1′-Methyl-4′-[4-(trifluoro­meth­yl)phen­yl]dispiro­[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione

Wei, A.C.; Ali, M.A.; Choon, T.S.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536811044527

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3125

doi:10.1107/S1600536811044527

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1′-Methyl-4′-[4-(trifluoromethyl)phenyl]dispiro[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione

Ang Chee Wei,^a Mohamed Ashraf Ali,^a Tan Soo Choon,^a Madhukar Hemamalini ^b and Hoong-Kun Fun ^b ^*‡

^aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 19 October 2011; accepted 25 October 2011; online 29 October 2011)

In the title compound, C₂₈H₂₀F₃NO₃, the pyrrolidine ring adopts a half-chair conformation. The other five-membered rings adopt envelope conformations with the spiro and methylene C atoms as the flap atoms. In the crystal, molecules are connected via weak C—H⋯O hydrogen bonds, forming sheets parallel to the bc plane.

Related literature

For a related structure and background references, see: Wei et al. (2011 ). For ring puckering parameters, see: Cremer & Pople (1975 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₈H₂₀F₃NO₃
M_r = 475.45
Monoclinic, P 2₁ /n
a = 7.8070 (2) Å
b = 22.0878 (5) Å
c = 13.1278 (3) Å
β = 101.420 (2)°
V = 2218.93 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.27 × 0.15 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.971, T_max = 0.986
22102 measured reflections
6530 independent reflections
3872 reflections with I > 2σ(I)
R_int = 0.077

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.162
S = 1.04
6530 reflections
317 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯O3ⁱ	0.95	2.52	3.130 (3)	122
C23—H23A⋯O1ⁱⁱ	0.95	2.51	3.104 (3)	121
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+2, -y, -z+2.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811044527/hb6459sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811044527/hb6459Isup2.hkl

checkCIF report

Comment top

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

The asymmetric unit of the title compound is shown in Fig. 1. The pyrrolidine ring (N1/C5/C10–C12) is twisted about the C5 and C12 bonds, with puckering parameters (Cremer & Pople, 1975) Q = 0.457 (2) Å and f = 46.8 (3)°, and adopting a half-chair conformation. The two five- membered carbocyclic rings, C3–C7 and C12–C14/C19,C20, are in envelope conformations: puckering parameters Q = 0.213 (2) Å and f = 76.2 (7)° with atom C5 at the flap; and Q = 0.234 (2) Å and f = 189.1 (6)° with atom C13 at the flap, respectively. The indane (C1–C9) ring is essentially planar [maximum deviation of 0.208 (2) Å for atom C5] and forms dihedral angles of 28.51 (10)° and 61.94 (9) ° with the terminal phenyl (C14–C19/C21–C26) rings.

In the crystal (Fig. 2), the molecules are connected via weak intermolecular C—H···O (Table 1) hydrogen bonds, forming two- dimensional networks parallel to the bc-plane.

Related literature top

For a related structure and background references, see: Wei et al. (2011). For ring puckering parameters, see: Cremer & Pople (1975). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of (E)2-(4-trifluoromethylbenzylidene)-2,3-dihydro-1H- indene-1-one (0.001 mmol), ninhydrin (0.001 mmol) and sarcosine (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 water. The precipitated solid was filtered, washed and recrystallised from petroleum ether-ethyl acetate mixture (1:1) to reveal the title compound as yellow blocks.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound (I). H atoms not involved in hydrogen bonding are omitted.

