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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 68| Part 8| August 2012| Page o2353
https://doi.org/10.1107/S1600536812030176

3-Acetyl-1-(2,3-di­chloro­phen­yl)thio­urea

B. Thimme Gowda,a* Sabine Forob and Sharatha Kumara

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 30 June 2012; accepted 2 July 2012; online 7 July 2012)

In the crystal structure of the title compound, C9H8Cl2N2OS, there are two mol­ecules in the asymmetric unit which are connected by a pair of N—H⋯S hydrogen bonds. An intra­molecular N—H⋯O hydrogen bond stabilizes the mol­ecular conformation of each molecule.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2001[Gowda, B. T., Paulus, H. & Fuess, H. (2001). Z. Naturforsch. Teil A, 56, 386-394.]); Kumar et al. (2012[Kumar, S., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o2191.]); Shahwar et al. (2012[Shahwar, D., Tahir, M. N., Chohan, M. M., Ahmad, N. & Raza, M. A. (2012). Acta Cryst. E68, o1160.]). For N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007[Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2570.]). For N-chloro­aryl­sulfonamides, see: Gowda & Ramachandra (1989[Gowda, B. T. & Ramachandra, P. (1989). J. Chem. Soc. Perkin Trans. 2, pp. 1067-1071.]), Shetty & Gowda (2004[Shetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63-72.]).

[Scheme 1]

Experimental

Crystal data

  • C9H8Cl2N2OS

  • Mr = 263.13

  • Triclinic, [P \overline 1]

  • a = 7.8475 (6) Å

  • b = 9.5987 (7) Å

  • c = 15.141 (1) Å

  • α = 90.044 (6)°

  • β = 91.099 (6)°

  • γ = 100.208 (6)°

  • V = 1122.24 (14) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.74 mm−1

  • T = 293 K

  • 0.46 × 0.44 × 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, Oxfordshire, England.]) Tmin = 0.728, Tmax = 0.777

  • 7971 measured reflections

  • 4578 independent reflections

  • 3885 reflections with I > 2σ(I)

  • Rint = 0.011
Refinement

  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.106

  • S = 1.04

  • 4578 reflections

  • 285 parameters

  • 4 restraints

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

  • Δρmax = 0.67 e Å−3

  • Δρmin = −0.72 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O1 0.85 (2) 1.91 (2) 2.625 (3) 141 (3)
N2—H2N⋯S2 0.84 (2) 2.56 (2) 3.393 (2) 171 (2)
N3—H3N⋯O2 0.81 (2) 1.93 (2) 2.619 (3) 143 (3)
N4—H4N⋯S1 0.84 (2) 2.59 (2) 3.418 (2) 170 (2)

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, 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/S1600536812030176/bt5964sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812030176/bt5964Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812030176/bt5964Isup3.cml

checkCIF report


Comment top

As part of studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2001; Kumar et al., 2012: Shahwar et al., 2012); N-(aryl)-methanesulfonamides (Gowda et al., 2007) and N-chloroarylsulfonamides (Gowda & Ramachandra, 1989; Shetty & Gowda, 2004), in the present work, the crystal structure of 3-acetyl-1-(2,3-dichlorophenyl)thiourea has been determined (Fig. 1).

The asymmetric unit of the structure contains two molecules. The conformation of the two N—H bonds are anti to each other. Furthermore, the conformations of the amide C═S and the C═O are also anti to each other and both the bonds are anti to the adjacent N—H bonds, similar to the anti conformation observed in 3-acetyl-1-(2,3-dimethylphenyl)thiourea (I)(Kumar et al., 2012). The N—H bond adjacent to the 2,3-dichlorophenyl ring is syn to the ortho- and meta-Cl atoms in one of the molecules and anti in the other molecule, compared to the anti conformation observed with respect to the ortho- and meta-methyl groups in the 2,3-dimethylphenyl ring of (I).

The side chains are oriented themselves with respect to the 2,3-dichlorophenyl rings with the torsion angles, C2—C1—N1—C7 = 116.47 (26)° and C6—C1—N1—C7 = -65.77 (33)° in molecule 1 and C11—C10—N3—C16 = 129.96 (25)° and C15—C10—N3—C16 = -53.71 (35)° in molecule 2 of the title compound, compared to the torsion angles of C2—C1—N1—C7 = 83.59 (47)° and C6—C1—N1—C7 = -99.89 (44)° for in (I). The dihedral angles between the phenyl rings and the side chains are 62.5 (1)° and 51.3 (1)°, in the two molecules, compared to the value of 81.33 (10)° in (I).

