##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_journal_date_recd_electronic     2016-04-16
_journal_date_accepted     2016-04-23
_journal_name_full     'IUCrData'
_journal_year     2016
_journal_volume     1
_journal_issue      4
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314616006891
_journal_coeditor_code     SJ4026
_publ_contact_author_name     'David R. Manke'
_publ_contact_author_address
;
Department of Chemistry and Biochemistry
University of Massachusetts Dartmouth
285 Old Westport Road
North Dartmouth, MA 02747,
USA
;
_publ_contact_author_email     'dmanke@umassd.edu'
_publ_contact_author_fax     '(508)999-9167'
_publ_contact_author_phone     '(508)910-6554'
_publ_section_title
;
4-Chloro-1H-indole-2,3-dione
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Juma, Rashid M.' .
;
Department of Chemistry and Biochemistry
University of Massachusetts Dartmouth
285 Old Westport Road
North Dartmouth, MA 02747,
USA
;
    'Golen, James A.' .
;
Department of Chemistry and Biochemistry
University of Massachusetts Dartmouth
285 Old Westport Road
North Dartmouth, MA 02747,
USA
;
    'Manke, David R.' .
;
Department of Chemistry and Biochemistry
University of Massachusetts Dartmouth
285 Old Westport Road
North Dartmouth, MA 02747,
USA
;
_publ_section_synopsis
;
The crystal structure of 4-chloro-1H-indole-2,3-dione is reported. In
the crystal, N---H...O and C---H...Cl interactions are present.
;
_chemical_name_systematic
;
4-Chloro-1H-indole-2,3-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H4 Cl N O2'
_chemical_formula_sum     'C8 H4 Cl N O2'
_chemical_formula_iupac     'C8 H4 Cl N O2'
_chemical_formula_weight     181.57
_chemical_melting_point     ?
_symmetry_space_group_name_hall     'P 2yb'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     8.2745(8)
_cell_length_b     6.0367(6)
_cell_length_c     14.8609(14)
_cell_angle_alpha     90
_cell_angle_beta     104.746(5)
_cell_angle_gamma     90
_cell_volume     717.86(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6743
_cell_measurement_theta_min     3.08
_cell_measurement_theta_max     68.50
_cell_measurement_temperature     120(2)
_exptl_crystal_description     block
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.04
_exptl_crystal_size_min     0.04
_exptl_crystal_density_diffrn     1.680
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     368
_exptl_absorpt_coefficient_mu     4.314
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.2052
_exptl_absorpt_correction_T_max     0.3107
_diffrn_ambient_temperature     120.06
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator     'HELIOS MX'
_diffrn_measurement_device_type     'Bruker CMOS'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9961
_diffrn_reflns_av_R_equivalents     0.0580
_diffrn_reflns_theta_min     3.075
_diffrn_reflns_theta_max     68.494
_diffrn_reflns_theta_full     68.000
_diffrn_measured_fraction_theta_max     0.997
_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     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     0
_refine_special_details
;
 Refined as a 2-component inversion twin.
;
_reflns_number_total     2579
_reflns_number_gt     2388
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0423
_refine_ls_R_factor_gt     0.0379
_refine_ls_wR_factor_gt     0.0923
_refine_ls_wR_factor_ref     0.0959
_refine_ls_goodness_of_fit_ref     1.037
_refine_ls_restrained_S_all     1.036
_refine_ls_number_reflns     2579
_refine_ls_number_parameters     224
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0531P)²+0.1710P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.579
_refine_diff_density_min     -0.269
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack     0.11(3)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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'
    'Cl' 'Cl' 0.3639 0.7018
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009) and publCIF (Westrip,
2010)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.82671(11) -0.28031(19) 0.40490(7) 0.0329(3) Uani d 1 . .
    Cl Cl2 1.05021(12) 1.19333(19) 0.35368(6) 0.0317(3) Uani d 1 . .
