(5,7-Dimethyl-2-oxo-2H-chromen-4-yl)methyl diethyl­dithio­carbamate

Kumar, K.M.; Devarajegowda, H.C.; Jeyaseelan, S.; Mahabaleshwaraiah, N.M.; Kotresh, O.

doi:10.1107/S1600536812019757

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1657

doi:10.1107/S1600536812019757

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(5,7-Dimethyl-2-oxo-2H-chromen-4-yl)methyl diethyldithiocarbamate

K. Mahesh Kumar,^a H. C. Devarajegowda,^b ^* S Jeyaseelan,^b N. M. Mahabaleshwaraiah ^a and O. Kotresh ^a

^aDepartment of Chemistry, Karnatak Science College, Dharwad 580 001, Karnataka, India, and ^bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 29 April 2012; accepted 2 May 2012; online 5 May 2012)

In the title compound, C₁₇H₂₁NO₂S₂, the coumarin ring system is nearly planar, with a maximum deviation of 0.080 (2) Å from the mean plane. An intramolecular C—H⋯S hydrogen bond occurs. The crystal structure features C—H⋯S hydrogen bonds and weak π–π interactions with a centroid–centroid distance of 3.679 (1) Å.

Related literature

For biological applications of coumarins and dithiocarbamates, see: Smith et al. (1998 ); Nawrot-Modraka et al. (2006 ); Basanagouda et al. (2009 ); Kalkhambkar et al. (2007 ); El-Shorbagi (2000 ); Ronconi et al. (2006 ); Cvek & Dvorak (2007 ). For a related structure, see: Kumar et al. (2012 ). For the synthesis of the title compound, see: Shastri et al. (2004 ).

Experimental

Crystal data

C₁₇H₂₁NO₂S₂
M_r = 335.47
Monoclinic, P 2₁ /n
a = 7.8570 (2) Å
b = 23.7745 (5) Å
c = 9.7684 (2) Å
β = 109.483 (1)°
V = 1720.22 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 293 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: ψ scan (SADABS; Sheldrick, 2007 ) T_min = 0.770, T_max = 1.000
14939 measured reflections
3033 independent reflections
2803 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.135
S = 1.04
3033 reflections
204 parameters
H-atom parameters constrained
Δρ_max = 0.90 e Å⁻³
Δρ_min = −0.73 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯S2ⁱ	0.93	2.86	3.751 (2)	161
C16—H16C⋯S1	0.96	2.53	3.282 (3)	135
Symmetry code: (i) x, y, z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812019757/wn2474sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019757/wn2474Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812019757/wn2474Isup3.cml

checkCIF report

Comment top

Coumarins constitute a class of compounds which are found widely in nature and possess diverse biological activities. Over recent decades, medicinal chemists have paid great attention to the isolation, screening and structural modifications of new coumarins. They have been found to exhibit a wide range of applications in cancer, the HIV drug development arena (Smith et al., 1998), anti-tumor, anti-bacterial and cytotoxic activity (Nawrot-Modraka et al., 2006). In 4-substituted coumarins, the groups attached at the C-4 methylene carbon been shown to influence their solid state conformations, as observed in 4-aryloxymethyl (Basanagouda et al., 2009) and 4-arylaminomethyl coumarins (Kalkhambkar et al., 2007).

Dithiocarbamates have shown wide applications as pesticides,fungicides in agriculture (El-Shorbagi, 2000), potent anticancer agents (Ronconi et al., 2006), organic intermediates, rubber additives, additives of polluted water and vulcanizing agents (Cvek & Dvorak, 2007).

In view of the above observations,we proposed that 4-substituted coumarins bearing the dithiocarbamate (DTC)group should display some interesting biological activity and the title compound was screened for fungicidal, bacterial and DNA cleavage properties.The crystal structure of a coumarin derivative linked to the DTC group has been reported (Kumar et al., 2012).

The title compound is one of a series of dithiocarbamate coumarins with potential as possible anti-microbial agents. For these reasons, in continuation of our interest in the crystal structures of coumarin derivatives, we report here its crystal structure.

