#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/48/2224842.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_2224842
loop_
_publ_author_name
'Zhang, Guang-You'
'Chen, Di-Juan'
'Guo, Xiang-Yang'
'Wang, Shu-Hong'
'Chang, Jian-Guo'
_publ_section_title
;
 Methyl 2-(p-toluenesulfonamido)benzoate
;
_journal_coeditor_code           BH2263
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o346
_journal_paper_doi               10.1107/S1600536810000814
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H15 N O4 S'
_chemical_formula_moiety         'C15 H15 N O4 S'
_chemical_formula_sum            'C15 H15 N O4 S'
_chemical_formula_weight         305.34
_chemical_melting_point          380
_chemical_name_systematic
;
Methyl 2-(p-toluenesulfonamido)benzoate
;
_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                 96.854(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.0129(13)
_cell_length_b                   8.3593(7)
_cell_length_c                   11.9664(11)
_cell_measurement_reflns_used    3425
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.96
_cell_measurement_theta_min      2.32
_cell_volume                     1491.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7663
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.9683
_exptl_absorpt_correction_T_min  0.9465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.323
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0360
_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)+(0.0512P)²+0.3683P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                2230
_reflns_number_total             2639
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2263.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224842
_cod_database_fobs_code          2224842
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 S1 0.78611(3) 0.16418(5) 0.77097(4) 0.04976(17) Uani d . 1 . .
O O1 0.56582(10) 0.0349(2) 0.36179(12) 0.0866(5) Uani d . 1 . .
O O2 0.61287(10) 0.2115(2) 0.49515(14) 0.0784(4) Uani d . 1 . .
O O3 0.80078(9) 0.05619(17) 0.86305(10) 0.0642(4) Uani d . 1 . .
O O4 0.76453(10) 0.32689(16) 0.79146(12) 0.0677(4) Uani d . 1 . .
N N1 0.70193(9) 0.10160(18) 0.68303(13) 0.0536(4) Uani d . 1 . .
H H1 0.6798 0.1762 0.6367 0.082(7) Uiso d R 1 . .
C C1 0.52814(17) 0.1643(4) 0.2920(2) 0.1100(11) Uani d . 1 . .
H H1A 0.4763 0.2057 0.3221 0.165 Uiso calc R 1 . .
H H1B 0.5111 0.1258 0.2169 0.165 Uiso calc R 1 . .
H H1C 0.5720 0.2477 0.2906 0.165 Uiso calc R 1 . .
C C2 0.60786(12) 0.0751(3) 0.46213(17) 0.0623(5) Uani d . 1 . .
C C3 0.64536(11) -0.0668(2) 0.52490(15) 0.0524(4) Uani d . 1 . .
C C4 0.69256(10) -0.0513(2) 0.63324(14) 0.0474(4) Uani d . 1 . .
C C5 0.72532(13) -0.1874(2) 0.68995(18) 0.0604(5) Uani d . 1 . .
H H5 0.7568 -0.1781 0.7615 0.072 Uiso calc R 1 . .
C C6 0.71195(15) -0.3359(2) 0.6419(2) 0.0748(6) Uani d . 1 . .
H H6 0.7343 -0.4261 0.6812 0.090 Uiso calc R 1 . .
C C7 0.66594(16) -0.3525(3) 0.5364(2) 0.0810(7) Uani d . 1 . .
H H7 0.6571 -0.4534 0.5042 0.097 Uiso calc R 1 . .
C C8 0.63345(15) -0.2203(3) 0.47946(19) 0.0716(6) Uani d . 1 . .
H H8 0.6023 -0.2324 0.4080 0.086 Uiso calc R 1 . .
C C9 0.88094(11) 0.16066(19) 0.69848(13) 0.0436(4) Uani d . 1 . .
C C10 0.88227(13) 0.2541(2) 0.60377(15) 0.0556(5) Uani d . 1 . .
H H10 0.8323 0.3146 0.5766 0.067 Uiso calc R 1 . .
C C11 0.95774(14) 0.2569(3) 0.55021(16) 0.0626(5) Uani d . 1 . .
H H11 0.9585 0.3201 0.4864 0.075 Uiso calc R 1 . .
C C12 1.03322(12) 0.1678(2) 0.58876(16) 0.0581(5) Uani d . 1 . .
C C13 1.03009(13) 0.0749(2) 0.68292(17) 0.0623(5) Uani d . 1 . .
H H13 1.0800 0.0144 0.7101 0.075 Uiso calc R 1 . .
C C14 0.95457(12) 0.0694(2) 0.73804(15) 0.0541(4) Uani d . 1 . .
H H14 0.9533 0.0048 0.8011 0.065 Uiso calc R 1 . .
C C15 1.11567(15) 0.1736(3) 0.5291(2) 0.0877(8) Uani d . 1 . .
H H15A 1.1455 0.2744 0.5438 0.132 Uiso calc R 1 . .
H H15B 1.0988 0.1620 0.4495 0.132 Uiso calc R 1 . .
H H15C 1.1555 0.0883 0.5557 0.132 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 S1 O4 . . 119.33(9) ?
O3 S1 N1 . . 109.45(8) ?
O4 S1 N1 . . 104.03(8) ?
O3 S1 C9 . . 108.24(8) ?
O4 S1 C9 . . 108.40(8) ?
N1 S1 C9 . . 106.73(8) ?
C2 O1 C1 . . 116.4(2) ?
C4 N1 S1 . . 126.43(12) ?
