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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 9| September 2012| Page o2766
doi:10.1107/S1600536812036331

N-(2-Methyl­phen­yl)-4-nitro­benzene­sulfonamide

U. Chaithanya,a Sabine Forob and B. Thimme Gowdaa*

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 August 2012; accepted 20 August 2012; online 25 August 2012)

In the title compound, C13H12N2O4S, the dihedral angle between the planes of the rings is 51.11 (10)°. In the crystal, mol­ecules are linked into inversion dimers through pairs of N—H⋯O(S) hydrogen bonds.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Alkan et al. (2011[Alkan, C., Tek, Y. & Kahraman, D. (2011). Turk. J. Chem. 35, 769-777.]); 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 & Weiss (1994[Gowda, B. T. & Weiss, A. (1994). Z. Naturforsch. Teil A, 49, 695-702.]); Saeed et al. (2010[Saeed, A., Arshad, M. & Simpson, J. (2010). Acta Cryst. E66, o2808-o2809.]); Shahwar et al. (2012[Shahwar, D., Tahir, M. N., Chohan, M. M., Ahmad, N. & Raza, M. A. (2012). Acta Cryst. E68, o1160.]), of N-aryl­sulfonamides, see: Chaithanya et al. (2012[Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o2745.]); Gowda et al. (2005[Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.]) and of N-chloro­aryl­sulfonamides, see: Gowda & Shetty (2004[Gowda, B. T. & Shetty, M. (2004). J. Phys. Org. Chem. 17, 848-864.]); Shetty & Gowda (2004[Shetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63-72.]).

[Scheme 1]

Experimental

Crystal data

  • C13H12N2O4S

  • Mr = 292.31

  • Monoclinic, P 21 /n

  • a = 14.106 (1) Å

  • b = 7.0082 (5) Å

  • c = 14.854 (2) Å

  • β = 110.84 (1)°

  • V = 1372.4 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.25 mm−1

  • T = 293 K

  • 0.44 × 0.44 × 0.24 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 = 0.898, Tmax = 0.942

  • 4889 measured reflections

  • 2781 independent reflections

  • 2198 reflections with I > 2σ(I)

  • Rint = 0.016
Refinement

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.119

  • S = 1.08

  • 2781 reflections

  • 185 parameters

  • 1 restraint

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

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O2i 0.83 (2) 2.11 (2) 2.923 (2) 166 (2)
Symmetry code: (i) -x, -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 RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812036331/bt6824sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812036331/bt6824Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812036331/bt6824Isup3.cml

checkCIF report


Comment top

As a part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Alkan et al., 2011; Bowes et al., 2003; Gowda & Weiss, 1994; Saeed et al., 2010; Shahwar et al., 2012); N-arylsulfonamides (Chaithanya et al., 2012; Gowda et al., 2005) and N-chloroarylsulfonamides (Gowda & Shetty, 2004; Shetty & Gowda, 2004), in the present work, the crystal structure of N-(2-methylphenyl)-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 S═O bonds (Fig.1). Further, the conformation of the N—H bond in the —SO2—NH— segment is syn to the ortho-methyl group in the anilino ring, compared to syn conformation observed between the N—H bond and ortho- nitro group in the sulfonyl benzene ring in N-(4-methylphenyl)-2-nitrobenzenesulfonamide (I) (Chaithanya et al., 2012). The molecule is twisted at the S—N bond with the torsional angle of -58.97 (21)°, compared to the value of 76.55 (18)° in (I).

The dihedral angle between the sulfonyl and the anilino rings is 51.11 (10)°, compared to the value of 72.64 (8)° in (I).

In the crystal structure, the pairs of intermolecular N–H···O (S) hydrogen bonds (Table 1) link the molecules into inversion dimers. 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-(aryl)-amides, see: Alkan et al. (2011); Bowes et al. (2003); Gowda & Weiss (1994); Saeed et al. (2010); Shahwar et al. (2012), of N-arylsulfonamides, see: Chaithanya et al. (2012); Gowda et al. (2005) and of N-chloroarylsulfonamides, see: Gowda & Shetty (2004); Shetty & Gowda (2004).

