4-Amino-3-(4-chloro­phen­yl)-1H-1,2,4-triazole-5(4H)-thione

Natarajan, S.; Mathews, R.

doi:10.1107/S1600536812000785

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o443

doi:10.1107/S1600536812000785

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4-Amino-3-(4-chlorophenyl)-1H-1,2,4-triazole-5(4H)-thione

Sampath Natarajan ^a ^* and Rita Mathews ^a

^aDepartment of Advanced Technology Fusion, Konkuk University, 1 Hwayang-dong, Gwangjin-gu, Seoul 143 701, Republic of Korea
^*Correspondence e-mail: sampath@konkuk.ac.kr;sams76@gmail.com

(Received 28 December 2011; accepted 8 January 2012; online 18 January 2012)

In the title compound, C₈H₇ClN₄S, the benzene ring is statistically disordered over two conformations rotated about the Cl—C⋯C—C axis, which subtend dihedral angles of 24.7 (3) and 9.9 (2) ° with respect to the triazole ring. An intramolecular C—H⋯N close contact occurs. In the crystal, N—H⋯N and N—H⋯S hydrogen bonds link the molecules into (001) sheets: R₂²(8) and R₂²(10) graph-set motifs result. Weak C—H⋯N hydrogen bonds and aromatic π–π stacking interactions [shortest centroid–centroid separation = 3.681 (7) Å] complete the structure.

Related literature

For a related structure and background references, see: Natarajan & Mathews (2011 ). For a related structure, see: Ambalavanan et al. (2003 ).

Experimental

Crystal data

C₈H₇ClN₄S
M_r = 226.69
Triclinic, $[P \overline 1]$
a = 6.0765 (9) Å
b = 8.0268 (7) Å
c = 10.9873 (16) Å
α = 72.501 (10)°
β = 87.597 (10)°
γ = 67.88 (2)°
V = 471.94 (12) Å³
Z = 2
Cu Kα radiation
μ = 5.35 mm⁻¹
T = 293 K
0.24 × 0.18 × 0.12 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: part of the refinement model (ΔF) (SHELXA; Sheldrick, 2008) T_min = 0.146, T_max = 0.618
1912 measured reflections
1818 independent reflections
1670 reflections with I > 2σ(I)
R_int = 0.054
3 standard reflections every 60 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.080
wR(F²) = 0.236
S = 1.09
1818 reflections
173 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4B—H4B⋯N4	0.93	2.32	2.98	128
N3—H3⋯S1ⁱ	0.86	2.55	3.332 (3)	152
C5B—H5B⋯N4ⁱⁱ	0.93	2.72	3.582 (8)	155
C8A—H8A⋯N4ⁱⁱⁱ	0.93	2.53	3.416 (9)	158
C7B—H7B⋯N2^iv	0.93	2.64	3.541 (10)	162
N4—H4C⋯S1^v	0.91 (6)	2.70 (6)	3.552 (4)	155 (5)
N4—H4D⋯N2^vi	0.96 (7)	2.42 (7)	3.349 (5)	164 (5)
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1, -y+1, -z; (iii) x+1, y, z; (iv) -x+2, -y+2, -z; (v) -x+1, -y+1, -z+1; (vi) x-1, y, z.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms, 1996 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812000785/hb6583sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812000785/hb6583Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812000785/hb6583Isup3.cml

checkCIF report

Comment top

As part of our onging studies of 1,2,4-triazole derivatives (Natarajan & Mathews, 2011), we now describe the title compound.

The title molecule (Fig.1) contains the rings 1,2,4-triazole and 4-chlorophenyl. All the bond lengths and bond angles are well agreed with previously reported structure (Ambalavanan et al., 2003; Natarajan and Mathews, 2011). The phenyl ring substituted on the atom C2 shows rotational disorder by the atoms of C4, C5, C7 & C8. The rotational disorder of phenyl ring results in two phenyl ring orientations A (C3/C4A/C5A/C6/C7A/C8A) and B (C3/C4B/C5B/CB/C7B/C8B) with respect to 1,2,4-triazole ring. The dihedral angles of these phenyl rings with triazole moiety are 24.7 (3) and 9.9 (2)°, respectively for phenyl rings A and B.

