(1R,4R,5R)-1,3,4-Triphenyl-7-[(R)-1-phenyl­ethyl]-2-oxa-3,7-diaza­spiro­[4.5]decan-10-one

Malathy, A.; Kumar, R.S.; Perumal, S.; Suresh, J.; Lakshman, N.

doi:10.1107/S1600536807067256

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o343

https://doi.org/10.1107/S1600536807067256

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(1R,4R,5R)-1,3,4-Triphenyl-7-[(R)-1-phenylethyl]-2-oxa-3,7-diazaspiro[4.5]decan-10-one

A. Malathy,^a R. Suresh Kumar,^b S. Perumal,^b J. Suresh ^c and Nilantha Lakshman ^d ^*

^aDepartment of Physics, Madurai Kamaraj University, Madurai 625 021, India, ^bSchool of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, ^cDepartment of Physics, Madura College, Madurai 625 011, India, and ^dDepartment of Food science and Technology, Faculty of Agriculture, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
^*Correspondence e-mail: nilanthalakshman@yahoo.co.uk

(Received 4 December 2007; accepted 17 December 2007; online 21 December 2007)

In the title compound, C₃₃H₃₂N₂O₂, the polysubstituted piperidine ring adopts a chair conformation. The isoxazolidine ring is in an envelope conformation. In the crystal structure, intra- and intermolecular C—H⋯π interactions involving the phenyl rings are observed.

Related literature

For related literature, see: Ali Dondas et al. (2001 ); Alibés et al. (2003 ); Blanarikova-Hlobilova et al. (2003 ); Carda et al. (2000 ); Carruthers (1990 ); Herrera et al. (2001 ); Huisgen (1963 ); Ishar et al. (2000 ). For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₃₃H₃₂N₂O₂
M_r = 488.61
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.589 (5) Å
b = 14.582 (7) Å
c = 17.443 (8) Å
V = 2693 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 273 (2) K
0.20 × 0.16 × 0.12 mm

Data collection

Nonius MACH-3 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.986, T_max = 0.991
13617 measured reflections
2701 independent reflections
1899 reflections with I > 2σ(I)
R_int = 0.074
2 standard reflections frequency: 60 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.118
S = 1.09
2701 reflections
335 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the phenyl rings C71–C76, C91–C96 and C81–C86, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1	0.98	2.35	2.775 (5)	106
C26—H26⋯O2	0.93	2.29	2.623 (5)	101
C82—H82⋯O2	0.93	2.43	2.757 (5)	101
C3—H3A⋯Cg1	0.97	2.90	3.659 (5)	136
C2—H2A⋯Cg2ⁱ	0.97	2.93	3.707 (5)	138
C74—H74⋯Cg3ⁱⁱ	0.93	2.96	3.722 (6)	141
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y, z+{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807067256/ci2540sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807067256/ci2540Isup2.hkl

checkCIF report

Comment top

1,3-Dipolar cycloaddition is a versatile reaction for the construction of five-membered ring heterocycles of biological importance (Huisgen, 1963). Among the 1,3-dipoles, nitrones have been subjected to numerous 1,3-dipolar cycloadditions, ascribable to their stability and ease of generation (Blanarikova-Hlobilova et al., 2003; Herrera et al., 2001). The 1,3-dipolar cycloaddition of nitrones to alkenes afford isoxazolidines with generation of as many as three new contiguous stereocenters in a single step (Ishar et al., 2000; Carda et al., 2000; Ali Dondas et al., 2001; Alibés et al., 2003). These isoxazolidines can be further elaborated into polyfunctional cyclic or acyclic bioactive compounds with complete control of relative stereochemistry (Carruthers, 1990).

The molecular structure of (I) is shown in Fig.1. The five-membered isoxazolidine ring has an envelope conformation, as indicated by the Cremer & Pople (1975) puckering parameters Q = 0.454 (3) Å and φ = 3.3 (5)°. The piperidine ring adopts a chair conformation. The dihedral angle between the C21–C26 and C71–C76 phenyl rings is 77.7 (1)°. The C21–C26, C71–C76 and C81–C86 phenyl rings form dihedral angles of 35.8 (2)°, 77.5 (1)° and 72.3 (2)°, respectively, with the N2/C7/C5/C8 plane.

