#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/75/2227572.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227572
loop_
_publ_author_name
'Wei, Wen-Bin'
'Tian, Shuo'
'Zhou, Hao'
'Sun, Jie'
'Wang, Hai-Bo'
_publ_section_title
;
 5-Chloroindoline-2,3-dione
;
_journal_coeditor_code           HB5688
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3024
_journal_paper_doi               10.1107/S1600536810042522
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H4 Cl N O2'
_chemical_formula_moiety         'C8 H4 Cl N O2'
_chemical_formula_sum            'C8 H4 Cl N O2'
_chemical_formula_weight         181.57
_chemical_melting_point          520
_chemical_name_systematic
;
5-Chloroindoline-2,3-dione
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.706(5)
_cell_length_b                   5.6890(11)
_cell_length_c                   5.2090(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     732.1(2)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0563
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1746
_diffrn_reflns_theta_full        26.97
_diffrn_reflns_theta_max         26.97
_diffrn_reflns_theta_min         1.65
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.468
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_correction_T_min  0.9547
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.242
_refine_ls_abs_structure_details 'Flack (1983), 862 Friedel pairs'
_refine_ls_abs_structure_Flack   0.11(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         884
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0374
_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/[σ²(Fo²)+(0.0650P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1015
_reflns_number_gt                734
_reflns_number_total             884
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5688.cif
_cod_data_source_block           I
_cod_database_code               2227572
_cod_database_fobs_code          2227572
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
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 Cl 0.26410(4) 0.6028(2) 0.2215(3) 0.0588(4) Uani d . 1 . .
N N 0.45038(11) 0.1571(5) 0.7251(9) 0.0378(8) Uani d . 1 . .
H H0A 0.4676 0.0291 0.6924 0.045 Uiso calc R 1 . .
O O1 0.49964(12) 0.2818(5) 1.0752(7) 0.0441(7) Uani d . 1 . .
C C1 0.46351(13) 0.3075(6) 0.9153(9) 0.0335(8) Uani d D 1 . .
O O2 0.42293(11) 0.6781(5) 1.0449(7) 0.0446(7) Uani d . 1 . .
C C2 0.42335(13) 0.5098(6) 0.9018(8) 0.0332(8) Uani d D 1 . .
C C3 0.38713(13) 0.4525(6) 0.6867(8) 0.0321(8) Uani d . 1 . .
C C4 0.34278(14) 0.5650(7) 0.5820(9) 0.0351(9) Uani d . 1 . .
H H4A 0.3300 0.7058 0.6497 0.042 Uiso calc R 1 . .
C C5 0.31808(13) 0.4609(7) 0.3733(8) 0.0373(9) Uani d . 1 . .
C C6 0.33568(15) 0.2468(7) 0.2760(8) 0.0409(10) Uani d . 1 . .
H H6A 0.3175 0.1793 0.1381 0.049 Uiso calc R 1 . .
C C7 0.37976(16) 0.1329(6) 0.3811(10) 0.0390(9) Uani d . 1 . .
H H7A 0.3920 -0.0093 0.3148 0.047 Uiso calc R 1 . .
C C8 0.40480(13) 0.2366(6) 0.5864(9) 0.0333(8) 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
Cl 0.0493(6) 0.0757(8) 0.0512(6) 0.0147(5) -0.0117(6) 0.0048(8)
N 0.0425(16) 0.0279(14) 0.0430(19) 0.0100(12) -0.0008(19) -0.002(2)
O1 0.0477(13) 0.0415(14) 0.0431(17) 0.0070(13) -0.0070(15) 0.0018(16)
C1 0.0351(18) 0.0309(18) 0.034(2) 0.0025(15) 0.0050(19) 0.0035(19)
O2 0.0524(16) 0.0387(14) 0.0427(17) 0.0069(13) 0.0030(15) -0.0108(15)
C2 0.0398(18) 0.0263(15) 0.033(2) 0.0039(15) 0.0081(18) -0.0007(18)
C3 0.0341(16) 0.0284(15) 0.034(2) 0.0043(14) 0.0069(18) 0.0027(17)
C4 0.0402(18) 0.0330(17) 0.032(2) 0.0046(15) 0.0074(18) -0.0012(18)
C5 0.0326(16) 0.045(2) 0.034(2) 0.0015(16) 0.0002(18) 0.006(2)
C6 0.0439(19) 0.045(2) 0.033(2) -0.0096(18) 0.0013(18) -0.0013(19)
C7 0.049(2) 0.0302(17) 0.038(2) -0.0020(16) 0.009(2) -0.0053(18)
C8 0.0352(17) 0.0294(17) 0.035(2) -0.0004(15) 0.0059(18) -0.0018(18)
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'
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 N C8 . . 111.4(3) ?
