1-(Adamantan-1-yl)-3-(4-fluoro-phen-yl)thio-urea.

In the title mol-ecule, C(17)H(21)FN(2)S, the mean planes of the benzene ring and the thio-urea fragment form a dihedral angle of 61.93 (9)°. In the crystal, pairs of weak N-H⋯S inter-actions link the mol-ecules, forming inversion dimers.

Related literature

For background to the biological activity of adamantane and thio­urea derivatives, see: Vernier et al. (1969 ▶); El-Emam et al. (2004 ▶); Li et al. (2009 ▶); Hunter et al. (2008 ▶); Kadi et al. (2007 ▶, 2010 ▶). For the crystal structures of related adamantane deriv­atives, see: Kadi et al. (2011 ▶); Almutairi et al. (2012 ▶); Al-Abdullah et al. (2012 ▶).

Experimental

Crystal data

C17H21FN2S

M = 304.42

Triclinic,

a = 6.4274 (5) Å

b = 11.4727 (9) Å

c = 11.5870 (9) Å

α = 113.510 (6)°

β = 94.721 (6)°

γ = 94.837 (6)°

V = 774.39 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.80 × 0.35 × 0.11 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.847, T max = 0.977

11154 measured reflections

3048 independent reflections

2224 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.118

S = 1.01

3048 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812017515/cv5285sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017515/cv5285Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812017515/cv5285Isup3.cml

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

C17H21FN2S	Z = 2
Mr = 304.42	F(000) = 324
Triclinic, P1	Dx = 1.306 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4274 (5) Å	Cell parameters from 14319 reflections
b = 11.4727 (9) Å	θ = 3.2–27.9°
c = 11.5870 (9) Å	µ = 0.22 mm−1
α = 113.510 (6)°	T = 296 K
β = 94.721 (6)°	Prism, colourless
γ = 94.837 (6)°	0.80 × 0.35 × 0.11 mm
V = 774.39 (10) Å3

