1'-Methyl-4'-phenyldispiro-[indan-2,2'-pyrrolidine-3',2''-indan]-1,3,1''-trione.

The conformation of the title compound, C(27)H(21)NO(3), is stabilized by a weak intra-molecular C-H⋯O hydrogen bond, which generates an S(6) ring motif. The pyrrolidine ring adopts a half-chair conformation. Both of the other five-membered rings are in envelope conformations. No significant inter-molecular hydrogen bonds are observed.

Related literature

For general background to and the biological activity of the title compound, see: Amalraj et al. (2003 ▶); Karthikeyan et al. (2010 ▶); Chande et al. (2005 ▶); Sriram et al. (2009 ▶); Duncan & Barry (2004 ▶). For reference bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Kumar et al. (2010 ▶); Wei et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C27H21NO3

M = 407.45

Monoclinic,

a = 8.4578 (7) Å

b = 11.6194 (9) Å

c = 22.6360 (16) Å

β = 109.693 (2)°

V = 2094.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.34 × 0.26 × 0.15 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.972, T max = 0.988

23854 measured reflections

6084 independent reflections

3982 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.163

S = 1.03

6084 reflections

281 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.21 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032934/wn2448sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032934/wn2448Isup2.hkl

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

C27H21NO3	F(000) = 856
Mr = 407.45	Dx = 1.292 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5963 reflections
a = 8.4578 (7) Å	θ = 2.6–28.2°
b = 11.6194 (9) Å	µ = 0.08 mm−1
c = 22.6360 (16) Å	T = 296 K
β = 109.693 (2)°	Block, yellow
V = 2094.4 (3) Å3	0.34 × 0.26 × 0.15 mm
Z = 4

Bruker SMART APEXII DUO CCD area-detector diffractometer	6084 independent reflections
Radiation source: fine-focus sealed tube	3982 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 30.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.972, Tmax = 0.988	k = −15→16
23854 measured reflections	l = −31→31

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0731P)2 + 0.4081P] where P = (Fo2 + 2Fc2)/3
6084 reflections	(Δ/σ)max = 0.001
281 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	1.34827 (16)	0.31094 (11)	0.95641 (6)	0.0717 (4)
O2	1.00814 (19)	0.39487 (11)	0.75292 (5)	0.0679 (4)
O3	0.98637 (17)	0.36481 (11)	0.97255 (5)	0.0622 (3)
N1	1.15973 (17)	0.19994 (11)	0.83324 (7)	0.0517 (3)
C1	0.7927 (4)	0.0968 (2)	0.94738 (12)	0.0926 (8)
H1A	0.8054	0.1696	0.9654	0.111*
C2	0.6731 (4)	0.0227 (2)	0.95567 (14)	0.1032 (9)
H2A	0.6047	0.0476	0.9778	0.124*
C3	0.6549 (3)	−0.0845 (2)	0.93209 (12)	0.0863 (7)
H3A	0.5778	−0.1352	0.9390	0.104*
C4	0.7512 (4)	−0.1166 (2)	0.89819 (17)	0.1153 (10)
H4A	0.7393	−0.1902	0.8812	0.138*
C5	0.8678 (3)	−0.04216 (18)	0.88813 (14)	0.0938 (8)
H5A	0.9306	−0.0661	0.8637	0.113*
C6	0.89185 (19)	0.06577 (13)	0.91353 (7)	0.0457 (3)
C7	1.02348 (18)	0.14830 (12)	0.90680 (7)	0.0415 (3)
H7A	1.0976	0.1668	0.9494	0.050*
C8	1.1369 (2)	0.10356 (15)	0.87084 (10)	0.0607 (5)
H8A	1.2442	0.0783	0.8999	0.073*
H8B	1.0839	0.0394	0.8441	0.073*
C9	1.3153 (3)	0.2003 (2)	0.81922 (12)	0.0852 (7)
H9A	1.3127	0.2618	0.7906	0.128*
H9B	1.3275	0.1282	0.8005	0.128*
H9C	1.4084	0.2112	0.8573	0.128*
C10	1.11262 (17)	0.30515 (12)	0.85686 (7)	0.0414 (3)
C11	1.24588 (18)	0.36203 (13)	0.91420 (7)	0.0466 (3)
C12	1.22771 (17)	0.48842 (13)	0.90556 (7)	0.0424 (3)
C13	1.2992 (2)	0.57672 (14)	0.94769 (8)	0.0504 (4)
H13A	1.3671	0.5608	0.9886	0.060*
C14	1.2661 (2)	0.68821 (15)	0.92684 (9)	0.0575 (4)
H14A	1.3126	0.7485	0.9542	0.069*
C15	1.1648 (2)	0.71263 (15)	0.86571 (9)	0.0599 (4)
H15A	1.1453	0.7889	0.8529	0.072*
C16	1.0922 (2)	0.62575 (14)	0.82347 (8)	0.0523 (4)
H16A	1.0239	0.6422	0.7826	0.063*
C17	1.12528 (18)	0.51301 (13)	0.84439 (7)	0.0428 (3)
C18	1.07040 (19)	0.40499 (14)	0.80921 (7)	0.0461 (3)
C19	0.95609 (16)	0.26431 (12)	0.87430 (6)	0.0378 (3)
C20	0.91217 (19)	0.35346 (12)	0.91692 (7)	0.0428 (3)
C21	0.76765 (19)	0.42024 (13)	0.87730 (8)	0.0477 (4)
C22	0.7002 (3)	0.52158 (15)	0.89235 (11)	0.0663 (5)
H22A	0.7461	0.5559	0.9316	0.080*
C23	0.5639 (3)	0.5683 (2)	0.84708 (15)	0.0856 (7)
H23A	0.5155	0.6354	0.8555	0.103*
C24	0.4974 (3)	0.5161 (2)	0.78866 (14)	0.0898 (8)
H24A	0.4044	0.5491	0.7588	0.108*
C25	0.5656 (2)	0.41625 (19)	0.77349 (10)	0.0710 (6)
H25A	0.5206	0.3829	0.7340	0.085*
C26	0.70320 (18)	0.36772 (13)	0.81919 (8)	0.0477 (4)
C27	0.79686 (18)	0.25889 (13)	0.81565 (7)	0.0456 (3)
H27A	0.8256	0.2571	0.7776	0.055*
H27B	0.7304	0.1914	0.8167	0.055*

