#------------------------------------------------------------------------------
#$Date: 2025-08-19 08:12:48 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301798 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/86/2018632.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_2018632
loop_
_publ_author_name
'Wang, Yi'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 The inner-salt zwitterion, the dihydrochloride dihydrate and the dimethyl
 sulfoxide disolvate of 3,6-bis(pyridin-2-yl)pyrazine-2,5-dicarboxylic
 acid
;
_journal_coeditor_code           FG3272
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o431
_journal_page_last               o435
_journal_paper_doi               10.1107/S0108270112039534
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C16 H12 N4 O4 2+ , 2Cl - , 2H2 O'
_chemical_formula_moiety         'C16 H12 N4 O4 2+, 2(Cl -), 2(H2 O)'
_chemical_formula_sum            'C16 H16 Cl2 N4 O6'
_chemical_formula_weight         431.23
_chemical_name_systematic
;
2,2'-(3,6-Dicarboxypyrazine-2,5-diyl)bis(pyridin-1-ium) dichloride dihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                63.400(10)
_cell_angle_beta                 81.940(10)
_cell_angle_gamma                87.470(10)
_cell_formula_units_Z            1
_cell_length_a                   6.8570(10)
_cell_length_b                   8.5760(10)
_cell_length_c                   9.187(2)
_cell_measurement_reflns_used    21
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      20.0
_cell_measurement_theta_min      14.0
_cell_volume                     478.19(14)
_computing_cell_refinement       'STADI-4 Software (Stoe & Cie, 1997)'
_computing_data_collection       'STADI-4 Software (Stoe & Cie, 1997)'
_computing_data_reduction        'X-RED (Stoe & Cie, 1997)'
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Stoe AED-2 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     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3504
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.50
_diffrn_standards_decay_%        7
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.381
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             222
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.323
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         1681
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0596P)²+0.0431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0927
_reflns_number_gt                1463
_reflns_number_total             1681
_reflns_threshold_expression     I>2Ĭ)
_cod_data_source_file            fg3272.cif
_cod_data_source_block           Ib
_cod_database_code               2018632
_cod_database_fobs_code          2018632
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 1.00015(17) 0.49490(17) 0.31111(14) 0.0275(4) Uani d . 1.000
O O2 0.92722(19) 0.23783(17) 0.53000(16) 0.0339(4) Uani d D 1.000
N N1 0.5886(2) 0.35779(19) 0.61518(16) 0.0213(4) Uani d . 1.000
N N2 0.2702(2) 0.38465(19) 0.92225(16) 0.0224(4) Uani d D 1.000
C C1 0.4106(2) 0.4098(2) 0.65399(19) 0.0209(5) Uani d . 1.000
C C2 0.6788(2) 0.4478(2) 0.46210(19) 0.0201(5) Uani d . 1.000
C C5 0.3229(2) 0.3023(2) 0.82833(19) 0.0203(5) Uani d . 1.000
C C6 0.3015(3) 0.1241(2) 0.8968(2) 0.0258(5) Uani d . 1.000
C C7 0.2197(3) 0.0334(2) 1.0613(2) 0.0304(5) Uani d . 1.000
