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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2649
https://doi.org/10.1107/S1600536811036968

2,4-Di­chloro-N-(2,5-di­methyl­phen­yl)benzene­sulfonamide

Vinola Z. Rodrigues,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 11 September 2011; accepted 12 September 2011; online 17 September 2011)

The asymmetric unit of the title compound, C14H13Cl2NO2S, contains three independent moleules. The torsion angles of the C—SO2—NH—C segments in the three mol­ecules are 67.5 (2), 83.4 (2) and −77.5 (2)°. The two aromatic rings are tilted relative to each other by 68.8 (1), 64.1 (1) and 68.5 (1)°. The crystal structure features dimers linked by pairs of N—H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006[Savitha, M. B. & Gowda, B. T. (2006). Z. Naturforsch. Teil A, 61, 600-606.]). For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001[Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058-2077.]). For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Arjunan et al. (2004[Arjunan, V., Mohan, S., Subramanian, S. & Gowda, B. T. (2004). Spectrochim. Acta Part A, 60, 1141-1159.]); Gowda et al. (2000[Gowda, B. T., Paulus, H. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 791-800.]), on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007[Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2337.]) and on N-(ar­yl)-aryl­sulfonamides, 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.]); Gowda et al. (2010[Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010). Acta Cryst. E66, o2542.]).

[Scheme 1]

Experimental

Crystal data

  • C14H13Cl2NO2S

  • Mr = 330.21

  • Monoclinic, P 21 /c

  • a = 24.3070 (8) Å

  • b = 14.8880 (6) Å

  • c = 12.4365 (5) Å

  • β = 94.929 (3)°

  • V = 4483.9 (3) Å3

  • Z = 12

  • Mo Kα radiation

  • μ = 0.57 mm−1

  • T = 293 K

  • 0.42 × 0.36 × 0.36 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, England.]) Tmin = 0.795, Tmax = 0.820

  • 18567 measured reflections

  • 9151 independent reflections

  • 6822 reflections with I > 2σ(I)

  • Rint = 0.015
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.099

  • S = 1.01

  • 9151 reflections

  • 556 parameters

  • 3 restraints

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

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O5i 0.83 (2) 2.24 (2) 3.033 (2) 160 (2)
N2—H2N⋯O4ii 0.82 (2) 2.16 (2) 2.956 (2) 167 (2)
N3—H3N⋯O2iii 0.82 (2) 2.34 (2) 3.082 (2) 151 (2)
Symmetry codes: (i) x, y, z-1; (ii) -x, -y+1, -z+2; (iii) x, y, z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; 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/S1600536811036968/bt5642sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036968/bt5642Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811036968/bt5642Isup3.cml

checkCIF report


Comment top

The sulfonamide moiety is the constituent of many biologically important compounds. The hydrogen bonding preferences of sulfonamides have been investigated (Adsmond & Grant, 2001). As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Arjunan et al., 2004; Gowda et al., 2000), N-(aryl)-methanesulfonamides (Gowda et al., 2007) and N-(aryl)-arylsulfonamides (Gowda et al., 2010), in the present work, the crystal structure of 2,4-dichloro-N- (2,5-dimethylphenyl)-benzenesulfonamide (I) has been determined (Fig. 1).

The asymmetric unit of (I) contains three independent moleules. The molecules are twisted at the S atom with the C—SO2—NH—C torsion angles of 67.5 (2)° (molecule 1), 83.4 (2)° (molecule 2) and -77.5 (2)° (molecule 3), compared to the values of -85.1 (3)° and -47.2 (5)° in the major and minor components, respectively, of 2,4-dichloro-N-(2-methylphenyl)-benzenesulfonamide (II) (Gowda et al., 2010)

The sulfonyl and the aniline benzene rings in (I) are tilted relative to each other by 68.8 (1)° in molecule 1, 64.1 (1)° in molecule 2 and 68.5 (1)° in molecule 3, compared to the values of 74.9 (1)° and 71.0 (3)° in the two components of(II)

The other bond parameters in (I) are similar to those observed in (II) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).

In the crystal structure, the pairs of intermolecular N–H···O hydrogen bonds (Table 1) link the molecules into dimers. Part of the crystal structure is shown in Fig. 2.

Related literature top

For the preparation of the title compound, see: Savitha & Gowda (2006). For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Arjunan et al. (2004); Gowda et al. (2000), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and on N-(aryl)-arylsulfonamides, see: Gelbrich et al. (2007); Perlovich et al. (2006); Gowda et al. (2010).

Experimental top

The solution of 1,3-dichlorobenzene (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-dichlorobenzenesulfonylchloride 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 2,4-dichloro-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 (Savitha & Gowda, 2006).

Prism like light pink single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Refinement top

The H atoms of the NH groups were located in a difference map and refined with the N—H distance restrained to 0.86 (2) %A. The other H atoms were positioned with idealized geometry using a riding model with the aromatic C—H = 0.93Å and methyl C—H = 0.96 Å. Their isotropic displacement parameters were set to 1.2Ueq(C-aromatic, N) and 1.5Ueq(C-methyl).

