(E)-Methyl 2-[(2-formyl-6-meth-oxy-phen-oxy)meth-yl]-3-phenyl-acrylate.

The title compound, C(19)H(18)O(5), crystallizes with two independent mol-ecules (A and B) in an asymmetric unit in both of which the two aromatic rings are in a bis-ectional orientation as evidenced by the dihedral angle between them [41.7 (1)° in mol-ecule A and 35.6 (1)° in mol-ecule B]. Both mol-ecules adopt an E configuration with respect to the C=C bond. An intra-molecular C-H⋯O hydrogen-bond occurs in mol-ecule A. The crystal packing features inter-molecular C-H⋯O inter-actions.

Related literature

For background to the synthesis, see: Bakthadoss et al. (2009 ▶). For related phenyl acrylate compounds, see: Wang et al. (2006 ▶); Jones & Jäger (2003 ▶). For their biological properties, see: Kim et al. (2004 ▶); Zhu et al. (2000 ▶).

Experimental

Crystal data

C19H18O5

M = 326.33

Triclinic,

a = 8.4696 (5) Å

b = 12.1662 (7) Å

c = 16.9860 (9) Å

α = 94.423 (3)°

β = 100.038 (3)°

γ = 103.475 (3)°

V = 1663.33 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

30114 measured reflections

8303 independent reflections

5258 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.137

S = 0.93

8303 reflections

433 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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, PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811054365/kp2375sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054365/kp2375Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811054365/kp2375Isup3.cml

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

C19H18O5	Z = 4
Mr = 326.33	F(000) = 688
Triclinic, P1	Dx = 1.303 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4696 (5) Å	Cell parameters from 8303 reflections
b = 12.1662 (7) Å	θ = 1.2–28.4°
c = 16.9860 (9) Å	µ = 0.09 mm−1
α = 94.423 (3)°	T = 293 K
β = 100.038 (3)°	Block, colourless
γ = 103.475 (3)°	0.20 × 0.20 × 0.20 mm
V = 1663.33 (16) Å3

Bruker SMART APEXII area-detector diffractometer	5258 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
graphite	θmax = 28.4°, θmin = 1.2°
ω and φ scans	h = −11→11
30114 measured reflections	k = −16→16
8303 independent reflections	l = −21→22

