#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/17/2221715.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_2221715
loop_
_publ_author_name
'Arshad, Muhammad Nadeem'
'Tahir, M. Nawaz'
'Khan, Islam Ullah'
'Bilal, Muhammad Humayun'
'Mubashar-ur-Rehman, Hafiz'
_publ_section_title
;
 2-(3-Methylbut-2-en-1-yl)-1,2-benzisothiazol-3(2H)-one
 1,1-dioxide
;
_journal_coeditor_code           HK2656
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o986
_journal_paper_doi               10.1107/S1600536809012021
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H13 N O3 S'
_chemical_formula_moiety         'C12 H13 N O3 S'
_chemical_formula_sum            'C12 H13 N O3 S'
_chemical_formula_weight         251.29
_chemical_name_systematic
;
2-(3-Methylbut-2-en-1-yl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4120(5)
_cell_length_b                   19.4108(11)
_cell_length_c                   6.5261(4)
_cell_measurement_reflns_used    2818
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.81
_cell_measurement_theta_min      2.40
_cell_volume                     1192.28(12)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'Ortep3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGx publication routines (Farrugia, 1999) and PLATON (Spek,
2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.40
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD area-detector'
_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  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7340
_diffrn_reflns_theta_full        28.81
_diffrn_reflns_theta_max         28.81
_diffrn_reflns_theta_min         2.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.202
_refine_ls_abs_structure_details 'Flack  (1983), 837 Friedel pairs'
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2525
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0289
_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)+(0.05P)²+0.1276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0829
_reflns_number_gt                2304
_reflns_number_total             2525
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2656.cif
_cod_data_source_block           I
_cod_database_code               2221715
_cod_database_fobs_code          2221715
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,1/2+y,1/2+z
4 1/2+x,1/2-y,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
S S1 0.39059(4) 0.43722(2) 0.22028(8) 0.03600(10) Uani . . 1.000
O O1 0.47203(15) 0.49780(6) 0.1846(2) 0.0527(5) Uani . . 1.000
O O2 0.27683(15) 0.44174(7) 0.3626(3) 0.0501(5) Uani . . 1.000
O O3 0.34253(18) 0.31180(9) -0.2062(3) 0.0681(6) Uani . . 1.000
N N1 0.32910(16) 0.40665(8) -0.0015(3) 0.0420(5) Uani . . 1.000
C C1 0.47927(19) 0.31849(9) 0.1051(3) 0.0430(6) Uani . . 1.000
C C2 0.5491(2) 0.25556(10) 0.1123(4) 0.0571(7) Uani . . 1.000
C C3 0.6312(2) 0.24143(11) 0.2810(5) 0.0643(8) Uani . . 1.000
C C4 0.6463(2) 0.28766(11) 0.4407(4) 0.0582(8) Uani . . 1.000
C C5 0.5766(2) 0.35100(10) 0.4341(4) 0.0474(6) Uani . . 1.000
C C6 0.49541(17) 0.36438(8) 0.2640(3) 0.0377(5) Uani . . 1.000