Experimental top

The title compound was prepared by treating 4-nitrobenzenesulfonylchloride with 2-methylaniline 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-methylphenyl)-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 (429 K) from dilute ethanol. The purity of the compound was checked and characterized by its infrared spectra.

Prism like light brown 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, methyl C—H = 0.96 Å. The coordinates of the amino H atom were 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(C-aromatic, N) or 1.5 Ueq(C-methyl) 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
Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme and with displacement ellipsoids drawn at the 50% probability level.

Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
N-(2-Methylphenyl)-4-nitrobenzenesulfonamide top
Crystal data top
C13H12N2O4SF(000) = 608
Mr = 292.31Dx = 1.415 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2269 reflections
a = 14.106 (1) Åθ = 2.6–27.7°
b = 7.0082 (5) ŵ = 0.25 mm−1
c = 14.854 (2) ÅT = 293 K
β = 110.84 (1)°Prism, light brown
V = 1372.4 (2) Å30.44 × 0.44 × 0.24 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2781 independent reflections
Radiation source: fine-focus sealed tube2198 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
Rotation method data acquisition using ω scansθmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		h = −16→17
Tmin = 0.898, Tmax = 0.942k = −8→8
4889 measured reflectionsl = −11→18
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0444P)2 + 0.7236P]
where P = (Fo2 + 2Fc2)/3
2781 reflections(Δ/σ)max < 0.001
185 parametersΔρmax = 0.19 e Å−3
1 restraintΔρmin = −0.33 e Å−3
Crystal data top
C13H12N2O4SV = 1372.4 (2) Å3
Mr = 292.31Z = 4
Monoclinic, P21/nMo Kα radiation
a = 14.106 (1) ŵ = 0.25 mm−1
b = 7.0082 (5) ÅT = 293 K
c = 14.854 (2) Å0.44 × 0.44 × 0.24 mm
β = 110.84 (1)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2781 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		2198 reflections with I > 2σ(I)
Tmin = 0.898, Tmax = 0.942Rint = 0.016
4889 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0461 restraint
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.19 e Å−3
2781 reflectionsΔρmin = −0.33 e Å−3
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
S10.16315 (4)0.55405 (8)0.49925 (4)0.05191 (19)
O10.22495 (12)0.6861 (2)0.47241 (13)0.0623 (4)
O20.11524 (13)0.6116 (2)0.56500 (13)0.0680 (5)
O30.3815 (2)−0.2517 (4)0.69841 (19)0.1191 (9)
O40.45351 (17)−0.2122 (3)0.59408 (18)0.0960 (7)
N10.07213 (13)0.4839 (3)0.40317 (15)0.0539 (5)
H1N0.0239 (16)0.439 (3)0.4158 (18)0.065*
N20.3977 (2)−0.1605 (4)0.63546 (19)0.0804 (7)
C10.23798 (16)0.3504 (3)0.54651 (16)0.0493 (5)
