4-Meth-oxy-5-[4-(4-meth-oxy-1,3-benzodioxol-5-yl)perhydro-1H,3H-furo[3,4-c]furan-1-yl]-1,3-benzodioxole.

The 1,3-benzodioxole ring systems in the title compound, C(22)H(22)O(8), are almost planar. The perhydro-furofuranyl system linking them adopts a distorted double-envelope conformation. Supra-molecular aggregation is effected by C-H⋯O, C-H⋯π and π-π [centroid-centroid distance of 3.755 Å, inter-planar distance of 3.633 Å and dihedral angle of 14.6°] inter-actions.

Related literature

For related literature, see: Fu et al. (2006 ▶); Sonar et al. (2006 ▶); Hu et al. (2007 ▶); Zhou et al. (2007 ▶); Liang (2004 ▶); Wang et al. (2004 ▶); Zheng et al. (2005a ▶,b ▶); Hu et al. (2005 ▶); Qi et al. (2006 ▶); Hussain et al. (2006 ▶); Yu et al. (2006 ▶); Zhang et al. (2007 ▶); Betz et al. (2007 ▶); Yin et al. (2007 ▶); Beroza & Barthel (1957 ▶); Mitscher et al. (1979 ▶); Chien & Cheng (1970 ▶); Rao et al. (1981 ▶). For hydrogen bonds, see: Desiraju & Steiner (1999 ▶); Desiraju (1989 ▶). For graph-set notations, see: Bernstein et al. (1995 ▶); Etter (1990 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C22H22O8

M = 414.40

Monoclinic,

a = 4.754 (5) Å

b = 13.982 (4) Å

c = 14.672 (5) Å

β = 97.97 (6)°

V = 965.8 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 293 (2) K

0.3 × 0.3 × 0.3 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.805, T max = 0.999

2000 measured reflections

1777 independent reflections

1505 reflections with I > 2σ(I)

R int = 0.009

2 standard reflections every 100 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.110

S = 1.05

1777 reflections

272 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018138/dn2355sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018138/dn2355Isup2.hkl

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

C22H22O8	F000 = 436
Mr = 414.40	Dx = 1.425 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 4.754 (5) Å	θ = 10–14º
b = 13.982 (4) Å	µ = 0.11 mm−1
c = 14.672 (5) Å	T = 293 (2) K
β = 97.97 (6)º	Prismatic, colorless
V = 965.8 (10) Å3	0.3 × 0.3 × 0.3 mm
Z = 2

Enraf–Nonius CAD-4 diffractometer	Rint = 0.009
Radiation source: fine-focus sealed tube	θmax = 25.0º
Monochromator: graphite	θmin = 2.0º
T = 293(2) K	h = 0→5
ω–2θ scans	k = 0→16
Absorption correction: ψ scan(North et al., 1968)	l = −17→17
Tmin = 0.805, Tmax = 0.999	2 standard reflections
2000 measured reflections	every 100 reflections
1777 independent reflections	intensity decay: none
1505 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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0741P)2 + 0.1102P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1777 reflections	Δρmax = 0.20 e Å−3
272 parameters	Δρmin = −0.20 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (4)

Experimental. Psi-scan (North, et al.,1968). Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied.

