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

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ISSN: 2056-9890

N-(2-Chloro­phen­yl)-4-nitro­benzene­sulfonamide

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 16 November 2012; accepted 27 November 2012; online 30 November 2012)

In the title compound, C12H9ClN2O4S, the dihedral angle between the benzene rings is 70.60 (11)°. An intra­molecular N—H⋯Cl contact occurs. In the crystal, mol­ecules form inversion dimers via pairs of N—H⋯O hydrogen bonds.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-aryl­sulfonamides, see: Chaithanya et al. (2012[Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o2766.]); Gowda et al. (2005[Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.]) and of N-chloro­aryl­amides, see: Gowda & Shetty (2004[Gowda, B. T. & Shetty, M. (2004). J. Phys. Org. Chem. 17, 848-864.]); Gowda & Weiss (1994[Gowda, B. T. & Weiss, A. (1994). Z. Naturforsch. Teil A, 49, 695-702.]); Shetty & Gowda (2004[Shetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63-72.]). For hydrogen-bonding patterns and motifs, see: Adsmond et al. (2001[Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058-2077.]); Allen et al. (1998[Allen, F. H., Raithby, P. R., Shields, G. P. & Taylor, R. (1998). Chem. Commun. pp. 1043-1044.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]).

[Scheme 1]

Experimental

Crystal data
  • C12H9ClN2O4S

  • Mr = 312.72

  • Monoclinic, P 21 /n

  • a = 9.2762 (9) Å

  • b = 12.981 (1) Å

  • c = 11.970 (1) Å

  • β = 110.97 (1)°

  • V = 1345.9 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.45 mm−1

  • T = 293 K

  • 0.42 × 0.20 × 0.10 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.833, Tmax = 0.956

  • 5256 measured reflections

  • 2748 independent reflections

  • 2019 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.110

  • S = 1.16

  • 2748 reflections

  • 185 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O1i 0.84 (2) 2.20 (2) 3.003 (3) 159 (3)
N1—H1N⋯Cl1 0.84 (2) 2.56 (3) 2.984 (3) 112 (3)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); 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

As a part of our studies on the substituent effects on the structures and other aspects of N-arylsulfoamides (Chaithanya et al., 2012; Gowda et al., 2005) and N-chloroarylamides (Gowda & Shetty, 2004; Gowda & Weiss, 1994; Shetty & Gowda, 2004), in the present work, the crystal structure of N-(2-chlorophenyl)-4-nitrobenzenesulfonamide has been determined (Fig. 1).

The conformation of the N—C bond in the —SO2—NH—C segment has gauche torsion with respect to the SO bonds (Fig.1). Further, the conformation of the N—H bond in the —SO2—NH— segment is syn to the ortho-Cl atom in the anilino ring, compared to anti conformation observed between the N—H bond and ortho- methyl group in N-(2-methylphenyl)-4-nitrobenzenesulfonamide (I) (Chaithanya et al., 2012). The molecule is twisted at the S—N bond with the torsional angle of -59.12 (29)°, compared to the value of -58.97 (21)° in (II).

The dihedral angle between the sulfonyl and the anilino rings is 70.60 (11)°, compared to the value of 51.11 (10)° in (II).

The amide H-atom showed bifurcated intramolecular H-bonding with the ortho-Cl atom in the anilino benzene ring and the intermolecular H-bonding with the sulfonyl oxygen atom of the other molecule, generating C(6) and R22(8) motifs (Adsmond et al., 2001; Allen et al., 1998; Bernstein et al., 1995; Etter, 1990).

In the crystal structure, the molecules form centrosymmetric dimers vi N—H···O hydrogen bonds. Part of the crystal structure is shown in Fig. 2.

Related literature top

For studies on the effects of substituents on the structures and other aspects of N-arylsulfonamides, see: Chaithanya et al. (2012); Gowda et al. (2005) and of N-chloroarylamides, see: Gowda & Shetty (2004); Gowda & Weiss (1994); Shetty & Gowda (2004). For hydrogen-bonding patterns and motifs, see: Adsmond et al. (2001); Allen et al. (1998); Bernstein et al. (1995); Etter (1990).