Weak intramolecular C—H···O and C—H···π interactions are observed in the molecular structure. The packing of molecules is governed by weak C—H···π interactions (Table 1) and van der Walls interactions. In the Table 1, Cg1, Cg2 and Cg3 denote the centroids of the C71–C76, C91–C96 and C81–C86 phenyl rings.

Related literature top

For related literature, see: Ali Dondas et al. (2001); Alibés et al. (2003); Blanarikova-Hlobilova et al. (2003); Carda et al. (2000); Carruthers (1990); Herrera et al. (2001); Huisgen (1963); Ishar et al. (2000). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of [(R)-1-phenylethyl]-3-[(E)-phenylmethylidene]tetrahydro-4(1H)- pyridinone (0.300 g, 1 mmol) and nitrone (0.244 g, 1.2 mmol) in toluene (25 ml) was refluxed for 10 h. The progress of the reaction was monitored by thin-layer chromatography (TLC) and after completion of the reaction, the solvent was evaporated in vacuo. The residue was then subjected to flash column chromatography on silica gel using petroleum ether-ethyl acetate (10:1) as eluent to obtain crystals of the title compound in 8% yield (0.040 g) along with two other products in semi-solid form.

Structure description top

For related literature, see: Ali Dondas et al. (2001); Alibés et al. (2003); Blanarikova-Hlobilova et al. (2003); Carda et al. (2000); Carruthers (1990); Herrera et al. (2001); Huisgen (1963); Ishar et al. (2000). For ring puckering parameters, see: Cremer & Pople (1975).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.

(1R,4R,5R)-1,3,4-Triphenyl-7-[(R)-1-phenylethyl]-2-oxa-3,7-\ diazaspiro[4.5]decan-10-one top

Crystal data top

C₃₃H₃₂N₂O₂	F(000) = 1040
M_r = 488.61	D_x = 1.205 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 10.589 (5) Å	θ = 2–25°
b = 14.582 (7) Å	µ = 0.08 mm⁻¹
c = 17.443 (8) Å	T = 273 K
V = 2693 (2) Å³	Needle, colourless
Z = 4	0.20 × 0.16 × 0.12 mm

Data collection top

Nonius MACH-3 diffractometer	1899 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.074
Graphite monochromator	θ_max = 25.0°, θ_min = 1.8°
ω/2θ scans	h = −12→11
Absorption correction: ψ scan (North et al., 1968)	k = −17→16
T_min = 0.986, T_max = 0.991	l = −20→20
13617 measured reflections	2 standard reflections every 60 min
2701 independent reflections	intensity decay: none

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0519P)²] where P = (F_o² + 2F_c²)/3
2701 reflections	(Δ/σ)_max < 0.001
335 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₃₃H₃₂N₂O₂	V = 2693 (2) Å³
M_r = 488.61	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.589 (5) Å	µ = 0.08 mm⁻¹
b = 14.582 (7) Å	T = 273 K
c = 17.443 (8) Å	0.20 × 0.16 × 0.12 mm

Data collection top

Nonius MACH-3 diffractometer	1899 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.074
T_min = 0.986, T_max = 0.991	2 standard reflections every 60 min
13617 measured reflections	intensity decay: none
2701 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.09	Δρ_max = 0.16 e Å⁻³
2701 reflections	Δρ_min = −0.14 e Å⁻³
335 parameters

