N-Phenyl­formamide

B Thimme Gowda; Sabine Foro; Hartmut Fuess

doi:10.1107/S1600536809022776

. 2009 Jun 20;65(Pt 7):o1633. doi: 10.1107/S1600536809022776

N-Phenylformamide

B Thimme Gowda ^a,^*, Sabine Foro ^b, Hartmut Fuess ^b

PMCID: PMC2969504 PMID: 21582899

Abstract

There are two independent molecules in the asymmetric unit of the title compound, C₇H₇NO. The conformation of the N—H bond in the structure is syn to the C=O bond in one of the molecules and anti in the other. In the crystal, molecules are packed into chains diagonally in the ac plane via N—H⋯O hydrogen bonds.

Related literature

For related structures, see: Gowda et al. (2006 ▶); Brown (1966 ▶). For our study of the effect of ring and side chain substitutions on the crystal structures of aromatic amides, see: Gowda et al. (2000 ▶, 2007 ▶, 2009 ▶).

Experimental

Crystal data

C₇H₇NO
M _r = 121.14
Monoclinic,
a = 30.923 (3) Å
b = 6.1737 (6) Å
c = 14.814 (1) Å
β = 113.14 (1)°
V = 2600.6 (4) Å³
Z = 16
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.48 × 0.44 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.966, T _max = 0.969
8394 measured reflections
2383 independent reflections
1679 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.115
S = 1.12
2383 reflections
170 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.10 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022776/rk2151sup1.cif

e-65-o1633-sup1.cif^{(17KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022776/rk2151Isup2.hkl

e-65-o1633-Isup2.hkl^{(117.2KB, 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—H1N⋯O2ⁱ	0.888 (16)	1.936 (16)	2.8239 (17)	178.1 (14)
N2—H2N⋯O1ⁱⁱ	0.857 (16)	2.007 (16)	2.8637 (17)	177.0 (14)

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

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany for the resumption of his research fellowship.

supplementary crystallographic information

Comment

As part of a study of the effect of ring and side chain substitutions on the crystal structures of aromatic amides (Gowda et al., 2000; 2007; 2009), the structure of N–(phenyl)–formamide (I) has been determined. The asymmetric unit contains two independent molecules (Fig. 1). The conformation of the N—H bond is syn to the C═O bond in the side chain, in one of the molecules and is anti in the other, in contrast to the anti conformation observed in N–(2,6–dichlorophenyl)–formamide (Gowda et al., 2000 and N–(phenyl)–acetamide (Brown et al., 1966). The molecules in (I) are linked through intermolecular N—H···O hydrogen bonding (Tab. 1) and the chains formed diagonally as viewed in the ac plane (Fig. 2).

Experimental

The purity of the commmercial sample (Aldrich Chemicals) was checked by determining its melting point and characterized by recording its infrared and NMR spectra (Gowda et al., 2006). The single crystals used in X–ray diffraction studies were grown in ethanol solution by slow evaporation at room temperature.