3-tert-Butyl-1H-isochromene-1-thione

Khan, F.N.; Manivel, P.; Roopan, S.M.; Hathwar, V.R.; Akkurt, M.

doi:10.1107/S1600536810019422

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1470

https://doi.org/10.1107/S1600536810019422

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3-tert-Butyl-1H-isochromene-1-thione

F. Nawaz Khan,^a P. Manivel,^a S. Mohana Roopan,^a Venkatesha R. Hathwar ^b and Mehmet Akkurt ^c ^*

^aOrganic and Medicinal Chemistry Research Laboratory, Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, Tamil Nadu, India, ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and ^cDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 18 May 2010; accepted 24 May 2010; online 26 May 2010)

The title compound, C₁₃H₁₄OS, crystallizes with two independent molecules in the asymmetric unit. The unit cell contains three voids of 197 Å³, but the residual electron density (highest peak = 0.24 e Å⁻³ and deepest hole = −0.18 e Å⁻³) in the difference Fourier map suggests no solvent molecule occupies this void. The crystal structure is stabilized by π–π interactions between the isocoumarin ring systems, with centroid–centroid distances of 3.6793 (14) and 3.6566 (15) Å.

Related literature

For the crystal structure and synthesis of isocoumarin and its thioanalogues, see: Hathwar et al. (2007a ,b , 2009 ); Manivel et al. (2008 ); Basvanag et al. (2009 ); Henerson & Hill (1982 ).

Experimental

Crystal data

C₁₃H₁₄OS
M_r = 218.31
Trigonal, $[R \overline 3]$
a = 43.2799 (16) Å
c = 6.9025 (5) Å
V = 11197.2 (10) Å³
Z = 36
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.31 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.932, T_max = 0.966
33028 measured reflections
5943 independent reflections
3409 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.074
wR(F²) = 0.161
S = 1.09
5943 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810019422/fj2306sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810019422/fj2306Isup2.hkl

checkCIF report

Comment top

Isocoumarins are isolated in a great variety of microorganisms, plants, and insects, and have been shown to have considerable biological activity. Isocoumarins and its derivatives are secondary metabolites of a wide variety of microbial plant and insect sources and in synthesis of other medicinal compounds (Manivel et al., 2008, Basvanag et al., 2009). Sulfur containing isocoumarins have been known and a number of substituted thioisocoumarins, (Henerson et al., 1982) have been prepared. Most methods available for the construction of thioisocoumarin nucleus suffer from one or more drawbacks, such as the long reaction time required obtaining a good yield of the desired product or the use of expensive and hazardous reagents and solvents. Herewith, we are reporting the synthesis of 3-tert-butyl-1H-isochromene-1-thione using Lawessons reagent.

The isocoumarin moieties in the symmetric unit of the title compound, (I), (Fig. 1a and Fig. 1 b), are essentially parallel to each other with a small dihedral angle of 1.20 (7) °.

In the molecular structure of (I), there exist C—H···S and C—H···O intramolecular interactions (Table 1, Fig. 2). In adition, π-π interactions are observed between the isocoumarin ring systems [Cg2···Cg4(x, y, z) = 3.6793 (14) Å and Cg2···Cg5(x, y, 1 + z) = 3.6566 (15) Å; where Cg2, Cg4 and Cg5 are the centroids of the C1–C6, O2'/C1'/C6'–C9' and C1'–C6' rings, respectively]. There is no classic hydrogen bonds in the structure.

Related literature top

For the crystal structure and synthesis of isocoumarin and its thioanalogues, see: Hathwar et al. (2007a,b, 2009); Manivel et al. (2008); Basvanag et al. (2009); Henerson & Hill (1982).

Experimental top

The 3-tert-butyl-1H-isochromen-1-one and Lawessons reagent were taken in toluene (1:1 ratio) and refluxed for 1 h. Then the reaction mass was quenched with water, extracted with dichloromethane, washed with water, dried, concentrated and purified by column chromatography to get the titled compound. Single crystals of the title compound were obtained via recrystalization from a chloroform solution.

Structure description top

The isocoumarin moieties in the symmetric unit of the title compound, (I), (Fig. 1a and Fig. 1 b), are essentially parallel to each other with a small dihedral angle of 1.20 (7) °.

