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

The title mol-ecule, C(19)H(19)FN(4)S, displays C(s) mol-ecular symmetry, in which the crystallographic mirror plane bis-ects the adamantan-1-yl unit while the 3-fluoro-phenyl triazole ring is located on the mirror plane. The F atom of the 3-fluoro-phenyl ring is positionally disordered [occupancy ratio 0.9:0.1]. In the crystal, π-π inter-actions between the triazole and phenyl rings occur [centroid-centroid distance = 3.5849 (7) Å] and weak C-H⋯F inter-actions form a ribbon propagating in [010].

Related literature

For the biological significance of fused heterocycles, see: Khan et al. (2010a ▶,b ▶); Demirbas et al. (2005 ▶); Amir et al. (2007 ▶); Ashok et al. (2007 ▶); Palekar et al. (2009 ▶); Serwar et al. (2009 ▶); Akhtar et al. (2007 ▶, 2008a ▶,b ▶). For the activity of adamantyl derivatives, see: Kadi et al. (2007 ▶); Kouatly et al. (2009 ▶); Zahid et al. (2009 ▶). For a related structure, see: Khan et al. (2009 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H19FN4S

M = 354.44

Monoclinic,

a = 11.6385 (16) Å

b = 6.6555 (5) Å

c = 11.6634 (16) Å

β = 117.379 (14)°

V = 802.25 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 173 K

0.34 × 0.30 × 0.11 mm

Data collection

Stoe IPDS-2 diffractometer

6164 measured reflections

1708 independent reflections

1223 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.074

S = 0.95

1708 reflections

154 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.26 e Å−3

Data collection: X-AREA (Stoe & Cie, 2006 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶), PLATON and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046428/kp2286sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046428/kp2286Isup2.hkl

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

C19H19FN4S	F(000) = 372
Mr = 354.44	Dx = 1.467 Mg m−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 4261 reflections
a = 11.6385 (16) Å	θ = 3.1–26.0°
b = 6.6555 (5) Å	µ = 0.22 mm−1
c = 11.6634 (16) Å	T = 173 K
β = 117.379 (14)°	Plate, colourless
V = 802.25 (17) Å3	0.34 × 0.30 × 0.11 mm
Z = 2

Stoe IPDS-2 diffractometer	1223 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 26.1°, θmin = 3.4°
φ and ω scans	h = −14→14
6164 measured reflections	k = −7→8
1708 independent reflections	l = −14→14