1'-Methyl-4'-[4-(trifluoromethyl)phenyl]dispiro[indan-2,2'-pyrrolidine- 3',2''-indan]-1,3,1''-trione top

Crystal data top

C₂₈H₂₀F₃NO₃	F(000) = 984
M_r = 475.45	D_x = 1.423 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3175 reflections
a = 7.8070 (2) Å	θ = 2.4–29.0°
b = 22.0878 (5) Å	µ = 0.11 mm⁻¹
c = 13.1278 (3) Å	T = 100 K
β = 101.420 (2)°	Block, yellow
V = 2218.93 (9) Å³	0.27 × 0.15 × 0.13 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	6530 independent reflections
Radiation source: fine-focus sealed tube	3872 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
ϕ and ω scans	θ_max = 30.2°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.971, T_max = 0.986	k = −30→31
22102 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0624P)² + 0.6034P] where P = (F_o² + 2F_c²)/3
6530 reflections	(Δ/σ)_max < 0.001
317 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₂₈H₂₀F₃NO₃	V = 2218.93 (9) Å³
M_r = 475.45	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.8070 (2) Å	µ = 0.11 mm⁻¹
b = 22.0878 (5) Å	T = 100 K
c = 13.1278 (3) Å	0.27 × 0.15 × 0.13 mm
β = 101.420 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	6530 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3872 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.986	R_int = 0.077
22102 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.04	Δρ_max = 0.48 e Å⁻³
6530 reflections	Δρ_min = −0.40 e Å⁻³
317 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1	1.4957 (2)	−0.05331 (7)	0.55766 (14)	0.0444 (4)
F2	1.4706 (2)	−0.11963 (8)	0.67246 (11)	0.0414 (4)
F3	1.3006 (2)	−0.12198 (7)	0.52402 (12)	0.0404 (4)
O1	0.8027 (2)	0.12100 (8)	1.06182 (12)	0.0259 (4)
O2	0.5579 (2)	0.16217 (8)	0.71690 (12)	0.0283 (4)
O3	0.9907 (2)	0.18882 (7)	0.73016 (11)	0.0249 (4)
N1	0.6695 (2)	0.05913 (9)	0.86261 (14)	0.0208 (4)
C1	0.6883 (3)	0.33200 (12)	0.90164 (19)	0.0264 (5)
H1A	0.6643	0.3729	0.8813	0.032*
C2	0.6425 (3)	0.28631 (11)	0.82908 (18)	0.0236 (5)
H2A	0.5879	0.2952	0.7594	0.028*
C3	0.6793 (3)	0.22679 (10)	0.86166 (16)	0.0200 (5)
C4	0.6483 (3)	0.16958 (11)	0.80161 (16)	0.0207 (5)
C5	0.7496 (3)	0.11868 (10)	0.87093 (16)	0.0172 (5)
C6	0.7754 (3)	0.14805 (11)	0.97970 (16)	0.0195 (5)
C7	0.7564 (3)	0.21422 (10)	0.96488 (16)	0.0194 (5)
C8	0.8017 (3)	0.26022 (11)	1.03752 (17)	0.0228 (5)
H8A	0.8534	0.2514	1.1077	0.027*
C9	0.7691 (3)	0.31913 (11)	1.00426 (18)	0.0252 (5)
H9A	0.8021	0.3515	1.0518	0.030*
C10	0.7002 (3)	0.03124 (11)	0.76618 (17)	0.0227 (5)
H10A	0.5973	0.0367	0.7093	0.027*
H10B	0.7239	−0.0126	0.7763	0.027*
C11	0.8606 (3)	0.06418 (10)	0.74080 (16)	0.0183 (5)
H11A	0.8158	0.0925	0.6822	0.022*
C12	0.9279 (3)	0.10405 (10)	0.83779 (15)	0.0160 (4)
C13	1.0579 (3)	0.07642 (10)	0.93124 (16)	0.0172 (5)
H13A	0.9951	0.0585	0.9824	0.021*
H13B	1.1316	0.0449	0.9078	0.021*
C14	1.1665 (3)	0.13004 (10)	0.97689 (16)	0.0171 (5)
C15	1.2772 (3)	0.13615 (11)	1.07356 (16)	0.0209 (5)
H15A	1.2924	0.1037	1.1221	0.025*
C16	1.3649 (3)	0.19073 (11)	1.09748 (17)	0.0235 (5)
H16A	1.4384	0.1957	1.1638	0.028*
C17	1.3475 (3)	0.23843 (11)	1.02646 (17)	0.0239 (5)
H17A	1.4090	0.2752	1.0448	0.029*
C18	1.2409 (3)	0.23229 (10)	0.92931 (17)	0.0210 (5)
H18A	1.2293	0.2642	0.8798	0.025*
C19	1.1512 (3)	0.17805 (10)	0.90651 (16)	0.0173 (5)
C20	1.0218 (3)	0.16199 (10)	0.81240 (16)	0.0178 (5)
C21	0.9976 (3)	0.02506 (10)	0.70611 (16)	0.0172 (5)
C22	1.0503 (3)	−0.03063 (10)	0.75231 (16)	0.0195 (5)
H22A	0.9989	−0.0449	0.8076	0.023*
C23	1.1761 (3)	−0.06544 (11)	0.71882 (16)	0.0200 (5)
H23A	1.2106	−0.1032	0.7510	0.024*
C24	1.2516 (3)	−0.04479 (10)	0.63779 (16)	0.0185 (5)
C25	1.2032 (3)	0.01078 (10)	0.59215 (16)	0.0203 (5)
H25A	1.2559	0.0252	0.5375	0.024*
C26	1.0776 (3)	0.04543 (10)	0.62653 (16)	0.0194 (5)
H26A	1.0456	0.0836	0.5953	0.023*
C27	1.3791 (3)	−0.08444 (11)	0.59856 (17)	0.0223 (5)
C28	0.4895 (3)	0.05533 (12)	0.8773 (2)	0.0291 (6)
H28A	0.4807	0.0739	0.9439	0.044*
H28B	0.4542	0.0128	0.8771	0.044*
H28C	0.4127	0.0768	0.8207	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0479 (11)	0.0266 (9)	0.0723 (12)	0.0028 (7)	0.0446 (9)	0.0036 (8)
F2	0.0411 (10)	0.0529 (11)	0.0326 (8)	0.0268 (8)	0.0128 (7)	0.0114 (7)
F3	0.0405 (10)	0.0351 (9)	0.0443 (9)	0.0066 (7)	0.0053 (7)	−0.0204 (7)
O1	0.0308 (10)	0.0292 (10)	0.0189 (7)	0.0075 (7)	0.0077 (7)	0.0047 (7)
O2	0.0281 (10)	0.0321 (10)	0.0215 (8)	0.0070 (8)	−0.0032 (7)	−0.0025 (7)
O3	0.0298 (10)	0.0234 (9)	0.0200 (8)	−0.0010 (7)	0.0013 (7)	0.0043 (7)