For the crystal structure and synthesis of isocoumarin and its thioanalogues, see: Hathwar et al. (2007a,b, 2009); Manivel et al. (2008); Basvanag et al. (2009); Henerson & Hill (1982).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); 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).

Figures top

	Fig. 1. The first molecule in the asymmetric unit with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. The second molecule in the asymmetric unit with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 3. The packing diagram of the title compound down c axis in the unitcell.

3-tert-Butyl-1H-isochromene-1-thione top

Crystal data top

C₁₃H₁₄OS	D_x = 1.166 Mg m⁻³
M_r = 218.31	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 856 reflections
Hall symbol: -R 3	θ = 1.9–24.7°
a = 43.2799 (16) Å	µ = 0.23 mm⁻¹
c = 6.9025 (5) Å	T = 293 K
V = 11197.2 (10) Å³	Block, yellow
Z = 36	0.31 × 0.18 × 0.15 mm
F(000) = 4176

Data collection top

Bruker SMART CCD area-detector diffractometer	5943 independent reflections
Radiation source: fine-focus sealed tube	3409 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ω scans	θ_max = 28.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −57→57
T_min = 0.932, T_max = 0.966	k = −56→56
33028 measured reflections	l = −9→9

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0599P)² + 4.5485P] where P = (F_o² + 2F_c²)/3
5943 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₃H₁₄OS	Z = 36
M_r = 218.31	Mo Kα radiation
Trigonal, R3	µ = 0.23 mm⁻¹
a = 43.2799 (16) Å	T = 293 K
c = 6.9025 (5) Å	0.31 × 0.18 × 0.15 mm
V = 11197.2 (10) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	5943 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3409 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.966	R_int = 0.047
33028 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	0 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 1.09	Δρ_max = 0.24 e Å⁻³
5943 reflections	Δρ_min = −0.18 e Å⁻³
271 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 esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
S1	0.81419 (2)	−0.00817 (2)	0.78291 (13)	0.0811 (3)
O1	0.87826 (4)	0.04385 (4)	0.7757 (3)	0.0606 (7)
C1	0.86386 (7)	0.09888 (6)	0.7809 (3)	0.0502 (8)
C2	0.85585 (8)	0.12659 (7)	0.7850 (4)	0.0631 (10)
C3	0.82145 (9)	0.11923 (8)	0.7911 (4)	0.0729 (11)
C4	0.79363 (8)	0.08436 (9)	0.7932 (4)	0.0720 (11)
C5	0.80057 (7)	0.05677 (7)	0.7903 (4)	0.0635 (10)
C6	0.83556 (6)	0.06358 (6)	0.7841 (3)	0.0492 (8)
C7	0.84331 (7)	0.03469 (6)	0.7812 (4)	0.0548 (9)
C8	0.90635 (6)	0.07871 (6)	0.7703 (3)	0.0516 (8)
C9	0.89948 (7)	0.10530 (6)	0.7739 (3)	0.0535 (8)
C10	0.94129 (7)	0.07913 (7)	0.7620 (4)	0.0639 (10)
C11	0.97229 (7)	0.11727 (8)	0.7400 (5)	0.0878 (13)
C12	0.94624 (9)	0.06357 (9)	0.9523 (5)	0.0979 (16)
C13	0.94106 (9)	0.05714 (9)	0.5875 (5)	0.1021 (16)
S1'	0.77849 (2)	0.11691 (2)	0.28420 (12)	0.0772 (3)
O2'	0.76501 (4)	0.05251 (4)	0.2971 (3)	0.0574 (6)
C1'	0.83413 (6)	0.06544 (6)	0.2874 (3)	0.0465 (8)
C2'	0.86926 (6)	0.07253 (7)	0.2822 (4)	0.0574 (9)
C3'	0.89714 (7)	0.10670 (8)	0.2764 (4)	0.0649 (10)
C4'	0.89068 (7)	0.13502 (7)	0.2747 (4)	0.0660 (10)
C5'	0.85652 (7)	0.12899 (6)	0.2800 (3)	0.0579 (9)
C6'	0.82767 (6)	0.09412 (6)	0.2863 (3)	0.0459 (8)
C7'	0.79136 (6)	0.08729 (6)	0.2900 (3)	0.0520 (8)
C8'	0.77110 (6)	0.02397 (6)	0.2971 (4)	0.0521 (8)
C9'	0.80418 (6)	0.02988 (6)	0.2925 (3)	0.0524 (9)
C10'	0.73624 (7)	−0.01086 (6)	0.3019 (5)	0.0680 (10)
