Adamantane-1-thio­amide

Zahid, M.; Khawar Rauf, M.; Bolte, M.; Hameed, S.

doi:10.1107/S1600536809027470

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1891

doi:10.1107/S1600536809027470

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Adamantane-1-thioamide

Maryam Zahid,^a M. Khawar Rauf,^a Michael Bolte ^b and Shahid Hameed ^a ^*

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: shameed@qau.edu.pk

(Received 9 July 2009; accepted 13 July 2009; online 18 July 2009)

The title compound, C₁₁H₁₇NS, is an important intermediate for the synthesis of biologically active adamantlythiazolo-oxadiazoles. 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 intermolecular N—H⋯S hydrogen-bonding interactions.

Related literature

Adamantane derivatives include well known drugs such as 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_r = 195.32
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.103
S = 1.07
2002 reflections
163 parameters
35 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Adamantane derivatives have found widespread use as biologically active agents to combat various human pathogens. These derivatives include the well known drugs like Rimantadine, Memantine, Adapalene and Adatanserin (Krasnikov et al., 2004). A broad spectrum of biological activities like antimalarial (Singh et al., 2007), glucosylceramide metabolism inhibitors (Wennekes et al., 2007), vitamin D receptor modulators (Inaba et al., 2007) and anti-influenza (Kolocouris et al., 2007), is associated with adamantane containing preparations and compounds. Thioamides, on the other hand, 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). The title compound, adamantane-1-thioamide (1), was synthesized in this laboratory as an intermediate in the synthesis of adamantlythiazolo-oxadiazoles to explore their potential as antitumour agents. The synthesis was accomplished by treating adamantane-1-carbonitrile with P₄S₁₀ according to a known procedure (Kaboudin et al., 2006). Here, we are going to report the crystal structure of (1). The crystal structure is stabilized by intermolecular N—H···S, hydrogen-bond interactions.

Related literature top

Adamantane derivatives include well known drugs such as 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 et al. (2006).

Experimental top

A solution of P₄S₁₀ (3.1 g, 7.0 mmol.) in ethanol (10 ml) was stirred for 1 h. Adamantane-1-carbonitrile (0.5 g, 3.5 mmol.) was added and the mixture refluxed for 12 h. The mixture was concentrated, water (25 ml) was added and extracted with dichloromethane (3 × 25 ml). The combined organic extracts were dried (anhydrous Na₂SO₄, concentrated on rotary and refrigerated. The white precipitates separated were recrystallized from ethanol. Yield: 62%; m.p.: 159–162 °C; Rf: 0.40 (n-hexane: ethylacetate; 7:3); IR (ν_max, KBr, cm^-1): 3424, 3323, 3144, 2907, 2848, 1656, 1449, 1384, 1310, 1240; ¹H-NMR (CDCl₃): δ 7.9 (1H, b), 7.1 (1H, b), 1.9 (9H, b), 1.71 (6H, b); ¹³C-NMR (CDCl₃): δ 218.8, 45.6, 41.7, 36.2, 28.4; EIMS: (m/z %) 195 (80), 162 (15), 135 (100), 107 (13),93 (20), 79 (23), 60 (13); Elemental analysis for C₁₁H₁₇NS (195.32):C, 67.64; H, 8.77; N, 7.17. Found: C, 67.87; H, 8.88; N, 7.38.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level. The disordered atoms of the minor occupied site have been omitted for clarity.
	Fig. 2. Molecular structure of the title compound (I) showing both the major and minor occupied positions of the disordered atoms.

Adamantane-1-thioamide top

Crystal data top

C₁₁H₁₇NS	F(000) = 848
M_r = 195.32	D_x = 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

Data collection top

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

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)] = 0.038	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(F_o²) + (0.0572P)² + 0.6628P] where P = (F_o² + 2F_c²)/3
2002 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.20 e Å⁻³
35 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₁H₁₇NS	V = 2148.8 (3) Å³
M_r = 195.32	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.255 (2) Å	µ = 0.26 mm⁻¹
b = 7.9879 (5) Å	T = 173 K
c = 11.2928 (9) Å	0.39 × 0.26 × 0.25 mm
β = 100.859 (7)°

Data collection top

Stoe IPDS-II two-circle diffractometer	2002 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	1703 reflections with I > 2σ(I)
T_min = 0.907, T_max = 0.939	R_int = 0.040
7423 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	35 restraints
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.20 e Å⁻³
2002 reflections	Δρ_min = −0.30 e Å⁻³
163 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Symmetry codes: (i) x, −y+1, z−1/2; (ii) −x+1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₇NS
M_r	195.32
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	24.255 (2), 7.9879 (5), 11.2928 (9)
β (°)	100.859 (7)
V (Å³)	2148.8 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.39 × 0.26 × 0.25

Data collection
Diffractometer	Stoe IPDS-II two-circle diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2009; Blessing, 1995)
T_min, T_max	0.907, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	7423, 2002, 1703
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.607

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.103, 1.07
No. of reflections	2002
No. of parameters	163
No. of restraints	35
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.30

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x, −y+1, z−1/2; (ii) −x+1/2, −y+3/2, −z+1.

Acknowledgements

MKR is grateful to the HEC-Pakistan for financial support for a PhD program under scholarship No.[ILC–0363104].

References

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