The packing diagram of the title compound viewed down a axis is shown in Fig. 2. The crystal structure is stabilized by the intra and intermolecular hydrogen bonds namely N—H···N, C—H···N and N—H···S. One of them (N—H···S) is involved in self-complementary interactions of triazole rings and forms R₂²(8) and R₂²(10) types graph set motifs. The motif, R₂²(10) is formed by the dimer interactions between the symmetry related 1,2,4-triazole-3-thione moieties and it is connected by the motif R₂²(8) along the b axis in the unit cell packing. In addition, three π···π weak interactions {Cg1···Cg1= 3.681 (7) Å, Cg1···Cg2= 3.691 (7)Å & Cg2···Cg2 = 3.701 (7)Å (2 - x, 1 - y, -z); Cg is the centroid of the rings; Cg1= C3/C4A/C5A/C6/C7A/C8A and Cg2= C3/C4B/C5B/C6/C7B/C8B} are also helping to consolidate the molecules in crystal packing. The detailed geometry of the non-bonded interactions is presented in Table 1.

Related literature top

For a related structure and background references, see: Natarajan & Mathews (2011). For a related structure, see: Ambalavanan et al. (2003).

Experimental top

A mixture of β-4-chlorophenyldithiocarbazinate potassium salt (0.1 mol) and hydrazine hydrate (0.25 mol) was heated on an oil-bath at 150° C for 5 h (until evolution of H2S gas in the reaction). The reaction mixture was then cooled and poured into the cold water and then acidified with conc. HCl. The filtered product was washed extensively with cold water and recrystallized using ethanol to yield yellow needles.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. ORTEP diagram of the title molecule with displacement ellipsoid drawn at 30% probability level.
	Fig. 2. A unit cell packing of the crystal structure of the title compound viewed down a axis. Dashed lines are indicating the hydrogen bonds between the molecules.

4-Amino-3-(4-chlorophenyl)-1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₈H₇ClN₄S	Z = 2
M_r = 226.69	F(000) = 232
Triclinic, P1	D_x = 1.595 Mg m⁻³
a = 6.0765 (9) Å	Cu Kα radiation, λ = 1.54184 Å
b = 8.0268 (7) Å	Cell parameters from 25 reflections
c = 10.9873 (16) Å	θ = 1–60°
α = 72.501 (10)°	µ = 5.35 mm⁻¹
β = 87.597 (10)°	T = 293 K
γ = 67.88 (2)°	Needle, yellow
V = 471.94 (12) Å³	0.24 × 0.18 × 0.12 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1670 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.054
Graphite monochromator	θ_max = 72.5°, θ_min = 4.2°
ω scans	h = −6→7
Absorption correction: part of the refinement model (ΔF) (SHELXA; Sheldrick, 2008)	k = −9→9
T_min = 0.146, T_max = 0.618	l = −9→13
1912 measured reflections	3 standard reflections every 60 min
1818 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.080	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.236	w = 1/[σ²(F_o²) + (0.1913P)² + 0.1469P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
1818 reflections	Δρ_max = 0.62 e Å⁻³
173 parameters	Δρ_min = −0.51 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.031 (8)

