(4S)-4-(3,4-Dichloro­phen­yl)-1′-methyl-4′-phenyl-3,4-dihydronaphthalene-2-spiro-3′-pyrrolidine-2′-spiro-1′′-acenaphthyl­ene-1,2′′(2H,1′′H)-dione

R Murugan; B Gunasekaran; S Sriman Narayanan; V Manivannan

doi:10.1107/S1600536808013846

. 2008 May 17;64(Pt 6):o1089. doi: 10.1107/S1600536808013846

(4S)-4-(3,4-Dichlorophenyl)-1′-methyl-4′-phenyl-3,4-dihydronaphthalene-2-spiro-3′-pyrrolidine-2′-spiro-1′′-acenaphthylene-1,2′′(2H,1′′H)-dione

R Murugan ^a, B Gunasekaran ^b, S Sriman Narayanan ^a, V Manivannan ^c,^*

PMCID: PMC2961525 PMID: 21202604

Abstract

In the title compound, C₃₇H₂₇Cl₂NO₂, the 3,4-dichlorophenyl ring makes a dihedral angle of 46.66 (6)° with the phenyl ring. The molecular structure is stabilized by weak intramolecular C—H⋯O interactions and the crystal structure is stabilized by weak intermolecular C—H⋯O interactions. The C–C–C–C–C five-membered ring is planar, while the C–C–C–C–N five-membered ring adopts a half-chair conformation.

Related literature

For related lituerature, see: Sarala et al. (2006 ▶); Ramesh et al. (2007 ▶); Welch et al. (1984 ▶).

Experimental

Crystal data

C₃₇H₂₇Cl₂NO₂
M _r = 588.50
Monoclinic,
a = 39.6142 (12) Å
b = 8.3031 (2) Å
c = 18.1810 (5) Å
β = 101.135 (3)°
V = 5867.5 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 293 (2) K
0.3 × 0.2 × 0.2 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.976, T _max = 0.979
67467 measured reflections
8160 independent reflections
5776 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.152
S = 1.06
8160 reflections
380 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.32 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: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013846/bt2710sup1.cif

e-64-o1089-sup1.cif^{(23.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013846/bt2710Isup2.hkl

e-64-o1089-Isup2.hkl^{(391.2KB, 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
C8—H8A⋯O2	0.97	2.49	3.045 (2)	116
C17—H17⋯O1	0.98	2.33	2.794 (2)	108
C32—H32⋯O2ⁱ	0.93	2.48	3.351 (3)	156

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

The title compound acts in the central nervous system as a serotonine uptake inhibitor. Another similar compound sertraline hydrochloride is a very effective antidepressant. It selectively blocks serotonine re-uptake and is used for the treatment of depression, as well as dependency and other anxiety-related disorders (Welch et al., 1984).

The geometric parameters in the title compound agree with the reported values of a similar structure (Sarala et al., 2006; Ramesh et al., 2007). The 3,4-dichlorophenyl ring makes a dihedral angle of 46.66 (6) ° with the 4-phenyl ring. The 3,4-dihydro-1(2H)-naphthalenone ring adopts half-chair conformation [torsion angles: C(7)—C(16)—C(11)—C(10) -3.61 (3) °, and C(7)—C(8)—C(9)—C(10) -58.20 (17) °].

The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak intermolecular C—H···O interactions.

Experimental

1.0 mol of (E) -2-benzylidene-4-(3,4-dichlorophenyl)-3,4-dihydronaphthale-1 (2H)-one (1.0 g), 1.0 mol of acenaphthaquinoline (0.65 g) and 1.0 mol of sarcosine was refluxed in 10 ml of methanol for about 5.0 hrs. The solvent was removedand the crude solid was recrystallized from ethanol.