1′-Methyl-4′-[4-(trifluoro­meth­yl)phen­yl]dispiro­[acenaphthyl­ene-1,2′-pyrrolidine-3′,2′′-indane]-2,1′′(1H)-dione

Ang Chee Wei; Mohamed Ashraf Ali; Tan Soo Choon; Suhana Arshad; Ibrahim Abdul Razak

doi:10.1107/S1600536812013645

. 2012 Apr 4;68(Pt 5):o1296–o1297. doi: 10.1107/S1600536812013645

1′-Methyl-4′-[4-(trifluoromethyl)phenyl]dispiro[acenaphthylene-1,2′-pyrrolidine-3′,2′′-indane]-2,1′′(1H)-dione

Ang Chee Wei ^a, Mohamed Ashraf Ali ^a, Tan Soo Choon ^a, Suhana Arshad ^b, Ibrahim Abdul Razak ^b,^*,^‡

PMCID: PMC3344443 PMID: 22590205

Abstract

In the title compound, C₃₁H₂₂F₃NO₂, the pyrrolidine and cyclopentane rings within the dihydroindene ring system are in envelope conformations, with the N atom and the spiro-C atom at the flap, respectively. An intramolecular C—H⋯O hydrogen bond forms an S(8) ring motif. The mean plane through the pyrrolidine ring [r.m.s. deviation = 0.179 (2) Å] makes dihedral angles of 86.30 (13), 88.99 (10) and 79.69 (11)° with the benzene ring, the dihydroacenaphthylene ring and the mean plane of the indane system, respectively. In the crystal, molecules are linked by C—H⋯O and C—H⋯N hydrogen bonds into a two-dimensional network parallel to the ac plane. C—H⋯π interactions further stabilize the crystal structure.

Related literature

For the structures of related heterocyclic compounds with antitubercular activity, see: Wei, Ali, Choon et al. (2011 ▶, 2012 ▶); Wei, Ali, Ismail et al. (2011 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₃₁H₂₂F₃NO₂
M _r = 497.50
Monoclinic,
a = 8.8373 (2) Å
b = 20.1333 (5) Å
c = 13.7129 (3) Å
β = 96.243 (1)°
V = 2425.39 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.30 × 0.28 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.971, T _max = 0.980
27133 measured reflections
7039 independent reflections
4753 reflections with I > 2σ(I)
R _int = 0.072

Refinement

R[F ² > 2σ(F ²)] = 0.082
wR(F ²) = 0.186
S = 1.10
7039 reflections
335 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.37 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) global, I. DOI: 10.1107/S1600536812013645/rz2729sup1.cif

e-68-o1296-sup1.cif^{(35KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013645/rz2729Isup2.hkl

e-68-o1296-Isup2.hkl^{(344.5KB, hkl)}

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

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

Cg1 is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C29—H29A⋯O1	0.95	2.29	3.166 (3)	153
C4—H4A⋯O2ⁱ	0.95	2.52	3.364 (3)	147
C16—H16A⋯N1ⁱⁱ	0.95	2.51	3.429 (3)	163
C26—H26A⋯O1ⁱⁱⁱ	0.95	2.51	3.324 (3)	144
C5—H5A⋯Cg1^iv	0.95	2.74	3.417 (3)	129

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

Acknowledgments

The authors wish to express their thanks to the Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine, Universiti of Sains Malysia, Penang, and the Malaysian Goverment for the Research University Grant Nos. 1001/PSK/8620012 and 1001/PFIZIK/811151 and also for providing research facilities.

supplementary crystallographic information

Comment

As part of our ongoing search to discover novel heterocyclic compounds with antitubercular activity (Wei, Ali, Choon et al., 2012; Wei, Ali, Ismail et al., 2011), our group has synthesized the title compound as described below.

The molecular structure is shown in Fig. 1. The bond lengths and angles are within normal ranges and comparable to those found in related structures (Wei, Ali, Choon et al., 2012; Wei, Ali, Ismail et al., 2011; Wei, Ali, Choon et al., 2011). The pyrrolidine ring (N1/C12/C13/C22/C23) and the cyclopentane ring (C13–C15/C20/C21) within the dihydroindene moiety are in envelope conformations, with puckering parameters (Cremer & Pople, 1975) Q = 0.403 (2) Å and φ= 3.9 (4)° with atom N1 at the flap, and Q = 0.246 (3) Å and φ= 7.8 (6)° with atom C13 at the flap, respectively. An intramolecular C29—H29A···O1 hydrogen bond (Table 1) forms an S(8) ring motif (Bernstein et al., 1995). The dihedral angles between the mean plane through the pyrrolidine ring (N1/C12/C13/C22/C23) [r.m.s deviation of 0.179 (2) Å] with the benzene ring (C24–C29), the dihydroacenaphthylene ring (C1–C10/C12) and the mean plane of the dihydroindene ring (C13–C21) are 86.30 (13), 88.99 (10) and 79.69 (11)°, respectively.

In the crystal packing (Fig. 2), the molecules are linked into two-dimensional layers parallel to ac plane via intermolecular C4—H4A···O2, C16—H16A···N1 and C26—H26A···O1 (Table 1) hydrogen bonds. The crystal structure are further stabilized by intermolecular C5—H5A···Cg1 (Table 1) interactions (Cg1 is the centroid of the C15–C20 ring).

Experimental

A mixture of (E)-2-[4-(trifluoromethyl)benzylidene]-2,3-dihydro-1H-indene-1-one (0.001 mol), acenaphthenequinone (0.001 mol) and sarcosine (0.002 mol) were dissolved in methanol (10 ml) and refluxed for 4 h. After completion of the reaction as evident from TLC, the excess solvent was evaporated slowly and the product was separated and recrystallized from methanol to give the title compound as yellow crystals.