organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

N-(4-Chloro­benzo­yl)benzene­sulfonamide

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[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o1825.], 2009a[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009a). Acta Cryst. E65, o2516.],b[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009b). Acta Cryst. E65, o2750.]).

[Scheme 1]

Experimental

Crystal data
  • C13H10ClNO3S

  • Mr = 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[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.232, Tmax = 0.438

  • 2490 measured reflections

  • 2233 independent reflections

  • 2058 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.57 e Å−3

  • Δρmin = −0.52 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Enraf-Nonius (1996). CAD-4-PC. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987[Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


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.

Refinement top

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 Ueq of the parent atom).

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
[Figure 1] Fig. 1. Molecular structure of (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.
N-(4-Chlorobenzoyl)benzenesulfonamide top
Crystal data top
C13H10ClNO3SZ = 2
Mr = 295.73F(000) = 304
Triclinic, P1Dx = 1.567 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54180 Å
a = 5.4176 (4) ÅCell parameters from 25 reflections
b = 10.717 (1) Åθ = 5.9–21.0°
c = 10.980 (1) ŵ = 4.30 mm1
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 tubeRint = 0.014
Graphite monochromatorθmax = 66.9°, θmin = 4.1°
ω/2θ scansh = 06
Absorption correction: ψ scan
(North et al., 1968)
k = 1212
Tmin = 0.232, Tmax = 0.438l = 1313
2490 measured reflections3 standard reflections every 120 min
2233 independent reflections intensity decay: 1.5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.152 w = 1/[σ2(Fo2) + (0.1034P)2 + 0.2756P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
2233 reflectionsΔρmax = 0.57 e Å3
173 parametersΔρmin = 0.52 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.063 (5)
Crystal data top
C13H10ClNO3Sγ = 81.823 (8)°
Mr = 295.73V = 626.85 (9) Å3
Triclinic, P1Z = 2
a = 5.4176 (4) ÅCu Kα radiation
b = 10.717 (1) ŵ = 4.30 mm1
c = 10.980 (1) ÅT = 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)
Rint = 0.014
Tmin = 0.232, Tmax = 0.4383 standard reflections every 120 min
2490 measured reflections intensity decay: 1.5%
2233 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.152H-atom parameters constrained
S = 1.07Δρmax = 0.57 e Å3
2233 reflectionsΔρmin = 0.52 e Å3
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
xyzUiso*/Ueq
C10.5435 (4)0.1733 (2)0.8771 (2)0.0411 (6)