Special details top

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
C2	0.1883 (4)	0.3386 (3)	0.0817 (2)	0.0554 (11)
H2A	0.1260	0.2938	0.0978	0.066*
H2B	0.1896	0.3399	0.0261	0.066*
C3	0.1521 (4)	0.4324 (3)	0.1120 (2)	0.0544 (11)
H3A	0.2006	0.4784	0.0847	0.065*
H3B	0.0636	0.4430	0.1007	0.065*
C4	0.1724 (4)	0.4453 (3)	0.1961 (2)	0.0443 (10)
C5	0.2865 (3)	0.3966 (2)	0.2314 (2)	0.0390 (9)
C6	0.3004 (4)	0.3021 (2)	0.1937 (2)	0.0428 (10)
H6A	0.3743	0.2713	0.2142	0.051*
H6B	0.2269	0.2649	0.2054	0.051*
C7	0.4141 (4)	0.4506 (2)	0.22225 (19)	0.0406 (9)
H7	0.4773	0.4089	0.2006	0.049*
C8	0.2734 (4)	0.3908 (3)	0.3199 (2)	0.0438 (10)
H8	0.2265	0.4444	0.3382	0.053*
C9	0.3577 (4)	0.2247 (3)	0.0750 (2)	0.0481 (11)
H9	0.3031	0.1748	0.0928	0.058*
C10	0.4920 (4)	0.2034 (3)	0.0992 (2)	0.0643 (13)
H10A	0.4945	0.1932	0.1535	0.096*
H10B	0.5457	0.2542	0.0864	0.096*
H10C	0.5208	0.1494	0.0730	0.096*
C21	0.5823 (4)	0.4778 (2)	0.31879 (19)	0.0383 (9)
C22	0.6625 (4)	0.5250 (3)	0.2706 (2)	0.0528 (10)
H22	0.6305	0.5506	0.2258	0.063*
C23	0.7890 (4)	0.5351 (3)	0.2874 (2)	0.0562 (11)
H23	0.8411	0.5680	0.2544	0.067*
C24	0.8378 (4)	0.4969 (3)	0.3523 (3)	0.0617 (12)
H24	0.9233	0.5027	0.3635	0.074*
C25	0.7593 (5)	0.4500 (3)	0.4008 (3)	0.0723 (14)
H25	0.7921	0.4239	0.4452	0.087*
C26	0.6322 (4)	0.4408 (3)	0.3848 (2)	0.0590 (12)
H26	0.5800	0.4096	0.4188	0.071*
C71	0.4083 (4)	0.5349 (3)	0.1730 (2)	0.0429 (9)
C72	0.4473 (4)	0.5300 (3)	0.0971 (2)	0.0573 (12)
H72	0.4842	0.4764	0.0788	0.069*
C73	0.4319 (5)	0.6035 (4)	0.0490 (3)	0.0742 (14)
H73	0.4565	0.5987	−0.0021	0.089*
C74	0.3810 (5)	0.6836 (4)	0.0748 (3)	0.0781 (16)
H74	0.3696	0.7329	0.0417	0.094*
C75	0.3467 (4)	0.6905 (3)	0.1509 (3)	0.0673 (13)
H75	0.3150	0.7456	0.1696	0.081*
C76	0.3589 (4)	0.6165 (3)	0.1994 (2)	0.0523 (11)
H76	0.3336	0.6216	0.2502	0.063*
C81	0.2124 (4)	0.3053 (3)	0.3508 (2)	0.0453 (10)
C82	0.2819 (4)	0.2315 (3)	0.3763 (2)	0.0559 (12)
H82	0.3696	0.2350	0.3767	0.067*
C83	0.2234 (5)	0.1530 (3)	0.4014 (3)	0.0680 (14)
H83	0.2718	0.1037	0.4182	0.082*
C84	0.0949 (6)	0.1466 (4)	0.4019 (2)	0.0737 (15)
H84	0.0559	0.0933	0.4191	0.088*
C85	0.0232 (5)	0.2193 (4)	0.3767 (3)	0.0758 (15)
H85	−0.0644	0.2153	0.3766	0.091*
C86	0.0824 (4)	0.2987 (3)	0.3515 (2)	0.0571 (12)
H86	0.0339	0.3481	0.3349	0.068*
C91	0.3510 (4)	0.2279 (3)	−0.0116 (2)	0.0496 (11)
C92	0.3106 (5)	0.1525 (3)	−0.0517 (3)	0.0711 (14)
H92	0.2824	0.1011	−0.0253	0.085*
C93	0.3112 (6)	0.1519 (5)	−0.1306 (3)	0.099 (2)
H93	0.2846	0.0998	−0.1568	0.119*
C94	0.3506 (6)	0.2269 (6)	−0.1706 (3)	0.103 (2)
H94	0.3513	0.2259	−0.2239	0.124*
C95	0.3891 (5)	0.3036 (5)	−0.1320 (3)	0.0862 (17)
H95	0.4133	0.3559	−0.1588	0.103*
C96	0.3919 (4)	0.3029 (4)	−0.0530 (2)	0.0661 (13)
H96	0.4221	0.3542	−0.0270	0.079*
