1-(2,4-Dichloro­phen­yl)-2-[5-(1H-1,2,4-triazol-1-ylmeth­yl)-1,3,4-thia­diazol-2-yl­sulfan­yl]ethanone

The mol­ecule of the title compound, C₁₃H₉Cl₂N₅OS₂, is essentially non-planar, with a dihedral angle of 68.6 (2)° between the thia­diazole and triazole rings, and a dihedral angle of 62.8 (1)° between the thia­diazole and benzene rings. The crystal packing is stabilized by inter­molecular C—H...N hydrogen bonds, which link dimers into zigzag chains along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.094
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  S2      ..       3.44 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C13 H9 Cl2 N5 O S2

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

1,2,4-Triazole and 1,3,4-thiadiazol derivatives are known to possess broad-range fungicides and insecticidal (Pachhamia & Parikh, 1988; Zhang et al., 2002; Xu et al., 2005). As part of our ongoing studies to search for the compounds with higher properties, the title compound (I) has been synthesized and its crystal structure is presented here.

In the molecular of (I) (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The whole molecule is non-planar. The thiadiazole (C4/C5/N4/N5/S1) ring makes dihedral angles of 68.6 (2)° and 62.8 (1)° with the triazole (C1/C2/N1—N3) ring and benzene (C8—C13) ring, respectively.

In the crystal structure, molecules are linked into inversion-related dimers by C1—H1B···N4 intermolecular hydrogen bonds (Table 1 and Fig. 2). The crystal packing is also stabilized by intermolecular C13—H13A···N2 hydrogen bonds, which link the dimers into zigzag chains along the b axis.

Related literature

For related literature, see: Allen et al. (1987); Pachhamia & Parikh (1988); Zhang et al. (2002); Xu et al. (2005).

S2. Experimental

A mixture of 5-(1H-1,2,4-triazol-1-yl)methyl)-1,3,4-thiadiazole-2(3H)-thione (0.02 mol) and 2-bromo-1-(2,4-dichlorophenyl)ethanone (0.02 mol) was stirred in acetone (20 ml) for 4 h at 298 K to afford the title compound (5.33 g, yield 69%). Single crystals of (I) suitable for X-ray measurements were obtained by slow evaporation of ethylacetate solution at room temperature.

S3. Refinement

All H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, and with U_iso(H) = 1.2 U_eq(C).

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures

	Fig. 1. The structure of the compound (I) showing 30% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. Packing diagram of the title compound (I). Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

1-(2,4-Dichlorophenyl)-2-[5-(1H-1,2,4-triazol-1-ylmethyl)- 1,3,4-thiadiazol-2-ylsulfanyl)ethanone

Crystal data

C13H9Cl2N5OS2	Z = 2
Mr = 386.27	F(000) = 392
Triclinic, P1	Dx = 1.590 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3081 (8) Å	Cell parameters from 2332 reflections
b = 11.5302 (12) Å	θ = 3.0–25.7°
c = 11.5865 (12) Å	µ = 0.67 mm^−1
α = 114.784 (1)°	T = 293 K
β = 97.618 (1)°	Column, white
γ = 107.483 (1)°	0.32 × 0.18 × 0.12 mm
V = 806.90 (15) Å^3

