9-(4-Methyl­benzyl­idene)-4,8-di­phenyl-6-p-tolyl-2-oxa-3,7-di­aza­spiro­[4.4]­nona-3,7-dien-1-one

The title compounds, C₃₃H₂₆N₂O₂, is the unexpected spiran product of a synthetic reaction. The crystal structure has been determined at room temperature. The skeleton is composed of a spiro­[4.4] system formed by an isoxazolone and a substituted pyrroline ring obtained by a series of tandem reactions. The carbonyl group of the isoxazolone ring shows the usual asymmetry of the exocyclic bond angles [121.7 (3) versus 130.7 (4)°].

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.049
• wR factor = 0.126
• Data-to-parameter ratio = 13.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

The formation of the title compound, (I), like the o-MeOC₆H₄– derivative (Bruno et al., 2001a), was rationalized in terms of a series of tandem reactions involving Michael- and retro-Michael reactions, C-alkylation, aldol addition and diastereospecific cyclization (Risitano et al., 2001).

The stereochemistry around the C═C double bond and the newly created tetrahedral C atoms in the spiro compounds could not easily be established by any spectral technique. Therefore, the present study was undertaken in order to obtain unambiguous structural characterization of this new molecule.

The compound consists of a spiro[4.4] system formed by an isoxazolone and a three-substituted pyrroline rings. The pivot atom C1 of the spiro-center and the C4 pyrroline atom are two chiral centers having the same configuration (R,R for the molecule depicted in Fig. 1). Since the compound crystallizes in a centrosymmetric space group, in the solid state we have a racemic mixture.

Bond distances and angles are in good agreement with the literature values (Bertolasi et al., 1994; Brehm et al., 1992). Here we observe the usual asymmetry in bond angles around the carbonyl group. This significant asymmetry is systematically present in all 2800 five-membered rings reported in the last release (5.19) of the Cambridge Structural Database (Allen et al., 1991) that contain a carbonyl group as well as in cumarine derivatives (Bruno et al., 2001b). The main discrepancy between the title compound and the o-MeO derivative rises from the rotation of the phenyl rings as evidenced by the significant difference of the corresponding torsion angles N1—C2—C14—C15 and C6—C26—C27—C28 of 32.7 (5) and 20.0 (5)°, respectively. All the heteroatoms of the spiranic fragments are engaged in some weak intra- and intermolecular hydrogen bonds which determine the relative orientations of substituents with respect to the spiranic moiety and the whole crystal packing.

S2. Experimental

The title compound was obtained as a single diastereomer from 4-arylmethyleneisoxazol-5-one, (I), and the in situ prepared N-ylide (II) (Risitano et al., 1997).

S3. Refinement

Due to the small crystal size, the diffraction data were collected twice at room temperature. A preliminary data collection of a small crystal was collected up to 2θ = 46°. The structure determination was carried out using the data of this reduced 2θ shell. When it was possible to obtain bigger crystals, a complete data collection was performed up to 2θ = 50° and this was used to refine the structure model. Reflection intensities were evaluated by profile fitting of a 96-steps peak scan among 2θ shells procedure (Diamond, 1969) and then corrected for Lorentz–polarization effects. Standard uncertainties σ(I) were estimated from counting statistics. H atoms have been located at idealized positions and were allowed to ride on their parent C atoms with a unique fixed isotropic displacement parameter (0.08 Ų).

Computing details

Data collection: XSCANS (Siemens, 1999); cell refinement: XSCANS; data reduction: SHELXTL-Plus (Sheldrick, 1990); program(s) used to solve structure: SIR92 (Altomare, 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XPW (Siemens, 1996); software used to prepare material for publication: PARST97 (Nardelli, 1995) and SHELXL97.

Figures

Fig. 1. Perspective view of the title compound showing the atomic numbering scheme. The displacement ellipsoids are drawn at 30% of probability level for non-H atoms.

