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

Wei, A.C.; Ali, M.A.; Choon, T.S.; Arshad, S.; Razak, I.A.

doi:10.1107/S1600536812013645

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1296-o1297

doi:10.1107/S1600536812013645

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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 and Ibrahim Abdul Razak ^b ^*‡

^aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia, and ^bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 22 March 2012; accepted 29 March 2012; online 4 April 2012)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.082
wR(F²) = 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

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
Symmetry codes: (i) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x-1, y, z; (iv) x+1, y, z.

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/S1600536812013645/rz2729sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

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 top

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.

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 molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. H atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.

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

Crystal data top

C₃₁H₂₂F₃NO₂	F(000) = 1032
M_r = 497.50	D_x = 1.362 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5213 reflections
a = 8.8373 (2) Å	θ = 2.5–30.1°
b = 20.1333 (5) Å	µ = 0.10 mm⁻¹
c = 13.7129 (3) Å	T = 100 K
β = 96.243 (1)°	Block, yellow
V = 2425.39 (10) Å³	0.30 × 0.28 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7039 independent reflections
Radiation source: fine-focus sealed tube	4753 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
ϕ and ω scans	θ_max = 30.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→12
T_min = 0.971, T_max = 0.980	k = −28→23
27133 measured reflections	l = −19→19

