organic compounds
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—HO, O—HO, C—HO and C—HS intermolecular hydrogen bonds, forming a two-dimensional network.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806036816/at2108sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806036816/at2108Isup2.hkl |
CCDC reference: 623970
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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·H2O | F(000) = 624 |
Mr = 296.34 | Dx = 1.360 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 694 reflections |
a = 9.05 (4) Å | θ = 2.3–25.0° |
b = 12.00 (6) Å | µ = 0.24 mm−1 |
c = 13.33 (6) Å | T = 298 K |
V = 1448 (12) Å3 | Block, colourless |
Z = 4 | 0.50 × 0.30 × 0.10 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2527 independent reflections |
Radiation source: fine-focus sealed tube | 2047 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
Detector resolution: 83.66 pixels mm-1 | θmax = 25.0°, θmin = 2.3° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −12→14 |
Tmin = 0.890, Tmax = 0.977 | l = −15→12 |
6893 measured reflections |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H 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 reflections | Δρmax = 0.17 e Å−3 |
191 parameters | Δρmin = −0.15 e Å−3 |
14 restraints | Absolute structure: Flack (1983), 634 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.01 (10) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.25676 (9) | −0.43079 (5) | −0.46911 (5) | 0.0591 (2) | |
O1 | 0.3018 (2) | −0.15137 (15) | −0.64794 (13) | 0.0584 (5) | |
O2 | 0.3655 (2) | −0.46979 (14) | −0.72748 (13) | 0.0535 (5) | |
O3 | 0.2513 (2) | −0.63497 (11) | −0.70096 (11) | 0.0518 (4) | |
H3 | 0.3191 | −0.6604 | −0.7348 | 0.062* | |
O4 | −0.4521 (2) | −0.26865 (15) | −0.70101 (16) | 0.0552 (5) | |
H4A | −0.478 (3) | −0.3274 (15) | −0.727 (2) | 0.083* | |
H4B | −0.524 (2) | −0.2315 (19) | −0.684 (2) | 0.083* | |
N1 | 0.1786 (2) | −0.22089 (13) | −0.51478 (15) | 0.0427 (5) | |
H1A | 0.1312 | −0.2044 | −0.4609 | 0.051* | |
N2 | 0.1201 (2) | −0.35932 (14) | −0.63133 (13) | 0.0413 (5) | |
C1 | 0.2466 (3) | −0.02107 (17) | −0.51956 (16) | 0.0408 (5) | |
C2 | 0.3510 (3) | 0.0556 (2) | −0.5538 (2) | 0.0579 (7) | |
H2 | 0.4181 | 0.0351 | −0.6032 | 0.069* | |
C3 | 0.3549 (4) | 0.1635 (2) | −0.5137 (3) | 0.0716 (9) | |
H3A | 0.4238 | 0.2147 | −0.5373 | 0.086* | |
C4 | 0.2579 (4) | 0.1939 (2) | −0.4403 (2) | 0.0724 (9) | |