N1	0.3132 (3)	0.3116 (2)	0.11050 (15)	0.0403 (8)
N2	0.4506 (3)	0.4721 (2)	0.30247 (16)	0.0423 (8)
O1	0.1026 (3)	0.4923 (2)	0.23424 (16)	0.0660 (8)
O2	0.4005 (2)	0.39618 (18)	0.34690 (13)	0.0483 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.045 (3)	0.080 (3)	0.041 (2)	0.002 (3)	−0.006 (2)	−0.009 (2)
C3	0.037 (2)	0.071 (3)	0.055 (3)	0.007 (2)	−0.009 (2)	0.000 (2)
C4	0.039 (2)	0.043 (2)	0.051 (3)	−0.004 (2)	0.004 (2)	0.002 (2)
C5	0.041 (2)	0.041 (2)	0.035 (2)	−0.001 (2)	0.0020 (17)	0.0005 (18)
C6	0.044 (2)	0.042 (2)	0.042 (2)	0.001 (2)	0.0011 (19)	−0.0026 (19)
C7	0.040 (2)	0.046 (2)	0.036 (2)	0.000 (2)	0.0019 (18)	−0.0049 (19)
C8	0.042 (2)	0.051 (2)	0.039 (2)	−0.002 (2)	0.0009 (18)	−0.007 (2)
C9	0.059 (3)	0.049 (2)	0.036 (2)	−0.006 (2)	0.007 (2)	−0.0012 (19)
C10	0.074 (3)	0.074 (3)	0.044 (3)	0.025 (3)	0.009 (2)	−0.002 (2)
C21	0.045 (2)	0.037 (2)	0.033 (2)	0.000 (2)	−0.0034 (19)	−0.0061 (18)
C22	0.050 (3)	0.070 (3)	0.038 (2)	−0.001 (2)	0.000 (2)	0.003 (2)
C23	0.053 (3)	0.064 (3)	0.052 (3)	−0.006 (2)	0.005 (2)	−0.001 (2)
C24	0.046 (3)	0.068 (3)	0.071 (3)	−0.004 (3)	−0.007 (2)	−0.002 (3)
C25	0.066 (3)	0.083 (3)	0.068 (3)	−0.002 (3)	−0.025 (3)	0.015 (3)
C26	0.060 (3)	0.065 (3)	0.052 (3)	−0.011 (2)	−0.005 (2)	0.015 (2)
C71	0.041 (2)	0.046 (2)	0.042 (2)	−0.007 (2)	−0.0045 (19)	0.002 (2)
C72	0.069 (3)	0.062 (3)	0.041 (3)	−0.009 (2)	−0.001 (2)	0.007 (2)
C73	0.085 (4)	0.090 (4)	0.048 (3)	−0.012 (3)	−0.003 (3)	0.017 (3)
C74	0.072 (4)	0.082 (4)	0.080 (4)	−0.012 (3)	−0.011 (3)	0.040 (3)
C75	0.060 (3)	0.059 (3)	0.084 (4)	0.001 (3)	−0.005 (3)	0.016 (3)
C76	0.050 (3)	0.056 (3)	0.050 (3)	−0.007 (2)	0.001 (2)	0.006 (2)
C81	0.051 (3)	0.056 (3)	0.029 (2)	−0.004 (2)	0.0061 (19)	−0.005 (2)
C82	0.055 (3)	0.063 (3)	0.050 (3)	−0.002 (3)	0.009 (2)	0.005 (2)
C83	0.087 (4)	0.060 (3)	0.056 (3)	−0.003 (3)	0.005 (3)	0.006 (3)
C84	0.095 (4)	0.071 (3)	0.055 (3)	−0.034 (4)	0.010 (3)	−0.002 (3)
C85	0.058 (3)	0.104 (4)	0.066 (3)	−0.024 (3)	0.002 (3)	−0.005 (3)
C86	0.049 (3)	0.071 (3)	0.051 (3)	−0.004 (3)	0.003 (2)	0.001 (2)
C91	0.051 (3)	0.061 (3)	0.037 (2)	0.008 (2)	0.002 (2)	−0.005 (2)
C92	0.084 (4)	0.068 (3)	0.061 (3)	0.006 (3)	−0.009 (3)	−0.024 (3)
C93	0.105 (5)	0.125 (5)	0.068 (4)	0.033 (5)	−0.027 (4)	−0.047 (4)
C94	0.105 (5)	0.165 (7)	0.040 (3)	0.061 (5)	−0.010 (3)	−0.012 (4)
C95	0.086 (4)	0.122 (5)	0.050 (4)	0.025 (4)	0.010 (3)	0.024 (3)
C96	0.070 (3)	0.084 (3)	0.044 (3)	0.008 (3)	0.004 (2)	0.004 (3)
N1	0.0415 (19)	0.0506 (18)	0.0287 (18)	0.0008 (17)	−0.0027 (14)	−0.0007 (15)
N2	0.050 (2)	0.0451 (19)	0.0324 (18)	−0.0084 (16)	0.0004 (14)	0.0052 (16)
O1	0.0558 (18)	0.073 (2)	0.0693 (19)	0.0207 (17)	0.0077 (16)	−0.0070 (17)
O2	0.0513 (17)	0.0588 (17)	0.0346 (14)	−0.0115 (15)	−0.0023 (13)	0.0056 (14)

