Phenyl N-(4-methoxy­phen­yl)carbamate

Zheng Fang; Yong-Lu Wang; Li-Li Ren; Ping Wei

doi:10.1107/S1600536809028785

. 2009 Jul 25;65(Pt 8):o1997. doi: 10.1107/S1600536809028785

Phenyl N-(4-methoxyphenyl)carbamate

Zheng Fang ^a,^*, Yong-Lu Wang ^a, Li-Li Ren ^a, Ping Wei ^b

PMCID: PMC2977260 PMID: 21583669

Abstract

The asymmetric unit of the title compound, C₁₄H₁₃NO₃, contains two crystallographically independent molecules, in which the aromatic rings are oriented at dihedral angles of 75.64 (3) and 83.14 (3)°. An N—H⋯O hydrogen bond links the two molecules. Weak intramolecular C—H⋯O interactions are observed in the two molecules. In the crystal structure, intermolecular N—H⋯O and C—H⋯O interactions link the molecules into a two-dimensional network.

Related literature

For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₁₃NO₃
M _r = 243.25
Monoclinic,
a = 9.869 (2) Å
b = 10.870 (2) Å
c = 23.319 (5) Å
β = 100.27 (3)°
V = 2461.5 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.09 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 = 0.973, T _max = 0.991
4733 measured reflections
4459 independent reflections
2109 reflections with I > 2σ(I)
R _int = 0.045
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.069
wR(F ²) = 0.184
S = 1.03
4459 reflections
319 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028785/hk2744sup1.cif

e-65-o1997-sup1.cif^{(23.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028785/hk2744Isup2.hkl

e-65-o1997-Isup2.hkl^{(218.5KB, 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
N1—H1A⋯O5	0.86	2.19	3.038 (4)	170
N2—H2B⋯O2ⁱ	0.86	2.22	3.062 (4)	166
C6—H6A⋯O5ⁱⁱ	0.93	2.58	3.435 (5)	153
C9—H9A⋯O2	0.93	2.52	2.967 (5)	110
C23—H23A⋯O2ⁱ	0.93	2.60	3.390 (4)	144
C27—H27A⋯O5	0.93	2.30	2.907 (5)	122

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

Acknowledgments

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

supplementary crystallographic information

Comment

Some derivatives of benzoic acid are important chemical materials. We report herein the crystal structure of the title compound.

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 (C1-C6), B (C8-C13) and C (C15-C20), D (C22-C27) are, of course, planar and they are oriented at dihedral angles of A/B = 75.64 (3) and C/D = 83.14 (3)°. Intramolecular N-H···O hydrogen bond (Table 1) link the two molecules (Fig. 1). There also exist two intramolecular C-H···O interactions (Table 1).

In the crystal structure, intramolecular N-H···O and intermolecular N-H···O and C-H···O interactions (Table 1) link the molecules into a two dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, to a cold stirring solution of 4-methoxybenzenamine (1.0 g) and triethylamine (0.8 ml) in methylene chloride (10 ml) was added phenyl chloroformate (1.0 ml) slowly at 273 K. The mixture was then warmed and stirred for 1 h at room temperature. The mixture was washed with water (20 ml), dried over sodium sulfate, and concentrated to near dryness. The crude product was purified by recrystallization from petroleum ether (yield; 1.3 g). Crystals suitable for X-ray analysis were obtained by slow evaporation of a petroleum ether solution.