(3R*,4R*,5S*)-4-(4-Methyl­phen­yl)-2,3-diphenyl-7-[(R*)-1-phenyl­ethyl]-1-oxa-2,7-diaza­spiro­[4.5]decan-10-one oxime

Begum, G.C.; Kumar, R.S.; Suresh, J.; Gopinathan, C.; Lakshman, P.L.N.

doi:10.1107/S1600536808004121

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o590

doi:10.1107/S1600536808004121

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

G. Chanthini Begum,^a R. Suresh Kumar,^b J. Suresh,^a C. Gopinathan ^a and P. L. Nilantha Lakshman ^c ^*

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

(Received 31 January 2008; accepted 9 February 2008; online 15 February 2008)

In the title compound, C₃₄H₃₅N₃O₂, the polysubstituted piperidine ring adopts a chair conformation and the isoxazolidine ring is in an envelope form. The molecules are linked into a chain along the b axis by O—H⋯N, C—H⋯O and C—H⋯N interactions. The chains are cross-linked via weak C—H⋯π interactions.

Related literature

For related literature, see: Ali et al. (1988 ); Annuziata et al. (1987 ); Colombi et al. (1978 ); Gothelf & Jorgensen (2000 ); Goti et al. (1997 ); Hossain et al. (1993 ); Kumar et al. (2003 ).

Experimental

Crystal data

C₃₄H₃₅N₃O₂
M_r = 517.65
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.448 (7) Å
b = 10.588 (9) Å
c = 26.490 (16) Å
V = 2930 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 (2) K
0.18 × 0.16 × 0.11 mm

Data collection

Nonius MACH-3 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.986, T_max = 0.991
3068 measured reflections
2933 independent reflections
1037 reflections with I > 2σ(I)
R_int = 0.049
2 standard reflections frequency: 60 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.119
S = 0.95
2933 reflections
355 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C31–C36 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.82	1.98	2.791 (6)	170
C3—H3B⋯N2ⁱⁱ	0.97	2.61	3.353 (8)	133
C96—H96⋯O1ⁱⁱ	0.93	2.60	3.456 (9)	154
C94—H94⋯Cg1ⁱⁱⁱ	0.93	2.80	3.721 (11)	170
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x+1, y, z.

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, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808004121/ci2561sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808004121/ci2561Isup2.hkl

checkCIF report

Comment top

1,3-dipolar cycloaddition of nitrones with olefinic dipolarophiles proceeds through a concerted mechanism yielding highly substituted isoxazolidines with generation of as many as three new contiguous stereogenic centers in a single step (Gothelf & Jorgensen, 2000). Isoxazolidines are potential precursors for biologically important compounds such as amino sugars, alkaloids (Goti et al., 1997; Ali et al., 1988), β-lactams (Ali et al., 1988), and amino acids (Annuziata et al., 1987), and exhibit antibacterial and antifungal activities (Kumar et al., 2003). Among the dipoles, nitrones have been extensively used as they readily undergo both inter- and intra-molecular 1,3-dipolar cycloaddition with olefins. 1,3-dipolar cycloaddition of exocyclic olefins with nitrones result in highly substituted spiro-isoxazolidines (Hossain et al., 1993) and they have also been transformed into complex heterocycles (Colombi et al., 1978).

The molecular structure of the title compound is shown in Fig.1. The isoxazolidine ring has an envelope conformation, as indicated by the puckering parameters Q = 0.492 (6) Å and ϕ = 34.1 (7)°. The piperidine ring adopts a chair conformation. The C31—C36, C81—C86 and C71—C76 phenyl rings form dihedral angles of 37.5 (3)°, 77.5 (3)° and 71.8 (2)°, respectively, with the O2/C5/C7/C8 plane. The C31—C36 and C71—C76 phenyl rings are oriented at angles of 74.1 (3)° and 70.9 (3)°, respectively, with respect to the C81—C86 phenyl ring. The C2—N1—C9—C91 and C6—N1—C9—C10 torsion angles are 175.9 (6) and 178.4 (5)°, respectively.

