1-Acetyl-3-[benzoyl(4-methoxy­phenyl)­methyl­ene]-2,3-di­hydro-1H-indol-2-one

In the title compound, C₂₅H₁₉NO₄, the indole moiety is not completely planar, the heterocyclic ring being distorted very slightly towards a half-chair conformation. The benzoyl and 4-­methoxy­phenyl substituents are individually almost planar and are in a bisecting and nearly perpendicular configuration, respectively, with respect to the plane of the indole moiety. The molecular and packing structures in the crystal are stabilized by intramolecular and intermolecular C—H...O interactions.

S1. Comment

1,3-Dihydro-3-methylene-2H-indol-2-one derivatives are synthetic precursors for biologically active spirocyclohexenindoles and certain alkaloids (Beccali et al., 1999). The stereochemistry, including the configuration and conformation, and their correlations with other spectroscopic properties are also of current research interest (Coda et al., 1984). The photoreaction of 1-acetylisatin with 1,2-phenylacetylenes is one of the synthetic routes for obtaining such derivatives (Zhang et al., 2000). In order to investigate the effect of the attached substituents of 1,2-diphenylacetylene on the regioselectivity of the photoreaction and the stereochemical properties of the product, we have synthesized the title compound, 1-acetyl-3-[benzoyl(4-methoxyphenyl)methylene]-2,3-dihydro-1H-indol-2-one, (I), which is the product of the photoreaction of 1-acetylisatin with 1-(4-methoxyphenyl)-2-phenylacetylene. As part of this research interest, we determined the X-ray crystal structure of (I) in order to confirm its conformation and stereochemistry.

The bond lengths and angles in the title compound (Table 1) have normal values (Allen et al., 1987), except for the bond lengths around C11, due to the steric effects of the bulky substituents. The bond lengths and angles within the indole moiety agree with those of a related structure (Usman et al., 2001).

In the title structure (Fig. 1), the indole moiety is not completely planar, with the heterocyclic ring being distorted very slightly towards a half-chair conformation. This conformation is confirmed by its puckering parameters [Q₂ = 0.090 (2) Å and ϕ₂ = 133 (1)°; Cremer & Pople, 1975] and the deviations of C7 and C8 from the N1/C1/C6/C7/C8 mean plane are -0.052 (2) and 0.056 (2) Å, respectively. The dihedral angle between the mean planes of the heterocyclic and benzene rings in the indole moiety is 5.5 (1)°.

The benzoyl and 4-methoxyphenyl substituents attached at C11 are almost planar, although the carbonyl group of the benzoyl moiety is twisted slightly out of the plane of the benzene ring, so that O3 deviates by 0.390 (1) Å from this plane. The O3/C11/C19/C20 plane is twisted by 22.1 (1)° from that of the benzene ring. The maximum deviation from the plane of the 4-methoxyphenyl substituent is 0.022 (2) Å at C12. The angle between the mean planes of these two substituents is 63.6 (1)°.

Although the mean plane of the 4-methoxyphenyl group is in a bisecting configuration with respect to that of the indole moiety, the benzoyl ring lies nearly perpendicular to the plane of the indole ring system. The corresponding dihedral angles are 48.1 (1) and 85.0 (1)°, respectively. The ketone O2 atom deviates by 0.324 (1) Å from the mean plane of the indole moiety, while the acetyl group attached at N1 is twisted by 10.3 (1)° from the indole-ring plane.

In the title compound, three intramolecular C—H···O interactions form closed rings, viz. O2/C8/N1/C9/C10/H10A, O1/C9/N1/C1/C2/H2A and O3/C19/C11/C12/C17/H17A. The molecules are linked by an intermolecular C23—H23A···O3 interaction into columns along the x axis, and another intermolecular C10—H10B···O3 interaction interconnects the columns into a three-dimensional framework. These interactions, as well as van der Waals interactions, stabilize the molecular and the packing structure in the crystal.

