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

In the title compound, C₁₃H₁₂F₂N₄OS, the thia­diazine ring adopts a screw-boat conformation. Weak O—H...N hydrogen bonds are found in the crystal structure. These link the mol­ecules into a zigzag chain.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.062
• wR factor = 0.166
• 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-(3-hydroxypropyl)-7H-1,2,4- triazolo[3,4-b][1,3,4]thiadiazine

Crystal data

C13H12F2N4OS	F(000) = 640
Mr = 310.33	Dx = 1.509 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2391 reflections
a = 16.0230 (14) Å	θ = 2.3–25.1°
b = 11.0368 (10) Å	µ = 0.26 mm^−1
c = 7.8738 (7) Å	T = 298 K
β = 101.174 (2)°	Block, colorless
V = 1366.0 (2) Å^3	0.38 × 0.28 × 0.08 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	2454 independent reflections
Radiation source: fine-focus sealed tube	2269 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 25.2°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −19→18
Tmin = 0.906, Tmax = 0.969	k = −13→10
7092 measured reflections	l = −9→8

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.166	H-atom parameters constrained
S = 1.27	w = 1/[σ^2(Fo^2) + (0.0803P)^2 + 0.4963P] where P = (Fo^2 + 2Fc^2)/3
2454 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.32 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	0.86205 (5)	0.30131 (7)	0.02864 (11)	0.0452 (3)
F1	0.97050 (12)	0.61200 (18)	0.1265 (4)	0.0767 (7)
F2	0.89332 (16)	1.01841 (17)	0.0490 (3)	0.0739 (7)
O1	0.4116 (2)	0.5129 (3)	0.1878 (4)	0.0859 (10)
H1	0.4020	0.5692	0.2493	0.129*
N1	0.74191 (14)	0.4995 (2)	0.1420 (3)	0.0350 (6)
N2	0.71763 (14)	0.3783 (2)	0.1226 (3)	0.0330 (5)
N3	0.72191 (16)	0.1807 (2)	0.0935 (4)	0.0426 (6)
N4	0.64671 (16)	0.2141 (2)	0.1479 (4)	0.0424 (6)
C1	0.90852 (19)	0.6980 (3)	0.0939 (5)	0.0448 (8)
C2	0.9337 (2)	0.8161 (3)	0.0898 (5)	0.0533 (9)
H2	0.9909	0.8376	0.1072	0.064*
C3	0.8705 (2)	0.9011 (3)	0.0586 (4)	0.0461 (8)
C4	0.7862 (2)	0.8729 (3)	0.0379 (4)	0.0470 (8)
H4	0.7449	0.9332	0.0201	0.056*
C5	0.76378 (19)	0.7525 (3)	0.0438 (4)	0.0408 (7)
H5	0.7066	0.7319	0.0300	0.049*
C6	0.82504 (17)	0.6609 (2)	0.0703 (4)	0.0341 (6)
C7	0.79985 (17)	0.5318 (2)	0.0607 (4)	0.0345 (6)
