7,7',8,8'-Tetra-meth-oxy-4,4'-dimethyl-3,5'-bichromene-2,2'-dione.

In the title mol-ecule, C(24)H(22)O(8), the mean planes of the two coumarin units are inclined to each other at a dihedral angle of 79.93 (3)°. The attached meth-oxy groups form torsion angles of 7.65 (19) and 78.36 (14)° with respect to one coumarin unit, and angles of 9.01 (16) and 99.08 (11)° with respect to the other coumarin unit. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds connect pairs of mol-ecules to form dimers, generating R(2) (2)(16) and R(2) (2)(18) rings; the dimers are linked by further weak inter-molecular C-H⋯O hydrogen bonds, forming extended chains. Additional stabil-ization is provided by weak C-H⋯π inter-actions.

Related literature

For the biological activity of coumarins, see: El-Agrody et al. (2001 ▶); El-Farargy (1991 ▶); Emmanuel-Giota et al. (2001 ▶); Ghate et al. (2005 ▶); Laakso et al. (1994 ▶); Nofal et al. (2000 ▶); Pratibha et al. (1999 ▶); Shaker (1996 ▶); Yang et al. (2005 ▶). For the pharmaceutical properties of coumarin derivatives, see: Kennedy et al. (1997 ▶). For related literature on natural and synthetic coumarins, see: Carlton et al. (1996 ▶); Zhou et al. (2000 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C24H22O8

M = 438.42

Monoclinic,

a = 9.4724 (1) Å

b = 23.4766 (3) Å

c = 9.3525 (1) Å

β = 96.254 (1)°

V = 2067.43 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.50 × 0.27 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.949, T max = 0.985

58385 measured reflections

7006 independent reflections

6023 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.125

S = 1.07

7006 reflections

295 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018029/lh2822sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018029/lh2822Isup2.hkl

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

C24H22O8	F(000) = 920
Mr = 438.42	Dx = 1.409 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9875 reflections
a = 9.4724 (1) Å	θ = 2.7–33.0°
b = 23.4766 (3) Å	µ = 0.11 mm−1
c = 9.3525 (1) Å	T = 100 K
β = 96.254 (1)°	Plate, colourless
V = 2067.43 (4) Å3	0.50 × 0.27 × 0.14 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	7006 independent reflections
Radiation source: fine-focus sealed tube	6023 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 31.7°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.949, Tmax = 0.985	k = −34→34
58385 measured reflections	l = −13→13

