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

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

doi:10.1107/S1600536811050495

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3491

https://doi.org/10.1107/S1600536811050495

Open

access

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

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

^aCenter for Advanced Materials and Department of Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, ^bDepartment of PG Studies and Research in Physics, Tumkur University, Tumkur, Karnataka 572 103, India, and ^cDepartment of Chemistry, Kuvempu University, Shankaraghatta, Shimoga, Karnataka, India
^*Correspondence e-mail: spal12pm@gmail.com

(Received 14 September 2011; accepted 24 November 2011; online 30 November 2011)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.041
wR(F²) = 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

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)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811050495/ds2146sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050495/ds2146Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811050495/ds2146Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Structure description top

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

Computing details top

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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom-labllling scheme.
	Fig. 2. Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₁₉H₁₃NO₄S	F(000) = 728
M_r = 351.36	1.447 Mg m-3
Monoclinic, P2₁/c	D_x = 1.447 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.8504 (10) Å	Cell parameters from 2986 reflections
b = 12.2166 (8) Å	θ = 2.2°
c = 9.7164 (6) Å	µ = 0.23 mm⁻¹
β = 101.248 (2)°	T = 299 K
V = 1612.48 (19) Å³	Prism, colourless
Z = 4	0.35 × 0.3 × 0.25 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2986 independent reflections
Radiation source: fine-focus sealed tube	2394 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
phi and scans	θ_max = 25.5°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.924, T_max = 0.945	k = −14→14
15289 measured reflections	l = −11→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.133	w = 1/[σ²(F_o²) + (0.0827P)² + 1.1854P] where P = (F_o² + 2F_c²)/3
S = 0.85	(Δ/σ)_max = 0.001
2986 reflections	Δρ_max = 0.25 e Å⁻³
231 parameters	Δρ_min = −0.38 e Å⁻³
1 restraint	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0054 (12)