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
C1	1.0773 (8)	0.1633 (3)	1.4216 (2)	0.0526 (8)
C2	1.2921 (8)	0.1468 (3)	1.4925 (2)	0.0561 (9)
C3	1.4503 (8)	0.2198 (3)	1.5347 (2)	0.0570 (9)
C4	1.4085 (9)	0.3134 (3)	1.5089 (3)	0.0639 (10)
H4	1.5187	0.3627	1.5376	0.077*
C5	1.1918 (8)	0.3303 (3)	1.4372 (2)	0.0573 (9)
H5	1.1555	0.3931	1.4182	0.069*
C6	1.0278 (7)	0.2588 (2)	1.3927 (2)	0.0453 (7)
C7	0.7982 (7)	0.2786 (2)	1.3134 (2)	0.0442 (7)
H7	0.6163	0.2557	1.3294	0.053*
C8	0.8479 (6)	0.2337 (2)	1.2209 (2)	0.0427 (7)
H8	1.0446	0.2118	1.2232	0.051*
C9	0.7821 (6)	0.3148 (2)	1.1502 (2)	0.0447 (7)
H9	0.9549	0.3388	1.1285	0.054*
C10	0.6472 (8)	0.3900 (3)	1.2056 (2)	0.0538 (8)
H10A	0.6794	0.4537	1.1829	0.065*
H10B	0.4442	0.3795	1.2016	0.065*
C11	0.6397 (8)	0.1550 (3)	1.1852 (2)	0.0539 (8)
H11A	0.7398	0.1024	1.1609	0.065*
H11B	0.5436	0.1308	1.2346	0.065*
C12	0.5768 (6)	0.2704 (3)	1.0716 (2)	0.0464 (7)
H12	0.4349	0.3185	1.0483	0.056*
C13	0.7205 (6)	0.2343 (2)	0.9919 (2)	0.0456 (7)
C14	0.7185 (8)	0.1376 (3)	0.9672 (2)	0.0536 (8)
H14	0.6241	0.0944	1.0004	0.064*
C15	0.8500 (8)	0.1038 (3)	0.8959 (3)	0.0589 (9)
H15	0.8475	0.0391	0.8809	0.071*
C16	0.9849 (7)	0.1695 (3)	0.8480 (2)	0.0517 (8)
C17	0.9892 (7)	0.2650 (3)	0.8700 (2)	0.0488 (8)
C18	0.8592 (8)	0.2999 (2)	0.9410 (2)	0.0477 (8)
C19	0.7762 (12)	0.4613 (3)	0.8991 (3)	0.0808 (13)
H19A	0.7930	0.5244	0.9249	0.121*
H19B	0.5812	0.4488	0.8754	0.121*
H19C	0.8900	0.4567	0.8500	0.121*
C20	1.0043 (15)	0.0036 (3)	1.3671 (4)	0.1010 (18)
H20A	0.8569	−0.0359	1.3354	0.151*
H20B	1.0690	−0.0234	1.4264	0.151*
H20C	1.1598	0.0070	1.3319	0.151*
C21	1.6026 (13)	0.0854 (4)	1.6057 (3)	0.0889 (15)
H21A	1.5541	0.0659	1.6650	0.107*
H21B	1.7749	0.0522	1.5956	0.107*
C22	1.2286 (9)	0.2467 (3)	0.7507 (3)	0.0673 (11)
H22A	1.4341	0.2467	0.7551	0.081*
H22B	1.1501	0.2621	0.6878	0.081*
O1	0.4386 (5)	0.19560 (19)	1.11427 (16)	0.0549 (6)
O2	0.7797 (5)	0.37966 (17)	1.29739 (16)	0.0551 (6)
O3	0.8695 (7)	0.39473 (18)	0.96665 (16)	0.0666 (8)
O4	0.8987 (7)	0.0950 (2)	1.3780 (2)	0.0811 (9)
O5	1.3775 (8)	0.0610 (2)	1.5348 (2)	0.0890 (10)
O6	1.6475 (7)	0.1843 (3)	1.60497 (19)	0.0784 (9)
O7	1.1404 (7)	0.3157 (2)	0.81173 (18)	0.0717 (8)
O8	1.1315 (7)	0.1546 (2)	0.77478 (18)	0.0698 (8)

	U11	U22	U33	U12	U13	U23
C1	0.066 (2)	0.0420 (19)	0.0494 (16)	−0.0059 (16)	0.0081 (15)	−0.0034 (15)
C2	0.072 (2)	0.049 (2)	0.0470 (16)	0.0097 (18)	0.0078 (16)	0.0039 (15)
C3	0.066 (2)	0.064 (2)	0.0413 (16)	0.0050 (18)	0.0093 (15)	−0.0087 (16)
C4	0.070 (2)	0.060 (2)	0.060 (2)	−0.0094 (19)	0.0025 (18)	−0.0160 (18)
C5	0.072 (2)	0.0424 (19)	0.0578 (19)	−0.0023 (18)	0.0101 (17)	−0.0048 (16)
C6	0.0534 (17)	0.0396 (18)	0.0451 (16)	−0.0021 (14)	0.0140 (13)	−0.0019 (14)
C7	0.0504 (16)	0.0331 (15)	0.0510 (17)	0.0020 (14)	0.0133 (14)	−0.0033 (12)
C8	0.0403 (15)	0.0387 (16)	0.0506 (17)	0.0012 (13)	0.0114 (12)	−0.0020 (13)
C9	0.0425 (15)	0.0436 (18)	0.0485 (16)	−0.0009 (14)	0.0076 (13)	0.0026 (14)
C10	0.0589 (19)	0.0419 (18)	0.0607 (19)	0.0068 (16)	0.0085 (15)	0.0016 (15)
C11	0.0611 (19)	0.042 (2)	0.0588 (19)	−0.0079 (15)	0.0077 (16)	−0.0042 (15)
C12	0.0387 (14)	0.0482 (18)	0.0520 (17)	0.0019 (14)	0.0055 (13)	−0.0007 (15)
C13	0.0396 (15)	0.0458 (18)	0.0492 (16)	0.0050 (14)	−0.0017 (12)	−0.0042 (14)
C14	0.0576 (19)	0.0450 (19)	0.0572 (18)	−0.0077 (16)	0.0045 (15)	−0.0040 (16)
C15	0.069 (2)	0.0413 (19)	0.065 (2)	0.0019 (17)	0.0010 (18)	−0.0112 (16)
C16	0.0542 (18)	0.052 (2)	0.0465 (16)	0.0090 (16)	−0.0004 (14)	−0.0085 (15)
C17	0.0527 (17)	0.0468 (19)	0.0455 (16)	0.0056 (15)	0.0018 (13)	0.0025 (14)
C18	0.0589 (18)	0.0386 (17)	0.0449 (16)	0.0080 (14)	0.0049 (14)	−0.0018 (13)
C19	0.119 (4)	0.043 (2)	0.078 (3)	0.010 (2)	0.006 (3)	0.008 (2)
C20	0.138 (5)	0.050 (3)	0.106 (4)	−0.008 (3)	−0.015 (4)	−0.011 (2)
C21	0.112 (4)	0.076 (3)	0.072 (3)	0.026 (3)	−0.012 (3)	−0.004 (2)
C22	0.066 (2)	0.084 (3)	0.054 (2)	0.002 (2)	0.0141 (17)	−0.010 (2)
O1	0.0417 (10)	0.0593 (16)	0.0635 (14)	−0.0085 (11)	0.0067 (10)	−0.0018 (12)
O2	0.0706 (15)	0.0394 (12)	0.0549 (13)	0.0086 (11)	0.0078 (12)	−0.0048 (10)
O3	0.109 (2)	0.0374 (13)	0.0530 (13)	0.0118 (14)	0.0112 (13)	−0.0009 (11)
O4	0.094 (2)	0.0412 (16)	0.098 (2)	−0.0100 (14)	−0.0195 (17)	0.0001 (14)
O5	0.127 (3)	0.0578 (18)	0.0730 (18)	0.0080 (18)	−0.0191 (18)	0.0092 (15)
O6	0.0845 (19)	0.086 (2)	0.0592 (15)	0.0131 (17)	−0.0101 (14)	−0.0071 (15)
O7	0.100 (2)	0.0573 (16)	0.0647 (15)	0.0025 (15)	0.0367 (15)	0.0019 (13)
O8	0.0881 (19)	0.0635 (18)	0.0603 (15)	0.0155 (15)	0.0191 (14)	−0.0102 (13)