Geometric parameters (Å, º) top

C2—N1	1.468 (5)	C25—C26	1.382 (6)
C2—C3	1.515 (5)	C25—H25	0.93
C2—H2A	0.97	C26—H26	0.93
C2—H2B	0.97	C71—C76	1.379 (5)
C3—C4	1.495 (5)	C71—C72	1.388 (5)
C3—H3A	0.97	C72—C73	1.372 (6)
C3—H3B	0.97	C72—H72	0.93
C4—O1	1.208 (4)	C73—C74	1.363 (7)
C4—C5	1.530 (5)	C73—H73	0.93
C5—C6	1.534 (5)	C74—C75	1.379 (6)
C5—C8	1.552 (5)	C74—H74	0.93
C5—C7	1.572 (5)	C75—C76	1.376 (5)
C6—N1	1.465 (4)	C75—H75	0.93
C6—H6A	0.97	C76—H76	0.93
C6—H6B	0.97	C81—C82	1.378 (5)
C7—N2	1.485 (4)	C81—C86	1.380 (5)
C7—C71	1.502 (5)	C82—C83	1.374 (6)
C7—H7	0.98	C82—H82	0.93
C8—O2	1.428 (4)	C83—C84	1.364 (7)
C8—C81	1.503 (5)	C83—H83	0.93
C8—H8	0.98	C84—C85	1.375 (7)
C9—N1	1.488 (5)	C84—H84	0.93
C9—C91	1.512 (5)	C85—C86	1.388 (6)
C9—C10	1.516 (6)	C85—H85	0.93
C9—H9	0.98	C86—H86	0.93
C10—H10A	0.96	C91—C92	1.372 (5)
C10—H10B	0.96	C91—C96	1.381 (6)
C10—H10C	0.96	C92—C93	1.375 (6)
C21—C26	1.376 (5)	C92—H92	0.93
C21—C22	1.379 (5)	C93—C94	1.363 (8)
C21—N2	1.425 (4)	C93—H93	0.93
C22—C23	1.380 (6)	C94—C95	1.369 (8)
C22—H22	0.93	C94—H94	0.93
C23—C24	1.365 (5)	C95—C96	1.378 (6)
C23—H23	0.93	C95—H95	0.93
C24—C25	1.369 (6)	C96—H96	0.93
C24—H24	0.93	N2—O2	1.452 (4)

N1—C2—C3	110.5 (3)	C26—C25—H25	119.5
N1—C2—H2A	109.5	C21—C26—C25	120.4 (4)
C3—C2—H2A	109.5	C21—C26—H26	119.8
N1—C2—H2B	109.5	C25—C26—H26	119.8
C3—C2—H2B	109.5	C76—C71—C72	118.4 (4)
H2A—C2—H2B	108.1	C76—C71—C7	122.1 (3)
C4—C3—C2	114.8 (3)	C72—C71—C7	119.4 (4)
C4—C3—H3A	108.6	C73—C72—C71	120.5 (4)
C2—C3—H3A	108.6	C73—C72—H72	119.8
C4—C3—H3B	108.6	C71—C72—H72	119.8
C2—C3—H3B	108.6	C74—C73—C72	120.9 (4)
H3A—C3—H3B	107.5	C74—C73—H73	119.5
O1—C4—C3	121.5 (4)	C72—C73—H73	119.5
O1—C4—C5	121.7 (4)	C73—C74—C75	119.0 (4)
C3—C4—C5	116.7 (3)	C73—C74—H74	120.5
C4—C5—C6	108.7 (3)	C75—C74—H74	120.5
C4—C5—C8	110.8 (3)	C76—C75—C74	120.6 (5)
C6—C5—C8	112.7 (3)	C76—C75—H75	119.7
C4—C5—C7	113.9 (3)	C74—C75—H75	119.7
C6—C5—C7	108.9 (3)	C75—C76—C71	120.5 (4)
C8—C5—C7	101.9 (3)	C75—C76—H76	119.8
N1—C6—C5	110.4 (3)	C71—C76—H76	119.8
N1—C6—H6A	109.6	C82—C81—C86	118.4 (4)
C5—C6—H6A	109.6	C82—C81—C8	122.2 (4)
N1—C6—H6B	109.6	C86—C81—C8	119.3 (4)
C5—C6—H6B	109.6	C83—C82—C81	120.8 (4)
H6A—C6—H6B	108.1	C83—C82—H82	119.6
N2—C7—C71	112.1 (3)	C81—C82—H82	119.6
N2—C7—C5	103.5 (3)	C84—C83—C82	120.6 (5)
C71—C7—C5	115.7 (3)	C84—C83—H83	119.7
N2—C7—H7	108.4	C82—C83—H83	119.7
C71—C7—H7	108.4	C83—C84—C85	119.7 (5)
C5—C7—H7	108.4	C83—C84—H84	120.1
O2—C8—C81	109.4 (3)	C85—C84—H84	120.1
O2—C8—C5	103.9 (3)	C84—C85—C86	119.7 (5)
C81—C8—C5	116.1 (3)	C84—C85—H85	120.2
O2—C8—H8	109.0	C86—C85—H85	120.2
C81—C8—H8	109.0	C81—C86—C85	120.7 (5)
C5—C8—H8	109.0	C81—C86—H86	119.6
N1—C9—C91	112.0 (3)	C85—C86—H86	119.6
N1—C9—C10	110.8 (3)	C92—C91—C96	117.7 (4)
C91—C9—C10	109.2 (3)	C92—C91—C9	120.0 (4)
N1—C9—H9	108.3	C96—C91—C9	122.2 (4)
C91—C9—H9	108.3	C91—C92—C93	121.0 (5)
C10—C9—H9	108.3	C91—C92—H92	119.5
C9—C10—H10A	109.5	C93—C92—H92	119.5
C9—C10—H10B	109.5	C94—C93—C92	120.6 (6)
H10A—C10—H10B	109.5	C94—C93—H93	119.7
C9—C10—H10C	109.5	C92—C93—H93	119.7
H10A—C10—H10C	109.5	C93—C94—C95	119.6 (5)
H10B—C10—H10C	109.5	C93—C94—H94	120.2
C26—C21—C22	117.9 (4)	C95—C94—H94	120.2
C26—C21—N2	121.3 (4)	C94—C95—C96	119.6 (6)
C22—C21—N2	120.6 (3)	C94—C95—H95	120.2
C21—C22—C23	121.5 (4)	C96—C95—H95	120.2
C21—C22—H22	119.2	C95—C96—C91	121.5 (5)
C23—C22—H22	119.2	C95—C96—H96	119.3
C24—C23—C22	120.0 (4)	C91—C96—H96	119.3
C24—C23—H23	120.0	C6—N1—C2	106.3 (3)
C22—C23—H23	120.0	C6—N1—C9	111.2 (3)
C23—C24—C25	119.2 (4)	C2—N1—C9	111.8 (3)
C23—C24—H24	120.4	C21—N2—O2	107.2 (3)
C25—C24—H24	120.4	C21—N2—C7	117.1 (3)
C24—C25—C26	121.0 (4)	O2—N2—C7	104.3 (2)
C24—C25—H25	119.5	C8—O2—N2	102.2 (3)