C11'	0.74338 (8)	−0.04203 (7)	0.2923 (5)	0.0903 (13)
C12'	0.71642 (9)	−0.01317 (8)	0.4895 (6)	0.1127 (16)
C13'	0.71430 (8)	−0.01215 (8)	0.1256 (6)	0.1090 (16)
H2	0.87430	0.15020	0.78360	0.0760*
H3	0.81660	0.13790	0.79390	0.0880*
H4	0.77020	0.07960	0.79660	0.0870*
H5	0.78180	0.03330	0.79240	0.0760*
H9	0.91830	0.12870	0.77170	0.0640*
H11A	0.96880	0.12780	0.62590	0.1320*
H11B	0.99420	0.11690	0.72860	0.1320*
H11C	0.97330	0.13100	0.85160	0.1320*
H12A	0.94830	0.07890	1.05820	0.1460*
H12B	0.96750	0.06190	0.94440	0.1460*
H12C	0.92600	0.04030	0.97290	0.1460*
H13A	0.92160	0.03310	0.59980	0.1540*
H13B	0.96320	0.05700	0.58270	0.1540*
H13C	0.93820	0.06750	0.47070	0.1540*
H2'	0.87380	0.05370	0.28280	0.0690*
H3'	0.92050	0.11100	0.27370	0.0780*
H4'	0.90970	0.15830	0.26980	0.0790*
H5'	0.85250	0.14820	0.27940	0.0700*
H9'	0.80810	0.01060	0.29270	0.0630*
H11D	0.75560	−0.04070	0.17380	0.1360*
H11E	0.72110	−0.06410	0.29670	0.1360*
H11F	0.75790	−0.04080	0.40050	0.1360*
H12D	0.72880	−0.01600	0.59730	0.1690*
H12E	0.69270	−0.03330	0.48330	0.1690*
H12F	0.71530	0.00830	0.50580	0.1690*
H13D	0.71030	0.00780	0.12930	0.1630*
H13E	0.69180	−0.03400	0.12730	0.1630*
H13F	0.72700	−0.01110	0.00950	0.1630*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0696 (5)	0.0415 (4)	0.1141 (7)	0.0142 (3)	−0.0067 (4)	−0.0026 (4)
O1	0.0547 (11)	0.0442 (10)	0.0807 (13)	0.0231 (8)	−0.0041 (9)	−0.0046 (8)
C1	0.0629 (16)	0.0480 (14)	0.0398 (14)	0.0278 (13)	0.0024 (11)	−0.0030 (11)
C2	0.082 (2)	0.0539 (16)	0.0593 (17)	0.0383 (15)	0.0031 (14)	−0.0037 (13)
C3	0.100 (2)	0.079 (2)	0.0639 (19)	0.063 (2)	0.0030 (16)	−0.0045 (15)
C4	0.0701 (19)	0.097 (2)	0.0658 (19)	0.0544 (19)	0.0005 (15)	−0.0057 (17)
C5	0.0550 (16)	0.0694 (18)	0.0613 (17)	0.0275 (14)	0.0006 (13)	−0.0017 (14)
C6	0.0540 (14)	0.0494 (14)	0.0420 (14)	0.0243 (12)	−0.0004 (11)	−0.0034 (11)
C7	0.0536 (15)	0.0482 (14)	0.0561 (16)	0.0206 (12)	−0.0047 (12)	−0.0036 (12)
C8	0.0493 (14)	0.0467 (14)	0.0497 (15)	0.0171 (12)	−0.0020 (11)	−0.0034 (11)
C9	0.0575 (15)	0.0429 (13)	0.0497 (15)	0.0173 (12)	0.0015 (12)	−0.0028 (11)
C10	0.0535 (16)	0.0663 (17)	0.0679 (19)	0.0270 (14)	−0.0014 (13)	−0.0039 (14)
C11	0.0572 (18)	0.082 (2)	0.107 (3)	0.0220 (16)	0.0055 (17)	0.0042 (18)
C12	0.080 (2)	0.115 (3)	0.111 (3)	0.058 (2)	0.0003 (19)	0.028 (2)
C13	0.081 (2)	0.117 (3)	0.121 (3)	0.059 (2)	−0.004 (2)	−0.037 (2)
S1'	0.0796 (5)	0.0522 (4)	0.1108 (7)	0.0413 (4)	0.0313 (4)	0.0127 (4)
O2'	0.0444 (9)	0.0391 (9)	0.0862 (13)	0.0191 (8)	0.0055 (8)	−0.0002 (8)
C1'	0.0473 (13)	0.0459 (13)	0.0432 (14)	0.0209 (11)	0.0008 (11)	−0.0034 (10)
C2'	0.0506 (15)	0.0635 (16)	0.0586 (17)	0.0288 (13)	−0.0024 (12)	−0.0038 (13)
C3'	0.0444 (15)	0.077 (2)	0.0610 (18)	0.0212 (14)	−0.0013 (12)	−0.0015 (14)
C4'	0.0506 (16)	0.0582 (17)	0.0604 (18)	0.0055 (13)	0.0034 (13)	−0.0005 (13)
C5'	0.0616 (17)	0.0445 (14)	0.0561 (16)	0.0178 (12)	0.0086 (13)	−0.0021 (12)
C6'	0.0447 (13)	0.0410 (12)	0.0430 (14)	0.0147 (11)	0.0056 (10)	−0.0042 (10)
C7'	0.0559 (15)	0.0414 (13)	0.0536 (16)	0.0205 (12)	0.0112 (12)	−0.0004 (11)
C8'	0.0507 (14)	0.0364 (12)	0.0675 (17)	0.0206 (11)	−0.0047 (12)	−0.0061 (11)
C9'	0.0539 (15)	0.0396 (13)	0.0665 (17)	0.0255 (12)	−0.0043 (12)	−0.0069 (11)
C10'	0.0500 (15)	0.0382 (14)	0.105 (2)	0.0140 (12)	−0.0103 (16)	−0.0065 (14)
C11'	0.0727 (19)	0.0383 (15)	0.147 (3)	0.0181 (14)	−0.023 (2)	−0.0098 (17)
C12'	0.078 (2)	0.061 (2)	0.158 (4)	0.0039 (17)	0.041 (2)	0.006 (2)
C13'	0.072 (2)	0.063 (2)	0.168 (4)	0.0157 (17)	−0.047 (2)	−0.012 (2)