	U11	U22	U33	U12	U13	U23
O1	0.0569 (7)	0.0572 (7)	0.0736 (8)	−0.0085 (6)	−0.0143 (6)	0.0166 (6)
O2	0.0945 (10)	0.0639 (8)	0.0383 (6)	−0.0176 (7)	0.0131 (6)	0.0000 (5)
O3	0.0805 (8)	0.0580 (7)	0.0440 (7)	−0.0050 (6)	0.0155 (6)	−0.0125 (5)
N1	0.0550 (7)	0.0446 (7)	0.0638 (9)	−0.0008 (6)	0.0309 (7)	−0.0027 (6)
C1	0.128 (2)	0.0670 (13)	0.119 (2)	−0.0339 (13)	0.0878 (18)	−0.0193 (13)
C2	0.122 (2)	0.0954 (19)	0.125 (2)	−0.0344 (16)	0.0859 (18)	−0.0022 (16)
C3	0.0723 (13)	0.0836 (16)	0.0965 (17)	−0.0276 (12)	0.0200 (12)	0.0272 (13)
C4	0.119 (2)	0.0597 (14)	0.181 (3)	−0.0419 (14)	0.069 (2)	−0.0216 (17)
C5	0.0971 (16)	0.0507 (11)	0.155 (2)	−0.0228 (11)	0.0698 (17)	−0.0251 (13)
C6	0.0477 (7)	0.0391 (7)	0.0461 (8)	−0.0035 (6)	0.0103 (6)	0.0053 (6)
C7	0.0449 (7)	0.0352 (7)	0.0431 (8)	−0.0017 (5)	0.0130 (6)	0.0005 (6)
C8	0.0684 (11)	0.0437 (9)	0.0810 (13)	0.0068 (8)	0.0396 (10)	0.0044 (8)
C9	0.0804 (14)	0.0779 (14)	0.122 (2)	0.0045 (11)	0.0670 (14)	0.0036 (13)
C10	0.0420 (7)	0.0378 (7)	0.0428 (8)	−0.0054 (5)	0.0120 (6)	−0.0010 (6)
C11	0.0398 (7)	0.0463 (8)	0.0475 (8)	−0.0071 (6)	0.0064 (6)	0.0056 (7)
C12	0.0391 (6)	0.0417 (7)	0.0457 (8)	−0.0060 (6)	0.0131 (6)	0.0017 (6)
C13	0.0497 (8)	0.0520 (9)	0.0476 (8)	−0.0098 (7)	0.0139 (7)	−0.0029 (7)
C14	0.0677 (10)	0.0469 (9)	0.0613 (11)	−0.0081 (8)	0.0260 (9)	−0.0119 (8)
C15	0.0736 (11)	0.0420 (9)	0.0670 (11)	0.0037 (8)	0.0275 (9)	0.0034 (8)
C16	0.0571 (9)	0.0498 (9)	0.0498 (9)	0.0016 (7)	0.0176 (7)	0.0083 (7)
C17	0.0429 (7)	0.0429 (8)	0.0426 (8)	−0.0046 (6)	0.0146 (6)	0.0033 (6)
C18	0.0485 (8)	0.0489 (8)	0.0396 (8)	−0.0080 (6)	0.0132 (6)	0.0010 (6)
C19	0.0380 (6)	0.0349 (7)	0.0383 (7)	−0.0038 (5)	0.0098 (5)	−0.0032 (5)
C20	0.0477 (7)	0.0362 (7)	0.0453 (8)	−0.0065 (6)	0.0170 (6)	−0.0035 (6)
C21	0.0480 (8)	0.0405 (8)	0.0611 (10)	0.0006 (6)	0.0267 (7)	0.0062 (7)
C22	0.0780 (12)	0.0463 (9)	0.0926 (14)	0.0087 (8)	0.0524 (11)	0.0089 (9)
C23	0.0805 (14)	0.0618 (13)	0.134 (2)	0.0262 (11)	0.0619 (16)	0.0306 (14)
C24	0.0582 (11)	0.0838 (16)	0.129 (2)	0.0260 (11)	0.0339 (13)	0.0571 (16)
C25	0.0481 (9)	0.0771 (13)	0.0796 (13)	0.0005 (9)	0.0108 (9)	0.0307 (11)
C26	0.0370 (7)	0.0469 (8)	0.0578 (9)	−0.0028 (6)	0.0141 (6)	0.0135 (7)
C27	0.0434 (7)	0.0443 (8)	0.0428 (8)	−0.0079 (6)	0.0064 (6)	−0.0026 (6)

