Propyl 2-(3-benzoyl­thio­ureido)acetate

Ibrahim N Hassan; Bohari M Yamin; Mohammad B Kassim

doi:10.1107/S1600536808030596

. 2008 Oct 9;64(Pt 11):o2083. doi: 10.1107/S1600536808030596

Propyl 2-(3-benzoylthioureido)acetate

Ibrahim N Hassan ^a, Bohari M Yamin ^a, Mohammad B Kassim ^a,^*

PMCID: PMC2959494 PMID: 21580948

Abstract

The title compound, C₁₃H₁₆N₂O₃S, is a thiourea derivative with benzoyl and propoxycarbonylmethyl groups attached to the two terminal N atoms. These groups adopt trans and cis configurations, respectively, with respect to the S atom across the thiourea C—N bonds. The compound crystallizes in the P2₁/c space group with Z = 8, resulting in two unique molecules in the asymmetric unit linked by C—H⋯S and C—H⋯O hydrogen bonds, forming a one-dimensional zigzag chain along the c axis.

Related literature

For information on bond lengths and angles, see: Allen et al. (1987 ▶). For related literature on an analogous molecule, see: Hassan et al. (2008 ▶). For related structures, see: Yamin & Hassan (2004 ▶); Yamin & Yusof (2003 ▶).

Experimental

Crystal data

C₁₃H₁₆N₂O₃S
M _r = 280.34
Monoclinic,
a = 11.6722 (19) Å
b = 15.105 (3) Å
c = 16.584 (3) Å
β = 104.737 (3)°
V = 2827.6 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 298 (2) K
0.34 × 0.29 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.925, T _max = 0.979
15002 measured reflections
5262 independent reflections
2854 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.162
S = 1.05
5262 reflections
359 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030596/at2635sup1.cif

e-64-o2083-sup1.cif^{(22.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030596/at2635Isup2.hkl

e-64-o2083-Isup2.hkl^{(257.7KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O1	0.87 (2)	1.92 (2)	2.617 (3)	136 (2)
N2—H2B⋯O2	0.87 (2)	2.33 (2)	2.663 (4)	103.1 (17)
N4—H4B⋯O4	0.87 (3)	1.97 (2)	2.605 (4)	129 (3)
N4—H4B⋯O5	0.87 (3)	2.23 (3)	2.671 (4)	111 (2)
C5—H5A⋯S2	0.93	2.84	3.396 (3)	120
C13—H13B⋯O4ⁱ	0.96	2.54	3.329 (6)	139
C14—H14A⋯S1	0.93	2.78	3.397 (3)	125
C24—H24A⋯O2ⁱⁱ	0.97	2.57	3.441 (4)	150
C26—H26B⋯O1ⁱⁱ	0.96	2.57	3.384 (4)	143

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank Universiti Kebangsaan Malaysia for providing facilities, and the Ministry of Science, Technology and Innovation for research fund No. UKM-ST-01FRGS0016-2006.

supplementary crystallographic information

Comment

The title compound, (I), is an analog of the previously reported ethyl 2-(3-benzoylthioureido) acetate (II) (Hassan et al., 2008). As in most carbonylthiourea derivatives of the type R¹C(O)NHC(S)NHR², such as in N-benzoyl-N'-phenylthiourea (Yamin & Yusof, 2003) and 1-(2-morpholinoethyl)-3-(3-phenylacryloyl)thiourea (Yamin & Hassan, 2004), the molecule maintains its cis–trans configuration with respect to the positions of the propyl acetate and benzoyl groups, respectively, relative to the S atom across the C—N bonds (Fig. 1). The bond lengths and angles in the molecules are in normal ranges (Allen et al., 1987) and comparable to those in (II). However, the C═S bond length [1.658 (3) Å] is slightly shorter than that of (II) [1.666 (2) Å]. The phenyl ring [C1–C6 (A)] and the carbonyl thiourea [(S1/N1/N2/O1/C7/C8/C9) (B)] fragments are essentially planar. In the acetate fragment, [O2/O3/C9/C10 (C)], the maximum deviation from the mean plane is 0.013 (3) Å for atom C10. The dihedral angles A/B and B/C are 18.58 (15)° and 20.51 (16)°, respectively. The phenyl ring is inclined to the acetate mean plane with a dihedral angle of 37.07 (19)°. The intramolecular hydrogen bonds N2—H2B···O1 and N2—H2B···O2 (Table 2) form a pseudo-six-member ring (N2/H2B/O1/C7/N1/C8) and pseudo-five-member ring (N2/H2B/O2/C10/C9), respectively. In the crystal structure, molecules are linked by intermolecular C—H···S, C—H···O and N—H···S hydrogen bonds (Table 2), forming a one-dimensional chain parallel to the c axis as seen in (II) (Fig. 2).

Experimental

The title compound (I) was synthesized according to a previously reported compound (Hassan et al., 2008). A yellowish crystal, suitable for X-ray crystallography, was obtained by a recrystallization from dichloromethane (yield 75%).