Intermolecular O—H···N and weak C—H···O and C—H···N interactions form a linear chain running parallel to the b axis (Table 1). The chains are cross-linked via weak C—H···π interactions involving the C31—C36 phenyl ring (centroid Cg1).

Related literature top

For related literature, see: Ali et al. (1988); Annuziata et al. (1987); Colombi et al. (1978); Gothelf & Jorgensen (2000); Goti et al. (1997); Hossain et al. (1993); Kumar et al. (2003).

Experimental top

4-(4-Methylphenyl)-2,3-diphenyl-7-[(R)-1-phenylethyl]-1-oxa-2,7-diazaspiro[4.5] decan-10-one (0.05 g, 0.01 mmol), hydroxylammonium chloride (0.010 g, 0.015 mmol) and sodium acetate (0.012 g, 0.015 mmol) in ethanol (3 ml) was refluxed for 30 min. After completion of the reaction, as evident from TLC the excess solvent was evaporated in vacuo and the residue was subjected to flash column chromatography on silica gel using petroleum ether-ethyl acetate (10:2) as eluent. The product was recrystallized from ethanol (yield 72%, m.p 418 K)

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, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

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

(3R*,4R*,5S*)-4-(4-Methylphenyl)-2,3-diphenyl-7- [(R*)-1-phenylethyl]-1-oxa-2,7-diazaspiro[4.5]decan-10-one oxime top

Crystal data top

C₃₄H₃₅N₃O₂	F(000) = 1104
M_r = 517.65	D_x = 1.173 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 10.448 (7) Å	θ = 2–25°
b = 10.588 (9) Å	µ = 0.07 mm⁻¹
c = 26.490 (16) Å	T = 293 K
V = 2930 (4) Å³	Block, colourless
Z = 4	0.18 × 0.16 × 0.11 mm

Data collection top

Nonius MACH-3 diffractometer	1037 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.049
Graphite monochromator	θ_max = 25.0°, θ_min = 2.1°
ω–2θ scans	h = 0→12
Absorption correction: ψ scan (North et al., 1968)	k = 0→12
T_min = 0.986, T_max = 0.991	l = −1→31
3068 measured reflections	2 standard reflections every 60 min
2933 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0339P)²] where P = (F_o² + 2F_c²)/3
2933 reflections	(Δ/σ)_max = 0.001
355 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₃₄H₃₅N₃O₂	V = 2930 (4) Å³
M_r = 517.65	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.448 (7) Å	µ = 0.07 mm⁻¹
b = 10.588 (9) Å	T = 293 K
c = 26.490 (16) Å	0.18 × 0.16 × 0.11 mm

