2,5-Dimethyl-1-phenyl­sulfonyl-1H-pyrrole-3,4-dicarbaldehyde

P R Seshadri; B Balakrishnan; K Ilangovan; R Sureshbabu; A K Mohanakrishnan

doi:10.1107/S1600536809004425

. 2009 Feb 18;65(Pt 3):o531. doi: 10.1107/S1600536809004425

2,5-Dimethyl-1-phenylsulfonyl-1H-pyrrole-3,4-dicarbaldehyde

P R Seshadri ^a,^*, B Balakrishnan ^b, K Ilangovan ^c, R Sureshbabu ^d, A K Mohanakrishnan ^d

PMCID: PMC2968504 PMID: 21582192

Abstract

In the title compound, C₁₄H₁₃NO₄S, the mean planes of the pyrrole and phenyl rings form a dihedral angle of 88.7 (1)°. The aldehyde groups are slightly twisted from the pyrrole plane. In the crystal structure, molecules are linked into a three-dimensional framework by C—H⋯O hydrogen bonds.

Related literature

For general background, see: Ali et al. (1989 ▶); Amal Raj et al. (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶). For N-atom hybridization details, see: Beddoes et al. (1986 ▶).

Experimental

Crystal data

C₁₄H₁₃NO₄S
M _r = 291.31
Monoclinic,
a = 9.0257 (3) Å
b = 12.6240 (5) Å
c = 11.9914 (5) Å
β = 97.700 (2)°
V = 1353.99 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.940, T _max = 0.952
19609 measured reflections
4736 independent reflections
3164 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.154
S = 1.00
4736 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: PARST (Nardelli, 1995 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809004425/wn2307sup1.cif

e-65-0o531-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004425/wn2307Isup2.hkl

e-65-0o531-Isup2.hkl^{(227.3KB, 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
C6—H6⋯O3	0.93	2.46	3.077 (2)	124
C7—H7A⋯O4	0.96	2.33	3.021 (3)	128
C11—H11⋯O4ⁱ	0.93	2.53	3.456 (2)	174
C13—H13⋯O2	0.93	2.52	3.304 (2)	143
C14—H14⋯O3ⁱⁱ	0.93	2.57	3.383 (2)	146

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

Acknowledgments

BB and RS thank Dr Babu Varghese, SAIF, IIT Madras, India, for his help with the data collection.

supplementary crystallographic information

Comment

Heterocyclic compounds, especially five-membered rings, have occupied an important place among organic compounds because of their biological activities. The fungicidal activity of novel heterocycles has been reported by Ali et al. (1989). These are crucial intermediates for various pyrrole natural products possessing antitumour properties. They are found to have antifungal activity against various pathogens (Amal Raj et al., 2003). Against this background and in order to obtain detailed information on molecular conformation in the solid state, an X-ray crystallographic study of the title compound has been carried out and the results are presented here.

The geometric parameters are normal (Allen et al., 1987). The mean planes of the pyrrole and phenyl rings form a dihedral angle of 88.7 (1)°. The aldehyde groups are slightly twisted from the pyrrole plane, with O3 towards C2 and O4 towards C1, as evidenced by the torsion angles C2—C3—C5—O3 = 2.1 (3)° and C1—C2—C6—O4 = 5.9 (3)° (Fig. 1). The sum of the angles at N is 360.0, which is an indication of sp² hybridization (Beddoes et al., 1986). In the crystal structure, the molecules are linked into a three-dimensional framework by C—H···O hydrogen bonds (Fig. 2 and Table 1).

Experimental

To a suspension of 3°-butoxide (4.4 g, 39.7 mmol) in dry THF (20 ml), 18-crown-6 (catalyst) and 2,5-dimethyl-1H-pyrrole-3,4-dicarbaldehyde (4 g, 26.5 mmol) in dry THF were added slowly at room temperature and the reaction mixture was stirred for 15 min. To this, PhSO₂Cl (6.1 g, 34.4 mmol) in dry THF (15 ml) was added and stirred for another 4 h. The mixture was then poured over ice–water (500 ml) and the solid obtained was filtered. The product, 2,5-dimethyl-1-(phenyl sulfonyl)-1H-pyrrole-3,4-dicarbaldehyde, was recrystallized from methanol. Yield 4.9 g (64%). M.p = 395 K.