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ2(Fo2) + (0.0449P)2] where P = (Fo2 + 2Fc2)/3
1708 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.20 e Å−3
4 restraints	Δρmin = −0.26 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	Occ. (<1)
S1	0.42509 (5)	0.75000	0.98501 (5)	0.0307 (2)
F1A	−0.2195 (2)	0.75000	1.1429 (2)	0.0500 (6)	0.900
N1	0.17319 (15)	0.75000	0.85412 (15)	0.0251 (5)
N2	0.20898 (15)	0.75000	0.98446 (16)	0.0243 (5)
N3	0.35605 (17)	0.75000	1.18934 (17)	0.0325 (6)
N4	0.23242 (17)	0.75000	1.18047 (16)	0.0311 (6)
C1	0.27709 (18)	0.75000	0.84027 (19)	0.0249 (6)
C2	0.33636 (19)	0.75000	1.06956 (19)	0.0268 (6)
C3	0.14499 (19)	0.75000	1.05806 (19)	0.0257 (6)
C4	0.00535 (19)	0.75000	1.0101 (2)	0.0248 (6)
C5	−0.0419 (2)	0.75000	1.1000 (2)	0.0318 (7)
C6	−0.1732 (2)	0.75000	1.0556 (2)	0.0342 (7)
C7	−0.2599 (2)	0.75000	0.9272 (2)	0.0378 (8)
C8	−0.2117 (2)	0.75000	0.8390 (2)	0.0367 (8)
C9	−0.08020 (19)	0.75000	0.8790 (2)	0.0299 (7)
C10	0.27522 (18)	0.75000	0.71113 (18)	0.0254 (6)
C11	0.34448 (16)	0.9374 (3)	0.69694 (15)	0.0362 (5)
C12	0.34071 (17)	0.9366 (3)	0.56371 (15)	0.0413 (6)
C13	0.20148 (17)	0.9360 (3)	0.45854 (15)	0.0428 (6)
C14	0.1337 (2)	0.75000	0.4720 (2)	0.0382 (8)
C15	0.1355 (2)	0.75000	0.6040 (2)	0.0368 (7)
C16	0.4093 (2)	0.75000	0.5501 (2)	0.0441 (9)
F1B	−0.2859 (18)	0.75000	0.7166 (11)	0.052 (5)	0.100
H7	−0.3504 (11)	0.75000	0.902 (2)	0.0450*
H8A	−0.276 (4)	0.75000	0.7516 (18)	0.0440*	0.900
H9	−0.04830	0.75000	0.81730	0.0360*
H11A	0.30140	1.05980	0.70660	0.0440*
H11B	0.43540	0.93830	0.76530	0.0440*
H12	0.38550	1.05930	0.55460	0.0490*
H5	0.01550	0.75000	1.19000	0.0380*
H13B	0.19930	0.93710	0.37270	0.0510*
H14	0.04200	0.75000	0.40260	0.0460*
H15A	0.08990	0.87050	0.61220	0.0440*	0.500
H15B	0.08990	0.62950	0.61220	0.0440*	0.500
H16A	0.40810	0.75000	0.46460	0.0530*
H16B	0.50060	0.75000	0.61760	0.0530*
H13A	0.15650	1.05780	0.46590	0.0510*
H6B	−0.21 (3)	0.75000	1.11 (2)	0.0410*	0.100

	U11	U22	U33	U12	U13	U23
S1	0.0210 (3)	0.0411 (4)	0.0298 (3)	0.0000	0.0116 (2)	0.0000
F1A	0.0514 (10)	0.0583 (11)	0.0639 (12)	0.0000	0.0467 (9)	0.0000
N1	0.0251 (8)	0.0263 (10)	0.0252 (8)	0.0000	0.0128 (7)	0.0000
N2	0.0218 (8)	0.0275 (9)	0.0245 (8)	0.0000	0.0115 (6)	0.0000
N3	0.0268 (9)	0.0403 (12)	0.0291 (9)	0.0000	0.0118 (7)	0.0000
N4	0.0285 (9)	0.0371 (12)	0.0285 (9)	0.0000	0.0139 (7)	0.0000
C1	0.0219 (9)	0.0230 (11)	0.0301 (10)	0.0000	0.0123 (8)	0.0000
C2	0.0207 (9)	0.0285 (12)	0.0289 (10)	0.0000	0.0095 (8)	0.0000
C3	0.0283 (10)	0.0249 (12)	0.0269 (10)	0.0000	0.0153 (9)	0.0000
C4	0.0260 (10)	0.0206 (11)	0.0320 (10)	0.0000	0.0169 (9)	0.0000
C5	0.0344 (12)	0.0298 (13)	0.0361 (11)	0.0000	0.0205 (9)	0.0000
C6	0.0368 (12)	0.0282 (12)	0.0520 (14)	0.0000	0.0329 (11)	0.0000
C7	0.0270 (11)	0.0337 (14)	0.0581 (15)	0.0000	0.0243 (11)	0.0000
C8	0.0254 (11)	0.0401 (15)	0.0414 (13)	0.0000	0.0126 (10)	0.0000
C9	0.0256 (10)	0.0336 (13)	0.0326 (11)	0.0000	0.0153 (9)	0.0000
C10	0.0217 (10)	0.0288 (12)	0.0276 (10)	0.0000	0.0131 (8)	0.0000
C11	0.0436 (9)	0.0339 (10)	0.0359 (8)	−0.0108 (7)	0.0223 (7)	−0.0049 (7)
C12	0.0535 (10)	0.0393 (10)	0.0405 (9)	−0.0168 (8)	0.0298 (8)	−0.0033 (7)
C13	0.0565 (11)	0.0416 (11)	0.0355 (8)	0.0138 (8)	0.0257 (8)	0.0081 (7)
C14	0.0291 (11)	0.0576 (17)	0.0279 (11)	0.0000	0.0132 (9)	0.0000
C15	0.0232 (10)	0.0586 (17)	0.0290 (10)	0.0000	0.0123 (9)	0.0000
C16	0.0313 (12)	0.073 (2)	0.0357 (12)	0.0000	0.0220 (10)	0.0000
F1B	0.030 (7)	0.084 (12)	0.031 (7)	0.0000	0.006 (7)	0.0000

