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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2763.
Published online 2009 October 17. doi:  10.1107/S1600536809041841
PMCID: PMC2971132

N-(2,5-Dimethyl­phen­yl)benzene­sulfonamide

Abstract

In the title compound, C14H15NO2S, the dihedral angle between the aromatic rings is 40.4 (1)° relative to each other. In the crystal, inversion dimers linked by pairs of N—H(...)O hydrogen bonds occur.

Related literature

For the preparation of the title compound, see: Gowda et al. (2005 [triangle]). For related structures, see: Gowda et al. (2008a [triangle],b [triangle]; 2009 [triangle]). For bond-length data for other aryl sulfonamides, see: Gelbrich et al. (2007 [triangle]); Perlovich et al. (2006 [triangle]).

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Object name is e-65-o2763-scheme1.jpg

Experimental

Crystal data

  • C14H15NO2S
  • M r = 261.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2763-efi1.jpg
  • a = 10.523 (1) Å
  • b = 8.5631 (7) Å
  • c = 15.135 (2) Å
  • β = 101.86 (1)°
  • V = 1334.7 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 299 K
  • 0.44 × 0.40 × 0.34 mm

Data collection

  • Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 [triangle]) T min = 0.903, T max = 0.924
  • 5236 measured reflections
  • 2727 independent reflections
  • 2221 reflections with I > 2σ(I)
  • R int = 0.010

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.108
  • S = 1.10
  • 2727 reflections
  • 169 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809041841/pk2200sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041841/pk2200Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for an extension of his research fellowship.

supplementary crystallographic information

Comment

In the present work, as part of a study of substituent effects on the structures of N-(aryl)-arylsulfonamides, the structure of N-(2,5-dimethylphenyl)benzenesulfonamide (I) has been determined (Gowda et al., 2008a, 2008b, 2009). The conformation of the N—C bond in the C—SO2—NH—C segment has gauche torsions with the S=O bonds (Fig. 1). The molecule is bent at the S atom with the C—SO2—NH—C torsion angle of 62.7 (2)°. The two benzene rings in (I) are tilted relative to each other by 40.4 (1)°, compared to the values of 61.5 (1)° in N-(2-methylphenyl)benzenesulfonamide (II) (Gowda et al., 2008b), 64.8 (1)° in N-(2,3-dimethylphenyl)- benzenesulfonamide (III) (Gowda et al., 2009) and 44.9 (1)° in N-(2,6-dimethylphenyl)benzenesulfonamide (IV) (Gowda et al., 2008a). The other bond parameters are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007). The crystal packing of (I) showing dimers linked via N—H···O(S) hydrogen bonds (Table 1) is given in Fig.2.

Experimental

A solution of benzene (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 0 ° C. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual benzenesulfonylchloride was treated with 2,5-dimethylaniline in the stoichiometric ratio and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid N-(2,5-dimethylphenyl)benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by recording its infrared and NMR spectra (Gowda et al., 2005). The single crystals used in X-ray diffraction studies were grown in ethanolic solution by a slow evaporation at room temperature.

Refinement

The H atom of the NH group was located in a difference map and its position refined with N—H = 0.83 (2) %A. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93–0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

Figures

Fig. 1.
Molecular structure of (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Molecular packing of (I) with hydrogen bonding shown as dashed lines, viewed down the b axis.

Crystal data

C14H15NO2SF(000) = 552
Mr = 261.33Dx = 1.301 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2374 reflections
a = 10.523 (1) Åθ = 2.6–27.8°
b = 8.5631 (7) ŵ = 0.24 mm1
c = 15.135 (2) ÅT = 299 K
β = 101.86 (1)°Prism, colourless
V = 1334.7 (2) Å30.44 × 0.40 × 0.34 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur (TM) Single Crystal X-ray Diffractometer with Sapphire CCD Detector.2727 independent reflections
Radiation source: fine-focus sealed tube2221 reflections with I > 2σ(I)
graphiteRint = 0.010
Detector resolution: 0 pixels mm-1θmax = 26.4°, θmin = 2.6°
Rotation method data acquisition using ω and phi scans.h = −10→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)k = −10→7
Tmin = 0.903, Tmax = 0.924l = −17→18
5236 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108w = 1/[σ2(Fo2) + (0.0568P)2 + 0.2974P] where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
2727 reflectionsΔρmax = 0.27 e Å3
169 parametersΔρmin = −0.25 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0149 (18)

