Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3489
https://doi.org/10.1107/S1600536811050574

N-(3-Chloro­benzo­yl)-2-methyl­benzene­sulfonamide

P. A. Suchetan,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 23 November 2011; accepted 24 November 2011; online 30 November 2011)

In the title compound, C14H12ClNO3S, the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond. Further, the C=O bond and the meta-Cl atom in the benzoyl ring are also anti to each other. The dihedral angle between the sulfonyl and the benzoyl benzene rings is 72.4 (1)°. In the crystal, mol­ecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers.

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.]), on N-(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. (2010[Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o1024.]) and on N-chloro­aryl­amides, see: Gowda et al. (1996[Gowda, B. T., Dou, S. Q. & Weiss, A. (1996). Z. Naturforsch. Teil A, 51, 627-636.]).

[Scheme 1]

Experimental

Crystal data

  • C14H12ClNO3S

  • Mr = 309.76

  • Monoclinic, C 2/c

  • a = 18.043 (2) Å

  • b = 12.046 (1) Å

  • c = 15.596 (2) Å

  • β = 118.77 (2)°

  • V = 2971.3 (6) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.40 mm−1

  • T = 293 K

  • 0.40 × 0.36 × 0.32 mm
Data collection

  • Oxford Diffraction Xcalibur diffractometer with 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 = 0.856, Tmax = 0.882

  • 5996 measured reflections

  • 3024 independent reflections

  • 2463 reflections with I > 2σ(I)

  • Rint = 0.012
Refinement

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.113

  • S = 1.03

  • 3024 reflections

  • 185 parameters

  • 1 restraint

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

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.64 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O2i 0.82 (2) 2.06 (2) 2.876 (2) 174 (2)
Symmetry code: (i) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+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

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811050574/bt5728sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050574/bt5728Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811050574/bt5728Isup3.cml

checkCIF report


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., 2010) and N-chloro-arylsulfonamides (Gowda et al., 1996), in the present work, the crystal structure of N-(3-Chlorobenzoyl)- 2-methylbenzenesulfonamide (I) has been determined (Fig.1).

The conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond (Fig.1), similar to that observed in N-(benzoyl)-2-methylbenzenesulfonamide (II)(Suchetan et al., 2010). Further, the conformation between the C=O bond and the meta-Cl in the benzoyl ring is also anti to each other.

The molecules are twisted at the S atom with the torsional angle of 66.9 (2)°, compared to the value of 68.8 (4)° in (II).

The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 82.4 (1)°, compared to the value of 84.8 (1)° in (II). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 72.4 (1)°, compared to the value of 73.9 (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), on N-(aryl)-arylsulfonamides, see: Gowda et al. (2003), on N-(substitutedbenzoyl)-arylsulfonamides, see: Suchetan et al. (2010) and on N-chloroarylamides, see: Gowda et al. (1996).

Experimental top

The title compound was prepared by refluxing a mixture of 3-chlorobenzoic acid (0.02 mole), 2-methylbenzenesulfonamide (0.02 mole) and excess phosphorous oxy chloride for 3 h on a water bath. The resultant mixture was cooled and poured into crushed ice. The solid, N-(3-chlorobenzoyl)2-methylbenzenesulfonamide, 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.

Prism 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 later restrained to N—H = 0.86 (2) %A. The other H atoms were positioned with idealized geometry using a riding model with C—H distances of 0.93Å (C-aromatic) and 0.96Å (C-methyl).

All H atoms were refined with isotropic displacement parameters were set at 1.2 Ueq(C-aromatic, N) and 1.5 Ueq(C-methyl).

Structure description 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., 2010) and N-chloro-arylsulfonamides (Gowda et al., 1996), in the present work, the crystal structure of N-(3-Chlorobenzoyl)- 2-methylbenzenesulfonamide (I) has been determined (Fig.1).

The conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond (Fig.1), similar to that observed in N-(benzoyl)-2-methylbenzenesulfonamide (II)(Suchetan et al., 2010). Further, the conformation between the C=O bond and the meta-Cl in the benzoyl ring is also anti to each other.

The molecules are twisted at the S atom with the torsional angle of 66.9 (2)°, compared to the value of 68.8 (4)° in (II).

The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 82.4 (1)°, compared to the value of 84.8 (1)° in (II). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 72.4 (1)°, compared to the value of 73.9 (1)° in (II).

