##############################################################################
###                                                                        ###
###        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.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL97
_journal_data_validation_number     ?
_journal_date_recd_electronic     2007-04-07
_journal_date_accepted     2007-04-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      5
_journal_page_first     o2460
_journal_page_last     o2460
_journal_paper_category     QO
_journal_coeditor_code     HB2366
_publ_contact_author_name     'Zu-Pei Liang'
_publ_contact_author_address
;
Department of Chemistry and Chemical Engineering
Weifang University
Weifang 261061
People's Republic of China
;
_publ_contact_author_email     zupeiliang@yahoo.com.cn
_publ_contact_author_fax     '86536 887 7561'
_publ_contact_author_phone     '86536 887 7561'
_publ_section_title
;
Tetrachloroisoindoline-1,3-dione N,N-dimethylformamide solvate
;
loop_
    _publ_author_name
    _publ_author_address
    'Liang, Zu-Pei'
;
Department of Chemistry and Chemical Engineering
Weifang University
Weifang 261061
People's Republic of China
;
    'Li, Jian'
;
Department of Chemistry and Chemical Engineering
Weifang University
Weifang 261061
People's Republic of China
;
    'Zhang, Yun-Chen'
;
Department of Chemistry and Chemical Engineering
Weifang University
Weifang 261061
People's Republic of China
;
    'Tai, Xi-Shi'
;
Department of Chemistry and Chemical Engineering
Weifang University
Weifang 261061
People's Republic of China
;
data_I
_chemical_name_systematic
;
Tetrachloroisoindoline-1,3-dione N,N-dimethylformamide solvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H Cl4 N O2 , C3 H7 N O'
_chemical_formula_sum     'C11 H8 Cl4 N2 O3'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C8 H Cl4 N O2 , C3 H7 N O'
_chemical_formula_weight     357.99
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     5.6583(16)
_cell_length_b     11.268(3)
_cell_length_c     11.817(3)
_cell_angle_alpha     73.244(4)
_cell_angle_beta     82.518(5)
_cell_angle_gamma     80.991(5)
_cell_volume     709.6(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1410
_cell_measurement_theta_min     3.60
_cell_measurement_theta_max     24.84
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.26
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.675
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     360
_exptl_absorpt_coefficient_mu     0.840
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 1997)'
_exptl_absorpt_correction_T_min     0.811
_exptl_absorpt_correction_T_max     0.906
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3691
_diffrn_reflns_av_R_equivalents     0.0252
_diffrn_reflns_av_sigmaI/netI     0.0447
_diffrn_reflns_theta_min     1.81
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     13
_diffrn_reflns_reduction_process     ?
_diffrn_standards_number     .
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     .
_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 > 2sigma(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     2488
_reflns_number_gt     1776
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0681
_refine_ls_R_factor_gt     0.0463
_refine_ls_wR_factor_gt     0.1168
_refine_ls_wR_factor_ref     0.1316
_refine_ls_goodness_of_fit_ref     1.039
_refine_ls_restrained_S_all     1.039
_refine_ls_number_reflns     2488
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
        'calc w = 1/[σ²(Fo²)+(0.062P)²+0.5593P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.982
_refine_diff_density_min     -0.295
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_extinction_coef     0.031(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    'N' 'N' 0.0061 0.0033
                         '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     'SMART (Bruker, 1997)'
_computing_cell_refinement     'SAINT (Bruker, 1997)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material     'SHELXTL'
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
    Cl Cl1 1.31478(18) 0.50354(9) 0.38085(9) 0.0521(3) Uani d . 1 . .
    Cl Cl2 1.0432(2) 0.53339(11) 0.15763(10) 0.0718(4) Uani d . 1 . .
    Cl Cl3 0.6824(2) 0.35207(11) 0.16242(9) 0.0616(4) Uani d . 1 . .
    Cl Cl4 0.59312(17) 0.13136(9) 0.38830(9) 0.0509(3) Uani d . 1 . .
    O O1 1.3399(6) 0.3021(3) 0.6299(3) 0.0657(8) Uani d . 1 . .
    O O2 0.8175(5) 0.0305(3) 0.6327(2) 0.0588(8) Uani d . 1 . .
    N N1 1.0840(6) 0.1529(3) 0.6599(3) 0.0494(8) Uani d . 1 . .
    H H1 1.1143 0.1118 0.7310 0.059 Uiso calc R 1 . .
    C C1 1.1895(7) 0.2577(4) 0.5967(3) 0.0458(9) Uani d . 1 . .
    C C2 1.0819(6) 0.3003(3) 0.4800(3) 0.0364(8) Uani d . 1 . .
    C C3 1.1208(6) 0.4000(3) 0.3818(3) 0.0402(8) Uani d . 1 . .
    C C4 0.9965(7) 0.4132(3) 0.2833(3) 0.0431(9) Uani d . 1 . .
    C C5 0.8359(6) 0.3311(3) 0.2847(3) 0.0411(8) Uani d . 1 . .
