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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 70| Part 1| January 2014| Pages o57-o58
https://doi.org/10.1107/S1600536813033527

4-[(E)-(4-Chloro­benzyl­­idene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione

B. K. Sarojini,a,b P. S. Manjula,a Manpreet Kaur,c Brian J. Andersond and Jerry P. Jasinskid*

aDepartment of Chemistry, P.A. College of Engineering, Nadupadavu 574 153, D.K., Mangalore, India, bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and dDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
*Correspondence e-mail: jjasinski@keene.edu

(Received 8 December 2013; accepted 11 December 2013; online 14 December 2013)

In the title compound, C10H9ClN4S, the dihedral angle between the mean planes of the phenyl and 1H-1,2,4-triazole-5(4H)-thione rings is 25.3 (9)°. The latter ring is essentially planar, with maximum deviations of 0.010 and −0.010 Å for the ring N atom in the 4-position and ring C atom bearing the methyl group, respectively. An intra­molecular C—H⋯S contact occurs. In the crystal, pairs of weak N—H⋯S inter­actions link the mol­ecules into inversion dimers in the ac plane, forming R22(8) graph-set motifs. In addition, weak π–π inter­actions [centroid–centroid distances = 3.3463 (14) and 3.6127 (13)Å] are observed.

CCDC reference: 976444

Related literature

For the chemistry of Schiff base compounds, see: Dubey & Vaid (1991[Dubey, S. N. & Vaid, B. K. (1991). Synth. React. Inorg. Met.Org. Chem. 21, 1299-1311.]); Yadav et al. (1994[Yadav, S., Srivastava, S. & Pandey, O. P. (1994). Synth. React. Inorg. Met. Org. Chem. 24, 925-939.]). For the use of Schiff bases containing different donor atoms in analytical applications and metal coordination, see: Galic et al. (2001[Galic, N., Peric, B., Prodic, K. B. & Cimerman, Z. (2001). J. Med. Chem. 559, 187-194.]); Wyrzykiewicz & Prukah (1998[Wyrzykiewicz, E. & Prukah, D. (1998). J. Heterocycl. Chem. 35, 381-387.]); Reddy & Lirgappa (1994[Reddy, H. & Lirgappa, Y. (1994). Indian J. Heterocycl. Chem. 33, 919-923.]). Many compounds containing S and N atoms are anti­hypertensive (Wei et al., 1981[Wei, P. H. L. & Bell, C. S. (1981). Chem. Abstr. 96, 104227.],1982[Wei, P. H. L. & Bell, C. S. (1982). American Home Products Corporation, US Patent No. 4302585.]), analgesic (Thieme et al., 1973a[Thieme, P., Konig, H. & Amann, A. (1973a). BASF, Ger. Patent 2228259.],b[Thieme, P., Konig, H. & Amann, A. (1973b). Chem. Abstr. 80, 83034q.]), anti­inflammatory (Dornow et al., 1964[Dornow, A., Menzel, H. & Marx, P. (1964). Chem. Ber. 97, 2173-2178.]), sedative (Barrera et al.,1985[Barrera, H., Vinas, J. M., Font-Altaba, M. & Solans, X. (1985). Polyhedron, 4, 2027-2030.]), or fungicidal (Malik et al., 2011[Malik, S., Ghosh, S. & Mitu, L. (2011). J. Serb. Chem. Soc. 76, 1387-1394.]). For the crystal structures of related Schiff bases, see: Jeyaseelan et al. (2012[Jeyaseelan, S., Devarajegowda, H. C., Sathishkumar, R., D'souza, A. S. & D'souza, A. (2012). Acta Cryst. E68, o1407.]); Devarajegowda et al. (2012[Devarajegowda, H. C., Jeyaseelan, S., Sathishkumar, R., D'souza, A. S. & D'souza, A. (2012). Acta Cryst. E68, o1607.]); Vinduvahini et al. (2011[Vinduvahini, M., Roopashree, K. R., Bhattacharya, S., Krishna, K. M. & Devaru, V. B. (2011). Acta Cryst. E67, o2535-o2536.]); Almutairi et al. (2012[Almutairi, M. S., Al-Shehri, M. M., El-Emam, A. A., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o656.]); Kubicki et al. (2012[Kubicki, M., Dutkiewicz, G., Praveen, A. S., Mayekar, A. N., Narayana, B. & Yathirajan, H. S. (2012). J. Chem. Crystallogr. 42, 432-437.]); Praveen et al. (2012[Praveen, A. S., Jasinski, J. P., Keeley, A. C., Yathirajan, H. S. & Narayana, B. (2012). Acta Cryst. E68, o3435.]); Kant et al. (2012[Kant, R., Gupta, V. K., Kapoor, K., Sapnakumari, M., Sarojini, B. K. & Narayana, B. (2012). Acta Cryst. E68, o2193.]); Ding et al. (2009[Ding, Q.-C., Huang, Y.-L., Jin, J.-Y., Zhang, L.-X., Zhou, C.-F. & Hu, M.-L. (2009). Z. Kristallogr. New Cryst. Struct. 224, 105-106.]). For the crystal structures of Schiff bases reported by our group, see: Sarojini et al. (2007a[Sarojini, B. K., Yathirajan, H. S., Narayana, B., Sunil, K. & Bolte, M. (2007a). Acta Cryst. E63, o3521.],b[Sarojini, B. K., Narayana, B., Sunil, K., Yathirajan, H. S. & Bolte, M. (2007b). Acta Cryst. E63, o3551.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For π–π stacking, see: Grimme (2008[Grimme, S. (2008). Angew. Chem. Int. Ed. 47, 3430-3434.]).

