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ISSN: 2056-9890

N-(4-Methyl­phen­yl)-2-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 3 August 2012; accepted 15 August 2012; online 23 August 2012)

In the crystal of the title compound, C13H12N2O4S, the conformation of the N—H bond in the –SO2—NH– segment is syn to the ortho-nitro group in the sulfonyl benzene ring. The mol­ecule is twisted at the S—N bond with a torsion angle of 76.55 (18)°. The dihedral angle between the planes of the rings is 72.64 (8)°. In the crystal, mol­ecules are linked by pairs of N—H⋯O(S) hydrogen bonds to form inversion dimers.

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.]). For N-aryl­sulfonamides, see: Chaithanya et al. (2012[Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o2577.]); Gowda et al. (2005[Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.]). For 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 = 292.32

  • Monoclinic, P 21 /c

  • a = 8.2787 (5) Å

  • b = 11.2017 (7) Å

  • c = 14.6435 (8) Å

  • β = 91.116 (5)°

  • V = 1357.72 (14) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.25 mm−1

  • T = 295 K

  • 0.48 × 0.40 × 0.40 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, Oxfordshire, England.]) Tmin = 0.888, Tmax = 0.906

  • 5351 measured reflections

  • 2766 independent reflections

  • 2353 reflections with I > 2σ(I)

  • Rint = 0.013

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.108

  • S = 1.06

  • 2766 reflections

  • 184 parameters

  • 1 restraint

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

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.42 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) 2.27 (2) 3.099 (2) 169 (2)
Symmetry code: (i) -x+1, -y, -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 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 molecular structure of N-(4-methylphenyl)-2-nitrobenzenesulfonamide has been determined (Fig. 1).

The conformation of the N–H bond in the –SO2–NH– segment is syn to the ortho-nitro group in the sulfonyl benzene ring, similar to that observed in N-(4-chlorophenyl)-2-nitrobenzenesulfonamide I (Chaithanya et al., 2012). The molecule is twisted at the S–N bond with the torsional angle of 76.55 (18)°, compared to the value of 79.17 (18)° in I.

The dihedral angle between the sulfonyl and the anilino rings is 72.64 (8)°, compared to the value of 70.27 (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). For N-arylsulfonamides, see: Chaithanya et al. (2012); Gowda et al. (2005). For N-chloroarylsulfonamides, see: Gowda & Shetty (2004); Shetty & Gowda (2004).

Experimental top

The title compound was prepared by treating 2-nitrobenzenesulfonylchloride with 4-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-(4-methylphenyl)-2-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 (385 K) from dilute ethanol. The purity of the compound was checked and characterized by its infrared spectra.

Prism like yellow 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 = 0.93Å, methyl C–H = 0.96Å. 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(C-aromatic, N) and 1.5 Ueq(C-methyl) 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
Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbiterary radius.

Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
N-(4-Methylphenyl)-2-nitrobenzenesulfonamide top
Crystal data top
C13H12N2O4SF(000) = 608
Mr = 292.32Dx = 1.430 Mg m3
Monoclinic, P21/cMelting point: 385 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 8.2787 (5) ÅCell parameters from 2975 reflections
b = 11.2017 (7) Åθ = 2.9–27.8°
c = 14.6435 (8) ŵ = 0.25 mm1
β = 91.116 (5)°T = 295 K
V = 1357.72 (14) Å3Prism, yellow
Z = 40.48 × 0.40 × 0.40 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2766 independent reflections
Radiation source: fine-focus sealed tube2353 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
Rotation method data acquisition using ω scansθmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 1010
Tmin = 0.888, Tmax = 0.906k = 1411
5351 measured reflectionsl = 1813
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.056P)2 + 0.5176P]
where P = (Fo2 + 2Fc2)/3
2766 reflections(Δ/σ)max < 0.001
184 parametersΔρmax = 0.27 e Å3
1 restraintΔρmin = 0.42 e Å3
Crystal data top
C13H12N2O4SV = 1357.72 (14) Å3
Mr = 292.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.2787 (5) ŵ = 0.25 mm1
b = 11.2017 (7) ÅT = 295 K
c = 14.6435 (8) Å0.48 × 0.40 × 0.40 mm
β = 91.116 (5)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2766 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
2353 reflections with I > 2σ(I)
Tmin = 0.888, Tmax = 0.906Rint = 0.013
5351 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0381 restraint
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.27 e Å3
2766 reflectionsΔρmin = 0.42 e Å3
184 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C10.3224 (2)0.15569 (16)0.18420 (11)0.0364 (4)
C20.1752 (2)0.11277 (16)0.15102 (12)0.0401 (4)
C30.0303 (2)0.1524 (2)0.18391 (16)0.0571 (5)
H30.06670.12040.16220.068*
C40.0316 (3)0.2405 (2)0.24967 (17)0.0669 (7)
H40.06550.26870.27220.080*
C50.1747 (3)0.2869 (2)0.28221 (15)0.0626 (6)
H50.17410.34760.32550.075*
C60.3206 (3)0.24352 (19)0.25080 (13)0.0485 (5)
H60.41740.27350.27450.058*
C70.6251 (2)0.27979 (16)0.04577 (12)0.0373 (4)
C80.6677 (3)0.35516 (19)0.11701 (14)0.0565 (6)
H80.65330.33140.17720.068*
C90.7320 (3)0.46652 (19)0.09806 (15)0.0588 (6)
H90.76020.51670.14640.071*
C100.7555 (2)0.50554 (18)0.01005 (14)0.0480 (5)
C110.7119 (3)0.4285 (2)0.05929 (14)0.0610 (6)
H110.72520.45250.11950.073*
C120.6490 (3)0.3172 (2)0.04227 (13)0.0541 (5)
H120.62250.26680.09080.065*
C130.8262 (3)0.6268 (2)0.00946 (18)0.0665 (6)
H13A0.93180.63260.01850.100*
H13B0.75760.68750.01500.100*
H13C0.83410.63740.07430.100*
N10.5608 (2)0.16250 (14)0.05726 (10)0.0425 (4)
H1N0.535 (3)0.1265 (18)0.0090 (12)0.051*
N20.16650 (18)0.02534 (14)0.07570 (12)0.0465 (4)
O10.48358 (16)0.02622 (11)0.12570 (9)0.0459 (3)
O20.62478 (16)0.12592 (13)0.22019 (9)0.0503 (4)
O30.22587 (19)0.05430 (15)0.00333 (10)0.0592 (4)
O40.0967 (2)0.06803 (16)0.08834 (14)0.0770 (5)
S10.51096 (5)0.09646 (4)0.14959 (3)0.03688 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0385 (9)0.0381 (9)0.0326 (8)0.0024 (7)0.0034 (7)0.0054 (7)
C20.0390 (9)0.0412 (10)0.0403 (9)0.0001 (7)0.0037 (7)0.0042 (8)
C30.0390 (10)0.0669 (14)0.0655 (13)0.0028 (10)0.0086 (9)0.0010 (11)
C40.0542 (13)0.0830 (17)0.0643 (14)0.0177 (12)0.0183 (11)0.0067 (13)
C50.0699 (15)0.0674 (15)0.0509 (12)0.0141 (12)0.0108 (11)0.0132 (11)
C60.0513 (11)0.0551 (12)0.0390 (10)0.0018 (9)0.0013 (8)0.0033 (9)
C70.0365 (9)0.0372 (9)0.0385 (9)0.0009 (7)0.0024 (7)0.0010 (7)
C80.0853 (16)0.0478 (11)0.0368 (10)0.0110 (11)0.0101 (10)0.0022 (9)
C90.0868 (16)0.0428 (11)0.0470 (11)0.0104 (11)0.0053 (11)0.0089 (9)
C100.0519 (11)0.0392 (10)0.0528 (11)0.0008 (8)0.0014 (9)0.0059 (9)
C110.0830 (16)0.0606 (13)0.0391 (10)0.0181 (12)0.0052 (10)0.0124 (10)
