(4) ?
    C6 H6 .  .99(3) ?
    C7 H7 .  .92(3) ?
    O1W H1WA .  .79(4) ?
    O1W H1WB .  .89(4) ?
    O2W H2WA .  .8946 ?
    P1 F3 2 1.5897(14) ?
    P1 F3 . 1.5897(14) ?
    P1 F2 . 1.591(2) ?
    P1 F4 2 1.5948(14) ?
    P1 F4 . 1.5948(14) ?
    P1 F1 . 1.615(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
    C2 N1 C1 . . 120.49(17) ?
    C7 N2 C3 . . 122.12(19) ?
    C7 N2 H2N . . 116.9(18) ?
    C3 N2 H2N . . 121.0(19) ?
    C8 O2 H2O . . 107(3) ?
    N1 C1 C1 . 2_655 118.69(12) ?
    N1 C1 C8 . . 112.74(17) ?
    C1 C1 C8 2_655 . 128.56(12) ?
    N1 C2 C2 . 2_655 118.84(11) ?
    N1 C2 C3 . . 115.22(16) ?
    C2 C2 C3 2_655 . 125.84(11) ?
    N2 C3 C4 . . 119.21(18) ?
    N2 C3 C2 . . 117.27(17) ?
    C4 C3 C2 . . 123.29(17) ?
    C3 C4 C5 . . 119.3(2) ?
    C3 C4 H4 . . 126.3(15) ?
    C5 C4 H4 . . 114.3(15) ?
    C6 C5 C4 . . 119.8(2) ?
    C6 C5 H5 . . 119.8(19) ?
    C4 C5 H5 . . 120.3(19) ?
    C7 C6 C5 . . 119.1(2) ?
    C7 C6 H6 . . 119.7(18) ?
    C5 C6 H6 . . 121.1(18) ?
    N2 C7 C6 . . 120.4(2) ?
    N2 C7 H7 . . 112.7(17) ?
    C6 C7 H7 . . 126.8(17) ?
    O1 C8 O2 . . 123.6(2) ?
    O1 C8 C1 . . 117.53(19) ?
    O2 C8 C1 . . 118.9(2) ?
    H1WA O1W H1WB . . 104(4) ?
    F3 P1 F3 2 . 178.51(13) ?
    F3 P1 F2 2 . 90.75(6) ?
    F3 P1 F2 . . 90.75(6) ?
    F3 P1 F4 2 2 89.88(8) ?
    F3 P1 F4 . 2 90.11(8) ?
    F2 P1 F4 . 2 90.30(7) ?
    F3 P1 F4 2 . 90.11(8) ?
    F3 P1 F4 . . 89.88(8) ?
    F2 P1 F4 . . 90.30(7) ?
    F4 P1 F4 2 . 179.41(13) ?
    F3 P1 F1 2 . 89.25(6) ?
    F3 P1 F1 . . 89.25(6) ?
    F2 P1 F1 . . 180.0 ?
    F4 P1 F1 2 . 89.70(7) ?
    F4 P1 F1 . . 89.70(7) ?
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
    C2 N1 C1 C1 . . . 2_655 9.0(3) ?
    C2 N1 C1 C8 . . . . -169.71(17) ?
    C1 N1 C2 C2 . . . 2_655 9.2(3) ?
    C1 N1 C2 C3 . . . . -167.13(17) ?
    C7 N2 C3 C4 . . . . 1.0(3) ?
    C7 N2 C3 C2 . . . . 175.63(17) ?
    N1 C2 C3 N2 . . . . -30.2(2) ?
    C2 C2 C3 N2 2_655 . . . 153.7(2) ?
    N1 C2 C3 C4 . . . . 144.14(19) ?
    C2 C2 C3 C4 2_655 . . . -31.9(3) ?
    N2 C3 C4 C5 . . . .  -.9(3) ?
    C2 C3 C4 C5 . . . . -175.14(19) ?
    C3 C4 C5 C6 . . . .  .4(3) ?
    C4 C5 C6 C7 . . . .  .0(3) ?
    C3 N2 C7 C6 . . . .  -.7(3) ?
    C5 C6 C7 N2 . . . .  .2(3) ?
    N1 C1 C8 O1 . . . . 13.5(3) ?
    C1 C1 C8 O1 2_655 . . . -165.0(3) ?
    N1 C1 C8 O2 . . . . -168.02(19) ?
    C1 C1 C8 O2 2_655 . . . 13.5(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
    O2 H2O O2 2_655 1.206(5) 1.206(5) 2.405(4) 171(6)
    N2 H2N O1W .  .91(3) 1.77(3) 2.683(3) 177(3)
    O1W H1WA O1 3_556  .79(4) 1.98(4) 2.739(2) 160(4)
    O1W H1WB O1 .  .89(4) 1.96(4) 2.841(3) 171(4)
    O2W H2WA O2 2  .89 2.07 2.815(4) 140