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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.186	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.062P)² + 2.6644P] where P = (F_o² + 2F_c²)/3
7039 reflections	(Δ/σ)_max < 0.001
335 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₃₁H₂₂F₃NO₂	V = 2425.39 (10) Å³
M_r = 497.50	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.8373 (2) Å	µ = 0.10 mm⁻¹
b = 20.1333 (5) Å	T = 100 K
c = 13.7129 (3) Å	0.30 × 0.28 × 0.20 mm
β = 96.243 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7039 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4753 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.980	R_int = 0.072
27133 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	0 restraints
wR(F²) = 0.186	H-atom parameters constrained
S = 1.10	Δρ_max = 0.55 e Å⁻³
7039 reflections	Δρ_min = −0.37 e Å⁻³
335 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 e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.0010 (2)	0.42817 (7)	0.71415 (11)	0.0310 (4)
F2	0.0624 (2)	0.49747 (9)	0.82994 (11)	0.0382 (5)
F3	−0.1474 (2)	0.50882 (9)	0.73716 (14)	0.0416 (5)
O1	0.6473 (2)	0.62588 (9)	0.59831 (12)	0.0197 (4)
O2	0.2586 (2)	0.76005 (9)	0.33429 (12)	0.0218 (4)
N1	0.5391 (2)	0.65334 (10)	0.38454 (14)	0.0159 (4)
C1	0.6585 (3)	0.67919 (12)	0.55815 (16)	0.0149 (5)
C2	0.7746 (3)	0.73053 (12)	0.58287 (16)	0.0159 (5)
C3	0.8914 (3)	0.73588 (13)	0.65826 (17)	0.0189 (5)
H3A	0.9055	0.7031	0.7083	0.023*
C4	0.9887 (3)	0.79137 (13)	0.65863 (18)	0.0220 (6)
H4A	1.0681	0.7963	0.7107	0.026*
C5	0.9720 (3)	0.83884 (13)	0.58523 (17)	0.0206 (5)
H5A	1.0404	0.8754	0.5877	0.025*
C6	0.8547 (3)	0.83393 (12)	0.50641 (17)	0.0181 (5)
C7	0.8279 (3)	0.87667 (13)	0.42369 (18)	0.0218 (5)
H7A	0.8897	0.9149	0.4186	0.026*
C8	0.7125 (3)	0.86261 (13)	0.35127 (17)	0.0212 (5)
H8A	0.6971	0.8913	0.2961	0.025*
C9	0.6154 (3)	0.80682 (13)	0.35583 (16)	0.0196 (5)
H9A	0.5375	0.7981	0.3040	0.024*
C10	0.6352 (3)	0.76561 (12)	0.43570 (16)	0.0151 (5)
C11	0.7565 (3)	0.77944 (12)	0.50919 (16)	0.0162 (5)
C12	0.5532 (3)	0.70278 (11)	0.46338 (15)	0.0146 (5)
C13	0.3835 (3)	0.71004 (12)	0.48642 (16)	0.0151 (5)
C14	0.3684 (3)	0.73745 (12)	0.59096 (16)	0.0162 (5)
H14A	0.2760	0.7198	0.6167	0.019*
H14B	0.4586	0.7256	0.6369	0.019*
C15	0.3574 (3)	0.81157 (12)	0.57692 (16)	0.0171 (5)
C16	0.3775 (3)	0.86177 (13)	0.64670 (18)	0.0201 (5)
H16A	0.4036	0.8516	0.7141	0.024*
C17	0.3584 (3)	0.92734 (13)	0.61549 (19)	0.0233 (6)
H17A	0.3737	0.9622	0.6622	0.028*
C18	0.3172 (3)	0.94303 (13)	0.5170 (2)	0.0264 (6)
H18A	0.3039	0.9881	0.4976	0.032*
C19	0.2956 (3)	0.89312 (13)	0.44737 (18)	0.0222 (5)
H19A	0.2663	0.9032	0.3803	0.027*
C20	0.3181 (3)	0.82781 (12)	0.47853 (16)	0.0164 (5)
C21	0.3106 (3)	0.76631 (12)	0.41957 (16)	0.0159 (5)
C22	0.3086 (3)	0.64178 (12)	0.45501 (16)	0.0165 (5)
H22A	0.2291	0.6511	0.3991	0.020*
C23	0.4350 (3)	0.60207 (12)	0.41273 (17)	0.0182 (5)
H23A	0.4869	0.5719	0.4627	0.022*
H23B	0.3934	0.5756	0.3551	0.022*
C24	0.2298 (3)	0.60506 (12)	0.53182 (17)	0.0167 (5)
C25	0.0724 (3)	0.60120 (13)	0.52232 (18)	0.0197 (5)
H25A	0.0153	0.6231	0.4690	0.024*
C26	−0.0042 (3)	0.56580 (13)	0.58934 (19)	0.0225 (5)
H26A	−0.1121	0.5631	0.5812	0.027*
C27	0.0790 (3)	0.53456 (12)	0.66806 (17)	0.0187 (5)
C28	0.2365 (3)	0.53925 (12)	0.68008 (17)	0.0199 (5)
H28A	0.2929	0.5187	0.7349	0.024*
C29	0.3123 (3)	0.57388 (12)	0.61240 (17)	0.0198 (5)
H29A	0.4202	0.5765	0.6207	0.024*
C30	0.6816 (3)	0.62840 (13)	0.35438 (18)	0.0225 (6)
H30A	0.6606	0.6025	0.2940	0.034*
H30B	0.7321	0.6001	0.4063	0.034*
H30C	0.7481	0.6659	0.3426	0.034*
C31	−0.0011 (3)	0.49303 (13)	0.73694 (18)	0.0217 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0516 (11)	0.0162 (8)	0.0285 (8)	−0.0061 (7)	0.0187 (7)	−0.0013 (6)
F2	0.0565 (12)	0.0422 (10)	0.0176 (7)	−0.0214 (9)	0.0121 (7)	−0.0018 (7)
F3	0.0346 (10)	0.0408 (11)	0.0548 (11)	0.0048 (8)	0.0291 (9)	0.0143 (9)
O1	0.0204 (9)	0.0198 (9)	0.0192 (8)	−0.0005 (7)	0.0044 (7)	0.0053 (7)
O2	0.0281 (10)	0.0237 (9)	0.0130 (7)	−0.0003 (8)	0.0002 (7)	0.0007 (7)
N1	0.0189 (11)	0.0157 (10)	0.0141 (9)	−0.0004 (8)	0.0060 (8)	−0.0035 (7)
C1	0.0160 (11)	0.0183 (12)	0.0115 (10)	0.0010 (9)	0.0068 (8)	−0.0005 (9)
C2	0.0178 (12)	0.0172 (11)	0.0136 (10)	0.0009 (10)	0.0060 (9)	−0.0023 (9)
C3	0.0195 (12)	0.0242 (13)	0.0139 (10)	0.0012 (10)	0.0053 (9)	−0.0015 (9)
C4	0.0187 (13)	0.0274 (14)	0.0197 (11)	−0.0005 (11)	0.0014 (9)	−0.0060 (10)
C5	0.0190 (13)	0.0225 (13)	0.0212 (12)	−0.0035 (10)	0.0055 (9)	−0.0054 (10)
C6	0.0200 (12)	0.0194 (12)	0.0162 (11)	−0.0006 (10)	0.0082 (9)	−0.0038 (9)
C7	0.0267 (14)	0.0195 (12)	0.0206 (12)	−0.0056 (11)	0.0094 (10)	−0.0012 (10)
C8	0.0282 (14)	0.0228 (13)	0.0142 (11)	−0.0025 (11)	0.0090 (10)	0.0026 (10)
C9	0.0237 (13)	0.0241 (13)	0.0118 (10)	−0.0001 (11)	0.0053 (9)	0.0001 (9)
C10	0.0163 (11)	0.0175 (11)	0.0125 (10)	0.0012 (9)	0.0067 (8)	−0.0023 (9)
C11	0.0179 (12)	0.0194 (12)	0.0121 (10)	0.0021 (10)	0.0051 (8)	−0.0023 (9)
C12	0.0172 (12)	0.0157 (11)	0.0111 (9)	−0.0002 (9)	0.0025 (8)	0.0008 (8)
C13	0.0182 (12)	0.0157 (11)	0.0118 (10)	0.0012 (9)	0.0033 (8)	0.0004 (8)
C14	0.0211 (12)	0.0165 (11)	0.0116 (10)	0.0007 (10)	0.0053 (8)	0.0005 (9)
C15	0.0162 (12)	0.0215 (12)	0.0142 (10)	0.0018 (10)	0.0051 (9)	−0.0015 (9)
C16	0.0202 (13)	0.0236 (13)	0.0174 (11)	0.0003 (10)	0.0067 (9)	−0.0021 (10)
C17	0.0272 (14)	0.0216 (13)	0.0228 (12)	−0.0023 (11)	0.0105 (10)	−0.0073 (10)
C18	0.0336 (16)	0.0173 (13)	0.0298 (13)	0.0024 (11)	0.0093 (11)	0.0036 (10)
C19	0.0263 (14)	0.0213 (13)	0.0200 (11)	0.0032 (11)	0.0072 (10)	0.0036 (10)
C20	0.0176 (12)	0.0171 (11)	0.0154 (10)	0.0010 (10)	0.0050 (9)	0.0012 (9)
C21	0.0158 (11)	0.0188 (12)	0.0137 (10)	0.0001 (10)	0.0045 (8)	0.0027 (9)
C22	0.0179 (12)	0.0166 (11)	0.0155 (10)	−0.0015 (9)	0.0035 (9)	0.0004 (9)
C23	0.0229 (13)	0.0168 (12)	0.0156 (10)	−0.0028 (10)	0.0056 (9)	−0.0019 (9)
C24	0.0216 (13)	0.0134 (11)	0.0162 (10)	−0.0021 (10)	0.0076 (9)	−0.0008 (9)
C25	0.0204 (13)	0.0196 (12)	0.0198 (11)	0.0015 (10)	0.0056 (9)	0.0000 (9)
C26	0.0182 (13)	0.0227 (13)	0.0280 (13)	0.0002 (11)	0.0082 (10)	0.0002 (10)
C27	0.0257 (13)	0.0157 (11)	0.0170 (11)	−0.0013 (10)	0.0129 (9)	−0.0027 (9)
C28	0.0259 (14)	0.0183 (12)	0.0163 (11)	−0.0009 (10)	0.0058 (9)	0.0012 (9)
C29	0.0192 (13)	0.0205 (12)	0.0203 (11)	−0.0008 (10)	0.0049 (9)	0.0001 (10)
C30	0.0231 (13)	0.0237 (13)	0.0217 (12)	0.0012 (11)	0.0069 (10)	−0.0045 (10)
C31	0.0250 (14)	0.0202 (13)	0.0225 (12)	−0.0011 (11)	0.0144 (10)	−0.0019 (10)

