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In the title compound, C13H14N2O3S·H2O, the benzoyl group lies out of the plane of the N2CS thiourea unit, having a Ccarbon­yl—N—C—S torsion angle of 119.4 (4)°. The crystal structure is stabilized by N—H...O, O—H...O, C—H...O and C—H...S inter­molecular hydrogen bonds, forming a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806036816/at2108sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806036816/at2108Isup2.hkl
Contains datablock I

CCDC reference: 623970

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.008 Å
  • Disorder in main residue
  • R factor = 0.037
  • wR factor = 0.088
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT411_ALERT_2_B Short Inter H...H Contact H4 .. H10C .. 2.03 Ang.
Alert level C PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT732_ALERT_1_C Angle Calc 118.52(19), Rep 118.5(4) ...... 2.11 su-Ra N1 -C7 -C1 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 34.80 Deg. C10B -C9 -C10A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 34.80 Deg. C10B -C11 -C10A 1.555 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C13 H14 N2 O3 S PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 H2 O
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 2527 Count of symmetry unique reflns 1478 Completeness (_total/calc) 170.97% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1049 Fraction of Friedel pairs measured 0.710 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12 = . S
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

(2S)-1-(Benzoylthiocarbamoyl)pyrrolidine-2-carboxylic acid monohydrate top
Crystal data top
C13H14N2O3S·H2OF(000) = 624
Mr = 296.34Dx = 1.360 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 694 reflections
a = 9.05 (4) Åθ = 2.3–25.0°
b = 12.00 (6) ŵ = 0.24 mm1
c = 13.33 (6) ÅT = 298 K
V = 1448 (12) Å3Block, colourless
Z = 40.50 × 0.30 × 0.10 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2527 independent reflections
Radiation source: fine-focus sealed tube2047 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
Detector resolution: 83.66 pixels mm-1θmax = 25.0°, θmin = 2.3°
ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
k = 1214
Tmin = 0.890, Tmax = 0.977l = 1512
6893 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.0468P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
2527 reflectionsΔρmax = 0.17 e Å3
191 parametersΔρmin = 0.15 e Å3
14 restraintsAbsolute structure: Flack (1983), 634 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (10)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.25676 (9)0.43079 (5)0.46911 (5)0.0591 (2)
O10.3018 (2)0.15137 (15)0.64794 (13)0.0584 (5)
O20.3655 (2)0.46979 (14)0.72748 (13)0.0535 (5)
O30.2513 (2)0.63497 (11)0.70096 (11)0.0518 (4)
H30.31910.66040.73480.062*
O40.4521 (2)0.26865 (15)0.70101 (16)0.0552 (5)
H4A0.478 (3)0.3274 (15)0.727 (2)0.083*
H4B0.524 (2)0.2315 (19)0.684 (2)0.083*