Data collection top

Nonius MACH-3 diffractometer	1037 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.049
T_min = 0.986, T_max = 0.991	2 standard reflections every 60 min
3068 measured reflections	intensity decay: none
2933 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 0.96	Δρ_max = 0.15 e Å⁻³
2933 reflections	Δρ_min = −0.17 e Å⁻³
355 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	0.1491 (7)	0.2999 (7)	0.2896 (2)	0.057 (2)
H2A	0.1502	0.3589	0.3176	0.068*
H2B	0.1778	0.2185	0.3020	0.068*
C3	0.0135 (7)	0.2879 (6)	0.2695 (2)	0.061 (2)
H3A	−0.0421	0.2557	0.2959	0.073*
H3B	−0.0178	0.3704	0.2594	0.073*
C4	0.0111 (6)	0.2011 (7)	0.2257 (2)	0.0428 (19)
C5	0.1068 (6)	0.2330 (6)	0.1843 (2)	0.0440 (19)
C6	0.2378 (6)	0.2497 (7)	0.2084 (2)	0.0495 (19)
H6A	0.2663	0.1691	0.2218	0.059*
H6B	0.2985	0.2757	0.1827	0.059*
C7	0.1025 (6)	0.1445 (6)	0.1374 (2)	0.0453 (19)
H7	0.0322	0.0849	0.1430	0.054*
C8	0.0593 (6)	0.2344 (6)	0.0951 (2)	0.0459 (19)
H8	0.1348	0.2757	0.0806	0.055*
C9	0.3678 (7)	0.3610 (7)	0.2705 (3)	0.059 (2)
H9	0.3949	0.2804	0.2852	0.070*
C10	0.3704 (8)	0.4613 (7)	0.3123 (2)	0.092 (3)
H10A	0.3400	0.5402	0.2990	0.138*
H10B	0.4564	0.4714	0.3243	0.138*
H10C	0.3163	0.4350	0.3396	0.138*
C31	−0.0448 (7)	0.4453 (7)	0.0987 (3)	0.049 (2)
C32	−0.1389 (8)	0.4467 (8)	0.0614 (3)	0.069 (2)
H32	−0.1766	0.3712	0.0515	0.083*
C33	−0.1768 (8)	0.5572 (10)	0.0391 (3)	0.081 (3)
H33	−0.2395	0.5554	0.0142	0.098*
C34	−0.1238 (10)	0.6699 (8)	0.0530 (3)	0.078 (3)
H34	−0.1507	0.7451	0.0383	0.094*
C35	−0.0303 (9)	0.6693 (8)	0.0890 (3)	0.084 (3)
H35	0.0081	0.7452	0.0980	0.101*
C36	0.0098 (8)	0.5574 (8)	0.1127 (3)	0.065 (2)
H36	0.0726	0.5595	0.1376	0.078*
C71	0.2166 (7)	0.0680 (7)	0.1229 (2)	0.047 (2)
C72	0.3230 (7)	0.1135 (7)	0.0978 (3)	0.057 (2)
H72	0.3307	0.1998	0.0921	0.068*
C73	0.4189 (8)	0.0327 (7)	0.0807 (3)	0.065 (2)
H73	0.4884	0.0662	0.0633	0.078*
C74	0.4133 (9)	−0.0953 (8)	0.0889 (3)	0.065 (2)
C75	0.3100 (9)	−0.1418 (8)	0.1145 (3)	0.081 (3)
H75	0.3036	−0.2281	0.1207	0.098*
C76	0.2152 (8)	−0.0616 (8)	0.1312 (3)	0.067 (2)
H76	0.1467	−0.0960	0.1489	0.081*
C77	0.5171 (7)	−0.1818 (8)	0.0674 (3)	0.093 (3)
H77A	0.5320	−0.1608	0.0327	0.139*
H77B	0.4897	−0.2681	0.0699	0.139*
H77C	0.5948	−0.1707	0.0863	0.139*
C81	−0.0138 (8)	0.1710 (7)	0.0537 (3)	0.057 (2)
C82	0.0338 (8)	0.1661 (7)	0.0054 (3)	0.079 (3)
H82	0.1112	0.2050	−0.0022	0.094*
C83	−0.0344 (13)	0.1023 (11)	−0.0326 (4)	0.116 (5)
H83	−0.0023	0.0992	−0.0654	0.139*
C84	−0.1453 (13)	0.0462 (13)	−0.0216 (6)	0.136 (6)
H84	−0.1877	0.0016	−0.0468	0.163*
C85	−0.1984 (11)	0.0517 (11)	0.0251 (5)	0.120 (4)
H85	−0.2780	0.0161	0.0316	0.144*
C86	−0.1287 (10)	0.1135 (8)	0.0636 (3)	0.088 (3)
H86	−0.1613	0.1151	0.0962	0.105*
C91	0.4635 (7)	0.3974 (8)	0.2304 (3)	0.056 (2)
C92	0.5805 (9)	0.3409 (10)	0.2280 (4)	0.105 (4)
H92	0.5980	0.2731	0.2492	0.126*
C93	0.6745 (11)	0.3822 (11)	0.1947 (5)	0.125 (5)
H93	0.7541	0.3430	0.1938	0.150*
C94	0.6480 (11)	0.4818 (11)	0.1631 (4)	0.107 (4)
H94	0.7107	0.5117	0.1412	0.128*
C95	0.5312 (9)	0.5363 (8)	0.1637 (3)	0.081 (3)