Structure description top

The sulfonamide moiety is the constituent of many biologically important compounds. The hydrogen bonding preferences of sulfonamides have been investigated (Adsmond & Grant, 2001). As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Arjunan et al., 2004; Gowda et al., 2000), N-(aryl)-methanesulfonamides (Gowda et al., 2007) and N-(aryl)-arylsulfonamides (Gowda et al., 2010), in the present work, the crystal structure of 2,4-dichloro-N- (2,5-dimethylphenyl)-benzenesulfonamide (I) has been determined (Fig. 1).

The asymmetric unit of (I) contains three independent moleules. The molecules are twisted at the S atom with the C—SO2—NH—C torsion angles of 67.5 (2)° (molecule 1), 83.4 (2)° (molecule 2) and -77.5 (2)° (molecule 3), compared to the values of -85.1 (3)° and -47.2 (5)° in the major and minor components, respectively, of 2,4-dichloro-N-(2-methylphenyl)-benzenesulfonamide (II) (Gowda et al., 2010)

The sulfonyl and the aniline benzene rings in (I) are tilted relative to each other by 68.8 (1)° in molecule 1, 64.1 (1)° in molecule 2 and 68.5 (1)° in molecule 3, compared to the values of 74.9 (1)° and 71.0 (3)° in the two components of(II)

The other bond parameters in (I) are similar to those observed in (II) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).

In the crystal structure, the pairs of intermolecular N–H···O hydrogen bonds (Table 1) link the molecules into dimers. Part of the crystal structure is shown in Fig. 2.

For the preparation of the title compound, see: Savitha & Gowda (2006). For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Arjunan et al. (2004); Gowda et al. (2000), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and on N-(aryl)-arylsulfonamides, see: Gelbrich et al. (2007); Perlovich et al. (2006); Gowda et al. (2010).

