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

In the title compound, C₁₇H₁₂F₂N₄OS, the thia­diazine ring is non-planar and adopts a half-chair conformation. The crystal packing is stabilized by C—H...N, C—H...O and C—H...F inter­molecular hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.050
• wR factor = 0.119
• Data-to-parameter ratio = 12.3

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-methoxyphenyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine

Crystal data

C17H12F2N4OS	F(000) = 736
Mr = 358.37	Dx = 1.509 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2351 reflections
a = 12.9203 (7) Å	θ = 2.7–24.4°
b = 13.9490 (11) Å	µ = 0.24 mm^−1
c = 8.7609 (10) Å	T = 298 K
β = 92.502 (1)°	Plate, colourless
V = 1577.4 (2) Å^3	0.30 × 0.22 × 0.13 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	2782 independent reflections
Radiation source: fine-focus sealed tube	2387 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −15→15
Tmin = 0.931, Tmax = 0.959	k = −16→8
8091 measured reflections	l = −10→10

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0534P)^2 + 0.5462P] where P = (Fo^2 + 2Fc^2)/3
2782 reflections	(Δ/σ)max = 0.001
227 parameters	Δρmax = 0.23 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	0.50405 (5)	0.89092 (5)	0.11850 (7)	0.0487 (2)
F1	0.83812 (14)	1.27967 (11)	0.5736 (2)	0.0741 (5)
F2	0.62500 (13)	1.13043 (11)	0.20091 (17)	0.0625 (5)
O1	0.97784 (15)	0.55338 (14)	0.7366 (2)	0.0670 (6)
N1	0.69686 (14)	0.87487 (13)	0.3473 (2)	0.0342 (4)
N2	0.64866 (13)	0.79316 (13)	0.2880 (2)	0.0345 (4)
N3	0.55762 (16)	0.70096 (15)	0.1280 (2)	0.0479 (5)
N4	0.63027 (16)	0.64509 (15)	0.2106 (2)	0.0455 (5)
C1	0.7883 (2)	1.19999 (18)	0.5198 (3)	0.0485 (6)
C2	0.7267 (2)	1.20802 (17)	0.3896 (3)	0.0491 (7)
H2	0.7170	1.2665	0.3399	0.059*
C3	0.67985 (19)	1.12580 (17)	0.3356 (3)	0.0417 (6)
C4	0.69034 (17)	1.03805 (16)	0.4080 (2)	0.0349 (5)
C5	0.75317 (18)	1.03556 (17)	0.5411 (3)	0.0409 (6)
H5	0.7617	0.9778	0.5931	0.049*
C6	0.8032 (2)	1.11594 (18)	0.5983 (3)	0.0477 (6)
H6	0.8454	1.1132	0.6869	0.057*
C7	0.63962 (17)	0.95010 (16)	0.3477 (2)	0.0351 (5)
C8	0.52640 (18)	0.94972 (18)	0.3016 (3)	0.0435 (6)
H8A	0.5012	1.0152	0.2951	0.052*
H8B	0.4883	0.9166	0.3786	0.052*
C9	0.57016 (18)	0.78853 (17)	0.1772 (3)	0.0385 (6)
C10	0.68445 (18)	0.70027 (16)	0.3048 (3)	0.0364 (5)
C11	0.76342 (17)	0.66464 (16)	0.4163 (3)	0.0368 (5)
C12	0.83657 (19)	0.72188 (17)	0.4937 (3)	0.0486 (6)
