2-((E)-{[4-(Hy­droxy­meth­yl)phen­yl]imino}­meth­yl)phenol

Mohamed, S.K.; Abdelhamid, A.A.; Akkurt, M.; Fanwick, P.E.; Maharramov, A.M.

doi:10.1107/S1600536812019368

Volume 68
Part 6
Page o1618
June 2012

Received 25 April 2012
Accepted 30 April 2012
Online 5 May 2012

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.107
Data-to-parameter ratio = 12.0
Details

2-((E)-{[4-(Hydroxymethyl)phenyl]imino}methyl)phenol

Shaaban K. Mohamed,^a Antar A. Abdelhamid,^a Mehmet Akkurt,^b ^* Phillip E. Fanwick ^c and A. M. Maharramov ^d

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,^cDepartment of Chemistry, Purdue University, W. Lafayette, IN 47907, USA, and ^dDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan
Correspondence e-mail: akkurt@erciyes.edu.tr

The title compound, C₁₄H₁₃NO₂, adopts the enol-imine tautomeric form, with an intramolecular O-HN hydrogen bond which generates an S(6) ring motif. The dihedral angle between the aromatic rings is 7.85 (7)°. The crystal structure is stabilized by O-HO, O-HN and C-HO hydrogen bonds, forming a two-dimensional array that stacks along the a axis. In addition, a C-H [pi] interaction contributes to the stabilization of the crystal packing.

Related literature

For background to Schiff base compounds, see: Elena et al. (2000); Mohamed et al. (2006); Rajavel et al. (2008); Ugras et al. (2006); Wadher et al. (2009). For similar structures, see: Deveci et al. (2008); Karadayi et al. (2003); Kosar et al. (2010); Ünver et al. (2002). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₄H₁₃NO₂
M_r = 227.25
Monoclinic, P 2₁ /c
a = 19.8172 (14) Å
b = 4.7217 (1) Å
c = 12.3106 (2) Å
= 104.005 (7)°
V = 1117.67 (9) Å³
Z = 4
Cu K radiation
= 0.73 mm^-1
T = 150 K
0.25 × 0.20 × 0.08 mm

Data collection

Rigaku RAPID II diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2001) T_min = 0.838, T_max = 0.944
10711 measured reflections
1958 independent reflections
1641 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.107
S = 1.14
1958 reflections
163 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.23 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2-C7 benzene ring.

D-HA	D-H	HA	DA	D-HA
O1-H1O1ⁱ	0.94 (3)	1.79 (2)	2.7235 (14)	172 (2)
O2-H2N1	0.93 (2)	1.74 (2)	2.5990 (15)	151.7 (19)
C7-H7O1ⁱⁱ	0.95	2.57	3.4288 (16)	150
C8-H8O2ⁱⁱⁱ	0.95	2.59	3.4492 (16)	151
C1-H1BCg1^iv	0.99	2.56	3.5050 (15)	160
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{5\over 2}}, z-{\script{1\over 2}}]$ ; (iv) x, y-1, z.

Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5090 ).

Acknowledgements

The authors are grateful to the Higher Education Ministry of Egypt for financial support of this project. Manchester Metropolitan University and Purdue University are also acknowledged for the data collection and support of this study.

References

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organic compounds