N10.1786 (2)0.22089 (13)0.51478 (15)0.0427 (5)
H1A0.13120.20440.46090.051*
N20.1201 (2)0.35932 (14)0.63133 (13)0.0413 (5)
C10.2466 (3)0.02107 (17)0.51956 (16)0.0408 (5)
C20.3510 (3)0.0556 (2)0.5538 (2)0.0579 (7)
H20.41810.03510.60320.069*
C30.3549 (4)0.1635 (2)0.5137 (3)0.0716 (9)
H3A0.42380.21470.53730.086*
C40.2579 (4)0.1939 (2)0.4403 (2)0.0724 (9)
H40.26120.26540.41340.087*
C50.1548 (4)0.1179 (2)0.4059 (2)0.0689 (9)
H50.08930.13850.35550.083*
C60.1478 (3)0.0108 (2)0.44597 (19)0.0507 (7)
H60.07680.03920.42320.061*
C70.2453 (3)0.13519 (18)0.56626 (16)0.0420 (5)
C80.1821 (3)0.33573 (19)0.54430 (16)0.0409 (6)
C90.0278 (3)0.2830 (2)0.69270 (19)0.0488 (7)
H9A0.08720.24380.74190.059*
H9B0.02280.22900.65080.059*
C10A0.0811 (4)0.3609 (2)0.7430 (3)0.0580 (11)0.916 (7)
H10A0.11320.33120.80710.070*0.916 (7)
H10B0.16690.37310.70090.070*0.916 (7)
C10B0.004 (3)0.3486 (8)0.7841 (10)0.0580 (11)0.084 (7)
H10C0.06630.33090.83630.070*0.084 (7)
H10D0.10270.33130.80860.070*0.084 (7)
C110.0057 (3)0.4679 (2)0.7570 (2)0.0617 (8)
H11A0.06060.46580.81950.074*
H11B0.06040.53150.75840.074*
C120.1110 (3)0.47585 (18)0.66789 (17)0.0404 (6)
H120.06760.52330.61580.048*
C130.2597 (3)0.52311 (18)0.70019 (15)0.0394 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0795 (5)0.0500 (4)0.0476 (4)0.0117 (4)0.0124 (4)0.0034 (3)
O10.0619 (12)0.0651 (11)0.0482 (10)0.0032 (9)0.0159 (9)0.0075 (9)
O20.0498 (11)0.0474 (9)0.0633 (12)0.0080 (9)0.0074 (9)0.0087 (9)
O30.0507 (11)0.0371 (8)0.0676 (11)0.0044 (9)0.0097 (11)0.0066 (7)
O40.0501 (11)0.0449 (10)0.0706 (14)0.0059 (9)0.0056 (10)0.0007 (9)
N10.0556 (13)0.0362 (11)0.0364 (11)0.0030 (10)0.0066 (9)0.0056 (8)
N20.0526 (13)0.0347 (10)0.0368 (11)0.0081 (9)0.0019 (10)0.0046 (8)
C10.0392 (13)0.0442 (11)0.0391 (12)0.0013 (13)0.0059 (14)0.0032 (10)
C20.0529 (17)0.0578 (17)0.0630 (18)0.0110 (14)0.0022 (14)0.0067 (13)
C30.074 (2)0.0526 (17)0.088 (2)0.0230 (16)0.016 (2)0.0124 (17)
C40.094 (2)0.0402 (14)0.084 (2)0.0020 (18)0.024 (2)0.0073 (14)
C50.085 (2)0.0533 (17)0.068 (2)0.0056 (16)0.0027 (18)0.0173 (14)
C60.0555 (17)0.0443 (14)0.0523 (16)0.0007 (12)0.0050 (14)0.0019 (12)
C70.0397 (14)0.0471 (13)0.0392 (13)0.0020 (13)0.0007 (13)0.0003 (10)
C80.0446 (15)0.0439 (13)0.0342 (13)0.0044 (11)0.0064 (11)0.0034 (11)
C90.0578 (17)0.0435 (14)0.0450 (16)0.0114 (13)0.0069 (14)0.0012 (11)
C10A0.051 (2)0.0570 (18)0.066 (2)0.0080 (16)0.0108 (17)0.0096 (15)
C10B0.051 (2)0.0570 (18)0.066 (2)0.0080 (16)0.0108 (17)0.0096 (15)
C110.0547 (17)0.0573 (16)0.073 (2)0.0084 (13)0.0198 (15)0.0266 (15)
C120.0429 (15)0.0340 (11)0.0443 (14)0.0015 (11)0.0015 (12)0.0018 (10)
C130.0463 (15)0.0379 (11)0.0340 (11)0.0011 (14)0.0047 (13)0.0032 (9)
Geometric parameters (Å, º) top
S1—C81.662 (5)C4—C51.383 (6)
O1—C71.219 (5)C4—H40.9300
O2—C131.208 (5)C5—C61.393 (7)
O3—C131.345 (7)C5—H50.9300
O3—H30.8200C6—H60.9300
O4—H4A0.820 (10)C9—C10B1.479 (11)
O4—H4B0.826 (10)C9—C10A1.515 (6)
N1—C71.376 (5)C9—H9A0.9700
N1—C81.433 (7)C9—H9B0.9700
N1—H1A0.8599C10A—C111.516 (7)
