2,4-Dimeth-oxy-6-[(E)-2-(4-meth-oxy-phenyl)ethen-yl]benzaldehyde.

There are two conformationally similar mol-ecules in the asymmetric unit of he title compound, C18H18O4, in which the dihedral angles between the benzene rings are 23.54 (12) and 31.11 (12)°. In the crystal, C-H⋯π inter-actions (minimum H⋯ring centroid distance = 2.66 Å) link the mol-ecules into a layered structure extending down a.

Related literature

The title compound is a derivative of the natural product resveratrol (trans-3,4,5-trihy­droxy­stilbene). For background to resveratrol, see: Jang et al. (1997 ▶); Orsini et al. (1997 ▶); Pettit et al. (2002 ▶). For standard bond lengths and angles, see: Boumendjel et al. (2008 ▶). For the synthesis of the title compound, see: Huang et al. (2007 ▶).

Experimental

Crystal data

C18H18O4

M = 298.32

Triclinic,

a = 9.292 (5) Å

b = 9.448 (5) Å

c = 17.547 (5) Å

α = 84.097 (5)°

β = 84.040 (5)°

γ = 83.315 (5)°

V = 1515.3 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.973, T max = 0.982

10535 measured reflections

5272 independent reflections

3060 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.168

S = 0.79

5272 reflections

404 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813007964/zs2252sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007964/zs2252Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007964/zs2252Isup3.ps

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007964/zs2252Isup4.mol

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007964/zs2252Isup5.cml

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

C18H18O4	Z = 4
Mr = 298.32	F(000) = 632
Triclinic, P1	Dx = 1.308 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 9.292 (5) Å	Cell parameters from 1909 reflections
b = 9.448 (5) Å	θ = 2.2–26.7°
c = 17.547 (5) Å	µ = 0.09 mm−1
α = 84.097 (5)°	T = 298 K
β = 84.040 (5)°	Block, colourless
γ = 83.315 (5)°	0.30 × 0.20 × 0.20 mm
V = 1515.3 (12) Å3

Bruker SMART CCD area-detector diffractometer	5272 independent reflections
Radiation source: fine-focus sealed tube	3060 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→10
Tmin = 0.973, Tmax = 0.982	k = −11→11
10535 measured reflections	l = −20→19

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.168	w = 1/[σ2(Fo2) + (0.1P)2 + 0.699P] where P = (Fo2 + 2Fc2)/3
S = 0.79	(Δ/σ)max < 0.001
5272 reflections	Δρmax = 0.15 e Å−3
404 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: 0.017 (2)

