5-(Adamantan-1-yl)-3-[(4-fluoro-anilino)meth-yl]-2,3-di-hydro-1,3,4-oxa-diazole-2-thione.

In the title compound, C19H22FN3OS, the dihedral angle between the inclined oxa-diazole and benzene rings is 52.7 (3)°. In the crystal, helical supra-molecular chains along [100] are sustained by N-H⋯S hydrogen bonds supported by methyl-ene-benzene C-H⋯π inter-actions. The crystal studied was an inversion twin with the fractional contribution of the minor component being 0.33 (14).

Related literature

For biological background to adamantyl-1,3,4-oxa­diazole derivatives and for the structure of the phenyl derivative, see: Al-Tamimi et al. (2013 ▶).

Experimental

Crystal data

C19H22FN3OS

M = 359.47

Orthorhombic,

a = 7.1683 (8) Å

b = 10.6621 (11) Å

c = 23.592 (3) Å

V = 1803.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 295 K

0.30 × 0.10 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.698, T max = 1.000

7867 measured reflections

3902 independent reflections

2177 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.158

S = 0.98

3902 reflections

231 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1501 Friedel pairs

Flack parameter: 0.67 (14)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813009823/hb7069sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009823/hb7069Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009823/hb7069Isup3.cml

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

C19H22FN3OS	F(000) = 760
Mr = 359.47	Dx = 1.324 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1361 reflections
a = 7.1683 (8) Å	θ = 2.8–27.5°
b = 10.6621 (11) Å	µ = 0.20 mm−1
c = 23.592 (3) Å	T = 295 K
V = 1803.1 (3) Å3	Prism, colourless
Z = 4	0.30 × 0.10 × 0.10 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	3902 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2177 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.043
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 3.0°
ω scan	h = −9→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→13
Tmin = 0.698, Tmax = 1.000	l = −30→30
7867 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.158	w = 1/[σ2(Fo2) + (0.0632P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max < 0.001
3902 reflections	Δρmax = 0.26 e Å−3
231 parameters	Δρmin = −0.18 e Å−3
1 restraint	Absolute structure: Flack (1983), 1501 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.67 (14)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.06569 (15)	0.33471 (10)	0.03304 (5)	0.0836 (4)
F1	−0.2851 (7)	−0.4312 (3)	0.12970 (14)	0.1582 (16)
O1	0.3173 (4)	0.2563 (2)	0.10859 (11)	0.0620 (6)
N1	0.3424 (4)	0.0519 (3)	0.09315 (12)	0.0587 (8)
N2	0.2100 (4)	0.1064 (3)	0.05696 (13)	0.0611 (8)
N3	−0.0577 (5)	−0.0053 (3)	0.01856 (17)	0.0778 (10)
H3	−0.147 (5)	0.037 (4)	0.0020 (17)	0.098 (15)*
C1	0.1962 (5)	0.2294 (3)	0.06489 (17)	0.0612 (9)
C2	0.4025 (5)	0.1442 (3)	0.12294 (15)	0.0541 (8)
C3	0.5497 (5)	0.1445 (3)	0.16727 (14)	0.0511 (8)
C4	0.7151 (6)	0.2249 (4)	0.14706 (16)	0.0696 (11)
H4A	0.7643	0.1911	0.1119	0.083*
H4B	0.6736	0.3100	0.1400	0.083*
C5	0.8671 (6)	0.2249 (4)	0.19230 (18)	0.0777 (13)
H5	0.9729	0.2756	0.1793	0.093*
C6	0.7903 (7)	0.2793 (4)	0.24685 (19)	0.0832 (13)
H6A	0.7476	0.3644	0.2403	0.100*
H6B	0.8879	0.2819	0.2753	0.100*
C7	0.6290 (6)	0.1993 (3)	0.26791 (17)	0.0675 (11)
H7	0.5808	0.2339	0.3035	0.081*
C8	0.4746 (5)	0.1993 (3)	0.22315 (15)	0.0623 (10)
H8A	0.4311	0.2843	0.2169	0.075*
H8B	0.3701	0.1494	0.2363	0.075*
C9	0.6160 (5)	0.0102 (3)	0.17771 (15)	0.0592 (9)
H9A	0.5122	−0.0409	0.1905	0.071*
H9B	0.6633	−0.0255	0.1427	0.071*
C10	0.7691 (6)	0.0105 (4)	0.22242 (17)	0.0670 (11)
H10	0.8114	−0.0757	0.2290	0.080*
C11	0.6935 (7)	0.0645 (4)	0.27741 (17)	0.0738 (11)
H11A	0.7900	0.0627	0.3062	0.089*
H11B	0.5896	0.0140	0.2906	0.089*
C12	0.9315 (6)	0.0890 (5)	0.2021 (2)	0.0875 (13)
H12A	0.9801	0.0545	0.1670	0.105*
H12B	1.0304	0.0875	0.2301	0.105*
C13	0.1279 (6)	0.0329 (4)	0.01020 (16)	0.0736 (11)
H13A	0.1337	0.0827	−0.0242	0.088*
H13B	0.2040	−0.0412	0.0042	0.088*
C14	−0.1079 (6)	−0.1144 (3)	0.04713 (15)	0.0643 (10)
C15	−0.2947 (6)	−0.1525 (4)	0.04433 (18)	0.0758 (11)
H15	−0.3804	−0.1057	0.0236	0.091*
C16	−0.3509 (9)	−0.2588 (5)	0.0722 (2)	0.0968 (16)
H16	−0.4748	−0.2843	0.0704	0.116*
C17	−0.2266 (12)	−0.3262 (5)	0.1021 (2)	0.1003 (18)
C18	−0.0461 (10)	−0.2929 (5)	0.1046 (2)	0.1024 (17)
H18	0.0378	−0.3429	0.1245	0.123*
C19	0.0173 (7)	−0.1844 (4)	0.07792 (17)	0.0835 (13)
H19	0.1414	−0.1598	0.0809	0.100*