    O O1 0.2975(4) -0.0106(5) 0.09037(18) 0.0293(7) Uani d 1 . .
    O O2 0.5638(3) -0.2926(6) 0.19884(19) 0.0332(7) Uani d 1 . .
    O O3 1.1154(3) 0.4626(5) 0.11689(18) 0.0279(7) Uani d 1 . .
    O O4 1.1901(3) 0.7341(6) 0.28454(17) 0.0289(7) Uani d 1 . .
    N N1 0.3652(4) 0.2002(7) 0.2246(2) 0.0246(7) Uani d 1 . .
    H H1 0.295(5) 0.309(6) 0.208(3) 0.029 Uiso d 1 . .
    N N2 0.9124(4) 0.7291(7) 0.0657(2) 0.0248(8) Uani d 1 . .
    H H2 0.868(5) 0.688(9) 0.0088(14) 0.030 Uiso d 1 . .
    C C1 0.3785(5) 0.0273(7) 0.1694(3) 0.0240(9) Uani d 1 . .
    C C2 0.5204(5) -0.1236(7) 0.2281(3) 0.0251(9) Uani d 1 . .
    C C3 0.5750(5) -0.0089(7) 0.3177(3) 0.0235(9) Uani d 1 . .
    C C4 0.6994(5) -0.0499(8) 0.3987(3) 0.0267(9) Uani d 1 . .
    C C5 0.7209(5) 0.0939(8) 0.4734(3) 0.0285(10) Uani d 1 . .
    H H5 0.8050 0.0660 0.5290 0.034 Uiso calc 1 . .
    C C6 0.6195(5) 0.2785(8) 0.4667(3) 0.0285(10) Uani d 1 . .
    H H6 0.6340 0.3741 0.5189 0.034 Uiso calc 1 . .
    C C7 0.4963(5) 0.3293(8) 0.3859(3) 0.0281(9) Uani d 1 . .
    H H7 0.4289 0.4582 0.3815 0.034 Uiso calc 1 . .
    C C8 0.4775(4) 0.1828(8) 0.3127(2) 0.0226(8) Uani d 1 . .
    C C9 1.0412(5) 0.6310(7) 0.1266(3) 0.0229(9) Uani d 1 . .
    C C10 1.0799(5) 0.7769(7) 0.2159(3) 0.0221(9) Uani d 1 . .
    C C11 0.9586(5) 0.9583(7) 0.1941(3) 0.0229(9) Uani d 1 . .
    C C12 0.9285(5) 1.1431(7) 0.2424(3) 0.0252(9) Uani d 1 . .
    C C13 0.8008(5) 1.2893(8) 0.2018(3) 0.0290(10) Uani d 1 . .
    H H13 0.7766 1.4130 0.2357 0.035 Uiso calc 1 . .
    C C14 0.7089(5) 1.2512(8) 0.1105(3) 0.0297(10) Uani d 1 . .
    H H14 0.6232 1.3527 0.0823 0.036 Uiso calc 1 . .
    C C15 0.7387(5) 1.0694(8) 0.0594(3) 0.0273(10) Uani d 1 . .
    H H15 0.6758 1.0467 -0.0029 0.033 Uiso calc 1 . .
    C C16 0.8623(5) 0.9235(7) 0.1022(3) 0.0237(9) Uani d 1 . .
_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 C4 . 1.733(5) ?
    Cl2 C12 . 1.730(4) ?
    O1 C1 . 1.217(5) ?
    O2 C2 . 1.200(6) ?
    O3 C9 . 1.215(5) ?
    O4 C10 . 1.210(5) ?
    N1 H1 . 0.869(7) ?
    N1 C1 . 1.349(6) ?
    N1 C8 . 1.404(4) ?
    N2 H2 . 0.869(7) ?
    N2 C9 . 1.347(5) ?
    N2 C16 . 1.399(6) ?
    C1 C2 . 1.564(6) ?
