7′-Phenyl-1′,3′,5′,6′,7′,7a’-hexa­hydro­dipiro[acenaphthyl­ene-1,5′-pyrrolo­[1,2-c]thia­zole-6′,2′′-indane]-2,1′′(1H)-dione

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

doi:10.1107/S1600536812013293

. 2012 Mar 31;68(Pt 4):o1265–o1266. doi: 10.1107/S1600536812013293

7′-Phenyl-1′,3′,5′,6′,7′,7a’-hexahydrodipiro[acenaphthylene-1,5′-pyrrolo[1,2-c]thiazole-6′,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: PMC3344191 PMID: 22606194

Abstract

In the title compound, C₃₁H₂₃NO₂S, the pyrrolidine ring adopts an envelope conformation (with the spiro C atom as the flap), while the thiazolidine ring and the two cyclopentane rings adopt twisted conformations. The mean plane through the hexahydropyrrolo[1,2-c]thiazole ring [r.m.s deviation = 0.400 (1) Å] forms dihedral angles of 76.83 (4), 80.70 (5) and 79.00 (4)° with the benzene ring and the mean planes of the dihydroacenaphthylene and the dihydroindene rings, respectively. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into sheets lying parallel to the bc plane. One of the ketone O atoms accepts three such bonds. Weak C—H⋯π interactions are also observed.

Related literature

For related structures, see: Wei et al. (2011a ▶,b ▶, 2012 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₃₁H₂₃NO₂S
M _r = 473.56
Monoclinic,
a = 8.4054 (1) Å
b = 11.3716 (1) Å
c = 23.5194 (2) Å
β = 92.259 (1)°
V = 2246.30 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 100 K
0.30 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.949, T _max = 0.972
39597 measured reflections
10047 independent reflections
7694 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.124
S = 1.03
10047 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.29 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/S1600536812013293/hb6700sup1.cif

e-68-o1265-sup1.cif^{(34.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013293/hb6700Isup2.hkl

e-68-o1265-Isup2.hkl^{(491.3KB, hkl)}

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

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

Cg1 and Cg2 are the centroids of the C2–C6/C11 and C15–C20 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O1ⁱ	0.95	2.58	3.2598 (14)	129
C23—H23A⋯O1ⁱⁱ	1.00	2.46	3.4180 (14)	160
C31—H31A⋯O1ⁱⁱ	0.95	2.56	3.4434 (14)	155
C7—H7A⋯O2ⁱⁱⁱ	0.95	2.54	3.4111 (14)	152
C18—H18A⋯Cg1^iv	0.95	2.91	3.5502 (14)	126
C25—H25A⋯Cg2^v	0.99	2.68	3.5182 (13)	142

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

Acknowledgments

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

supplementary crystallographic information

Comment

As part of our ongoing search to prepare heterocyclic compounds with potential antitubercular activity (Wei et al., 2011a,b), we have synthesized the title compound as described below.

In the molecular structure (Fig 1), the pyrrolidine ring (N1/C12/C13/C22/C23) is in envelope conformation (Cremer & Pople, 1975) [puckering parameters, Q= 0.4480 (11) Å and φ= 68.75 (14)° with atom C13 at the flap]. Meanwhile, the thiazolidine ring and the two cyclopentane rings (S1/N1/C23–C25, C1/C2/C10–C12 & C13–C15/C20/C21) are twisted about C25–S1 bond [puckering parameters, Q= 0.3450 (11) Å and φ= 339.37 (19)°], C12–C1 bond [puckering parameters, Q= 0.1209 (11) Å and φ= 167.0 (5)°] and C13–S14 bond [puckering parameters, Q= 0.2875 (11) Å and φ= 190.5 (2)°], respectively, adopting half-chair conformation. In addition, the dihedral angles between the mean plane through the hexahydropyrrolo [1,2-c]thiazole ring (S1/N1/C12/C13/C22–C25) [r.m.s deviation of 0.400 (1) Å] with the benzene ring (C26–C31) and the mean planes of the dihydroacenaphthylene and the dihydro-indene rings (C1–C10/C12 & C13–C21) are 76.83 (4), 80.70 (5) and 79.00 (4)°, respectively. The bond lengths and angles are within normal ranges and comparable to the related structure (Wei, et al., 2011b; Wei, et al., 2012).

The crystal packing is shown in Fig. 2. The molecules are linked into sheets lying parallel to bc-plane via C7—H7A···O2, C4—H4A···O1, C23—H23A···O1 and C31—H31A···O1 (Table 1) hydrogen bonds. The crystal structure also features C18—H18A···Cg1 and C25—H25A···Cg2 (Table 1) interactions (Cg1 and Cg2 are the centroids of the C2–C6/C11 and C15–C20 rings, respectively).

Experimental

A mixture of (E)-(2-benzylidene)-2,3-dihydro-1H-indene-1-one (0.001 mol), acenaphthenequinone (0.001 mol) and thiazolidine-4-carboxylic acid (0.002 mol) (1:1:2) 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 reveal the title compound as yellow crystals.