The asymmetric unit of 5,7-dimethyl-2-oxo-2H-chromen-4-yl)methyl diethyldithiocarbamate is shown in Fig. 1.The coumarin ring system (O3/C6–C14) is nearly planar, with a maximum deviation from the mean plane of 0.080 (2) Å for atom C12.

In the crystal structure (Fig. 2), the molecules are connected via weak intramolecular C8—H8···S2 and intermolecular C16—H16C···S1 hydrogen bonds (Table 1). Furthermore, the crystal structure features π-π stacking interactions between the pyran ring (O3/C10–C14; centroid Cg1) and the benzene ring (C6–C11; centroid Cg2), with a Cg1···Cg2 distance of 3.679 (1) Å.

Related literature top

For biological applications of coumarins and dithiocarbamates, see: Smith et al. (1998); Nawrot-Modraka et al. (2006); Basanagouda et al. (2009); Kalkhambkar et al. (2007); El-Shorbagi (2000); Ronconi et al. (2006); Cvek & Dvorak (2007). For a related structure, see: Kumar et al. (2012). For the synthesis of the title compound, see: Shastri et al. (2004).

Experimental top

All the chemicals were of analytical reagent grade and were used directly without further purification. 4-Bromomethyl coumarin required for the synthesis of the target molecule was synthesized according to an already reported procedure involving Pechmann cyclization of phenols with 4-bromoethyl acetoacetate (Shastri et al., 2004) and sodium diethyldithiocarbamate purchased from Sigma- Aldrich.

A mixture of 2.6 g (0.01 mol) of 5,7-dimethyl-4-bromomethylcoumarin and 1.71 g (0.01 mol) of sodium diethyldithiocarbamate in 30 ml dry alcohol was stirred for 24 h at room temperature (the reaction was monitored by TLC). The solvent was evaporated and the resulting solid was extracted twice with a dichloromethane-H₂O mixture. The organic layer was dried over anhydrous CaCl₂ and evaporation of the organic solvent gave the title compound. The compound was recrystallized from an ethanol-chloroform mixture. Colour: Colourless. Yield: 91%. M.P.: 409 K.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius. The dashed line indicates the intramolecular hydrogen bond.
	Fig. 2. The packing of the molecules in the crystal structure.

(5,7-Dimethyl-2-oxo-2H-chromen-4-yl)methyl diethyldithiocarbamate top

Crystal data top

C₁₇H₂₁NO₂S₂	F(000) = 712
M_r = 335.47	D_x = 1.295 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 409 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.8570 (2) Å	Cell parameters from 3033 reflections
b = 23.7745 (5) Å	θ = 1.7–25.0°
c = 9.7684 (2) Å	µ = 0.32 mm⁻¹
β = 109.483 (1)°	T = 293 K
V = 1720.22 (7) Å³	Plate, colourless
Z = 4	0.24 × 0.20 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3033 independent reflections
Radiation source: fine-focus sealed tube	2803 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω and ϕ scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: ψ scan (SADABS; Sheldrick, 2007)	h = −9→9
T_min = 0.770, T_max = 1.000	k = −26→28
14939 measured reflections	l = −11→11

Refinement top

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)] = 0.051	H-atom parameters constrained
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.0643P)² + 1.5942P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.003
3033 reflections	Δρ_max = 0.90 e Å⁻³
204 parameters	Δρ_min = −0.73 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0052 (14)

Crystal data top

C₁₇H₂₁NO₂S₂	V = 1720.22 (7) Å³
M_r = 335.47	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.8570 (2) Å	µ = 0.32 mm⁻¹
b = 23.7745 (5) Å	T = 293 K
c = 9.7684 (2) Å	0.24 × 0.20 × 0.12 mm
β = 109.483 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3033 independent reflections
Absorption correction: ψ scan (SADABS; Sheldrick, 2007)	2803 reflections with I > 2σ(I)
T_min = 0.770, T_max = 1.000	R_int = 0.020
14939 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.04	Δρ_max = 0.90 e Å⁻³
3033 reflections	Δρ_min = −0.73 e Å⁻³
204 parameters

Special details top

Experimental. IR (KBr) 670 c m^-1 (C—S), 1204 c m^-1 (C=S), 1047 c m^-1 (C—O), 823 c m^-1 (C—N),1279 c m^-1 (C—O—C), 1716 c m^-1 (C=O).GCMS data m/e = 335. 1H NMR (400 MHz, CDCl₃, δ, p.p.m.): 1.58 (d Ethylene-6H, CH₃), 2.46 (s,3H, CH₃), 2.71 (s,3H, CH₃), 3.88 (s,2H, Ethylene-CH₂), 4.21 (s,2H, Ethylene-CH₂), 4.50 (s 2H, Methylene-CH₂), 6.53 (s,1H, Ar—H), 6.92 (s,1H, Ar—H), 7.03 (s,1H, Ar—H).

