1′-Methyl-4′-(1-naphth­yl)-1′′,2′′,3′′,4′′-tetra­hydro­indane-2-spiro-2′-pyrrolidine-3′-spiro-2′′-naphthalene-1,3,1′′-trione

Selvanayagam, S.; Sridhar, B.; Ravikumar, K.; Saravanan, P.; Raghunathan, R.

doi:10.1107/S1600536811004880

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o629

doi:10.1107/S1600536811004880

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1′-Methyl-4′-(1-naphthyl)-1′′,2′′,3′′,4′′-tetrahydroindane-2-spiro-2′-pyrrolidine-3′-spiro-2′′-naphthalene-1,3,1′′-trione

S. Selvanayagam,^a ^* B. Sridhar,^b K. Ravikumar,^b P. Saravanan ^c and R. Raghunathan ^c

^aDepartment of Physics, Kalasalingam University, Krishnankoil 626 190, India, ^bLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India, and ^cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: s_selvanayagam@rediffmail.com

(Received 8 February 2011; accepted 9 February 2011; online 12 February 2011)

In the title compound, C₃₂H₂₅NO₃, the pyrrolidine ring adopts an envelope conformation, whereas the cyclohexanone ring in the tetrahydronaphthalene fused-ring system adopts a half-chair conformation. The indanedione unit is oriented at an angle of 58.9 (1)° with respect to the naphthyl ring system. Three intramolecular C—H⋯O close contacts and an intramolecular C—H⋯π interaction are observed. In the crystal, molecules associate via C—H⋯O hydrogen bonds, forming a helical chain with a C(10) motif along the b axis.

Related literature

For general background to pyrrolidine derivatives, see: Bello et al. (2010 ); Pettersson et al. (2011 ). For related structures, see: Abdul Ajees et al. (2002 ); Selvanayagam et al. (2005 ). For ring puckering parameters, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₃₂H₂₅NO₃
M_r = 471.53
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.8442 (9) Å
b = 11.431 (1) Å
c = 19.2701 (16) Å
V = 2388.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 292 K
0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
28122 measured reflections
3233 independent reflections
2941 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.112
S = 1.10
3233 reflections
326 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is centroid of the C1/C5/C6/C11/C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3	0.98	2.23	2.772 (2)	114
C4—H4A⋯O1	0.97	2.53	3.072 (3)	115
C13—H13B⋯O1	0.97	2.59	3.246 (3)	125
C29—H29⋯O2ⁱ	0.93	2.40	3.218 (2)	146
C17—H17⋯O1ⁱⁱ	0.93	2.55	3.442 (3)	163
C14—H14B⋯Cg1	0.97	2.51	3.146 (2)	123
Symmetry codes: (i) x, y-1, z; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004880/ng5116sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811004880/ng5116Isup2.hkl

checkCIF report

Comment top

Pyrrolidine derivatives are used as norepinephrine reuptake inhibitors and 5-HT(1A) partial agonists for treating neuropsychiatric disorders including depression and anxiety (Pettersson et al., 2011). These derivatives are used as alpha-mannosidase inhibitors and with antitumor activities against hematological and solid malignancies (Bello et al., 2010). In view of these importance, we have undertaken the crystal structure determination of the title compound, a pyrrolidine derivative, and the results are presented here.

The molecular structure of (I) is illustrated in Fig. 1. The C—C bond lengths in the pyrrolidine ring are somewhat longer in particular at two spiro junctions C1 and C2 and the C—N bond lengths are somewhat shorter than normal values. This may be due to steric forces of the bulky substituents at atoms C1 and C2 of the pyrrolidine ring (Abdul Ajees et al., 2002; Selvanayagam et al., 2005).

The sum of the angles at N1 of the pyrrolidine ring [336.3°] is in accordance with sp³ hybridization. The short contacts H3···H24 (2.12 Å) and H4A···H31 (1.96 Å) result in substantial widening of the C24—C23—C22 and C31—C22—C3 bond angles [123.8 (2)° and 122.4 (2)°, respectively].

The indanedione moiety is planar with a maximum deviation of 0.051 (3) Å for atom C9. The keto O atoms O1 and O2 deviate from this system by 0.115 (2) and 0.177 (2) Å, respectively. The naphthyl group is also planar with a maximum deviation of 0.013 (2) Å for atom C30. This group is oriented at an angle of 58.9° with respect to the indanedione moiety.