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

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), on N-(aryl)-arylsulfonamides, see: Gowda et al. (2003), on N-(substitutedbenzoyl)-arylsulfonamides, see: Suchetan et al. (2010) and on N-chloroarylamides, see: Gowda et al. (1996).

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
[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)-2-methylbenzenesulfonamide top
Crystal data top
C14H12ClNO3SF(000) = 1280
Mr = 309.76Dx = 1.385 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3176 reflections
a = 18.043 (2) Åθ = 2.8–27.8°
b = 12.046 (1) ŵ = 0.40 mm−1
c = 15.596 (2) ÅT = 293 K
β = 118.77 (2)°Prism, colourless
V = 2971.3 (6) Å30.40 × 0.36 × 0.32 mm
Z = 8
Data collection top
Oxford Diffraction Xcalibur
diffractometer with Sapphire CCD detector		3024 independent reflections
Radiation source: fine-focus sealed tube2463 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.012
Rotation method data acquisition using ω and phi scans.θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		h = −22→18
Tmin = 0.856, Tmax = 0.882k = −15→11
5996 measured reflectionsl = −18→19
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0488P)2 + 4.0385P]
where P = (Fo2 + 2Fc2)/3
3024 reflections(Δ/σ)max < 0.001
185 parametersΔρmax = 0.45 e Å−3
1 restraintΔρmin = −0.64 e Å−3
Crystal data top
C14H12ClNO3SV = 2971.3 (6) Å3
Mr = 309.76Z = 8
Monoclinic, C2/cMo Kα radiation
a = 18.043 (2) ŵ = 0.40 mm−1
b = 12.046 (1) ÅT = 293 K
c = 15.596 (2) Å0.40 × 0.36 × 0.32 mm
β = 118.77 (2)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with Sapphire CCD detector		3024 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		2463 reflections with I > 2σ(I)
Tmin = 0.856, Tmax = 0.882Rint = 0.012
5996 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0421 restraint
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.45 e Å−3
3024 reflectionsΔρmin = −0.64 e Å−3
185 parameters
Special details top