Special details

Experimental. 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)

xyzUiso*/Ueq
S10.78193 (4)0.44572 (5)−0.00630 (3)0.03753 (16)
O10.88777 (11)0.35489 (14)−0.02510 (9)0.0504 (3)
O20.68808 (12)0.37259 (15)0.03523 (9)0.0476 (3)
N10.84891 (13)0.58790 (18)0.05948 (10)0.0417 (4)
H1N0.9148 (19)0.619 (2)0.0428 (13)0.050*
C10.70021 (15)0.53338 (19)−0.10743 (11)0.0381 (4)
C20.57570 (16)0.5897 (2)−0.11257 (13)0.0474 (4)
H20.53350.5753−0.06490.057*
C30.5152 (2)0.6672 (3)−0.18942 (16)0.0647 (6)
H30.43150.7057−0.19370.078*
C40.5778 (2)0.6880 (3)−0.25983 (16)0.0722 (7)
H40.53610.7404−0.31150.087*
C50.7015 (2)0.6322 (3)−0.25444 (14)0.0672 (6)
H50.74290.6467−0.30250.081*
C60.76449 (19)0.5545 (2)−0.17803 (13)0.0513 (5)
H60.84840.5170−0.17390.062*
C70.76772 (16)0.7043 (2)0.08868 (12)0.0437 (4)
C80.7529 (2)0.8517 (2)0.04985 (15)0.0607 (5)
C90.6695 (3)0.9543 (3)0.0839 (2)0.0831 (8)
H90.65501.05380.05930.100*
C100.6091 (3)0.9108 (3)0.1524 (2)0.0825 (8)
H100.55400.98150.17220.099*
C110.62731 (19)0.7668 (3)0.19244 (15)0.0622 (6)
C120.70773 (16)0.6642 (2)0.15926 (13)0.0486 (4)
H120.72210.56550.18490.058*
C130.8207 (3)0.9011 (3)−0.0238 (2)0.0899 (8)
H13A0.90910.8655−0.00990.108*
H13B0.81931.0129−0.02850.108*
H13C0.77710.8565−0.08010.108*
C140.5648 (2)0.7236 (4)0.27002 (18)0.0873 (9)
H14A0.56220.81360.30740.105*
H14B0.61430.64250.30500.105*
H14C0.47800.68730.24710.105*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0331 (2)0.0359 (2)0.0443 (3)0.00200 (16)0.00952 (16)0.00318 (17)
O10.0408 (7)0.0461 (7)0.0665 (8)0.0092 (5)0.0160 (6)0.0016 (6)
O20.0451 (7)0.0453 (7)0.0557 (7)−0.0032 (5)0.0178 (6)0.0076 (6)
N10.0323 (7)0.0464 (8)0.0455 (8)−0.0026 (6)0.0059 (6)0.0000 (6)
C10.0367 (8)0.0365 (9)0.0401 (9)−0.0039 (7)0.0057 (6)−0.0013 (7)
C20.0361 (9)0.0486 (10)0.0563 (11)−0.0009 (8)0.0065 (7)0.0057 (8)
C30.0464 (11)0.0637 (13)0.0759 (15)−0.0004 (10)−0.0062 (10)0.0161 (11)
C40.0747 (15)0.0708 (15)0.0588 (13)−0.0115 (12)−0.0145 (11)0.0211 (11)
C50.0848 (16)0.0733 (15)0.0435 (11)−0.0153 (13)0.0134 (10)0.0075 (10)
C60.0522 (10)0.0533 (11)0.0513 (11)−0.0013 (9)0.0174 (8)0.0003 (9)
C70.0362 (8)0.0413 (9)0.0479 (10)−0.0017 (7)−0.0048 (7)−0.0071 (8)
C80.0646 (13)0.0414 (10)0.0685 (14)−0.0071 (9)−0.0041 (10)−0.0037 (9)
C90.0940 (19)0.0369 (11)0.105 (2)0.0072 (12)−0.0096 (16)−0.0086 (12)
C100.0697 (15)0.0679 (16)0.106 (2)0.0097 (13)0.0097 (14)−0.0323 (15)
C110.0484 (11)0.0638 (14)0.0715 (14)−0.0028 (10)0.0057 (9)−0.0311 (11)
C120.0402 (9)0.0514 (11)0.0507 (10)−0.0020 (8)0.0016 (7)−0.0129 (8)
C130.113 (2)0.0534 (14)0.097 (2)−0.0199 (15)0.0091 (16)0.0187 (13)
C140.0714 (15)0.109 (2)0.0881 (18)−0.0067 (15)0.0315 (13)−0.0484 (16)

Geometric parameters (Å, °)

