N-(4-Chloro­butano­yl)-N′-(2,5-dimeth­oxy­phen­yl)thio­urea

M Sukeri M Yusof; Norafiqah R Azmi; Bohari M Yamin

doi:10.1107/S1600536811036002

. 2011 Sep 14;67(Pt 10):o2609. doi: 10.1107/S1600536811036002

N-(4-Chlorobutanoyl)-N′-(2,5-dimethoxyphenyl)thiourea

M Sukeri M Yusof ^a,^*, Norafiqah R Azmi ^a, Bohari M Yamin ^b

PMCID: PMC3201256 PMID: 22058755

Abstract

The title molecule, C₁₃H₁₇ClN₂O₃S, shows an anti and syn disposition of the butanoyl and 2,5-dimethoxyphenyl groups with respect to the thione and is stabilized by intramolecular N—H⋯O and weak C—H⋯S hydrogen bonds. In the crystal, intermolecular N—H⋯S hydrogen bonds link the molecules into centrosymmetric dimers. The crystal structure is stabilized by weak C—H⋯O and C—H⋯S contacts.

Related literature

For the structures of related thioureas, see: Yamin et al. (2011 ▶); Yusof et al. (2011 ▶).

Experimental

Crystal data

C₁₃H₁₇ClN₂O₃S
M _r = 316.80
Triclinic,
a = 7.6882 (18) Å
b = 9.151 (2) Å
c = 10.939 (3) Å
α = 98.536 (5)°
β = 97.787 (5)°
γ = 101.489 (5)°
V = 734.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 298 K
0.29 × 0.25 × 0.19 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.890, T _max = 0.926
9303 measured reflections
3351 independent reflections
2928 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.105
S = 1.06
3351 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.22 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, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036002/bh2378sup1.cif

e-67-o2609-sup1.cif^{(21KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036002/bh2378Isup2.hkl

e-67-o2609-Isup2.hkl^{(164.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811036002/bh2378Isup3.cml

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—H2A⋯O1	0.86	1.93	2.663 (2)	141
C7—H7A⋯S1	0.93	2.51	3.1853 (18)	129
N1—H1A⋯S1ⁱ	0.86	2.58	3.4058 (16)	161
C3—H3A⋯S1ⁱ	0.97	2.83	3.5633 (19)	133
C12—H12A⋯O2ⁱⁱ	0.96	2.50	3.259 (3)	136

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

Acknowledgments

The authors thank the Malaysian Government, Universiti Kebangsaan Malaysia, the Faculty of Science and Technology, Universiti Malaysia Terengganu, and the Ministry of Higher Education, Malaysia, for research grants UKM-GUP-NBT-08–27–110 and FRGS 59178.

supplementary crystallographic information

Comment

The title compound (Fig. 1) is analogous to the previously reported N-(4-chlorobutanoyl)-N'-(2-fluorophenyl)thiourea (Yusof et al., 2011) except that the methoxy groups are attached at the 2 and 5 positions of the phenyl ring. The carbonylthiourea fragment C4/O1/N1/C5/S1/N2 and the benzene ring, C6···C11, are each planar with the maximum deviation from the least-squares planes of 0.024 (2) Å for atom C4. The benzene ring and carbonylthiourea moiety form a dihedral angle of 5.67 (6)°, much smaller than angles observed in the previously reported thioureas N-(4-chlorobutanoyl)-N'-(2-fluorophenyl)thiourea [74.78 (19)° and 82.3 (2)° for two independent molecules] and N-(4-chlorobutanoyl)-N'-phenylthiourea [72.98 (12)° and 81.47 (14)° for two independent molecules] (Yusof et al., 2011; Yamin et al., 2011). The bond lengths and angles in the title thiourea are in normal ranges and comparable to those in the analogous compounds. The molecule maintains the trans-cis configuration with respect to the position of the butanoyl and 2,5-dimethoxyphenyl groups against the thiono C=S group bond across their C—N bonds.

The molecule is stabilized by three intramolecular contacts, N—H···O and C—H···S. In the crystal packing, the molecules are linked by N—H···S, C—H···S and C—H···O intermolecular hydrogen bonds (symmetry codes as in Table 1) and form dimers (Fig. 2).

Experimental

A solution of 4-chlorobutanoylisothiocyanate (1.25 g, 6.33 mmol) in 30 ml of acetone was added into a flask containing 30 ml acetone solution of 2,5-dimethoxyaniline (0.82 g, 6.33 mmol). The mixture was refluxed for 1 h. Then, the solution was filtered-off and left to evaporate at room temperature. The colourless solid was obtained after one day of evaporation (yield 74%).