Experimental top

The title compound was prepared by treating 4-nitrobenzenesulfonylchloride with 2-chloroaniline in the stoichiometric ratio and boiling the reaction mixture for 15 minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid N-(2-chlorophenyl)-4-nitrobenzenesulfonamide was filtered under suction and washed thoroughly with cold water and dilute HCl to remove the excess sulfonylchloride and aniline, respectively. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by its infrared spectra.

Prism like light pink single crystals of the title compound used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation of the solvent at room temperature.

Refinement top

H atoms bonded to C were positioned with idealized geometry using a riding model with the aromatic C—H = 0.93 Å. The amino H atom was freely refined with the N—H distance restrained to 0.86 (2) Å. All H atoms were refined with isotropic displacement parameters set at 1.2 Ueq of the parent atom.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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 the title compound, showing the atom labelling scheme and with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Bifurcated hydrogen bonding in the title compound.
N-(2-Chlorophenyl)-4-nitrobenzenesulfonamide top
Crystal data top
C12H9ClN2O4SF(000) = 640
Mr = 312.72Dx = 1.543 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1413 reflections
a = 9.2762 (9) Åθ = 2.9–27.9°
b = 12.981 (1) ŵ = 0.45 mm1
c = 11.970 (1) ÅT = 293 K
β = 110.97 (1)°Prism, light pink
V = 1345.9 (2) Å30.42 × 0.20 × 0.10 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2748 independent reflections
Radiation source: fine-focus sealed tube2019 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Rotation method data acquisition using ω scansθmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 1110
Tmin = 0.833, Tmax = 0.956k = 1116
5256 measured reflectionsl = 1114
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)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0185P)2 + 1.7246P]
where P = (Fo2 + 2Fc2)/3
S = 1.16(Δ/σ)max = 0.001
2748 reflectionsΔρmax = 0.29 e Å3
185 parametersΔρmin = 0.30 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0098 (7)
Crystal data top
C12H9ClN2O4SV = 1345.9 (2) Å3
Mr = 312.72Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.2762 (9) ŵ = 0.45 mm1
b = 12.981 (1) ÅT = 293 K
c = 11.970 (1) Å0.42 × 0.20 × 0.10 mm
β = 110.97 (1)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2748 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
2019 reflections with I > 2σ(I)
Tmin = 0.833, Tmax = 0.956Rint = 0.025
5256 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0531 restraint
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.16Δρmax = 0.29 e Å3
2748 reflectionsΔρmin = 0.30 e Å3
185 parameters
Special details top

