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 66| Part 12| December 2010| Page o3144
https://doi.org/10.1107/S1600536810045563

N-(2,4-Di­chloro­phen­yl)-2,4-di­methyl­benzene­sulfonamide

P. G. Nirmala,a Sabine Foro,b B. Thimme Gowdaa* and Hartmut Fuessb

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 5 November 2010; accepted 6 November 2010; online 13 November 2010)

In the title compound, C14H13Cl2NO2S, the mol­ecule is bent at the S atom with an C—SO2—NH—C torsion angle of −69.9 (2)°. The dihedral angle between the sulfonyl and aniline benzene rings is 44.0 (1)°. The crystal structure features inversion dimers linked by pairs of N—H⋯O hydrogen bonds. An intra­molecular N—H⋯Cl hydrogen bond is also observed.

Related literature

For the preparation of the compound, see: Savitha & Gowda (2006[Savitha, M. B. & Gowda, B. T. (2006). Z. Naturforsch. Teil A, 60, 600-606.]). For our study of the effect of substituents on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2009[Gowda, B. T., Foro, S., Nirmala, P. G., Babitha, K. S. & Fuess, H. (2009). Acta Cryst. E65, o576.]); Nirmala et al. (2010a[Nirmala, P. G., Gowda, B. T., Foro, S. & Fuess, H. (2010a). Acta Cryst. E66, o1059.],b[Nirmala, P. G., Gowda, B. T., Foro, S. & Fuess, H. (2010b). Acta Cryst. E66, o1090.]). For related structures, see: Gelbrich et al. (2007[Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621-632.]); Perlovich et al. (2006[Perlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780-o782.]).

[Scheme 1]

Experimental

Crystal data

  • C14H13Cl2NO2S

  • Mr = 330.21

  • Triclinic, [P \overline 1]

  • a = 8.2407 (9) Å

  • b = 8.3418 (9) Å

  • c = 10.849 (1) Å

  • α = 84.59 (1)°

  • β = 89.06 (1)°

  • γ = 85.07 (1)°

  • V = 739.69 (13) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 5.27 mm−1

  • T = 293 K

  • 0.45 × 0.40 × 0.13 mm
Data collection

  • Ennraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.200, Tmax = 0.547

  • 5173 measured reflections

  • 2629 independent reflections

  • 2496 reflections with I > 2σ(I)

  • Rint = 0.033

  • 3 standard reflections every 120 min intensity decay: 1.0%
Refinement

  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.159

  • S = 1.05

  • 2629 reflections

  • 187 parameters

  • 1 restraint

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

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.80 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O2i 0.85 (2) 2.24 (2) 3.056 (3) 159 (3)
N1—H1N⋯Cl1 0.85 (2) 2.68 (3) 3.020 (2) 105 (2)
Symmetry code: (i) -x, -y+1, -z.

Data collection: CAD-4-PC (Enraf–Nonius, 1996[Enraf-Nonius (1996). CAD-4-PC. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987[Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.]); 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/S1600536810045563/bq2251sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045563/bq2251Isup2.hkl

checkCIF report


Comment top

In the present work, as part of a study of the substituent effects on the structures of N-(aryl)arylsulfonamides (Gowda et al., 2009; Nirmala et al., 2010a,b), the structure of 2,4-dimethyl-N-(2,4-dichlorophenyl)benzenesulfonamide (I) has been determined (Fig. 1). The molecule is bent at the N atom with the C1—SO2—NH—C7 torsion angle of -69.9 (2)°, compared to the values of 46.1 (3)° (glide image of molecule 1) and 47.7 (3)° (molecule 2) in the two independent molecules of 2,4-dimethyl-N-(phenyl)benzenesulfonamide (II) (Gowda et al., 2009), -54.9 (3)° in 2,4-dimethyl-N-(3,5-dichlorophenyl)benzenesulfonamide (III) (Nirmala et al., 2010b) and 66.5 (2)° in 2,4-dimethyl-N-(2,4-dimethylphenyl)-benzenesulfonamide (IV) (Nirmala et al., 2010a)

The two benzene rings in (I) are tilted relative to each other by 44.0 (1)°, compared to the values of 67.5 (1)° (molecule 1) and 72.9 (1)° (molecule 2) in the two independent molecules of(II), 82.3 (1)° in (III) and 41.0 (1)° in (IV). The other bond parameters in (I) are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).