[Scheme 1]

Experimental

Crystal data

  • C10H9ClN4S

  • Mr = 252.72

  • Triclinic, [P \overline 1]

  • a = 7.0718 (8) Å

  • b = 7.2901 (8) Å

  • c = 11.8434 (7) Å

  • α = 92.778 (7)°

  • β = 94.986 (7)°

  • γ = 109.752 (10)°

  • V = 570.50 (10) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 4.49 mm−1

  • T = 173 K

  • 0.42 × 0.08 × 0.06 mm
Data collection

  • Agilent Gemini EOS diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.544, Tmax = 1.000

  • 3413 measured reflections

  • 2195 independent reflections

  • 1860 reflections with I > 2σ(I)

  • Rint = 0.030
Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.120

  • S = 1.02

  • 2195 reflections

  • 146 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.39 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N4—H4⋯S1i 0.86 2.43 3.2926 (19) 176
C1—H1⋯S1 0.93 2.62 3.199 (2) 121
Symmetry code: (i) -x-1, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 976444

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536813033527/qm2102sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813033527/qm2102Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813033527/qm2102Isup3.cml

checkCIF report


Comment top

During the last few decades, there has been a considerable interest in the chemistry of Schiff base compounds (Dubey & Vaid, 1991; Yadav et al., 1994). Schiff bases, containing different donor atoms, also find use in analytical applications and metal coordination (Galic et al., 2001; Wyrzykiewicz & Pruka, 1998; Reddy & Lirgappa, 1994). Since many compounds containing sulfur and nitrogen atoms are antihypertensive (Wei et al., 1981,1982), analgesic (Thieme et al., 1973a,b), antiinflammatory (Dornow et al., 1964), sedative (Barrera et al.,1985), or fungicidal (Malik et al., 2011), synthesis of the corresponding heterocyclic compounds could be of interest from the viewpoint of chemical reactivity and biological activity. The crystal structures of some of the related Schiff bases viz: 3-ethyl-4-[(E)-(4-fluorobenzylidene)amino]-1H-1,2,4-triazole-5(4H)-thione (Jeyaseelan et al., 2012); 4-[(E)-(4-fluorobenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione (Devarajegowda et al., 2012); 3-[2-(2,6-dichloro-anilino)benzyl]-4-[(4-methoxybenzylidene)amino]-1H-1,2,4-triazole-5(4H)-thione (Vinduvahini et al., 2011); 3-(adamantan-1-yl)-1-[(4-ethylpiperazin-1-yl)methyl]-4-[(E)-(4-hydroxy-benzylidene)amino]-1H-1,2,4-triazole-5(4H)-thione (Almutairi et al., 2012); 4-{(2E)-2-[1-(4-Methoxyphenyl)ethylidene]hydrazinyl}-8-(trifluoromethyl)quinoline (Kubicki et al., 2012); (E)-N'-(4-Methoxybenzylidene)-2-m-tolylacetohydrazide (Praveen et al., 2012); (1Z)-1-[(2E)-3-(4-bromophenyl)-1-(4-fluorophenyl)prop-2-en-1-ylidene]-2-(2,4-dinitrophenyl)hydrazine (Kant et al., 2012); (E)-3-(2-ethoxyphenyl)-4-(2-fluorobenzylideneamino)-1H-1,2,4-triazole-5(4H)-thione (Ding et al.,2009) have been reported. Crystal structures of some of the Schiff bases were also reported from our group (Sarojini et al., 2007a,b). In continuation of our work on the synthesis of acetamides derivatives, we report herein the crystal structure of the title compound, C10H9ClN4S, (I).