O1—C11	1.2073 (18)	C11—C12	1.483 (2)
O2—C18	1.2092 (18)	C12—C13	1.393 (2)
O3—C20	1.2102 (18)	C12—C17	1.393 (2)
N1—C10	1.4432 (19)	C13—C14	1.375 (2)
N1—C9	1.454 (2)	C13—H13A	0.9300
N1—C8	1.459 (2)	C14—C15	1.389 (3)
C1—C6	1.362 (3)	C14—H14A	0.9300
C1—C2	1.388 (3)	C15—C16	1.384 (2)
C1—H1A	0.9300	C15—H15A	0.9300
C2—C3	1.344 (4)	C16—C17	1.389 (2)
C2—H2A	0.9300	C16—H16A	0.9300
C3—C4	1.346 (4)	C17—C18	1.475 (2)
C3—H3A	0.9300	C19—C27	1.5411 (19)
C4—C5	1.387 (3)	C19—C20	1.5438 (19)
C4—H4A	0.9300	C20—C21	1.470 (2)
C5—C6	1.366 (3)	C21—C26	1.384 (2)
C5—H5A	0.9300	C21—C22	1.400 (2)
C6—C7	1.515 (2)	C22—C23	1.370 (3)
C7—C8	1.542 (2)	C22—H22A	0.9300
C7—C19	1.549 (2)	C23—C24	1.390 (4)
C7—H7A	0.9800	C23—H23A	0.9300
C8—H8A	0.9700	C24—C25	1.390 (3)
C8—H8B	0.9700	C24—H24A	0.9300
C9—H9A	0.9600	C25—C26	1.389 (2)
C9—H9B	0.9600	C25—H25A	0.9300
C9—H9C	0.9600	C26—C27	1.508 (2)
C10—C18	1.542 (2)	C27—H27A	0.9700
C10—C11	1.551 (2)	C27—H27B	0.9700
C10—C19	1.5766 (19)
C10—N1—C9	117.49 (14)	C14—C13—C12	117.91 (16)
C10—N1—C8	109.06 (12)	C14—C13—H13A	121.0
C9—N1—C8	115.95 (15)	C12—C13—H13A	121.0
C6—C1—C2	121.8 (2)	C13—C14—C15	121.34 (16)
C6—C1—H1A	119.1	C13—C14—H14A	119.3
C2—C1—H1A	119.1	C15—C14—H14A	119.3
C3—C2—C1	120.8 (2)	C16—C15—C14	121.36 (16)
C3—C2—H2A	119.6	C16—C15—H15A	119.3
C1—C2—H2A	119.6	C14—C15—H15A	119.3
C2—C3—C4	118.2 (2)	C15—C16—C17	117.45 (15)
C2—C3—H3A	120.9	C15—C16—H16A	121.3
C4—C3—H3A	120.9	C17—C16—H16A	121.3
C3—C4—C5	121.4 (2)	C16—C17—C12	121.24 (14)
C3—C4—H4A	119.3	C16—C17—C18	128.89 (14)
C5—C4—H4A	119.3	C12—C17—C18	109.83 (13)
C6—C5—C4	121.1 (2)	O2—C18—C17	126.70 (14)
C6—C5—H5A	119.4	O2—C18—C10	125.44 (14)
C4—C5—H5A	119.4	C17—C18—C10	107.82 (12)
C1—C6—C5	116.57 (17)	C27—C19—C20	103.96 (11)
C1—C6—C7	120.11 (15)	C27—C19—C7	116.64 (11)
C5—C6—C7	123.30 (16)	C20—C19—C7	114.48 (12)
C6—C7—C8	116.63 (13)	C27—C19—C10	111.13 (11)
C6—C7—C19	115.67 (12)	C20—C19—C10	110.71 (11)