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
C10.34287 (11)0.11403 (15)0.87322 (14)0.0349 (4)
C20.29479 (13)0.18523 (18)0.79536 (16)0.0449 (5)
C30.30275 (17)0.1707 (2)0.71180 (18)0.0604 (6)
H30.27160.21610.65800.072*
C40.35502 (18)0.0918 (2)0.70565 (19)0.0627 (7)
H40.35910.08540.64860.075*
C50.40121 (16)0.0224 (2)0.78294 (19)0.0546 (6)
H50.4363−0.03120.77850.065*
C60.39508 (13)0.03297 (18)0.86754 (16)0.0434 (5)
H60.4257−0.01390.92030.052*
C70.22402 (13)−0.03082 (17)0.94079 (16)0.0418 (5)
C80.13770 (14)−0.06030 (18)0.92343 (16)0.0451 (5)
C90.07257 (14)0.0159 (2)0.89365 (18)0.0535 (6)
H90.08140.09050.88590.064*
C10−0.00629 (16)−0.0220 (3)0.8757 (2)0.0736 (8)
C11−0.0197 (2)−0.1309 (3)0.8889 (3)0.0970 (12)
H11−0.0729−0.15450.87700.116*
C120.0461 (2)−0.2054 (3)0.9201 (3)0.0981 (12)
H120.0372−0.27930.92980.118*
C130.12381 (17)−0.1717 (2)0.9368 (2)0.0633 (7)
H130.1678−0.22270.95710.076*
C140.23804 (18)0.2758 (2)0.7967 (2)0.0657 (7)
H14A0.27190.33530.83800.079*
H14B0.20250.24690.82140.079*
H14C0.20360.30320.73140.079*
N10.24872 (11)0.07910 (15)0.96409 (14)0.0425 (4)
H1N0.2195 (14)0.1279 (17)0.9688 (18)0.051*
O10.40644 (10)0.05491 (15)1.05526 (11)0.0546 (4)
O20.34229 (10)0.23938 (13)1.01017 (13)0.0547 (4)
O30.27146 (10)−0.09871 (13)0.93618 (14)0.0578 (4)
Cl1−0.08922 (5)0.07097 (11)0.83538 (9)0.1187 (4)
S10.34256 (3)0.12455 (4)0.98556 (4)0.03864 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0307 (9)0.0335 (10)0.0424 (10)−0.0031 (8)0.0192 (8)−0.0026 (8)
C20.0401 (11)0.0408 (11)0.0523 (12)0.0002 (9)0.0210 (10)0.0047 (10)
C30.0678 (16)0.0615 (15)0.0487 (13)0.0021 (13)0.0255 (12)0.0117 (12)
C40.0773 (18)0.0704 (17)0.0510 (14)−0.0068 (14)0.0393 (13)−0.0077 (13)
C50.0567 (14)0.0533 (14)0.0659 (15)0.0006 (11)0.0393 (12)−0.0115 (12)
C60.0397 (11)0.0412 (11)0.0517 (12)0.0025 (9)0.0239 (9)−0.0007 (9)
C70.0449 (11)0.0368 (11)0.0473 (11)−0.0006 (9)0.0251 (10)−0.0003 (9)
C80.0448 (12)0.0423 (12)0.0512 (12)−0.0074 (9)0.0254 (10)−0.0072 (10)
C90.0428 (12)0.0514 (13)0.0631 (14)−0.0037 (10)0.0229 (11)−0.0074 (11)
C100.0432 (14)0.092 (2)0.0811 (19)−0.0048 (14)0.0263 (13)−0.0196 (17)
C110.0587 (18)0.090 (2)0.149 (3)−0.0355 (18)0.055 (2)−0.034 (2)
C120.093 (3)0.0636 (19)0.155 (4)−0.0324 (19)0.073 (3)−0.015 (2)
C130.0608 (15)0.0442 (13)0.092 (2)−0.0093 (12)0.0422 (15)−0.0075 (13)
C140.0622 (16)0.0524 (14)0.0783 (18)0.0205 (13)0.0304 (14)0.0163 (13)
N10.0388 (9)0.0374 (9)0.0605 (11)−0.0007 (7)0.0312 (9)−0.0054 (8)
O10.0428 (8)0.0729 (11)0.0445 (8)0.0079 (8)0.0182 (7)0.0070 (8)
O20.0522 (9)0.0466 (9)0.0766 (11)−0.0129 (7)0.0401 (9)−0.0226 (8)
O30.0557 (10)0.0395 (8)0.0884 (13)0.0041 (7)0.0428 (9)−0.0047 (8)
Cl10.0500 (4)0.1486 (10)0.1396 (9)0.0240 (5)0.0313 (5)−0.0175 (7)
S10.0337 (3)0.0404 (3)0.0455 (3)−0.0024 (2)0.0219 (2)−0.0056 (2)
Geometric parameters (Å, º) top
C1—C61.389 (3)C9—C101.388 (3)
C1—C21.396 (3)C9—H90.9300
C1—S11.759 (2)C10—C111.368 (5)
C2—C31.389 (3)C10—Cl11.727 (3)
C2—C141.503 (3)C11—C121.376 (5)
C3—C41.375 (4)C11—H110.9300
C3—H30.9300C12—C131.359 (4)
C4—C51.370 (4)C12—H120.9300
C4—H40.9300C13—H130.9300
C5—C61.382 (3)C14—H14A0.9600
C5—H50.9300C14—H14B0.9600
C6—H60.9300C14—H14C0.9600
C7—O31.211 (2)N1—S11.6532 (17)
C7—N11.389 (3)N1—H1N0.816 (16)
C7—C81.490 (3)O1—S11.4170 (17)
C8—C91.384 (3)O2—S11.4361 (16)
C8—C131.399 (3)
C6—C1—C2122.21 (19)C11—C10—C9121.5 (3)
C6—C1—S1116.20 (16)C11—C10—Cl1119.5 (2)
C2—C1—S1121.57 (15)C9—C10—Cl1119.0 (3)
C3—C2—C1115.9 (2)C10—C11—C12119.6 (3)
C3—C2—C14118.8 (2)C10—C11—H11120.2
C1—C2—C14125.2 (2)C12—C11—H11120.2
C4—C3—C2122.4 (2)C13—C12—C11120.5 (3)
C4—C3—H3118.8C13—C12—H12119.7
C2—C3—H3118.8C11—C12—H12119.7
C5—C4—C3120.5 (2)C12—C13—C8120.0 (3)
C5—C4—H4119.8C12—C13—H13120.0
C3—C4—H4119.8C8—C13—H13120.0
C4—C5—C6119.3 (2)C2—C14—H14A109.5
C4—C5—H5120.3C2—C14—H14B109.5
C6—C5—H5120.3H14A—C14—H14B109.5
C5—C6—C1119.6 (2)C2—C14—H14C109.5
C5—C6—H6120.2H14A—C14—H14C109.5
C1—C6—H6120.2H14B—C14—H14C109.5
O3—C7—N1120.84 (19)C7—N1—S1122.50 (14)
O3—C7—C8122.37 (19)C7—N1—H1N124.8 (18)
N1—C7—C8116.78 (18)S1—N1—H1N112.7 (18)
C9—C8—C13120.2 (2)O1—S1—O2118.13 (11)
C9—C8—C7123.2 (2)O1—S1—N1109.57 (10)
C13—C8—C7116.6 (2)O2—S1—N1103.78 (9)
C8—C9—C10118.1 (2)O1—S1—C1109.27 (9)
C8—C9—H9120.9O2—S1—C1109.73 (10)
C10—C9—H9120.9N1—S1—C1105.56 (9)
C6—C1—C2—C3−0.5 (3)C8—C9—C10—Cl1−178.3 (2)
S1—C1—C2—C3177.92 (17)C9—C10—C11—C12−0.6 (6)
C6—C1—C2—C14−179.0 (2)Cl1—C10—C11—C12179.4 (3)
S1—C1—C2—C14−0.6 (3)C10—C11—C12—C13−0.6 (6)
C1—C2—C3—C4−0.4 (4)C11—C12—C13—C80.7 (6)
C14—C2—C3—C4178.2 (3)C9—C8—C13—C120.3 (4)
C2—C3—C4—C50.8 (4)C7—C8—C13—C12−178.5 (3)
C3—C4—C5—C6−0.3 (4)O3—C7—N1—S10.7 (3)
C4—C5—C6—C1−0.5 (3)C8—C7—N1—S1179.90 (15)
C2—C1—C6—C50.9 (3)C7—N1—S1—O1−50.7 (2)
S1—C1—C6—C5−177.54 (17)C7—N1—S1—O2−177.71 (18)
O3—C7—C8—C9−156.0 (2)C7—N1—S1—C166.88 (19)
N1—C7—C8—C924.8 (3)C6—C1—S1—O17.75 (19)
O3—C7—C8—C1322.7 (3)C2—C1—S1—O1−170.73 (16)
N1—C7—C8—C13−156.5 (2)C6—C1—S1—O2138.74 (16)
C13—C8—C9—C10−1.4 (4)C2—C1—S1—O2−39.75 (19)
C7—C8—C9—C10177.3 (2)C6—C1—S1—N1−110.00 (16)
C8—C9—C10—C111.6 (4)C2—C1—S1—N171.51 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.82 (2)2.06 (2)2.876 (2)174 (2)
Symmetry code: (i) −x+1/2, −y+1/2, −z+2.