C4 N1 H1 . . 111.6 ?
S1 N1 H1 . . 112.8 ?
O1 C1 H1A . . 109.5 ?
O1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O2 C2 O1 . . 122.6(2) ?
O2 C2 C3 . . 125.93(19) ?
O1 C2 C3 . . 111.5(2) ?
C8 C3 C4 . . 118.07(18) ?
C8 C3 C2 . . 121.06(18) ?
C4 C3 C2 . . 120.86(17) ?
C5 C4 C3 . . 119.06(17) ?
C5 C4 N1 . . 121.75(16) ?
C3 C4 N1 . . 119.14(16) ?
C6 C5 C4 . . 120.82(19) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C7 C6 C5 . . 120.6(2) ?
C7 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
C8 C7 C6 . . 119.4(2) ?
C8 C7 H7 . . 120.3 ?
C6 C7 H7 . . 120.3 ?
C7 C8 C3 . . 122.0(2) ?
C7 C8 H8 . . 119.0 ?
C3 C8 H8 . . 119.0 ?
C10 C9 C14 . . 120.39(17) ?
C10 C9 S1 . . 119.30(13) ?
C14 C9 S1 . . 120.27(13) ?
C11 C10 C9 . . 119.29(17) ?
C11 C10 H10 . . 120.4 ?
C9 C10 H10 . . 120.4 ?
C10 C11 C12 . . 121.63(18) ?
C10 C11 H11 . . 119.2 ?
C12 C11 H11 . . 119.2 ?
C13 C12 C11 . . 117.99(17) ?
C13 C12 C15 . . 121.3(2) ?
C11 C12 C15 . . 120.7(2) ?
C12 C13 C14 . . 121.46(18) ?
C12 C13 H13 . . 119.3 ?
C14 C13 H13 . . 119.3 ?
C13 C14 C9 . . 119.23(17) ?
C13 C14 H14 . . 120.4 ?
C9 C14 H14 . . 120.4 ?
C12 C15 H15A . . 109.5 ?
C12 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C12 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 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
S1 O3 . 1.4212(13) ?
S1 O4 . 1.4262(14) ?
S1 N1 . 1.6311(15) ?
S1 C9 . 1.7535(17) ?
O1 C2 . 1.331(2) ?
O1 C1 . 1.440(3) ?
O2 C2 . 1.206(3) ?
N1 C4 . 1.410(2) ?
N1 H1 . 0.8734 ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.479(3) ?
C3 C8 . 1.397(3) ?
C3 C4 . 1.407(2) ?
C4 C5 . 1.385(2) ?
C5 C6 . 1.373(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.372(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.358(3) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
C9 C10 . 1.379(2) ?
C9 C14 . 1.380(2) ?
C10 C11 . 1.367(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.388(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.374(3) ?
C12 C15 . 1.502(3) ?
C13 C14 . 1.379(3) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 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
N1 H1 O2 . 0.87 1.89 2.640(2) 143.4 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
O3 S1 N1 C4 . . . . -53.87(17) ?
O4 S1 N1 C4 . . . . 177.55(15) ?
C9 S1 N1 C4 . . . . 63.05(16) ?
C1 O1 C2 O2 . . . . 1.7(3) ?
C1 O1 C2 C3 . . . . -178.72(17) ?
O2 C2 C3 C8 . . . . 178.3(2) ?
O1 C2 C3 C8 . . . . -1.3(2) ?
O2 C2 C3 C4 . . . . -0.4(3) ?
O1 C2 C3 C4 . . . . -179.97(15) ?
C8 C3 C4 C5 . . . . 0.2(3) ?
C2 C3 C4 C5 . . . . 178.93(16) ?
C8 C3 C4 N1 . . . . -177.13(16) ?
C2 C3 C4 N1 . . . . 1.6(2) ?
S1 N1 C4 C5 . . . . 34.0(2) ?
S1 N1 C4 C3 . . . . -148.77(14) ?
C3 C4 C5 C6 . . . . -0.2(3) ?
N1 C4 C5 C6 . . . . 177.03(18) ?
C4 C5 C6 C7 . . . . 0.1(3) ?
C5 C6 C7 C8 . . . . 0.0(4) ?
C6 C7 C8 C3 . . . . 0.0(4) ?
C4 C3 C8 C7 . . . . -0.1(3) ?
C2 C3 C8 C7 . . . . -178.8(2) ?
O3 S1 C9 C10 . . . . 178.84(13) ?
O4 S1 C9 C10 . . . . -50.38(16) ?
N1 S1 C9 C10 . . . . 61.13(15) ?
O3 S1 C9 C14 . . . . -3.30(16) ?
O4 S1 C9 C14 . . . . 127.47(15) ?
N1 S1 C9 C14 . . . . -121.02(14) ?
C14 C9 C10 C11 . . . . -0.8(3) ?
S1 C9 C10 C11 . . . . 177.06(14) ?
C9 C10 C11 C12 . . . . 0.1(3) ?
C10 C11 C12 C13 . . . . 0.3(3) ?
C10 C11 C12 C15 . . . . -179.53(18) ?
C11 C12 C13 C14 . . . . 0.1(3) ?
C15 C12 C13 C14 . . . . 179.90(18) ?
C12 C13 C14 C9 . . . . -0.8(3) ?
C10 C9 C14 C13 . . . . 1.2(3) ?
S1 C9 C14 C13 . . . . -176.68(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 644637