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 and displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
2,4-Dichloro-N-(2,5-dimethylphenyl)benzenesulfonamide top
Crystal data top
C14H13Cl2NO2SF(000) = 2040
Mr = 330.21Dx = 1.467 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7968 reflections
a = 24.3070 (8) Åθ = 2.6–27.8°
b = 14.8880 (6) ŵ = 0.57 mm−1
c = 12.4365 (5) ÅT = 293 K
β = 94.929 (3)°Prism, light pink
V = 4483.9 (3) Å30.42 × 0.36 × 0.36 mm
Z = 12
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		9151 independent reflections
Radiation source: fine-focus sealed tube6822 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
Rotation method data acquisition using ω scansθmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		h = −26→30
Tmin = 0.795, Tmax = 0.820k = −14→18
18567 measured reflectionsl = −15→15
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) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0428P)2 + 2.5197P]
where P = (Fo2 + 2Fc2)/3
9151 reflections(Δ/σ)max = 0.001
556 parametersΔρmax = 0.34 e Å−3
3 restraintsΔρmin = −0.34 e Å−3
Crystal data top
C14H13Cl2NO2SV = 4483.9 (3) Å3
Mr = 330.21Z = 12
Monoclinic, P21/cMo Kα radiation
a = 24.3070 (8) ŵ = 0.57 mm−1
b = 14.8880 (6) ÅT = 293 K
c = 12.4365 (5) Å0.42 × 0.36 × 0.36 mm
β = 94.929 (3)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		9151 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		6822 reflections with I > 2σ(I)
Tmin = 0.795, Tmax = 0.820Rint = 0.015
18567 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0383 restraints
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.34 e Å−3
9151 reflectionsΔρmin = −0.34 e Å−3
556 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
C10.37117 (9)0.66784 (14)0.19972 (17)0.0352 (5)
C20.42435 (9)0.64017 (15)0.17972 (18)0.0393 (5)
C30.47007 (10)0.67249 (17)0.2413 (2)0.0478 (6)
H30.50540.65550.22640.057*
C40.46238 (11)0.73046 (17)0.3255 (2)0.0488 (6)
C50.41066 (11)0.75673 (16)0.3491 (2)0.0481 (6)
H50.40630.79500.40680.058*
C60.36519 (10)0.72543 (15)0.28586 (18)0.0427 (5)
H60.33000.74320.30120.051*
C70.28443 (9)0.49200 (14)0.23739 (17)0.0347 (5)
C80.22861 (9)0.48517 (16)0.25563 (19)0.0423 (5)
C90.21695 (11)0.43970 (17)0.3489 (2)0.0525 (6)
H90.18030.43360.36380.063*
C100.25731 (12)0.40370 (17)0.4193 (2)0.0543 (7)
H100.24740.37360.48030.065*
C110.31271 (10)0.41112 (16)0.40178 (19)0.0455 (6)
C120.32510 (9)0.45586 (14)0.30937 (18)0.0388 (5)
H120.36190.46180.29520.047*
C130.18268 (10)0.52347 (19)0.1809 (2)0.0566 (7)
H13A0.19230.51940.10780.068*
H13B0.17700.58530.19900.068*
H13C0.14940.49020.18830.068*
C140.35722 (12)0.3700 (2)0.4776 (2)0.0622 (7)
H14A0.34170.32270.51790.075*
H14B0.37270.41510.52630.075*
H14C0.38560.34590.43690.075*
N10.29977 (8)0.52955 (13)0.13736 (15)0.0383 (4)
H1N0.3196 (9)0.4971 (15)0.1025 (18)0.046*
O10.26641 (6)0.68499 (11)0.15806 (13)0.0464 (4)
O20.32113 (7)0.64305 (11)0.00710 (12)0.0478 (4)
Cl10.43532 (3)0.56301 (5)0.07956 (5)0.05525 (17)
Cl20.51978 (3)0.77011 (6)0.40399 (7)0.0827 (3)
S10.31057 (2)0.63530 (4)0.11853 (4)0.03675 (13)
C150.10849 (8)0.60065 (14)0.88706 (17)0.0341 (5)