C1 N H0A . . 124.3 ?
C8 N H0A . . 124.3 ?
O1 C1 N . . 126.7(3) ?
O1 C1 C2 . . 126.5(4) ?
N C1 C2 . . 106.8(3) ?
O2 C2 C3 . . 129.6(3) ?
O2 C2 C1 . . 125.1(4) ?
C3 C2 C1 . . 105.3(3) ?
C4 C3 C8 . . 120.3(4) ?
C4 C3 C2 . . 132.9(3) ?
C8 C3 C2 . . 106.7(3) ?
C5 C4 C3 . . 117.6(4) ?
C5 C4 H4A . . 121.2 ?
C3 C4 H4A . . 121.2 ?
C4 C5 C6 . . 121.7(4) ?
C4 C5 Cl . . 119.7(3) ?
C6 C5 Cl . . 118.6(3) ?
C7 C6 C5 . . 120.9(4) ?
C7 C6 H6A . . 119.5 ?
C5 C6 H6A . . 119.5 ?
C8 C7 C6 . . 117.6(4) ?
C8 C7 H7A . . 121.2 ?
C6 C7 H7A . . 121.2 ?
C7 C8 C3 . . 121.8(4) ?
C7 C8 N . . 128.5(3) ?
C3 C8 N . . 109.7(4) ?
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
Cl C5 . 1.748(4) ?
N C1 . 1.349(6) ?
N C8 . 1.412(5) ?
N H0A . 0.8600 ?
O1 C1 . 1.229(5) ?
C1 C2 . 1.521(4) ?
O2 C2 . 1.213(4) ?
C2 C3 . 1.471(5) ?
C3 C4 . 1.381(5) ?
C3 C8 . 1.404(5) ?
C4 C5 . 1.381(6) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.389(6) ?
C6 C7 . 1.380(6) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.369(6) ?
C7 H7A . 0.9300 ?
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
N H0A O1 2_654 0.86 2.04 2.893(4) 172
C7 H7A O2 1_544 0.93 2.39 3.301(5) 166
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 N C1 O1 . . . . 176.7(4) ?
C8 N C1 C2 . . . . -0.8(4) ?
O1 C1 C2 O2 . . . . 2.4(7) ?
N C1 C2 O2 . . . . 179.9(4) ?
O1 C1 C2 C3 . . . . -177.1(4) ?
N C1 C2 C3 . . . . 0.4(4) ?
O2 C2 C3 C4 . . . . -0.2(7) ?
C1 C2 C3 C4 . . . . 179.2(4) ?
O2 C2 C3 C8 . . . . -179.3(4) ?
C1 C2 C3 C8 . . . . 0.2(4) ?
C8 C3 C4 C5 . . . . -1.9(6) ?
C2 C3 C4 C5 . . . . 179.2(4) ?
C3 C4 C5 C6 . . . . 2.2(6) ?
C3 C4 C5 Cl . . . . -176.5(3) ?
C4 C5 C6 C7 . . . . -1.8(6) ?
Cl C5 C6 C7 . . . . 176.9(3) ?
C5 C6 C7 C8 . . . . 1.0(6) ?
C6 C7 C8 C3 . . . . -0.7(6) ?
C6 C7 C8 N . . . . -179.5(4) ?
C4 C3 C8 C7 . . . . 1.2(6) ?
C2 C3 C8 C7 . . . . -179.6(4) ?
C4 C3 C8 N . . . . -179.8(4) ?
C2 C3 C8 N . . . . -0.6(4) ?
C1 N C8 C7 . . . . 179.8(4) ?
C1 N C8 C3 . . . . 0.9(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 78664
2 PubChem 87203
