#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/20/2222040.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_2222040
loop_
_publ_author_name
'Syed, Tayyaba'
'Hameed, Shahid'
'Jones, Peter G.'
'Schmidt-Meier, Andrea'
_publ_section_title
;
 (2S)-Methyl 2-(p-toluenesulfonamido)propanoate
;
_journal_coeditor_code           HG2507
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1300
_journal_paper_doi               10.1107/S1600536809017371
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H15 N O4 S'
_chemical_formula_moiety         'C11 H15 N O4 S'
_chemical_formula_sum            'C11 H15 N O4 S'
_chemical_formula_weight         257.30
_chemical_melting_point_gt       363
_chemical_melting_point_lt       365
_chemical_name_systematic
;
(2S)-Methyl 2-(p-toluenesulfonamido)propanoate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1948(2)
_cell_length_b                   11.2552(3)
_cell_length_c                   15.3311(4)
_cell_measurement_reflns_used    40101
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.5914
_cell_measurement_theta_min      2.2373
_cell_volume                     1241.50(6)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2008)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2008)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2008)
;
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1419
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method       ω-scan
_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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0133
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            55416
_diffrn_reflns_theta_full        32.03
_diffrn_reflns_theta_max         32.03
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.312
_refine_ls_abs_structure_details 'Flack (1983), 1818 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         4284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0220
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0451P)²+0.0628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0631
_refine_ls_wR_factor_ref         0.0634
_reflns_number_gt                4060
_reflns_number_total             4284
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            hg2507.cif
_cod_data_source_block           I
_cod_database_code               2222040
_cod_database_fobs_code          2222040
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.77287(3) 0.499255(18) 0.576519(12) 0.01308(5) Uani d . 1 . .
O O1 0.26383(10) 0.24453(5) 0.58832(5) 0.01963(14) Uani d . 1 . .
O O2 0.29792(10) 0.39044(5) 0.68639(4) 0.01622(12) Uani d . 1 . .
O O3 0.95092(9) 0.44220(6) 0.58061(5) 0.02115(14) Uani d . 1 . .
O O4 0.70626(11) 0.56695(6) 0.64934(4) 0.02111(14) Uani d . 1 . .
C C1 0.31824(12) 0.34256(7) 0.60812(5) 0.01252(14) Uani d . 1 . .
C C2 0.42632(12) 0.42436(7) 0.54745(5) 0.01322(14) Uani d . 1 . .
H H2 0.4070 0.5085 0.5662 0.016 Uiso calc R 1 . .
C C3 0.36297(14) 0.41083(10) 0.45331(6) 0.0239(2) Uani d . 1 . .
H H3A 0.4314 0.4668 0.4164 0.036 Uiso calc R 1 . .
H H3B 0.2295 0.4275 0.4493 0.036 Uiso calc R 1 . .
H H3C 0.3872 0.3295 0.4336 0.036 Uiso calc R 1 . .
C C4 0.19070(16) 0.32121(10) 0.74852(7) 0.0258(2) Uani d . 1 . .
H H4A 0.0614 0.3160 0.7288 0.039 Uiso calc R 1 . .
H H4B 0.1950 0.3598 0.8058 0.039 Uiso calc R 1 . .
H H4C 0.2433 0.2411 0.7529 0.039 Uiso calc R 1 . .
C C5 0.77229(12) 0.59314(7) 0.48448(5) 0.01268(14) Uani d . 1 . .
C C6 0.69566(12) 0.70659(7) 0.48923(5) 0.01463(14) Uani d . 1 . .
H H6 0.6427 0.7348 0.5421 0.018 Uiso calc R 1 . .
C C7 0.69813(12) 0.77808(7) 0.41487(6) 0.01543(15) Uani d . 1 . .
H H7 0.6459 0.8555 0.4174 0.019 Uiso calc R 1 . .
C C8 0.77573(13) 0.73814(7) 0.33690(5) 0.01487(15) Uani d . 1 . .
C C9 0.84746(13) 0.62251(8) 0.33331(6) 0.01649(16) Uani d . 1 . .
H H9 0.8974 0.5933 0.2801 0.020 Uiso calc R 1 . .
C C10 0.84653(12) 0.55006(7) 0.40655(6) 0.01525(15) Uani d . 1 . .
H H10 0.8959 0.4719 0.4037 0.018 Uiso calc R 1 . .
C C11 0.78446(17) 0.81761(9) 0.25811(6) 0.02262(18) Uani d . 1 . .
H H11A 0.6738 0.8683 0.2564 0.034 Uiso calc R 1 . .
H H11B 0.7893 0.7689 0.2052 0.034 Uiso calc R 1 . .
H H11C 0.8960 0.8674 0.2614 0.034 Uiso calc R 1 . .
N N 0.62422(10) 0.39329(6) 0.55827(5) 0.01262(13) Uani d . 1 . .
H H01 0.661(2) 0.3437(14) 0.5189(10) 0.032(4) Uiso 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
O4 S O3 . . 120.15(5) ?
O4 S N . . 107.69(4) ?
O3 S N . . 105.46(4) ?