Crystal data top

C₈H₇ClN₄S	γ = 67.88 (2)°
M_r = 226.69	V = 471.94 (12) Å³
Triclinic, P1	Z = 2
a = 6.0765 (9) Å	Cu Kα radiation
b = 8.0268 (7) Å	µ = 5.35 mm⁻¹
c = 10.9873 (16) Å	T = 293 K
α = 72.501 (10)°	0.24 × 0.18 × 0.12 mm
β = 87.597 (10)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1670 reflections with I > 2σ(I)
Absorption correction: part of the refinement model (ΔF) (SHELXA; Sheldrick, 2008)	R_int = 0.054
T_min = 0.146, T_max = 0.618	3 standard reflections every 60 min
1912 measured reflections	intensity decay: none
1818 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.080	0 restraints
wR(F²) = 0.236	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.62 e Å⁻³
1818 reflections	Δρ_min = −0.51 e Å⁻³
173 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.91511 (17)	0.68117 (13)	−0.30339 (8)	0.0585 (5)
S1	0.31850 (16)	0.79307 (13)	0.50686 (8)	0.0534 (5)
N1	0.5022 (5)	0.7466 (4)	0.2844 (2)	0.0404 (7)
N2	0.7683 (6)	0.8756 (5)	0.2550 (3)	0.0569 (9)
N3	0.6640 (6)	0.8820 (5)	0.3677 (3)	0.0596 (9)
H3	0.7032	0.9292	0.4196	0.072*
N4	0.3603 (7)	0.6528 (5)	0.2662 (3)	0.0541 (8)
C1	0.4998 (6)	0.8091 (5)	0.3885 (3)	0.0453 (8)
C2	0.6627 (5)	0.7938 (4)	0.2044 (3)	0.0407 (7)
C3	0.7171 (5)	0.7637 (4)	0.0791 (3)	0.0395 (7)
C4A	0.5509 (19)	0.7474 (19)	0.0004 (9)	0.0404 (19)	0.50 (2)
H4A	0.4041	0.7494	0.0291	0.048*	0.50 (2)
C5A	0.6105 (19)	0.7284 (18)	−0.1214 (9)	0.048 (2)	0.50 (2)
H5A	0.5020	0.7227	−0.1757	0.057*	0.50 (2)
C4B	0.631 (2)	0.661 (2)	0.0331 (10)	0.041 (2)	0.50 (2)
H4B	0.5303	0.6072	0.0799	0.050*	0.50 (2)
C5B	0.694 (2)	0.636 (2)	−0.0856 (10)	0.047 (3)	0.50 (2)
H5B	0.6401	0.5606	−0.1156	0.056*	0.50 (2)
C6	0.8321 (6)	0.7185 (4)	−0.1578 (3)	0.0437 (8)
C7A	0.9891 (19)	0.737 (2)	−0.0863 (8)	0.047 (2)	0.50 (2)
H7A	1.1338	0.7384	−0.1168	0.057*	0.50 (2)
C8A	0.9324 (19)	0.755 (2)	0.0335 (8)	0.047 (2)	0.50 (2)
H8A	1.0451	0.7608	0.0850	0.057*	0.50 (2)
C7B	0.9186 (19)	0.831 (2)	−0.1110 (9)	0.046 (2)	0.50 (2)
H7B	1.0154	0.8880	−0.1592	0.056*	0.50 (2)
C8B	0.8574 (18)	0.856 (2)	0.0063 (8)	0.041 (2)	0.50 (2)
H8B	0.9085	0.9321	0.0371	0.050*	0.50 (2)
H4C	0.394 (11)	0.538 (9)	0.327 (6)	0.095 (19)*
H4D	0.198 (12)	0.724 (9)	0.277 (6)	0.096 (18)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0650 (7)	0.0717 (7)	0.0365 (6)	−0.0151 (5)	0.0119 (4)	−0.0289 (4)
S1	0.0548 (7)	0.0735 (7)	0.0408 (6)	−0.0209 (5)	0.0126 (4)	−0.0356 (5)
N1	0.0407 (14)	0.0474 (13)	0.0337 (13)	−0.0068 (10)	0.0014 (10)	−0.0258 (11)
N2	0.0591 (18)	0.090 (2)	0.0414 (16)	−0.0351 (16)	0.0129 (13)	−0.0406 (15)
N3	0.0627 (19)	0.098 (2)	0.0446 (16)	−0.0400 (17)	0.0151 (14)	−0.0490 (17)
N4	0.0587 (19)	0.073 (2)	0.0469 (17)	−0.0299 (15)	0.0138 (14)	−0.0360 (15)
C1	0.0451 (17)	0.0584 (17)	0.0326 (15)	−0.0081 (14)	0.0023 (12)	−0.0295 (13)
C2	0.0359 (15)	0.0500 (16)	0.0358 (15)	−0.0072 (12)	−0.0010 (11)	−0.0238 (12)
C3	0.0373 (15)	0.0435 (14)	0.0330 (14)	−0.0024 (11)	0.0001 (11)	−0.0213 (11)
C4A	0.033 (4)	0.049 (5)	0.035 (4)	−0.003 (4)	0.001 (3)	−0.023 (3)
C5A	0.050 (4)	0.051 (5)	0.033 (4)	−0.005 (4)	−0.003 (3)	−0.018 (4)
C4B	0.041 (4)	0.053 (6)	0.034 (4)	−0.012 (4)	0.008 (3)	−0.027 (4)
C5B	0.052 (5)	0.057 (6)	0.038 (4)	−0.016 (5)	0.004 (4)	−0.030 (4)
C6	0.0419 (16)	0.0468 (15)	0.0338 (16)	−0.0026 (13)	0.0028 (12)	−0.0188 (12)
C7A	0.047 (4)	0.054 (6)	0.040 (4)	−0.014 (4)	0.003 (3)	−0.020 (4)
C8A	0.045 (4)	0.055 (6)	0.045 (4)	−0.012 (4)	−0.004 (3)	−0.028 (4)
C7B	0.045 (4)	0.048 (6)	0.040 (4)	−0.011 (4)	0.010 (3)	−0.016 (4)
C8B	0.041 (4)	0.048 (6)	0.042 (4)	−0.012 (4)	0.006 (3)	−0.030 (4)

