(5,7-Dimethyl-2-oxo-2H-chromen-4-yl)methyl pyrrolidine-1-carbodithio­ate

Mahabaleshwaraiah, N.M.; Kumar, K.M.; Kotresh, O.; Al-eryani, W.F.A.; Devarajegowda, H.C.

doi:10.1107/S1600536812018004

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1584

doi:10.1107/S1600536812018004

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(5,7-Dimethyl-2-oxo-2H-chromen-4-yl)methyl pyrrolidine-1-carbodithioate

N. M. Mahabaleshwaraiah,^a K. Mahesh Kumar,^a O. Kotresh,^a Waleed Fadl Ali Al-eryani ^b and H. C. Devarajegowda ^b ^*

^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 21 April 2012; accepted 23 April 2012; online 2 May 2012)

In the title compound, C₁₇H₁₉NO₂S₂, the 2H-chromene ring system is almost planar, with a maximum deviation of 0.044 (2) Å, and the pyrrolidine ring adopts an envelope conformation. The dihedral angle between the 2H-chromene system and the planar part of the pyrrolidine ring is 83.65 (8)°. A weak intramolecular C—H⋯S hydrogen bond occurs. The crystal structure features C—H⋯O hydrogen bonds and π–π interactions, with a centroid–centroid distance of 3.5728 (16) Å.

Related literature

For biological properties of coumarins, see: Adavi et al. (2004 ); Laurin et al. (1999 ); Kulkarni et al. (2006 ). For related structures, see: Kumar et al. (2012 ); Kant et al. (2012 ). For synthetic details, see: Shastri et al. (2004 ); Vasilliev & Polackov (2000 ).

Experimental

Crystal data

C₁₇H₁₉NO₂S₂
M_r = 333.45
Monoclinic, P 2₁ /c
a = 13.7023 (4) Å
b = 15.9082 (4) Å
c = 7.5511 (2) Å
β = 103.358 (1)°
V = 1601.45 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.34 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
12677 measured reflections
2805 independent reflections
2410 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.099
S = 1.07
2805 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯S2	0.97	2.51	3.172 (2)	126
C18—H18⋯O4ⁱ	0.93	2.52	3.411 (3)	161
C22—H22C⋯S1	0.96	2.81	3.564 (2)	137
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536812018004/wn2472sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018004/wn2472Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812018004/wn2472Isup3.cml

checkCIF report

Comment top

Coumarins are a class of naturally occurring lactones. A number of coumarins have been isolated in recent years, mainly from plant sources and extracts of these have been employed as traditional medicines in different areas of the world. Coumarin derivatives with various thio substituents at the C-4 position have revealed potential as antibacterial (Adavi et al., 2004), DNA gyrase studies (Laurin et al., 1999) and anticancer activity (Kularni et al., 2006).

In our present work, we have been able to link a dithiocarbamate group at the C-4 methylene carbon and it was deemed of considerable interest to study the effect of this group on the total solid state conformation of the molecule. The synthesized compound was screened for antimicrobial, antidiabetic, DNA binding and DNA cleavage studies.In continuation of our interest in the crystal structures of coumarin derivatives (Kumar et al., 2012; Kant et al., 2012), we report here the crystal structure of the title compound.

The asymmetric unit of (5,7-dimethyl-2-oxo-2H-chromen-4-yl)methyl pyrrolidine-1-carbodithioate is shown in Fig. 1. The 2H-chromene ring system (O3/C12–C20) is essentially planar, with a maximum deviation of 0.044 (2)Å for atom C15.The pyrrolidine ring adopts an envelope conformation with C8 as the flap atom. The dihedral angle between the 2H-chromene ring system (O3/C12–C20) and the planar part of the pyrrolidine ring (N5, C6, C7, C9) is 83.65 (8)°.

In the crystal structure, (Fig. 2), the molecules are connected via weak intramolecular C11—H11B···S2 and C22—H22C···S1 and intermolecular C—H···O hydrogen bonds (Table 1).Furthermore, the crystal structure features a π-π interaction,with a centroid Cg2 (O3/C12–C16) to centroid Cg3 (C13/C14/C17–C20) distance of 3.5728 (16) Å.

