Methyl (2E)-2-({2-[(2E)-2-benzyl-idene-3-meth-oxy-3-oxoprop-yl]-1,3-dioxoindan-2-yl}meth-yl)-3-phenyl-prop-2-enoate.

In the title compound, C(31)H(26)O(6), the five-membered ring of the indane unit adopts a slight envelope conformation with the flap atom displaced by 1.38 (14) Å. The mol-ecular conformation is stabilized by an intra-molecular C-H⋯O hydrogen bond, which generates an S(9) ring motif. In the crystal, pairs of C-H⋯O hydrogen bonds link centrosymmetrically related mol-ecules into dimers, generating R(2) (2)(22) ring motifs. The crystal packing is further stabilized by C-H⋯π inter-actions.

Related literature

Indene ring systems are present in a large number of biologi­cally active compounds, and their metallocene complexes are able to catalyse olefin polymerization, see: Rayabarapu et al. (2003 ▶); Senanayake et al. (1995 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C31H26O6

M = 494.52

Triclinic,

a = 10.5657 (4) Å

b = 10.9275 (5) Å

c = 11.8961 (5) Å

α = 71.250 (2)°

β = 77.889 (3)°

γ = 76.656 (2)°

V = 1251.70 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.25 × 0.23 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.978, T max = 0.985

25995 measured reflections

6921 independent reflections

5016 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.128

S = 1.04

6921 reflections

337 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia (1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812017965/bt5874sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017965/bt5874Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812017965/bt5874Isup3.cml

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

C31H26O6	Z = 2
Mr = 494.52	F(000) = 520
Triclinic, P1	Dx = 1.312 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.5657 (4) Å	Cell parameters from 7169 reflections
b = 10.9275 (5) Å	θ = 2.0–29.8°
c = 11.8961 (5) Å	µ = 0.09 mm−1
α = 71.250 (2)°	T = 293 K
β = 77.889 (3)°	Block, colourless
γ = 76.656 (2)°	0.25 × 0.23 × 0.17 mm
V = 1251.70 (9) Å3

Bruker APEXII CCD diffractometer	6921 independent reflections
Radiation source: fine-focus sealed tube	5016 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 10.0 pixels mm-1	θmax = 29.8°, θmin = 2.0°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −15→15
Tmin = 0.978, Tmax = 0.985	l = −12→16
25995 measured reflections

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0592P)2 + 0.201P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
6921 reflections	Δρmax = 0.28 e Å−3
337 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0071 (18)

