#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/11/2211100.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_2211100
loop_
_publ_author_name
'Wen, Hui-Liang'
'Zuo, Jun-Hui'
'Ding, Liang'
'Lai, Bo-Wen'
'Liu, Chong-Bo'
_publ_section_title
;
 2-Benzyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide
;
_journal_coeditor_code           LH2193
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5061
_journal_page_last               o5062
_journal_paper_doi               10.1107/S160053680604116X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C14 H11 N O3 S'
_chemical_formula_sum            'C14 H11 N O3 S'
_chemical_formula_weight         273.30
_chemical_name_systematic
;
 ?
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.459(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6073(18)
_cell_length_b                   10.223(3)
_cell_length_c                   18.221(5)
_cell_measurement_reflns_used    4168
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.7
_cell_measurement_theta_min      2.3
_cell_volume                     1217.4(6)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure (Rigaku/MSC, 2005)'
_computing_publication_material  CrystalStructure
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11532
_diffrn_reflns_theta_full        28.68
_diffrn_reflns_theta_max         28.68
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  0.9384
_exptl_absorpt_correction_T_min  0.9190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.453
_refine_ls_extinction_coef       0.037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3095
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0319
_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)+(0.0593P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.0995
_reflns_number_gt                2407
_reflns_number_total             3095
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2193.cif
_cod_data_source_block           I
_cod_original_cell_volume        1217.3(6)
_cod_database_code               2211100
_cod_database_fobs_code          2211100
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
S S1 0.27468(5) 0.39036(3) 0.057657(18) 0.01345(12) Uani d . 1
O O1 0.78969(14) 0.37272(10) 0.17415(6) 0.0218(2) Uani d . 1
O O2 0.12807(13) 0.28842(9) 0.06234(6) 0.0186(2) Uani d . 1
O O3 0.26725(14) 0.45438(10) -0.01269(5) 0.0193(2) Uani d . 1
N N1 0.50961(16) 0.33409(11) 0.08645(6) 0.0143(2) Uani d . 1
C C1 0.6151(2) 0.39697(13) 0.14796(8) 0.0147(3) Uani d . 1
C C2 0.47716(19) 0.49523(12) 0.17553(7) 0.0145(3) Uani d . 1
C C3 0.28609(19) 0.50127(13) 0.13159(7) 0.0142(3) Uani d . 1
C C4 0.1324(2) 0.58406(13) 0.14819(8) 0.0175(3) Uani d . 1
H H4 0.0023 0.5873 0.1181 0.021 Uiso calc R 1
C C5 0.1777(2) 0.66163(14) 0.21070(9) 0.0203(3) Uani d . 1
H H5 0.0758 0.7191 0.2238 0.024 Uiso calc R 1
C C6 0.3692(2) 0.65783(14) 0.25519(8) 0.0192(3) Uani d . 1
H H6 0.3958 0.7128 0.2976 0.023 Uiso calc R 1
C C7 0.5210(2) 0.57381(14) 0.23761(8) 0.0177(3) Uani d . 1
H H7 0.6513 0.5706 0.2675 0.021 Uiso calc R 1
C C8 0.61192(19) 0.24306(13) 0.04181(8) 0.0158(3) Uani d . 1
H H8A 0.7479 0.2789 0.0360 0.019 Uiso calc R 1
H H8B 0.5307 0.2362 -0.0082 0.019 Uiso calc R 1
C C9 0.6394(2) 0.10802(12) 0.07527(7) 0.0147(3) Uani d . 1
C C10 0.4931(2) 0.05155(14) 0.11285(8) 0.0190(3) Uani d . 1
H H10 0.3730 0.0992 0.1187 0.023 Uiso calc R 1
C C11 0.5206(2) -0.07371(15) 0.14194(9) 0.0226(3) Uani d . 1
H H11 0.4208 -0.1107 0.1683 0.027 Uiso calc R 1
C C12 0.6938(2) -0.14523(14) 0.13261(9) 0.0227(3) Uani d . 1
H H12 0.7122 -0.2312 0.1523 0.027 Uiso calc R 1
C C13 0.8393(2) -0.09053(14) 0.09447(9) 0.0220(3) Uani d . 1
H H13 0.9568 -0.1396 0.0872 0.026 Uiso calc R 1
C C14 0.8139(2) 0.03614(14) 0.06678(8) 0.0182(3) Uani d . 1
H H14 0.9161 0.0740 0.0419 0.022 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'
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'
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 116.77(6) yes
O3 S1 N1 110.30(6) yes
O2 S1 N1 109.67(6) yes
O3 S1 C3 112.56(7) yes
O2 S1 C3 112.16(6) yes
N1 S1 C3 92.78(6) yes
C1 N1 C8 121.65(11) yes
C1 N1 S1 115.36(9) yes
C8 N1 S1 121.94(9) yes
O1 C1 N1 124.14(13) ?
O1 C1 C2 126.90(13) ?
N1 C1 C2 108.95(11) ?
C7 C2 C3 120.48(12) ?