The structure shows simultaneous N—H···Cl intramolecular and N—H···O intermolecular H-bonding (Table 1). The crystal packing of molecules in (I) via N—H···O(S) hydrogen bonds is shown in Fig.2.

Related literature top

For the preparation of the compound, see: Savitha & Gowda (2006). For our study of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009); Nirmala et al. (2010a,b). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).

Experimental top

The solution of 1,3-xylene (1,3-dimethylbenzene) (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 2,4-dimethylbenzenesulfonylchloride was treated with 2,4-dichloroaniline 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 2,4-dimethyl-N-(2,4-dichlorophenyl)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 (Savitha & Gowda, 2006).

The plate like colorless single crystals used in X-ray diffraction studies were grown in ethanolic solution by a slow evaporation at room temperature.

Refinement top

The H atoms of the NH groups were located in a difference map and later restrained to N—H = 0.86 (2) Å. 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).

Structure description top

In the present work, as part of a study of the substituent effects on the structures of N-(aryl)arylsulfonamides (Gowda et al., 2009; Nirmala et al., 2010a,b), the structure of 2,4-dimethyl-N-(2,4-dichlorophenyl)benzenesulfonamide (I) has been determined (Fig. 1). The molecule is bent at the N atom with the C1—SO2—NH—C7 torsion angle of -69.9 (2)°, compared to the values of 46.1 (3)° (glide image of molecule 1) and 47.7 (3)° (molecule 2) in the two independent molecules of 2,4-dimethyl-N-(phenyl)benzenesulfonamide (II) (Gowda et al., 2009), -54.9 (3)° in 2,4-dimethyl-N-(3,5-dichlorophenyl)benzenesulfonamide (III) (Nirmala et al., 2010b) and 66.5 (2)° in 2,4-dimethyl-N-(2,4-dimethylphenyl)-benzenesulfonamide (IV) (Nirmala et al., 2010a)

The two benzene rings in (I) are tilted relative to each other by 44.0 (1)°, compared to the values of 67.5 (1)° (molecule 1) and 72.9 (1)° (molecule 2) in the two independent molecules of(II), 82.3 (1)° in (III) and 41.0 (1)° in (IV). The other bond parameters in (I) are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).

The structure shows simultaneous N—H···Cl intramolecular and N—H···O intermolecular H-bonding (Table 1). The crystal packing of molecules in (I) via N—H···O(S) hydrogen bonds is shown in Fig.2.