N1	0.0169 (10)	0.0217 (11)	0.0247 (9)	−0.0028 (8)	0.0065 (8)	−0.0023 (8)
C1	0.0215 (12)	0.0231 (13)	0.0346 (13)	0.0046 (10)	0.0054 (10)	0.0021 (10)
C2	0.0190 (12)	0.0252 (13)	0.0259 (11)	0.0034 (10)	0.0028 (9)	0.0038 (10)
C3	0.0174 (11)	0.0214 (13)	0.0212 (10)	0.0023 (9)	0.0036 (9)	0.0008 (9)
C4	0.0182 (11)	0.0258 (13)	0.0187 (10)	0.0036 (9)	0.0048 (8)	0.0022 (9)
C5	0.0163 (11)	0.0180 (12)	0.0178 (9)	0.0022 (9)	0.0043 (8)	−0.0002 (8)
C6	0.0161 (11)	0.0235 (13)	0.0189 (10)	0.0026 (9)	0.0034 (8)	−0.0008 (9)
C7	0.0155 (11)	0.0212 (12)	0.0216 (10)	0.0029 (9)	0.0040 (8)	−0.0007 (9)
C8	0.0221 (12)	0.0259 (13)	0.0202 (10)	0.0034 (10)	0.0037 (9)	−0.0017 (9)
C9	0.0226 (13)	0.0212 (13)	0.0312 (12)	−0.0011 (10)	0.0035 (10)	−0.0072 (10)
C10	0.0180 (12)	0.0239 (13)	0.0276 (11)	−0.0023 (9)	0.0081 (9)	−0.0055 (10)
C11	0.0182 (11)	0.0186 (12)	0.0177 (10)	0.0003 (9)	0.0024 (8)	−0.0012 (9)
C12	0.0164 (11)	0.0153 (11)	0.0162 (9)	0.0001 (8)	0.0028 (8)	0.0000 (8)
C13	0.0145 (11)	0.0178 (12)	0.0190 (10)	0.0018 (8)	0.0023 (8)	0.0013 (8)
C14	0.0161 (11)	0.0162 (12)	0.0196 (10)	0.0012 (9)	0.0050 (8)	−0.0013 (8)
C15	0.0186 (11)	0.0235 (13)	0.0201 (10)	0.0020 (9)	0.0025 (9)	0.0027 (9)
C16	0.0219 (12)	0.0276 (14)	0.0194 (10)	−0.0018 (10)	0.0004 (9)	−0.0047 (9)
C17	0.0232 (12)	0.0212 (13)	0.0280 (11)	−0.0037 (10)	0.0064 (9)	−0.0049 (10)
C18	0.0220 (12)	0.0173 (12)	0.0241 (11)	−0.0027 (9)	0.0059 (9)	0.0005 (9)
C19	0.0178 (11)	0.0163 (12)	0.0182 (10)	0.0007 (8)	0.0049 (8)	−0.0009 (8)
C20	0.0171 (11)	0.0188 (12)	0.0172 (10)	0.0022 (9)	0.0031 (8)	−0.0002 (8)
C21	0.0168 (11)	0.0176 (12)	0.0169 (9)	−0.0030 (8)	0.0022 (8)	−0.0033 (8)
C22	0.0226 (12)	0.0181 (12)	0.0193 (10)	−0.0017 (9)	0.0078 (9)	−0.0001 (9)
C23	0.0248 (12)	0.0160 (12)	0.0195 (10)	0.0011 (9)	0.0051 (9)	0.0006 (8)
C24	0.0184 (11)	0.0188 (12)	0.0185 (10)	−0.0017 (9)	0.0041 (8)	−0.0019 (9)
C25	0.0229 (12)	0.0211 (12)	0.0180 (10)	−0.0020 (9)	0.0064 (9)	0.0022 (9)
C26	0.0220 (12)	0.0164 (12)	0.0195 (10)	0.0017 (9)	0.0034 (9)	0.0014 (8)
C27	0.0259 (13)	0.0201 (13)	0.0221 (10)	−0.0006 (10)	0.0077 (9)	0.0014 (9)
C28	0.0203 (13)	0.0342 (15)	0.0344 (13)	−0.0006 (11)	0.0092 (10)	−0.0032 (11)