Geometric parameters (Å, º) top

Cl1—C6	1.735 (3)	C4A—C5A	1.410 (9)
S1—C1	1.675 (3)	C4A—H4A	0.9300
N1—C2	1.368 (4)	C5A—C6	1.368 (9)
N1—C1	1.378 (4)	C5A—H5A	0.9300
N1—N4	1.394 (4)	C4B—C5B	1.395 (9)
N2—C2	1.311 (4)	C4B—H4B	0.9300
N2—N3	1.373 (4)	C5B—C6	1.346 (9)
N3—C1	1.315 (5)	C5B—H5B	0.9300
N3—H3	0.8572	C6—C7A	1.339 (9)
N4—H4C	0.91 (6)	C6—C7B	1.421 (10)
N4—H4D	0.96 (7)	C7A—C8A	1.381 (10)
C2—C3	1.471 (4)	C7A—H7A	0.9300
C3—C4B	1.344 (8)	C8A—H8A	0.9300
C3—C8A	1.365 (9)	C7B—C8B	1.377 (10)
C3—C8B	1.405 (9)	C7B—H7B	0.9300
C3—C4A	1.423 (8)	C8B—H8B	0.9300

C2—N1—C1	108.7 (3)	C6—C5A—H5A	120.8
C2—N1—N4	127.1 (3)	C4A—C5A—H5A	120.8
C1—N1—N4	124.3 (3)	C3—C4B—C5B	119.3 (7)
C2—N2—N3	104.2 (3)	C3—C4B—H4B	120.4
C1—N3—N2	114.0 (3)	C5B—C4B—H4B	120.4
C1—N3—H3	123.3	C6—C5B—C4B	121.7 (6)
N2—N3—H3	122.7	C6—C5B—H5B	119.1
N1—N4—H4C	113 (4)	C4B—C5B—H5B	119.1
N1—N4—H4D	109 (4)	C7A—C6—C5B	112.0 (5)
H4C—N4—H4D	104 (5)	C7A—C6—C5A	123.0 (5)
N3—C1—N1	103.3 (3)	C5B—C6—C5A	30.8 (4)
N3—C1—S1	131.5 (3)	C7A—C6—C7B	28.6 (3)
N1—C1—S1	125.2 (3)	C5B—C6—C7B	119.2 (5)
N2—C2—N1	109.8 (3)	C5A—C6—C7B	113.4 (5)
N2—C2—C3	122.3 (3)	C7A—C6—Cl1	118.0 (4)
N1—C2—C3	127.9 (3)	C5B—C6—Cl1	121.1 (4)
C4B—C3—C8A	110.6 (5)	C5A—C6—Cl1	119.0 (4)
C4B—C3—C8B	121.1 (5)	C7B—C6—Cl1	119.7 (4)
C8A—C3—C8B	30.7 (3)	C6—C7A—C8A	118.8 (7)
C4B—C3—C4A	28.1 (3)	C6—C7A—H7A	120.6
C8A—C3—C4A	117.7 (5)	C8A—C7A—H7A	120.6
C8B—C3—C4A	111.9 (5)	C3—C8A—C7A	122.4 (6)
C4B—C3—C2	122.7 (4)	C3—C8A—H8A	118.8
C8A—C3—C2	119.7 (4)	C7A—C8A—H8A	118.8
C8B—C3—C2	116.1 (4)	C8B—C7B—C6	119.3 (7)
C4A—C3—C2	122.6 (4)	C8B—C7B—H7B	120.3
C5A—C4A—C3	119.5 (6)	C6—C7B—H7B	120.3
C5A—C4A—H4A	120.2	C7B—C8B—C3	119.3 (6)
C3—C4A—H4A	120.2	C7B—C8B—H8B	120.4
C6—C5A—C4A	118.3 (6)	C3—C8B—H8B	120.4

