1-(4-Bromo­phen­yl)-3-butano­ylthio­urea

Saeed, S.; Rashid, N.; Jasinski, J.P.; Butcher, R.J.; Shoaib, M.

doi:10.1107/S1600536810050373

Volume 67
Part 1
Page o46
January 2011

Received 8 November 2010
Accepted 1 December 2010
Online 8 December 2010

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R = 0.043
wR = 0.095
Data-to-parameter ratio = 17.5
Details

1-(4-Bromophenyl)-3-butanoylthiourea

Sohail Saeed,^a ^* Naghmana Rashid,^a Jerry P. Jasinski,^b Ray J. Butcher ^c and Muhammad Shoaib ^d

^aDepartment of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad, Pakistan,^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA,^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and ^dNational Engineering & Scientific Commission, PO Box 2801, Islamabad, Pakistan
Correspondence e-mail: sohail262001@yahoo.com

In the title compound, C₁₁H₁₃BrN₂OS, there are two independent molecules (A and B) in the asymmetric unit. The dihedral angle between the mean planes of the benzene ring and the carbamothioyl group is 63.66 (molecule A) and 80.3 (0)° (molecule B). The butanamide group in molecule A is disordered [0.532 (6) and 0.468 (6) occupancy]. The carbamothioyl group is twisted by 63.6 (6) (molecule A) and 80.3 (0)° (molecule B) from the respective benzene ring. A strong intramolecular N-HO hydrogen bond occurs in each molecule. The crystal packing is stabilized by weak intermolecular N-HO and N-HS hydrogen-bond interactions, the latter forming an infinite co-operative hydrogen-bonded two-dimensional network along [110].

Related literature

For general background to the chemistry of thiourea derivatives, see: Zhang et al. (2004); For related structures, see: Saeed et al. (2008a,b, 2009). For an epoxy resin curing agent, see: Saeed et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₁H₁₃BrN₂OS
M_r = 301.20
Triclinic, $[P \overline 1]$
a = 6.1746 (3) Å
b = 10.7883 (4) Å
c = 19.6450 (8) Å
= 87.719 (3)°
= 81.557 (4)°
= 76.047 (4)°
V = 1256.23 (9) Å³
Z = 4
Mo K radiation
= 3.42 mm^-1
T = 123 K
0.53 × 0.24 × 0.11 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.187, T_max = 1.000
13276 measured reflections
5362 independent reflections
3535 reflections with I > 2(I)
R_int = 0.054

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.095
S = 0.92
5362 reflections
307 parameters
18 restraints
H-atom parameters constrained
_max = 0.83 e Å^-3
_min = -0.74 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1A-H1AAO1A	0.88	1.97	2.666 (5)	135
N1A-H1AAO1Aⁱ	0.88	2.36	3.083 (6)	140
N2A-H2ABS1Aⁱⁱ	0.88	2.54	3.382 (4)	160
N1B-H1BAO1B	0.88	1.98	2.662 (4)	134
N2B-H2BBS1Bⁱⁱⁱ	0.88	2.50	3.370 (3)	169
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y, -z; (iii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; 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: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2247 ).

Acknowledgements

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Saeed, S., Bhatti, M. H., Tahir, M. K. & Jones, P. G. (2008a). Acta Cryst. E64, o1369.
Saeed, S., Bhatti, M. H., Yunus, U. & Jones, P. G. (2008b). Acta Cryst. E64, o1566.
Saeed, S., Rashid, N., Tahir, A. & Jones, P. G. (2009). Acta Cryst. E65, o1870-o1871.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Zhang, Y.-M., Wei, T.-B., Xian, L. & &Gao, L.-M. (2004). Phosphorus Sulphur Silicon Relat. Elem. 179, 2007-2013.

organic compounds