(1S,3R)-3-Isobutyl-2,3-dihydro­spiro[benzo[f]isoindole-1,3′-indoline]-2′,4,9-trione methanol monosolvate

Garima Sharma; S Vasanth Kumar; Habibah A Wahab; Mohd Mustaqim Rosli; Hoong-Kun Fun

doi:10.1107/S1600536812032643

. 2012 Jul 25;68(Pt 8):o2522–o2523. doi: 10.1107/S1600536812032643

(1S,3R)-3-Isobutyl-2,3-dihydrospiro[benzo[f]isoindole-1,3′-indoline]-2′,4,9-trione methanol monosolvate

Garima Sharma ^a,^b, S Vasanth Kumar ^a, Habibah A Wahab ^b,^c,^‡, Mohd Mustaqim Rosli ^d, Hoong-Kun Fun ^d,^*,^§

PMCID: PMC3414972 PMID: 22904959

Abstract

In the title compound, C₂₃H₂₀N₂O₃·CH₃OH, the hexahydro-1H-benzo[f]isoindole and indoline rings are planar, with maximum deviations of 0.092 (1) and −0.095 (1) Å, respectively. The dihedral angle between these two rings is 88.03 (4)°. An O—H⋯N interaction links the main molecule and the methanol solvent molecule. An intramolecular C—H⋯O interaction forms an S(6) ring motif. In the crystal, the molecules form two-dimensional layers parallel to the bc plane through N—H⋯O and C—H⋯O interactions.

Related literature

For biological activities of naphthoquinones, see: Babula et al. (2007 ▶). For detailed literature on naphthoquinone chemistry, see: Chen et al. (2011 ▶); Silva et al. (2002 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₃H₂₀N₂O₃·CH₄O
M _r = 404.45
Monoclinic,
a = 10.8485 (2) Å
b = 11.9605 (2) Å
c = 16.5705 (3) Å
β = 111.246 (1)°
V = 2003.95 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.32 × 0.20 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.971, T _max = 0.990
23197 measured reflections
5871 independent reflections
4460 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.135
S = 1.03
5871 reflections
286 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812032643/xu5595sup1.cif

e-68-o2522-sup1.cif^{(31.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032643/xu5595Isup2.hkl

e-68-o2522-Isup2.hkl^{(287.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812032643/xu5595Isup3.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
N1—H1N1⋯O2ⁱ	0.903 (19)	2.249 (19)	3.1410 (16)	169.7 (17)
N2—H1N2⋯O4ⁱⁱ	0.89 (2)	1.97 (2)	2.8346 (18)	165 (2)
O4—H1O4⋯N1	0.93 (3)	1.88 (3)	2.8085 (18)	174 (2)
C13—H13B⋯O1	0.99	2.56	3.1919 (18)	121
C19—H19A⋯O3ⁱ	0.95	2.57	3.3368 (18)	138

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

Acknowledgments

HAW gratefully acknowledges the Malaysian Ministry of Science, Technology and Innovation for funding for the synthesis work (grant Nos. 09-05-lfn-meb-004 and 304/PFARMASI/650545/I121). GS and SVK thank the management and administration of Karunya University for their encouragement and support. HKF thanks USM for a Research University grant (No. 1001/PFIZIK/811160).

supplementary crystallographic information

Comment

Naphthoquinones are known to possess various biological activities such as cyto-toxicity as well as antibacterial, antifungal, antiviral, insecticidal, anti-inflammatory, and antipyretic (Babula et al., 2007) properties. Recently, there have been a few efforts to conduct 1,3-cycloaddition involving naphthoquinones (Chen et al., 2011; Silva et al., 2002).

In the title compound, Fig. 1, the hexahydro-1H-benzo[f]isoindole (N1/C1–C12) and indoline (N2/C10/C17–C23) rings are planar with the maximum deviations of 0.092 (1) Å from atom N1 and -0.095 (1) Å from atom C10. The two rings make a dihedral angle of 88.03 (4)°. An O4—H1O4···N1 interaction links the main molecule with the methanol solvent molecule. An intramolecular interaction of C13—H13B···O1 forms an S(6) ring motif (Fig. 1).

In the crystal, the molecules form two-dimensional layers parallel to the bc-plane through the intermolecular interactions of N1—H1N1···O2ⁱ, N2—H1N2···O4ⁱⁱ and C19—H19A···O3ⁱ (Fig. 2).

Experimental

A mixture of isatin (0.147 g, 1 mmol), L-leucine (0.131 g, 1 mmol) and 1,4-napthoquinone (0.158 g, 1 mmol) was refluxed in methanol (6 ml) until the disappearance of the starting material (monitored by thin layer chromatography, TLC). After standing for 1 h, the product of the reaction mixture was washed with cool water (2 × 25 ml) and cool ethanol (2 × 0.5 ml). The crude product was recrystallized from appropriate solvent to afford pure product (90% yield).