H95	0.5127	0.6016	0.1415	0.097*
C96	0.4391 (7)	0.4953 (8)	0.1974 (3)	0.067 (2)
H96	0.3594	0.5343	0.1978	0.081*
N1	0.2373 (5)	0.3445 (5)	0.2497 (2)	0.0447 (15)
N2	−0.0569 (5)	0.1010 (5)	0.2211 (2)	0.0442 (15)
N3	−0.0164 (5)	0.3297 (5)	0.12360 (19)	0.0462 (15)
O1	−0.1378 (5)	0.0870 (4)	0.26317 (17)	0.0568 (14)
H1	−0.1726	0.0177	0.2621	0.085*
O2	0.0736 (4)	0.3573 (4)	0.16451 (15)	0.0469 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.077 (6)	0.051 (5)	0.042 (4)	−0.012 (5)	0.010 (5)	−0.003 (4)
C3	0.074 (6)	0.051 (5)	0.057 (5)	−0.007 (5)	0.021 (5)	−0.007 (4)
C4	0.041 (5)	0.046 (4)	0.041 (4)	0.004 (4)	0.013 (4)	−0.001 (4)
C5	0.049 (5)	0.042 (5)	0.041 (4)	−0.001 (4)	0.002 (4)	−0.001 (4)
C6	0.058 (5)	0.049 (4)	0.042 (4)	0.000 (4)	0.002 (4)	0.004 (4)
C7	0.058 (5)	0.038 (4)	0.040 (4)	−0.008 (4)	0.007 (4)	−0.003 (4)
C8	0.042 (5)	0.053 (5)	0.043 (4)	0.000 (4)	0.007 (4)	−0.011 (4)
C9	0.056 (6)	0.066 (6)	0.053 (5)	0.005 (5)	−0.013 (5)	0.009 (5)
C10	0.106 (7)	0.120 (7)	0.050 (5)	−0.019 (6)	−0.019 (5)	−0.026 (6)
C31	0.050 (5)	0.049 (5)	0.047 (5)	0.000 (5)	0.012 (4)	−0.011 (5)
C32	0.055 (6)	0.073 (7)	0.080 (6)	0.004 (5)	−0.003 (5)	0.002 (6)
C33	0.085 (7)	0.093 (7)	0.066 (6)	0.027 (7)	−0.008 (5)	0.014 (7)
C34	0.116 (9)	0.058 (7)	0.061 (6)	0.011 (6)	0.012 (6)	−0.001 (5)
C35	0.114 (8)	0.071 (7)	0.068 (6)	−0.005 (6)	−0.020 (6)	0.006 (5)
C36	0.087 (7)	0.053 (5)	0.057 (5)	0.004 (6)	−0.012 (5)	0.011 (5)
C71	0.064 (6)	0.031 (5)	0.047 (5)	−0.004 (5)	0.011 (4)	−0.003 (4)
C72	0.061 (5)	0.051 (5)	0.058 (5)	0.005 (5)	0.008 (5)	0.006 (5)
C73	0.063 (6)	0.068 (6)	0.065 (5)	0.010 (5)	0.015 (5)	0.014 (5)
C74	0.081 (7)	0.064 (6)	0.050 (5)	0.031 (6)	−0.002 (5)	−0.006 (5)
C75	0.107 (8)	0.049 (5)	0.087 (7)	0.016 (6)	0.019 (6)	0.002 (5)
C76	0.078 (6)	0.065 (6)	0.059 (6)	−0.004 (6)	0.012 (5)	0.005 (5)
C77	0.100 (7)	0.090 (7)	0.088 (6)	0.042 (6)	0.008 (6)	−0.017 (5)
C81	0.057 (6)	0.061 (5)	0.052 (5)	0.012 (5)	−0.002 (5)	−0.011 (5)
C82	0.086 (6)	0.089 (6)	0.060 (5)	0.029 (6)	−0.011 (5)	−0.021 (5)
C83	0.174 (13)	0.117 (11)	0.056 (6)	0.065 (10)	−0.037 (8)	−0.044 (7)
C84	0.132 (14)	0.090 (10)	0.187 (15)	0.019 (10)	−0.070 (13)	−0.049 (11)
C85	0.089 (9)	0.085 (8)	0.186 (13)	0.013 (7)	−0.012 (10)	−0.017 (10)
C86	0.094 (8)	0.076 (7)	0.093 (8)	−0.010 (6)	−0.033 (7)	−0.028 (6)
C91	0.037 (5)	0.066 (6)	0.064 (5)	0.013 (5)	−0.011 (4)	−0.025 (5)
C92	0.062 (7)	0.110 (8)	0.144 (10)	0.024 (7)	−0.005 (7)	−0.021 (8)
C93	0.056 (7)	0.138 (12)	0.181 (14)	0.028 (9)	0.000 (8)	−0.036 (10)
C94	0.064 (8)	0.135 (11)	0.122 (10)	−0.025 (8)	0.048 (7)	−0.063 (8)
C95	0.083 (7)	0.090 (7)	0.070 (5)	−0.012 (7)	0.021 (6)	−0.016 (5)
C96	0.048 (5)	0.073 (6)	0.082 (6)	0.001 (5)	0.017 (5)	0.003 (5)
N1	0.044 (4)	0.043 (3)	0.047 (3)	−0.001 (3)	−0.004 (3)	−0.004 (3)
N2	0.044 (4)	0.042 (3)	0.046 (4)	0.000 (3)	0.011 (3)	−0.002 (3)
N3	0.052 (4)	0.042 (4)	0.044 (3)	−0.003 (3)	0.000 (3)	0.005 (3)
O1	0.062 (4)	0.053 (4)	0.056 (3)	−0.015 (3)	0.024 (3)	−0.001 (3)
O2	0.052 (3)	0.047 (3)	0.042 (3)	−0.001 (3)	0.001 (3)	0.002 (3)

