#------------------------------------------------------------------------------
#$Date: 2018-11-10 05:36:18 +0200 (Sat, 10 Nov 2018) $
#$Revision: 211887 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/27/2242718.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_2242718
loop_
_publ_author_name
'Gotoh, Kazuma'
'Ishida, Hiroyuki'
_publ_section_title
;
 Crystal structures of two hydrogen-bonded compounds of chloranilic
 acid--ethyleneurea (1/1) and chloranilic acid--hydantoin (1/2)
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1727
_journal_page_last               1730
_journal_paper_doi               10.1107/S205698901801561X
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C6 H2 Cl2 O4, C3 H6 N2 O'
_chemical_formula_moiety         'C6 H2 Cl2 O4, C3 H6 N2 O'
_chemical_formula_sum            'C9 H8 Cl2 N2 O5'
_chemical_formula_weight         295.08
_chemical_name_common
;
Chloranilic acid--ethyleneurea (1/1)
;
_chemical_name_systematic
;
2,5-Dichloro-3,6-dihydroxy-1,4-benzoquinone--imidazolidin-2-one (1/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 105.563(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   5.0180(4)
_cell_length_b                   14.6142(10)
_cell_length_c                   15.8882(11)
_cell_measurement_reflns_used    19204
_cell_measurement_temperature    180.0(10)
_cell_measurement_theta_max      30.11
_cell_measurement_theta_min      3.00
_cell_volume                     1122.43(14)
_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) and
Mercury (Macrae et al.,  2006)
;
_computing_publication_material
;
CrystalStructure (Rigaku, 2018) and PLATON (Spek, 2015)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SIR92 (Altomare et al.,  1993)
;
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0569
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21546
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.020
_diffrn_reflns_theta_min         3.005
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_T_max  0.873
_exptl_absorpt_correction_T_min  0.716
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600.00
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.306
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3266
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0333
_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)+(0.0573P)²+0.2007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0917
_reflns_number_gt                3040
_reflns_number_total             3266
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh5884sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1122.43(15)
_cod_database_code               2242718
_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.
;
_shelx_estimated_absorpt_t_min   0.776
_shelx_estimated_absorpt_t_max   0.876
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_occupancy
Cl Cl1 1.06653(5) 0.00389(2) 0.64704(2) 0.02517(9) Uani d 1
Cl Cl2 0.28647(6) 0.43040(2) 0.69108(2) 0.03101(9) Uani d 1
O O1 0.64834(18) -0.14266(6) 0.60507(6) 0.03198(19) Uani d 1
O O2 0.83758(17) 0.15225(5) 0.51887(5) 0.02612(17) Uani d 1
O O3 -0.17821(19) 0.55990(6) 0.63245(6) 0.03138(19) Uani d 1
O O4 0.43441(18) 0.37722(6) 0.52805(6) 0.03039(19) Uani d 1
O O5 0.70481(17) 0.29928(5) 0.42370(5) 0.02644(17) Uani d 1
N N1 0.8521(2) 0.24152(9) 0.30842(7) 0.0372(3) Uani d 1
N N2 0.4933(2) 0.33134(8) 0.27881(7) 0.0323(2) Uani d 1