C8—C7—C19	103.73 (12)	C7—C19—C10	100.09 (11)
C6—C7—H7A	106.7	O3—C20—C21	127.61 (14)
C8—C7—H7A	106.7	O3—C20—C19	125.02 (14)
C19—C7—H7A	106.7	C21—C20—C19	107.37 (12)
N1—C8—C7	106.11 (12)	C26—C21—C22	122.67 (16)
N1—C8—H8A	110.5	C26—C21—C20	109.10 (13)
C7—C8—H8A	110.5	C22—C21—C20	128.23 (17)
N1—C8—H8B	110.5	C23—C22—C21	117.4 (2)
C7—C8—H8B	110.5	C23—C22—H22A	121.3
H8A—C8—H8B	108.7	C21—C22—H22A	121.3
N1—C9—H9A	109.5	C22—C23—C24	120.5 (2)
N1—C9—H9B	109.5	C22—C23—H23A	119.7
H9A—C9—H9B	109.5	C24—C23—H23A	119.7
N1—C9—H9C	109.5	C23—C24—C25	122.1 (2)
H9A—C9—H9C	109.5	C23—C24—H24A	119.0
H9B—C9—H9C	109.5	C25—C24—H24A	119.0
N1—C10—C18	113.94 (12)	C26—C25—C24	117.9 (2)
N1—C10—C11	117.22 (13)	C26—C25—H25A	121.0
C18—C10—C11	101.33 (11)	C24—C25—H25A	121.0
N1—C10—C19	101.41 (11)	C21—C26—C25	119.43 (17)
C18—C10—C19	112.68 (12)	C21—C26—C27	111.98 (13)
C11—C10—C19	110.70 (11)	C25—C26—C27	128.58 (17)
O1—C11—C12	127.32 (14)	C26—C27—C19	104.01 (12)
O1—C11—C10	125.30 (15)	C26—C27—H27A	111.0
C12—C11—C10	107.33 (12)	C19—C27—H27A	111.0
C13—C12—C17	120.70 (14)	C26—C27—H27B	111.0
C13—C12—C11	129.62 (14)	C19—C27—H27B	111.0
C17—C12—C11	109.66 (13)	H27A—C27—H27B	109.0
C6—C1—C2—C3	2.3 (5)	N1—C10—C18—O2	32.0 (2)
C1—C2—C3—C4	−2.5 (5)	C11—C10—C18—O2	158.81 (16)
C2—C3—C4—C5	0.7 (5)	C19—C10—C18—O2	−82.9 (2)
C3—C4—C5—C6	1.5 (5)	N1—C10—C18—C17	−145.92 (13)
C2—C1—C6—C5	0.0 (4)	C11—C10—C18—C17	−19.09 (15)
C2—C1—C6—C7	−178.7 (2)	C19—C10—C18—C17	99.24 (14)
C4—C5—C6—C1	−1.8 (4)	C6—C7—C19—C27	−42.73 (18)
C4—C5—C6—C7	176.8 (2)	C8—C7—C19—C27	86.27 (15)
C1—C6—C7—C8	176.65 (19)	C6—C7—C19—C20	78.95 (15)
C5—C6—C7—C8	−1.9 (3)	C8—C7—C19—C20	−152.06 (13)
C1—C6—C7—C19	−61.0 (2)	C6—C7—C19—C10	−162.65 (12)
C5—C6—C7—C19	120.5 (2)	C8—C7—C19—C10	−33.65 (14)
C10—N1—C8—C7	16.59 (18)	N1—C10—C19—C27	−80.25 (14)
C9—N1—C8—C7	151.92 (17)	C18—C10—C19—C27	41.96 (16)
C6—C7—C8—N1	140.91 (14)	C11—C10—C19—C27	154.64 (12)
