(3-Oxo-3H-benzo[f]chromen-1-yl)methyl piperidine-1-carbodithio­ate

O Kotresh; K Mahesh Kumar; N M Mahabaleshwaraiah; H K Arunkashi; H C Devarajegowda

doi:10.1107/S1600536812042870

. 2012 Oct 20;68(Pt 11):o3167. doi: 10.1107/S1600536812042870

(3-Oxo-3H-benzo[f]chromen-1-yl)methyl piperidine-1-carbodithioate

O Kotresh ^a, K Mahesh Kumar ^a, N M Mahabaleshwaraiah ^a, H K Arunkashi ^b, H C Devarajegowda ^b,^*

PMCID: PMC3515261 PMID: 23284481

Abstract

In the title compound, C₂₀H₁₉N O₂S₂,the 3Hbenzo-chromene ring system is nearly planar, with a maximum deviation of 0.036 (2) Å, and the piperidine ring adopts a chair conformation: the bond-angle sum for its N atom is 358.7°. The dihedral angle between the 3H-benzo[f]chromene ring and the piperidine ring is 89.07 (8)°. In the crystal, C—H⋯O hydrogen bonds lead to [010] C(6) chains and weak aromatic π–π interactions between the fused pyran ring and fused benzene ring of benzochromene [centroid–centroid distance = 3.652 (1) Å] are also observed.

Related literature

For a related structure, background to coumarins and details of the synthesis of the title compound, see: Kumar et al. (2012 ▶).

Experimental

Crystal data

C₂₀H₁₉NO₂S₂
M _r = 369.48
Monoclinic,
a = 12.4508 (3) Å
b = 10.1924 (3) Å
c = 14.0188 (4) Å
β = 100.953 (2)°
V = 1746.63 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 296 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.770, T _max = 1.000
12000 measured reflections
2993 independent reflections
2380 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.082
S = 1.06
2993 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 e Å⁻³

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.

Supplementary Material

Click here for additional data file.^{(19KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812042870/hb6973sup1.cif

e-68-o3167-sup1.cif^{(19KB, cif)}

Click here for additional data file.^{(143.9KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042870/hb6973Isup2.hkl

e-68-o3167-Isup2.hkl^{(143.9KB, hkl)}

Click here for additional data file.^{(6.8KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812042870/hb6973Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O4ⁱ	0.93	2.56	3.308 (2)	138

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

As part of our ongoing studies of coumarins (or 2H-chromen-2-ones) with possible biological activities (Kumar et al., 2012), we now describe the structure of the title compound, (I).

The asymmetric unit of (I) is shown in Fig. 1. The 3Hbenzo- chromene ring system (O3/C6–C18) is essentially planar, with a maximum deviation of 0.036 (2) Å for atom C15 and the piperidine ring adopts a chair conformation. The dihedral angle between the 3Hbenzo- chromene (O3/C6–C18) ring and the piperidine (N5/C21–C25) ring is 81.07 (8)°.

In the crystal structure, (Fig. 2), C11—H11···O4 hydrogen bonds and π–π interactions between the fused pyran ring (O3/C6–C10) and fused benzene(C13–C18) ring of benzo-chromene [shortest centroid–centroid distance = 3.652 (1) Å] are observed.

Experimental

This compound was prepared according to the reported method (Kumar et al., 2012). Colourless needles of the title compound were grown from a mixed solution of EtOH / CHCl₃(V/V = 1/1) by slow evaporation at room temperature. Yield= 85%, m.p. 455 K.