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

The title compound, C₁₃H₁₂F₂N₄S, was prepared by the reaction of propanoic acid and thio­carbohydrazide. The bond lengths in the triazole ring show normal values.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.064
• wR factor = 0.132
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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

Crystal data

C13H12F2N4S	F(000) = 608
Mr = 294.33	Dx = 1.484 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1299 reflections
a = 12.6930 (14) Å	θ = 2.8–24.1°
b = 14.5268 (16) Å	µ = 0.26 mm^−1
c = 7.2715 (8) Å	T = 298 K
β = 100.667 (2)°	Block, colorless
V = 1317.6 (3) Å^3	0.21 × 0.19 × 0.08 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	2375 independent reflections
Radiation source: fine-focus sealed tube	1974 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 25.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→15
Tmin = 0.937, Tmax = 0.969	k = −16→17
6940 measured reflections	l = −8→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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0433P)^2 + 0.8585P] where P = (Fo^2 + 2Fc^2)/3
2375 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.30 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	0.53450 (6)	0.82851 (6)	0.20194 (12)	0.0439 (3)
F1	−0.03189 (19)	0.58687 (17)	0.1204 (4)	0.0962 (9)
N1	0.30719 (19)	0.90677 (16)	0.2227 (3)	0.0359 (6)
N2	0.39521 (19)	0.96393 (15)	0.2331 (3)	0.0355 (6)
N3	0.5616 (2)	1.01362 (18)	0.2750 (4)	0.0479 (7)
N4	0.4937 (2)	1.08668 (18)	0.3037 (4)	0.0475 (7)
F2	0.09515 (15)	0.88649 (13)	0.1293 (3)	0.0689 (7)
C1	0.0517 (3)	0.6450 (3)	0.1219 (5)	0.0567 (10)
C2	0.0326 (3)	0.7371 (3)	0.1277 (5)	0.0556 (9)
H2	−0.0358	0.7594	0.1301	0.067*
C3	0.1173 (2)	0.7959 (2)	0.1300 (4)	0.0425 (8)
C4	0.2211 (2)	0.76568 (19)	0.1292 (4)	0.0332 (7)
C5	0.2342 (2)	0.6706 (2)	0.1213 (4)	0.0399 (7)
H5	0.3020	0.6474	0.1175	0.048*
C6	0.1511 (3)	0.6099 (2)	0.1188 (5)	0.0505 (9)
H6	0.1622	0.5467	0.1152	0.061*
C7	0.3134 (2)	0.8292 (2)	0.1401 (4)	0.0332 (7)
C8	0.4077 (2)	0.8017 (2)	0.0528 (4)	0.0393 (7)