    C2 C3 . 1.467(6) ?
    C3 C4 . 1.393(6) ?
    C3 C8 . 1.402(6) ?
    C4 C5 . 1.385(6) ?
    C5 H5 . 0.9500 ?
    C5 C6 . 1.383(7) ?
    C6 H6 . 0.9500 ?
    C6 C7 . 1.398(6) ?
    C7 H7 . 0.9500 ?
    C7 C8 . 1.379(6) ?
    C9 C10 . 1.557(6) ?
    C10 C11 . 1.465(6) ?
    C11 C12 . 1.383(6) ?
    C11 C16 . 1.410(6) ?
    C12 C13 . 1.391(6) ?
    C13 H13 . 0.9500 ?
    C13 C14 . 1.395(6) ?
    C14 H14 . 0.9500 ?
    C14 C15 . 1.392(6) ?
    C15 H15 . 0.9500 ?
    C15 C16 . 1.376(6) ?
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
    C1 N1 H1 . . 124(3) ?
    C1 N1 C8 . . 111.9(4) ?
    C8 N1 H1 . . 124(3) ?
    C9 N2 H2 . . 127(4) ?
    C9 N2 C16 . . 111.7(3) ?
    C16 N2 H2 . . 122(4) ?
    O1 C1 N1 . . 128.5(4) ?
    O1 C1 C2 . . 125.4(4) ?
    N1 C1 C2 . . 106.1(3) ?
    O2 C2 C1 . . 123.0(4) ?
    O2 C2 C3 . . 132.8(4) ?
    C3 C2 C1 . . 104.2(3) ?
    C4 C3 C2 . . 133.7(4) ?
    C4 C3 C8 . . 118.8(4) ?
    C8 C3 C2 . . 107.5(3) ?
    C3 C4 Cl1 . . 119.6(3) ?
    C5 C4 Cl1 . . 120.6(3) ?
    C5 C4 C3 . . 119.8(4) ?
    C4 C5 H5 . . 120.2 ?
    C6 C5 C4 . . 119.7(4) ?
    C6 C5 H5 . . 120.2 ?
    C5 C6 H6 . . 118.8 ?
    C5 C6 C7 . . 122.4(4) ?
    C7 C6 H6 . . 118.8 ?
    C6 C7 H7 . . 121.7 ?
    C8 C7 C6 . . 116.6(4) ?
    C8 C7 H7 . . 121.7 ?
    C3 C8 N1 . . 110.3(4) ?
    C7 C8 N1 . . 127.1(4) ?
    C7 C8 C3 . . 122.7(4) ?
    O3 C9 N2 . . 128.7(4) ?
    O3 C9 C10 . . 125.0(4) ?
    N2 C9 C10 . . 106.3(3) ?
    O4 C10 C9 . . 123.0(4) ?
    O4 C10 C11 . . 132.3(4) ?
    C11 C10 C9 . . 104.7(3) ?
    C12 C11 C10 . . 133.8(4) ?
    C12 C11 C16 . . 119.4(4) ?
    C16 C11 C10 . . 106.9(3) ?
    C11 C12 Cl2 . . 120.0(3) ?
    C11 C12 C13 . . 120.3(4) ?
    C13 C12 Cl2 . . 119.7(3) ?
    C12 C13 H13 . . 120.6 ?
    C12 C13 C14 . . 118.9(4) ?
    C14 C13 H13 . . 120.6 ?
    C13 C14 H14 . . 118.9 ?
    C15 C14 C13 . . 122.1(4) ?
    C15 C14 H14 . . 118.9 ?
    C14 C15 H15 . . 121.1 ?
    C16 C15 C14 . . 117.8(4) ?
    C16 C15 H15 . . 121.1 ?
    N2 C16 C11 . . 110.5(3) ?
    C15 C16 N2 . . 128.0(4) ?
    C15 C16 C11 . . 121.5(4) ?