H4 | 0.2612 | 0.2654 | −0.4134 | 0.087* | |
C5 | 0.1548 (4) | 0.1179 (2) | −0.4059 (2) | 0.0689 (9) | |
H5 | 0.0893 | 0.1385 | −0.3555 | 0.083* | |
C6 | 0.1478 (3) | 0.0108 (2) | −0.44597 (19) | 0.0507 (7) | |
H6 | 0.0768 | −0.0392 | −0.4232 | 0.061* | |
C7 | 0.2453 (3) | −0.13519 (18) | −0.56626 (16) | 0.0420 (5) | |
C8 | 0.1821 (3) | −0.33573 (19) | −0.54430 (16) | 0.0409 (6) | |
C9 | 0.0278 (3) | −0.2830 (2) | −0.69270 (19) | 0.0488 (7) | |
H9A | 0.0872 | −0.2438 | −0.7419 | 0.059* | |
H9B | −0.0228 | −0.2290 | −0.6508 | 0.059* | |
C10A | −0.0811 (4) | −0.3609 (2) | −0.7430 (3) | 0.0580 (11) | 0.916 (7) |
H10A | −0.1132 | −0.3312 | −0.8071 | 0.070* | 0.916 (7) |
H10B | −0.1669 | −0.3731 | −0.7009 | 0.070* | 0.916 (7) |
C10B | −0.004 (3) | −0.3486 (8) | −0.7841 (10) | 0.0580 (11) | 0.084 (7) |
H10C | 0.0663 | −0.3309 | −0.8363 | 0.070* | 0.084 (7) |
H10D | −0.1027 | −0.3313 | −0.8086 | 0.070* | 0.084 (7) |
C11 | 0.0057 (3) | −0.4679 (2) | −0.7570 (2) | 0.0617 (8) | |
H11A | 0.0606 | −0.4658 | −0.8195 | 0.074* | |
H11B | −0.0604 | −0.5315 | −0.7584 | 0.074* | |
C12 | 0.1110 (3) | −0.47585 (18) | −0.66789 (17) | 0.0404 (6) | |
H12 | 0.0676 | −0.5233 | −0.6158 | 0.048* | |
C13 | 0.2597 (3) | −0.52311 (18) | −0.70019 (15) | 0.0394 (5) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0795 (5) | 0.0500 (4) | 0.0476 (4) | 0.0117 (4) | −0.0124 (4) | 0.0034 (3) |
O1 | 0.0619 (12) | 0.0651 (11) | 0.0482 (10) | −0.0032 (9) | 0.0159 (9) | −0.0075 (9) |
O2 | 0.0498 (11) | 0.0474 (9) | 0.0633 (12) | −0.0080 (9) | 0.0074 (9) | −0.0087 (9) |
O3 | 0.0507 (11) | 0.0371 (8) | 0.0676 (11) | 0.0044 (9) | 0.0097 (11) | −0.0066 (7) |
O4 | 0.0501 (11) | 0.0449 (10) | 0.0706 (14) | −0.0059 (9) | 0.0056 (10) | −0.0007 (9) |
N1 | 0.0556 (13) | 0.0362 (11) | 0.0364 (11) | 0.0030 (10) | 0.0066 (9) | −0.0056 (8) |
N2 | 0.0526 (13) | 0.0347 (10) | 0.0368 (11) | 0.0081 (9) | −0.0019 (10) | −0.0046 (8) |
C1 | 0.0392 (13) | 0.0442 (11) | 0.0391 (12) | 0.0013 (13) | −0.0059 (14) | 0.0032 (10) |
C2 | 0.0529 (17) | 0.0578 (17) | 0.0630 (18) | −0.0110 (14) | −0.0022 (14) | 0.0067 (13) |
C3 | 0.074 (2) | 0.0526 (17) | 0.088 (2) | −0.0230 (16) | −0.016 (2) | 0.0124 (17) |
C4 | 0.094 (2) | 0.0402 (14) | 0.084 (2) | −0.0020 (18) | −0.024 (2) | −0.0073 (14) |
C5 | 0.085 (2) | 0.0533 (17) | 0.068 (2) | 0.0056 (16) | −0.0027 (18) | −0.0173 (14) |
C6 | 0.0555 (17) | 0.0443 (14) | 0.0523 (16) | −0.0007 (12) | 0.0050 (14) | −0.0019 (12) |
