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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 7| July 2015| Pages o489-o490
doi:10.1107/S2056989015011007

Crystal structure of (6-bromo-2-oxo-2H-chromen-4-yl)methyl morpholine-4-carbodi­thio­ate

CROSSMARK_Color_square_no_text.svg
K. Mahesh Kumar,a K. R. Roopashree,b M. Vinduvahini,c O. Kotresha and H. C. Devarajegowdab*

aDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580 001, India, bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, and cDepartment of Physics, Sri D. Devaraja Urs Govt. First Grade College, Hunsur 571 105, Mysore District, Karnataka, India
*Correspondence e-mail: devarajegowda@yahoo.com

Edited by O. Büyükgüngör, Ondokuz Mayıs University, Turkey (Received 6 May 2015; accepted 6 June 2015; online 13 June 2015)

In the title compound, C15H14BrNO3S2, the 2H-chromene ring system is nearly planar, with a maximum deviation of 0.034 (2) Å, and the morpholine ring adopts a chair conformation. The dihedral angle between best plane through the 2H-chromene ring system and the morpholine ring is 86.32 (9)°. Intra­molecular C—H⋯S hydrogen bonds are observed. In the crystal, inversion-related C—H⋯S and C—H⋯O inter­actions generate R22(10) and R22(8) rings patterns, respectively. In addition, the crystal packing features π–π inter­actions between fused benzene rings [centroid–centroid distance = 3.7558 (12) Å].

CCDC reference: 1405247

1. Related literature

For biological applications of coumarins and di­thio­carbamates, see: D'hooghe & De Kimpe (2006[D'hooghe, M. & De Kimpe, N. (2006). Tetrahedron, 62, 513-535.]); Hesse & Kirsch (2002[Hesse, S. & Kirsch, G. (2002). Tetrahedron Lett. 43, 1213-1215.]); Jung et al. (2001[Jung, J.-C., Jung, Y.-J. & Park, O.-S. (2001). Synth. Commun. 31, 1195-1200.], 2004[Jung, J.-C., Lee, J.-H., Oh, S., Lee, J.-G. & Park, O.-S. (2004). Bioorg. Med. Chem. Lett. 14, 5527-5531.]); Lee et al. (1998[Lee, B. H., Clothier, M. F., Dutton, F. E., Conder, G. A. & Johnson, S. S. (1998). Bioorg. Med. Chem. Lett. 8, 3317-3320.]); Melagraki et al. (2009[Melagraki, G., Afantitis, A., Igglessi-Markopoulou, O., Detsi, A., Koufaki, M., Kontogiorgis, C. & Hadjipavlou-Litina, D. J. (2009). Eur. J. Med. Chem. 44, 3020-3026.]); Schönenberger & Lippert (1972[Schönenberger, H. & Lippert, P. (1972). Pharmazie, 27, 139-145.]). For standard bond lengths, see: Devarajegowda et al. (2013[Devarajegowda, H. C., Kumar, K. M., Seenivasa, S., Arunkashi, H. K. & Kotresh, O. (2013). Acta Cryst. E69, o192.]). For a related structure and the synthesis of the title compound, see: Devarajegowda et al. (2013[Devarajegowda, H. C., Kumar, K. M., Seenivasa, S., Arunkashi, H. K. & Kotresh, O. (2013). Acta Cryst. E69, o192.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C15H14BrNO3S2

  • Mr = 400.30

  • Triclinic, [P \overline 1]

  • a = 7.0500 (3) Å

  • b = 7.6049 (3) Å

  • c = 15.1376 (7) Å

  • α = 78.782 (2)°

  • β = 88.549 (2)°

  • γ = 78.515 (2)°

  • V = 780.07 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.91 mm−1

  • T = 296 K

  • 0.24 × 0.20 × 0.12 mm

2.2. Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: ψ scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.]) Tmin = 0.770, Tmax = 1.000

  • 13789 measured reflections

  • 3224 independent reflections

  • 2806 reflections with I > 2σ(I)

  • Rint = 0.027

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.065

  • S = 1.03

  • 3224 reflections

  • 199 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C17—H17A⋯O5i 0.97 2.53 3.501 (2) 176
C17—H17B⋯S3 0.97 2.55 3.1633 (16) 121
C19—H19A⋯S2 0.97 2.37 2.864 (2) 111
C22—H22B⋯S3 0.97 2.61 3.0486 (19) 108
Symmetry code: (i) x, y-1, z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL2014.