S1—C1	1.773 (2)	C10—C15	1.529 (3)
S1—C2	1.725 (2)	C11—C12	1.534 (2)
F1A—C6	1.353 (3)	C12—C13	1.517 (3)
F1B—C8	1.285 (12)	C12—C16	1.524 (3)
N1—N2	1.379 (2)	C13—C14	1.514 (3)
N1—C1	1.292 (3)	C14—C15	1.530 (3)
N2—C3	1.371 (3)	C5—H5	0.9500
N2—C2	1.353 (3)	C6—H6B	0.9 (3)
N3—N4	1.394 (3)	C7—H7	0.955 (17)
N3—C2	1.308 (3)	C8—H8A	0.95 (2)
N4—C3	1.318 (3)	C9—H9	0.9500
C1—C10	1.496 (3)	C11—H11A	0.9900
C3—C4	1.455 (3)	C11—H11B	0.9900
C4—C9	1.389 (3)	C12—H12	1.0000
C4—C5	1.390 (3)	C13—H13A	0.9900
C5—C6	1.370 (4)	C13—H13B	0.9900
C6—C7	1.368 (3)	C14—H14	1.0000
C7—C8	1.380 (3)	C15—H15A	0.9900
C8—C9	1.380 (4)	C15—H15B	0.9900
C10—C11	1.535 (2)	C16—H16A	0.9900
C10—C11i	1.535 (2)	C16—H16B	0.9900
C1—S1—C2	88.25 (11)	C13—C14—C13i	109.66 (19)
N2—N1—C1	108.20 (17)	C13i—C14—C15	109.73 (12)
N1—N2—C2	118.84 (18)	C10—C15—C14	109.9 (2)
N1—N2—C3	135.60 (19)	C12—C16—C12i	109.20 (19)
C2—N2—C3	105.56 (17)	C4—C5—H5	121.00
N4—N3—C2	104.65 (18)	C6—C5—H5	121.00
N3—N4—C3	109.67 (18)	C5—C6—H6B	122.00
S1—C1—N1	115.88 (15)	C7—C6—H6B	115.00
S1—C1—C10	121.10 (17)	C6—C7—H7	119.4 (13)
N1—C1—C10	123.02 (19)	C8—C7—H7	122.7 (13)
S1—C2—N2	108.83 (15)	C7—C8—H8A	114 (3)
S1—C2—N3	138.93 (19)	C9—C8—H8A	125 (3)
N2—C2—N3	112.2 (2)	C4—C9—H9	120.00
N2—C3—N4	107.9 (2)	C8—C9—H9	120.00
N2—C3—C4	126.26 (18)	C10—C11—H11A	110.00
N4—C3—C4	125.9 (2)	C10—C11—H11B	110.00
C3—C4—C5	117.99 (19)	C12—C11—H11A	110.00
C3—C4—C9	122.1 (2)	C12—C11—H11B	110.00
C5—C4—C9	119.9 (2)	H11A—C11—H11B	108.00
C4—C5—C6	118.3 (2)	C11—C12—H12	109.00
F1A—C6—C5	118.5 (2)	C13—C12—H12	109.00
F1A—C6—C7	118.4 (2)	C16—C12—H12	109.00
C5—C6—C7	123.2 (2)	C12—C13—H13A	110.00
C6—C7—C8	117.9 (2)	C12—C13—H13B	110.00
C7—C8—C9	121.1 (2)	C14—C13—H13A	110.00
F1B—C8—C7	122.2 (10)	C14—C13—H13B	110.00
F1B—C8—C9	116.8 (10)	H13A—C13—H13B	108.00
C4—C9—C8	119.6 (2)	C13—C14—H14	109.00
C1—C10—C11	110.08 (11)	C15—C14—H14	109.00
C1—C10—C15	109.90 (19)	C13i—C14—H14	109.00
C1—C10—C11i	110.08 (11)	C10—C15—H15A	110.00
C11—C10—C15	109.02 (11)	C10—C15—H15B	110.00
C11—C10—C11i	108.71 (18)	C14—C15—H15A	110.00
C11i—C10—C15	109.02 (11)	C14—C15—H15B	110.00
C10—C11—C12	109.55 (15)	H15A—C15—H15B	108.00
C11—C12—C13	109.96 (17)	C12—C16—H16A	110.00
C11—C12—C16	109.64 (15)	C12—C16—H16B	110.00
C13—C12—C16	109.24 (16)	H16A—C16—H16B	108.00
C12—C13—C14	109.39 (16)	C12i—C16—H16A	110.00
C13—C14—C15	109.73 (12)	C12i—C16—H16B	110.00
C2—S1—C1—N1	0.00 (1)	N4—C3—C4—C5	0.00 (1)
C2—S1—C1—C10	180.00 (1)	N4—C3—C4—C9	180.00 (1)
C1—S1—C2—N2	0.00 (1)	C3—C4—C5—C6	180.00 (1)
C1—S1—C2—N3	−180.00 (1)	C9—C4—C5—C6	0.00 (1)
C1—N1—N2—C2	0.00 (1)	C3—C4—C9—C8	180.00 (1)
C1—N1—N2—C3	180.00 (1)	C5—C4—C9—C8	0.00 (1)
N2—N1—C1—S1	0.00 (1)	C4—C5—C6—F1A	180.00 (1)
N2—N1—C1—C10	180.00 (1)	C4—C5—C6—C7	0.00 (1)
N1—N2—C3—C4	0.00 (1)	F1A—C6—C7—C8	180.00 (1)
C3—N2—C2—N3	0.00 (1)	C5—C6—C7—C8	0.00 (1)
N1—N2—C2—S1	0.00 (1)	C6—C7—C8—C9	0.00 (1)
C3—N2—C2—S1	180.00 (1)	C7—C8—C9—C4	0.00 (1)
N1—N2—C3—N4	−180.00 (1)	C1—C10—C11—C12	−179.45 (16)
C2—N2—C3—C4	180.00 (1)	C15—C10—C11—C12	−58.8 (2)
C2—N2—C3—N4	0.00 (1)	C11i—C10—C11—C12	59.90 (19)
N1—N2—C2—N3	180.00 (1)	C1—C10—C15—C14	180.00 (1)
N4—N3—C2—S1	180.00 (1)	C11—C10—C15—C14	59.27 (12)
N4—N3—C2—N2	0.00 (1)	C10—C11—C12—C13	59.6 (2)
C2—N3—N4—C3	0.00 (1)	C10—C11—C12—C16	−60.5 (2)
N3—N4—C3—C4	−180.00 (1)	C11—C12—C13—C14	−60.1 (2)
N3—N4—C3—N2	0.00 (1)	C16—C12—C13—C14	60.2 (2)
N1—C1—C10—C11	120.09 (13)	C11—C12—C16—C12i	60.3 (2)
N1—C1—C10—C15	0.00 (1)	C13—C12—C16—C12i	−60.27 (19)
S1—C1—C10—C15	180.00 (1)	C12—C13—C14—C15	60.2 (2)
S1—C1—C10—C11	−59.91 (13)	C12—C13—C14—C13i	−60.4 (2)
N2—C3—C4—C5	180.00 (1)	C13—C14—C15—C10	−60.28 (14)
N2—C3—C4—C9	0.00 (1)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···F1Aii	0.99	2.67	3.526 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯F1Ai	0.99	2.67	3.526 (3)	145

Symmetry code: (i) .