The hydrogen atoms of the NH attached to the phenyl rings and the amide O atoms are involved in the intramolecular hydrogen bonding. In the crystal, the molecules form inversion dimers through pairs of N—H···S intermolecular hydrogen bonds (Table 1, Fig.2).

Related literature top

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2001); Kumar et al. (2012); Shahwar et al. (2012). For N-(aryl)-methanesulfonamides, see: Gowda et al. (2007). For N-chloroarylsulfonamides, see: Gowda & Ramachandra (1989), Shetty & Gowda (2004).

Experimental top

3-Acetyl-1-(2,3-dichlorophenyl)thiourea was synthesized by adding a solution of acetyl chloride (0.10 mol) in acetone (30 ml) dropwise to a suspension of ammonium thiocyanate (0.10 mol) in acetone (30 ml). The reaction mixture was refluxed for 30 min. After cooling to room temperature, a solution of 2,3-dichloroaniline (0.10 mol) in acetone (10 ml) was added and refluxed for 3 h. The reaction mixture was poured into acidified cold water. The precipitated title compound was recrystallized to constant melting point from acetonitrile. The purity of the compound was checked and characterized by its infrared spectrum.

Prism like light yellow single crystals used in X-ray diffraction studies were grown in acetonitrile solution by slow evaporation of the solvent at room temperature.

Refinement top

The coordinates of the amino H atoms were refined with the N—H distances restrained to 0.86 (2) Å. H atoms bonded to C were positioned with idealized geometry using a riding model with the aromatic C—H = 0.93 Å, methyl C—H = 0.96 Å. All H atoms were refined with their isotropic displacement parameter set to 1.2 times of the Ueq of the parent atom.

Structure description top

As part of studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2001; Kumar et al., 2012: Shahwar et al., 2012); N-(aryl)-methanesulfonamides (Gowda et al., 2007) and N-chloroarylsulfonamides (Gowda & Ramachandra, 1989; Shetty & Gowda, 2004), in the present work, the crystal structure of 3-acetyl-1-(2,3-dichlorophenyl)thiourea has been determined (Fig. 1).

The asymmetric unit of the structure contains two molecules. The conformation of the two N—H bonds are anti to each other. Furthermore, the conformations of the amide C═S and the C═O are also anti to each other and both the bonds are anti to the adjacent N—H bonds, similar to the anti conformation observed in 3-acetyl-1-(2,3-dimethylphenyl)thiourea (I)(Kumar et al., 2012). The N—H bond adjacent to the 2,3-dichlorophenyl ring is syn to the ortho- and meta-Cl atoms in one of the molecules and anti in the other molecule, compared to the anti conformation observed with respect to the ortho- and meta-methyl groups in the 2,3-dimethylphenyl ring of (I).

The side chains are oriented themselves with respect to the 2,3-dichlorophenyl rings with the torsion angles, C2—C1—N1—C7 = 116.47 (26)° and C6—C1—N1—C7 = -65.77 (33)° in molecule 1 and C11—C10—N3—C16 = 129.96 (25)° and C15—C10—N3—C16 = -53.71 (35)° in molecule 2 of the title compound, compared to the torsion angles of C2—C1—N1—C7 = 83.59 (47)° and C6—C1—N1—C7 = -99.89 (44)° for in (I). The dihedral angles between the phenyl rings and the side chains are 62.5 (1)° and 51.3 (1)°, in the two molecules, compared to the value of 81.33 (10)° in (I).

The hydrogen atoms of the NH attached to the phenyl rings and the amide O atoms are involved in the intramolecular hydrogen bonding. In the crystal, the molecules form inversion dimers through pairs of N—H···S intermolecular hydrogen bonds (Table 1, Fig.2).

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2001); Kumar et al. (2012); Shahwar et al. (2012). For N-(aryl)-methanesulfonamides, see: Gowda et al. (2007). For N-chloroarylsulfonamides, see: Gowda & Ramachandra (1989), Shetty & Gowda (2004).

