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ISSN: 2056-9890

N-(3-Chloro­benzo­yl)-2-nitro­benzene­sulfonamide

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany, and cDepartment of Chemistry, University College of Science, Tumkur University, Tumkur 572 102, India
*Correspondence e-mail: gowdabt@yahoo.com

(Received 8 February 2012; accepted 13 February 2012; online 17 February 2012)

In the title compound, C13H9ClN2O5S, the N—C bond in the C—SO2—NH—C segment has a gauche torsion with respect to the S=O bonds. The conformation between the N—H bond and the ortho-nitro group in the sulfonyl benzene ring is syn, and that between the C=O and the meta-Cl atom in the benzoyl ring is anti. The mol­ecule is twisted at the S—N bond, with a torsion angle of 65.41 (38)°. The dihedral angle between the sulfonyl benzene ring and the –SO2—NH—C—O segment is 75.0 (1)°, and that between the sulfonyl and the benzoyl benzene ring is 89.1 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O(S) hydrogen bonds.

Related literature

For our studies of the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (1999[Gowda, B. T., Bhat, D. K., Fuess, H. & Weiss, A. (1999). Z. Naturforsch. Teil A, 54, 261-267.], 2006[Gowda, B. T., Kozisek, J. & Fuess, H. (2006). Z. Naturforsch. Teil A, 61, 588-594.]); N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007[Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2597.]); N-(substitutedbenzo­yl)-aryl­sulfonamides, see: Suchetan et al. (2012[Suchetan, P. A., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o274.]); N-chloro­aryl­amides, see: Jyothi & Gowda (2004[Jyothi, K. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 64-68.]) and N-bromo­aryl­sulfonamides, see: Usha & Gowda (2006[Usha, K. M. & Gowda, B. T. (2006). J. Chem. Sci. 118, 351-359.])..

[Scheme 1]

Experimental

Crystal data
  • C13H9ClN2O5S

  • Mr = 340.73

  • Orthorhombic, P b c a

  • a = 12.2046 (8) Å

  • b = 12.6121 (9) Å

  • c = 18.433 (1) Å

  • V = 2837.3 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.44 mm−1

  • T = 293 K

  • 0.28 × 0.28 × 0.08 mm

Data collection
  • Oxford Xcalibur diffractometer with Sapphire CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.886, Tmax = 0.966

  • 11298 measured reflections

  • 2889 independent reflections

  • 1911 reflections with I > 2σ(I)

  • Rint = 0.051

Refinement
  • R[F2 > 2σ(F2)] = 0.074

  • wR(F2) = 0.147

  • S = 1.20

  • 2889 reflections

  • 202 parameters

  • 1 restraint

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

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.29 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) 2.41 (3) 3.193 (4) 153 (4)
Symmetry code: (i) -x, -y+2, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, 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 part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 1999, 2006), N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-(substitutedbenzoyl)-arylsulfonamides (Suchetan et al., 2012), N-chloroarylsulfonamides (Jyothi & Gowda, 2004) and N-bromoarylsulfonamides (Usha & Gowda, 2006), in the present work, the crystal structure of N-(3-chlorobenzoyl)-2-nitrobenzenesulfonamide has been determined (Fig.1).

The conformation between the N—H and CO bonds in the C—SO2—NH—C(O) segment is anti and the N—C bond in the segment has gauche torsion with respect to the SO bonds (Fig. 1), similar to that observed in N-(2-chlorobenzoyl)-2-nitrobenzenesulfonamide (I) (Suchetan et al., 2012). In the title compound, the conformation between the N—H bond and the ortho-nitro group in the sulfonyl benzene ring is syn, similar to that observed in (I). Further, the conformation of the CO is anti to the meta-Cl atom in the benzoyl ring, similar to that observed between the CO and the ortho-Cl atom in (I).

The molecule is twisted at the S—N bond with the torsional angle of 65.41 (38)°, compared to the value of -59.68 (17)° in (I).

The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 75.0 (1)°, compared to the value of 77.5 (1)° in (I). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 89.1 (1)°, compared to the value of 71.2 (1)° in (I).

In the crystal structure two molecules each are linked by pairs of intermolecular N—H···O (S) hydrogen bonds into dimers that are located around centers of inversion (Fig. 2 and Table 1).

