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

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ISSN: 2056-9890

N-(3-Chloro­benzo­yl)-3-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 19 December 2011; accepted 20 December 2011; online 23 December 2011)

In the title compound, C13H9ClN2O5S, the dihedral angle between the two benzene rings is 83.5 (1)°. In the crystal, mol­ecules are linked via N—H⋯O(S) hydrogen bonds into helical chains running along the b axis.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Bowes et al. (2003[Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1-o3.]); Gowda et al. (2004[Gowda, B. T., Svoboda, I. & Fuess, H. (2004). Z. Naturforsch. Teil A, 59, 845-852.]), on N-(ar­yl)-methane­sulfonamides, see: Jayalakshmi & Gowda (2004[Jayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 491-500.]), onN-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2003[Gowda, B. T., Jyothi, K., Kozisek, J. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 656-660.]), on N-(substitutedbenzo­yl)-aryl­sulfonamides, see: Suchetan et al. (2011[Suchetan, P. A., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o3515.]) and on N-chloro­aryl­amides, see: Gowda & Mahadevappa (1983[Gowda, B. T. & Mahadevappa, D. S. (1983). Talanta, 30, 359-362.]).

[Scheme 1]

Experimental

Crystal data
  • C13H9ClN2O5S

  • Mr = 340.73

  • Monoclinic, P 21 /c

  • a = 11.891 (2) Å

  • b = 5.0577 (6) Å

  • c = 23.488 (3) Å

  • β = 90.43 (1)°

  • V = 1412.6 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.44 mm−1

  • T = 293 K

  • 0.46 × 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 = 0.822, Tmax = 0.957

  • 4873 measured reflections

  • 2840 independent reflections

  • 2204 reflections with I > 2σ(I)

  • Rint = 0.017

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.105

  • S = 1.20

  • 2840 reflections

  • 202 parameters

  • 1 restraint

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

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O2i 0.82 (2) 2.29 (2) 3.100 (3) 169 (3)
Symmetry code: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

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

Diaryl acylsulfonamides are known as potent antitumor agents against a broad spectrum of human tumor xenografts in nude mice. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al., 2003; Gowda et al., 2004), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004), N-(aryl)-arylsulfonamides (Gowda et al., 2003); N-(substitutedbenzoyl)-arylsulfonamides (Suchetan et al., 2011) and N-chloro-arylsulfonamides (Gowda & Mahadevappa, 1983), in the present work, the crystal structure of N-(3-chlorobenzoyl)-3-nitrobenzenesulfonamide (I) has been determined (Fig.1).

The conformation between the N—H and C=O 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-(benzoyl)-3-nitrobenzenesulfonamide (II)(Suchetan et al., 2011). Further, in (I), the conformation between the N—H bond and the meta-nitro group in the sulfonyl benzene ring is syn, similar to that observed in (II). But the conformation of the CO is anti to the meta-Cl atom in the benzoyl ring.

The molecule is twisted at the S—N bond with the torsional angle of -60.40 (29)°, compared to the value of -62.80 (17)° in (II).

The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 77.0 (1)°, compared to the value of 79.2 (1)° in (II). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 83.5 (1)°, compared to the value of 86.7 (1)° in (II).

The packing of molecules linked by of N—H···O(S) hydrogen bonds(Table 1) is shown in Fig. 2.

Related literature top

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003); Gowda et al. (2004), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004), onN-(aryl)-arylsulfonamides, see: Gowda et al. (2003), on N-(substitutedbenzoyl)-arylsulfonamides, see: Suchetan et al. (2011) and on N-chloroarylamides, see: Gowda & Mahadevappa (1983).

Experimental top

The title compound was prepared by refluxing a mixture of 3-chlorobenzoic acid (0.02 mole), 3-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)-3-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 its toluene solution at room temperature.