C C7 0.37937(19) 0.34237(10) -0.0545(3) 0.0449(6) Uani . . 1.000
C C8 0.2217(2) 0.44531(10) -0.1171(4) 0.0480(6) Uani . . 1.000
C C9 0.0741(2) 0.43125(10) -0.0398(4) 0.0492(7) Uani . . 1.000
C C10 -0.0319(2) 0.40469(9) -0.1434(4) 0.0476(6) Uani . . 1.000
C C11 -0.0249(3) 0.38285(16) -0.3615(5) 0.0740(10) Uani . . 1.000
C C12 -0.1738(2) 0.39260(14) -0.0418(5) 0.0718(9) Uani . . 1.000
H H2 0.54056 0.22393 0.00600 0.0685 Uiso . . 1.000
H H3 0.67821 0.19935 0.28810 0.0770 Uiso . . 1.000
H H4 0.70306 0.27651 0.55253 0.0698 Uiso . . 1.000
H H5 0.58470 0.38275 0.54021 0.0569 Uiso . . 1.000
H H8A 0.22741 0.43275 -0.26069 0.0577 Uiso . . 1.000
H H8B 0.24147 0.49421 -0.10592 0.0577 Uiso . . 1.000
H H9 0.05601 0.44262 0.09618 0.0591 Uiso . . 1.000
H H11A 0.06668 0.39430 -0.41673 0.1109 Uiso . . 1.000
H H11B -0.09740 0.40615 -0.43825 0.1109 Uiso . . 1.000
H H11C -0.03930 0.33398 -0.37040 0.1109 Uiso . . 1.000
H H12A -0.16911 0.40717 0.09857 0.1074 Uiso . . 1.000
H H12B -0.19663 0.34444 -0.04742 0.1074 Uiso . . 1.000
H H12C -0.24574 0.41849 -0.11203 0.1074 Uiso . . 1.000
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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . . 117.53(8) no
O1 S1 N1 . . . 109.81(8) no
O1 S1 C6 . . . 113.03(8) no
O2 S1 N1 . . . 109.14(9) no
O2 S1 C6 . . . 111.65(9) no
N1 S1 C6 . . . 92.85(8) no
S1 N1 C7 . . . 114.88(14) no
S1 N1 C8 . . . 120.21(14) no
C7 N1 C8 . . . 124.76(18) no
C2 C1 C6 . . . 119.48(18) no
C2 C1 C7 . . . 126.96(18) no
C6 C1 C7 . . . 113.49(16) no
C1 C2 C3 . . . 118.0(2) no
C2 C3 C4 . . . 122.2(2) no
C3 C4 C5 . . . 120.1(2) no
C4 C5 C6 . . . 117.0(2) no
S1 C6 C1 . . . 109.79(14) no
S1 C6 C5 . . . 126.83(15) no
C1 C6 C5 . . . 123.28(16) no
O3 C7 N1 . . . 123.57(19) no
O3 C7 C1 . . . 127.42(18) no
N1 C7 C1 . . . 108.99(16) no
N1 C8 C9 . . . 111.79(19) no
C8 C9 C10 . . . 127.0(2) no
C9 C10 C11 . . . 124.9(2) no
C9 C10 C12 . . . 120.5(2) no
C11 C10 C12 . . . 114.6(2) no
C1 C2 H2 . . . 121.00 no
C3 C2 H2 . . . 121.00 no
C2 C3 H3 . . . 119.00 no
C4 C3 H3 . . . 119.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C4 C5 H5 . . . 122.00 no
C6 C5 H5 . . . 121.00 no
N1 C8 H8A . . . 109.00 no
N1 C8 H8B . . . 109.00 no
C9 C8 H8A . . . 109.00 no
C9 C8 H8B . . . 109.00 no
H8A C8 H8B . . . 108.00 no
C8 C9 H9 . . . 117.00 no
C10 C9 H9 . . . 116.00 no
C10 C11 H11A . . . 109.00 no
C10 C11 H11B . . . 109.00 no
C10 C11 H11C . . . 109.00 no
H11A C11 H11B . . . 109.00 no
H11A C11 H11C . . . 109.00 no
H11B C11 H11C . . . 109.00 no
C10 C12 H12A . . . 109.00 no
C10 C12 H12B . . . 109.00 no
C10 C12 H12C . . . 109.00 no
H12A C12 H12B . . . 109.00 no
H12A C12 H12C . . . 110.00 no
H12B C12 H12C . . . 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . . 1.4229(13) no
S1 O2 . . 1.4201(17) no
S1 N1 . . 1.6679(19) no
S1 C6 . . 1.7475(16) no
O3 C7 . . 1.205(3) no
N1 C7 . . 1.379(2) no
N1 C8 . . 1.468(3) no
C1 C2 . . 1.388(3) no
C1 C6 . . 1.376(3) no
C1 C7 . . 1.478(3) no
C2 C3 . . 1.373(4) no
C3 C4 . . 1.383(4) no
C4 C5 . . 1.394(3) no
C5 C6 . . 1.373(3) no
C8 C9 . . 1.503(3) no
