Butyl 2-(3-benzoyl­thio­ureido)acetate

Ibrahim N Hassan; Bohari M Yamin; Mohammad B Kassim

doi:10.1107/S1600536808033540

. 2008 Oct 22;64(Pt 11):o2167. doi: 10.1107/S1600536808033540

Butyl 2-(3-benzoylthioureido)acetate

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

PMCID: PMC2959747 PMID: 21581027

Abstract

In the title compound, C₁₄H₁₈N₂O₃S, the butyl acetate fragment and the benzoyl group adopt a cis–trans configuration, respectively, with respect to the thiono S atom across the C—N bonds. In the crystal packing, the molecules are linked by intermolecular N—H⋯O and C—H⋯O hydrogen bonds to form a one-dimensional chain along the c axis. The terminal butyl C atom is disordered with occupancies 0.82 (2)and 0.18 (2).

Related literature

For information on bond lengths, see: Allen et al. (1987 ▶); For related structures, see: Hassan et al. (2008a ▶,b ▶); Yamin & Hassan (2004 ▶); Yamin & Yusof (2003 ▶).

Experimental

Crystal data

C₁₄H₁₈N₂O₃S
M _r = 294.36
Monoclinic,
a = 14.051 (3) Å
b = 7.9482 (18) Å
c = 14.116 (3) Å
β = 102.753 (3)°
V = 1537.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 298 (2) K
0.46 × 0.28 × 0.25 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.906, T _max = 0.947
7933 measured reflections
2853 independent reflections
2098 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.136
S = 1.03
2853 reflections
187 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.27 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/S1600536808033540/at2648sup1.cif

e-64-o2167-sup1.cif^{(17.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033540/at2648Isup2.hkl

e-64-o2167-Isup2.hkl^{(140.1KB, 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
N1—H1A⋯O2ⁱ	0.86	2.39	3.203 (2)	158
N2—H2A⋯O1	0.86	1.96	2.631 (2)	134
C2—H2⋯O1ⁱ	0.93	2.53	3.328 (3)	144

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

The title compound (I) is a thiourea derivative of glycine analogous to ethyl-2-(3-benzoylthioureido)acetate (II) (Hassan et al., 2008a) and propyl-2-(3-benzoylthioureido)acetate (III) (Hassan et al., 2008b), with the shorter alkyl groups replaced by a butyl group. The molecule maintains the same cis–trans configuration with respect to the positions of the butyl acetate and benzoyl groups, relative to the S atom across the C—N bonds (Fig. 1 and Fig. 2), respectively. There is a disorder in the molecules involving the terminal butyl carbon atom. 'Soft' restrains, SIMU and EADP, were applied to the disorder components, C14 and C14', to resolve the overlapping components. In the final refinement the main disorder component, C14, resides in about 80% occupancy whereas the minor component, C14', occupies 20% at a time.

The compound was synthesized by a similar procedure to that of reported in (II). The bond lengths and angles in the molecules are in normal ranges (Allen et al., 1987) and comparable to those in II and III. The phenyl ring, (C1–C6), and the central fragment, (C6/C7/C8/C9/N1/N2/S1), are essentially planar and the dihedral angle between them is 27.82 (9)°. In the butyl fragment, (C11/C12/C13/O3), the maximum deviation from the mean plane is 0.017 (3)Å for the atom C12. The dihedral angle between the phenyl ring and the butyl group is 14.5 (3)°. The intramolecular N2—H2···O1 and C9—H9B···S1 hydrogen bonds, (Table 1), force the molecule to adopt the present molecular conformation. The intermolecular N1—H1B···O2 and C2—H4A···O1 hydrogen bonds, (Table 2), link the molecules into a chain parallel to the c axis (Fig. 3).

Experimental

Preparation of the compound was carried out according to a previously reported experimental procedures (Hassan et al., 2008a). A yellowish crystal, suitable for X-ray crystallography, was obtained by a slow evaporation from CH₂Cl₂ solution at room temperature (yield 75%).