1-Acetyl-7a′-phenylspiro­[3H-indole-3,2′(2a′H)-oxeto­[2,3-b]­benzo­furan]-2(1H)-one

In the title compound, C₂₄H₁₇NO₄, the oxetane ring deviates from planarity. The benzo­furan and indole moieties are in synclinal configurations, and the attached phenyl ring forms a dihedral angle of 68.0 (2)° with respect to the oxetane ring. Intramolecular C—H...O interactions stabilize the molecular structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.064
• wR factor = 0.169
• Data-to-parameter ratio = 12.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

The photoinduced reactions of 1H-indole-2,3-dione (isatin) derivatives, which are compounds of interest mainly due to their biological activities (Bieck et al., 1993) and their widespread use as synthetic precursors of many natural and unnatural products (Popp, 1975; Shvekhgeimer, 1996), have been investigated intensively (Ling et al., 1998; Xue et al., 2000, 2001) in order to extend the scope of the photoinduced reactions of carbonyl compounds. The title compound, (I), was one of the two diastereomers obtained in the photoinduced reaction of 1-acetylisatin with 2-phenylbenzofuran. To confirm its conformation and stereochemistry an X-ray structure determination of (I) was undertaken.

The bond lengths and angles observed in the title compound show normal values (Allen et al., 1987). These values within the indole and oxetene moieties agree with those of the corresponding related structures previously studied (Zukerman-Schpector et al., 1992; Prakash et al., 1997). The oxetane ring shows a slight puckering and therefore deviates from planarity, with a maximum deviation of -0.025 (3) Å and a dihedral angle of 174.6 (3)° between the O3/C8/C16 and C8/C9/C16 planes. Non-planar oxetanes also are observed in other derivatives (Morris et al., 1987; Khan et al., 1991; Prakash et al., 1997). The benzofuran and indole moieties are almost planar and make dihedral angles of 65.5 (2) and 89.0 (2)° with the mean plane through the oxetane. This corresponds to the synclinal configuration for the two moieties with respect to the oxetane. The angle C9—C16—C17 is 123.4 (2)°, implying that the attached phenyl ring is pushed slightly away from the benzofuran and indole moieties, and it forms a dihedral angle of 68.0 (2)° with the oxetane ring. Atom O2 deviates by -0.092 (2) Å from the mean plane of the indole moiety, while the acetyl group attached at N1 is twisted by 13.9 (2)° from the plane. The O1 atom of the acetyl group and the O2 atom show weak intramolecular hydrogen-bond interactions (Table 2) forming closed rings O1—C23—N1—C2—C3—H3A and O3—C16—C17—C22—H22A. These interactions stabilize the molecular structure.

S2. Experimental

The title compound, (I), was prepared by the photoinduced reaction (Peterno-Büchi reaction; Arnold, 1968) of a benzene solution (40 ml) of 1-acetylisatin (0.05 M) and 2-phenylbenzofuran (0.1 M) with a Pyrex-filtered light of a medium-pressure mercury lamp (500 W, λ > 400 nm). The reaction was carried out under constant nitrogen purging. After irradiation, the solvent was removed in vacuo and the residue was separated by column chromatography. Compound (I) was obtained as the main diastereomer of the product and was recrystallized from a mixture of petroleum ether and ethyl acetate.

S3. Refinement

After checking their presence in the difference map, all H atoms were geometrically fixed and allowed to ride on the parent C atoms and refined isotropically. Due to a large fraction of weak data at higher angles, the 2θ maximum was limited to 50°.

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 (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme.

1-Acetyl-7a'-phenyl-spiro[3H-indole-3,2'(2a'H)oxeto [2,3-b]benzofuran-2(1H)-one

Crystal data

C24H17NO4	F(000) = 400
Mr = 383.39	Dx = 1.370 Mg m^−3
Triclinic, P1	Melting point: 477 K
a = 9.2136 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2904 (3) Å	Cell parameters from 3227 reflections
c = 10.9603 (3) Å	θ = 2.0–28.3°
α = 68.119 (1)°	µ = 0.09 mm^−1
β = 80.830 (1)°	T = 293 K
γ = 75.083 (1)°	Slab, colourless
V = 929.47 (4) Å^3	0.36 × 0.28 × 0.18 mm
Z = 2

Data collection

Siemens SMART CCD area-detector diffractometer	2148 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
Detector resolution: 8.33 pixels mm^-1	h = −10→9
ω scans	k = −12→8
5322 measured reflections	l = −13→12
3231 independent 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)] = 0.064	H-atom parameters constrained
wR(F^2) = 0.169	w = 1/[σ^2(Fo^2) + (0.0957P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.94	(Δ/σ)max < 0.001
3231 reflections	Δρmax = 0.29 e Å^−3
264 parameters	Δρmin = −0.31 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: 0.081 (8)