Geometric parameters (Å, º) top

F1—C27	1.336 (3)	C12—C20	1.544 (3)
F2—C27	1.335 (3)	C12—C13	1.554 (3)
F3—C27	1.335 (3)	C13—C14	1.510 (3)
O1—C6	1.214 (3)	C13—H13A	0.9900
O2—C4	1.204 (2)	C13—H13B	0.9900
O3—C20	1.213 (2)	C14—C15	1.393 (3)
N1—C5	1.451 (3)	C14—C19	1.396 (3)
N1—C28	1.458 (3)	C15—C16	1.391 (3)
N1—C10	1.470 (3)	C15—H15A	0.9500
C1—C2	1.385 (3)	C16—C17	1.396 (3)
C1—C9	1.399 (3)	C16—H16A	0.9500
C1—H1A	0.9500	C17—C18	1.385 (3)
C2—C3	1.395 (3)	C17—H17A	0.9500
C2—H2A	0.9500	C18—C19	1.390 (3)
C3—C7	1.397 (3)	C18—H18A	0.9500
C3—C4	1.484 (3)	C19—C20	1.476 (3)
C4—C5	1.560 (3)	C21—C26	1.393 (3)
C5—C6	1.545 (3)	C21—C22	1.397 (3)
C5—C12	1.572 (3)	C22—C23	1.386 (3)
C6—C7	1.478 (3)	C22—H22A	0.9500
C7—C8	1.390 (3)	C23—C24	1.391 (3)
C8—C9	1.380 (3)	C23—H23A	0.9500
C8—H8A	0.9500	C24—C25	1.385 (3)
C9—H9A	0.9500	C24—C27	1.492 (3)
C10—C11	1.541 (3)	C25—C26	1.388 (3)
C10—H10A	0.9900	C25—H25A	0.9500
C10—H10B	0.9900	C26—H26A	0.9500
C11—C21	1.513 (3)	C28—H28A	0.9800
C11—C12	1.552 (3)	C28—H28B	0.9800
C11—H11A	1.0000	C28—H28C	0.9800

