#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/24/2212452.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_2212452
loop_
_publ_author_name
'Czapik, Agnieszka'
'Gdaniec, Maria'
_publ_section_title
;
 Quinoxalinium 2,6-dihydroxybenzoate
;
_journal_coeditor_code           BH2084
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1480
_journal_page_last               o1482
_journal_paper_doi               10.1107/S1600536807008707
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C8 H7 N2 +, C7 H5 O4 -'
_chemical_formula_moiety         'C8 H7 N2 +, C7 H5 O4 -'
_chemical_formula_sum            'C15 H12 N2 O4'
_chemical_formula_weight         284.27
_chemical_melting_point          393
_chemical_name_systematic
;
quinoxalinium 2,6-dihydroxybenzoate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.872(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.0557(5)
_cell_length_b                   9.0755(4)
_cell_length_c                   24.7931(10)
_cell_measurement_reflns_used    7496
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      29.48
_cell_measurement_theta_min      2.52
_cell_volume                     2644.48(19)
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics
;
Stereochemical Workstation Operation Manual (Siemens, 1989)
and MERCURY (Macrae et al.,  2006)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Kuma KM-4-CCD κ geometry'
_diffrn_measurement_method       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  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0112
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14871
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.10
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            light-brown
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.150
_refine_ls_extinction_coef       0.0019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0408
_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)+(0.0514P)²+1.2986P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1268
_reflns_number_gt                1935
_reflns_number_total             2701
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2084.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2212452
_cod_database_fobs_code          2212452
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N1 0.71111(12) 0.07788(17) 0.42705(5) 0.0571(4) Uani d . 1
H H1N 0.6643(19) 0.120(2) 0.4556(10) 0.103(7) Uiso d . 1
C C2 0.77627(16) -0.0371(2) 0.43929(7) 0.0678(5) Uani d . 1
H H2 0.7844 -0.0821 0.4737 0.081 Uiso calc R 1
C C3 0.83458(17) -0.0936(2) 0.40046(8) 0.0718(5) Uani d . 1
H H3 0.8818 -0.1748 0.4103 0.086 Uiso calc R 1
N N4 0.82508(13) -0.03669(18) 0.35128(6) 0.0680(4) Uani d . 1
C C5 0.73804(19) 0.1463(2) 0.28515(8) 0.0745(6) Uani d . 1
H H5 0.7744 0.1071 0.2590 0.089 Uiso calc R 1
C C6 0.6691(2) 0.2637(3) 0.27217(8) 0.0862(7) Uani d . 1
H H6 0.6572 0.3038 0.2368 0.103 Uiso calc R 1
C C7 0.6150(2) 0.3265(2) 0.31119(8) 0.0810(6) Uani d . 1
H H7 0.5697 0.4095 0.3017 0.097 Uiso calc R 1
C C8 0.62814(17) 0.2674(2) 0.36280(7) 0.0660(5) Uani d . 1
H H8 0.5913 0.3085 0.3884 0.079 Uiso calc R 1
C C9 0.69763(13) 0.14428(19) 0.37646(6) 0.0523(4) Uani d . 1
C C10 0.75528(14) 0.0825(2) 0.33807(6) 0.0570(4) Uani d . 1
C C1A 0.55856(12) 0.14053(18) 0.58511(6) 0.0484(4) Uani d . 1
C C2A 0.48711(14) 0.2638(2) 0.57994(6) 0.0565(4) Uani d . 1
C C3A 0.43115(15) 0.2989(2) 0.62148(8) 0.0674(5) Uani d . 1
H H3A 0.3826 0.3797 0.6177 0.081 Uiso calc R 1
C C4A 0.44808(16) 0.2131(2) 0.66825(7) 0.0695(5) Uani d . 1
H H4A 0.4105 0.2371 0.6960 0.083 Uiso calc R 1
C C5A 0.51872(17) 0.0936(2) 0.67513(7) 0.0685(5) Uani d . 1
H H5A 0.5294 0.0375 0.7073 0.082 Uiso calc R 1
C C6A 0.57425(15) 0.05657(19) 0.63378(7) 0.0573(4) Uani d . 1
C C7A 0.61814(14) 0.0978(2) 0.54123(6) 0.0570(4) Uani d . 1
O O1A 0.60323(11) 0.17983(16) 0.49778(5) 0.0729(4) Uani d . 1
O O2A 0.68085(12) -0.01277(16) 0.54706(5) 0.0790(4) Uani d . 1
O O3A 0.47071(13) 0.35293(18) 0.53483(6) 0.0859(5) Uani d . 1
H H3OA 0.519(2) 0.306(3) 0.5106(12) 0.130(9) Uiso d . 1
O O4A 0.64385(14) -0.06200(16) 0.64183(6) 0.0878(5) Uani d . 1
H H4OA 0.665(2) -0.068(3) 0.6071(11) 0.110(8) Uiso d . 1
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'
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
_geom_angle_publ_flag
C2 N1 C9 120.62(14) y
C2 N1 H1N 120.9(12) ?
