7′-[4-(Trifluoro­meth­yl)phen­yl]-5′,6′,7′,7a’-tetra­hydrodispiro­[indan-2,5′-pyrrolo­[1,2-c][1,3]thia­zole-6′,2′′-indan]-1,3,1′′-trione

Ang Chee Wei; Mohamed Ashraf Ali; Rusli Ismail; Ching Kheng Quah; Hoong-Kun Fun

doi:10.1107/S1600536811047118

. 2011 Nov 12;67(Pt 12):o3293–o3294. doi: 10.1107/S1600536811047118

7′-[4-(Trifluoromethyl)phenyl]-5′,6′,7′,7a’-tetrahydrodispiro[indan-2,5′-pyrrolo[1,2-c][1,3]thiazole-6′,2′′-indan]-1,3,1′′-trione

Ang Chee Wei ^a, Mohamed Ashraf Ali ^a, Rusli Ismail ^a, Ching Kheng Quah ^b,^‡, Hoong-Kun Fun ^b,^*,^§

PMCID: PMC3238947 PMID: 22199796

Abstract

In the title compound, C₂₉H₂₀F₃NO₃S, the thiazolidine ringadopts a half-chair conformation. The pyrrolidine and two five-membered carbocyclic rings are in envelope conformations with the spiro C atoms at the flaps. The trifluoromethyl-substituted benzene ring forms dihedral angles of 62.37 (14) and 87.40 (14)° with the benzene rings of the dihydro-1H-indene units. The two benzene rings form a dihedral angle of 36.94 (15)°. The molecular structure is stabilized by intramolecular C—H⋯O hydrogen bonds, which generate S(6) ring motifs. In the crystal, molecules are linked into inversion dimers by pairs of intermolecular C—H⋯O hydrogen bonds, generating R ₂ ²(10) ring motifs.

Related literature

For related structures, see: Wei, Ali, Choon et al. (2011a ▶,b ▶); Wei, Ali, Ismail et al. (2011 ▶); Wei, Ali, Yoon et al. (2011 ▶); Kumar et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₉H₂₀F₃NO₃S
M _r = 519.52
Triclinic,
a = 8.5894 (9) Å
b = 12.3144 (13) Å
c = 12.6109 (15) Å
α = 68.181 (1)°
β = 87.589 (2)°
γ = 74.960 (2)°
V = 1193.7 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 296 K
0.23 × 0.22 × 0.09 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.957, T _max = 0.983
25475 measured reflections
6922 independent reflections
4508 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.063
wR(F ²) = 0.216
S = 1.05
6922 reflections
334 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.69 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/S1600536811047118/is5003sup1.cif

e-67-o3293-sup1.cif^{(26.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047118/is5003Isup2.hkl

e-67-o3293-Isup2.hkl^{(338.7KB, 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
C3—H3A⋯O1ⁱ	0.93	2.57	3.227 (3)	128
C18—H18A⋯O2	0.97	2.47	3.091 (3)	122
C19—H19A⋯O1	0.98	2.50	3.145 (3)	123

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine, Universiti Sains Malysia (USM), Penang. This work was funded through Research Grant No. RUC (1001/PSK/8620012). HKF and CKQ also thank USM for the Research University Grant (No. 1001/PFIZIK/811160).

supplementary crystallographic information

Comment

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

The molecular structure is shown in Fig. 1. The thiazolidine (S1/N1/C27-C29) ring is twisted about the S1—C28 bond, with puckering parameters (Cremer & Pople, 1975) Q = 0.405 (3) Å and φ = 204.5 (4)°, thereby adopting a half-chair conformation. The pyrrolidine (N1/C9/C10/C19/C27) and two five-membered carbocyclic (C1/C2/C7-C9 and C10-C12/C17/C18) rings are in envelope conformations, puckering parameters (Cremer & Pople, 1975) Q = 0.458 (2) Å and φ = 65.6 (3)° with atom C10 at the flap; Q = 0.178 (3) Å and φ = 322.2 (8)° with atom C9 at the flap; and Q = 0.202 (3) Å and φ = 352.7 (8)° with atom C10 at the flap, respectively. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Kumar et al., 2010; Wei, Ali, Choon et al., 2011a,b; Wei, Ali, Ismail et al., 2011; Wei, Ali, Yoon et al., 2011). The trifluoromethyl-bound benzene (C20–C25) ring forms dihedral angles of 62.37 (14) and 87.40 (14)° with the other two benzene (C2–C7 and C12–C17) rings, respectively. The two benzene rings form a dihedral angle of 36.94 (15)°. The molecular structure is stabilized by intramolecular C18—H18A···O2 and C19—H19A···O1 hydrogen bonds (Table 1), which generate S(6) ring motifs (Fig. 1; Bernstein et al., 1995).

In the crystal (Fig. 2), molecules are linked into inversion dimers by pairs of intermolecular C3—H3A···O1 hydrogen bonds (Table 1), generating ten-membered R²₂(10) ring motifs (Bernstein et al., 1995).

Experimental

A mixture of (Z)-2-(4-trifluoromethylbenzylidene)-2,3-dihydro-1 H-indene-1-one (0.001 mmol), ninhydrin (0.001 mmol) and thiazolidine -4-carboxylic acid (0.002 mmol) (1:1:2) were dissolved in methanol (10 ml) and refluxed for 4 h. After completion of the reaction as evident from TLC, the mixture was poured into crushed ice. The precipitated solid was filtered, washed with water and recrystallised from petroleum ether-ethyl acetate mixture (1:1) to reveal the title compound as yellow crystals.