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	0.25024 (11)	0.03216 (11)	0.19693 (10)	0.0334 (2)
C2	0.29043 (12)	−0.11776 (12)	0.22493 (11)	0.0379 (3)
C3	0.27268 (11)	−0.15476 (12)	0.12061 (11)	0.0357 (3)
C4	0.31247 (13)	−0.27427 (13)	0.09515 (13)	0.0441 (3)
H4	0.3578	−0.3463	0.1468	0.053*
C5	0.28266 (14)	−0.28279 (15)	−0.00914 (14)	0.0508 (4)
H5	0.3097	−0.3616	−0.0288	0.061*
C6	0.21335 (15)	−0.17655 (16)	−0.08524 (14)	0.0525 (4)
H6	0.1929	−0.1857	−0.1541	0.063*
C7	0.17414 (13)	−0.05732 (14)	−0.06069 (12)	0.0455 (3)
H7	0.1277	0.0142	−0.1120	0.055*
C8	0.20613 (11)	−0.04741 (12)	0.04293 (11)	0.0352 (3)
C9	0.17798 (11)	0.06785 (11)	0.08894 (10)	0.0335 (2)
C10	0.17153 (12)	0.08121 (12)	0.30306 (11)	0.0364 (3)
H10A	0.2062	0.0235	0.3749	0.044*
H10B	0.1909	0.1673	0.2916	0.044*
C11	0.02411 (12)	0.09234 (11)	0.32861 (10)	0.0344 (2)
C12	−0.05926 (13)	0.20136 (12)	0.33956 (12)	0.0395 (3)
H12	−0.1460	0.1918	0.3706	0.047*
C13	−0.03082 (12)	0.33552 (12)	0.30845 (12)	0.0404 (3)
C14	0.02253 (14)	0.39710 (14)	0.19283 (14)	0.0496 (3)
H14	0.0492	0.3504	0.1364	0.060*
C15	0.03664 (16)	0.52755 (15)	0.16017 (17)	0.0594 (4)
H15	0.0699	0.5686	0.0815	0.071*
C16	0.00162 (16)	0.59609 (15)	0.24355 (18)	0.0610 (4)
H16	0.0123	0.6832	0.2221	0.073*
C17	−0.04925 (17)	0.53541 (15)	0.35889 (17)	0.0610 (4)
H17	−0.0714	0.5814	0.4158	0.073*
C18	−0.06809 (16)	0.40642 (14)	0.39177 (14)	0.0517 (3)
H18	−0.1056	0.3675	0.4695	0.062*
C19	−0.02906 (13)	−0.02882 (12)	0.34965 (11)	0.0389 (3)
C20	−0.21535 (18)	−0.13120 (16)	0.41099 (18)	0.0694 (5)
H20A	−0.2102	−0.1496	0.3363	0.104*
H20B	−0.3058	−0.1147	0.4460	0.104*
H20C	−0.1688	−0.2052	0.4648	0.104*
C21	0.38551 (12)	0.08067 (12)	0.16164 (12)	0.0387 (3)
H21A	0.4251	0.0591	0.2337	0.046*
H21B	0.4434	0.0330	0.1089	0.046*
C22	0.37728 (11)	0.22488 (13)	0.10063 (11)	0.0379 (3)
C23	0.38335 (13)	0.31646 (13)	0.15049 (12)	0.0411 (3)
H23	0.3673	0.4022	0.1013	0.049*
C24	0.41114 (12)	0.30482 (12)	0.27018 (12)	0.0392 (3)
C25	0.51220 (13)	0.21207 (14)	0.32403 (13)	0.0459 (3)
H25	0.5591	0.1478	0.2881	0.055*
C26	0.54314 (14)	0.21504 (16)	0.43022 (14)	0.0529 (4)
H26	0.6109	0.1528	0.4650	0.063*
C27	0.47525 (16)	0.30853 (17)	0.48491 (14)	0.0569 (4)
H27	0.4971	0.3102	0.5561	0.068*
C28	0.37445 (16)	0.39995 (16)	0.43375 (14)	0.0549 (4)
H28	0.3275	0.4632	0.4709	0.066*
C29	0.34272 (14)	0.39827 (13)	0.32762 (13)	0.0463 (3)
H29	0.2744	0.4607	0.2939	0.056*
C30	0.36793 (13)	0.26335 (14)	−0.02990 (12)	0.0437 (3)
C31	0.3415 (2)	0.4347 (2)	−0.20839 (15)	0.0730 (5)
H31A	0.4247	0.4020	−0.2489	0.110*
H31B	0.3243	0.5289	−0.2364	0.110*
H31C	0.2732	0.4010	−0.2247	0.110*
O1	0.10725 (9)	0.17082 (9)	0.05059 (8)	0.0454 (2)
O2	0.33508 (11)	−0.18975 (10)	0.31315 (9)	0.0565 (3)
O3	−0.15730 (10)	−0.01759 (9)	0.38974 (10)	0.0549 (3)
O4	0.03542 (11)	−0.12708 (10)	0.32961 (12)	0.0659 (3)