C2—N2—N3—C1	−0.2 (5)	C2—C3—C4B—C5B	−178.8 (6)
N2—N3—C1—N1	1.7 (4)	C3—C4B—C5B—C6	−2.7 (14)
N2—N3—C1—S1	−177.0 (3)	C4B—C5B—C6—C7A	31.8 (11)
C2—N1—C1—N3	−2.5 (3)	C4B—C5B—C6—C5A	−86.1 (12)
N4—N1—C1—N3	178.0 (3)	C4B—C5B—C6—C7B	1.1 (11)
C2—N1—C1—S1	176.3 (2)	C4B—C5B—C6—Cl1	178.4 (7)
N4—N1—C1—S1	−3.2 (4)	C4A—C5A—C6—C7A	−4.1 (11)
N3—N2—C2—N1	−1.4 (4)	C4A—C5A—C6—C5B	73.4 (10)
N3—N2—C2—C3	178.1 (3)	C4A—C5A—C6—C7B	−34.8 (9)
C1—N1—C2—N2	2.5 (4)	C4A—C5A—C6—Cl1	176.3 (5)
N4—N1—C2—N2	−178.0 (3)	C5B—C6—C7A—C8A	−28.2 (10)
C1—N1—C2—C3	−176.9 (3)	C5A—C6—C7A—C8A	4.5 (11)
N4—N1—C2—C3	2.5 (5)	C7B—C6—C7A—C8A	82.8 (12)
N2—C2—C3—C4B	172.1 (9)	Cl1—C6—C7A—C8A	−175.9 (6)
N1—C2—C3—C4B	−8.5 (9)	C4B—C3—C8A—C7A	32.1 (10)
N2—C2—C3—C8A	24.1 (9)	C8B—C3—C8A—C7A	−84.4 (11)
N1—C2—C3—C8A	−156.5 (8)	C4A—C3—C8A—C7A	2.2 (11)
N2—C2—C3—C8B	−10.5 (7)	C2—C3—C8A—C7A	−176.4 (7)
N1—C2—C3—C8B	168.9 (7)	C6—C7A—C8A—C3	−3.5 (13)
N2—C2—C3—C4A	−154.4 (7)	C7A—C6—C7B—C8B	−83.4 (12)
N1—C2—C3—C4A	25.0 (8)	C5B—C6—C7B—C8B	−0.8 (10)
C4B—C3—C4A—C5A	−83.7 (11)	C5A—C6—C7B—C8B	33.1 (9)
C8A—C3—C4A—C5A	−1.8 (10)	Cl1—C6—C7B—C8B	−178.1 (5)
C8B—C3—C4A—C5A	31.6 (9)	C6—C7B—C8B—C3	2.0 (11)
C2—C3—C4A—C5A	176.8 (6)	C4B—C3—C8B—C7B	−3.6 (10)
C3—C4A—C5A—C6	2.6 (11)	C8A—C3—C8B—C7B	74.2 (9)
C8A—C3—C4B—C5B	−28.3 (10)	C4A—C3—C8B—C7B	−33.5 (9)
C8B—C3—C4B—C5B	3.9 (11)	C2—C3—C8B—C7B	178.9 (6)
C4A—C3—C4B—C5B	82.2 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4B—H4B···N4	0.93	2.32	2.98	128
N3—H3···S1ⁱ	0.86	2.55	3.332 (3)	152
C5B—H5B···N4ⁱⁱ	0.93	2.72	3.582 (8)	155
C8A—H8A···N4ⁱⁱⁱ	0.93	2.53	3.416 (9)	158
C7B—H7B···N2^iv	0.93	2.64	3.541 (10)	162
N4—H4C···S1^v	0.91 (6)	2.70 (6)	3.552 (4)	155 (5)
N4—H4D···N2^vi	0.96 (7)	2.42 (7)	3.349 (5)	164 (5)

