N-(4-Chloro­benzo­yl)benzene­sulfonamide

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

doi:10.1107/S1600536809048399

organic compounds

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Volume 65| Part 12| December 2009| Page o3156

doi:10.1107/S1600536809048399

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N-(4-Chlorobenzoyl)benzenesulfonamide

P. A. Suchetan,^a B. Thimme Gowda,^a ^* Sabine Foro ^b 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 14 November 2009; accepted 14 November 2009; online 21 November 2009)

In the crystal structure of the title compound, C₁₃H₁₀ClNO₃S, the conformation of the N—H bond in the C—SO₂—NH—C(O) segment is anti to the C=O bond. The dihedral angle between the two aromatic rings is 68.6 (1)°. The molecule is twisted at the S atom with a dihedral angle of 75.7 (1)° between the sulfonyl benzene ring and the —SO₂—NH—C—O segment; the dihedral angle between the latter and the benzoyl ring is 8.3 (2)°. In the crystal, molecules are linked by N—H⋯O(S) hydrogen bonds.

Related literature

For background literature and similar structures, see: Gowda et al. (2008 , 2009a ,b ).

Experimental

Crystal data

C₁₃H₁₀ClNO₃S
M_r = 295.73
Triclinic, $[P \overline 1]$
a = 5.4176 (4) Å
b = 10.717 (1) Å
c = 10.980 (1) Å
α = 86.666 (9)°
β = 83.903 (9)°
γ = 81.823 (8)°
V = 626.85 (9) Å³
Z = 2
Cu Kα radiation
μ = 4.30 mm⁻¹
T = 296 K
0.48 × 0.42 × 0.23 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.232, T_max = 0.438
2490 measured reflections
2233 independent reflections
2058 reflections with I > 2σ(I)
R_int = 0.014
3 standard reflections frequency: 120 min intensity decay: 1.5%

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.152
S = 1.07
2233 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.86	2.47	3.281 (3)	158
Symmetry code: (i) x+1, y, z.

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/S1600536809048399/ng2687sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048399/ng2687Isup2.hkl

checkCIF report

Comment top

Diaryl acylsulfonamides are known as potent antitumor 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 crystal structures of N-aromatic sulfonamides (Gowda et al., 2008, 2009a,b), in the present work, the structure of N-(4-chlorobenzoyl)benzenesulfonamide (I) has been determined (Fig.1). The conformation of the N—H bond in the C—SO₂—NH—C(O) segment of the structure is anti to the C=O bond, similar to that observed in N-(benzoyl)benzenesulfonamide (II) (Gowda et al., 2009a) and N-(3-chlorobenzoyl)- benzenesulfonamide (III)(Gowda et al., 2009b). The molecule is twisted at the S atom with a dihedral angle of 75.7 (1)° between the sulfonyl benzene ring and the C—SO₂—NH—C—O segment, compared to the values of 86.5(0.1) in (II) and 89.9 (1)° in (III). Furthermore, the dihedral angle between the two benzene rings is 68.6 (1)° in (I) and 80.3(0.1) in (II) and 87.5 (1)° in (III). The packing of molecules linked by of N—H···O(S) hydrogen bonds (Table 1) is shown in Fig. 2.

Related literature top

For background literature and similar structures, see: Gowda et al. (2008, 2009a,b).

Experimental top

The title compound was prepared by refluxing a mixture of 4-chlorobenzoic 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, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The filtered and dried solid was recrystallized to the constant melting point.