C7 | 0.0397 (14) | 0.0471 (13) | 0.0392 (13) | 0.0020 (13) | 0.0007 (13) | −0.0003 (10) |
C8 | 0.0446 (15) | 0.0439 (13) | 0.0342 (13) | 0.0044 (11) | 0.0064 (11) | −0.0034 (11) |
C9 | 0.0578 (17) | 0.0435 (14) | 0.0450 (16) | 0.0114 (13) | −0.0069 (14) | −0.0012 (11) |
C10A | 0.051 (2) | 0.0570 (18) | 0.066 (2) | 0.0080 (16) | −0.0108 (17) | −0.0096 (15) |
C10B | 0.051 (2) | 0.0570 (18) | 0.066 (2) | 0.0080 (16) | −0.0108 (17) | −0.0096 (15) |
C11 | 0.0547 (17) | 0.0573 (16) | 0.073 (2) | 0.0084 (13) | −0.0198 (15) | −0.0266 (15) |
C12 | 0.0429 (15) | 0.0340 (11) | 0.0443 (14) | 0.0015 (11) | 0.0015 (12) | −0.0018 (10) |
C13 | 0.0463 (15) | 0.0379 (11) | 0.0340 (11) | −0.0011 (14) | −0.0047 (13) | −0.0032 (9) |
Geometric parameters (Å, º) top
S1—C8 | 1.662 (5) | C4—C5 | 1.383 (6) |
O1—C7 | 1.219 (5) | C4—H4 | 0.9300 |
O2—C13 | 1.208 (5) | C5—C6 | 1.393 (7) |
O3—C13 | 1.345 (7) | C5—H5 | 0.9300 |
O3—H3 | 0.8200 | C6—H6 | 0.9300 |
O4—H4A | 0.820 (10) | C9—C10B | 1.479 (11) |
O4—H4B | 0.826 (10) | C9—C10A | 1.515 (6) |
N1—C7 | 1.376 (5) | C9—H9A | 0.9700 |
N1—C8 | 1.433 (7) | C9—H9B | 0.9700 |
N1—H1A | 0.8599 | C10A—C11 | 1.516 (7) |
N2—C8 | 1.319 (5) | C10A—H10A | 0.9700 |
N2—C12 | 1.483 (7) | C10A—H10B | 0.9700 |
N2—C9 | 1.485 (5) | C10B—C11 | 1.479 (12) |
C1—C6 | 1.381 (5) | C10B—H10C | 0.9700 |
C1—C2 | 1.395 (5) | C10B—H10D | 0.9700 |
C1—C7 | 1.504 (7) | C11—C12 | 1.527 (6) |
C2—C3 | 1.401 (7) | C11—H11A | 0.9700 |
C2—H2 | 0.9300 | C11—H11B | 0.9700 |
C3—C4 | 1.364 (6) | C12—C13 | 1.522 (6) |
C3—H3A | 0.9300 | C12—H12 | 0.9800 |
C13—O3—H3 | 109.5 | C10A—C9—H9A | 111.1 |
H4A—O4—H4B | 110.7 (17) | C10B—C9—H9B | 137.4 |
C7—N1—C8 | 124.9 (3) | N2—C9—H9B | 111.1 |
C7—N1—H1A | 117.6 | C10A—C9—H9B | 111.1 |
C8—N1—H1A | 117.5 | H9A—C9—H9B | 109.1 |
C8—N2—C12 | 120.98 (18) | C9—C10A—C11 | 103.9 (4) |
C8—N2—C9 | 126.2 (3) | C9—C10A—H10A | 111.0 |
C12—N2—C9 | 111.7 (3) | C11—C10A—H10A | 111.0 |
C6—C1—C2 | 119.2 (3) | C9—C10A—H10B | 111.0 |
C6—C1—C7 | 122.7 (2) | C11—C10A—H10B | 111.0 |
C2—C1—C7 | 118.1 (3) | H10A—C10A—H10B | 109.0 |
C1—C2—C3 | 120.2 (4) | C9—C10B—C11 | 107.6 (8) |
C1—C2—H2 | 119.9 | C9—C10B—H10C | 110.2 |
C3—C2—H2 | 119.9 | C11—C10B—H10C | 110.2 |
C4—C3—C2 | 120.3 (3) | C9—C10B—H10D | 110.2 |
C4—C3—H3A | 119.9 | C11—C10B—H10D | 110.2 |
C2—C3—H3A | 119.9 | H10C—C10B—H10D | 108.5 |
C3—C4—C5 | 119.7 (4) | C10B—C11—C10A | 34.8 (9) |
C3—C4—H4 | 120.2 | C10B—C11—C12 | 106.8 (7) |
C5—C4—H4 | 120.2 | C10A—C11—C12 | 106.3 (3) |