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z; (iii) x+1, y, z; (iv) −x+2, −y+2, −z; (v) −x+1, −y+1, −z+1; (vi) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₈H₇ClN₄S
M_r	226.69
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.0765 (9), 8.0268 (7), 10.9873 (16)
α, β, γ (°)	72.501 (10), 87.597 (10), 67.88 (2)
V (Å³)	471.94 (12)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	5.35
Crystal size (mm)	0.24 × 0.18 × 0.12

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	Part of the refinement model (ΔF) (SHELXA; Sheldrick, 2008)
T_min, T_max	0.146, 0.618
No. of measured, independent and observed [I > 2σ(I)] reflections	1912, 1818, 1670
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.236, 1.09
No. of reflections	1818
No. of parameters	173
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.51

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms, 1996), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4B—H4B···N4	0.93	2.32	2.98	128
N3—H3···S1ⁱ	0.86	2.55	3.332 (3)	152
C5B—H5B···N4ⁱⁱ	0.93	2.72	3.582 (8)	155
C8A—H8A···N4ⁱⁱⁱ	0.93	2.53	3.416 (9)	158
C7B—H7B···N2^iv	0.93	2.64	3.541 (10)	162
N4—H4C···S1^v	0.91 (6)	2.70 (6)	3.552 (4)	155 (5)
N4—H4D···N2^vi	0.96 (7)	2.42 (7)	3.349 (5)	164 (5)

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z; (iii) x+1, y, z; (iv) −x+2, −y+2, −z; (v) −x+1, −y+1, −z+1; (vi) x−1, y, z.

References

Ambalavanan, P., Palani, K., Ponnuswamy, M. N., Thirumuruhan, R. A., Yathirajan, S. H., Prabhuswamy, B., Raju, C. R., Nagaraja, P. & Mohana, K. N. (2003). Mol. Cryst. Liq. Cryst. 393, 67–73. Web of Science CSD CrossRef CAS Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Harms, K. (1996). XCAD4. University of Marburg, Germany. Google Scholar
Natarajan, S. & Mathews, R. (2011). Acta Cryst. E67, o2828. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 2| February 2012| Page o443

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