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 with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
3-Acetyl-1-(2,3-dichlorophenyl)thiourea top
Crystal data top
C9H8Cl2N2OSZ = 4
Mr = 263.13F(000) = 536
Triclinic, P1Dx = 1.557 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8475 (6) ÅCell parameters from 4895 reflections
b = 9.5987 (7) Åθ = 2.5–27.7°
c = 15.141 (1) ŵ = 0.74 mm−1
α = 90.044 (6)°T = 293 K
β = 91.099 (6)°Prism, light yellow
γ = 100.208 (6)°0.46 × 0.44 × 0.36 mm
V = 1122.24 (14) Å3
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		4578 independent reflections
Radiation source: fine-focus sealed tube3885 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.011
Rotation method data acquisition using ω scansθmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		h = −9→8
Tmin = 0.728, Tmax = 0.777k = −11→10
7971 measured reflectionsl = −18→17
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0403P)2 + 0.8845P]
where P = (Fo2 + 2Fc2)/3
4578 reflections(Δ/σ)max = 0.002
285 parametersΔρmax = 0.67 e Å−3
4 restraintsΔρmin = −0.72 e Å−3
Crystal data top
C9H8Cl2N2OSγ = 100.208 (6)°
Mr = 263.13V = 1122.24 (14) Å3
Triclinic, P1Z = 4
a = 7.8475 (6) ÅMo Kα radiation
b = 9.5987 (7) ŵ = 0.74 mm−1
c = 15.141 (1) ÅT = 293 K
α = 90.044 (6)°0.46 × 0.44 × 0.36 mm
β = 91.099 (6)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		4578 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		3885 reflections with I > 2σ(I)
Tmin = 0.728, Tmax = 0.777Rint = 0.011
7971 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0414 restraints
wR(F2) = 0.106H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.67 e Å−3
4578 reflectionsΔρmin = −0.72 e Å−3
285 parameters
Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) 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) top
xyzUiso*/Ueq
Cl10.39378 (10)0.64301 (8)−0.04620 (5)0.0675 (2)
Cl20.51017 (13)0.81095 (13)−0.21801 (5)0.0956 (3)
S10.86892 (8)0.69266 (7)0.15722 (5)0.05361 (18)
O10.3014 (2)0.6735 (2)0.21951 (13)0.0687 (6)
N10.5647 (3)0.7665 (2)0.11819 (13)0.0457 (5)
H1N0.458 (2)0.754 (3)0.1305 (18)0.055*
N20.5747 (2)0.6306 (2)0.24233 (12)0.0397 (4)
H2N0.639 (3)0.591 (3)0.2760 (15)0.048*
C10.6232 (3)0.8420 (2)0.04055 (15)0.0412 (5)
C20.5487 (3)0.7949 (3)−0.04025 (16)0.0441 (5)
C30.5999 (3)0.8705 (3)−0.11636 (17)0.0526 (6)
C40.7246 (3)0.9910 (3)−0.11191 (19)0.0561 (7)
H40.75891.0412−0.16300.067*
C50.7983 (3)1.0369 (3)−0.0314 (2)0.0564 (7)
H50.88271.1182−0.02830.068*
C60.7479 (3)0.9632 (3)0.04515 (18)0.0512 (6)
H60.79770.99510.09930.061*
C70.6603 (3)0.6990 (2)0.17092 (14)0.0374 (5)
C80.4039 (3)0.6220 (3)0.26475 (16)0.0451 (5)
C90.3545 (3)0.5463 (3)0.34875 (18)0.0607 (7)
H9A0.23360.54390.35870.073*
H9B0.42140.59490.39690.073*
H9C0.37680.45130.34490.073*
Cl30.68592 (11)−0.06753 (7)0.35412 (5)0.0693 (2)
Cl40.60530 (13)−0.20874 (9)0.53971 (7)0.0884 (3)
S20.78757 (8)0.45828 (6)0.39216 (4)0.04733 (16)
O21.0172 (3)0.1780 (2)0.20337 (14)0.0772 (6)
N30.9002 (3)0.2163 (2)0.36075 (13)0.0453 (5)