O5	0.34473 (12)	0.39300 (10)	−0.08061 (9)	0.0581 (3)
O6	0.38424 (11)	0.18503 (11)	−0.08508 (9)	0.0588 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0328 (5)	0.0355 (6)	0.0339 (6)	−0.0033 (4)	−0.0080 (5)	−0.0124 (5)
C2	0.0363 (6)	0.0370 (6)	0.0400 (7)	−0.0031 (5)	−0.0089 (5)	−0.0107 (5)
C3	0.0314 (5)	0.0373 (6)	0.0389 (6)	−0.0072 (5)	−0.0020 (5)	−0.0129 (5)
C4	0.0413 (7)	0.0373 (6)	0.0543 (8)	−0.0094 (5)	−0.0011 (6)	−0.0160 (6)
C5	0.0496 (8)	0.0499 (8)	0.0620 (9)	−0.0160 (6)	0.0051 (7)	−0.0316 (7)
C6	0.0507 (8)	0.0688 (10)	0.0513 (8)	−0.0167 (7)	−0.0036 (6)	−0.0337 (8)
C7	0.0428 (7)	0.0575 (8)	0.0408 (7)	−0.0080 (6)	−0.0090 (6)	−0.0192 (6)
C8	0.0314 (6)	0.0405 (6)	0.0357 (6)	−0.0072 (5)	−0.0033 (5)	−0.0141 (5)
C9	0.0301 (5)	0.0375 (6)	0.0323 (6)	−0.0052 (4)	−0.0038 (4)	−0.0101 (5)
C10	0.0394 (6)	0.0395 (6)	0.0335 (6)	−0.0062 (5)	−0.0070 (5)	−0.0142 (5)
C11	0.0402 (6)	0.0346 (6)	0.0295 (6)	−0.0086 (5)	−0.0023 (5)	−0.0109 (5)
C12	0.0383 (6)	0.0384 (6)	0.0428 (7)	−0.0099 (5)	0.0010 (5)	−0.0153 (5)
C13	0.0372 (6)	0.0356 (6)	0.0507 (7)	−0.0030 (5)	−0.0072 (5)	−0.0174 (6)
C14	0.0503 (8)	0.0433 (7)	0.0570 (9)	−0.0119 (6)	0.0022 (6)	−0.0205 (6)
C15	0.0567 (9)	0.0449 (8)	0.0729 (11)	−0.0169 (7)	0.0007 (8)	−0.0130 (7)
C16	0.0551 (9)	0.0371 (7)	0.0962 (13)	−0.0076 (6)	−0.0189 (9)	−0.0217 (8)
C17	0.0724 (10)	0.0440 (8)	0.0787 (12)	0.0041 (7)	−0.0265 (9)	−0.0344 (8)
C18	0.0603 (9)	0.0432 (7)	0.0536 (8)	0.0021 (6)	−0.0142 (7)	−0.0207 (6)
C19	0.0453 (7)	0.0360 (6)	0.0339 (6)	−0.0095 (5)	0.0016 (5)	−0.0111 (5)
C20	0.0665 (10)	0.0526 (9)	0.0910 (13)	−0.0333 (8)	0.0190 (9)	−0.0265 (9)
C21	0.0317 (6)	0.0418 (6)	0.0442 (7)	−0.0032 (5)	−0.0073 (5)	−0.0155 (5)
C22	0.0298 (5)	0.0454 (7)	0.0386 (6)	−0.0076 (5)	−0.0044 (5)	−0.0118 (5)
C23	0.0407 (6)	0.0418 (7)	0.0405 (7)	−0.0106 (5)	−0.0073 (5)	−0.0085 (5)
C24	0.0365 (6)	0.0425 (7)	0.0405 (7)	−0.0140 (5)	−0.0049 (5)	−0.0100 (5)
C25	0.0363 (6)	0.0542 (8)	0.0496 (8)	−0.0072 (6)	−0.0054 (6)	−0.0192 (6)
C26	0.0405 (7)	0.0676 (9)	0.0510 (8)	−0.0086 (6)	−0.0135 (6)	−0.0139 (7)
C27	0.0559 (9)	0.0772 (11)	0.0461 (8)	−0.0196 (8)	−0.0102 (7)	−0.0223 (8)
C28	0.0583 (9)	0.0600 (9)	0.0536 (9)	−0.0114 (7)	−0.0029 (7)	−0.0286 (7)
C29	0.0455 (7)	0.0440 (7)	0.0509 (8)	−0.0093 (6)	−0.0072 (6)	−0.0144 (6)
C30	0.0355 (6)	0.0536 (8)	0.0428 (7)	−0.0125 (5)	−0.0025 (5)	−0.0135 (6)
C31	0.0816 (12)	0.0871 (13)	0.0457 (9)	−0.0209 (10)	−0.0202 (8)	−0.0016 (9)
O1	0.0458 (5)	0.0430 (5)	0.0455 (5)	0.0049 (4)	−0.0157 (4)	−0.0133 (4)
O2	0.0703 (7)	0.0465 (6)	0.0492 (6)	0.0059 (5)	−0.0277 (5)	−0.0085 (5)
O3	0.0466 (5)	0.0408 (5)	0.0757 (7)	−0.0176 (4)	0.0115 (5)	−0.0207 (5)
O4	0.0585 (6)	0.0452 (6)	0.0961 (9)	−0.0152 (5)	0.0167 (6)	−0.0367 (6)
O5	0.0748 (7)	0.0553 (6)	0.0427 (6)	−0.0113 (5)	−0.0180 (5)	−0.0061 (5)
O6	0.0670 (7)	0.0698 (7)	0.0467 (6)	−0.0169 (5)	−0.0023 (5)	−0.0268 (5)

