4-{2-[(Z)-(5-Methyl-2-fur­yl)methyl­idene­amino]­eth­yl}benzene­sulfonamide

Khalid Mahmood; Muhammad Yaqub; M Nawaz Tahir; Zahid Shafiq; Ashfaq Mahmood Qureshi

doi:10.1107/S1600536810034045

. 2010 Aug 28;66(Pt 9):o2436. doi: 10.1107/S1600536810034045

4-{2-[(Z)-(5-Methyl-2-furyl)methylideneamino]ethyl}benzenesulfonamide

Khalid Mahmood ^a, Muhammad Yaqub ^a, M Nawaz Tahir ^b,^*, Zahid Shafiq ^a, Ashfaq Mahmood Qureshi ^a

PMCID: PMC3008043 PMID: 21588759

Abstract

In the title compound, C₁₄H₁₆N₂O₃S, the dihedral angle between the phenyl and 5-methylfuran groups is 54.89 (14)° and the C=N bond assumes a trans conformation. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R ₂ ²(8) ring motifs. The dimers are interlinked by N—H⋯N hydrogen bonds, resulting in the formation of infinite chains extending along the b axis. The packing is consolidated by weak C—H⋯π interactions.

Related literature

For biochemical background and related crystal structures, see: Chohan et al. (2008 ▶); Davis et al. (2007 ▶); Li (2006 ▶); Suo (2008 ▶); For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₁₆N₂O₃S
M _r = 292.35
Triclinic,
a = 9.1947 (14) Å
b = 9.7592 (14) Å
c = 9.8493 (15) Å
α = 61.027 (6)°
β = 70.650 (6)°
γ = 81.574 (7)°
V = 729.4 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.20 × 0.16 × 0.08 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.956, T _max = 0.977
10058 measured reflections
2638 independent reflections
1461 reflections with I > 2σ(I)
R _int = 0.068

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.153
S = 0.97
2638 reflections
188 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034045/hb5617sup1.cif

e-66-o2436-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034045/hb5617Isup2.hkl

e-66-o2436-Isup2.hkl^{(126.9KB, hkl)}

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

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

Cg1 and Cg2 are the centroids of furan (C10—C13/O3) and phenyl (C1—C6) rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.80 (4)	2.18 (4)	2.928 (5)	155 (4)
N1—H1B⋯N2ⁱⁱ	0.82 (4)	2.25 (5)	3.015 (5)	156 (5)
C6—H6⋯Cg1ⁱⁱⁱ	0.93	2.87	3.596 (4)	136
C11—H11⋯Cg2^iv	0.93	2.75	3.535 (4)	143
C14—H14C⋯Cg2^v	0.96	2.84	3.743 (5)	157

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

Acknowledgments

The authors would like to thank the Higher Education Commission (HEC), Pakistan, for financial assistance to KM under the National Research Program for Universities.

supplementary crystallographic information

Comment

The title compound (I, Fig. 1) is being reported here in the context of our new project of synthesizing Schiff basis of various sulfonamide drugs, studying their bio-activity and the formation of their metal complexes.

The crystal structures of (II) 4-(2-(3-ethyl-4-methyl-2-oxo-3-pyrrolidine-1-carboxamido)ethyl) benzenesulfonamide (Li, 2006), (III) N-(2-(4-(aminosulfonyl)phenyl)ethyl)-2-(4-hydroxyphenyl)acetamide (Davis et al., 2007), (IV) 4-(2-((5-chloro-2-hydroxybenzylidene)amino)ethyl)benzenesulfonamide (Chohan et al., 2008) and (V) (E)-4-[(5-methyl-2-furyl)methyleneamino]benzenesulfonic acid (Suo, 2008) have been published which are related to the title compound.

In (I), the thiophenol A (C1–C6/S1) and 5-methylfuran-2-yl B (C10–C14/O3) are planar with r. m. s. deviations of 0.0037 and 0.0029 Å, respectively. The dihedral angle between A/B is 54.89 (14)°. The S-atom is at a distance of -0.4487 (19) Å from the plane formed by (O1/O2/N1). The central group of N-methylideneethanamine makes a torsion angle of -136.6 (4)°. In the title compound an S(5) ring motif (Bernstein et al., 1995) is formed due to C—H···O type of intramolecular H-bonding. The molecules are dimerized due to N—H···O type of intermolecular H-bonding (Table 1, Fig. 2) with R₂²(8) ring motif. The dimers are interlinked through H-bondings of N—H···N type resulting in the formation of infinite one dimensional polymeric chains extending along the b axis. In the stabilization of molecules C—H···π interactions (Table 1) play an important role.

Experimental

An ethanol solution (15 ml) of sulfonamide (0.20 g, 1 mmol) was added to the solution of 5-methylfuran-2-carbaldehyde (0.099 ml, 1 mmol) in ethanol (10 ml). The reaction mixture was refluxed for 4 h. The solution was cooled to room temperature, filtered and volume reduced to about one-third using rotary evaporator. It was then allowed to stand for 5 days, after which dark yellow plates of (I) were obtained.