Geometric parameters (Å, º) top

F1—C31	1.343 (3)	C14—H14A	0.9900
F2—C31	1.339 (3)	C14—H14B	0.9900
F3—C31	1.332 (3)	C15—C16	1.390 (3)
O1—C1	1.215 (3)	C15—C20	1.395 (3)
O2—C21	1.216 (3)	C16—C17	1.392 (4)
N1—C30	1.457 (3)	C16—H16A	0.9500
N1—C23	1.462 (3)	C17—C18	1.397 (4)
N1—C12	1.465 (3)	C17—H17A	0.9500
C1—C2	1.470 (3)	C18—C19	1.385 (4)
C1—C12	1.586 (3)	C18—H18A	0.9500
C2—C3	1.383 (3)	C19—C20	1.390 (3)
C2—C11	1.408 (3)	C19—H19A	0.9500
C3—C4	1.410 (4)	C20—C21	1.476 (3)
C3—H3A	0.9500	C22—C24	1.517 (3)
C4—C5	1.384 (4)	C22—C23	1.538 (4)
C4—H4A	0.9500	C22—H22A	1.0000
C5—C6	1.417 (3)	C23—H23A	0.9900
C5—H5A	0.9500	C23—H23B	0.9900
C6—C11	1.402 (3)	C24—C25	1.385 (4)
C6—C7	1.423 (3)	C24—C29	1.404 (3)
C7—C8	1.374 (3)	C25—C26	1.395 (4)
C7—H7A	0.9500	C25—H25A	0.9500
C8—C9	1.419 (4)	C26—C27	1.389 (3)
C8—H8A	0.9500	C26—H26A	0.9500
C9—C10	1.370 (3)	C27—C28	1.387 (4)
C9—H9A	0.9500	C27—C31	1.495 (4)
C10—C11	1.417 (3)	C28—C29	1.390 (4)
C10—C12	1.526 (3)	C28—H28A	0.9500
C12—C13	1.573 (4)	C29—H29A	0.9500
C13—C21	1.553 (3)	C30—H30A	0.9800
C13—C14	1.555 (3)	C30—H30B	0.9800
C13—C22	1.565 (3)	C30—H30C	0.9800
C14—C15	1.506 (3)

C30—N1—C23	114.8 (2)	C17—C16—H16A	120.8
C30—N1—C12	115.90 (19)	C16—C17—C18	121.5 (2)
C23—N1—C12	106.87 (18)	C16—C17—H17A	119.3
O1—C1—C2	127.3 (2)	C18—C17—H17A	119.3
O1—C1—C12	124.5 (2)	C19—C18—C17	120.3 (2)
C2—C1—C12	108.11 (19)	C19—C18—H18A	119.9
C3—C2—C11	120.0 (2)	C17—C18—H18A	119.9
C3—C2—C1	132.3 (2)	C18—C19—C20	118.1 (2)
C11—C2—C1	107.72 (19)	C18—C19—H19A	121.0
C2—C3—C4	118.0 (2)	C20—C19—H19A	121.0
C2—C3—H3A	121.0	C19—C20—C15	122.1 (2)
C4—C3—H3A	121.0	C19—C20—C21	128.9 (2)
C5—C4—C3	121.9 (2)	C15—C20—C21	109.0 (2)
C5—C4—H4A	119.1	O2—C21—C20	127.1 (2)
C3—C4—H4A	119.1	O2—C21—C13	125.6 (2)
C4—C5—C6	121.2 (2)	C20—C21—C13	107.31 (18)
C4—C5—H5A	119.4	C24—C22—C23	114.6 (2)
C6—C5—H5A	119.4	C24—C22—C13	116.69 (19)
C11—C6—C5	115.9 (2)	C23—C22—C13	104.93 (19)
C11—C6—C7	116.4 (2)	C24—C22—H22A	106.7
C5—C6—C7	127.6 (2)	C23—C22—H22A	106.7
C8—C7—C6	119.9 (2)	C13—C22—H22A	106.7
C8—C7—H7A	120.1	N1—C23—C22	103.67 (19)
C6—C7—H7A	120.1	N1—C23—H23A	111.0
C7—C8—C9	122.4 (2)	C22—C23—H23A	111.0
C7—C8—H8A	118.8	N1—C23—H23B	111.0
C9—C8—H8A	118.8	C22—C23—H23B	111.0
C10—C9—C8	119.3 (2)	H23A—C23—H23B	109.0
C10—C9—H9A	120.3	C25—C24—C29	118.6 (2)
C8—C9—H9A	120.4	C25—C24—C22	119.6 (2)
C9—C10—C11	118.1 (2)	C29—C24—C22	121.7 (2)
C9—C10—C12	132.7 (2)	C24—C25—C26	121.4 (2)
C11—C10—C12	109.21 (19)	C24—C25—H25A	119.3
C6—C11—C2	123.0 (2)	C26—C25—H25A	119.3
C6—C11—C10	123.9 (2)	C27—C26—C25	119.4 (2)
C2—C11—C10	113.0 (2)	C27—C26—H26A	120.3
N1—C12—C10	112.60 (19)	C25—C26—H26A	120.3
N1—C12—C13	101.81 (18)	C28—C27—C26	120.0 (2)
C10—C12—C13	117.51 (19)	C28—C27—C31	120.0 (2)
N1—C12—C1	113.36 (18)	C26—C27—C31	119.9 (2)
C10—C12—C1	101.53 (17)	C27—C28—C29	120.3 (2)
C13—C12—C1	110.51 (18)	C27—C28—H28A	119.8
C21—C13—C14	102.34 (18)	C29—C28—H28A	119.8
C21—C13—C22	110.03 (17)	C28—C29—C24	120.2 (2)
C14—C13—C22	119.3 (2)	C28—C29—H29A	119.9
C21—C13—C12	107.02 (19)	C24—C29—H29A	119.9
C14—C13—C12	113.39 (18)	N1—C30—H30A	109.5
C22—C13—C12	104.30 (19)	N1—C30—H30B	109.5
C15—C14—C13	104.15 (18)	H30A—C30—H30B	109.5
C15—C14—H14A	110.9	N1—C30—H30C	109.5
C13—C14—H14A	110.9	H30A—C30—H30C	109.5
C15—C14—H14B	110.9	H30B—C30—H30C	109.5
C13—C14—H14B	110.9	F3—C31—F2	106.7 (2)
H14A—C14—H14B	108.9	F3—C31—F1	105.7 (2)
C16—C15—C20	119.7 (2)	F2—C31—F1	105.8 (2)
C16—C15—C14	129.1 (2)	F3—C31—C27	113.2 (2)
C20—C15—C14	111.2 (2)	F2—C31—C27	112.7 (2)
C15—C16—C17	118.4 (2)	F1—C31—C27	112.2 (2)
C15—C16—H16A	120.8

