2-Oxo-2-(2-oxo-2H-chromen-3-yl)ethyl pyrrolidine-1-carbodi­thio­ate

K Mahesh Kumar; N M Mahabhaleshwaraiah; O Kotresh; K R Roopashree; H C Devarajegowda

doi:10.1107/S1600536813020965

. 2013 Aug 3;69(Pt 9):o1382. doi: 10.1107/S1600536813020965

2-Oxo-2-(2-oxo-2H-chromen-3-yl)ethyl pyrrolidine-1-carbodithioate

K Mahesh Kumar ^a, N M Mahabhaleshwaraiah ^a, O Kotresh ^a, K R Roopashree ^b, H C Devarajegowda ^b,^*

PMCID: PMC3884401 PMID: 24427024

Abstract

There are two independent molecules in the asymmetric unit of the title compound, C₁₆H₁₅NO₃S₂, in which the pyrrolidine rings adopt envelope conformations, with a methylene C atom as the flap. The dihedral angles betweeen the near-planar 2H-chromene ring systems [maximum deviations = 0.0167 (20) and 0.0136 (19) Å] and the pyrrolidine rings (all atoms) are 83.83 (11) and 82.43 (11)°. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds occur for one of the molecules. Further C—H⋯O links involving both molecules generate a three-dimensional network.

Related literature

For a related structure and the synthesis of the title compound, see: Mahabaleshwaraiah et al. (2012 ▶). graphic file with name e-69-o1382-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₅NO₃S₂
M _r = 333.41
Triclinic,
a = 9.7158 (2) Å
b = 12.5040 (2) Å
c = 13.5925 (2) Å
α = 106.415 (1)°
β = 100.882 (1)°
γ = 94.854 (1)°
V = 1538.74 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 296 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.770, T _max = 1.000
21575 measured reflections
5420 independent reflections
4477 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.109
S = 1.09
5420 reflections
397 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.38 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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813020965/hb7109sup1.cif

e-69-o1382-sup1.cif^{(29KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020965/hb7109Isup2.hkl

e-69-o1382-Isup2.hkl^{(260KB, hkl)}

Click here for additional data file.^{(5.8KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813020965/hb7109Isup3.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
C9A—H9A⋯O5B ⁱ	0.93	2.48	3.307 (2)	149
C15A—H15A⋯O5B ⁱ	0.93	2.50	3.319 (3)	147
C9B—H9B⋯O5A ⁱ	0.93	2.46	3.288 (3)	149
C15B—H15B⋯O5A ⁱ	0.93	2.50	3.319 (3)	146
C17B—H17B⋯O3B ⁱⁱ	0.97	2.47	3.432 (3)	170

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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

supplementary crystallographic information

1. Comment

As part of our ongoing structural studies of coumarin derivatives with possible biological activity (Mahabaleshwaraiah et al., 2012), we now describe the structure of the title compound, (I).

There are two independent molecules in the asymmetric unit of 2-oxo-2- (2-oxo-2H-chromen-3-yl)ethyl pyrrolidine-1-carbodithioate is shown in Fig. 1. The 2H-chromene ring systems (O3a/C7a–C15a) and (O3b/C7b–C15b) are nearly planar, with a maximum deviation of 0.0167 (20) Å and 0.0136 (19) Å respectively. The pyrrolidine rings (N6a/C19a—C22a) and (N6b/C19b—C22b) are not coplanar with the 2H-chromene ring systems (O3a/C7a–C15a) and (O3b/C7b–C15b); the dihedral angles between two planes being 83.83 (11)° and 82.43 (11)° in the two molecules. In the crystal, inversion related C17B—H17B···O3B hydrogen bonds generate R₂²(12) loops.

2. Experimental

This compound was prepared according to the reported method (Mahabaleshwaraiah et al., 2012). Colourless needles were grown from a mixed solution of EtOH/CHCl₃ (v/v = 2/1) by slow evaporation at room temperature. Yield = 88%, m.p. 441 K.