Related literature

For related literature, see: Allen et al. (1987); Coda et al. (1984); Cremer & Pople (1975); Zhang et al. (2000).

S2. Experimental

The title compound, (I), was prepared by a photoinduced reaction of 1-acetylisatin with 1-methoxyphenyl-2-phenylacetylene (Zhang et al., 2000). The primary product in the photoreaction is supposed to be a spiroxetene which rearranges under reaction conditions to the Z and E isomers of 3-[benzoyl(4-methoxyphenyl)methylene]-2,3-dihydro-1H-indol-2-one. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a petroleum ether–ethyl acetate solution.

S3. Refinement

After checking their presence in a difference Fourier synthesis, the positions of all H atoms were geometrically idealized and allowed to ride on their parent C atoms, with C—H distances of 0.93 and 0.96 Å for aromatic and methyl H atoms, respectively, and fixed displacement parameters defined by U_iso(H) = 1.2U_eq(C_aromatic) or 1.5U_eq(C_methyl).

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures

	Fig. 1. The structure of title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Packing of the title compound viewed down the a axis.

3-[Benzoyl(4-methoxyphenyl)methylene]-2,3-dihydro-1H-indol-2-one

Crystal data

C25H19NO4	Dx = 1.327 Mg m^−3
Mr = 397.41	Melting point: 453K K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.0395 (3) Å	Cell parameters from 5444 reflections
b = 16.7881 (5) Å	θ = 1.8–28.4°
c = 14.8438 (5) Å	µ = 0.09 mm^−1
β = 96.954 (1)°	T = 293 K
V = 1988.7 (1) Å^3	Block, yellow
Z = 4	0.34 × 0.26 × 0.22 mm
F(000) = 832

Data collection

Siemens SMART CCD area-detector diffractometer	4857 independent reflections
Radiation source: fine-focus sealed tube	2603 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
Detector resolution: 8.33 pixels mm^-1	θmax = 28.3°, θmin = 1.8°
ω scans	h = −9→10
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −19→22
Tmin = 0.970, Tmax = 0.980	l = −19→19
13734 measured reflections

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)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.058P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.91	(Δ/σ)max < 0.001
4857 reflections	Δρmax = 0.18 e Å^−3
274 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: 0.0066 (12)