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	0.4871 (2)	0.1249 (3)	0.2689 (2)	0.0686 (7)
O2	0.6613 (2)	0.2085 (2)	0.54998 (19)	0.0495 (5)
O3	0.38393 (19)	0.38228 (18)	0.64948 (16)	0.0403 (5)
O4	0.3178 (2)	0.3650 (2)	0.87177 (18)	0.0472 (5)
N1	0.4705 (2)	0.1806 (2)	0.45250 (19)	0.0332 (5)
C1	0.5315 (3)	0.2088 (3)	0.5471 (2)	0.0336 (6)
C2	0.3150 (3)	0.1753 (3)	0.4911 (2)	0.0328 (6)
C3	0.2134 (3)	0.1497 (3)	0.4279 (3)	0.0437 (7)
H3A	0.2424	0.1266	0.3520	0.052*
C4	0.0660 (3)	0.1599 (3)	0.4823 (3)	0.0484 (7)
H4A	−0.0050	0.1429	0.4417	0.058*
C5	0.0217 (3)	0.1945 (3)	0.5946 (3)	0.0509 (8)
H5A	−0.0782	0.2012	0.6283	0.061*
C6	0.1242 (3)	0.2193 (3)	0.6570 (3)	0.0463 (7)
H6A	0.0946	0.2429	0.7327	0.056*
C7	0.2721 (3)	0.2086 (3)	0.6059 (2)	0.0357 (6)
C8	0.4033 (3)	0.2369 (3)	0.6491 (2)	0.0347 (6)
C9	0.4514 (3)	0.1737 (3)	0.7929 (2)	0.0329 (6)
H9A	0.5527	0.1125	0.8058	0.039*
C10	0.3338 (3)	0.1269 (3)	0.9002 (2)	0.0355 (6)
C11	0.2916 (3)	−0.0022 (3)	0.9607 (2)	0.0432 (7)
H11A	0.3401	−0.0808	0.9361	0.052*
C12	0.1750 (3)	−0.0135 (4)	1.0594 (3)	0.0560 (8)
H12A	0.1449	−0.1003	1.1009	0.067*
C13	0.1040 (4)	0.1030 (4)	1.0961 (3)	0.0621 (9)
H13A	0.0266	0.0935	1.1625	0.075*
C14	0.1454 (3)	0.2346 (4)	1.0360 (3)	0.0545 (8)
H14A	0.0969	0.3133	1.0604	0.065*
C15	0.2618 (3)	0.2433 (3)	0.9387 (2)	0.0410 (7)
C16	0.4378 (3)	0.3324 (3)	0.7788 (2)	0.0378 (7)
C17	0.5684 (3)	0.3908 (3)	0.7850 (2)	0.0375 (6)
C18	0.6015 (3)	0.3906 (3)	0.9045 (3)	0.0468 (7)
H18A	0.5379	0.3608	0.9795	0.056*
C19	0.7282 (4)	0.4345 (3)	0.9125 (3)	0.0572 (8)
H19A	0.7497	0.4333	0.9930	0.069*
C20	0.8231 (4)	0.4800 (3)	0.8018 (3)	0.0559 (8)
H20A	0.9085	0.5090	0.8077	0.067*
C21	0.7908 (3)	0.4822 (3)	0.6834 (3)	0.0494 (8)
H21A	0.8550	0.5122	0.6089	0.059*
C22	0.6631 (3)	0.4400 (3)	0.6737 (3)	0.0444 (7)
H22A	0.6407	0.4446	0.5922	0.053*
C23	0.5448 (3)	0.1673 (3)	0.3331 (3)	0.0431 (7)
C24	0.6938 (3)	0.2084 (4)	0.2925 (3)	0.0580 (9)
H24C	0.7254	0.2086	0.2046	0.087*
H24A	0.7668	0.1407	0.3519	0.087*
H24B	0.6853	0.3025	0.2947	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0626 (14)	0.113 (2)	0.0514 (13)	−0.0160 (13)	−0.0005 (11)	−0.0565 (14)
