6-(1-Adamant-yl)-3-(2-fluoro-phen-yl)-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

In the title compound, C(19)H(19)FN(4)S, the planes of the 2-fluoro-phenyl and 1,2,4-triazolo[3,4-b][1,3,4]thia-diazole ring systems are oriented at a dihedral angle of 48.98 (6)°. In the crystal, weak C-H⋯S and C-H⋯π inter-actions may help to establish the packing and π-π inter-actions between the centroids of the benzene rings at a distance of 3.8792 (13) Å occur.

Related literature

For a related structure, see: Holm et al. (2008 ▶). For our previous studies on related compounds, see: Akhtar et al. (2007 ▶, 2008a ▶,b ▶). For background to the biological activity of related compounds, see: El-Emam et al. (2004 ▶); Kadi et al. (2007 ▶); Zhang et al. (2002 ▶).

Experimental

Crystal data

C19H19FN4S

M = 354.44

Orthorhombic,

a = 13.2684 (9) Å

b = 12.4293 (9) Å

c = 20.2231 (15) Å

V = 3335.1 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.25 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.945, T max = 0.956

22695 measured reflections

4486 independent reflections

3116 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.136

S = 1.04

4486 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019692/hb2984sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019692/hb2984Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H19FN4S	F(000) = 1488
Mr = 354.44	Dx = 1.412 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3116 reflections
a = 13.2684 (9) Å	θ = 2.5–29.1°
b = 12.4293 (9) Å	µ = 0.21 mm−1
c = 20.2231 (15) Å	T = 296 K
V = 3335.1 (4) Å3	Prism, colourless
Z = 8	0.25 × 0.22 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	4486 independent reflections
Radiation source: fine-focus sealed tube	3116 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 7.40 pixels mm-1	θmax = 29.1°, θmin = 2.5°
ω scans	h = −12→18
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −17→14
Tmin = 0.945, Tmax = 0.956	l = −26→27
22695 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0579P)2 + 1.3259P] where P = (Fo2 + 2Fc2)/3
4486 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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.

	x	y	z	Uiso*/Ueq
S1	0.25232 (4)	−0.15058 (4)	0.23126 (2)	0.0517 (2)
F1	0.35571 (14)	−0.27396 (11)	0.52074 (7)	0.0839 (6)
N1	0.20243 (13)	−0.22822 (13)	0.41446 (9)	0.0543 (6)
N2	0.17459 (14)	−0.24778 (14)	0.34844 (9)	0.0591 (6)
N3	0.29443 (10)	−0.12526 (11)	0.35182 (7)	0.0360 (4)
N4	0.36117 (10)	−0.05549 (11)	0.32199 (7)	0.0343 (4)
C1	0.32252 (13)	−0.10525 (14)	0.47314 (9)	0.0392 (5)
C2	0.36251 (16)	−0.16551 (17)	0.52410 (10)	0.0517 (6)
C3	0.41073 (19)	−0.1200 (2)	0.57717 (10)	0.0639 (8)
C4	0.41784 (17)	−0.0094 (2)	0.58048 (10)	0.0611 (8)
C5	0.37749 (16)	0.05301 (18)	0.53119 (10)	0.0549 (7)
C6	0.33120 (14)	0.00584 (15)	0.47758 (9)	0.0463 (6)
C7	0.27374 (13)	−0.15494 (14)	0.41576 (9)	0.0403 (5)
C8	0.23167 (13)	−0.18403 (14)	0.31343 (10)	0.0437 (5)
C9	0.34740 (12)	−0.06062 (13)	0.25887 (8)	0.0348 (5)
C10	0.40431 (12)	0.00535 (13)	0.20943 (8)	0.0337 (4)
C11	0.48759 (15)	0.07039 (18)	0.24376 (9)	0.0504 (6)
C12	0.54359 (15)	0.13979 (18)	0.19241 (10)	0.0543 (7)
C13	0.47109 (16)	0.21626 (17)	0.15982 (11)	0.0581 (7)
C14	0.38813 (17)	0.15387 (18)	0.12638 (12)	0.0626 (8)
C15	0.33138 (15)	0.08502 (16)	0.17677 (11)	0.0527 (6)
C16	0.4512 (2)	−0.06639 (17)	0.15637 (11)	0.0657 (8)
C17	0.5082 (3)	0.0039 (2)	0.10590 (12)	0.0802 (9)
C18	0.59042 (18)	0.0674 (2)	0.14102 (13)	0.0730 (9)
C19	0.4329 (3)	0.0822 (2)	0.07399 (11)	0.0855 (10)
H3	0.43812	−0.16293	0.61028	0.0767*
H4	0.45004	0.02286	0.61619	0.0733*
H5	0.38143	0.12757	0.53400	0.0658*
H6	0.30545	0.04888	0.44397	0.0555*
H11A	0.45818	0.11629	0.27742	0.0604*
H11B	0.53468	0.02185	0.26512	0.0604*
H12	0.59673	0.18097	0.21460	0.0651*
H13A	0.44245	0.26409	0.19273	0.0697*
H13B	0.50652	0.25966	0.12744	0.0697*
H14	0.34099	0.20433	0.10564	0.0751*
H15A	0.30145	0.13091	0.21022	0.0633*
H15B	0.27764	0.04595	0.15483	0.0633*
H16A	0.49735	−0.11705	0.17670	0.0789*
H16B	0.39877	−0.10692	0.13405	0.0789*
H17	0.53836	−0.04191	0.07176	0.0963*
H18A	0.62742	0.11032	0.10915	0.0876*
H18B	0.63734	0.01826	0.16203	0.0876*
H19A	0.37972	0.04208	0.05216	0.1027*
H19B	0.46694	0.12570	0.04103	0.1027*

	U11	U22	U33	U12	U13	U23
S1	0.0578 (3)	0.0481 (3)	0.0492 (3)	−0.0163 (2)	−0.0141 (2)	−0.0060 (2)
F1	0.1293 (14)	0.0492 (8)	0.0733 (9)	0.0040 (8)	−0.0198 (9)	0.0189 (7)
N1	0.0552 (10)	0.0455 (9)	0.0623 (11)	−0.0141 (8)	−0.0018 (8)	0.0070 (8)
N2	0.0611 (10)	0.0483 (9)	0.0678 (12)	−0.0202 (8)	−0.0068 (9)	0.0020 (9)
N3	0.0342 (7)	0.0312 (7)	0.0427 (8)	−0.0025 (5)	−0.0031 (6)	−0.0002 (6)
N4	0.0330 (7)	0.0324 (7)	0.0375 (7)	−0.0016 (5)	−0.0019 (6)	−0.0014 (6)
C1	0.0351 (8)	0.0425 (9)	0.0401 (9)	−0.0011 (7)	0.0052 (7)	0.0042 (7)
C2	0.0615 (12)	0.0487 (11)	0.0450 (10)	0.0004 (9)	0.0043 (9)	0.0110 (9)
C3	0.0733 (15)	0.0777 (16)	0.0407 (10)	0.0016 (12)	−0.0069 (10)	0.0148 (10)
C4	0.0616 (13)	0.0810 (16)	0.0406 (10)	−0.0128 (12)	0.0007 (9)	−0.0047 (10)
C5	0.0585 (12)	0.0528 (12)	0.0533 (12)	−0.0067 (10)	0.0026 (10)	−0.0077 (9)
C6	0.0470 (10)	0.0432 (10)	0.0487 (10)	−0.0015 (8)	−0.0022 (8)	0.0024 (8)
C7	0.0390 (9)	0.0342 (8)	0.0478 (10)	−0.0005 (7)	0.0006 (7)	0.0048 (7)
C8	0.0425 (9)	0.0356 (9)	0.0530 (10)	−0.0064 (7)	−0.0083 (8)	−0.0036 (8)
C9	0.0338 (8)	0.0313 (7)	0.0394 (9)	0.0013 (6)	−0.0055 (7)	−0.0054 (7)
C10	0.0355 (8)	0.0340 (8)	0.0315 (7)	0.0043 (6)	−0.0038 (6)	−0.0048 (6)
C11	0.0423 (10)	0.0682 (13)	0.0406 (9)	−0.0147 (9)	−0.0045 (8)	0.0014 (9)
C12	0.0401 (10)	0.0728 (14)	0.0499 (11)	−0.0137 (9)	−0.0001 (8)	0.0052 (10)
C13	0.0550 (12)	0.0478 (11)	0.0716 (14)	−0.0041 (9)	0.0134 (11)	0.0044 (10)
C14	0.0527 (12)	0.0602 (13)	0.0748 (15)	0.0024 (10)	−0.0127 (11)	0.0291 (12)
C15	0.0402 (10)	0.0453 (10)	0.0727 (13)	0.0009 (8)	−0.0095 (9)	0.0140 (10)
C16	0.0922 (18)	0.0451 (11)	0.0599 (13)	0.0105 (11)	0.0243 (12)	−0.0122 (10)
C17	0.123 (2)	0.0619 (15)	0.0558 (13)	0.0071 (15)	0.0433 (15)	−0.0135 (12)
C18	0.0537 (13)	0.0819 (17)	0.0834 (17)	0.0217 (12)	0.0285 (12)	0.0241 (14)
C19	0.114 (2)	0.105 (2)	0.0374 (11)	−0.0375 (19)	−0.0114 (13)	0.0115 (13)

S1—C8	1.735 (2)	C14—C15	1.529 (3)
S1—C9	1.7758 (17)	C14—C19	1.506 (4)
F1—C2	1.353 (3)	C16—C17	1.542 (4)
N1—N2	1.407 (3)	C17—C18	1.522 (4)
N1—C7	1.314 (2)	C17—C19	1.537 (5)
N2—C8	1.305 (3)	C3—H3	0.9300
N3—N4	1.3784 (19)	C4—H4	0.9300
N3—C7	1.372 (2)	C5—H5	0.9300
N3—C8	1.353 (2)	C6—H6	0.9300
N4—C9	1.291 (2)	C11—H11A	0.9700
C1—C2	1.380 (3)	C11—H11B	0.9700
C1—C6	1.389 (3)	C12—H12	0.9800
C1—C7	1.465 (3)	C13—H13A	0.9700
C2—C3	1.372 (3)	C13—H13B	0.9700
C3—C4	1.380 (4)	C14—H14	0.9800
C4—C5	1.372 (3)	C15—H15A	0.9700
C5—C6	1.377 (3)	C15—H15B	0.9700
C9—C10	1.497 (2)	C16—H16A	0.9700
C10—C11	1.535 (3)	C16—H16B	0.9700
C10—C15	1.534 (3)	C17—H17	0.9800
C10—C16	1.528 (3)	C18—H18A	0.9700
C11—C12	1.541 (3)	C18—H18B	0.9700
C12—C13	1.504 (3)	C19—H19A	0.9700
C12—C18	1.509 (3)	C19—H19B	0.9700
C13—C14	1.507 (3)
C8—S1—C9	87.82 (8)	C2—C3—H3	121.00
N2—N1—C7	109.15 (16)	C4—C3—H3	121.00
N1—N2—C8	104.93 (16)	C3—C4—H4	120.00
N4—N3—C7	135.23 (14)	C5—C4—H4	120.00
N4—N3—C8	118.95 (14)	C4—C5—H5	120.00
C7—N3—C8	105.81 (14)	C6—C5—H5	120.00
N3—N4—C9	108.10 (13)	C1—C6—H6	120.00
C2—C1—C6	117.36 (17)	C5—C6—H6	120.00
C2—C1—C7	122.17 (17)	C10—C11—H11A	110.00
C6—C1—C7	120.47 (16)	C10—C11—H11B	110.00
F1—C2—C1	118.53 (18)	C12—C11—H11A	110.00
F1—C2—C3	118.78 (19)	C12—C11—H11B	110.00
C1—C2—C3	122.7 (2)	H11A—C11—H11B	108.00
C2—C3—C4	118.7 (2)	C11—C12—H12	109.00
C3—C4—C5	120.1 (2)	C13—C12—H12	109.00
C4—C5—C6	120.4 (2)	C18—C12—H12	109.00
C1—C6—C5	120.75 (18)	C12—C13—H13A	110.00
N1—C7—N3	108.16 (16)	C12—C13—H13B	110.00
N1—C7—C1	128.78 (17)	C14—C13—H13A	110.00
N3—C7—C1	122.99 (15)	C14—C13—H13B	110.00
S1—C8—N2	139.20 (16)	H13A—C13—H13B	108.00
S1—C8—N3	108.85 (13)	C13—C14—H14	109.00
N2—C8—N3	111.95 (18)	C15—C14—H14	109.00
S1—C9—N4	116.26 (12)	C19—C14—H14	109.00
S1—C9—C10	119.54 (12)	C10—C15—H15A	110.00
N4—C9—C10	124.18 (15)	C10—C15—H15B	110.00
C9—C10—C11	110.45 (14)	C14—C15—H15A	110.00
C9—C10—C15	108.84 (14)	C14—C15—H15B	110.00
C9—C10—C16	110.78 (14)	H15A—C15—H15B	108.00
C11—C10—C15	107.99 (15)	C10—C16—H16A	110.00
C11—C10—C16	109.38 (16)	C10—C16—H16B	110.00
C15—C10—C16	109.35 (15)	C17—C16—H16A	110.00
C10—C11—C12	109.70 (15)	C17—C16—H16B	110.00
C11—C12—C13	109.91 (17)	H16A—C16—H16B	108.00
C11—C12—C18	109.21 (18)	C16—C17—H17	110.00
C13—C12—C18	109.78 (18)	C18—C17—H17	110.00
C12—C13—C14	109.79 (18)	C19—C17—H17	110.00
C13—C14—C15	110.41 (19)	C12—C18—H18A	110.00
C13—C14—C19	109.4 (2)	C12—C18—H18B	110.00
C15—C14—C19	109.39 (19)	C17—C18—H18A	110.00
C10—C15—C14	109.73 (16)	C17—C18—H18B	110.00
C10—C16—C17	109.51 (17)	H18A—C18—H18B	108.00
C16—C17—C18	109.7 (2)	C14—C19—H19A	110.00
C16—C17—C19	108.5 (3)	C14—C19—H19B	110.00
C18—C17—C19	109.5 (2)	C17—C19—H19A	110.00
C12—C18—C17	109.6 (2)	C17—C19—H19B	110.00
C14—C19—C17	109.61 (19)	H19A—C19—H19B	108.00
C9—S1—C8—N2	−179.0 (2)	C4—C5—C6—C1	1.5 (3)
C9—S1—C8—N3	1.05 (13)	S1—C9—C10—C11	−175.71 (12)
C8—S1—C9—N4	−0.64 (14)	S1—C9—C10—C15	65.90 (17)
C8—S1—C9—C10	−179.31 (14)	S1—C9—C10—C16	−54.36 (19)
C7—N1—N2—C8	−0.1 (2)	N4—C9—C10—C11	5.7 (2)
N2—N1—C7—N3	−0.2 (2)	N4—C9—C10—C15	−112.66 (18)
N2—N1—C7—C1	176.70 (17)	N4—C9—C10—C16	127.08 (18)
N1—N2—C8—S1	−179.67 (17)	C9—C10—C11—C12	−178.63 (15)
N1—N2—C8—N3	0.3 (2)	C15—C10—C11—C12	−59.7 (2)
C7—N3—N4—C9	179.60 (18)	C16—C10—C11—C12	59.2 (2)
C8—N3—N4—C9	0.9 (2)	C9—C10—C15—C14	179.60 (16)
N4—N3—C7—N1	−178.48 (16)	C11—C10—C15—C14	59.7 (2)
N4—N3—C7—C1	4.4 (3)	C16—C10—C15—C14	−59.3 (2)
C8—N3—C7—N1	0.33 (19)	C9—C10—C16—C17	179.4 (2)
C8—N3—C7—C1	−176.77 (16)	C11—C10—C16—C17	−58.6 (2)
N4—N3—C8—S1	−1.38 (18)	C15—C10—C16—C17	59.5 (2)
N4—N3—C8—N2	178.67 (15)	C10—C11—C12—C13	60.2 (2)
C7—N3—C8—S1	179.58 (12)	C10—C11—C12—C18	−60.3 (2)
C7—N3—C8—N2	−0.4 (2)	C11—C12—C13—C14	−59.2 (2)
N3—N4—C9—S1	0.02 (17)	C18—C12—C13—C14	61.0 (2)
N3—N4—C9—C10	178.62 (14)	C11—C12—C18—C17	61.0 (2)
C6—C1—C2—F1	−179.52 (18)	C13—C12—C18—C17	−59.6 (2)
C6—C1—C2—C3	−1.0 (3)	C12—C13—C14—C15	59.4 (2)
C7—C1—C2—F1	−0.3 (3)	C12—C13—C14—C19	−61.0 (2)
C7—C1—C2—C3	178.2 (2)	C13—C14—C15—C10	−60.1 (2)
C2—C1—C6—C5	−0.4 (3)	C19—C14—C15—C10	60.3 (2)
C7—C1—C6—C5	−179.61 (18)	C13—C14—C19—C17	59.7 (3)
C2—C1—C7—N1	50.7 (3)	C15—C14—C19—C17	−61.4 (3)
C2—C1—C7—N3	−132.83 (19)	C10—C16—C17—C18	59.5 (3)
C6—C1—C7—N1	−130.1 (2)	C10—C16—C17—C19	−60.1 (2)
C6—C1—C7—N3	46.3 (3)	C16—C17—C18—C12	−60.8 (3)
F1—C2—C3—C4	179.9 (2)	C19—C17—C18—C12	58.2 (3)
C1—C2—C3—C4	1.3 (3)	C16—C17—C19—C14	61.2 (3)
C2—C3—C4—C5	−0.3 (3)	C18—C17—C19—C14	−58.5 (3)
C3—C4—C5—C6	−1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···S1i	0.97	2.84	3.640 (2)	140
C12—H12···Cg1ii	0.98	2.90	3.713 (2)	140
C18—H18B···Cg1iii	0.97	2.83	3.787 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯S1i	0.97	2.84	3.640 (2)	140
C12—H12⋯Cg1ii	0.98	2.90	3.713 (2)	140
C18—H18B⋯Cg1iii	0.97	2.83	3.787 (3)	170

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the S1/C8/N3/N4/C9 ring.