C1—C2	1.373 (5)	C12—H12	0.9800
C1—O4	1.375 (5)	C13—C14	1.399 (5)
C1—C6	1.411 (5)	C13—C18	1.403 (5)
C2—C3	1.364 (6)	C14—C15	1.374 (5)
C2—O5	1.385 (5)	C14—H14	0.9300
C3—C4	1.370 (6)	C15—C16	1.370 (6)
C3—O6	1.385 (5)	C15—H15	0.9300
C4—C5	1.387 (6)	C16—C17	1.372 (5)
C4—H4	0.9300	C16—O8	1.375 (4)
C5—C6	1.376 (5)	C17—C18	1.373 (5)
C5—H5	0.9300	C17—O7	1.386 (5)
C6—C7	1.506 (5)	C18—O3	1.377 (4)
C7—O2	1.433 (4)	C19—O3	1.387 (5)
C7—C8	1.544 (4)	C19—H19A	0.9600
C7—H7	0.9800	C19—H19B	0.9600
C8—C11	1.524 (5)	C19—H19C	0.9600
C8—C9	1.539 (4)	C20—O4	1.390 (6)
C8—H8	0.9800	C20—H20A	0.9600
C9—C10	1.525 (5)	C20—H20B	0.9600
C9—C12	1.535 (5)	C20—H20C	0.9600
C9—H9	0.9800	C21—O6	1.400 (6)
C10—O2	1.412 (4)	C21—O5	1.426 (6)
C10—H10A	0.9700	C21—H21A	0.9700
C10—H10B	0.9700	C21—H21B	0.9700
C11—O1	1.430 (5)	C22—O7	1.419 (5)
C11—H11A	0.9700	C22—O8	1.428 (6)
C11—H11B	0.9700	C22—H22A	0.9700
C12—O1	1.425 (4)	C22—H22B	0.9700
C12—C13	1.520 (4)
C2—C1—O4	125.6 (3)	C13—C12—H12	108.7
C2—C1—C6	117.5 (3)	C9—C12—H12	108.7
O4—C1—C6	116.8 (3)	C14—C13—C18	118.7 (3)
C3—C2—C1	121.6 (3)	C14—C13—C12	122.2 (3)
C3—C2—O5	109.6 (3)	C18—C13—C12	119.1 (3)
C1—C2—O5	128.8 (4)	C15—C14—C13	122.8 (3)
C2—C3—C4	122.7 (3)	C15—C14—H14	118.6
C2—C3—O6	110.1 (4)	C13—C14—H14	118.6
C4—C3—O6	127.2 (4)	C16—C15—C14	117.0 (3)
C3—C4—C5	115.9 (4)	C16—C15—H15	121.5
C3—C4—H4	122.1	C14—C15—H15	121.5
C5—C4—H4	122.1	C15—C16—C17	121.6 (3)
C6—C5—C4	123.3 (4)	C15—C16—O8	128.6 (3)
C6—C5—H5	118.4	C17—C16—O8	109.8 (3)
C4—C5—H5	118.4	C16—C17—C18	122.1 (3)
C5—C6—C1	119.1 (3)	C16—C17—O7	110.1 (3)
C5—C6—C7	122.3 (3)	C18—C17—O7	127.8 (3)
C1—C6—C7	118.6 (3)	C17—C18—O3	123.2 (3)
O2—C7—C6	109.3 (3)	C17—C18—C13	117.7 (3)
O2—C7—C8	105.6 (3)	O3—C18—C13	119.1 (3)
C6—C7—C8	114.9 (3)	O3—C19—H19A	109.5
O2—C7—H7	109.0	O3—C19—H19B	109.5
C6—C7—H7	109.0	H19A—C19—H19B	109.5
C8—C7—H7	109.0	O3—C19—H19C	109.5
C11—C8—C9	103.8 (3)	H19A—C19—H19C	109.5
C11—C8—C7	115.1 (3)	H19B—C19—H19C	109.5