In the title compound, (I), C10H9ClN4S, the dihedral angle between the mean planes of the phenyl ring and the1H-1,2,4-triazole-5(4H)-thione ring is 25.3 (9)° (Fig.1). The 1,2,4-triazole-5(4H)-thione ring is essentially planar with a maximum deviation of 0.010Å and -0.010Å for the N2 nitrogen and C9 carbon atom, respectively. Bond lengths and bond angles are in normal ranges (Allen et al., 1987).In the crystal, weak N4—H4···S1 intermolecular interactions forming R22(8) graph set motifs link the molecules into dimers diagonally in the ac plane (Fig. 2). In addition, weak Cg–Cg π–π intermolecular interactions are observed which may contribute to crystal packing (Cg1–Cg1 = 3.3463 (14)Å; -x, 1-y, -z; Cg2–Cg2 = 3.6127 (13)Å; 1-x, 2-y, 1-z; Cg1 = N2/C81/N4/N3/C9; Cg2 = C2–C7) (Grimme, 1987). No classical hydrogen bonds were observed.

Related literature top

For the chemistry of Schiff base compounds, see: Dubey & Vaid (1991); Yadav et al. (1994). For the use of Schiff bases containing different donor atoms in analytical applications and metal coordination, see: Galic et al. (2001); Wyrzykiewicz & Prukah (1998); Reddy & Lirgappa (1994). Since many compounds containing sulfur and nitrogen atoms are antihypertensive (Wei et al., 1981,1982), analgesic (Thieme et al., 1973a,b), antiinflammatory (Dornow et al., 1964), sedative (Barrera et al.,1985), or fungicidal (Malik et al., 2011), synthesis of the corresponding heterocyclic compounds could be of interest from the viewpoint of chemical reactivity and biological activity. For the crystal structures of related Schiff bases, see: Jeyaseelan et al. (2012); Devarajegowda et al. (2012); Vinduvahini et al. (2011); Almutairi et al. (2012); Kubicki et al. (2012); Praveen et al. (2012); Kant et al. (2012); Ding et al. (2009). For the crystal structures of Schiff bases reported by our group, see: Sarojini et al. (2007a,b). For standard bond lengths, see: Allen et al. (1987). For π–π stacking, see: Grimme (2008). AUTHOR: please remember to sub-dvide this section in future

Experimental top

To a suspension of 4-chlorobenzaldehyde (1.405 g, 0.01 mol) in ethanol (15 ml), 4-amino-5-methyl-2,4-dihydro-3H-1,2,4-triazole- 3-thione (0.01 mol, 1.3 g) was added and heated to get a clear solution. To this a few drops of conc.H2SO4 was added as a catalyst and refluxed for 36 h on a water bath. The precipitate formed was filtered and recrystallized from methanol to get the titled compound. The single crystals were grown from methanol (M.P.:.463 - 465 K).

Refinement top

All of the H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.93Å (CH), 0.96Å (CH3) or 0.86Å (NH). Isotropic displacement parameters for these atoms were set to 1.2 (CH, NH) or 1.5 (CH3) times Ueq of the parent atom.Idealised Me refined as rotating groups.

Structure description top

During the last few decades, there has been a considerable interest in the chemistry of Schiff base compounds (Dubey & Vaid, 1991; Yadav et al., 1994). Schiff bases, containing different donor atoms, also find use in analytical applications and metal coordination (Galic et al., 2001; Wyrzykiewicz & Pruka, 1998; Reddy & Lirgappa, 1994). Since many compounds containing sulfur and nitrogen atoms are antihypertensive (Wei et al., 1981,1982), analgesic (Thieme et al., 1973a,b), antiinflammatory (Dornow et al., 1964), sedative (Barrera et al.,1985), or fungicidal (Malik et al., 2011), synthesis of the corresponding heterocyclic compounds could be of interest from the viewpoint of chemical reactivity and biological activity. The crystal structures of some of the related Schiff bases viz: 3-ethyl-4-[(E)-(4-fluorobenzylidene)amino]-1H-1,2,4-triazole-5(4H)-thione (Jeyaseelan et al., 2012); 4-[(E)-(4-fluorobenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione (Devarajegowda et al., 2012); 3-[2-(2,6-dichloro-anilino)benzyl]-4-[(4-methoxybenzylidene)amino]-1H-1,2,4-triazole-5(4H)-thione (Vinduvahini et al., 2011); 3-(adamantan-1-yl)-1-[(4-ethylpiperazin-1-yl)methyl]-4-[(E)-(4-hydroxy-benzylidene)amino]-1H-1,2,4-triazole-5(4H)-thione (Almutairi et al., 2012); 4-{(2E)-2-[1-(4-Methoxyphenyl)ethylidene]hydrazinyl}-8-(trifluoromethyl)quinoline (Kubicki et al., 2012); (E)-N'-(4-Methoxybenzylidene)-2-m-tolylacetohydrazide (Praveen et al., 2012); (1Z)-1-[(2E)-3-(4-bromophenyl)-1-(4-fluorophenyl)prop-2-en-1-ylidene]-2-(2,4-dinitrophenyl)hydrazine (Kant et al., 2012); (E)-3-(2-ethoxyphenyl)-4-(2-fluorobenzylideneamino)-1H-1,2,4-triazole-5(4H)-thione (Ding et al.,2009) have been reported. Crystal structures of some of the Schiff bases were also reported from our group (Sarojini et al., 2007a,b). In continuation of our work on the synthesis of acetamides derivatives, we report herein the crystal structure of the title compound, C10H9ClN4S, (I).

In the title compound, (I), C10H9ClN4S, the dihedral angle between the mean planes of the phenyl ring and the1H-1,2,4-triazole-5(4H)-thione ring is 25.3 (9)° (Fig.1). The 1,2,4-triazole-5(4H)-thione ring is essentially planar with a maximum deviation of 0.010Å and -0.010Å for the N2 nitrogen and C9 carbon atom, respectively. Bond lengths and bond angles are in normal ranges (Allen et al., 1987).In the crystal, weak N4—H4···S1 intermolecular interactions forming R22(8) graph set motifs link the molecules into dimers diagonally in the ac plane (Fig. 2). In addition, weak Cg–Cg π–π intermolecular interactions are observed which may contribute to crystal packing (Cg1–Cg1 = 3.3463 (14)Å; -x, 1-y, -z; Cg2–Cg2 = 3.6127 (13)Å; 1-x, 2-y, 1-z; Cg1 = N2/C81/N4/N3/C9; Cg2 = C2–C7) (Grimme, 1987). No classical hydrogen bonds were observed.

For the chemistry of Schiff base compounds, see: Dubey & Vaid (1991); Yadav et al. (1994). For the use of Schiff bases containing different donor atoms in analytical applications and metal coordination, see: Galic et al. (2001); Wyrzykiewicz & Prukah (1998); Reddy & Lirgappa (1994). Since many compounds containing sulfur and nitrogen atoms are antihypertensive (Wei et al., 1981,1982), analgesic (Thieme et al., 1973a,b), antiinflammatory (Dornow et al., 1964), sedative (Barrera et al.,1985), or fungicidal (Malik et al., 2011), synthesis of the corresponding heterocyclic compounds could be of interest from the viewpoint of chemical reactivity and biological activity. For the crystal structures of related Schiff bases, see: Jeyaseelan et al. (2012); Devarajegowda et al. (2012); Vinduvahini et al. (2011); Almutairi et al. (2012); Kubicki et al. (2012); Praveen et al. (2012); Kant et al. (2012); Ding et al. (2009). For the crystal structures of Schiff bases reported by our group, see: Sarojini et al. (2007a,b). For standard bond lengths, see: Allen et al. (1987). For π–π stacking, see: Grimme (2008). AUTHOR: please remember to sub-dvide this section in future

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. ORTEP drawing of (I) (C10H9ClN4S) showing the labeling scheme with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Molecular packing for (I) viewed along the b axis. Dashed lines indicate weak N4—H4···S1 intermolecular interactions forming R22(8) graph set motifs linking the molecules into dimers diagonally in the ac plane. H atoms not involved in hydrogen bonding have been removed for clarity.
[Figure 3] Fig. 3. Synthesis scheme for (I).
4-[(E)-(4-Chlorobenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione top
Crystal data top
C10H9ClN4SZ = 2
Mr = 252.72F(000) = 260
Triclinic, P1Dx = 1.471 Mg m−3
a = 7.0718 (8) ÅCu Kα radiation, λ = 1.54184 Å
b = 7.2901 (8) ÅCell parameters from 1400 reflections
c = 11.8434 (7) Åθ = 3.8–72.2°
α = 92.778 (7)°µ = 4.49 mm−1
β = 94.986 (7)°T = 173 K
γ = 109.752 (10)°Irregular, colourless
V = 570.50 (10) Å30.42 × 0.08 × 0.06 mm
Data collection top
Agilent Gemini EOS
diffractometer		2195 independent reflections
Radiation source: Enhance (Cu) X-ray Source1860 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1Rint = 0.030
ω scansθmax = 72.3°, θmin = 3.8°
Absorption correction: multi-scan
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)		h = −8→8
Tmin = 0.544, Tmax = 1.000k = −8→8
3413 measured reflectionsl = −10→14
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.120 w = 1/[σ2(Fo2) + (0.0694P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2195 reflectionsΔρmax = 0.34 e Å−3
146 parametersΔρmin = −0.39 e Å−3
0 restraints
Crystal data top
C10H9ClN4Sγ = 109.752 (10)°
Mr = 252.72V = 570.50 (10) Å3
Triclinic, P1Z = 2
a = 7.0718 (8) ÅCu Kα radiation
b = 7.2901 (8) ŵ = 4.49 mm−1
c = 11.8434 (7) ÅT = 173 K
α = 92.778 (7)°0.42 × 0.08 × 0.06 mm
β = 94.986 (7)°
Data collection top
Agilent Gemini EOS
diffractometer		2195 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)		1860 reflections with I > 2σ(I)
Tmin = 0.544, Tmax = 1.000Rint = 0.030
3413 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.120H-atom parameters constrained
S = 1.02Δρmax = 0.34 e Å−3
2195 reflectionsΔρmin = −0.39 e Å−3
146 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.50541 (9)0.96033 (9)0.77738 (5)0.03752 (19)
S1−0.33106 (9)0.64930 (9)0.16551 (5)0.03564 (19)
N10.0401 (3)0.4905 (3)0.27296 (16)0.0295 (4)
N2−0.0729 (3)0.4344 (3)0.16664 (15)0.0287 (4)
N3−0.1813 (3)0.2442 (3)0.00660 (17)0.0353 (4)
N4−0.2891 (3)0.3680 (3)0.02140 (16)0.0317 (4)
H4−0.38620.3696−0.02710.038*
C10.0775 (3)0.6667 (3)0.31206 (19)0.0311 (5)
H10.03640.75200.26840.037*
C20.1852 (3)0.7342 (3)0.42579 (19)0.0289 (5)
C30.2005 (3)0.9179 (3)0.4726 (2)0.0320 (5)
H30.14600.99570.43010.038*
C40.2955 (3)0.9876 (3)0.5816 (2)0.0318 (5)
H4A0.30261.10950.61310.038*
C50.3788 (3)0.8714 (3)0.64183 (19)0.0307 (5)
C60.3682 (3)0.6889 (3)0.5977 (2)0.0329 (5)
H60.42650.61360.64000.039*
C70.2703 (3)0.6195 (3)0.4903 (2)0.0333 (5)
H70.26060.49590.46050.040*
C8−0.2301 (3)0.4851 (3)0.11732 (19)0.0291 (5)
C9−0.0524 (3)0.2861 (3)0.0975 (2)0.0322 (5)
C100.1023 (4)0.1949 (4)0.1262 (2)0.0431 (6)
H10A0.05900.10600.18370.065*
H10B0.22840.29490.15410.065*
H10C0.11950.12480.05940.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0398 (3)0.0455 (3)0.0282 (3)0.0191 (3)−0.0056 (2)−0.0031 (2)
S10.0364 (3)0.0421 (3)0.0329 (3)0.0242 (3)−0.0099 (2)−0.0080 (2)
N10.0255 (9)0.0372 (10)0.0263 (10)0.0134 (7)−0.0047 (7)0.0010 (7)
N20.0270 (9)0.0321 (9)0.0274 (10)0.0132 (7)−0.0046 (7)−0.0007 (7)
N30.0369 (10)0.0397 (10)0.0325 (11)0.0212 (8)−0.0063 (8)−0.0057 (8)
N40.0318 (10)0.0394 (10)0.0272 (10)0.0198 (8)−0.0066 (8)−0.0030 (8)
C10.0260 (10)0.0337 (11)0.0334 (12)0.0113 (8)−0.0029 (9)0.0044 (9)
C20.0208 (10)0.0344 (11)0.0296 (12)0.0087 (8)−0.0020 (8)0.0007 (9)
C30.0264 (10)0.0364 (12)0.0355 (12)0.0153 (9)−0.0017 (9)0.0010 (9)
C40.0282 (10)0.0353 (11)0.0339 (12)0.0152 (9)−0.0004 (9)−0.0041 (9)
C50.0248 (10)0.0406 (12)0.0260 (11)0.0112 (9)0.0007 (8)−0.0001 (9)
C60.0331 (11)0.0350 (11)0.0328 (12)0.0155 (9)−0.0015 (9)0.0064 (9)