Pyrrolidine ring is in an envelope conformation, with puckering parameters q₂ = 0.406 (2) Å and ϕ = 5.3 (2) °, and with atom N1 deviating 0.601 (2) Å from the least-squares plane passing through the remaining four atoms (C1-C4) of that ring (Cremer & Pople, 1975). The cyclohexanone ring in the tetrahydro naphthalin ring system has a half-chair conformation with the lowest asymmetry parameters of ΔC₂(C2-C13) = 0.070 (1)° (Nardelli, 1983).

The molecular structure is influenced by an intramolecular C—H···O hydrogen bonds and weak C—H···π interactions. In the molecular packing, C—H···O hydrogen bonds involving atoms C17 and O1 link symmetry related molecules to form a helical shape arrangement in the unit cell (Fig. 2 and Table 1). In addition to this another C—H···O hydrogen bonds form a C(10) chain motif in the unit cell.

Related literature top

For general background to pyrrolidine derivatives, see: Bello et al. (2010); Pettersson et al. (2011). For related structures, see: Abdul Ajees et al. (2002); Selvanayagam et al. (2005). For ring puckering parameters, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

To a mixture of ninhydrin (1mmol), sarcosine (1mmol) and 2-napthalidene- 1,2,3,4-tetrahydronaphthalene-1-ones (1mmol) was added and heated under reflux in methanol (20ml) until the disappearance of the starting materials as evidenced by TLC. The solvent was removed under vacuo. The crude product was subjected to column chromatography using petroleum ether-ethyl acetate as eluent. Single crystals were grown by slow evaporation from methanol.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level
	Fig. 2. Molecular packing of the title compound, viewed along the a axis; H-bonds are shown as dashed lines. For the sake of clarity, H atoms, not involved in hydrogen bonds, have been omitted

1'-Methyl-4'-(1-naphthyl)-1'',2'',3'',4''-tetrahydroindane-2-spiro-2'- pyrrolidine-3'-spiro-2''-naphthalene-1,3,1''-trione top

Crystal data top

C₃₂H₂₅NO₃	F(000) = 992
M_r = 471.53	D_x = 1.311 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 18128 reflections
a = 10.8442 (9) Å	θ = 2.2–27.7°
b = 11.431 (1) Å	µ = 0.08 mm⁻¹
c = 19.2701 (16) Å	T = 292 K
V = 2388.7 (3) Å³	Block, colourless
Z = 4	0.24 × 0.22 × 0.20 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2941 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 28.0°, θ_min = 2.1°
ω scans	h = −14→14
28122 measured reflections	k = −15→14
3233 independent reflections	l = −24→25

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0796P)² + 0.0432P] where P = (F_o² + 2F_c²)/3
3233 reflections	(Δ/σ)_max < 0.001
326 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₃₂H₂₅NO₃	V = 2388.7 (3) Å³
M_r = 471.53	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.8442 (9) Å	µ = 0.08 mm⁻¹
b = 11.431 (1) Å	T = 292 K
c = 19.2701 (16) Å	0.24 × 0.22 × 0.20 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2941 reflections with I > 2σ(I)
28122 measured reflections	R_int = 0.025
3233 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.10	Δρ_max = 0.23 e Å⁻³
3233 reflections	Δρ_min = −0.16 e Å⁻³
326 parameters