Geometric parameters (Å, º) top

C2—N1	1.480 (7)	C71—C72	1.383 (8)
C2—C3	1.518 (8)	C71—C76	1.390 (8)
C2—H2A	0.97	C72—C73	1.393 (9)
C2—H2B	0.97	C72—H72	0.93
C3—C4	1.482 (8)	C73—C74	1.374 (9)
C3—H3A	0.97	C73—H73	0.93
C3—H3B	0.97	C74—C75	1.367 (10)
C4—N2	1.282 (7)	C74—C77	1.529 (9)
C4—C5	1.520 (8)	C75—C76	1.377 (10)
C5—O2	1.460 (7)	C75—H75	0.93
C5—C6	1.521 (8)	C76—H76	0.93
C5—C7	1.557 (8)	C77—H77A	0.96
C6—N1	1.485 (7)	C77—H77B	0.96
C6—H6A	0.97	C77—H77C	0.96
C6—H6B	0.97	C81—C86	1.371 (10)
C7—C71	1.491 (8)	C81—C82	1.374 (8)
C7—C8	1.537 (8)	C82—C83	1.406 (11)
C7—H7	0.98	C82—H82	0.93
C8—N3	1.487 (7)	C83—C84	1.335 (14)
C8—C81	1.496 (9)	C83—H83	0.93
C8—H8	0.98	C84—C85	1.358 (15)
C9—N1	1.481 (7)	C84—H84	0.93
C9—C91	1.508 (9)	C85—C86	1.412 (12)
C9—C10	1.534 (8)	C85—H85	0.93
C9—H9	0.98	C86—H86	0.93
C10—H10A	0.96	C91—C92	1.362 (10)
C10—H10B	0.96	C91—C96	1.379 (9)
C10—H10C	0.96	C92—C93	1.391 (13)
C31—C36	1.368 (8)	C92—H92	0.93
C31—C32	1.393 (9)	C93—C94	1.374 (13)
C31—N3	1.422 (8)	C93—H93	0.93
C32—C33	1.369 (10)	C94—C95	1.350 (11)
C32—H32	0.93	C94—H94	0.93
C33—C34	1.366 (10)	C95—C96	1.382 (9)
C33—H33	0.93	C95—H95	0.93
C34—C35	1.365 (10)	C96—H96	0.93
C34—H34	0.93	N2—O1	1.406 (6)
C35—C36	1.405 (10)	N3—O2	1.464 (6)
C35—H35	0.93	O1—H1	0.82
C36—H36	0.93