9-(4-Methyl-benzylidene)-4,8-diphenyl-6-p-tolyl-2-oxa- 3,7-diazaspiro[4.4]nona-3,7-dien-1-one

Crystal data

C33H26N2O2	F(000) = 1016
Mr = 482.56	Dx = 1.222 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.909 (3) Å	Cell parameters from 28 reflections
b = 18.502 (7) Å	θ = 2.2–12.5°
c = 13.092 (4) Å	µ = 0.08 mm^−1
β = 97.143 (12)°	T = 298 K
V = 2621.9 (15) Å^3	Prism, colourless
Z = 4	0.46 × 0.27 × 0.22 mm

Data collection

Siemens P4 diffractometer	Rint = 0.032
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.9°
Graphite monochromator	h = −1→12
ω scans	k = −1→21
5738 measured reflections	l = −15→15
4602 independent reflections	3 standard reflections every 97 reflections
1712 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.126	w = 1/[σ^2(Fo^2) + (0.0278P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max < 0.001
4602 reflections	Δρmax = 0.21 e Å^−3
335 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0063 (6)

Special details

Experimental. due to the small size of crystal samples of compound III, diffraction data have been recolleted on a new bigger sample.

All calculations were performed on a µ-VAX 3400 and on a DEC-alpha 3000/400.

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 (Ų)