    C C6 0.7955(6) 0.2318(3) 0.3850(3) 0.0377(8) Uani d . 1 . .
    C C7 0.9221(6) 0.2174(3) 0.4818(3) 0.0352(8) Uani d . 1 . .
    C C8 0.9253(7) 0.1202(3) 0.5982(3) 0.0442(9) Uani d . 1 . .
    O O3 0.2152(6) 1.0015(3) 0.8760(3) 0.0703(9) Uani d . 1 . .
    N N2 0.5006(6) 0.8550(3) 0.9699(3) 0.0575(9) Uani d . 1 . .
    C C9 0.4085(11) 0.9480(5) 0.8766(5) 0.0736(14) Uani d . 1 . .
    H H9 0.5104 0.9702 0.8076 0.088 Uiso calc R 1 . .
    C C10 0.3708(13) 0.8099(6) 1.0762(5) 0.113(2) Uani d . 1 . .
    H H10A 0.2469 0.8740 1.0905 0.170 Uiso calc R 1 . .
    H H10B 0.4755 0.7853 1.1390 0.170 Uiso calc R 1 . .
    H H10C 0.2993 0.7390 1.0736 0.170 Uiso calc R 1 . .
    C C11 0.7448(11) 0.8044(6) 0.9431(7) 0.114(2) Uani d . 1 . .
    H H11A 0.7946 0.8409 0.8611 0.171 Uiso calc R 1 . .
    H H11B 0.7545 0.7155 0.9579 0.171 Uiso calc R 1 . .
    H H11C 0.8480 0.8231 0.9923 0.171 Uiso calc R 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
    Cl1 0.0567(6) 0.0435(6) 0.0610(6) -0.0187(5) -0.0079(5) -0.0144(5)
    Cl2 0.0916(9) 0.0616(7) 0.0538(6) -0.0304(6) -0.0212(6) 0.0149(5)
    Cl3 0.0682(7) 0.0733(8) 0.0461(6) -0.0149(6) -0.0246(5) -0.0093(5)
    Cl4 0.0471(6) 0.0533(6) 0.0588(6) -0.0178(4) -0.0076(4) -0.0180(5)
    O1 0.076(2) 0.070(2) 0.0603(18) -0.0251(16) -0.0292(15) -0.0129(15)
    O2 0.0666(19) 0.0518(17) 0.0534(17) -0.0236(15) -0.0044(14) 0.0008(13)
    N1 0.061(2) 0.0493(19) 0.0348(16) -0.0105(16) -0.0143(15) -0.0010(14)
    C1 0.050(2) 0.044(2) 0.045(2) -0.0022(18) -0.0114(17) -0.0134(18)
    C2 0.0383(19) 0.0362(19) 0.0366(18) -0.0049(15) -0.0053(14) -0.0119(15)
    C3 0.0393(19) 0.0371(19) 0.046(2) -0.0078(15) -0.0055(16) -0.0126(16)
    C4 0.049(2) 0.038(2) 0.0397(19) -0.0062(17) -0.0082(16) -0.0039(16)
    C5 0.043(2) 0.044(2) 0.0376(19) -0.0048(16) -0.0119(16) -0.0098(16)
    C6 0.0347(18) 0.0374(19) 0.0434(19) -0.0056(15) -0.0043(15) -0.0139(16)
    C7 0.0366(19) 0.0325(18) 0.0356(18) -0.0022(15) -0.0041(14) -0.0088(14)
    C8 0.048(2) 0.039(2) 0.043(2) -0.0036(18) -0.0070(17) -0.0070(17)
    O3 0.070(2) 0.076(2) 0.0573(19) 0.0034(18) -0.0231(16) -0.0056(16)
    N2 0.058(2) 0.052(2) 0.067(2) -0.0059(17) -0.0295(18) -0.0125(18)
    C9 0.085(4) 0.080(4) 0.068(3) -0.028(3) -0.012(3) -0.029(3)
    C10 0.147(6) 0.119(5) 0.082(4) -0.084(5) -0.019(4) -0.001(4)
    C11 0.081(4) 0.102(5) 0.175(7) 0.001(4) -0.023(4) -0.067(5)
_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
    Cl1 C3 . 1.719(4) ?
    Cl2 C4 . 1.720(4) ?
    Cl3 C5 . 1.722(3) ?
    Cl4 C6 . 1.721(4) ?
    O1 C1 . 1.208(5) ?
    O2 C8 . 1.205(5) ?
    N1 C8 . 1.379(5) ?
    N1 C1 . 1.380(5) ?
    N1 H1 . 0.8600 ?
    C1 C2 . 1.500(5) ?
    C2 C3 . 1.385(5) ?
    C2 C7 . 1.392(5) ?
    C3 C4 . 1.397(5) ?
    C4 C5 . 1.390(5) ?
    C5 C6 . 1.398(5) ?
    C6 C7 . 1.385(5) ?
    C7 C8 . 1.491(5) ?
    O3 C9 . 1.163(6) ?