Related literature top

For biological properties of coumarins, see: Adavi et al. (2004, 2006); Laurin et al. (1999). For related structures, see: Kumar et al. (2012); Kant et al. (2012). For synthetic details, see: Shastri et al. (2004); Vasilliev & Polackov (2000).

Experimental top

All the chemicals used 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 pyrrolidine-1-carbodithioate was synthesized according to the reported procedure (Vasilliev & Polackov, 2000). A mixture of 2.67 g (0.01 mol) of 5,7-dimethyl-4-bromomethyl coumarin and1.69 g (0.01 mol) of sodium pyrrolidine-1-carbodithioate 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 88%, m.p.443 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. Dashed lines indicate intramolecular hydrogen bonds.
	Fig. 2. The packing of molecules in the title structure, viewed down the c-axis. Dashed lines indicate intermolecular hydrogen bonds.

(5,7-Dimethyl-2-oxo-2H-chromen-4-yl)methyl pyrrolidine-1-carbodithioate top

Crystal data top

C₁₇H₁₉NO₂S₂	F(000) = 704
M_r = 333.45	D_x = 1.383 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 443 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.7023 (4) Å	Cell parameters from 2805 reflections
b = 15.9082 (4) Å	θ = 1.5–25.0°
c = 7.5511 (2) Å	µ = 0.34 mm⁻¹
β = 103.358 (1)°	T = 293 K
V = 1601.45 (7) Å³	Plate, colourless
Z = 4	0.24 × 0.20 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2805 independent reflections
Radiation source: fine-focus sealed tube	2410 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω and ϕ scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: ψ scan (SADABS; Sheldrick, 2007)	h = −12→16
T_min = 0.770, T_max = 1.000	k = −17→18
12677 measured reflections	l = −8→8

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.052P)² + 0.452P] where P = (F_o² + 2F_c²)/3
2805 reflections	(Δ/σ)_max = 0.001
201 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₇H₁₉NO₂S₂	V = 1601.45 (7) Å³
M_r = 333.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.7023 (4) Å	µ = 0.34 mm⁻¹
b = 15.9082 (4) Å	T = 293 K
c = 7.5511 (2) Å	0.24 × 0.20 × 0.12 mm
β = 103.358 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2805 independent reflections
Absorption correction: ψ scan (SADABS; Sheldrick, 2007)	2410 reflections with I > 2σ(I)
T_min = 0.770, T_max = 1.000	R_int = 0.024
12677 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.07	Δρ_max = 0.33 e Å⁻³
2805 reflections	Δρ_min = −0.26 e Å⁻³
201 parameters

Special details top

Experimental. IR (KBr): 686 cm^-1 (C—S), 1226.8 cm^-1 (C=S), 1000 cm^-1 (C—O), 859 cm^-1 (C—N),1153 cm^-1 (C—O—C), 1719.7 cm^-1 (C=O). GCMS: m/e: 333. 1H NMR (400 MHz, DMSO.D6, \?, p.p.m.): 1.91 (m,2H, C₁₁), 2.02 (m,2H, C₁), 2.49 (s,3H, C₁₇), 2.74 (s,3H, C₁₀), 3.66 (t,2H, C₂), 4.8 (d,2H, C₄), 6.5 (s,1H, C₁₄), 7.03 (s,1H, C₁₅), 7.10 (s,1H, C₈). Elemental analysis: C, 61.20; H, 5.70; N, 4.16; O, 9.57; S, 19.19.