C1—C9	1.5289 (16)	C17—C18	1.386 (2)
C1—C10	1.5368 (17)	C17—H17	0.9300
C1—C2	1.5370 (17)	C18—H18	0.9300
C1—C21	1.5668 (16)	C19—O4	1.1970 (15)
C2—O2	1.2035 (15)	C19—O3	1.3297 (16)
C2—C3	1.4812 (17)	C20—O3	1.4374 (17)
C3—C8	1.3855 (17)	C20—H20A	0.9600
C3—C4	1.3862 (17)	C20—H20B	0.9600
C4—C5	1.378 (2)	C20—H20C	0.9600
C4—H4	0.9300	C21—C22	1.4985 (18)
C5—C6	1.383 (2)	C21—H21A	0.9700
C5—H5	0.9300	C21—H21B	0.9700
C6—C7	1.378 (2)	C22—C23	1.3359 (18)
C6—H6	0.9300	C22—C30	1.4911 (19)
C7—C8	1.3868 (17)	C23—C24	1.4735 (18)
C7—H7	0.9300	C23—H23	0.9300
C8—C9	1.4752 (17)	C24—C29	1.3902 (19)
C9—O1	1.2073 (14)	C24—C25	1.3957 (19)
C10—C11	1.5070 (17)	C25—C26	1.381 (2)
C10—H10A	0.9700	C25—H25	0.9300
C10—H10B	0.9700	C26—C27	1.369 (2)
C11—C12	1.3339 (17)	C26—H26	0.9300
C11—C19	1.4841 (17)	C27—C28	1.376 (2)
C12—C13	1.4779 (17)	C27—H27	0.9300
C12—H12	0.9300	C28—C29	1.379 (2)
C13—C14	1.385 (2)	C28—H28	0.9300
C13—C18	1.3882 (19)	C29—H29	0.9300
C14—C15	1.387 (2)	C30—O6	1.1994 (17)
C14—H14	0.9300	C30—O5	1.3354 (17)
C15—C16	1.370 (2)	C31—O5	1.4453 (19)
C15—H15	0.9300	C31—H31A	0.9600
C16—C17	1.372 (3)	C31—H31B	0.9600
C16—H16	0.9300	C31—H31C	0.9600
C9—C1—C10	114.88 (10)	C16—C17—H17	119.5
C9—C1—C2	102.63 (9)	C18—C17—H17	119.5
C10—C1—C2	114.96 (10)	C17—C18—C13	119.89 (15)
C9—C1—C21	112.06 (10)	C17—C18—H18	120.1
C10—C1—C21	108.52 (9)	C13—C18—H18	120.1
C2—C1—C21	103.19 (9)	O4—C19—O3	122.35 (12)
O2—C2—C3	126.87 (12)	O4—C19—C11	123.84 (12)
O2—C2—C1	125.44 (12)	O3—C19—C11	113.78 (10)
C3—C2—C1	107.57 (10)	O3—C20—H20A	109.5
C8—C3—C4	120.86 (12)	O3—C20—H20B	109.5
C8—C3—C2	109.67 (10)	H20A—C20—H20B	109.5
C4—C3—C2	129.47 (12)	O3—C20—H20C	109.5
C5—C4—C3	117.82 (13)	H20A—C20—H20C	109.5
C5—C4—H4	121.1	H20B—C20—H20C	109.5
C3—C4—H4	121.1	C22—C21—C1	114.63 (10)
C4—C5—C6	121.34 (13)	C22—C21—H21A	108.6
C4—C5—H5	119.3	C1—C21—H21A	108.6
C6—C5—H5	119.3	C22—C21—H21B	108.6
C7—C6—C5	121.08 (13)	C1—C21—H21B	108.6
C7—C6—H6	119.5	H21A—C21—H21B	107.6