N1—C2—C3—C4	−47.1 (5)	O2—C8—C81—C82	−21.0 (5)
C2—C3—C4—O1	−145.8 (4)	C5—C8—C81—C82	96.2 (4)
C2—C3—C4—C5	34.6 (5)	O2—C8—C81—C86	161.1 (3)
O1—C4—C5—C6	142.2 (3)	C5—C8—C81—C86	−81.7 (5)
C3—C4—C5—C6	−38.3 (4)	C86—C81—C82—C83	0.5 (6)
O1—C4—C5—C8	17.9 (5)	C8—C81—C82—C83	−177.4 (4)
C3—C4—C5—C8	−162.6 (3)	C81—C82—C83—C84	−0.4 (7)
O1—C4—C5—C7	−96.3 (4)	C82—C83—C84—C85	0.3 (7)
C3—C4—C5—C7	83.3 (4)	C83—C84—C85—C86	−0.4 (7)
C4—C5—C6—N1	57.2 (4)	C82—C81—C86—C85	−0.6 (6)
C8—C5—C6—N1	−179.7 (3)	C8—C81—C86—C85	177.4 (3)
C7—C5—C6—N1	−67.4 (4)	C84—C85—C86—C81	0.5 (7)
C4—C5—C7—N2	116.1 (3)	N1—C9—C91—C92	−139.4 (4)
C6—C5—C7—N2	−122.4 (3)	C10—C9—C91—C92	97.5 (5)
C8—C5—C7—N2	−3.2 (3)	N1—C9—C91—C96	44.8 (5)
C4—C5—C7—C71	−6.9 (4)	C10—C9—C91—C96	−78.4 (5)
C6—C5—C7—C71	114.5 (3)	C96—C91—C92—C93	0.2 (7)
C8—C5—C7—C71	−126.3 (3)	C9—C91—C92—C93	−175.9 (4)
C4—C5—C8—O2	−147.5 (3)	C91—C92—C93—C94	−0.9 (9)
C6—C5—C8—O2	90.5 (4)	C92—C93—C94—C95	−0.4 (9)
C7—C5—C8—O2	−26.0 (4)	C93—C94—C95—C96	2.3 (9)
C4—C5—C8—C81	92.2 (4)	C94—C95—C96—C91	−3.1 (8)
C6—C5—C8—C81	−29.7 (5)	C92—C91—C96—C95	1.8 (7)
C7—C5—C8—C81	−146.2 (3)	C9—C91—C96—C95	177.8 (4)
C26—C21—C22—C23	0.2 (6)	C5—C6—N1—C2	−71.9 (4)
N2—C21—C22—C23	176.7 (4)	C5—C6—N1—C9	166.2 (3)
C21—C22—C23—C24	0.9 (6)	C3—C2—N1—C6	64.9 (4)
C22—C23—C24—C25	−1.0 (6)	C3—C2—N1—C9	−173.7 (3)
C23—C24—C25—C26	0.1 (7)	C91—C9—N1—C6	170.6 (3)
C22—C21—C26—C25	−1.1 (6)	C10—C9—N1—C6	−67.2 (4)
N2—C21—C26—C25	−177.6 (4)	C91—C9—N1—C2	52.0 (4)
C24—C25—C26—C21	1.0 (7)	C10—C9—N1—C2	174.1 (3)
N2—C7—C71—C76	−40.4 (5)	C26—C21—N2—O2	−21.8 (4)
C5—C7—C71—C76	78.0 (4)	C22—C21—N2—O2	161.8 (3)
N2—C7—C71—C72	143.3 (4)	C26—C21—N2—C7	−138.4 (3)
C5—C7—C71—C72	−98.4 (4)	C22—C21—N2—C7	45.2 (5)
C76—C71—C72—C73	−2.7 (6)	C71—C7—N2—C21	−85.5 (4)
C7—C71—C72—C73	173.8 (4)	C5—C7—N2—C21	149.1 (3)
C71—C72—C73—C74	1.6 (7)	C71—C7—N2—O2	156.3 (3)
C72—C73—C74—C75	1.0 (8)	C5—C7—N2—O2	31.0 (3)
C73—C74—C75—C76	−2.5 (7)	C81—C8—O2—N2	170.9 (3)
C74—C75—C76—C71	1.4 (7)	C5—C8—O2—N2	46.2 (3)
C72—C71—C76—C75	1.2 (6)	C21—N2—O2—C8	−173.9 (3)
C7—C71—C76—C75	−175.2 (4)	C7—N2—O2—C8	−49.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.98	2.35	2.775 (5)	106
C26—H26···O2	0.93	2.29	2.623 (5)	101
C82—H82···O2	0.93	2.43	2.757 (5)	101
C3—H3A···Cg1	0.97	2.90	3.659 (5)	136
C2—H2A···Cg2ⁱ	0.97	2.93	3.707 (5)	138
C74—H74···Cg3ⁱⁱ	0.93	2.96	3.722 (6)	141