C19—C7—C8—N1	12.50 (17)	N1—C10—C19—C20	164.75 (12)
C9—N1—C10—C18	66.1 (2)	C18—C10—C19—C20	−73.04 (15)
C8—N1—C10—C18	−159.39 (14)	C11—C10—C19—C20	39.63 (16)
C9—N1—C10—C11	−52.0 (2)	N1—C10—C19—C7	43.60 (13)
C8—N1—C10—C11	82.57 (16)	C18—C10—C19—C7	165.81 (12)
C9—N1—C10—C19	−172.61 (16)	C11—C10—C19—C7	−81.52 (13)
C8—N1—C10—C19	−38.06 (16)	C27—C19—C20—O3	162.64 (14)
N1—C10—C11—O1	−34.0 (2)	C7—C19—C20—O3	34.26 (19)
C18—C10—C11—O1	−158.66 (17)	C10—C19—C20—O3	−77.95 (18)
C19—C10—C11—O1	81.6 (2)	C27—C19—C20—C21	−17.88 (14)
N1—C10—C11—C12	143.58 (13)	C7—C19—C20—C21	−146.26 (12)
C18—C10—C11—C12	18.94 (15)	C10—C19—C20—C21	101.54 (13)
C19—C10—C11—C12	−100.80 (14)	O3—C20—C21—C26	−169.99 (15)
O1—C11—C12—C13	−13.2 (3)	C19—C20—C21—C26	10.55 (16)
C10—C11—C12—C13	169.23 (15)	O3—C20—C21—C22	10.7 (3)
O1—C11—C12—C17	165.01 (17)	C19—C20—C21—C22	−168.81 (15)
C10—C11—C12—C17	−12.52 (16)	C26—C21—C22—C23	0.6 (2)
C17—C12—C13—C14	−0.4 (2)	C20—C21—C22—C23	179.92 (17)
C11—C12—C13—C14	177.69 (16)	C21—C22—C23—C24	−0.3 (3)
C12—C13—C14—C15	0.0 (2)	C22—C23—C24—C25	−0.5 (3)
C13—C14—C15—C16	0.4 (3)	C23—C24—C25—C26	0.9 (3)
C14—C15—C16—C17	−0.3 (3)	C22—C21—C26—C25	−0.2 (2)
C15—C16—C17—C12	0.0 (2)	C20—C21—C26—C25	−179.63 (14)
C15—C16—C17—C18	−177.50 (16)	C22—C21—C26—C27	−179.01 (14)
C13—C12—C17—C16	0.4 (2)	C20—C21—C26—C27	1.59 (17)
C11—C12—C17—C16	−178.01 (14)	C24—C25—C26—C21	−0.5 (3)
C13—C12—C17—C18	178.31 (13)	C24—C25—C26—C27	178.03 (16)
C11—C12—C17—C18	−0.12 (17)	C21—C26—C27—C19	−12.89 (16)
C16—C17—C18—O2	12.6 (3)	C25—C26—C27—C19	168.47 (16)
C12—C17—C18—O2	−165.04 (16)	C20—C19—C27—C26	18.05 (14)
C16—C17—C18—C10	−169.50 (15)	C7—C19—C27—C26	145.09 (12)
C12—C17—C18—C10	12.82 (16)	C10—C19—C27—C26	−101.08 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27A···O2	0.97	2.42	3.069 (2)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C27—H27A⋯O2	0.97	2.42	3.069 (2)	124