#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/77/2217755.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2217755
loop_
_publ_author_name
'De, Amitabha'
_publ_section_title
;
 5'-Chlorospiro[1,3-dioxolane-2,3'-indolin]-2'-one: a potential
 anticonvulsant
;
_journal_coeditor_code           ER2049
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o562
_journal_paper_doi               10.1107/S160053680800336X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C10 H8 Cl N O3'
_chemical_formula_moiety         'C10 H8 Cl N O3'
_chemical_formula_sum            'C10 H8 Cl N O3'
_chemical_formula_weight         225.62
_chemical_melting_point          460
_chemical_name_systematic
;
5'-Chlorospiro[1,3-dioxolane-2,3'-indolin]-2'-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-I 2yc'
_symmetry_space_group_name_H-M   'I 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 92.855(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.266(2)
_cell_length_b                   7.3600(10)
_cell_length_c                   14.8210(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.23
_cell_volume                     1990.0(4)
_computing_cell_refinement
'AFC-4 Diffractometer Control Software (Rigaku, 1997)'
_computing_data_collection
'AFC-4 Diffractometer Control Software (Rigaku, 1997)'
_computing_data_reduction
'AFC-4 Diffractometer Control Software (Rigaku, 1997)'
_computing_molecular_graphics    'ORTEP (Johnson, 1965)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1983)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device       'Rigaku AFC-4'
_diffrn_measurement_method       ω
_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  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2479
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        0.2
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.368
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      1.498
_exptl_crystal_density_method    flotation
_exptl_crystal_description       needle
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.521
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.832
_refine_ls_goodness_of_fit_ref   0.802
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.832
_refine_ls_restrained_S_obs      0.802
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/esd_mean        0.001
_refine_ls_shift/su_max          0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1365P)²+2.6179P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1892
_reflns_number_gt                1591
_reflns_number_total             2297
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            er2049.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'I 2/c'
_cod_database_code               2217755
_cod_database_fobs_code          2217755
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z'
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cl Cl1 0.40898(6) -0.00775(11) 0.43060(5) 0.0825(4) Uani d . 1
O O1 0.3184(2) 0.5049(4) 0.0001(2) 0.0931(9) Uani d . 1
O O2 0.37608(10) 0.5934(2) 0.18885(12) 0.0534(5) Uani d . 1
O O3 0.45532(9) 0.4244(2) 0.11210(12) 0.0494(4) Uani d . 1
N N1 0.28723(12) 0.2542(4) 0.0815(2) 0.0612(6) Uani d . 1
C C1 0.3263(2) 0.4038(4) 0.0651(2) 0.0596(7) Uani d . 1