	x	y	z	Uiso*/Ueq
C3	0.8696 (4)	0.23869 (19)	0.2732 (3)	0.0657 (10)
O2	0.9447 (2)	0.20392 (13)	0.23488 (18)	0.0828 (8)
C1	0.8783 (3)	0.27669 (17)	0.3770 (2)	0.0542 (8)
C2	0.7621 (3)	0.31989 (18)	0.3618 (2)	0.0568 (9)
N1	0.6886 (3)	0.30278 (16)	0.2801 (2)	0.0752 (9)
O1	0.7530 (2)	0.25016 (13)	0.22350 (17)	0.0810 (8)
C14	0.7272 (3)	0.38018 (18)	0.4265 (3)	0.0585 (9)
C15	0.6598 (3)	0.4372 (2)	0.3791 (3)	0.0773 (11)
H15	0.6331	0.4353	0.3089	0.093*
C16	0.6323 (4)	0.4968 (2)	0.4353 (4)	0.0946 (14)
H16	0.5887	0.5352	0.4025	0.113*
C17	0.6688 (4)	0.4997 (2)	0.5397 (4)	0.0980 (14)
H17	0.6487	0.5397	0.5774	0.118*
C18	0.7351 (4)	0.4437 (2)	0.5881 (3)	0.0891 (12)
H18	0.7592	0.4455	0.6587	0.107*
C19	0.7664 (3)	0.38412 (19)	0.5317 (3)	0.0732 (11)
H19	0.8135	0.3469	0.5643	0.088*
C4	0.8801 (3)	0.21671 (17)	0.4665 (2)	0.0591 (9)
H4	0.8351	0.2367	0.5203	0.071*
N2	1.0105 (3)	0.20973 (15)	0.5103 (2)	0.0646 (8)
C5	1.0739 (3)	0.26304 (19)	0.4793 (2)	0.0587 (9)
C6	1.0018 (3)	0.31331 (19)	0.4075 (2)	0.0563 (9)
C7	0.8206 (3)	0.14485 (19)	0.4336 (2)	0.0609 (9)
C8	0.8888 (3)	0.0855 (2)	0.4104 (2)	0.0710 (10)
H8	0.9743	0.0889	0.4148	0.085*
C9	0.8309 (4)	0.0207 (2)	0.3805 (3)	0.0811 (12)
H9	0.8786	−0.0186	0.3653	0.097*
C10	0.7049 (5)	0.0133 (3)	0.3730 (3)	0.0932 (14)
C11	0.6373 (4)	0.0725 (3)	0.3966 (3)	0.1070 (16)
H11	0.5518	0.0687	0.3922	0.128*
C12	0.6935 (4)	0.1377 (2)	0.4267 (3)	0.0927 (13)
H12	0.6455	0.1768	0.4424	0.111*
C13	0.6431 (4)	−0.0589 (2)	0.3402 (3)	0.143 (2)
H13A	0.5552	−0.0542	0.3379	0.171*
H13B	0.6724	−0.0957	0.3890	0.171*
H13C	0.6631	−0.0719	0.2733	0.171*
C20	1.2067 (3)	0.27094 (17)	0.5154 (3)	0.0611 (9)
C21	1.2897 (3)	0.29086 (18)	0.4488 (3)	0.0756 (11)
H21	1.2612	0.3009	0.3804	0.091*
C22	1.4142 (4)	0.2960 (2)	0.4825 (4)	0.0928 (13)
H22	1.4693	0.3082	0.4365	0.111*
C23	1.4565 (4)	0.2833 (2)	0.5838 (4)	0.1046 (16)
H23	1.5404	0.2877	0.6067	0.125*
C24	1.3756 (4)	0.2639 (2)	0.6521 (4)	0.1035 (15)
H24	1.4048	0.2551	0.7208	0.124*
C25	1.2506 (4)	0.25749 (19)	0.6180 (3)	0.0821 (12)
H25	1.1959	0.2442	0.6638	0.099*
C26	1.0358 (3)	0.38088 (18)	0.3855 (2)	0.0609 (9)
H26	1.1133	0.3954	0.4164	0.073*
C27	0.9665 (3)	0.43470 (19)	0.3192 (3)	0.0589 (9)
C28	0.9031 (3)	0.41793 (18)	0.2233 (3)	0.0675 (10)
H28	0.9081	0.3714	0.1974	0.081*
C29	0.8324 (3)	0.4695 (2)	0.1655 (3)	0.0721 (11)
H29	0.7890	0.4567	0.1024	0.087*
C30	0.8260 (3)	0.5397 (2)	0.2010 (3)	0.0688 (10)
C31	0.8929 (3)	0.55711 (19)	0.2943 (3)	0.0741 (11)
H31	0.8911	0.6043	0.3186	0.089*
C32	0.9623 (3)	0.50596 (19)	0.3519 (3)	0.0676 (10)
H32	1.0073	0.5194	0.4140	0.081*
C33	0.7501 (4)	0.5968 (2)	0.1383 (3)	0.1054 (14)
H33A	0.7104	0.5755	0.0759	0.127*