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0593P)2 + 0.8142P] where P = (Fo2 + 2Fc2)/3
7006 reflections	(Δ/σ)max < 0.001
295 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	0.69654 (9)	0.68242 (4)	0.29953 (11)	0.0282 (2)
O2	0.43643 (8)	0.65723 (3)	0.37372 (10)	0.02296 (17)
O3	0.26852 (8)	0.73969 (3)	0.46388 (9)	0.01987 (16)
O4	0.05685 (9)	0.76180 (3)	0.52477 (10)	0.02502 (18)
O5	0.03012 (9)	0.95276 (4)	0.88144 (9)	0.02254 (17)
O6	−0.18774 (8)	0.99197 (3)	0.69969 (9)	0.02027 (16)
O7	−0.22134 (8)	0.96109 (3)	0.42722 (8)	0.01782 (15)
O8	−0.35251 (9)	0.97343 (4)	0.21952 (10)	0.02664 (18)
C1	0.17182 (11)	0.77961 (4)	0.50060 (12)	0.01762 (19)
C2	0.40061 (11)	0.75552 (4)	0.43041 (12)	0.01703 (19)
C3	0.48594 (11)	0.71220 (4)	0.38541 (13)	0.0191 (2)
C4	0.62110 (12)	0.72617 (5)	0.34739 (13)	0.0217 (2)
C5	0.66991 (12)	0.78230 (5)	0.36156 (16)	0.0274 (3)
H5A	0.7607	0.7914	0.3398	0.033*
C6	0.58343 (12)	0.82435 (5)	0.40787 (15)	0.0247 (2)
H6A	0.6174	0.8615	0.4172	0.030*
C7	0.44578 (11)	0.81239 (4)	0.44116 (12)	0.01799 (19)
C8	0.34781 (11)	0.85546 (4)	0.48140 (12)	0.01690 (18)
C9	0.21437 (11)	0.83939 (4)	0.50522 (11)	0.01574 (18)
C10	0.10535 (11)	0.88049 (4)	0.54652 (11)	0.01548 (18)
C11	0.12224 (11)	0.89822 (4)	0.68924 (11)	0.01727 (19)
H11A	0.1996	0.8852	0.7502	0.021*
C12	0.02494 (11)	0.93527 (4)	0.74272 (11)	0.01696 (18)
C13	−0.09034 (11)	0.95541 (4)	0.65136 (11)	0.01643 (18)
C14	−0.10474 (10)	0.93843 (4)	0.50800 (11)	0.01503 (18)
C15	−0.24804 (11)	0.95111 (5)	0.28163 (12)	0.0192 (2)
C16	−0.15038 (12)	0.91360 (5)	0.21998 (12)	0.01956 (19)
H16A	−0.1646	0.9067	0.1215	0.023*
C17	−0.03892 (11)	0.88778 (4)	0.29753 (11)	0.01678 (18)
C18	−0.00961 (10)	0.90076 (4)	0.45039 (11)	0.01475 (17)
C19	0.82791 (13)	0.69680 (6)	0.24429 (17)	0.0318 (3)
H19A	0.8643	0.6639	0.1997	0.048*
H19B	0.8956	0.7094	0.3218	0.048*
H19C	0.8115	0.7267	0.1745	0.048*
C20	0.49521 (14)	0.62163 (6)	0.48972 (18)	0.0333 (3)
H20A	0.4725	0.5826	0.4674	0.050*
H20B	0.4560	0.6322	0.5763	0.050*
H20C	0.5965	0.6262	0.5031	0.050*
C21	0.39362 (12)	0.91653 (5)	0.49091 (15)	0.0257 (2)
H21A	0.3114	0.9406	0.4878	0.039*
H21B	0.4459	0.9254	0.4115	0.039*
H21C	0.4528	0.9227	0.5796	0.039*
C22	0.15479 (13)	0.93845 (5)	0.97486 (12)	0.0238 (2)
H22A	0.1452	0.9520	1.0701	0.036*
H22B	0.2362	0.9559	0.9401	0.036*
H22C	0.1667	0.8978	0.9770	0.036*
C23	−0.29354 (12)	0.96294 (5)	0.77235 (14)	0.0259 (2)
H23A	−0.3698	0.9887	0.7853	0.039*
H23B	−0.2515	0.9498	0.8645	0.039*
H23C	−0.3297	0.9310	0.7156	0.039*
C24	0.04626 (13)	0.84603 (5)	0.22071 (12)	0.0231 (2)
H24A	0.0104	0.8448	0.1207	0.035*
H24B	0.0389	0.8089	0.2622	0.035*
H24C	0.1440	0.8577	0.2301	0.035*