Geometric parameters (Å, º) top

S1—C7	1.641 (2)	C13—H13A	0.9600
S1'—C7'	1.634 (3)	C13—H13B	0.9600
O1—C8	1.386 (3)	C13—H13C	0.9600
O1—C7	1.359 (4)	C1'—C2'	1.393 (4)
O2'—C8'	1.386 (3)	C1'—C6'	1.402 (4)
O2'—C7'	1.361 (3)	C1'—C9'	1.434 (3)
C1—C6	1.401 (3)	C2'—C3'	1.364 (4)
C1—C2	1.405 (4)	C3'—C4'	1.387 (4)
C1—C9	1.424 (5)	C4'—C5'	1.367 (5)
C2—C3	1.359 (6)	C5'—C6'	1.398 (3)
C3—C4	1.382 (5)	C6'—C7'	1.447 (4)
C4—C5	1.369 (5)	C8'—C9'	1.323 (4)
C5—C6	1.391 (4)	C8'—C10'	1.509 (4)
C6—C7	1.448 (4)	C10'—C11'	1.529 (4)
C8—C9	1.325 (4)	C10'—C12'	1.529 (5)
C8—C10	1.504 (4)	C10'—C13'	1.527 (5)
C10—C11	1.528 (4)	C2'—H2'	0.9300
C10—C12	1.539 (5)	C3'—H3'	0.9300
C10—C13	1.532 (4)	C4'—H4'	0.9300
C2—H2	0.9300	C5'—H5'	0.9300
C3—H3	0.9300	C9'—H9'	0.9300
C4—H4	0.9300	C11'—H11D	0.9600
C5—H5	0.9300	C11'—H11E	0.9600
C9—H9	0.9300	C11'—H11F	0.9600
C11—H11A	0.9600	C12'—H12D	0.9600
C11—H11B	0.9600	C12'—H12E	0.9600
C11—H11C	0.9600	C12'—H12F	0.9600
C12—H12C	0.9600	C13'—H13D	0.9600
C12—H12A	0.9600	C13'—H13E	0.9600
C12—H12B	0.9600	C13'—H13F	0.9600