Crystal data top

C₁₉H₁₃NO₄S	V = 1612.48 (19) Å³
M_r = 351.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.8504 (10) Å	µ = 0.23 mm⁻¹
b = 12.2166 (8) Å	T = 299 K
c = 9.7164 (6) Å	0.35 × 0.3 × 0.25 mm
β = 101.248 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2986 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2394 reflections with I > 2σ(I)
T_min = 0.924, T_max = 0.945	R_int = 0.027
15289 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	Δρ_max = 0.25 e Å⁻³
2986 reflections	Δρ_min = −0.38 e Å⁻³
231 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
H1N	0.8221 (19)	0.1816 (19)	0.346 (3)	0.053 (8)*
S1	0.72588 (4)	0.25754 (5)	0.18450 (6)	0.0566 (2)
N1	0.82025 (14)	0.24177 (18)	0.3158 (2)	0.0527 (5)
O1	0.69636 (15)	0.14945 (17)	0.1467 (2)	0.0910 (7)
O2	0.75502 (14)	0.3299 (2)	0.08507 (18)	0.0853 (7)
O3	0.85990 (12)	0.42070 (13)	0.35980 (18)	0.0626 (5)
O4	0.96215 (10)	0.17651 (11)	0.52390 (14)	0.0448 (4)
C1	1.14610 (14)	0.26862 (18)	0.8155 (2)	0.0430 (5)
C2	1.18623 (16)	0.3662 (2)	0.8774 (2)	0.0545 (6)
H2	1.1644	0.4332	0.8376	0.065*
C3	1.25770 (18)	0.3628 (3)	0.9968 (2)	0.0663 (7)
H3	1.2841	0.4278	1.0377	0.08*
C4	1.29114 (18)	0.2631 (3)	1.0575 (3)	0.0703 (8)
H4	1.3395	0.2621	1.1387	0.084*
C5	1.25403 (17)	0.1678 (3)	0.9995 (2)	0.0636 (7)
H5	1.2771	0.102	1.0416	0.076*
C6	1.18038 (15)	0.16646 (19)	0.8755 (2)	0.0488 (5)
C7	1.14042 (17)	0.0666 (2)	0.8153 (2)	0.0566 (6)
H7	1.1644	0.0011	0.8573	0.068*
C8	1.06823 (17)	0.06330 (19)	0.6984 (2)	0.0550 (6)
H8	1.0426	−0.0025	0.6593	0.066*
C9	1.03480 (14)	0.16388 (17)	0.6404 (2)	0.0425 (5)
C10	1.06976 (14)	0.26419 (16)	0.6922 (2)	0.0395 (4)
C11	1.01546 (14)	0.34374 (17)	0.6020 (2)	0.0412 (4)
H11	1.0225	0.4194	0.609	0.049*
C12	0.95188 (13)	0.28806 (17)	0.5044 (2)	0.0404 (4)
C13	0.87507 (14)	0.32539 (18)	0.3889 (2)	0.0430 (5)
C14	0.63289 (15)	0.3220 (2)	0.2518 (2)	0.0502 (5)
C16	0.4993 (2)	0.3091 (5)	0.3712 (4)	0.1040 (13)
H16	0.4601	0.2673	0.4186	0.125*
C15	0.57551 (19)	0.2612 (3)	0.3241 (3)	0.0725 (8)
H15	0.5888	0.1872	0.3409	0.087*
C19	0.6169 (2)	0.4313 (3)	0.2335 (4)	0.0876 (9)
H19	0.6567	0.4741	0.1882	0.105*
C17	0.4807 (3)	0.4141 (5)	0.3499 (5)	0.1213 (18)
H17	0.4271	0.445	0.3801	0.146*
C18	0.5377 (3)	0.4776 (4)	0.2854 (5)	0.1210 (15)
H18	0.5249	0.5522	0.275	0.145*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0409 (3)	0.0788 (5)	0.0460 (3)	0.0105 (3)	−0.0012 (2)	−0.0159 (3)
N1	0.0427 (10)	0.0551 (13)	0.0552 (11)	0.0046 (8)	−0.0028 (8)	−0.0053 (9)
O1	0.0699 (12)	0.0851 (14)	0.1006 (15)	0.0202 (10)	−0.0264 (11)	−0.0464 (12)
O2	0.0582 (10)	0.154 (2)	0.0440 (9)	0.0078 (12)	0.0119 (8)	0.0091 (11)
O3	0.0571 (9)	0.0564 (10)	0.0672 (10)	−0.0011 (8)	−0.0051 (8)	0.0136 (8)
O4	0.0406 (7)	0.0441 (8)	0.0477 (8)	0.0006 (6)	0.0034 (6)	−0.0032 (6)
C1	0.0329 (10)	0.0591 (13)	0.0383 (10)	−0.0002 (8)	0.0104 (8)	0.0039 (9)
C2	0.0465 (12)	0.0679 (15)	0.0478 (12)	−0.0094 (10)	0.0056 (9)	0.0003 (10)
C3	0.0515 (13)	0.092 (2)	0.0534 (13)	−0.0177 (13)	0.0049 (11)	−0.0072 (13)
C4	0.0443 (13)	0.118 (2)	0.0443 (13)	−0.0070 (14)	−0.0007 (10)	0.0093 (14)
C5	0.0421 (12)	0.098 (2)	0.0498 (13)	0.0085 (13)	0.0078 (10)	0.0199 (13)
C6	0.0367 (10)	0.0675 (14)	0.0442 (11)	0.0060 (9)	0.0127 (9)	0.0108 (10)
C7	0.0541 (13)	0.0563 (14)	0.0599 (13)	0.0134 (11)	0.0124 (11)	0.0145 (11)
C8	0.0574 (13)	0.0458 (13)	0.0615 (13)	0.0057 (10)	0.0104 (11)	0.0033 (10)
C9	0.0364 (10)	0.0466 (11)	0.0444 (10)	0.0023 (8)	0.0082 (8)	0.0011 (9)
C10	0.0319 (9)	0.0480 (11)	0.0392 (10)	0.0002 (8)	0.0084 (8)	0.0028 (8)
C11	0.0387 (10)	0.0414 (11)	0.0436 (10)	−0.0016 (8)	0.0082 (8)	0.0009 (8)
C12	0.0350 (9)	0.0430 (11)	0.0441 (10)	0.0011 (8)	0.0096 (8)	0.0012 (8)
C13	0.0360 (10)	0.0519 (13)	0.0413 (10)	0.0003 (9)	0.0084 (8)	0.0004 (9)
C14	0.0348 (10)	0.0639 (14)	0.0491 (11)	0.0011 (9)	0.0009 (9)	−0.0112 (10)
C16	0.0497 (17)	0.190 (4)	0.075 (2)	−0.017 (2)	0.0200 (15)	−0.028 (3)
C15	0.0501 (14)	0.102 (2)	0.0630 (15)	−0.0128 (13)	0.0048 (12)	−0.0044 (14)
C19	0.0656 (17)	0.072 (2)	0.124 (3)	0.0113 (14)	0.0167 (17)	−0.0006 (18)
C17	0.0517 (18)	0.186 (5)	0.124 (3)	0.007 (3)	0.011 (2)	−0.077 (3)
C18	0.091 (3)	0.094 (3)	0.170 (4)	0.035 (2)	0.007 (3)	−0.037 (3)