C20.7400 (5)0.0803 (3)0.8980 (3)0.0532 (7)
H20.86010.09390.94850.064*
C30.7552 (6)0.0338 (3)0.8426 (3)0.0630 (8)
H30.88600.09760.85620.076*
C40.5779 (6)0.0531 (3)0.7674 (3)0.0583 (7)
H40.59040.12950.72960.070*
C50.3821 (6)0.0403 (3)0.7480 (3)0.0555 (7)
H50.26220.02630.69760.067*
C60.3620 (5)0.1542 (3)0.8027 (2)0.0469 (6)
H60.22920.21710.79000.056*
C70.6462 (5)0.4535 (2)0.7460 (2)0.0408 (6)
C80.7940 (4)0.5520 (2)0.6881 (2)0.0387 (5)
C90.7425 (5)0.5974 (3)0.5720 (2)0.0519 (7)
H90.62010.56570.53430.062*
C100.8682 (6)0.6884 (3)0.5111 (2)0.0534 (7)
H100.83060.71900.43320.064*
C111.0517 (5)0.7341 (2)0.5673 (2)0.0441 (6)
C121.1054 (5)0.6914 (3)0.6829 (3)0.0472 (6)
H121.22790.72360.72010.057*
C130.9770 (5)0.6006 (2)0.7438 (2)0.0426 (6)
H131.01250.57160.82240.051*
N10.7013 (4)0.4043 (2)0.8612 (2)0.0465 (5)
H1N0.83650.42000.88820.056*
O10.2646 (4)0.37670 (19)0.95259 (19)0.0590 (6)
O20.6378 (5)0.2966 (2)1.05960 (18)0.0655 (6)
O30.4823 (4)0.41570 (18)0.69711 (17)0.0524 (5)
Cl11.21303 (15)0.84797 (7)0.48922 (7)0.0649 (3)
S10.51961 (12)0.31704 (6)0.94915 (5)0.0456 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0404 (12)0.0423 (12)0.0425 (13)0.0149 (10)0.0024 (10)0.0009 (10)
C20.0439 (13)0.0557 (15)0.0621 (16)0.0112 (11)0.0109 (12)0.0003 (12)
C30.0506 (16)0.0514 (16)0.084 (2)0.0013 (13)0.0019 (15)0.0026 (15)
C40.0625 (17)0.0472 (14)0.0670 (19)0.0216 (13)0.0094 (14)0.0117 (13)
C50.0557 (16)0.0611 (17)0.0556 (16)0.0258 (13)0.0056 (12)0.0081 (13)
C60.0426 (13)0.0506 (14)0.0499 (14)0.0117 (11)0.0082 (11)0.0012 (11)
C70.0434 (12)0.0408 (12)0.0395 (12)0.0072 (10)0.0069 (10)0.0038 (10)
C80.0381 (12)0.0398 (12)0.0383 (12)0.0042 (9)0.0063 (9)0.0011 (9)
C90.0573 (15)0.0600 (16)0.0433 (14)0.0180 (13)0.0168 (12)0.0031 (12)
C100.0609 (16)0.0624 (16)0.0395 (13)0.0154 (13)0.0141 (11)0.0104 (12)
C110.0405 (12)0.0437 (13)0.0462 (13)0.0046 (10)0.0013 (10)0.0000 (10)
C120.0408 (13)0.0540 (14)0.0487 (14)0.0125 (11)0.0068 (10)0.0003 (11)
C130.0410 (12)0.0507 (14)0.0373 (12)0.0086 (10)0.0094 (10)0.0024 (10)
N10.0553 (12)0.0473 (11)0.0426 (12)0.0213 (10)0.0150 (9)0.0043 (9)
O10.0572 (12)0.0569 (11)0.0598 (12)0.0047 (9)0.0063 (9)0.0078 (9)
O20.0992 (17)0.0649 (13)0.0407 (11)0.0339 (12)0.0190 (10)0.0066 (9)
O30.0527 (11)0.0588 (11)0.0511 (10)0.0204 (9)0.0174 (8)0.0049 (8)
Cl10.0664 (5)0.0603 (5)0.0678 (5)0.0208 (3)0.0014 (4)0.0134 (4)
S10.0579 (5)0.0457 (4)0.0362 (4)0.0166 (3)0.0057 (3)0.0003 (3)
Geometric parameters (Å, º) top
C1—C21.379 (4)C8—C91.381 (3)
C1—C61.387 (4)C8—C131.393 (4)
C1—S11.755 (2)C9—C101.371 (4)
C2—C31.385 (4)C9—H90.9300
C2—H20.9300C10—C111.383 (4)
C3—C41.376 (5)C10—H100.9300
C3—H30.9300C11—C121.371 (4)
C4—C51.376 (5)C11—Cl11.735 (3)
C4—H40.9300C12—C131.377 (4)
C5—C61.377 (4)C12—H120.9300
C5—H50.9300C13—H130.9300
C6—H60.9300N1—S11.653 (2)
