#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/27/2222732.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_2222732
loop_
_publ_author_name
'Tang, Qiong'
'Feng, Qi'
'Xu, Jian'
'Yao, Cheng'
_publ_section_title
;
 2-[2-(Methylsulfonyl)ethyl]isoindoline-1,3-dione
;
_journal_coeditor_code           HK2730
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1932
_journal_paper_doi               10.1107/S160053680902580X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H11 N O4 S'
_chemical_formula_moiety         'C11 H11 N O4 S'
_chemical_formula_sum            'C11 H11 N O4 S'
_chemical_formula_weight         253.27
_chemical_name_systematic
;
2-[2-(Methylsulfonyl)ethyl]isoindoline-1,3-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 112.31(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6030(15)
_cell_length_b                   17.766(4)
_cell_length_c                   8.9940(18)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     1123.9(5)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2182
_diffrn_reflns_theta_full        25.26
_diffrn_reflns_theta_max         25.26
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.9716
_exptl_absorpt_correction_T_min  0.9443
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.354
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0477
_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)+(0.09P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1437
_reflns_number_gt                1567
_reflns_number_total             2027
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2730.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222732
_cod_database_fobs_code          2222732
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.44021(11) 0.29490(4) 0.03299(8) 0.0425(3) Uani d . 1 . .
O O1 0.8805(3) 0.29528(10) 0.4407(3) 0.0524(6) Uani d . 1 . .
O O2 0.7221(3) 0.50798(11) 0.1325(3) 0.0555(6) Uani d . 1 . .
O O3 0.3992(4) 0.33791(14) 0.1503(3) 0.0700(7) Uani d . 1 . .
O O4 0.5068(4) 0.21958(12) 0.0776(3) 0.0662(7) Uani d . 1 . .
N N 0.8004(3) 0.39124(12) 0.2541(3) 0.0394(6) Uani d . 1 . .
C C1 0.7239(5) 0.55296(19) 0.6247(4) 0.0582(9) Uani d . 1 . .
H H1A 0.6981 0.5972 0.6679 0.070 Uiso calc R 1 . .
C C2 0.7703(5) 0.4883(2) 0.7187(4) 0.0584(9) Uani d . 1 . .
H H2A 0.7765 0.4901 0.8239 0.070 Uiso calc R 1 . .
C C3 0.8074(4) 0.42096(18) 0.6577(4) 0.0496(8) Uani d . 1 . .
H H3A 0.8368 0.3774 0.7197 0.060 Uiso calc R 1 . .
C C4 0.7993(4) 0.42102(15) 0.5027(3) 0.0397(7) Uani d . 1 . .
C C5 0.8318(4) 0.35948(15) 0.4035(3) 0.0390(6) Uani d . 1 . .
C C6 0.7531(4) 0.46788(15) 0.2484(3) 0.0398(7) Uani d . 1 . .
C C7 0.7534(4) 0.48617(15) 0.4094(3) 0.0399(7) Uani d . 1 . .
C C8 0.7155(4) 0.55292(16) 0.4690(4) 0.0495(8) Uani d . 1 . .
H H8A 0.6854 0.5963 0.4066 0.059 Uiso calc R 1 . .
C C9 0.8028(4) 0.34924(16) 0.1157(3) 0.0447(7) Uani d . 1 . .
H H9A 0.8480 0.2986 0.1496 0.054 Uiso calc R 1 . .
H H9B 0.8919 0.3730 0.0766 0.054 Uiso calc R 1 . .
C C10 0.6092(4) 0.34476(15) -0.0211(3) 0.0399(7) Uani d . 1 . .
H H10A 0.6228 0.3201 -0.1123 0.048 Uiso calc R 1 . .
H H10B 0.5626 0.3954 -0.0538 0.048 Uiso calc R 1 . .
C C11 0.2381(5) 0.29295(18) -0.1438(4) 0.0541(8) Uani d . 1 . .
H H11A 0.1381 0.2665 -0.1253 0.081 Uiso calc R 1 . .
H H11B 0.2668 0.2677 -0.2263 0.081 Uiso calc R 1 . .
H H11C 0.1978 0.3435 -0.1773 0.081 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 S O4 . . 116.42(16) ?
O3 S C10 . . 108.61(14) ?
O3 S C11 . . 108.68(16) ?
O4 S C10 . . 109.11(14) ?
O4 S C11 . . 109.42(15) ?
C11 S C10 . . 103.86(15) ?
C5 N C6 . . 112.1(2) ?
C5 N C9 . . 124.3(2) ?
C6 N C9 . . 123.5(2) ?
C8 C1 C2 . . 121.4(3) ?
C8 C1 H1A . . 119.3 ?