    N2 C10 . 1.373(7) ?
    N2 C9 . 1.378(6) ?
    N2 C11 . 1.441(6) ?
    C9 H9 . 0.9300 ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
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
    C8 N1 C1 . . 113.8(3) ?
    C8 N1 H1 . . 123.1 ?
    C1 N1 H1 . . 123.1 ?
    O1 C1 N1 . . 126.2(3) ?
    O1 C1 C2 . . 128.6(4) ?
    N1 C1 C2 . . 105.2(3) ?
    C3 C2 C7 . . 121.5(3) ?
    C3 C2 C1 . . 130.9(3) ?
    C7 C2 C1 . . 107.5(3) ?
    C2 C3 C4 . . 117.4(3) ?
    C2 C3 Cl1 . . 121.3(3) ?
    C4 C3 Cl1 . . 121.2(3) ?
    C5 C4 C3 . . 121.3(3) ?
    C5 C4 Cl2 . . 119.3(3) ?
    C3 C4 Cl2 . . 119.4(3) ?
    C4 C5 C6 . . 120.7(3) ?
    C4 C5 Cl3 . . 119.9(3) ?
    C6 C5 Cl3 . . 119.3(3) ?
    C7 C6 C5 . . 117.9(3) ?
    C7 C6 Cl4 . . 121.2(3) ?
    C5 C6 Cl4 . . 121.0(3) ?
    C6 C7 C2 . . 121.1(3) ?
    C6 C7 C8 . . 130.7(3) ?
    C2 C7 C8 . . 108.2(3) ?
    O2 C8 N1 . . 126.2(3) ?
    O2 C8 C7 . . 128.6(3) ?
    N1 C8 C7 . . 105.2(3) ?
    C10 N2 C9 . . 123.8(5) ?
    C10 N2 C11 . . 122.8(5) ?
    C9 N2 C11 . . 113.3(5) ?
    O3 C9 N2 . . 126.1(5) ?
    O3 C9 H9 . . 116.9 ?
    N2 C9 H9 . . 116.9 ?
    N2 C10 H10A . . 109.5 ?
    N2 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    N2 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    N2 C11 H11A . . 109.5 ?
    N2 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    N2 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
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
    C8 N1 C1 O1 . . . . -177.3(4) ?
    C8 N1 C1 C2 . . . . 1.4(4) ?
    O1 C1 C2 C3 . . . . -1.1(7) ?
    N1 C1 C2 C3 . . . . -179.7(3) ?
    O1 C1 C2 C7 . . . . 178.2(4) ?
    N1 C1 C2 C7 . . . . -0.5(4) ?
    C7 C2 C3 C4 . . . . -1.1(5) ?
    C1 C2 C3 C4 . . . . 178.0(4) ?
    C7 C2 C3 Cl1 . . . . 179.0(3) ?
    C1 C2 C3 Cl1 . . . . -1.9(5) ?
    C2 C3 C4 C5 . . . . 1.4(5) ?
    Cl1 C3 C4 C5 . . . . -178.7(3) ?
    C2 C3 C4 Cl2 . . . . -178.5(3) ?
    Cl1 C3 C4 Cl2 . . . . 1.4(4) ?
    C3 C4 C5 C6 . . . . -0.5(6) ?
    Cl2 C4 C5 C6 . . . . 179.4(3) ?
    C3 C4 C5 Cl3 . . . . 178.9(3) ?
    Cl2 C4 C5 Cl3 . . . . -1.2(5) ?
    C4 C5 C6 C7 . . . . -0.6(5) ?
    Cl3 C5 C6 C7 . . . . 179.9(3) ?
    C4 C5 C6 Cl4 . . . . 178.9(3) ?
    Cl3 C5 C6 Cl4 . . . . -0.6(4) ?
    C5 C6 C7 C2 . . . . 0.9(5) ?
    Cl4 C6 C7 C2 . . . . -178.6(3) ?
    C5 C6 C7 C8 . . . . -177.7(3) ?
    Cl4 C6 C7 C8 . . . . 2.8(5) ?
    C3 C2 C7 C6 . . . . 0.0(5) ?
    C1 C2 C7 C6 . . . . -179.3(3) ?
    C3 C2 C7 C8 . . . . 178.9(3) ?
    C1 C2 C7 C8 . . . . -0.5(4) ?
    C1 N1 C8 O2 . . . . 177.4(4) ?
    C1 N1 C8 C7 . . . . -1.6(4) ?
    C6 C7 C8 O2 . . . . 1.0(7) ?
    C2 C7 C8 O2 . . . . -177.7(4) ?
    C6 C7 C8 N1 . . . . 180.0(3) ?
    C2 C7 C8 N1 . . . . 1.2(4) ?
    C10 N2 C9 O3 . . . . 1.7(7) ?
    C11 N2 C9 O3 . . . . 178.7(5) ?
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
    N1 H1 O3 1_645 0.86 1.90 2.752(4) 170
    C9 H9 O2 1_565 0.93 2.53 3.452(6) 175