Refinement top

The H atom of the NH group was located in a difference map and its coordinates were refined with the N—H distance restrained to 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 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. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines.
N-(3-Chlorobenzoyl)-3-nitrobenzenesulfonamide top
Crystal data top
C13H9ClN2O5SF(000) = 696
Mr = 340.73Dx = 1.602 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1638 reflections
a = 11.891 (2) Åθ = 2.4–27.9°
b = 5.0577 (6) ŵ = 0.44 mm1
c = 23.488 (3) ÅT = 293 K
β = 90.43 (1)°Rod, colourless
V = 1412.6 (3) Å30.46 × 0.20 × 0.10 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2840 independent reflections
Radiation source: fine-focus sealed tube2204 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
Rotation method data acquisition using ω scansθmax = 26.4°, θmin = 2.4°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 1414
Tmin = 0.822, Tmax = 0.957k = 36
4873 measured reflectionsl = 1429
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.20 w = 1/[σ2(Fo2) + (0.0074P)2 + 2.6391P]
where P = (Fo2 + 2Fc2)/3
2840 reflections(Δ/σ)max = 0.005
202 parametersΔρmax = 0.35 e Å3
1 restraintΔρmin = 0.35 e Å3
Crystal data top
C13H9ClN2O5SV = 1412.6 (3) Å3
Mr = 340.73Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.891 (2) ŵ = 0.44 mm1
b = 5.0577 (6) ÅT = 293 K
c = 23.488 (3) Å0.46 × 0.20 × 0.10 mm
β = 90.43 (1)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2840 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
2204 reflections with I > 2σ(I)
Tmin = 0.822, Tmax = 0.957Rint = 0.017
4873 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0581 restraint
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.20Δρmax = 0.35 e Å3
2840 reflectionsΔρmin = 0.35 e Å3
202 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
Cl10.01505 (9)0.2312 (2)0.06480 (5)0.0673 (3)
S10.16424 (7)1.19021 (16)0.25405 (3)0.0329 (2)
O10.1952 (2)1.4485 (5)0.23632 (10)0.0459 (6)
O20.06284 (18)1.1510 (5)0.28538 (9)0.0426 (6)
O30.3210 (2)1.0853 (6)0.16263 (11)0.0549 (7)
O40.2384 (3)0.4415 (6)0.40468 (13)0.0754 (9)
O50.4054 (3)0.4980 (8)0.43876 (14)0.0927 (12)
N10.1495 (2)0.9973 (5)0.19807 (11)0.0326 (6)
H1N0.099 (2)0.888 (6)0.2022 (14)0.039*
N20.3285 (3)0.5553 (7)0.40604 (14)0.0596 (10)
C10.2775 (3)1.0595 (6)0.29449 (13)0.0329 (7)
C20.2570 (3)0.8591 (7)0.33282 (14)0.0369 (8)
H20.18580.78550.33660.044*
C30.3472 (3)0.7720 (7)0.36558 (14)0.0427 (9)
C40.4536 (3)0.8782 (9)0.36104 (16)0.0529 (10)
H40.51240.81570.38360.063*
