2-[(4-Meth­oxy­anilino)meth­yl]phenol

Hong Shu; Ning-Shu Yu; Guo-Lan Xie; Li-Zhuang Chen

doi:10.1107/S1600536811031679

. 2011 Aug 11;67(Pt 9):o2304. doi: 10.1107/S1600536811031679

2-[(4-Methoxyanilino)methyl]phenol

Hong Shu ^a, Ning-Shu Yu ^a, Guo-Lan Xie ^a, Li-Zhuang Chen ^a,^*

PMCID: PMC3200731 PMID: 22064440

Abstract

In the title compound, C₁₄H₁₅NO₂, the dihedral angle between the two benzene rings is 71.10 (5)°. In the crystal, molecules are linked by intermolecular N—H⋯O, and O—H⋯N hydrogen bonds into a chain running parallel to the b axis.

Related literature

For the synthesis of the title compound, see: Noda (1959 ▶). For other related structures, see: Liu et al. (2007 ▶); Qu et al. (2007 ▶).

Experimental

Crystal data

C₁₄H₁₅NO₂
M _r = 229.27
Monoclinic,
a = 7.8132 (16) Å
b = 5.7947 (12) Å
c = 26.175 (5) Å
β = 95.02 (3)°
V = 1180.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.40 × 0.30 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.970, T _max = 0.983
10971 measured reflections
2693 independent reflections
1692 reflections with I > 2σ(I)
R _int = 0.056

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.128
S = 1.03
2693 reflections
163 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811031679/pv2441sup1.cif

e-67-o2304-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031679/pv2441Isup2.hkl

e-67-o2304-Isup2.hkl^{(132.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811031679/pv2441Isup3.cml

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
N1—H1⋯O2ⁱ	0.86 (1)	2.22 (1)	3.058 (2)	163 (2)
O2—H2⋯N1ⁱⁱ	0.86 (1)	1.89 (1)	2.741 (2)	172 (2)

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by a start-up grant from Jiangsu University of Science and Technology and by the Foundation of Jiangsu Educational Committee (11KJB150004), China.

supplementary crystallographic information

Comment

Recently, the crystal structures of compounds closely related to the title molecule, e.g., 2-[(4-chlorophenyl)aminomethyl]-6-methoxyphenol (Liu et al., 2007) and 2-(anilinomethyl)phenol (Qu et al., 2007) have been reported. We report here the crystal structure of a new member of this family of compounds.

In the title compound (Fig. 1), the dihedral angle between the two benzene ring planes is 71.10 (5)°. In the crystal structure, the molecules are linked by intermolecular N—H···O, and O—H···N hydrogen bonds into a one-dimensional chain lying parallel to the b-axis (Fig. 2).

Experimental

The title compound was synthesized by the reaction of 2-((4-methoxyphenylimino)- methyl)phenol (2.76 g, 10 mmol) with NaBH₄ (0.38 g, 10 mmol) in methanol (50 ml) according to the reported method (Noda, 1959). Crystals were obtained from an ethanolic (95%) solution by slow evaporation at room temperature.