Hydrogen-bonded structures of the 1:1 and 1:2 compounds of chloranilic acid with pyrrolidin-2-one and piperidin-2-one
Gotoh, Kazuma; Ishida, Hiroyuki; Acta Crystallographica Section C 67 (2011) o500–o504; doi:10.1107/S0108270111048165

data_2018314
_publ_section_title
;
 Hydrogen-bonded structures of the 1:1 and 1:2 compounds of chloranilic
 acid with pyrrolidin-2-one and piperidin-2-one
;
_journal_coeditor_code           FG3233
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o500
_journal_page_last               o504
_journal_paper_doi               10.1107/S0108270111048165
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C4 H7 N O , C6 H2 Cl2 O4'
_chemical_formula_moiety         'C4 H7 N O, C6 H2 Cl2 O4'
_chemical_formula_sum            'C10 H9 Cl2 N O5'
_chemical_formula_weight         294.09
_chemical_name_common
;
chloranilic acid--pyrrolidin-2-one (1/1)
;
_chemical_name_systematic
;
2,5-dichloro-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione--pyrrolidin-2-one (1/1)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.404(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   7.7256(4)
_cell_length_b                   19.3792(11)
_cell_length_c                   15.2486(8)
_cell_measurement_reflns_used    36720
_cell_measurement_temperature    180.0(10)
_cell_measurement_theta_max      30.2
_cell_measurement_theta_min      3.0
_cell_volume                     2276.2(2)
_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 (Farrugia, 1997)'
_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      180.0(10)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0126
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            47031
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.03
_exptl_absorpt_coefficient_mu    0.582
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(<i>NUMABS</i>; Higashi, 1999)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200.00
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.048
_refine_diff_density_min         -0.304
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         6636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0744P)^2^+0.1003P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1079
_reflns_number_gt                5477
_reflns_number_total             6636
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fg3233.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C10 H9 Cl2 N O5 '
_cod_database_code               2018314
_cod_database_fobs_code          2018314