6-(2,4-Difluoro­phen­yl)-3-(4-methyl­phen­yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazine

In the title compound, C₁₇H₁₂F₂N₄S, the six-membered thia­diazine ring is distorted from planarity and may be regarded as having a half-chair conformation, with an r.m.s deviation of 0.221 Å. The delocalized triazole ring has normal bond lengths.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.049
• wR factor = 0.123
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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, 2002); software used to prepare material for publication: SHELXL97.

6-(2,4-Difluorophenyl)-3-(4-methylphenyl)-7H-1,2,4-triazolo[3,4-b][1,3,4] thiadiazine

Crystal data

C17H12F2N4S	F(000) = 704
Mr = 342.37	Dx = 1.469 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2240 reflections
a = 12.0693 (11) Å	θ = 2.7–24.7°
b = 13.0368 (12) Å	µ = 0.24 mm^−1
c = 10.4572 (9) Å	T = 298 K
β = 109.827 (2)°	Block, colorless
V = 1547.9 (2) Å^3	0.36 × 0.25 × 0.18 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	2787 independent reflections
Radiation source: fine-focus sealed tube	2269 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scan	θmax = 25.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −14→11
Tmin = 0.913, Tmax = 0.952	k = −15→13
8050 measured reflections	l = −12→12

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0636P)^2 + 0.407P] where P = (Fo^2 + 2Fc^2)/3
2787 reflections	(Δ/σ)max = 0.001
218 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.23 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	1.03481 (5)	0.80444 (5)	1.24396 (6)	0.0478 (2)
F1	0.73830 (14)	0.76724 (11)	0.70989 (14)	0.0620 (4)
F2	0.62307 (17)	0.42587 (13)	0.68514 (18)	0.0886 (6)
N1	0.82516 (16)	0.83920 (14)	0.96963 (17)	0.0387 (4)
N2	0.88603 (15)	0.92174 (13)	1.04622 (18)	0.0381 (4)
N3	0.99200 (18)	1.01110 (16)	1.2232 (2)	0.0518 (5)
N4	0.91361 (18)	1.07673 (15)	1.1313 (2)	0.0513 (5)
C1	0.7436 (2)	0.67609 (17)	0.7725 (2)	0.0426 (5)
C2	0.6799 (2)	0.5973 (2)	0.6968 (3)	0.0524 (6)
H2	0.6334	0.6067	0.6063	0.063*
C3	0.6871 (2)	0.5040 (2)	0.7590 (3)	0.0555 (7)
C4	0.7562 (2)	0.4874 (2)	0.8911 (3)	0.0593 (7)
H4	0.7601	0.4229	0.9304	0.071*
C5	0.8201 (2)	0.56838 (18)	0.9645 (2)	0.0495 (6)
H5	0.8680	0.5578	1.0541	0.059*
C6	0.81474 (19)	0.66567 (17)	0.9079 (2)	0.0379 (5)
C7	0.87967 (19)	0.75313 (17)	0.9893 (2)	0.0374 (5)
C8	1.0043 (2)	0.73736 (18)	1.0841 (2)	0.0438 (6)
H8A	1.0585	0.7611	1.0400	0.053*
H8B	1.0179	0.6646	1.1020	0.053*
