#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/77/2227744.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_2227744
loop_
_publ_author_name
'Wang, Yao'
'Wan, Chong-Qing'
'Zheng, Tingting'
'Cao, Sheng-Li'
_publ_section_title
;
 3,3-Dichloro-1-(chloromethyl)indolin-2-one
;
_journal_coeditor_code           KJ2158
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2858
_journal_paper_doi               10.1107/S1600536810040717
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C9 H6 Cl3 N O'
_chemical_formula_moiety         'C9 H6 Cl3 N O'
_chemical_formula_sum            'C9 H6 Cl3 N O'
_chemical_formula_weight         250.50
_chemical_name_systematic
;
3,3-Dichloro-1-(chloromethyl)indolin-2-one
;
_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                 93.3810(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.61020(10)
_cell_length_b                   14.5573(2)
_cell_length_c                   8.24610(10)
_cell_measurement_reflns_used    7007
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.839
_cell_measurement_theta_min      2.475
_cell_volume                     1031.78(2)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0163
_diffrn_reflns_av_sigmaI/netI    0.0115
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13146
_diffrn_reflns_theta_full        27.92
_diffrn_reflns_theta_max         27.92
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_meas      1.613
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.488
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0347
_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)+(0.0433P)²+0.4377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0943
_reflns_number_gt                2156
_reflns_number_total             2450
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            kj2158.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227744
_cod_database_fobs_code          2227744
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C C9 0.4139(2) 0.66723(13) 0.5958(2) 0.0448(4) Uani d . 1 . .
H H9A 0.3747 0.6171 0.5275 0.054 Uiso calc R 1 . .
H H9B 0.4404 0.7176 0.5255 0.054 Uiso calc R 1 . .
Cl Cl1 0.72991(7) 0.48322(4) 0.99637(6) 0.06304(17) Uani d . 1 . .
Cl Cl3 0.87749(7) 0.48989(4) 0.69017(7) 0.06607(17) Uani d . 1 . .
Cl Cl2 0.26419(5) 0.70402(4) 0.72483(7) 0.06448(17) Uani d . 1 . .
C C1 0.9042(2) 0.68812(13) 0.9240(2) 0.0478(4) Uani d . 1 . .
H H1 0.9838 0.6541 0.9762 0.057 Uiso calc R 1 . .
C C2 0.9062(2) 0.78348(14) 0.9279(3) 0.0533(4) Uani d . 1 . .
H H2 0.9882 0.8138 0.9836 0.064 Uiso calc R 1 . .
C C3 0.7883(2) 0.83366(12) 0.8503(2) 0.0497(4) Uani d . 1 . .
H H3 0.7922 0.8975 0.8545 0.060 Uiso calc R 1 . .
C C4 0.66346(19) 0.79124(11) 0.7659(2) 0.0415(4) Uani d . 1 . .
H H4 0.5837 0.8252 0.7139 0.050 Uiso calc R 1 . .
C C5 0.66323(17) 0.69655(10) 0.76292(19) 0.0345(3) Uani d . 1 . .
C C6 0.78112(18) 0.64512(11) 0.84075(19) 0.0373(3) Uani d . 1 . .
C C7 0.74369(19) 0.54609(11) 0.8146(2) 0.0410(3) Uani d . 1 . .
C C8 0.58313(19) 0.54734(11) 0.7189(2) 0.0402(3) Uani d . 1 . .
N N1 0.54994(15) 0.63781(9) 0.68728(17) 0.0385(3) Uani d . 1 . .
O O1 0.50408(18) 0.48209(9) 0.68047(17) 0.0562(3) Uani d . 1 . .
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'
Cl Cl 0.1484 0.1585 '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'
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
N1 C9 Cl2 . . 111.84(12) ?
N1 C9 H9A . . 109.2 ?
Cl2 C9 H9A . . 109.2 ?
N1 C9 H9B . . 109.2 ?
Cl2 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
C6 C1 C2 . . 118.30(16) ?
C6 C1 H1 . . 120.9 ?
C2 C1 H1 . . 120.9 ?
C3 C2 C1 . . 120.73(17) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C2 C3 C4 . . 121.61(16) ?
C2 C3 H3 . . 119.2 ?
C4 C3 H3 . . 119.2 ?
C5 C4 C3 . . 116.96(16) ?
C5 C4 H4 . . 121.5 ?
C3 C4 H4 . . 121.5 ?
C4 C5 C6 . . 122.06(15) ?
C4 C5 N1 . . 127.79(14) ?
C6 C5 N1 . . 110.15(13) ?
C1 C6 C5 . . 120.33(15) ?
C1 C6 C7 . . 131.67(15) ?
C5 C6 C7 . . 107.99(14) ?
C6 C7 C8 . . 103.95(12) ?
C6 C7 Cl1 . . 113.78(12) ?
C8 C7 Cl1 . . 109.59(12) ?
C6 C7 Cl3 . . 112.65(12) ?
C8 C7 Cl3 . . 107.40(11) ?
Cl1 C7 Cl3 . . 109.15(8) ?
O1 C8 N1 . . 127.02(16) ?
O1 C8 C7 . . 126.84(15) ?
N1 C8 C7 . . 106.13(13) ?
C8 N1 C5 . . 111.52(13) ?
C8 N1 C9 . . 123.16(14) ?
C5 N1 C9 . . 125.26(13) ?
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
C9 N1 . 1.422(2) ?
C9 Cl2 . 1.8009(18) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
Cl1 C7 . 1.7664(17) ?
Cl3 C7 . 1.7856(16) ?
C1 C6 . 1.378(2) ?
C1 C2 . 1.389(3) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.378(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.390(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.379(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.388(2) ?
C5 N1 . 1.414(2) ?
C6 C7 . 1.490(2) ?
C7 C8 . 1.551(2) ?
C8 O1 . 1.200(2) ?
C8 N1 . 1.369(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
_geom_hbond_publ_flag
C4 H4 O1 2_656 0.93 2.57 3.173(2) 123. yes
C9 H9A O1 . 0.9700 2.5600 2.879(2) 100.00 no
C9 H9A O1 3_666 0.97 2.52 3.256(2) 133 no
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
C6 C1 C2 C3 . . . . -0.1(3) ?
C1 C2 C3 C4 . . . . 0.1(3) ?
C2 C3 C4 C5 . . . . -0.2(3) ?
C3 C4 C5 C6 . . . . 0.3(2) ?
C3 C4 C5 N1 . . . . 179.42(16) ?
C2 C1 C6 C5 . . . . 0.2(3) ?
C2 C1 C6 C7 . . . . -179.47(18) ?
C4 C5 C6 C1 . . . . -0.3(2) ?
N1 C5 C6 C1 . . . . -179.56(15) ?
C4 C5 C6 C7 . . . . 179.42(15) ?
N1 C5 C6 C7 . . . . 0.16(18) ?
C1 C6 C7 C8 . . . . 176.63(17) ?
C5 C6 C7 C8 . . . . -3.04(17) ?
C1 C6 C7 Cl1 . . . . 57.5(2) ?
C5 C6 C7 Cl1 . . . . -122.18(13) ?
C1 C6 C7 Cl3 . . . . -67.4(2) ?
C5 C6 C7 Cl3 . . . . 112.91(13) ?
C6 C7 C8 O1 . . . . -175.08(17) ?
Cl1 C7 C8 O1 . . . . -53.1(2) ?
Cl3 C7 C8 O1 . . . . 65.3(2) ?
C6 C7 C8 N1 . . . . 4.91(17) ?
Cl1 C7 C8 N1 . . . . 126.87(12) ?
Cl3 C7 C8 N1 . . . . -114.67(12) ?
O1 C8 N1 C5 . . . . 174.89(17) ?
C7 C8 N1 C5 . . . . -5.10(18) ?
O1 C8 N1 C9 . . . . -2.4(3) ?
C7 C8 N1 C9 . . . . 177.62(14) ?
C4 C5 N1 C8 . . . . -175.89(16) ?
C6 C5 N1 C8 . . . . 3.31(19) ?
C4 C5 N1 C9 . . . . 1.3(3) ?
C6 C5 N1 C9 . . . . -179.48(15) ?
Cl2 C9 N1 C8 . . . . 98.78(17) ?
Cl2 C9 N1 C5 . . . . -78.12(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656276