C160.10887 (9)0.65759 (15)0.97592 (17)0.0371 (5)
C170.14506 (9)0.72894 (16)0.98750 (18)0.0417 (5)
H170.14630.76521.04850.050*
C180.17939 (9)0.74567 (16)0.90733 (19)0.0417 (5)
C190.17843 (10)0.69315 (16)0.8165 (2)0.0456 (6)
H190.20090.70670.76190.055*
C200.14345 (9)0.61981 (16)0.80740 (18)0.0415 (5)
H200.14330.58280.74710.050*
C21−0.02186 (8)0.57033 (16)0.74447 (17)0.0374 (5)
C22−0.02921 (10)0.66073 (17)0.7207 (2)0.0472 (6)
C23−0.05413 (12)0.6814 (2)0.6184 (2)0.0639 (8)
H23−0.05950.74130.59910.077*
C24−0.07089 (11)0.6157 (2)0.5453 (2)0.0633 (8)
H24−0.08740.63220.47800.076*
C25−0.06385 (10)0.5257 (2)0.5695 (2)0.0517 (6)
C26−0.03908 (9)0.50430 (17)0.67050 (19)0.0436 (5)
H26−0.03380.44420.68920.052*
C27−0.01135 (13)0.73384 (19)0.7994 (3)0.0681 (8)
H27A0.02790.74140.80150.082*
H27B−0.02130.71780.87000.082*
H27C−0.02930.78900.77710.082*
C28−0.08357 (13)0.4536 (2)0.4908 (2)0.0771 (10)
H28A−0.07940.47370.41860.092*
H28B−0.12180.44100.49830.092*
H28C−0.06210.40010.50510.092*
N20.00272 (8)0.54195 (14)0.84816 (15)0.0397 (4)
H2N−0.0133 (10)0.5490 (16)0.9025 (16)0.048*
O30.07967 (7)0.46077 (11)0.77479 (13)0.0462 (4)
O40.06783 (7)0.45703 (11)0.96970 (13)0.0476 (4)
Cl30.06310 (3)0.64443 (5)1.07415 (5)0.05622 (18)
Cl40.22360 (3)0.83646 (5)0.92104 (6)0.0652 (2)
S20.06476 (2)0.50518 (4)0.86965 (4)0.03674 (13)
C290.29694 (9)0.33765 (14)0.81101 (17)0.0355 (5)
C300.24190 (9)0.35952 (15)0.82580 (18)0.0397 (5)
C310.19879 (10)0.32037 (16)0.7636 (2)0.0472 (6)
H310.16240.33490.77410.057*
C320.21059 (11)0.25911 (16)0.6851 (2)0.0479 (6)
C330.26383 (11)0.23590 (16)0.66867 (19)0.0466 (6)
H330.27090.19430.61580.056*
C340.30681 (10)0.27513 (15)0.73174 (18)0.0411 (5)
H340.34300.25950.72110.049*
C350.37412 (9)0.52663 (14)0.75746 (17)0.0367 (5)
C360.33740 (10)0.56036 (16)0.67582 (19)0.0444 (6)
C370.35960 (11)0.59760 (19)0.5871 (2)0.0562 (7)
H370.33610.62170.53160.067*
C380.41565 (12)0.59976 (19)0.5793 (2)0.0609 (7)
H380.42920.62460.51820.073*
C390.45216 (11)0.56595 (18)0.6600 (2)0.0541 (7)
C400.43062 (10)0.52978 (16)0.7496 (2)0.0451 (6)
H400.45440.50720.80570.054*
C410.27599 (11)0.5588 (2)0.6826 (2)0.0670 (8)
H41A0.26790.57200.75510.080*
H41B0.26190.50040.66250.080*
H41C0.25890.60300.63440.080*
C420.51378 (13)0.5707 (3)0.6520 (3)0.0872 (11)
H42A0.52270.62600.61790.105*
H42B0.52520.52100.61010.105*
H42C0.53260.56820.72310.105*
N30.35468 (8)0.49250 (12)0.85565 (15)0.0384 (4)
H3N0.3345 (9)0.5232 (15)0.8909 (18)0.046*
O50.34473 (7)0.38367 (11)0.99890 (12)0.0468 (4)
O60.40211 (6)0.34595 (11)0.85093 (14)0.0477 (4)
Cl50.22596 (3)0.43853 (5)0.92023 (5)0.05357 (17)
Cl60.15616 (3)0.21002 (6)0.60671 (7)0.0780 (2)
S30.35411 (2)0.38736 (4)0.88676 (4)0.03727 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0373 (11)0.0319 (11)0.0368 (11)0.0014 (9)0.0061 (9)0.0055 (9)
C20.0406 (12)0.0384 (12)0.0393 (12)0.0058 (10)0.0057 (10)0.0018 (10)
C30.0383 (13)0.0463 (14)0.0589 (15)0.0034 (11)0.0053 (11)−0.0005 (12)
C40.0510 (14)0.0435 (14)0.0504 (15)−0.0018 (11)−0.0053 (11)0.0013 (11)
C50.0599 (16)0.0412 (14)0.0431 (13)0.0054 (12)0.0040 (12)−0.0045 (11)
C60.0455 (13)0.0387 (13)0.0449 (13)0.0058 (10)0.0094 (11)0.0019 (10)