N1—C2—C3	111.0 (5)	C72—C71—C76	115.4 (7)
N1—C2—H2A	109.4	C72—C71—C7	125.2 (6)
C3—C2—H2A	109.4	C76—C71—C7	119.2 (7)
N1—C2—H2B	109.4	C71—C72—C73	121.4 (7)
C3—C2—H2B	109.4	C71—C72—H72	119.3
H2A—C2—H2B	108.0	C73—C72—H72	119.3
C4—C3—C2	110.0 (6)	C74—C73—C72	121.6 (8)
C4—C3—H3A	109.7	C74—C73—H73	119.2
C2—C3—H3A	109.7	C72—C73—H73	119.2
C4—C3—H3B	109.7	C75—C74—C73	117.9 (8)
C2—C3—H3B	109.7	C75—C74—C77	121.9 (8)
H3A—C3—H3B	108.2	C73—C74—C77	120.1 (9)
N2—C4—C3	126.6 (6)	C74—C75—C76	120.3 (8)
N2—C4—C5	118.7 (6)	C74—C75—H75	119.8
C3—C4—C5	114.6 (6)	C76—C75—H75	119.8
O2—C5—C4	107.6 (5)	C75—C76—C71	123.4 (8)
O2—C5—C6	105.1 (5)	C75—C76—H76	118.3
C4—C5—C6	108.4 (6)	C71—C76—H76	118.3
O2—C5—C7	104.4 (5)	C74—C77—H77A	109.5
C4—C5—C7	115.0 (5)	C74—C77—H77B	109.5
C6—C5—C7	115.5 (6)	H77A—C77—H77B	109.5
N1—C6—C5	112.6 (5)	C74—C77—H77C	109.5
N1—C6—H6A	109.1	H77A—C77—H77C	109.5
C5—C6—H6A	109.1	H77B—C77—H77C	109.5
N1—C6—H6B	109.1	C86—C81—C82	118.5 (8)
C5—C6—H6B	109.1	C86—C81—C8	120.5 (7)
H6A—C6—H6B	107.8	C82—C81—C8	121.0 (8)
C71—C7—C8	112.6 (5)	C81—C82—C83	120.1 (9)
C71—C7—C5	120.6 (6)	C81—C82—H82	119.9
C8—C7—C5	102.6 (5)	C83—C82—H82	119.9
C71—C7—H7	106.7	C84—C83—C82	119.8 (12)
C8—C7—H7	106.7	C84—C83—H83	120.1
C5—C7—H7	106.7	C82—C83—H83	120.1
N3—C8—C81	113.9 (6)	C83—C84—C85	122.4 (15)
N3—C8—C7	101.9 (5)	C83—C84—H84	118.8
C81—C8—C7	114.0 (5)	C85—C84—H84	118.8
N3—C8—H8	108.9	C84—C85—C86	117.8 (13)
C81—C8—H8	108.9	C84—C85—H85	121.1
C7—C8—H8	108.9	C86—C85—H85	121.1
N1—C9—C91	112.2 (6)	C81—C86—C85	121.3 (10)
N1—C9—C10	111.5 (6)	C81—C86—H86	119.3
C91—C9—C10	108.6 (6)	C85—C86—H86	119.3
N1—C9—H9	108.1	C92—C91—C96	117.8 (9)
C91—C9—H9	108.1	C92—C91—C9	121.1 (9)
C10—C9—H9	108.1	C96—C91—C9	121.0 (7)
C9—C10—H10A	109.5	C91—C92—C93	121.7 (11)
C9—C10—H10B	109.5	C91—C92—H92	119.1
H10A—C10—H10B	109.5	C93—C92—H92	119.1
C9—C10—H10C	109.5	C94—C93—C92	119.0 (12)
H10A—C10—H10C	109.5	C94—C93—H93	120.5
H10B—C10—H10C	109.5	C92—C93—H93	120.5
C36—C31—C32	118.5 (7)	C95—C94—C93	120.1 (12)
C36—C31—N3	122.3 (7)	C95—C94—H94	119.9
C32—C31—N3	119.1 (7)	C93—C94—H94	119.9
C33—C32—C31	121.3 (8)	C94—C95—C96	120.3 (9)
C33—C32—H32	119.4	C94—C95—H95	119.9
C31—C32—H32	119.4	C96—C95—H95	119.9
C34—C33—C32	120.9 (8)	C91—C96—C95	121.0 (8)
C34—C33—H33	119.5	C91—C96—H96	119.5
C32—C33—H33	119.5	C95—C96—H96	119.5
C35—C34—C33	118.3 (9)	C2—N1—C9	110.2 (5)
C35—C34—H34	120.9	C2—N1—C6	108.2 (5)
C33—C34—H34	120.9	C9—N1—C6	110.5 (5)
C34—C35—C36	122.0 (9)	C4—N2—O1	110.3 (5)
C34—C35—H35	119.0	C31—N3—O2	107.8 (5)
C36—C35—H35	119.0	C31—N3—C8	117.4 (5)
C31—C36—C35	119.1 (7)	O2—N3—C8	99.8 (5)
C31—C36—H36	120.5	N2—O1—H1	109.5
C35—C36—H36	120.5	C5—O2—N3	103.8 (4)