Special details top

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
O1	0.39079 (16)	0.65842 (13)	0.26515 (8)	0.0626 (4)
O2	0.27742 (18)	1.00671 (13)	0.15142 (9)	0.0670 (4)
O3	0.19107 (14)	0.83352 (13)	0.03036 (7)	0.0548 (4)
N1	0.42985 (14)	0.79880 (14)	0.13310 (8)	0.0437 (3)
C1	0.32344 (15)	0.80317 (14)	0.17897 (8)	0.0373 (3)
C2	0.22397 (15)	0.73033 (13)	0.13771 (8)	0.0344 (3)
C3	0.30573 (15)	0.64431 (14)	0.09301 (8)	0.0379 (3)
H3	0.2908	0.6644	0.0443	0.045*
C4	0.43936 (17)	0.67881 (18)	0.10855 (11)	0.0500 (4)
H4A	0.4747	0.6285	0.1439	0.060*
H4B	0.4897	0.6743	0.0670	0.060*
C5	0.34951 (17)	0.75451 (17)	0.25266 (9)	0.0453 (4)
C6	0.32235 (18)	0.8468 (2)	0.30327 (9)	0.0526 (5)
C7	0.3266 (2)	0.8410 (3)	0.37595 (11)	0.0731 (7)
H7	0.3516	0.7735	0.3989	0.088*
C8	0.2919 (3)	0.9403 (4)	0.41183 (14)	0.0961 (12)
H8	0.2931	0.9388	0.4601	0.115*
C9	0.2557 (3)	1.0410 (4)	0.37891 (19)	0.0943 (11)
H9	0.2323	1.1056	0.4051	0.113*
C10	0.2536 (2)	1.0476 (2)	0.30753 (15)	0.0730 (7)
H10	0.2307	1.1161	0.2849	0.088*
C11	0.28692 (19)	0.94840 (19)	0.27055 (11)	0.0530 (5)
C12	0.29105 (18)	0.93236 (16)	0.19442 (10)	0.0463 (4)
C13	0.12866 (17)	0.66910 (15)	0.18410 (9)	0.0412 (4)
H13A	0.0767	0.6198	0.1554	0.049*
H13B	0.1716	0.6188	0.2166	0.049*
C14	0.04745 (18)	0.75315 (19)	0.22442 (9)	0.0474 (4)
H14A	−0.0166	0.7092	0.2480	0.057*
H14B	0.0968	0.7921	0.2595	0.057*
C15	−0.01132 (16)	0.84350 (17)	0.17879 (9)	0.0451 (4)
C16	−0.1179 (2)	0.90178 (19)	0.19927 (13)	0.0607 (6)
H16	−0.1524	0.8854	0.2424	0.073*
C17	−0.17298 (18)	0.9832 (2)	0.15681 (15)	0.0664 (6)
H17	−0.2446	1.0208	0.1713	0.080*
C18	−0.1227 (2)	1.0096 (2)	0.09295 (15)	0.0639 (6)
H18	−0.1602	1.0648	0.0644	0.077*
C19	−0.01693 (18)	0.95372 (18)	0.07168 (11)	0.0517 (4)
H19	0.0173	0.9716	0.0287	0.062*
C20	0.03943 (16)	0.87038 (16)	0.11414 (9)	0.0417 (4)
C21	0.15470 (15)	0.81437 (15)	0.08854 (8)	0.0379 (3)
C22	0.27640 (16)	0.51479 (15)	0.10044 (9)	0.0392 (3)
C23	0.17262 (16)	0.46728 (15)	0.06386 (8)	0.0394 (3)
C24	0.09433 (18)	0.53423 (18)	0.02056 (10)	0.0481 (4)
H24	0.1111	0.6134	0.0144	0.058*
C25	−0.0049 (2)	0.4864 (2)	−0.01248 (12)	0.0605 (5)
H25	−0.0552	0.5332	−0.0400	0.073*
C26	−0.0314 (2)	0.3677 (2)	−0.00510 (14)	0.0702 (6)
H26	−0.0985	0.3352	−0.0281	0.084*
C27	0.0406 (2)	0.3001 (2)	0.03549 (13)	0.0656 (6)
H27	0.0218	0.2211	0.0401	0.079*
C28	0.1443 (2)	0.34598 (15)	0.07131 (10)	0.0480 (4)
C29	0.2201 (2)	0.27509 (17)	0.11260 (11)	0.0577 (5)
H29	0.2024	0.1958	0.1169	0.069*
C30	0.3187 (2)	0.32053 (19)	0.14624 (12)	0.0600 (5)
H30	0.3686	0.2725	0.1732	0.072*
C31	0.34582 (19)	0.44138 (18)	0.14031 (10)	0.0509 (4)
H31	0.4130	0.4716	0.1644	0.061*
C32	0.54458 (19)	0.8442 (2)	0.16095 (12)	0.0592 (5)
H32A	0.5318	0.9224	0.1777	0.089*
H32B	0.6061	0.8450	0.1251	0.089*