H12	0.8379	0.7875	0.4747	0.058*
C13	0.9071 (2)	0.68237 (19)	0.5983 (3)	0.0550 (7)
H13	0.9554	0.7216	0.6493	0.066*
C14	0.90663 (18)	0.58472 (18)	0.6282 (3)	0.0458 (6)
C15	0.83532 (19)	0.52712 (18)	0.5505 (3)	0.0451 (6)
H15	0.8349	0.4614	0.5682	0.054*
C16	0.76497 (18)	0.56695 (17)	0.4470 (3)	0.0424 (6)
H16	0.7170	0.5274	0.3961	0.051*
C17	0.9809 (2)	0.4538 (2)	0.7717 (4)	0.0635 (8)
H17A	0.9143	0.4336	0.8039	0.095*
H17B	1.0322	0.4424	0.8522	0.095*
H17C	0.9984	0.4183	0.6825	0.095*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0510 (4)	0.0457 (4)	0.0482 (4)	0.0025 (3)	−0.0133 (3)	−0.0002 (3)
F1	0.0896 (12)	0.0405 (10)	0.0922 (12)	−0.0222 (8)	0.0044 (10)	−0.0180 (8)
F2	0.0817 (11)	0.0557 (10)	0.0487 (9)	0.0019 (8)	−0.0116 (8)	0.0125 (7)
O1	0.0614 (12)	0.0472 (12)	0.0897 (14)	0.0026 (9)	−0.0261 (11)	0.0043 (10)
N1	0.0390 (11)	0.0269 (10)	0.0366 (10)	−0.0032 (8)	0.0002 (8)	−0.0025 (8)
N2	0.0361 (10)	0.0294 (11)	0.0379 (10)	−0.0020 (8)	0.0003 (8)	−0.0062 (8)
N3	0.0531 (13)	0.0439 (13)	0.0462 (11)	−0.0049 (10)	−0.0044 (10)	−0.0097 (10)
N4	0.0519 (12)	0.0358 (12)	0.0485 (12)	−0.0015 (10)	−0.0015 (10)	−0.0107 (10)
C1	0.0528 (15)	0.0310 (14)	0.0626 (16)	−0.0080 (11)	0.0111 (13)	−0.0132 (12)
C2	0.0630 (17)	0.0280 (14)	0.0569 (15)	0.0014 (12)	0.0112 (14)	0.0061 (12)
C3	0.0494 (14)	0.0372 (14)	0.0384 (12)	0.0028 (11)	0.0018 (11)	0.0022 (10)
C4	0.0369 (12)	0.0293 (12)	0.0386 (12)	0.0008 (10)	0.0037 (10)	−0.0014 (10)
C5	0.0470 (14)	0.0293 (13)	0.0461 (13)	0.0024 (10)	−0.0022 (11)	0.0023 (10)
C6	0.0520 (15)	0.0407 (15)	0.0498 (14)	−0.0037 (12)	−0.0058 (12)	−0.0059 (12)
C7	0.0409 (13)	0.0308 (13)	0.0335 (11)	0.0004 (10)	0.0020 (10)	−0.0003 (10)
C8	0.0423 (13)	0.0366 (14)	0.0511 (14)	0.0030 (11)	−0.0015 (11)	−0.0058 (11)
C9	0.0395 (13)	0.0402 (14)	0.0357 (11)	−0.0034 (10)	0.0011 (10)	−0.0043 (10)
C10	0.0402 (12)	0.0287 (13)	0.0409 (12)	−0.0030 (10)	0.0079 (10)	−0.0063 (10)
C11	0.0387 (12)	0.0289 (12)	0.0433 (12)	0.0020 (10)	0.0073 (10)	−0.0051 (10)
C12	0.0496 (15)	0.0281 (13)	0.0675 (17)	−0.0011 (11)	−0.0044 (13)	−0.0038 (12)
C13	0.0506 (15)	0.0370 (15)	0.0759 (18)	−0.0025 (12)	−0.0153 (14)	−0.0083 (13)
C14	0.0405 (13)	0.0403 (15)	0.0563 (15)	0.0045 (11)	−0.0020 (12)	0.0010 (12)
C15	0.0497 (14)	0.0300 (13)	0.0556 (15)	0.0009 (11)	0.0037 (12)	0.0014 (11)
C16	0.0452 (14)	0.0341 (13)	0.0476 (13)	−0.0044 (11)	−0.0003 (11)	−0.0056 (11)
C17	0.0619 (18)	0.0539 (19)	0.0738 (19)	0.0048 (14)	−0.0057 (15)	0.0177 (15)

