1-Acetyl-4'-ethyl-2a'-phenyl-2',2a',5',5a'-tetrahydrospiro­[1H-indole-3,2'-oxeto[5,4-b]­oxazol]-2(3H)-one and 1-acetyl-4',5a'-­di­phenyl-2',2a',5',5a'-tetrahydro­spiro­[1H-indole-3,2'-oxeto­[5,4-b]­­oxazol]-2(3H)-one

In the title compounds, C₂₁H₁₈N₂O₄ and C₂₅H₁₈N₂O₄, respectively, the five-membered ring of the indole system is almost planar. The oxetane and oxazole rings are individually planar. The orientations of the indole, oxetane, oxazole and phenyl moieties are conditioned by the sp³ nature of the spiro-C atoms. In both compounds, the relative orientation of the indole and oxazole rings is opposite.

S1. Comment

Recently, we have studied the photocycloaddition reactions of some α-dicarbonyl compounds with oxazole derivatives (Zhang et al., 2003). For the photoinduced reactions of 1-acetylisatin with oxazole derivatives, some of the separable products are the corresponding [indole-3,2'-oxeto[5,4-b]oxazol]-2(1H)-one derivatives. We have structurally analysed two of these derivatives, viz. (I) and (II), and the results are presented here.

The bond lengths and angles in compounds (I) and (II) (Figs. 1 and 2, respectively) are within normal ranges (Allen et al., 1987). The corresponding values agree with each other. Those within the indole moieties (C1–C6/N1/C7/C8) are comparable to the corresponding values in the related structure spiro[1H-indole-3,2'-oxetan]-2(3H)-one, hereafter (III) (Usman et al., 2002).

An elongation of the Csp³–Csp³ bond C8—C11 of the spiroxetane ring (C8/C9/C11/O1) is observed, especially in compound (I), due to the bulky substituents attached at C11. This elongation is also found in compound (III).

The spiroxetane is nearly planar with the dihedral angle between the O1/C8/C11 and O1/C9/C11 planes being 178.6 (2)° in compound (I) and 176.6 (3)° in compound (II). This is in contrast to the corresponding dihedral angle of 163.0 (3)° in (III) (Usman et al., 2002).

The planes through the oxetane and its fused oxazole ring (C9/C11/N2/C10/O2) make a dihedral angle of 66.5 (1)° in compound (I) and 67.0 (2)° in molecule (II). This is conditioned by the eclipsed configuration of the sp³ state of the shared atoms C9 and C11. The angles around these two atoms are listed in Tables 1 and 3 for (I) and (II), repectively.

The oxetane ring and the indole system are nearly orthogonal, with dihedral angles of 89.8 (1) and 83.6 (1)° between their planes in (I) and (II), respectively, and the C12–C17 phenyl ring makes dihedral angles with the oxetane ring of 56.9 (1) and 61.1 (2)° in (I) and (II), respectively. The relative orientation of the oxazole ring and indole moiety in (I) is opposite compared with that in (II). This is determined by the C1—C8—C11—N2 and C7—C8—C11—N2 torsion angles which are −134.9 (1) and −12.2 (2)°, respectively, for compound (I), and 19.9 (3) and 141.0 (2)° for compound (II).

In (I) and (II), the orientations and the relative distribution of the indole moiety and C12–C17 phenyl ring are conditioned by the eclipsed configuration of the atom pairs C8—C11 and C9—C11. These are supported by the torsion angles involving C8—C11 and C9—C11 (see Tables 1 and 3).

The indole moiety almost planar, with its five-membered ring adopting a conformation intermediate between envelope and half-chair for (I) and a half-chair conformation for (II). The Q₂ puckering amplitude is 0.129 (2) Å for (I) and 0.150 (3) Å for (I). The dihedral angle between the five-membered ring and the fused benzene ring is 4.2 (1)° in (I) and 4.6 (2)° in (II). Ketone atom O4 attached at C7 deviates from the mean plane of the five-membered ring by 0.280 (1) Å in (I) and 0.308 (2)° in (II).

In (I) and (II), the acetyl group (O3/C18/C19) attached at N1 is twisted by angles of 8.9 (1) and 11.6 (1)°, respectively, from the mean plane of the indole moiety. This indicates that the acetyl group tends to be coplanar with the indole moiety, as is usually observed for 1-acetylindole derivatives due to the interactions of the π-conjugation of the acetyl group. In (I) and (II), the intramolecular interaction which forms a O3—C18—N1—C6—C5—H5 S(6) graph ring (Etter et al., 1990) also participates in the π-conjugation.

In (I), the ethyl group (C20/C21) attached to C10 shows a positional disorder, so that the major and minor component (C21A and C21B) are displaced in opposite directions, by 0.421 (8) and 0.993 (4) Å, from the oxazole plane. In (II), the C20–C25 phenyl ring attached to C10 is twisted by an angle of 21.1 (2)° with respect to the oxazole plane.

For (I) and (II), the asymmetric units (Figs. 1 and 2) have atom C8 as an S chiral center. However, while atoms C9 and C11 of (I) are S chiral centers, these atoms are R chiral centers in (II) in Fig. 2. Moreover, since both compounds crystallized in centrosymmetric space groups, the samples used in this study are racemic crystals.

S2. Experimental

Compounds (I) and (II) were prepared by the photoinduced reactions of 1-acetylisatin with an excess amount of 2-ethyl-4-phenyloxazole and 2,5-diphenyloxazole, respectively, in benzene, and were separated by silica-gel column chromatography with petroleum ether–ethyl acetate as eluant. Single crystals of (I) and (II) were obtained from slow evaporation of petroleum ether–acetone solutions.

S3. Refinement

The H atoms of (I) were fixed geometrically and treated as riding on their parent C atoms, with C—H distances in the range 0.93–0.98 Å and U_iso(H) = 1.2–1.5U_eq(C). For (II), the H atoms were located from difference maps and were refined isotropically [C—H = 0.91 (3)–1.02 (4) Å], except for those attached to the methyl C atoms, which were fixed geometrically fixed and treated as riding. Rotating group refinement was used for the methyl groups of (I) and (II).

Computing details

For both compounds, 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, 2003).

Figures

	Fig. 1. The structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. The major and minor components of the disorder are shown for atom C21.
	Fig. 2. The structure of (II), showing 50% probability displacement ellipsoids and the atom-numbering scheme.

(I) 1-Acetyl-2a'-phenyl-4'-ethylspiro[indole-3,2'-[2a'H,5a'H]oxeto[5,4-b]oxazol]- 2(1H)-one

Crystal data

C21H18N2O4	Dx = 1.387 Mg m^−3
Mr = 362.37	Melting point: 392(1) K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.8569 (6) Å	Cell parameters from 6010 reflections
b = 12.4129 (6) Å	θ = 2.3–28.3°
c = 12.9849 (6) Å	µ = 0.10 mm^−1
β = 97.386 (1)°	T = 213 K
V = 1735.4 (2) Å^3	Block, colorless
Z = 4	0.48 × 0.44 × 0.42 mm
F(000) = 760

Data collection

Siemens SMART CCD area-detector diffractometer	4238 independent reflections
Radiation source: fine-focus sealed tube	3439 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
Detector resolution: 8.33 pixels mm^-1	θmax = 28.3°, θmin = 2.3°
ω scans	h = −14→6
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −16→16
Tmin = 0.899, Tmax = 0.960	l = −17→17
10582 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0644P)^2 + 0.7497P] where P = (Fo^2 + 2Fc^2)/3
4238 reflections	(Δ/σ)max < 0.001
257 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

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	Occ. (<1)
O1	0.33060 (10)	0.43585 (10)	0.20936 (8)	0.0392 (3)
O2	0.15416 (12)	0.41369 (11)	0.29910 (9)	0.0475 (3)
O3	0.2776 (2)	0.68099 (15)	−0.17305 (12)	0.0822 (6)
O4	0.20403 (12)	0.62977 (9)	0.13021 (9)	0.0416 (3)
N1	0.26945 (12)	0.58189 (10)	−0.02832 (10)	0.0335 (3)
N2	0.04952 (12)	0.42914 (11)	0.13637 (10)	0.0367 (3)
C1	0.34922 (14)	0.41368 (13)	0.01835 (12)	0.0344 (3)
C2	0.41497 (15)	0.31978 (14)	0.00799 (16)	0.0457 (4)
H2	0.4246	0.2686	0.0607	0.055*
C3	0.46650 (17)	0.30404 (18)	−0.08403 (19)	0.0567 (6)
H3	0.5117	0.2418	−0.0927	0.068*
C4	0.45093 (17)	0.38003 (19)	−0.16219 (16)	0.0562 (5)
H4	0.4849	0.3673	−0.2232	0.067*
C5	0.38621 (17)	0.47455 (18)	−0.15234 (14)	0.0493 (4)
H5	0.3767	0.5256	−0.2052	0.059*
C6	0.33586 (14)	0.49036 (13)	−0.06022 (12)	0.0355 (3)
C7	0.24238 (14)	0.56448 (12)	0.07382 (11)	0.0313 (3)
C8	0.27546 (14)	0.44720 (12)	0.10211 (11)	0.0305 (3)
C9	0.23545 (15)	0.36518 (13)	0.23500 (11)	0.0353 (3)
H9	0.2644	0.2930	0.2570	0.042*
C10	0.05268 (17)	0.44954 (17)	0.23200 (13)	0.0473 (4)
C11	0.16401 (13)	0.37062 (12)	0.12461 (11)	0.0296 (3)
C12	0.14160 (13)	0.27252 (12)	0.05758 (11)	0.0306 (3)
C13	0.16555 (16)	0.16968 (13)	0.09640 (13)	0.0380 (4)
H13	0.1960	0.1600	0.1660	0.046*
C14	0.1441 (2)	0.08116 (14)	0.03138 (15)	0.0499 (4)
H14	0.1597	0.0121	0.0577	0.060*
C15	0.0997 (2)	0.09501 (16)	−0.07210 (15)	0.0514 (5)
H15	0.0856	0.0353	−0.1153	0.062*
C16	0.07611 (18)	0.19712 (16)	−0.11167 (13)	0.0459 (4)
H16	0.0469	0.2063	−0.1816	0.055*
C17	0.09600 (15)	0.28597 (14)	−0.04718 (12)	0.0373 (3)
H17	0.0789	0.3547	−0.0737	0.045*
C18	0.24998 (17)	0.67809 (15)	−0.08627 (14)	0.0444 (4)
C19	0.19732 (18)	0.77318 (15)	−0.03783 (16)	0.0490 (4)
H19A	0.1839	0.8303	−0.0879	0.073*
H19B	0.2543	0.7969	0.0204	0.073*
H19C	0.1198	0.7538	−0.0148	0.073*
C20	−0.0427 (3)	0.5096 (3)	0.28200 (18)	0.0933 (11)
H20A	−0.1206	0.4969	0.2396	0.112*	0.40
H20B	−0.0243	0.5847	0.2750	0.112*	0.40
H20C	−0.0835	0.4599	0.3230	0.112*	0.60
H20D	−0.1041	0.5356	0.2278	0.112*	0.60
C21A	−0.0616 (8)	0.4970 (6)	0.3825 (5)	0.087 (2)	0.40
H21A	−0.1126	0.5548	0.4021	0.130*	0.40
H21B	0.0168	0.4979	0.4260	0.130*	0.40
H21C	−0.1025	0.4295	0.3905	0.130*	0.40
C21B	−0.0045 (4)	0.5913 (3)	0.3410 (3)	0.0682 (10)	0.60
H21D	−0.0740	0.6238	0.3677	0.102*	0.60
H21E	0.0343	0.6433	0.3009	0.102*	0.60
H21F	0.0544	0.5667	0.3976	0.102*	0.60

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0378 (6)	0.0446 (6)	0.0327 (6)	−0.0054 (5)	−0.0044 (4)	0.0012 (5)
O2	0.0489 (7)	0.0664 (8)	0.0276 (5)	0.0105 (6)	0.0063 (5)	−0.0013 (5)
O3	0.1238 (16)	0.0799 (12)	0.0495 (9)	0.0178 (11)	0.0366 (10)	0.0237 (8)
O4	0.0546 (7)	0.0354 (6)	0.0363 (6)	0.0023 (5)	0.0119 (5)	−0.0054 (5)
N1	0.0343 (6)	0.0374 (7)	0.0295 (6)	−0.0043 (5)	0.0066 (5)	−0.0014 (5)
N2	0.0315 (6)	0.0460 (8)	0.0335 (7)	0.0033 (5)	0.0082 (5)	0.0039 (5)
C1	0.0262 (7)	0.0369 (8)	0.0408 (8)	−0.0061 (6)	0.0069 (6)	−0.0092 (6)
C2	0.0311 (8)	0.0405 (9)	0.0665 (12)	−0.0018 (7)	0.0097 (7)	−0.0097 (8)
C3	0.0325 (8)	0.0572 (11)	0.0823 (15)	−0.0028 (8)	0.0150 (9)	−0.0345 (11)
C4	0.0425 (10)	0.0767 (14)	0.0525 (11)	−0.0087 (9)	0.0187 (8)	−0.0277 (11)
C5	0.0431 (9)	0.0687 (12)	0.0384 (9)	−0.0084 (9)	0.0145 (7)	−0.0118 (8)
C6	0.0284 (7)	0.0446 (8)	0.0342 (7)	−0.0080 (6)	0.0069 (6)	−0.0091 (6)
C7	0.0321 (7)	0.0331 (7)	0.0288 (7)	−0.0049 (6)	0.0046 (5)	−0.0023 (6)
C8	0.0298 (7)	0.0323 (7)	0.0290 (7)	−0.0023 (6)	0.0026 (5)	−0.0018 (6)
C9	0.0382 (8)	0.0387 (8)	0.0286 (7)	0.0014 (6)	0.0024 (6)	0.0013 (6)
C10	0.0418 (9)	0.0664 (12)	0.0345 (8)	0.0116 (8)	0.0077 (7)	0.0027 (8)
C11	0.0290 (7)	0.0337 (7)	0.0262 (6)	−0.0008 (6)	0.0044 (5)	0.0040 (5)
C12	0.0263 (7)	0.0366 (7)	0.0291 (7)	−0.0048 (6)	0.0047 (5)	0.0015 (6)
C13	0.0423 (8)	0.0380 (8)	0.0333 (7)	−0.0034 (7)	0.0030 (6)	0.0043 (6)
C14	0.0656 (12)	0.0352 (8)	0.0484 (10)	−0.0029 (8)	0.0056 (9)	0.0022 (7)
C15	0.0677 (12)	0.0445 (9)	0.0421 (9)	−0.0076 (9)	0.0077 (9)	−0.0097 (8)
C16	0.0518 (10)	0.0551 (10)	0.0302 (8)	−0.0082 (8)	0.0035 (7)	−0.0025 (7)
C17	0.0381 (8)	0.0415 (8)	0.0317 (7)	−0.0062 (7)	0.0030 (6)	0.0049 (6)
C18	0.0446 (9)	0.0502 (10)	0.0389 (8)	−0.0047 (8)	0.0070 (7)	0.0100 (7)
C19	0.0457 (10)	0.0418 (9)	0.0595 (11)	−0.0002 (8)	0.0075 (8)	0.0134 (8)
C20	0.0726 (16)	0.164 (3)	0.0447 (11)	0.0585 (19)	0.0121 (11)	−0.0109 (15)
C21A	0.119 (6)	0.095 (5)	0.059 (3)	0.061 (4)	0.062 (4)	0.027 (3)
C21B	0.065 (2)	0.068 (2)	0.071 (2)	0.0104 (19)	0.0068 (19)	−0.025 (2)

Geometric parameters (Å, º)

O1—C9	1.427 (2)	C12—C17	1.396 (2)
O1—C8	1.450 (2)	C13—C14	1.387 (2)
O2—C10	1.387 (2)	C13—H13	0.9300
O2—C9	1.422 (2)	C14—C15	1.379 (3)
O3—C18	1.203 (2)	C14—H14	0.9300
O4—C7	1.202 (2)	C15—C16	1.379 (3)
N1—C7	1.412 (2)	C15—H15	0.9300
N1—C18	1.413 (2)	C16—C17	1.385 (2)
N1—C6	1.435 (2)	C16—H16	0.9300
N2—C10	1.263 (2)	C17—H17	0.9300
N2—C11	1.465 (2)	C18—C19	1.486 (3)
C1—C2	1.382 (2)	C19—H19A	0.9600
C1—C6	1.389 (2)	C19—H19B	0.9600
C1—C8	1.490 (2)	C19—H19C	0.9600
C2—C3	1.397 (3)	C20—C21B	1.306 (5)
C2—H2	0.9300	C20—C21A	1.355 (5)
C3—C4	1.380 (3)	C20—H20A	0.9602
C3—H3	0.9300	C20—H20B	0.9601
C4—C5	1.382 (3)	C20—H20C	0.9600
C4—H4	0.9300	C20—H20D	0.9602
C5—C6	1.391 (2)	C21A—H20C	0.9045
C5—H5	0.9300	C21A—H21A	0.9600
C7—C8	1.533 (2)	C21A—H21B	0.9600
C8—C11	1.595 (2)	C21A—H21C	0.9600
C9—C11	1.541 (2)	C21B—H20B	0.8602
C9—H9	0.9800	C21B—H21D	0.9600
C10—C20	1.491 (3)	C21B—H21E	0.9600
C11—C12	1.498 (2)	C21B—H21F	0.9600
C12—C13	1.385 (2)
C9—O1—C8	93.6 (1)	C15—C14—H14	119.8
C10—O2—C9	105.7 (1)	C13—C14—H14	119.8
C7—N1—C18	126.5 (1)	C14—C15—C16	120.2 (2)
C7—N1—C6	108.8 (1)	C14—C15—H15	119.9
C18—N1—C6	124.2 (1)	C16—C15—H15	119.9
C10—N2—C11	106.6 (1)	C15—C16—C17	120.0 (2)
C2—C1—C6	120.8 (2)	C15—C16—H16	120.0
C2—C1—C8	129.7 (2)	C17—C16—H16	120.0
C6—C1—C8	109.2 (1)	C16—C17—C12	120.1 (2)
C1—C2—C3	118.0 (2)	C16—C17—H17	119.9
C1—C2—H2	121.0	C12—C17—H17	119.9
C3—C2—H2	121.0	O3—C18—N1	119.1 (2)
C4—C3—C2	120.6 (2)	O3—C18—C19	121.9 (2)
C4—C3—H3	119.7	N1—C18—C19	119.0 (2)
C2—C3—H3	119.7	C18—C19—H19A	109.5
C3—C4—C5	121.9 (2)	C18—C19—H19B	109.5
C3—C4—H4	119.1	H19A—C19—H19B	109.5
C5—C4—H4	119.1	C18—C19—H19C	109.5
C4—C5—C6	117.4 (2)	H19A—C19—H19C	109.5
C4—C5—H5	121.3	H19B—C19—H19C	109.5
C6—C5—H5	121.3	C21B—C20—C21A	66.5 (4)
C1—C6—C5	121.3 (2)	C21B—C20—C10	117.2 (3)
C1—C6—N1	109.8 (1)	C21A—C20—C10	124.1 (3)
C5—C6—N1	128.9 (2)	C21B—C20—H20A	130.8
O4—C7—N1	126.8 (1)	C21A—C20—H20A	107.6
O4—C7—C8	125.7 (1)	C10—C20—H20A	106.2
N1—C7—C8	107.5 (1)	C21B—C20—H20B	41.2
O1—C8—C1	118.7 (1)	C21A—C20—H20B	105.2
O1—C8—C7	112.2 (1)	C10—C20—H20B	106.2
C1—C8—C7	102.8 (1)	H20A—C20—H20B	106.5
O1—C8—C11	89.7 (1)	C21B—C20—H20C	108.0
C1—C8—C11	117.3 (1)	C21A—C20—H20C	41.8
C7—C8—C11	116.7 (1)	C10—C20—H20C	108.4
O2—C9—O1	113.5 (1)	H20A—C20—H20C	77.2
O2—C9—C11	104.5 (1)	H20B—C20—H20C	142.5
O1—C9—C11	92.8 (1)	C21B—C20—H20D	107.9
O2—C9—H9	114.6	C21A—C20—H20D	124.6
O1—C9—H9	114.6	C10—C20—H20D	107.7
C11—C9—H9	114.6	H20A—C20—H20D	32.8
N2—C10—O2	118.2 (2)	H20B—C20—H20D	74.8
N2—C10—C20	126.6 (2)	H20C—C20—H20D	107.3
O2—C10—C20	115.3 (2)	C20—C21A—H20C	45.0
N2—C11—C12	112.8 (1)	C20—C21A—H21A	109.5
N2—C11—C9	104.9 (1)	H20C—C21A—H21A	120.7
C12—C11—C9	122.0 (1)	C20—C21A—H21B	109.5
N2—C11—C8	113.4 (1)	H20C—C21A—H21B	128.6
C12—C11—C8	116.6 (1)	C20—C21A—H21C	109.5
C9—C11—C8	83.9 (1)	H20C—C21A—H21C	64.7
C13—C12—C17	119.4 (1)	C20—C21B—H20B	47.3
C13—C12—C11	121.9 (1)	C20—C21B—H21D	109.5
C17—C12—C11	118.7 (1)	C20—C21B—H21E	109.5
C12—C13—C14	120.0 (1)	H21D—C21B—H21E	109.5
C12—C13—H13	120.0	C20—C21B—H21F	109.5
C14—C13—H13	120.0	H21D—C21B—H21F	109.5
C15—C14—C13	120.3 (2)	H21E—C21B—H21F	109.5
C6—C1—C2—C3	−0.5 (2)	C9—O2—C10—C20	−176.6 (2)
C8—C1—C2—C3	173.8 (2)	C10—N2—C11—C12	133.2 (2)
C1—C2—C3—C4	−0.5 (3)	C10—N2—C11—C9	−1.7 (2)
C2—C3—C4—C5	1.0 (3)	C10—N2—C11—C8	−91.4 (2)
C3—C4—C5—C6	−0.5 (3)	O2—C9—C11—N2	3.5 (2)
C2—C1—C6—C5	1.1 (2)	O1—C9—C11—N2	−111.7 (1)
C8—C1—C6—C5	−174.3 (1)	O2—C9—C11—C12	−126.2 (1)
C2—C1—C6—N1	−177.2 (1)	O1—C9—C11—C12	118.7 (1)
C8—C1—C6—N1	7.5 (2)	O2—C9—C11—C8	116.1 (1)
C4—C5—C6—C1	−0.6 (2)	O1—C9—C11—C8	1.0 (1)
C4—C5—C6—N1	177.3 (2)	O1—C8—C11—N2	102.7 (1)
C7—N1—C6—C1	1.4 (2)	C1—C8—C11—N2	−134.9 (1)
C18—N1—C6—C1	174.0 (1)	C7—C8—C11—N2	−12.2 (2)
C7—N1—C6—C5	−176.6 (2)	O1—C8—C11—C12	−123.8 (1)
C18—N1—C6—C5	−4.0 (3)	C1—C8—C11—C12	−1.3 (2)
C18—N1—C7—O4	−3.9 (3)	C7—C8—C11—C12	121.4 (1)
C6—N1—C7—O4	168.5 (2)	O1—C8—C11—C9	−1.0 (1)
C18—N1—C7—C8	178.2 (1)	C1—C8—C11—C9	121.5 (1)
C6—N1—C7—C8	−9.4 (2)	C7—C8—C11—C9	−115.8 (1)
C9—O1—C8—C1	−120.3 (1)	N2—C11—C12—C13	−115.5 (2)
C9—O1—C8—C7	120.0 (1)	C9—C11—C12—C13	10.7 (2)
C9—O1—C8—C11	1.0 (1)	C8—C11—C12—C13	110.7 (2)
C2—C1—C8—O1	48.3 (2)	N2—C11—C12—C17	65.0 (2)
C6—C1—C8—O1	−136.9 (1)	C9—C11—C12—C17	−168.8 (1)
C2—C1—C8—C7	172.7 (2)	C8—C11—C12—C17	−68.9 (2)
C6—C1—C8—C7	−12.5 (2)	C17—C12—C13—C14	−0.1 (2)
C2—C1—C8—C11	−57.8 (2)	C11—C12—C13—C14	−179.6 (2)
C6—C1—C8—C11	117.1 (1)	C12—C13—C14—C15	0.4 (3)
O4—C7—C8—O1	−36.2 (2)	C13—C14—C15—C16	−0.1 (3)
N1—C7—C8—O1	141.8 (1)	C14—C15—C16—C17	−0.6 (3)
O4—C7—C8—C1	−164.8 (2)	C15—C16—C17—C12	0.9 (3)
N1—C7—C8—C1	13.2 (2)	C13—C12—C17—C16	−0.6 (2)
O4—C7—C8—C11	65.4 (2)	C11—C12—C17—C16	179.0 (2)
N1—C7—C8—C11	−116.7 (1)	C7—N1—C18—O3	−179.9 (2)
C10—O2—C9—O1	95.8 (2)	C6—N1—C18—O3	8.8 (3)
C10—O2—C9—C11	−3.9 (2)	C7—N1—C18—C19	0.8 (3)
C8—O1—C9—O2	−108.2 (1)	C6—N1—C18—C19	−170.5 (2)
C8—O1—C9—C11	−1.1 (1)	N2—C10—C20—C21B	−126.6 (3)
C11—N2—C10—O2	−0.9 (2)	O2—C10—C20—C21B	53.2 (4)
C11—N2—C10—C20	178.9 (3)	N2—C10—C20—C21A	154.6 (6)
C9—O2—C10—N2	3.3 (2)	O2—C10—C20—C21A	−25.6 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3	0.93	2.27	2.819 (3)	117

(II) 1-Acetyl-4',5a'-diphenylspiro[indole-3,2'-(2'H,5'H)oxeto[5,4-b]oxazol]-2(1H)- one

Crystal data

C25H18N2O4	Dx = 1.367 Mg m^−3
Mr = 410.41	Melting point: 426(1) K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.7908 (10) Å	Cell parameters from 3856 reflections
b = 8.7717 (7) Å	θ = 2.8–28.3°
c = 17.8346 (13) Å	µ = 0.09 mm^−1
β = 94.515 (2)°	T = 293 K
V = 1994.8 (3) Å^3	Needle, colorless
Z = 4	0.50 × 0.34 × 0.16 mm
F(000) = 856

Data collection

Siemens SMART CCD area-detector diffractometer	2826 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 25.0°, θmin = 2.8°
Detector resolution: 8.33 pixels mm^-1	h = −14→15
ω scans	k = −10→10
9586 measured reflections	l = −21→18
3505 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ^2(Fo^2) + (0.0375P)^2 + 1.5031P] where P = (Fo^2 + 2Fc^2)/3
3505 reflections	(Δ/σ)max < 0.001
341 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

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 5 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	0.12370 (13)	0.4653 (2)	0.22582 (10)	0.0381 (5)
O2	0.16984 (13)	0.6713 (2)	0.30749 (9)	0.0368 (5)
O3	−0.23260 (19)	0.0523 (3)	0.23692 (13)	0.0735 (8)
O4	−0.07084 (17)	0.3987 (3)	0.13512 (11)	0.0568 (6)
N1	−0.10004 (17)	0.2197 (3)	0.22777 (12)	0.0389 (6)
N2	0.02444 (16)	0.5968 (2)	0.36336 (12)	0.0351 (5)
C1	0.0423 (2)	0.2785 (3)	0.31117 (15)	0.0368 (6)
C2	0.1148 (2)	0.2561 (4)	0.37144 (17)	0.0478 (8)
H2	0.171 (2)	0.325 (3)	0.3827 (15)	0.041 (8)*
C3	0.1053 (3)	0.1290 (4)	0.41632 (19)	0.0562 (9)
H3	0.155 (2)	0.115 (3)	0.4593 (17)	0.055 (9)*
C4	0.0249 (3)	0.0272 (4)	0.40014 (19)	0.0557 (9)
H4	0.017 (3)	−0.059 (4)	0.4307 (18)	0.066 (10)*
C5	−0.0481 (3)	0.0468 (4)	0.33960 (18)	0.0489 (8)
H5	−0.101 (2)	−0.025 (4)	0.3275 (15)	0.048 (8)*
C6	−0.0380 (2)	0.1741 (3)	0.29502 (15)	0.0384 (6)
C7	−0.0516 (2)	0.3460 (3)	0.19673 (15)	0.0390 (7)
C8	0.03037 (19)	0.4066 (3)	0.25677 (14)	0.0341 (6)
C9	0.10082 (19)	0.6201 (3)	0.24561 (14)	0.0339 (6)
C10	0.1173 (2)	0.6494 (3)	0.37100 (14)	0.0327 (6)
C11	0.0025 (2)	0.5702 (3)	0.28350 (14)	0.0319 (6)
H11	−0.0671 (19)	0.603 (3)	0.2622 (13)	0.027 (6)*
C12	0.10247 (19)	0.7299 (3)	0.18164 (14)	0.0340 (6)
C13	0.0917 (2)	0.6806 (4)	0.10793 (16)	0.0455 (7)
H13	0.086 (2)	0.575 (3)	0.0991 (14)	0.040 (8)*
C14	0.0914 (3)	0.7843 (5)	0.04992 (18)	0.0597 (10)
H14	0.084 (2)	0.752 (4)	0.0003 (17)	0.053 (9)*
C15	0.1009 (3)	0.9379 (4)	0.06495 (19)	0.0587 (10)
H15	0.102 (2)	1.008 (4)	0.0240 (18)	0.066 (10)*
C16	0.1104 (3)	0.9886 (4)	0.13825 (19)	0.0535 (8)
H16	0.118 (3)	1.102 (4)	0.1515 (19)	0.075 (11)*
C17	0.1120 (2)	0.8846 (4)	0.19644 (17)	0.0452 (7)
H17	0.116 (2)	0.917 (4)	0.2473 (17)	0.057 (9)*
C18	−0.1962 (2)	0.1537 (4)	0.20135 (16)	0.0461 (7)
C19	−0.2502 (2)	0.2163 (4)	0.13127 (18)	0.0589 (9)
H19A	−0.3206	0.1776	0.1253	0.088*
H19B	−0.2131	0.1862	0.0890	0.088*
H19C	−0.2520	0.3255	0.1343	0.088*
C20	0.1759 (2)	0.6936 (3)	0.44198 (14)	0.0346 (6)
C21	0.1467 (2)	0.6347 (4)	0.50954 (16)	0.0438 (7)
H21	0.090 (2)	0.567 (3)	0.5099 (15)	0.042 (8)*
C22	0.2020 (3)	0.6752 (4)	0.57602 (18)	0.0540 (9)
H22	0.183 (2)	0.634 (3)	0.6196 (18)	0.054 (9)*
C23	0.2848 (3)	0.7740 (4)	0.57593 (19)	0.0583 (9)
H23	0.322 (2)	0.804 (4)	0.6191 (18)	0.061 (9)*
C24	0.3135 (3)	0.8347 (4)	0.50964 (18)	0.0528 (8)
H24	0.369 (2)	0.908 (4)	0.5076 (16)	0.053 (9)*
C25	0.2597 (2)	0.7939 (3)	0.44229 (17)	0.0426 (7)
H25	0.281 (2)	0.832 (3)	0.3960 (16)	0.048 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0340 (10)	0.0387 (11)	0.0419 (11)	0.0007 (8)	0.0056 (8)	−0.0006 (9)
O2	0.0331 (10)	0.0451 (11)	0.0316 (10)	−0.0069 (8)	−0.0019 (8)	0.0024 (8)
O3	0.0657 (16)	0.0875 (19)	0.0665 (16)	−0.0394 (14)	−0.0002 (12)	0.0084 (14)
O4	0.0679 (14)	0.0599 (14)	0.0399 (12)	−0.0202 (11)	−0.0125 (10)	0.0082 (11)
N1	0.0398 (13)	0.0366 (13)	0.0399 (13)	−0.0064 (10)	0.0009 (10)	−0.0009 (11)
N2	0.0324 (12)	0.0384 (13)	0.0345 (12)	0.0012 (10)	0.0015 (9)	−0.0013 (10)
C1	0.0396 (15)	0.0326 (15)	0.0383 (15)	0.0028 (12)	0.0046 (12)	−0.0005 (12)
C2	0.0477 (18)	0.0448 (18)	0.0492 (18)	0.0052 (15)	−0.0068 (15)	0.0039 (15)
C3	0.063 (2)	0.053 (2)	0.052 (2)	0.0176 (17)	−0.0023 (17)	0.0108 (17)
C4	0.072 (2)	0.0439 (19)	0.053 (2)	0.0128 (17)	0.0139 (18)	0.0154 (17)
C5	0.056 (2)	0.0372 (18)	0.0548 (19)	−0.0022 (15)	0.0117 (16)	0.0040 (15)
C6	0.0444 (16)	0.0321 (15)	0.0394 (15)	0.0029 (12)	0.0084 (12)	−0.0016 (12)
C7	0.0418 (16)	0.0376 (16)	0.0369 (16)	−0.0032 (12)	−0.0001 (12)	−0.0007 (13)
C8	0.0323 (14)	0.0322 (15)	0.0373 (15)	−0.0014 (11)	0.0003 (11)	0.0021 (12)
C9	0.0305 (13)	0.0350 (15)	0.0356 (14)	−0.0006 (11)	−0.0016 (11)	−0.0025 (12)
C10	0.0357 (15)	0.0272 (14)	0.0351 (14)	0.0034 (11)	0.0018 (11)	0.0040 (11)
C11	0.0288 (13)	0.0322 (14)	0.0338 (14)	0.0002 (11)	−0.0030 (11)	0.0013 (12)
C12	0.0286 (13)	0.0408 (16)	0.0326 (14)	−0.0031 (12)	0.0024 (11)	0.0025 (12)
C13	0.0512 (18)	0.051 (2)	0.0343 (16)	−0.0140 (15)	0.0004 (13)	0.0006 (14)
C14	0.063 (2)	0.083 (3)	0.0319 (17)	−0.0227 (19)	−0.0034 (15)	0.0087 (18)
C15	0.052 (2)	0.068 (3)	0.055 (2)	−0.0101 (17)	−0.0043 (16)	0.0333 (19)
C16	0.055 (2)	0.046 (2)	0.060 (2)	−0.0010 (15)	0.0102 (16)	0.0175 (17)
C17	0.0526 (18)	0.0439 (18)	0.0399 (17)	0.0007 (14)	0.0078 (14)	0.0042 (14)
C18	0.0448 (17)	0.0487 (19)	0.0451 (17)	−0.0091 (15)	0.0063 (14)	−0.0117 (15)
C19	0.0445 (18)	0.071 (2)	0.060 (2)	−0.0133 (16)	−0.0049 (15)	−0.0059 (18)
C20	0.0382 (15)	0.0292 (14)	0.0358 (15)	0.0055 (12)	−0.0009 (11)	−0.0007 (12)
C21	0.0473 (18)	0.0459 (18)	0.0382 (17)	0.0003 (15)	0.0041 (14)	0.0012 (14)
C22	0.073 (2)	0.057 (2)	0.0330 (17)	0.0093 (18)	0.0051 (16)	0.0009 (16)
C23	0.072 (2)	0.058 (2)	0.042 (2)	0.0024 (18)	−0.0161 (17)	−0.0130 (17)
C24	0.060 (2)	0.0459 (19)	0.050 (2)	−0.0069 (16)	−0.0115 (16)	−0.0092 (16)
C25	0.0479 (17)	0.0389 (17)	0.0403 (17)	−0.0002 (13)	−0.0016 (14)	−0.0002 (14)

Geometric parameters (Å, º)

O1—C9	1.439 (3)	C11—H11	0.98 (2)
O1—C8	1.449 (3)	C12—C13	1.380 (4)
O2—C10	1.375 (3)	C12—C17	1.386 (4)
O2—C9	1.430 (3)	C13—C14	1.377 (4)
O3—C18	1.207 (4)	C13—H13	0.94 (3)
O4—C7	1.200 (3)	C14—C15	1.377 (5)
N1—C7	1.404 (3)	C14—H14	0.93 (3)
N1—C18	1.406 (3)	C15—C16	1.377 (5)
N1—C6	1.442 (3)	C15—H15	0.95 (3)
N2—C10	1.271 (3)	C16—C17	1.380 (4)
N2—C11	1.449 (3)	C16—H16	1.02 (4)
C1—C2	1.377 (4)	C17—H17	0.95 (3)
C1—C6	1.389 (4)	C18—C19	1.485 (4)
C1—C8	1.484 (4)	C19—H19A	0.9600
C2—C3	1.383 (4)	C19—H19B	0.9600
C2—H2	0.95 (3)	C19—H19C	0.9600
C3—C4	1.375 (5)	C20—C25	1.387 (4)
C3—H3	0.97 (3)	C20—C21	1.389 (4)
C4—C5	1.382 (5)	C21—C22	1.378 (4)
C4—H4	0.95 (3)	C21—H21	0.94 (3)
C5—C6	1.382 (4)	C22—C23	1.368 (5)
C5—H5	0.94 (3)	C22—H22	0.91 (3)
C7—C8	1.534 (4)	C23—C24	1.373 (5)
C8—C11	1.563 (4)	C23—H23	0.91 (3)
C9—C12	1.494 (4)	C24—C25	1.383 (4)
C9—C11	1.537 (4)	C24—H24	0.97 (3)
C10—C20	1.472 (4)	C25—H25	0.95 (3)
C9—O1—C8	93.0 (2)	C8—C11—H11	111.9 (15)
C10—O2—C9	106.2 (2)	C13—C12—C17	119.2 (3)
C7—N1—C18	126.4 (2)	C13—C12—C9	121.3 (3)
C7—N1—C6	108.4 (2)	C17—C12—C9	119.5 (2)
C18—N1—C6	125.1 (2)	C14—C13—C12	120.2 (3)
C10—N2—C11	105.7 (2)	C14—C13—H13	122 (2)
C2—C1—C6	120.6 (3)	C12—C13—H13	118 (2)
C2—C1—C8	130.3 (3)	C13—C14—C15	120.3 (3)
C6—C1—C8	109.1 (2)	C13—C14—H14	121 (2)
C1—C2—C3	118.9 (3)	C15—C14—H14	119 (2)
C1—C2—H2	122 (2)	C16—C15—C14	120.0 (3)
C3—C2—H2	119 (2)	C16—C15—H15	121 (2)
C4—C3—C2	120.0 (3)	C14—C15—H15	119 (2)
C4—C3—H3	121 (2)	C15—C16—C17	119.7 (3)
C2—C3—H3	119 (2)	C15—C16—H16	122.1 (19)
C3—C4—C5	122.1 (3)	C17—C16—H16	118.2 (19)
C3—C4—H4	121 (2)	C16—C17—C12	120.5 (3)
C5—C4—H4	117 (2)	C16—C17—H17	121 (2)
C4—C5—C6	117.5 (3)	C12—C17—H17	118 (2)
C4—C5—H5	122 (2)	O3—C18—N1	119.4 (3)
C6—C5—H5	121 (2)	O3—C18—C19	122.8 (3)
C5—C6—C1	121.0 (3)	N1—C18—C19	117.8 (3)
C5—C6—N1	129.2 (3)	C18—C19—H19A	109.5
C1—C6—N1	109.8 (2)	C18—C19—H19B	109.5
O4—C7—N1	126.9 (2)	H19A—C19—H19B	109.5
O4—C7—C8	125.8 (2)	C18—C19—H19C	109.5
N1—C7—C8	107.3 (2)	H19A—C19—H19C	109.5
O1—C8—C1	118.2 (2)	H19B—C19—H19C	109.5
O1—C8—C7	113.3 (2)	C25—C20—C21	119.5 (3)
C1—C8—C7	102.9 (2)	C25—C20—C10	120.8 (2)
O1—C8—C11	90.3 (2)	C21—C20—C10	119.7 (2)
C1—C8—C11	120.7 (2)	C22—C21—C20	119.7 (3)
C7—C8—C11	111.8 (2)	C22—C21—H21	120 (2)
O2—C9—O1	111.1 (2)	C20—C21—H21	120 (2)
O2—C9—C12	110.0 (2)	C23—C22—C21	120.5 (3)
O1—C9—C12	113.9 (2)	C23—C22—H22	121 (2)
O2—C9—C11	103.1 (2)	C21—C22—H22	119 (2)
O1—C9—C11	91.6 (2)	C22—C23—C24	120.4 (3)
