Methyl 3-(4-methoxy­phen­yl)-1-methyl-1,2,3,3a,4,11b-hexa­hydro­benzo[f]chromeno[4,3-b]pyrrole-3a-carboxyl­ate

S Thenmozhi; A SubbiahPandi; S Kathiravan; R Raghunathan

doi:10.1107/S1600536810010056

. 2010 Mar 20;66(Pt 4):o893. doi: 10.1107/S1600536810010056

Methyl 3-(4-methoxyphenyl)-1-methyl-1,2,3,3a,4,11b-hexahydrobenzo[f]chromeno[4,3-b]pyrrole-3a-carboxylate

S Thenmozhi ^a, A SubbiahPandi ^a,^*, S Kathiravan ^b, R Raghunathan ^b

PMCID: PMC2983994 PMID: 21580710

Abstract

In the title compound, C₂₅H₂₅NO₄, the pyrrolidine ring exhibits an envelope conformation and the tetrahydropyran ring exhibits a half-chair conformation. The crystal structure is stabilized by intermolecular C–H⋯π interactions.

Related literature

For general background to the applications and biological activity of chromenopyrrole compounds, see: Caine (1993 ▶); Carlson (1993 ▶); Sokoloff et al. (1990 ▶); Wilner (1985 ▶); Biava et al. (2005 ▶); Fernandes et al. (2004 ▶); Borthwick et al. (2000 ▶); Jiang et al. (2004 ▶). For a related structure, see: Nirmala et al. (2009 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C₂₅H₂₅NO₄
M _r = 403.46
Triclinic,
a = 7.9287 (5) Å
b = 10.8707 (6) Å
c = 11.6884 (7) Å
α = 95.662 (3)°
β = 92.332 (4)°
γ = 91.797 (4)°
V = 1001.05 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.981, T _max = 0.985
21741 measured reflections
4776 independent reflections
3836 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.164
S = 1.05
4776 reflections
274 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010056/bt5203sup1.cif

e-66-0o893-sup1.cif^{(23.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010056/bt5203Isup2.hkl

e-66-0o893-Isup2.hkl^{(229.2KB, hkl)}

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

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

Cg4 is the centroid of the C1/C6–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17B⋯Cg4ⁱ	0.97	2.94	3.502 (2)	119

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Symmetry code: (i) Inline graphic .

Acknowledgments

ST and ASP thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

supplementary crystallographic information

Comment

Chromenopyrrole compounds are used in the treatment of impulsive disorders (Caine, 1993), parkinson's disease (Carlson, 1993), psychoses, memory disorders (Sokoloff et al., 1990), anxiety and depression (Wilner, 1985). Pyrrole derivatives have good in vitro activities against mycobacteria and candidae (Biava et al., 2005). These derivatives also possess anti-inflammatory (Fernandes et al., 2004) and antiviral (Borthwick et al., 2000) activities. It has also been shown that N-substituted pyrrole derivatives inhibit human immuno deficiency virus type-I (HIV-I) (Jiang et al., 2004). Against this background, and in order to obtain detailed information on molecular conformation in the solid state, an X-ray study of the title compounds has been carried out.

The geometric parameters of the title molecule (Fig. 1) agree well with those reported for a similar structure (Nirmala et al., 2009). The naphthalene ring system (C1—C10) and the benzene ring (C19—C24) are oriented at an angle of 71.1 (6)° with respect to each other. The pyrrolidine ring makes dihedral angles of 57.7 (7), 60.2 (7) and 64.0 (8)° with the naphthalene ring system and the tetrahydropyran and phenyl rings, respectively.

The pyrrolodine ring adopt an envelope conformation, with the puckering parameters q₂ and φ (Cremer & Pople, 1975) and the smallest displacement asymmetric parameters,Δ, (Nardelli, 1983) as follows: q₂=0.4285 (14) Å, φ=222.37 (19)°, Δ_s(C13)= 3.46 (11) and the tetrahydropyran ring adopt a half-chair conformation, with the puckering parameters q₂ and φ (Cremer & Pople, 1975) and the smallest displacement asymmetric parameters,Δ, (Nardelli, 1983) as follows: q₂=0.3644 (14) Å, φ=73.5 (2)°, Δ_s(C14)= 12.11 (13).

The crystal packing is stabilized by C–H···π (Table. 1) hydrogen bonds

Experimental

A mixture of (2)-methyl-4-(1-formyl naphthalen-2-ylony)-3-(4-methoxy phenyl) but-2-enoate and sarcosine were refluxed in benzene for 20hr and the solvent was removed under reduced pressure. The crude product was subjected to column chromatography to get the pure product. Crystals were obtained by slow evaporation of a solution of the title compound in methanol at room temperature.