#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/04/2210475.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_2210475
loop_
_publ_author_name
'Ngah, Nurziana'
'Kassim, Mohammad B.'
'Yamin, Bohari M.'
_publ_section_title
;
 (2S)-1-(Benzoylthiocarbamoyl)pyrrolidine-2-carboxylic acid
 monohydrate
;
_journal_coeditor_code           AT2108
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4501
_journal_page_last               o4502
_journal_paper_doi               10.1107/S1600536806036816
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H14 N2 O3 S, H2 O'
_chemical_formula_moiety         'C13 H14 N2 O3 S, H2 O'
_chemical_formula_sum            'C13 H16 N2 O4 S'
_chemical_formula_weight         296.34
_chemical_name_systematic
;
(2S)-1-(Benzoylthiocarbamoyl)pyrrolidine-2-carboxylic acid monohydrate
;
_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                   9.05(4)
_cell_length_b                   12.00(6)
_cell_length_c                   13.33(6)
_cell_measurement_reflns_used    694
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.3
_cell_volume                     1448(12)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 1.0
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method       ω
_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  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6893
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.9766
_exptl_absorpt_correction_T_min  0.8903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.15
_refine_ls_abs_structure_details 'Flack (1983), 634 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.99
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2527
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.00
_refine_ls_R_factor_all          0.050
_refine_ls_R_factor_gt           0.037
_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)+(0.0468P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.083
_refine_ls_wR_factor_ref         0.088
_reflns_number_gt                2047
_reflns_number_total             2527
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2108.cif
_cod_data_source_block           I
_cod_database_code               2210475
_cod_database_fobs_code          2210475
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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 0.25676(9) -0.43079(5) -0.46911(5) 0.0591(2) Uani d . 1 . .
O O1 0.3018(2) -0.15137(15) -0.64794(13) 0.0584(5) Uani d . 1 . .
O O2 0.3655(2) -0.46979(14) -0.72748(13) 0.0535(5) Uani d . 1 B .
O O3 0.2513(2) -0.63497(11) -0.70096(11) 0.0518(4) Uani d . 1 B .
H H3 0.3191 -0.6604 -0.7348 0.062 Uiso calc R 1 . .
O O4 -0.4521(2) -0.26865(15) -0.70101(16) 0.0552(5) Uani d D 1 . .
H H4A -0.478(3) -0.3274(15) -0.727(2) 0.083 Uiso d D 1 . .
H H4B -0.524(2) -0.2315(19) -0.684(2) 0.083 Uiso d D 1 . .
N N1 0.1786(2) -0.22089(13) -0.51478(15) 0.0427(5) Uani d . 1 . .
H H1A 0.1312 -0.2044 -0.4609 0.051 Uiso d R 1 . .
N N2 0.1201(2) -0.35932(14) -0.63133(13) 0.0413(5) Uani d . 1 B .
C C1 0.2466(3) -0.02107(17) -0.51956(16) 0.0408(5) Uani d . 1 . .
C C2 0.3510(3) 0.0556(2) -0.5538(2) 0.0579(7) Uani d . 1 . .
H H2 0.4181 0.0351 -0.6032 0.069 Uiso calc R 1 . .
C C3 0.3549(4) 0.1635(2) -0.5137(3) 0.0716(9) Uani d . 1 . .
H H3A 0.4238 0.2147 -0.5373 0.086 Uiso calc R 1 . .
C C4 0.2579(4) 0.1939(2) -0.4403(2) 0.0724(9) Uani d . 1 . .
H H4 0.2612 0.2654 -0.4134 0.087 Uiso calc R 1 . .
C C5 0.1548(4) 0.1179(2) -0.4059(2) 0.0689(9) Uani d . 1 . .
H H5 0.0893 0.1385 -0.3555 0.083 Uiso calc R 1 . .
C C6 0.1478(3) 0.0108(2) -0.44597(19) 0.0507(7) Uani d . 1 . .
H H6 0.0768 -0.0392 -0.4232 0.061 Uiso calc R 1 . .
C C7 0.2453(3) -0.13519(18) -0.56626(16) 0.0420(5) Uani d . 1 . .
C C8 0.1821(3) -0.33573(19) -0.54430(16) 0.0409(6) Uani d . 1 . .
C C9 0.0278(3) -0.2830(2) -0.69270(19) 0.0488(7) Uani d D 1 . .
