#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/33/8103339.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_8103339
loop_
_publ_author_name
'Ai-Guo Zhong'
_publ_section_title
;
 Crystal structure of
 S-1-[(carboxymethyl)sulfanyl]-N-(2-oxotetrahydro-3-thienyl)acetamide,
 C8H11NO4S2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              255
_journal_volume                  227
_journal_year                    2012
_chemical_formula_moiety         'C8 H11 N O4 S2'
_chemical_formula_sum            'C8 H11 N O4 S2'
_chemical_formula_weight         249.30
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   12.0032(13)
_cell_length_b                   9.1488(10)
_cell_length_c                   19.634(2)
_cell_measurement_reflns_used    3383
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.92
_cell_measurement_theta_min      2.36
_cell_volume                     2156.1(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX II area-detector diffractometer'
_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  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14261
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.487
_exptl_absorpt_correction_T_max  0.9439
_exptl_absorpt_correction_T_min  0.9046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0438
_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)+(0.0476P)²+0.7807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1152
_reflns_number_gt                1381
_reflns_number_total             1996
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            1267-3682.cff
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               8103339
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'
'-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_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
S1 S 0.14843(6) 0.13515(8) 0.45416(4) 0.0449(2) Uani 1 1 d .
S2 S 0.42676(9) 0.13946(10) 0.80575(5) 0.0690(3) Uani 1 1 d .
O1 O 0.2500(2) -0.0011(3) 0.76274(12) 0.0902(10) Uani 1 1 d .
O2 O 0.16616(16) 0.3055(2) 0.59793(10) 0.0451(5) Uani 1 1 d .
O3 O 0.46881(18) 0.0694(2) 0.42059(13) 0.0589(6) Uani 1 1 d .
H3 H 0.5244 0.1193 0.4275 0.088 Uiso 1 1 calc R
O4 O 0.38821(18) 0.2346(2) 0.48752(11) 0.0581(6) Uani 1 1 d .
N1 N 0.26612(18) 0.1098(2) 0.63134(11) 0.0387(6) Uani 1 1 d .
H1 H 0.2830 0.0201 0.6234 0.046 Uiso 1 1 calc R
C1 C 0.4413(3) 0.2266(4) 0.67586(16) 0.0559(9) Uani 1 1 d .
H1A H 0.4467 0.3080 0.6444 0.067 Uiso 1 1 calc R
H1B H 0.4833 0.1449 0.6576 0.067 Uiso 1 1 calc R
C2 C 0.4852(3) 0.2698(4) 0.74585(19) 0.0649(10) Uani 1 1 d .
H2A H 0.4619 0.3683 0.7573 0.078 Uiso 1 1 calc R
H2B H 0.5659 0.2657 0.7467 0.078 Uiso 1 1 calc R
C3 C 0.3173(3) 0.0931(3) 0.75099(15) 0.0524(8) Uani 1 1 d .
C4 C 0.3213(2) 0.1845(3) 0.68706(13) 0.0376(7) Uani 1 1 d .
H4 H 0.2796 0.2745 0.6961 0.045 Uiso 1 1 calc R
C5 C 0.1906(2) 0.1741(3) 0.59198(13) 0.0355(6) Uani 1 1 d .
C6 C 0.1324(2) 0.0773(3) 0.54102(13) 0.0403(7) Uani 1 1 d .
H6A H 0.0536 0.0744 0.5519 0.048 Uiso 1 1 calc R
H6B H 0.1613 -0.0213 0.5455 0.048 Uiso 1 1 calc R
C7 C 0.2773(2) 0.0495(3) 0.43211(15) 0.0498(8) Uani 1 1 d .
