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Volume 69 
Part 5 
Page o762  
May 2013  

Received 31 March 2013
Accepted 1 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.005 Å
R = 0.042
wR = 0.114
Data-to-parameter ratio = 15.0
Details
Open access

5-Bromo-2-hydroxybenzaldehyde 4-ethylthiosemicarbazone

aInstitute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga, Fukuoka 816-8580, Japan
Correspondence e-mail: sato@cm.kyushu-u.ac.jp

In the title Schiff base compound, C10H12BrN3OS, the C-N-N-C torsion angle is 172.07 (11)°. An intramolecular hydrogen bond exists between the hydroxy H atom and the azomethine N atom. In the crystal, pairs of hydrogen bonds involving the imino H atom and the S atom give rise to supramolecular dimers.

Related literature

For the isostructural compound 5-chloro-2-hydroxybenzaldehyde 4-ethylthiosemicarbazone, see: Lo et al. (2011[Lo, K. M. & Ng, S. W. (2011). Acta Cryst. E67, o1453.])

[Scheme 1]

Experimental

Crystal data
  • C10H12BrN3OS

  • Mr = 302.20

  • Monoclinic, C 2/c

  • a = 22.040 (4) Å

  • b = 11.844 (2) Å

  • c = 9.5102 (19) Å

  • [beta] = 101.69 (3)°

  • V = 2431.1 (8) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 3.54 mm-1

  • T = 123 K

  • 0.20 × 0.10 × 0.05 mm

Data collection
  • Rigaku Saturn70 diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.661, Tmax = 0.838

  • 4201 measured reflections

  • 2331 independent reflections

  • 1760 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.114

  • S = 0.95

  • 2331 reflections

  • 155 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.70 e Å-3

  • [Delta][rho]min = -1.01 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...N1 0.84 (3) 2.00 (2) 2.674 (3) 137 (3)
N2-H2A...S1i 0.88 (3) 2.47 (3) 3.316 (3) 161 (2)
N3-H3A...S1ii 0.87 (3) 2.75 (3) 3.510 (3) 146 (3)
Symmetry codes: (i) [-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z+1]; (ii) [x, -y+1, z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5322 ).


Acknowledgements

The authors would like to thank the China Scholarship Council (CSC).

References

Lo, K. M. & Ng, S. W. (2011). Acta Cryst. E67, o1453.  [CSD] [CrossRef] [details]
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o762  [ doi:10.1107/S1600536813008787 ]

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