For the preparation of the compound, see: Savitha & Gowda (2006). For our study of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009); Nirmala et al. (2010a,b). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); 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 (I), showing the atom labeling scheme and displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.
N-(2,4-Dichlorophenyl)-2,4-dimethylbenzenesulfonamide top
Crystal data top
C14H13Cl2NO2SZ = 2
Mr = 330.21F(000) = 340
Triclinic, P1Dx = 1.483 Mg m−3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54180 Å
a = 8.2407 (9) ÅCell parameters from 25 reflections
b = 8.3418 (9) Åθ = 6.7–18.3°
c = 10.849 (1) ŵ = 5.27 mm−1
α = 84.59 (1)°T = 293 K
β = 89.06 (1)°Plate, colorless
γ = 85.07 (1)°0.45 × 0.40 × 0.13 mm
V = 739.69 (13) Å3
Data collection top
Ennraf–Nonius CAD-4
diffractometer		2496 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 66.9°, θmin = 4.1°
ω/2θ scansh = −9→9
Absorption correction: ψ scan
(North et al., 1968)		k = −9→9
Tmin = 0.200, Tmax = 0.547l = −12→12
5173 measured reflections3 standard reflections every 120 min
2629 independent reflections intensity decay: 1.0%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.159 w = 1/[σ2(Fo2) + (0.1122P)2 + 0.3056P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.003
2629 reflectionsΔρmax = 0.41 e Å−3
187 parametersΔρmin = −0.80 e Å−3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0131 (18)
Crystal data top
C14H13Cl2NO2Sγ = 85.07 (1)°
Mr = 330.21V = 739.69 (13) Å3
Triclinic, P1Z = 2
a = 8.2407 (9) ÅCu Kα radiation
b = 8.3418 (9) ŵ = 5.27 mm−1
c = 10.849 (1) ÅT = 293 K
α = 84.59 (1)°0.45 × 0.40 × 0.13 mm
β = 89.06 (1)°
Data collection top
Ennraf–Nonius CAD-4
diffractometer		2496 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.033
Tmin = 0.200, Tmax = 0.5473 standard reflections every 120 min
5173 measured reflections intensity decay: 1.0%
2629 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0561 restraint
wR(F2) = 0.159H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.41 e Å−3
2629 reflectionsΔρmin = −0.80 e Å−3
187 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
C10.0771 (3)0.4275 (3)0.2785 (2)0.0417 (5)
C20.1504 (3)0.3433 (3)0.3839 (2)0.0494 (6)
C30.0454 (4)0.2704 (4)0.4696 (3)0.0593 (7)
H30.09030.21330.54050.071*
C4−0.1211 (4)0.2779 (4)0.4556 (3)0.0586 (7)
C5−0.1883 (4)0.3659 (4)0.3526 (3)0.0571 (7)
H5−0.30070.37640.34280.069*
C6−0.0905 (3)0.4382 (3)0.2642 (2)0.0497 (6)
H6−0.13720.49520.19390.060*
C70.3576 (3)0.2472 (3)0.0982 (2)0.0385 (5)
C80.3155 (3)0.0907 (3)0.1315 (2)0.0394 (5)
C90.4329 (3)−0.0337 (3)0.1657 (2)0.0440 (6)
H90.4039−0.13810.18720.053*
C100.5934 (3)0.0004 (3)0.1671 (2)0.0448 (6)
C110.6398 (3)0.1535 (3)0.1328 (2)0.0496 (6)
H110.74900.17410.13310.060*
C120.5214 (3)0.2753 (3)0.0980 (2)0.0459 (6)
H120.55160.37850.07390.055*
C130.3296 (4)0.3251 (5)0.4112 (3)0.0705 (9)
H13A0.36850.43000.41340.085*
H13B0.38690.26980.34770.085*
H13C0.34780.26390.48990.085*
C14−0.2268 (5)0.1923 (5)0.5518 (4)0.0833 (11)
H14A−0.17030.17450.62920.100*
H14B−0.25030.09040.52500.100*
H14C−0.32680.25790.56210.100*