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
O4	0.14160 (19)	0.29091 (17)	0.65390 (9)	0.0490 (5)
O8	0.6445 (2)	0.3074 (2)	0.65049 (10)	0.0584 (5)
O2	0.6991 (2)	−0.0498 (2)	0.13171 (10)	0.0641 (6)
O6	1.2124 (2)	−0.0612 (2)	0.13477 (10)	0.0663 (6)
C12	0.3000 (2)	0.2119 (2)	0.42976 (13)	0.0377 (6)
C15	0.1936 (2)	0.2736 (2)	0.57966 (13)	0.0368 (6)
O5	0.9275 (2)	0.3222 (2)	0.00997 (10)	0.0698 (6)
O1	0.4129 (2)	0.3330 (2)	0.00836 (10)	0.0674 (6)
C33	0.6939 (3)	0.2778 (2)	0.57720 (13)	0.0393 (6)
C29	0.8934 (3)	0.1922 (2)	0.35458 (13)	0.0413 (6)
H29	0.9886	0.1486	0.3536	0.050*
C13	0.2388 (2)	0.3479 (2)	0.44573 (13)	0.0400 (6)
H13	0.2332	0.4200	0.4055	0.048*
C11	0.3571 (3)	0.1739 (3)	0.35295 (14)	0.0444 (6)
H11	0.4007	0.0807	0.3497	0.053*
C30	0.8207 (3)	0.2192 (2)	0.43039 (13)	0.0367 (6)
C35	0.8980 (3)	0.1892 (2)	0.49504 (13)	0.0404 (6)
H35	0.9942	0.1490	0.4892	0.048*
C31	0.6761 (3)	0.2748 (2)	0.44293 (13)	0.0394 (6)
H31	0.6201	0.2922	0.4013	0.047*
C16	0.2576 (3)	0.1382 (2)	0.56550 (13)	0.0401 (6)
H16	0.2659	0.0670	0.6060	0.048*
C4	0.5278 (3)	0.1016 (3)	0.20863 (14)	0.0463 (6)
H4	0.5554	0.0505	0.2539	0.056*
C19	0.9651 (3)	0.2384 (3)	0.07433 (14)	0.0491 (7)
C24	0.8850 (3)	0.2751 (3)	0.14382 (14)	0.0436 (6)
C3	0.5943 (3)	0.0623 (3)	0.13922 (15)	0.0471 (6)
O7	0.7066 (2)	0.4560 (2)	0.19247 (11)	0.0734 (6)
C32	0.6124 (3)	0.3051 (2)	0.51476 (13)	0.0410 (6)
H32	0.5156	0.3435	0.5211	0.049*
C34	0.8365 (3)	0.2172 (3)	0.56693 (14)	0.0443 (6)
H34	0.8908	0.1954	0.6090	0.053*
C23	0.9194 (3)	0.1940 (2)	0.21264 (13)	0.0421 (6)
C20	1.0740 (3)	0.1273 (3)	0.07344 (15)	0.0522 (7)
H20	1.1262	0.1047	0.0273	0.063*
C1	0.4531 (3)	0.2517 (3)	0.07286 (14)	0.0473 (6)
C5	0.4200 (3)	0.2160 (3)	0.21234 (13)	0.0430 (6)
C2	0.5590 (3)	0.1378 (3)	0.07091 (14)	0.0516 (7)
H2	0.6062	0.1118	0.0243	0.062*
C28	0.8397 (3)	0.2227 (2)	0.28713 (14)	0.0444 (6)
H28	0.7443	0.2654	0.2869	0.053*
C21	1.1053 (3)	0.0493 (3)	0.14175 (15)	0.0481 (6)
C14	0.1858 (3)	0.3803 (2)	0.51919 (13)	0.0395 (6)
H14	0.1453	0.4726	0.5280	0.047*
C6	0.3793 (3)	0.2931 (3)	0.14320 (14)	0.0441 (6)
O3	0.1938 (3)	0.4673 (3)	0.19099 (12)	0.0913 (8)
C17	0.3091 (3)	0.1078 (2)	0.49209 (13)	0.0396 (6)
H17	0.3509	0.0157	0.4837	0.047*
C22	1.0291 (3)	0.0813 (3)	0.21013 (14)	0.0475 (6)
H22	1.0513	0.0267	0.2554	0.057*
C10	0.3540 (3)	0.2567 (3)	0.28771 (14)	0.0492 (7)
H10	0.3060	0.3484	0.2896	0.059*
C27	0.7704 (3)	0.3951 (3)	0.13975 (16)	0.0545 (7)
H27	0.7437	0.4282	0.0909	0.065*
C18	0.0775 (3)	0.4283 (3)	0.67268 (16)	0.0655 (9)
H18A	0.1483	0.4957	0.6614	0.098*
H18B	0.0444	0.4241	0.7265	0.098*
H18C	−0.0035	0.4581	0.6429	0.098*
C9	0.2627 (3)	0.4111 (3)	0.13893 (17)	0.0593 (8)
H9	0.2396	0.4467	0.0898	0.071*
C25	1.0115 (4)	0.2970 (3)	−0.06044 (15)	0.0743 (9)
H25A	1.1114	0.3084	−0.0557	0.111*
H25B	0.9758	0.3642	−0.1008	0.111*
H25C	1.0042	0.2014	−0.0725	0.111*
C8	0.7351 (4)	−0.1367 (3)	0.19987 (16)	0.0722 (9)
H8A	0.7697	−0.0791	0.2346	0.108*
H8B	0.8097	−0.2118	0.1868	0.108*
H8C	0.6502	−0.1779	0.2241	0.108*
C36	0.5076 (3)	0.3858 (3)	0.66358 (16)	0.0632 (8)
H36A	0.5030	0.4724	0.6297	0.095*
H36B	0.4933	0.4091	0.7160	0.095*
H36C	0.4329	0.3295	0.6540	0.095*
C26	1.2461 (4)	−0.1482 (3)	0.20355 (16)	0.0727 (9)
H26A	1.2762	−0.0899	0.2394	0.109*
H26B	1.3232	−0.2215	0.1914	0.109*
H26C	1.1613	−0.1917	0.2260	0.109*
C7	0.4947 (4)	0.3057 (3)	−0.06241 (15)	0.0728 (9)
H7A	0.5953	0.3159	−0.0586	0.109*
H7B	0.4589	0.3728	−0.1028	0.109*
H7C	0.4855	0.2101	−0.0738	0.109*

