#------------------------------------------------------------------------------
#$Date: 2019-12-25 22:26:10 +0200 (Wed, 25 Dec 2019) $
#$Revision: 245890 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/14/2311442.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_2311442
loop_
_publ_author_name
'Gotoh, Kazuma'
'Ishida, Hiroyuki'
_publ_section_title
;
 Crystal structures of three hydrogen-bonded 1:2 compounds of chloranilic
 acid with 2-pyridone, 3-hy-droxy-pyridine and 4-hyroxypyridine.
;
_journal_coeditor_code           LH5855
_journal_issue                   'Pt 10'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1546
_journal_page_last               1550
_journal_paper_doi               10.1107/S2056989017013536
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          '2C5 H5 N O , C6 H2 Cl2 O4'
_chemical_formula_moiety         '2(C5 H5 N O) , C6 H2 Cl2 O4'
_chemical_formula_sum            'C16 H12 Cl2 N2 O6'
_chemical_formula_weight         399.19
_chemical_name_common            'bis(2-pyridone) chloranilic acid'
_chemical_name_systematic
'Bis[pyridin-2(1H)-one] 2,5-dichloro-3,6-dihydroxy-1,4-bebzoquinone'
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90.0000
_cell_angle_beta                 121.278(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   11.9402(7)
_cell_length_b                   3.7005(2)
_cell_length_c                   21.7919(13)
_cell_measurement_reflns_used    20111
_cell_measurement_temperature    120.0(10)
_cell_measurement_theta_max      30.07
_cell_measurement_theta_min      3.29
_cell_volume                     822.92(8)
_computing_cell_refinement
;
RAPID-AUTO (Rigaku, 2006)
;
_computing_data_collection
;
RAPID-AUTO (Rigaku, 2006)
;
_computing_data_reduction
;
RAPID-AUTO (Rigaku, 2006)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
CrystalStructure (Rigaku, 2010), PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPIDII'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0129
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            22767
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         3.415
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.432
_exptl_absorpt_correction_T_max  0.913
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Higashi, 1995)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408.00
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.244
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0443P)²+0.3557P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0763
_reflns_number_gt                2316
_reflns_number_total             2401
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5855sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        822.92(9)
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_database_code               2311442
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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_occupancy
Cl Cl1 0.60869(2) 0.78653(6) 0.40403(2) 0.01704(8) Uani d 1
O O1 0.33921(7) 0.8229(2) 0.37552(4) 0.02149(16) Uani d 1
O O2 0.75999(6) 0.4050(2) 0.54453(4) 0.01794(15) Uani d 1
H H2 0.8039(15) 0.289(4) 0.5870(8) 0.027 Uiso d 1
O O3 0.92219(7) 0.1199(2) 0.66164(4) 0.02094(16) Uani d 1
N N1 1.13199(8) -0.0736(2) 0.72858(4) 0.01604(16) Uani d 1
H H1 1.1281(13) -0.016(4) 0.7672(8) 0.024 Uiso d 1
C C1 0.41591(9) 0.6765(2) 0.43248(5) 0.01361(17) Uani d 1
C C2 0.55361(8) 0.6274(3) 0.45806(5) 0.01311(16) Uani d 1
C C3 0.63639(8) 0.4587(2) 0.52136(5) 0.01342(17) Uani d 1
C C4 1.02174(9) -0.0153(3) 0.66317(5) 0.01563(17) Uani d 1
C C5 1.02800(9) -0.1116(3) 0.60168(5) 0.01779(18) Uani d 1
H H5 0.953363 -0.080221 0.554948 0.021 Uiso calc 1
C C6 1.14171(10) -0.2497(3) 0.60990(5) 0.01837(19) Uani d 1
H H6 1.145376 -0.312374 0.568705 0.022 Uiso calc 1
C C7 1.25330(10) -0.2995(3) 0.67902(5) 0.01870(19) Uani d 1
H H7 1.332337 -0.392760 0.684778 0.022 Uiso calc 1
C C8 1.24515(9) -0.2109(3) 0.73732(5) 0.01775(18) Uani d 1
H H8 1.318846 -0.245048 0.784277 0.021 Uiso calc 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
C3 O2 H2 . 114.1(10)
C8 N1 C4 . 123.66(8)
C8 N1 H1 . 119.5(9)
C4 N1 H1 . 116.9(9)
O1 C1 C2 . 123.32(8)
O1 C1 C3 3_666 118.05(8)
C2 C1 C3 3_666 118.63(7)
C3 C2 C1 . 121.99(8)
C3 C2 Cl1 . 121.00(7)
C1 C2 Cl1 . 117.01(7)
O2 C3 C2 . 122.88(8)
O2 C3 C1 3_666 117.75(8)
C2 C3 C1 3_666 119.37(8)
O3 C4 N1 . 118.06(8)
O3 C4 C5 . 125.24(8)
N1 C4 C5 . 116.69(8)
C6 C5 C4 . 120.10(9)
C6 C5 H5 . 120.0
C4 C5 H5 . 120.0
C5 C6 C7 . 120.62(9)
C5 C6 H6 . 119.7
C7 C6 H6 . 119.7
C8 C7 C6 . 118.57(9)
C8 C7 H7 . 120.7
C6 C7 H7 . 120.7
N1 C8 C7 . 120.35(9)
N1 C8 H8 . 119.8
C7 C8 H8 . 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1 C2 . 1.7233(9)
O1 C1 . 1.2217(11)
O2 C3 . 1.3033(10)
O2 H2 . 0.901(16)
O3 C4 . 1.2739(11)
N1 C8 . 1.3611(12)
N1 C4 . 1.3648(11)
N1 H1 . 0.892(15)
C1 C2 . 1.4475(12)
C1 C3 3_666 1.5182(12)
C2 C3 . 1.3614(12)
C4 C5 . 1.4256(13)
C5 C6 . 1.3726(14)
C5 H5 . 0.9500
C6 C7 . 1.4120(14)
C6 H6 . 0.9500
C7 C8 . 1.3636(14)
C7 H7 . 0.9500
C8 H8 . 0.9500
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
O2 H2 O3 . 0.901(15) 1.627(16) 2.4989(11) 161.9(19) y
N1 H1 O3 2_756 0.893(16) 1.996(17) 2.8743(12) 167.6(16) y
C7 H7 Cl1 3_756 0.95 2.79 3.5122(13) 134 y
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 . . -179.08(9)
C3 C1 C2 C3 3_666 . 1.18(15)
O1 C1 C2 Cl1 . . -0.05(13)
C3 C1 C2 Cl1 3_666 . -179.79(6)
C1 C2 C3 O2 . . 178.46(9)
Cl1 C2 C3 O2 . . -0.53(14)
C1 C2 C3 C1 . 3_666 -1.19(15)
Cl1 C2 C3 C1 . 3_666 179.82(7)
C8 N1 C4 O3 . . -178.90(9)
C8 N1 C4 C5 . . 1.04(15)
O3 C4 C5 C6 . . 178.84(10)
N1 C4 C5 C6 . . -1.09(15)
C4 C5 C6 C7 . . 0.28(16)
C5 C6 C7 C8 . . 0.64(16)
C4 N1 C8 C7 . . -0.13(16)
C6 C7 C8 N1 . . -0.73(15)
