Space group revsion of the triclinic polymorph of salicyl­aldehyde azine

Saeed, A.; Bolte, M.; Arshad, M.

doi:10.1107/S160053681105478X

Volume 68
Part 2
Page o255
February 2012

Received 25 November 2011
Accepted 20 December 2011
Online 7 January 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.045
wR = 0.116
Data-to-parameter ratio = 12.7
Details

Space group revsion of the triclinic polymorph of salicylaldehyde azine

Aamer Saeed,^a ^* Michael Bolte ^b and Muhammad Arshad ^c

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan,^bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany, and ^cChemistry Division, Directorate of Science, PINSTECH, Nilore, Islamabad, Pakistan
Correspondence e-mail: aamersaeed@yahoo.com

The structure of the title compound, C₁₄H₁₂N₂O₂ {systematic name: 2,2'-[hydrazinediylidenebis(methanylylidene)]diphenol}, has already been determined in the triclinic space group P $[\overline{1}]$ with Z = 4 [El-Medani, Aboaly, Abdalla & Ramadan (2004). Spectrosc. Lett. 37, 619-632]. However, the correct space group should be P2₁/c with Z = 4. This structure is a new polymorph of the already known monoclinic polymorph of salicyladehyde azine, which crystallizes in space group P2₁/n with Z = 2. The benzene rings form a dihedral angle of 46.12 (9)°. Two intramolucular O-HN hydrogen bonds occur.

Related literature

For the structure of salicylaldehyde azine in P $[\overline{1}]$ with Z=4, see El-Medani et al. (2004). For the other monoclinic polymorph of salicyladehyde azine, see for example Xue et al. (1994).

Experimental

Crystal data

C₁₄H₁₂N₂O₂
M_r = 240.26
Monoclinic, P 2₁ /c
a = 16.3621 (11) Å
b = 5.9180 (4) Å
c = 13.1706 (9) Å
= 113.639 (5)°
V = 1168.31 (14) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 173 K
0.28 × 0.19 × 0.12 mm

Data collection

Stoe IPDS II two-circle diffractometer
14742 measured reflections
2189 independent reflections
1977 reflections with I > 2(I)
R_int = 0.079

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.116
S = 1.17
2189 reflections
172 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.18 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.95 (3)	1.81 (3)	2.6454 (19)	145 (2)
O1A-H1AN1A	0.95 (3)	1.82 (3)	2.6532 (19)	145 (2)

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZJ2044 ).

References

El-Medani, S. M., Aboaly, M. M., Abdalla, H. H. & Ramadan, R. M. (2004). Spectrosc. Lett. 37, 619-632.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.
Xu, X.-X., You, X.-Z., Sun, Z.-F., Wang, X. & Liu, H.-X. (1994). Acta Cryst. C50, 1169-1171.

organic compounds