	U11	U22	U33	U12	U13	U23
O4	0.0641 (12)	0.0468 (10)	0.0339 (10)	0.0028 (9)	−0.0014 (9)	−0.0061 (8)
O8	0.0587 (12)	0.0752 (13)	0.0359 (11)	0.0159 (10)	−0.0024 (9)	−0.0079 (9)
O2	0.0753 (14)	0.0640 (12)	0.0428 (11)	0.0229 (11)	0.0027 (10)	0.0008 (9)
O6	0.0766 (14)	0.0687 (13)	0.0430 (11)	0.0281 (11)	0.0005 (10)	−0.0008 (9)
C12	0.0364 (13)	0.0377 (13)	0.0383 (14)	−0.0038 (10)	−0.0014 (11)	−0.0023 (10)
C15	0.0364 (13)	0.0404 (13)	0.0336 (14)	−0.0026 (11)	−0.0040 (11)	−0.0048 (10)
O5	0.0817 (14)	0.0805 (14)	0.0353 (11)	0.0236 (11)	0.0019 (10)	0.0076 (10)
O1	0.0782 (14)	0.0788 (14)	0.0348 (11)	0.0208 (11)	0.0007 (10)	0.0044 (9)
C33	0.0438 (15)	0.0380 (13)	0.0347 (14)	−0.0009 (11)	−0.0027 (11)	−0.0016 (10)
C29	0.0428 (14)	0.0406 (13)	0.0391 (15)	−0.0001 (11)	−0.0019 (12)	−0.0034 (11)
C13	0.0452 (15)	0.0379 (13)	0.0353 (14)	−0.0010 (11)	−0.0065 (11)	0.0039 (11)
C11	0.0488 (15)	0.0438 (14)	0.0392 (15)	−0.0006 (12)	−0.0005 (12)	−0.0062 (12)
C30	0.0395 (14)	0.0331 (12)	0.0371 (14)	−0.0032 (10)	−0.0033 (11)	−0.0022 (10)
C35	0.0334 (13)	0.0438 (14)	0.0440 (15)	−0.0008 (11)	−0.0076 (11)	−0.0035 (11)
C31	0.0423 (15)	0.0405 (13)	0.0350 (14)	−0.0011 (11)	−0.0105 (11)	0.0018 (10)
C16	0.0483 (15)	0.0328 (12)	0.0385 (14)	−0.0036 (11)	−0.0077 (12)	0.0028 (10)
C4	0.0518 (16)	0.0506 (15)	0.0336 (14)	0.0021 (13)	−0.0040 (12)	0.0007 (11)
C19	0.0574 (17)	0.0488 (15)	0.0383 (15)	0.0006 (13)	−0.0054 (13)	0.0030 (12)
C24	0.0491 (15)	0.0428 (14)	0.0368 (15)	0.0013 (12)	−0.0022 (12)	−0.0033 (11)
C3	0.0511 (16)	0.0482 (15)	0.0399 (15)	0.0024 (13)	−0.0018 (12)	−0.0050 (12)
O7	0.0889 (16)	0.0706 (13)	0.0507 (13)	0.0321 (12)	−0.0004 (11)	−0.0093 (10)
C32	0.0351 (14)	0.0435 (14)	0.0421 (15)	0.0026 (11)	−0.0037 (11)	−0.0012 (11)