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

Experimental details

Crystal data
Chemical formula	C₃₃H₃₂N₂O₂
M_r	488.61
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	273
a, b, c (Å)	10.589 (5), 14.582 (7), 17.443 (8)
V (Å³)	2693 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.16 × 0.12

Data collection
Diffractometer	Nonius MACH-3
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.986, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	13617, 2701, 1899
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.118, 1.09
No. of reflections	2701
No. of parameters	335
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.14

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.98	2.35	2.775 (5)	106
C26—H26···O2	0.93	2.29	2.623 (5)	101
C82—H82···O2	0.93	2.43	2.757 (5)	101
C3—H3A···Cg1	0.97	2.90	3.659 (5)	136
C2—H2A···Cg2ⁱ	0.97	2.93	3.707 (5)	138
C74—H74···Cg3ⁱⁱ	0.93	2.96	3.722 (6)	141

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

Acknowledgements

SP thanks the CSIR, New Delhi, for a Major Research Project.

References

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

(1R,4R,5R)-1,3,4-Tri­phenyl-7-[(R)-1-phenyl­ethyl]-2-oxa-3,7-di­aza­spiro­[4.5]decan-10-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(1R,4R,5R)-1,3,4-Triphenyl-7-[(R)-1-phenylethyl]-2-oxa-3,7-diazaspiro[4.5]decan-10-one