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

In the title compound, C₁₁H₉FN₄S, the triazole ring is planar, whereas the thia­diazine may be regarded as having a screw-boat conformation.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.077
• wR factor = 0.169
• Data-to-parameter ratio = 12.6

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
PLAT410_ALERT_2_C Short Intra H...H Contact  H5     ..  H8B     ..       1.98 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   1 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, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

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

Crystal data

C11H9FN4S	F(000) = 512
Mr = 248.28	Dx = 1.517 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1125 reflections
a = 4.0626 (5) Å	θ = 2.5–24.2°
b = 25.530 (3) Å	µ = 0.29 mm^−1
c = 10.5576 (12) Å	T = 273 K
β = 96.909 (2)°	Block, colourless
V = 1087.1 (2) Å^3	0.17 × 0.14 × 0.13 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	1946 independent reflections
Radiation source: fine-focus sealed tube	1613 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 25.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −4→4
Tmin = 0.956, Tmax = 0.958	k = −25→30
5662 measured reflections	l = −12→11

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.169	H-atom parameters constrained
S = 1.25	w = 1/[σ^2(Fo^2) + (0.0679P)^2 + 0.5536P] where P = (Fo^2 + 2Fc^2)/3
1946 reflections	(Δ/σ)max = 0.001
155 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.21 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	0.8735 (3)	0.24151 (4)	0.72499 (11)	0.0480 (4)
F1	1.0076 (8)	0.03966 (10)	0.1569 (2)	0.0795 (9)
N1	0.7069 (8)	0.12193 (11)	0.6884 (3)	0.0364 (7)
N2	0.6314 (7)	0.14918 (11)	0.7955 (3)	0.0343 (7)
N3	0.5017 (9)	0.16212 (14)	0.9870 (3)	0.0514 (9)
N4	0.6276 (9)	0.20906 (13)	0.9430 (3)	0.0501 (9)
C1	0.9444 (11)	0.06735 (17)	0.2609 (3)	0.0473 (10)
C2	0.8215 (12)	0.04057 (16)	0.3574 (4)	0.0559 (12)
H2	0.7821	0.0047	0.3509	0.067*
C3	0.7578 (11)	0.06797 (15)	0.4643 (4)	0.0454 (10)
H3	0.6749	0.0503	0.5307	0.055*
C4	0.8152 (9)	0.12138 (14)	0.4744 (3)	0.0334 (8)
C5	0.9368 (10)	0.14676 (15)	0.3726 (3)	0.0406 (9)
H5	0.9739	0.1827	0.3770	0.049*
C6	1.0032 (11)	0.11961 (16)	0.2654 (3)	0.0461 (10)
H6	1.0860	0.1367	0.1982	0.055*
C7	0.7389 (8)	0.14991 (13)	0.5889 (3)	0.0326 (8)
C8	0.6819 (10)	0.20808 (13)	0.5836 (3)	0.0387 (9)
H8A	0.4453	0.2149	0.5738	0.046*
H8B	0.7705	0.2222	0.5094	0.046*
C9	0.7015 (9)	0.19973 (15)	0.8291 (3)	0.0389 (9)
C10	0.5113 (10)	0.12712 (15)	0.8988 (3)	0.0439 (10)
C11	0.4010 (12)	0.07198 (16)	0.9011 (4)	0.0546 (12)
H11A	0.3308	0.0643	0.9827	0.082*
H11B	0.5812	0.0493	0.8867	0.082*
H11C	0.2193	0.0666	0.8354	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0475 (7)	0.0363 (6)	0.0623 (7)	−0.0066 (5)	0.0153 (5)	−0.0098 (5)
F1	0.129 (3)	0.0714 (18)	0.0458 (14)	−0.0161 (17)	0.0434 (16)	−0.0199 (13)
N1	0.0475 (19)	0.0335 (17)	0.0299 (16)	0.0033 (14)	0.0112 (14)	−0.0032 (13)
N2	0.0423 (18)	0.0327 (16)	0.0292 (15)	0.0023 (14)	0.0091 (13)	−0.0041 (12)
N3	0.063 (2)	0.060 (2)	0.0327 (18)	0.0035 (19)	0.0137 (16)	−0.0105 (16)
N4	0.054 (2)	0.050 (2)	0.047 (2)	0.0022 (17)	0.0084 (17)	−0.0184 (16)
C1	0.063 (3)	0.056 (3)	0.0253 (19)	−0.005 (2)	0.0141 (18)	−0.0078 (18)
C2	0.081 (3)	0.040 (2)	0.051 (2)	−0.012 (2)	0.029 (2)	−0.009 (2)
C3	0.067 (3)	0.038 (2)	0.035 (2)	−0.008 (2)	0.0218 (19)	0.0013 (17)
C4	0.032 (2)	0.041 (2)	0.0283 (18)	0.0029 (16)	0.0057 (15)	0.0035 (15)
C5	0.052 (2)	0.037 (2)	0.034 (2)	−0.0041 (18)	0.0091 (17)	0.0028 (16)
C6	0.062 (3)	0.052 (3)	0.0279 (19)	−0.006 (2)	0.0164 (18)	0.0048 (17)
C7	0.0305 (19)	0.0345 (19)	0.0334 (19)	−0.0001 (16)	0.0062 (15)	0.0043 (15)
C8	0.044 (2)	0.036 (2)	0.038 (2)	0.0052 (16)	0.0135 (17)	0.0029 (16)
C9	0.036 (2)	0.041 (2)	0.040 (2)	0.0047 (17)	0.0050 (16)	−0.0097 (17)
C10	0.052 (3)	0.051 (2)	0.0293 (19)	0.006 (2)	0.0104 (17)	0.0015 (18)
C11	0.080 (3)	0.052 (3)	0.036 (2)	−0.003 (2)	0.023 (2)	0.0042 (19)

Geometric parameters (Å, º)

S1—C9	1.737 (4)	C3—C4	1.385 (5)
S1—C8	1.812 (4)	C3—H3	0.9300
F1—C1	1.356 (4)	C4—C5	1.396 (5)
N1—C7	1.289 (4)	C4—C7	1.476 (5)
N1—N2	1.393 (4)	C5—C6	1.381 (5)
N2—C9	1.360 (5)	C5—H5	0.9300
N2—C10	1.368 (4)	C6—H6	0.9300
N3—C10	1.294 (5)	C7—C8	1.503 (5)
N3—N4	1.404 (5)	C8—H8A	0.9700
N4—C9	1.296 (5)	C8—H8B	0.9700
C1—C6	1.355 (6)	C10—C11	1.479 (6)
C1—C2	1.370 (5)	C11—H11A	0.9600
C2—C3	1.378 (5)	C11—H11B	0.9600
C2—H2	0.9300	C11—H11C	0.9600
C9—S1—C8	93.81 (17)	C1—C6—H6	120.9
C7—N1—N2	116.0 (3)	C5—C6—H6	120.9
C9—N2—C10	105.5 (3)	N1—C7—C4	116.4 (3)
C9—N2—N1	128.8 (3)	N1—C7—C8	123.2 (3)
C10—N2—N1	125.2 (3)	C4—C7—C8	120.2 (3)
C10—N3—N4	107.9 (3)	C7—C8—S1	112.7 (3)
C9—N4—N3	106.5 (3)	C7—C8—H8A	109.1
C6—C1—F1	119.4 (3)	S1—C8—H8A	109.1
C6—C1—C2	123.0 (3)	C7—C8—H8B	109.1
F1—C1—C2	117.6 (4)	S1—C8—H8B	109.1
C1—C2—C3	118.5 (4)	H8A—C8—H8B	107.8
C1—C2—H2	120.8	N4—C9—N2	110.6 (3)
C3—C2—H2	120.8	N4—C9—S1	129.0 (3)
C2—C3—C4	121.1 (3)	N2—C9—S1	120.4 (3)
C2—C3—H3	119.5	N3—C10—N2	109.5 (3)
C4—C3—H3	119.5	N3—C10—C11	127.6 (4)
C3—C4—C5	118.0 (3)	N2—C10—C11	122.9 (3)
C3—C4—C7	119.9 (3)	C10—C11—H11A	109.5
C5—C4—C7	122.1 (3)	C10—C11—H11B	109.5
C6—C5—C4	121.3 (4)	H11A—C11—H11B	109.5
C6—C5—H5	119.3	C10—C11—H11C	109.5
C4—C5—H5	119.3	H11A—C11—H11C	109.5
C1—C6—C5	118.1 (3)	H11B—C11—H11C	109.5
C7—N1—N2—C9	−26.7 (5)	C5—C4—C7—C8	20.1 (5)
C7—N1—N2—C10	163.7 (3)	N1—C7—C8—S1	45.0 (4)
C10—N3—N4—C9	1.0 (4)	C4—C7—C8—S1	−139.0 (3)
C6—C1—C2—C3	−0.6 (7)	C9—S1—C8—C7	−50.6 (3)
F1—C1—C2—C3	179.6 (4)	N3—N4—C9—N2	−0.1 (4)
C1—C2—C3—C4	0.2 (7)	N3—N4—C9—S1	−178.9 (3)
C2—C3—C4—C5	0.6 (6)	C10—N2—C9—N4	−0.9 (4)
C2—C3—C4—C7	178.9 (4)	N1—N2—C9—N4	−172.1 (3)
C3—C4—C5—C6	−0.9 (6)	C10—N2—C9—S1	178.1 (3)
C7—C4—C5—C6	−179.2 (4)	N1—N2—C9—S1	6.8 (5)
F1—C1—C6—C5	−179.9 (4)	C8—S1—C9—N4	−152.1 (4)
C2—C1—C6—C5	0.2 (7)	C8—S1—C9—N2	29.2 (3)
C4—C5—C6—C1	0.5 (6)	N4—N3—C10—N2	−1.6 (4)
N2—N1—C7—C4	−179.3 (3)	N4—N3—C10—C11	−179.2 (4)
N2—N1—C7—C8	−3.2 (5)	C9—N2—C10—N3	1.5 (4)
C3—C4—C7—N1	18.2 (5)	N1—N2—C10—N3	173.2 (3)
C5—C4—C7—N1	−163.6 (3)	C9—N2—C10—C11	179.3 (4)
C3—C4—C7—C8	−158.1 (4)	N1—N2—C10—C11	−9.0 (6)