C70.0384 (12)0.0294 (11)0.0373 (12)−0.0009 (9)0.0090 (9)−0.0030 (9)
C80.0375 (12)0.0390 (13)0.0517 (14)−0.0008 (10)0.0105 (10)−0.0070 (11)
C90.0457 (14)0.0483 (15)0.0669 (17)−0.0044 (12)0.0231 (13)−0.0014 (13)
C100.0674 (17)0.0469 (15)0.0526 (15)−0.0055 (13)0.0272 (13)0.0055 (12)
C110.0577 (15)0.0362 (13)0.0436 (13)−0.0019 (11)0.0096 (11)0.0021 (10)
C120.0380 (12)0.0347 (12)0.0445 (13)−0.0028 (9)0.0078 (10)−0.0004 (10)
C130.0374 (13)0.0649 (18)0.0675 (18)0.0017 (12)0.0040 (12)−0.0047 (14)
C140.0745 (19)0.0589 (17)0.0530 (16)0.0013 (15)0.0048 (14)0.0155 (13)
N10.0403 (11)0.0387 (11)0.0368 (10)0.0018 (8)0.0093 (8)−0.0011 (8)
O10.0395 (9)0.0445 (9)0.0558 (10)0.0102 (7)0.0072 (7)0.0018 (8)
O20.0497 (10)0.0573 (11)0.0365 (9)0.0044 (8)0.0047 (7)0.0112 (8)
Cl10.0479 (3)0.0647 (4)0.0534 (4)0.0141 (3)0.0061 (3)−0.0154 (3)
Cl20.0625 (5)0.0876 (6)0.0929 (6)−0.0034 (4)−0.0223 (4)−0.0240 (5)
S10.0353 (3)0.0389 (3)0.0364 (3)0.0050 (2)0.0052 (2)0.0058 (2)
C150.0293 (10)0.0362 (11)0.0366 (11)0.0000 (9)0.0017 (9)0.0024 (9)
C160.0320 (11)0.0454 (13)0.0341 (11)0.0007 (9)0.0045 (9)0.0022 (10)
C170.0452 (13)0.0412 (13)0.0381 (12)−0.0032 (10)−0.0004 (10)−0.0029 (10)
C180.0385 (12)0.0392 (13)0.0468 (13)−0.0072 (10)0.0005 (10)0.0056 (10)
C190.0427 (13)0.0490 (14)0.0466 (14)−0.0050 (11)0.0136 (11)0.0029 (11)
C200.0430 (13)0.0435 (13)0.0391 (12)−0.0021 (10)0.0094 (10)−0.0029 (10)
C210.0285 (10)0.0463 (13)0.0379 (12)−0.0026 (9)0.0055 (9)0.0074 (10)
C220.0390 (13)0.0453 (14)0.0571 (15)−0.0008 (10)0.0029 (11)0.0069 (12)
C230.0589 (17)0.0561 (17)0.075 (2)0.0013 (14)−0.0031 (15)0.0264 (15)
C240.0519 (16)0.085 (2)0.0505 (16)−0.0086 (15)−0.0092 (13)0.0214 (16)
C250.0401 (13)0.0713 (19)0.0438 (14)−0.0142 (12)0.0047 (11)0.0035 (13)
C260.0387 (12)0.0470 (14)0.0455 (13)−0.0083 (10)0.0059 (10)0.0050 (11)
C270.0690 (19)0.0429 (15)0.091 (2)0.0041 (14)−0.0038 (17)−0.0007 (15)
C280.068 (2)0.105 (3)0.0572 (18)−0.0259 (18)−0.0007 (15)−0.0113 (18)
N20.0341 (10)0.0495 (12)0.0359 (10)−0.0009 (9)0.0057 (8)0.0063 (9)
O30.0443 (9)0.0413 (9)0.0532 (10)−0.0003 (7)0.0058 (7)−0.0080 (8)
O40.0459 (9)0.0474 (10)0.0491 (10)−0.0008 (8)0.0023 (7)0.0144 (8)
Cl30.0553 (4)0.0695 (4)0.0468 (3)−0.0092 (3)0.0211 (3)−0.0064 (3)
Cl40.0691 (4)0.0592 (4)0.0670 (4)−0.0302 (4)0.0048 (3)−0.0005 (3)
S20.0340 (3)0.0359 (3)0.0404 (3)−0.0019 (2)0.0032 (2)0.0029 (2)
C290.0373 (11)0.0322 (11)0.0381 (12)0.0039 (9)0.0098 (9)0.0061 (9)
C300.0427 (12)0.0371 (12)0.0407 (12)0.0058 (10)0.0120 (10)0.0015 (10)
C310.0406 (13)0.0447 (14)0.0570 (15)0.0050 (11)0.0074 (11)0.0031 (12)
C320.0526 (15)0.0384 (13)0.0514 (15)0.0026 (11)−0.0039 (12)0.0006 (11)
C330.0602 (16)0.0365 (13)0.0435 (13)0.0069 (11)0.0075 (12)−0.0030 (10)
C340.0449 (13)0.0376 (12)0.0422 (13)0.0074 (10)0.0116 (10)0.0059 (10)
C350.0451 (13)0.0286 (11)0.0373 (12)0.0003 (9)0.0097 (10)0.0000 (9)
C360.0485 (14)0.0407 (13)0.0446 (13)0.0073 (11)0.0080 (11)0.0051 (11)
C370.0623 (17)0.0594 (17)0.0473 (15)0.0129 (13)0.0077 (13)0.0170 (13)
C380.0698 (19)0.0608 (18)0.0554 (16)0.0054 (15)0.0241 (14)0.0214 (14)
C390.0513 (15)0.0510 (15)0.0627 (17)0.0016 (12)0.0204 (13)0.0103 (13)