Supporting information

CCDC reference: 1405247

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2056989015011007/bq2399sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015011007/bq2399Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015011007/bq2399Isup3.cml

checkCIF report


Comment top

In recent years, much attention has been directed towards the synthesis of substituted coumarins owing to their tremendous application in various research fields including biological science and medicinal chemistry. Substituted coumarin derivatives are components of numerous natural products like warfarin, phenprocoumon, coumatetralyl, carbochromen, bromadialone, etc. These compounds also exhibit a wide band of biological activities including antibacterial, anti-HIV (Hesse & Kirsch, 2002), antiviral (Lee et al., 1998), anticoagulant (Jung et al., 2001), antioxidant (Melagraki et al., 2009) and anticancer activities (Jung et al.,(2004). Carbon–sulfur bond formation is a fundamental approach to bring sulfur into organic compounds, and this has received much attention due to its occurrence in many molecules that are of biological and pharmaceutical importance. The antibacterial and antifungal activities of dithiocarbamates were reported to arise by the reaction with HS-groups of the physiologically important enzymes by transferring the alkyl group of the dithioester to the HS-function of the enzyme (Schönenberger & Lippert, 1972). Organic dithiocarbamates, ubiquitously found in a variety of biologically active molecules (Dhooghe & De Kimpe, 2006), are of high importance in academia as well as in industry.

In view of the various physiological activities of coumarins and dithiocarbamates, our current studies are focused on the development of new routes for the synthesis of coumarins incorporating dithiocarbamate moieties.

The asymmetric unit of (6-bromo-2-oxo-2H-chromen-4-yl)methyl morpholine-4-carbodi thioate is shown in Fig. 1. The 2H-chromene ring systems is nearly planar, with a maximum deviation of 0.0337 (23) Å for the atom C16 and the morpholine ring adopts a chair conformation. The dihedral angle between the 2H-chromene ring and the morpholine ring is 86.32 (9) °. In the crystal structure, intermolecular C—H···O and intramolecular C–H···S hydrogen bonds are observed (Table 1) and inversion related C—H···S and C—H···O interactions generate R2 2(10) and R2 2(8) rings pattern respectively. In addition, the crystal packing is stabilized by π–π [Cg (3)– Cg(3);C8–C13] interactions between fused benzene rings [centroid- centroid distance = 3.7558 (12)].

Related literature top

For biological applications of coumarins and dithiocarbamates, see: Dhooghe & De Kimpe (2006); Hesse & Kirsch (2002); Jung et al. (2001, 2004); Lee et al. (1998); Melagraki et al. (2009); Schönenberger & Lippert (1972). For standard bond lengths, see: Devarajegowda et al. (2013). For a related structure and the synthesis of the title compound, see: Devarajegowda et al. (2013).

Experimental top

All the chemicals used were of analytical reagent grade and were used directly without further purification. The title compound was synthesized according to the reported method (Devarajegowda et al., 2013). The compound is recrystallized by ethanol-chloroform mixture. Colourless needles of the title compound were grown from a mixed solution of Ethanol/Chloroform (V/V = 2/1) by slow evaporation at room temperature. Yield =72%, m.p.: 433–435 K

Refinement top

All H atoms were positioned geometrically, with C—H = 0.93 Å for aromatic H and C—H = 0.97 Å for methylene H and refined using a riding model with Uiso(H) = 1.2Ueq(C) for aromatic and methylene H.