C12—C9—C11	125.5 (2)	C22—C23—H23	122 (2)
N2—C10—O2	118.4 (2)	C24—C23—H23	117 (2)
N2—C10—C20	126.6 (2)	C23—C24—C25	119.9 (3)
O2—C10—C20	115.0 (2)	C23—C24—H24	123 (2)
N2—C11—C9	106.5 (2)	C25—C24—H24	117 (2)
N2—C11—C8	114.6 (2)	C24—C25—C20	119.9 (3)
C9—C11—C8	85.0 (2)	C24—C25—H25	120 (2)
N2—C11—H11	116 (1)	C20—C25—H25	120 (2)
C9—C11—H11	120 (1)
C6—C1—C2—C3	−1.0 (4)	C10—N2—C11—C9	−0.8 (3)
C8—C1—C2—C3	176.6 (3)	C10—N2—C11—C8	91.3 (3)
C1—C2—C3—C4	0.4 (5)	O2—C9—C11—N2	−0.3 (3)
C2—C3—C4—C5	0.1 (5)	O1—C9—C11—N2	111.9 (2)
C3—C4—C5—C6	−0.1 (5)	C12—C9—C11—N2	−126.9 (3)
C4—C5—C6—C1	−0.5 (4)	O2—C9—C11—C8	−114.5 (2)
C4—C5—C6—N1	177.7 (3)	O1—C9—C11—C8	−2.3 (2)
C2—C1—C6—C5	1.1 (4)	C12—C9—C11—C8	118.9 (3)
C8—C1—C6—C5	−177.0 (2)	O1—C8—C11—N2	−103.6 (2)
C2—C1—C6—N1	−177.4 (2)	C1—C8—C11—N2	19.9 (3)
C8—C1—C6—N1	4.5 (3)	C7—C8—C11—N2	141.0 (2)
C7—N1—C6—C5	−172.2 (3)	O1—C8—C11—C9	2.3 (2)
C18—N1—C6—C5	11.6 (4)	C1—C8—C11—C9	125.8 (2)
C7—N1—C6—C1	6.2 (3)	C7—C8—C11—C9	−113.1 (2)
C18—N1—C6—C1	−170.0 (3)	O2—C9—C12—C13	145.9 (2)
C18—N1—C7—O4	−17.0 (5)	O1—C9—C12—C13	20.3 (3)
C6—N1—C7—O4	166.9 (3)	C11—C9—C12—C13	−90.4 (3)
C18—N1—C7—C8	162.3 (2)	O2—C9—C12—C17	−36.0 (3)
C6—N1—C7—C8	−13.8 (3)	O1—C9—C12—C17	−161.5 (2)
C9—O1—C8—C1	−128.0 (2)	C11—C9—C12—C17	87.8 (3)
C9—O1—C8—C7	111.5 (2)	C17—C12—C13—C14	0.5 (4)
C9—O1—C8—C11	−2.5 (2)	C9—C12—C13—C14	178.7 (3)
C2—C1—C8—O1	44.2 (4)	C12—C13—C14—C15	−0.5 (5)
C6—C1—C8—O1	−138.0 (2)	C13—C14—C15—C16	−0.3 (5)
C2—C1—C8—C7	169.9 (3)	C14—C15—C16—C17	1.1 (5)
C6—C1—C8—C7	−12.2 (3)	C15—C16—C17—C12	−1.1 (5)
C2—C1—C8—C11	−64.7 (4)	C13—C12—C17—C16	0.3 (4)
C6—C1—C8—C11	113.1 (3)	C9—C12—C17—C16	−177.9 (3)
O4—C7—C8—O1	−36.0 (4)	C7—N1—C18—O3	−174.4 (3)
N1—C7—C8—O1	144.7 (2)	C6—N1—C18—O3	1.1 (4)
O4—C7—C8—C1	−164.9 (3)	C7—N1—C18—C19	3.8 (4)
N1—C7—C8—C1	15.9 (3)	C6—N1—C18—C19	179.3 (3)
O4—C7—C8—C11	64.2 (4)	N2—C10—C20—C25	−158.4 (3)
N1—C7—C8—C11	−115.1 (2)	O2—C10—C20—C25	20.3 (4)
C10—O2—C9—O1	−95.9 (2)	N2—C10—C20—C21	21.4 (4)
C10—O2—C9—C12	137.0 (2)	O2—C10—C20—C21	−159.9 (2)
C10—O2—C9—C11	1.1 (2)	C25—C20—C21—C22	−0.6 (4)
C8—O1—C9—O2	107.2 (2)	C10—C20—C21—C22	179.6 (3)
C8—O1—C9—C12	−127.9 (2)	C20—C21—C22—C23	0.5 (5)
C8—O1—C9—C11	2.49 (18)	C21—C22—C23—C24	0.4 (5)
C11—N2—C10—O2	1.7 (3)	C22—C23—C24—C25	−1.1 (5)
C11—N2—C10—C20	−179.6 (2)	C23—C24—C25—C20	1.0 (5)
C9—O2—C10—N2	−1.9 (3)	C21—C20—C25—C24	−0.1 (4)
C9—O2—C10—C20	179.3 (2)	C10—C20—C25—C24	179.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3	0.92 (3)	2.36 (3)	2.872 (4)	115 (3)