(2-Methyl-3-nitro­phen­yl)methanol

Jian-hong Zhang; You-sheng Chen; Xi Wang

doi:10.1107/S160053680902707X

. 2009 Jul 18;65(Pt 8):o1925. doi: 10.1107/S160053680902707X

(2-Methyl-3-nitrophenyl)methanol

Jian-hong Zhang ^a, You-sheng Chen ^a, Xi Wang ^a,^*

PMCID: PMC2977451 PMID: 21583608

Abstract

The asymmetric unit of the title compound, C₈H₉NO₃, contains two crystallographically independent molecules, whose aromatic rings are oriented at a dihedral angle of 83.29 (3)°. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the molecules into chains.

Related literature

The title compound is an intermediate in the synthesis of the monomer 2-methyl-3-nitrobenzaldehyde, utilized to synthesize ergoline derivatives which have potential use in the treatment of Parkinson’s disease, see: Kozikowski et al. (1980 ▶). For a related structure, see: Wu et al. (1994 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₈H₉NO₃
M _r = 167.16
Monoclinic,
a = 13.601 (3) Å
b = 7.8650 (16) Å
c = 15.433 (3) Å
β = 92.73 (3)°
V = 1649.0 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 294 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.969, T _max = 0.990
3123 measured reflections
2990 independent reflections
1783 reflections with I > 2σ(I)
R _int = 0.020
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.061
wR(F ²) = 0.189
S = 1.00
2990 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902707X/hk2709sup1.cif

e-65-o1925-sup1.cif^{(18.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902707X/hk2709Isup2.hkl

e-65-o1925-Isup2.hkl^{(146.8KB, 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
O1—H1A⋯O4ⁱ	0.82	1.97	2.725 (3)	153
O4—H4B⋯O1ⁱⁱ	0.82	1.95	2.706 (3)	153

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

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

The tittle compound is an important intermediate used to synthesize the monomer 2-methyl-3-nitrobenzaldehyde, which can be utilized to synthesize ergoline derivatives and it has been reported to have some useful physiological and pharmacological functions to parkinson's disease (Kozikowski et al., 1980). We report herein the crystal structure of the title compound, which is of interest to us in the field.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1), in which the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C2-C7) and B (C10-C15) are, of course, planar. The dihedral angle between them is 83.29 (3)°. Atoms N1, C1, C8 and N2, C9, C16 are -0.006 (3), 0.029 (3), -0.022 (3) and 0.077 (3), -0.075 (3), -0.076 (3) Å away from the adjacent ring planes, respectively.

In the crystal structure, intermolecular O-H···O hydrogen bonds (Table 1) link the molecules into chains (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

The title compound was prepared according to a literature method (Wu et al., 1994). Crystals suitable for X-ray analysis were obtained by slow evaporation of methanol for about 20 d.