Experimental details

Crystal data
Chemical formulaC14H12ClNO3S
Mr309.76
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)18.043 (2), 12.046 (1), 15.596 (2)
β (°) 118.77 (2)
V (Å3)2971.3 (6)
Z8
Radiation typeMo Kα
µ (mm−1)0.40
Crystal size (mm)0.40 × 0.36 × 0.32
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.856, 0.882
No. of measured, independent and
observed [I > 2σ(I)] reflections		5996, 3024, 2463
Rint0.012
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.113, 1.03
No. of reflections3024
No. of parameters185
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.45, −0.64

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···O2i0.816 (16)2.063 (17)2.876 (2)174 (2)
Symmetry code: (i) −x+1/2, −y+1/2, −z+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 the faculty.

References

First citationBowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1–o3.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationGowda, B. T., Dou, S. Q. & Weiss, A. (1996). Z. Naturforsch. Teil A, 51, 627–636.  CAS Google Scholar
 First citationGowda, B. T., Jyothi, K., Kozisek, J. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 656–660.  CAS Google Scholar
 First citationGowda, B. T., Svoboda, I. & Fuess, H. (2004). Z. Naturforsch. Teil A, 59, 845–852.  CAS Google Scholar
 First citationJayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch.Teil A, 59, 491–500.  CAS Google Scholar
 First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSuchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o1024.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3489
https://doi.org/10.1107/S1600536811050574
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS