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

Sarojini, B.K.; Manjula, P.S.; Kaur, M.; Anderson, B.J.; Jasinski, J.P.

doi:10.1107/S1600536813033527

organic compounds

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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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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. Anderson ^d and Jerry P. Jasinski ^d ^*

^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 ); 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 ). Many compounds containing S and N 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 ). 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 ).

Experimental

Crystal data

C₁₀H₉ClN₄S
M_r = 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 ) T_min = 0.544, T_max = 1.000
3413 measured reflections
2195 independent reflections
1860 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.120
S = 1.02
2195 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −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); cell refinement: CrysAlis PRO; 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.

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).

Structure description 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

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

	Fig. 1. ORTEP drawing of (I) (C₁₀H₉ClN₄S) showing the labeling scheme with 50% probability displacement ellipsoids.
	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.
	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

C₁₀H₉ClN₄S	Z = 2
M_r = 252.72	F(000) = 260
Triclinic, P1	D_x = 1.471 Mg m⁻³
a = 7.0718 (8) Å	Cu Kα radiation, λ = 1.54184 Å
b = 7.2901 (8) Å	Cell parameters from 1400 reflections
c = 11.8434 (7) Å	θ = 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) Å³	0.42 × 0.08 × 0.06 mm

Data collection top

Agilent Gemini EOS diffractometer	2195 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1860 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm^-1	R_int = 0.030
ω scans	θ_max = 72.3°, θ_min = 3.8°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −8→8
T_min = 0.544, T_max = 1.000	k = −8→8
3413 measured reflections	l = −10→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0694P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2195 reflections	Δρ_max = 0.34 e Å⁻³
146 parameters	Δρ_min = −0.39 e Å⁻³
0 restraints

Crystal data top

C₁₀H₉ClN₄S	γ = 109.752 (10)°
M_r = 252.72	V = 570.50 (10) Å³
Triclinic, P1	Z = 2
a = 7.0718 (8) Å	Cu Kα radiation
b = 7.2901 (8) Å	µ = 4.49 mm⁻¹
c = 11.8434 (7) Å	T = 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)
T_min = 0.544, T_max = 1.000	R_int = 0.030
3413 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.02	Δρ_max = 0.34 e Å⁻³
2195 reflections	Δρ_min = −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

	x	y	z	U_iso*/U_eq
Cl1	0.50541 (9)	0.96033 (9)	0.77738 (5)	0.03752 (19)
S1	−0.33106 (9)	0.64930 (9)	0.16551 (5)	0.03564 (19)
N1	0.0401 (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	−0.3862	0.3696	−0.0271	0.038*
C1	0.0775 (3)	0.6667 (3)	0.31206 (19)	0.0311 (5)
H1	0.0364	0.7520	0.2684	0.037*
C2	0.1852 (3)	0.7342 (3)	0.42579 (19)	0.0289 (5)
C3	0.2005 (3)	0.9179 (3)	0.4726 (2)	0.0320 (5)
H3	0.1460	0.9957	0.4301	0.038*
C4	0.2955 (3)	0.9876 (3)	0.5816 (2)	0.0318 (5)
H4A	0.3026	1.1095	0.6131	0.038*
C5	0.3788 (3)	0.8714 (3)	0.64183 (19)	0.0307 (5)
C6	0.3682 (3)	0.6889 (3)	0.5977 (2)	0.0329 (5)
H6	0.4265	0.6136	0.6400	0.039*
C7	0.2703 (3)	0.6195 (3)	0.4903 (2)	0.0333 (5)
H7	0.2606	0.4959	0.4605	0.040*
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)
C10	0.1023 (4)	0.1949 (4)	0.1262 (2)	0.0431 (6)
H10A	0.0590	0.1060	0.1837	0.065*
H10B	0.2284	0.2949	0.1541	0.065*
H10C	0.1195	0.1248	0.0594	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0398 (3)	0.0455 (3)	0.0282 (3)	0.0191 (3)	−0.0056 (2)	−0.0031 (2)
S1	0.0364 (3)	0.0421 (3)	0.0329 (3)	0.0242 (3)	−0.0099 (2)	−0.0080 (2)
N1	0.0255 (9)	0.0372 (10)	0.0263 (10)	0.0134 (7)	−0.0047 (7)	0.0010 (7)
N2	0.0270 (9)	0.0321 (9)	0.0274 (10)	0.0132 (7)	−0.0046 (7)	−0.0007 (7)
N3	0.0369 (10)	0.0397 (10)	0.0325 (11)	0.0212 (8)	−0.0063 (8)	−0.0057 (8)
N4	0.0318 (10)	0.0394 (10)	0.0272 (10)	0.0198 (8)	−0.0066 (8)	−0.0030 (8)
C1	0.0260 (10)	0.0337 (11)	0.0334 (12)	0.0113 (8)	−0.0029 (9)	0.0044 (9)
C2	0.0208 (10)	0.0344 (11)	0.0296 (12)	0.0087 (8)	−0.0020 (8)	0.0007 (9)
C3	0.0264 (10)	0.0364 (12)	0.0355 (12)	0.0153 (9)	−0.0017 (9)	0.0010 (9)
C4	0.0282 (10)	0.0353 (11)	0.0339 (12)	0.0152 (9)	−0.0004 (9)	−0.0041 (9)
C5	0.0248 (10)	0.0406 (12)	0.0260 (11)	0.0112 (9)	0.0007 (8)	−0.0001 (9)
C6	0.0331 (11)	0.0350 (11)	0.0328 (12)	0.0155 (9)	−0.0015 (9)	0.0064 (9)
C7	0.0346 (11)	0.0307 (11)	0.0342 (12)	0.0122 (9)	−0.0009 (10)	−0.0001 (9)
C8	0.0284 (10)	0.0330 (11)	0.0269 (11)	0.0138 (8)	−0.0036 (8)	0.0003 (9)
C9	0.0314 (11)	0.0350 (11)	0.0311 (12)	0.0148 (9)	−0.0021 (9)	−0.0024 (9)
C10	0.0420 (14)	0.0460 (14)	0.0481 (16)	0.0288 (12)	−0.0086 (12)	−0.0060 (12)

Geometric parameters (Å, º) top

Cl1—C5	1.748 (2)	C2—C7	1.402 (3)
S1—C8	1.689 (2)	C3—H3	0.9300
N1—N2	1.395 (2)	C3—C4	1.390 (3)
N1—C1	1.275 (3)	C4—H4A	0.9300
N2—C8	1.378 (3)	C4—C5	1.377 (3)
N2—C9	1.379 (3)	C5—C6	1.381 (3)
N3—N4	1.378 (2)	C6—H6	0.9300
N3—C9	1.301 (3)	C6—C7	1.379 (3)
N4—H4	0.8600	C7—H7	0.9300
N4—C8	1.333 (3)	C9—C10	1.484 (3)
C1—H1	0.9300	C10—H10A	0.9600
C1—C2	1.463 (3)	C10—H10B	0.9600
C2—C3	1.390 (3)	C10—H10C	0.9600

C1—N1—N2	116.28 (19)	C4—C5—C6	122.1 (2)
C8—N2—N1	131.27 (18)	C6—C5—Cl1	119.20 (18)
C8—N2—C9	108.25 (18)	C5—C6—H6	120.4
C9—N2—N1	119.99 (18)	C7—C6—C5	119.2 (2)
C9—N3—N4	103.61 (18)	C7—C6—H6	120.4
N3—N4—H4	122.9	C2—C7—H7	119.8
C8—N4—N3	114.29 (18)	C6—C7—C2	120.4 (2)
C8—N4—H4	122.9	C6—C7—H7	119.8
N1—C1—H1	120.1	N2—C8—S1	129.63 (17)
N1—C1—C2	119.8 (2)	N4—C8—S1	127.48 (17)
C2—C1—H1	120.1	N4—C8—N2	102.87 (18)
C3—C2—C1	118.6 (2)	N2—C9—C10	122.4 (2)
C3—C2—C7	118.7 (2)	N3—C9—N2	110.94 (19)
C7—C2—C1	122.6 (2)	N3—C9—C10	126.6 (2)
C2—C3—H3	119.3	C9—C10—H10A	109.5
C4—C3—C2	121.3 (2)	C9—C10—H10B	109.5
C4—C3—H3	119.3	C9—C10—H10C	109.5
C3—C4—H4A	120.9	H10A—C10—H10B	109.5
C5—C4—C3	118.2 (2)	H10A—C10—H10C	109.5
C5—C4—H4A	120.9	H10B—C10—H10C	109.5
C4—C5—Cl1	118.70 (18)

Cl1—C5—C6—C7	−179.28 (17)	C1—C2—C3—C4	178.0 (2)
N1—N2—C8—S1	5.3 (4)	C1—C2—C7—C6	−179.2 (2)
N1—N2—C8—N4	−173.2 (2)	C2—C3—C4—C5	1.4 (3)
N1—N2—C9—N3	174.80 (19)	C3—C2—C7—C6	−0.4 (3)
N1—N2—C9—C10	−6.5 (3)	C3—C4—C5—Cl1	178.09 (17)
N1—C1—C2—C3	−171.5 (2)	C3—C4—C5—C6	−0.8 (3)
N1—C1—C2—C7	7.2 (3)	C4—C5—C6—C7	−0.4 (4)
N2—N1—C1—C2	176.53 (18)	C5—C6—C7—C2	1.0 (3)
N3—N4—C8—S1	−177.92 (17)	C7—C2—C3—C4	−0.8 (3)
N3—N4—C8—N2	0.6 (3)	C8—N2—C9—N3	2.0 (3)
N4—N3—C9—N2	−1.5 (3)	C8—N2—C9—C10	−179.3 (2)
N4—N3—C9—C10	179.8 (2)	C9—N2—C8—S1	177.00 (18)
C1—N1—N2—C8	−35.9 (3)	C9—N2—C8—N4	−1.5 (2)
C1—N1—N2—C9	153.2 (2)	C9—N3—N4—C8	0.5 (3)

Hydrogen-bond geometry (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···S1ⁱ	0.86	2.43	3.2926 (19)	176.2
C1—H1···S1	0.93	2.62	3.199 (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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