H32C	0.5718	0.7954	0.1985	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0718 (9)	0.0584 (8)	0.0577 (8)	0.0018 (8)	−0.0114 (7)	0.0189 (7)
O2	0.0855 (12)	0.0406 (7)	0.0750 (10)	0.0010 (8)	−0.0074 (9)	0.0104 (7)
O3	0.0616 (8)	0.0629 (8)	0.0400 (6)	0.0169 (7)	0.0096 (6)	0.0150 (6)
N1	0.0374 (7)	0.0486 (8)	0.0451 (7)	−0.0078 (6)	0.0025 (6)	0.0002 (7)
C1	0.0399 (8)	0.0374 (8)	0.0346 (7)	−0.0028 (7)	−0.0015 (6)	0.0035 (6)
C2	0.0358 (7)	0.0346 (7)	0.0327 (7)	−0.0020 (6)	0.0013 (6)	0.0028 (6)
C3	0.0376 (8)	0.0387 (8)	0.0373 (7)	0.0012 (6)	0.0013 (6)	−0.0007 (6)
C4	0.0375 (8)	0.0540 (10)	0.0584 (10)	−0.0019 (8)	0.0070 (8)	−0.0072 (9)
C5	0.0437 (9)	0.0532 (10)	0.0391 (8)	−0.0092 (8)	−0.0046 (7)	0.0081 (7)
C6	0.0436 (9)	0.0732 (13)	0.0409 (8)	−0.0159 (9)	−0.0009 (7)	−0.0064 (9)
C7	0.0628 (13)	0.115 (2)	0.0416 (9)	−0.0265 (14)	−0.0014 (9)	−0.0075 (12)
C8	0.0746 (17)	0.162 (3)	0.0520 (13)	−0.036 (2)	0.0115 (13)	−0.0458 (19)
C9	0.0712 (17)	0.124 (3)	0.0873 (19)	−0.0207 (19)	0.0137 (15)	−0.062 (2)
C10	0.0568 (12)	0.0728 (14)	0.0895 (17)	−0.0096 (12)	0.0046 (12)	−0.0365 (14)
C11	0.0445 (9)	0.0590 (11)	0.0554 (10)	−0.0092 (9)	0.0025 (8)	−0.0154 (9)
C12	0.0448 (9)	0.0405 (8)	0.0535 (9)	−0.0047 (8)	−0.0013 (8)	−0.0034 (8)
C13	0.0425 (8)	0.0435 (8)	0.0377 (7)	−0.0075 (7)	0.0048 (7)	0.0055 (7)
C14	0.0445 (8)	0.0577 (10)	0.0399 (8)	−0.0105 (8)	0.0119 (7)	−0.0032 (8)
C15	0.0366 (8)	0.0483 (9)	0.0505 (9)	−0.0072 (7)	0.0051 (7)	−0.0137 (8)
C16	0.0459 (10)	0.0619 (12)	0.0744 (14)	−0.0072 (9)	0.0156 (10)	−0.0261 (11)
C17	0.0381 (9)	0.0605 (12)	0.1007 (17)	0.0060 (9)	0.0001 (11)	−0.0292 (13)
C18	0.0488 (10)	0.0517 (11)	0.0913 (17)	0.0112 (9)	−0.0177 (11)	−0.0161 (11)
C19	0.0484 (10)	0.0489 (10)	0.0577 (10)	0.0064 (8)	−0.0114 (8)	−0.0061 (9)
C20	0.0362 (8)	0.0430 (8)	0.0459 (8)	0.0014 (7)	−0.0026 (7)	−0.0069 (7)
C21	0.0363 (7)	0.0403 (8)	0.0370 (7)	0.0020 (7)	0.0021 (6)	0.0024 (6)
C22	0.0406 (8)	0.0386 (8)	0.0383 (7)	0.0046 (7)	0.0025 (7)	−0.0006 (6)
C23	0.0432 (8)	0.0371 (8)	0.0379 (7)	0.0018 (7)	0.0034 (7)	−0.0026 (6)
C24	0.0519 (10)	0.0474 (9)	0.0449 (9)	−0.0006 (8)	−0.0057 (8)	0.0011 (7)
C25	0.0532 (11)	0.0731 (14)	0.0551 (11)	−0.0015 (11)	−0.0117 (9)	−0.0020 (11)
C26	0.0621 (13)	0.0746 (15)	0.0740 (15)	−0.0168 (12)	−0.0070 (11)	−0.0181 (13)
C27	0.0706 (14)	0.0475 (10)	0.0789 (14)	−0.0110 (11)	0.0082 (12)	−0.0151 (11)
C28	0.0580 (11)	0.0361 (8)	0.0501 (9)	0.0004 (8)	0.0097 (8)	−0.0059 (7)
C29	0.0759 (14)	0.0347 (8)	0.0625 (11)	0.0090 (9)	0.0135 (11)	0.0012 (8)
C30	0.0762 (14)	0.0471 (10)	0.0566 (11)	0.0250 (10)	0.0023 (11)	0.0087 (9)
C31	0.0531 (10)	0.0507 (10)	0.0488 (10)	0.0124 (9)	−0.0060 (8)	−0.0002 (8)
C32	0.0446 (9)	0.0717 (13)	0.0613 (11)	−0.0167 (10)	−0.0039 (9)	0.0028 (11)