	U11	U22	U33	U12	U13	U23
O1	0.0195 (4)	0.0190 (4)	0.0486 (6)	0.0025 (3)	0.0146 (4)	−0.0069 (4)
O2	0.0185 (4)	0.0128 (3)	0.0376 (5)	−0.0003 (3)	0.0030 (3)	−0.0021 (3)
O3	0.0148 (3)	0.0137 (3)	0.0323 (4)	0.0002 (3)	0.0084 (3)	0.0006 (3)
O4	0.0187 (4)	0.0191 (4)	0.0394 (5)	−0.0007 (3)	0.0131 (3)	0.0040 (3)
O5	0.0217 (4)	0.0293 (4)	0.0165 (4)	0.0057 (3)	0.0015 (3)	−0.0044 (3)
O6	0.0202 (4)	0.0194 (3)	0.0224 (4)	0.0060 (3)	0.0074 (3)	−0.0010 (3)
O7	0.0160 (3)	0.0176 (3)	0.0196 (4)	0.0032 (3)	0.0009 (3)	0.0009 (3)
O8	0.0217 (4)	0.0313 (4)	0.0257 (4)	0.0055 (3)	−0.0034 (3)	0.0020 (3)
C1	0.0160 (4)	0.0151 (4)	0.0225 (5)	0.0022 (3)	0.0059 (4)	0.0022 (3)
C2	0.0130 (4)	0.0153 (4)	0.0234 (5)	0.0004 (3)	0.0045 (4)	0.0005 (3)
C3	0.0156 (4)	0.0136 (4)	0.0283 (5)	0.0003 (3)	0.0039 (4)	−0.0018 (4)
C4	0.0172 (5)	0.0167 (4)	0.0326 (6)	0.0026 (3)	0.0078 (4)	−0.0031 (4)
C5	0.0171 (5)	0.0187 (5)	0.0485 (7)	−0.0010 (4)	0.0136 (5)	−0.0040 (5)
C6	0.0175 (5)	0.0156 (4)	0.0428 (7)	−0.0013 (4)	0.0106 (5)	−0.0032 (4)
C7	0.0147 (4)	0.0138 (4)	0.0263 (5)	0.0005 (3)	0.0057 (4)	−0.0005 (3)
C8	0.0151 (4)	0.0137 (4)	0.0220 (5)	0.0010 (3)	0.0030 (4)	−0.0002 (3)
C9	0.0154 (4)	0.0139 (4)	0.0184 (4)	0.0017 (3)	0.0041 (3)	0.0004 (3)
C10	0.0148 (4)	0.0137 (4)	0.0185 (4)	0.0010 (3)	0.0044 (3)	0.0007 (3)
C11	0.0156 (4)	0.0187 (4)	0.0176 (4)	0.0030 (3)	0.0022 (3)	0.0003 (3)
C12	0.0172 (4)	0.0179 (4)	0.0161 (4)	0.0009 (3)	0.0031 (3)	−0.0010 (3)
C13	0.0165 (4)	0.0153 (4)	0.0181 (4)	0.0029 (3)	0.0047 (3)	−0.0006 (3)
C14	0.0132 (4)	0.0143 (4)	0.0176 (4)	0.0009 (3)	0.0019 (3)	0.0012 (3)
C15	0.0184 (5)	0.0194 (4)	0.0194 (5)	−0.0014 (3)	0.0007 (4)	0.0014 (4)
C16	0.0205 (5)	0.0215 (5)	0.0167 (4)	−0.0011 (4)	0.0020 (4)	−0.0004 (4)
C17	0.0181 (4)	0.0156 (4)	0.0173 (4)	−0.0018 (3)	0.0049 (3)	−0.0005 (3)
C18	0.0152 (4)	0.0132 (4)	0.0165 (4)	0.0004 (3)	0.0043 (3)	0.0004 (3)
C19	0.0205 (5)	0.0279 (6)	0.0496 (8)	0.0011 (4)	0.0157 (5)	−0.0096 (5)
C20	0.0235 (6)	0.0236 (5)	0.0527 (8)	0.0009 (4)	0.0034 (5)	0.0119 (5)
C21	0.0184 (5)	0.0143 (4)	0.0451 (7)	−0.0001 (4)	0.0063 (5)	−0.0029 (4)
C22	0.0240 (5)	0.0293 (5)	0.0176 (5)	0.0024 (4)	−0.0006 (4)	−0.0004 (4)
C23	0.0184 (5)	0.0284 (5)	0.0322 (6)	0.0002 (4)	0.0078 (4)	−0.0034 (5)
C24	0.0285 (6)	0.0238 (5)	0.0178 (5)	0.0052 (4)	0.0057 (4)	−0.0028 (4)