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.

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

	x	y	z	U_iso*/U_eq
S1	0.15831 (9)	0.15127 (3)	0.66095 (6)	0.0434 (2)
S2	0.25909 (15)	0.14818 (4)	0.38884 (10)	0.0773 (3)
O3	0.77521 (19)	0.04484 (8)	0.88072 (17)	0.0414 (4)
O4	0.8065 (3)	0.01657 (10)	0.6765 (2)	0.0610 (6)
N5	0.1516 (4)	0.23806 (10)	0.4975 (3)	0.0583 (6)
C6	0.7641 (3)	0.06546 (11)	1.1089 (2)	0.0395 (5)
H6	0.8887	0.0606	1.1437	0.047*
C7	0.6727 (3)	0.07803 (10)	1.2025 (2)	0.0401 (5)
C8	0.4863 (3)	0.08315 (10)	1.1453 (2)	0.0378 (5)
H8	0.4236	0.0902	1.2091	0.045*
C9	0.3886 (3)	0.07847 (9)	0.9997 (2)	0.0329 (5)
C10	0.4826 (3)	0.06808 (9)	0.9000 (2)	0.0294 (5)
C11	0.6692 (3)	0.06000 (9)	0.9621 (2)	0.0327 (5)
C12	0.4095 (3)	0.06440 (9)	0.7418 (2)	0.0312 (5)
C13	0.5170 (3)	0.04836 (10)	0.6673 (2)	0.0380 (5)
H13	0.4675	0.0459	0.5668	0.046*
C14	0.7056 (3)	0.03479 (11)	0.7350 (3)	0.0405 (5)
C15	0.7704 (4)	0.08551 (15)	1.3626 (3)	0.0628 (8)
H15A	0.7936	0.0493	1.4088	0.094*
H15B	0.6971	0.1074	1.4042	0.094*
H15C	0.8827	0.1046	1.3770	0.094*
C16	0.1861 (3)	0.08263 (12)	0.9590 (3)	0.0465 (6)
H16A	0.1543	0.0847	1.0456	0.070*
H16B	0.1310	0.0500	0.9041	0.070*
H16C	0.1442	0.1158	0.9016	0.070*
C17	0.2169 (3)	0.07796 (10)	0.6516 (2)	0.0369 (5)
H17A	0.1363	0.0548	0.6844	0.044*
H17B	0.1982	0.0683	0.5512	0.044*
C18	0.1913 (4)	0.18349 (11)	0.5078 (3)	0.0480 (6)
C19	0.1622 (6)	0.27172 (15)	0.3738 (4)	0.0795 (11)
H19A	0.1363	0.2478	0.2887	0.095*
H19B	0.0718	0.3012	0.3524	0.095*
C20	0.0865 (5)	0.26865 (13)	0.6014 (4)	0.0666 (9)
H20A	0.1272	0.3074	0.6075	0.080*
H20B	0.1384	0.2519	0.6968	0.080*
C21	−0.1163 (5)	0.26762 (16)	0.5582 (4)	0.0793 (10)
H21A	−0.1682	0.2849	0.4647	0.119*
H21B	−0.1529	0.2879	0.6286	0.119*
H21C	−0.1570	0.2294	0.5538	0.119*
C22	0.3417 (7)	0.29714 (19)	0.4049 (7)	0.1145 (17)
H22A	0.3700	0.3194	0.4917	0.172*
H22B	0.3420	0.3206	0.3251	0.172*
H22C	0.4303	0.2680	0.4184	0.172*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0513 (4)	0.0436 (4)	0.0340 (3)	0.0154 (3)	0.0127 (3)	0.0011 (2)
S2	0.1254 (8)	0.0562 (5)	0.0777 (6)	0.0240 (5)	0.0703 (6)	0.0081 (4)
O3	0.0260 (8)	0.0627 (11)	0.0369 (9)	0.0014 (7)	0.0124 (6)	0.0009 (8)
O4	0.0491 (11)	0.0906 (16)	0.0508 (11)	0.0181 (10)	0.0267 (9)	−0.0012 (10)
N5	0.0738 (16)	0.0432 (13)	0.0683 (16)	0.0112 (11)	0.0373 (13)	0.0056 (11)
C6	0.0270 (11)	0.0512 (14)	0.0360 (12)	−0.0054 (10)	0.0046 (9)	0.0016 (10)
C7	0.0441 (13)	0.0425 (13)	0.0300 (11)	−0.0084 (10)	0.0074 (10)	−0.0005 (9)
C8	0.0424 (13)	0.0403 (13)	0.0351 (12)	−0.0017 (10)	0.0188 (10)	−0.0017 (9)
C9	0.0311 (11)	0.0325 (11)	0.0361 (12)	0.0004 (9)	0.0126 (9)	0.0013 (9)
C10	0.0270 (10)	0.0287 (10)	0.0318 (11)	−0.0028 (8)	0.0090 (9)	0.0004 (8)
C11	0.0279 (11)	0.0383 (12)	0.0331 (11)	−0.0031 (9)	0.0117 (9)	0.0024 (9)
C12	0.0303 (11)	0.0283 (10)	0.0320 (11)	−0.0002 (8)	0.0065 (9)	0.0002 (8)
C13	0.0389 (12)	0.0439 (13)	0.0294 (11)	0.0050 (10)	0.0091 (9)	0.0002 (9)
C14	0.0389 (12)	0.0498 (14)	0.0366 (12)	0.0040 (11)	0.0177 (10)	0.0036 (10)
C15	0.0609 (18)	0.087 (2)	0.0334 (14)	−0.0135 (16)	0.0061 (12)	−0.0067 (14)
C16	0.0348 (13)	0.0618 (16)	0.0475 (14)	0.0073 (11)	0.0199 (11)	0.0059 (12)
C17	0.0332 (12)	0.0381 (12)	0.0338 (12)	0.0033 (9)	0.0035 (9)	−0.0026 (9)
C18	0.0528 (15)	0.0451 (14)	0.0500 (15)	0.0078 (11)	0.0224 (12)	0.0020 (11)
C19	0.104 (3)	0.0531 (18)	0.101 (3)	0.0124 (18)	0.060 (2)	0.0154 (18)
C20	0.097 (2)	0.0421 (15)	0.069 (2)	0.0145 (15)	0.0382 (18)	−0.0025 (14)
C21	0.094 (3)	0.072 (2)	0.086 (2)	0.0324 (19)	0.049 (2)	0.0158 (19)
C22	0.132 (4)	0.079 (3)	0.165 (5)	−0.026 (3)	0.093 (4)	−0.017 (3)

