(E)-4-Amino-N-(1,2-dihydro­pyridin-2-yl­idene)benzene­sulfonamide nitro­methane monosolvate

Mostafa M Ghorab; Mansour S Al-Said; Hazem A Ghabbour; Suchada Chantrapromma; Hoong-Kun Fun

doi:10.1107/S1600536812009865

. 2012 Mar 10;68(Pt 4):o1030. doi: 10.1107/S1600536812009865

(E)-4-Amino-N-(1,2-dihydropyridin-2-ylidene)benzenesulfonamide nitromethane monosolvate

Mostafa M Ghorab ^a, Mansour S Al-Said ^a, Hazem A Ghabbour ^b, Suchada Chantrapromma ^c,^‡, Hoong-Kun Fun ^d,^*,^§

PMCID: PMC3343993 PMID: 22589902

Abstract

In the title solvate, C₁₁H₁₁N₃O₂S·CH₃NO₂, the dihedral angle between the benzene ring and the N-containing ring is 85.94 (11)°, and an approximate V shape arises for the sulfonamide molecule. In the crystal, N—H⋯O and N—H⋯N hydrogen bonds and weak C—H⋯O interactions link the sulfonamide molecules into a three-dimensional network. The nitromethane solvent molecules are located in the interstitial sites in the sulfonamide network.

Related literature

For background to the applications of sulfonamide compounds, see: Ghorab et al. (2009 ▶);

Experimental

Crystal data

C₁₁H₁₁N₃O₂S·CH₃NO₂
M _r = 310.34
Orthorhombic,
a = 10.5179 (3) Å
b = 12.4857 (3) Å
c = 22.7237 (6) Å
V = 2984.15 (14) Å³
Z = 8
Cu Kα radiation
μ = 2.14 mm⁻¹
T = 296 K
0.54 × 0.43 × 0.31 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.392, T _max = 0.554
14569 measured reflections
2799 independent reflections
2386 reflections with I > 2σ(I)
R _int = 0.062

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.144
S = 1.07
2799 reflections
196 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812009865/hb6660sup1.cif

e-68-o1030-sup1.cif^{(24.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009865/hb6660Isup2.hkl

e-68-o1030-Isup2.hkl^{(137.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812009865/hb6660Isup3.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
N2—H1N2⋯O2ⁱ	0.87	2.10	2.971 (3)	174
N2—H2N2⋯O1ⁱⁱ	0.87	2.34	3.162 (3)	157
N3—H1N3⋯N1ⁱⁱⁱ	0.86 (2)	2.09 (2)	2.948 (2)	178 (2)
C8—H8A⋯O1ⁱⁱⁱ	0.93	2.52	3.160 (3)	126

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

Acknowledgments

The authors are grateful for the sponsorship of the Research Center, College of Pharmacy and the Deanship of Scientific Research, King Saud University, Riyadh, Saudi Arabia. HKF and SC thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. HKF also thanks the King Saud University, Riyadh, Saudi Arabia, for the award of a visiting Professorship (December 23rd 2011 to January 14th 2012).

supplementary crystallographic information

Comment

As part of our ongoing studies of sulfonamides with potential biological activities (Ghorab et al. (2009), the present investigation deals with the synthesis of the title compound, (I), (Fig. 1) a sulfonamide bearing a pyridine moiety to be evaluated as anticancer agent.

The environment of S atom is distorted tetrahedral geometry [angles around S atom are 104.49 (9) - 115.82 (10)°] with two O atoms, one N atom of the amide group and one C atom of the benzene ring. The dihedral angle between the benzene ring and the N atom-containing ring is 85.94 (11)°. The amino group is co-planar with its bound benzene ring with r.m.s. 0.0126 (2) Å for the seven non H atoms (C1–C6/N2).

In the crystal (Fig. 2), the molecules of sulfonamide derivative are linked by N—H···O and N—H···N hydrogen bonds and weak C···H···O interactions (Table 1) into a three dimensional network. The nitromethane solvent molecules are located in the interstitial sites of the sulfonamide network.

Experimental

A mixture of (E)-3-(dimethylamino)-1-(thiophen-2-yl)prop-2-en-1-one (1.81 g, 0.01 mole) and sulfapyridine (2.49 g, 0.01 mole) in absolute ethanol (30 ml) was heated under reflux for 12 hr. The reaction mixture was filtered and pink blocks of (I) were obtained by the slow evaporation of an ethanol/nitromethane (3:1) solution at room temperature.