5-{2-[(2-Hydroxy-5-methyl­phen­yl)(phenyl)methyl­eneamino]phenyl­imino­meth­yl}­pyrrole-2-carbaldehyde

Ge Liu; Jianhui Wang; Liqin Guo; Wen-Juan Ruan

doi:10.1107/S1600536808021922

. 2008 Jul 19;64(Pt 8):o1552. doi: 10.1107/S1600536808021922

5-{2-[(2-Hydroxy-5-methylphenyl)(phenyl)methyleneamino]phenyliminomethyl}pyrrole-2-carbaldehyde

Ge Liu ^a,^b, Jianhui Wang ^a, Liqin Guo ^a, Wen-Juan Ruan ^a,^*

PMCID: PMC2962098 PMID: 21203255

Abstract

The title compound, C₂₆H₂₁N₃O₂, is an unsymmetrical tetradentate Schiff base ligand. The hydroxy group forms an intramolecular O—H⋯N hydrogen bond with an adjacent N atom. An intermolecular N—H⋯O hydrogen bond creates centrosymmetric dimers in the crystal packing.

Related literature

For background, see: Ainscough et al. (1995 ▶); Aruffo et al. (1984 ▶). For further synthetic details, see: Atkins et al. (1985 ▶); Miller & Olsson (1981 ▶); Olsson & Pernemalm (1979 ▶); Zhu et al. (2004 ▶).

Experimental

Crystal data

C₂₆H₂₁N₃O₂
M _r = 407.46
Triclinic,
a = 8.8299 (18) Å
b = 9.4816 (19) Å
c = 13.130 (3) Å
α = 94.05 (3)°
β = 106.32 (3)°
γ = 94.88 (3)°
V = 1046.0 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 113 (2) K
0.22 × 0.16 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2001 ▶) T _min = 0.98, T _max = 0.99
10760 measured reflections
3695 independent reflections
3065 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.129
S = 1.08
3695 reflections
286 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021922/bg2193sup1.cif

e-64-o1552-sup1.cif^{(22.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021922/bg2193Isup2.hkl

e-64-o1552-Isup2.hkl^{(181.4KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O2ⁱ	0.95 (2)	1.98 (2)	2.902 (2)	164.2 (18)
O1—H1⋯N1	0.82	1.81	2.536 (2)	147

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Nankai University for supporting this work.

supplementary crystallographic information

Comment

Unsymmetrical Schiff base ligands have been widely investigated due to their structural versatility; specially their metal complexes have been of interest to chemists (Aruffo et al., 1984; Ainscough et al.,1995). In the course of the synthesis of one such a complex (Zhu et al., 2004; Atkins et al.,1985), single crystals of the title compound C₂₆H₂₁N₃O₂ (I) were obtained, and its crystal and molecular structure is reported here (Fig.1). An intermolecular N—H···O hydrogen bond is formed between the H(pyrrole) atom of one molecule and O(aldehyde) of an adjacent molecule (Table 1), giving raise to centrosymmetric dimers in the crystal packing, piled as columnar arrays along a, as shown in Fig. 2

Moreover, the hydroxy group is involved in an intramolecular O—H···N hydrogen bond (Table 1, Fig.1), though which atoms O1, H1, N1, C8, C1 and C2 form a six-membered ring.

Experimental

To a solution of 2-[(2-Aminophenyl)(phenyl)methyl]-4-methylphenol (0.2 mmol)(Atkins et al.,1985) in toluene (20 ml) was added pyrrole-2,5-dicarboxaldehyde (0.2 mmol)(Miller & Olsson, 1981; Olsso & Pernemalm, 1979) the mixture was stired and refluxed for two hours, then cooled. Rotary evaporation of solvent yielded the crude product; after chromatographic fractionating, it was recrystallized from the mixture of dichloromethane and hexane. Orange columnar crystals were obtained by evaporating the solvent at room temperature for about a week. yield: 53%, mp = 175°. Anal. for (C₂₆H₂₁N₃O₂), Calc. C, 76.64; H, 5.19; N, 10.31; Found: C, 76.12; H, 5.62; N, 10.19.