Geometric parameters (Å, º) top

S1—C18	1.775 (3)	C13—C14	1.443 (3)
S1—C17	1.813 (2)	C13—H13	0.9300
S2—C18	1.659 (3)	C15—H15A	0.9600
O3—C14	1.365 (3)	C15—H15B	0.9600
O3—C11	1.377 (3)	C15—H15C	0.9600
O4—C14	1.202 (3)	C16—H16A	0.9600
N5—C18	1.330 (4)	C16—H16B	0.9600
N5—C20	1.472 (4)	C16—H16C	0.9600
N5—C19	1.474 (4)	C17—H17A	0.9700
C6—C7	1.371 (3)	C17—H17B	0.9700
C6—C11	1.384 (3)	C19—C22	1.469 (6)
C6—H6	0.9300	C19—H19A	0.9700
C7—C8	1.388 (3)	C19—H19B	0.9700
C7—C15	1.505 (3)	C20—C21	1.506 (5)
C8—C9	1.377 (3)	C20—H20A	0.9700
C8—H8	0.9300	C20—H20B	0.9700
C9—C10	1.426 (3)	C21—H21A	0.9600
C9—C16	1.510 (3)	C21—H21B	0.9600
C10—C11	1.400 (3)	C21—H21C	0.9600
C10—C12	1.461 (3)	C22—H22A	0.9600
C12—C13	1.341 (3)	C22—H22B	0.9600
C12—C17	1.510 (3)	C22—H22C	0.9600