Geometric parameters (Å, º) top

S1—O1	1.410 (2)	C7—C8	1.360 (3)
S1—O2	1.425 (2)	C7—H7	0.93
S1—N1	1.650 (2)	C8—C9	1.393 (3)
S1—C14	1.742 (2)	C8—H8	0.93
N1—C13	1.383 (3)	C9—C10	1.376 (3)
N1—H1N	0.79 (2)	C10—C11	1.422 (3)
O3—C13	1.207 (2)	C11—C12	1.346 (3)
O4—C9	1.369 (2)	C11—H11	0.93
O4—C12	1.379 (2)	C12—C13	1.461 (3)
C1—C2	1.400 (3)	C14—C19	1.360 (4)
C1—C6	1.419 (3)	C14—C15	1.377 (3)
C1—C10	1.436 (3)	C16—C17	1.316 (6)
C2—C3	1.371 (3)	C16—C15	1.362 (5)
C2—H2	0.93	C16—H16	0.93
C3—C4	1.393 (4)	C15—H15	0.93
C3—H3	0.93	C19—C18	1.412 (5)
C4—C5	1.350 (4)	C19—H19	0.93
C4—H4	0.93	C17—C18	1.346 (6)
C5—C6	1.419 (3)	C17—H17	0.93
C5—H5	0.93	C18—H18	0.93
C6—C7	1.418 (3)

O1—S1—O2	120.71 (14)	O4—C9—C10	110.56 (17)
O1—S1—N1	103.77 (12)	O4—C9—C8	124.53 (19)
O2—S1—N1	108.08 (11)	C10—C9—C8	124.91 (19)
O1—S1—C14	108.85 (12)	C9—C10—C11	106.10 (17)
O2—S1—C14	107.57 (12)	C9—C10—C1	119.19 (18)
N1—S1—C14	107.12 (10)	C11—C10—C1	134.70 (19)
C13—N1—S1	125.68 (18)	C12—C11—C10	106.48 (18)
C13—N1—H1N	121.3 (19)	C12—C11—H11	126.8
S1—N1—H1N	111.1 (19)	C10—C11—H11	126.8
C9—O4—C12	105.34 (15)	C11—C12—O4	111.50 (17)
C2—C1—C6	119.94 (19)	C11—C12—C13	131.45 (19)
C2—C1—C10	123.80 (19)	O4—C12—C13	117.01 (17)
C6—C1—C10	116.25 (19)	O3—C13—N1	122.6 (2)
C3—C2—C1	119.9 (2)	O3—C13—C12	123.26 (19)
C3—C2—H2	120.1	N1—C13—C12	114.10 (19)
C1—C2—H2	120.1	C19—C14—C15	120.1 (2)
C2—C3—C4	120.7 (2)	C19—C14—S1	120.5 (2)
C2—C3—H3	119.7	C15—C14—S1	119.4 (2)
C4—C3—H3	119.7	C17—C16—C15	120.4 (4)
C5—C4—C3	120.6 (2)	C17—C16—H16	119.8
C5—C4—H4	119.7	C15—C16—H16	119.8
C3—C4—H4	119.7	C16—C15—C14	120.1 (4)
C4—C5—C6	121.1 (2)	C16—C15—H15	119.9
C4—C5—H5	119.4	C14—C15—H15	119.9
C6—C5—H5	119.4	C14—C19—C18	117.7 (3)
C1—C6—C5	117.8 (2)	C14—C19—H19	121.2
C1—C6—C7	120.97 (19)	C18—C19—H19	121.2
C5—C6—C7	121.2 (2)	C16—C17—C18	121.4 (4)
C8—C7—C6	122.3 (2)	C16—C17—H17	119.3
C8—C7—H7	118.8	C18—C17—H17	119.3
C6—C7—H7	118.8	C17—C18—C19	120.2 (4)
C7—C8—C9	116.4 (2)	C17—C18—H18	119.9
C7—C8—H8	121.8	C19—C18—H18	119.9
C9—C8—H8	121.8