C34	0.0406 (15)	0.0536 (15)	0.0386 (15)	0.0018 (12)	−0.0113 (12)	−0.0037 (12)
C23	0.0475 (15)	0.0406 (13)	0.0377 (14)	−0.0028 (12)	−0.0022 (12)	−0.0052 (11)
C20	0.0574 (17)	0.0561 (16)	0.0388 (16)	0.0063 (14)	0.0032 (13)	−0.0062 (13)
C1	0.0549 (16)	0.0515 (15)	0.0335 (14)	−0.0017 (13)	−0.0058 (12)	0.0026 (12)
C5	0.0472 (15)	0.0472 (14)	0.0351 (14)	−0.0050 (12)	−0.0052 (12)	−0.0047 (11)
C2	0.0611 (18)	0.0555 (16)	0.0344 (15)	0.0036 (14)	0.0016 (13)	−0.0035 (12)
C28	0.0486 (15)	0.0427 (14)	0.0403 (15)	0.0015 (12)	−0.0029 (12)	−0.0050 (11)
C21	0.0515 (16)	0.0460 (15)	0.0441 (16)	0.0047 (12)	−0.0025 (13)	−0.0051 (12)
C14	0.0439 (14)	0.0323 (12)	0.0412 (15)	0.0031 (11)	−0.0073 (11)	−0.0031 (11)
C6	0.0463 (15)	0.0476 (15)	0.0369 (15)	−0.0012 (12)	−0.0023 (12)	−0.0034 (11)
O3	0.1072 (18)	0.0979 (17)	0.0522 (14)	0.0503 (15)	0.0014 (13)	−0.0063 (12)
C17	0.0452 (14)	0.0311 (12)	0.0414 (15)	−0.0005 (10)	−0.0030 (11)	−0.0036 (10)
C22	0.0546 (16)	0.0511 (15)	0.0346 (15)	0.0019 (13)	−0.0033 (12)	−0.0035 (12)
C10	0.0545 (16)	0.0524 (15)	0.0390 (15)	0.0053 (13)	−0.0042 (12)	−0.0078 (12)
C27	0.0600 (18)	0.0560 (17)	0.0437 (16)	0.0056 (14)	−0.0046 (14)	−0.0004 (13)
C18	0.088 (2)	0.0557 (17)	0.0473 (18)	0.0156 (16)	0.0027 (16)	−0.0153 (14)
C9	0.0634 (19)	0.0636 (18)	0.0450 (17)	0.0100 (15)	0.0002 (15)	−0.0005 (14)
C25	0.091 (2)	0.086 (2)	0.0361 (17)	0.0159 (19)	0.0019 (16)	0.0065 (15)
C8	0.087 (2)	0.0664 (19)	0.0513 (19)	0.0222 (17)	−0.0011 (16)	0.0105 (15)
C36	0.0549 (18)	0.076 (2)	0.0524 (18)	0.0074 (15)	0.0112 (14)	−0.0083 (15)
C26	0.084 (2)	0.070 (2)	0.0526 (19)	0.0292 (17)	−0.0030 (16)	0.0004 (15)
C7	0.091 (2)	0.080 (2)	0.0374 (17)	0.0167 (18)	0.0009 (16)	0.0060 (15)