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
O1	0.8466 (2)	−0.11836 (9)	0.51135 (11)	0.0818 (5)
O2	0.92050 (19)	0.05665 (8)	0.70865 (9)	0.0587 (4)
O3	0.85943 (16)	0.22279 (7)	0.78816 (8)	0.0464 (3)
O4	0.7318 (2)	0.52297 (8)	0.48966 (11)	0.0748 (5)
N1	0.82185 (19)	0.00548 (8)	0.56590 (10)	0.0417 (4)
C1	0.7254 (2)	0.03884 (10)	0.48790 (11)	0.0397 (4)
C2	0.6493 (3)	−0.00042 (12)	0.41222 (13)	0.0538 (6)
H2A	0.6624	−0.0550	0.4047	0.065*
C3	0.5527 (3)	0.04500 (13)	0.34811 (14)	0.0598 (6)
H3A	0.5001	0.0201	0.2964	0.072*
C4	0.5313 (3)	0.12558 (13)	0.35797 (13)	0.0568 (6)
H4A	0.4639	0.1540	0.3138	0.068*
C5	0.6105 (3)	0.16458 (12)	0.43394 (13)	0.0494 (5)
H5A	0.5971	0.2192	0.4408	0.059*
C6	0.7095 (2)	0.12134 (10)	0.49923 (11)	0.0390 (4)
C7	0.8035 (2)	0.14297 (10)	0.58651 (11)	0.0353 (4)
C8	0.8573 (2)	0.06629 (10)	0.63084 (12)	0.0388 (4)
C9	0.8729 (3)	−0.07465 (11)	0.57524 (14)	0.0488 (5)
C10	0.9613 (3)	−0.10116 (13)	0.66339 (15)	0.0694 (7)
H10A	1.0541	−0.0663	0.6812	0.104*
H10B	1.0017	−0.1545	0.6576	0.104*
H10C	0.8854	−0.0999	0.7086	0.104*
C11	0.8464 (2)	0.21246 (9)	0.62867 (11)	0.0340 (4)
C12	0.8138 (2)	0.29326 (10)	0.58980 (11)	0.0351 (4)
C13	0.8507 (2)	0.31184 (11)	0.50349 (12)	0.0414 (4)
H13A	0.8939	0.2724	0.4689	0.050*
C14	0.8252 (2)	0.38720 (11)	0.46736 (12)	0.0451 (5)
H14A	0.8504	0.3981	0.4091	0.054*
C15	0.7623 (3)	0.44627 (11)	0.51813 (13)	0.0483 (5)
C16	0.7274 (3)	0.42918 (11)	0.60552 (13)	0.0557 (6)
H16A	0.6858	0.4689	0.6403	0.067*
C17	0.7538 (3)	0.35421 (11)	0.64088 (12)	0.0461 (5)
H17A	0.7314	0.3439	0.6998	0.055*
C18	0.7631 (4)	0.54352 (14)	0.40031 (16)	0.0808 (8)
H18A	0.7332	0.5982	0.3885	0.121*
H18B	0.6973	0.5100	0.3573	0.121*
H18C	0.8799	0.5362	0.3948	0.121*
C19	0.9387 (2)	0.21135 (9)	0.72443 (11)	0.0351 (4)
C20	1.1223 (2)	0.20053 (10)	0.73653 (12)	0.0388 (4)
C21	1.2186 (2)	0.21474 (11)	0.66717 (14)	0.0475 (5)
H21A	1.1681	0.2323	0.6110	0.057*
C22	1.3900 (3)	0.20283 (13)	0.68117 (17)	0.0633 (6)
H22A	1.4549	0.2139	0.6349	0.076*
C23	1.4647 (3)	0.17483 (14)	0.76303 (19)	0.0711 (7)
H23A	1.5797	0.1659	0.7717	0.085*
C24	1.3702 (3)	0.15992 (13)	0.83217 (18)	0.0661 (6)
H24A	1.4211	0.1405	0.8874	0.079*
C25	1.2004 (3)	0.17361 (12)	0.81995 (14)	0.0546 (5)