S1'···C5'ⁱ	3.681 (2)	H9···H11A	2.4200
S1···H3'ⁱⁱ	3.0200	H9···H11C	2.4000
S1···H11Cⁱⁱⁱ	3.0800	H9'···C11'	2.5800
S1···H5	2.7800	H9'···H2'	2.5000
S1'···H11E^iv	3.1800	H9'···H11D	2.3900
S1'···H5'	2.7900	H9'···H11F	2.3200
S1'···H5'ⁱ	3.0100	H11A···H9	2.4200
S1'···H2^v	3.2000	H11A···H13C	2.5000
O1···H13A	2.4700	H11A···C9	2.8400
O1···H12C	2.5400	H11B···H12B	2.5400
O2'···H12F	2.5000	H11B···H13B	2.4600
O2'···H13D	2.4700	H11C···H9	2.4000
C1'···C6	3.431 (3)	H11C···C9	2.8600
C1'···C6^vi	3.476 (3)	H11C···H12A	2.4200
C2···C5'	3.487 (3)	H11C···S1^ix	3.0800
C2···C5'^vii	3.418 (3)	H11D···H13F	2.4600
C3'···C9^vi	3.471 (3)	H11D···C9'	2.8300
C3'···C9	3.437 (3)	H11D···H9'	2.3900
C4···C7'^vii	3.435 (3)	H11E···H12E	2.5700
C4···C7'	3.479 (3)	H11E···H13E	2.5100
C5'···S1'ⁱ	3.681 (2)	H11E···S1'^x	3.1800
C5'···C2	3.487 (3)	H11F···C9'	2.7900
C5'···C2^vi	3.418 (3)	H11F···H12D	2.4400
C6···C1'^vii	3.476 (3)	H11F···H9'	2.3200
C6···C1'	3.431 (3)	H12A···H11C	2.4200
C7'···C4^vi	3.435 (3)	H12B···H13B	2.5000
C7'···C4	3.479 (3)	H12B···H11B	2.5400
C9···C3'	3.437 (3)	H12C···H13A	2.5900
C9···C3'^vii	3.471 (3)	H12C···O1	2.5400
C9···H11A	2.8400	H12D···H11F	2.4400
C9···H11C	2.8600	H12D···H5	2.5900
C9'···H11F	2.7900	H12E···H13E	2.4600
C9'···H11D	2.8300	H12E···H11E	2.5700
C11···H9	2.6300	H12F···O2'	2.5000
C11'···H9'	2.5800	H12F···H13E^iv	2.5900
H2···H9	2.5000	H13A···H12C	2.5900
H2···S1'^v	3.2000	H13A···O1	2.4700
H2'···H9'	2.5000	H13B···H12B	2.5000
H3'···S1^viii	3.0200	H13B···H11B	2.4600
H5···H12D	2.5900	H13C···H11A	2.5000
H5···S1	2.7800	H13D···O2'	2.4700
H5'···S1'	2.7900	H13E···H11E	2.5100
H5'···S1'ⁱ	3.0100	H13E···H12E	2.4600
H9···C11	2.6300	H13E···H12F^x	2.5900
H9···H2	2.5000	H13F···H11D	2.4600