Experimental. Absorption correction: CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C10.1263 (3)0.5209 (2)0.4016 (3)0.0343 (7)
C20.1763 (4)0.6204 (3)0.4357 (3)0.0507 (9)
H20.28020.63310.47840.061*
C30.0722 (4)0.7003 (3)0.4066 (3)0.0539 (9)
H30.10400.76760.42890.065*
C40.0808 (4)0.6778 (3)0.3434 (3)0.0444 (8)
C50.1329 (4)0.5798 (3)0.3102 (3)0.0430 (8)
H50.23720.56730.26880.052*
C60.0280 (3)0.4996 (3)0.3394 (3)0.0375 (7)
H60.06060.43240.31750.045*
C70.2457 (3)0.4074 (2)0.2074 (3)0.0366 (7)
C80.2726 (3)0.4687 (2)0.1220 (3)0.0401 (7)
C90.1904 (4)0.4540 (3)0.0011 (3)0.0520 (9)
H90.21150.49430.05540.062*
C100.0775 (4)0.3798 (3)0.0351 (3)0.0573 (10)
H100.02150.37010.11610.069*
C110.0477 (4)0.3202 (3)0.0484 (3)0.0550 (10)
H110.03070.27130.02370.066*
C120.1327 (4)0.3317 (3)0.1695 (3)0.0486 (9)
H120.11410.28890.22510.058*
N10.3366 (3)0.4207 (2)0.3307 (2)0.0399 (6)
H1N0.407 (3)0.465 (2)0.348 (3)0.048*
N20.1922 (4)0.7636 (3)0.3102 (3)0.0653 (9)
O10.3880 (2)0.44640 (19)0.54360 (19)0.0490 (6)
O20.1828 (2)0.32555 (17)0.4305 (2)0.0460 (6)
O30.3263 (3)0.7440 (3)0.2546 (3)0.0967 (11)
O40.1448 (4)0.8497 (3)0.3400 (4)0.1119 (14)
Cl10.40864 (11)0.56660 (7)0.16532 (8)0.0596 (3)
S10.26320 (9)0.41991 (6)0.43645 (7)0.0372 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0355 (16)0.0356 (17)0.0334 (16)0.0036 (14)0.0144 (13)0.0015 (13)
C20.0380 (18)0.045 (2)0.063 (2)0.0078 (16)0.0104 (17)0.0001 (18)
C30.053 (2)0.0350 (19)0.072 (2)0.0039 (17)0.0198 (19)0.0011 (18)
C40.0448 (18)0.043 (2)0.050 (2)0.0092 (16)0.0232 (16)0.0072 (16)
C50.0344 (16)0.051 (2)0.0433 (18)0.0011 (16)0.0141 (14)0.0003 (17)
C60.0348 (16)0.0393 (18)0.0392 (17)0.0051 (14)0.0144 (14)0.0047 (14)
C70.0358 (15)0.0373 (17)0.0371 (16)0.0028 (14)0.0136 (13)0.0044 (14)
C80.0391 (17)0.0385 (18)0.0419 (18)0.0003 (15)0.0135 (14)0.0026 (15)
C90.058 (2)0.056 (2)0.042 (2)0.0009 (19)0.0178 (17)0.0003 (17)
C100.056 (2)0.069 (3)0.042 (2)0.004 (2)0.0126 (18)0.0138 (19)
C110.047 (2)0.058 (2)0.060 (2)0.0154 (18)0.0185 (18)0.023 (2)
C120.0500 (19)0.048 (2)0.051 (2)0.0104 (17)0.0220 (17)0.0074 (17)
N10.0346 (14)0.0450 (16)0.0398 (14)0.0029 (13)0.0131 (12)0.0010 (13)
N20.061 (2)0.053 (2)0.086 (3)0.0140 (18)0.033 (2)0.0111 (19)
O10.0384 (12)0.0669 (17)0.0355 (12)0.0016 (11)0.0056 (10)0.0057 (11)
O20.0487 (13)0.0389 (13)0.0511 (14)0.0024 (11)0.0188 (11)0.0085 (11)
O30.0542 (18)0.076 (2)0.145 (3)0.0226 (17)0.018 (2)0.014 (2)
O40.090 (2)0.0459 (19)0.187 (4)0.0172 (18)0.034 (3)0.002 (2)
Cl10.0682 (6)0.0530 (6)0.0543 (6)0.0196 (5)0.0179 (5)0.0023 (4)
S10.0343 (4)0.0411 (5)0.0348 (4)0.0007 (4)0.0106 (3)0.0052 (4)
Geometric parameters (Å, º) top
C1—C21.383 (4)C8—C91.386 (4)
C1—C61.385 (4)C8—Cl11.735 (3)
C1—S11.768 (3)C9—C101.374 (5)
C2—C31.375 (5)C9—H90.9300
C2—H20.9300C10—C111.367 (5)
C3—C41.380 (5)C10—H100.9300
C3—H30.9300C11—C121.388 (5)
C4—C51.369 (5)C11—H110.9300
C4—N21.474 (4)C12—H120.9300
C5—C61.381 (4)N1—S11.637 (3)