C9 C10 . . 1.311(3) no
C10 C11 . . 1.487(4) no
C10 C12 . . 1.510(3) no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C8 H8A . . 0.9700 no
C8 H8B . . 0.9700 no
C9 H9 . . 0.9300 no
C11 H11A . . 0.9600 no
C11 H11B . . 0.9600 no
C11 H11C . . 0.9600 no
C12 H12A . . 0.9600 no
C12 H12B . . 0.9600 no
C12 H12C . . 0.9600 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C5 3.391(2) . 2_664 no
O1 C8 3.347(2) . 2_665 no
O2 C9 3.253(3) . . no
O2 C12 3.416(3) . 2_565 no
O3 C5 3.308(3) . 1_554 no
O1 H8B 2.8800 . . no
O1 H5 2.5600 . 2_664 no
O2 H9 2.7100 . . no
O2 H8A 2.5100 . 1_556 no
O2 H12C 2.7300 . 2_565 no
O2 H11A 2.6100 . 1_556 no
O3 H2 2.8800 . . no
O3 H8A 2.6100 . . no
O3 H4 2.6700 . 4_454 no
C3 C7 3.591(3) . 4_555 no
C5 O1 3.391(2) . 2_665 no
C5 O3 3.308(3) . 1_556 no
C7 C3 3.591(3) . 4_455 no
C8 O1 3.347(2) . 2_664 no
C9 O2 3.253(3) . . no
C12 O2 3.416(3) . 2_564 no
C1 H3 3.0900 . 4_455 no
C7 H3 3.0400 . 4_455 no
C8 H11A 2.6300 . . no
C9 H2 3.0400 . 4_455 no
C10 H2 2.7700 . 4_455 no
C11 H8A 2.6500 . . no
C12 H2 3.0500 . 4_455 no
H2 O3 2.8800 . . no
H2 C9 3.0400 . 4_555 no
H2 C10 2.7700 . 4_555 no
H2 C12 3.0500 . 4_555 no
H3 C1 3.0900 . 4_555 no
H3 C7 3.0400 . 4_555 no
H4 O3 2.6700 . 4_556 no
H5 O1 2.5600 . 2_665 no
H8A O2 2.5100 . 1_554 no
H8A O3 2.6100 . . no
H8A C11 2.6500 . . no
H8A H11A 1.9700 . . no
H8B O1 2.8800 . . no
H9 O2 2.7100 . . no
H9 H12A 2.2300 . . no
H11A O2 2.6100 . 1_554 no
H11A C8 2.6300 . . no
H11A H8A 1.9700 . . no
H11B H12C 2.5600 . . no
H11C H12B 2.5800 . . no
H12A H9 2.2300 . . no
H12B H11C 2.5800 . . no
H12C H11B 2.5600 . . no
H12C O2 2.7300 . 2_564 no
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
C5 H5 O1 2_665 0.93 2.56 3.391(2) 149 yes
C8 H8A O2 1_554 0.97 2.51 3.436(3) 160 yes
C3 H3 Cg1 4_555 0.93 2.89 3.664(2) 141 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 N1 C7 . . . . 116.40(14) no
O1 S1 N1 C8 . . . . -67.88(16) no
O2 S1 N1 C7 . . . . -113.44(14) no
O2 S1 N1 C8 . . . . 62.29(17) no
C6 S1 N1 C7 . . . . 0.66(15) no
C6 S1 N1 C8 . . . . 176.38(15) no
O1 S1 C6 C1 . . . . -113.04(13) no
O1 S1 C6 C5 . . . . 70.51(19) no
O2 S1 C6 C1 . . . . 111.81(14) no
O2 S1 C6 C5 . . . . -64.64(19) no
N1 S1 C6 C1 . . . . -0.09(14) no
N1 S1 C6 C5 . . . . -176.54(17) no
S1 N1 C7 O3 . . . . 177.61(17) no
S1 N1 C7 C1 . . . . -1.0(2) no
C8 N1 C7 O3 . . . . 2.1(3) no
C8 N1 C7 C1 . . . . -176.49(17) no
S1 N1 C8 C9 . . . . -83.37(19) no
C7 N1 C8 C9 . . . . 91.9(2) no
C6 C1 C2 C3 . . . . 0.6(3) no
C7 C1 C2 C3 . . . . -176.00(19) no
C2 C1 C6 S1 . . . . -177.54(15) no
C2 C1 C6 C5 . . . . -0.9(3) no
C7 C1 C6 S1 . . . . -0.5(2) no
C7 C1 C6 C5 . . . . 176.15(17) no
C2 C1 C7 O3 . . . . -0.8(3) no
C2 C1 C7 N1 . . . . 177.73(19) no
C6 C1 C7 O3 . . . . -177.6(2) no
C6 C1 C7 N1 . . . . 0.9(2) no
C1 C2 C3 C4 . . . . -0.3(3) no
C2 C3 C4 C5 . . . . 0.2(3) no
C3 C4 C5 C6 . . . . -0.4(3) no
C4 C5 C6 S1 . . . . 176.81(15) no
C4 C5 C6 C1 . . . . 0.8(3) no
N1 C8 C9 C10 . . . . -119.5(2) no
C8 C9 C10 C11 . . . . 0.3(3) no
C8 C9 C10 C12 . . . . 178.9(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742094
