N-Benzo­ylbenzene­sulfonamide

Gowda, B.T.; Foro, S.; Suchetan, P.A.; Fuess, H.

doi:10.1107/S1600536809037222

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2516

doi:10.1107/S1600536809037222

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N-Benzoylbenzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. A. Suchetan ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287, Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 11 September 2009; accepted 14 September 2009; online 26 September 2009)

In the crystal structure of the title compound, C₁₃H₁₁NO₃S, the conformation of the N—H bond in the C—SO₂—NH—C(O)—C segment is anti to the C=O bond. The molecule is twisted at theN atom with a dihedral angle of 86.5(1)° between the sulfonyl benzene ring and the —SO₂—NH—C=O segment. Furthermore, the dihedral angle between the two benzene rings is 80.3(1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O(S) hydrogen bonds.

Related literature

For related structures, see: Gowda et al. (2008a ,b ; 2009 ).

Experimental

Crystal data

C₁₃H₁₁NO₃S
M_r = 261.29
Triclinic, $[P \overline 1]$
a = 5.8396 (7) Å
b = 10.178 (1) Å
c = 10.405 (1) Å
α = 90.187 (8)°
β = 99.074 (9)°
γ = 99.617 (9)°
V = 601.83 (11) Å³
Z = 2
Cu Kα radiation
μ = 2.40 mm⁻¹
T = 299 K
0.50 × 0.33 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan North et al., 1968 T_min = 0.380, T_max = 0.889
2354 measured reflections
2125 independent reflections
1962 reflections with I > 2σ(I)
R_int = 0.011
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.171
S = 1.18
2125 reflections
167 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.79 (3)	2.22 (3)	2.981 (4)	163 (4)
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809037222/tk2540sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037222/tk2540Isup2.hkl

checkCIF report

Comment top

Diaryl acylsulfonamides are known as potent anti-tumor agents against a broad spectrum of human tumor xenografts (colon, lung, breast, ovary, and prostate) in nude mice. As part of a study of the effect of ring and the side chain substituents on the solid-state structures of N-aromatic sulfonamides (Gowda et al., 2008a,b; 2009), in the present work the structure of N-(benzoyl)benzenesulfonamide (I) has been determined (Fig. 1). The conformation of the N—H bond in the structure is anti to the C═O bond in the side-chain, similar to that observed in the acid anilides. The conformation of the N—C bond in the C—SO₂—NH—C(O) segment of the structure has "gauche" torsions with respect to the SO bonds (Fig. 1). The molecule is twisted at the C(O) atom with the C—SO₂—NH—C(O) torsion angle being -66.9 (3)°. The packing of molecules via N—H···O(S) hydrogen bonds (Table 1) into supramolecular dimers is shown in Fig. 2.

Related literature top

For related structures, see: Gowda et al. (2008a,b; 2009).

Experimental top

Compound (I) was prepared by refluxing a mixture of benzoic acid, benzene sulfonamide and phosphorous oxy chloride for 5 h on a water bath. The resultant mixture was cooled and poured into ice-cold water. The solid obtained was filtered and washed thoroughly with water and then dissolved in sodium bicarbonate solution. Compound (I) was later reprecipitated by acidifying the filtered solution with dilute HCl. The filtered and dried solid was recrystallized to the constant melting point. The compound was characterized by its characteristic aromatic C—H stretching (3061.1 cm^-1), carbonyl C═O (1696.7 cm^-1), N—H stretching (3280.1 cm^-1), symmetric (1176.3 cm^-1), and asymmetric SO₂ (1335.1 cm^-1) infrared absorption frequencies.

Long colorless plates of (I) were obtained from a slow evaporation of its toluene solution at room temperature.