O2	0.0356 (12)	0.0732 (14)	0.0490 (12)	−0.0110 (9)	0.0006 (9)	−0.0336 (11)
O3	0.0535 (11)	0.0343 (10)	0.0319 (10)	−0.0038 (8)	−0.0086 (8)	−0.0118 (8)
O4	0.0573 (12)	0.0472 (12)	0.0394 (11)	−0.0095 (9)	0.0094 (9)	−0.0240 (9)
N1	0.0371 (12)	0.0384 (12)	0.0245 (11)	−0.0053 (9)	−0.0015 (9)	−0.0135 (9)
C1	0.0369 (15)	0.0363 (15)	0.0285 (13)	−0.0059 (10)	−0.0028 (11)	−0.0134 (11)
C2	0.0392 (15)	0.0333 (14)	0.0242 (13)	−0.0058 (11)	−0.0053 (11)	−0.0083 (11)
C3	0.0491 (17)	0.0462 (17)	0.0385 (15)	−0.0082 (12)	−0.0071 (13)	−0.0178 (13)
C4	0.0452 (17)	0.0501 (18)	0.0546 (18)	−0.0137 (13)	−0.0153 (14)	−0.0163 (14)
C5	0.0377 (16)	0.064 (2)	0.0481 (18)	−0.0119 (13)	−0.0034 (13)	−0.0149 (15)
C6	0.0390 (16)	0.0587 (19)	0.0390 (16)	−0.0063 (13)	−0.0020 (12)	−0.0175 (14)
C7	0.0370 (14)	0.0372 (15)	0.0306 (14)	−0.0046 (11)	−0.0053 (11)	−0.0103 (11)
C8	0.0402 (15)	0.0367 (15)	0.0281 (13)	−0.0043 (11)	−0.0044 (11)	−0.0142 (11)
C9	0.0404 (14)	0.0377 (15)	0.0226 (12)	−0.0079 (11)	−0.0038 (10)	−0.0125 (11)
C10	0.0431 (15)	0.0432 (16)	0.0201 (12)	−0.0087 (11)	−0.0054 (11)	−0.0102 (11)
C11	0.0546 (18)	0.0438 (17)	0.0309 (14)	−0.0132 (13)	−0.0053 (13)	−0.0099 (12)
C12	0.060 (2)	0.070 (2)	0.0394 (16)	−0.0295 (16)	0.0032 (15)	−0.0131 (16)
C13	0.056 (2)	0.091 (3)	0.0418 (17)	−0.0266 (18)	0.0118 (15)	−0.0244 (18)
C14	0.0515 (18)	0.074 (2)	0.0436 (17)	−0.0108 (15)	0.0088 (14)	−0.0328 (16)
C15	0.0460 (16)	0.0508 (18)	0.0284 (14)	−0.0110 (13)	−0.0023 (12)	−0.0158 (13)
C16	0.0494 (16)	0.0400 (16)	0.0244 (13)	−0.0052 (12)	−0.0022 (11)	−0.0150 (11)
C17	0.0516 (16)	0.0296 (14)	0.0325 (14)	−0.0088 (11)	−0.0025 (12)	−0.0122 (11)
C18	0.066 (2)	0.0441 (17)	0.0354 (15)	−0.0178 (14)	−0.0022 (13)	−0.0157 (13)
C19	0.077 (2)	0.060 (2)	0.0423 (17)	−0.0212 (16)	−0.0138 (16)	−0.0189 (15)
C20	0.065 (2)	0.0475 (19)	0.059 (2)	−0.0215 (15)	−0.0082 (16)	−0.0154 (15)
C21	0.0581 (19)	0.0396 (17)	0.0468 (17)	−0.0162 (13)	0.0037 (14)	−0.0101 (13)
C22	0.0611 (19)	0.0374 (16)	0.0325 (14)	−0.0115 (13)	−0.0025 (13)	−0.0096 (12)
C23	0.0483 (17)	0.0529 (18)	0.0257 (14)	−0.0021 (13)	−0.0022 (12)	−0.0170 (13)
C24	0.056 (2)	0.082 (2)	0.0345 (16)	−0.0188 (16)	0.0116 (14)	−0.0216 (16)