H8A	0.4033	0.8335	−0.0657	0.047*
H8B	0.4043	0.7361	0.0276	0.047*
C9	0.5001 (2)	0.9420 (2)	0.2338 (4)	0.0372 (7)
C10	0.3956 (3)	1.0553 (2)	0.2803 (4)	0.0400 (7)
C11	0.2974 (3)	1.1077 (2)	0.2951 (5)	0.0509 (9)
H11A	0.3150	1.1536	0.3927	0.061*
H11B	0.2455	1.0659	0.3321	0.061*
C12	0.2460 (3)	1.1557 (2)	0.1129 (6)	0.0632 (10)
H12A	0.1863	1.1928	0.1367	0.076*
H12B	0.2982	1.1971	0.0756	0.076*
C13	0.2061 (3)	1.0914 (3)	−0.0464 (6)	0.0710 (12)
H13A	0.2641	1.0535	−0.0697	0.106*
H13B	0.1782	1.1264	−0.1566	0.106*
H13C	0.1504	1.0531	−0.0146	0.106*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0354 (4)	0.0443 (5)	0.0512 (5)	0.0036 (4)	0.0058 (4)	0.0005 (4)
F1	0.0653 (16)	0.0793 (17)	0.150 (3)	−0.0386 (13)	0.0341 (16)	−0.0183 (16)
N1	0.0375 (14)	0.0312 (13)	0.0390 (14)	−0.0024 (11)	0.0070 (11)	−0.0003 (11)
N2	0.0375 (14)	0.0294 (13)	0.0399 (14)	−0.0022 (11)	0.0081 (11)	−0.0006 (11)
N3	0.0445 (16)	0.0471 (16)	0.0513 (17)	−0.0093 (13)	0.0069 (13)	0.0023 (13)
N4	0.0556 (18)	0.0403 (15)	0.0466 (16)	−0.0112 (13)	0.0095 (14)	−0.0005 (13)
F2	0.0447 (12)	0.0436 (12)	0.1174 (19)	0.0107 (9)	0.0125 (12)	0.0009 (12)
C1	0.050 (2)	0.056 (2)	0.064 (2)	−0.0230 (18)	0.0102 (18)	−0.0089 (18)
C2	0.0330 (18)	0.063 (2)	0.070 (2)	−0.0023 (17)	0.0086 (16)	−0.0015 (19)
C3	0.0367 (18)	0.0417 (18)	0.0481 (19)	0.0016 (14)	0.0052 (15)	−0.0006 (15)
C4	0.0351 (17)	0.0345 (16)	0.0292 (15)	−0.0021 (12)	0.0036 (12)	−0.0003 (12)
C5	0.0392 (17)	0.0388 (17)	0.0409 (17)	−0.0006 (14)	0.0053 (14)	−0.0034 (14)
C6	0.057 (2)	0.0356 (18)	0.059 (2)	−0.0094 (16)	0.0121 (18)	−0.0062 (16)
C7	0.0352 (16)	0.0335 (15)	0.0300 (15)	0.0016 (13)	0.0036 (12)	0.0050 (13)
C8	0.0425 (18)	0.0356 (16)	0.0408 (18)	−0.0037 (13)	0.0108 (14)	−0.0050 (14)
C9	0.0378 (17)	0.0415 (18)	0.0323 (16)	−0.0034 (14)	0.0063 (13)	0.0049 (13)
C10	0.049 (2)	0.0323 (16)	0.0386 (17)	−0.0059 (14)	0.0077 (14)	0.0010 (13)
C11	0.061 (2)	0.0369 (18)	0.057 (2)	−0.0011 (16)	0.0165 (18)	−0.0094 (16)
C12	0.062 (2)	0.048 (2)	0.079 (3)	0.0120 (18)	0.011 (2)	0.001 (2)
C13	0.067 (3)	0.068 (3)	0.073 (3)	0.008 (2)	0.000 (2)	−0.002 (2)

Geometric parameters (Å, º)

S1—C9	1.733 (3)	C4—C7	1.482 (4)
S1—C8	1.809 (3)	C5—C6	1.373 (4)
F1—C1	1.355 (4)	C5—H5	0.9300
N1—C7	1.286 (3)	C6—H6	0.9300
N1—N2	1.383 (3)	C7—C8	1.510 (4)
N2—C9	1.367 (4)	C8—H8A	0.9700
N2—C10	1.371 (4)	C8—H8B	0.9700
N3—C9	1.302 (4)	C10—C11	1.481 (4)
N3—N4	1.406 (4)	C11—C12	1.532 (5)
N4—C10	1.308 (4)	C11—H11A	0.9700
F2—C3	1.346 (3)	C11—H11B	0.9700
C1—C2	1.362 (5)	C12—C13	1.502 (5)
C1—C6	1.365 (5)	C12—H12A	0.9700
C2—C3	1.371 (4)	C12—H12B	0.9700
C2—H2	0.9300	C13—H13A	0.9600
C3—C4	1.389 (4)	C13—H13B	0.9600
C4—C5	1.393 (4)	C13—H13C	0.9600
C9—S1—C8	93.83 (14)	C7—C8—H8A	109.2
C7—N1—N2	115.7 (2)	S1—C8—H8A	109.2
C9—N2—C10	105.4 (2)	C7—C8—H8B	109.2
C9—N2—N1	129.5 (2)	S1—C8—H8B	109.2
C10—N2—N1	124.1 (2)	H8A—C8—H8B	107.9
C9—N3—N4	106.2 (3)	N3—C9—N2	110.9 (3)
C10—N4—N3	108.2 (2)	N3—C9—S1	129.5 (3)
F1—C1—C2	118.0 (3)	N2—C9—S1	119.4 (2)
F1—C1—C6	119.5 (3)	N4—C10—N2	109.2 (3)
C2—C1—C6	122.6 (3)	N4—C10—C11	127.3 (3)
C1—C2—C3	117.9 (3)	N2—C10—C11	123.5 (3)
C1—C2—H2	121.0	C10—C11—C12	113.6 (3)
C3—C2—H2	121.0	C10—C11—H11A	108.8
F2—C3—C2	116.5 (3)	C12—C11—H11A	108.8
F2—C3—C4	120.4 (3)	C10—C11—H11B	108.8
C2—C3—C4	123.1 (3)	C12—C11—H11B	108.8
C3—C4—C5	115.7 (3)	H11A—C11—H11B	107.7
C3—C4—C7	122.9 (3)	C13—C12—C11	114.3 (3)
C5—C4—C7	121.3 (3)	C13—C12—H12A	108.7
C6—C5—C4	122.7 (3)	C11—C12—H12A	108.7
C6—C5—H5	118.6	C13—C12—H12B	108.7
C4—C5—H5	118.6	C11—C12—H12B	108.7
C1—C6—C5	118.0 (3)	H12A—C12—H12B	107.6
C1—C6—H6	121.0	C12—C13—H13A	109.5
C5—C6—H6	121.0	C12—C13—H13B	109.5
N1—C7—C4	117.1 (3)	H13A—C13—H13B	109.5
N1—C7—C8	123.4 (3)	C12—C13—H13C	109.5
C4—C7—C8	119.6 (3)	H13A—C13—H13C	109.5
C7—C8—S1	112.2 (2)	H13B—C13—H13C	109.5
C7—N1—N2—C9	−26.7 (4)	C5—C4—C7—C8	29.5 (4)
C7—N1—N2—C10	166.2 (3)	N1—C7—C8—S1	44.4 (3)
C9—N3—N4—C10	0.7 (3)	C4—C7—C8—S1	−136.8 (2)
F1—C1—C2—C3	179.7 (3)	C9—S1—C8—C7	−51.7 (2)
C6—C1—C2—C3	0.2 (6)	N4—N3—C9—N2	0.2 (3)
C1—C2—C3—F2	177.8 (3)	N4—N3—C9—S1	−174.0 (2)
C1—C2—C3—C4	−0.9 (5)	C10—N2—C9—N3	−0.9 (3)
F2—C3—C4—C5	−177.1 (3)	N1—N2—C9—N3	−169.9 (3)
C2—C3—C4—C5	1.5 (5)	C10—N2—C9—S1	173.9 (2)
F2—C3—C4—C7	4.1 (5)	N1—N2—C9—S1	4.9 (4)
C2—C3—C4—C7	−177.2 (3)	C8—S1—C9—N3	−154.8 (3)
C3—C4—C5—C6	−1.5 (4)	C8—S1—C9—N2	31.4 (2)
C7—C4—C5—C6	177.3 (3)	N3—N4—C10—N2	−1.2 (3)
F1—C1—C6—C5	−179.7 (3)	N3—N4—C10—C11	−179.5 (3)
C2—C1—C6—C5	−0.2 (6)	C9—N2—C10—N4	1.3 (3)
C4—C5—C6—C1	0.9 (5)	N1—N2—C10—N4	171.1 (3)
N2—N1—C7—C4	179.1 (2)	C9—N2—C10—C11	179.7 (3)
N2—N1—C7—C8	−2.1 (4)	N1—N2—C10—C11	−10.6 (4)
C3—C4—C7—N1	27.0 (4)	N4—C10—C11—C12	86.3 (4)
C5—C4—C7—N1	−151.6 (3)	N2—C10—C11—C12	−91.7 (4)
C3—C4—C7—C8	−151.8 (3)	C10—C11—C12—C13	63.5 (4)