Related literature top

For our studies of the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (1999, 2006); N-(aryl)-methanesulfonamides, see: Gowda et al. (2007); N-(substitutedbenzoyl)-arylsulfonamides, see: Suchetan et al. (2012); N-chloroarylamides, see: Jyothi & Gowda (2004) and N-bromoarylsulfonamides, see: Usha & Gowda (2006)..

Experimental top

The title compound was prepared by refluxing a mixture of 3-chlorobenzoic acid (0.02 mole), 2-nitrobenzenesulfonamide (0.02 mole) and excess phosphorous oxychloride for 3 h on a water bath. The resultant mixture was cooled and poured into crushed ice. The solid, N-(3-chlorobenzoyl)-2-nitrobenzenesulfonamide, 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. It was filtered, dried and recrystallized.

Rod like colourless single crystals of the title compound used in X-ray diffraction studies were obtained by slow evaporation of the solvent from its toluene solution at room temperature.

Refinement top

The H atom of the NH group was located in a difference map and later restrained to N—H = 0.86 (2) %A. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (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. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. View of the inversion-related dimers linked by pairs of N—H···O(S) hydrogen bonds (Hydrogen bonding is shown as dashed lines)..
N-(3-Chlorobenzoyl)-2-nitrobenzenesulfonamide top
Crystal data top
C13H9ClN2O5SF(000) = 1392
Mr = 340.73Dx = 1.595 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 1818 reflections
a = 12.2046 (8) Åθ = 2.6–27.9°
b = 12.6121 (9) ŵ = 0.44 mm1
c = 18.433 (1) ÅT = 293 K
V = 2837.3 (3) Å3Rod, colourless
Z = 80.28 × 0.28 × 0.08 mm
Data collection top
Oxford Xcalibur
diffractometer with Sapphire CCD detector
2889 independent reflections
Radiation source: fine-focus sealed tube1911 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
Rotation method data acquisition using ω and ϕ scansθmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 1315
Tmin = 0.886, Tmax = 0.966k = 1511
11298 measured reflectionsl = 2223
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 1.20 w = 1/[σ2(Fo2) + (0.0362P)2 + 4.7309P]
where P = (Fo2 + 2Fc2)/3
2889 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.34 e Å3
1 restraintΔρmin = 0.29 e Å3
Crystal data top
C13H9ClN2O5SV = 2837.3 (3) Å3
Mr = 340.73Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 12.2046 (8) ŵ = 0.44 mm1
b = 12.6121 (9) ÅT = 293 K
c = 18.433 (1) Å0.28 × 0.28 × 0.08 mm
Data collection top
Oxford Xcalibur
diffractometer with Sapphire CCD detector
2889 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
1911 reflections with I > 2σ(I)
Tmin = 0.886, Tmax = 0.966Rint = 0.051
11298 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0741 restraint
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 1.20Δρmax = 0.34 e Å3
2889 reflectionsΔρmin = 0.29 e Å3
202 parameters
Special details top

