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#$Date: 2023-01-06 12:30:01 +0200 (Fri, 06 Jan 2023) $
#$Revision: 280231 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106434.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106434
loop_
_publ_author_name
'Chen, Qing-Wu'
'Shen, De-Long'
_publ_section_title
;
 Crystal structure of
 2-[(2-oxo-thiazolidine-3-carbonyl)sulfamoyl]-methy-benzoic acid methyl
 ester, C13H14N2O6S2
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              67
_journal_page_last               68
_journal_paper_doi               10.1515/ncrs-2016-0150
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C13 H14 N2 O6 S2'
_chemical_formula_sum            'C13 H14 N2 O6 S2'
_chemical_formula_weight         358.38
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 98.4457(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.1174(10)
_cell_length_b                   9.8677(4)
_cell_length_c                   11.2738(4)
_cell_measurement_reflns_used    9987
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.0
_cell_volume                     3094.0(2)
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(1)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rolling anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14936
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  0.9633
_exptl_absorpt_correction_T_min  0.8819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, T. (1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0382
_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)+(0.0400P)²+3.9144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.1141
_reflns_number_gt                2326
_reflns_number_total             3529
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0150_suppl.cif
_cod_data_source_block           s2
_cod_database_code               8106434
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.38056(2) 0.58058(6) 0.71532(5) 0.04198(18) Uani 1 1 d . . .
S2 S 0.21754(3) 0.62282(8) 0.28584(8) 0.0711(3) Uani 1 1 d . . .
C1 C 0.34043(8) 0.6800(2) 0.5013(2) 0.0403(5) Uani 1 1 d . . .
O2 O 0.35616(6) 0.50676(18) 0.79716(14) 0.0520(4) Uani 1 1 d . . .
N2 N 0.29830(6) 0.68091(19) 0.41667(17) 0.0409(4) Uani 1 1 d . . .
N1 N 0.33947(7) 0.58930(19) 0.59385(17) 0.0438(5) Uani 1 1 d . . .
H1 H 0.3159 0.5331 0.5883 0.053 Uiso 1 1 calc R . .
O3 O 0.37315(6) 0.75475(18) 0.49105(15) 0.0534(4) Uani 1 1 d . . .
O4 O 0.25432(7) 0.5098(2) 0.48893(18) 0.0636(5) Uani 1 1 d . . .
C4 C 0.25991(9) 0.5947(3) 0.4137(2) 0.0473(6) Uani 1 1 d . . .
O5 O 0.46193(7) 0.39568(19) 0.90780(17) 0.0632(5) Uani 1 1 d . . .
O1 O 0.39832(7) 0.71296(17) 0.74628(15) 0.0550(5) Uani 1 1 d . . .
O6 O 0.47368(6) 0.17356(19) 0.93706(16) 0.0604(5) Uani 1 1 d . . .
C6 C 0.41671(8) 0.3334(2) 0.6607(2) 0.0431(5) Uani 1 1 d . . .
C10 C 0.41887(9) 0.1029(2) 0.7323(2) 0.0538(6) Uani 1 1 d . . .
H10 H 0.4281 0.0401 0.7929 0.065 Uiso 1 1 calc R . .
C12 C 0.45661(8) 0.2809(3) 0.8724(2) 0.0455(6) Uani 1 1 d . . .
C11 C 0.43044(8) 0.2389(2) 0.7525(2) 0.0412(5) Uani 1 1 d . . .
C5 C 0.42798(8) 0.4825(2) 0.6710(2) 0.0474(6) Uani 1 1 d . . .
H5A H 0.4348 0.5154 0.5941 0.057 Uiso 1 1 calc R . .
H5B H 0.4567 0.4953 0.7290 0.057 Uiso 1 1 calc R . .
C2 C 0.29779(10) 0.7727(3) 0.3141(2) 0.0578(7) Uani 1 1 d . . .
H2A H 0.3260 0.7573 0.2756 0.069 Uiso 1 1 calc R . .
H2B H 0.2982 0.8661 0.3410 0.069 Uiso 1 1 calc R . .
C7 C 0.39179(10) 0.2869(3) 0.5528(2) 0.0596(7) Uani 1 1 d . . .
H7 H 0.3825 0.3482 0.4911 0.072 Uiso 1 1 calc R . .
C8 C 0.38054(12) 0.1516(3) 0.5354(3) 0.0734(9) Uani 1 1 d . . .
H8 H 0.3636 0.1229 0.4626 0.088 Uiso 1 1 calc R . .
C13 C 0.49567(11) 0.1999(4) 1.0589(3) 0.0777(9) Uani 1 1 d . . .
H13A H 0.5182 0.2732 1.0596 0.116 Uiso 1 1 calc R . .
H13B H 0.5122 0.1201 1.0916 0.116 Uiso 1 1 calc R . .
H13C H 0.4713 0.2239 1.1064 0.116 Uiso 1 1 calc R . .
C9 C 0.39415(11) 0.0591(3) 0.6246(3) 0.0683(8) Uani 1 1 d . . .
H9 H 0.3868 -0.0322 0.6126 0.082 Uiso 1 1 calc R . .
C3 C 0.25320(13) 0.7463(4) 0.2273(3) 0.0856(10) Uani 1 1 d . . .
H3A H 0.2618 0.7148 0.1518 0.103 Uiso 1 1 calc R . .
H3B H 0.2350 0.8296 0.2122 0.103 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 S1 O2 119.62(11) . .
O1 S1 N1 109.35(10) . .
O2 S1 N1 102.56(10) . .
O1 S1 C5 108.54(11) . .
O2 S1 C5 110.83(11) . .
N1 S1 C5 104.85(11) . .
C4 S2 C3 93.56(14) . .
O3 C1 N1 125.0(2) . .
O3 C1 N2 120.8(2) . .
N1 C1 N2 114.2(2) . .
C4 N2 C1 126.4(2) . .
C4 N2 C2 116.6(2) . .
C1 N2 C2 116.61(19) . .
C1 N1 S1 124.75(16) . .
C1 N1 H1 117.6 . .
S1 N1 H1 117.6 . .
O4 C4 N2 126.3(2) . .
O4 C4 S2 122.7(2) . .
N2 C4 S2 111.06(18) . .
C12 O6 C13 116.5(2) . .
C7 C6 C11 118.3(2) . .
C7 C6 C5 117.6(2) . .
C11 C6 C5 124.1(2) . .
C9 C10 C11 121.5(3) . .
C9 C10 H10 119.3 . .
C11 C10 H10 119.3 . .
O5 C12 O6 123.3(2) . .
O5 C12 C11 125.5(2) . .
O6 C12 C11 111.2(2) . .
C10 C11 C6 119.2(2) . .
C10 C11 C12 119.1(2) . .
C6 C11 C12 121.7(2) . .
C6 C5 S1 113.29(16) . .
C6 C5 H5A 108.9 . .
S1 C5 H5A 108.9 . .
C6 C5 H5B 108.9 . .
S1 C5 H5B 108.9 . .
H5A C5 H5B 107.7 . .
N2 C2 C3 108.6(2) . .
N2 C2 H2A 110.0 . .
C3 C2 H2A 110.0 . .
N2 C2 H2B 110.0 . .
C3 C2 H2B 110.0 . .
H2A C2 H2B 108.4 . .
C8 C7 C6 121.3(3) . .
C8 C7 H7 119.3 . .
C6 C7 H7 119.3 . .
C9 C8 C7 120.4(3) . .
C9 C8 H8 119.8 . .
C7 C8 H8 119.8 . .
O6 C13 H13A 109.5 . .
O6 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
O6 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C8 C9 C10 119.3(3) . .
C8 C9 H9 120.4 . .
C10 C9 H9 120.4 . .
C2 C3 S2 110.0(2) . .
C2 C3 H3A 109.7 . .
S2 C3 H3A 109.7 . .
C2 C3 H3B 109.7 . .
S2 C3 H3B 109.7 . .
H3A C3 H3B 108.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.4234(17) .
S1 O2 1.4278(17) .
S1 N1 1.6592(19) .
S1 C5 1.777(2) .
S2 C4 1.752(3) .
S2 C3 1.766(4) .
C1 O3 1.198(3) .
C1 N1 1.378(3) .
C1 N2 1.408(3) .
N2 C4 1.371(3) .
N2 C2 1.467(3) .
N1 H1 0.8600 .
O4 C4 1.218(3) .
O5 C12 1.203(3) .
O6 C12 1.335(3) .
O6 C13 1.445(3) .
C6 C7 1.390(3) .
C6 C11 1.405(3) .
C6 C5 1.506(3) .
C10 C9 1.376(4) .
C10 C11 1.392(3) .
C10 H10 0.9300 .
C12 C11 1.499(3) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C2 C3 1.496(4) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C7 C8 1.379(4) .
C7 H7 0.9300 .
C8 C9 1.371(4) .
C8 H8 0.9300 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C9 H9 0.9300 .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O3 C1 N2 C4 175.2(2) . . . .
N1 C1 N2 C4 -5.8(3) . . . .
O3 C1 N2 C2 2.7(3) . . . .
N1 C1 N2 C2 -178.3(2) . . . .
O3 C1 N1 S1 7.6(3) . . . .
N2 C1 N1 S1 -171.31(15) . . . .
O1 S1 N1 C1 33.8(2) . . . .
O2 S1 N1 C1 161.73(18) . . . .
C5 S1 N1 C1 -82.4(2) . . . .
C1 N2 C4 O4 6.0(4) . . . .
C2 N2 C4 O4 178.5(2) . . . .
C1 N2 C4 S2 -174.96(17) . . . .
C2 N2 C4 S2 -2.5(3) . . . .
C3 S2 C4 O4 -177.2(2) . . . .
C3 S2 C4 N2 3.7(2) . . . .
C13 O6 C12 O5 5.6(4) . . . .
C13 O6 C12 C11 -174.3(2) . . . .
C9 C10 C11 C6 -0.3(4) . . . .
C9 C10 C11 C12 178.9(2) . . . .
C7 C6 C11 C10 0.2(3) . . . .
C5 C6 C11 C10 -178.8(2) . . . .
C7 C6 C11 C12 -178.9(2) . . . .
C5 C6 C11 C12 2.1(3) . . . .
O5 C12 C11 C10 -167.5(3) . . . .
O6 C12 C11 C10 12.4(3) . . . .
O5 C12 C11 C6 11.6(4) . . . .
O6 C12 C11 C6 -168.5(2) . . . .
C7 C6 C5 S1 85.8(2) . . . .
C11 C6 C5 S1 -95.2(2) . . . .
O1 S1 C5 C6 168.08(17) . . . .
O2 S1 C5 C6 34.8(2) . . . .
N1 S1 C5 C6 -75.15(19) . . . .
C4 N2 C2 C3 -0.5(3) . . . .
C1 N2 C2 C3 172.7(2) . . . .
C11 C6 C7 C8 0.1(4) . . . .
C5 C6 C7 C8 179.2(3) . . . .
C6 C7 C8 C9 -0.5(5) . . . .
C7 C8 C9 C10 0.5(5) . . . .
C11 C10 C9 C8 -0.1(4) . . . .
N2 C2 C3 S2 3.2(3) . . . .
C4 S2 C3 C2 -4.0(3) . . . .