O1—S1—N1—C13	179.8 (2)	C6—C1—C10—C11	179.5 (2)
O2—S1—N1—C13	50.5 (2)	C9—C10—C11—C12	0.6 (2)
C14—S1—N1—C13	−65.2 (2)	C1—C10—C11—C12	−178.9 (2)
C6—C1—C2—C3	−0.8 (3)	C10—C11—C12—O4	−0.9 (2)
C10—C1—C2—C3	178.7 (2)	C10—C11—C12—C13	177.01 (19)
C1—C2—C3—C4	0.1 (4)	C9—O4—C12—C11	0.8 (2)
C2—C3—C4—C5	0.2 (4)	C9—O4—C12—C13	−177.41 (15)
C3—C4—C5—C6	0.2 (4)	S1—N1—C13—O3	−2.0 (3)
C2—C1—C6—C5	1.1 (3)	S1—N1—C13—C12	177.46 (15)
C10—C1—C6—C5	−178.44 (17)	C11—C12—C13—O3	3.4 (3)
C2—C1—C6—C7	179.6 (2)	O4—C12—C13—O3	−178.81 (18)
C10—C1—C6—C7	0.0 (3)	C11—C12—C13—N1	−176.1 (2)
C4—C5—C6—C1	−0.8 (3)	O4—C12—C13—N1	1.7 (2)
C4—C5—C6—C7	−179.3 (2)	O1—S1—C14—C19	−147.8 (2)
C1—C6—C7—C8	0.1 (3)	O2—S1—C14—C19	−15.4 (2)
C5—C6—C7—C8	178.5 (2)	N1—S1—C14—C19	100.6 (2)
C6—C7—C8—C9	−0.3 (3)	O1—S1—C14—C15	32.2 (2)
C12—O4—C9—C10	−0.4 (2)	O2—S1—C14—C15	164.60 (19)
C12—O4—C9—C8	179.38 (19)	N1—S1—C14—C15	−79.4 (2)
C7—C8—C9—O4	−179.39 (19)	C17—C16—C15—C14	−1.1 (5)
C7—C8—C9—C10	0.4 (3)	C19—C14—C15—C16	3.4 (4)
O4—C9—C10—C11	−0.1 (2)	S1—C14—C15—C16	−176.6 (2)
C8—C9—C10—C11	−179.9 (2)	C15—C14—C19—C18	−2.7 (4)
O4—C9—C10—C1	179.47 (15)	S1—C14—C19—C18	177.3 (3)
C8—C9—C10—C1	−0.3 (3)	C15—C16—C17—C18	−2.0 (6)
C2—C1—C10—C9	−179.43 (19)	C16—C17—C18—C19	2.7 (7)
C6—C1—C10—C9	0.1 (3)	C14—C19—C18—C17	−0.3 (6)
C2—C1—C10—C11	0.0 (3)

Hydrogen-bond geometry (Å, º) top

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)
C19—H19···O2	0.93	2.55	2.890 (4)	102
N1—H1N···O2ⁱ	0.79 (3)	2.66 (1)	3.057 (2)	113 (2)

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₃NO₄S
M_r	351.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	299
a, b, c (Å)	13.8504 (10), 12.2166 (8), 9.7164 (6)
β (°)	101.248 (2)
V (Å³)	1612.48 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.35 × 0.3 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.924, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	15289, 2986, 2394
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.133, 0.85
No. of reflections	2986
No. of parameters	231
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.38

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

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)	2.656 (3)	3.057 (2)	113 (2)

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

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.

References

Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010). Acta Cryst. E66, o1284. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar