Redetermination of 1-benzyl-3-furoyl-1-phenyl­thio­urea

Estévez-Hernández, O.; Corrêa, R.S.; Ellena, J.; Duque, J.

doi:10.1107/S1600536808044085

Volume 65
Part 3
Page o648
March 2009

Received 2 December 2008
Accepted 27 December 2008
Online 28 February 2009

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.114
Data-to-parameter ratio = 12.6
Details

Redetermination of 1-benzyl-3-furoyl-1-phenylthiourea

O. Estévez-Hernández,^a ^* Rodrigo S. Corrêa,^b J. Ellena ^b and J. Duque ^a

^aLaboratory of Molecular Engineering, Institute of Materials, University of Havana, Cuba, and ^bGrupo de Cristalografía, Instituto de Física de São Carlos, Universidade de São Paulo, São Carlos, Brazil
Correspondence e-mail: osvaldo@imre.oc.uh.cu

The title compound, C₁₉H₁₆N₂O₂S, was synthesized from furoyl isothiocyanate and N-benzylaniline in dry acetone and the structure redetermined. The structure [Otazo-Sánchez et al. (2001). J. Chem. Soc. Perkin Trans. 2, pp. 2211-2218] has been re-determined in order to establish the intramolecular and intermolecular interactions. The thiourea group is in the thioamide form. The thiourea group makes a dihedral angle of 29.2 (6)° with the furoyl group. In the crystal structure, molecules are linked by intermolecular C-HO interactions, forming one-dimensional chains along the a axis. An intramolecular N-HO hydrogen bond is also present.

Related literature

For general background, see: Aly et al. (2007), Koch (2001), Estévez-Hernández et al. (2006). For related structures, see: Pérez et al. (2008). For the synthesis, see: Otazo-Sánchez et al. (2001).

Experimental

Crystal data

C₁₉H₁₆N₂O₂S
M_r = 336.41
Orthorhombic, P b c a
a = 12.7737 (3) Å
b = 8.8047 (2) Å
c = 31.2345 (7) Å
V = 3512.90 (14) Å³
Z = 8
Mo K radiation
= 0.20 mm^-1
T = 294 (2) K
0.54 × 0.22 × 0.19 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: gaussian (Coppens et al., 1965) T_min = 0.92, T_max = 0.971
19732 measured reflections
3536 independent reflections
2565 reflections with I > 2(I)
R_int = 0.058

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.114
S = 1.03
3536 reflections
281 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.12 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O2	0.84 (2)	2.25 (2)	2.677 (2)	111 (2)
C6-H6O1ⁱ	0.92 (2)	2.40 (2)	3.315 (3)	172 (2)
C8-H8O1ⁱⁱ	0.92 (2)	2.57 (2)	3.242 (2)	131 (2)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2112 ).

Acknowledgements

The authors acknowledge financial support from the Brazilian agency CNPq. OEH thanks CONACyT of Mexico for research grant No. 61541.

References

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organic compounds