2,4-Dihydroxy­benzaldehyde 4-methyl­thio­semicarbazone

Tan, K.W.; Ng, C.H.; Maah, M.J.; Ng, S.W.

doi:10.1107/S1600536808033308

Volume 64
Part 11
Page o2224
November 2008

Received 11 October 2008
Accepted 14 October 2008
Online 31 October 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R = 0.038
wR = 0.109
Data-to-parameter ratio = 13.9
Details

2,4-Dihydroxybenzaldehyde 4-methylthiosemicarbazone

Kong Wai Tan,^a Chew Hee Ng,^b Mohd. Jamil Maah ^a ^* and Seik Weng Ng ^a

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^bFaculty of Engineering and Science, Universiti Tunku Abdul Rahman, 53300 Kuala Lumpur, Malaysia
Correspondence e-mail: mjamil@um.edu.my

The approximately planar molecule of the title compound, C₉H₁₁N₃O₂S, is linked to adjacent molecules by O-HS hydrogen bonds to form a zigzag chain. Adjacent chains are consolidated by N-HO hydrogen bonds into a two-dimensional array. An intramolecular O-HN link is also present.

Related literature

For the structure of isomeric 2,5-dihydroxybenzaldehyde 4-methylthiosemicarbazone, see: Tan et al. (2008).

Experimental

Crystal data

C₉H₁₁N₃O₂S
M_r = 225.27
Monoclinic, C c
a = 18.0046 (6) Å
b = 4.6436 (1) Å
c = 12.2842 (4) Å
= 106.695 (2)°
V = 983.74 (5) Å³
Z = 4
Mo K radiation
= 0.31 mm^-1
T = 100 (2) K
0.09 × 0.06 × 0.03 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.973, T_max = 0.991
4390 measured reflections
2128 independent reflections
1925 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.109
S = 1.11
2128 reflections
153 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.31 e Å^-3
_min = -0.22 e Å^-3
Absolute structure: Flack (1983), with 814 Friedel pairs
Flack parameter: 0.00 (1)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1ON1	0.84 (1)	1.93 (3)	2.694 (3)	151 (6)
O2-H2OS1ⁱ	0.84 (1)	2.54 (1)	3.365 (2)	170 (4)
N2-H2NO1ⁱⁱ	0.87 (1)	2.11 (1)	2.950 (4)	162 (3)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2316 ).

Acknowledgements

We thank the University of Malaya (PJP FS316/2008 C) for supporting this study. KWT thanks the Ministry of Higher Education for an SLAI scholarship.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tan, K. W., Ng, C. H., Maah, M. J. & Ng, S. W. (2008). Acta Cryst. E64, o1344.
Westrip, S. P. (2008). publCIF. In preparation.

organic compounds