C7—O1—C8	124.1 (2)	H13A—C13—H13B	109.00
C7'—O2'—C8'	123.9 (2)	C2'—C1'—C6'	118.9 (2)
C2—C1—C6	118.4 (3)	C2'—C1'—C9'	122.6 (2)
C2—C1—C9	122.6 (2)	C6'—C1'—C9'	118.5 (3)
C6—C1—C9	119.0 (2)	C1'—C2'—C3'	121.1 (3)
C1—C2—C3	120.6 (3)	C2'—C3'—C4'	119.9 (3)
C2—C3—C4	120.7 (3)	C3'—C4'—C5'	120.5 (3)
C3—C4—C5	120.1 (4)	C4'—C5'—C6'	120.3 (3)
C4—C5—C6	120.4 (3)	C1'—C6'—C5'	119.3 (3)
C1—C6—C7	119.2 (3)	C1'—C6'—C7'	119.7 (2)
C5—C6—C7	121.0 (2)	C5'—C6'—C7'	120.9 (2)
C1—C6—C5	119.8 (2)	S1'—C7'—O2'	116.3 (2)
S1—C7—C6	126.7 (2)	S1'—C7'—C6'	126.93 (18)
O1—C7—C6	117.0 (2)	O2'—C7'—C6'	116.8 (2)
S1—C7—O1	116.3 (2)	O2'—C8'—C9'	119.8 (2)
O1—C8—C10	110.1 (2)	O2'—C8'—C10'	110.5 (2)
C9—C8—C10	130.6 (2)	C9'—C8'—C10'	129.7 (2)
O1—C8—C9	119.3 (3)	C1'—C9'—C8'	121.2 (2)
C1—C9—C8	121.5 (2)	C8'—C10'—C11'	109.8 (3)
C8—C10—C12	108.7 (3)	C8'—C10'—C12'	109.4 (2)
C8—C10—C13	109.2 (3)	C8'—C10'—C13'	108.2 (2)
C8—C10—C11	110.6 (2)	C11'—C10'—C12'	109.5 (3)
C11—C10—C13	108.8 (3)	C11'—C10'—C13'	109.2 (3)
C12—C10—C13	111.0 (3)	C12'—C10'—C13'	110.8 (3)
C11—C10—C12	108.6 (3)	C1'—C2'—H2'	120.00
C3—C2—H2	120.00	C3'—C2'—H2'	119.00
C1—C2—H2	120.00	C2'—C3'—H3'	120.00
C2—C3—H3	120.00	C4'—C3'—H3'	120.00
C4—C3—H3	120.00	C3'—C4'—H4'	120.00
C3—C4—H4	120.00	C5'—C4'—H4'	120.00
C5—C4—H4	120.00	C4'—C5'—H5'	120.00
C6—C5—H5	120.00	C6'—C5'—H5'	120.00
C4—C5—H5	120.00	C1'—C9'—H9'	119.00
C1—C9—H9	119.00	C8'—C9'—H9'	119.00
C8—C9—H9	119.00	C10'—C11'—H11D	109.00
C10—C11—H11B	109.00	C10'—C11'—H11E	109.00
C10—C11—H11C	109.00	C10'—C11'—H11F	109.00
C10—C11—H11A	109.00	H11D—C11'—H11E	110.00
H11A—C11—H11C	110.00	H11D—C11'—H11F	109.00
H11B—C11—H11C	110.00	H11E—C11'—H11F	110.00
H11A—C11—H11B	109.00	C10'—C12'—H12D	110.00
C10—C12—H12A	109.00	C10'—C12'—H12E	109.00
C10—C12—H12B	109.00	C10'—C12'—H12F	110.00
H12A—C12—H12B	109.00	H12D—C12'—H12E	109.00
H12A—C12—H12C	109.00	H12D—C12'—H12F	110.00
C10—C12—H12C	109.00	H12E—C12'—H12F	110.00
H12B—C12—H12C	110.00	C10'—C13'—H13D	109.00
C10—C13—H13B	110.00	C10'—C13'—H13E	109.00
C10—C13—H13C	109.00	C10'—C13'—H13F	109.00
C10—C13—H13A	109.00	H13D—C13'—H13E	110.00
H13A—C13—H13C	109.00	H13D—C13'—H13F	110.00
H13B—C13—H13C	110.00	H13E—C13'—H13F	109.00