Stoe IPDS 2 diffractometer	3048 independent reflections
Radiation source: fine-focus sealed tube	2224 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.078
rotation method scans	θmax = 26.0°, θmin = 3.2°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −7→7
Tmin = 0.847, Tmax = 0.977	k = −14→14
11154 measured 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0575P)2 + 0.0575P] where P = (Fo2 + 2Fc2)/3
3048 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.3269 (3)	0.96011 (19)	0.2888 (2)	0.0449 (5)
C2	0.4940 (4)	1.0491 (2)	0.3639 (2)	0.0522 (6)
H2	0.4918	1.0899	0.4510	0.063*
C3	0.6639 (4)	1.0781 (2)	0.3108 (3)	0.0603 (6)
H3	0.7754	1.1393	0.3608	0.072*
C4	0.6651 (4)	1.0152 (2)	0.1836 (3)	0.0579 (6)
C5	0.5006 (4)	0.9293 (2)	0.1057 (2)	0.0587 (6)
H5	0.5045	0.8894	0.0186	0.070*
C6	0.3282 (4)	0.9030 (2)	0.1589 (2)	0.0538 (6)
H6	0.2125	0.8467	0.1073	0.065*
C7	0.0960 (3)	0.80999 (19)	0.3412 (2)	0.0434 (5)
C8	0.2048 (3)	0.58337 (18)	0.25944 (19)	0.0371 (4)
C9	−0.0095 (3)	0.50477 (19)	0.1946 (2)	0.0414 (5)
H9A	−0.0449	0.5111	0.1145	0.050*
H9B	−0.1178	0.5382	0.2481	0.050*
C10	0.0005 (3)	0.3639 (2)	0.1715 (2)	0.0484 (6)
H10	−0.1371	0.3139	0.1315	0.058*
C11	0.0577 (4)	0.3544 (2)	0.2966 (3)	0.0555 (6)
H11A	0.0617	0.2654	0.2821	0.067*
H11B	−0.0482	0.3873	0.3521	0.067*
C12	0.2722 (4)	0.4314 (2)	0.3594 (3)	0.0553 (6)
H12	0.3091	0.4242	0.4398	0.066*
C13	0.2620 (3)	0.5721 (2)	0.3845 (2)	0.0479 (5)
H13A	0.1572	0.6054	0.4407	0.057*
H13B	0.3972	0.6221	0.4255	0.057*
C14	0.3707 (3)	0.5295 (2)	0.1712 (2)	0.0467 (5)
H14A	0.3351	0.5364	0.0914	0.056*
H14B	0.5073	0.5789	0.2097	0.056*
C15	0.3806 (3)	0.3894 (2)	0.1469 (2)	0.0524 (6)
H15	0.4880	0.3562	0.0912	0.063*
C16	0.1668 (3)	0.3114 (2)	0.0831 (3)	0.0565 (6)
H16A	0.1725	0.2219	0.0662	0.068*
H16B	0.1305	0.3176	0.0030	0.068*
C17	0.4373 (3)	0.3789 (2)	0.2715 (3)	0.0630 (7)
H17A	0.5744	0.4269	0.3112	0.076*
H17B	0.4443	0.2899	0.2563	0.076*
N1	0.1550 (3)	0.92729 (17)	0.34457 (19)	0.0536 (5)
H1	0.0822	0.9873	0.3838	0.064*
N2	0.2119 (3)	0.71831 (16)	0.27757 (18)	0.0471 (5)
H2A	0.3069	0.7428	0.2410	0.057*
F1	0.8343 (3)	1.04002 (17)	0.12965 (18)	0.0899 (6)
S1	−0.10933 (9)	0.78832 (5)	0.41551 (6)	0.0557 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0514 (11)	0.0311 (10)	0.0520 (14)	0.0071 (8)	0.0101 (10)	0.0159 (9)
C2	0.0629 (13)	0.0420 (12)	0.0466 (13)	0.0011 (10)	0.0050 (11)	0.0140 (10)
C3	0.0571 (13)	0.0512 (14)	0.0647 (17)	−0.0051 (11)	0.0007 (12)	0.0191 (12)
C4	0.0603 (14)	0.0453 (12)	0.0703 (17)	0.0038 (10)	0.0204 (12)	0.0244 (12)
C5	0.0801 (16)	0.0432 (12)	0.0509 (15)	0.0033 (11)	0.0193 (13)	0.0159 (11)
C6	0.0588 (13)	0.0428 (12)	0.0504 (14)	−0.0041 (10)	0.0040 (11)	0.0119 (11)
C7	0.0427 (10)	0.0373 (11)	0.0453 (13)	0.0058 (8)	0.0080 (9)	0.0110 (9)
C8	0.0326 (9)	0.0344 (10)	0.0412 (12)	0.0041 (7)	0.0065 (8)	0.0121 (8)
C9	0.0341 (9)	0.0443 (11)	0.0417 (12)	0.0075 (8)	0.0021 (8)	0.0134 (9)
C10	0.0326 (10)	0.0395 (11)	0.0594 (15)	−0.0005 (8)	0.0024 (9)	0.0076 (10)
C11	0.0512 (12)	0.0471 (12)	0.0744 (17)	0.0048 (10)	0.0152 (12)	0.0302 (12)
C12	0.0545 (13)	0.0573 (14)	0.0604 (15)	0.0069 (10)	−0.0038 (11)	0.0328 (12)
C13	0.0424 (11)	0.0506 (13)	0.0446 (13)	0.0009 (9)	−0.0025 (10)	0.0157 (10)
C14	0.0389 (10)	0.0433 (11)	0.0569 (14)	0.0084 (8)	0.0149 (10)	0.0171 (10)
C15	0.0395 (11)	0.0414 (11)	0.0711 (17)	0.0119 (9)	0.0176 (11)	0.0144 (11)
C16	0.0519 (12)	0.0405 (12)	0.0624 (16)	0.0068 (10)	0.0092 (11)	0.0051 (11)
C17	0.0415 (12)	0.0531 (14)	0.098 (2)	0.0128 (10)	0.0018 (13)	0.0353 (14)
N1	0.0594 (11)	0.0350 (9)	0.0655 (13)	0.0110 (8)	0.0234 (10)	0.0158 (9)
N2	0.0465 (9)	0.0376 (9)	0.0614 (12)	0.0091 (7)	0.0235 (9)	0.0207 (9)
F1	0.0811 (10)	0.0808 (11)	0.1042 (14)	−0.0079 (8)	0.0415 (10)	0.0320 (10)
S1	0.0505 (3)	0.0416 (3)	0.0672 (4)	0.0066 (2)	0.0261 (3)	0.0106 (3)

C1—C2	1.381 (3)	C10—C16	1.533 (3)
C1—C6	1.383 (3)	C10—H10	0.9800
C1—N1	1.421 (3)	C11—C12	1.526 (3)
C2—C3	1.376 (3)	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700
C3—C4	1.359 (4)	C12—C17	1.524 (3)
C3—H3	0.9300	C12—C13	1.530 (3)
C4—F1	1.362 (3)	C12—H12	0.9800
C4—C5	1.364 (4)	C13—H13A	0.9700
C5—C6	1.380 (3)	C13—H13B	0.9700
C5—H5	0.9300	C14—C15	1.526 (3)
C6—H6	0.9300	C14—H14A	0.9700
C7—N2	1.345 (2)	C14—H14B	0.9700
C7—N1	1.351 (3)	C15—C17	1.514 (4)
C7—S1	1.687 (2)	C15—C16	1.527 (3)
C8—N2	1.473 (2)	C15—H15	0.9800
C8—C13	1.524 (3)	C16—H16A	0.9700
C8—C14	1.533 (3)	C16—H16B	0.9700
C8—C9	1.535 (3)	C17—H17A	0.9700
C9—C10	1.537 (3)	C17—H17B	0.9700
C9—H9A	0.9700	N1—H1	0.8600
C9—H9B	0.9700	N2—H2A	0.8600
C10—C11	1.514 (4)
C2—C1—C6	119.4 (2)	H11A—C11—H11B	108.2
C2—C1—N1	120.3 (2)	C17—C12—C11	109.3 (2)
C6—C1—N1	120.3 (2)	C17—C12—C13	109.9 (2)
C3—C2—C1	120.5 (2)	C11—C12—C13	109.09 (18)
C3—C2—H2	119.7	C17—C12—H12	109.5
C1—C2—H2	119.7	C11—C12—H12	109.5
C4—C3—C2	118.5 (2)	C13—C12—H12	109.5
C4—C3—H3	120.7	C8—C13—C12	109.58 (18)
C2—C3—H3	120.7	C8—C13—H13A	109.8
C3—C4—F1	119.4 (2)	C12—C13—H13A	109.8
C3—C4—C5	122.7 (2)	C8—C13—H13B	109.8
F1—C4—C5	117.8 (2)	C12—C13—H13B	109.8
C4—C5—C6	118.5 (2)	H13A—C13—H13B	108.2
C4—C5—H5	120.7	C15—C14—C8	110.05 (17)
C6—C5—H5	120.7	C15—C14—H14A	109.7
C5—C6—C1	120.2 (2)	C8—C14—H14A	109.7
C5—C6—H6	119.9	C15—C14—H14B	109.7
C1—C6—H6	119.9	C8—C14—H14B	109.7
N2—C7—N1	115.40 (17)	H14A—C14—H14B	108.2
N2—C7—S1	125.04 (16)	C17—C15—C14	109.59 (19)
N1—C7—S1	119.56 (14)	C17—C15—C16	109.8 (2)
N2—C8—C13	111.51 (17)	C14—C15—C16	109.42 (18)
N2—C8—C14	105.19 (16)	C17—C15—H15	109.3
C13—C8—C14	109.26 (17)	C14—C15—H15	109.3
N2—C8—C9	112.54 (16)	C16—C15—H15	109.3
C13—C8—C9	109.88 (16)	C15—C16—C10	108.83 (18)
C14—C8—C9	108.27 (16)	C15—C16—H16A	109.9
C8—C9—C10	109.31 (16)	C10—C16—H16A	109.9
C8—C9—H9A	109.8	C15—C16—H16B	109.9
C10—C9—H9A	109.8	C10—C16—H16B	109.9
C8—C9—H9B	109.8	H16A—C16—H16B	108.3
C10—C9—H9B	109.8	C15—C17—C12	109.70 (18)
H9A—C9—H9B	108.3	C15—C17—H17A	109.7
C11—C10—C16	109.86 (19)	C12—C17—H17A	109.7
C11—C10—C9	109.71 (18)	C15—C17—H17B	109.7
C16—C10—C9	109.11 (19)	C12—C17—H17B	109.7
C11—C10—H10	109.4	H17A—C17—H17B	108.2
C16—C10—H10	109.4	C7—N1—C1	125.69 (17)
C9—C10—H10	109.4	C7—N1—H1	117.2
C10—C11—C12	109.87 (19)	C1—N1—H1	117.2
C10—C11—H11A	109.7	C7—N2—C8	131.37 (17)
C12—C11—H11A	109.7	C7—N2—H2A	114.3
C10—C11—H11B	109.7	C8—N2—H2A	114.3
C12—C11—H11B	109.7
C6—C1—C2—C3	−2.1 (3)	C11—C12—C13—C8	−60.2 (2)
N1—C1—C2—C3	177.9 (2)	N2—C8—C14—C15	179.09 (18)
C1—C2—C3—C4	−1.4 (4)	C13—C8—C14—C15	59.3 (2)
C2—C3—C4—F1	−178.3 (2)	C9—C8—C14—C15	−60.4 (2)
C2—C3—C4—C5	3.3 (4)	C8—C14—C15—C17	−59.6 (2)
C3—C4—C5—C6	−1.6 (4)	C8—C14—C15—C16	60.8 (3)
F1—C4—C5—C6	179.9 (2)	C17—C15—C16—C10	59.9 (2)
C4—C5—C6—C1	−1.9 (4)	C14—C15—C16—C10	−60.4 (3)
C2—C1—C6—C5	3.7 (3)	C11—C10—C16—C15	−59.5 (3)
N1—C1—C6—C5	−176.2 (2)	C9—C10—C16—C15	60.9 (3)
N2—C8—C9—C10	176.37 (17)	C14—C15—C17—C12	59.6 (2)
C13—C8—C9—C10	−58.7 (2)	C16—C15—C17—C12	−60.6 (2)
C14—C8—C9—C10	60.5 (2)	C11—C12—C17—C15	59.8 (3)
C8—C9—C10—C11	59.0 (2)	C13—C12—C17—C15	−59.8 (3)
C8—C9—C10—C16	−61.4 (2)	N2—C7—N1—C1	−0.8 (3)
C16—C10—C11—C12	59.6 (2)	S1—C7—N1—C1	178.58 (18)
C9—C10—C11—C12	−60.3 (2)	C2—C1—N1—C7	−117.2 (3)
C10—C11—C12—C17	−59.4 (2)	C6—C1—N1—C7	62.7 (3)
C10—C11—C12—C13	60.7 (2)	N1—C7—N2—C8	176.0 (2)
N2—C8—C13—C12	−174.86 (16)	S1—C7—N2—C8	−3.4 (4)
C14—C8—C13—C12	−59.0 (2)	C13—C8—N2—C7	−64.7 (3)
C9—C8—C13—C12	59.6 (2)	C14—C8—N2—C7	177.0 (2)
C17—C12—C13—C8	59.6 (2)	C9—C8—N2—C7	59.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.86	2.67	3.3939 (19)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.86	2.67	3.3939 (19)	142

Symmetry code: (i) .