6-(2,4-Dichloro­phen­yl)-3-[(1H-1,2,4-triazol-1-yl)meth­yl]-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazine

In the title compound, C₁₃H₉Cl₂N₇S, the thia­zolothia­diazine ring system is delocalized. The dihedral angles made by the plane of the triazole ring in the fused heterocycle with the second triazole and the benzene ring are 84.86 (2) and 23.89 (3)°, respectively. Inter­molecular π–π stacking inter­actions stabilize the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.116
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

6-(2,4-Dichlorophenyl)-3-[(1H-1,2,4-triazol-1-yl)methyl]-7H-1,2,4- triazolo[3,4-b][1,3,4]thiadiazine

Crystal data

C13H9Cl2N7S	F(000) = 744
Mr = 366.23	Dx = 1.568 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4194 reflections
a = 15.283 (2) Å	θ = 2.8–26.4°
b = 5.2277 (7) Å	µ = 0.56 mm^−1
c = 20.398 (3) Å	T = 294 K
β = 107.811 (2)°	Platelet, colorless
V = 1551.6 (4) Å^3	0.22 × 0.18 × 0.14 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3205 independent reflections
Radiation source: fine-focus sealed tube	2531 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 26.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→19
Tmin = 0.886, Tmax = 0.926	k = −6→6
8287 measured reflections	l = −25→17

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0512P)^2 + 1.0076P] where P = (Fo^2 + 2Fc^2)/3
3205 reflections	(Δ/σ)max = 0.002
208 parameters	Δρmax = 0.57 e Å^−3
0 restraints	Δρmin = −0.56 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	0.91962 (4)	0.63960 (11)	1.04406 (3)	0.04009 (17)
Cl1	0.56092 (7)	−0.44989 (18)	1.12625 (5)	0.0844 (3)
Cl2	0.80846 (6)	0.3016 (2)	1.17108 (4)	0.0848 (3)
N1	0.74144 (12)	0.3563 (4)	0.95463 (9)	0.0377 (4)
N2	0.79074 (13)	0.5174 (4)	0.92496 (8)	0.0369 (4)
N3	0.87584 (15)	0.8431 (4)	0.91366 (10)	0.0506 (5)
N4	0.80818 (16)	0.7965 (5)	0.85023 (10)	0.0554 (6)
N5	0.61001 (14)	0.6739 (4)	0.77429 (9)	0.0479 (5)
N6	0.57308 (17)	0.8255 (6)	0.81284 (12)	0.0659 (7)
N7	0.51375 (19)	0.9192 (6)	0.70046 (13)	0.0780 (8)
C1	0.66890 (17)	−0.0718 (5)	1.00051 (12)	0.0471 (6)
H1	0.6620	−0.0699	0.9536	0.057*
C2	0.6163 (2)	−0.2365 (6)	1.02496 (14)	0.0583 (7)
H2	0.5746	−0.3454	0.9951	0.070*
C3	0.6261 (2)	−0.2386 (6)	1.09422 (15)	0.0567 (7)
C4	0.6865 (2)	−0.0779 (6)	1.13889 (13)	0.0585 (7)
H4	0.6922	−0.0797	1.1856	0.070*
C5	0.73873 (18)	0.0864 (5)	1.11357 (12)	0.0485 (6)