C50.4710 (3)1.0782 (9)0.32241 (17)0.0540 (10)
H50.54231.15190.31890.065*
C60.3836 (3)1.1707 (8)0.28888 (15)0.0436 (8)
H60.39571.30600.26280.052*
C70.2344 (3)0.9602 (7)0.15852 (14)0.0373 (8)
C80.2142 (3)0.7600 (7)0.11301 (13)0.0374 (8)
C90.1165 (3)0.6101 (7)0.10919 (14)0.0399 (8)
H90.05800.63870.13450.048*
C100.1067 (3)0.4200 (8)0.06786 (14)0.0451 (9)
C110.1915 (4)0.3747 (9)0.02952 (15)0.0571 (11)
H110.18400.24450.00180.069*
C120.2877 (4)0.5261 (9)0.03305 (16)0.0607 (12)
H120.34540.49760.00720.073*
C130.3000 (3)0.7185 (8)0.07404 (14)0.0473 (9)
H130.36510.82020.07570.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0696 (7)0.0659 (7)0.0663 (7)0.0096 (6)0.0136 (5)0.0209 (6)
S10.0345 (4)0.0284 (4)0.0357 (4)0.0021 (4)0.0005 (3)0.0003 (4)
O10.0571 (16)0.0278 (13)0.0526 (15)0.0010 (11)0.0058 (12)0.0028 (11)
O20.0355 (12)0.0516 (15)0.0408 (13)0.0068 (11)0.0062 (10)0.0020 (12)
O30.0418 (14)0.0674 (18)0.0557 (16)0.0170 (14)0.0096 (12)0.0107 (15)
O40.093 (2)0.062 (2)0.072 (2)0.0072 (19)0.0132 (19)0.0273 (18)
O50.104 (3)0.108 (3)0.066 (2)0.040 (2)0.0120 (19)0.031 (2)
N10.0338 (15)0.0324 (15)0.0318 (14)0.0039 (12)0.0040 (12)0.0014 (12)
N20.081 (3)0.058 (2)0.0409 (18)0.031 (2)0.0058 (19)0.0080 (17)
C10.0352 (17)0.0316 (17)0.0320 (16)0.0022 (14)0.0005 (13)0.0031 (15)
C20.0380 (18)0.0339 (19)0.0388 (18)0.0029 (15)0.0026 (14)0.0020 (15)
C30.054 (2)0.042 (2)0.0327 (17)0.0148 (18)0.0003 (15)0.0013 (16)
C40.047 (2)0.066 (3)0.045 (2)0.020 (2)0.0072 (17)0.012 (2)
C50.0344 (19)0.072 (3)0.056 (2)0.002 (2)0.0006 (17)0.010 (2)
C60.0395 (19)0.045 (2)0.046 (2)0.0034 (17)0.0036 (16)0.0016 (18)
C70.0375 (18)0.0384 (19)0.0360 (18)0.0004 (16)0.0017 (15)0.0049 (15)
C80.0418 (18)0.039 (2)0.0313 (17)0.0070 (16)0.0047 (14)0.0034 (15)
C90.0410 (19)0.047 (2)0.0314 (17)0.0049 (17)0.0038 (14)0.0014 (16)
C100.057 (2)0.047 (2)0.0319 (18)0.0084 (18)0.0062 (16)0.0074 (17)
C110.077 (3)0.060 (3)0.035 (2)0.014 (2)0.0030 (19)0.0113 (19)
C120.065 (3)0.076 (3)0.041 (2)0.015 (2)0.018 (2)0.005 (2)
C130.049 (2)0.054 (2)0.0388 (19)0.0050 (19)0.0087 (16)0.0026 (19)
Geometric parameters (Å, º) top
Cl1—C101.736 (4)C4—C51.376 (6)
S1—O11.420 (2)C4—H40.9300
S1—O21.431 (2)C5—C61.381 (5)
S1—N11.645 (3)C5—H50.9300
S1—C11.770 (3)C6—H60.9300
O3—C71.212 (4)C7—C81.490 (5)
O4—N21.217 (5)C8—C91.390 (5)
O5—N21.225 (4)C8—C131.391 (4)
N1—C71.390 (4)C9—C101.371 (5)
N1—H1N0.823 (18)C9—H90.9300
N2—C31.468 (5)C10—C111.376 (5)
C1—C21.378 (4)C11—C121.379 (6)
C1—C61.388 (4)C11—H110.9300
C2—C31.387 (5)C12—C131.376 (5)
C2—H20.9300C12—H120.9300
C3—C41.380 (5)C13—H130.9300
O1—S1—O2119.97 (15)C6—C5—H5119.7
O1—S1—N1109.70 (15)C5—C6—C1119.3 (4)