O4—C15	1.361 (3)	C3—C2	1.380 (3)
O4—C18	1.420 (3)	O7—C27	1.206 (3)
O8—C33	1.365 (3)	C32—H32	0.9300
O8—C36	1.405 (3)	C34—H34	0.9300
O2—C3	1.360 (3)	C23—C22	1.386 (3)
O2—C8	1.426 (3)	C23—C28	1.468 (3)
O6—C21	1.362 (3)	C20—C21	1.380 (3)
O6—C26	1.430 (3)	C20—H20	0.9300
C12—C13	1.387 (3)	C1—C2	1.372 (3)
C12—C17	1.396 (3)	C1—C6	1.417 (3)
C12—C11	1.461 (3)	C5—C6	1.412 (3)
C15—C16	1.382 (3)	C5—C10	1.468 (3)
C15—C14	1.388 (3)	C2—H2	0.9300
O5—C19	1.363 (3)	C28—H28	0.9300
O5—C25	1.418 (3)	C21—C22	1.372 (3)
O1—C1	1.361 (3)	C14—H14	0.9300
O1—C7	1.418 (3)	C6—C9	1.463 (4)
C33—C32	1.382 (3)	O3—C9	1.194 (3)
C33—C34	1.383 (3)	C17—H17	0.9300
C29—C28	1.324 (3)	C22—H22	0.9300
C29—C30	1.461 (3)	C10—H10	0.9300
C29—H29	0.9300	C27—H27	0.9300
C13—C14	1.383 (3)	C18—H18A	0.9600
C13—H13	0.9300	C18—H18B	0.9600
C11—C10	1.319 (3)	C18—H18C	0.9600
C11—H11	0.9300	C9—H9	0.9300
C30—C31	1.389 (3)	C25—H25A	0.9600
C30—C35	1.392 (3)	C25—H25B	0.9600
C35—C34	1.368 (3)	C25—H25C	0.9600
C35—H35	0.9300	C8—H8A	0.9600
C31—C32	1.379 (3)	C8—H8B	0.9600
C31—H31	0.9300	C8—H8C	0.9600
C16—C17	1.374 (3)	C36—H36A	0.9600
C16—H16	0.9300	C36—H36B	0.9600
C4—C3	1.373 (3)	C36—H36C	0.9600
C4—C5	1.387 (3)	C26—H26A	0.9600
C4—H4	0.9300	C26—H26B	0.9600
C19—C20	1.371 (3)	C26—H26C	0.9600
C19—C24	1.414 (3)	C7—H7A	0.9600
C24—C23	1.407 (3)	C7—H7B	0.9600
C24—C27	1.464 (3)	C7—H7C	0.9600
C15—O4—C18	118.68 (19)	C1—C2—C3	119.0 (2)
C33—O8—C36	119.0 (2)	C1—C2—H2	120.5
C3—O2—C8	117.7 (2)	C3—C2—H2	120.5
C21—O6—C26	117.2 (2)	C29—C28—C23	124.8 (2)
C13—C12—C17	116.8 (2)	C29—C28—H28	117.6
C13—C12—C11	123.9 (2)	C23—C28—H28	117.6
C17—C12—C11	119.2 (2)	O6—C21—C22	124.1 (2)
O4—C15—C16	115.8 (2)	O6—C21—C20	114.9 (2)
O4—C15—C14	124.9 (2)	C22—C21—C20	121.0 (2)
C16—C15—C14	119.3 (2)	C13—C14—C15	119.3 (2)
C19—O5—C25	117.6 (2)	C13—C14—H14	120.4
C1—O1—C7	117.6 (2)	C15—C14—H14	120.4
O8—C33—C32	124.7 (2)	C5—C6—C1	118.2 (2)
O8—C33—C34	115.8 (2)	C5—C6—C9	124.4 (2)
C32—C33—C34	119.5 (2)	C1—C6—C9	117.4 (2)
C28—C29—C30	127.5 (2)	C16—C17—C12	121.5 (2)
C28—C29—H29	116.2	C16—C17—H17	119.2
C30—C29—H29	116.2	C12—C17—H17	119.2
C14—C13—C12	122.5 (2)	C21—C22—C23	120.9 (2)
C14—C13—H13	118.8	C21—C22—H22	119.6
