3-[3-(2-Fluoro­benzo­yl)thio­ureido]propionic acid

Nurziana Ngah; Nor Azanita Mohamed; Bohari M Yamin; Hamizah Mohd Zaki

doi:10.1107/S1600536814011404

. 2014 May 24;70(Pt 6):o705. doi: 10.1107/S1600536814011404

3-[3-(2-Fluorobenzoyl)thioureido]propionic acid

Nurziana Ngah ^a,^*, Nor Azanita Mohamed ^a, Bohari M Yamin ^b, Hamizah Mohd Zaki ^c,^d

PMCID: PMC4051025 PMID: 24940277

Abstract

In the title compound, C₁₀H₁₁FN₃O₃S, the 2-fluorobenzoyl and proponic acid groups maintain a trans–cis conformation with respect to the thiono C=S bond across their C—N bonds. The propionic acid group adopts an anti conformation about the C—C bond, with an N—C—C—C torsion angle of 173.8 (2)°. The amino groups are involved in the formation of intramolecular N—H⋯O and N—H⋯F hydrogen bonds. In the crystal, pairs of O—H⋯O hydrogen bonds link molecules into inversion dimers.

Related literature

For related structures, see: Yusof et al. (2003 ▶); Ngah et al. (2006 ▶). graphic file with name e-70-0o705-scheme1.jpg

Experimental

Crystal data

C₁₁H₁₁FN₂O₃S
M _r = 270.28
Monoclinic,
a = 11.7103 (7) Å
b = 11.1289 (7) Å
c = 9.6760 (7) Å
β = 108.407 (2)°
V = 1196.49 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 296 K
0.41 × 0.30 × 0.28 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.892, T _max = 0.924
21544 measured reflections
2188 independent reflections
1816 reflections with I > 2/s(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.134
S = 1.13
2188 reflections
167 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.31 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814011404/cv5458sup1.cif

e-70-0o705-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814011404/cv5458Isup2.hkl

e-70-0o705-Isup2.hkl^{(107.6KB, hkl)}

Click here for additional data file.^{(4.6KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814011404/cv5458Isup3.cml

CCDC reference: 1003660

Additional supporting information: 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⋯F1	0.86	2.04	2.708 (3)	134
N2—H2A⋯O1	0.86	1.97	2.642 (3)	135
O3—H3A⋯O2ⁱ	0.83 (2)	1.82 (2)	2.645 (3)	175 (4)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thanks the Ministry of Higher Education of Malaysia for funding the synthetic chemistry project under research grant scheme FRGS11–002-0150, International Islamic University Malaysia, Universiti Kebangsaan Malaysia and Universiti Teknologi MARA for providing access to research facilities.

supplementary crystallographic information

1. Comment

In continuation of our study of thiourea derivatives containing propionic acid fragments (Yusof et al., 2003; Ngah et al., 2006), we report here the crystal structure of the title compound (I).

In (I) (Fig.1), all bond lengths and angles are normal and correspond well to those observed in the related compounds (Yusof et al., 2003; Ngah et al., 2006). However, the C11—O3 is slightly shorter [1.306 (3) Å] compared to its analogue [1.325 (4) Å; Ngah et al. (2006)] due to electron delocalization along carboxyl group. The molecule maintains its trans-cis configuration with respect to the positions of 2-fluorobenzoyl and propionic acid relative to the thino C=S bond across the C8—N1 and C8—N2, respectively. The molecule adopts an anti conformation with N2—C9—C10—C11 torsion angle of 173.8 (2)°. In the contrary the analogue adopts a gauche conformation with torsion angle of 64.9 (4)°. The 2-fluorophenyl [C1—C6/F1], thiourea [N1/C8/N2/S1] and propionic acid [C9/C10C11/O2/O3] fragments are essentially planar with maximum deviation of 031 (2) Å for atom C10 from the least square plane of propionic acid. The thiourea makes dihedral angles of 20.84 (12)° and 85.78 (11)° with 2-fluorophenyl and propionic acid fragments, respectively. The 2-fluorophenyl is inclined to propionic acid fragments by 65.65 (13)°, compared to 54.29 (19)° in the analogue. There are two intramolecular N1—H1A···F1 and N2—H2A···O1 hydrogen bonds (Table 1) furnishing in the formation of two pseudo six-membered rings (N1—H1A—F1—C5—C6—C7) and (N2—H2A—O1—C7—N1—C8), respectively.

In the crystal structure, the molecules are connected via O3—H3A···O2 intermolecular hydrogen bonds to form centrosymmetric dimers (Fig. 2).

2. Experimental

30 ml acetone solution of β-alanine (2.92 g, 32.80 mmol) was added into a round-bottom flask containing a solution of 2-fluorobenzoylchloride (5.21 g, 32.80 mmol) and ammonium thiocyanate (2.50 g, 32.80 mmol). The solution mixture was refluxed for 5 h then filtered off into a beaker containing some ice and left to evaporate at room temperature. The yellowish precipitate obtained was washed with water and cold ethanol. The yellowish crytals were obtained by recrystallization of the precipitate in acetonitrile, suitable for X-ray analysis.