C400.0416 (13)0.0430 (13)0.0511 (14)0.0017 (10)0.0063 (11)0.0068 (11)
C410.0513 (16)0.085 (2)0.0652 (18)0.0148 (15)0.0054 (14)0.0245 (16)
C420.0575 (19)0.103 (3)0.105 (3)0.0012 (18)0.0330 (18)0.029 (2)
N30.0469 (11)0.0332 (10)0.0367 (10)0.0046 (8)0.0128 (8)0.0012 (8)
O50.0526 (10)0.0508 (10)0.0372 (9)0.0010 (8)0.0051 (7)0.0088 (7)
O60.0405 (9)0.0440 (10)0.0598 (10)0.0093 (7)0.0109 (8)0.0056 (8)
Cl50.0490 (3)0.0585 (4)0.0551 (4)0.0110 (3)0.0150 (3)−0.0127 (3)
Cl60.0680 (5)0.0682 (5)0.0927 (6)0.0053 (4)−0.0235 (4)−0.0205 (4)
S30.0379 (3)0.0366 (3)0.0380 (3)0.0047 (2)0.0075 (2)0.0061 (2)
Geometric parameters (Å, º) top
C1—C61.390 (3)C23—C241.372 (4)
C1—C21.399 (3)C23—H230.9300
C1—S11.780 (2)C24—C251.381 (4)
C2—C31.381 (3)C24—H240.9300
C2—Cl11.732 (2)C25—C261.382 (3)
C3—C41.382 (3)C25—C281.503 (4)
C3—H30.9300C26—H260.9300
C4—C51.372 (4)C27—H27A0.9600
C4—Cl21.736 (3)C27—H27B0.9600
C5—C61.381 (3)C27—H27C0.9600
C5—H50.9300C28—H28A0.9600
C6—H60.9300C28—H28B0.9600
C7—C121.384 (3)C28—H28C0.9600
C7—C81.398 (3)N2—S21.6049 (19)
C7—N11.442 (3)N2—H2N0.815 (16)
C8—C91.393 (3)O3—S21.4261 (16)
C8—C131.502 (3)O4—S21.4324 (16)
C9—C101.367 (4)C29—C341.392 (3)
C9—H90.9300C29—C301.404 (3)
C10—C111.387 (4)C29—S31.772 (2)
C10—H100.9300C30—C311.378 (3)
C11—C121.384 (3)C30—Cl51.729 (2)
C11—C141.503 (4)C31—C321.383 (3)
C12—H120.9300C31—H310.9300
C13—H13A0.9600C32—C331.372 (3)
C13—H13B0.9600C32—Cl61.736 (3)
C13—H13C0.9600C33—C341.381 (3)
C14—H14A0.9600C33—H330.9300
C14—H14B0.9600C34—H340.9300
C14—H14C0.9600C35—C401.386 (3)
N1—S11.616 (2)C35—C361.387 (3)
N1—H1N0.830 (16)C35—N31.439 (3)
O1—S11.4254 (16)C36—C371.385 (3)
O2—S11.4356 (16)C36—C411.502 (4)
C15—C201.389 (3)C37—C381.374 (4)
C15—C161.392 (3)C37—H370.9300
C15—S21.777 (2)C38—C391.376 (4)
C16—C171.379 (3)C38—H380.9300
C16—Cl31.733 (2)C39—C401.381 (3)
C17—C181.377 (3)C39—C421.511 (4)
C17—H170.9300C40—H400.9300
C18—C191.373 (3)C41—H41A0.9600
C18—Cl41.726 (2)C41—H41B0.9600
C19—C201.382 (3)C41—H41C0.9600
C19—H190.9300C42—H42A0.9600
C20—H200.9300C42—H42B0.9600
C21—C261.386 (3)C42—H42C0.9600
C21—C221.386 (3)N3—S31.6128 (19)
C21—N21.437 (3)N3—H3N0.824 (16)
C22—C231.396 (4)O5—S31.4335 (16)
C22—C271.503 (4)O6—S31.4243 (16)
C6—C1—C2118.6 (2)C25—C24—H24119.2
C6—C1—S1117.97 (17)C24—C25—C26117.2 (2)
C2—C1—S1123.44 (17)C24—C25—C28121.6 (3)
C3—C2—C1120.7 (2)C26—C25—C28121.2 (3)
C3—C2—Cl1117.63 (18)C25—C26—C21121.5 (2)
C1—C2—Cl1121.66 (18)C25—C26—H26119.2
C2—C3—C4118.9 (2)C21—C26—H26119.2
C2—C3—H3120.6C22—C27—H27A109.5
C4—C3—H3120.6C22—C27—H27B109.5
C5—C4—C3121.7 (2)H27A—C27—H27B109.5
C5—C4—Cl2119.3 (2)C22—C27—H27C109.5
C3—C4—Cl2119.0 (2)H27A—C27—H27C109.5
C4—C5—C6119.0 (2)H27B—C27—H27C109.5
C4—C5—H5120.5C25—C28—H28A109.5
C6—C5—H5120.5C25—C28—H28B109.5
C5—C6—C1121.0 (2)H28A—C28—H28B109.5
C5—C6—H6119.5C25—C28—H28C109.5
C1—C6—H6119.5H28A—C28—H28C109.5
C12—C7—C8121.1 (2)H28B—C28—H28C109.5
C12—C7—N1119.03 (19)C21—N2—S2124.18 (15)
C8—C7—N1119.6 (2)C21—N2—H2N120.9 (18)
C9—C8—C7116.1 (2)S2—N2—H2N114.6 (18)
C9—C8—C13120.4 (2)O3—S2—O4119.25 (10)
C7—C8—C13123.5 (2)O3—S2—N2108.80 (10)
C10—C9—C8122.5 (2)O4—S2—N2107.06 (10)
C10—C9—H9118.7O3—S2—C15106.25 (10)
