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_2242718
_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
;
<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
;
SIR92 (Altomare <i>et al.</i>,  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       \w
_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/[\s^2^(Fo^2^)+(0.0573P)^2^+0.2007P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            lh5884sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1122.43(15)
_cod_database_code               2242718
_cod_database_fobs_code          2242718
_shelx_estimated_absorpt_t_min   0.776
_shelx_estimated_absorpt_t_max   0.876
_shelx_hkl_checksum              53191
_shelx_res_checksum              69445