C9 N1 H1N 118.5(12) ?
N1 C2 C3 119.99(17) ?
N1 C2 H2 120.0 ?
C3 C2 H2 120.0 ?
N4 C3 C2 122.75(19) ?
N4 C3 H3 118.6 ?
C2 C3 H3 118.6 ?
C3 N4 C10 117.30(14) y
C6 C5 C10 120.27(17) ?
C6 C5 H5 119.9 ?
C10 C5 H5 119.9 ?
C5 C6 C7 120.94(19) ?
C5 C6 H6 119.5 ?
C7 C6 H6 119.5 ?
C8 C7 C6 120.9(2) ?
C8 C7 H7 119.6 ?
C6 C7 H7 119.6 ?
C7 C8 C9 118.79(17) ?
C7 C8 H8 120.6 ?
C9 C8 H8 120.6 ?
N1 C9 C8 121.24(14) ?
N1 C9 C10 117.82(16) ?
C8 C9 C10 120.94(15) ?
N4 C10 C5 120.34(15) ?
N4 C10 C9 121.49(15) ?
C5 C10 C9 118.16(18) ?
C2A C1A C6A 118.34(13) ?
C2A C1A C7A 122.04(15) ?
C6A C1A C7A 119.62(15) ?
O3A C2A C3A 117.91(16) ?
O3A C2A C1A 121.66(14) ?
C3A C2A C1A 120.43(16) ?
C4A C3A C2A 119.39(17) ?
C4A C3A H3A 120.3 ?
C2A C3A H3A 120.3 ?
C5A C4A C3A 121.78(15) ?
C5A C4A H4A 119.1 ?
C3A C4A H4A 119.1 ?
C4A C5A C6A 119.39(17) ?
C4A C5A H5A 120.3 ?
C6A C5A H5A 120.3 ?
O4A C6A C5A 118.05(16) ?
O4A C6A C1A 121.30(14) ?
C5A C6A C1A 120.66(16) ?
O2A C7A O1A 122.04(14) ?
O2A C7A C1A 120.43(15) ?
O1A C7A C1A 117.53(16) ?
C2A O3A H3OA 103.8(16) ?
C6A O4A H4OA 101.1(15) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.301(2) y
N1 C9 1.368(2) y
N1 H1N 1.07(2) ?
C2 C3 1.409(2) ?
C2 H2 0.9300 ?
C3 N4 1.305(2) y
C3 H3 0.9300 ?
N4 C10 1.364(2) y
C5 C6 1.346(3) ?
C5 C10 1.407(2) ?
C5 H5 0.9300 ?
C6 C7 1.402(3) ?
C6 H6 0.9300 ?
C7 C8 1.364(3) ?
C7 H7 0.9300 ?
C8 C9 1.392(2) ?
C8 H8 0.9300 ?
C9 C10 1.414(2) ?
C1A C2A 1.400(2) ?
C1A C6A 1.404(2) ?
C1A C7A 1.483(2) ?
C2A O3A 1.359(2) ?
C2A C3A 1.388(2) ?
C3A C4A 1.374(3) ?
C3A H3A 0.9300 ?
C4A C5A 1.366(3) ?
C4A H4A 0.9300 ?
C5A C6A 1.385(2) ?
C5A H5A 0.9300 ?
C6A O4A 1.352(2) ?
C7A O2A 1.245(2) y
C7A O1A 1.289(2) y
O3A H3OA 1.02(3) ?
O4A H4OA 0.95(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
O4A H4OA O2A . 0.95(3) 1.62(3) 2.5273(18) 157(2)
O3A H3OA O1A . 1.02(3) 1.61(3) 2.5531(18) 152(3)
N1 H1N O1A . 1.07(2) 1.51(2) 2.5765(17) 177(2)
N1 H1N O2A . 1.07(2) 2.54(2) 3.1852(18) 118.3(15)
C6 H6 N4 4_655 0.93 2.67 3.571(2) 164
C2 H2 O2A . 0.93 2.51 3.143(2) 126
C2 H2 O3A 3_545 0.93 2.49 3.103(2) 124
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
C2A C1A C7A O2A -179.77(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21125283