Geometric parameters (Å, º) top

O1—C5	1.210 (3)	C14—H14B	0.9700
O2—C12	1.196 (2)	C15—C16	1.391 (3)
O3—C21	1.208 (2)	C15—C20	1.396 (3)
N1—C32	1.451 (2)	C16—C17	1.376 (4)
N1—C1	1.454 (2)	C16—H16	0.9300
N1—C4	1.455 (3)	C17—C18	1.379 (4)
C1—C12	1.547 (2)	C17—H17	0.9300
C1—C5	1.551 (2)	C18—C19	1.376 (3)
C1—C2	1.578 (2)	C18—H18	0.9300
C2—C13	1.535 (2)	C19—C20	1.397 (3)
C2—C21	1.544 (2)	C19—H19	0.9300
C2—C3	1.580 (2)	C20—C21	1.489 (2)
C3—C22	1.521 (2)	C22—C31	1.364 (3)
C3—C4	1.531 (2)	C22—C23	1.435 (2)
C3—H3	0.9800	C23—C24	1.415 (3)
C4—H4A	0.9700	C23—C28	1.428 (2)
C4—H4B	0.9700	C24—C25	1.365 (3)
C5—C6	1.466 (3)	C24—H24	0.9300
C6—C11	1.376 (3)	C25—C26	1.394 (4)
C6—C7	1.403 (3)	C25—H25	0.9300
C7—C8	1.381 (5)	C26—C27	1.348 (4)
C7—H7	0.9300	C26—H26	0.9300
C8—C9	1.372 (5)	C27—C28	1.419 (3)
C8—H8	0.9300	C27—H27	0.9300
C9—C10	1.378 (5)	C28—C29	1.402 (3)
C9—H9	0.9300	C29—C30	1.354 (3)
C10—C11	1.387 (3)	C29—H29	0.9300
C10—H10	0.9300	C30—C31	1.417 (3)
C11—C12	1.479 (3)	C30—H30	0.9300
C13—C14	1.517 (3)	C31—H31	0.9300
C13—H13A	0.9700	C32—H32A	0.9600
C13—H13B	0.9700	C32—H32B	0.9600
C14—C15	1.499 (3)	C32—H32C	0.9600
C14—H14A	0.9700