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: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures top
[Figure 1] 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.
[Figure 2] Fig. 2. Crystal packing for the title compound with hydrogen bonds drawn as dashed lines.
(6-Bromo-2-oxo-2H-chromen-4-yl)methyl morpholine-4-carbodithioate top
Crystal data top
C15H14BrNO3S2F(000) = 404
Mr = 400.30Dx = 1.704 Mg m−3
Triclinic, P1Melting point: 435 K
a = 7.0500 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.6049 (3) ÅCell parameters from 3224 reflections
c = 15.1376 (7) Åθ = 2.7–26.5°
α = 78.782 (2)°µ = 2.91 mm−1
β = 88.549 (2)°T = 296 K
γ = 78.515 (2)°Plate, colourless
V = 780.07 (6) Å30.24 × 0.20 × 0.12 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer		3224 independent reflections
Radiation source: fine-focus sealed tube2806 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω and ϕ scansθmax = 26.5°, θmin = 2.7°
Absorption correction: ψ scan
(SADABS; Sheldrick, 2007)		h = −8→8
Tmin = 0.770, Tmax = 1.000k = −9→9
13789 measured reflectionsl = −18→18
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0328P)2 + 0.2957P]
where P = (Fo2 + 2Fc2)/3
3224 reflections(Δ/σ)max = 0.001
199 parametersΔρmax = 0.26 e Å−3
0 restraintsΔρmin = −0.43 e Å−3
Crystal data top
C15H14BrNO3S2γ = 78.515 (2)°
Mr = 400.30V = 780.07 (6) Å3
Triclinic, P1Z = 2
a = 7.0500 (3) ÅMo Kα radiation
b = 7.6049 (3) ŵ = 2.91 mm−1
c = 15.1376 (7) ÅT = 296 K
α = 78.782 (2)°0.24 × 0.20 × 0.12 mm
β = 88.549 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		3224 independent reflections
Absorption correction: ψ scan
(SADABS; Sheldrick, 2007)		2806 reflections with I > 2σ(I)
Tmin = 0.770, Tmax = 1.000Rint = 0.027
13789 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.065H-atom parameters constrained
S = 1.03Δρmax = 0.26 e Å−3
3224 reflectionsΔρmin = −0.43 e Å−3
199 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.19477 (3)0.33461 (3)0.89681 (2)0.05002 (9)
S20.70559 (7)0.58659 (7)0.62666 (3)0.03418 (12)
S31.06683 (7)0.72703 (8)0.56091 (3)0.03905 (13)
O60.5420 (2)0.9077 (2)0.29823 (10)0.0520 (4)
O40.6263 (2)0.94245 (19)0.89038 (9)0.0404 (3)
O50.8534 (3)1.0955 (2)0.84135 (14)0.0650 (5)
N70.7479 (2)0.7625 (2)0.46382 (10)0.0303 (3)
C80.3315 (3)0.5266 (3)0.89259 (13)0.0373 (4)
C90.4939 (3)0.5289 (3)0.84039 (12)0.0337 (4)
H90.53460.43790.80700.040*
C100.5976 (3)0.6687 (2)0.83777 (11)0.0299 (4)
C110.5313 (3)0.8021 (3)0.88881 (12)0.0345 (4)
C120.3686 (3)0.7987 (3)0.94128 (14)0.0441 (5)
H120.32720.88890.97500.053*
C130.2683 (3)0.6601 (3)0.94310 (14)0.0450 (5)
H130.15850.65610.97820.054*
C140.7717 (3)0.6820 (2)0.78610 (11)0.0302 (4)
C150.8595 (3)0.8222 (3)0.78884 (14)0.0381 (4)
H150.97290.82890.75670.046*
C160.7858 (3)0.9630 (3)0.83943 (15)0.0428 (5)
C170.8495 (3)0.5444 (3)0.72867 (12)0.0328 (4)
H17A0.84810.42230.76220.039*