H3N0.932 (3)0.169 (3)0.3223 (15)0.054*
N40.9362 (3)0.3818 (2)0.24969 (13)0.0432 (4)
H4N0.924 (3)0.463 (2)0.2336 (17)0.052*
C100.8602 (3)0.1564 (2)0.44498 (15)0.0405 (5)
C110.7626 (3)0.0208 (2)0.44964 (16)0.0440 (5)
C120.7286 (3)−0.0417 (3)0.53190 (18)0.0531 (6)
C130.7920 (4)0.0296 (3)0.60792 (18)0.0591 (7)
H130.7690−0.01260.66270.071*
C140.8890 (4)0.1627 (3)0.60259 (17)0.0570 (7)
H140.93170.21070.65400.068*
C150.9241 (3)0.2264 (3)0.52160 (16)0.0494 (6)
H150.99080.31660.51870.059*
C160.8777 (3)0.3440 (2)0.33372 (14)0.0378 (5)
C171.0071 (3)0.3013 (3)0.18971 (17)0.0509 (6)
C181.0707 (4)0.3771 (3)0.10721 (18)0.0633 (7)
H18A1.08010.30930.06180.076*
H18B1.18220.43440.11870.076*
H18C0.99060.43640.08820.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0655 (4)0.0654 (4)0.0644 (4)−0.0075 (3)−0.0080 (3)0.0111 (3)
Cl20.0922 (6)0.1402 (9)0.0462 (4)−0.0007 (6)−0.0098 (4)0.0234 (5)
S10.0414 (3)0.0606 (4)0.0619 (4)0.0158 (3)0.0148 (3)0.0243 (3)
O10.0413 (10)0.1009 (16)0.0665 (12)0.0190 (10)0.0075 (9)0.0325 (11)
N10.0369 (10)0.0585 (12)0.0425 (11)0.0101 (9)0.0053 (8)0.0153 (9)
N20.0370 (10)0.0457 (10)0.0369 (10)0.0085 (8)0.0031 (8)0.0084 (8)
C10.0373 (11)0.0450 (12)0.0440 (12)0.0140 (9)0.0063 (9)0.0114 (10)
C20.0390 (12)0.0481 (13)0.0469 (13)0.0124 (10)0.0013 (10)0.0109 (10)
C30.0494 (14)0.0666 (16)0.0448 (13)0.0184 (12)0.0053 (11)0.0165 (12)
C40.0547 (15)0.0618 (16)0.0570 (16)0.0228 (13)0.0183 (12)0.0259 (13)
C50.0490 (14)0.0439 (13)0.0766 (19)0.0075 (11)0.0175 (13)0.0136 (12)
C60.0496 (14)0.0492 (14)0.0549 (15)0.0084 (11)0.0046 (11)0.0040 (11)
C70.0406 (11)0.0359 (11)0.0352 (11)0.0054 (9)0.0019 (9)−0.0002 (8)
C80.0404 (12)0.0504 (13)0.0435 (13)0.0054 (10)0.0047 (10)0.0039 (10)
C90.0482 (14)0.0785 (19)0.0559 (16)0.0111 (13)0.0135 (12)0.0228 (14)
Cl30.0901 (5)0.0490 (4)0.0630 (4)−0.0018 (3)−0.0183 (4)−0.0066 (3)
Cl40.1007 (6)0.0566 (4)0.0989 (7)−0.0115 (4)0.0078 (5)0.0281 (4)
S20.0601 (4)0.0442 (3)0.0409 (3)0.0175 (3)0.0060 (3)0.0027 (2)
O20.1154 (18)0.0608 (13)0.0642 (13)0.0367 (12)0.0298 (12)0.0009 (10)
N30.0624 (13)0.0365 (10)0.0384 (10)0.0122 (9)0.0063 (9)−0.0002 (8)
N40.0492 (11)0.0402 (10)0.0407 (10)0.0088 (9)0.0072 (8)0.0048 (8)
C100.0456 (12)0.0361 (11)0.0413 (12)0.0115 (9)0.0024 (9)0.0030 (9)
C110.0471 (13)0.0383 (12)0.0470 (13)0.0096 (10)−0.0026 (10)0.0009 (10)
C120.0540 (14)0.0435 (13)0.0625 (16)0.0096 (11)0.0084 (12)0.0135 (11)
C130.0730 (18)0.0640 (17)0.0450 (14)0.0233 (14)0.0111 (13)0.0147 (12)
C140.0720 (18)0.0622 (16)0.0406 (13)0.0232 (14)−0.0027 (12)−0.0037 (11)
C150.0575 (15)0.0424 (13)0.0480 (14)0.0082 (11)−0.0027 (11)−0.0019 (10)
C160.0360 (11)0.0369 (11)0.0385 (11)0.0015 (9)−0.0010 (9)0.0004 (9)
C170.0534 (14)0.0553 (15)0.0454 (13)0.0127 (12)0.0066 (11)−0.0024 (11)
C180.0667 (17)0.078 (2)0.0479 (15)0.0187 (15)0.0160 (13)0.0028 (13)
Geometric parameters (Å, º) top
Cl1—C21.726 (2)Cl3—C111.719 (2)
Cl2—C31.734 (3)Cl4—C121.725 (3)
S1—C71.666 (2)S2—C161.669 (2)
O1—C81.217 (3)O2—C171.218 (3)
N1—C71.330 (3)N3—C161.332 (3)
N1—C11.422 (3)N3—C101.417 (3)