C C1 0.5873(2) -0.07583(7) 0.55745(7) 0.02118(19) Uani d 1
C C2 0.7619(2) 0.00483(7) 0.56565(7) 0.02058(19) Uani d 1
C C3 0.6846(2) 0.07805(7) 0.51226(6) 0.02064(19) Uani d 1
C C4 -0.0902(2) 0.53136(7) 0.57314(7) 0.0233(2) Uani d 1
C C5 0.1390(2) 0.46653(7) 0.58624(7) 0.0238(2) Uani d 1
C C6 0.2263(2) 0.43578(7) 0.51801(7) 0.0236(2) Uani d 1
C C7 0.6858(2) 0.29121(7) 0.34329(7) 0.0224(2) Uani d 1
C C8 0.7865(2) 0.24974(8) 0.21442(8) 0.0275(2) Uani d 1
H H8A 0.737465 0.189643 0.185683 0.033 Uiso calc 1
H H8B 0.943169 0.276222 0.195803 0.033 Uiso calc 1
C C9 0.5369(3) 0.31466(9) 0.19376(8) 0.0325(2) Uani d 1
H H9A 0.578932 0.372186 0.166986 0.039 Uiso calc 1
H H9B 0.372898 0.285493 0.153938 0.039 Uiso calc 1
H H1N 0.989(4) 0.2121(14) 0.3405(14) 0.059(6) Uiso d 1
H H2N 0.381(4) 0.3687(13) 0.2915(12) 0.041(5) Uiso d 1
H H2 0.766(4) 0.1933(16) 0.4861(14) 0.056(6) Uiso d 1
H H4 0.476(4) 0.3613(13) 0.4811(13) 0.045(5) 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'
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(14)
C6 O4 H4 . 115.8(13)
C7 N1 C8 . 112.92(10)
C7 N1 H1N . 121.2(15)
C8 N1 H1N . 125.7(15)
C7 N2 C9 . 112.46(10)
C7 N2 H2N . 119.3(12)
C9 N2 H2N . 127.5(12)
O1 C1 C2 . 123.17(9)
O1 C1 C3 3_656 117.64(9)
C2 C1 C3 3_656 119.19(8)
C3 C2 C1 . 121.28(9)
C3 C2 Cl1 . 121.68(8)
C1 C2 Cl1 . 117.03(7)
O2 C3 C2 . 122.48(9)
O2 C3 C1 3_656 117.99(9)
C2 C3 C1 3_656 119.53(9)
O3 C4 C5 . 123.19(10)
O3 C4 C6 3_566 118.08(10)
C5 C4 C6 3_566 118.73(9)
C6 C5 C4 . 120.92(9)
C6 C5 Cl2 . 121.94(8)
C4 C5 Cl2 . 117.13(8)
O4 C6 C5 . 122.18(10)
O4 C6 C4 3_566 117.46(9)
C5 C6 C4 3_566 120.35(9)
O5 C7 N1 . 125.87(10)
O5 C7 N2 . 125.24(10)
N1 C7 N2 . 108.88(10)
N1 C8 C9 . 102.65(9)
N1 C8 H8A . 111.2
C9 C8 H8A . 111.2
N1 C8 H8B . 111.2
C9 C8 H8B . 111.2
H8A C8 H8B . 109.2
N2 C9 C8 . 102.92(9)
N2 C9 H9A . 111.2
C8 C9 H9A . 111.2
N2 C9 H9B . 111.2
C8 C9 H9B . 111.2
H9A C9 H9B . 109.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1 C2 . 1.7169(10)
Cl2 C5 . 1.7145(11)
O1 C1 . 1.2230(13)
O2 C3 . 1.3165(12)
O2 H2 . 0.81(2)
O3 C4 . 1.2168(13)
O4 C6 . 1.3264(12)
O4 H4 . 0.86(2)
O5 C7 . 1.2609(13)
N1 C7 . 1.3338(14)
N1 C8 . 1.4455(15)
N1 H1N . 0.85(2)
N2 C7 . 1.3397(14)
N2 C9 . 1.4464(15)
N2 H2N . 0.849(19)
C1 C2 . 1.4537(14)
C1 C3 3_656 1.5092(14)
C2 C3 . 1.3560(14)
C4 C5 . 1.4612(14)
C4 C6 3_566 1.5045(15)
C5 C6 . 1.3504(15)
C8 C9 . 1.5348(15)
C8 H8A . 0.9900
C8 H8B . 0.9900
C9 H9A . 0.9900
C9 H9B . 0.9900
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 O5 . 0.81(2) 1.82(2) 2.6090(11) 164(2) y
O4 H4 O5 . 0.86(2) 1.88(2) 2.6635(12) 151.0(19) y
N1 H1N O1 3_756 0.85(2) 2.06(2) 2.9003(15) 168(2) y
N2 H2N O3 3_566 0.85(2) 2.06(2) 2.8654(15) 158.6(17) 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 . . -179.04(11)
C3 C1 C2 C3 3_656 . 0.34(16)
O1 C1 C2 Cl1 . . -0.19(14)
C3 C1 C2 Cl1 3_656 . 179.19(7)
C1 C2 C3 O2 . . 179.32(9)
Cl1 C2 C3 O2 . . 0.52(15)
C1 C2 C3 C1 . 3_656 -0.34(16)
Cl1 C2 C3 C1 . 3_656 -179.14(7)
O3 C4 C5 C6 . . 178.94(11)
C6 C4 C5 C6 3_566 . -0.60(17)
O3 C4 C5 Cl2 . . -0.07(15)
C6 C4 C5 Cl2 3_566 . -179.61(8)
C4 C5 C6 O4 . . 179.73(10)
Cl2 C5 C6 O4 . . -1.31(16)
C4 C5 C6 C4 . 3_566 0.61(17)
Cl2 C5 C6 C4 . 3_566 179.57(8)
C8 N1 C7 O5 . . -176.92(10)
C8 N1 C7 N2 . . 3.23(15)
C9 N2 C7 O5 . . 175.71(11)
C9 N2 C7 N1 . . -4.43(15)
C7 N1 C8 C9 . . -0.84(14)
C7 N2 C9 C8 . . 3.73(14)
N1 C8 C9 N2 . . -1.64(13)

_cod_database_fobs_code 2242718
