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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2855.
Published online 2010 October 20. doi:  10.1107/S1600536810041206
PMCID: PMC3009279

N-(5-Chloro-2-meth­oxy­phen­yl)benzene­sulfonamide

Abstract

In the title compound, C13H12ClNO3S, the dihedral angle between the two aromatic rings is 73.94 (9)°. An intra­molecular C—H(...)O hydrogen bond occurs. In the crystal, inter­molecular N—H(...)O hydrogen bonds connect the mol­ecules to centrosymmetric dimers, forming an R 2 2(8) ring motif. The packing is consolidated by C—H(...)O hydrogen bonds and weak π–π inter­actions [centroid–centroid distances = 3.81 (3) and 3.81 (3) Å].

Related literature

For the biological properties of sulfonamide derivatives, see: Berredjem et al. (2000 [triangle]); Lee & Lee (2002 [triangle]); Soledade et al. (2006 [triangle]); Xiao & Timberlake (2000 [triangle]). For related structures, see: Aziz-ur-Rehman et al. (2010a [triangle],b [triangle]); Khan et al. (2010 [triangle]); Akkurt et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2855-scheme1.jpg

Experimental

Crystal data

  • C13H12ClNO3S
  • M r = 297.76
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2855-efi1.jpg
  • a = 8.2201 (2) Å
  • b = 8.9395 (2) Å
  • c = 10.5544 (2) Å
  • α = 77.206 (1)°
  • β = 76.366 (1)°
  • γ = 66.408 (1)°
  • V = 683.65 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.43 mm−1
  • T = 296 K
  • 0.24 × 0.16 × 0.08 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • 12007 measured reflections
  • 3333 independent reflections
  • 2906 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.096
  • S = 1.02
  • 3333 reflections
  • 177 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041206/bt5375sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041206/bt5375Isup2.hkl

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

Acknowledgments

The authors are grateful to the Higher Education Commission for providing financial support.

supplementary crystallographic information

Comment

Sulfonamide is found in a number of synthetic as well as natural compounds. These molecules posses many biological activities e.g., herbicidal, anti-malarial, anti-convulsant and anti- hypertensive (Soledade et al., 2006; Xiao & Timberlake, 2000; Berredjem et al., 2000; Lee & Lee, 2002). In the present paper, the structure of N-(5-chloro-2-methoxyphenyl) benzenesulfonamide has been determined as part of a research program involving the synthesis and biological evaluation of sulfur containing compounds.

In the title molecule (I), (Fig. 1), both sulfonamido-O atoms lie on the opposite side of the S-bound phenyl ring to the sulfonamido-N1 atom [the O1–S1–C1–C6, O2–S1–C1–C2 and N1–S1–C1–C2 torsion angles are -34.32 (13), 14.43 (13) and -101.83 (12) °, respectively]. The dihedral angle formed between the phenyl (C1–C6) and benzene (C7–C12) rings in (I) is 73.94 (9) °.

The molecules of (I) are dimerized due to the intermolecular N—H···O hydrogen bonding (Table 1, Fig. 2) producing a R22(8) ring motif.

In addition, there are C—H···O hydrogen bonds, as well as π-π interactions [Cg1···Cg1(1 - x, -y, 2 - z) = 3.8163 (11) Å and cg2···Cg2(-x, 1 - y, 1 - z) = 3.9472 (12) Å; where Cg1 and Cg2 are centroids of the phenyl and benzene rings (C1–C6 and C7–C12), respectively], between the aromatic rings of each dimer.

Experimental

A mixture benzenesulfonyl chloride (10.0 mmol; 1.45 ml), 5-chloro-2-methoxy aniline (10.0 mmol; 1.47 g), aqueous sodium carbonate (10%; 20.0 ml) and water (25 ml) was stirred for one and half hour at room temperature. The crude mixture was washed with water and dried. The product was dissolved in methanol and recrystallized by slow evaporation of the solvent, to generate colourless crystal of N-(5-chloro-2-methoxyphenyl)benzenesulfonamide in 71% yield.

Refinement

The amino H atom is located in a difference Fourier map and refined freely. The remaining H atoms were positioned geometrically (C—H = 0.93 and 0.96 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The title molecule drawn with displacement ellipsoids drawn at the 30% probability level.
Fig. 2.
View of the dimeric N—H···O interactions between two moleculs in the unit cell.