C8	0.8364 (2)	0.4511 (3)	−0.0607 (4)	0.0399 (7)
H8A	0.8875	0.4882	−0.0859	0.048*
H8B	0.7957	0.4438	−0.1688	0.048*
C9	0.76282 (18)	0.2808 (2)	0.0809 (4)	0.0347 (6)
C10	0.64569 (18)	0.3315 (2)	0.1651 (4)	0.0355 (7)
C11	0.57841 (18)	0.4055 (3)	0.2206 (4)	0.0408 (7)
H11A	0.5661	0.4749	0.1442	0.049*
H11B	0.5996	0.4357	0.3366	0.049*
C12	0.4967 (2)	0.3360 (3)	0.2195 (5)	0.0494 (8)
H12A	0.4728	0.3112	0.1019	0.059*
H12B	0.5094	0.2634	0.2891	0.059*
C13	0.4322 (2)	0.4100 (3)	0.2887 (5)	0.0554 (9)
H13A	0.3815	0.3620	0.2880	0.066*
H13B	0.4551	0.4334	0.4073	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0404 (5)	0.0322 (5)	0.0679 (6)	0.0071 (3)	0.0227 (4)	0.0042 (3)
F1	0.0377 (11)	0.0442 (11)	0.144 (2)	0.0070 (9)	0.0077 (12)	−0.0022 (13)
F2	0.0902 (16)	0.0271 (10)	0.1149 (19)	−0.0131 (10)	0.0454 (14)	−0.0015 (10)
O1	0.104 (2)	0.089 (2)	0.0694 (18)	0.0534 (19)	0.0278 (17)	0.0014 (16)
N1	0.0354 (13)	0.0268 (12)	0.0433 (14)	−0.0009 (10)	0.0092 (10)	−0.0006 (10)
N2	0.0331 (12)	0.0245 (12)	0.0427 (13)	−0.0021 (9)	0.0106 (10)	0.0008 (10)
N3	0.0427 (14)	0.0274 (13)	0.0597 (17)	0.0012 (10)	0.0149 (12)	0.0018 (11)
N4	0.0413 (14)	0.0311 (14)	0.0575 (17)	−0.0009 (11)	0.0166 (12)	0.0020 (11)
C1	0.0365 (16)	0.0340 (17)	0.065 (2)	0.0045 (13)	0.0139 (15)	−0.0014 (14)
C2	0.0429 (18)	0.0419 (19)	0.079 (2)	−0.0124 (15)	0.0211 (17)	−0.0091 (17)
C3	0.063 (2)	0.0249 (16)	0.0560 (19)	−0.0070 (14)	0.0257 (16)	−0.0053 (13)
C4	0.055 (2)	0.0295 (16)	0.058 (2)	0.0089 (14)	0.0134 (16)	−0.0009 (14)
C5	0.0379 (16)	0.0347 (16)	0.0509 (18)	0.0014 (13)	0.0115 (13)	−0.0032 (13)
C6	0.0357 (15)	0.0286 (15)	0.0399 (16)	−0.0012 (11)	0.0120 (12)	−0.0015 (12)
C7	0.0328 (15)	0.0288 (15)	0.0420 (16)	0.0005 (11)	0.0075 (12)	0.0000 (12)
C8	0.0467 (17)	0.0264 (15)	0.0510 (18)	0.0000 (12)	0.0206 (14)	0.0005 (12)
C9	0.0370 (15)	0.0268 (14)	0.0409 (16)	0.0047 (11)	0.0092 (12)	0.0016 (12)
C10	0.0375 (16)	0.0295 (15)	0.0401 (16)	−0.0017 (12)	0.0088 (12)	0.0019 (12)
C11	0.0384 (16)	0.0328 (17)	0.0544 (18)	0.0009 (12)	0.0170 (14)	−0.0015 (13)
C12	0.0410 (18)	0.0399 (18)	0.071 (2)	−0.0003 (14)	0.0202 (16)	−0.0055 (16)
C13	0.0468 (19)	0.051 (2)	0.073 (2)	−0.0041 (16)	0.0215 (18)	−0.0057 (18)