C6	0.73272 (15)	0.0937 (4)	1.04425 (11)	0.0379 (5)
C7	0.78708 (15)	0.2636 (4)	1.01362 (10)	0.0347 (5)
C8	0.88900 (15)	0.3044 (4)	1.04468 (11)	0.0385 (5)
H8A	0.9213	0.2065	1.0189	0.046*
H8B	0.9082	0.2421	1.0917	0.046*
C9	0.86326 (15)	0.6736 (4)	0.95658 (11)	0.0378 (5)
C10	0.75864 (17)	0.6056 (5)	0.85866 (11)	0.0444 (6)
C11	0.6791 (2)	0.4849 (5)	0.80631 (12)	0.0553 (7)
H11A	0.7003	0.4023	0.7713	0.066*
H11B	0.6523	0.3549	0.8282	0.066*
C12	0.5733 (2)	0.7343 (7)	0.70836 (13)	0.0651 (8)
H12	0.5882	0.6548	0.6724	0.078*
C13	0.5160 (2)	0.9668 (7)	0.76569 (16)	0.0743 (10)
H13	0.4796	1.0919	0.7767	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0425 (3)	0.0382 (3)	0.0332 (3)	−0.0049 (2)	0.0022 (2)	−0.0008 (2)
Cl1	0.1024 (6)	0.0841 (6)	0.0845 (6)	−0.0454 (5)	0.0549 (5)	−0.0144 (5)
Cl2	0.0982 (6)	0.1149 (7)	0.0427 (4)	−0.0591 (6)	0.0237 (4)	−0.0298 (4)
N1	0.0395 (10)	0.0404 (10)	0.0313 (9)	−0.0043 (8)	0.0081 (7)	−0.0013 (8)
N2	0.0410 (10)	0.0400 (10)	0.0265 (9)	−0.0020 (8)	0.0054 (7)	0.0012 (8)
N3	0.0538 (12)	0.0526 (13)	0.0399 (11)	−0.0076 (10)	0.0061 (9)	0.0086 (10)
N4	0.0664 (14)	0.0587 (14)	0.0354 (11)	−0.0090 (12)	0.0068 (10)	0.0100 (10)
N5	0.0501 (11)	0.0585 (13)	0.0297 (9)	−0.0018 (10)	0.0042 (8)	−0.0047 (9)
N6	0.0618 (15)	0.091 (2)	0.0437 (12)	−0.0008 (14)	0.0147 (11)	−0.0182 (13)
N7	0.0695 (16)	0.101 (2)	0.0509 (14)	0.0336 (16)	−0.0007 (12)	−0.0076 (14)
C1	0.0499 (13)	0.0540 (15)	0.0376 (12)	−0.0123 (12)	0.0138 (10)	−0.0083 (11)
C2	0.0590 (16)	0.0632 (17)	0.0538 (15)	−0.0259 (14)	0.0190 (12)	−0.0180 (13)
C3	0.0626 (16)	0.0549 (16)	0.0611 (16)	−0.0193 (14)	0.0315 (14)	−0.0063 (13)
C4	0.0708 (18)	0.0682 (19)	0.0407 (13)	−0.0211 (15)	0.0233 (12)	−0.0048 (13)
C5	0.0529 (14)	0.0559 (15)	0.0349 (12)	−0.0159 (12)	0.0109 (10)	−0.0072 (11)
C6	0.0387 (11)	0.0404 (12)	0.0335 (11)	−0.0034 (10)	0.0095 (9)	−0.0024 (9)
C7	0.0383 (11)	0.0349 (11)	0.0291 (10)	−0.0011 (9)	0.0076 (8)	−0.0029 (9)
C8	0.0387 (11)	0.0369 (12)	0.0363 (11)	−0.0025 (10)	0.0063 (9)	0.0042 (9)
C9	0.0398 (11)	0.0372 (12)	0.0333 (11)	−0.0007 (10)	0.0066 (9)	0.0002 (9)
C10	0.0539 (14)	0.0463 (13)	0.0286 (11)	0.0008 (12)	0.0060 (10)	0.0034 (10)
C11	0.0678 (17)	0.0529 (15)	0.0328 (12)	−0.0041 (14)	−0.0033 (11)	0.0016 (11)
C12	0.0647 (17)	0.090 (2)	0.0316 (12)	0.0237 (17)	0.0018 (11)	−0.0056 (13)
C13	0.0516 (16)	0.097 (3)	0.0656 (19)	0.0132 (17)	0.0054 (14)	−0.0252 (18)