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	0.65286 (3)	0.09638 (3)	0.11104 (6)	0.04453 (16)
S2	0.49960 (4)	0.17744 (4)	−0.20084 (7)	0.05921 (19)
O3	0.92005 (10)	0.33298 (8)	0.23621 (19)	0.0473 (3)
O4	0.81069 (13)	0.42553 (9)	0.0928 (2)	0.0666 (4)
N5	0.46456 (11)	0.11498 (9)	0.1028 (2)	0.0407 (4)
C6	0.35762 (14)	0.13604 (14)	0.0441 (3)	0.0529 (5)
H6A	0.3243	0.1002	−0.0556	0.063*
H6B	0.3485	0.1943	0.0058	0.063*
C7	0.31788 (18)	0.12064 (18)	0.2114 (4)	0.0707 (7)
H7A	0.3155	0.1728	0.2766	0.085*
H7B	0.2508	0.0973	0.1779	0.085*
C8	0.38742 (17)	0.06053 (18)	0.3262 (3)	0.0705 (7)
H8A	0.3658	0.0031	0.2966	0.085*
H8B	0.3904	0.0703	0.4541	0.085*
C9	0.48806 (15)	0.07603 (13)	0.2847 (3)	0.0501 (5)
H9A	0.5282	0.1135	0.3740	0.060*
H9B	0.5243	0.0237	0.2837	0.060*
C10	0.52973 (13)	0.13150 (11)	0.0029 (2)	0.0387 (4)
C11	0.72925 (14)	0.13642 (12)	−0.0367 (3)	0.0451 (4)
H11A	0.7657	0.0904	−0.0757	0.054*
H11B	0.6862	0.1612	−0.1443	0.054*
C12	0.80249 (13)	0.20148 (11)	0.0595 (2)	0.0393 (4)
C13	0.89901 (13)	0.18216 (11)	0.1824 (2)	0.0373 (4)
C14	0.95351 (13)	0.25130 (11)	0.2690 (2)	0.0391 (4)
C15	0.83239 (15)	0.35208 (12)	0.1143 (3)	0.0477 (5)
C16	0.77386 (14)	0.28199 (12)	0.0298 (3)	0.0455 (4)
H16	0.7126	0.2929	−0.0501	0.055*
C17	0.94441 (14)	0.10202 (11)	0.2242 (3)	0.0424 (4)
C18	1.03608 (15)	0.09721 (13)	0.3483 (3)	0.0490 (5)
H18	1.0654	0.0446	0.3742	0.059*
C19	1.08660 (14)	0.16670 (13)	0.4363 (3)	0.0473 (5)
C20	1.04425 (14)	0.24450 (13)	0.3941 (3)	0.0459 (4)
H20	1.0765	0.2924	0.4495	0.055*
C21	1.18405 (16)	0.15628 (17)	0.5764 (3)	0.0660 (6)
H21A	1.2304	0.1991	0.5594	0.099*
H21B	1.2119	0.1019	0.5628	0.099*
H21C	1.1719	0.1611	0.6962	0.099*
C22	0.90076 (17)	0.02021 (13)	0.1408 (3)	0.0652 (6)
H22A	0.9452	−0.0251	0.1893	0.098*
H22B	0.8926	0.0226	0.0112	0.098*
H22C	0.8367	0.0111	0.1688	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0365 (3)	0.0496 (3)	0.0446 (3)	−0.0019 (2)	0.00356 (19)	0.0083 (2)
S2	0.0570 (3)	0.0720 (4)	0.0455 (3)	0.0119 (3)	0.0052 (2)	0.0175 (2)
O3	0.0530 (8)	0.0355 (7)	0.0542 (8)	−0.0048 (6)	0.0141 (6)	0.0003 (6)
O4	0.0780 (11)	0.0392 (8)	0.0832 (11)	0.0045 (7)	0.0199 (9)	0.0115 (7)
N5	0.0378 (8)	0.0393 (8)	0.0424 (8)	0.0008 (6)	0.0040 (6)	0.0018 (6)
C6	0.0391 (10)	0.0573 (13)	0.0595 (12)	0.0071 (9)	0.0059 (9)	0.0022 (10)
C7	0.0510 (13)	0.0842 (18)	0.0813 (17)	0.0068 (12)	0.0243 (12)	0.0095 (14)
C8	0.0605 (14)	0.0930 (18)	0.0605 (14)	−0.0091 (13)	0.0189 (11)	0.0084 (13)
C9	0.0501 (11)	0.0541 (12)	0.0444 (11)	−0.0031 (9)	0.0072 (8)	0.0071 (9)
C10	0.0410 (10)	0.0315 (9)	0.0402 (9)	−0.0008 (7)	0.0023 (7)	−0.0030 (7)
C11	0.0425 (10)	0.0512 (12)	0.0418 (10)	−0.0034 (8)	0.0104 (8)	−0.0031 (8)
C12	0.0392 (9)	0.0450 (10)	0.0366 (9)	−0.0011 (8)	0.0146 (7)	0.0016 (7)
C13	0.0358 (9)	0.0412 (10)	0.0383 (9)	−0.0022 (7)	0.0157 (7)	0.0002 (7)
C14	0.0409 (9)	0.0394 (10)	0.0408 (9)	−0.0022 (8)	0.0172 (7)	0.0008 (7)
C15	0.0536 (12)	0.0427 (11)	0.0507 (11)	0.0021 (9)	0.0197 (9)	0.0071 (8)
C16	0.0443 (10)	0.0477 (11)	0.0451 (10)	0.0020 (9)	0.0114 (8)	0.0080 (8)
C17	0.0402 (10)	0.0392 (10)	0.0512 (11)	0.0009 (8)	0.0177 (8)	0.0008 (8)
C18	0.0436 (11)	0.0486 (12)	0.0573 (12)	0.0076 (9)	0.0166 (9)	0.0074 (9)
C19	0.0354 (10)	0.0655 (13)	0.0432 (10)	0.0005 (9)	0.0139 (8)	0.0035 (9)
C20	0.0410 (10)	0.0539 (12)	0.0445 (10)	−0.0091 (9)	0.0135 (8)	−0.0039 (8)
C21	0.0441 (12)	0.0919 (18)	0.0591 (14)	0.0032 (12)	0.0062 (10)	0.0067 (12)
C22	0.0555 (13)	0.0413 (12)	0.0949 (17)	0.0030 (10)	0.0093 (12)	−0.0052 (11)