H33B	0.8033	0.6352	0.1217	0.127*
H33C	0.6887	0.6156	0.1776	0.127*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C3	0.072 (3)	0.063 (3)	0.060 (2)	−0.005 (2)	0.001 (2)	0.005 (2)
O2	0.097 (2)	0.0794 (18)	0.0742 (17)	−0.0003 (16)	0.0208 (16)	−0.0103 (14)
C1	0.050 (2)	0.063 (2)	0.0482 (19)	−0.0031 (19)	−0.0004 (16)	−0.0003 (17)
C2	0.050 (2)	0.063 (2)	0.056 (2)	−0.0063 (19)	−0.0007 (18)	0.0039 (19)
N1	0.064 (2)	0.085 (2)	0.072 (2)	−0.0039 (18)	−0.0083 (17)	−0.0061 (18)
O1	0.0822 (19)	0.0867 (18)	0.0686 (16)	−0.0029 (16)	−0.0127 (14)	−0.0155 (14)
C14	0.045 (2)	0.066 (2)	0.064 (2)	−0.0017 (19)	0.0048 (18)	0.004 (2)
C15	0.067 (3)	0.083 (3)	0.084 (3)	0.013 (2)	0.019 (2)	0.008 (2)
C16	0.072 (3)	0.090 (4)	0.125 (4)	0.020 (3)	0.028 (3)	0.015 (3)
C17	0.077 (3)	0.078 (3)	0.144 (5)	0.007 (3)	0.034 (3)	−0.018 (3)
C18	0.083 (3)	0.094 (3)	0.093 (3)	−0.008 (3)	0.020 (3)	−0.027 (3)
C19	0.072 (3)	0.072 (3)	0.074 (3)	−0.001 (2)	0.002 (2)	−0.007 (2)
C4	0.058 (2)	0.062 (2)	0.057 (2)	−0.001 (2)	0.0095 (18)	0.0007 (18)
N2	0.060 (2)	0.0633 (19)	0.0672 (18)	−0.0036 (17)	−0.0049 (15)	0.0037 (15)
C5	0.059 (2)	0.060 (2)	0.056 (2)	0.005 (2)	0.0009 (18)	−0.0042 (18)
C6	0.054 (2)	0.062 (2)	0.052 (2)	0.000 (2)	0.0038 (17)	0.0001 (18)
C7	0.057 (2)	0.058 (2)	0.066 (2)	−0.005 (2)	0.0022 (19)	0.0050 (19)
C8	0.075 (3)	0.069 (3)	0.071 (2)	−0.006 (2)	0.019 (2)	−0.005 (2)
C9	0.107 (4)	0.066 (3)	0.072 (3)	−0.008 (3)	0.018 (3)	−0.011 (2)
C10	0.106 (4)	0.084 (3)	0.082 (3)	−0.027 (3)	−0.015 (3)	0.004 (3)
C11	0.066 (3)	0.100 (4)	0.148 (4)	−0.025 (3)	−0.016 (3)	0.020 (3)
C12	0.071 (3)	0.073 (3)	0.131 (4)	−0.002 (3)	0.000 (3)	0.015 (3)
C13	0.189 (5)	0.108 (4)	0.119 (4)	−0.068 (4)	−0.035 (3)	0.000 (3)
C20	0.056 (2)	0.056 (2)	0.067 (2)	0.0028 (19)	−0.008 (2)	−0.0018 (19)
C21	0.059 (3)	0.078 (3)	0.086 (3)	0.002 (2)	−0.003 (2)	−0.001 (2)
C22	0.062 (3)	0.095 (3)	0.119 (4)	0.003 (3)	0.002 (3)	0.007 (3)
C23	0.058 (3)	0.097 (3)	0.149 (5)	0.003 (3)	−0.025 (3)	−0.002 (3)
C24	0.082 (3)	0.111 (4)	0.107 (4)	0.000 (3)	−0.029 (3)	0.010 (3)
C25	0.071 (3)	0.092 (3)	0.078 (3)	0.000 (2)	−0.013 (2)	0.008 (2)
C26	0.054 (2)	0.068 (2)	0.060 (2)	−0.004 (2)	0.0043 (18)	0.0003 (19)
C27	0.056 (2)	0.064 (2)	0.057 (2)	−0.005 (2)	0.0061 (18)	0.0035 (19)
C28	0.080 (3)	0.059 (2)	0.064 (2)	−0.004 (2)	0.012 (2)	0.003 (2)
C29	0.079 (3)	0.079 (3)	0.058 (2)	−0.003 (2)	0.006 (2)	0.004 (2)
C30	0.069 (3)	0.067 (3)	0.071 (3)	0.003 (2)	0.011 (2)	0.016 (2)
C31	0.085 (3)	0.059 (2)	0.080 (3)	−0.002 (2)	0.015 (2)	0.005 (2)
C32	0.076 (3)	0.063 (2)	0.065 (2)	−0.012 (2)	0.012 (2)	0.002 (2)
C33	0.107 (3)	0.099 (3)	0.110 (3)	0.023 (3)	0.011 (3)	0.030 (3)