H25A	1.1373	0.1649	0.8676	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1294 (16)	0.0465 (9)	0.0646 (10)	0.0160 (9)	−0.0084 (10)	−0.0150 (8)
O2	0.0831 (11)	0.0451 (8)	0.0415 (8)	−0.0040 (7)	−0.0183 (8)	0.0058 (6)
O3	0.0464 (8)	0.0599 (9)	0.0335 (7)	−0.0034 (6)	0.0076 (6)	−0.0019 (6)
O4	0.1147 (15)	0.0429 (9)	0.0668 (11)	0.0140 (8)	0.0110 (10)	0.0128 (7)
N1	0.0528 (10)	0.0335 (8)	0.0375 (9)	−0.0029 (7)	−0.0001 (8)	−0.0007 (6)
C1	0.0455 (11)	0.0409 (10)	0.0319 (10)	−0.0061 (8)	0.0015 (8)	−0.0010 (8)
C2	0.0723 (15)	0.0441 (12)	0.0428 (12)	−0.0113 (10)	−0.0018 (11)	−0.0067 (9)
C3	0.0727 (15)	0.0648 (15)	0.0374 (11)	−0.0152 (11)	−0.0110 (11)	−0.0036 (10)
C4	0.0637 (14)	0.0602 (14)	0.0417 (12)	−0.0078 (11)	−0.0134 (10)	0.0075 (10)
C5	0.0549 (13)	0.0481 (12)	0.0425 (11)	−0.0022 (9)	−0.0045 (10)	0.0049 (9)
C6	0.0420 (11)	0.0412 (10)	0.0332 (10)	−0.0038 (8)	0.0020 (8)	0.0017 (8)
C7	0.0376 (10)	0.0364 (10)	0.0312 (9)	−0.0014 (7)	0.0013 (8)	0.0013 (7)
C8	0.0411 (11)	0.0371 (10)	0.0368 (11)	−0.0052 (8)	−0.0013 (9)	−0.0003 (8)
C9	0.0620 (13)	0.0348 (11)	0.0496 (12)	0.0009 (9)	0.0068 (10)	−0.0012 (9)
C10	0.101 (2)	0.0443 (12)	0.0600 (14)	0.0147 (12)	−0.0009 (14)	0.0095 (10)
C11	0.0361 (10)	0.0368 (10)	0.0290 (9)	−0.0005 (7)	0.0041 (8)	−0.0008 (7)
C12	0.0378 (10)	0.0351 (10)	0.0319 (10)	−0.0011 (7)	0.0017 (8)	−0.0025 (7)
C13	0.0511 (11)	0.0387 (10)	0.0353 (10)	−0.0011 (8)	0.0083 (9)	−0.0047 (8)
C14	0.0583 (13)	0.0421 (11)	0.0350 (10)	−0.0044 (9)	0.0063 (9)	0.0028 (8)
C15	0.0589 (13)	0.0369 (11)	0.0476 (12)	0.0018 (9)	0.0003 (10)	0.0056 (9)
C16	0.0770 (15)	0.0425 (12)	0.0496 (12)	0.0117 (10)	0.0152 (11)	−0.0046 (10)
C17	0.0590 (13)	0.0444 (11)	0.0362 (11)	0.0046 (9)	0.0110 (10)	−0.0019 (8)
C18	0.109 (2)	0.0626 (15)	0.0672 (16)	0.0021 (14)	−0.0034 (15)	0.0279 (12)
C19	0.0419 (10)	0.0315 (9)	0.0319 (10)	−0.0050 (7)	0.0038 (8)	−0.0012 (7)
C20	0.0404 (11)	0.0351 (10)	0.0400 (11)	−0.0057 (8)	0.0018 (9)	−0.0082 (8)
C21	0.0482 (12)	0.0463 (11)	0.0486 (12)	−0.0083 (9)	0.0087 (10)	−0.0120 (9)
C22	0.0483 (13)	0.0671 (15)	0.0773 (17)	−0.0131 (11)	0.0191 (13)	−0.0192 (12)
C23	0.0407 (13)	0.0686 (16)	0.101 (2)	−0.0051 (11)	−0.0032 (15)	−0.0198 (14)
C24	0.0490 (14)	0.0661 (15)	0.0767 (16)	−0.0054 (11)	−0.0184 (13)	−0.0014 (12)
C25	0.0493 (13)	0.0609 (13)	0.0511 (13)	−0.0074 (10)	−0.0043 (10)	0.0040 (10)