H H9A 0.0872 -0.2438 -0.7419 0.059 Uiso calc R 1 A 1
H H9B -0.0228 -0.2290 -0.6508 0.059 Uiso calc R 1 A 1
C C10A -0.0811(4) -0.3609(2) -0.7430(3) 0.0580(11) Uani d PDU 0.916(7) B 1
H H10A -0.1132 -0.3312 -0.8071 0.070 Uiso calc PR 0.916(7) B 1
H H10B -0.1669 -0.3731 -0.7009 0.070 Uiso calc PR 0.916(7) B 1
C C10B -0.004(3) -0.3486(8) -0.7841(10) 0.0580(11) Uani d PDU 0.084(7) B 2
H H10C 0.0663 -0.3309 -0.8363 0.070 Uiso calc PR 0.084(7) B 2
H H10D -0.1027 -0.3313 -0.8086 0.070 Uiso calc PR 0.084(7) B 2
C C11 0.0057(3) -0.4679(2) -0.7570(2) 0.0617(8) Uani d D 1 . .
H H11A 0.0606 -0.4658 -0.8195 0.074 Uiso calc RD 1 B 1
H H11B -0.0604 -0.5315 -0.7584 0.074 Uiso calc R 1 B 1
C C12 0.1110(3) -0.47585(18) -0.66789(17) 0.0404(6) Uani d . 1 B .
H H12 0.0676 -0.5233 -0.6158 0.048 Uiso calc R 1 . .
C C13 0.2597(3) -0.52311(18) -0.70019(15) 0.0394(5) 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
_geom_angle_publ_flag
C13 O3 H3 109.5 ?
H4A O4 H4B 110.7(17) yes
C7 N1 C8 124.9(3) ?
C7 N1 H1A 117.6 ?
C8 N1 H1A 117.5 ?
C8 N2 C12 120.98(18) ?
C8 N2 C9 126.2(3) ?
C12 N2 C9 111.7(3) ?
C6 C1 C2 119.2(3) ?
C6 C1 C7 122.7(2) ?
C2 C1 C7 118.1(3) ?
C1 C2 C3 120.2(4) ?
C1 C2 H2 119.9 ?
C3 C2 H2 119.9 ?
C4 C3 C2 120.3(3) ?
C4 C3 H3A 119.9 ?
C2 C3 H3A 119.9 ?
C3 C4 C5 119.7(4) ?
C3 C4 H4 120.2 ?
C5 C4 H4 120.2 ?
C4 C5 C6 120.8(4) ?
C4 C5 H5 119.6 ?
C6 C5 H5 119.6 ?
C1 C6 C5 119.9(3) ?
C1 C6 H6 120.1 ?
C5 C6 H6 120.1 ?
O1 C7 N1 120.7(3) ?
O1 C7 C1 120.8(2) ?
N1 C7 C1 118.5(4) ?
N2 C8 N1 116.0(2) ?
N2 C8 S1 123.8(3) ?
N1 C8 S1 120.2(3) ?
C10B C9 N2 103.7(6) ?
C10B C9 C10A 34.8(10) ?
N2 C9 C10A 103.2(4) ?
C10B C9 H9A 79.1 ?
N2 C9 H9A 111.1 ?
C10A C9 H9A 111.1 ?
C10B C9 H9B 137.4 ?
N2 C9 H9B 111.1 ?
C10A C9 H9B 111.1 ?
H9A C9 H9B 109.1 ?
C9 C10A C11 103.9(4) ?
C9 C10A H10A 111.0 ?
C11 C10A H10A 111.0 ?
C9 C10A H10B 111.0 ?
C11 C10A H10B 111.0 ?
H10A C10A H10B 109.0 ?
C9 C10B C11 107.6(8) ?
C9 C10B H10C 110.2 ?
C11 C10B H10C 110.2 ?
C9 C10B H10D 110.2 ?
C11 C10B H10D 110.2 ?
H10C C10B H10D 108.5 ?
C10B C11 C10A 34.8(9) ?
C10B C11 C12 106.8(7) ?
C10A C11 C12 106.3(3) ?
C10B C11 H11A 78.4 ?
C10A C11 H11A 110.5 ?
C12 C11 H11A 110.5 ?
C10B C11 H11B 136.0 ?
C10A C11 H11B 110.5 ?
C12 C11 H11B 110.5 ?
H11A C11 H11B 108.7 ?
N2 C12 C13 113.3(2) ?
N2 C12 C11 103.4(2) ?
C13 C12 C11 110.8(3) ?