Geometric parameters (Å, º) top

S1—C10	1.7858 (18)	C11—H11B	0.9700
S1—C11	1.8128 (19)	C12—C16	1.343 (3)
S2—C10	1.6667 (18)	C12—C13	1.462 (2)
O3—C15	1.368 (2)	C13—C14	1.403 (2)
O3—C14	1.381 (2)	C13—C17	1.422 (2)
O4—C15	1.207 (2)	C14—C20	1.381 (3)
N5—C10	1.322 (2)	C15—C16	1.434 (3)
N5—C6	1.468 (2)	C16—H16	0.9300
N5—C9	1.473 (2)	C17—C18	1.385 (3)
C6—C7	1.507 (3)	C17—C22	1.508 (3)
C6—H6A	0.9700	C18—C19	1.389 (3)
C6—H6B	0.9700	C18—H18	0.9300
C7—C8	1.481 (3)	C19—C20	1.373 (3)
C7—H7A	0.9700	C19—C21	1.509 (3)
C7—H7B	0.9700	C20—H20	0.9300
C8—C9	1.503 (3)	C21—H21A	0.9600
C8—H8A	0.9700	C21—H21B	0.9600
C8—H8B	0.9700	C21—H21C	0.9600
C9—H9A	0.9700	C22—H22A	0.9600
C9—H9B	0.9700	C22—H22B	0.9600
C11—C12	1.506 (3)	C22—H22C	0.9600
C11—H11A	0.9700

