#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/85/2238505.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_2238505
loop_
_publ_author_name
'Gotoh, Kazuma'
'Ishida, Hiroyuki'
_publ_section_title
;
 Bis(4-methoxy-3,4-dihydroquinazolin-1-ium) chloranilate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1482
_journal_paper_doi               10.1107/S1600536813023635
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '2C9 H11 N2 O +, C6 Cl2 O4 2-'
_chemical_formula_moiety         '2(C9 H11 N2 O +), C6 Cl2 O4 2-'
_chemical_formula_sum            'C24 H22 Cl2 N4 O6'
_chemical_formula_weight         533.37
_chemical_name_common
;
Bis(4-methoxy-3,4-dihydroquinazolin-1-ium) chloranilate
;
_chemical_name_systematic
;
Bis(4-methoxy-3,4-dihydroquinazolin-1-ium)
2,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,4-diolate
;
_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
_cell_angle_alpha                97.869(4)
_cell_angle_beta                 91.660(6)
_cell_angle_gamma                100.968(5)
_cell_formula_units_Z            1
_cell_length_a                   4.9971(4)
_cell_length_b                   8.6363(4)
_cell_length_c                   13.5808(9)
_cell_measurement_reflns_used    6359
_cell_measurement_temperature    200.0(10)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      3.0
_cell_volume                     569.06(7)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_collection       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200.0(10)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1990
_diffrn_reflns_av_sigmaI/netI    0.2257
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7422
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_exptl_absorpt_coefficient_mu    0.337
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             276.00
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.887
_refine_diff_density_min         -0.543
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.843
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.843
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0824
_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1680
_refine_ls_wR_factor_ref         0.1770
_reflns_number_gt                1913
_reflns_number_total             2692
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            hg5342.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C24 H22 Cl2 N4 O6 '
_cod_database_code               2238505
_cod_database_fobs_code          2238505
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cl Cl1 0.92850(10) -0.01581(6) 0.33371(4) 0.0289(2) Uani d . 1 1
O O1 0.6877(3) 0.26227(17) 0.41520(12) 0.0253(4) Uani d . 1 1
O O2 0.6806(3) -0.27488(17) 0.44963(13) 0.0273(4) Uani d . 1 1
O O3 0.0538(3) 0.67492(19) 0.17432(13) 0.0325(4) Uani d . 1 1
N N1 0.3013(4) 0.3978(2) 0.33662(15) 0.0238(4) Uani d . 1 1
N N2 0.0001(4) 0.5674(2) 0.32482(16) 0.0264(4) Uani d . 1 1
C C1 0.6067(4) 0.1368(2) 0.45169(16) 0.0202(5) Uani d . 1 1
C C2 0.6949(4) -0.0070(2) 0.42490(16) 0.0216(5) Uani d . 1 1
C C3 0.6061(4) -0.1443(2) 0.46922(16) 0.0208(5) Uani d . 1 1
C C4 0.1661(4) 0.5056(2) 0.37648(17) 0.0239(5) Uani d . 1 1
H H4 0.1907 0.5399 0.4462 0.029 Uiso calc R 1 1
C C5 -0.0403(4) 0.5353(3) 0.21674(18) 0.0276(5) Uani d . 1 1
H H5 -0.2413 0.5032 0.2003 0.033 Uiso calc R 1 1
C C6 0.0872(4) 0.3967(3) 0.17605(18) 0.0252(5) Uani d . 1 1
C C7 0.0414(5) 0.3326(3) 0.07619(19) 0.0329(5) Uani d . 1 1
H H7 -0.0787 0.3723 0.0350 0.039 Uiso calc R 1 1
C C8 0.1683(6) 0.2118(3) 0.0362(2) 0.0375(6) Uani d . 1 1