C12—C13—H13	118.8	C23—C22—H22	119.6
C10—C11—C12	127.4 (2)	C11—C10—C5	125.5 (2)
C10—C11—H11	116.3	C11—C10—H10	117.3
C12—C11—H11	116.3	C5—C10—H10	117.3
C31—C30—C35	116.5 (2)	O7—C27—C24	127.4 (3)
C31—C30—C29	123.9 (2)	O7—C27—H27	116.3
C35—C30—C29	119.6 (2)	C24—C27—H27	116.3
C34—C35—C30	121.9 (2)	O4—C18—H18A	109.5
C34—C35—H35	119.0	O4—C18—H18B	109.5
C30—C35—H35	119.0	H18A—C18—H18B	109.5
C32—C31—C30	122.4 (2)	O4—C18—H18C	109.5
C32—C31—H31	118.8	H18A—C18—H18C	109.5
C30—C31—H31	118.8	H18B—C18—H18C	109.5
C17—C16—C15	120.6 (2)	O3—C9—C6	127.8 (3)
C17—C16—H16	119.7	O3—C9—H9	116.1
C15—C16—H16	119.7	C6—C9—H9	116.1
C3—C4—C5	121.1 (2)	O5—C25—H25A	109.5
C3—C4—H4	119.4	O5—C25—H25B	109.5
C5—C4—H4	119.4	H25A—C25—H25B	109.5
O5—C19—C20	123.4 (2)	O5—C25—H25C	109.5
O5—C19—C24	115.3 (2)	H25A—C25—H25C	109.5
C20—C19—C24	121.3 (2)	H25B—C25—H25C	109.5
C23—C24—C19	118.3 (2)	O2—C8—H8A	109.5
C23—C24—C27	123.8 (2)	O2—C8—H8B	109.5
C19—C24—C27	117.9 (2)	H8A—C8—H8B	109.5
O2—C3—C4	123.9 (2)	O2—C8—H8C	109.5
O2—C3—C2	114.9 (2)	H8A—C8—H8C	109.5
C4—C3—C2	121.1 (2)	H8B—C8—H8C	109.5
C31—C32—C33	119.3 (2)	O8—C36—H36A	109.5
C31—C32—H32	120.3	O8—C36—H36B	109.5
C33—C32—H32	120.3	H36A—C36—H36B	109.5
C35—C34—C33	120.2 (2)	O8—C36—H36C	109.5
C35—C34—H34	119.9	H36A—C36—H36C	109.5
C33—C34—H34	119.9	H36B—C36—H36C	109.5
C22—C23—C24	119.3 (2)	O6—C26—H26A	109.5
C22—C23—C28	118.8 (2)	O6—C26—H26B	109.5
C24—C23—C28	121.9 (2)	H26A—C26—H26B	109.5
C19—C20—C21	119.2 (2)	O6—C26—H26C	109.5
C19—C20—H20	120.4	H26A—C26—H26C	109.5
C21—C20—H20	120.4	H26B—C26—H26C	109.5
O1—C1—C2	122.8 (2)	O1—C7—H7A	109.5
O1—C1—C6	115.6 (2)	O1—C7—H7B	109.5
C2—C1—C6	121.5 (2)	H7A—C7—H7B	109.5
C4—C5—C6	119.0 (2)	O1—C7—H7C	109.5
C4—C5—C10	119.5 (2)	H7A—C7—H7C	109.5
C6—C5—C10	121.6 (2)	H7B—C7—H7C	109.5
C18—O4—C15—C16	178.6 (2)	C7—O1—C1—C6	173.1 (2)
C18—O4—C15—C14	−1.7 (3)	C3—C4—C5—C6	−0.2 (4)
C36—O8—C33—C32	−7.7 (4)	C3—C4—C5—C10	−178.5 (2)
C36—O8—C33—C34	171.8 (2)	O1—C1—C2—C3	179.1 (2)
C17—C12—C13—C14	−1.4 (3)	C6—C1—C2—C3	−0.2 (4)
C11—C12—C13—C14	−179.9 (2)	O2—C3—C2—C1	179.2 (2)
C13—C12—C11—C10	−3.6 (4)	C4—C3—C2—C1	−1.5 (4)
C17—C12—C11—C10	177.9 (2)	C30—C29—C28—C23	179.3 (2)