S1—O21.4205 (12)C7—C81.387 (3)
S1—O11.4340 (12)C7—C121.391 (3)
S1—N11.6377 (15)C8—C91.412 (3)
S1—C11.7620 (17)C8—C131.503 (4)
N1—C71.440 (2)C9—C101.374 (4)
N1—H1N0.828 (19)C9—H90.9300
C1—C21.383 (2)C10—C111.370 (4)
C1—C61.389 (2)C10—H100.9300
C2—C31.376 (3)C11—C121.384 (3)
C2—H20.9300C11—C141.505 (3)
C3—C41.375 (3)C12—H120.9300
C3—H30.9300C13—H13A0.9600
C4—C51.373 (3)C13—H13B0.9600
C4—H40.9300C13—H13C0.9600
C5—C61.380 (3)C14—H14A0.9600
C5—H50.9300C14—H14B0.9600
C6—H60.9300C14—H14C0.9600
O2—S1—O1119.19 (8)C12—C7—N1117.14 (16)
O2—S1—N1108.07 (8)C7—C8—C9115.8 (2)
O1—S1—N1105.61 (8)C7—C8—C13122.8 (2)
O2—S1—C1108.22 (8)C9—C8—C13121.4 (2)
O1—S1—C1108.61 (8)C10—C9—C8121.7 (2)
N1—S1—C1106.47 (8)C10—C9—H9119.2
C7—N1—S1119.53 (11)C8—C9—H9119.2
C7—N1—H1N117.4 (15)C11—C10—C9122.3 (2)
S1—N1—H1N109.5 (14)C11—C10—H10118.9
C2—C1—C6121.13 (16)C9—C10—H10118.9
C2—C1—S1119.01 (13)C10—C11—C12116.8 (2)
C6—C1—S1119.72 (13)C10—C11—C14121.5 (2)
C3—C2—C1118.92 (18)C12—C11—C14121.7 (2)
C3—C2—H2120.5C11—C12—C7122.0 (2)
C1—C2—H2120.5C11—C12—H12119.0
C4—C3—C2120.4 (2)C7—C12—H12119.0
C4—C3—H3119.8C8—C13—H13A109.5
C2—C3—H3119.8C8—C13—H13B109.5
C5—C4—C3120.5 (2)H13A—C13—H13B109.5
C5—C4—H4119.7C8—C13—H13C109.5
C3—C4—H4119.7H13A—C13—H13C109.5
C4—C5—C6120.3 (2)H13B—C13—H13C109.5
C4—C5—H5119.9C11—C14—H14A109.5
C6—C5—H5119.9C11—C14—H14B109.5
C5—C6—C1118.76 (19)H14A—C14—H14B109.5
C5—C6—H6120.6C11—C14—H14C109.5
C1—C6—H6120.6H14A—C14—H14C109.5
C8—C7—C12121.37 (18)H14B—C14—H14C109.5
C8—C7—N1121.47 (18)
O2—S1—N1—C7−53.36 (15)S1—C1—C6—C5−175.98 (16)
O1—S1—N1—C7178.05 (13)S1—N1—C7—C8−102.82 (18)
C1—S1—N1—C762.70 (15)S1—N1—C7—C1278.98 (18)
O2—S1—C1—C231.30 (16)C12—C7—C8—C9−2.6 (3)
O1—S1—C1—C2162.03 (14)N1—C7—C8—C9179.28 (17)
N1—S1—C1—C2−84.66 (15)C12—C7—C8—C13177.4 (2)
O2—S1—C1—C6−153.10 (14)N1—C7—C8—C13−0.8 (3)
O1—S1—C1—C6−22.37 (16)C7—C8—C9—C101.2 (3)
N1—S1—C1—C690.94 (15)C13—C8—C9—C10−178.8 (2)
C6—C1—C2—C30.2 (3)C8—C9—C10—C110.8 (4)
S1—C1—C2—C3175.78 (15)C9—C10—C11—C12−1.5 (3)
C1—C2—C3—C40.1 (3)C9—C10—C11—C14177.4 (2)
C2—C3—C4—C5−0.1 (4)C10—C11—C12—C70.0 (3)
C3—C4—C5—C6−0.1 (4)C14—C11—C12—C7−178.80 (18)
C4—C5—C6—C10.4 (3)C8—C7—C12—C112.1 (3)
C2—C1—C6—C5−0.5 (3)N1—C7—C12—C11−179.74 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.828 (19)2.16 (2)2.9634 (19)163.3 (19)

Symmetry codes: (i) −x+2, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2200).

References

  • Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621–632. [PubMed]
  • Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008a). Acta Cryst. E64, o1691. [PMC free article] [PubMed]
  • Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008b). Acta Cryst. E64, o1692. [PMC free article] [PubMed]
  • Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2009). Acta Cryst. E65, o366. [PMC free article] [PubMed]
  • Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106–112.
  • Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Abingdon, England.
  • Perlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780–o782.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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