5′-([1,1′-Biphen­yl]-4-yl)-1′,1′′,3′′-tri­methyl­dispiro[indane-2,2′-pyrrolidine-4′,5′′-[1,3]diazin­ane]-1,3,2′′,4′′,6′′-penta­one

Subramanyahegde; Hosamani Amar; Yellappa Shivaraj; Giriyapura R Vijayakumar; Bandrehalli Siddagangaiah Palakshamurthy

doi:10.1107/S1600536814013117

. 2014 Jun 11;70(Pt 7):o759. doi: 10.1107/S1600536814013117

5′-([1,1′-Biphenyl]-4-yl)-1′,1′′,3′′-trimethyldispiro[indane-2,2′-pyrrolidine-4′,5′′-[1,3]diazinane]-1,3,2′′,4′′,6′′-pentaone

Subramanyahegde ^a, Hosamani Amar ^b, Yellappa Shivaraj ^a,^*, Giriyapura R Vijayakumar ^c, Bandrehalli Siddagangaiah Palakshamurthy ^d

PMCID: PMC4120593 PMID: 25161552

Abstract

In the title compound, C₃₀H₂₅N₃O₅, the central five-membered heterocyclic ring adopts an envelope conformation, with the N atom as the flap. The dihedral angles between this central ring and the pendant indane ring system, the trione and benzene rings are 87.49 (5), 82.95 (10) and 72.42 (10)°, respectively. The dihedral angle between the rings of the biphenyl group is 45.99 (13)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into [101] C(12) chains.

Related literature

For background to multi-component or tandem reactions, see: Bunce et al. (2007 ▶); Duan et al. (2005 ▶); Ohno et al. (2007 ▶); Pache et al. (2003 ▶). graphic file with name e-70-0o759-scheme1.jpg

Experimental

Crystal data

C₃₀H₂₅N₃O₅
M _r = 507.53
Monoclinic,
a = 8.3301 (10) Å
b = 26.070 (4) Å
c = 12.0441 (14) Å
β = 94.496 (6)°
V = 2607.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.24 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.979, T _max = 0.982
18992 measured reflections
4569 independent reflections
3332 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.130
S = 1.04
4569 reflections
346 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus; 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 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814013117/hb7231sup1.cif

e-70-0o759-sup1.cif^{(36KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814013117/hb7231Isup2.hkl

e-70-0o759-Isup2.hkl^{(223.9KB, hkl)}

CCDC reference: 1006972

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C29—H29⋯O2ⁱ	0.93	2.44	3.269 (3)	149

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Professor T. N. Guru Row, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for his help with the data collection.

supplementary crystallographic information

S1. Comment

One strategy that potentially meets the goals of synthesis and library production is multicomponent reactions (MCRs), in which three or more starting materials are brought together to build up molecular structure and complexity (Bunce et al. 2007; Duan et al. 2005; Ohno et al. 2007). The tandem reactions are significant in the context of green chemistry, as they offer convenient strategy for the rapid, elegant, and convergent construction of complex organic molecules without isolating and purifying the intermediates (Pache et al. 2003). In this context the title compound has been synthesized by using four components such as bi phenyl carboxaldehdyde, N,N-dimethyl barbituric acid, ninhydrin and sarcosine. Also its structure has been determined.

In the title compoud, C₃₀H₂₅N₃O₅, the dihedral angles between the rings A and B,C,D,E are 88.73 (11)°, 86.80 (11)°, 82.95 (12)°, 72.42 (10)° respectively, and between A and F, E and F are 45.99 (13)° and 36.43 (13)° respectively. In the crystal, molecules are linked by C29—H29···O2 hydrogen bonds along [101] shown in Fig.2.

S2. Experimental

To a suspension of biphenyl carboxaldehdyde, (1.0 mmol) in MeOH was added N,N-dimethyl barbituric acid (1.0 mmol), ninhydrin (1.0 mmol), sarcosine (1.0 mmol) and magnesium silicate catalyst (5 mol %) at room temperature. The reaction mass was stirred at 60°C for 20 minutes. Title compound was precipitated as yellow solid on standing the reaction mass. Then it was filtered and washed with cold methanol to remove polar impurities. The compound was further re-crystallized using dichloromethane: methanol: tetrahydrofuron (3:1:1) to yield colourless prisms.