2-Amino-N-(2-hydr­oxy-3-methoxy­benzyl­idene)aniline

Al-Douh, M.H.; Hamid, S.A.; Osman, H.; Kia, R.; Fun, H.-K.

doi:10.1107/S1600536808016292

Volume 64
Part 7
Pages o1201-o1202
July 2008

Received 24 May 2008
Accepted 29 May 2008
Online 7 June 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.073
wR = 0.206
Data-to-parameter ratio = 17.5
Details

2-Amino-N-(2-hydroxy-3-methoxybenzylidene)aniline

Mohammed H. Al-Douh,^a Shafida A. Hamid,^a ⁺ Hasnah Osman,^a Reza Kia ^b and Hoong-Kun Fun ^b ^*

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title compound, C₁₄H₁₄N₂O₂, the dihedral angle between the two benzene rings is 9.67 (10)°. Two intramolecular O-HN and N-HN hydrogen bonds involving the hydroxy and amino groups generate S(6) and S(5) ring motifs, respectively. In the crystal structure, N-HO hydrogen bonds link neighboring molecules. Molecules are also stacked in a head-to-tail fashion along the c axis through [pi] - [pi] interactions [centroid-centroid separation of 3.7357 (12) Å] and are further linked by weak intermolecular C-H [pi] interactions, giving a zigzag arrangement along the b axis.

Related literature

For related literature on hydrogen bond motifs, see: Bernstein et al. (1995). For values of bond lengths, see: Allen et al. (1987). For the biological activity of imines, see, for example: Singh & Dash (1988); More et al. (2001); Baseer et al. (2000); El-Masry et al. (2000); Kabeer et al. (2001); Kuz'min et al. (2000); Desai et al. (2001). For related structures, see, for example: Corden et al. (1996); Govindasamy et al. (1999). For synthesis, see: Al-Douh et al. (2006, 2007). For related literature, see: Berger (2001); Elerman & Kabak (1997); Latif et al. (1983); Liu et al. (2006); Shah et al. (2008).

Experimental

Crystal data

C₁₄H₁₄N₂O₂
M_r = 242.27
Monoclinic, P 2₁ /c
a = 13.2790 (6) Å
b = 14.4810 (6) Å
c = 6.1928 (3) Å
= 103.116 (3)°
V = 1159.77 (9) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 100.0 (1) K
0.45 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.959, T_max = 0.996
19968 measured reflections
3402 independent reflections
2532 reflections with I > 2(I)
R_int = 0.052

Refinement

R[F² > 2(F²)] = 0.072
wR(F²) = 0.206
S = 1.06
3402 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.66 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are centroids of the C1-C6 and C8-C13 rings, respectively.

D-HA	D-H	HA	DA	D-HA
O1-H1O1N1	0.88	1.77	2.602 (2)	158
N2-H1N2O1ⁱ	0.93 (3)	2.56 (3)	3.030 (3)	111 (2)
N2-H1N2O2ⁱ	0.93 (3)	2.29 (3)	3.181 (3)	161 (3)
N2-H2N2N1	0.87 (3)	2.23 (3)	2.759 (3)	119 (2)
C3-H3Cg1ⁱⁱ	0.94 (3)	2.64 (3)	3.458 (2)	145 (2)
C11-H11Cg2ⁱⁱⁱ	0.91 (3)	2.87 (3)	3.538 (2)	142 (2)
Symmetry codes: (i) -x, -y+2, -z; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2510 ).

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for an IRPA short-term grant (No. 304/PKIMIA/638007) to conduct this work. MHA thanks the Yemen Government and Hadhramout University of Science and Technology (HUST) for financial scholarship support. HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

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organic compounds