C120.0717 (14)0.0545 (12)0.0359 (10)0.0158 (10)0.0054 (9)0.0009 (9)
C130.0814 (17)0.0459 (12)0.0720 (15)0.0096 (11)0.0013 (13)0.0118 (11)
N10.0512 (9)0.0412 (9)0.0353 (8)0.0074 (7)0.0066 (7)0.0040 (6)
N20.0368 (8)0.0437 (9)0.0587 (10)0.0018 (7)0.0039 (7)0.0016 (8)
O10.0465 (7)0.0362 (7)0.0550 (8)0.0030 (5)0.0038 (6)0.0047 (6)
O20.0429 (7)0.0616 (9)0.0462 (7)0.0010 (6)0.0077 (6)0.0073 (6)
O30.0638 (9)0.0675 (10)0.0464 (8)0.0009 (8)0.0024 (7)0.0072 (7)
O40.0710 (11)0.0558 (10)0.1045 (14)0.0252 (8)0.0067 (10)0.0084 (9)
S10.0344 (2)0.0384 (3)0.0378 (2)0.00117 (17)0.00018 (17)0.00418 (18)
Geometric parameters (Å, º) top
C1—C61.386 (3)C9—C101.378 (3)
C1—C21.389 (3)C9—H90.9300
C1—S11.7786 (18)C10—C111.375 (3)
C2—C31.375 (3)C10—C131.508 (3)
C2—N21.476 (2)C11—C121.376 (3)
C3—C41.378 (3)C11—H110.9300
C3—H30.9300C12—H120.9300
C4—C51.371 (4)C13—H13A0.9600
C4—H40.9300C13—H13B0.9600
C5—C61.388 (3)C13—H13C0.9600
C5—H50.9300N1—S11.6022 (16)
C6—H60.9300N1—H1N0.837 (15)
C7—C121.374 (3)N2—O41.211 (2)
C7—C81.382 (3)N2—O31.221 (2)
C7—N11.429 (2)O1—S11.4349 (14)
C8—C91.386 (3)O2—S11.4240 (14)
C8—H80.9300
C6—C1—C2118.06 (17)C11—C10—C9116.84 (19)
C6—C1—S1119.16 (14)C11—C10—C13121.48 (19)
C2—C1—S1122.68 (14)C9—C10—C13121.7 (2)
C3—C2—C1122.09 (19)C10—C11—C12121.98 (19)
C3—C2—N2116.46 (17)C10—C11—H11119.0
C1—C2—N2121.40 (16)C12—C11—H11119.0
C2—C3—C4118.7 (2)C7—C12—C11120.55 (19)
C2—C3—H3120.6C7—C12—H12119.7
C4—C3—H3120.6C11—C12—H12119.7
C5—C4—C3120.6 (2)C10—C13—H13A109.5
C5—C4—H4119.7C10—C13—H13B109.5
C3—C4—H4119.7H13A—C13—H13B109.5
C4—C5—C6120.2 (2)C10—C13—H13C109.5
C4—C5—H5119.9H13A—C13—H13C109.5
C6—C5—H5119.9H13B—C13—H13C109.5
C1—C6—C5120.2 (2)C7—N1—S1128.79 (13)
C1—C6—H6119.9C7—N1—H1N115.7 (15)
C5—C6—H6119.9S1—N1—H1N115.1 (15)
C12—C7—C8118.87 (18)O4—N2—O3124.30 (19)
C12—C7—N1116.85 (16)O4—N2—C2118.40 (18)
C8—C7—N1124.26 (16)O3—N2—C2117.25 (16)
C7—C8—C9119.45 (19)O2—S1—O1119.88 (8)
C7—C8—H8120.3O2—S1—N1109.16 (8)
C9—C8—H8120.3O1—S1—N1106.17 (8)
C10—C9—C8122.30 (19)O2—S1—C1106.18 (8)
C10—C9—H9118.8O1—S1—C1106.94 (8)
C8—C9—H9118.8N1—S1—C1108.05 (8)
C6—C1—C2—C31.7 (3)C8—C7—C12—C111.0 (3)
S1—C1—C2—C3174.45 (16)N1—C7—C12—C11179.4 (2)
C6—C1—C2—N2175.75 (16)C10—C11—C12—C71.1 (4)
S1—C1—C2—N28.0 (2)C12—C7—N1—S1176.43 (16)
C1—C2—C3—C42.3 (3)C8—C7—N1—S15.2 (3)
N2—C2—C3—C4175.36 (19)C3—C2—N2—O458.7 (2)
C2—C3—C4—C50.6 (4)C1—C2—N2—O4123.6 (2)
C3—C4—C5—C61.6 (4)C3—C2—N2—O3118.8 (2)
C2—C1—C6—C50.4 (3)C1—C2—N2—O358.9 (2)
S1—C1—C6—C5176.78 (16)C7—N1—S1—O238.49 (19)
C4—C5—C6—C12.1 (3)C7—N1—S1—O1169.02 (16)
C12—C7—C8—C90.5 (3)C7—N1—S1—C176.55 (18)
N1—C7—C8—C9178.8 (2)C6—C1—S1—O218.56 (17)
C7—C8—C9—C100.1 (4)C2—C1—S1—O2157.61 (15)
C8—C9—C10—C110.1 (4)C6—C1—S1—O1147.65 (15)
C8—C9—C10—C13179.8 (2)C2—C1—S1—O128.52 (17)
C9—C10—C11—C120.6 (4)C6—C1—S1—N198.44 (16)
C13—C10—C11—C12179.2 (2)C2—C1—S1—N185.40 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.84 (2)2.27 (2)3.099 (2)169 (2)
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC13H12N2O4S
Mr292.32
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)8.2787 (5), 11.2017 (7), 14.6435 (8)
β (°) 91.116 (5)
V3)1357.72 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.48 × 0.40 × 0.40
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.888, 0.906
No. of measured, independent and
observed [I > 2σ(I)] reflections
5351, 2766, 2353
Rint0.013
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.108, 1.06
No. of reflections2766
No. of parameters184
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.42

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 (15)2.273 (16)3.099 (2)169 (2)
Symmetry code: (i) x+1, y, z.
 

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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