C9—C8—C7	104.6 (2)	O4—C20—H20A	109.5
C11—C8—H8	111.0	O4—C20—H20B	109.5
C9—C8—H8	111.0	H20A—C20—H20B	109.5
C7—C8—H8	111.0	O4—C20—H20C	109.5
C10—C9—C12	114.1 (3)	H20A—C20—H20C	109.5
C10—C9—C8	102.1 (2)	H20B—C20—H20C	109.5
C12—C9—C8	104.9 (3)	O6—C21—O5	109.3 (4)
C10—C9—H9	111.7	O6—C21—H21A	109.8
C12—C9—H9	111.7	O5—C21—H21A	109.8
C8—C9—H9	111.7	O6—C21—H21B	109.8
O2—C10—C9	105.8 (3)	O5—C21—H21B	109.8
O2—C10—H10A	110.6	H21A—C21—H21B	108.3
C9—C10—H10A	110.6	O7—C22—O8	108.8 (3)
O2—C10—H10B	110.6	O7—C22—H22A	109.9
C9—C10—H10B	110.6	O8—C22—H22A	109.9
H10A—C10—H10B	108.7	O7—C22—H22B	109.9
O1—C11—C8	107.4 (3)	O8—C22—H22B	109.9
O1—C11—H11A	110.2	H22A—C22—H22B	108.3
C8—C11—H11A	110.2	C12—O1—C11	108.0 (2)
O1—C11—H11B	110.2	C10—O2—C7	105.5 (3)
C8—C11—H11B	110.2	C18—O3—C19	117.0 (3)
H11A—C11—H11B	108.5	C1—O4—C20	118.8 (4)
O1—C12—C13	112.2 (3)	C2—O5—C21	105.2 (4)
O1—C12—C9	104.5 (2)	C3—O6—C21	105.7 (3)
C13—C12—C9	113.9 (3)	C17—O7—C22	105.4 (3)
O1—C12—H12	108.7	C16—O8—C22	105.8 (3)
O4—C1—C2—C3	−176.8 (4)	C9—C12—C13—C18	−63.3 (4)
C6—C1—C2—C3	0.9 (5)	C18—C13—C14—C15	0.9 (5)
O4—C1—C2—O5	0.5 (6)	C12—C13—C14—C15	−179.3 (3)
C6—C1—C2—O5	178.1 (4)	C13—C14—C15—C16	−0.5 (5)
C1—C2—C3—C4	−0.7 (6)	C14—C15—C16—C17	0.1 (5)
O5—C2—C3—C4	−178.5 (4)	C14—C15—C16—O8	179.8 (3)
C1—C2—C3—O6	178.7 (3)	C15—C16—C17—C18	0.0 (5)
O5—C2—C3—O6	0.9 (4)	O8—C16—C17—C18	−179.8 (3)
C2—C3—C4—C5	0.7 (6)	C15—C16—C17—O7	179.6 (3)
O6—C3—C4—C5	−178.6 (3)	O8—C16—C17—O7	−0.2 (4)
C3—C4—C5—C6	−0.8 (6)	C16—C17—C18—O3	177.5 (3)
C4—C5—C6—C1	1.0 (5)	O7—C17—C18—O3	−2.0 (5)
C4—C5—C6—C7	−178.5 (3)	C16—C17—C18—C13	0.4 (5)
C2—C1—C6—C5	−1.0 (5)	O7—C17—C18—C13	−179.1 (3)
O4—C1—C6—C5	176.9 (3)	C14—C13—C18—C17	−0.8 (4)
C2—C1—C6—C7	178.5 (3)	C12—C13—C18—C17	179.4 (3)
O4—C1—C6—C7	−3.6 (5)	C14—C13—C18—O3	−178.0 (3)
C5—C6—C7—O2	−2.0 (4)	C12—C13—C18—O3	2.2 (4)
C1—C6—C7—O2	178.5 (3)	C13—C12—O1—C11	89.0 (3)
C5—C6—C7—C8	116.5 (3)	C9—C12—O1—C11	−34.9 (3)
C1—C6—C7—C8	−63.0 (4)	C8—C11—O1—C12	29.6 (3)
O2—C7—C8—C11	−126.6 (3)	C9—C10—O2—C7	−42.3 (3)
C6—C7—C8—C11	112.9 (3)	C6—C7—O2—C10	158.5 (3)
O2—C7—C8—C9	−13.3 (3)	C8—C7—O2—C10	34.3 (3)
C6—C7—C8—C9	−133.8 (3)	C17—C18—O3—C19	55.8 (5)
C11—C8—C9—C10	110.4 (3)	C13—C18—O3—C19	−127.2 (4)
C7—C8—C9—C10	−10.7 (3)	C2—C1—O4—C20	−34.0 (6)
C11—C8—C9—C12	−9.0 (3)	C6—C1—O4—C20	148.4 (4)
C7—C8—C9—C12	−130.0 (3)	C3—C2—O5—C21	−0.7 (5)
C12—C9—C10—O2	144.6 (3)	C1—C2—O5—C21	−178.2 (4)
C8—C9—C10—O2	32.0 (3)	O6—C21—O5—C2	0.2 (6)
C9—C8—C11—O1	−11.5 (3)	C2—C3—O6—C21	−0.8 (5)
C7—C8—C11—O1	102.2 (3)	C4—C3—O6—C21	178.6 (5)
C10—C9—C12—O1	−84.5 (3)	O5—C21—O6—C3	0.3 (6)
C8—C9—C12—O1	26.4 (3)	C16—C17—O7—C22	0.7 (4)
C10—C9—C12—C13	152.6 (3)	C18—C17—O7—C22	−179.7 (3)
C8—C9—C12—C13	−96.4 (3)	O8—C22—O7—C17	−1.0 (4)
O1—C12—C13—C14	−1.6 (4)	C15—C16—O8—C22	179.8 (4)
C9—C12—C13—C14	116.9 (4)	C17—C16—O8—C22	−0.4 (4)
O1—C12—C13—C18	178.2 (3)	O7—C22—O8—C16	0.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2	0.93	2.34	2.721 (5)	104
C9—H9···O3	0.98	2.48	2.997 (4)	113
C11—H11B···O4	0.97	2.56	3.042 (5)	111
C14—H14···O1	0.93	2.45	2.808 (5)	103
C19—H19C···O7	0.96	2.41	3.065 (6)	125
C20—H20B···O5	0.96	2.33	2.939 (7)	121
C7—H7···Cg5i	0.98	2.86	3.724	148
C22—H22A···Cg6ii	0.97	2.97	3.646	128

Table 1

Selected torsion angles (°)

O2—C7—C8—C9	−13.3 (3)
C7—C8—C9—C10	−10.7 (3)
C11—C8—C9—C12	−9.0 (3)
C8—C9—C10—O2	32.0 (3)
C9—C8—C11—O1	−11.5 (3)
C8—C9—C12—O1	26.4 (3)

Table 2

Hydrogen-bond geometry (Å, °)

Cg5 is the centroid of the C1–C6 ring and Cg6 is the centroid of the C13—C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2	0.93	2.34	2.721 (5)	104
C9—H9⋯O3	0.98	2.48	2.997 (4)	113
C11—H11B⋯O4	0.97	2.56	3.042 (5)	111
C14—H14⋯O1	0.93	2.45	2.808 (5)	103
C19—H19C⋯O7	0.96	2.41	3.065 (6)	125
C20—H20B⋯O5	0.96	2.33	2.939 (7)	121
C7—H7⋯Cg5i	0.98	2.85	3.724	148
C22—H22A⋯Cg6ii	0.97	2.97	3.646	128

Symmetry codes: (i) ; (ii) .