C32—N1—C1	116.31 (15)	C15—C14—H14B	109.1
C32—N1—C4	113.40 (16)	C13—C14—H14B	109.1
C1—N1—C4	106.64 (14)	H14A—C14—H14B	107.8
N1—C1—C12	109.27 (14)	C16—C15—C20	118.4 (2)
N1—C1—C5	113.54 (14)	C16—C15—C14	121.12 (18)
C12—C1—C5	101.98 (14)	C20—C15—C14	120.50 (16)
N1—C1—C2	102.60 (12)	C17—C16—C15	121.1 (2)
C12—C1—C2	116.46 (14)	C17—C16—H16	119.5
C5—C1—C2	113.37 (13)	C15—C16—H16	119.5
C13—C2—C21	108.26 (13)	C16—C17—C18	120.4 (2)
C13—C2—C1	114.05 (12)	C16—C17—H17	119.8
C21—C2—C1	108.27 (12)	C18—C17—H17	119.8
C13—C2—C3	114.30 (13)	C19—C18—C17	119.6 (2)
C21—C2—C3	109.00 (12)	C19—C18—H18	120.2
C1—C2—C3	102.69 (12)	C17—C18—H18	120.2
C22—C3—C4	115.47 (15)	C18—C19—C20	120.5 (2)
C22—C3—C2	115.93 (13)	C18—C19—H19	119.8
C4—C3—C2	105.32 (13)	C20—C19—H19	119.8
C22—C3—H3	106.5	C15—C20—C19	120.02 (17)
C4—C3—H3	106.5	C15—C20—C21	122.15 (17)
C2—C3—H3	106.5	C19—C20—C21	117.83 (16)
N1—C4—C3	103.85 (14)	O3—C21—C20	120.24 (16)
N1—C4—H4A	111.0	O3—C21—C2	121.55 (15)
C3—C4—H4A	111.0	C20—C21—C2	118.21 (14)
N1—C4—H4B	111.0	C31—C22—C23	118.48 (17)
C3—C4—H4B	111.0	C31—C22—C3	122.43 (17)
H4A—C4—H4B	109.0	C23—C22—C3	119.09 (15)
O1—C5—C6	126.50 (17)	C24—C23—C28	117.09 (17)
O1—C5—C1	125.10 (17)	C24—C23—C22	123.75 (16)
C6—C5—C1	108.31 (16)	C28—C23—C22	119.15 (16)
C11—C6—C7	120.4 (2)	C25—C24—C23	122.1 (2)
C11—C6—C5	111.01 (16)	C25—C24—H24	118.9
C7—C6—C5	128.6 (2)	C23—C24—H24	118.9
C8—C7—C6	116.9 (3)	C24—C25—C26	120.3 (2)
C8—C7—H7	121.5	C24—C25—H25	119.9
C6—C7—H7	121.5	C26—C25—H25	119.9
C9—C8—C7	122.4 (3)	C27—C26—C25	119.9 (2)
C9—C8—H8	118.8	C27—C26—H26	120.1
C7—C8—H8	118.8	C25—C26—H26	120.1
C8—C9—C10	120.8 (3)	C26—C27—C28	121.9 (2)
C8—C9—H9	119.6	C26—C27—H27	119.0
C10—C9—H9	119.6	C28—C27—H27	119.0
C9—C10—C11	117.7 (3)	C29—C28—C27	121.79 (19)
C9—C10—H10	121.2	C29—C28—C23	119.48 (19)
C11—C10—H10	121.2	C27—C28—C23	118.72 (19)
C6—C11—C10	121.8 (2)	C30—C29—C28	120.87 (18)
C6—C11—C12	109.95 (17)	C30—C29—H29	119.6
C10—C11—C12	128.2 (2)	C28—C29—H29	119.6
O2—C12—C11	126.53 (19)	C29—C30—C31	119.94 (19)
O2—C12—C1	124.96 (17)	C29—C30—H30	120.0
C11—C12—C1	108.43 (16)	C31—C30—H30	120.0
C14—C13—C2	113.59 (14)	C22—C31—C30	122.0 (2)
C14—C13—H13A	108.8	C22—C31—H31	119.0
C2—C13—H13A	108.8	C30—C31—H31	119.0
C14—C13—H13B	108.8	N1—C32—H32A	109.5
C2—C13—H13B	108.8	N1—C32—H32B	109.5
H13A—C13—H13B	107.7	H32A—C32—H32B	109.5
C15—C14—C13	112.50 (14)	N1—C32—H32C	109.5
C15—C14—H14A	109.1	H32A—C32—H32C	109.5
C13—C14—H14A	109.1	H32B—C32—H32C	109.5

C32—N1—C1—C12	64.5 (2)	C5—C1—C12—C11	−5.58 (18)
C4—N1—C1—C12	−167.92 (15)	C2—C1—C12—C11	118.38 (16)
C32—N1—C1—C5	−48.6 (2)	C21—C2—C13—C14	−55.95 (19)
C4—N1—C1—C5	78.99 (18)	C1—C2—C13—C14	64.64 (19)
C32—N1—C1—C2	−171.34 (16)	C3—C2—C13—C14	−177.63 (14)
C4—N1—C1—C2	−43.74 (17)	C2—C13—C14—C15	51.9 (2)
N1—C1—C2—C13	151.52 (14)	C13—C14—C15—C16	157.93 (17)
C12—C1—C2—C13	−89.21 (17)	C13—C14—C15—C20	−21.5 (2)
C5—C1—C2—C13	28.67 (19)	C20—C15—C16—C17	0.6 (3)
N1—C1—C2—C21	−87.90 (15)	C14—C15—C16—C17	−178.84 (18)
C12—C1—C2—C21	31.37 (18)	C15—C16—C17—C18	−0.6 (3)
C5—C1—C2—C21	149.25 (14)	C16—C17—C18—C19	0.1 (3)
N1—C1—C2—C3	27.30 (15)	C17—C18—C19—C20	0.3 (3)
C12—C1—C2—C3	146.57 (14)	C16—C15—C20—C19	−0.2 (3)
C5—C1—C2—C3	−95.55 (15)	C14—C15—C20—C19	179.24 (17)
C13—C2—C3—C22	1.7 (2)	C16—C15—C20—C21	178.65 (16)
C21—C2—C3—C22	−119.53 (15)	C14—C15—C20—C21	−1.9 (3)
C1—C2—C3—C22	125.80 (14)	C18—C19—C20—C15	−0.2 (3)
C13—C2—C3—C4	−127.23 (16)	C18—C19—C20—C21	−179.14 (17)
C21—C2—C3—C4	111.49 (16)	C15—C20—C21—O3	174.69 (18)
C1—C2—C3—C4	−3.18 (16)	C19—C20—C21—O3	−6.4 (3)
C32—N1—C4—C3	171.27 (16)	C15—C20—C21—C2	−4.2 (2)
C1—N1—C4—C3	41.97 (18)	C19—C20—C21—C2	174.68 (16)
C22—C3—C4—N1	−151.38 (14)	C13—C2—C21—O3	−146.97 (17)
C2—C3—C4—N1	−22.13 (18)	C1—C2—C21—O3	88.92 (19)
N1—C1—C5—O1	−54.7 (2)	C3—C2—C21—O3	−22.1 (2)
C12—C1—C5—O1	−172.11 (18)	C13—C2—C21—C20	31.93 (19)
C2—C1—C5—O1	61.9 (2)	C1—C2—C21—C20	−92.19 (16)
N1—C1—C5—C6	122.12 (16)	C3—C2—C21—C20	156.82 (14)
C12—C1—C5—C6	4.71 (18)	C4—C3—C22—C31	22.4 (2)
C2—C1—C5—C6	−121.30 (15)	C2—C3—C22—C31	−101.47 (19)
O1—C5—C6—C11	174.55 (19)	C4—C3—C22—C23	−157.10 (15)
C1—C5—C6—C11	−2.2 (2)	C2—C3—C22—C23	79.05 (19)
O1—C5—C6—C7	−6.6 (3)	C31—C22—C23—C24	−179.52 (17)
C1—C5—C6—C7	176.6 (2)	C3—C22—C23—C24	0.0 (3)
C11—C6—C7—C8	1.1 (3)	C31—C22—C23—C28	1.1 (2)
C5—C6—C7—C8	−177.6 (2)	C3—C22—C23—C28	−179.40 (15)
C6—C7—C8—C9	−0.6 (4)	C28—C23—C24—C25	0.6 (3)
C7—C8—C9—C10	−0.6 (5)	C22—C23—C24—C25	−178.80 (18)
C8—C9—C10—C11	1.3 (4)	C23—C24—C25—C26	−0.9 (3)
C7—C6—C11—C10	−0.5 (3)	C24—C25—C26—C27	0.8 (4)
C5—C6—C11—C10	178.48 (18)	C25—C26—C27—C28	−0.3 (4)
C7—C6—C11—C12	179.53 (19)	C26—C27—C28—C29	−179.0 (2)
C5—C6—C11—C12	−1.5 (2)	C26—C27—C28—C23	−0.1 (3)
C9—C10—C11—C6	−0.7 (4)	C24—C23—C28—C29	178.86 (18)
C9—C10—C11—C12	179.3 (2)	C22—C23—C28—C29	−1.7 (3)
C6—C11—C12—O2	−172.2 (2)	C24—C23—C28—C27	−0.1 (3)
C10—C11—C12—O2	7.8 (4)	C22—C23—C28—C27	179.34 (17)
C6—C11—C12—C1	4.7 (2)	C27—C28—C29—C30	179.9 (2)
C10—C11—C12—C1	−175.3 (2)	C23—C28—C29—C30	0.9 (3)
N1—C1—C12—O2	50.9 (2)	C28—C29—C30—C31	0.4 (3)
C5—C1—C12—O2	171.4 (2)	C23—C22—C31—C30	0.3 (3)
C2—C1—C12—O2	−64.7 (2)	C3—C22—C31—C30	−179.19 (18)
N1—C1—C12—C11	−126.03 (16)	C29—C30—C31—C22	−1.1 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is centroid of the C1/C5/C6/C11/C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3	0.98	2.23	2.772 (2)	114
C4—H4A···O1	0.97	2.53	3.072 (3)	115
C13—H13B···O1	0.97	2.59	3.246 (3)	125
C29—H29···O2ⁱ	0.93	2.40	3.218 (2)	146
C17—H17···O1ⁱⁱ	0.93	2.55	3.442 (3)	163
C14—H14B···Cg1	0.97	2.51	3.146 (2)	123

