#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/54/2215486.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_2215486
loop_
_publ_author_name
'Siddiqui, Waseeq Ahmad'
'Ahmad, Saeed'
'Khan, Islam Ullah'
'Siddiqui, Hamid Latif'
'Parvez, Masood'
_publ_section_title
;
 2-Chloromethyl-1,2-benzisothiazole-1,1,3(2H)-trione
;
_journal_coeditor_code           GG2045
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4116
_journal_page_last               o4116
_journal_paper_doi               10.1107/S1600536807044923
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C8 H6 Cl N O3 S'
_chemical_formula_moiety         'C8 H6 Cl N O3 S'
_chemical_formula_sum            'C8 H6 Cl N O3 S'
_chemical_formula_weight         231.65
_chemical_name_common
;
N-Chloromethylsaccharin
;
_chemical_name_systematic
;
2-Chloromethyl-1,2-benzisothiazole-1,1,3(2H)-trione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 107.46(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.208(5)
_cell_length_b                   8.643(4)
_cell_length_c                   12.458(6)
_cell_measurement_reflns_used    4086
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.31
_cell_volume                     945.8(8)
_computing_cell_refinement       'HKL DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SAPI91 (Fan, 1991)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'ω and φ'
_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  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4086
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.404
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0437P)²+0.6083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1020
_reflns_number_gt                1671
_reflns_number_total             2161
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg2045.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_database_code               2215486
_cod_database_fobs_code          2215486
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Cl Cl1 0.13760(9) 0.96958(7) -0.09257(6) 0.0450(2) Uani d . 1
S S1 0.21025(6) 0.61766(6) 0.09596(4) 0.02421(16) Uani d . 1
O O1 0.17085(19) 0.58867(19) -0.21198(12) 0.0307(4) Uani d . 1
O O2 0.07883(19) 0.5821(2) 0.13012(13) 0.0349(4) Uani d . 1
O O3 0.31276(19) 0.73035(19) 0.16087(12) 0.0311(4) Uani d . 1
N N1 0.1551(2) 0.6681(2) -0.03988(14) 0.0243(4) Uani d . 1
C C1 0.3062(3) 0.4538(2) 0.07062(17) 0.0236(5) Uani d . 1
C C2 0.3863(3) 0.3462(3) 0.14818(19) 0.0320(6) Uani d . 1
H H2 0.3917 0.3532 0.2254 0.038 Uiso calc R 1
C C3 0.4585(3) 0.2278(3) 0.1091(2) 0.0359(6) Uani d . 1
H H3 0.5138 0.1517 0.1602 0.043 Uiso calc R 1
C C4 0.4512(3) 0.2185(3) -0.0042(2) 0.0345(6) Uani d . 1
H H4 0.5030 0.1372 -0.0286 0.041 Uiso calc R 1
C C5 0.3699(3) 0.3257(3) -0.08149(19) 0.0280(5) Uani d . 1
H H5 0.3646 0.3186 -0.1587 0.034 Uiso calc R 1
C C6 0.2963(3) 0.4440(2) -0.04326(17) 0.0226(5) Uani d . 1
C C7 0.2032(3) 0.5687(3) -0.11165(17) 0.0234(5) Uani d . 1
C C8 0.0460(3) 0.7888(3) -0.08138(19) 0.0296(5) Uani d . 1
H H8A -0.0169 0.8017 -0.0300 0.036 Uiso calc R 1
H H8B -0.0224 0.7593 -0.1563 0.036 Uiso calc R 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
Cl1 0.0490(5) 0.0296(3) 0.0581(4) 0.0029(3) 0.0184(3) 0.0067(3)
S1 0.0253(3) 0.0299(3) 0.0174(3) -0.0027(2) 0.0063(2) -0.0028(2)
O1 0.0385(10) 0.0359(9) 0.0182(7) 0.0017(8) 0.0092(7) 0.0021(7)
O2 0.0295(10) 0.0503(10) 0.0292(8) -0.0062(8) 0.0153(7) -0.0047(8)
O3 0.0318(10) 0.0349(9) 0.0238(8) -0.0067(8) 0.0042(7) -0.0086(7)
N1 0.0269(11) 0.0276(9) 0.0174(8) 0.0026(8) 0.0053(7) -0.0009(7)
C1 0.0247(12) 0.0234(11) 0.0228(10) -0.0038(9) 0.0073(9) 0.0001(9)
C2 0.0333(14) 0.0353(13) 0.0257(11) -0.0050(11) 0.0059(10) 0.0079(10)
C3 0.0353(15) 0.0259(11) 0.0430(14) -0.0004(11) 0.0064(11) 0.0102(11)
C4 0.0319(14) 0.0232(11) 0.0514(15) -0.0001(11) 0.0171(12) 0.0008(11)
C5 0.0291(13) 0.0273(11) 0.0299(11) -0.0041(10) 0.0122(10) -0.0033(9)
C6 0.0208(12) 0.0234(10) 0.0236(10) -0.0048(9) 0.0066(9) 0.0001(9)
C7 0.0250(12) 0.0256(10) 0.0203(10) -0.0030(9) 0.0081(9) -0.0004(8)
C8 0.0272(13) 0.0307(12) 0.0281(11) 0.0039(10) 0.0038(10) -0.0004(10)
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'
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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
_geom_angle_publ_flag
O3 S1 O2 116.90(10) no
O3 S1 N1 110.12(10) no
O2 S1 N1 109.25(10) no
O3 S1 C1 111.79(11) no
O2 S1 C1 113.48(11) no
N1 S1 C1 92.56(10) no
C7 N1 C8 122.46(18) no
C7 N1 S1 115.29(15) no
C8 N1 S1 121.46(15) no
C2 C1 C6 121.8(2) ?