Rod like colourless single crystals of the title compound were obtained from a slow evaporation of its toluene solution at room temperature and the X-ray diffraction studies were also carried out 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-(4-Chlorobenzoyl)benzenesulfonamide top

Crystal data top

C₁₃H₁₀ClNO₃S	Z = 2
M_r = 295.73	F(000) = 304
Triclinic, P1	D_x = 1.567 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 5.4176 (4) Å	Cell parameters from 25 reflections
b = 10.717 (1) Å	θ = 5.9–21.0°
c = 10.980 (1) Å	µ = 4.30 mm⁻¹
α = 86.666 (9)°	T = 296 K
β = 83.903 (9)°	Rod, colourless
γ = 81.823 (8)°	0.48 × 0.42 × 0.23 mm
V = 626.85 (9) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	2058 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.014
Graphite monochromator	θ_max = 66.9°, θ_min = 4.1°
ω/2θ scans	h = 0→6
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
T_min = 0.232, T_max = 0.438	l = −13→13
2490 measured reflections	3 standard reflections every 120 min
2233 independent reflections	intensity decay: 1.5%

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)] = 0.051	H-atom parameters constrained
wR(F²) = 0.152	w = 1/[σ²(F_o²) + (0.1034P)² + 0.2756P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
2233 reflections	Δρ_max = 0.57 e Å⁻³
173 parameters	Δρ_min = −0.52 e Å⁻³
0 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: 0.063 (5)

Crystal data top

C₁₃H₁₀ClNO₃S	γ = 81.823 (8)°
M_r = 295.73	V = 626.85 (9) Å³
Triclinic, P1	Z = 2
a = 5.4176 (4) Å	Cu Kα radiation
b = 10.717 (1) Å	µ = 4.30 mm⁻¹
c = 10.980 (1) Å	T = 296 K
α = 86.666 (9)°	0.48 × 0.42 × 0.23 mm
β = 83.903 (9)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2058 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.014
T_min = 0.232, T_max = 0.438	3 standard reflections every 120 min
2490 measured reflections	intensity decay: 1.5%
2233 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.07	Δρ_max = 0.57 e Å⁻³
2233 reflections	Δρ_min = −0.52 e Å⁻³
173 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	0.5435 (4)	0.1733 (2)	0.8771 (2)	0.0411 (6)
C2	0.7400 (5)	0.0803 (3)	0.8980 (3)	0.0532 (7)
H2	0.8601	0.0939	0.9485	0.064*
C3	0.7552 (6)	−0.0338 (3)	0.8426 (3)	0.0630 (8)
H3	0.8860	−0.0976	0.8562	0.076*
C4	0.5779 (6)	−0.0531 (3)	0.7674 (3)	0.0583 (7)
H4	0.5904	−0.1295	0.7296	0.070*
C5	0.3821 (6)	0.0403 (3)	0.7480 (3)	0.0555 (7)
H5	0.2622	0.0263	0.6976	0.067*
C6	0.3620 (5)	0.1542 (3)	0.8027 (2)	0.0469 (6)
H6	0.2292	0.2171	0.7900	0.056*
C7	0.6462 (5)	0.4535 (2)	0.7460 (2)	0.0408 (6)
C8	0.7940 (4)	0.5520 (2)	0.6881 (2)	0.0387 (5)
C9	0.7425 (5)	0.5974 (3)	0.5720 (2)	0.0519 (7)
H9	0.6201	0.5657	0.5343	0.062*
C10	0.8682 (6)	0.6884 (3)	0.5111 (2)	0.0534 (7)
H10	0.8306	0.7190	0.4332	0.064*
C11	1.0517 (5)	0.7341 (2)	0.5673 (2)	0.0441 (6)
C12	1.1054 (5)	0.6914 (3)	0.6829 (3)	0.0472 (6)
H12	1.2279	0.7236	0.7201	0.057*
C13	0.9770 (5)	0.6006 (2)	0.7438 (2)	0.0426 (6)
H13	1.0125	0.5716	0.8224	0.051*
N1	0.7013 (4)	0.4043 (2)	0.8612 (2)	0.0465 (5)
H1N	0.8365	0.4200	0.8882	0.056*
O1	0.2646 (4)	0.37670 (19)	0.95259 (19)	0.0590 (6)
O2	0.6378 (5)	0.2966 (2)	1.05960 (18)	0.0655 (6)
O3	0.4823 (4)	0.41570 (18)	0.69711 (17)	0.0524 (5)
Cl1	1.21303 (15)	0.84797 (7)	0.48922 (7)	0.0649 (3)
S1	0.51961 (12)	0.31704 (6)	0.94915 (5)	0.0456 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0404 (12)	0.0423 (12)	0.0425 (13)	−0.0149 (10)	−0.0024 (10)	0.0009 (10)
C2	0.0439 (13)	0.0557 (15)	0.0621 (16)	−0.0112 (11)	−0.0109 (12)	−0.0003 (12)
C3	0.0506 (16)	0.0514 (16)	0.084 (2)	−0.0013 (13)	−0.0019 (15)	−0.0026 (15)
C4	0.0625 (17)	0.0472 (14)	0.0670 (19)	−0.0216 (13)	0.0094 (14)	−0.0117 (13)
C5	0.0557 (16)	0.0611 (17)	0.0556 (16)	−0.0258 (13)	−0.0056 (12)	−0.0081 (13)
C6	0.0426 (13)	0.0506 (14)	0.0499 (14)	−0.0117 (11)	−0.0082 (11)	−0.0012 (11)
C7	0.0434 (12)	0.0408 (12)	0.0395 (12)	−0.0072 (10)	−0.0069 (10)	−0.0038 (10)
C8	0.0381 (12)	0.0398 (12)	0.0383 (12)	−0.0042 (9)	−0.0063 (9)	−0.0011 (9)
C9	0.0573 (15)	0.0600 (16)	0.0433 (14)	−0.0180 (13)	−0.0168 (12)	0.0031 (12)
C10	0.0609 (16)	0.0624 (16)	0.0395 (13)	−0.0154 (13)	−0.0141 (11)	0.0104 (12)
C11	0.0405 (12)	0.0437 (13)	0.0462 (13)	−0.0046 (10)	0.0013 (10)	0.0000 (10)
C12	0.0408 (13)	0.0540 (14)	0.0487 (14)	−0.0125 (11)	−0.0068 (10)	−0.0003 (11)
C13	0.0410 (12)	0.0507 (14)	0.0373 (12)	−0.0086 (10)	−0.0094 (10)	0.0024 (10)
N1	0.0553 (12)	0.0473 (11)	0.0426 (12)	−0.0213 (10)	−0.0150 (9)	0.0043 (9)
O1	0.0572 (12)	0.0569 (11)	0.0598 (12)	−0.0047 (9)	0.0063 (9)	−0.0078 (9)
O2	0.0992 (17)	0.0649 (13)	0.0407 (11)	−0.0339 (12)	−0.0190 (10)	0.0066 (9)
O3	0.0527 (11)	0.0588 (11)	0.0511 (10)	−0.0204 (9)	−0.0174 (8)	0.0049 (8)
Cl1	0.0664 (5)	0.0603 (5)	0.0678 (5)	−0.0208 (3)	0.0014 (4)	0.0134 (4)
S1	0.0579 (5)	0.0457 (4)	0.0362 (4)	−0.0166 (3)	−0.0057 (3)	−0.0003 (3)