Geometric parameters (Å, º)

S1—C9	1.733 (3)	C4—C5	1.379 (4)
S1—C8	1.812 (3)	C4—H4	0.9300
F1—C1	1.362 (3)	C5—C6	1.396 (4)
F2—C3	1.352 (3)	C5—H5	0.9300
O1—C13	1.389 (4)	C6—C7	1.479 (4)
O1—H1	0.8200	C7—C8	1.505 (4)
N1—C7	1.277 (4)	C8—H8A	0.9700
N1—N2	1.393 (3)	C8—H8B	0.9700
N2—C10	1.363 (4)	C10—C11	1.484 (4)
N2—C9	1.372 (3)	C11—C12	1.516 (4)
N3—C9	1.298 (4)	C11—H11A	0.9700
N3—N4	1.404 (4)	C11—H11B	0.9700
N4—C10	1.303 (4)	C12—C13	1.499 (4)
C1—C2	1.367 (4)	C12—H12A	0.9700
C1—C6	1.377 (4)	C12—H12B	0.9700
C2—C3	1.368 (5)	C13—H13A	0.9700
C2—H2	0.9300	C13—H13B	0.9700
C3—C4	1.365 (5)
C9—S1—C8	93.56 (13)	C7—C8—H8A	109.1
C13—O1—H1	109.5	S1—C8—H8A	109.1
C7—N1—N2	115.3 (2)	C7—C8—H8B	109.1
C10—N2—C9	105.8 (2)	S1—C8—H8B	109.1
C10—N2—N1	124.6 (2)	H8A—C8—H8B	107.9
C9—N2—N1	129.1 (2)	N3—C9—N2	110.6 (2)
C9—N3—N4	106.0 (2)	N3—C9—S1	129.0 (2)
C10—N4—N3	108.7 (2)	N2—C9—S1	120.3 (2)
F1—C1—C2	117.5 (3)	N4—C10—N2	108.8 (2)
F1—C1—C6	118.2 (3)	N4—C10—C11	127.0 (3)
C2—C1—C6	124.4 (3)	N2—C10—C11	124.1 (2)
C1—C2—C3	116.5 (3)	C10—C11—C12	113.3 (2)
C1—C2—H2	121.8	C10—C11—H11A	108.9
C3—C2—H2	121.8	C12—C11—H11A	108.9
F2—C3—C4	119.0 (3)	C10—C11—H11B	108.9
F2—C3—C2	117.9 (3)	C12—C11—H11B	108.9
C4—C3—C2	123.2 (3)	H11A—C11—H11B	107.7
C3—C4—C5	118.3 (3)	C13—C12—C11	112.2 (3)
C3—C4—H4	120.9	C13—C12—H12A	109.2
C5—C4—H4	120.9	C11—C12—H12A	109.2
C4—C5—C6	121.5 (3)	C13—C12—H12B	109.2
C4—C5—H5	119.3	C11—C12—H12B	109.2
C6—C5—H5	119.3	H12A—C12—H12B	107.9
C1—C6—C5	116.2 (3)	O1—C13—C12	110.0 (3)
C1—C6—C7	122.8 (3)	O1—C13—H13A	109.7
C5—C6—C7	120.9 (3)	C12—C13—H13A	109.7
N1—C7—C6	117.5 (2)	O1—C13—H13B	109.7
N1—C7—C8	124.3 (2)	C12—C13—H13B	109.7
C6—C7—C8	117.8 (2)	H13A—C13—H13B	108.2
C7—C8—S1	112.3 (2)
C7—N1—N2—C10	−164.9 (3)	N1—C7—C8—S1	−45.9 (4)
C7—N1—N2—C9	24.4 (4)	C6—C7—C8—S1	141.8 (2)
C9—N3—N4—C10	0.1 (3)	C9—S1—C8—C7	50.7 (2)
F1—C1—C2—C3	−179.4 (3)	N4—N3—C9—N2	−0.7 (3)
C6—C1—C2—C3	−0.4 (5)	N4—N3—C9—S1	177.0 (2)
C1—C2—C3—F2	−178.2 (3)	C10—N2—C9—N3	1.0 (3)
C1—C2—C3—C4	2.1 (5)	N1—N2—C9—N3	173.1 (3)
F2—C3—C4—C5	178.5 (3)	C10—N2—C9—S1	−176.9 (2)
C2—C3—C4—C5	−1.9 (5)	N1—N2—C9—S1	−4.8 (4)
C3—C4—C5—C6	0.0 (5)	C8—S1—C9—N3	152.4 (3)
F1—C1—C6—C5	177.6 (3)	C8—S1—C9—N2	−30.2 (3)
C2—C1—C6—C5	−1.3 (5)	N3—N4—C10—N2	0.5 (3)
F1—C1—C6—C7	−6.5 (5)	N3—N4—C10—C11	−179.8 (3)
C2—C1—C6—C7	174.6 (3)	C9—N2—C10—N4	−0.9 (3)
C4—C5—C6—C1	1.5 (4)	N1—N2—C10—N4	−173.4 (2)
C4—C5—C6—C7	−174.4 (3)	C9—N2—C10—C11	179.4 (3)
N2—N1—C7—C6	177.2 (2)	N1—N2—C10—C11	6.9 (4)
N2—N1—C7—C8	4.8 (4)	N4—C10—C11—C12	−13.2 (5)
C1—C6—C7—N1	137.2 (3)	N2—C10—C11—C12	166.4 (3)
C5—C6—C7—N1	−47.1 (4)	C10—C11—C12—C13	175.7 (3)
C1—C6—C7—C8	−50.0 (4)	C11—C12—C13—O1	60.4 (4)
C5—C6—C7—C8	125.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N4^i	0.82	2.02	2.819 (4)	166

Symmetry code: (i) −x+1, y+1/2, −z+1/2.