H7A H 0.2794 -0.0459 0.4536 0.060 Uiso 1 1 calc R
H7B H 0.2781 0.0340 0.3832 0.060 Uiso 1 1 calc R
C8 C 0.3816(2) 0.1300(3) 0.45126(14) 0.0418(7) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0467(5) 0.0478(5) 0.0401(4) 0.0022(3) -0.0091(3) -0.0022(4)
S2 0.0962(8) 0.0582(6) 0.0526(6) 0.0043(4) -0.0276(5) -0.0096(5)
O1 0.126(2) 0.095(2) 0.0496(14) 0.0032(14) 0.0034(14) -0.0656(19)
O2 0.0449(13) 0.0339(12) 0.0566(13) -0.0092(9) -0.0108(10) 0.0032(9)
O3 0.0493(14) 0.0483(14) 0.0790(16) -0.0143(12) 0.0143(12) -0.0044(11)
O4 0.0518(14) 0.0552(15) 0.0675(15) -0.0238(12) 0.0019(11) -0.0060(11)
N1 0.0479(15) 0.0303(13) 0.0379(13) -0.0051(10) -0.0019(11) 0.0034(11)
C1 0.048(2) 0.067(2) 0.053(2) -0.0011(16) 0.0057(15) -0.0131(16)
C2 0.052(2) 0.072(3) 0.070(2) -0.0031(19) -0.0124(17) -0.0131(18)
C3 0.069(2) 0.049(2) 0.0393(18) -0.0042(14) 0.0009(15) -0.0137(18)
C4 0.0426(16) 0.0365(16) 0.0337(15) -0.0033(12) -0.0025(12) 0.0020(13)
C5 0.0336(15) 0.0371(18) 0.0357(15) -0.0022(12) 0.0036(12) -0.0053(13)
C6 0.0426(18) 0.0392(17) 0.0390(16) -0.0043(12) 0.0000(12) -0.0085(13)
C7 0.0500(19) 0.052(2) 0.0477(18) -0.0118(15) 0.0076(14) -0.0108(15)
C8 0.0472(18) 0.0397(18) 0.0385(16) 0.0022(14) 0.0061(13) 0.0020(14)
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
C7 S1 C6 101.14(15)
C3 S2 C2 92.93(16)
C8 O3 H3 109.5
C5 N1 C4 122.8(2)
C5 N1 H1 118.6
C4 N1 H1 118.6
C4 C1 C2 105.3(3)
C4 C1 H1A 110.7
C2 C1 H1A 110.7
C4 C1 H1B 110.7
C2 C1 H1B 110.7
H1A C1 H1B 108.8
C1 C2 S2 106.3(2)
C1 C2 H2A 110.5
S2 C2 H2A 110.5
C1 C2 H2B 110.5
S2 C2 H2B 110.5
H2A C2 H2B 108.7
O1 C3 C4 125.2(3)
O1 C3 S2 124.1(3)
C4 C3 S2 110.7(2)
N1 C4 C1 116.5(2)
N1 C4 C3 110.6(2)
C1 C4 C3 107.0(2)
N1 C4 H4 107.4
C1 C4 H4 107.4
C3 C4 H4 107.4
O2 C5 N1 122.3(3)
O2 C5 C6 121.4(3)
N1 C5 C6 116.2(2)
C5 C6 S1 114.04(19)
C5 C6 H6A 108.7
S1 C6 H6A 108.7
C5 C6 H6B 108.7
S1 C6 H6B 108.7
H6A C6 H6B 107.6
C8 C7 S1 116.5(2)
C8 C7 H7A 108.2
S1 C7 H7A 108.2
C8 C7 H7B 108.2
S1 C7 H7B 108.2
H7A C7 H7B 107.3
O4 C8 O3 123.5(3)
O4 C8 C7 126.7(3)
O3 C8 C7 109.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C7 1.787(3)
S1 C6 1.796(3)
S2 C3 1.750(3)
S2 C2 1.815(4)
O1 C3 1.204(4)
O2 C5 1.243(3)
O3 C8 1.329(3)
O3 H3 0.8200
O4 C8 1.195(3)
N1 C5 1.328(3)
N1 C4 1.450(3)
N1 H1 0.8600
C1 C4 1.508(4)
C1 C2 1.523(4)
C1 H1A 0.9700
C1 H1B 0.9700
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.509(4)
C4 H4 0.9800
C5 C6 1.508(4)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C8 1.500(4)
C7 H7A 0.9700
C7 H7B 0.9700
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.86 2.12 2.973(3) 175.3 8_655
O3 H3 O2 0.82 1.90 2.656(3) 152.4 4_556
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
C4 C1 C2 S2 40.3(3)
C3 S2 C2 C1 -21.7(3)
C2 S2 C3 O1 175.5(3)
C2 S2 C3 C4 -3.1(3)
C5 N1 C4 C1 -106.4(3)
C5 N1 C4 C3 131.1(3)
C2 C1 C4 N1 -167.5(3)
C2 C1 C4 C3 -43.1(3)
O1 C3 C4 N1 -23.2(5)
S2 C3 C4 N1 155.4(2)
O1 C3 C4 C1 -151.1(3)
S2 C3 C4 C1 27.5(3)
C4 N1 C5 O2 3.9(4)
C4 N1 C5 C6 -173.8(2)
O2 C5 C6 S1 60.6(3)
N1 C5 C6 S1 -121.7(2)
C7 S1 C6 C5 86.1(2)
C6 S1 C7 C8 -84.1(3)
S1 C7 C8 O4 11.0(4)
S1 C7 C8 O3 -167.9(2)
