3-Methyl-6-trichloro-methyl-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

In the crystal structure of the title compound, C(5)H(3)Cl(3)N(4)S, two mol-ecules related by a centre of symmetry demonstrate extremely short inter-molecular S⋯N contacts of 2.783 (2) Å. The crystal packing also exhibits π-π inter-actions indicated by a short distance of 3.340 (1) Å between the centroids of the triazole rings of neighbouring mol-ecules.

Related literature

For the anti­microbial and anti-inflammatory activity of 1,2,4-triazole and 1,3,4-thio­diazole derivatives, see: Karabasanagouda et al. (2007 ▶); Mathew et al. (2007 ▶); For related structures, see: Du et al. (2008 ▶); Khan et al. (2009 ▶); Haugwitz et al. (1977 ▶).

Experimental

Crystal data

C5H3Cl3N4S

M = 257.52

Monoclinic,

a = 5.8732 (12) Å

b = 9.4164 (19) Å

c = 16.750 (3) Å

β = 91.82 (3)°

V = 925.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.17 mm−1

T = 153 K

0.30 × 0.20 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.721, T max = 0.892

9841 measured reflections

2196 independent reflections

1934 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.113

S = 1.24

2196 reflections

120 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.44 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012748/cv5070sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012748/cv5070Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C5H3Cl3N4S	F(000) = 512
Mr = 257.52	Dx = 1.847 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2918 reflections
a = 5.8732 (12) Å	θ = 3.3–27.9°
b = 9.4164 (19) Å	µ = 1.17 mm−1
c = 16.750 (3) Å	T = 153 K
β = 91.82 (3)°	Prism, colorless
V = 925.9 (3) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	2196 independent reflections
Radiation source: rotating anode	1934 reflections with I > 2σ(I)
multilayer	Rint = 0.038
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 2.4°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −10→12
Tmin = 0.721, Tmax = 0.892	l = −22→22
9841 measured reflections

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)] = 0.029	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0693P)2] where P = (Fo2 + 2Fc2)/3
S = 1.24	(Δ/σ)max < 0.001
2196 reflections	Δρmax = 0.49 e Å−3
120 parameters	Δρmin = −0.44 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: 0.071 (6)

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.

	x	y	z	Uiso*/Ueq
S1	0.13777 (9)	0.52705 (5)	0.13657 (3)	0.01622 (19)
Cl1	0.55694 (10)	0.67616 (5)	0.27560 (3)	0.0242 (2)
Cl2	0.15047 (9)	0.53079 (6)	0.32341 (3)	0.02410 (19)
Cl3	0.58496 (8)	0.38759 (5)	0.33267 (3)	0.01648 (18)
N1	0.3533 (3)	0.30847 (19)	−0.04370 (11)	0.0193 (4)
N2	0.1853 (3)	0.40411 (19)	−0.01768 (11)	0.0191 (4)
N3	0.4320 (3)	0.35972 (16)	0.08095 (10)	0.0134 (4)
N4	0.5132 (3)	0.37661 (17)	0.15796 (10)	0.0133 (4)
C1	0.7018 (4)	0.1903 (2)	0.01481 (13)	0.0223 (5)
H1A	0.7271	0.1594	−0.0401	0.033*
H1B	0.6776	0.1070	0.0486	0.033*
H1C	0.8353	0.2430	0.0352	0.033*
C2	0.4981 (3)	0.2833 (2)	0.01591 (12)	0.0158 (4)
C3	0.2385 (3)	0.4306 (2)	0.05699 (12)	0.0151 (4)
C4	0.3744 (3)	0.46089 (19)	0.19257 (12)	0.0135 (4)
C5	0.4165 (3)	0.5096 (2)	0.27709 (11)	0.0136 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0153 (3)	0.0166 (3)	0.0165 (3)	0.00419 (18)	−0.0027 (2)	−0.00059 (17)
Cl1	0.0359 (4)	0.0136 (3)	0.0227 (3)	−0.0086 (2)	−0.0055 (2)	0.00025 (18)
Cl2	0.0186 (3)	0.0337 (4)	0.0202 (3)	0.0075 (2)	0.0050 (2)	−0.0021 (2)
Cl3	0.0186 (3)	0.0164 (3)	0.0143 (3)	0.00304 (18)	−0.00199 (19)	0.00178 (16)
N1	0.0204 (9)	0.0206 (9)	0.0169 (9)	−0.0011 (7)	−0.0001 (7)	−0.0020 (7)
N2	0.0201 (9)	0.0214 (9)	0.0157 (9)	0.0021 (7)	−0.0023 (7)	−0.0011 (7)
N3	0.0142 (8)	0.0127 (8)	0.0133 (8)	−0.0010 (6)	−0.0022 (6)	0.0002 (6)
N4	0.0132 (8)	0.0145 (8)	0.0122 (8)	−0.0015 (6)	−0.0015 (6)	0.0002 (6)
C1	0.0240 (12)	0.0254 (11)	0.0176 (10)	0.0059 (9)	0.0015 (8)	−0.0031 (8)
C2	0.0180 (10)	0.0155 (9)	0.0142 (9)	−0.0029 (8)	0.0017 (7)	−0.0013 (7)
C3	0.0133 (10)	0.0135 (9)	0.0184 (10)	0.0013 (8)	−0.0018 (8)	0.0022 (7)
C4	0.0145 (10)	0.0121 (9)	0.0136 (9)	−0.0009 (7)	−0.0007 (7)	0.0027 (7)
C5	0.0138 (9)	0.0110 (8)	0.0162 (10)	0.0023 (7)	0.0008 (7)	0.0009 (7)