C20.2147 (2)0.2341 (4)0.61097 (19)0.0690 (7)
H20.16330.26780.63340.083*
C30.2686 (2)0.0682 (4)0.6414 (2)0.0757 (8)
H30.2546−0.01160.68520.091*
C40.34313 (18)0.0224 (4)0.60623 (17)0.0613 (6)
C50.36773 (18)0.1362 (4)0.54339 (19)0.0642 (6)
H50.41900.10120.52100.077*
C60.31531 (17)0.3033 (4)0.51386 (18)0.0595 (6)
H60.33170.38450.47210.071*
C70.09202 (15)0.3986 (3)0.32411 (16)0.0516 (5)
C80.06673 (17)0.2084 (4)0.30017 (18)0.0605 (6)
C90.0841 (2)0.1372 (5)0.2200 (2)0.0808 (9)
H90.06570.01210.20060.097*
C100.1274 (2)0.2459 (7)0.1691 (2)0.0949 (11)
H100.13860.19380.11620.114*
C110.1544 (2)0.4303 (6)0.1948 (2)0.0906 (11)
H110.18540.50270.16060.109*
C120.13538 (18)0.5092 (5)0.27233 (19)0.0704 (7)
H120.15180.63600.28930.084*
C130.0228 (3)0.0823 (4)0.3571 (2)0.0861 (9)
H13A−0.04550.12150.34680.129*
H13B0.06310.09230.42430.129*
H13C0.0227−0.04760.33650.129*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0489 (3)0.0462 (3)0.0676 (4)−0.0081 (2)0.0293 (3)−0.0158 (3)
O10.0589 (9)0.0503 (9)0.0836 (12)−0.0129 (7)0.0325 (9)−0.0083 (8)
O20.0634 (10)0.0686 (11)0.0845 (12)−0.0109 (8)0.0416 (9)−0.0321 (9)
O30.140 (2)0.1042 (19)0.0991 (18)0.0273 (16)0.0256 (16)0.0432 (15)
O40.0757 (13)0.0803 (14)0.1144 (18)0.0190 (11)0.0122 (13)−0.0008 (13)
N10.0436 (10)0.0542 (11)0.0688 (12)−0.0043 (8)0.0263 (9)−0.0118 (9)
N20.0741 (15)0.0728 (16)0.0712 (16)0.0040 (13)−0.0026 (13)0.0051 (13)
C10.0481 (11)0.0503 (12)0.0524 (12)−0.0083 (10)0.0216 (10)−0.0114 (10)
C20.0742 (16)0.0780 (18)0.0681 (16)−0.0030 (14)0.0418 (14)−0.0009 (14)
C30.0884 (19)0.0779 (19)0.0641 (16)−0.0036 (16)0.0313 (15)0.0141 (14)
C40.0569 (13)0.0594 (14)0.0550 (13)−0.0014 (11)0.0044 (11)−0.0034 (11)
C50.0534 (13)0.0703 (16)0.0696 (16)0.0039 (12)0.0229 (12)0.0001 (13)
C60.0533 (13)0.0629 (14)0.0695 (15)−0.0008 (11)0.0306 (12)0.0032 (12)
C70.0370 (10)0.0633 (14)0.0532 (12)0.0069 (10)0.0142 (9)−0.0045 (11)
C80.0497 (12)0.0661 (15)0.0635 (14)0.0088 (11)0.0174 (11)−0.0150 (12)
C90.0664 (16)0.097 (2)0.0754 (18)0.0128 (16)0.0213 (15)−0.0277 (17)
C100.0700 (18)0.153 (4)0.0624 (18)0.019 (2)0.0248 (15)−0.021 (2)
C110.0658 (17)0.149 (4)0.0614 (17)0.002 (2)0.0279 (14)0.012 (2)
C120.0561 (14)0.0890 (19)0.0644 (15)0.0011 (13)0.0193 (12)0.0088 (14)
C130.108 (2)0.0572 (16)0.102 (2)−0.0184 (16)0.049 (2)−0.0244 (16)
Geometric parameters (Å, º) top
S1—O11.4221 (16)C5—H50.9300
S1—O21.4292 (16)C6—H60.9300
S1—N11.620 (2)C7—C121.379 (3)
S1—C11.765 (2)C7—C81.393 (3)
O3—N21.220 (3)C8—C91.391 (3)
O4—N21.214 (3)C8—C131.501 (4)
N1—C71.431 (3)C9—C101.361 (5)
N1—H1N0.830 (16)C9—H90.9300
N2—C41.479 (3)C10—C111.363 (5)
C1—C61.382 (3)C10—H100.9300
C1—C21.383 (3)C11—C121.387 (4)
C2—C31.375 (4)C11—H110.9300
C2—H20.9300C12—H120.9300
C3—C41.369 (4)C13—H13A0.9600
C3—H30.9300C13—H13B0.9600
C4—C51.363 (3)C13—H13C0.9600
C5—C61.371 (3)