N1—C2—C3—C4	57.3 (8)	N3—C8—C81—C82	128.0 (7)
C2—C3—C4—N2	123.3 (8)	C7—C8—C81—C82	−115.7 (8)
C2—C3—C4—C5	−52.3 (7)	C86—C81—C82—C83	−0.5 (12)
N2—C4—C5—O2	121.4 (6)	C8—C81—C82—C83	177.8 (7)
C3—C4—C5—O2	−62.5 (7)	C81—C82—C83—C84	−0.2 (16)
N2—C4—C5—C6	−125.4 (6)	C82—C83—C84—C85	2 (2)
C3—C4—C5—C6	50.6 (8)	C83—C84—C85—C86	−4 (2)
N2—C4—C5—C7	5.6 (9)	C82—C81—C86—C85	−0.9 (13)
C3—C4—C5—C7	−178.4 (5)	C8—C81—C86—C85	−179.2 (8)
O2—C5—C6—N1	60.0 (6)	C84—C85—C86—C81	2.9 (16)
C4—C5—C6—N1	−54.9 (7)	N1—C9—C91—C92	−135.1 (7)
C7—C5—C6—N1	174.4 (5)	C10—C9—C91—C92	101.2 (9)
O2—C5—C7—C71	123.6 (6)	N1—C9—C91—C96	49.8 (9)
C4—C5—C7—C71	−118.7 (7)	C10—C9—C91—C96	−73.9 (8)
C6—C5—C7—C71	8.8 (9)	C96—C91—C92—C93	2.0 (13)
O2—C5—C7—C8	−2.5 (7)	C9—C91—C92—C93	−173.3 (9)
C4—C5—C7—C8	115.2 (6)	C91—C92—C93—C94	−0.6 (17)
C6—C5—C7—C8	−117.3 (6)	C92—C93—C94—C95	−1.6 (17)
C71—C7—C8—N3	−159.2 (5)	C93—C94—C95—C96	2.3 (15)
C5—C7—C8—N3	−28.1 (6)	C92—C91—C96—C95	−1.2 (11)
C71—C7—C8—C81	77.7 (7)	C9—C91—C96—C95	174.0 (7)
C5—C7—C8—C81	−151.2 (6)	C94—C95—C96—C91	−0.9 (12)
C36—C31—C32—C33	−0.2 (11)	C3—C2—N1—C9	177.5 (6)
N3—C31—C32—C33	174.9 (7)	C3—C2—N1—C6	−61.6 (7)
C31—C32—C33—C34	−0.3 (13)	C91—C9—N1—C2	175.9 (6)
C32—C33—C34—C35	1.2 (13)	C10—C9—N1—C2	−62.0 (7)
C33—C34—C35—C36	−1.7 (13)	C91—C9—N1—C6	56.3 (7)
C32—C31—C36—C35	−0.3 (11)	C10—C9—N1—C6	178.4 (5)
N3—C31—C36—C35	−175.1 (7)	C5—C6—N1—C2	61.5 (7)
C34—C35—C36—C31	1.2 (13)	C5—C6—N1—C9	−177.8 (6)
C8—C7—C71—C72	42.9 (9)	C3—C4—N2—O1	3.8 (9)
C5—C7—C71—C72	−78.4 (9)	C5—C4—N2—O1	179.3 (5)
C8—C7—C71—C76	−131.6 (7)	C36—C31—N3—O2	1.4 (8)
C5—C7—C71—C76	107.0 (8)	C32—C31—N3—O2	−173.4 (6)
C76—C71—C72—C73	2.1 (11)	C36—C31—N3—C8	−110.1 (7)
C7—C71—C72—C73	−172.6 (7)	C32—C31—N3—C8	75.0 (8)
C71—C72—C73—C74	−1.2 (12)	C81—C8—N3—C31	−72.3 (8)
C72—C73—C74—C75	0.1 (13)	C7—C8—N3—C31	164.5 (6)
C72—C73—C74—C77	177.1 (6)	C81—C8—N3—O2	171.7 (5)
C73—C74—C75—C76	0.1 (13)	C7—C8—N3—O2	48.5 (5)
C77—C74—C75—C76	−176.8 (7)	C4—C5—O2—N3	−89.7 (5)
C74—C75—C76—C71	0.9 (13)	C6—C5—O2—N3	154.9 (4)
C72—C71—C76—C75	−1.9 (12)	C7—C5—O2—N3	33.0 (6)
C7—C71—C76—C75	173.1 (7)	C31—N3—O2—C5	−174.5 (5)
N3—C8—C81—C86	−53.8 (9)	C8—N3—O2—C5	−51.4 (5)
C7—C8—C81—C86	62.6 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.82	1.98	2.791 (6)	170
C3—H3B···N2ⁱⁱ	0.97	2.61	3.353 (8)	133
C96—H96···O1ⁱⁱ	0.93	2.60	3.456 (9)	154
C94—H94···Cg1ⁱⁱⁱ	0.93	2.80	3.721 (11)	170