C8—O1—C7—S1	178.89 (18)	C10—C8—C9—C1	179.7 (2)
C8—O1—C7—C6	−0.9 (4)	O1—C8—C10—C11	175.6 (2)
C7—O1—C8—C9	1.2 (3)	O1—C8—C10—C12	−65.3 (3)
C7—O1—C8—C10	−179.1 (2)	O1—C8—C10—C13	55.9 (3)
C8'—O2'—C7'—S1'	178.1 (2)	C6'—C1'—C2'—C3'	0.1 (4)
C8'—O2'—C7'—C6'	−1.3 (3)	C9'—C1'—C2'—C3'	179.7 (2)
C7'—O2'—C8'—C9'	0.9 (4)	C2'—C1'—C6'—C5'	0.0 (3)
C7'—O2'—C8'—C10'	−178.9 (2)	C2'—C1'—C6'—C7'	179.5 (2)
C9—C1—C2—C3	179.8 (2)	C9'—C1'—C6'—C5'	−179.56 (19)
C2—C1—C6—C5	0.3 (3)	C9'—C1'—C6'—C7'	−0.1 (3)
C6—C1—C2—C3	−0.3 (4)	C2'—C1'—C9'—C8'	−179.9 (2)
C6—C1—C9—C8	0.0 (3)	C6'—C1'—C9'—C8'	−0.4 (3)
C9—C1—C6—C5	−179.8 (2)	C1'—C2'—C3'—C4'	−0.3 (4)
C9—C1—C6—C7	0.3 (3)	C2'—C3'—C4'—C5'	0.4 (4)
C2—C1—C6—C7	−179.6 (2)	C3'—C4'—C5'—C6'	−0.3 (4)
C2—C1—C9—C8	180.0 (2)	C4'—C5'—C6'—C1'	0.1 (3)
C1—C2—C3—C4	−0.1 (4)	C4'—C5'—C6'—C7'	−179.4 (2)
C2—C3—C4—C5	0.4 (4)	C1'—C6'—C7'—S1'	−178.42 (17)
C3—C4—C5—C6	−0.4 (4)	C1'—C6'—C7'—O2'	0.9 (3)
C4—C5—C6—C7	179.9 (2)	C5'—C6'—C7'—S1'	1.1 (3)
C4—C5—C6—C1	0.0 (4)	C5'—C6'—C7'—O2'	−179.7 (2)
C1—C6—C7—O1	0.1 (3)	O2'—C8'—C9'—C1'	0.0 (4)
C5—C6—C7—S1	0.5 (4)	C10'—C8'—C9'—C1'	179.7 (3)
C5—C6—C7—O1	−179.8 (2)	O2'—C8'—C10'—C11'	177.4 (2)
C1—C6—C7—S1	−179.63 (19)	O2'—C8'—C10'—C12'	−62.5 (3)
O1—C8—C9—C1	−0.8 (3)	O2'—C8'—C10'—C13'	58.3 (3)
C9—C8—C10—C11	−4.8 (4)	C9'—C8'—C10'—C11'	−2.4 (4)
C9—C8—C10—C12	114.3 (3)	C9'—C8'—C10'—C12'	117.8 (3)
C9—C8—C10—C13	−124.5 (3)	C9'—C8'—C10'—C13'	−121.5 (3)

Symmetry codes: (i) −x+5/3, −y+1/3, −z+1/3; (ii) x−y, x−1, −z+1; (iii) x−y, x−1, −z+2; (iv) −y+2/3, x−y−2/3, z+1/3; (v) −x+5/3, −y+1/3, −z+4/3; (vi) x, y, z−1; (vii) x, y, z+1; (viii) y+1, −x+y+1, −z+1; (ix) y+1, −x+y+1, −z+2; (x) −x+y+4/3, −x+2/3, z−1/3.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···S1	0.93	2.78	3.148 (3)	105
C5′—H5′···S1′	0.93	2.79	3.149 (3)	104
C12—H12C···O1	0.96	2.54	2.891 (5)	102
C12′—H12F···O2′	0.96	2.50	2.879 (4)	103
C13—H13A···O1	0.96	2.47	2.800 (5)	100
C13′—H13D···O2′	0.96	2.47	2.812 (4)	101

Experimental details

Crystal data
Chemical formula	C₁₃H₁₄OS
M_r	218.31
Crystal system, space group	Trigonal, R3
Temperature (K)	293
a, c (Å)	43.2799 (16), 6.9025 (5)
V (Å³)	11197.2 (10)
Z	36
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.31 × 0.18 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.932, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	33028, 5943, 3409
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.161, 1.09
No. of reflections	5943
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.18

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···S1	0.93	2.78	3.148 (3)	105
C5'—H5'···S1'	0.93	2.79	3.149 (3)	104
C12—H12C···O1	0.96	2.54	2.891 (5)	102
C12'—H12F···O2'	0.96	2.50	2.879 (4)	103
C13—H13A···O1	0.96	2.47	2.800 (5)	100
C13'—H13D···O2'	0.96	2.47	2.812 (4)	101

Acknowledgements

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA–DST program at IISc. We thank Professor T. N. Guru Row, IISc, Bangalore, for the data collection. FNK thanks the DST for Fast Track Proposal funding.

References

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