#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/99/2229970.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_2229970
loop_
_publ_author_name
'Shakuntala, K.'
'Foro, Sabine'
'Gowda, B. Thimme'
_publ_section_title
;
 N-(2-Methylphenylsulfonyl)propanamide
;
_journal_coeditor_code           DS2108
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1187
_journal_paper_doi               10.1107/S1600536811014164
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H13 N O3 S'
_chemical_formula_moiety         'C10 H13 N O3 S'
_chemical_formula_sum            'C10 H13 N O3 S'
_chemical_formula_weight         227.27
_chemical_name_systematic
;
N-(2-Methylphenylsulfonyl)propanamide
;
_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                 97.876(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3050(8)
_cell_length_b                   13.3390(10)
_cell_length_c                   9.9948(9)
_cell_measurement_reflns_used    1271
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.76
_cell_measurement_theta_min      2.56
_cell_volume                     1096.78(17)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using 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  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4277
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.56
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  0.9563
_exptl_absorpt_correction_T_min  0.8861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.353
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2241
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0435
_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)+(0.0396P)²+0.5309P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1076
_reflns_number_gt                1607
_reflns_number_total             2241
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ds2108.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229970
_cod_database_fobs_code          2229970
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
C C1 0.6604(2) 0.45905(16) 0.3478(2) 0.0403(5) Uani d . 1 . .
C C2 0.5397(3) 0.38655(18) 0.3512(2) 0.0456(6) Uani d . 1 . .
C C3 0.5387(3) 0.3371(2) 0.4736(3) 0.0586(7) Uani d . 1 . .
H H3 0.4597 0.2886 0.4800 0.070 Uiso calc R 1 . .
C C4 0.6499(3) 0.3571(2) 0.5856(3) 0.0622(7) Uani d . 1 . .
H H4 0.6454 0.3221 0.6655 0.075 Uiso calc R 1 . .
C C5 0.7679(3) 0.4288(2) 0.5794(2) 0.0584(7) Uani d . 1 . .
H H5 0.8431 0.4427 0.6550 0.070 Uiso calc R 1 . .
C C6 0.7736(3) 0.47990(19) 0.4607(2) 0.0484(6) Uani d . 1 . .
H H6 0.8530 0.5284 0.4557 0.058 Uiso calc R 1 . .
C C7 0.8782(3) 0.40395(18) 0.0980(2) 0.0461(6) Uani d . 1 . .
C C8 0.9020(3) 0.34442(19) -0.0249(2) 0.0501(6) Uani d . 1 . .
H H8A 0.9198 0.3903 -0.0967 0.060 Uiso calc R 1 . .
H H8B 0.8032 0.3072 -0.0548 0.060 Uiso calc R 1 . .
C C9 1.0421(3) 0.2722(2) -0.0023(3) 0.0646(7) Uani d . 1 . .
H H9A 1.0251 0.2259 0.0679 0.078 Uiso calc R 1 . .
H H9B 1.1412 0.3086 0.0237 0.078 Uiso calc R 1 . .
H H9C 1.0495 0.2359 -0.0843 0.078 Uiso calc R 1 . .
C C10 0.4116(3) 0.3615(2) 0.2348(3) 0.0633(7) Uani d . 1 . .
H H10A 0.4601 0.3585 0.1530 0.076 Uiso calc R 1 . .
H H10B 0.3288 0.4122 0.2264 0.076 Uiso calc R 1 . .
H H10C 0.3641 0.2977 0.2506 0.076 Uiso calc R 1 . .
N N1 0.7295(2) 0.45380(16) 0.08882(19) 0.0497(5) Uani d D 1 . .
H H1N 0.664(3) 0.4451(19) 0.020(2) 0.060 Uiso d D 1 . .
O O1 0.5187(2) 0.56595(14) 0.14397(17) 0.0616(5) Uani d . 1 . .
O O2 0.8011(2) 0.60402(13) 0.23614(19) 0.0673(5) Uani d . 1 . .
O O3 0.9760(2) 0.41109(16) 0.19851(18) 0.0681(5) Uani d . 1 . .