O1—C4	1.3548 (13)	C11—C12	1.3988 (14)
O1—C19	1.4386 (15)	C11—H11A	0.9300
O2—C3	1.3733 (12)	C12—C13	1.3939 (14)
O2—C20	1.4332 (16)	C13—C14	1.3911 (14)
O3—C2	1.3736 (12)	C14—C18	1.4107 (13)
O3—C1	1.3798 (12)	C15—C16	1.4421 (15)
O4—C1	1.2106 (13)	C16—C17	1.3569 (15)
O5—C12	1.3565 (13)	C16—H16A	0.9300
O5—C22	1.4305 (14)	C17—C18	1.4586 (14)
O6—C13	1.3723 (12)	C17—C24	1.5015 (15)
O6—C23	1.4419 (14)	C19—H19A	0.9600
O7—C14	1.3755 (12)	C19—H19B	0.9600
O7—C15	1.3777 (13)	C19—H19C	0.9600
O8—C15	1.2108 (13)	C20—H20A	0.9600
C1—C9	1.4594 (14)	C20—H20B	0.9600
C2—C3	1.3924 (14)	C20—H20C	0.9600
C2—C7	1.4023 (14)	C21—H21A	0.9600
C3—C4	1.4043 (15)	C21—H21B	0.9600
C4—C5	1.3980 (15)	C21—H21C	0.9600
C5—C6	1.3822 (15)	C22—H22A	0.9600
C5—H5A	0.9300	C22—H22B	0.9600
C6—C7	1.4016 (15)	C22—H22C	0.9600
C6—H6A	0.9300	C23—H23A	0.9600
C7—C8	1.4496 (14)	C23—H23B	0.9600
C8—C9	1.3605 (14)	C23—H23C	0.9600
C8—C21	1.4977 (14)	C24—H24A	0.9600
C9—C10	1.4945 (14)	C24—H24B	0.9600
C10—C11	1.3906 (14)	C24—H24C	0.9600
C10—C18	1.4168 (14)
C4—O1—C19	116.67 (9)	O8—C15—O7	116.93 (10)
C3—O2—C20	112.74 (10)	O8—C15—C16	126.78 (10)
C2—O3—C1	121.26 (8)	O7—C15—C16	116.26 (9)
C12—O5—C22	117.03 (9)	C17—C16—C15	123.69 (10)
C13—O6—C23	112.73 (8)	C17—C16—H16A	118.2
C14—O7—C15	121.80 (8)	C15—C16—H16A	118.2
O4—C1—O3	116.55 (9)	C16—C17—C18	118.98 (9)
O4—C1—C9	125.29 (9)	C16—C17—C24	117.60 (10)
O3—C1—C9	118.15 (9)	C18—C17—C24	123.41 (9)
O3—C2—C3	116.39 (9)	C14—C18—C10	116.55 (9)
O3—C2—C7	121.30 (9)	C14—C18—C17	116.36 (9)
C3—C2—C7	122.30 (9)	C10—C18—C17	127.08 (9)
O2—C3—C2	120.39 (9)	O1—C19—H19A	109.5
O2—C3—C4	120.81 (9)	O1—C19—H19B	109.5
C2—C3—C4	118.76 (9)	H19A—C19—H19B	109.5
O1—C4—C5	124.40 (10)	O1—C19—H19C	109.5
O1—C4—C3	115.77 (10)	H19A—C19—H19C	109.5
C5—C4—C3	119.82 (10)	H19B—C19—H19C	109.5
C6—C5—C4	120.12 (10)	O2—C20—H20A	109.5
C6—C5—H5A	119.9	O2—C20—H20B	109.5
C4—C5—H5A	119.9	H20A—C20—H20B	109.5
C5—C6—C7	121.60 (10)	O2—C20—H20C	109.5
C5—C6—H6A	119.2	H20A—C20—H20C	109.5
C7—C6—H6A	119.2	H20B—C20—H20C	109.5
C6—C7—C2	117.31 (9)	C8—C21—H21A	109.5
C6—C7—C8	123.73 (9)	C8—C21—H21B	109.5
C2—C7—C8	118.93 (9)	H21A—C21—H21B	109.5
C9—C8—C7	118.78 (9)	C8—C21—H21C	109.5
C9—C8—C21	121.61 (9)	H21A—C21—H21C	109.5
C7—C8—C21	119.58 (9)	H21B—C21—H21C	109.5
C8—C9—C1	121.36 (9)	O5—C22—H22A	109.5
C8—C9—C10	122.93 (9)	O5—C22—H22B	109.5
C1—C9—C10	115.60 (9)	H22A—C22—H22B	109.5
C11—C10—C18	120.57 (9)	O5—C22—H22C	109.5
C11—C10—C9	115.52 (9)	H22A—C22—H22C	109.5
C18—C10—C9	123.91 (9)	H22B—C22—H22C	109.5
C10—C11—C12	121.19 (9)	O6—C23—H23A	109.5
C10—C11—H11A	119.4	O6—C23—H23B	109.5
C12—C11—H11A	119.4	H23A—C23—H23B	109.5
O5—C12—C13	115.33 (9)	O6—C23—H23C	109.5
O5—C12—C11	125.00 (9)	H23A—C23—H23C	109.5
C13—C12—C11	119.63 (9)	H23B—C23—H23C	109.5
O6—C13—C14	119.86 (9)	C17—C24—H24A	109.5