C70.0346 (11)0.0307 (11)0.0342 (12)0.0122 (9)−0.0009 (10)−0.0001 (9)
C80.0284 (10)0.0330 (11)0.0269 (11)0.0138 (8)−0.0036 (8)0.0003 (9)
C90.0314 (11)0.0350 (11)0.0311 (12)0.0148 (9)−0.0021 (9)−0.0024 (9)
C100.0420 (14)0.0460 (14)0.0481 (16)0.0288 (12)−0.0086 (12)−0.0060 (12)
Geometric parameters (Å, º) top
Cl1—C51.748 (2)C2—C71.402 (3)
S1—C81.689 (2)C3—H30.9300
N1—N21.395 (2)C3—C41.390 (3)
N1—C11.275 (3)C4—H4A0.9300
N2—C81.378 (3)C4—C51.377 (3)
N2—C91.379 (3)C5—C61.381 (3)
N3—N41.378 (2)C6—H60.9300
N3—C91.301 (3)C6—C71.379 (3)
N4—H40.8600C7—H70.9300
N4—C81.333 (3)C9—C101.484 (3)
C1—H10.9300C10—H10A0.9600
C1—C21.463 (3)C10—H10B0.9600
C2—C31.390 (3)C10—H10C0.9600
C1—N1—N2116.28 (19)C4—C5—C6122.1 (2)
C8—N2—N1131.27 (18)C6—C5—Cl1119.20 (18)
C8—N2—C9108.25 (18)C5—C6—H6120.4
C9—N2—N1119.99 (18)C7—C6—C5119.2 (2)
C9—N3—N4103.61 (18)C7—C6—H6120.4
N3—N4—H4122.9C2—C7—H7119.8
C8—N4—N3114.29 (18)C6—C7—C2120.4 (2)
C8—N4—H4122.9C6—C7—H7119.8
N1—C1—H1120.1N2—C8—S1129.63 (17)
N1—C1—C2119.8 (2)N4—C8—S1127.48 (17)
C2—C1—H1120.1N4—C8—N2102.87 (18)
C3—C2—C1118.6 (2)N2—C9—C10122.4 (2)
C3—C2—C7118.7 (2)N3—C9—N2110.94 (19)
C7—C2—C1122.6 (2)N3—C9—C10126.6 (2)
C2—C3—H3119.3C9—C10—H10A109.5
C4—C3—C2121.3 (2)C9—C10—H10B109.5
C4—C3—H3119.3C9—C10—H10C109.5
C3—C4—H4A120.9H10A—C10—H10B109.5
C5—C4—C3118.2 (2)H10A—C10—H10C109.5
C5—C4—H4A120.9H10B—C10—H10C109.5
C4—C5—Cl1118.70 (18)
Cl1—C5—C6—C7−179.28 (17)C1—C2—C3—C4178.0 (2)
N1—N2—C8—S15.3 (4)C1—C2—C7—C6−179.2 (2)
N1—N2—C8—N4−173.2 (2)C2—C3—C4—C51.4 (3)
N1—N2—C9—N3174.80 (19)C3—C2—C7—C6−0.4 (3)
N1—N2—C9—C10−6.5 (3)C3—C4—C5—Cl1178.09 (17)
N1—C1—C2—C3−171.5 (2)C3—C4—C5—C6−0.8 (3)
N1—C1—C2—C77.2 (3)C4—C5—C6—C7−0.4 (4)
N2—N1—C1—C2176.53 (18)C5—C6—C7—C21.0 (3)
N3—N4—C8—S1−177.92 (17)C7—C2—C3—C4−0.8 (3)
N3—N4—C8—N20.6 (3)C8—N2—C9—N32.0 (3)
N4—N3—C9—N2−1.5 (3)C8—N2—C9—C10−179.3 (2)
N4—N3—C9—C10179.8 (2)C9—N2—C8—S1177.00 (18)
C1—N1—N2—C8−35.9 (3)C9—N2—C8—N4−1.5 (2)
C1—N1—N2—C9153.2 (2)C9—N3—N4—C80.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···S1i0.862.433.2926 (19)176
C1—H1···S10.932.623.199 (2)121
Symmetry code: (i) −x−1, −y+1, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···S1i0.862.433.2926 (19)176.2
C1—H1···S10.932.623.199 (2)121.2
Symmetry code: (i) −x−1, −y+1, −z.
 

Acknowledgements

BKS and PSM gratefully acknowledge the Department of Chemistry, P. A. College of Engineering, for providing research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

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ISSN: 2056-9890
Volume 70| Part 1| January 2014| Pages o57-o58
https://doi.org/10.1107/S1600536813033527
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