(R)-1-(4-Bromo­benzo­yl)-4-(1-phenyl­prop­yl)thio­semicarbazide

Serwer, M.; Khawar Rauf, M.; Ebihara, M.; Hameed, S.

doi:10.1107/S1600536808006806

Volume 64
Part 5
Page o812
May 2008

Received 9 March 2008
Accepted 11 March 2008
Online 10 April 2008

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.005 Å
R = 0.048
wR = 0.074
Data-to-parameter ratio = 17.5
Details

(R)-1-(4-Bromobenzoyl)-4-(1-phenylpropyl)thiosemicarbazide

Monazza Serwer,^a M. Khawar Rauf,^b Masahiro Ebihara ^b and Shahid Hameed ^a ^*

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan
Correspondence e-mail: shameed@qau.edu.pk

The title compound, C₁₇H₁₈BrN₃OS, is an important intermediate for the synthesis of biologically active heterocyclic compounds. The thiourea group is approximately planar. The crystal structure is stabilized by intermolecular N-HO hydrogen-bonding interactions.

Related literature

For related literature, see: Akhtar et al. (2006, 2007); Cardia et al. (2006); Dolman et al. (2006); Hassan et al. (2006); Jalilian et al. (2000); Kucukguzel et al. (2006); Mohareb et al. (2007); Singh et al. (2003, 2005).

Experimental

Crystal data

C₁₇H₁₈BrN₃OS
M_r = 392.31
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.263 (3) Å
b = 9.698 (5) Å
c = 27.651 (15) Å
V = 1679.5 (15) Å³
Z = 4
Mo K radiation
= 2.58 mm^-1
T = 123 (2) K
0.30 × 0.25 × 0.20 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer
Absorption correction: integration (NUMABS; Higashi, 1999) T_min = 0.512, T_max = 0.626
13732 measured reflections
3824 independent reflections
3516 reflections with I > 2(I)
R_int = 0.057

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.074
S = 1.13
3824 reflections
219 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.34 e Å^-3
_min = -0.35 e Å^-3
Absolute structure: Flack (1983), 1584 Friedel pairs
Flack parameter: 0.020 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.84 (4)	2.03 (4)	2.834 (4)	161 (4)
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and TEXSAN.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2385 ).

Acknowledgements

MKR is grateful to the Higher Education Commission of Pakistan for financial support under the International Support Initiative program for Doctoral Fellowships at Gifu University, Japan.

References

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organic compounds