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###        Electronic paper (Acta Crystallographica Section E)             ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
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# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
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#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
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#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Chloranilic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C6 H2 Cl2 O4'
_chemical_formula_sum     'C6 H2 Cl2 O4'
_chemical_formula_iupac     'C6 H2 Cl2 O4'
_chemical_formula_weight     208.98
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     7.5338(12)
_cell_length_b     5.5225(10)
_cell_length_c     8.5720(12)
_cell_angle_alpha     90.00
_cell_angle_beta     104.868(11)
_cell_angle_gamma     90.00
_cell_volume     344.70(10)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4539
_cell_measurement_theta_min     2.7910
_cell_measurement_theta_max     27.8185
_cell_measurement_temperature     100.0(10)
_exptl_crystal_description     prism
_exptl_crystal_colour     red
_exptl_crystal_size_max     0.3
_exptl_crystal_size_mid     0.1
_exptl_crystal_size_min     0.1
_exptl_crystal_density_diffrn     2.014
_exptl_crystal_density_meas     .
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     208
_exptl_absorpt_coefficient_mu     0.903
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details
;
(CrysAlis Pro; Oxford Diffraction (2009))
;
_exptl_absorpt_correction_T_min     0.85711
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details
;
;
_diffrn_ambient_temperature     100.0(10)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method     'ω-scan'
_diffrn_detector_area_resol_mean     16.1544
_diffrn_reflns_number     6154
_diffrn_reflns_av_R_equivalents     0.0321
_diffrn_reflns_av_sigmaI/netI     0.0170
_diffrn_reflns_theta_min     3.22
_diffrn_reflns_theta_max     27.85
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.935
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     10
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors
based on F² are statistically about twice as large as those based on
F, and R- factors based on ALL data will be even larger.
;
_reflns_number_total     774
_reflns_number_gt     698
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0284
_refine_ls_R_factor_gt     0.0251
_refine_ls_wR_factor_gt     0.0555
_refine_ls_wR_factor_ref     0.0561
_refine_ls_goodness_of_fit_ref     1.086
_refine_ls_restrained_S_all     1.086
_refine_ls_number_reflns     774
_refine_ls_number_parameters     59
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0204P)²+0.3502P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.369
_refine_diff_density_min     -0.271
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_cell_refinement     'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_reduction     'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_structure_solution     'SIR92 (Altomare et al.,  1993)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                   'Stereochemical Workstation Operation Manual (Siemens, 1989)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.8496(2) -0.1699(3) 0.47066(18) 0.0102(3) Uani d . 1 . .
    Cl Cl1 0.66487(5) -0.36207(7) 0.44138(4) 0.01295(13) Uani d . 1 . .
    C C2 0.9798(2) -0.1990(3) 0.38967(18) 0.0101(3) Uani d . 1 . .
    O O2 0.97189(15) -0.3741(2) 0.28296(13) 0.0132(3) Uani d . 1 . .
    H H2 1.064(3) -0.381(4) 0.249(3) 0.034(7) Uiso d . 1 . .
    C C3 1.14042(19) -0.0274(3) 0.41584(17) 0.0095(3) Uani d . 1 . .
    O O3 1.25301(15) -0.0641(2) 0.33789(13) 0.0126(2) Uani d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C1 0.0081(7) 0.0100(8) 0.0122(7) -0.0022(6) 0.0020(6) 0.0014(6)
    Cl1 0.01094(19) 0.0138(2) 0.0150(2) -0.00495(14) 0.00488(13) -0.00150(14)
    C2 0.0113(7) 0.0081(7) 0.0102(7) 0.0005(6) 0.0016(6) 0.0013(6)
    O2 0.0121(5) 0.0133(6) 0.0163(6) -0.0014(4) 0.0075(5) -0.0045(4)
    C3 0.0084(7) 0.0103(7) 0.0098(7) 0.0010(6) 0.0021(6) 0.0041(6)
    O3 0.0121(5) 0.0131(6) 0.0147(5) 0.0003(4) 0.0072(4) 0.0008(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell esds are taken into
account individually in the estimation of esds in distances, angles and
torsion angles; correlations between esds in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . 1.349(2) ?
    C1 C3 3_756 1.450(2) ?
    C1 Cl1 . 1.7164(15) ?
    C2 O2 . 1.3217(19) ?
    C2 C3 . 1.508(2) ?
    O2 H2 . 0.82(2) ?
    C3 O3 . 1.2240(18) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 C3 . 3_756 121.02(14) ?
    C2 C1 Cl1 . . 121.38(12) ?
    C3 C1 Cl1 3_756 . 117.59(11) ?
    O2 C2 C1 . . 122.23(14) ?
    O2 C2 C3 . . 117.05(13) ?
    C1 C2 C3 . . 120.71(14) ?
    C2 O2 H2 . . 112.9(17) ?
    O3 C3 C1 . 3_756 124.53(14) ?
    O3 C3 C2 . . 117.19(14) ?
    C1 C3 C2 3_756 . 118.27(13) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C3 C1 C2 O2 3_756 . . . -178.48(14) ?
    Cl1 C1 C2 O2 . . . . 0.7(2) ?
    C3 C1 C2 C3 3_756 . . . 0.4(2) ?
    Cl1 C1 C2 C3 . . . . 179.51(11) ?
    O2 C2 C3 O3 . . . . -0.8(2) ?
    C1 C2 C3 O3 . . . . -179.74(14) ?
    O2 C2 C3 C1 . . . 3_756 178.55(13) ?
    C1 C2 C3 C1 . . . 3_756 -0.4(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    O2 H2 O3 2_745 0.82(2) 2.00(2) 2.7516(15) 152(2)
data_global
_journal_date_recd_electronic     2010-01-09
_journal_date_accepted     2010-01-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      2
_journal_page_first     o497
_journal_page_last     o498
_journal_paper_category     QO
_journal_coeditor_code     DS2017
_publ_contact_author
;
Maciej Kubicki
Faculty of Chemistry
Adam Mickiewicz University
Grunwaldzka 6
60-780 Poznań
Poland
;
_publ_contact_author_email     mkubicki@amu.edu.pl
_publ_section_title
;
Chloranilic acid: a redetermination at 100 K
;
loop_
    _publ_author_name
    _publ_author_address
    'Dutkiewicz, Grzegorz'
;  Department of Chemistry
Adam Mickiewicz University
Grunwaldzka 6
60-780 Poznań
Poland
;
    'Yathirajan, H. S.'
;  Department of Studies in Chemistry
Mangalore University
Mangalagangotri 574 199
India
;
    'Al-arique, Q. N. M. Hakim'
;  Department of Studies in Chemistry
Mangalore University
Mangalagangotri 574 199
India
;
    'Narayana, B.'
;  Department of Studies in Chemistry
University of Mysore
Manasagangotri
Mysore 570 006
India
;
    'Kubicki, Maciej'
;  Department of Chemistry
Adam Mickiewicz University
Grunwaldzka 6
60-780 Poznań
Poland
;
_publ_section_synopsis     .