S S1 0.67655(7) 0.53152(5) 0.20265(6) 0.04798(19) Uani d . 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
C6 C1 C2 . . 121.7(2) ?
C6 C1 S1 . . 115.96(18) ?
C2 C1 S1 . . 122.38(16) ?
C3 C2 C1 . . 116.2(2) ?
C3 C2 C10 . . 119.1(2) ?
C1 C2 C10 . . 124.7(2) ?
C4 C3 C2 . . 122.6(3) ?
C4 C3 H3 . . 118.7 ?
C2 C3 H3 . . 118.7 ?
C3 C4 C5 . . 120.0(3) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C6 C5 C4 . . 119.4(2) ?
C6 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
C5 C6 C1 . . 120.1(2) ?
C5 C6 H6 . . 120.0 ?
C1 C6 H6 . . 120.0 ?
O3 C7 N1 . . 120.4(2) ?
O3 C7 C8 . . 125.1(2) ?
N1 C7 C8 . . 114.42(19) ?
C7 C8 C9 . . 113.7(2) ?
C7 C8 H8A . . 108.8 ?
C9 C8 H8A . . 108.8 ?
C7 C8 H8B . . 108.8 ?
C9 C8 H8B . . 108.8 ?
H8A C8 H8B . . 107.7 ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C2 C10 H10A . . 109.5 ?
C2 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C2 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C7 N1 S1 . . 125.02(16) ?
C7 N1 H1N . . 117.6(18) ?
S1 N1 H1N . . 117.3(18) ?
O2 S1 O1 . . 118.19(12) ?
O2 S1 N1 . . 109.70(11) ?
O1 S1 N1 . . 103.59(10) ?
O2 S1 C1 . . 108.31(11) ?
O1 S1 C1 . . 110.06(10) ?
N1 S1 C1 . . 106.35(11) ?
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
C1 C6 . 1.394(3) ?
C1 C2 . 1.397(3) ?
C1 S1 . 1.763(2) ?
C2 C3 . 1.391(3) ?
C2 C10 . 1.503(3) ?
C3 C4 . 1.377(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.377(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.375(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O3 . 1.206(3) ?
C7 N1 . 1.395(3) ?
C7 C8 . 1.499(3) ?
C8 C9 . 1.504(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
N1 S1 . 1.643(2) ?
N1 H1N . 0.822(16) ?
O1 S1 . 1.4363(17) ?
O2 S1 . 1.4219(18) ?
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
N1 H1N O1 3_665 0.822(16) 2.083(17) 2.901(2) 173(3)
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
C6 C1 C2 C3 . . . . 0.3(3) ?
S1 C1 C2 C3 . . . . -178.22(17) ?
C6 C1 C2 C10 . . . . 178.7(2) ?
S1 C1 C2 C10 . . . . 0.1(3) ?
C1 C2 C3 C4 . . . . -0.4(4) ?
C10 C2 C3 C4 . . . . -178.8(2) ?
C2 C3 C4 C5 . . . . 0.3(4) ?
C3 C4 C5 C6 . . . . -0.1(4) ?
C4 C5 C6 C1 . . . . 0.1(4) ?
C2 C1 C6 C5 . . . . -0.2(3) ?
S1 C1 C6 C5 . . . . 178.44(18) ?
O3 C7 C8 C9 . . . . 14.4(4) ?
N1 C7 C8 C9 . . . . -166.1(2) ?
O3 C7 N1 S1 . . . . 4.7(4) ?
C8 C7 N1 S1 . . . . -174.80(17) ?
C7 N1 S1 O2 . . . . 50.2(2) ?
C7 N1 S1 O1 . . . . 177.3(2) ?
C7 N1 S1 C1 . . . . -66.7(2) ?
C6 C1 S1 O2 . . . . -4.0(2) ?
C2 C1 S1 O2 . . . . 174.62(18) ?
C6 C1 S1 O1 . . . . -134.60(17) ?
C2 C1 S1 O1 . . . . 44.0(2) ?
C6 C1 S1 N1 . . . . 113.82(18) ?
C2 C1 S1 N1 . . . . -67.5(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 19002944