Geometric parameters (Å, º)

O1—C23	1.199 (3)	C10—C15	1.391 (4)
O2—C1	1.201 (3)	C11—C12	1.393 (4)
O3—C16	1.439 (3)	C11—H11A	0.930
O3—C8	1.462 (3)	C12—C13	1.378 (4)
O4—C15	1.378 (3)	C12—H12A	0.930
O4—C16	1.442 (3)	C13—C14	1.390 (4)
N1—C1	1.403 (3)	C13—H13A	0.930
N1—C23	1.414 (3)	C14—C15	1.382 (4)
N1—C2	1.437 (3)	C14—H14A	0.930
C1—C8	1.541 (3)	C16—C17	1.497 (4)
C2—C3	1.376 (4)	C17—C18	1.390 (4)
C2—C7	1.396 (3)	C17—C22	1.391 (4)
C3—C4	1.388 (4)	C18—C19	1.381 (4)
C3—H3A	0.930	C18—H18A	0.930
C4—C5	1.379 (4)	C19—C20	1.380 (4)
C4—H4A	0.930	C19—H19A	0.930
C5—C6	1.373 (4)	C20—C21	1.367 (4)
C5—H5A	0.930	C20—H20A	0.930
C6—C7	1.382 (4)	C21—C22	1.386 (4)
C6—H6A	0.930	C21—H21A	0.930
C7—C8	1.495 (3)	C22—H22A	0.930
C8—C9	1.553 (3)	C23—C24	1.492 (4)
C9—C10	1.493 (3)	C24—H24C	0.960
C9—C16	1.555 (3)	C24—H24A	0.960
C9—H9A	0.980	C24—H24B	0.960
C10—C11	1.372 (4)
C16—O3—C8	93.09 (16)	C13—C12—H12A	119.8
C15—O4—C16	107.99 (19)	C11—C12—H12A	119.8
C1—N1—C23	126.5 (2)	C12—C13—C14	121.5 (3)
C1—N1—C2	109.43 (18)	C12—C13—H13A	119.2
C23—N1—C2	124.0 (2)	C14—C13—H13A	119.2
O2—C1—N1	126.2 (2)	C15—C14—C13	117.2 (3)
O2—C1—C8	125.7 (2)	C15—C14—H14A	121.4
N1—C1—C8	108.1 (2)	C13—C14—H14A	121.4
C3—C2—C7	121.5 (2)	O4—C15—C14	124.2 (3)
C3—C2—N1	128.8 (2)	O4—C15—C10	113.8 (2)
C7—C2—N1	109.6 (2)	C14—C15—C10	121.9 (3)
C2—C3—C4	117.2 (3)	O3—C16—O4	110.5 (2)
C2—C3—H3A	121.4	O3—C16—C17	114.3 (2)
C4—C3—H3A	121.4	O4—C16—C17	109.1 (2)
C5—C4—C3	121.9 (3)	O3—C16—C9	91.08 (17)
C5—C4—H4A	119.1	O4—C16—C9	107.13 (19)
C3—C4—H4A	119.1	C17—C16—C9	123.4 (2)
C6—C5—C4	120.3 (3)	C18—C17—C22	118.5 (3)
C6—C5—H5A	119.8	C18—C17—C16	120.3 (2)
C4—C5—H5A	119.8	C22—C17—C16	121.2 (2)
C5—C6—C7	119.0 (3)	C19—C18—C17	120.4 (3)
C5—C6—H6A	120.5	C19—C18—H18A	119.8
C7—C6—H6A	120.5	C17—C18—H18A	119.8
C6—C7—C2	120.0 (2)	C20—C19—C18	120.4 (3)
C6—C7—C8	130.1 (2)	C20—C19—H19A	119.8
C2—C7—C8	109.7 (2)	C18—C19—H19A	119.8
O3—C8—C7	115.07 (19)	C21—C20—C19	119.6 (3)
O3—C8—C1	110.00 (19)	C21—C20—H20A	120.2
C7—C8—C1	102.86 (19)	C19—C20—H20A	120.2
O3—C8—C9	90.29 (16)	C20—C21—C22	120.5 (3)
C7—C8—C9	124.6 (2)	C20—C21—H21A	119.7
C1—C8—C9	113.71 (19)	C22—C21—H21A	119.7
C10—C9—C8	117.0 (2)	C21—C22—C17	120.4 (3)
C10—C9—C16	103.13 (19)	C21—C22—H22A	119.8
C8—C9—C16	85.28 (17)	C17—C22—H22A	119.8
C10—C9—H9A	115.6	O1—C23—N1	119.8 (3)
C8—C9—H9A	115.6	O1—C23—C24	122.8 (2)
C16—C9—H9A	115.6	N1—C23—C24	117.5 (2)
C11—C10—C15	120.1 (2)	C23—C24—H24C	109.5