Crystal data

C13H12ClNO3SZ = 2
Mr = 297.76F(000) = 308
Triclinic, P1Dx = 1.446 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2201 (2) ÅCell parameters from 6946 reflections
b = 8.9395 (2) Åθ = 2.5–28.2°
c = 10.5544 (2) ŵ = 0.43 mm1
α = 77.206 (1)°T = 296 K
β = 76.366 (1)°Prism, colourless
γ = 66.408 (1)°0.24 × 0.16 × 0.08 mm
V = 683.65 (3) Å3

Data collection

Bruker APEXII CCD diffractometer2906 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.023
graphiteθmax = 28.3°, θmin = 4.0°
[var phi] and ω scansh = −10→10
12007 measured reflectionsk = −11→11
3333 independent reflectionsl = −14→12

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0504P)2 + 0.1401P] where P = (Fo2 + 2Fc2)/3
3333 reflections(Δ/σ)max = 0.001
177 parametersΔρmax = 0.35 e Å3
1 restraintΔρmin = −0.27 e Å3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl10.29733 (8)0.24190 (8)0.34117 (5)0.0934 (2)
S10.14406 (4)0.27960 (4)0.88801 (3)0.0380 (1)
O10.03295 (14)0.31471 (13)1.01239 (9)0.0510 (3)
O20.13974 (14)0.15335 (13)0.82861 (10)0.0506 (3)
O30.1709 (2)0.71184 (16)0.69335 (12)0.0734 (5)
N10.08081 (16)0.45288 (14)0.78854 (10)0.0429 (3)
C10.36916 (18)0.23297 (16)0.90100 (12)0.0398 (4)
C20.5039 (2)0.11582 (19)0.83059 (15)0.0521 (5)
C30.6805 (2)0.0782 (2)0.8436 (2)0.0696 (6)
C40.7178 (3)0.1563 (3)0.9253 (2)0.0767 (7)
C50.5824 (3)0.2731 (3)0.9938 (2)0.0731 (7)
C60.4049 (2)0.3136 (2)0.98279 (16)0.0557 (5)
C70.16189 (18)0.47011 (17)0.65422 (12)0.0422 (4)
C80.1896 (2)0.35789 (19)0.57270 (13)0.0505 (4)
C90.2635 (2)0.3861 (2)0.44138 (15)0.0616 (5)
C100.3044 (3)0.5227 (3)0.39090 (16)0.0756 (7)
C110.2737 (3)0.6360 (3)0.47153 (17)0.0739 (7)
C120.2046 (2)0.6098 (2)0.60401 (14)0.0541 (5)
C130.1961 (3)0.8625 (3)0.6504 (3)0.0875 (9)
H10.058 (2)0.5318 (19)0.8273 (16)0.052 (4)*
H20.476900.063500.775800.0630*
H30.773800.000000.797000.0830*
H40.836500.129600.934100.0920*
H50.610100.325401.048100.0880*
H60.312200.392701.029000.0670*
H80.159400.265200.605200.0600*
H100.352900.539400.302400.0910*
H110.299400.730700.437000.0890*
H13A0.320500.841900.614400.1310*
H13B0.161500.922500.723600.1310*
H13C0.123400.926200.583900.1310*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.1058 (4)0.0954 (4)0.0594 (3)0.0032 (3)−0.0179 (2)−0.0448 (3)
S10.0403 (2)0.0368 (2)0.0370 (2)−0.0163 (1)0.0011 (1)−0.0095 (1)
O10.0538 (6)0.0510 (6)0.0416 (5)−0.0206 (5)0.0098 (4)−0.0100 (4)
O20.0566 (6)0.0459 (5)0.0577 (6)−0.0253 (5)−0.0063 (5)−0.0146 (4)
O30.1093 (11)0.0642 (8)0.0596 (7)−0.0505 (8)0.0026 (7)−0.0160 (6)
N10.0491 (6)0.0385 (6)0.0360 (5)−0.0107 (5)−0.0019 (4)−0.0111 (4)
C10.0435 (7)0.0381 (6)0.0381 (6)−0.0193 (5)−0.0049 (5)0.0003 (5)
C20.0465 (8)0.0504 (8)0.0515 (8)−0.0145 (6)−0.0008 (6)−0.0058 (6)
C30.0437 (8)0.0664 (11)0.0793 (11)−0.0144 (8)0.0003 (8)0.0052 (9)
C40.0524 (10)0.0787 (13)0.0975 (14)−0.0378 (10)−0.0255 (10)0.0310 (11)
C50.0829 (13)0.0731 (12)0.0857 (13)−0.0494 (11)−0.0375 (11)0.0098 (10)
C60.0643 (9)0.0529 (8)0.0591 (9)−0.0286 (7)−0.0153 (7)−0.0068 (7)
C70.0419 (7)0.0437 (7)0.0351 (6)−0.0092 (5)−0.0058 (5)−0.0073 (5)
C80.0535 (8)0.0491 (8)0.0420 (7)−0.0073 (6)−0.0100 (6)−0.0131 (6)
C90.0611 (9)0.0675 (10)0.0397 (7)0.0007 (8)−0.0109 (6)−0.0189 (7)
C100.0797 (12)0.0875 (14)0.0370 (7)−0.0161 (10)0.0030 (7)−0.0062 (8)
C110.0871 (13)0.0748 (12)0.0503 (9)−0.0341 (10)0.0042 (8)0.0014 (8)
C120.0602 (9)0.0554 (9)0.0442 (7)−0.0219 (7)−0.0022 (6)−0.0080 (6)
C130.1028 (17)0.0654 (12)0.1064 (17)−0.0453 (12)−0.0112 (13)−0.0149 (11)