C5—N1—C28	117.03 (19)	C14—C13—H13B	111.1
C5—N1—C10	107.67 (18)	C12—C13—H13B	111.1
C28—N1—C10	114.55 (18)	H13A—C13—H13B	109.0
C2—C1—C9	121.3 (2)	C15—C14—C19	119.1 (2)
C2—C1—H1A	119.3	C15—C14—C13	129.5 (2)
C9—C1—H1A	119.3	C19—C14—C13	111.44 (17)
C1—C2—C3	117.8 (2)	C16—C15—C14	118.6 (2)
C1—C2—H2A	121.1	C16—C15—H15A	120.7
C3—C2—H2A	121.1	C14—C15—H15A	120.7
C2—C3—C7	120.5 (2)	C15—C16—C17	121.7 (2)
C2—C3—C4	129.64 (19)	C15—C16—H16A	119.2
C7—C3—C4	109.86 (19)	C17—C16—H16A	119.2
O2—C4—C3	127.6 (2)	C18—C17—C16	120.2 (2)
O2—C4—C5	125.3 (2)	C18—C17—H17A	119.9
C3—C4—C5	107.07 (17)	C16—C17—H17A	119.9
N1—C5—C6	115.19 (18)	C17—C18—C19	117.9 (2)
N1—C5—C4	116.63 (18)	C17—C18—H18A	121.1
C6—C5—C4	101.22 (17)	C19—C18—H18A	121.1
N1—C5—C12	100.66 (17)	C18—C19—C14	122.61 (19)
C6—C5—C12	112.44 (17)	C18—C19—C20	128.3 (2)
C4—C5—C12	111.17 (17)	C14—C19—C20	109.03 (19)
O1—C6—C7	126.8 (2)	O3—C20—C19	127.6 (2)
O1—C6—C5	125.6 (2)	O3—C20—C12	125.24 (19)
C7—C6—C5	107.60 (17)	C19—C20—C12	107.10 (17)
C8—C7—C3	121.5 (2)	C26—C21—C22	118.2 (2)
C8—C7—C6	128.83 (19)	C26—C21—C11	119.3 (2)
C3—C7—C6	109.68 (19)	C22—C21—C11	122.5 (2)
C9—C8—C7	117.8 (2)	C23—C22—C21	121.1 (2)
C9—C8—H8A	121.1	C23—C22—H22A	119.4
C7—C8—H8A	121.1	C21—C22—H22A	119.4
C8—C9—C1	121.1 (2)	C22—C23—C24	119.7 (2)
C8—C9—H9A	119.5	C22—C23—H23A	120.2
C1—C9—H9A	119.5	C24—C23—H23A	120.2
N1—C10—C11	105.46 (18)	C25—C24—C23	120.1 (2)
N1—C10—H10A	110.6	C25—C24—C27	121.0 (2)
C11—C10—H10A	110.6	C23—C24—C27	119.0 (2)
N1—C10—H10B	110.6	C24—C25—C26	119.9 (2)
C11—C10—H10B	110.6	C24—C25—H25A	120.1
H10A—C10—H10B	108.8	C26—C25—H25A	120.1
C21—C11—C10	116.65 (19)	C25—C26—C21	121.1 (2)
C21—C11—C12	115.24 (17)	C25—C26—H26A	119.5
C10—C11—C12	104.37 (17)	C21—C26—H26A	119.5
C21—C11—H11A	106.6	F2—C27—F3	105.84 (19)
C10—C11—H11A	106.6	F2—C27—F1	106.4 (2)
C12—C11—H11A	106.6	F3—C27—F1	106.00 (19)
C20—C12—C11	113.04 (17)	F2—C27—C24	112.87 (18)
C20—C12—C13	103.42 (16)	F3—C27—C24	112.13 (19)
C11—C12—C13	119.14 (18)	F1—C27—C24	113.0 (2)
C20—C12—C5	111.96 (18)	N1—C28—H28A	109.5
C11—C12—C5	99.75 (16)	N1—C28—H28B	109.5
C13—C12—C5	109.75 (17)	H28A—C28—H28B	109.5
C14—C13—C12	103.47 (17)	N1—C28—H28C	109.5
C14—C13—H13A	111.1	H28A—C28—H28C	109.5
C12—C13—H13A	111.1	H28B—C28—H28C	109.5