C28—C29—C30—C31	4.4 (4)	C22—C23—C28—C29	27.9 (4)
C28—C29—C30—C35	−175.4 (2)	C24—C23—C28—C29	−153.8 (2)
C31—C30—C35—C34	−2.1 (3)	C26—O6—C21—C22	0.1 (4)
C29—C30—C35—C34	177.7 (2)	C26—O6—C21—C20	−178.1 (3)
C35—C30—C31—C32	2.7 (3)	C19—C20—C21—O6	178.3 (2)
C29—C30—C31—C32	−177.0 (2)	C19—C20—C21—C22	0.1 (4)
O4—C15—C16—C17	177.7 (2)	C12—C13—C14—C15	0.0 (4)
C14—C15—C16—C17	−2.0 (3)	O4—C15—C14—C13	−178.0 (2)
C25—O5—C19—C20	−3.6 (4)	C16—C15—C14—C13	1.7 (3)
C25—O5—C19—C24	175.3 (2)	C4—C5—C6—C1	−1.4 (4)
O5—C19—C24—C23	−179.3 (2)	C10—C5—C6—C1	176.9 (2)
C20—C19—C24—C23	−0.3 (4)	C4—C5—C6—C9	176.9 (2)
O5—C19—C24—C27	1.1 (4)	C10—C5—C6—C9	−4.8 (4)
C20—C19—C24—C27	−179.9 (2)	O1—C1—C6—C5	−177.7 (2)
C8—O2—C3—C4	4.0 (4)	C2—C1—C6—C5	1.6 (4)
C8—O2—C3—C2	−176.8 (3)	O1—C1—C6—C9	3.8 (4)
C5—C4—C3—O2	−179.1 (2)	C2—C1—C6—C9	−176.8 (2)
C5—C4—C3—C2	1.7 (4)	C15—C16—C17—C12	0.6 (4)
C30—C31—C32—C33	−0.9 (3)	C13—C12—C17—C16	1.0 (3)
O8—C33—C32—C31	177.8 (2)	C11—C12—C17—C16	179.7 (2)
C34—C33—C32—C31	−1.7 (3)	O6—C21—C22—C23	−178.8 (2)
C30—C35—C34—C33	−0.4 (4)	C20—C21—C22—C23	−0.7 (4)
O8—C33—C34—C35	−177.2 (2)	C24—C23—C22—C21	0.8 (4)
C32—C33—C34—C35	2.3 (4)	C28—C23—C22—C21	179.1 (2)
C19—C24—C23—C22	−0.3 (4)	C12—C11—C10—C5	176.5 (2)
C27—C24—C23—C22	179.3 (2)	C4—C5—C10—C11	−19.5 (4)
C19—C24—C23—C28	−178.6 (2)	C6—C5—C10—C11	162.3 (3)
C27—C24—C23—C28	1.0 (4)	C23—C24—C27—O7	12.8 (5)
O5—C19—C20—C21	179.3 (3)	C19—C24—C27—O7	−167.6 (3)
C24—C19—C20—C21	0.4 (4)	C5—C6—C9—O3	6.5 (5)
C7—O1—C1—C2	−6.2 (4)	C1—C6—C9—O3	−175.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1	0.93	2.29	2.681 (4)	105
C10—H10···O3	0.93	2.25	2.863 (4)	123
C27—H27···O5	0.93	2.31	2.681 (4)	103
C28—H28···O7	0.93	2.34	2.861 (3)	115
C14—H14···Cg4i	0.93	2.88	3.597 (3)	135
C17—H14···Cg4ii	0.93	2.76	3.471 (3)	134
C32—H14···Cg2	0.93	2.82	3.530 (3)	135
C15—H14···Cg2iii	0.93	2.66	3.371 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the C12–C17 and C30–C35 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯Cg4i	0.93	2.88	3.597 (3)	135
C17—H14⋯Cg4ii	0.93	2.76	3.471 (3)	134
C32—H14⋯Cg2	0.93	2.82	3.530 (3)	135
C15—H14⋯Cg2iii	0.93	2.66	3.371 (3)	134

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