Geometric parameters (Å, °)

Cl1—C91.7424 (17)C7—C81.380 (2)
S1—O11.4296 (10)C8—C91.387 (2)
S1—O21.4227 (12)C9—C101.358 (3)
S1—N11.6323 (12)C10—C111.375 (3)
S1—C11.7588 (16)C11—C121.386 (2)
O3—C121.361 (2)C2—H20.9300
O3—C131.404 (3)C3—H30.9300
N1—C71.4205 (16)C4—H40.9300
N1—H10.828 (16)C5—H50.9300
C1—C21.380 (2)C6—H60.9300
C1—C61.384 (2)C8—H80.9300
C2—C31.386 (3)C10—H100.9300
C3—C41.374 (3)C11—H110.9300
C4—C51.370 (3)C13—H13A0.9600
C5—C61.383 (3)C13—H13B0.9600
C7—C121.391 (2)C13—H13C0.9600
Cl1···C6i3.6473 (17)C7···Cl1iii3.6152 (17)
Cl1···C2ii3.6292 (17)C7···C9iii3.520 (2)
Cl1···C7iii3.6152 (17)C8···C8iii3.566 (2)
Cl1···H2ii2.9600C8···O22.9491 (17)
Cl1···H13Aiv3.0500C8···C9iii3.524 (2)
S1···H82.9900C9···C8iii3.524 (2)
O1···N1v3.0096 (15)C9···C7iii3.520 (2)
O1···O1v3.0957 (15)C13···O2xi3.362 (3)
O1···O3v3.1699 (16)C3···H11iv3.0800
O2···C13vi3.362 (3)C11···H13A2.8100
O2···C4vii3.368 (3)C11···H13C2.7900
O2···C82.9491 (17)C13···H112.5800
O2···C4viii3.382 (2)H1···O32.241 (17)
O3···O1v3.1699 (16)H1···O1v2.217 (16)
O3···N12.6284 (19)H2···O22.5100
O1···H62.7000H2···Cl1ii2.9600
O1···H1v2.217 (16)H4···O2ix2.5500
O2···H13Bvi2.4800H6···O12.7000
O2···H4vii2.5500H8···S12.9900
O2···H82.3400H8···O22.3400
O2···H22.5100H11···C132.5800
O3···H12.241 (17)H11···H13A2.3700
N1···O32.6284 (19)H11···H13C2.3800
N1···O1v3.0096 (15)H11···C3iv3.0800
C1···C3viii3.499 (2)H13A···C112.8100
C2···Cl1ii3.6292 (17)H13A···H112.3700
C3···C1viii3.499 (2)H13A···Cl1iv3.0500
C4···O2ix3.368 (3)H13B···O2xi2.4800
C4···O2viii3.382 (2)H13C···C112.7900
C6···Cl1x3.6473 (17)H13C···H112.3800
O1—S1—O2118.95 (7)C10—C11—C12120.3 (2)
O1—S1—N1105.06 (6)C7—C12—C11119.51 (16)
O1—S1—C1109.15 (7)O3—C12—C7114.94 (13)
O2—S1—N1108.21 (6)O3—C12—C11125.55 (17)
O2—S1—C1107.73 (7)C1—C2—H2121.00
N1—S1—C1107.19 (7)C3—C2—H2121.00
C12—O3—C13119.30 (17)C2—C3—H3120.00
S1—N1—C7122.57 (10)C4—C3—H3120.00
C7—N1—H1115.2 (11)C3—C4—H4120.00
S1—N1—H1110.4 (11)C5—C4—H4120.00
S1—C1—C6118.85 (11)C4—C5—H5120.00
S1—C1—C2118.88 (12)C6—C5—H5120.00
C2—C1—C6122.27 (16)C1—C6—H6121.00
C1—C2—C3118.25 (15)C5—C6—H6121.00
C2—C3—C4120.09 (18)C7—C8—H8121.00
C3—C4—C5120.9 (2)C9—C8—H8121.00
C4—C5—C6120.5 (2)C9—C10—H10120.00
C1—C6—C5118.07 (17)C11—C10—H10120.00
N1—C7—C12117.82 (12)C10—C11—H11120.00
N1—C7—C8121.96 (13)C12—C11—H11120.00
C8—C7—C12120.14 (12)O3—C13—H13A109.00
C7—C8—C9118.69 (15)O3—C13—H13B109.00
Cl1—C9—C8117.57 (13)O3—C13—H13C109.00
C8—C9—C10121.73 (16)H13A—C13—H13B109.00
Cl1—C9—C10120.68 (13)H13A—C13—H13C109.00
C9—C10—C11119.57 (17)H13B—C13—H13C109.00
O1—S1—N1—C7179.00 (12)C1—C2—C3—C40.2 (3)
O2—S1—N1—C7−52.96 (14)C2—C3—C4—C5−0.7 (3)
C1—S1—N1—C762.98 (14)C3—C4—C5—C60.6 (3)
O1—S1—C1—C2144.89 (11)C4—C5—C6—C10.0 (3)
O2—S1—C1—C214.43 (13)C12—C7—C8—C91.2 (2)
N1—S1—C1—C2−101.83 (12)N1—C7—C12—O33.1 (2)
O1—S1—C1—C6−34.32 (13)C8—C7—C12—O3179.75 (16)
O2—S1—C1—C6−164.78 (11)C8—C7—C12—C110.5 (3)
N1—S1—C1—C678.96 (12)N1—C7—C12—C11−176.09 (18)
C13—O3—C12—C7−175.04 (19)N1—C7—C8—C9177.65 (15)
C13—O3—C12—C114.1 (3)C7—C8—C9—C10−1.8 (3)
S1—N1—C7—C12−135.26 (14)C7—C8—C9—Cl1179.83 (13)
S1—N1—C7—C848.2 (2)C8—C9—C10—C110.6 (3)
C2—C1—C6—C5−0.4 (2)Cl1—C9—C10—C11178.93 (19)
C6—C1—C2—C30.3 (2)C9—C10—C11—C121.2 (4)
S1—C1—C2—C3−178.87 (12)C10—C11—C12—C7−1.7 (3)
S1—C1—C6—C5178.76 (14)C10—C11—C12—O3179.1 (2)

Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y, −z+1; (iii) −x, −y+1, −z+1; (iv) −x+1, −y+1, −z+1; (v) −x, −y+1, −z+2; (vi) x, y−1, z; (vii) x−1, y, z; (viii) −x+1, −y, −z+2; (ix) x+1, y, z; (x) x, y, z+1; (xi) x, y+1, z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O1v0.828 (16)2.217 (16)3.0096 (15)160.2 (16)
C4—H4···O2ix0.932.553.368 (3)147
C8—H8···O20.932.342.9491 (17)123
C13—H13B···O2xi0.962.483.362 (3)153

Symmetry codes: (v) −x, −y+1, −z+2; (ix) x+1, y, z; (xi) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5375).

References

  • Akkurt, M., Çelik, Í., Cihan, G., Çapan, G. & Büyükgüngör, O. (2010). Acta Cryst. E66, o974–o975. [PMC free article] [PubMed]
  • Aziz-ur-Rehman, Rafique, H., Akkurt, M., Dilber, N., Abbasi, M. A. & Khan, I. U. (2010a). Acta Cryst. E66, o1728. [PMC free article] [PubMed]
  • Aziz-ur-Rehman, Sajjad, M. A., Akkurt, M., Sharif, S., Abbasi, M. A. & Khan, I. U. (2010b). Acta Cryst. E66, o1769. [PMC free article] [PubMed]
  • Berredjem, M., Régainia, Z., Djahoudi, A., Aouf, N. E., Dewinter, G. & Montero, J. L. (2000). Phosphorus Sulfur Silicon Relat. Elem.165, 249–264.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Khan, I. U., Sharif, S., Akkurt, M., Sajjad, A. & Ahmad, J. (2010). Acta Cryst. E66, o786. [PMC free article] [PubMed]
  • Lee, J. S. & Lee, C. H. (2002). Bull. Korean Chem. Soc.23, 167–169.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Soledade, M., Pedras, C. & Jha, M. (2006). Bioorg. Med. Chem.14, 4958–4979. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Xiao, Z. & Timberlake, J. W. (2000). J. Heterocycl. Chem.37, 773–777.

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