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

Experimental details

Crystal data
Chemical formula	C₃₄H₃₅N₃O₂
M_r	517.65
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	10.448 (7), 10.588 (9), 26.490 (16)
V (Å³)	2930 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.18 × 0.16 × 0.11

Data collection
Diffractometer	Nonius MACH-3 diffractometer
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	3068, 2933, 1037
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.119, 0.96
No. of reflections	2933
No. of parameters	355
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.17

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.82	1.98	2.791 (6)	170
C3—H3B···N2ⁱⁱ	0.97	2.61	3.353 (8)	133
C96—H96···O1ⁱⁱ	0.93	2.60	3.456 (9)	154
C94—H94···Cg1ⁱⁱⁱ	0.93	2.80	3.721 (11)	170

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

Acknowledgements

RSK thanks CSIR, New Delhi, for a Major Research Project.

References

Ali, Sk. A., Khan, J. H. & Wazeer, M. I. M. (1988). Tetrahedron, 44, 5911–5920. CrossRef CAS Web of Science Google Scholar
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Enraf–Nonius (1994). CAD-4 EXPRESS. Version 5.0. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Gothelf, K. V. & Jorgensen, K. A. (2000). Chem. Commun. pp. 1449–1458. Web of Science CrossRef Google Scholar
Goti, A., Fedi, V., Nanneli, L., De Sarlo, F. & Brandi, A. (1997). Synlett, pp. 577–579. CrossRef Google Scholar
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Hossain, N., Papchikhin, A., Plavec, J. & Chattopadhyaya, J. (1993). Tetrahedron, 49, 10133–10156. CrossRef CAS Web of Science Google Scholar
Kumar, K. R. R., Mallesha, H. & Rangappa, K. S. (2003). Synth. Commun. 33, 1545–1555. Web of Science CrossRef CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(3R*,4R*,5S*)-4-(4-Methyl­phen­yl)-2,3-di­phenyl-7-[(R*)-1-phenyl­ethyl]-1-oxa-2,7-di­aza­spiro­[4.5]decan-10-one oxime

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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