Geometric parameters (Å, º)

O1—C9	1.198 (2)	C11—C19	1.522 (2)
O2—C8	1.215 (2)	C12—C13	1.385 (2)
O3—C19	1.2184 (19)	C12—C17	1.394 (2)
O4—C15	1.368 (2)	C13—C14	1.380 (2)
O4—C18	1.422 (3)	C13—H13A	0.9300
N1—C9	1.409 (2)	C14—C15	1.378 (3)
N1—C8	1.409 (2)	C14—H14A	0.9300
N1—C1	1.427 (2)	C15—C16	1.390 (3)
C1—C2	1.380 (3)	C16—C17	1.370 (3)
C1—C6	1.403 (2)	C16—H16A	0.9300
C2—C3	1.383 (3)	C17—H17A	0.9300
C2—H2A	0.9300	C18—H18A	0.9600
C3—C4	1.374 (3)	C18—H18B	0.9600
C3—H3A	0.9300	C18—H18C	0.9600
C4—C5	1.390 (3)	C19—C20	1.476 (3)
C4—H4A	0.9300	C20—C21	1.382 (2)
C5—C6	1.383 (3)	C20—C25	1.394 (3)
C5—H5A	0.9300	C21—C22	1.383 (3)
C6—C7	1.464 (2)	C21—H21A	0.9300
C7—C11	1.349 (2)	C22—C23	1.372 (3)
C7—C8	1.486 (2)	C22—H22A	0.9300
C9—C10	1.480 (3)	C23—C24	1.372 (3)
C10—H10A	0.9600	C23—H23A	0.9300
C10—H10B	0.9600	C24—C25	1.375 (3)
C10—H10C	0.9600	C24—H24A	0.9300
C11—C12	1.485 (2)	C25—H25A	0.9300
C15—O4—C18	118.11 (17)	C14—C13—C12	121.85 (16)
C9—N1—C8	126.30 (16)	C14—C13—H13A	119.1
C9—N1—C1	125.30 (15)	C12—C13—H13A	119.1
C8—N1—C1	108.40 (14)	C15—C14—C13	119.62 (17)
C2—C1—C6	122.09 (17)	C15—C14—H14A	120.2
C2—C1—N1	128.07 (17)	C13—C14—H14A	120.2
C6—C1—N1	109.78 (15)	O4—C15—C14	124.90 (17)
C1—C2—C3	116.98 (19)	O4—C15—C16	115.70 (17)
C1—C2—H2A	121.5	C14—C15—C16	119.39 (17)
C3—C2—H2A	121.5	C17—C16—C15	120.50 (18)
C4—C3—C2	122.46 (19)	C17—C16—H16A	119.7
C4—C3—H3A	118.8	C15—C16—H16A	119.7
C2—C3—H3A	118.8	C16—C17—C12	120.91 (17)
C3—C4—C5	119.97 (19)	C16—C17—H17A	119.5
C3—C4—H4A	120.0	C12—C17—H17A	119.5
C5—C4—H4A	120.0	O4—C18—H18A	109.5
C6—C5—C4	119.31 (19)	O4—C18—H18B	109.5
C6—C5—H5A	120.3	H18A—C18—H18B	109.5
C4—C5—H5A	120.3	O4—C18—H18C	109.5
C5—C6—C1	119.16 (17)	H18A—C18—H18C	109.5
C5—C6—C7	132.95 (17)	H18B—C18—H18C	109.5
C1—C6—C7	107.83 (15)	O3—C19—C20	122.30 (16)
C11—C7—C6	134.47 (16)	O3—C19—C11	118.77 (15)
C11—C7—C8	119.96 (16)	C20—C19—C11	118.86 (14)
C6—C7—C8	105.57 (14)	C21—C20—C25	119.01 (18)
O2—C8—N1	125.48 (16)	C21—C20—C19	122.02 (17)
O2—C8—C7	127.03 (16)	C25—C20—C19	118.95 (16)
N1—C8—C7	107.50 (15)	C20—C21—C22	120.1 (2)
O1—C9—N1	119.06 (18)	C20—C21—H21A	120.0
O1—C9—C10	122.41 (19)	C22—C21—H21A	120.0
N1—C9—C10	118.51 (17)	C23—C22—C21	120.3 (2)
C9—C10—H10A	109.5	C23—C22—H22A	119.9
C9—C10—H10B	109.5	C21—C22—H22A	119.9
H10A—C10—H10B	109.5	C22—C23—C24	120.2 (2)
