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_2018317
_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          'C6 H0.88 Cl2 O4 , 2C5 H9.56 N O'
_chemical_formula_moiety         'C6 H0.88 Cl2 O4, 2(C5 H9.56 N O)'
_chemical_formula_sum            'C16 H20 Cl2 N2 O6'
_chemical_formula_weight         407.25
_chemical_name_common
;
chloranilic acid--piperidin-2-one (1/2)
;
_chemical_name_systematic
;
2,5-dichloro-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione--piperidin-2-one (1/2)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 114.0658(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   17.8438(5)
_cell_length_b                   5.4253(3)
_cell_length_c                   19.5958(5)
_cell_measurement_reflns_used    16592
_cell_measurement_temperature    180.0(10)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      3.1
_cell_volume                     1732.14(12)
_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) and WinGX (Farrugia, 1999)
;
_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 0.997
_diffrn_measured_fraction_theta_max 0.996
_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  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17611
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.03
_exptl_absorpt_coefficient_mu    0.412
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(<i>NUMABS</i>; Higashi, 1999)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848.00
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.237
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2524
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0457P)^2^+1.3417P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0831
_reflns_number_gt                2382
_reflns_number_total             2524
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fg3233.cif
_cod_data_source_block           IV
_cod_original_cell_volume        1732.12(12)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2018317
_cod_database_fobs_code          2018317