H H8 0.1365 0.1689 -0.0323 0.045 Uiso calc R 1 1
C C9 0.3429(5) 0.1532(3) 0.0965(2) 0.0367(6) Uani d . 1 1
H H9 0.4315 0.0707 0.0688 0.044 Uiso calc R 1 1
C C10 0.3890(5) 0.2130(3) 0.19591(19) 0.0305(5) Uani d . 1 1
H H10 0.5075 0.1721 0.2370 0.037 Uiso calc R 1 1
C C11 0.2585(4) 0.3353(3) 0.23554(17) 0.0234(5) Uani d . 1 1
C C12 0.3396(6) 0.7357(3) 0.1882(2) 0.0405(6) Uani d . 1 1
H H12A 0.3821 0.8406 0.1661 0.061 Uiso calc R 1 1
H H12B 0.4377 0.6626 0.1493 0.061 Uiso calc R 1 1
H H12C 0.3958 0.7459 0.2589 0.061 Uiso calc R 1 1
H H1 0.413(6) 0.351(3) 0.377(2) 0.037(7) Uiso d . 1 1
H H2 -0.097(6) 0.628(4) 0.362(2) 0.043(8) Uiso d . 1 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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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_3
_geom_angle
C5 O3 C12 . 115.09(18)
C4 N1 C11 . 120.69(19)
C4 N1 H1 . 120.9(17)
C11 N1 H1 . 118.0(17)
C4 N2 C5 . 124.17(18)
C4 N2 H2 . 114.4(19)
C5 N2 H2 . 121.4(19)
O1 C1 C2 . 124.72(19)
O1 C1 C3 2_656 116.54(16)
C2 C1 C3 2_656 118.73(18)
C1 C2 C3 . 123.38(19)
C1 C2 Cl1 . 118.46(16)
C3 C2 Cl1 . 118.15(14)
O2 C3 C2 . 126.28(19)
O2 C3 C1 2_656 115.86(18)
C2 C3 C1 2_656 117.85(16)
N2 C4 N1 . 123.2(2)
N2 C4 H4 . 118.4
N1 C4 H4 . 118.4
O3 C5 N2 . 110.61(19)
O3 C5 C6 . 113.51(18)
N2 C5 C6 . 110.36(18)
O3 C5 H5 . 107.4
N2 C5 H5 . 107.4
C6 C5 H5 . 107.4
C11 C6 C7 . 118.93(19)
C11 C6 C5 . 121.3(2)
C7 C6 C5 . 119.7(2)
C8 C7 C6 . 120.7(2)
C8 C7 H7 . 119.7
C6 C7 H7 . 119.7
C7 C8 C9 . 119.7(2)
C7 C8 H8 . 120.2
C9 C8 H8 . 120.2
C10 C9 C8 . 120.8(2)
C10 C9 H9 . 119.6
C8 C9 H9 . 119.6
C9 C10 C11 . 118.9(2)
C9 C10 H10 . 120.6
C11 C10 H10 . 120.6
C6 C11 C10 . 121.0(2)
C6 C11 N1 . 119.03(18)
C10 C11 N1 . 120.0(2)
O3 C12 H12A . 109.5
O3 C12 H12B . 109.5
H12A C12 H12B . 109.5
O3 C12 H12C . 109.5
H12A C12 H12C . 109.5
H12B C12 H12C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1 C2 . 1.730(2)
O1 C1 . 1.255(3)
O2 C3 . 1.251(2)
O3 C5 . 1.413(3)
O3 C12 . 1.422(3)
N1 C4 . 1.319(2)
N1 C11 . 1.399(3)
N1 H1 . 0.95(3)
N2 C4 . 1.305(3)
N2 C5 . 1.457(3)
N2 H2 . 0.90(3)
C1 C2 . 1.401(3)
C1 C3 2_656 1.537(3)
C2 C3 . 1.405(3)
C3 C1 2_656 1.537(3)
C4 H4 . 0.9500
C5 C6 . 1.508(3)
C5 H5 . 1.0000
C6 C11 . 1.384(3)
C6 C7 . 1.388(4)
C7 C8 . 1.379(3)
C7 H7 . 0.9500
C8 C9 . 1.389(4)
C8 H8 . 0.9500
C9 C10 . 1.374(4)
C9 H9 . 0.9500
C10 C11 . 1.398(3)
C10 H10 . 0.9500
C12 H12A . 0.9800
C12 H12B . 0.9800
C12 H12C . 0.9800
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
N1 H1 O1 . 0.95(3) 1.79(3) 2.706(2) 160(3)
N1 H1 O2 2_656 0.95(3) 2.56(3) 3.229(3) 127(2)
N2 H2 O2 1_465 0.90(3) 1.87(3) 2.762(3) 171(3)
C4 H4 O1 2_666 0.95 2.34 3.214(3) 152
C10 H10 O1 . 0.95 2.52 3.230(3) 131
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_4
_geom_torsion
O1 C1 C2 C3 . . 178.1(2)
C3 C1 C2 C3 2_656 . -2.3(3)
O1 C1 C2 Cl1 . . -1.1(3)
C3 C1 C2 Cl1 2_656 . 178.50(14)
C1 C2 C3 O2 . . -178.8(2)
Cl1 C2 C3 O2 . . 0.4(3)
C1 C2 C3 C1 . 2_656 2.3(3)
Cl1 C2 C3 C1 . 2_656 -178.52(14)
C5 N2 C4 N1 . . -5.1(3)
C11 N1 C4 N2 . . -4.4(3)
C12 O3 C5 N2 . . 64.7(2)
C12 O3 C5 C6 . . -60.0(3)
C4 N2 C5 O3 . . -114.4(2)
C4 N2 C5 C6 . . 12.1(3)
O3 C5 C6 C11 . . 113.8(2)
N2 C5 C6 C11 . . -11.0(3)
O3 C5 C6 C7 . . -63.7(3)
N2 C5 C6 C7 . . 171.5(2)
C11 C6 C7 C8 . . -1.3(4)
C5 C6 C7 C8 . . 176.3(2)
C6 C7 C8 C9 . . 0.3(4)
C7 C8 C9 C10 . . 0.6(4)
C8 C9 C10 C11 . . -0.5(4)
C7 C6 C11 C10 . . 1.4(3)
C5 C6 C11 C10 . . -176.1(2)
C7 C6 C11 N1 . . -178.9(2)
C5 C6 C11 N1 . . 3.6(3)
C9 C10 C11 C6 . . -0.5(3)
C9 C10 C11 N1 . . 179.8(2)
C4 N1 C11 C6 . . 4.8(3)
C4 N1 C11 C10 . . -175.5(2)