C8—C9—H9118.7O4—S2—C15107.97 (10)
C9—C10—C11121.4 (2)N2—S2—C15106.93 (10)
C9—C10—H10119.3C34—C29—C30118.2 (2)
C11—C10—H10119.3C34—C29—S3118.74 (17)
C12—C11—C10116.9 (2)C30—C29—S3123.09 (17)
C12—C11—C14121.4 (2)C31—C30—C29121.0 (2)
C10—C11—C14121.7 (2)C31—C30—Cl5117.74 (18)
C11—C12—C7122.0 (2)C29—C30—Cl5121.21 (18)
C11—C12—H12119.0C30—C31—C32118.8 (2)
C7—C12—H12119.0C30—C31—H31120.6
C8—C13—H13A109.5C32—C31—H31120.6
C8—C13—H13B109.5C33—C32—C31121.8 (2)
H13A—C13—H13B109.5C33—C32—Cl6119.6 (2)
C8—C13—H13C109.5C31—C32—Cl6118.7 (2)
H13A—C13—H13C109.5C32—C33—C34119.1 (2)
H13B—C13—H13C109.5C32—C33—H33120.5
C11—C14—H14A109.5C34—C33—H33120.5
C11—C14—H14B109.5C33—C34—C29121.2 (2)
H14A—C14—H14B109.5C33—C34—H34119.4
C11—C14—H14C109.5C29—C34—H34119.4
H14A—C14—H14C109.5C40—C35—C36121.0 (2)
H14B—C14—H14C109.5C40—C35—N3118.1 (2)
C7—N1—S1124.04 (15)C36—C35—N3120.8 (2)
C7—N1—H1N115.5 (17)C37—C36—C35117.2 (2)
S1—N1—H1N112.4 (18)C37—C36—C41120.5 (2)
O1—S1—O2119.58 (10)C35—C36—C41122.2 (2)
O1—S1—N1108.61 (10)C38—C37—C36121.5 (2)
O2—S1—N1105.24 (10)C38—C37—H37119.3
O1—S1—C1105.90 (10)C36—C37—H37119.3
O2—S1—C1108.53 (10)C37—C38—C39121.4 (2)
N1—S1—C1108.64 (10)C37—C38—H38119.3
C20—C15—C16118.6 (2)C39—C38—H38119.3
C20—C15—S2118.27 (17)C38—C39—C40117.8 (2)
C16—C15—S2123.16 (16)C38—C39—C42121.0 (3)
C17—C16—C15120.8 (2)C40—C39—C42121.2 (3)
C17—C16—Cl3117.13 (17)C39—C40—C35121.1 (2)
C15—C16—Cl3122.00 (17)C39—C40—H40119.5
C18—C17—C16119.0 (2)C35—C40—H40119.5
C18—C17—H17120.5C36—C41—H41A109.5
C16—C17—H17120.5C36—C41—H41B109.5
C19—C18—C17121.6 (2)H41A—C41—H41B109.5
C19—C18—Cl4119.60 (18)C36—C41—H41C109.5
C17—C18—Cl4118.75 (19)H41A—C41—H41C109.5
C18—C19—C20118.9 (2)H41B—C41—H41C109.5
C18—C19—H19120.5C39—C42—H42A109.5
C20—C19—H19120.5C39—C42—H42B109.5
C19—C20—C15120.9 (2)H42A—C42—H42B109.5
C19—C20—H20119.5C39—C42—H42C109.5
C15—C20—H20119.5H42A—C42—H42C109.5
C26—C21—C22121.4 (2)H42B—C42—H42C109.5
C26—C21—N2117.7 (2)C35—N3—S3123.80 (15)
C22—C21—N2120.8 (2)C35—N3—H3N120.6 (18)
C21—C22—C23116.5 (2)S3—N3—H3N113.2 (18)
C21—C22—C27122.7 (2)O6—S3—O5119.40 (10)
C23—C22—C27120.9 (2)O6—S3—N3108.72 (10)
C24—C23—C22121.8 (3)O5—S3—N3106.01 (10)
C24—C23—H23119.1O6—S3—C29106.19 (10)
C22—C23—H23119.1O5—S3—C29108.55 (10)
C23—C24—C25121.5 (3)N3—S3—C29107.47 (10)
C23—C24—H24119.2
C6—C1—C2—C3−2.8 (3)C22—C23—C24—C25−0.1 (4)
S1—C1—C2—C3175.64 (18)C23—C24—C25—C26−0.1 (4)
C6—C1—C2—Cl1175.86 (17)C23—C24—C25—C28178.3 (3)
S1—C1—C2—Cl1−5.7 (3)C24—C25—C26—C21−0.1 (4)
C1—C2—C3—C42.1 (4)C28—C25—C26—C21−178.6 (2)
Cl1—C2—C3—C4−176.62 (19)C22—C21—C26—C250.6 (3)
C2—C3—C4—C5−0.1 (4)N2—C21—C26—C25179.0 (2)
C2—C3—C4—Cl2179.23 (19)C26—C21—N2—S276.8 (2)
C3—C4—C5—C6−1.1 (4)C22—C21—N2—S2−104.7 (2)
Cl2—C4—C5—C6179.57 (19)C21—N2—S2—O3−31.0 (2)
C4—C5—C6—C10.3 (4)C21—N2—S2—O4−161.10 (18)
C2—C1—C6—C51.6 (3)C21—N2—S2—C1583.4 (2)
S1—C1—C6—C5−176.95 (18)C20—C15—S2—O35.4 (2)
C12—C7—C8—C9−0.5 (3)C16—C15—S2—O3−175.35 (18)
N1—C7—C8—C9173.5 (2)C20—C15—S2—O4134.45 (18)
C12—C7—C8—C13179.6 (2)C16—C15—S2—O4−46.3 (2)
N1—C7—C8—C13−6.4 (3)C20—C15—S2—N2−110.64 (18)
C7—C8—C9—C100.2 (4)C16—C15—S2—N268.6 (2)
C13—C8—C9—C10−180.0 (2)C34—C29—C30—C31−0.1 (3)