S1—C3	1.732 (2)	N3—N4	1.370 (2)
S1—C4	1.765 (2)	N3—C2	1.372 (3)
Cl1—C5	1.772 (2)	N4—C4	1.289 (3)
Cl2—C5	1.778 (2)	C1—C2	1.483 (3)
Cl3—C5	1.763 (2)	C1—H1A	0.9800
N1—C2	1.313 (3)	C1—H1B	0.9800
N1—N2	1.415 (2)	C1—H1C	0.9800
N2—C3	1.304 (3)	C4—C5	1.501 (3)
N3—C3	1.367 (3)
Cg1···Cg1i	3.340 (1)	Cg1···Cg2i	3.682 (1)
C3—S1—C4	86.65 (9)	N1—C2—C1	126.9 (2)
C2—N1—N2	108.78 (17)	N3—C2—C1	124.63 (18)
C3—N2—N1	105.63 (17)	N2—C3—N3	111.08 (18)
C3—N3—N4	118.75 (16)	N2—C3—S1	139.59 (16)
C3—N3—C2	106.06 (17)	N3—C3—S1	109.33 (14)
N4—N3—C2	135.19 (17)	N4—C4—C5	121.67 (18)
C4—N4—N3	106.78 (16)	N4—C4—S1	118.48 (15)
C2—C1—H1A	109.5	C5—C4—S1	119.77 (15)
C2—C1—H1B	109.5	C4—C5—Cl3	111.82 (14)
H1A—C1—H1B	109.5	C4—C5—Cl1	108.66 (13)
C2—C1—H1C	109.5	Cl3—C5—Cl1	109.30 (11)
H1A—C1—H1C	109.5	C4—C5—Cl2	108.97 (14)
H1B—C1—H1C	109.5	Cl3—C5—Cl2	109.20 (10)
N1—C2—N3	108.44 (17)	Cl1—C5—Cl2	108.84 (10)
C2—N1—N2—C3	−0.4 (2)	C2—N3—C3—S1	178.46 (13)
C3—N3—N4—C4	0.9 (2)	C4—S1—C3—N2	179.8 (3)
C2—N3—N4—C4	−178.6 (2)	C4—S1—C3—N3	0.80 (14)
N2—N1—C2—N3	−0.2 (2)	N3—N4—C4—C5	−176.81 (17)
N2—N1—C2—C1	−179.41 (19)	N3—N4—C4—S1	−0.2 (2)
C3—N3—C2—N1	0.6 (2)	C3—S1—C4—N4	−0.36 (16)
N4—N3—C2—N1	−179.8 (2)	C3—S1—C4—C5	176.31 (16)
C3—N3—C2—C1	179.86 (19)	N4—C4—C5—Cl3	−25.8 (2)
N4—N3—C2—C1	−0.6 (3)	S1—C4—C5—Cl3	157.64 (11)
N1—N2—C3—N3	0.7 (2)	N4—C4—C5—Cl1	94.93 (19)
N1—N2—C3—S1	−178.24 (19)	S1—C4—C5—Cl1	−81.63 (16)
N4—N3—C3—N2	179.50 (16)	N4—C4—C5—Cl2	−146.61 (16)
C2—N3—C3—N2	−0.8 (2)	S1—C4—C5—Cl2	36.83 (18)
N4—N3—C3—S1	−1.2 (2)