	U11	U22	U33	U12	U13	U23
S1	0.0517 (6)	0.0873 (7)	0.1118 (8)	0.0022 (6)	−0.0058 (6)	0.0342 (7)
F1	0.245 (5)	0.104 (2)	0.126 (2)	−0.040 (3)	0.038 (3)	0.021 (2)
O1	0.0485 (14)	0.0574 (14)	0.0800 (16)	−0.0034 (13)	−0.0044 (14)	0.0029 (13)
N1	0.0481 (18)	0.0599 (18)	0.0681 (18)	−0.0007 (16)	−0.0024 (15)	0.0012 (16)
N2	0.0510 (19)	0.0658 (19)	0.0666 (19)	−0.0018 (16)	−0.0026 (15)	0.0062 (16)
N3	0.050 (2)	0.075 (2)	0.108 (3)	−0.003 (2)	−0.021 (2)	0.013 (2)
C1	0.042 (2)	0.069 (2)	0.073 (2)	−0.006 (2)	0.0028 (19)	0.012 (2)
C2	0.0405 (19)	0.0489 (19)	0.073 (2)	0.0026 (17)	0.0036 (17)	0.0031 (18)
C3	0.0438 (19)	0.0481 (18)	0.0613 (19)	−0.0078 (17)	−0.0004 (16)	−0.0019 (16)
C4	0.052 (2)	0.079 (2)	0.077 (2)	−0.019 (2)	0.002 (2)	0.007 (2)
C5	0.052 (2)	0.098 (3)	0.084 (3)	−0.029 (2)	0.002 (2)	0.010 (2)
C6	0.083 (3)	0.070 (2)	0.097 (3)	−0.023 (3)	−0.026 (3)	0.001 (2)
C7	0.070 (3)	0.064 (2)	0.068 (2)	−0.015 (2)	0.001 (2)	−0.014 (2)
C8	0.053 (2)	0.057 (2)	0.077 (2)	−0.0014 (19)	0.0070 (19)	−0.006 (2)
C9	0.052 (2)	0.056 (2)	0.070 (2)	0.0021 (18)	−0.0048 (18)	−0.0083 (17)
C10	0.057 (3)	0.059 (2)	0.086 (3)	0.004 (2)	−0.012 (2)	−0.002 (2)
C11	0.073 (3)	0.074 (3)	0.075 (3)	−0.010 (2)	−0.007 (2)	0.004 (2)
C12	0.048 (2)	0.120 (4)	0.095 (3)	0.008 (3)	−0.001 (2)	−0.003 (3)
C13	0.076 (3)	0.079 (3)	0.067 (2)	−0.013 (2)	−0.011 (2)	0.005 (2)
C14	0.067 (3)	0.061 (2)	0.065 (2)	−0.002 (2)	−0.004 (2)	−0.009 (2)
C15	0.070 (3)	0.071 (2)	0.086 (3)	−0.006 (2)	0.001 (2)	−0.019 (2)
C16	0.105 (4)	0.086 (3)	0.099 (4)	−0.024 (3)	0.021 (3)	−0.024 (3)
C17	0.158 (6)	0.072 (3)	0.071 (3)	−0.020 (4)	0.014 (4)	−0.001 (3)
C18	0.138 (5)	0.086 (3)	0.083 (3)	0.003 (4)	−0.027 (3)	0.012 (3)
C19	0.086 (3)	0.084 (3)	0.080 (3)	0.000 (3)	−0.025 (2)	0.007 (3)