C18—S1—C17	105.17 (12)	C9—C16—H16B	109.5
C14—O3—C11	122.57 (17)	H16A—C16—H16B	109.5
C18—N5—C20	123.8 (2)	C9—C16—H16C	109.5
C18—N5—C19	121.0 (2)	H16A—C16—H16C	109.5
C20—N5—C19	115.1 (2)	H16B—C16—H16C	109.5
C7—C6—C11	119.4 (2)	C12—C17—S1	113.43 (15)
C7—C6—H6	120.3	C12—C17—H17A	108.9
C11—C6—H6	120.3	S1—C17—H17A	108.9
C6—C7—C8	117.8 (2)	C12—C17—H17B	108.9
C6—C7—C15	121.3 (2)	S1—C17—H17B	108.9
C8—C7—C15	120.8 (2)	H17A—C17—H17B	107.7
C9—C8—C7	124.0 (2)	N5—C18—S2	124.2 (2)
C9—C8—H8	118.0	N5—C18—S1	112.87 (19)
C7—C8—H8	118.0	S2—C18—S1	122.90 (16)
C8—C9—C10	118.8 (2)	C22—C19—N5	111.5 (4)
C8—C9—C16	116.2 (2)	C22—C19—H19A	109.3
C10—C9—C16	124.9 (2)	N5—C19—H19A	109.3
C11—C10—C9	115.73 (19)	C22—C19—H19B	109.3
C11—C10—C12	115.79 (19)	N5—C19—H19B	109.3
C9—C10—C12	128.48 (19)	H19A—C19—H19B	108.0
O3—C11—C6	113.68 (19)	N5—C20—C21	112.2 (3)
O3—C11—C10	122.26 (19)	N5—C20—H20A	109.2
C6—C11—C10	124.0 (2)	C21—C20—H20A	109.2
C13—C12—C10	119.62 (19)	N5—C20—H20B	109.2
C13—C12—C17	115.74 (19)	C21—C20—H20B	109.2
C10—C12—C17	124.64 (19)	H20A—C20—H20B	107.9
C12—C13—C14	123.5 (2)	C20—C21—H21A	109.5
C12—C13—H13	118.3	C20—C21—H21B	109.5
C14—C13—H13	118.3	H21A—C21—H21B	109.5
O4—C14—O3	117.4 (2)	C20—C21—H21C	109.5
O4—C14—C13	127.0 (2)	H21A—C21—H21C	109.5
O3—C14—C13	115.58 (19)	H21B—C21—H21C	109.5
C7—C15—H15A	109.5	C19—C22—H22A	109.5
C7—C15—H15B	109.5	C19—C22—H22B	109.5
H15A—C15—H15B	109.5	H22A—C22—H22B	109.5
C7—C15—H15C	109.5	C19—C22—H22C	109.5
H15A—C15—H15C	109.5	H22A—C22—H22C	109.5
H15B—C15—H15C	109.5	H22B—C22—H22C	109.5
C9—C16—H16A	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···S2ⁱ	0.93	2.86	3.751 (2)	161
C16—H16C···S1	0.96	2.53	3.282 (3)	135

Symmetry code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₁NO₂S₂
M_r	335.47
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.8570 (2), 23.7745 (5), 9.7684 (2)
β (°)	109.483 (1)
V (Å³)	1720.22 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.24 × 0.20 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	ψ scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.770, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14939, 3033, 2803
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.135, 1.04
No. of reflections	3033
No. of parameters	204
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.90, −0.73

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···S2ⁱ	0.93	2.86	3.751 (2)	161
C16—H16C···S1	0.96	2.53	3.282 (3)	135

Symmetry code: (i) x, y, z+1.

Acknowledgements

The authors thank the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the CCD X-ray facilities, X-ray data collection, GCMS, IR, CHNS and NMR data. KMK is grateful to Karnatak Science College, Dharwad, for providing laboratory facilities.

References

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