Geometric parameters (Å, º)

S1—C9	1.731 (2)	C5—C6	1.377 (3)
S1—C8	1.813 (2)	C5—H5	0.93
F1—C1	1.358 (3)	C6—H6	0.93
F2—C3	1.351 (3)	C7—C8	1.500 (3)
O1—C14	1.365 (3)	C8—H8A	0.97
O1—C17	1.423 (3)	C8—H8B	0.97
N1—C7	1.284 (3)	C10—C11	1.468 (3)
N1—N2	1.389 (2)	C11—C16	1.389 (3)
N2—C9	1.375 (3)	C11—C12	1.391 (3)
N2—C10	1.381 (3)	C12—C13	1.378 (4)
N3—C9	1.303 (3)	C12—H12	0.93
N3—N4	1.398 (3)	C13—C14	1.387 (4)
N4—C10	1.309 (3)	C13—H13	0.93
C1—C2	1.367 (4)	C14—C15	1.379 (3)
C1—C6	1.368 (4)	C15—C16	1.373 (3)
C2—C3	1.371 (3)	C15—H15	0.93
C2—H2	0.93	C16—H16	0.93
C3—C4	1.383 (3)	C17—H17A	0.96
C4—C5	1.392 (3)	C17—H17B	0.96
C4—C7	1.478 (3)	C17—H17C	0.96
C9—S1—C8	93.04 (11)	S1—C8—H8B	109.5
C14—O1—C17	118.3 (2)	H8A—C8—H8B	108.1
C7—N1—N2	115.01 (18)	N3—C9—N2	110.8 (2)
C9—N2—C10	105.32 (18)	N3—C9—S1	128.51 (19)
C9—N2—N1	127.42 (18)	N2—C9—S1	120.69 (17)
C10—N2—N1	125.99 (18)	N4—C10—N2	108.5 (2)
C9—N3—N4	106.28 (19)	N4—C10—C11	123.9 (2)
C10—N4—N3	109.10 (19)	N2—C10—C11	127.44 (19)
F1—C1—C2	118.2 (2)	C16—C11—C12	117.7 (2)
F1—C1—C6	118.2 (2)	C16—C11—C10	117.7 (2)
C2—C1—C6	123.6 (2)	C12—C11—C10	124.6 (2)
C1—C2—C3	116.8 (2)	C13—C12—C11	120.6 (2)
C1—C2—H2	121.6	C13—C12—H12	119.7
C3—C2—H2	121.6	C11—C12—H12	119.7
F2—C3—C2	117.9 (2)	C12—C13—C14	120.7 (2)
F2—C3—C4	118.7 (2)	C12—C13—H13	119.7
C2—C3—C4	123.3 (2)	C14—C13—H13	119.7
C3—C4—C5	116.7 (2)	O1—C14—C15	124.9 (2)
C3—C4—C7	122.5 (2)	O1—C14—C13	116.0 (2)
C5—C4—C7	120.8 (2)	C15—C14—C13	119.1 (2)
C6—C5—C4	122.1 (2)	C16—C15—C14	119.9 (2)
C6—C5—H5	118.9	C16—C15—H15	120.0
C4—C5—H5	118.9	C14—C15—H15	120.0
C1—C6—C5	117.5 (2)	C15—C16—C11	121.9 (2)
C1—C6—H6	121.3	C15—C16—H16	119.0
C5—C6—H6	121.3	C11—C16—H16	119.0
N1—C7—C4	115.65 (19)	O1—C17—H17A	109.5
N1—C7—C8	123.5 (2)	O1—C17—H17B	109.5
C4—C7—C8	120.73 (19)	H17A—C17—H17B	109.5
C7—C8—S1	110.81 (16)	O1—C17—H17C	109.5
C7—C8—H8A	109.5	H17A—C17—H17C	109.5
S1—C8—H8A	109.5	H17B—C17—H17C	109.5
C7—C8—H8B	109.5
C7—N1—N2—C9	29.9 (3)	N1—N2—C9—N3	167.43 (19)
C7—N1—N2—C10	−165.0 (2)	C10—N2—C9—S1	−179.22 (16)
C9—N3—N4—C10	−0.7 (3)	N1—N2—C9—S1	−11.6 (3)
F1—C1—C2—C3	178.2 (2)	C8—S1—C9—N3	153.0 (2)
C6—C1—C2—C3	−1.4 (4)	C8—S1—C9—N2	−28.1 (2)
C1—C2—C3—F2	−175.1 (2)	N3—N4—C10—N2	0.5 (3)
C1—C2—C3—C4	1.6 (4)	N3—N4—C10—C11	176.0 (2)
F2—C3—C4—C5	175.9 (2)	C9—N2—C10—N4	−0.2 (2)
C2—C3—C4—C5	−0.8 (4)	N1—N2—C10—N4	−168.08 (19)
F2—C3—C4—C7	−3.1 (3)	C9—N2—C10—C11	−175.5 (2)
C2—C3—C4—C7	−179.7 (2)	N1—N2—C10—C11	16.7 (3)
C3—C4—C5—C6	−0.3 (4)	N4—C10—C11—C16	−14.7 (3)
C7—C4—C5—C6	178.6 (2)	N2—C10—C11—C16	159.9 (2)
F1—C1—C6—C5	−179.2 (2)	N4—C10—C11—C12	165.5 (2)
C2—C1—C6—C5	0.3 (4)	N2—C10—C11—C12	−19.9 (4)
C4—C5—C6—C1	0.6 (4)	C16—C11—C12—C13	−0.7 (4)
N2—N1—C7—C4	−179.02 (17)	C10—C11—C12—C13	179.1 (2)
N2—N1—C7—C8	5.4 (3)	C11—C12—C13—C14	0.2 (4)
C3—C4—C7—N1	134.7 (2)	C17—O1—C14—C15	1.1 (4)
C5—C4—C7—N1	−44.2 (3)	C17—O1—C14—C13	−179.9 (2)
C3—C4—C7—C8	−49.6 (3)	C12—C13—C14—O1	−178.3 (2)
C5—C4—C7—C8	131.5 (2)	C12—C13—C14—C15	0.7 (4)
N1—C7—C8—S1	−50.3 (3)	O1—C14—C15—C16	177.9 (2)
C4—C7—C8—S1	134.33 (18)	C13—C14—C15—C16	−1.1 (4)
C9—S1—C8—C7	53.25 (18)	C14—C15—C16—C11	0.5 (4)
N4—N3—C9—N2	0.5 (3)	C12—C11—C16—C15	0.4 (3)
N4—N3—C9—S1	179.45 (18)	C10—C11—C16—C15	−179.4 (2)
C10—N2—C9—N3	−0.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1^i	0.93	2.50	3.241 (3)	137
C8—H8A···F2	0.97	2.44	2.976 (3)	115
C8—H8A···N4^ii	0.97	2.48	3.394 (3)	156
C12—H12···N1	0.93	2.42	3.042 (3)	124
C15—H15···F1^iii	0.93	2.54	3.458 (3)	171
C16—H16···N4	0.93	2.54	2.862 (3)	101

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x, y−1, z.