N2 C12 H12 109.7 ?
C13 C12 H12 109.7 ?
C11 C12 H12 109.7 ?
O2 C13 O3 124.8(3) ?
O2 C13 C12 126.1(4) ?
O3 C13 C12 108.9(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 1.662(5) yes
O1 C7 1.219(5) yes
O2 C13 1.208(5) yes
O3 C13 1.345(7) yes
O3 H3 0.8200 ?
O4 H4A 0.820(10) yes
O4 H4B 0.826(10) yes
N1 C7 1.376(5) yes
N1 C8 1.433(7) yes
N1 H1A 0.8599 ?
N2 C8 1.319(5) yes
N2 C12 1.483(7) yes
N2 C9 1.485(5) yes
C1 C6 1.381(5) ?
C1 C2 1.395(5) ?
C1 C7 1.504(7) ?
C2 C3 1.401(7) ?
C2 H2 0.9300 ?
C3 C4 1.364(6) ?
C3 H3A 0.9300 ?
C4 C5 1.383(6) ?
C4 H4 0.9300 ?
C5 C6 1.393(7) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C9 C10B 1.479(11) ?
C9 C10A 1.515(6) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10A C11 1.516(7) ?
C10A H10A 0.9700 ?
C10A H10B 0.9700 ?
C10B C11 1.479(12) ?
C10B H10C 0.9700 ?
C10B H10D 0.9700 ?
C11 C12 1.527(6) ?
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 C13 1.522(6) ?
C12 H12 0.9800 ?
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
C9 H9A O1 1_555 0.97 2.56 3.000(15) 107 no
N1 H1A O4 3_544 0.86 2.31 3.113(16) 156 yes
O3 H3 O4 4_543 0.82 1.97 2.754(14) 160 yes
O4 H4A O2 1_455 0.82(2) 2.22(2) 2.945(15) 148(3) yes
O4 H4B O1 1_455 0.82(2) 1.91(2) 2.728(14) 177(3) yes
C11 H11A S1 2_544 0.97 2.87 3.754(19) 152 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
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.1(4) ?
C7 C1 C2 C3 178.9(2) ?
C1 C2 C3 C4 0.8(4) ?
C2 C3 C4 C5 -0.5(5) ?
C3 C4 C5 C6 -0.5(5) ?
C2 C1 C6 C5 -0.9(4) ?
C7 C1 C6 C5 -179.9(2) ?
C4 C5 C6 C1 1.2(4) ?
C8 N1 C7 O1 7.1(4) ?
C8 N1 C7 C1 -173.0(2) ?
C6 C1 C7 O1 158.8(2) ?
C2 C1 C7 O1 -20.1(4) ?
C6 C1 C7 N1 -21.1(4) ?
C2 C1 C7 N1 160.0(2) ?
C12 N2 C8 N1 -177.3(2) ?
C9 N2 C8 N1 -10.4(3) ?
C12 N2 C8 S1 0.9(3) yes
C9 N2 C8 S1 167.9(2) yes
C7 N1 C8 N2 -62.4(5) ?
C7 N1 C8 S1 119.4(4) ?
C8 N2 C9 C10B 176.6(11) ?
C12 N2 C9 C10B -15.4(11) ?
C8 N2 C9 C10A -147.6(3) ?
C12 N2 C9 C10A 20.4(3) ?
C10B C9 C10A C11 62.9(8) ?
N2 C9 C10A C11 -32.1(4) ?
N2 C9 C10B C11 25.3(17) ?
C10A C9 C10B C11 -68.3(13) ?
C9 C10B C11 C10A 68.2(10) ?
C9 C10B C11 C12 -26.3(17) ?
C9 C10A C11 C10B -62.9(11) ?
C9 C10A C11 C12 33.2(3) ?
C8 N2 C12 C13 -71.4(3) ?
C9 N2 C12 C13 119.9(3) ?
C8 N2 C12 C11 168.6(2) ?
C9 N2 C12 C11 -0.1(3) ?
C10B C11 C12 N2 15.8(10) ?
C10A C11 C12 N2 -20.5(3) ?
C10B C11 C12 C13 -105.8(10) ?
C10A C11 C12 C13 -142.1(2) ?
N2 C12 C13 O2 -24.2(4) ?
C11 C12 C13 O2 91.4(3) ?
N2 C12 C13 O3 160.4(2) ?
C11 C12 C13 O3 -83.9(2) ?