N1—H1N0.846 (17)N3—H3N0.808 (17)
N2—C81.378 (3)N4—C171.379 (3)
N2—C71.387 (3)N4—C161.388 (3)
N2—H2N0.843 (16)N4—H4N0.836 (16)
C1—C61.382 (3)C10—C151.381 (3)
C1—C21.386 (3)C10—C111.391 (3)
C2—C31.390 (3)C11—C121.392 (3)
C3—C41.378 (4)C12—C131.377 (4)
C4—C51.377 (4)C13—C141.370 (4)
C4—H40.9300C13—H130.9300
C5—C61.385 (4)C14—C151.381 (4)
C5—H50.9300C14—H140.9300
C6—H60.9300C15—H150.9300
C8—C91.489 (3)C17—C181.495 (4)
C9—H9A0.9600C18—H18A0.9600
C9—H9B0.9600C18—H18B0.9600
C9—H9C0.9600C18—H18C0.9600
C7—N1—C1125.50 (19)C16—N3—C10126.43 (19)
C7—N1—H1N114.5 (19)C16—N3—H3N114 (2)
C1—N1—H1N119.6 (19)C10—N3—H3N120 (2)
C8—N2—C7128.45 (19)C17—N4—C16128.0 (2)
C8—N2—H2N117.7 (18)C17—N4—H4N116.8 (19)
C7—N2—H2N113.8 (18)C16—N4—H4N115.1 (19)
C6—C1—C2120.1 (2)C15—C10—C11119.8 (2)
C6—C1—N1121.0 (2)C15—C10—N3121.4 (2)
C2—C1—N1118.9 (2)C11—C10—N3118.8 (2)
C1—C2—C3119.6 (2)C10—C11—C12119.3 (2)
C1—C2—Cl1120.12 (18)C10—C11—Cl3119.74 (18)
C3—C2—Cl1120.3 (2)C12—C11—Cl3120.92 (19)
C4—C3—C2120.4 (2)C13—C12—C11120.4 (2)
C4—C3—Cl2119.6 (2)C13—C12—Cl4119.3 (2)
C2—C3—Cl2120.0 (2)C11—C12—Cl4120.3 (2)
C5—C4—C3119.6 (2)C14—C13—C12119.8 (2)
C5—C4—H4120.2C14—C13—H13120.1
C3—C4—H4120.2C12—C13—H13120.1
C4—C5—C6120.6 (2)C13—C14—C15120.7 (2)
C4—C5—H5119.7C13—C14—H14119.7
C6—C5—H5119.7C15—C14—H14119.7
C1—C6—C5119.7 (3)C10—C15—C14120.0 (2)
C1—C6—H6120.2C10—C15—H15120.0
C5—C6—H6120.2C14—C15—H15120.0
N1—C7—N2115.39 (19)N3—C16—N4115.5 (2)
N1—C7—S1125.13 (17)N3—C16—S2125.53 (17)
N2—C7—S1119.48 (16)N4—C16—S2118.93 (16)
O1—C8—N2122.4 (2)O2—C17—N4122.3 (2)
O1—C8—C9122.6 (2)O2—C17—C18122.8 (2)
N2—C8—C9115.0 (2)N4—C17—C18114.9 (2)
C8—C9—H9A109.5C17—C18—H18A109.5
C8—C9—H9B109.5C17—C18—H18B109.5
H9A—C9—H9B109.5H18A—C18—H18B109.5
C8—C9—H9C109.5C17—C18—H18C109.5
H9A—C9—H9C109.5H18A—C18—H18C109.5
H9B—C9—H9C109.5H18B—C18—H18C109.5
C7—N1—C1—C6−65.8 (3)C16—N3—C10—C15−53.7 (3)
C7—N1—C1—C2116.5 (3)C16—N3—C10—C11130.0 (2)
C6—C1—C2—C3−0.1 (3)C15—C10—C11—C120.9 (3)
N1—C1—C2—C3177.6 (2)N3—C10—C11—C12177.3 (2)
C6—C1—C2—Cl1179.65 (18)C15—C10—C11—Cl3−178.97 (19)
N1—C1—C2—Cl1−2.6 (3)N3—C10—C11—Cl3−2.6 (3)
C1—C2—C3—C40.4 (4)C10—C11—C12—C13−0.4 (4)
Cl1—C2—C3—C4−179.44 (19)Cl3—C11—C12—C13179.4 (2)
C1—C2—C3—Cl2178.94 (18)C10—C11—C12—Cl4179.07 (18)
Cl1—C2—C3—Cl2−0.9 (3)Cl3—C11—C12—Cl4−1.1 (3)
C2—C3—C4—C5−0.2 (4)C11—C12—C13—C140.0 (4)
Cl2—C3—C4—C5−178.8 (2)Cl4—C12—C13—C14−179.5 (2)
C3—C4—C5—C6−0.2 (4)C12—C13—C14—C150.0 (4)
C2—C1—C6—C5−0.2 (4)C11—C10—C15—C14−0.9 (4)
N1—C1—C6—C5−177.9 (2)N3—C10—C15—C14−177.2 (2)
C4—C5—C6—C10.4 (4)C13—C14—C15—C100.5 (4)
C1—N1—C7—N2−179.0 (2)C10—N3—C16—N4176.4 (2)
C1—N1—C7—S11.4 (4)C10—N3—C16—S2−3.3 (4)
C8—N2—C7—N11.1 (3)C17—N4—C16—N33.3 (3)
C8—N2—C7—S1−179.31 (19)C17—N4—C16—S2−177.0 (2)
C7—N2—C8—O12.5 (4)C16—N4—C17—O24.5 (4)
C7—N2—C8—C9−177.0 (2)C16—N4—C17—C18−175.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.85 (2)1.91 (2)2.625 (3)141 (3)
N2—H2N···S20.84 (2)2.56 (2)3.393 (2)171 (2)
N3—H3N···O20.81 (2)1.93 (2)2.619 (3)143 (3)
N4—H4N···S10.84 (2)2.59 (2)3.418 (2)170 (2)