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

Experimental details

Crystal data
Chemical formula	C₃₂H₂₅NO₃
M_r	471.53
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	292
a, b, c (Å)	10.8442 (9), 11.431 (1), 19.2701 (16)
V (Å³)	2388.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.24 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	28122, 3233, 2941
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.112, 1.10
No. of reflections	3233
No. of parameters	326
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.16

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is centroid of the C1/C5/C6/C11/C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3	0.98	2.23	2.772 (2)	114
C4—H4A···O1	0.97	2.53	3.072 (3)	115
C13—H13B···O1	0.97	2.59	3.246 (3)	125
C29—H29···O2ⁱ	0.93	2.40	3.218 (2)	146
C17—H17···O1ⁱⁱ	0.93	2.55	3.442 (3)	163
C14—H14B···Cg1	0.97	2.51	3.146 (2)	123

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

Acknowledgements

SS acknowledges the Department of Science and Technology (DST), India, for providing computing facilities under the DST-Fast Track Scheme and also thanks the Vice Chancellor and management of Kalasalingam University, Krishnankoil, for their support and encouragement.

References

Abdul Ajees, A., Manikandan, S. & Raghunathan, R. (2002). Acta Cryst. E58, o802–o804. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bello, C., Cea, M., Dal Bello, G., Garuti, A., Rocco, I., Cirmena, G., Moran, E., Nahimana, A., Duchosal, M. A., Fruscione, F., Pronzato, P., Grossi, F., Patrone, F., Ballestro, A., Dupuis, M., Sordat, B., Nencioni, A. & Vogel, P. (2010). Bioorg. Med. Chem. 18, 3320–3334. Web of Science CrossRef CAS PubMed Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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Pettersson, M., Campbell, B. M., Dounary, A. B., Gray, D. L., Xie, L., O^'Donnell, C. J., Stratman, N. C., Zoski, K., Drummond, E., Bora, G., Probert, A. & Whisman, T. (2011). Bioorg. Med. Chem. Lett. 21, 865–868. Web of Science CrossRef CAS PubMed Google Scholar
Selvanayagam, S., Velmurugan, D., Ravikumar, K., Jayashankaran, J. & Raghunathan, R. (2005). Acta Cryst. E61, o1582–o1584. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1′-Methyl-4′-(1-naphth­yl)-1′′,2′′,3′′,4′′-tetra­hydro­indane-2-spiro-2′-pyrrolidine-3′-spiro-2′′-naphthalene-1,3,1′′-trione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1′-Methyl-4′-(1-naphthyl)-1′′,2′′,3′′,4′′-tetrahydroindane-2-spiro-2′-pyrrolidine-3′-spiro-2′′-naphthalene-1,3,1′′-trione