(1R,4R,5R)-1,3,4-Triphenyl-7-[(R)-1-phenyl-ethyl]-2-oxa-3,7-diaza-spiro-[4.5]decan-10-one.

In the title compound, C(33)H(32)N(2)O(2), the polysubstituted piperidine ring adopts a chair conformation. The isoxazolidine ring is in an envelope conformation. In the crystal structure, intra- and inter-molecular C-H⋯π inter-actions 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 = 488.61

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.118

S = 1.09

2701 reflections

335 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.14 e Å−3

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067256/ci2540Isup2.hkl

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

C33H32N2O2	F000 = 1040
Mr = 488.61	Dx = 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 = 2–25º
b = 14.582 (7) Å	µ = 0.08 mm−1
c = 17.443 (8) Å	T = 273 (2) K
V = 2693 (2) Å3	Needle, colourless
Z = 4	0.20 × 0.16 × 0.12 mm

Nonius MACH-3 diffractometer	Rint = 0.074
Radiation source: fine-focus sealed tube	θmax = 25.0º
Monochromator: graphite	θmin = 1.8º
T = 273(2) K	h = −12→11
ω/2θ scans	k = −17→16
Absorption correction: ψ scan(North et al., 1968)	l = −20→20
Tmin = 0.986, Tmax = 0.991	2 standard reflections
13617 measured reflections	every 60 min
2701 independent reflections	intensity decay: none
1899 reflections with I > 2σ(I)

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.065	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0519P)2] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2701 reflections	Δρmax = 0.16 e Å−3
335 parameters	Δρmin = −0.14 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) .