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	3000 independent reflections
Radiation source: fine-focus sealed tube	2633 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
Detector resolution: 8.33 pixels mm^-1	θmax = 25.7°, θmin = 2.0°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→8
Tmin = 0.814, Tmax = 0.924	l = −13→14
4453 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.046P)^2 + 0.3504P] where P = (Fo^2 + 2Fc^2)/3
3000 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.18898 (9)	0.88995 (5)	0.12622 (5)	0.04774 (17)
S2	−0.05128 (9)	1.06974 (6)	0.15303 (5)	0.04834 (17)
Cl1	0.08220 (10)	1.21982 (8)	0.67037 (8)	0.0727 (2)
Cl2	0.56331 (13)	1.75973 (9)	0.91989 (7)	0.0992 (3)
N3	0.3817 (3)	0.72299 (17)	0.24843 (16)	0.0412 (4)
N5	0.2411 (3)	1.10266 (17)	0.34432 (17)	0.0442 (4)
N4	0.3763 (3)	1.04975 (17)	0.37369 (17)	0.0439 (4)
O1	−0.1538 (2)	1.16754 (17)	0.41346 (17)	0.0619 (5)
C7	−0.0064 (3)	1.2523 (2)	0.4152 (2)	0.0415 (5)
C9	0.1837 (3)	1.3715 (2)	0.6617 (2)	0.0452 (5)
N1	0.2790 (4)	0.6229 (2)	0.12138 (19)	0.0650 (6)
C4	0.3667 (3)	0.9404 (2)	0.2716 (2)	0.0390 (4)
C13	0.2396 (3)	1.4985 (2)	0.5429 (2)	0.0448 (5)
H13A	0.2169	1.5020	0.4638	0.054*
C3	0.4986 (3)	0.8651 (2)	0.2801 (2)	0.0453 (5)
H3A	0.5772	0.8635	0.2187	0.054*
H3B	0.5911	0.9147	0.3694	0.054*
C8	0.1426 (3)	1.3732 (2)	0.5417 (2)	0.0383 (4)
N2	0.2214 (3)	0.54035 (19)	0.2638 (2)	0.0571 (5)
C1	0.3436 (4)	0.6723 (2)	0.3299 (2)	0.0497 (5)
H1B	0.3964	0.7235	0.4222	0.060*
C5	0.1343 (3)	1.02984 (19)	0.2199 (2)	0.0395 (4)
C12	0.3678 (3)	1.6167 (2)	0.6581 (2)	0.0528 (6)
H12A	0.4303	1.6994	0.6573	0.063*
C6	0.0275 (3)	1.2450 (2)	0.2857 (2)	0.0445 (5)
H6A	0.1692	1.2952	0.3019	0.053*
H6B	−0.0459	1.2910	0.2579	0.053*
C2	0.1871 (4)	0.5162 (2)	0.1377 (3)	0.0632 (7)
H2B	0.1036	0.4294	0.0661	0.076*
C11	0.4018 (3)	1.6104 (3)	0.7741 (2)	0.0567 (6)
C10	0.3127 (3)	1.4892 (3)	0.7780 (2)	0.0570 (6)
H10B	0.3388	1.4866	0.8574	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0637 (4)	0.0385 (3)	0.0350 (3)	0.0231 (3)	0.0064 (2)	0.0131 (2)
S2	0.0539 (3)	0.0415 (3)	0.0383 (3)	0.0197 (3)	0.0022 (2)	0.0124 (2)
Cl1	0.0632 (4)	0.0811 (5)	0.0947 (5)	0.0178 (3)	0.0230 (4)	0.0684 (4)
Cl2	0.0849 (5)	0.0838 (6)	0.0523 (4)	−0.0113 (4)	0.0080 (4)	0.0011 (4)
N3	0.0471 (10)	0.0335 (9)	0.0378 (9)	0.0133 (7)	0.0065 (7)	0.0165 (7)
N5	0.0467 (10)	0.0371 (9)	0.0378 (9)	0.0144 (8)	0.0056 (8)	0.0123 (8)
N4	0.0448 (9)	0.0365 (9)	0.0402 (9)	0.0116 (8)	0.0043 (8)	0.0152 (8)
O1	0.0504 (9)	0.0524 (10)	0.0611 (10)	0.0024 (8)	0.0193 (8)	0.0203 (8)
C7	0.0401 (11)	0.0373 (11)	0.0479 (12)	0.0163 (9)	0.0158 (9)	0.0201 (9)
C9	0.0387 (11)	0.0524 (13)	0.0536 (13)	0.0179 (10)	0.0201 (10)	0.0319 (11)
N1	0.0887 (16)	0.0413 (11)	0.0403 (10)	0.0082 (10)	0.0004 (10)	0.0158 (9)
C4	0.0411 (10)	0.0318 (10)	0.0394 (11)	0.0079 (8)	0.0075 (8)	0.0189 (9)
C13	0.0491 (12)	0.0398 (11)	0.0448 (12)	0.0159 (9)	0.0140 (10)	0.0212 (10)
C3	0.0446 (11)	0.0363 (11)	0.0515 (12)	0.0120 (9)	0.0086 (10)	0.0226 (10)
C8	0.0377 (10)	0.0384 (11)	0.0429 (11)	0.0170 (8)	0.0166 (9)	0.0204 (9)
N2	0.0670 (13)	0.0417 (11)	0.0578 (12)	0.0122 (9)	0.0128 (10)	0.0281 (10)
C1	0.0612 (14)	0.0430 (12)	0.0407 (11)	0.0153 (10)	0.0111 (10)	0.0217 (10)
C5	0.0452 (11)	0.0311 (10)	0.0379 (11)	0.0117 (8)	0.0108 (9)	0.0157 (9)
C12	0.0534 (13)	0.0391 (12)	0.0560 (14)	0.0112 (10)	0.0179 (11)	0.0188 (11)
C6	0.0543 (12)	0.0347 (11)	0.0431 (11)	0.0188 (9)	0.0130 (10)	0.0174 (9)
C2	0.0757 (17)	0.0328 (12)	0.0528 (14)	0.0050 (11)	−0.0018 (12)	0.0136 (11)
C11	0.0445 (12)	0.0545 (14)	0.0457 (13)	0.0084 (11)	0.0121 (10)	0.0103 (11)
C10	0.0456 (12)	0.0749 (17)	0.0439 (13)	0.0154 (12)	0.0133 (10)	0.0288 (12)

Geometric parameters (Å, º)

