N-(Phenyl­sulfon­yl)naphtho­[2,1-b]furan-1-carboxamide

M Shetprakash; P A Suchetan; B S Palakshamurthy; K M Mahadevan; V P Vaidya

doi:10.1107/S1600536811050495

. 2011 Nov 30;67(Pt 12):o3491. doi: 10.1107/S1600536811050495

N-(Phenylsulfonyl)naphtho[2,1-b]furan-1-carboxamide

M Shetprakash ^a, P A Suchetan ^a, B S Palakshamurthy ^b,^*, K M Mahadevan ^c, V P Vaidya ^c

PMCID: PMC3239115 PMID: 22199963

Abstract

In the title compound, C₁₉H₁₃NO₄S, the molecule is twisted at the S atom with a C—S—N—C torsion angle of −65.2 (2)° between the benzene ring and the –SO₂—NH—C=O segment. The dihedral angle between the benzene and the naphthofuran ring system is 83.3 (1)°. In the crystal, molecules are linked by N—H⋯O hydrogen bonds into chains running along the c axis. An intramolecular N—H⋯O(furan) interaction is also observed.

Related literature

For related structures, see: Gowda et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C₁₉H₁₃NO₄S
M _r = 351.36
Monoclinic,
a = 13.8504 (10) Å
b = 12.2166 (8) Å
c = 9.7164 (6) Å
β = 101.248 (2)°
V = 1612.48 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 299 K
0.35 × 0.3 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.924, T _max = 0.945
15289 measured reflections
2986 independent reflections
2394 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.133
S = 0.85
2986 reflections
231 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811050495/ds2146sup1.cif

e-67-o3491-sup1.cif^{(19.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050495/ds2146Isup2.hkl

e-67-o3491-Isup2.hkl^{(146.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811050495/ds2146Isup3.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—H1N⋯O4	0.79 (3)	2.33 (3)	2.653 (2)	106 (2)
N1—H1N⋯O2ⁱ	0.79 (3)	2.66 (1)	3.057 (2)	113 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge Dr K. Gunasekaran and Jagadeesan CAS in Crystallography and Biophysics, University of Madras, and Dr H. C. Devarajegowda, Yuvaraja’s College, Mysore, for useful discusions. The Department of Chemistry, IIT Madras, is acknowledged for the data collection.

supplementary crystallographic information

Comment

Aryl Acyl sulfonamides are known as a potent antitumor agent against a broad spectrum of human tumor xenografts in nude mice. Further,the title compound exhibits antibacterial and antifungal activities (our unpublished results). In order to study the effect of the ring substituents on the solid-state structures of N-naphthofuroyl-sulfonamides, in the present work the structure of N-(Naphthofuroyl)benzenesulfonamide has been determined. The title compound (I) crystallizes in Monoclinic P2₁/c space group compared to N-(benzoyl)benzenesulfonamide (II) (Gowda et al., 2009) and N-(Phenylsulfonyl)acetamide (III)(Gowda et al., 2010) which crystallizes in Triclinic P-1 and Tetragonal P4₃space groups respectively. In III, the packing of molecules is linked by N—H···.O(C) hydrogen bonds and in II by N—H···.O(S) bonds, whereas in I, the molecules are linked by intermolecular N—H···.O(S) hydrogen bonds. Intramolecular C—H···..O(S) and N—H···..O(furan) interactions are also observed.The molecules are twisted at S atoms with the C—S(O2)—NH—C(O) torsion angle of -65.2 (2)°, compared to the values of -66.9 (3)° in (II) and -58.8 (4)° in (III). The dihedral angle between the benzene ring and the naphthofuran ring in (I) is 83.3 (1)°, compared to 80.3 (1)° observed between the two benzene rings in (II) and 38.7 (0)° in (III) between the benzene ring and the mean plane of CH3 fragement respectively. The packing of the molecules via intermolecular N—H···.O(S) hydrogen bonds is shown in Fig. 2.

Experimental

The title compound was prepared by refluxing a mixture of naphthofuran-2-carboxylic acid (10 mmol),benzenesulfonamide(10 mmol) and phosphorous oxychloride for 1 h on a water bath.The resultant mixture was cooled and poured into ice cold water. The solid, N-(Naphthofuroyl)benzenesulfonamide obtained was filtered, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute hydrochloric acid. The filtered and dried compound was recrystallized to constant melting point. The compound was characterized by its characteristic carbonyl C=O stretching (1698.2 cm-1), N—H stretching (3233.1 cm-1), symmetric SO2(1173.3 cm-1) and asymmetric SO2 (1326.2 cm-1) infrared absorption frequencies. Single crystals suitable for x-ray diffraction were grown from a slow evaporation of its ethanolic solution at room temperature.