O2—S1—N1104.11 (14)C5—C6—H6120.4
O1—S1—C1107.63 (15)C1—C6—H6120.4
O2—S1—C1108.23 (15)O3—C7—N1119.8 (3)
N1—S1—C1106.45 (14)O3—C7—C8123.0 (3)
C7—N1—S1122.8 (2)N1—C7—C8117.2 (3)
C7—N1—H1N121 (2)C9—C8—C13119.5 (3)
S1—N1—H1N112 (2)C9—C8—C7123.1 (3)
O4—N2—O5123.9 (4)C13—C8—C7117.4 (3)
O4—N2—C3118.2 (3)C10—C9—C8119.6 (3)
O5—N2—C3117.8 (4)C10—C9—H9120.2
C2—C1—C6121.7 (3)C8—C9—H9120.2
C2—C1—S1119.2 (2)C9—C10—C11121.5 (4)
C6—C1—S1119.1 (3)C9—C10—Cl1118.8 (3)
C1—C2—C3117.2 (3)C11—C10—Cl1119.8 (3)
C1—C2—H2121.4C10—C11—C12118.7 (4)
C3—C2—H2121.4C10—C11—H11120.7
C4—C3—C2122.6 (3)C12—C11—H11120.7
C4—C3—N2118.9 (3)C13—C12—C11121.2 (4)
C2—C3—N2118.5 (3)C13—C12—H12119.4
C5—C4—C3118.7 (3)C11—C12—H12119.4
C5—C4—H4120.7C12—C13—C8119.5 (4)
C3—C4—H4120.7C12—C13—H13120.2
C4—C5—C6120.6 (4)C8—C13—H13120.2
C4—C5—H5119.7
O1—S1—N1—C755.8 (3)C4—C5—C6—C10.0 (6)
O2—S1—N1—C7174.6 (3)C2—C1—C6—C50.1 (5)
C1—S1—N1—C760.4 (3)S1—C1—C6—C5176.8 (3)
O1—S1—C1—C2157.3 (3)S1—N1—C7—O34.7 (5)
O2—S1—C1—C226.2 (3)S1—N1—C7—C8174.1 (2)
N1—S1—C1—C285.2 (3)O3—C7—C8—C9177.9 (3)
O1—S1—C1—C619.5 (3)N1—C7—C8—C90.8 (5)
O2—S1—C1—C6150.5 (3)O3—C7—C8—C130.0 (5)
N1—S1—C1—C698.1 (3)N1—C7—C8—C13178.7 (3)
C6—C1—C2—C30.2 (5)C13—C8—C9—C101.3 (5)
S1—C1—C2—C3176.9 (2)C7—C8—C9—C10176.5 (3)
C1—C2—C3—C40.2 (5)C8—C9—C10—C110.5 (5)
C1—C2—C3—N2178.9 (3)C8—C9—C10—Cl1178.8 (3)
O4—N2—C3—C4171.0 (4)C9—C10—C11—C120.3 (6)
O5—N2—C3—C48.2 (5)Cl1—C10—C11—C12179.6 (3)
O4—N2—C3—C28.1 (5)C10—C11—C12—C130.3 (6)
O5—N2—C3—C2172.7 (3)C11—C12—C13—C80.6 (6)
C2—C3—C4—C50.1 (5)C9—C8—C13—C121.4 (5)
N2—C3—C4—C5179.0 (3)C7—C8—C13—C12176.6 (3)
C3—C4—C5—C60.0 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.82 (2)2.29 (2)3.100 (3)169 (3)
Symmetry code: (i) x, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC13H9ClN2O5S
Mr340.73
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)11.891 (2), 5.0577 (6), 23.488 (3)
β (°) 90.43 (1)
V3)1412.6 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.44
Crystal size (mm)0.46 × 0.20 × 0.10
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.822, 0.957
No. of measured, independent and
observed [I > 2σ(I)] reflections
4873, 2840, 2204
Rint0.017
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.105, 1.20
No. of reflections2840
No. of parameters202
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.35, 0.35

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···O2i0.823 (18)2.288 (19)3.100 (3)169 (3)
Symmetry code: (i) x, y1/2, z+1/2.
 

Acknowledgements

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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