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
    Cl1 C4 C5 C6 . . . . 179.2(3) ?
    Cl2 C12 C13 C14 . . . . 177.2(3) ?
    O1 C1 C2 O2 . . . . 1.0(7) ?
    O1 C1 C2 C3 . . . . -178.8(4) ?
    O2 C2 C3 C4 . . . . 2.8(8) ?
    O2 C2 C3 C8 . . . . -179.3(4) ?
    O3 C9 C10 O4 . . . . 0.3(6) ?
    O3 C9 C10 C11 . . . . -179.9(4) ?
    O4 C10 C11 C12 . . . . 1.0(8) ?
    O4 C10 C11 C16 . . . . 179.0(4) ?
    N1 C1 C2 O2 . . . . -179.9(4) ?
    N1 C1 C2 C3 . . . . 0.3(4) ?
    N2 C9 C10 O4 . . . . -180.0(4) ?
    N2 C9 C10 C11 . . . . -0.2(4) ?
    C1 N1 C8 C3 . . . . 1.3(5) ?
    C1 N1 C8 C7 . . . . -179.6(4) ?
    C1 C2 C3 C4 . . . . -177.4(4) ?
    C1 C2 C3 C8 . . . . 0.4(4) ?
    C2 C3 C4 Cl1 . . . . 0.0(6) ?
    C2 C3 C4 C5 . . . . 179.7(4) ?
    C2 C3 C8 N1 . . . . -1.0(4) ?
    C2 C3 C8 C7 . . . . 179.8(4) ?
    C3 C4 C5 C6 . . . . -0.5(6) ?
    C4 C3 C8 N1 . . . . 177.2(3) ?
    C4 C3 C8 C7 . . . . -2.0(6) ?
    C4 C5 C6 C7 . . . . -1.3(6) ?
    C5 C6 C7 C8 . . . . 1.4(6) ?
    C6 C7 C8 N1 . . . . -178.8(4) ?
    C6 C7 C8 C3 . . . . 0.3(6) ?
    C8 N1 C1 O1 . . . . 178.1(4) ?
    C8 N1 C1 C2 . . . . -1.0(4) ?
    C8 C3 C4 Cl1 . . . . -177.6(3) ?
    C8 C3 C4 C5 . . . . 2.1(6) ?
    C9 N2 C16 C11 . . . . -1.7(4) ?
    C9 N2 C16 C15 . . . . 178.1(4) ?
    C9 C10 C11 C12 . . . . -178.7(4) ?
    C9 C10 C11 C16 . . . . -0.8(4) ?
    C10 C11 C12 Cl2 . . . . 0.0(6) ?
    C10 C11 C12 C13 . . . . 179.9(4) ?
    C10 C11 C16 N2 . . . . 1.5(4) ?
    C10 C11 C16 C15 . . . . -178.4(4) ?
    C11 C12 C13 C14 . . . . -2.7(6) ?
    C12 C11 C16 N2 . . . . 179.8(3) ?
    C12 C11 C16 C15 . . . . 0.0(6) ?
    C12 C13 C14 C15 . . . . 1.3(6) ?
    C13 C14 C15 C16 . . . . 0.7(6) ?
    C14 C15 C16 N2 . . . . 178.9(4) ?
    C14 C15 C16 C11 . . . . -1.3(6) ?
    C16 N2 C9 O3 . . . . -179.2(4) ?
    C16 N2 C9 C10 . . . . 1.1(4) ?
    C16 C11 C12 Cl2 . . . . -177.8(3) ?
    C16 C11 C12 C13 . . . . 2.1(6) ?
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_455 0.869(7) 1.97(2) 2.768(5) 152(4)
    N2 H2 O1 2_655 0.869(7) 2.11(2) 2.905(4) 152(5)
    C5 H5 Cl2 2_736 0.95 2.91 3.682(5) 139.2
_shelxl_version_number     2014/6