Geometric parameters (Å, º)

C3—O2	1.199 (4)	C7—C8	1.382 (4)
C3—O1	1.372 (4)	C7—C12	1.384 (4)
C3—C1	1.522 (4)	C8—C9	1.388 (4)
C1—C2	1.490 (4)	C9—C10	1.373 (5)
C1—C6	1.517 (4)	C10—C11	1.377 (5)
C1—C4	1.612 (4)	C10—C13	1.532 (5)
C2—N1	1.293 (3)	C11—C12	1.389 (5)
C2—C14	1.479 (4)	C20—C21	1.382 (4)
N1—O1	1.456 (3)	C20—C25	1.392 (4)
C14—C15	1.388 (4)	C21—C22	1.378 (5)
C14—C19	1.392 (4)	C22—C23	1.369 (5)
C15—C16	1.378 (5)	C23—C24	1.381 (5)
C16—C17	1.376 (5)	C24—C25	1.386 (5)
C17—C18	1.373 (5)	C26—C27	1.468 (4)
C18—C19	1.393 (4)	C27—C32	1.389 (4)
C4—N2	1.471 (4)	C27—C28	1.390 (4)
C4—C7	1.518 (4)	C28—C29	1.390 (4)
N2—C5	1.298 (4)	C29—C30	1.384 (4)
C5—C20	1.475 (4)	C30—C31	1.381 (4)
C5—C6	1.477 (4)	C30—C33	1.517 (4)
C6—C26	1.345 (4)	C31—C32	1.377 (4)
O2—C3—O1	121.7 (3)	C5—C6—C1	105.7 (3)
O2—C3—C1	130.7 (4)	C8—C7—C12	118.2 (4)
O1—C3—C1	107.6 (3)	C8—C7—C4	122.4 (3)
C2—C1—C6	120.6 (3)	C12—C7—C4	119.4 (4)
C2—C1—C3	99.9 (3)	C7—C8—C9	120.6 (4)
C6—C1—C3	113.3 (3)	C10—C9—C8	121.5 (4)
C2—C1—C4	113.6 (3)	C9—C10—C11	117.6 (4)
C6—C1—C4	100.7 (2)	C9—C10—C13	120.6 (5)
C3—C1—C4	108.9 (3)	C11—C10—C13	121.8 (5)
N1—C2—C14	118.7 (3)	C10—C11—C12	121.7 (4)
N1—C2—C1	114.1 (3)	C7—C12—C11	120.3 (4)
C14—C2—C1	127.1 (3)	C21—C20—C25	118.9 (3)
C2—N1—O1	107.2 (3)	C21—C20—C5	121.3 (3)
C3—O1—N1	109.9 (3)	C25—C20—C5	119.8 (3)
C15—C14—C19	118.9 (3)	C22—C21—C20	120.9 (4)
C15—C14—C2	118.5 (3)	C23—C22—C21	119.9 (4)
C19—C14—C2	122.5 (3)	C22—C23—C24	120.4 (4)
C16—C15—C14	120.5 (4)	C23—C24—C25	119.7 (4)
C17—C16—C15	120.4 (4)	C24—C25—C20	120.2 (4)
C18—C17—C16	119.9 (4)	C6—C26—C27	128.4 (3)
C17—C18—C19	120.2 (4)	C32—C27—C28	117.3 (3)
C14—C19—C18	120.0 (4)	C32—C27—C26	119.7 (3)
N2—C4—C7	113.1 (3)	C28—C27—C26	123.0 (3)
N2—C4—C1	105.5 (2)	C27—C28—C29	121.2 (3)
C7—C4—C1	115.5 (3)	C30—C29—C28	120.6 (3)
C5—N2—C4	109.8 (3)	C31—C30—C29	118.2 (3)
N2—C5—C20	121.0 (3)	C31—C30—C33	120.6 (4)
N2—C5—C6	114.5 (3)	C29—C30—C33	121.2 (3)
C20—C5—C6	124.4 (3)	C32—C31—C30	121.3 (3)
C26—C6—C5	125.6 (3)	C31—C32—C27	121.3 (3)
C26—C6—C1	128.2 (3)
O2—C3—C1—C2	169.0 (4)	C4—C1—C6—C26	−155.3 (3)
O1—C3—C1—C2	−11.2 (3)	C2—C1—C6—C5	142.9 (3)
O2—C3—C1—C6	39.4 (5)	C3—C1—C6—C5	−99.0 (3)