C4—C5—C6 | 120.8 (4) | C10B—C11—H11A | 78.4 |
C4—C5—H5 | 119.6 | C10A—C11—H11A | 110.5 |
C6—C5—H5 | 119.6 | C12—C11—H11A | 110.5 |
C1—C6—C5 | 119.9 (3) | C10B—C11—H11B | 136.0 |
C1—C6—H6 | 120.1 | C10A—C11—H11B | 110.5 |
C5—C6—H6 | 120.1 | C12—C11—H11B | 110.5 |
O1—C7—N1 | 120.7 (3) | H11A—C11—H11B | 108.7 |
O1—C7—C1 | 120.8 (2) | N2—C12—C13 | 113.3 (2) |
N1—C7—C1 | 118.5 (4) | N2—C12—C11 | 103.4 (2) |
N2—C8—N1 | 116.0 (2) | C13—C12—C11 | 110.8 (3) |
N2—C8—S1 | 123.8 (3) | N2—C12—H12 | 109.7 |
N1—C8—S1 | 120.2 (3) | C13—C12—H12 | 109.7 |
C10B—C9—N2 | 103.7 (6) | C11—C12—H12 | 109.7 |
C10B—C9—C10A | 34.8 (10) | O2—C13—O3 | 124.8 (3) |
N2—C9—C10A | 103.2 (4) | O2—C13—C12 | 126.1 (4) |
C10B—C9—H9A | 79.1 | O3—C13—C12 | 108.9 (3) |
N2—C9—H9A | 111.1 | ||
C6—C1—C2—C3 | −0.1 (4) | C8—N2—C9—C10A | −147.6 (3) |
C7—C1—C2—C3 | 178.9 (2) | C12—N2—C9—C10A | 20.4 (3) |
C1—C2—C3—C4 | 0.8 (4) | C10B—C9—C10A—C11 | 62.9 (8) |
C2—C3—C4—C5 | −0.5 (5) | N2—C9—C10A—C11 | −32.1 (4) |
C3—C4—C5—C6 | −0.5 (5) | N2—C9—C10B—C11 | 25.3 (17) |
C2—C1—C6—C5 | −0.9 (4) | C10A—C9—C10B—C11 | −68.3 (13) |
C7—C1—C6—C5 | −179.9 (2) | C9—C10B—C11—C10A | 68.2 (10) |
C4—C5—C6—C1 | 1.2 (4) | C9—C10B—C11—C12 | −26.3 (17) |
C8—N1—C7—O1 | 7.1 (4) | C9—C10A—C11—C10B | −62.9 (11) |
C8—N1—C7—C1 | −173.0 (2) | C9—C10A—C11—C12 | 33.2 (3) |
C6—C1—C7—O1 | 158.8 (2) | C8—N2—C12—C13 | −71.4 (3) |
C2—C1—C7—O1 | −20.1 (4) | C9—N2—C12—C13 | 119.9 (3) |
C6—C1—C7—N1 | −21.1 (4) | C8—N2—C12—C11 | 168.6 (2) |
C2—C1—C7—N1 | 160.0 (2) | C9—N2—C12—C11 | −0.1 (3) |
C12—N2—C8—N1 | −177.3 (2) | C10B—C11—C12—N2 | 15.8 (10) |
C9—N2—C8—N1 | −10.4 (3) | C10A—C11—C12—N2 | −20.5 (3) |
C12—N2—C8—S1 | 0.9 (3) | C10B—C11—C12—C13 | −105.8 (10) |
C9—N2—C8—S1 | 167.9 (2) | C10A—C11—C12—C13 | −142.1 (2) |
C7—N1—C8—N2 | −62.4 (5) | N2—C12—C13—O2 | −24.2 (4) |
C7—N1—C8—S1 | 119.4 (4) | C11—C12—C13—O2 | 91.4 (3) |
C8—N2—C9—C10B | 176.6 (11) | N2—C12—C13—O3 | 160.4 (2) |
C12—N2—C9—C10B | −15.4 (11) | C11—C12—C13—O3 | −83.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O1 | 0.97 | 2.56 | 3.000 (15) | 107 |
N1—H1A···O4i | 0.86 | 2.31 | 3.113 (16) | 156 |
O3—H3···O4ii | 0.82 | 1.97 | 2.754 (14) | 160 |
O4—H4A···O2iii | 0.82 (2) | 2.22 (2) | 2.945 (15) | 148 (3) |
O4—H4B···O1iii | 0.82 (2) | 1.91 (2) | 2.728 (14) | 177 (3) |
C11—H11A···S1iv | 0.97 | 2.87 | 3.754 (19) | 152 |
Symmetry codes: (i) x+1/2, −y−1/2, −z−1; (ii) −x, y−1/2, −z−3/2; (iii) x−1, y, z; (iv) −x+1/2, −y−1, z−1/2. |