Experimental. 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
C10.0112 (3)0.7252 (3)0.0676 (2)0.0347 (9)
C20.0862 (3)0.7030 (3)0.0131 (2)0.0402 (10)
C30.1369 (4)0.6063 (4)0.0079 (3)0.0503 (12)
H30.18540.59240.02980.060*
C40.1152 (4)0.5307 (4)0.0590 (3)0.0552 (13)
H40.14980.46520.05630.066*
C50.0427 (4)0.5506 (4)0.1143 (3)0.0537 (13)
H50.02860.49860.14880.064*
C60.0092 (4)0.6469 (3)0.1188 (2)0.0450 (11)
H60.05820.65980.15640.054*
C70.0490 (3)0.9234 (3)0.1845 (2)0.0389 (10)
C80.1239 (3)1.0094 (3)0.2089 (2)0.0354 (9)
C90.1284 (3)1.1061 (3)0.1738 (2)0.0390 (10)
H90.08121.12050.13540.047*
C100.2036 (4)1.1812 (3)0.1960 (2)0.0400 (10)
C110.2730 (4)1.1613 (4)0.2528 (2)0.0456 (11)
H110.32401.21190.26720.055*
C120.2663 (4)1.0654 (4)0.2884 (2)0.0499 (12)
H120.31271.05180.32730.060*
C130.1921 (4)0.9897 (3)0.2670 (2)0.0452 (11)
H130.18790.92540.29150.054*
N10.0153 (3)0.9315 (3)0.11212 (18)0.0400 (9)
H1N0.050 (3)0.966 (3)0.0794 (18)0.048*
N20.1148 (3)0.7825 (3)0.0428 (2)0.0528 (10)
O10.0765 (2)0.8844 (2)0.00038 (15)0.0478 (8)
O20.1576 (2)0.8265 (2)0.11536 (16)0.0514 (8)
O30.0201 (3)0.8509 (2)0.22210 (16)0.0538 (8)
O40.1559 (3)0.8640 (3)0.0218 (2)0.0730 (11)
O50.0955 (3)0.7592 (3)0.10577 (18)0.0747 (11)
Cl10.20968 (12)1.29932 (10)0.14917 (7)0.0697 (4)
S10.06425 (8)0.84464 (8)0.07160 (6)0.0381 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.036 (2)0.030 (2)0.038 (2)0.0025 (18)0.0033 (19)0.0001 (18)
C20.037 (2)0.044 (3)0.040 (2)0.007 (2)0.0002 (19)0.011 (2)
C30.042 (3)0.054 (3)0.055 (3)0.004 (2)0.008 (2)0.004 (2)
C40.063 (3)0.037 (3)0.066 (3)0.011 (2)0.001 (3)0.007 (2)
C50.068 (3)0.041 (3)0.052 (3)0.005 (2)0.005 (3)0.013 (2)
C60.052 (3)0.043 (3)0.040 (2)0.007 (2)0.010 (2)0.003 (2)
C70.044 (3)0.037 (2)0.035 (2)0.004 (2)0.0004 (19)0.0011 (19)
C80.039 (2)0.036 (2)0.031 (2)0.003 (2)0.0033 (18)0.0040 (17)
C90.043 (3)0.041 (2)0.033 (2)0.004 (2)0.0097 (19)0.0018 (18)
C100.049 (3)0.033 (2)0.037 (2)0.004 (2)0.001 (2)0.0022 (18)
C110.047 (3)0.048 (3)0.042 (2)0.002 (2)0.009 (2)0.013 (2)
C120.060 (3)0.050 (3)0.040 (2)0.008 (3)0.018 (2)0.005 (2)
C130.061 (3)0.037 (2)0.037 (2)0.006 (2)0.009 (2)0.0048 (19)
N10.048 (2)0.040 (2)0.0329 (19)0.0065 (18)0.0043 (16)0.0036 (16)
N20.049 (2)0.057 (3)0.053 (3)0.004 (2)0.012 (2)0.016 (2)
O10.0518 (19)0.0507 (18)0.0411 (16)0.0011 (15)0.0137 (14)0.0022 (14)
O20.0366 (17)0.060 (2)0.0577 (19)0.0028 (16)0.0076 (15)0.0045 (16)
O30.068 (2)0.0485 (19)0.0450 (17)0.0083 (18)0.0041 (16)0.0094 (16)
O40.090 (3)0.052 (2)0.077 (3)0.018 (2)0.007 (2)0.0162 (19)
O50.087 (3)0.098 (3)0.0394 (19)0.011 (2)0.0108 (19)0.0131 (19)
Cl10.0894 (11)0.0479 (7)0.0718 (9)0.0188 (7)0.0221 (7)0.0146 (6)
S10.0379 (6)0.0399 (6)0.0365 (5)0.0018 (5)0.0035 (5)0.0007 (5)
Geometric parameters (Å, º) top
C1—C61.388 (5)C8—C91.382 (5)
C1—C21.389 (6)C9—C101.381 (6)
C1—S11.767 (4)C9—H90.9300
C2—C31.371 (6)C10—C111.369 (6)
C2—N21.479 (5)C10—Cl11.723 (4)
C3—C41.366 (6)C11—C121.378 (6)
C3—H30.9300C11—H110.9300
C4—C51.373 (6)C12—C131.374 (6)