C9—C1—C2—C3	0.2 (4)	C6—C5—C12—C11	168.65 (18)
C1—C2—C3—C7	1.3 (4)	C4—C5—C12—C11	−78.7 (2)
C1—C2—C3—C4	−178.9 (2)	N1—C5—C12—C13	−80.37 (19)
C2—C3—C4—O2	−14.0 (4)	C6—C5—C12—C13	42.7 (2)
C7—C3—C4—O2	165.8 (2)	C4—C5—C12—C13	155.43 (17)
C2—C3—C4—C5	168.4 (2)	C20—C12—C13—C14	22.8 (2)
C7—C3—C4—C5	−11.9 (3)	C11—C12—C13—C14	149.22 (19)
C28—N1—C5—C6	65.2 (2)	C5—C12—C13—C14	−96.8 (2)
C10—N1—C5—C6	−164.16 (18)	C12—C13—C14—C15	164.5 (2)
C28—N1—C5—C4	−53.3 (3)	C12—C13—C14—C19	−17.6 (2)
C10—N1—C5—C4	77.4 (2)	C19—C14—C15—C16	1.8 (3)
C28—N1—C5—C12	−173.66 (17)	C13—C14—C15—C16	179.6 (2)
C10—N1—C5—C12	−43.0 (2)	C14—C15—C16—C17	−1.5 (4)
O2—C4—C5—N1	−32.4 (3)	C15—C16—C17—C18	0.1 (4)
C3—C4—C5—N1	145.4 (2)	C16—C17—C18—C19	1.0 (4)
O2—C4—C5—C6	−158.2 (2)	C17—C18—C19—C14	−0.7 (4)
C3—C4—C5—C6	19.6 (2)	C17—C18—C19—C20	175.5 (2)
O2—C4—C5—C12	82.2 (3)	C15—C14—C19—C18	−0.7 (3)
C3—C4—C5—C12	−100.1 (2)	C13—C14—C19—C18	−178.9 (2)
N1—C5—C6—O1	31.2 (3)	C15—C14—C19—C20	−177.5 (2)
C4—C5—C6—O1	158.0 (2)	C13—C14—C19—C20	4.3 (3)
C12—C5—C6—O1	−83.3 (3)	C18—C19—C20—O3	13.6 (4)
N1—C5—C6—C7	−147.48 (19)	C14—C19—C20—O3	−169.8 (2)
C4—C5—C6—C7	−20.7 (2)	C18—C19—C20—C12	−165.5 (2)
C12—C5—C6—C7	98.0 (2)	C14—C19—C20—C12	11.1 (2)
C2—C3—C7—C8	−1.2 (4)	C11—C12—C20—O3	29.4 (3)
C4—C3—C7—C8	179.0 (2)	C13—C12—C20—O3	159.7 (2)
C2—C3—C7—C6	178.0 (2)	C5—C12—C20—O3	−82.3 (3)
C4—C3—C7—C6	−1.9 (3)	C11—C12—C20—C19	−151.44 (18)
O1—C6—C7—C8	15.4 (4)	C13—C12—C20—C19	−21.2 (2)
C5—C6—C7—C8	−165.9 (2)	C5—C12—C20—C19	96.9 (2)
O1—C6—C7—C3	−163.7 (2)	C10—C11—C21—C26	140.2 (2)
C5—C6—C7—C3	15.0 (2)	C12—C11—C21—C26	−96.9 (2)
C3—C7—C8—C9	−0.4 (4)	C10—C11—C21—C22	−41.1 (3)
C6—C7—C8—C9	−179.4 (2)	C12—C11—C21—C22	81.9 (3)
C7—C8—C9—C1	1.9 (4)	C26—C21—C22—C23	−1.3 (3)
C2—C1—C9—C8	−1.8 (4)	C11—C21—C22—C23	−180.0 (2)
C5—N1—C10—C11	22.4 (2)	C21—C22—C23—C24	0.0 (3)
C28—N1—C10—C11	154.43 (19)	C22—C23—C24—C25	1.1 (3)
N1—C10—C11—C21	136.47 (19)	C22—C23—C24—C27	−176.4 (2)
N1—C10—C11—C12	8.1 (2)	C23—C24—C25—C26	−0.9 (3)
C21—C11—C12—C20	79.4 (2)	C27—C24—C25—C26	176.6 (2)
C10—C11—C12—C20	−151.33 (18)	C24—C25—C26—C21	−0.5 (3)
C21—C11—C12—C13	−42.3 (3)	C22—C21—C26—C25	1.5 (3)
C10—C11—C12—C13	86.9 (2)	C11—C21—C26—C25	−179.70 (19)
C21—C11—C12—C5	−161.54 (18)	C25—C24—C27—F2	151.1 (2)
C10—C11—C12—C5	−32.3 (2)	C23—C24—C27—F2	−31.4 (3)
N1—C5—C12—C20	165.38 (16)	C25—C24—C27—F3	−89.5 (3)
C6—C5—C12—C20	−71.5 (2)	C23—C24—C27—F3	88.0 (2)
C4—C5—C12—C20	41.2 (2)	C25—C24—C27—F1	30.2 (3)
N1—C5—C12—C11	45.54 (19)	C23—C24—C27—F1	−152.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O3ⁱ	0.95	2.52	3.130 (3)	122
C23—H23A···O1ⁱⁱ	0.95	2.51	3.104 (3)	121

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+2, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₀F₃NO₃
M_r	475.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.8070 (2), 22.0878 (5), 13.1278 (3)
β (°)	101.420 (2)
V (Å³)	2218.93 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.27 × 0.15 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.971, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	22102, 6530, 3872
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.708

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.162, 1.04
No. of reflections	6530
No. of parameters	317
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.40

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O3ⁱ	0.95	2.52	3.130 (3)	122
C23—H23A···O1ⁱⁱ	0.95	2.51	3.104 (3)	121

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+2, −y, −z+2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

ACW, MAA and TSC thank the Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine, Universiti of Sains Malaysia, Penang. This work was funded through Research Grant No. RUC (1001/PSK/8620012). HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wei, A. C., Ali, M. A., Ismail, R., Hemamalini, M. & Fun, H. K. (2011). Acta Cryst. E67, o3124. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 11| November 2011| Page o3125

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1′-Methyl-4′-[4-(tri­fluoro­meth­yl)phen­yl]di­spiro­[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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Acknowledgements

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organic compounds

1′-Methyl-4′-[4-(trifluoromethyl)phenyl]dispiro[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione