4-Isopropyl­amino-3-nitro­benzonitrile

Hong-sheng Jia

doi:10.1107/S1600536811051737

. 2011 Dec 21;68(Pt 1):o183. doi: 10.1107/S1600536811051737

4-Isopropylamino-3-nitrobenzonitrile

Hong-sheng Jia ^a,^*

PMCID: PMC3254521 PMID: 22259467

Abstract

In the title compound, C₁₀H₁₁N₃O₂, the nitro group is essentially coplanar with the aromatic ring [dihedral angle = 3.4 (3)°] and forms an intramolecular N—H⋯O hydrogen bond with the amine group. In the crystal, weak aromatic C—H⋯O and C—H⋯N hydrogen bonds link the molecules. Weak aromatic ring π–π interactions [minimum ring centroid–centroid separation = 3.9841 (16) Å] are also present.

Related literature

For the synthesis of the title compound, see: Ates-Alagoz & Buyukbingol (2001 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₀H₁₁N₃O₂
M _r = 205.22
Monoclinic,
a = 6.6640 (13) Å
b = 20.678 (4) Å
c = 7.8900 (16) Å
β = 105.74 (3)°
V = 1046.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 four-circle diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.982, T _max = 0.991
2821 measured reflections
1926 independent reflections
1228 reflections with I > 2σ(I)
R _int = 0.020
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.170
S = 1.00
1926 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1994) ▶; 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811051737/zs2168sup1.cif

e-68-0o183-sup1.cif^{(15.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051737/zs2168Isup2.hkl

e-68-0o183-Isup2.hkl^{(94.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811051737/zs2168Isup3.cml

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
N3—H3A⋯O2	0.86	1.99	2.643 (2)	132
C1—H1A⋯N1ⁱ	0.93	2.61	3.469 (3)	153
C4—H4A⋯O1ⁱⁱ	0.93	2.40	3.298 (3)	163
C5—H5A⋯N1ⁱⁱⁱ	0.93	2.60	3.529 (4)	175

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

Acknowledgments

The authors thank Liu Bo Nian from Nanjing University of Technology for useful discussions and the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

We report herein the crystal structure of the title compound C₁₀H₁₁N₃O₂. In this molecule (Fig. 1), the bond lengths and angles (Allen et al., 1987) are within normal ranges. The nitro group is essentially coplanar with the aromatic ring forming a dihedral angle of 3.4 (3)° with the ring. The amine H atom forms an intramolecular hydrogen bond with a nitro O-atom acceptor (O2) (Table 1). In the crystal structure, intermolecular aromatic C—H···O and C—H···N hydrogen bonds link the molecules (Fig. 2) while also present are weak aromatic ring π–π interactions [minimum ring centroid separation, 3.9841 (16) Å].

Experimental

The title compound was synthesized using the procedure of (Ates-Alagoz & Buyukbingol, 2001). 4-Chloro-3-nitrobenzonitrile (4.2 g, 0.023 mol) was refluxed in 25 ml of t-propylamine and 50 ml of tetrahydrofuran for 4 h. The solvent was then evaporated and water was added to give a precipitate which was collected by filtration and washed with cold ethanol (2 × 15 ml) to afford the yellow solid (4.2 g, 89%). The pure title compound was obtained by crystallizing from ethanol, with crystals suitable for X-ray diffraction obtained by slow room-temperature evaporation of an ethanol solution.