6-(Adamantan-1-yl)-3-(3-fluoro­phen­yl)-1,2,4-triazolo[3,4-b][1,3,4]thia­diazole

Khan, M.-H.; Hameed, S.; Akhtar, T.; Stoeckli-Evans, H.

doi:10.1107/S1600536810046428

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages o3215-o3216

https://doi.org/10.1107/S1600536810046428

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6-(Adamantan-1-yl)-3-(3-fluorophenyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole

Mahmood-ul-Hassan Khan,^a Shahid Hameed,^a ^* Tashfeen Akhtar ^a and Helen Stoeckli-Evans ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bInstitute of Physics, University of Neuchâtel, rue Emile-Argand 11, CH-2009 Neuchâtel, Switzerland
^*Correspondence e-mail: shameed@qau.edu.pk

(Received 4 November 2010; accepted 10 November 2010; online 17 November 2010)

The title molecule, C₁₉H₁₉FN₄S, displays C_s molecular symmetry, in which the crystallographic mirror plane bisects the adamantan-1-yl unit while the 3-fluorophenyl triazole ring is located on the mirror plane. The F atom of the 3-fluorophenyl ring is positionally disordered [occupancy ratio 0.9:0.1]. In the crystal, π–π interactions between the triazole and phenyl rings occur [centroid–centroid distance = 3.5849 (7) Å] and weak C—H⋯F interactions 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_r = 354.44
Monoclinic, P 2₁ /m
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[F² > 2σ(F²)] = 0.030
wR(F²) = 0.074
S = 0.95
1708 reflections
154 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) $[-x, y+{\script{1\over 2}}, -z+2]$ .

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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046428/kp2286Isup2.hkl

checkCIF report

Comment top

Fused heterocycles have received widespread attention in the recent years due to their outstanding biological applications [Khan et al. 2010a; Demirbas et al., 2005; Amir et al., 2007; Ashok et al., 2007; Palekar et al., 2009]. Moreover, compounds bearing an adamantyl moiety are gaining prominence due to their biological and pharmaceutical potential [Kadi et al., 2007; Kouatly et al., 2009; Zahid et al., 2009]. The title compound was synthesised in continuation of our previous studies on the synthesis and biological screening of five membered heterocycles [Akhtar et al., 2007, 2008a, 2008b; Serwar et al.,2009; Khan et al., 2009, 2010b].

Bond distances (Allen et al., 1987) and bond angles are normal and similar to those reported for the 2-fluorophenyl derivative (Khan et al., 2009). The 3-fluorophenyl moiety is positionally disordered, with atom F1 having occupancies of 0.45/0.05 (F1A/F1B), where F1A is bonded to atom C6, while atom F1B is bonded to atom C8 (Fig. 1).

The title molecule possesses crystallographic mirror symmetry; the mirror plane bisects the adamantane moiety while the rest of the molecule lies in the mirror plane. The 3-fluorophenyl moiety is positionally disordered. The 2-fluorophenyl derivative, however, crystallised in the orthorhombic space group Pbca and the molecule possess no crystallographic symmetry. The 2-fluorophenyl ring is inclined to the triazole ring by 48.6 (1)°, to eliviate steric hindrance.

In the crystal of the title compound there are weak C—H···F interactions [C11—H11A···F1Aⁱ, H···F 2.67 Å, C—H···F 145 °, symmetry code (i) -x, y + 1/2, -z + 2)] leading to the formation of a one-dimensional ribbon-like structure running in [010] (Fig. 2). There are also π–π interactions with the centroid-to centroid distance between the mean planes of the triazole ring (N2,C2,N3,N4,C3) and symmetry related phenyl rings (C4—C9) being 3.5849 (7) Å [the perpendicular distance is 3.3278 (1) Å with a slippage of 1.333 Å].

Related literature top

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 top

A mixture of 4-amino-5-(3-fluorophenyl)-2H-1,2,4-triazole-3(4H)-thione (0.2 g, 0.56 mmol) and adamantane-1-carboxylic acid (0.10 g, 0.56 mmol) was refluxed in the presence of POCl₃ (5.0 mL) for 4 h [Khan et al. 2010a]. The reaction mixture was cooled to RT, poured into crushed ice and neutralized using solid potassium carbonate until p_H 8. The precipitated solid was filtered off, washed with excess water and recrystallised from chloroform to give colourless plate-like crystals, suitable for X-ray analysis.

Structure description top

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).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2006); cell refinement: X-AREA (Stoe & Cie, 2006); 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 (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. A view of the molecular structure of the title molecule with the displacement ellipsoids drawn at the 50% probability level [symmetry code (a) = x, 3/2 - y, z; The positional disorder of the 3-fluorophenyl group is also illustrated: atoms F1A and H8A (occupancy 0.45) and atoms F1B and H6B (occupancy 0.05)].
	Fig. 2. The crystal packing of the title compound along the a axis. The C—H···F interactions are shown as dashed cyan lines.

6-(Adamantan-1-yl)-3-(3-fluorophenyl)-1,2,4- triazolo[3,4-b][1,3,4]thiadiazole top

Crystal data top

C₁₉H₁₉FN₄S	F(000) = 372
M_r = 354.44	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0449P)²] where P = (F_o² + 2F_c²)/3
1708 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 0.20 e Å⁻³
4 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₉H₁₉FN₄S	V = 802.25 (17) Å³
M_r = 354.44	Z = 2
Monoclinic, P2₁/m	Mo Kα radiation
a = 11.6385 (16) Å	µ = 0.22 mm⁻¹
b = 6.6555 (5) Å	T = 173 K
c = 11.6634 (16) Å	0.34 × 0.30 × 0.11 mm
β = 117.379 (14)°

Data collection top

Stoe IPDS-2 diffractometer	1223 reflections with I > 2σ(I)
6164 measured reflections	R_int = 0.031
1708 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	4 restraints
wR(F²) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.20 e Å⁻³
1708 reflections	Δρ_min = −0.26 e Å⁻³
154 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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

Atomic displacement parameters (Å²) top

	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

Geometric parameters (Å, º) top

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)

Symmetry code: (i) x, −y+3/2, z.

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (ii) −x, y+1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉FN₄S
M_r	354.44
Crystal system, space group	Monoclinic, P2₁/m
Temperature (K)	173
a, b, c (Å)	11.6385 (16), 6.6555 (5), 11.6634 (16)
β (°)	117.379 (14)
V (Å³)	802.25 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.34 × 0.30 × 0.11

Data collection
Diffractometer	Stoe IPDS2
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6164, 1708, 1223
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.620

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.074, 0.95
No. of reflections	1708
No. of parameters	154
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.26

Computer programs: X-AREA (Stoe & Cie, 2006), X-RED32 (Stoe & Cie, 2006), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) −x, y+1/2, −z+2.

Acknowledgements

HSE thanks the staff of the X-ray Application Lab of the CSEM, Neuchâtel, for access to the X-ray diffraction equipment.

References

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Volume 66| Part 12| December 2010| Pages o3215-o3216

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

6-(Adamantan-1-yl)-3-(3-fluoro­phen­yl)-1,2,4-triazolo[3,4-b][1,3,4]thia­diazole

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6-(Adamantan-1-yl)-3-(3-fluorophenyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole