1-Acetyl-4-(phenyl­sulfan­yl)imidazolidin-2-one

Abdel-Aziz, A.A.-M.; El-Azab, A.S.; Alanazi, A.M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812007908

Volume 68
Part 3
Page o908
March 2012

Received 20 February 2012
Accepted 22 February 2012
Online 29 February 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.028
wR = 0.073
Data-to-parameter ratio = 14.6
Details

1-Acetyl-4-(phenylsulfanyl)imidazolidin-2-one

Alaa A.-M. Abdel-Aziz,^a,^b ⁺ Adel S. El-Azab,^a,^c Amer M. Alanazi,^a Seik Weng Ng ^d,^e and Edward R. T. Tiekink ^d ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia,^bDepartment of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt,^cDepartment of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt,^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^eChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

The five-membered ring in the title imidazolidinone derivative, C₁₁H₁₂N₂O₂S, adopts an envelope conformation with the S-bound C atom being the flap atom. Overall, the molecule has a U-shaped conformation as both rings are folded towards each other [dihedral angle = 31.66 (6)°]. An eight-membered amide {HNCO}₂ synthon leads to hydrogen-bonded dimeric aggregates in the crystal: these are additionally linked by C-H [pi] interactions.

Related literature

For the antitumour potential of imidazolidinones, see: Abdel-Aziz et al. (2012). For ring conformational analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₁H₁₂N₂O₂S
M_r = 236.29
Monoclinic, P 2₁ /n
a = 7.0473 (1) Å
b = 14.3274 (3) Å
c = 10.7796 (2) Å
= 96.921 (2)°
V = 1080.48 (3) Å³
Z = 4
Cu K radiation
= 2.56 mm^-1
T = 100 K
0.35 × 0.30 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) T_min = 0.754, T_max = 1.000
8437 measured reflections
2186 independent reflections
2135 reflections with I > 2(I)
R_int = 0.015

Refinement

R[F² > 2(F²)] = 0.028
wR(F²) = 0.073
S = 1.01
2186 reflections
150 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.25 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C6-C11 ring.

D-HA	D-H	HA	DA	D-HA
N2-H1O1ⁱ	0.876 (19)	2.032 (19)	2.8989 (13)	169.8 (17)
C1-H1ACg1ⁱⁱ	0.98	2.72	3.6360 (13)	155
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5824 ).

Acknowledgements

This work was supported by the Research Center of Pharmacy, King Saud University, Riyadh, Saudi Arabia. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research Scheme (grant No. UM.C/HIR/MOHE/SC/12).

References

Abdel-Aziz, A. A.-M., El-Azab, A. S., El-Subbagh, H. I., Al-Obaid, A. M., Alanazi, A. M. & Al-Omar, M. A. (2012). Bioorg. Med. Chem. Lett. 22, 2008-2014.
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds