Adamantane-1-thio-amide.

The title compound, C(11)H(17)NS, is an important inter-mediate for the synthesis of biologically active adamantlythia-zolo-oxadiazo-les. The adamantyl residue is disordered about a twofold rotation axis over two sites with site-occupation factors of 0.817 (3) and 0.183 (3). The crystal structure is stabilized by inter-molecular N-H⋯S hydrogen-bonding inter-actions.

Related literature

Adamantane derivatives include well known drugs such as n class="Chemical">Rimantadine, Memantine, Adapalene and Adatanserin, see: Krasnikov et al. (2004 ▶). For their biological activity, see: Singh et al. (2007 ▶); Wennekes et al. (2007 ▶); Inaba et al. (2007 ▶); Kolocouris et al. (2007 ▶). Thio­amides are not only widely used as fungicides (Klimesova et al., 1999 ▶) and herbicides (Bahadir et al., 1979 ▶) but are also valuable inter­mediates in the synthesis of heterocyclic compounds (Jagodzinski, 2003 ▶). For the synthesis of the title compound, see: Kaboudin & Elhamifar (2006 ▶).

Experimental

Crystal data

C11H17NS

M = 195.32

Monoclinic,

a = 24.255 (2) Å

b = 7.9879 (5) Å

c = 11.2928 (9) Å

β = 100.859 (7)°

V = 2148.8 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 173 K

0.39 × 0.26 × 0.25 mm

Data collection

Stoe IPDS-II two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2009 ▶; Blessing, 1995 ▶) T min = 0.907, T max = 0.939

7423 measured reflections

2002 independent reflections

1703 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.103

S = 1.07

2002 reflections

163 parameters

35 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.30 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027470/hg2536sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027470/hg2536Isup2.hkl

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

C11H17NS	F(000) = 848
Mr = 195.32	Dx = 1.208 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7109 reflections
a = 24.255 (2) Å	θ = 3.5–25.9°
b = 7.9879 (5) Å	µ = 0.26 mm−1
c = 11.2928 (9) Å	T = 173 K
β = 100.859 (7)°	Block, colourless
V = 2148.8 (3) Å3	0.39 × 0.26 × 0.25 mm
Z = 8

Stoe IPDS-II two-circle diffractometer	2002 independent reflections
Radiation source: fine-focus sealed tube	1703 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω scans	θmax = 25.5°, θmin = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −29→29
Tmin = 0.907, Tmax = 0.939	k = −9→8
7423 measured reflections	l = −13→13

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0572P)2 + 0.6628P] where P = (Fo2 + 2Fc2)/3
2002 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.20 e Å−3
35 restraints	Δρmin = −0.30 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	Occ. (<1)
S1	0.21599 (2)	0.61925 (7)	0.64064 (3)	0.0548 (2)
N1	0.20667 (6)	0.55153 (18)	0.41220 (11)	0.0355 (3)
H1A	0.1949 (7)	0.495 (2)	0.3461 (12)	0.041 (5)*
H1B	0.2299 (7)	0.6339 (18)	0.4094 (17)	0.044 (5)*
C1	0.19018 (6)	0.51441 (19)	0.51351 (12)	0.0307 (3)
C2	0.14709 (6)	0.37457 (18)	0.51046 (12)	0.0280 (3)
C3	0.09531 (7)	0.4503 (2)	0.55352 (17)	0.0346 (5)	0.817 (2)
H3A	0.1071	0.4995	0.6348	0.041*	0.817 (2)
H3B	0.0789	0.5406	0.4978	0.041*	0.817 (2)
C4	0.05109 (9)	0.3143 (4)	0.5574 (2)	0.0449 (6)	0.817 (2)
H4	0.0179	0.3640	0.5855	0.054*	0.817 (2)
C5	0.03278 (11)	0.2407 (4)	0.4326 (2)	0.0535 (7)	0.817 (2)
H5A	0.0040	0.1535	0.4346	0.064*	0.817 (2)
H5B	0.0159	0.3294	0.3760	0.064*	0.817 (2)
C6	0.08243 (15)	0.1650 (4)	0.3893 (3)	0.0553 (10)	0.817 (2)
H6	0.0697	0.1172	0.3068	0.066*	0.817 (2)
C7	0.12688 (9)	0.3016 (3)	0.38385 (17)	0.0424 (5)	0.817 (2)
H7A	0.1591	0.2529	0.3534	0.051*	0.817 (2)
H7B	0.1104	0.3916	0.3279	0.051*	0.817 (2)
C8	0.17150 (8)	0.2349 (3)	0.59767 (19)	0.0401 (5)	0.817 (2)
H8A	0.1842	0.2821	0.6793	0.048*	0.817 (2)
H8B	0.2044	0.1845	0.5709	0.048*	0.817 (2)
C9	0.07646 (14)	0.1784 (3)	0.6434 (2)	0.0466 (6)	0.817 (2)
H9A	0.0479	0.0913	0.6479	0.056*	0.817 (2)
H9B	0.0884	0.2263	0.7251	0.056*	0.817 (2)
C10	0.10857 (13)	0.0264 (3)	0.4743 (3)	0.0591 (7)	0.817 (2)
H10A	0.1415	−0.0210	0.4460	0.071*	0.817 (2)
H10B	0.0809	−0.0645	0.4756	0.071*	0.817 (2)
C11	0.12686 (11)	0.0991 (3)	0.6021 (2)	0.0493 (6)	0.817 (2)
H11	0.1429	0.0084	0.6594	0.059*	0.817 (2)
C3'	0.0918 (3)	0.4290 (11)	0.4335 (8)	0.037 (2)*	0.183 (2)
H3'1	0.0980	0.4610	0.3523	0.045*	0.183 (2)
H3'2	0.0774	0.5284	0.4703	0.045*	0.183 (2)
C4'	0.0475 (5)	0.2869 (14)	0.4214 (10)	0.046 (3)*	0.183 (2)
H4'	0.0109	0.3238	0.3721	0.055*	0.183 (2)
C5'	0.0714 (5)	0.1404 (17)	0.3637 (12)	0.040 (4)*	0.183 (2)
H5'1	0.0429	0.0503	0.3489	0.048*	0.183 (2)
H5'2	0.0794	0.1758	0.2846	0.048*	0.183 (2)
C6'	0.1241 (4)	0.0722 (14)	0.4391 (9)	0.043 (3)*	0.183 (2)
H6'	0.1372	−0.0283	0.3994	0.052*	0.183 (2)
C7'	0.1683 (3)	0.2123 (10)	0.4505 (8)	0.039 (2)*	0.183 (2)
H7'1	0.1757	0.2408	0.3696	0.046*	0.183 (2)
H7'2	0.2039	0.1727	0.5006	0.046*	0.183 (2)
C8'	0.1384 (3)	0.3213 (10)	0.6373 (7)	0.0338 (19)*	0.183 (2)
H8'1	0.1244	0.4179	0.6778	0.041*	0.183 (2)
H8'2	0.1749	0.2865	0.6862	0.041*	0.183 (2)
C9'	0.0414 (5)	0.2430 (18)	0.5496 (11)	0.057 (4)*	0.183 (2)
H9'1	0.0112	0.1585	0.5460	0.068*	0.183 (2)
H9'2	0.0295	0.3445	0.5885	0.068*	0.183 (2)
C10'	0.1166 (5)	0.0295 (15)	0.5663 (11)	0.045 (3)*	0.183 (2)
H10C	0.0897	−0.0645	0.5626	0.055*	0.183 (2)
H10D	0.1530	−0.0084	0.6136	0.055*	0.183 (2)
C11'	0.0957 (5)	0.1737 (16)	0.6295 (11)	0.041 (4)*	0.183 (2)
H11'	0.0892	0.1408	0.7112	0.049*	0.183 (2)

	U11	U22	U33	U12	U13	U23
S1	0.0758 (4)	0.0683 (4)	0.0212 (2)	−0.0451 (3)	0.01175 (19)	−0.00661 (18)
N1	0.0424 (7)	0.0430 (8)	0.0228 (6)	−0.0139 (6)	0.0104 (5)	−0.0023 (6)
C1	0.0332 (7)	0.0362 (8)	0.0227 (7)	−0.0052 (6)	0.0053 (5)	0.0032 (6)
C2	0.0324 (7)	0.0308 (8)	0.0207 (6)	−0.0046 (6)	0.0048 (5)	0.0004 (5)
C3	0.0337 (9)	0.0358 (10)	0.0338 (10)	−0.0021 (8)	0.0052 (7)	−0.0008 (8)
C4	0.0373 (11)	0.0496 (16)	0.0490 (13)	−0.0057 (11)	0.0111 (9)	−0.0014 (11)
C5	0.0488 (15)	0.0577 (16)	0.0497 (15)	−0.0226 (13)	−0.0013 (11)	0.0048 (12)
C6	0.078 (2)	0.0540 (17)	0.0329 (14)	−0.0292 (15)	0.0086 (13)	−0.0115 (12)
C7	0.0573 (12)	0.0448 (12)	0.0262 (9)	−0.0168 (9)	0.0111 (8)	−0.0075 (8)
C8	0.0404 (11)	0.0374 (11)	0.0406 (11)	0.0012 (8)	0.0025 (8)	0.0096 (9)
C9	0.0510 (16)	0.0478 (15)	0.0425 (13)	−0.0167 (12)	0.0124 (12)	0.0020 (10)
C10	0.0797 (18)	0.0336 (13)	0.0666 (19)	−0.0123 (12)	0.0206 (15)	−0.0110 (12)
C11	0.0638 (15)	0.0329 (12)	0.0483 (13)	−0.0030 (11)	0.0032 (11)	0.0106 (11)

S1—C1	1.6780 (14)	C9—H9B	0.9900
N1—C1	1.3149 (19)	C10—C11	1.542 (4)
N1—H1A	0.874 (9)	C10—H10A	0.9900
N1—H1B	0.870 (9)	C10—H10B	0.9900
C1—C2	1.5257 (19)	C11—H11	1.0000
C2—C3'	1.518 (7)	C3'—C4'	1.550 (12)
C2—C8	1.532 (2)	C3'—H3'1	0.9900
C2—C7	1.536 (2)	C3'—H3'2	0.9900
C2—C8'	1.546 (8)	C4'—C5'	1.507 (14)
C2—C3	1.552 (2)	C4'—C9'	1.524 (14)
C2—C7'	1.592 (8)	C4'—H4'	1.0000
C3—C4	1.533 (3)	C5'—C6'	1.498 (13)
C3—H3A	0.9900	C5'—H5'1	0.9900
C3—H3B	0.9900	C5'—H5'2	0.9900
C4—C9	1.509 (4)	C6'—C10'	1.521 (13)
C4—C5	1.515 (3)	C6'—C7'	1.538 (12)
C4—H4	1.0000	C6'—H6'	1.0000
C5—C6	1.509 (5)	C7'—H7'1	0.9900
C5—H5A	0.9900	C7'—H7'2	0.9900
C5—H5B	0.9900	C8'—C11'	1.561 (12)
C6—C10	1.523 (4)	C8'—H8'1	0.9900
C6—C7	1.543 (4)	C8'—H8'2	0.9900
C6—H6	1.0000	C9'—C11'	1.553 (14)
C7—H7A	0.9900	C9'—H9'1	0.9900
C7—H7B	0.9900	C9'—H9'2	0.9900
C8—C11	1.540 (3)	C10'—C11'	1.492 (13)
C8—H8A	0.9900	C10'—H10C	0.9900
C8—H8B	0.9900	C10'—H10D	0.9900
C9—C11	1.526 (4)	C11'—H11'	1.0000
C9—H9A	0.9900
C1—N1—H1A	121.5 (13)	H9A—C9—H9B	108.1
C1—N1—H1B	120.4 (13)	C6—C10—C11	109.2 (2)
H1A—N1—H1B	118.0 (18)	C6—C10—H10A	109.8
N1—C1—C2	117.69 (13)	C11—C10—H10A	109.8
N1—C1—S1	120.42 (11)	C6—C10—H10B	109.8
C2—C1—S1	121.89 (11)	C11—C10—H10B	109.8
C3'—C2—C1	109.3 (3)	H10A—C10—H10B	108.3
C3'—C2—C8	140.3 (3)	C9—C11—C8	109.1 (2)
C1—C2—C8	109.80 (12)	C9—C11—C10	109.7 (2)
C3'—C2—C7	58.9 (4)	C8—C11—C10	108.4 (2)
C1—C2—C7	113.32 (13)	C9—C11—H11	109.9
C8—C2—C7	109.82 (15)	C8—C11—H11	109.9
C3'—C2—C8'	110.5 (4)	C10—C11—H11	109.9
C1—C2—C8'	113.1 (3)	C2—C3'—C4'	111.3 (7)
C8—C2—C8'	46.1 (3)	C2—C3'—H3'1	109.4
C7—C2—C8'	133.0 (3)	C4'—C3'—H3'1	109.4
C3'—C2—C3	52.3 (4)	C2—C3'—H3'2	109.4
C1—C2—C3	107.40 (13)	C4'—C3'—H3'2	109.4
C8—C2—C3	108.66 (14)	H3'1—C3'—H3'2	108.0
C7—C2—C3	107.70 (14)	C5'—C4'—C9'	110.3 (10)
C8'—C2—C3	63.8 (3)	C5'—C4'—C3'	106.9 (9)
C3'—C2—C7'	108.1 (5)	C9'—C4'—C3'	106.0 (9)
C1—C2—C7'	109.3 (3)	C5'—C4'—H4'	111.2
C8—C2—C7'	64.1 (3)	C9'—C4'—H4'	111.2
C7—C2—C7'	50.8 (3)	C3'—C4'—H4'	111.2
C8'—C2—C7'	106.3 (5)	C6'—C5'—C4'	113.1 (10)
C3—C2—C7'	142.7 (3)	C6'—C5'—H5'1	109.0
C4—C3—C2	110.17 (16)	C4'—C5'—H5'1	109.0
C4—C3—H3A	109.6	C6'—C5'—H5'2	109.0
C2—C3—H3A	109.6	C4'—C5'—H5'2	109.0
C4—C3—H3B	109.6	H5'1—C5'—H5'2	107.8
C2—C3—H3B	109.6	C5'—C6'—C10'	112.2 (10)
H3A—C3—H3B	108.1	C5'—C6'—C7'	106.9 (9)
C9—C4—C5	109.4 (2)	C10'—C6'—C7'	106.8 (8)
C9—C4—C3	109.02 (19)	C5'—C6'—H6'	110.3
C5—C4—C3	109.4 (2)	C10'—C6'—H6'	110.3
C9—C4—H4	109.7	C7'—C6'—H6'	110.3
C5—C4—H4	109.7	C6'—C7'—C2	110.6 (6)
C3—C4—H4	109.7	C6'—C7'—H7'1	109.5
C6—C5—C4	110.2 (2)	C2—C7'—H7'1	109.5
C6—C5—H5A	109.6	C6'—C7'—H7'2	109.5
C4—C5—H5A	109.6	C2—C7'—H7'2	109.5
C6—C5—H5B	109.6	H7'1—C7'—H7'2	108.1
C4—C5—H5B	109.6	C2—C8'—C11'	111.1 (6)
H5A—C5—H5B	108.1	C2—C8'—H8'1	109.4
C5—C6—C10	110.5 (3)	C11'—C8'—H8'1	109.4
C5—C6—C7	109.6 (2)	C2—C8'—H8'2	109.4
C10—C6—C7	109.2 (3)	C11'—C8'—H8'2	109.4
C5—C6—H6	109.2	H8'1—C8'—H8'2	108.0
C10—C6—H6	109.2	C4'—C9'—C11'	114.2 (10)
C7—C6—H6	109.2	C4'—C9'—H9'1	108.7
C2—C7—C6	109.51 (17)	C11'—C9'—H9'1	108.7
C2—C7—H7A	109.8	C4'—C9'—H9'2	108.7
C6—C7—H7A	109.8	C11'—C9'—H9'2	108.7
C2—C7—H7B	109.8	H9'1—C9'—H9'2	107.6
C6—C7—H7B	109.8	C11'—C10'—C6'	112.9 (9)
H7A—C7—H7B	108.2	C11'—C10'—H10C	109.0
C2—C8—C11	110.19 (15)	C6'—C10'—H10C	109.0
C2—C8—H8A	109.6	C11'—C10'—H10D	109.0
C11—C8—H8A	109.6	C6'—C10'—H10D	109.0
C2—C8—H8B	109.6	H10C—C10'—H10D	107.8
C11—C8—H8B	109.6	C10'—C11'—C9'	108.9 (10)
H8A—C8—H8B	108.1	C10'—C11'—C8'	109.2 (10)
C4—C9—C11	110.8 (2)	C9'—C11'—C8'	104.2 (9)
C4—C9—H9A	109.5	C10'—C11'—H11'	111.4
C11—C9—H9A	109.5	C9'—C11'—H11'	111.4
C4—C9—H9B	109.5	C8'—C11'—H11'	111.4
C11—C9—H9B	109.5
N1—C1—C2—C3'	−66.3 (4)	C4—C9—C11—C8	60.1 (3)
S1—C1—C2—C3'	113.5 (4)	C4—C9—C11—C10	−58.4 (3)
N1—C1—C2—C8	120.45 (17)	C2—C8—C11—C9	−59.3 (2)
S1—C1—C2—C8	−59.78 (17)	C2—C8—C11—C10	60.1 (2)
N1—C1—C2—C7	−2.7 (2)	C6—C10—C11—C9	57.2 (3)
S1—C1—C2—C7	177.02 (13)	C6—C10—C11—C8	−61.8 (3)
N1—C1—C2—C8'	170.1 (4)	C1—C2—C3'—C4'	176.7 (6)
S1—C1—C2—C8'	−10.1 (4)	C8—C2—C3'—C4'	−13.3 (10)
N1—C1—C2—C3	−121.57 (16)	C7—C2—C3'—C4'	70.5 (7)
S1—C1—C2—C3	58.20 (16)	C8'—C2—C3'—C4'	−58.2 (8)
N1—C1—C2—C7'	51.9 (4)	C3—C2—C3'—C4'	−85.9 (7)
S1—C1—C2—C7'	−128.3 (3)	C7'—C2—C3'—C4'	57.8 (8)
C3'—C2—C3—C4	80.9 (4)	C2—C3'—C4'—C5'	−59.7 (10)
C1—C2—C3—C4	−177.77 (14)	C2—C3'—C4'—C9'	57.9 (10)
C8—C2—C3—C4	−59.06 (18)	C9'—C4'—C5'—C6'	−51.8 (15)
C7—C2—C3—C4	59.85 (19)	C3'—C4'—C5'—C6'	63.0 (13)
C8'—C2—C3—C4	−70.1 (4)	C4'—C5'—C6'—C10'	53.5 (15)
C7'—C2—C3—C4	12.4 (6)	C4'—C5'—C6'—C7'	−63.2 (13)
C2—C3—C4—C9	59.8 (2)	C5'—C6'—C7'—C2	58.7 (10)
C2—C3—C4—C5	−59.8 (2)	C10'—C6'—C7'—C2	−61.6 (9)
C9—C4—C5—C6	−59.6 (3)	C3'—C2—C7'—C6'	−57.6 (8)
C3—C4—C5—C6	59.8 (3)	C1—C2—C7'—C6'	−176.6 (6)
C4—C5—C6—C10	60.0 (3)	C8—C2—C7'—C6'	80.2 (6)
C4—C5—C6—C7	−60.3 (3)	C7—C2—C7'—C6'	−71.8 (6)
C3'—C2—C7—C6	−79.3 (4)	C8'—C2—C7'—C6'	61.0 (7)
C1—C2—C7—C6	−178.50 (19)	C3—C2—C7'—C6'	−6.9 (10)
C8—C2—C7—C6	58.3 (2)	C3'—C2—C8'—C11'	59.2 (8)
C8'—C2—C7—C6	10.5 (5)	C1—C2—C8'—C11'	−177.9 (6)
C3—C2—C7—C6	−59.9 (2)	C8—C2—C8'—C11'	−82.1 (7)
C7'—C2—C7—C6	85.0 (4)	C7—C2—C8'—C11'	−6.8 (9)
C5—C6—C7—C2	61.0 (3)	C3—C2—C8'—C11'	83.4 (7)
C10—C6—C7—C2	−60.2 (3)	C7'—C2—C8'—C11'	−57.9 (8)
C3'—C2—C8—C11	5.9 (6)	C5'—C4'—C9'—C11'	52.5 (15)
C1—C2—C8—C11	175.91 (18)	C3'—C4'—C9'—C11'	−62.8 (13)
C7—C2—C8—C11	−58.9 (2)	C5'—C6'—C10'—C11'	−55.3 (13)
C8'—C2—C8—C11	72.4 (4)	C7'—C6'—C10'—C11'	61.5 (11)
C3—C2—C8—C11	58.7 (2)	C6'—C10'—C11'—C9'	53.7 (13)
C7'—C2—C8—C11	−81.6 (4)	C6'—C10'—C11'—C8'	−59.5 (12)
C5—C4—C9—C11	59.2 (3)	C4'—C9'—C11'—C10'	−53.6 (14)
C3—C4—C9—C11	−60.5 (3)	C4'—C9'—C11'—C8'	62.9 (13)
C5—C6—C10—C11	−58.5 (3)	C2—C8'—C11'—C10'	58.0 (10)
C7—C6—C10—C11	62.1 (3)	C2—C8'—C11'—C9'	−58.2 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1i	0.87 (1)	2.63 (1)	3.4027 (14)	148 (2)
N1—H1B···S1ii	0.87 (1)	2.49 (1)	3.3485 (14)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1i	0.874 (9)	2.631 (13)	3.4027 (14)	147.9 (16)
N1—H1B⋯S1ii	0.870 (9)	2.492 (10)	3.3485 (14)	168.1 (17)

Symmetry codes: (i) ; (ii) .