N-(4-Chloro­benzo­yl)benzene­sulfonamide

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.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.051
• wR factor = 0.152
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

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Alert level G
PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large..       0.10

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   0 ALERT level B = Potentially serious problem
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   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
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S1. Comment

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

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

S2. Experimental

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.

S3. Refinement

The H atoms were positioned with idealized geometry using a riding model [N—H = 0.86 Å, C—H = 0.93 Å] and were refined with isotropic displacement parameters (set to 1.2 times of the U_eq of the parent atom).

Computing details

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

	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

Crystal data

C13H10ClNO3S	Z = 2
Mr = 295.73	F(000) = 304
Triclinic, P1	Dx = 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) Å^3

Data collection

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

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.152	w = 1/[σ^2(Fo^2) + (0.1034P)^2 + 0.2756P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
2233 reflections	Δρmax = 0.57 e Å^−3
173 parameters	Δρmin = −0.52 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.063 (5)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.86	2.47	3.281 (3)	158

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