C9—C10—H10C	109.5	C22—C23—H23A	119.9
H10A—C10—H10C	109.5	C24—C23—H23A	119.9
H10B—C10—H10C	109.5	C23—C24—C25	120.1 (2)
C7—C11—C12	125.92 (16)	C23—C24—H24A	119.9
C7—C11—C19	119.41 (15)	C25—C24—H24A	119.9
C12—C11—C19	114.66 (13)	C24—C25—C20	120.3 (2)
C13—C12—C17	117.69 (16)	C24—C25—H25A	119.8
C13—C12—C11	121.17 (15)	C20—C25—H25A	119.8
C17—C12—C11	121.04 (15)
C9—N1—C1—C2	7.5 (3)	C8—C7—C11—C19	−4.5 (2)
C8—N1—C1—C2	−172.86 (19)	C7—C11—C12—C13	−47.7 (3)
C9—N1—C1—C6	−175.17 (17)	C19—C11—C12—C13	131.52 (18)
C8—N1—C1—C6	4.5 (2)	C7—C11—C12—C17	135.99 (19)
C6—C1—C2—C3	−1.4 (3)	C19—C11—C12—C17	−44.8 (2)
N1—C1—C2—C3	175.67 (19)	C17—C12—C13—C14	−1.8 (3)
C1—C2—C3—C4	−0.1 (3)	C11—C12—C13—C14	−178.27 (17)
C2—C3—C4—C5	1.0 (3)	C12—C13—C14—C15	0.4 (3)
C3—C4—C5—C6	−0.4 (3)	C18—O4—C15—C14	1.6 (3)
C4—C5—C6—C1	−1.0 (3)	C18—O4—C15—C16	−179.1 (2)
C4—C5—C6—C7	−177.65 (19)	C13—C14—C15—O4	180.0 (2)
C2—C1—C6—C5	2.0 (3)	C13—C14—C15—C16	0.8 (3)
N1—C1—C6—C5	−175.57 (16)	O4—C15—C16—C17	−179.8 (2)
C2—C1—C6—C7	179.37 (17)	C14—C15—C16—C17	−0.5 (3)
N1—C1—C6—C7	1.8 (2)	C15—C16—C17—C12	−0.9 (3)
C5—C6—C7—C11	−10.8 (4)	C13—C12—C17—C16	2.1 (3)
C1—C6—C7—C11	172.27 (19)	C11—C12—C17—C16	178.53 (19)
C5—C6—C7—C8	169.9 (2)	C7—C11—C19—O3	−99.9 (2)
C1—C6—C7—C8	−7.05 (19)	C12—C11—C19—O3	80.78 (19)
C9—N1—C8—O2	−9.2 (3)	C7—C11—C19—C20	83.1 (2)
C1—N1—C8—O2	171.19 (18)	C12—C11—C19—C20	−96.15 (18)
C9—N1—C8—C7	170.81 (16)	O3—C19—C20—C21	−157.28 (17)
C1—N1—C8—C7	−8.83 (19)	C11—C19—C20—C21	19.5 (2)
C11—C7—C8—O2	10.3 (3)	O3—C19—C20—C25	24.0 (2)
C6—C7—C8—O2	−170.26 (18)	C11—C19—C20—C25	−159.15 (16)
C11—C7—C8—N1	−169.68 (15)	C25—C20—C21—C22	−0.5 (3)
C6—C7—C8—N1	9.76 (19)	C19—C20—C21—C22	−179.16 (17)
C8—N1—C9—O1	−173.37 (19)	C20—C21—C22—C23	1.8 (3)
C1—N1—C9—O1	6.2 (3)	C21—C22—C23—C24	−1.3 (3)
C8—N1—C9—C10	5.1 (3)	C22—C23—C24—C25	−0.5 (3)
C1—N1—C9—C10	−175.28 (18)	C23—C24—C25—C20	1.8 (3)
C6—C7—C11—C12	−4.5 (3)	C21—C20—C25—C24	−1.3 (3)
C8—C7—C11—C12	174.70 (16)	C19—C20—C25—C24	177.41 (18)
C6—C7—C11—C19	176.28 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1	0.93	2.29	2.835 (3)	117
C10—H10A···O2	0.96	2.39	2.762 (3)	103
C10—H10B···O3^i	0.96	2.43	3.328 (3)	155
C17—H17A···O3	0.93	2.57	3.149 (2)	121
C23—H23A···O3^ii	0.93	2.43	3.251 (3)	148

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