O1—C1—C2—C3	−5.3 (5)	C22—C13—C14—C15	−145.3 (2)
C12—C1—C2—C3	178.6 (3)	C12—C13—C14—C15	91.2 (2)
O1—C1—C2—C11	171.9 (2)	C13—C14—C15—C16	−163.4 (3)
C12—C1—C2—C11	−4.2 (3)	C13—C14—C15—C20	18.0 (3)
C11—C2—C3—C4	0.4 (4)	C20—C15—C16—C17	−0.4 (4)
C1—C2—C3—C4	177.3 (3)	C14—C15—C16—C17	−178.8 (3)
C2—C3—C4—C5	−1.4 (4)	C15—C16—C17—C18	1.2 (4)
C3—C4—C5—C6	0.5 (4)	C16—C17—C18—C19	−0.6 (4)
C4—C5—C6—C11	1.4 (4)	C17—C18—C19—C20	−0.8 (4)
C4—C5—C6—C7	−176.6 (3)	C18—C19—C20—C15	1.7 (4)
C11—C6—C7—C8	−1.2 (4)	C18—C19—C20—C21	−176.6 (3)
C5—C6—C7—C8	176.8 (3)	C16—C15—C20—C19	−1.1 (4)
C6—C7—C8—C9	0.9 (4)	C14—C15—C20—C19	177.6 (2)
C7—C8—C9—C10	0.9 (4)	C16—C15—C20—C21	177.5 (2)
C8—C9—C10—C11	−2.2 (4)	C14—C15—C20—C21	−3.8 (3)
C8—C9—C10—C12	−179.9 (3)	C19—C20—C21—O2	−13.3 (4)
C5—C6—C11—C2	−2.5 (4)	C15—C20—C21—O2	168.3 (3)
C7—C6—C11—C2	175.8 (2)	C19—C20—C21—C13	166.2 (3)
C5—C6—C11—C10	−178.5 (2)	C15—C20—C21—C13	−12.3 (3)
C7—C6—C11—C10	−0.2 (4)	C14—C13—C21—O2	−158.2 (2)
C3—C2—C11—C6	1.6 (4)	C22—C13—C21—O2	−30.4 (3)
C1—C2—C11—C6	−176.0 (2)	C12—C13—C21—O2	82.3 (3)
C3—C2—C11—C10	178.0 (2)	C14—C13—C21—C20	22.3 (2)
C1—C2—C11—C10	0.4 (3)	C22—C13—C21—C20	150.1 (2)
C9—C10—C11—C6	1.9 (4)	C12—C13—C21—C20	−97.1 (2)
C12—C10—C11—C6	−179.9 (2)	C21—C13—C22—C24	−120.0 (2)
C9—C10—C11—C2	−174.4 (2)	C14—C13—C22—C24	−2.2 (3)
C12—C10—C11—C2	3.8 (3)	C12—C13—C22—C24	125.5 (2)
C30—N1—C12—C10	61.1 (3)	C21—C13—C22—C23	112.0 (2)
C23—N1—C12—C10	−169.48 (19)	C14—C13—C22—C23	−130.3 (2)
C30—N1—C12—C13	−172.15 (19)	C12—C13—C22—C23	−2.5 (2)
C23—N1—C12—C13	−42.7 (2)	C30—N1—C23—C22	171.83 (18)
C30—N1—C12—C1	−53.5 (3)	C12—N1—C23—C22	41.8 (2)
C23—N1—C12—C1	76.0 (2)	C24—C22—C23—N1	−151.82 (18)
C9—C10—C12—N1	50.4 (4)	C13—C22—C23—N1	−22.5 (2)
C11—C10—C12—N1	−127.4 (2)	C23—C22—C24—C25	−128.6 (2)
C9—C10—C12—C13	−67.4 (3)	C13—C22—C24—C25	108.2 (2)
C11—C10—C12—C13	114.8 (2)	C23—C22—C24—C29	50.6 (3)
C9—C10—C12—C1	172.0 (3)	C13—C22—C24—C29	−72.5 (3)
C11—C10—C12—C1	−5.8 (2)	C29—C24—C25—C26	−1.7 (4)
O1—C1—C12—N1	−49.2 (3)	C22—C24—C25—C26	177.6 (2)
C2—C1—C12—N1	127.1 (2)	C24—C25—C26—C27	0.9 (4)
O1—C1—C12—C10	−170.2 (2)	C25—C26—C27—C28	0.6 (4)
C2—C1—C12—C10	6.0 (2)	C25—C26—C27—C31	−176.3 (2)
O1—C1—C12—C13	64.4 (3)	C26—C27—C28—C29	−1.5 (4)
C2—C1—C12—C13	−119.4 (2)	C31—C27—C28—C29	175.4 (2)
N1—C12—C13—C21	−90.2 (2)	C27—C28—C29—C24	0.7 (4)
C10—C12—C13—C21	33.3 (2)	C25—C24—C29—C28	0.8 (4)
