Phenyl N-phenyl­carbamate

Durre Shahwar; M Nawaz Tahir; M Sharif Mughal; Muhammad Akmal Khan; Naeem Ahmad

doi:10.1107/S1600536809017887

. 2009 May 23;65(Pt 6):o1363. doi: 10.1107/S1600536809017887

Phenyl N-phenylcarbamate

Durre Shahwar ^a, M Nawaz Tahir ^b,^*, M Sharif Mughal ^c, Muhammad Akmal Khan ^a, Naeem Ahmad ^a

PMCID: PMC2969800 PMID: 21583214

Abstract

In the title compound, C₁₃H₁₁NO₂, the aromatic rings are oriented at a dihedral angle of 42.52 (12)°. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds, which form infinite one-dimensional polymeric chains extending along the a axis. C—H⋯π interactions between the aromatic rings are also present.

Related literature

For related structures, see: Haufe et al. (2003 ▶); Shah et al. (2008 ▶, 2009 ▶); Xu & Qu (2008 ▶).

Experimental

Crystal data

C₁₃H₁₁NO₂
M _r = 213.23
Orthorhombic,
a = 9.4734 (9) Å
b = 19.5825 (17) Å
c = 5.8509 (5) Å
V = 1085.42 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.22 × 0.12 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.985, T _max = 0.988
6579 measured reflections
1505 independent reflections
751 reflections with I > 2σ(I)
R _int = 0.071

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.086
S = 0.97
1505 reflections
145 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017887/at2785sup1.cif

e-65-o1363-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017887/at2785Isup2.hkl

e-65-o1363-Isup2.hkl^{(74.2KB, 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—H1⋯O2ⁱ	0.86	2.14	2.976 (3)	165
C3—H3⋯Cg2ⁱⁱ	0.93	2.80	3.673 (4)	156
C10—H10⋯Cg1ⁱⁱⁱ	0.93	2.86	3.599 (4)	137

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

Acknowledgments

NA gratefully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing a scholarship under the Indigenous PhD Program (PIN 042-120599-PS2-156).

supplementary crystallographic information

Comment

The title compound (I), (Fig. 1), is synthesized for investigation of biological activity like enzyme inhibition and antimicrobial activity. It is one of the members of a series of carbamates being synthesized in our laboratory.

Various crystal structures of N-phenylcarbamates with different attachments have been reported. Examples include (II) 4-nitrophenyl N-phenylcarbamate (Xu & Qu, 2008), (III) cis-4-fluorocyclohexyl N-phenylcarbamate, cis-4-hydroxycyclohexyl N-phenylcarbamate and 4-oxocyclohexyl N-phenylcarbamate (Haufe et al., 2003). The title compound is a N-phenylcarbamate with the simplest type of aromatic ring. In (I), the rings A (C1—C6) and B (C8—C13) are oriented at a dihedral angle of 42.49 (13)°. The title compound is stabilized in the form of infinite one-dimensional polymeric chains due to intermolecular N—H···O H-bonding. These chains extend along the crystallographic a axis (Table 1, Fig. 2). Similar infinite chains also due to intermolecular N—H···O H-bonding have also been found in 3-[(3,4-dichlorophenyl)aminocarbonyl]-propionic acid (Shah et al., 2009), 4-[(2-fluorophenyl)amino]-4-oxobutanoic acid (Shah et al., 2008). The packing may also be stabilized due to C—H···π interactions (Table 1).

Experimental

A solution of aniline (0.913 ml, 0.01 mol) and dichloromethane (20 ml) was prepared. Phenylchloroformate (1.26 ml, 0.01 mol) was added dropwise to the magnetically stirring solution. The mixture turned to a suspension after 1 h due to stirring at room temperature. To obtain the final product, n-hexane (30 ml) was added and a precipitate was formed. The precipitate was filtered and recrystalized from ethylacetate and methanol (9:1).