C8—C9—C10—C110.4 (4)S3—C29—C30—C31178.74 (18)
C9—C10—C11—C12−0.6 (4)C34—C29—C30—Cl5−178.42 (17)
C9—C10—C11—C14−178.7 (2)S3—C29—C30—Cl50.4 (3)
C10—C11—C12—C70.2 (3)C29—C30—C31—C32−0.4 (4)
C14—C11—C12—C7178.3 (2)Cl5—C30—C31—C32177.96 (18)
C8—C7—C12—C110.4 (3)C30—C31—C32—C330.6 (4)
N1—C7—C12—C11−173.7 (2)C30—C31—C32—Cl6−179.90 (18)
C12—C7—N1—S1−96.7 (2)C31—C32—C33—C34−0.3 (4)
C8—C7—N1—S189.1 (2)Cl6—C32—C33—C34−179.79 (18)
C7—N1—S1—O1−47.2 (2)C32—C33—C34—C29−0.2 (3)
C7—N1—S1—O2−176.39 (17)C30—C29—C34—C330.4 (3)
C7—N1—S1—C167.5 (2)S3—C29—C34—C33−178.48 (18)
C6—C1—S1—O14.7 (2)C40—C35—C36—C37−0.4 (3)
C2—C1—S1—O1−173.71 (18)N3—C35—C36—C37175.7 (2)
C6—C1—S1—O2134.30 (17)C40—C35—C36—C41−179.3 (2)
C2—C1—S1—O2−44.2 (2)N3—C35—C36—C41−3.2 (4)
C6—C1—S1—N1−111.77 (18)C35—C36—C37—C381.1 (4)
C2—C1—S1—N169.8 (2)C41—C36—C37—C38180.0 (3)
C20—C15—C16—C17−3.2 (3)C36—C37—C38—C39−0.8 (5)
S2—C15—C16—C17177.61 (17)C37—C38—C39—C40−0.2 (4)
C20—C15—C16—Cl3174.91 (17)C37—C38—C39—C42−178.4 (3)
S2—C15—C16—Cl3−4.3 (3)C38—C39—C40—C350.8 (4)
C15—C16—C17—C182.8 (3)C42—C39—C40—C35179.0 (3)
Cl3—C16—C17—C18−175.37 (18)C36—C35—C40—C39−0.5 (4)
C16—C17—C18—C190.0 (4)N3—C35—C40—C39−176.7 (2)
C16—C17—C18—Cl4178.69 (17)C40—C35—N3—S3−75.5 (3)
C17—C18—C19—C20−2.3 (4)C36—C35—N3—S3108.3 (2)
Cl4—C18—C19—C20178.97 (19)C35—N3—S3—O637.0 (2)
C18—C19—C20—C151.9 (4)C35—N3—S3—O5166.52 (18)
C16—C15—C20—C190.8 (3)C35—N3—S3—C29−77.5 (2)
S2—C15—C20—C19−179.97 (18)C34—C29—S3—O6−3.0 (2)
C26—C21—C22—C23−0.8 (3)C30—C29—S3—O6178.14 (18)
N2—C21—C22—C23−179.2 (2)C34—C29—S3—O5−132.55 (17)
C26—C21—C22—C27179.6 (2)C30—C29—S3—O548.6 (2)
N2—C21—C22—C271.2 (4)C34—C29—S3—N3113.20 (18)
C21—C22—C23—C240.5 (4)C30—C29—S3—N3−65.6 (2)
C27—C22—C23—C24−179.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O5i0.83 (2)2.24 (2)3.033 (2)160 (2)
N2—H2N···O4ii0.82 (2)2.16 (2)2.956 (2)167 (2)
N3—H3N···O2iii0.82 (2)2.34 (2)3.082 (2)151 (2)
Symmetry codes: (i) x, y, z−1; (ii) −x, −y+1, −z+2; (iii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC14H13Cl2NO2S
Mr330.21
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)24.3070 (8), 14.8880 (6), 12.4365 (5)
β (°) 94.929 (3)
V (Å3)4483.9 (3)
Z12
Radiation typeMo Kα
µ (mm−1)0.57
Crystal size (mm)0.42 × 0.36 × 0.36
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.795, 0.820
No. of measured, independent and
observed [I > 2σ(I)] reflections		18567, 9151, 6822
Rint0.015
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.099, 1.01
No. of reflections9151
No. of parameters556
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.34, −0.34

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···O5i0.830 (16)2.241 (18)3.033 (2)160 (2)
N2—H2N···O4ii0.815 (16)2.157 (17)2.956 (2)167 (2)
N3—H3N···O2iii0.824 (16)2.336 (19)3.082 (2)151 (2)
Symmetry codes: (i) x, y, z−1; (ii) −x, −y+1, −z+2; (iii) x, y, z+1.
 

Acknowledgements

VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of a RFSMS fellowship.

References

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ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2649
https://doi.org/10.1107/S1600536811036968
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