N-(2-Eth­oxy­phen­yl)formamide

Mohammad Kazem Rofouei; Jafar Attar Gharamaleki; Fereshteh Younesian; Giuseppe Bruno; Hadi Amiri Rudbari

doi:10.1107/S160053681200205X

. 2012 Jan 21;68(Pt 2):o505. doi: 10.1107/S160053681200205X

N-(2-Ethoxyphenyl)formamide

Mohammad Kazem Rofouei ^a, Jafar Attar Gharamaleki ^a,^*, Fereshteh Younesian ^b, Giuseppe Bruno ^c, Hadi Amiri Rudbari ^c

PMCID: PMC3275250 PMID: 22347106

Abstract

The title compound, C₉H₁₁NO₂, was obtained as an unexpected product in an attempt to synthesize a triazene ligand. The title molecule is almost planar, with the formamide and ethoxy groups oriented at 2.7 (3) and 12.9 (2)°, respectively, with respect to the mean plane of the benzene ring. In the crystal, molecules are linked by intermolecular N—H⋯O hydrogen bonds, forming a chain along the a axis. Weak C—H⋯π interactions with an H⋯π distance of 2.78 Å reinforce the crystal packing, resulting in a three-dimensional network.

Related literature

For preparation of several trizene compounds in our laboratory, see: Melardi et al. (2011 ▶). For similar crystal structures, see: Landman et al. (2011 ▶); Chitanda et al. (2008 ▶); Hu et al. (2010 ▶).

Experimental

Crystal data

C₉H₁₁NO₂
M _r = 165.19
Orthorhombic,
a = 7.9079 (4) Å
b = 14.1253 (6) Å
c = 15.9555 (7) Å
V = 1782.25 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.45 × 0.23 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007) ▶ T _min = 0.671, T _max = 0.746
8725 measured reflections
1961 independent reflections
1248 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.120
S = 1.03
1961 reflections
110 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.14 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: XPW in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681200205X/pv2505sup1.cif

e-68-0o505-sup1.cif^{(14.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200205X/pv2505Isup2.hkl

e-68-0o505-Isup2.hkl^{(94.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681200205X/pv2505Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C3–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.86	2.24	2.9741 (18)	144
C2—H2A⋯Cgⁱⁱ	0.97	2.78	3.5853 (19)	141

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

supplementary crystallographic information

Comment

The preparation of several trizene compounds as ligands in our laboratory has already been reported (Melardi et al., 2011). However, the title compound was formed as an unexpected product in an attempt for the synthesis of a triazene ligand, 1-(2-methylphenyl)-3(2-ethoxyphenyl)triazene). In this article, we report the synthesis and crystal structure of the title compound.

The title molecule (Fig. 1) is almost planar with formamide and ethoxy groups oriented at 2.7 (3) and 12.9 (2)°, respectively, with respect to the mean-plane of the benzene ring. The bond lengths and angles in the title molecule are in accord with the corresponding bond lengths and angles reported in a few similar structures (Landman et al., 2011; Chitanda et al., 2008; Hu et al., 2010).

In the crystal structure molecules are linked by intermolecular N—H···O hydrogen bonds (Table 1) to form a chain along the a-axis. Weak edge-to-face C—H···Cg1 stacking interaction between an ethoxy hydrogen and a benzene ring with H···π distance of 2.78 Å, (Cg1 is the center of benzene ring atoms C3/C4/C6—C9) reinforce the crystal packing resulting in a three-dimensional network (Fig. 2).

Experimental

The title compound was obtained as an unexpected product in an attempt for the synthesis of a triazene ligand, 1-(2-methylphenyl)-3(2-ethoxyphenyl)triazene). A 100 ml flask was charged with 10 g of ice and 15 ml of water and then cooled to 273 K in an ice-bath. To this were added 2-methylaniline (0.215 g, 2 mmol), hydrochloric acid (36.5%, 2 mmol) and 2 ml water. To this solution was then added a solution containing NaNO₂ (0.16 g, 2 mmol) in 2 ml water during a 15 min period. After mixing for 15 min, the obtained solution was added to a solution of o-phenetidin (0.261 ml, 2 mmol), 2 ml methanol and 2 ml water. After that a solution containing sodium acetate (2.95 g, 36 mmol) in 10 ml water was added. After mixing for 24 h the colorless material was filtered off and dissolved in DMSO. By recrystallization from DMSO, the crystals of the title compound were obtained instead of the expected triazene.