C C8 0.1635(3) 0.1233(3) 1.1525(2) 0.0317(6) Uani d . 1.000
C C9 0.1921(3) 0.3007(2) 1.0801(2) 0.0286(5) Uani d . 1.000
C C10 0.8865(2) 0.3959(2) 0.42515(19) 0.0222(5) Uani d . 1.000
Cl Cl1 0.35647(7) 0.77154(6) 0.77915(6) 0.0328(2) Uani d . 1.000
O O1W 0.2839(2) 0.1436(2) 0.5001(2) 0.0400(5) Uani d . 1.000
H H2N 0.288(3) 0.500(2) 0.880(2) 0.037(6) Uiso d D 1.000
H H2O 1.044(3) 0.211(4) 0.511(3) 0.065(8) Uiso d D 1.000
H H6 0.34130 0.06410 0.83390 0.0310 Uiso c R 1.000
H H7 0.20300 -0.08850 1.10970 0.0360 Uiso c R 1.000
H H8 0.10640 0.06370 1.26270 0.0380 Uiso c R 1.000
H H9 0.15690 0.36330 1.14140 0.0340 Uiso c R 1.000
H H1WA 0.305(5) 0.044(4) 0.565(4) 0.071(10) Uiso d . 1.000
H H2WB 0.370(4) 0.164(3) 0.423(3) 0.050(7) Uiso d . 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C10 O2 H2O . . 113(2) no
H1WA O1W H2WB . . 104(3) no
C1 N1 C2 . . 117.62(14) no
C5 N2 C9 . . 122.74(17) no
C9 N2 H2N . . 117.2(11) no
C5 N2 H2N . . 120.0(11) no
N1 C1 C5 . . 113.61(14) no
C2 C1 C5 2_666 . 125.20(14) no
N1 C1 C2 . 2_666 121.20(14) no
N1 C2 C1 . 2_666 121.18(14) no
N1 C2 C10 . . 116.60(14) no
C1 C2 C10 2_666 . 122.08(14) no
N2 C5 C6 . . 119.33(15) no
C1 C5 C6 . . 122.73(16) no
N2 C5 C1 . . 117.90(16) no
C5 C6 C7 . . 119.02(17) no
C6 C7 C8 . . 119.82(18) no
C7 C8 C9 . . 119.12(16) no
N2 C9 C8 . . 119.93(17) no
O1 C10 C2 . . 121.69(16) no
O2 C10 C2 . . 113.08(13) no
O1 C10 O2 . . 125.22(15) no
C5 C6 H6 . . 120.00 no
C7 C6 H6 . . 121.00 no
C8 C7 H7 . . 120.00 no
C6 C7 H7 . . 120.00 no
C7 C8 H8 . . 120.00 no
C9 C8 H8 . . 120.00 no
N2 C9 H9 . . 120.00 no
C8 C9 H9 . . 120.00 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
O1 C10 . 1.208(2) no
O2 C10 . 1.310(2) no
O2 H2O . 0.84(2) no
O1W H2WB . 0.81(3) no
O1W H1WA . 0.81(4) no
N1 C1 . 1.337(2) no
N1 C2 . 1.335(2) no
N2 C9 . 1.338(2) no
N2 C5 . 1.345(2) no
N2 H2N . 0.893(19) no
C1 C2 2_666 1.398(2) no
C1 C5 . 1.495(2) no
C2 C10 . 1.512(2) no
C5 C6 . 1.373(3) no
C6 C7 . 1.397(2) no
C7 C8 . 1.381(3) no
C8 C9 . 1.371(3) no
C6 H6 . 0.9400 no
C7 H7 . 0.9400 no
C8 H8 . 0.9400 no
C9 H9 . 0.9400 no
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
O1W H1WA Cl1 1_545 0.81(4) 2.34(3) 3.1453(19) 172(3) yes
O1W H2WB Cl1 2_666 0.81(3) 2.34(3) 3.1472(17) 173(2) yes
N2 H2N Cl1 . 0.893(19) 2.132(19) 3.0226(19) 175.2(19) yes
O2 H2O O1W 1_655 0.84(2) 1.72(2) 2.559(2) 172(3) yes
C6 H6 Cl1 1_545 0.94 2.77 3.628(2) 153 yes
C8 H8 O2 2_657 0.94 2.43 3.172(3) 136 yes
C9 H9 O1 1_456 0.94 2.42 3.346(2) 168 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 C5 . . . -179.32(16) no
C2 N1 C1 C2 . . 2_666 0.7(3) no
C1 N1 C2 C10 . . . 175.11(16) no
C1 N1 C2 C1 . . 2_666 -0.7(3) no
C9 N2 C5 C1 . . . -179.39(15) no
C9 N2 C5 C6 . . . -1.8(2) no
C5 N2 C9 C8 . . . 0.2(3) no
N1 C1 C5 N2 . . . 123.35(17) no
N1 C1 C5 C6 . . . -54.1(2) no
C2 C1 C5 N2 2_666 . . -56.7(2) no
C2 C1 C5 C6 2_666 . . 125.9(2) no
N1 C1 C2 N1 . 2_666 2_666 -0.7(3) no
N1 C1 C2 C10 . 2_666 2_666 174.85(16) no
C5 C1 C2 N1 . 2_666 2_666 179.30(17) no
C5 C1 C2 C10 . 2_666 2_666 -5.2(3) no
N1 C2 C10 O1 . . . -158.32(17) no
N1 C2 C10 O2 . . . 20.5(2) no
C1 C2 C10 O1 2_666 . . 17.4(3) no
C1 C2 C10 O2 2_666 . . -163.80(16) no
N2 C5 C6 C7 . . . 2.0(3) no
C1 C5 C6 C7 . . . 179.39(16) no
C5 C6 C7 C8 . . . -0.6(3) no
C6 C7 C8 C9 . . . -1.0(3) no
C7 C8 C9 N2 . . . 1.2(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139061384