C9	0.97367 (19)	0.91937 (18)	1.1708 (2)	0.0419 (5)
C10	0.84938 (19)	1.02217 (17)	1.0271 (2)	0.0401 (5)
C11	0.75565 (19)	1.06402 (17)	0.9093 (2)	0.0411 (5)
C12	0.7039 (2)	1.15618 (18)	0.9252 (3)	0.0497 (6)
H12	0.7277	1.1887	1.0093	0.060*
C13	0.6174 (2)	1.1993 (2)	0.8164 (3)	0.0551 (7)
H13	0.5839	1.2612	0.8284	0.066*
C14	0.5789 (2)	1.1535 (2)	0.6901 (3)	0.0500 (6)
C15	0.6317 (2)	1.0620 (2)	0.6756 (3)	0.0565 (7)
H15	0.6076	1.0297	0.5913	0.068*
C16	0.7186 (2)	1.01748 (19)	0.7823 (2)	0.0506 (6)
H16	0.7527	0.9561	0.7695	0.061*
C17	0.4837 (2)	1.2022 (2)	0.5724 (3)	0.0687 (8)
H17A	0.5174	1.2552	0.5335	0.103*
H17B	0.4247	1.2312	0.6042	0.103*
H17C	0.4485	1.1510	0.5048	0.103*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0508 (4)	0.0507 (4)	0.0316 (3)	0.0062 (3)	0.0007 (2)	0.0022 (3)
F1	0.0865 (11)	0.0459 (8)	0.0370 (8)	0.0007 (7)	−0.0005 (7)	0.0060 (6)
F2	0.1134 (14)	0.0609 (11)	0.0753 (12)	−0.0330 (10)	0.0111 (10)	−0.0197 (9)
N1	0.0436 (10)	0.0359 (10)	0.0313 (9)	−0.0021 (8)	0.0060 (8)	−0.0024 (8)
N2	0.0405 (10)	0.0366 (10)	0.0306 (9)	−0.0004 (8)	0.0037 (8)	−0.0018 (8)
N3	0.0541 (12)	0.0485 (12)	0.0410 (12)	0.0002 (10)	0.0005 (9)	−0.0071 (9)
N4	0.0557 (12)	0.0430 (11)	0.0456 (12)	−0.0005 (10)	0.0049 (10)	−0.0048 (9)
C1	0.0495 (13)	0.0379 (13)	0.0369 (12)	0.0021 (10)	0.0101 (10)	0.0005 (10)
C2	0.0555 (15)	0.0549 (16)	0.0385 (13)	−0.0002 (12)	0.0052 (11)	−0.0083 (12)
C3	0.0625 (17)	0.0450 (15)	0.0544 (16)	−0.0116 (12)	0.0139 (13)	−0.0135 (12)
C4	0.0760 (18)	0.0398 (14)	0.0581 (17)	−0.0056 (13)	0.0177 (14)	0.0016 (12)
C5	0.0573 (15)	0.0452 (14)	0.0404 (13)	0.0006 (12)	0.0093 (11)	0.0032 (11)
C6	0.0401 (12)	0.0378 (12)	0.0335 (11)	0.0031 (10)	0.0093 (9)	−0.0002 (9)
C7	0.0419 (12)	0.0405 (13)	0.0281 (11)	0.0000 (10)	0.0097 (9)	0.0016 (9)
C8	0.0446 (13)	0.0435 (13)	0.0371 (12)	0.0018 (10)	0.0058 (10)	0.0002 (10)
C9	0.0404 (12)	0.0478 (14)	0.0322 (12)	−0.0015 (10)	0.0056 (9)	−0.0021 (10)
C10	0.0439 (13)	0.0358 (12)	0.0386 (12)	−0.0016 (10)	0.0112 (10)	−0.0017 (10)
C11	0.0427 (12)	0.0390 (13)	0.0383 (12)	−0.0025 (10)	0.0093 (10)	0.0035 (10)
C12	0.0592 (15)	0.0427 (14)	0.0455 (14)	0.0028 (12)	0.0156 (12)	0.0007 (11)
C13	0.0562 (15)	0.0460 (15)	0.0639 (17)	0.0122 (12)	0.0214 (13)	0.0118 (13)
C14	0.0433 (13)	0.0530 (15)	0.0492 (15)	−0.0033 (12)	0.0096 (11)	0.0153 (12)
C15	0.0591 (16)	0.0575 (17)	0.0418 (14)	−0.0036 (13)	0.0027 (12)	0.0036 (12)
C16	0.0549 (15)	0.0425 (14)	0.0474 (15)	0.0030 (11)	0.0083 (12)	−0.0026 (11)
C17	0.0530 (16)	0.082 (2)	0.0621 (18)	0.0041 (15)	0.0070 (13)	0.0257 (16)

