#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/80/2208017.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_2208017
loop_
_publ_author_name
'Zhi-Qiang Hu'
'Guo-Dong Si'
'Kai Zhou'
'Guan-Ping Yu'
'Liang-Zhong Xu'
_publ_section_title
;
 2-(4-Chlorobenzyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide
;
_journal_coeditor_code           CV2002
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o427
_journal_page_last               o428
_journal_paper_doi               10.1107/S1600536806001140
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H10 Cl N O3 S'
_chemical_formula_moiety         'C14 H10 Cl N O3 S'
_chemical_formula_sum            'C14 H10 Cl N O3 S'
_chemical_formula_weight         307.74
_chemical_name_systematic
;
2-(4-Chlorobenzyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.50(3)
_cell_angle_beta                 102.82(3)
_cell_angle_gamma                111.25(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2657(15)
_cell_length_b                   7.4743(15)
_cell_length_c                   13.317(3)
_cell_measurement_reflns_used    5601
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      1.61
_cell_volume                     639.3(3)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1999)'
_computing_data_reduction        RAPID-AUTO
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0130
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2851
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.61
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.468
_exptl_absorpt_correction_T_max  0.9526
_exptl_absorpt_correction_T_min  0.7534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.554
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0500
_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)+(0.0884P)²+0.4878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1448
_refine_ls_wR_factor_ref         0.1516
_reflns_number_gt                2065
_reflns_number_total             2201
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2002.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2208017
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
Cl1 1.10855(13) 0.79585(16) 0.58256(7) 0.0666(3) Uani d . 1 Cl
S1 0.25031(10) 0.87871(10) 0.19147(5) 0.0401(3) Uani d . 1 S
O1 0.4305(3) 1.0408(3) 0.25773(17) 0.0554(6) Uani d . 1 O
O2 0.0578(3) 0.8686(3) 0.20338(18) 0.0541(6) Uani d . 1 O
O3 0.2781(4) 0.3960(3) 0.10868(18) 0.0555(6) Uani d . 1 O
N1 0.2725(4) 0.6683(4) 0.20488(19) 0.0433(6) Uani d . 1 N
C1 0.2467(4) 0.8388(4) 0.0586(2) 0.0367(6) Uani d . 1 C
C2 0.2309(4) 0.9585(4) -0.0094(2) 0.0435(6) Uani d . 1 C
H2B 0.2241 1.0787 0.0125 0.052 Uiso calc R 1 H
C3 0.2258(4) 0.8923(5) -0.1120(2) 0.0474(7) Uani d . 1 C
H3A 0.2132 0.9687 -0.1608 0.057 Uiso calc R 1 H
C4 0.2388(5) 0.7153(5) -0.1438(2) 0.0478(7) Uani d . 1 C
H4A 0.2365 0.6750 -0.2133 0.057 Uiso calc R 1 H
C5 0.2552(4) 0.5970(4) -0.0737(2) 0.0435(6) Uani d . 1 C
H5A 0.2643 0.4777 -0.0950 0.052 Uiso calc R 1 H
C6 0.2578(4) 0.6604(4) 0.0285(2) 0.0368(6) Uani d . 1 C
C7 0.2700(4) 0.5548(4) 0.1141(2) 0.0409(6) Uani d . 1 C
C8 0.2727(5) 0.6030(5) 0.3038(2) 0.0511(7) Uani d . 1 C
H8A 0.2005 0.4605 0.2873 0.061 Uiso calc R 1 H
H8B 0.1975 0.6589 0.3404 0.061 Uiso calc R 1 H
C9 0.4850(5) 0.6610(4) 0.3760(2) 0.0433(6) Uani d . 1 C
C10 0.6353(6) 0.6226(7) 0.3420(3) 0.0698(11) Uani d . 1 C
H10A 0.6028 0.5636 0.2708 0.084 Uiso calc R 1 H
C11 0.8223(5) 0.6631(6) 0.4029(2) 0.0543(8) Uani d . 1 C
H11A 0.9188 0.6345 0.3762 0.065 Uiso calc R 1 H
C12 0.8643(5) 0.7447(5) 0.5016(2) 0.0463(7) Uani d . 1 C
C13 0.7316(5) 0.7926(5) 0.5457(2) 0.0515(7) Uani d . 1 C
H13A 0.7701 0.8517 0.6173 0.062 Uiso calc R 1 H
C14 0.5394(5) 0.7505(5) 0.4808(2) 0.0502(7) Uani d . 1 C
H14A 0.4452 0.7828 0.5081 0.060 Uiso calc R 1 H
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'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
O2 S1 O1 . 117.21(14) yes
O2 S1 N1 . 109.46(14) ?
O1 S1 N1 . 109.51(14) ?
O2 S1 C1 . 112.09(13) ?
O1 S1 C1 . 113.01(14) ?
N1 S1 C1 . 92.78(12) ?
C7 N1 C8 . 123.4(2) ?
C7 N1 S1 . 115.0(2) yes
C8 N1 S1 . 121.3(2) ?
C2 C1 C6 . 122.9(3) ?
C2 C1 S1 . 127.5(2) ?
C6 C1 S1 . 109.6(2) ?
C1 C2 C3 . 116.8(3) ?
C1 C2 H2B . 121.6 ?
C3 C2 H2B . 121.6 ?
C2 C3 C4 . 121.5(3) ?
C2 C3 H3A . 119.3 ?
C4 C3 H3A . 119.3 ?
