5-Bromo-2-hy­droxy­benzaldehyde thio­semicarbazone

Kargar, H.; Kia, R.; Akkurt, M.; Büyükgüngör, O.

doi:10.1107/S1600536810043357

Volume 66
Part 11
Page o2999
November 2010

Received 24 October 2010
Accepted 24 October 2010
Online 31 October 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R = 0.030
wR = 0.063
Data-to-parameter ratio = 13.4
Details

5-Bromo-2-hydroxybenzaldehyde thiosemicarbazone

Hadi Kargar,^a Reza Kia,^b Mehmet Akkurt ^c ^* and Orhan Büyükgüngör ^d

^aDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran,^bDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran,^cDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, 55139 Samsun, Turkey
Correspondence e-mail: akkurt@erciyes.edu.tr

The molecule of the title compound, C₈H₈BrN₃OS, is close to being planar, with maximum deviations of -0.127 (3) and 0.135 (5) Å for the N atoms of the -NH- and NH₂- groups, respectively. Intramolecular N-HN and O-HN hydrogen bonds to the same acceptor N atom generate S(5) and S(6) ring motifs. In the crystal structure, molecules are connected into [010] chains by pairs of N-HS hydrogen bonds with R₂²(8) graph-set motifs. The crystal used for data collection was found to be an inversion twin.

Related literature

For background on the biological activities and pharmaceutical properties of thiosemicarbazones and their derivatives, see: Casas et al. (2000); Ferrari et al. (2000); Maccioni et al. (2003). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₈H₈BrN₃OS
M_r = 274.14
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.4564 (2) Å
b = 8.3515 (3) Å
c = 27.7153 (14) Å
V = 1031.50 (8) Å³
Z = 4
Mo K radiation
= 4.16 mm^-1
T = 296 K
0.13 × 0.09 × 0.05 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T_min = 0.614, T_max = 0.819
9532 measured reflections
1934 independent reflections
1782 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.030
wR(F²) = 0.063
S = 1.04
1934 reflections
144 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.54 e Å^-3
_min = -0.29 e Å^-3
Absolute structure: Flack (1983), with 744 Freidel pairs
Flack parameter: 0.477 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-HO1N1	0.81 (3)	1.97 (4)	2.685 (4)	149 (5)
N3-HN3N1	0.87 (4)	2.30 (4)	2.688 (5)	107 (3)
N2-HN1S1ⁱ	0.84 (3)	2.55 (3)	3.373 (3)	168 (3)
N3-HN2S1ⁱⁱ	0.86 (3)	2.50 (3)	3.363 (4)	176 (6)
Symmetry codes: (i) $[-x-1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x-1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5704 ).

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDS II diffractometer (purchased under grant F.279 of the University Research Fund). HK thanks Payame Noor University (PNU) for financial support of this work. RK thanks the Science and Research Branch of Islamic Azad University of Tehran.

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.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Casas, J. S., Garcia-Tasende, M. S. & Sordo, J. (2000). Coord. Chem. Rev. 209, 197-261.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Ferrari, M. B., Capacchi, S., Reffo, G., Pelosi, G., Tarasconi, P., Albertini, R., Pinelli, S. & Lunghi, P. (2000). J. Inorg. Biochem. 81, 89-97.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Maccioni, E., Cardia, M. C., Distinto, S., Bonsignore, L. & De Logu, A. (2003). Il Farmaco, 58, 951-959.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.

organic compounds