N10.2394 (3)0.3750 (2)0.06051 (18)0.0425 (5)
H1N0.156 (3)0.347 (4)0.026 (3)0.051*
O10.3348 (2)0.5697 (2)0.1953 (2)0.0564 (5)
O20.0776 (3)0.6299 (2)0.08078 (18)0.0559 (5)
Cl10.11490 (8)0.04794 (8)0.12875 (7)0.0581 (3)
Cl20.74198 (9)−0.15459 (9)0.20963 (7)0.0672 (3)
S10.18758 (7)0.51721 (7)0.15244 (5)0.0428 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0409 (12)0.0415 (13)0.0434 (12)−0.0039 (9)0.0029 (10)−0.0073 (10)
C20.0487 (15)0.0545 (16)0.0446 (13)0.0003 (11)−0.0017 (11)−0.0077 (11)
C30.0670 (18)0.0663 (18)0.0424 (13)0.0009 (14)−0.0003 (12)0.0003 (12)
C40.0614 (17)0.0637 (18)0.0516 (15)−0.0101 (14)0.0112 (13)−0.0078 (13)
C50.0440 (14)0.0716 (19)0.0575 (15)−0.0091 (13)0.0056 (12)−0.0119 (13)
C60.0450 (14)0.0559 (15)0.0475 (13)−0.0012 (11)−0.0019 (10)−0.0034 (11)
C70.0397 (12)0.0382 (12)0.0374 (11)−0.0034 (9)0.0025 (9)−0.0027 (9)
C80.0398 (12)0.0406 (13)0.0384 (11)−0.0086 (9)0.0006 (9)−0.0029 (9)
C90.0503 (14)0.0380 (12)0.0429 (12)−0.0041 (10)−0.0009 (10)0.0008 (9)
C100.0440 (13)0.0455 (13)0.0439 (12)0.0053 (10)−0.0032 (10)−0.0071 (10)
C110.0381 (13)0.0524 (15)0.0599 (15)−0.0058 (11)0.0026 (11)−0.0122 (12)
C120.0413 (13)0.0404 (13)0.0568 (14)−0.0082 (10)0.0079 (10)−0.0058 (10)
C130.0512 (17)0.097 (3)0.0608 (17)0.0054 (16)−0.0101 (13)−0.0045 (16)
C140.084 (3)0.092 (3)0.073 (2)−0.018 (2)0.0244 (19)0.0047 (19)
N10.0435 (11)0.0382 (11)0.0450 (11)−0.0008 (8)0.0010 (8)−0.0015 (8)
O10.0508 (11)0.0462 (11)0.0749 (12)−0.0120 (8)0.0031 (9)−0.0134 (9)
O20.0590 (12)0.0403 (10)0.0646 (11)0.0061 (8)0.0026 (9)0.0059 (8)
Cl10.0405 (4)0.0519 (4)0.0825 (5)−0.0131 (3)−0.0042 (3)−0.0001 (3)
Cl20.0586 (5)0.0630 (5)0.0758 (5)0.0180 (3)−0.0144 (4)−0.0036 (4)
S10.0434 (4)0.0333 (4)0.0512 (4)−0.0023 (2)0.0033 (3)−0.0024 (3)
Geometric parameters (Å, º) top
C1—C61.387 (4)C9—C101.378 (4)
C1—C21.402 (4)C9—H90.9300
C1—S11.773 (2)C10—C111.381 (4)
C2—C31.393 (4)C10—Cl21.737 (2)
C2—C131.502 (4)C11—C121.377 (4)
C3—C41.378 (5)C11—H110.9300
C3—H30.9300C12—H120.9300
C4—C51.374 (4)C13—H13A0.9600
C4—C141.515 (4)C13—H13B0.9600
C5—C61.372 (4)C13—H13C0.9600
C5—H50.9300C14—H14A0.9600
C6—H60.9300C14—H14B0.9600
C7—C121.389 (3)C14—H14C0.9600
C7—C81.393 (3)N1—S11.645 (2)
C7—N11.416 (3)N1—H1N0.853 (18)
C8—C91.384 (3)O1—S11.424 (2)
C8—Cl11.722 (2)O2—S11.4311 (19)
C6—C1—C2120.8 (2)C11—C10—Cl2119.1 (2)
C6—C1—S1115.43 (19)C12—C11—C10118.7 (2)
C2—C1—S1123.7 (2)C12—C11—H11120.6
C3—C2—C1115.9 (3)C10—C11—H11120.6
C3—C2—C13118.1 (3)C11—C12—C7121.4 (2)
C1—C2—C13125.9 (3)C11—C12—H12119.3
C4—C3—C2123.9 (3)C7—C12—H12119.3
C4—C3—H3118.1C2—C13—H13A109.5
C2—C3—H3118.1C2—C13—H13B109.5
C5—C4—C3118.2 (3)H13A—C13—H13B109.5
C5—C4—C14121.1 (3)C2—C13—H13C109.5
C3—C4—C14120.7 (3)H13A—C13—H13C109.5
C6—C5—C4120.4 (3)H13B—C13—H13C109.5
C6—C5—H5119.8C4—C14—H14A109.5
C4—C5—H5119.8C4—C14—H14B109.5
C5—C6—C1120.8 (3)H14A—C14—H14B109.5
C5—C6—H6119.6C4—C14—H14C109.5
C1—C6—H6119.6H14A—C14—H14C109.5
C12—C7—C8118.3 (2)H14B—C14—H14C109.5
C12—C7—N1119.8 (2)C7—N1—S1120.33 (16)
C8—C7—N1121.9 (2)C7—N1—H1N115 (2)
C9—C8—C7121.2 (2)S1—N1—H1N110 (2)
C9—C8—Cl1118.61 (18)O1—S1—O2119.34 (13)
C7—C8—Cl1120.21 (19)O1—S1—N1106.94 (12)
C10—C9—C8118.6 (2)O2—S1—N1104.56 (11)