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

N-Benzoylbenzenesulfonamide top

Crystal data top

C₁₃H₁₁NO₃S	Z = 2
M_r = 261.29	F(000) = 272
Triclinic, P1	D_x = 1.442 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 5.8396 (7) Å	Cell parameters from 25 reflections
b = 10.178 (1) Å	θ = 4.3–22.9°
c = 10.405 (1) Å	µ = 2.40 mm⁻¹
α = 90.187 (8)°	T = 299 K
β = 99.074 (9)°	Long plate, colorless
γ = 99.617 (9)°	0.50 × 0.33 × 0.05 mm
V = 601.83 (11) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	1962 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.011
Graphite monochromator	θ_max = 66.9°, θ_min = 4.3°
ω/2θ scans	h = 0→6
Absorption correction: ψ scan North et al., 1968	k = −12→11
T_min = 0.380, T_max = 0.889	l = −12→12
2354 measured reflections	3 standard reflections every 120 min
2125 independent reflections	intensity decay: 1.0%

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)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.171	w = 1/[σ²(F_o²) + (0.0862P)² + 0.5464P] where P = (F_o² + 2F_c²)/3
S = 1.18	(Δ/σ)_max = 0.008
2125 reflections	Δρ_max = 0.65 e Å⁻³
167 parameters	Δρ_min = −0.36 e Å⁻³
7 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (3)

Crystal data top

C₁₃H₁₁NO₃S	γ = 99.617 (9)°
M_r = 261.29	V = 601.83 (11) Å³
Triclinic, P1	Z = 2
a = 5.8396 (7) Å	Cu Kα radiation
b = 10.178 (1) Å	µ = 2.40 mm⁻¹
c = 10.405 (1) Å	T = 299 K
α = 90.187 (8)°	0.50 × 0.33 × 0.05 mm
β = 99.074 (9)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1962 reflections with I > 2σ(I)
Absorption correction: ψ scan North et al., 1968	R_int = 0.011
T_min = 0.380, T_max = 0.889	3 standard reflections every 120 min
2354 measured reflections	intensity decay: 1.0%
2125 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	7 restraints
wR(F²) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	Δρ_max = 0.65 e Å⁻³
2125 reflections	Δρ_min = −0.36 e Å⁻³
167 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
C1	0.3607 (5)	0.8198 (3)	0.8908 (3)	0.0337 (6)
C2	0.2344 (5)	0.9229 (3)	0.8901 (3)	0.0407 (7)
H2	0.1021	0.9143	0.9307	0.049*
C3	0.3058 (7)	1.0380 (3)	0.8289 (4)	0.0539 (9)
H3	0.2219	1.1081	0.8283	0.065*
C4	0.5004 (7)	1.0503 (4)	0.7686 (4)	0.0589 (10)
H4	0.5482	1.1288	0.7274	0.071*
C5	0.6248 (6)	0.9472 (4)	0.7688 (4)	0.0583 (10)
H5	0.7553	0.9559	0.7266	0.070*
C6	0.5584 (5)	0.8304 (4)	0.8311 (3)	0.0470 (8)
H6	0.6442	0.7611	0.8329	0.056*
C7	0.0114 (5)	0.5480 (3)	0.7670 (3)	0.0400 (7)
C8	−0.0390 (5)	0.4316 (3)	0.6753 (3)	0.0368 (7)
C9	−0.2525 (6)	0.4135 (4)	0.5908 (3)	0.0500 (8)
H9	−0.3577	0.4717	0.5965	0.060*
C10	−0.3098 (6)	0.3115 (4)	0.4997 (4)	0.0602 (10)
H10	−0.4533	0.3009	0.4441	0.072*
C11	−0.1570 (7)	0.2248 (4)	0.4897 (4)	0.0564 (9)
H11	−0.1958	0.1557	0.4273	0.068*
C12	0.0539 (7)	0.2408 (4)	0.5727 (4)	0.0589 (10)
H12	0.1576	0.1818	0.5664	0.071*
C13	0.1137 (6)	0.3429 (4)	0.6649 (3)	0.0492 (8)
H13	0.2571	0.3526	0.7205	0.059*
N1	0.2045 (5)	0.5551 (3)	0.8642 (3)	0.0436 (7)
H1N	0.262 (7)	0.491 (3)	0.882 (4)	0.052*
O1	0.4799 (5)	0.6424 (2)	1.0568 (3)	0.0629 (8)
O2	0.0786 (5)	0.6940 (3)	1.0349 (3)	0.0597 (7)
O3	−0.1033 (4)	0.6374 (3)	0.7564 (3)	0.0562 (7)
S1	0.27661 (14)	0.67612 (7)	0.97654 (7)	0.0416 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0246 (13)	0.0344 (14)	0.0396 (15)	0.0060 (10)	−0.0030 (11)	−0.0037 (11)
C2	0.0305 (15)	0.0399 (16)	0.0508 (18)	0.0101 (12)	−0.0009 (12)	−0.0029 (13)
C3	0.054 (2)	0.0397 (17)	0.064 (2)	0.0116 (15)	−0.0085 (17)	0.0005 (15)
C4	0.057 (2)	0.049 (2)	0.058 (2)	−0.0084 (16)	−0.0088 (18)	0.0092 (16)
C5	0.0344 (17)	0.081 (3)	0.054 (2)	−0.0073 (17)	0.0082 (15)	−0.0003 (18)
C6	0.0320 (16)	0.059 (2)	0.0508 (18)	0.0136 (14)	0.0041 (13)	−0.0049 (15)
C7	0.0280 (15)	0.0441 (17)	0.0469 (17)	0.0057 (12)	0.0030 (12)	0.0036 (13)
C8	0.0280 (14)	0.0415 (16)	0.0392 (15)	0.0050 (11)	0.0013 (11)	0.0046 (12)
C9	0.0314 (16)	0.063 (2)	0.0534 (19)	0.0125 (14)	−0.0044 (14)	−0.0042 (16)
C10	0.0408 (19)	0.076 (3)	0.056 (2)	0.0057 (17)	−0.0116 (16)	−0.0082 (18)
C11	0.061 (2)	0.056 (2)	0.0469 (19)	0.0034 (17)	−0.0017 (16)	−0.0092 (16)
C12	0.061 (2)	0.062 (2)	0.055 (2)	0.0257 (18)	−0.0035 (17)	−0.0090 (17)
C13	0.0401 (17)	0.056 (2)	0.0486 (18)	0.0154 (14)	−0.0082 (14)	−0.0067 (15)
N1	0.0414 (15)	0.0331 (13)	0.0525 (16)	0.0104 (11)	−0.0086 (12)	0.0001 (12)
O1	0.0787 (18)	0.0431 (13)	0.0567 (15)	0.0186 (12)	−0.0293 (13)	−0.0018 (11)
O2	0.0647 (16)	0.0593 (15)	0.0575 (15)	0.0008 (12)	0.0278 (13)	−0.0007 (12)
O3	0.0414 (13)	0.0604 (15)	0.0686 (16)	0.0248 (11)	−0.0031 (11)	−0.0111 (12)
S1	0.0460 (5)	0.0348 (5)	0.0405 (5)	0.0062 (3)	−0.0023 (3)	0.0006 (3)