O1—C3—C1—C6	−140.7 (3)	C4—C1—C6—C5	17.2 (3)
O2—C3—C1—C4	−71.8 (5)	N2—C4—C7—C8	−23.0 (4)
O1—C3—C1—C4	108.1 (3)	C1—C4—C7—C8	98.7 (4)
C6—C1—C2—N1	135.3 (3)	N2—C4—C7—C12	156.7 (3)
C3—C1—C2—N1	10.6 (4)	C1—C4—C7—C12	−81.6 (4)
C4—C1—C2—N1	−105.2 (3)	C12—C7—C8—C9	0.3 (5)
C6—C1—C2—C14	−41.9 (5)	C4—C7—C8—C9	−180.0 (3)
C3—C1—C2—C14	−166.6 (3)	C7—C8—C9—C10	0.0 (6)
C4—C1—C2—C14	77.6 (4)	C8—C9—C10—C11	−0.2 (6)
C14—C2—N1—O1	171.6 (3)	C8—C9—C10—C13	−179.8 (3)
C1—C2—N1—O1	−5.9 (4)	C9—C10—C11—C12	0.1 (7)
O2—C3—O1—N1	−171.3 (3)	C13—C10—C11—C12	179.7 (4)
C1—C3—O1—N1	8.8 (3)	C8—C7—C12—C11	−0.4 (6)
C2—N1—O1—C3	−2.1 (3)	C4—C7—C12—C11	179.9 (3)
N1—C2—C14—C15	−32.1 (5)	C10—C11—C12—C7	0.2 (7)
C1—C2—C14—C15	145.0 (3)	N2—C5—C20—C21	138.5 (3)
N1—C2—C14—C19	152.3 (3)	C6—C5—C20—C21	−42.0 (5)
C1—C2—C14—C19	−30.6 (5)	N2—C5—C20—C25	−40.9 (5)
C19—C14—C15—C16	0.0 (5)	C6—C5—C20—C25	138.7 (3)
C2—C14—C15—C16	−175.7 (3)	C25—C20—C21—C22	1.3 (5)
C14—C15—C16—C17	−1.5 (6)	C5—C20—C21—C22	−178.1 (3)
C15—C16—C17—C18	1.2 (6)	C20—C21—C22—C23	−1.8 (6)
C16—C17—C18—C19	0.6 (6)	C21—C22—C23—C24	1.2 (7)
C15—C14—C19—C18	1.7 (5)	C22—C23—C24—C25	−0.1 (7)
C2—C14—C19—C18	177.3 (3)	C23—C24—C25—C20	−0.3 (6)
C17—C18—C19—C14	−2.0 (6)	C21—C20—C25—C24	−0.2 (5)
C2—C1—C4—N2	−148.9 (3)	C5—C20—C25—C24	179.1 (3)
C6—C1—C4—N2	−18.7 (3)	C5—C6—C26—C27	−176.8 (3)
C3—C1—C4—N2	100.7 (3)	C1—C6—C26—C27	−5.7 (6)
C2—C1—C4—C7	85.4 (3)	C6—C26—C27—C32	135.8 (4)
C6—C1—C4—C7	−144.3 (3)	C6—C26—C27—C28	−44.1 (5)
C3—C1—C4—C7	−25.0 (4)	C32—C27—C28—C29	−3.8 (5)
C7—C4—N2—C5	140.7 (3)	C26—C27—C28—C29	176.1 (3)
C1—C4—N2—C5	13.5 (3)	C27—C28—C29—C30	1.7 (5)
C4—N2—C5—C20	177.4 (3)	C28—C29—C30—C31	0.9 (5)
C4—N2—C5—C6	−2.2 (4)	C28—C29—C30—C33	179.5 (3)
N2—C5—C6—C26	161.9 (3)	C29—C30—C31—C32	−1.3 (5)
C20—C5—C6—C26	−17.7 (5)	C33—C30—C31—C32	−179.9 (3)
N2—C5—C6—C1	−10.9 (4)	C30—C31—C32—C27	−0.9 (5)
C20—C5—C6—C1	169.6 (3)	C28—C27—C32—C31	3.4 (5)
C2—C1—C6—C26	−29.6 (5)	C26—C27—C32—C31	−176.5 (3)
C3—C1—C6—C26	88.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N2	0.93	2.57	2.886 (5)	100
C15—H15···N1	0.93	2.56	2.840 (5)	97
C25—H25···N2	0.93	2.74	2.951 (5)	94
C31—H31···O2^i	0.93	2.72	3.290 (4)	120

Symmetry code: (i) −x+2, y+1/2, −z+1/2.