The 1:1 proton-transfer compound of 8-quinolinol (oxine) with pyrazine-2,3-dicarboxylic acid: 8-hydroxyquinolinium 3-carboxypyrazine-2-carboxylate dihydrate
Graham Smith; Urs D. Wermuth; Peter C. Healy; Jonathan M. White; Acta Crystallographica Section E 62 (2006) o5089–o5091; doi:10.1107/S1600536806042322

data_2210997
_publ_section_title
;
 The 1:1 proton-transfer compound of 8-quinolinol (oxine) with
 pyrazine-2,3-dicarboxylic acid: 8-hydroxyquinolinium
 3-carboxypyrazine-2-carboxylate dihydrate
;
_journal_coeditor_code           FL2064
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5089
_journal_page_last               o5091
_journal_paper_doi               10.1107/S1600536806042322
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C9 H8 N O +, C6 H3 N2 O4 -, 2H2 O'
_chemical_formula_moiety         'C9 H8 N O +, C6 H3 N2 O4 -, 2(H2 O)'
_chemical_formula_sum            'C15 H15 N3 O7'
_chemical_formula_weight         349.30
_chemical_melting_point          443.9(13)
_chemical_name_common
'8-hydroxyquinolinium pyrazine-2,3-dicarboxylate dihydrate'
_chemical_name_systematic
;
8-hydroxyquinolinium 3-carboxypyrazine-2-carboxylate 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 (Sheldrick, 1997)'
_cell_angle_alpha                86.138(2)
_cell_angle_beta                 80.977(2)
_cell_angle_gamma                73.673(2)
_cell_formula_units_Z            4
_cell_length_a                   6.8754(9)
_cell_length_b                   12.0387(15)
_cell_length_c                   19.338(2)
_cell_measurement_reflns_used    2861
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.8
_cell_volume                     1516.6(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8060
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.07
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.238
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         5281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0402
_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/[\s^2^(Fo^2^)+(0.0503P)^2^+ 0.4013P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                4475
_reflns_number_total             5281
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fl2064.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '442.6-445.1' was changed to
'443.9(13)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '442.6-445.1' was changed to
'443.9(13)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2210997
_cod_database_fobs_code          2210997