C3 C4 C5 . 120.8(3) ?
C3 C4 H4A . 119.6 ?
C5 C4 H4A . 119.6 ?
C6 C5 C4 . 118.2(3) ?
C6 C5 H5A . 120.9 ?
C4 C5 H5A . 120.9 ?
C5 C6 C1 . 119.8(3) ?
C5 C6 C7 . 126.6(2) ?
C1 C6 C7 . 113.6(2) ?
O3 C7 N1 1 123.9(3) ?
O3 C7 N1 . 123.9(3) ?
O3 C7 C6 1 127.1(3) ?
O3 C7 C6 . 127.1(3) ?
N1 C7 C6 . 108.9(2) ?
N1 C8 C9 . 113.3(2) yes
N1 C8 H8A . 108.9 ?
C9 C8 H8A . 108.9 ?
N1 C8 H8B . 108.9 ?
C9 C8 H8B . 108.9 ?
H8A C8 H8B . 107.7 ?
C14 C9 C10 . 115.9(3) ?
C14 C9 C8 . 121.8(3) ?
C10 C9 C8 . 122.2(3) ?
C11 C10 C9 . 124.9(3) ?
C11 C10 H10A . 117.6 ?
C9 C10 H10A . 117.6 ?
C12 C11 C10 . 116.6(3) ?
C12 C11 H11A . 121.7 ?
C10 C11 H11A . 121.7 ?
C11 C12 C13 . 124.8(3) ?
C11 C12 Cl1 . 116.9(2) ?
C13 C12 Cl1 . 118.3(2) ?
C12 C13 C14 . 117.5(3) ?
C12 C13 H13A . 121.2 ?
C14 C13 H13A . 121.2 ?
C13 C14 C9 . 120.3(3) ?
C13 C14 H14A . 119.9 ?
C9 C14 H14A . 119.9 ?
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 C12 . 1.735(3) yes
S1 O2 . 1.418(2) yes
S1 O1 . 1.421(2) yes
S1 N1 . 1.666(2) yes
S1 C1 . 1.748(3) yes
O3 C7 . 1.203(3) ?
N1 C7 . 1.376(4) yes
N1 C8 . 1.463(4) yes
C1 C2 . 1.369(4) ?
C1 C6 . 1.378(4) ?
C2 C3 . 1.378(4) ?
C2 H2B . 0.9300 ?
C3 C4 . 1.379(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.383(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.375(4) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.474(4) ?
C7 O3 1 1.203(3) ?
C8 C9 . 1.497(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C14 . 1.369(4) ?
C9 C10 . 1.376(4) ?
C10 C11 . 1.321(5) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.293(4) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.360(4) ?
C13 C14 . 1.368(5) ?
C13 H13A . 0.9300 ?
C14 H14A . 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
C2 H2B O3 1_565 0.93 2.39 3.300(4) 165
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_4
_geom_torsion
O2 S1 N1 C7 . 112.1(2)
O1 S1 N1 C7 . -118.1(2)
C1 S1 N1 C7 . -2.5(2)
O2 S1 N1 C8 . -61.9(3)
O1 S1 N1 C8 . 67.9(3)
C1 S1 N1 C8 . -176.5(2)
O2 S1 C1 C2 . 67.8(3)
O1 S1 C1 C2 . -67.3(3)
N1 S1 C1 C2 . -179.9(3)
O2 S1 C1 C6 . -110.9(2)
O1 S1 C1 C6 . 114.0(2)
N1 S1 C1 C6 . 1.5(2)
C6 C1 C2 C3 . 0.2(4)
S1 C1 C2 C3 . -178.3(2)
C1 C2 C3 C4 . -0.9(4)
C2 C3 C4 C5 . 0.7(5)
C3 C4 C5 C6 . 0.1(4)
C4 C5 C6 C1 . -0.8(4)
C4 C5 C6 C7 . 178.7(3)
C2 C1 C6 C5 . 0.6(4)
S1 C1 C6 C5 . 179.4(2)
C2 C1 C6 C7 . -178.9(2)
S1 C1 C6 C7 . -0.2(3)
C8 N1 C7 O3 1 -3.8(4)
S1 N1 C7 O3 1 -177.7(2)
C8 N1 C7 O3 . -3.8(4)
S1 N1 C7 O3 . -177.7(2)
C8 N1 C7 C6 . 176.6(2)
S1 N1 C7 C6 . 2.8(3)
C5 C6 C7 O3 1 -0.6(5)
C1 C6 C7 O3 1 178.9(3)
C5 C6 C7 O3 . -0.6(5)
C1 C6 C7 O3 . 178.9(3)
C5 C6 C7 N1 . 178.9(3)
C1 C6 C7 N1 . -1.6(3)
C7 N1 C8 C9 . 91.5(3)
S1 N1 C8 C9 . -95.1(3)
N1 C8 C9 C14 . 131.0(3)
N1 C8 C9 C10 . -51.0(4)
C14 C9 C10 C11 . 0.9(6)
C8 C9 C10 C11 . -177.2(4)
C9 C10 C11 C12 . 0.1(7)
C10 C11 C12 C13 . -0.8(6)
C10 C11 C12 Cl1 . 179.3(3)
C11 C12 C13 C14 . 0.3(5)
Cl1 C12 C13 C14 . -179.8(2)
C12 C13 C14 C9 . 0.9(5)
C10 C9 C14 C13 . -1.4(5)
C8 C9 C14 C13 . 176.7(3)
