Ethyl 4′-ethenyl-2′-oxo-4-phenyl-2-(3,4,5-trimethoxy­phen­yl)spiro­[pyrrolidine-3,3′-indoline]-5-carboxyl­ate monohydrate

M Sathyanarayanan; P Ramesh; Ramalingam Murugan; S Sriman Narayanan; M N Ponnuswamy

doi:10.1107/S1600536808031206

. 2008 Oct 4;64(Pt 11):o2052–o2053. doi: 10.1107/S1600536808031206

Ethyl 4′-ethenyl-2′-oxo-4-phenyl-2-(3,4,5-trimethoxyphenyl)spiro[pyrrolidine-3,3′-indoline]-5-carboxylate monohydrate

M Sathyanarayanan ^a, P Ramesh ^b, Ramalingam Murugan ^c, S Sriman Narayanan ^c, M N Ponnuswamy ^d,^*

PMCID: PMC2959656 PMID: 21580920

Abstract

In the title compound, C₃₁H₃₂N₂O₆·H₂O, the pyrrolidine ring adopts an envelope conformation. The ethyl C atoms of the ethoxycabonyl group are disordered over two positions with occupancies of ca 0.80 and 0.20. Intramolecular N—H⋯O hydrogen bonds form S(5) and S(6) ring motifs. Molecules are linked into a three-dimensional framework by O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds, and by C—H⋯π interactions.

Related literature

For related literature, see: Amalraj et al. (2003 ▶); Beddoes et al. (1986 ▶); Cordell (1981 ▶); Suzuki et al. (1994 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C₃₁H₃₂N₂O₆·H₂O
M _r = 546.60
Hexagonal,
a = 38.8029 (10) Å
c = 11.0307 (3) Å
V = 14383.4 (7) Å³
Z = 18
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.23 × 0.21 × 0.17 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS, Sheldrick, 2001 ▶) T _min = 0.982, T _max = 0.986
111058 measured reflections
7909 independent reflections
5572 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.141
S = 1.05
7909 reflections
399 parameters
29 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 ▶); 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 and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808031206/ci2651sup1.cif

e-64-o2052-sup1.cif^{(29.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031206/ci2651Isup2.hkl

e-64-o2052-Isup2.hkl^{(379.5KB, hkl)}

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—H1⋯O1	0.86 (2)	2.419 (18)	2.8088 (18)	108 (1)
N1—H1⋯O3	0.86 (2)	2.376 (18)	2.9395 (17)	123 (1)
O4—H4B⋯O1ⁱ	0.85 (3)	2.142 (18)	2.909 (2)	150 (3)
N16—H16⋯O3ⁱⁱ	0.87 (2)	1.99 (2)	2.8449 (17)	166 (2)
C5—H5⋯O5ⁱⁱⁱ	0.98	2.45	3.3197 (18)	147
C18—H18⋯O4^iv	0.93	2.46	3.357 (2)	162
C24—H24B⋯Cg1ⁱⁱⁱ	0.93	2.93	3.776 (2)	153

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

Acknowledgments

MS thanks Dr Babu Varghese, SAIF, IIT-Madras, India, for his help with the data collection.

supplementary crystallographic information

Comment

Substituted pyrrolidine compounds possess antimicrobial and antifungal activity against various pathogens (Amalraj et al., 2003). Several optically active pyrrolidine compounds are used as intermediates in controlled asymmetric synthesis (Suzuki et al., 1994). The spiro-indole-pyrrolidine ring system is a frequently encountered structural motif in many biologically important and pharmacologically relevant alkaloids, e.g. vincrinstine, vinblastine and spirotypostatins (Cordell, 1981). Against this background and to ascertain the detailed information on its molecular conformation, the structure determination of the title compound has been carried out.

The pyrrolidine ring (N1—C5) adopts an envelope conformation, with puckering (Cremer & Pople, 1975) and asymmetry (Nardelli, 1983) parameters q₂ = 0.416 (2) Å, φ = 137.5 (2)° and Δ_s(C5) = 2.8 (2)°. The indoline ring system is planar and the keto atom O3 lies on the plane. The sum of angles at atom N1 of the pyrrolidine ring (323.3°) is in accordance with sp³ hybridization (Beddoes et al., 1986). The ethoxycarbonyl group is in an extended conformation as evidenced by torsion angles C2—C6—O2—C7 of -170.3 (3)° and C6—O2—C7—C8 of 170.3 (3)°.

Intramolecular N1—H1···O1 and N1—H1···O3 hydrogen bonds generate S(5) and S(6) ring motifs (Bernstein et al. 1995), respectively. The crystal packing is stabilized by O—H···O, O—H···N, N—H···O and C—H···O hydrogen bonds, and C—H···π intermolecular interactions (Table 1) which link the molecules into a three-dimensional framework.

Experimental

3-Arylidene-4-vinylindoline-2-one (0.5 g, 1.0 mol) and (E)-ethyl-2-(3,4,5-trimethoxybenzylideneamino)acetate (0.15 g, 1.0 mol) in acetonitrile (10 ml) was stirred in the presence of catalytic amount of AgOAc and triethylamine. The obtained crude product was recrystallized in n-hexane-acetone (8:2 v/v).