C C2 0.38452(12) 0.4261(3) 0.1450(2) 0.0442(5) Uani d . 1
C C3 0.36853(11) 0.2671(3) 0.20354(15) 0.0418(5) Uani d . 1
C C4 0.40017(12) 0.2147(3) 0.2858(2) 0.0446(5) Uani d . 1
C C5 0.3712(2) 0.0628(3) 0.3264(2) 0.0516(6) Uani d . 1
C C6 0.3125(2) -0.0317(4) 0.2873(2) 0.0634(8) Uani d . 1
C C7 0.2809(2) 0.0217(4) 0.2041(2) 0.0606(7) Uani d . 1
C C8 0.31030(12) 0.1704(3) 0.1639(2) 0.0484(5) Uani d . 1
C C9 0.4219(2) 0.7216(4) 0.1450(2) 0.0678(8) Uani d . 1
C C10 0.4787(2) 0.6085(4) 0.1035(3) 0.0759(9) Uani d . 1
H H4 0.4389(16) 0.275(4) 0.3142(18) 0.051(7) Uiso d . 1
H H6 0.2955(19) -0.126(5) 0.316(2) 0.069(9) Uiso d . 1
H H7 0.234(2) -0.037(5) 0.181(2) 0.077(10) Uiso d . 1
H H1 0.2565(18) 0.206(5) 0.047(2) 0.062(9) Uiso d . 1
H H91 0.393(2) 0.792(6) 0.102(3) 0.110(14) Uiso d . 1
H H92 0.441(2) 0.808(7) 0.189(3) 0.086(11) Uiso d . 1
H H101 0.5260 0.6263 0.1351 0.08 Uiso calc R 1
H H102 0.4822 0.6401 0.0403 0.08 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 O2 C9 106.6(2)
C2 O3 C10 107.9(2)
C1 N1 C8 112.1(2)
C1 N1 H1 127.(2)
C8 N1 H1 121.(2)
O1 C1 N1 127.0(3)
O1 C1 C2 125.8(3)
N1 C1 C2 107.3(2)
O3 C2 O2 107.0(2)
O3 C2 C3 113.9(2)
O2 C2 C3 112.9(2)
O3 C2 C1 109.8(2)
O2 C2 C1 110.9(2)
C3 C2 C1 102.3(2)
C4 C3 C8 120.7(2)
C4 C3 C2 130.3(2)
C8 C3 C2 108.9(2)
C3 C4 C5 117.2(2)
C3 C4 H4 123.2(17)
C5 C4 H4 119.6(17)
C6 C5 C4 122.0(3)
C6 C5 Cl1 119.2(2)
C4 C5 Cl1 118.8(2)
C5 C6 C7 120.6(2)
C5 C6 H6 119.(2)
C7 C6 H6 121.(2)
C8 C7 C6 117.2(2)
C8 C7 H7 123.(2)
C6 C7 H7 119.(2)
C7 C8 C3 122.4(2)
C7 C8 N1 128.2(2)
C3 C8 N1 109.4(2)
O2 C9 C10 104.7(2)
O2 C9 H91 110.(3)
C10 C9 H91 114.(3)
O2 C9 H92 109.(2)
C10 C9 H92 115.(2)
H91 C9 H92 105.(4)
O3 C10 C9 106.0(2)
O3 C10 H101 110.3
C9 C10 H101 111.0
O3 C10 H102 110.3
C9 C10 H102 110.3
H101 C10 H102 110.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C5 1.740(3) ?
O1 C1 1.220(4) ?
O2 C2 1.404(3) ?
O2 C9 1.438(3) ?
O3 C2 1.405(3) ?
O3 C10 1.429(4) ?
N1 C1 1.341(4) ?
N1 C8 1.412(4) ?
N1 H1 0.82(3) ?
C1 C2 1.560(3) ?
C2 C3 1.494(3) ?
C3 C4 1.378(3) ?
C3 C8 1.386(3) ?
C4 C5 1.386(3) ?
C4 H4 0.92(3) no
C5 C6 1.381(4) ?
C6 C7 1.392(5) ?
C6 H6 0.88(4) no
C7 C8 1.369(4) ?
C7 H7 1.01(4) no
C9 C10 1.487(4) ?
C9 H91 0.96(4) ?
C9 H92 0.96(4) ?
C10 H101 0.97 ?
C10 H102 0.97 ?
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 O1 4_545 0.82(3) 2.11(3) 2.885(4) 157.4(3)
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
C9 O2 C2 O3 28.9(2)
C9 O2 C2 C1 -90.9(2)
C9 O2 C2 C3 155.0(2)
C2 O2 C9 C10 -23.5(3)
C10 O3 C2 O2 -22.6(3)
C10 O3 C2 C1 97.9(2)
C10 O3 C2 C3 -148.1(2)
C2 O3 C10 C9 7.5(3)
C8 N1 C1 O1 -179.1(3)
C8 N1 C1 C2 0.8(3)
C1 N1 C8 C3 -1.1(3)
C1 N1 C8 C7 176.6(3)
O1 C1 C2 O2 59.0(4)
O1 C1 C2 O3 -59.1(4)
O1 C1 C2 C3 179.7(3)
N1 C1 C2 O2 -120.9(2)
N1 C1 C2 O3 121.0(2)
N1 C1 C2 C3 -0.2(3)
O2 C2 C3 C4 -58.7(3)
O2 C2 C3 C8 118.8(2)
O3 C2 C3 C4 63.6(3)
O3 C2 C3 C8 -118.9(2)
C1 C2 C3 C4 -177.9(2)
C1 C2 C3 C8 -0.4(2)
C2 C3 C4 C5 177.2(2)
C2 C3 C8 N1 0.9(3)
C2 C3 C8 C7 -176.9(2)
C4 C3 C8 N1 178.7(2)
C4 C3 C8 C7 0.9(4)
C3 C4 C5 Cl1 -179.6(2)
C3 C4 C5 C6 -0.9(4)
Cl1 C5 C6 C7 179.8(2)
C4 C5 C6 C7 1.0(4)
C5 C6 C7 C8 -0.2(4)
C6 C7 C8 N1 -178.1(3)
C6 C7 C8 C3 -0.7(4)
O2 C9 C10 O3 9.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3736810