C7—O31.212 (3)N1—H1N0.8600
C7—N11.387 (3)O1—S11.435 (2)
C7—C81.488 (3)O2—S11.422 (2)
C2—C1—C6121.3 (2)C10—C9—C8121.3 (2)
C2—C1—S1119.1 (2)C10—C9—H9119.4
C6—C1—S1119.5 (2)C8—C9—H9119.4
C1—C2—C3118.8 (3)C9—C10—C11118.9 (2)
C1—C2—H2120.6C9—C10—H10120.5
C3—C2—H2120.6C11—C10—H10120.5
C4—C3—C2120.3 (3)C12—C11—C10121.0 (2)
C4—C3—H3119.8C12—C11—Cl1120.2 (2)
C2—C3—H3119.8C10—C11—Cl1118.8 (2)
C3—C4—C5120.1 (3)C11—C12—C13119.7 (2)
C3—C4—H4119.9C11—C12—H12120.2
C5—C4—H4119.9C13—C12—H12120.2
C4—C5—C6120.6 (3)C12—C13—C8120.2 (2)
C4—C5—H5119.7C12—C13—H13119.9
C6—C5—H5119.7C8—C13—H13119.9
C5—C6—C1118.8 (3)C7—N1—S1123.18 (18)
C5—C6—H6120.6C7—N1—H1N118.4
C1—C6—H6120.6S1—N1—H1N118.4
O3—C7—N1119.6 (2)O2—S1—O1119.60 (14)
O3—C7—C8122.9 (2)O2—S1—N1103.57 (12)
N1—C7—C8117.5 (2)O1—S1—N1109.22 (12)
C9—C8—C13118.9 (2)O2—S1—C1109.18 (12)
C9—C8—C7116.9 (2)O1—S1—C1108.42 (12)
C13—C8—C7124.2 (2)N1—S1—C1106.02 (11)
C6—C1—C2—C30.4 (4)C10—C11—C12—C130.7 (4)
S1—C1—C2—C3178.9 (2)Cl1—C11—C12—C13179.7 (2)
C1—C2—C3—C40.4 (5)C11—C12—C13—C80.2 (4)
C2—C3—C4—C50.8 (5)C9—C8—C13—C120.8 (4)
C3—C4—C5—C60.5 (5)C7—C8—C13—C12179.8 (2)
C4—C5—C6—C10.3 (4)O3—C7—N1—S112.7 (3)
C2—C1—C6—C50.8 (4)C8—C7—N1—S1167.24 (17)
S1—C1—C6—C5179.2 (2)C7—N1—S1—O2175.7 (2)
O3—C7—C8—C91.9 (4)C7—N1—S1—O147.2 (2)
N1—C7—C8—C9178.1 (2)C7—N1—S1—C169.4 (2)
O3—C7—C8—C13177.6 (3)C2—C1—S1—O226.5 (3)
N1—C7—C8—C132.4 (4)C6—C1—S1—O2151.9 (2)
C13—C8—C9—C100.3 (4)C2—C1—S1—O1158.4 (2)
C7—C8—C9—C10179.8 (3)C6—C1—S1—O120.1 (2)
C8—C9—C10—C110.7 (4)C2—C1—S1—N184.5 (2)
C9—C10—C11—C121.2 (4)C6—C1—S1—N197.1 (2)
C9—C10—C11—Cl1179.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.862.473.281 (3)158
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC13H10ClNO3S
Mr295.73
Crystal system, space groupTriclinic, 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)
V3)626.85 (9)
Z2
Radiation typeCu Kα
µ (mm1)4.30
Crystal size (mm)0.48 × 0.42 × 0.23
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.232, 0.438
No. of measured, independent and
observed [I > 2σ(I)] reflections
2490, 2233, 2058
Rint0.014
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.152, 1.07
No. of reflections2233
No. of parameters173
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N1—H1N···O1i0.862.473.281 (3)157.7
Symmetry code: (i) x+1, y, z.
 

References

First citationEnraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationGowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o1825.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009a). Acta Cryst. E65, o2516.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009b). Acta Cryst. E65, o2750.  Web of Science CrossRef IUCr Journals Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.  Google Scholar

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