C2 C1 H1A . . 119.3 ?
C3 C2 C1 . . 120.9(3) ?
C3 C2 H2A . . 119.5 ?
C1 C2 H2A . . 119.5 ?
C4 C3 C2 . . 117.6(3) ?
C4 C3 H3A . . 121.2 ?
C2 C3 H3A . . 121.2 ?
C3 C4 C7 . . 121.1(3) ?
C3 C4 C5 . . 130.9(3) ?
C7 C4 C5 . . 108.0(2) ?
O1 C5 N . . 124.9(3) ?
O1 C5 C4 . . 129.1(3) ?
N C5 C4 . . 105.9(2) ?
O2 C6 N . . 124.4(3) ?
O2 C6 C7 . . 129.8(3) ?
N C6 C7 . . 105.8(2) ?
C8 C7 C4 . . 121.5(3) ?
C8 C7 C6 . . 130.2(3) ?
C4 C7 C6 . . 108.2(2) ?
C7 C8 C1 . . 117.4(3) ?
C7 C8 H8A . . 121.3 ?
C1 C8 H8A . . 121.3 ?
N C9 C10 . . 113.3(2) ?
N C9 H9A . . 108.9 ?
C10 C9 H9A . . 108.9 ?
N C9 H9B . . 108.9 ?
C10 C9 H9B . . 108.9 ?
H9A C9 H9B . . 107.7 ?
C9 C10 S . . 112.58(19) ?
C9 C10 H10A . . 109.1 ?
S C10 H10A . . 109.1 ?
C9 C10 H10B . . 109.1 ?
S C10 H10B . . 109.1 ?
H10A C10 H10B . . 107.8 ?
S C11 H11A . . 109.5 ?
S C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
S C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
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
S O3 . 1.430(2) ?
S O4 . 1.433(2) ?
S C11 . 1.743(3) ?
S C10 . 1.774(3) ?
O1 C5 . 1.207(3) ?
N C5 . 1.392(3) ?
N C6 . 1.404(3) ?
N C9 . 1.457(3) ?
C1 C8 . 1.377(5) ?
C1 C2 . 1.391(5) ?
C1 H1A . 0.9300 ?
O2 C6 . 1.210(3) ?
C2 C3 . 1.389(4) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.371(4) ?
C3 H3A . 0.9300 ?
C4 C7 . 1.394(4) ?
C4 C5 . 1.490(4) ?
C6 C7 . 1.483(4) ?
C7 C8 . 1.376(4) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.520(4) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
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
C1 H1A O3 3_666 0.93 2.34 3.189(5) 152 yes
C11 H11A O1 4_465 0.96 2.51 3.463(4) 175 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
C8 C1 C2 C3 . . . . -0.8(5) ?
C1 C2 C3 C4 . . . . 0.9(5) ?
C2 C3 C4 C7 . . . . -0.6(4) ?
C2 C3 C4 C5 . . . . 179.7(3) ?
C6 N C5 O1 . . . . -177.4(3) ?
C9 N C5 O1 . . . . 6.6(4) ?
C6 N C5 C4 . . . . 0.8(3) ?
C9 N C5 C4 . . . . -175.2(2) ?
C3 C4 C5 O1 . . . . -3.1(5) ?
C7 C4 C5 O1 . . . . 177.2(3) ?
C3 C4 C5 N . . . . 178.8(3) ?
C7 C4 C5 N . . . . -0.9(3) ?
C5 N C6 O2 . . . . 178.9(3) ?
C9 N C6 O2 . . . . -5.1(4) ?
C5 N C6 C7 . . . . -0.4(3) ?
C9 N C6 C7 . . . . 175.6(2) ?
C3 C4 C7 C8 . . . . 0.3(4) ?
C5 C4 C7 C8 . . . . -179.9(3) ?
C3 C4 C7 C6 . . . . -179.1(3) ?
C5 C4 C7 C6 . . . . 0.7(3) ?
O2 C6 C7 C8 . . . . 1.3(5) ?
N C6 C7 C8 . . . . -179.5(3) ?
O2 C6 C7 C4 . . . . -179.4(3) ?
N C6 C7 C4 . . . . -0.2(3) ?
C4 C7 C8 C1 . . . . -0.2(4) ?
C6 C7 C8 C1 . . . . 179.0(3) ?
C2 C1 C8 C7 . . . . 0.5(5) ?
C5 N C9 C10 . . . . 112.9(3) ?
C6 N C9 C10 . . . . -62.6(3) ?
N C9 C10 S . . . . -63.7(3) ?
O3 S C10 C9 . . . . 67.7(2) ?
O4 S C10 C9 . . . . -60.2(2) ?
C11 S C10 C9 . . . . -176.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 16170571