O6—C13—C12	121.34 (9)	C17—C24—H24B	109.5
C14—C13—C12	118.79 (9)	H24A—C24—H24B	109.5
O7—C14—C13	114.02 (8)	C17—C24—H24C	109.5
O7—C14—C18	122.74 (9)	H24A—C24—H24C	109.5
C13—C14—C18	123.23 (9)	H24B—C24—H24C	109.5
C2—O3—C1—O4	178.16 (10)	C8—C9—C10—C18	103.55 (13)
C2—O3—C1—C9	−0.94 (15)	C1—C9—C10—C18	−80.20 (12)
C1—O3—C2—C3	−175.74 (10)	C18—C10—C11—C12	1.57 (15)
C1—O3—C2—C7	4.15 (16)	C9—C10—C11—C12	−178.01 (9)
C20—O2—C3—C2	−103.96 (12)	C22—O5—C12—C13	−173.06 (9)
C20—O2—C3—C4	78.36 (14)	C22—O5—C12—C11	9.01 (16)
O3—C2—C3—O2	1.16 (16)	C10—C11—C12—O5	177.12 (10)
C7—C2—C3—O2	−178.72 (10)	C10—C11—C12—C13	−0.73 (16)
O3—C2—C3—C4	178.89 (10)	C23—O6—C13—C14	99.08 (11)
C7—C2—C3—C4	−1.00 (17)	C23—O6—C13—C12	−81.83 (12)
C19—O1—C4—C5	−7.65 (19)	O5—C12—C13—O6	2.19 (15)
C19—O1—C4—C3	172.97 (11)	C11—C12—C13—O6	−179.76 (9)
O2—C3—C4—O1	0.06 (17)	O5—C12—C13—C14	−178.71 (9)
C2—C3—C4—O1	−177.65 (10)	C11—C12—C13—C14	−0.66 (15)
O2—C3—C4—C5	−179.34 (11)	C15—O7—C14—C13	176.70 (9)
C2—C3—C4—C5	2.94 (18)	C15—O7—C14—C18	−4.07 (14)
O1—C4—C5—C6	178.29 (13)	O6—C13—C14—O7	−0.41 (14)
C3—C4—C5—C6	−2.4 (2)	C12—C13—C14—O7	−179.52 (9)
C4—C5—C6—C7	−0.2 (2)	O6—C13—C14—C18	−179.63 (9)
C5—C6—C7—C2	2.14 (19)	C12—C13—C14—C18	1.25 (15)
C5—C6—C7—C8	−175.98 (12)	C14—O7—C15—O8	−179.20 (9)
O3—C2—C7—C6	178.61 (11)	C14—O7—C15—C16	2.60 (14)
C3—C2—C7—C6	−1.51 (17)	O8—C15—C16—C17	−176.66 (11)
O3—C2—C7—C8	−3.18 (16)	O7—C15—C16—C17	1.34 (16)
C3—C2—C7—C8	176.71 (10)	C15—C16—C17—C18	−3.75 (16)
C6—C7—C8—C9	177.07 (11)	C15—C16—C17—C24	174.94 (10)
C2—C7—C8—C9	−1.03 (16)	O7—C14—C18—C10	−179.60 (9)
C6—C7—C8—C21	−0.87 (18)	C13—C14—C18—C10	−0.43 (14)
C2—C7—C8—C21	−178.97 (11)	O7—C14—C18—C17	1.53 (14)
C7—C8—C9—C1	4.21 (16)	C13—C14—C18—C17	−179.31 (9)
C21—C8—C9—C1	−177.89 (11)	C11—C10—C18—C14	−0.98 (14)
C7—C8—C9—C10	−179.74 (10)	C9—C10—C18—C14	178.57 (9)
C21—C8—C9—C10	−1.85 (17)	C11—C10—C18—C17	177.76 (10)
O4—C1—C9—C8	177.67 (11)	C9—C10—C18—C17	−2.69 (16)
O3—C1—C9—C8	−3.33 (15)	C16—C17—C18—C14	2.26 (14)
O4—C1—C9—C10	1.35 (16)	C24—C17—C18—C14	−176.35 (9)
O3—C1—C9—C10	−179.65 (9)	C16—C17—C18—C10	−176.47 (10)
C8—C9—C10—C11	−76.88 (13)	C24—C17—C18—C10	4.91 (16)
C1—C9—C10—C11	99.37 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21A···O6i	0.96	2.55	3.2921 (15)	134
C22—H22A···O6ii	0.96	2.52	3.4385 (14)	161
C22—H22B···O8i	0.96	2.56	3.4401 (15)	152
C6—H6A···Cg1iii	0.93	2.92	3.6706 (12)	138
C19—H19A···Cg2iv	0.96	2.60	3.5446 (14)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21A⋯O6i	0.96	2.55	3.2921 (15)	134
C22—H22A⋯O6ii	0.96	2.52	3.4385 (14)	161
C22—H22B⋯O8i	0.96	2.56	3.4401 (15)	152
C6—H6A⋯Cg1iii	0.93	2.92	3.6706 (12)	138
C19—H19A⋯Cg2iv	0.96	2.60	3.5446 (14)	170

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the O7/C14–C18 ring and Cg2 is the centroid of the C10–C18 ring.