2,3-Dichloro-1,4-hydroquinone 2,3-dichloro-1,4-benzoquinone monohydrate: a quinhydrone-type 1:1 donor-acceptor [<i>D</i>—<i>A</i>] charge-transfer complex
Guégano, Xavier; Hauser, Jürg; Liu, Shi-Xia; Decurtins, Silvio; Acta Crystallographica Section E 67 (2011) o2967–o2968; doi:10.1107/S1600536811041377

data_2232465
_publ_section_title
;
 2,3-Dichloro-1,4-hydroquinone 2,3-dichloro-1,4-benzoquinone monohydrate:
 a quinhydrone-type 1:1 donor-acceptor [<i>D</i>---<i>A</i>]
 charge-transfer complex
;
_journal_coeditor_code           SU2322
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2967
_journal_page_last               o2968
_journal_paper_doi               10.1107/S1600536811041377
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C6 H4 Cl2 O2, C6 H2 Cl2 O2, H2 O'
_chemical_formula_moiety         'C6 H4 Cl2 O2, C6 H2 Cl2 O2, H2 O'
_chemical_formula_sum            'C12 H8 Cl4 O5'
_chemical_formula_weight         373.98
_chemical_name_systematic
;
2,3-dichlorobenzene-1,4-diol 2,3-dichlorocyclohexa-2,5-diene-1,4-dione
monohydrate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.9738(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.15329(14)
_cell_length_b                   7.19541(15)
_cell_length_c                   27.2811(5)
_cell_measurement_reflns_used    7958
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.484
_cell_measurement_theta_min      2.752
_cell_volume                     1402.29(5)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'Mercury (Macrae <i>et al.</i>, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type
;
Siemens SMART 1K CCD area-detector
;
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            19255
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_T_max  0.9416
_exptl_absorpt_correction_T_min  0.8593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+0.5830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0771
_reflns_number_gt                2653
_reflns_number_total             3138
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            su2322.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2232465
_cod_database_fobs_code          2232465