Geometric parameters (Å, º) top

C1—C2	1.379 (4)	C8—C9	1.381 (3)
C1—C6	1.387 (4)	C8—C13	1.393 (4)
C1—S1	1.755 (2)	C9—C10	1.371 (4)
C2—C3	1.385 (4)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.383 (4)
C3—C4	1.376 (5)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.371 (4)
C4—C5	1.376 (5)	C11—Cl1	1.735 (3)
C4—H4	0.9300	C12—C13	1.377 (4)
C5—C6	1.377 (4)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	N1—S1	1.653 (2)
C7—O3	1.212 (3)	N1—H1N	0.8600
C7—N1	1.387 (3)	O1—S1	1.435 (2)
C7—C8	1.488 (3)	O2—S1	1.422 (2)

C2—C1—C6	121.3 (2)	C10—C9—C8	121.3 (2)
C2—C1—S1	119.1 (2)	C10—C9—H9	119.4
C6—C1—S1	119.5 (2)	C8—C9—H9	119.4
C1—C2—C3	118.8 (3)	C9—C10—C11	118.9 (2)
C1—C2—H2	120.6	C9—C10—H10	120.5
C3—C2—H2	120.6	C11—C10—H10	120.5
C4—C3—C2	120.3 (3)	C12—C11—C10	121.0 (2)
C4—C3—H3	119.8	C12—C11—Cl1	120.2 (2)
C2—C3—H3	119.8	C10—C11—Cl1	118.8 (2)
C3—C4—C5	120.1 (3)	C11—C12—C13	119.7 (2)
C3—C4—H4	119.9	C11—C12—H12	120.2
C5—C4—H4	119.9	C13—C12—H12	120.2
C4—C5—C6	120.6 (3)	C12—C13—C8	120.2 (2)
C4—C5—H5	119.7	C12—C13—H13	119.9
C6—C5—H5	119.7	C8—C13—H13	119.9
C5—C6—C1	118.8 (3)	C7—N1—S1	123.18 (18)
C5—C6—H6	120.6	C7—N1—H1N	118.4
C1—C6—H6	120.6	S1—N1—H1N	118.4
O3—C7—N1	119.6 (2)	O2—S1—O1	119.60 (14)
O3—C7—C8	122.9 (2)	O2—S1—N1	103.57 (12)
N1—C7—C8	117.5 (2)	O1—S1—N1	109.22 (12)
C9—C8—C13	118.9 (2)	O2—S1—C1	109.18 (12)
C9—C8—C7	116.9 (2)	O1—S1—C1	108.42 (12)
C13—C8—C7	124.2 (2)	N1—S1—C1	106.02 (11)

C6—C1—C2—C3	0.4 (4)	C10—C11—C12—C13	0.7 (4)
S1—C1—C2—C3	178.9 (2)	Cl1—C11—C12—C13	−179.7 (2)
C1—C2—C3—C4	0.4 (5)	C11—C12—C13—C8	0.2 (4)
C2—C3—C4—C5	−0.8 (5)	C9—C8—C13—C12	−0.8 (4)
C3—C4—C5—C6	0.5 (5)	C7—C8—C13—C12	179.8 (2)
C4—C5—C6—C1	0.3 (4)	O3—C7—N1—S1	−12.7 (3)
C2—C1—C6—C5	−0.8 (4)	C8—C7—N1—S1	167.24 (17)
S1—C1—C6—C5	−179.2 (2)	C7—N1—S1—O2	−175.7 (2)
O3—C7—C8—C9	−1.9 (4)	C7—N1—S1—O1	−47.2 (2)
N1—C7—C8—C9	178.1 (2)	C7—N1—S1—C1	69.4 (2)
O3—C7—C8—C13	177.6 (3)	C2—C1—S1—O2	−26.5 (3)
N1—C7—C8—C13	−2.4 (4)	C6—C1—S1—O2	151.9 (2)
C13—C8—C9—C10	0.3 (4)	C2—C1—S1—O1	−158.4 (2)
C7—C8—C9—C10	179.8 (3)	C6—C1—S1—O1	20.1 (2)
C8—C9—C10—C11	0.7 (4)	C2—C1—S1—N1	84.5 (2)
C9—C10—C11—C12	−1.2 (4)	C6—C1—S1—N1	−97.1 (2)
C9—C10—C11—Cl1	179.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.47	3.281 (3)	158

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀ClNO₃S
M_r	295.73
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	5.4176 (4), 10.717 (1), 10.980 (1)
α, β, γ (°)	86.666 (9), 83.903 (9), 81.823 (8)
V (Å³)	626.85 (9)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	4.30
Crystal size (mm)	0.48 × 0.42 × 0.23

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.232, 0.438
No. of measured, independent and observed [I > 2σ(I)] reflections	2490, 2233, 2058
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.152, 1.07
No. of reflections	2233
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.52

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	0.86	2.47	3.281 (3)	157.7

Symmetry code: (i) x+1, y, z.

References

Enraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o1825. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009a). Acta Cryst. E65, o2516. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009b). Acta Cryst. E65, o2750. Web of Science 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

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Volume 65| Part 12| December 2009| Page o3156

doi:10.1107/S1600536809048399

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