C11—C10—C9	132.1 (2)	C23—C24—H24A	109.5
C15—C10—C9	107.9 (2)	H24C—C24—H24A	109.5
C10—C11—C12	118.9 (3)	C23—C24—H24B	109.5
C10—C11—H11A	120.5	H24C—C24—H24B	109.5
C12—C11—H11A	120.5	H24A—C24—H24B	109.5
C13—C12—C11	120.4 (3)
C23—N1—C1—O2	−9.9 (4)	C15—C10—C11—C12	0.7 (4)
C2—N1—C1—O2	173.5 (2)	C9—C10—C11—C12	−179.7 (3)
C23—N1—C1—C8	171.4 (2)	C10—C11—C12—C13	−0.4 (4)
C2—N1—C1—C8	−5.2 (3)	C11—C12—C13—C14	0.3 (5)
C1—N1—C2—C3	−179.5 (2)	C12—C13—C14—C15	−0.5 (5)
C23—N1—C2—C3	3.8 (4)	C16—O4—C15—C14	179.9 (3)
C1—N1—C2—C7	3.6 (3)	C16—O4—C15—C10	0.3 (3)
C23—N1—C2—C7	−173.0 (2)	C13—C14—C15—O4	−178.7 (3)
C7—C2—C3—C4	0.6 (4)	C13—C14—C15—C10	0.9 (4)
N1—C2—C3—C4	−175.8 (2)	C11—C10—C15—O4	178.6 (2)
C2—C3—C4—C5	0.2 (4)	C9—C10—C15—O4	−1.1 (3)
C3—C4—C5—C6	−0.4 (5)	C11—C10—C15—C14	−1.0 (4)
C4—C5—C6—C7	−0.2 (4)	C9—C10—C15—C14	179.3 (2)
C5—C6—C7—C2	1.0 (4)	C8—O3—C16—O4	−112.7 (2)
C5—C6—C7—C8	176.5 (3)	C8—O3—C16—C17	123.9 (2)
C3—C2—C7—C6	−1.3 (4)	C8—O3—C16—C9	−3.93 (17)
N1—C2—C7—C6	175.8 (2)	C15—O4—C16—O3	98.4 (2)
C3—C2—C7—C8	−177.6 (2)	C15—O4—C16—C17	−135.2 (2)
N1—C2—C7—C8	−0.5 (3)	C15—O4—C16—C9	0.6 (2)
C16—O3—C8—C7	132.9 (2)	C10—C9—C16—O3	−112.98 (19)
C16—O3—C8—C1	−111.5 (2)	C8—C9—C16—O3	3.71 (16)
C16—O3—C8—C9	3.94 (18)	C10—C9—C16—O4	−1.2 (2)
C6—C7—C8—O3	−58.7 (4)	C8—C9—C16—O4	115.5 (2)
C2—C7—C8—O3	117.2 (2)	C10—C9—C16—C17	126.7 (2)
C6—C7—C8—C1	−178.3 (3)	C8—C9—C16—C17	−116.6 (2)
C2—C7—C8—C1	−2.5 (3)	O3—C16—C17—C18	159.5 (2)
C6—C7—C8—C9	50.5 (4)	O4—C16—C17—C18	35.3 (3)
C2—C7—C8—C9	−133.6 (2)	C9—C16—C17—C18	−91.7 (3)
O2—C1—C8—O3	62.9 (3)	O3—C16—C17—C22	−23.6 (3)
N1—C1—C8—O3	−118.4 (2)	O4—C16—C17—C22	−147.8 (2)
O2—C1—C8—C7	−174.1 (3)	C9—C16—C17—C22	85.2 (3)
N1—C1—C8—C7	4.6 (3)	C22—C17—C18—C19	−1.8 (4)
O2—C1—C8—C9	−36.7 (4)	C16—C17—C18—C19	175.2 (3)
N1—C1—C8—C9	142.0 (2)	C17—C18—C19—C20	0.4 (5)
O3—C8—C9—C10	98.7 (2)	C18—C19—C20—C21	0.3 (5)
C7—C8—C9—C10	−22.5 (3)	C19—C20—C21—C22	0.5 (5)
C1—C8—C9—C10	−149.2 (2)	C20—C21—C22—C17	−1.9 (4)
O3—C8—C9—C16	−3.65 (16)	C18—C17—C22—C21	2.6 (4)
C7—C8—C9—C16	−124.9 (2)	C16—C17—C22—C21	−174.4 (2)
C1—C8—C9—C16	108.4 (2)	C1—N1—C23—O1	170.4 (3)
C8—C9—C10—C11	90.3 (3)	C2—N1—C23—O1	−13.5 (4)
C16—C9—C10—C11	−178.3 (3)	C1—N1—C23—C24	−9.9 (4)
C8—C9—C10—C15	−90.1 (3)	C2—N1—C23—C24	166.2 (2)
C16—C9—C10—C15	1.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1	0.93	2.29	2.839 (4)	117
C22—H22A···O3	0.93	2.53	2.857 (3)	100