C7 C2 C1 127.00(12) ?
C3 C2 C1 112.52(12) ?
C4 C3 C2 122.11(13) ?
C4 C3 S1 127.66(10) ?
C2 C3 S1 110.22(10) ?
C5 C4 C3 116.86(12) ?
C5 C4 H4 121.6 ?
C3 C4 H4 121.6 ?
C4 C5 C6 121.91(13) ?
C4 C5 H5 119.0 ?
C6 C5 H5 119.0 ?
C7 C6 C5 120.26(14) ?
C7 C6 H6 119.9 ?
C5 C6 H6 119.9 ?
C2 C7 C6 118.38(13) ?
C2 C7 H7 120.8 ?
C6 C7 H7 120.8 ?
N1 C8 C9 113.25(11) ?
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 ?
C10 C9 C14 118.82(13) ?
C10 C9 C8 121.86(12) ?
C14 C9 C8 119.30(12) ?
C11 C10 C9 120.65(13) ?
C11 C10 H10 119.7 ?
C9 C10 H10 119.7 ?
C10 C11 C12 120.21(14) ?
C10 C11 H11 119.9 ?
C12 C11 H11 119.9 ?
C13 C12 C11 119.62(14) ?
C13 C12 H12 120.2 ?
C11 C12 H12 120.2 ?
C12 C13 C14 120.14(13) ?
C12 C13 H13 119.9 ?
C14 C13 H13 119.9 ?
C13 C14 C9 120.54(13) ?
C13 C14 H14 119.7 ?
C9 C14 H14 119.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O3 1.4336(10) yes
S1 O2 1.4339(10) yes
S1 N1 1.6661(12) yes
S1 C3 1.7538(14) yes
O1 C1 1.2076(16) yes
N1 C1 1.3875(18) yes
N1 C8 1.4651(17) yes
C1 C2 1.4921(19) ?
C2 C7 1.3828(19) ?
C2 C3 1.3933(18) ?
C3 C4 1.3891(19) ?
C4 C5 1.384(2) ?
C4 H4 0.9500 ?
C5 C6 1.399(2) ?
C5 H5 0.9500 ?
C6 C7 1.393(2) ?
C6 H6 0.9500 ?
C7 H7 0.9500 ?
C8 C9 1.5092(18) ?
C8 H8A 0.9900 ?
C8 H8B 0.9900 ?
C9 C10 1.3899(19) ?
C9 C14 1.3945(19) ?
C10 C11 1.388(2) ?
C10 H10 0.9500 ?
C11 C12 1.389(2) ?
C11 H11 0.9500 ?
C12 C13 1.385(2) ?
C12 H12 0.9500 ?
C13 C14 1.391(2) ?
C13 H13 0.9500 ?
C14 H14 0.9500 ?
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
C8 H8A O2 1_655 0.99 2.49 3.4074(18) 154 yes
C4 H4 O3 3_565 0.95 2.46 3.3623(19) 159 yes
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 C1 111.40(11)
O2 S1 N1 C1 -118.65(10)
C3 S1 N1 C1 -3.91(11)
O3 S1 N1 C8 -57.12(12)
O2 S1 N1 C8 72.84(11)
C3 S1 N1 C8 -172.42(11)
C8 N1 C1 O1 -8.1(2)
S1 N1 C1 O1 -176.61(11)
C8 N1 C1 C2 172.73(11)
S1 N1 C1 C2 4.18(14)
O1 C1 C2 C7 -2.3(2)
N1 C1 C2 C7 176.84(13)
O1 C1 C2 C3 178.56(13)
N1 C1 C2 C3 -2.26(16)
C7 C2 C3 C4 -0.7(2)
C1 C2 C3 C4 178.47(12)
C7 C2 C3 S1 -179.58(10)
C1 C2 C3 S1 -0.42(15)
O3 S1 C3 C4 70.20(14)
O2 S1 C3 C4 -63.89(14)
N1 S1 C3 C4 -176.45(13)
O3 S1 C3 C2 -110.99(10)
O2 S1 C3 C2 114.92(10)
N1 S1 C3 C2 2.36(11)
C2 C3 C4 C5 0.3(2)
S1 C3 C4 C5 178.99(11)
C3 C4 C5 C6 0.3(2)
C4 C5 C6 C7 -0.4(2)
C3 C2 C7 C6 0.5(2)
C1 C2 C7 C6 -178.54(13)
C5 C6 C7 C2 0.0(2)
C1 N1 C8 C9 80.73(15)
S1 N1 C8 C9 -111.47(11)
N1 C8 C9 C10 36.26(18)
N1 C8 C9 C14 -145.40(12)
C14 C9 C10 C11 0.5(2)
C8 C9 C10 C11 178.85(13)
C9 C10 C11 C12 -1.2(2)
C10 C11 C12 C13 0.4(2)
C11 C12 C13 C14 1.1(2)
C12 C13 C14 C9 -1.8(2)
C10 C9 C14 C13 1.0(2)
C8 C9 C14 C13 -177.43(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 86520