C1—C12—C13—C21	149.07 (18)	C22—C24—C29—C28	−178.4 (2)
N1—C12—C13—C14	157.69 (18)	C28—C27—C31—F3	160.1 (2)
C10—C12—C13—C14	−78.8 (2)	C26—C27—C31—F3	−23.0 (3)
C1—C12—C13—C14	37.0 (3)	C28—C27—C31—F2	38.9 (3)
N1—C12—C13—C22	26.4 (2)	C26—C27—C31—F2	−144.2 (2)
C10—C12—C13—C22	149.85 (18)	C28—C27—C31—F1	−80.4 (3)
C1—C12—C13—C22	−94.3 (2)	C26—C27—C31—F1	96.5 (3)
C21—C13—C14—C15	−23.7 (2)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) x, −y+3/2, z+1/2; (iii) x−1, y, z; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₃₁H₂₂F₃NO₂
M_r	497.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.8373 (2), 20.1333 (5), 13.7129 (3)
β (°)	96.243 (1)
V (Å³)	2425.39 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.28 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.971, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	27133, 7039, 4753
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.186, 1.10
No. of reflections	7039
No. of parameters	335
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.37

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C29—H29A···O1	0.9500	2.2900	3.166 (3)	153.00
C4—H4A···O2ⁱ	0.95	2.52	3.364 (3)	147.3
C16—H16A···N1ⁱⁱ	0.95	2.51	3.429 (3)	162.8
C26—H26A···O1ⁱⁱⁱ	0.9500	2.5100	3.324 (3)	144.00
C5—H5A···Cg1^iv	0.9500	2.74	3.417 (3)	129

Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) x, −y+3/2, z+1/2; (iii) x−1, y, z; (iv) x+1, y, z.

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

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.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. 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., Choon, T. S., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o2383. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wei, A. C., Ali, M. A., Choon, T. S., Razak, I. A. & Arshad, S. (2012). Acta Cryst. E68, o545–o546. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wei, A. C., Ali, M. A., Ismail, R., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o3293–o3294. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 5| May 2012| Pages o1296-o1297

doi:10.1107/S1600536812013645

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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[ace­naphthyl­ene-1,2′-pyrrolidine-3′,2′′-indane]-2,1′′(1H)-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

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