4-(2,3-Dimeth­oxy­phen­yl)-1H-pyrrole-3-carbonitrile

Qing-Hao Chen; Fan-Wei Meng; Gui-Jun Dong; Xiao-Dan Wang; Jin-Sheng Gao

doi:10.1107/S1600536812018302

. 2012 Apr 28;68(Pt 5):o1567. doi: 10.1107/S1600536812018302

4-(2,3-Dimethoxyphenyl)-1H-pyrrole-3-carbonitrile

Qing-Hao Chen ^a, Fan-Wei Meng ^a, Gui-Jun Dong ^b, Xiao-Dan Wang ^a, Jin-Sheng Gao ^a,^*

PMCID: PMC3344663 PMID: 22590425

Abstract

The asymmetric unit of the title compound, C₁₃H₁₂N₂O₂, obtained in a search for analogs of the fungicide fludioxonil [systematic name: 4-(2,2-difluoro-1,3-benzodioxol-4-yl)-1H-pyrrole-3-carbonitrile], contains two independent molecules, A and B. The benzene and pyrrole rings are inclined to each other at 38.5 (1) and 29.3 (1)° in molecules A and B, respectively. In the crystal, bifurcated N—H⋯(O,O) hydrogen bonds link A molecules into chains along [001], while B molecules are linked into layers parallel to the bc plane via bifurcated N—H⋯(N,N) hydrogen bonds.

Related literature

For the synthesis of the title compound, see: Pfluger et al. (1989 ▶).

Experimental

Crystal data

C₁₃H₁₂N₂O₂
M _r = 228.25
Monoclinic,
a = 17.527 (4) Å
b = 9.6576 (19) Å
c = 14.237 (3) Å
β = 106.92 (3)°
V = 2305.5 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.69 × 0.67 × 0.53 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.941, T _max = 0.954
21190 measured reflections
5215 independent reflections
3907 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.129
S = 1.07
5215 reflections
320 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812018302/cv5288sup1.cif

e-68-o1567-sup1.cif^{(28.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018302/cv5288Isup2.hkl

e-68-o1567-Isup2.hkl^{(255.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812018302/cv5288Isup3.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
N1—H11⋯N2ⁱ	0.90 (1)	2.38 (2)	3.086 (2)	136 (2)
N1—H11⋯N2ⁱⁱ	0.90 (1)	2.55 (2)	3.250 (2)	136 (2)
N3—H31⋯O4ⁱⁱⁱ	0.89 (1)	2.12 (1)	2.9327 (16)	151 (2)
N3—H31⋯O3ⁱⁱⁱ	0.89 (1)	2.38 (2)	3.0709 (18)	134 (2)

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

Acknowledgments

The authors thank the Project of Innovation Service Platform of Heilongjiang Province (PG09J001) and Heilongjiang University for supporting this work.

supplementary crystallographic information

Comment

The title compound, (I), is the analogue of Fludioxonil, which is kind of fungicide developed and produced by Novartis. Herein, we report the synthesis and crystal structure of (I).

The asymmetric unit of (I) (Fig. 1), obtained in a search for analogs of Fludioxonil, contains two independent molecules, A and B, respectively. The benzene and pyrrole rings are inclined to each other at 38.5 (1)° in molecules A and 29.3 (1)° in molecules B. In the crystal (Fig. 2), intermolecular bifurcated N—H···O hydrogen bonds (Table 1) link molecules A into chains in [001], while molecules B are linked into layers parallel to bc plane via bifurcated N—H···N hydrogen bonds (Table 1).

Experimental

The title compound was prepared by the reaction of (Z)-2-cyano-3-(2,3-dimethoxyphenyl)acrylamide and 1-(isocyanomethylsulfonyl)-4-methylbenzene under alkaline condition (Pfluger et al., 1989). A colourless block crystal suitable for X-ray diffraction was obtained by the recrystallization of (I) from methanol.