Geometric parameters (Å, º)

S1—C9	1.730 (2)	C6—C7	1.478 (3)
S1—C8	1.810 (2)	C7—C8	1.509 (3)
F1—C1	1.348 (3)	C8—H8A	0.9700
F2—C3	1.351 (3)	C8—H8B	0.9700
N1—C7	1.282 (3)	C10—C11	1.466 (3)
N1—N2	1.393 (2)	C11—C16	1.389 (3)
N2—C9	1.372 (3)	C11—C12	1.390 (3)
N2—C10	1.375 (3)	C12—C13	1.376 (3)
N3—C9	1.303 (3)	C12—H12	0.9300
N3—N4	1.391 (3)	C13—C14	1.378 (4)
N4—C10	1.312 (3)	C13—H13	0.9300
C1—C2	1.363 (3)	C14—C15	1.385 (4)
C1—C6	1.392 (3)	C14—C17	1.509 (3)
C2—C3	1.368 (4)	C15—C16	1.374 (3)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.368 (4)	C16—H16	0.9300
C4—C5	1.377 (3)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—C6	1.391 (3)	C17—H17C	0.9600
C5—H5	0.9300
C9—S1—C8	95.00 (10)	S1—C8—H8B	109.0
C7—N1—N2	116.25 (17)	H8A—C8—H8B	107.8
C9—N2—C10	105.44 (18)	N3—C9—N2	110.2 (2)
C9—N2—N1	127.95 (18)	N3—C9—S1	128.51 (17)
C10—N2—N1	124.83 (17)	N2—C9—S1	121.03 (17)
C9—N3—N4	107.16 (18)	N4—C10—N2	108.96 (19)
C10—N4—N3	108.21 (18)	N4—C10—C11	124.5 (2)
F1—C1—C2	117.2 (2)	N2—C10—C11	126.5 (2)
F1—C1—C6	119.4 (2)	C16—C11—C12	118.7 (2)
C2—C1—C6	123.3 (2)	C16—C11—C10	123.2 (2)
C1—C2—C3	117.5 (2)	C12—C11—C10	118.1 (2)
C1—C2—H2	121.3	C13—C12—C11	120.0 (2)
C3—C2—H2	121.3	C13—C12—H12	120.0
F2—C3—C4	119.5 (2)	C11—C12—H12	120.0
F2—C3—C2	117.9 (2)	C12—C13—C14	122.0 (2)
C4—C3—C2	122.6 (2)	C12—C13—H13	119.0
C3—C4—C5	118.4 (2)	C14—C13—H13	119.0
C3—C4—H4	120.8	C13—C14—C15	117.4 (2)
C5—C4—H4	120.8	C13—C14—C17	121.0 (2)
C4—C5—C6	121.7 (2)	C15—C14—C17	121.6 (3)
C4—C5—H5	119.1	C16—C15—C14	121.8 (2)
C6—C5—H5	119.1	C16—C15—H15	119.1
C5—C6—C1	116.4 (2)	C14—C15—H15	119.1
C5—C6—C7	121.3 (2)	C15—C16—C11	120.1 (2)
C1—C6—C7	122.3 (2)	C15—C16—H16	119.9
N1—C7—C6	116.10 (19)	C11—C16—H16	119.9
N1—C7—C8	124.6 (2)	C14—C17—H17A	109.5
C6—C7—C8	119.27 (19)	C14—C17—H17B	109.5
C7—C8—S1	112.75 (16)	H17A—C17—H17B	109.5
C7—C8—H8A	109.0	C14—C17—H17C	109.5
S1—C8—H8A	109.0	H17A—C17—H17C	109.5
C7—C8—H8B	109.0	H17B—C17—H17C	109.5
C7—N1—N2—C9	−26.6 (3)	C10—N2—C9—N3	−1.4 (3)
C7—N1—N2—C10	170.9 (2)	N1—N2—C9—N3	−166.6 (2)
C9—N3—N4—C10	0.8 (3)	C10—N2—C9—S1	173.14 (17)
F1—C1—C2—C3	178.5 (2)	N1—N2—C9—S1	7.9 (3)
C6—C1—C2—C3	0.3 (4)	C8—S1—C9—N3	−159.5 (2)
C1—C2—C3—F2	179.2 (2)	C8—S1—C9—N2	27.0 (2)
C1—C2—C3—C4	−1.2 (4)	N3—N4—C10—N2	−1.8 (3)
F2—C3—C4—C5	−179.6 (2)	N3—N4—C10—C11	179.3 (2)
C2—C3—C4—C5	0.7 (4)	C9—N2—C10—N4	2.0 (2)
C3—C4—C5—C6	0.6 (4)	N1—N2—C10—N4	167.7 (2)
C4—C5—C6—C1	−1.4 (4)	C9—N2—C10—C11	−179.1 (2)
C4—C5—C6—C7	177.4 (2)	N1—N2—C10—C11	−13.3 (4)
F1—C1—C6—C5	−177.3 (2)	N4—C10—C11—C16	155.8 (2)
C2—C1—C6—C5	1.0 (4)	N2—C10—C11—C16	−23.0 (4)
F1—C1—C6—C7	4.0 (3)	N4—C10—C11—C12	−22.4 (4)
C2—C1—C6—C7	−177.8 (2)	N2—C10—C11—C12	158.8 (2)
N2—N1—C7—C6	179.92 (18)	C16—C11—C12—C13	0.3 (4)
N2—N1—C7—C8	−2.3 (3)	C10—C11—C12—C13	178.6 (2)
C5—C6—C7—N1	−139.7 (2)	C11—C12—C13—C14	0.3 (4)
C1—C6—C7—N1	39.1 (3)	C12—C13—C14—C15	−0.6 (4)
C5—C6—C7—C8	42.5 (3)	C12—C13—C14—C17	179.8 (2)
C1—C6—C7—C8	−138.8 (2)	C13—C14—C15—C16	0.3 (4)
N1—C7—C8—S1	42.2 (3)	C17—C14—C15—C16	179.8 (2)
C6—C7—C8—S1	−140.07 (18)	C14—C15—C16—C11	0.3 (4)
C9—S1—C8—C7	−47.28 (18)	C12—C11—C16—C15	−0.6 (4)
N4—N3—C9—N2	0.4 (3)	C10—C11—C16—C15	−178.8 (2)
N4—N3—C9—S1	−173.65 (18)