C4—H40.9300C12—H120.9300
C5—C61.372 (6)C13—H130.9300
C5—H50.9300N1—S11.643 (4)
C6—H60.9300N1—H1N0.857 (19)
C7—O31.201 (5)N2—O41.207 (5)
C7—N11.399 (5)N2—O51.221 (5)
C7—C81.489 (6)O1—S11.426 (3)
C8—C131.379 (5)O2—S11.414 (3)
C6—C1—C2117.8 (4)C8—C9—H9120.2
C6—C1—S1119.0 (3)C11—C10—C9120.8 (4)
C2—C1—S1123.1 (3)C11—C10—Cl1121.0 (3)
C3—C2—C1121.9 (4)C9—C10—Cl1118.2 (3)
C3—C2—N2116.7 (4)C10—C11—C12119.2 (4)
C1—C2—N2121.5 (4)C10—C11—H11120.4
C4—C3—C2119.0 (4)C12—C11—H11120.4
C4—C3—H3120.5C13—C12—C11120.8 (4)
C2—C3—H3120.5C13—C12—H12119.6
C3—C4—C5120.7 (4)C11—C12—H12119.6
C3—C4—H4119.7C12—C13—C8119.7 (4)
C5—C4—H4119.7C12—C13—H13120.2
C6—C5—C4120.2 (4)C8—C13—H13120.2
C6—C5—H5119.9C7—N1—S1123.9 (3)
C4—C5—H5119.9C7—N1—H1N124 (3)
C5—C6—C1120.4 (4)S1—N1—H1N108 (3)
C5—C6—H6119.8O4—N2—O5126.1 (4)
C1—C6—H6119.8O4—N2—C2116.9 (4)
O3—C7—N1121.3 (4)O5—N2—C2117.0 (4)
O3—C7—C8124.1 (4)O2—S1—O1120.19 (19)
N1—C7—C8114.5 (4)O2—S1—N1108.94 (18)
C13—C8—C9119.9 (4)O1—S1—N1104.51 (18)
C13—C8—C7118.3 (4)O2—S1—C1107.76 (19)
C9—C8—C7121.7 (4)O1—S1—C1108.41 (19)
C10—C9—C8119.5 (4)N1—S1—C1106.23 (18)
C10—C9—H9120.2
C6—C1—C2—C31.8 (6)Cl1—C10—C11—C12179.3 (3)
S1—C1—C2—C3174.5 (3)C10—C11—C12—C130.7 (7)
C6—C1—C2—N2178.6 (4)C11—C12—C13—C80.4 (7)
S1—C1—C2—N25.0 (6)C9—C8—C13—C121.7 (6)
C1—C2—C3—C41.8 (7)C7—C8—C13—C12176.5 (4)
N2—C2—C3—C4178.7 (4)O3—C7—N1—S10.6 (6)
C2—C3—C4—C50.7 (7)C8—C7—N1—S1178.1 (3)
C3—C4—C5—C60.2 (7)C3—C2—N2—O4119.2 (5)
C4—C5—C6—C10.1 (7)C1—C2—N2—O461.2 (6)
C2—C1—C6—C50.9 (6)C3—C2—N2—O560.2 (6)
S1—C1—C6—C5175.6 (3)C1—C2—N2—O5119.4 (5)
O3—C7—C8—C1322.3 (6)C7—N1—S1—O250.4 (4)
N1—C7—C8—C13156.3 (4)C7—N1—S1—O1179.9 (3)
O3—C7—C8—C9159.5 (4)C7—N1—S1—C165.4 (4)
N1—C7—C8—C921.9 (6)C6—C1—S1—O217.3 (4)
C13—C8—C9—C101.7 (6)C2—C1—S1—O2159.0 (3)
C7—C8—C9—C10176.4 (4)C6—C1—S1—O1148.9 (3)
C8—C9—C10—C110.5 (6)C2—C1—S1—O127.4 (4)
C8—C9—C10—Cl1178.1 (3)C6—C1—S1—N199.3 (3)
C9—C10—C11—C120.7 (7)C2—C1—S1—N184.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.86 (2)2.41 (3)3.193 (4)153 (4)
Symmetry code: (i) x, y+2, z.

Experimental details

Crystal data
Chemical formulaC13H9ClN2O5S
Mr340.73
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)293
a, b, c (Å)12.2046 (8), 12.6121 (9), 18.433 (1)
V3)2837.3 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.44
Crystal size (mm)0.28 × 0.28 × 0.08
Data collection
DiffractometerOxford Xcalibur
diffractometer with Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.886, 0.966
No. of measured, independent and
observed [I > 2σ(I)] reflections
11298, 2889, 1911
Rint0.051
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.147, 1.20
No. of reflections2889
No. of parameters202
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.34, 0.29

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···O1i0.857 (19)2.41 (3)3.193 (4)153 (4)
Symmetry code: (i) x, y+2, z.
 

Acknowledgements

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

References

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