C2 C1 S1 127.66(18) ?
C6 C1 S1 110.49(16) ?
C3 C2 C1 117.5(2) ?
C3 C2 H2 121.2 ?
C1 C2 H2 121.2 ?
C2 C3 C4 121.0(2) ?
C2 C3 H3 119.5 ?
C4 C3 H3 119.5 ?
C5 C4 C3 121.2(2) ?
C5 C4 H4 119.4 ?
C3 C4 H4 119.4 ?
C4 C5 C6 118.2(2) ?
C4 C5 H5 120.9 ?
C6 C5 H5 120.9 ?
C5 C6 C1 120.2(2) ?
C5 C6 C7 126.72(19) ?
C1 C6 C7 113.05(19) ?
O1 C7 N1 123.0(2) ?
O1 C7 C6 128.4(2) ?
N1 C7 C6 108.55(17) ?
N1 C8 Cl1 111.45(17) ?
N1 C8 H8A 109.3 ?
Cl1 C8 H8A 109.3 ?
N1 C8 H8B 109.3 ?
Cl1 C8 H8B 109.3 ?
H8A C8 H8B 108.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C8 1.801(3) no
S1 O3 1.427(2) no
S1 O2 1.431(2) no
S1 N1 1.672(2) no
S1 C1 1.748(2) no
O1 C7 1.207(3) no
N1 C7 1.404(3) no
N1 C8 1.433(3) no
C1 C2 1.384(3) ?
C1 C6 1.397(3) ?
C2 C3 1.386(4) ?
C2 H2 0.9500 ?
C3 C4 1.394(4) ?
C3 H3 0.9500 ?
C4 C5 1.384(3) ?
C4 H4 0.9500 ?
C5 C6 1.387(3) ?
C5 H5 0.9500 ?
C6 C7 1.478(3) ?
C8 H8A 0.9900 ?
C8 H8B 0.9900 ?
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
C5 H5 O1 2_544 0.95 2.52 3.222(3) 131
C8 H8B O3 4_575 0.99 2.33 3.288(3) 163
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
O3 S1 N1 C7 114.39(17)
O2 S1 N1 C7 -115.93(17)
C1 S1 N1 C7 0.05(18)
O3 S1 N1 C8 -75.6(2)
O2 S1 N1 C8 54.1(2)
C1 S1 N1 C8 170.05(18)
O3 S1 C1 C2 67.0(2)
O2 S1 C1 C2 -67.8(2)
N1 S1 C1 C2 179.9(2)
O3 S1 C1 C6 -111.42(17)
O2 S1 C1 C6 113.75(17)
N1 S1 C1 C6 1.45(18)
C6 C1 C2 C3 0.6(3)
S1 C1 C2 C3 -177.65(19)
C1 C2 C3 C4 0.4(4)
C2 C3 C4 C5 -1.0(4)
C3 C4 C5 C6 0.5(4)
C4 C5 C6 C1 0.6(3)
C4 C5 C6 C7 -179.5(2)
C2 C1 C6 C5 -1.1(3)
S1 C1 C6 C5 177.41(18)
C2 C1 C6 C7 178.9(2)
S1 C1 C6 C7 -2.5(2)
C8 N1 C7 O1 9.2(3)
S1 N1 C7 O1 179.07(18)
C8 N1 C7 C6 -171.3(2)
S1 N1 C7 C6 -1.4(2)
C5 C6 C7 O1 2.1(4)
C1 C6 C7 O1 -178.0(2)
C5 C6 C7 N1 -177.4(2)
C1 C6 C7 N1 2.5(3)
C7 N1 C8 Cl1 -93.0(2)
S1 N1 C8 Cl1 97.72(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1721420