Geometric parameters (Å, º)

S1—C9	1.737 (2)	C1—C6	1.401 (3)
S1—C8	1.815 (2)	C1—H1	0.9300
Cl1—C3	1.742 (3)	C2—C3	1.375 (4)
Cl2—C5	1.736 (3)	C2—H2	0.9300
N1—C7	1.287 (3)	C3—C4	1.369 (4)
N1—N2	1.386 (3)	C4—C5	1.376 (4)
N2—C9	1.369 (3)	C4—H4	0.9300
N2—C10	1.370 (3)	C5—C6	1.389 (3)
N3—C9	1.300 (3)	C6—C7	1.479 (3)
N3—N4	1.409 (3)	C7—C8	1.506 (3)
N4—C10	1.295 (3)	C8—H8A	0.9700
N5—C12	1.327 (3)	C8—H8B	0.9700
N5—N6	1.355 (3)	C10—C11	1.491 (3)
N5—C11	1.448 (3)	C11—H11A	0.9700
N6—C13	1.311 (4)	C11—H11B	0.9700
N7—C12	1.303 (4)	C12—H12	0.9300
N7—C13	1.344 (4)	C13—H13	0.9300
C1—C2	1.371 (4)
C9—S1—C8	93.34 (11)	C1—C6—C7	118.3 (2)
C7—N1—N2	115.18 (18)	N1—C7—C6	114.05 (19)
C9—N2—C10	104.95 (19)	N1—C7—C8	122.3 (2)
C9—N2—N1	128.80 (17)	C6—C7—C8	123.33 (19)
C10—N2—N1	123.86 (19)	C7—C8—S1	111.67 (16)
C9—N3—N4	106.4 (2)	C7—C8—H8A	109.3
C10—N4—N3	107.81 (19)	S1—C8—H8A	109.3
C12—N5—N6	109.1 (2)	C7—C8—H8B	109.3
C12—N5—C11	130.0 (2)	S1—C8—H8B	109.3
N6—N5—C11	120.9 (2)	H8A—C8—H8B	107.9
C13—N6—N5	101.9 (2)	N3—C9—N2	110.76 (19)
C12—N7—C13	102.1 (3)	N3—C9—S1	129.23 (18)
C2—C1—C6	121.8 (2)	N2—C9—S1	119.89 (16)
C2—C1—H1	119.1	N4—C10—N2	110.1 (2)
C6—C1—H1	119.1	N4—C10—C11	127.8 (2)
C1—C2—C3	119.2 (2)	N2—C10—C11	122.1 (2)
C1—C2—H2	120.4	N5—C11—C10	110.9 (2)
C3—C2—H2	120.4	N5—C11—H11A	109.5
C4—C3—C2	121.2 (2)	C10—C11—H11A	109.5
C4—C3—Cl1	119.1 (2)	N5—C11—H11B	109.5
C2—C3—Cl1	119.7 (2)	C10—C11—H11B	109.5
C3—C4—C5	118.9 (2)	H11A—C11—H11B	108.1
C3—C4—H4	120.5	N7—C12—N5	111.4 (3)
C5—C4—H4	120.5	N7—C12—H12	124.3
C4—C5—C6	122.3 (2)	N5—C12—H12	124.3
C4—C5—Cl2	117.23 (19)	N6—C13—N7	115.6 (3)
C6—C5—Cl2	120.40 (19)	N6—C13—H13	122.2
C5—C6—C1	116.6 (2)	N7—C13—H13	122.2
C5—C6—C7	125.1 (2)
C7—N1—N2—C9	−29.9 (3)	C6—C7—C8—S1	−136.09 (19)
C7—N1—N2—C10	170.4 (2)	C9—S1—C8—C7	−52.63 (17)
C9—N3—N4—C10	0.7 (3)	N4—N3—C9—N2	−0.1 (3)
C12—N5—N6—C13	0.0 (3)	N4—N3—C9—S1	−175.96 (19)
C11—N5—N6—C13	179.3 (3)	C10—N2—C9—N3	−0.5 (3)
C6—C1—C2—C3	0.3 (4)	N1—N2—C9—N3	−163.2 (2)
C1—C2—C3—C4	0.6 (5)	C10—N2—C9—S1	175.81 (17)
C1—C2—C3—Cl1	−179.1 (2)	N1—N2—C9—S1	13.1 (3)
C2—C3—C4—C5	−0.6 (5)	C8—S1—C9—N3	−158.0 (2)
Cl1—C3—C4—C5	179.1 (2)	C8—S1—C9—N2	26.4 (2)
C3—C4—C5—C6	−0.4 (5)	N3—N4—C10—N2	−1.0 (3)
C3—C4—C5—Cl2	175.6 (2)	N3—N4—C10—C11	−179.6 (3)
C4—C5—C6—C1	1.3 (4)	C9—N2—C10—N4	0.9 (3)
Cl2—C5—C6—C1	−174.6 (2)	N1—N2—C10—N4	164.7 (2)
C4—C5—C6—C7	−179.6 (3)	C9—N2—C10—C11	179.6 (2)
Cl2—C5—C6—C7	4.5 (4)	N1—N2—C10—C11	−16.6 (4)
C2—C1—C6—C5	−1.3 (4)	C12—N5—C11—C10	123.6 (3)
C2—C1—C6—C7	179.5 (2)	N6—N5—C11—C10	−55.6 (3)
N2—N1—C7—C6	179.68 (18)	N4—C10—C11—N5	−54.5 (4)
N2—N1—C7—C8	−6.2 (3)	N2—C10—C11—N5	127.1 (3)
C5—C6—C7—N1	−140.4 (2)	C13—N7—C12—N5	−0.3 (4)
C1—C6—C7—N1	38.6 (3)	N6—N5—C12—N7	0.2 (4)
C5—C6—C7—C8	45.5 (4)	C11—N5—C12—N7	−179.0 (3)
C1—C6—C7—C8	−135.4 (2)	N5—N6—C13—N7	−0.3 (4)
N1—C7—C8—S1	50.4 (3)	C12—N7—C13—N6	0.4 (4)