S1—C5	1.725 (2)	N1—C2	1.316 (3)
S1—C4	1.734 (2)	C4—C3	1.497 (3)
S2—C5	1.745 (2)	C13—C12	1.376 (3)
S2—C6	1.800 (2)	C13—C8	1.398 (3)
Cl1—C9	1.734 (2)	C13—H13A	0.9300
Cl2—C11	1.739 (2)	C3—H3A	0.9700
N3—C1	1.321 (3)	C3—H3B	0.9700
N3—N1	1.351 (2)	N2—C1	1.313 (3)
N3—C3	1.457 (2)	N2—C2	1.339 (3)
N5—C5	1.298 (3)	C1—H1B	0.9300
N5—N4	1.382 (2)	C12—C11	1.370 (4)
N4—C4	1.292 (3)	C12—H12A	0.9300
O1—C7	1.209 (2)	C6—H6A	0.9700
C7—C8	1.493 (3)	C6—H6B	0.9700
C7—C6	1.525 (3)	C2—H2B	0.9300
C9—C10	1.381 (3)	C11—C10	1.375 (3)
C9—C8	1.393 (3)	C10—H10B	0.9300
C5—S1—C4	86.42 (10)	C9—C8—C7	123.84 (18)
C5—S2—C6	97.27 (10)	C13—C8—C7	118.69 (18)
C1—N3—N1	109.61 (18)	C1—N2—C2	101.74 (18)
C1—N3—C3	129.13 (18)	N2—C1—N3	111.2 (2)
N1—N3—C3	121.05 (17)	N2—C1—H1B	124.4
C5—N5—N4	111.87 (17)	N3—C1—H1B	124.4
C4—N4—N5	112.87 (16)	N5—C5—S1	114.74 (16)
O1—C7—C8	122.50 (19)	N5—C5—S2	122.62 (16)
O1—C7—C6	120.60 (19)	S1—C5—S2	122.64 (12)
C8—C7—C6	116.77 (17)	C11—C12—C13	118.8 (2)
C10—C9—C8	121.5 (2)	C11—C12—H12A	120.6
C10—C9—Cl1	117.04 (18)	C13—C12—H12A	120.6
C8—C9—Cl1	121.40 (17)	C7—C6—S2	113.16 (14)
C2—N1—N3	101.53 (19)	C7—C6—H6A	108.9
N4—C4—C3	122.20 (18)	S2—C6—H6A	108.9
N4—C4—S1	114.11 (16)	C7—C6—H6B	108.9
C3—C4—S1	123.69 (16)	S2—C6—H6B	108.9
C12—C13—C8	121.7 (2)	H6A—C6—H6B	107.8
C12—C13—H13A	119.1	N1—C2—N2	115.9 (2)
C8—C13—H13A	119.1	N1—C2—H2B	122.1
N3—C3—C4	111.73 (17)	N2—C2—H2B	122.1
N3—C3—H3A	109.3	C12—C11—C10	121.8 (2)
C4—C3—H3A	109.3	C12—C11—Cl2	118.86 (19)
N3—C3—H3B	109.3	C10—C11—Cl2	119.3 (2)
C4—C3—H3B	109.3	C11—C10—C9	118.8 (2)
H3A—C3—H3B	107.9	C11—C10—H10B	120.6
C9—C8—C13	117.4 (2)	C9—C10—H10B	120.6
C5—N5—N4—C4	0.1 (2)	C2—N2—C1—N3	−0.8 (3)
C1—N3—N1—C2	−1.0 (3)	N1—N3—C1—N2	1.2 (3)
C3—N3—N1—C2	−176.2 (2)	C3—N3—C1—N2	175.9 (2)
N5—N4—C4—C3	−179.72 (17)	N4—N5—C5—S1	−0.3 (2)
N5—N4—C4—S1	0.1 (2)	N4—N5—C5—S2	179.31 (14)
C5—S1—C4—N4	−0.23 (16)	C4—S1—C5—N5	0.29 (16)
C5—S1—C4—C3	179.61 (18)	C4—S1—C5—S2	−179.30 (14)
C1—N3—C3—C4	−98.8 (3)	C6—S2—C5—N5	16.65 (19)
N1—N3—C3—C4	75.4 (3)	C6—S2—C5—S1	−163.80 (13)
N4—C4—C3—N3	117.6 (2)	C8—C13—C12—C11	0.5 (4)
S1—C4—C3—N3	−62.2 (2)	O1—C7—C6—S2	−37.3 (3)
C10—C9—C8—C13	1.0 (3)	C8—C7—C6—S2	146.76 (16)
Cl1—C9—C8—C13	−176.64 (15)	C5—S2—C6—C7	−68.97 (17)
C10—C9—C8—C7	−175.4 (2)	N3—N1—C2—N2	0.5 (3)
Cl1—C9—C8—C7	6.9 (3)	C1—N2—C2—N1	0.1 (3)
C12—C13—C8—C9	−1.3 (3)	C13—C12—C11—C10	0.5 (4)
C12—C13—C8—C7	175.4 (2)	C13—C12—C11—Cl2	−179.85 (19)
O1—C7—C8—C9	29.9 (3)	C12—C11—C10—C9	−0.8 (4)
C6—C7—C8—C9	−154.2 (2)	Cl2—C11—C10—C9	179.59 (18)
O1—C7—C8—C13	−146.5 (2)	C8—C9—C10—C11	0.0 (3)
C6—C7—C8—C13	29.4 (3)	Cl1—C9—C10—C11	177.74 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···N4^i	0.93	2.52	3.348 (3)	149
C13—H13A···N2^ii	0.93	2.54	3.455 (3)	170

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