C5—C6—H6	119.5	C23—C22—C30	119.34 (12)
C6—C7—C8	117.83 (13)	C23—C22—C21	126.49 (12)
C6—C7—H7	121.1	C30—C22—C21	114.10 (11)
C8—C7—H7	121.1	C22—C23—C24	131.01 (12)
C3—C8—C7	121.04 (12)	C22—C23—H23	114.5
C3—C8—C9	110.18 (10)	C24—C23—H23	114.5
C7—C8—C9	128.78 (12)	C29—C24—C25	117.80 (12)
O1—C9—C8	126.17 (11)	C29—C24—C23	118.80 (12)
O1—C9—C1	125.91 (11)	C25—C24—C23	123.09 (12)
C8—C9—C1	107.88 (9)	C26—C25—C24	120.52 (13)
C11—C10—C1	120.19 (10)	C26—C25—H25	119.7
C11—C10—H10A	107.3	C24—C25—H25	119.7
C1—C10—H10A	107.3	C27—C26—C25	120.79 (14)
C11—C10—H10B	107.3	C27—C26—H26	119.6
C1—C10—H10B	107.3	C25—C26—H26	119.6
H10A—C10—H10B	106.9	C26—C27—C28	119.49 (14)
C12—C11—C19	118.89 (11)	C26—C27—H27	120.3
C12—C11—C10	124.08 (11)	C28—C27—H27	120.3
C19—C11—C10	116.93 (10)	C27—C28—C29	120.30 (14)
C11—C12—C13	128.02 (12)	C27—C28—H28	119.8
C11—C12—H12	116.0	C29—C28—H28	119.8
C13—C12—H12	116.0	C28—C29—C24	121.09 (13)
C14—C13—C18	118.65 (12)	C28—C29—H29	119.5
C14—C13—C12	120.66 (12)	C24—C29—H29	119.5
C18—C13—C12	120.43 (13)	O6—C30—O5	123.11 (13)
C13—C14—C15	120.79 (14)	O6—C30—C22	123.02 (13)
C13—C14—H14	119.6	O5—C30—C22	113.82 (12)
C15—C14—H14	119.6	O5—C31—H31A	109.5
C16—C15—C14	120.12 (16)	O5—C31—H31B	109.5
C16—C15—H15	119.9	H31A—C31—H31B	109.5
C14—C15—H15	119.9	O5—C31—H31C	109.5
C15—C16—C17	119.57 (14)	H31A—C31—H31C	109.5
C15—C16—H16	120.2	H31B—C31—H31C	109.5
C17—C16—H16	120.2	C19—O3—C20	116.63 (11)
C16—C17—C18	120.93 (14)	C30—O5—C31	115.67 (13)
C9—C1—C2—O2	−169.81 (13)	C11—C12—C13—C18	−127.96 (15)
C10—C1—C2—O2	−44.38 (17)	C18—C13—C14—C15	−1.0 (2)
C21—C1—C2—O2	73.58 (15)	C12—C13—C14—C15	173.24 (14)
C9—C1—C2—C3	13.99 (12)	C13—C14—C15—C16	2.1 (2)
C10—C1—C2—C3	139.42 (10)	C14—C15—C16—C17	−1.0 (3)
C21—C1—C2—C3	−102.62 (10)	C15—C16—C17—C18	−1.2 (2)
O2—C2—C3—C8	173.92 (13)	C16—C17—C18—C13	2.3 (2)
C1—C2—C3—C8	−9.95 (13)	C14—C13—C18—C17	−1.2 (2)
O2—C2—C3—C4	−6.3 (2)	C12—C13—C18—C17	−175.45 (13)
C1—C2—C3—C4	169.83 (12)	C12—C11—C19—O4	171.63 (14)