C10—S1—C11	103.15 (9)	C16—C12—C11	116.00 (17)
C15—O3—C14	122.22 (14)	C13—C12—C11	124.46 (16)
C10—N5—C6	122.74 (15)	C14—C13—C17	116.15 (16)
C10—N5—C9	125.80 (15)	C14—C13—C12	115.91 (16)
C6—N5—C9	111.45 (15)	C17—C13—C12	127.94 (16)
N5—C6—C7	103.79 (17)	C20—C14—O3	113.91 (16)
N5—C6—H6A	111.0	C20—C14—C13	123.74 (17)
C7—C6—H6A	111.0	O3—C14—C13	122.34 (16)
N5—C6—H6B	111.0	O4—C15—O3	117.15 (19)
C7—C6—H6B	111.0	O4—C15—C16	126.7 (2)
H6A—C6—H6B	109.0	O3—C15—C16	116.13 (16)
C8—C7—C6	106.72 (19)	C12—C16—C15	123.74 (18)
C8—C7—H7A	110.4	C12—C16—H16	118.1
C6—C7—H7A	110.4	C15—C16—H16	118.1
C8—C7—H7B	110.4	C18—C17—C13	118.81 (17)
C6—C7—H7B	110.4	C18—C17—C22	116.43 (17)
H7A—C7—H7B	108.6	C13—C17—C22	124.75 (17)
C7—C8—C9	105.61 (19)	C17—C18—C19	123.60 (18)
C7—C8—H8A	110.6	C17—C18—H18	118.2
C9—C8—H8A	110.6	C19—C18—H18	118.2
C7—C8—H8B	110.6	C20—C19—C18	117.98 (17)
C9—C8—H8B	110.6	C20—C19—C21	121.32 (19)
H8A—C8—H8B	108.7	C18—C19—C21	120.68 (19)
N5—C9—C8	104.47 (16)	C19—C20—C14	119.65 (18)
N5—C9—H9A	110.9	C19—C20—H20	120.2
C8—C9—H9A	110.9	C14—C20—H20	120.2
N5—C9—H9B	110.9	C19—C21—H21A	109.5
C8—C9—H9B	110.9	C19—C21—H21B	109.5
H9A—C9—H9B	108.9	H21A—C21—H21B	109.5
N5—C10—S2	123.94 (13)	C19—C21—H21C	109.5
N5—C10—S1	111.60 (13)	H21A—C21—H21C	109.5
S2—C10—S1	124.45 (11)	H21B—C21—H21C	109.5
C12—C11—S1	111.07 (12)	C17—C22—H22A	109.5
C12—C11—H11A	109.4	C17—C22—H22B	109.5
S1—C11—H11A	109.4	H22A—C22—H22B	109.5
C12—C11—H11B	109.4	C17—C22—H22C	109.5
S1—C11—H11B	109.4	H22A—C22—H22C	109.5
H11A—C11—H11B	108.0	H22B—C22—H22C	109.5
C16—C12—C13	119.52 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···S2	0.97	2.51	3.172 (2)	126
C18—H18···O4ⁱ	0.93	2.52	3.411 (3)	161
C22—H22C···S1	0.96	2.81	3.564 (2)	137

Symmetry code: (i) −x+2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉NO₂S₂
M_r	333.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.7023 (4), 15.9082 (4), 7.5511 (2)
β (°)	103.358 (1)
V (Å³)	1601.45 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
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	12677, 2805, 2410
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.099, 1.07
No. of reflections	2805
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.26

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
C11—H11B···S2	0.97	2.51	3.172 (2)	126
C18—H18···O4ⁱ	0.93	2.52	3.411 (3)	161
C22—H22C···S1	0.96	2.81	3.564 (2)	137

Symmetry code: (i) −x+2, y−1/2, −z+1/2.

Acknowledgements

The authors acknowledge the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for CCD X-ray facilities, single-crystal X-ray diffractometer, GCMS, IR, CHNS and NMR data. NMM is grateful to Karnatak Science College, Dharwad, for providing laboratory facilities. He is also thankful to P C Jabin Science College, Hubli and UGC for allowing him to do research under FIP.

References

Adavi, H. H., Kusanur, R. A., Kulkarni, M. V. (2004). J. Indian Chem. Soc. 81, 981–986. CAS Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Kant, R., Gupta, V. K., Kapoor, K., Kour, G., Kumar, K. M., Mahabaleshwaraiah, N. M. & Kotresh, O. (2012). Acta Cryst. E68, o1104–o1105. CSD CrossRef IUCr Journals Google Scholar
Kulkarni, M. V., Kulkarni, G. M., Lin, C. H. & Sun, C. M. (2006). Curr. Med. Chem. 13, 2795–2818. Web of Science CrossRef PubMed CAS Google Scholar
Kumar, K. M., Kour, D., Kapoor, K., Mahabaleshwaraiah, N. M., Kotresh, O., Gupta, V. K. & Kant, R. (2012). Acta Cryst. E68, o878–o879. CSD CrossRef CAS IUCr Journals Google Scholar
Laurin, P., Ferround, D., Schio, L., Klich, M., Hamelin, C. D., Mowais, P., Lassaigne, P., Bonnefoy, A. & Musicki, B. (1999). Bioorg. Med. Chem. Lett. 9, 2875–2877. Web of Science CrossRef PubMed CAS Google Scholar
Shastri, L. A., Ghate, M. D. & Kulkarni, M. V. (2004). Indian J. Chem. Sect. B, 43, 2416–2422. Google Scholar
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vasilliev, A. N. & Polackov, A. D. (2000). Molecules, 5, 1014–1017. Google Scholar