O4 S C5 . . 107.69(4) ?
O3 S C5 . . 107.79(4) ?
N S C5 . . 107.48(4) ?
C1 O2 C4 . . 115.78(7) ?
O1 C1 O2 . . 124.28(8) ?
O1 C1 C2 . . 124.32(8) ?
O2 C1 C2 . . 111.35(7) ?
N C2 C3 . . 111.84(7) ?
N C2 C1 . . 106.32(7) ?
C3 C2 C1 . . 111.48(7) ?
C6 C5 C10 . . 120.98(7) ?
C6 C5 S . . 120.57(6) ?
C10 C5 S . . 118.43(6) ?
C5 C6 C7 . . 118.74(7) ?
C8 C7 C6 . . 121.32(7) ?
C7 C8 C9 . . 118.74(7) ?
C7 C8 C11 . . 120.90(8) ?
C9 C8 C11 . . 120.36(8) ?
C10 C9 C8 . . 120.81(8) ?
C9 C10 C5 . . 119.37(8) ?
C2 N S . . 118.70(6) ?
N C2 H2 . . 109.0 ?
C3 C2 H2 . . 109.0 ?
C1 C2 H2 . . 109.0 ?
C2 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C2 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
O2 C4 H4A . . 109.5 ?
O2 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
O2 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C5 C6 H6 . . 120.6 ?
C7 C6 H6 . . 120.6 ?
C8 C7 H7 . . 119.3 ?
C6 C7 H7 . . 119.3 ?
C10 C9 H9 . . 119.6 ?
C8 C9 H9 . . 119.6 ?
C9 C10 H10 . . 120.3 ?
C5 C10 H10 . . 120.3 ?
C8 C11 H11A . . 109.5 ?
C8 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C8 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C2 N H01 . . 111.8(10) ?
S N H01 . . 113.1(10) ?
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 O4 . 1.4341(7) ?
S O3 . 1.4344(7) ?
S N . 1.6262(8) ?
S C5 . 1.7628(8) ?
O1 C1 . 1.2094(10) ?
O2 C1 . 1.3235(10) ?
O2 C4 . 1.4525(11) ?
C1 C2 . 1.5223(11) ?
C2 N . 1.4755(11) ?
C2 C3 . 1.5213(13) ?
C5 C6 . 1.3929(11) ?
C5 C10 . 1.3956(11) ?
C6 C7 . 1.3955(11) ?
C7 C8 . 1.3938(12) ?
C8 C9 . 1.4012(12) ?
C8 C11 . 1.5043(12) ?
C9 C10 . 1.3878(12) ?
C2 H2 . 1.0000 ?
C3 H3A . 0.9800 ?
C3 H3B . 0.9800 ?
C3 H3C . 0.9800 ?
C4 H4A . 0.9800 ?
C4 H4B . 0.9800 ?
C4 H4C . 0.9800 ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C9 H9 . 0.9500 ?
C10 H10 . 0.9500 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
N H01 . 0.865(16) ?
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
N H01 O1 4_556 0.865(16) 2.057(16) 2.9097(10) 168.6(14)
C10 H10 O1 4_556 0.95 2.62 3.3696(11) 136.4
C9 H9 O2 2_664 0.95 2.63 3.4065(11) 139.5
C7 H7 O3 4_466 0.95 2.67 3.6167(11) 171.5
C4 H4C O4 3_646 0.98 2.49 3.3453(13) 145.1
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
C4 O2 C1 O1 . . . . -4.64(13) ?
C4 O2 C1 C2 . . . . 177.89(8) ?
O1 C1 C2 N . . . . -87.54(10) ?
O2 C1 C2 N . . . . 89.93(8) ?
O1 C1 C2 C3 . . . . 34.58(12) ?
O2 C1 C2 C3 . . . . -147.95(8) ?
O4 S C5 C6 . . . . -6.70(9) ?
O3 S C5 C6 . . . . -137.70(7) ?
N S C5 C6 . . . . 109.07(7) ?
O4 S C5 C10 . . . . 174.70(7) ?
O3 S C5 C10 . . . . 43.70(8) ?
N S C5 C10 . . . . -69.53(8) ?
C10 C5 C6 C7 . . . . -1.48(13) ?
S C5 C6 C7 . . . . 179.97(6) ?
C5 C6 C7 C8 . . . . -0.17(13) ?
C6 C7 C8 C9 . . . . 1.82(13) ?
C6 C7 C8 C11 . . . . -177.58(9) ?
C7 C8 C9 C10 . . . . -1.88(13) ?
C11 C8 C9 C10 . . . . 177.52(9) ?
C8 C9 C10 C5 . . . . 0.29(13) ?
C6 C5 C10 C9 . . . . 1.42(13) ?
S C5 C10 C9 . . . . -179.99(7) ?
C3 C2 N S . . . . 108.25(8) ?
C1 C2 N S . . . . -129.86(6) ?
O4 S N C2 . . . . 52.67(7) ?
O3 S N C2 . . . . -177.90(6) ?
C5 S N C2 . . . . -63.10(7) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8553203