N2—C81.319 (5)C10A—H10A0.9700
N2—C121.483 (7)C10A—H10B0.9700
N2—C91.485 (5)C10B—C111.479 (12)
C1—C61.381 (5)C10B—H10C0.9700
C1—C21.395 (5)C10B—H10D0.9700
C1—C71.504 (7)C11—C121.527 (6)
C2—C31.401 (7)C11—H11A0.9700
C2—H20.9300C11—H11B0.9700
C3—C41.364 (6)C12—C131.522 (6)
C3—H3A0.9300C12—H120.9800
C13—O3—H3109.5C10A—C9—H9A111.1
H4A—O4—H4B110.7 (17)C10B—C9—H9B137.4
C7—N1—C8124.9 (3)N2—C9—H9B111.1
C7—N1—H1A117.6C10A—C9—H9B111.1
C8—N1—H1A117.5H9A—C9—H9B109.1
C8—N2—C12120.98 (18)C9—C10A—C11103.9 (4)
C8—N2—C9126.2 (3)C9—C10A—H10A111.0
C12—N2—C9111.7 (3)C11—C10A—H10A111.0
C6—C1—C2119.2 (3)C9—C10A—H10B111.0
C6—C1—C7122.7 (2)C11—C10A—H10B111.0
C2—C1—C7118.1 (3)H10A—C10A—H10B109.0
C1—C2—C3120.2 (4)C9—C10B—C11107.6 (8)
C1—C2—H2119.9C9—C10B—H10C110.2
C3—C2—H2119.9C11—C10B—H10C110.2
C4—C3—C2120.3 (3)C9—C10B—H10D110.2
C4—C3—H3A119.9C11—C10B—H10D110.2
C2—C3—H3A119.9H10C—C10B—H10D108.5
C3—C4—C5119.7 (4)C10B—C11—C10A34.8 (9)
C3—C4—H4120.2C10B—C11—C12106.8 (7)
C5—C4—H4120.2C10A—C11—C12106.3 (3)
C4—C5—C6120.8 (4)C10B—C11—H11A78.4
C4—C5—H5119.6C10A—C11—H11A110.5
C6—C5—H5119.6C12—C11—H11A110.5
C1—C6—C5119.9 (3)C10B—C11—H11B136.0
C1—C6—H6120.1C10A—C11—H11B110.5
C5—C6—H6120.1C12—C11—H11B110.5
O1—C7—N1120.7 (3)H11A—C11—H11B108.7
O1—C7—C1120.8 (2)N2—C12—C13113.3 (2)
N1—C7—C1118.5 (4)N2—C12—C11103.4 (2)
N2—C8—N1116.0 (2)C13—C12—C11110.8 (3)
N2—C8—S1123.8 (3)N2—C12—H12109.7
N1—C8—S1120.2 (3)C13—C12—H12109.7
C10B—C9—N2103.7 (6)C11—C12—H12109.7
C10B—C9—C10A34.8 (10)O2—C13—O3124.8 (3)
N2—C9—C10A103.2 (4)O2—C13—C12126.1 (4)
C10B—C9—H9A79.1O3—C13—C12108.9 (3)
N2—C9—H9A111.1
C6—C1—C2—C30.1 (4)C8—N2—C9—C10A147.6 (3)
C7—C1—C2—C3178.9 (2)C12—N2—C9—C10A20.4 (3)
C1—C2—C3—C40.8 (4)C10B—C9—C10A—C1162.9 (8)
C2—C3—C4—C50.5 (5)N2—C9—C10A—C1132.1 (4)
C3—C4—C5—C60.5 (5)N2—C9—C10B—C1125.3 (17)
C2—C1—C6—C50.9 (4)C10A—C9—C10B—C1168.3 (13)
C7—C1—C6—C5179.9 (2)C9—C10B—C11—C10A68.2 (10)
C4—C5—C6—C11.2 (4)C9—C10B—C11—C1226.3 (17)
C8—N1—C7—O17.1 (4)C9—C10A—C11—C10B62.9 (11)
C8—N1—C7—C1173.0 (2)C9—C10A—C11—C1233.2 (3)
C6—C1—C7—O1158.8 (2)C8—N2—C12—C1371.4 (3)
C2—C1—C7—O120.1 (4)C9—N2—C12—C13119.9 (3)
C6—C1—C7—N121.1 (4)C8—N2—C12—C11168.6 (2)
C2—C1—C7—N1160.0 (2)C9—N2—C12—C110.1 (3)
C12—N2—C8—N1177.3 (2)C10B—C11—C12—N215.8 (10)
C9—N2—C8—N110.4 (3)C10A—C11—C12—N220.5 (3)
C12—N2—C8—S10.9 (3)C10B—C11—C12—C13105.8 (10)
C9—N2—C8—S1167.9 (2)C10A—C11—C12—C13142.1 (2)
C7—N1—C8—N262.4 (5)N2—C12—C13—O224.2 (4)
C7—N1—C8—S1119.4 (4)C11—C12—C13—O291.4 (3)
C8—N2—C9—C10B176.6 (11)N2—C12—C13—O3160.4 (2)
C12—N2—C9—C10B15.4 (11)C11—C12—C13—O383.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O10.972.563.000 (15)107
N1—H1A···O4i0.862.313.113 (16)156
O3—H3···O4ii0.821.972.754 (14)160
O4—H4A···O2iii0.82 (2)2.22 (2)2.945 (15)148 (3)
O4—H4B···O1iii0.82 (2)1.91 (2)2.728 (14)177 (3)
C11—H11A···S1iv0.972.873.754 (19)152
Symmetry codes: (i) x+1/2, y1/2, z1; (ii) x, y1/2, z3/2; (iii) x1, y, z; (iv) x+1/2, y1, z1/2.
 

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