C5—H50.9300N1—H1N0.837 (18)
C6—H60.9300N2—O41.207 (4)
C7—C81.386 (4)N2—O31.210 (4)
C7—C121.390 (4)O1—S11.429 (2)
C7—N11.425 (4)O2—S11.423 (2)
C2—C1—C6121.2 (3)C10—C9—C8119.9 (3)
C2—C1—S1119.1 (2)C10—C9—H9120.1
C6—C1—S1119.7 (2)C8—C9—H9120.1
C3—C2—C1119.9 (3)C11—C10—C9119.8 (3)
C3—C2—H2120.0C11—C10—H10120.1
C1—C2—H2120.0C9—C10—H10120.1
C2—C3—C4118.0 (3)C10—C11—C12120.9 (3)
C2—C3—H3121.0C10—C11—H11119.5
C4—C3—H3121.0C12—C11—H11119.5
C5—C4—C3122.9 (3)C11—C12—C7119.8 (3)
C5—C4—N2119.0 (3)C11—C12—H12120.1
C3—C4—N2118.1 (3)C7—C12—H12120.1
C4—C5—C6118.9 (3)C7—N1—S1123.0 (2)
C4—C5—H5120.5C7—N1—H1N117 (2)
C6—C5—H5120.5S1—N1—H1N108 (2)
C5—C6—C1119.0 (3)O4—N2—O3123.4 (4)
C5—C6—H6120.5O4—N2—C4118.4 (4)
C1—C6—H6120.5O3—N2—C4118.2 (4)
C8—C7—C12118.6 (3)O2—S1—O1119.60 (14)
C8—C7—N1120.0 (3)O2—S1—N1108.81 (14)
C12—C7—N1121.4 (3)O1—S1—N1105.37 (13)
C9—C8—C7120.9 (3)O2—S1—C1107.88 (14)
C9—C8—Cl1118.9 (3)O1—S1—C1108.43 (15)
C7—C8—Cl1120.2 (2)N1—S1—C1105.99 (14)
C6—C1—C2—C30.8 (5)C10—C11—C12—C72.6 (5)
S1—C1—C2—C3178.2 (3)C8—C7—C12—C111.2 (5)
C1—C2—C3—C40.0 (5)N1—C7—C12—C11179.2 (3)
C2—C3—C4—C50.9 (5)C8—C7—N1—S1137.5 (3)
C2—C3—C4—N2179.0 (3)C12—C7—N1—S144.6 (4)
C3—C4—C5—C61.1 (5)C5—C4—N2—O4180.0 (4)
N2—C4—C5—C6178.8 (3)C3—C4—N2—O40.1 (6)
C4—C5—C6—C10.3 (5)C5—C4—N2—O30.0 (5)
C2—C1—C6—C50.6 (5)C3—C4—N2—O3179.9 (4)
S1—C1—C6—C5178.4 (2)C7—N1—S1—O256.7 (3)
C12—C7—C8—C90.9 (5)C7—N1—S1—O1173.9 (3)
N1—C7—C8—C9177.1 (3)C7—N1—S1—C159.1 (3)
C12—C7—C8—Cl1178.1 (2)C2—C1—S1—O2160.4 (3)
N1—C7—C8—Cl13.9 (4)C6—C1—S1—O220.6 (3)
C7—C8—C9—C101.8 (5)C2—C1—S1—O129.5 (3)
Cl1—C8—C9—C10177.3 (3)C6—C1—S1—O1151.5 (2)
C8—C9—C10—C110.5 (6)C2—C1—S1—N183.2 (3)
C9—C10—C11—C121.7 (6)C6—C1—S1—N195.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.84 (2)2.20 (2)3.003 (3)159 (3)
N1—H1N···Cl10.84 (2)2.56 (3)2.984 (3)112 (3)
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC12H9ClN2O4S
Mr312.72
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)9.2762 (9), 12.981 (1), 11.970 (1)
β (°) 110.97 (1)
V3)1345.9 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.45
Crystal size (mm)0.42 × 0.20 × 0.10
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.833, 0.956
No. of measured, independent and
observed [I > 2σ(I)] reflections
5256, 2748, 2019
Rint0.025
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.110, 1.16
No. of reflections2748
No. of parameters185
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.29, 0.30

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), 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···O1i0.837 (18)2.20 (2)3.003 (3)159 (3)
N1—H1N···Cl10.837 (18)2.56 (3)2.984 (3)112 (3)
Symmetry code: (i) x+1, y+1, z+1.
 

Acknowledgements

UC thanks Mangalore University for the award of a research fellowship. BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC–BSR one-time grant to faculty.

References

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