C10—C9—H9120.7O1—S1—C1110.04 (12)
C8—C9—H9120.7O2—S1—C1108.11 (12)
C9—C10—C11121.8 (2)N1—S1—C1107.11 (11)
C9—C10—Cl2119.1 (2)
C6—C1—C2—C31.3 (4)C8—C9—C10—C11−1.5 (4)
S1—C1—C2—C3−175.4 (2)C8—C9—C10—Cl2−179.91 (18)
C6—C1—C2—C13−179.0 (3)C9—C10—C11—C121.0 (4)
S1—C1—C2—C134.4 (4)Cl2—C10—C11—C12179.3 (2)
C1—C2—C3—C4−0.2 (4)C10—C11—C12—C70.7 (4)
C13—C2—C3—C4−180.0 (3)C8—C7—C12—C11−1.7 (4)
C2—C3—C4—C5−1.8 (5)N1—C7—C12—C11−179.3 (2)
C2—C3—C4—C14178.7 (3)C12—C7—N1—S1−74.9 (3)
C3—C4—C5—C62.6 (5)C8—C7—N1—S1107.6 (2)
C14—C4—C5—C6−177.8 (3)C7—N1—S1—O148.1 (2)
C4—C5—C6—C1−1.6 (4)C7—N1—S1—O2175.56 (18)
C2—C1—C6—C5−0.4 (4)C7—N1—S1—C1−69.8 (2)
S1—C1—C6—C5176.5 (2)C6—C1—S1—O1151.8 (2)
C12—C7—C8—C91.1 (4)C2—C1—S1—O1−31.4 (3)
N1—C7—C8—C9178.6 (2)C6—C1—S1—O219.9 (2)
C12—C7—C8—Cl1−178.02 (18)C2—C1—S1—O2−163.3 (2)
N1—C7—C8—Cl1−0.5 (3)C6—C1—S1—N1−92.3 (2)
C7—C8—C9—C100.5 (4)C2—C1—S1—N184.5 (2)
Cl1—C8—C9—C10179.62 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.85 (2)2.24 (2)3.056 (3)159 (3)
N1—H1N···Cl10.85 (2)2.68 (3)3.020 (2)105 (2)
Symmetry code: (i) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formulaC14H13Cl2NO2S
Mr330.21
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.2407 (9), 8.3418 (9), 10.849 (1)
α, β, γ (°)84.59 (1), 89.06 (1), 85.07 (1)
V (Å3)739.69 (13)
Z2
Radiation typeCu Kα
µ (mm−1)5.27
Crystal size (mm)0.45 × 0.40 × 0.13
Data collection
DiffractometerEnnraf–Nonius CAD-4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.200, 0.547
No. of measured, independent and
observed [I > 2σ(I)] reflections		5173, 2629, 2496
Rint0.033
(sin θ/λ)max (Å−1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.159, 1.05
No. of reflections2629
No. of parameters187
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.41, −0.80

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), 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···O2i0.853 (18)2.24 (2)3.056 (3)159 (3)
N1—H1N···Cl10.853 (18)2.68 (3)3.020 (2)105 (2)
Symmetry code: (i) −x, −y+1, −z.
 

References

First citationEnraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
 First citationGelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621–632.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Foro, S., Nirmala, P. G., Babitha, K. S. & Fuess, H. (2009). Acta Cryst. E65, o576.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationNirmala, P. G., Gowda, B. T., Foro, S. & Fuess, H. (2010a). Acta Cryst. E66, o1059.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationNirmala, P. G., Gowda, B. T., Foro, S. & Fuess, H. (2010b). Acta Cryst. E66, o1090.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
 First citationPerlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780–o782.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSavitha, M. B. & Gowda, B. T. (2006). Z. Naturforsch. Teil A, 60, 600–606.  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 citationStoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.  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 66| Part 12| December 2010| Page o3144
https://doi.org/10.1107/S1600536810045563
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