S1—C1	1.643 (4)	C7—H7	0.9800
F1—C17	1.361 (5)	C8—H8A	0.9700
O1—C1	1.378 (5)	C8—H8B	0.9700
O1—C2	1.385 (4)	C9—C10	1.522 (5)
N1—C2	1.283 (4)	C9—H9A	0.9700
N1—N2	1.402 (4)	C9—H9B	0.9700
N2—C1	1.328 (5)	C10—C12	1.512 (6)
N2—C13	1.476 (5)	C10—C11	1.519 (5)
N3—C14	1.392 (5)	C10—H10	0.9800
N3—C13	1.406 (5)	C11—H11A	0.9700
N3—H3	0.874 (19)	C11—H11B	0.9700
C2—C3	1.486 (5)	C12—H12A	0.9700
C3—C9	1.529 (5)	C12—H12B	0.9700
C3—C4	1.538 (5)	C13—H13A	0.9700
C3—C8	1.539 (5)	C13—H13B	0.9700
C4—C5	1.526 (6)	C14—C19	1.374 (5)
C4—H4A	0.9700	C14—C15	1.401 (6)
C4—H4B	0.9700	C15—C16	1.371 (6)
C5—C6	1.515 (6)	C15—H15	0.9300
C5—C12	1.538 (6)	C16—C17	1.345 (8)
C5—H5	0.9800	C16—H16	0.9300
C6—C7	1.521 (6)	C17—C18	1.343 (8)
C6—H6A	0.9700	C18—C19	1.394 (6)
C6—H6B	0.9700	C18—H18	0.9300
C7—C11	1.526 (5)	C19—H19	0.9300
C7—C8	1.530 (5)
C1—O1—C2	106.3 (3)	H8A—C8—H8B	108.2
C2—N1—N2	104.1 (3)	C10—C9—C3	109.5 (3)
C1—N2—N1	112.0 (3)	C10—C9—H9A	109.8
C1—N2—C13	126.8 (3)	C3—C9—H9A	109.8
N1—N2—C13	120.3 (3)	C10—C9—H9B	109.8
C14—N3—C13	123.7 (4)	C3—C9—H9B	109.8
C14—N3—H3	117 (3)	H9A—C9—H9B	108.2
C13—N3—H3	119 (3)	C12—C10—C9	109.7 (3)
N2—C1—O1	105.3 (3)	C12—C10—C11	109.6 (3)
N2—C1—S1	130.8 (3)	C9—C10—C11	109.6 (3)
O1—C1—S1	123.9 (3)	C12—C10—H10	109.3
N1—C2—O1	112.3 (3)	C9—C10—H10	109.3
N1—C2—C3	128.7 (3)	C11—C10—H10	109.3
O1—C2—C3	118.9 (3)	C10—C11—C7	109.8 (3)
C2—C3—C9	109.4 (3)	C10—C11—H11A	109.7
C2—C3—C4	109.3 (3)	C7—C11—H11A	109.7
C9—C3—C4	109.4 (3)	C10—C11—H11B	109.7
C2—C3—C8	110.8 (3)	C7—C11—H11B	109.7
C9—C3—C8	109.0 (3)	H11A—C11—H11B	108.2
C4—C3—C8	108.9 (3)	C10—C12—C5	109.8 (3)
C5—C4—C3	109.5 (3)	C10—C12—H12A	109.7
C5—C4—H4A	109.8	C5—C12—H12A	109.7
C3—C4—H4A	109.8	C10—C12—H12B	109.7
C5—C4—H4B	109.8	C5—C12—H12B	109.7
C3—C4—H4B	109.8	H12A—C12—H12B	108.2
H4A—C4—H4B	108.2	N3—C13—N2	115.2 (3)
C6—C5—C4	109.6 (4)	N3—C13—H13A	108.5
C6—C5—C12	110.0 (4)	N2—C13—H13A	108.5
C4—C5—C12	108.6 (4)	N3—C13—H13B	108.5
C6—C5—H5	109.6	N2—C13—H13B	108.5
C4—C5—H5	109.6	H13A—C13—H13B	107.5
C12—C5—H5	109.6	C19—C14—N3	122.8 (4)
C5—C6—C7	109.8 (3)	C19—C14—C15	119.5 (4)
C5—C6—H6A	109.7	N3—C14—C15	117.8 (4)
C7—C6—H6A	109.7	C16—C15—C14	119.8 (5)
C5—C6—H6B	109.7	C16—C15—H15	120.1
C7—C6—H6B	109.7	C14—C15—H15	120.1
H6A—C6—H6B	108.2	C17—C16—C15	119.9 (5)
C6—C7—C11	110.3 (4)	C17—C16—H16	120.0
C6—C7—C8	108.9 (3)	C15—C16—H16	120.0
C11—C7—C8	108.7 (3)	C18—C17—C16	121.3 (5)
C6—C7—H7	109.6	C18—C17—F1	119.6 (7)
C11—C7—H7	109.6	C16—C17—F1	119.1 (7)
C8—C7—H7	109.6	C17—C18—C19	120.9 (5)
C7—C8—C3	109.7 (3)	C17—C18—H18	119.6
C7—C8—H8A	109.7	C19—C18—H18	119.6
C3—C8—H8A	109.7	C14—C19—C18	118.5 (5)
C7—C8—H8B	109.7	C14—C19—H19	120.8
C3—C8—H8B	109.7	C18—C19—H19	120.8
C2—N1—N2—C1	1.2 (4)	C9—C3—C8—C7	59.9 (4)
C2—N1—N2—C13	171.3 (3)	C4—C3—C8—C7	−59.4 (4)
N1—N2—C1—O1	−2.0 (4)	C2—C3—C9—C10	179.1 (3)
C13—N2—C1—O1	−171.3 (3)	C4—C3—C9—C10	59.4 (4)
N1—N2—C1—S1	179.0 (3)	C8—C3—C9—C10	−59.6 (4)
C13—N2—C1—S1	9.8 (6)	C3—C9—C10—C12	−60.1 (4)
C2—O1—C1—N2	2.0 (4)	C3—C9—C10—C11	60.3 (4)
C2—O1—C1—S1	−179.0 (3)	C12—C10—C11—C7	59.6 (4)
N2—N1—C2—O1	0.1 (4)	C9—C10—C11—C7	−60.8 (4)
N2—N1—C2—C3	−177.7 (3)	C6—C7—C11—C10	−59.0 (4)
C1—O1—C2—N1	−1.3 (4)	C8—C7—C11—C10	60.4 (4)
C1—O1—C2—C3	176.7 (3)	C9—C10—C12—C5	60.8 (4)
N1—C2—C3—C9	−5.0 (5)	C11—C10—C12—C5	−59.5 (5)
O1—C2—C3—C9	177.4 (3)	C6—C5—C12—C10	59.2 (5)
N1—C2—C3—C4	114.8 (4)	C4—C5—C12—C10	−60.7 (5)
O1—C2—C3—C4	−62.9 (4)	C14—N3—C13—N2	−86.1 (5)
N1—C2—C3—C8	−125.2 (4)	C1—N2—C13—N3	−85.2 (5)
O1—C2—C3—C8	57.1 (4)	N1—N2—C13—N3	106.3 (4)
C2—C3—C4—C5	−179.7 (3)	C13—N3—C14—C19	11.1 (6)
C9—C3—C4—C5	−59.9 (4)	C13—N3—C14—C15	−169.5 (4)
C8—C3—C4—C5	59.1 (4)	C19—C14—C15—C16	−0.1 (6)
C3—C4—C5—C6	−60.2 (4)	N3—C14—C15—C16	−179.5 (4)
C3—C4—C5—C12	60.0 (4)	C14—C15—C16—C17	0.0 (6)
C4—C5—C6—C7	61.1 (5)	C15—C16—C17—C18	−1.2 (7)
C12—C5—C6—C7	−58.2 (5)	C15—C16—C17—F1	179.7 (4)
C5—C6—C7—C11	58.3 (5)	C16—C17—C18—C19	2.4 (8)
C5—C6—C7—C8	−60.9 (4)	F1—C17—C18—C19	−178.5 (4)
C6—C7—C8—C3	60.2 (4)	N3—C14—C19—C18	−179.4 (4)
C11—C7—C8—C3	−60.0 (4)	C15—C14—C19—C18	1.2 (6)
C2—C3—C8—C7	−179.7 (3)	C17—C18—C19—C14	−2.4 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···S1i	0.87 (2)	2.61 (2)	3.475 (4)	172 (4)
C9—H9A···Cg1ii	0.97	2.90	3.800 (5)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14–C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯S1i	0.87 (2)	2.61 (2)	3.475 (4)	172 (4)
C9—H9A⋯Cg1ii	0.97	2.90	3.800 (5)	154

Symmetry codes: (i) ; (ii) .