C8—C3—C4—C5	−0.54 (19)	C10—C11—C19—O4	−11.90 (19)
C2—C3—C4—C5	179.70 (12)	C12—C11—C19—O3	−6.35 (17)
C3—C4—C5—C6	−1.1 (2)	C10—C11—C19—O3	170.13 (11)
C4—C5—C6—C7	1.5 (2)	C9—C1—C21—C22	55.81 (13)
C5—C6—C7—C8	−0.2 (2)	C10—C1—C21—C22	−72.09 (13)
C4—C3—C8—C7	1.85 (19)	C2—C1—C21—C22	165.52 (10)
C2—C3—C8—C7	−178.35 (11)	C1—C21—C22—C23	102.49 (14)
C4—C3—C8—C9	−178.62 (11)	C1—C21—C22—C30	−80.62 (13)
C2—C3—C8—C9	1.18 (14)	C30—C22—C23—C24	−170.34 (12)
C6—C7—C8—C3	−1.47 (19)	C21—C22—C23—C24	6.4 (2)
C6—C7—C8—C9	179.09 (12)	C22—C23—C24—C29	−142.60 (15)
C3—C8—C9—O1	−169.82 (12)	C22—C23—C24—C25	44.0 (2)
C7—C8—C9—O1	9.7 (2)	C29—C24—C25—C26	−0.69 (19)
C3—C8—C9—C1	8.11 (13)	C23—C24—C25—C26	172.75 (13)
C7—C8—C9—C1	−172.40 (12)	C24—C25—C26—C27	0.2 (2)
C10—C1—C9—O1	39.12 (17)	C25—C26—C27—C28	0.5 (2)
C2—C1—C9—O1	164.60 (12)	C26—C27—C28—C29	−0.6 (2)
C21—C1—C9—O1	−85.33 (14)	C27—C28—C29—C24	0.1 (2)
C10—C1—C9—C8	−138.82 (10)	C25—C24—C29—C28	0.6 (2)
C2—C1—C9—C8	−13.33 (12)	C23—C24—C29—C28	−173.17 (13)
C21—C1—C9—C8	96.74 (11)	C23—C22—C30—O6	167.08 (13)
C9—C1—C10—C11	32.08 (15)	C21—C22—C30—O6	−10.05 (18)
C2—C1—C10—C11	−86.71 (13)	C23—C22—C30—O5	−10.50 (17)
C21—C1—C10—C11	158.36 (10)	C21—C22—C30—O5	172.37 (11)
C1—C10—C11—C12	−126.37 (13)	O4—C19—O3—C20	1.5 (2)
C1—C10—C11—C19	57.36 (15)	C11—C19—O3—C20	179.47 (13)
C19—C11—C12—C13	−171.64 (12)	O6—C30—O5—C31	−0.5 (2)
C10—C11—C12—C13	12.2 (2)	C22—C30—O5—C31	177.03 (13)
C11—C12—C13—C14	57.91 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1	0.93	2.40	3.288 (2)	161
C27—H27···O2i	0.93	2.46	3.207 (2)	137
C31—H31C···Cg1ii	0.96	2.87	3.554 (2)	129
C20—H20B···Cg2iii	0.96	2.86	3.500 (2)	125

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C13–C18 and C24–C29 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O1	0.93	2.40	3.288 (2)	161
C27—H27⋯O2i	0.93	2.46	3.207 (2)	137
C31—H31C⋯Cg1ii	0.96	2.87	3.554 (2)	129
C20—H20B⋯Cg2iii	0.96	2.86	3.500 (2)	125

Symmetry codes: (i) ; (ii) ; (iii) .