Experimental details

Crystal data
Chemical formulaC9H8Cl2N2OS
Mr263.13
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.8475 (6), 9.5987 (7), 15.141 (1)
α, β, γ (°)90.044 (6), 91.099 (6), 100.208 (6)
V (Å3)1122.24 (14)
Z4
Radiation typeMo Kα
µ (mm−1)0.74
Crystal size (mm)0.46 × 0.44 × 0.36
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.728, 0.777
No. of measured, independent and
observed [I > 2σ(I)] reflections		7971, 4578, 3885
Rint0.011
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.106, 1.04
No. of reflections4578
No. of parameters285
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.67, −0.72

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···O10.846 (17)1.91 (2)2.625 (3)141 (3)
N2—H2N···S20.843 (16)2.559 (17)3.393 (2)171 (2)
N3—H3N···O20.808 (17)1.93 (2)2.619 (3)143 (3)
N4—H4N···S10.836 (16)2.591 (17)3.418 (2)170 (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 faculty.

References

First citationGowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2570.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Paulus, H. & Fuess, H. (2001). Z. Naturforsch. Teil A, 56, 386–394.  CAS Google Scholar
 First citationGowda, B. T. & Ramachandra, P. (1989). J. Chem. Soc. Perkin Trans. 2, pp. 1067–1071.  CrossRef Google Scholar
 First citationKumar, S., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o2191.  CSD CrossRef IUCr Journals Google Scholar
 First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.  Google Scholar
 First citationShahwar, D., Tahir, M. N., Chohan, M. M., Ahmad, N. & Raza, M. A. (2012). Acta Cryst. E68, o1160.  CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationShetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63–72.  CAS Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS 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.

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ISSN: 2056-9890
Volume 68| Part 8| August 2012| Page o2353
https://doi.org/10.1107/S1600536812030176
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