H17B0.98260.55150.71330.039*
C180.8436 (2)0.7021 (2)0.54254 (12)0.0275 (4)
C190.5618 (3)0.7172 (3)0.44561 (14)0.0392 (5)
H19A0.49130.69730.50140.047*
H19B0.58480.60470.42230.047*
C200.4422 (3)0.8674 (3)0.37879 (14)0.0418 (5)
H20A0.32320.83090.36590.050*
H20B0.40810.97640.40470.050*
C210.7118 (3)0.9691 (4)0.31608 (16)0.0503 (6)
H21A0.67531.07990.34030.060*
H21B0.77850.99880.26000.060*
C220.8474 (3)0.8295 (3)0.38134 (13)0.0381 (4)
H22A0.90270.72730.35300.046*
H22B0.95250.88350.39690.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04201 (14)0.05131 (15)0.05488 (15)−0.01752 (10)−0.00222 (10)0.00309 (10)
S20.0345 (2)0.0421 (3)0.0294 (2)−0.0157 (2)0.00236 (18)−0.00731 (19)
S30.0262 (2)0.0502 (3)0.0414 (3)−0.0118 (2)−0.00145 (19)−0.0059 (2)
O60.0422 (8)0.0743 (11)0.0365 (8)−0.0190 (8)−0.0082 (6)0.0050 (7)
O40.0543 (9)0.0348 (7)0.0348 (7)−0.0096 (6)−0.0005 (6)−0.0120 (6)
O50.0792 (13)0.0475 (10)0.0813 (13)−0.0312 (9)0.0080 (10)−0.0262 (9)
N70.0259 (7)0.0327 (8)0.0322 (8)−0.0083 (6)0.0005 (6)−0.0036 (6)
C80.0350 (10)0.0413 (11)0.0321 (10)−0.0085 (9)−0.0031 (8)0.0025 (8)
C90.0386 (10)0.0339 (10)0.0278 (9)−0.0064 (8)−0.0018 (8)−0.0047 (7)
C100.0356 (9)0.0293 (9)0.0225 (8)−0.0036 (7)−0.0026 (7)−0.0022 (7)
C110.0438 (11)0.0321 (10)0.0260 (9)−0.0038 (8)−0.0029 (8)−0.0052 (7)
C120.0507 (12)0.0463 (12)0.0335 (10)−0.0010 (10)0.0067 (9)−0.0133 (9)
C130.0392 (11)0.0562 (14)0.0358 (11)−0.0049 (10)0.0067 (9)−0.0052 (10)
C140.0330 (9)0.0296 (9)0.0256 (8)−0.0035 (7)−0.0032 (7)−0.0018 (7)
C150.0382 (10)0.0375 (11)0.0395 (10)−0.0099 (8)0.0014 (8)−0.0073 (8)
C160.0522 (13)0.0352 (11)0.0422 (11)−0.0112 (9)−0.0040 (10)−0.0072 (9)
C170.0335 (10)0.0327 (10)0.0304 (9)−0.0033 (8)0.0009 (7)−0.0054 (8)
C180.0269 (9)0.0238 (8)0.0325 (9)−0.0037 (7)0.0026 (7)−0.0089 (7)
C190.0309 (10)0.0447 (12)0.0419 (11)−0.0153 (9)−0.0047 (8)0.0005 (9)
C200.0305 (10)0.0471 (12)0.0449 (11)−0.0067 (9)−0.0030 (8)−0.0022 (9)
C210.0423 (12)0.0611 (15)0.0435 (12)−0.0203 (11)−0.0036 (9)0.0103 (11)
C220.0293 (9)0.0480 (12)0.0356 (10)−0.0085 (9)0.0050 (8)−0.0044 (9)
Geometric parameters (Å, º) top
Br1—C81.894 (2)C12—C131.377 (3)
S2—C181.7839 (18)C12—H120.9300
S2—C171.8095 (19)C13—H130.9300
S3—C181.6585 (18)C14—C151.343 (3)
O6—C201.405 (3)C14—C171.501 (3)
O6—C211.418 (3)C15—C161.442 (3)
O4—C161.365 (3)C15—H150.9300
O4—C111.373 (2)C17—H17A0.9700
O5—C161.202 (3)C17—H17B0.9700
N7—C181.338 (2)C19—C201.500 (3)
N7—C191.466 (2)C19—H19A0.9700
N7—C221.470 (2)C19—H19B0.9700
C8—C91.376 (3)C20—H20A0.9700
C8—C131.385 (3)C20—H20B0.9700
C9—C101.400 (3)C21—C221.501 (3)
C9—H90.9300C21—H21A0.9700
C10—C111.394 (3)C21—H21B0.9700
C10—C141.448 (3)C22—H22A0.9700
C11—C121.380 (3)C22—H22B0.9700
C18—S2—C17104.28 (9)C14—C17—S2110.63 (13)
C20—O6—C21109.57 (16)C14—C17—H17A109.5
C16—O4—C11121.90 (15)S2—C17—H17A109.5
C18—N7—C19123.45 (15)C14—C17—H17B109.5
C18—N7—C22121.02 (15)S2—C17—H17B109.5