O1—S1—O2119.61 (10)C5—C6—C1119.7 (2)
O1—S1—N1108.86 (11)C5—C6—H6120.2
O2—S1—N1105.57 (10)C1—C6—H6120.2
O1—S1—C1107.34 (10)C12—C7—C8121.3 (2)
O2—S1—C1108.52 (11)C12—C7—N1118.6 (2)
N1—S1—C1106.21 (10)C8—C7—N1120.1 (2)
C7—N1—S1121.63 (14)C9—C8—C7117.0 (3)
C7—N1—H1N116.3 (18)C9—C8—C13120.3 (3)
S1—N1—H1N111.9 (18)C7—C8—C13122.6 (2)
O4—N2—O3124.3 (3)C10—C9—C8121.7 (3)
O4—N2—C4118.3 (3)C10—C9—H9119.2
O3—N2—C4117.3 (3)C8—C9—H9119.2
C6—C1—C2120.9 (2)C9—C10—C11120.7 (3)
C6—C1—S1119.24 (18)C9—C10—H10119.6
C2—C1—S1119.75 (18)C11—C10—H10119.6
C3—C2—C1119.2 (2)C10—C11—C12119.5 (3)
C3—C2—H2120.4C10—C11—H11120.2
C1—C2—H2120.4C12—C11—H11120.2
C4—C3—C2118.8 (2)C7—C12—C11119.6 (3)
C4—C3—H3120.6C7—C12—H12120.2
C2—C3—H3120.6C11—C12—H12120.2
C5—C4—C3122.8 (2)C8—C13—H13A109.5
C5—C4—N2118.4 (2)C8—C13—H13B109.5
C3—C4—N2118.8 (3)H13A—C13—H13B109.5
C4—C5—C6118.6 (2)C8—C13—H13C109.5
C4—C5—H5120.7H13A—C13—H13C109.5
C6—C5—H5120.7H13B—C13—H13C109.5
O1—S1—N1—C756.3 (2)C3—C4—C5—C6−0.3 (4)
O2—S1—N1—C7−174.08 (18)N2—C4—C5—C6178.1 (2)
C1—S1—N1—C7−59.0 (2)C4—C5—C6—C1−1.3 (4)
O1—S1—C1—C6−29.1 (2)C2—C1—C6—C52.0 (4)
O2—S1—C1—C6−159.71 (18)S1—C1—C6—C5−174.02 (19)
N1—S1—C1—C687.2 (2)S1—N1—C7—C12−66.4 (3)
O1—S1—C1—C2154.79 (19)S1—N1—C7—C8114.3 (2)
O2—S1—C1—C224.2 (2)C12—C7—C8—C9−2.1 (3)
N1—S1—C1—C2−88.9 (2)N1—C7—C8—C9177.3 (2)
C6—C1—C2—C3−1.0 (4)C12—C7—C8—C13177.8 (2)
S1—C1—C2—C3175.0 (2)N1—C7—C8—C13−2.9 (3)
C1—C2—C3—C4−0.6 (4)C7—C8—C9—C102.4 (4)
C2—C3—C4—C51.2 (4)C13—C8—C9—C10−177.5 (3)
C2—C3—C4—N2−177.1 (2)C8—C9—C10—C11−0.7 (5)
O4—N2—C4—C5−8.4 (4)C9—C10—C11—C12−1.5 (5)
O3—N2—C4—C5173.3 (3)C8—C7—C12—C110.0 (4)
O4—N2—C4—C3170.0 (3)N1—C7—C12—C11−179.4 (2)
O3—N2—C4—C3−8.2 (4)C10—C11—C12—C71.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.83 (2)2.11 (2)2.923 (2)166 (2)
Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC13H12N2O4S
Mr292.31
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)14.106 (1), 7.0082 (5), 14.854 (2)
β (°) 110.84 (1)
V (Å3)1372.4 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.25
Crystal size (mm)0.44 × 0.44 × 0.24
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.898, 0.942
No. of measured, independent and
observed [I > 2σ(I)] reflections		4889, 2781, 2198
Rint0.016
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.119, 1.08
No. of reflections2781
No. of parameters185
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.19, −0.33

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···O2i0.830 (16)2.111 (17)2.923 (2)166 (2)
Symmetry code: (i) −x, −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.

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ISSN: 2056-9890
Volume 68| Part 9| September 2012| Page o2766
doi:10.1107/S1600536812036331
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