Geometric parameters (Å, º) top

C1—C2	1.379 (4)	C8—C13	1.385 (5)
C1—C6	1.384 (4)	C8—C9	1.392 (4)
C1—S1	1.756 (3)	C9—C10	1.366 (5)
C2—C3	1.370 (5)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.370 (6)
C3—C4	1.370 (6)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.373 (5)
C4—C5	1.373 (6)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.375 (5)
C5—C6	1.383 (5)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	N1—S1	1.650 (3)
C7—O3	1.212 (4)	N1—H1N	0.79 (3)
C7—N1	1.383 (4)	O1—S1	1.432 (2)
C7—C8	1.479 (4)	O2—S1	1.425 (3)

C2—C1—C6	121.3 (3)	C10—C9—C8	121.0 (3)
C2—C1—S1	119.0 (2)	C10—C9—H9	119.5
C6—C1—S1	119.6 (2)	C8—C9—H9	119.5
C3—C2—C1	119.4 (3)	C9—C10—C11	120.4 (3)
C3—C2—H2	120.3	C9—C10—H10	119.8
C1—C2—H2	120.3	C11—C10—H10	119.8
C4—C3—C2	120.3 (3)	C10—C11—C12	119.4 (3)
C4—C3—H3	119.9	C10—C11—H11	120.3
C2—C3—H3	119.9	C12—C11—H11	120.3
C3—C4—C5	120.2 (3)	C11—C12—C13	120.8 (3)
C3—C4—H4	119.9	C11—C12—H12	119.6
C5—C4—H4	119.9	C13—C12—H12	119.6
C4—C5—C6	120.8 (3)	C12—C13—C8	120.2 (3)
C4—C5—H5	119.6	C12—C13—H13	119.9
C6—C5—H5	119.6	C8—C13—H13	119.9
C1—C6—C5	118.1 (3)	C7—N1—S1	122.6 (2)
C1—C6—H6	121.0	C7—N1—H1N	120 (3)
C5—C6—H6	121.0	S1—N1—H1N	114 (3)
O3—C7—N1	120.1 (3)	O2—S1—O1	119.09 (18)
O3—C7—C8	122.6 (3)	O2—S1—N1	110.97 (15)
N1—C7—C8	117.2 (3)	O1—S1—N1	103.63 (14)
C13—C8—C9	118.2 (3)	O2—S1—C1	108.38 (15)
C13—C8—C7	124.8 (3)	O1—S1—C1	109.23 (15)
C9—C8—C7	117.0 (3)	N1—S1—C1	104.55 (14)

C6—C1—C2—C3	0.1 (5)	C10—C11—C12—C13	−0.3 (6)
S1—C1—C2—C3	176.8 (2)	C11—C12—C13—C8	0.0 (6)
C1—C2—C3—C4	0.2 (5)	C9—C8—C13—C12	0.3 (5)
C2—C3—C4—C5	0.1 (5)	C7—C8—C13—C12	−177.3 (3)
C3—C4—C5—C6	−0.9 (5)	O3—C7—N1—S1	5.1 (4)
C2—C1—C6—C5	−0.9 (5)	C8—C7—N1—S1	−177.7 (2)
S1—C1—C6—C5	−177.5 (2)	C7—N1—S1—O2	49.8 (3)
C4—C5—C6—C1	1.3 (5)	C7—N1—S1—O1	178.7 (3)
O3—C7—C8—C13	164.9 (3)	C7—N1—S1—C1	−66.9 (3)
N1—C7—C8—C13	−12.2 (5)	C2—C1—S1—O2	−0.3 (3)
O3—C7—C8—C9	−12.7 (5)	C6—C1—S1—O2	176.3 (2)
N1—C7—C8—C9	170.2 (3)	C2—C1—S1—O1	−131.5 (2)
C13—C8—C9—C10	−0.3 (5)	C6—C1—S1—O1	45.2 (3)
C7—C8—C9—C10	177.5 (3)	C2—C1—S1—N1	118.1 (2)
C8—C9—C10—C11	−0.1 (6)	C6—C1—S1—N1	−65.2 (3)
C9—C10—C11—C12	0.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.79 (3)	2.22 (3)	2.981 (4)	163 (4)

Symmetry code: (i) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁NO₃S
M_r	261.29
Crystal system, space group	Triclinic, P1
Temperature (K)	299
a, b, c (Å)	5.8396 (7), 10.178 (1), 10.405 (1)
α, β, γ (°)	90.187 (8), 99.074 (9), 99.617 (9)
V (Å³)	601.83 (11)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.40
Crystal size (mm)	0.50 × 0.33 × 0.05

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan North et al., 1968
T_min, T_max	0.380, 0.889
No. of measured, independent and observed [I > 2σ(I)] reflections	2354, 2125, 1962
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.171, 1.18
No. of reflections	2125
No. of parameters	167
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.36

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.79 (3)	2.22 (3)	2.981 (4)	163 (4)

Symmetry code: (i) −x+1, −y+1, −z+2.

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for an extension of his research fellowship.

References

Enraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008a). Acta Cryst. E64, o1692. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008b). Acta Cryst. E64, o1825. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G., Terao, H. & Fuess, H. (2009). Acta Cryst. E65, o1219. Web of Science CSD CrossRef IUCr Journals Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany. Google Scholar