Crystal structures of two hydrogen-bonded compounds of chloranilic acid–ethyleneurea (1/1) and chloranilic acid–hydantoin (1/2)
Gotoh, Kazuma; Ishida, Hiroyuki; Acta Crystallographica Section E 74 (2018) 1727–1730; doi:10.1107/S205698901801561X

data_2242719
_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, 2C3 H4 N2 O2'
_chemical_formula_moiety         'C6 H2 Cl2 O4, 2(C3 H4 N2 O2)'
_chemical_formula_sum            'C12 H10 Cl2 N4 O8'
_chemical_formula_weight         409.14
_chemical_name_common
;
Chloranilic acid--hydantoin (1/2)
;
_chemical_name_systematic
;
2,5-Dichloro-3,6-dihydroxy-1,4-benzoquinone--imidazolidine-2,4-dione (1/2)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 117.965(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   19.5690(8)
_cell_length_b                   5.18661(10)
_cell_length_c                   16.6103(3)
_cell_measurement_reflns_used    13670
_cell_measurement_temperature    180.0(10)
_cell_measurement_theta_max      30.20
_cell_measurement_theta_min      3.25
_cell_volume                     1489.04(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
;
<i>ORTEP-3</i> for Windows (Farrugia, 2012) and
Mercury (Macrae <i>et al.</i>,  2006)
;
_computing_publication_material
;
CrystalStructure (Rigaku, 2018) and PLATON (Spek, 2015)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT2018</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      180(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       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14622
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.024
_diffrn_reflns_theta_min         4.102
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.493
_exptl_absorpt_correction_T_max  0.888
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832.00
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.398
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0633P)^2^+0.4572P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.0997
_reflns_number_gt                2029
_reflns_number_total             2181
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lh5884sup1.cif
_cod_data_source_block           II
_cod_original_cell_volume        1489.03(8)
_cod_database_code               2242719
_cod_database_fobs_code          2242719
_shelx_estimated_absorpt_t_min   0.794
_shelx_estimated_absorpt_t_max   0.891
_shelx_hkl_checksum              93386
_shelx_res_checksum              89206