C19—N7—C22112.94 (15)H17A—C17—H17B108.1
C9—C8—C13121.3 (2)N7—C18—S3124.57 (14)
C9—C8—Br1119.16 (16)N7—C18—S2112.39 (13)
C13—C8—Br1119.54 (16)S3—C18—S2123.03 (11)
C8—C9—C10119.64 (18)N7—C19—C20111.25 (16)
C8—C9—H9120.2N7—C19—H19A109.4
C10—C9—H9120.2C20—C19—H19A109.4
C11—C10—C9118.19 (18)N7—C19—H19B109.4
C11—C10—C14117.86 (17)C20—C19—H19B109.4
C9—C10—C14123.94 (17)H19A—C19—H19B108.0
O4—C11—C12116.55 (18)O6—C20—C19111.60 (17)
O4—C11—C10121.57 (18)O6—C20—H20A109.3
C12—C11—C10121.87 (19)C19—C20—H20A109.3
C13—C12—C11119.2 (2)O6—C20—H20B109.3
C13—C12—H12120.4C19—C20—H20B109.3
C11—C12—H12120.4H20A—C20—H20B108.0
C12—C13—C8119.8 (2)O6—C21—C22112.72 (18)
C12—C13—H13120.1O6—C21—H21A109.0
C8—C13—H13120.1C22—C21—H21A109.0
C15—C14—C10118.75 (17)O6—C21—H21B109.0
C15—C14—C17120.61 (18)C22—C21—H21B109.0
C10—C14—C17120.62 (16)H21A—C21—H21B107.8
C14—C15—C16122.92 (19)N7—C22—C21111.57 (16)
C14—C15—H15118.5N7—C22—H22A109.3
C16—C15—H15118.5C21—C22—H22A109.3
O5—C16—O4117.3 (2)N7—C22—H22B109.3
O5—C16—C15125.9 (2)C21—C22—H22B109.3
O4—C16—C15116.84 (18)H22A—C22—H22B108.0
C13—C8—C9—C10−0.2 (3)C11—O4—C16—O5176.05 (19)
Br1—C8—C9—C10−179.11 (13)C11—O4—C16—C15−4.6 (3)
C8—C9—C10—C110.0 (3)C14—C15—C16—O5−176.7 (2)
C8—C9—C10—C14179.09 (17)C14—C15—C16—O44.1 (3)
C16—O4—C11—C12−178.20 (18)C15—C14—C17—S2−102.79 (18)
C16—O4—C11—C102.7 (3)C10—C14—C17—S275.62 (18)
C9—C10—C11—O4179.34 (16)C18—S2—C17—C14100.78 (14)
C14—C10—C11—O40.2 (3)C19—N7—C18—S3171.30 (15)
C9—C10—C11—C120.3 (3)C22—N7—C18—S310.9 (3)
C14—C10—C11—C12−178.90 (18)C19—N7—C18—S2−7.7 (2)
O4—C11—C12—C13−179.37 (18)C22—N7—C18—S2−168.15 (14)
C10—C11—C12—C13−0.3 (3)C17—S2—C18—N7−173.01 (13)
C11—C12—C13—C80.0 (3)C17—S2—C18—S37.95 (14)
C9—C8—C13—C120.2 (3)C18—N7—C19—C20150.27 (18)
Br1—C8—C13—C12179.12 (16)C22—N7—C19—C20−47.9 (2)
C11—C10—C14—C15−0.7 (3)C21—O6—C20—C19−61.6 (2)
C9—C10—C14—C15−179.84 (17)N7—C19—C20—O656.1 (2)
C11—C10—C14—C17−179.15 (16)C20—O6—C21—C2259.8 (3)
C9—C10—C14—C171.7 (3)C18—N7—C22—C21−151.82 (19)
C10—C14—C15—C16−1.5 (3)C19—N7—C22—C2145.8 (2)
C17—C14—C15—C16176.98 (18)O6—C21—C22—N7−51.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17A···O5i0.972.533.501 (2)176
C17—H17B···S30.972.553.1633 (16)121
C19—H19A···S20.972.372.864 (2)111
C22—H22B···S30.972.613.0486 (19)108
Symmetry code: (i) x, y−1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17A···O5i0.972.53003.501 (2)176
C17—H17B···S30.972.55003.1633 (16)121
C19—H19A···S20.972.37002.864 (2)111
C22—H22B···S30.972.61003.0486 (19)108
Symmetry code: (i) x, y−1, z.
 

Acknowledgements

The authors thank the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for access to the CCD X-ray facilities, X-ray data collection, GCMS, IR, CHNS and NMR data.

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ISSN: 2056-9890
Volume 71| Part 7| July 2015| Pages o489-o490
doi:10.1107/S2056989015011007
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