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.0725P)2 + 0.2552P] where P = (Fo2 + 2Fc2)/3
8303 reflections	(Δ/σ)max = 0.001
433 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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
O1A	0.41536 (13)	0.75129 (9)	0.88919 (6)	0.0567 (3)
O2A	0.18473 (14)	0.61117 (9)	0.85240 (7)	0.0611 (3)
O3A	−0.05209 (15)	0.66404 (10)	0.52848 (7)	0.0641 (3)
O4A	0.10199 (11)	0.59456 (8)	0.65973 (6)	0.0449 (2)
O5A	−0.0729 (2)	0.29588 (11)	0.73737 (9)	0.0909 (5)
C1A	0.2947 (2)	0.85775 (14)	0.60506 (10)	0.0600 (4)
H1A	0.2651	0.7787	0.5951	0.072*
C2A	0.2924 (3)	0.92180 (17)	0.54131 (11)	0.0724 (5)
H2A	0.2621	0.8855	0.4887	0.087*
C3A	0.3346 (3)	1.03855 (17)	0.55494 (12)	0.0740 (5)
H3A	0.3322	1.0812	0.5118	0.089*
C4A	0.3800 (3)	1.09178 (16)	0.63207 (12)	0.0733 (5)
H4A	0.4077	1.1709	0.6414	0.088*
C5A	0.3851 (2)	1.02901 (14)	0.69644 (10)	0.0630 (4)
H5A	0.4185	1.0661	0.7488	0.076*
C6A	0.34062 (19)	0.91055 (13)	0.68349 (9)	0.0490 (3)
C7A	0.34918 (18)	0.84624 (12)	0.75324 (9)	0.0473 (3)
H7A	0.4384	0.8765	0.7957	0.057*
C8A	0.24490 (17)	0.74965 (12)	0.76346 (8)	0.0417 (3)
C9A	0.08546 (17)	0.69396 (12)	0.70716 (8)	0.0432 (3)
H9A1	−0.0012	0.6715	0.7376	0.052*
H9A2	0.0543	0.7474	0.6717	0.052*
C10A	−0.04856 (17)	0.52761 (12)	0.61780 (8)	0.0455 (3)
C11A	−0.11578 (19)	0.42426 (13)	0.64278 (9)	0.0512 (4)
C12A	−0.2642 (2)	0.35353 (15)	0.59765 (12)	0.0664 (5)
H12A	−0.3094	0.2836	0.6138	0.080*
C13A	−0.3422 (2)	0.38740 (18)	0.53019 (12)	0.0732 (5)
H13A	−0.4405	0.3402	0.5003	0.088*
C14A	−0.2767 (2)	0.49130 (17)	0.50553 (10)	0.0660 (5)
H14A	−0.3322	0.5136	0.4597	0.079*
C15A	−0.12979 (19)	0.56217 (14)	0.54836 (9)	0.0523 (4)
C16A	−0.1390 (3)	0.71142 (19)	0.46640 (11)	0.0779 (6)
H16A	−0.0706	0.7830	0.4586	0.117*
H16B	−0.2387	0.7232	0.4813	0.117*
H16C	−0.1667	0.6602	0.4173	0.117*
C17A	−0.0340 (2)	0.38920 (14)	0.71684 (11)	0.0613 (4)
H17A	0.0537	0.4427	0.7500	0.074*
C18A	0.27580 (17)	0.69571 (12)	0.83820 (8)	0.0436 (3)
C19A	0.4474 (2)	0.70544 (17)	0.96434 (10)	0.0729 (5)
H19A	0.5496	0.7507	0.9968	0.109*
H19B	0.4553	0.6284	0.9539	0.109*
H19C	0.3586	0.7067	0.9924	0.109*
O1B	1.29774 (17)	1.18987 (11)	1.37809 (7)	0.0731 (4)
O2B	1.1832 (2)	1.06673 (10)	1.26819 (7)	0.0812 (4)
O3B	1.12347 (15)	1.32548 (10)	1.01612 (7)	0.0654 (3)
O4B	1.04928 (12)	1.21083 (8)	1.14210 (5)	0.0453 (2)
O5B	0.7023 (2)	0.91721 (12)	1.11274 (8)	0.0979 (5)
C1B	1.2973 (2)	1.49121 (13)	1.18301 (9)	0.0533 (4)
H1B	1.1923	1.4422	1.1666	0.064*
C2B	1.3363 (2)	1.59176 (14)	1.15034 (11)	0.0637 (4)
H2B	1.2567	1.6106	1.1125	0.076*
C3B	1.4919 (2)	1.66485 (15)	1.17302 (11)	0.0667 (5)
H3B	1.5172	1.7326	1.1506	0.080*
C4B	1.6089 (2)	1.63690 (15)	1.22894 (11)	0.0685 (5)
H4B	1.7145	1.6854	1.2440	0.082*
C5B	1.5709 (2)	1.53742 (14)	1.26295 (10)	0.0587 (4)
H5B	1.6509	1.5200	1.3014	0.070*
C6B	1.41469 (18)	1.46261 (12)	1.24054 (8)	0.0460 (3)
C7B	1.37621 (18)	1.36008 (13)	1.28042 (9)	0.0473 (3)
H7B	1.4189	1.3692	1.3355	0.057*
C8B	1.28832 (17)	1.25531 (12)	1.24876 (8)	0.0435 (3)
C9B	1.22565 (18)	1.21970 (13)	1.16011 (8)	0.0447 (3)
H9B1	1.2822	1.2754	1.1299	0.054*
H9B2	1.2470	1.1468	1.1449	0.054*
C10B	0.96683 (17)	1.16893 (12)	1.06435 (8)	0.0426 (3)
C11B	0.84002 (18)	1.06988 (12)	1.05216 (9)	0.0476 (3)
C12B	0.7411 (2)	1.03311 (14)	0.97533 (10)	0.0594 (4)
H12B	0.6534	0.9685	0.9673	0.071*
C13B	0.7728 (2)	1.09160 (15)	0.91246 (10)	0.0632 (4)
H13B	0.7069	1.0662	0.8616	0.076*
C14B	0.9019 (2)	1.18846 (14)	0.92324 (9)	0.0577 (4)
H14B	0.9239	1.2266	0.8794	0.069*
C15B	0.99822 (19)	1.22864 (12)	0.99897 (9)	0.0484 (3)
C16B	1.1582 (3)	1.38958 (19)	0.95210 (12)	0.0898 (7)
H16D	1.2485	1.4552	0.9723	0.135*
H16E	1.0619	1.4136	0.9291	0.135*
H16F	1.1879	1.3433	0.9115	0.135*
C17B	0.8112 (2)	1.00228 (14)	1.11870 (10)	0.0616 (4)
H17B	0.8818	1.0270	1.1685	0.074*
C18B	1.2594 (2)	1.16990 (13)	1.30624 (9)	0.0508 (4)
C19B	1.1463 (4)	0.97776 (18)	1.31915 (15)	0.1193 (10)
H19D	1.0918	0.9068	1.2861	0.179*
H19E	1.0752	0.9967	1.3535	0.179*
H19F	1.2475	0.9708	1.3516	0.179*

	U11	U22	U33	U12	U13	U23
O1A	0.0527 (6)	0.0632 (7)	0.0429 (6)	−0.0024 (5)	−0.0035 (5)	0.0188 (5)
O2A	0.0648 (7)	0.0522 (6)	0.0551 (6)	−0.0041 (5)	0.0021 (5)	0.0186 (5)
O3A	0.0669 (7)	0.0720 (8)	0.0502 (6)	0.0178 (6)	−0.0018 (5)	0.0172 (6)
O4A	0.0418 (5)	0.0463 (5)	0.0446 (5)	0.0123 (4)	0.0035 (4)	0.0019 (4)
O5A	0.1161 (12)	0.0530 (8)	0.0974 (10)	0.0087 (7)	0.0142 (9)	0.0254 (7)
C1A	0.0791 (11)	0.0507 (9)	0.0529 (9)	0.0140 (8)	0.0204 (8)	0.0130 (7)
C2A	0.1036 (15)	0.0701 (12)	0.0463 (9)	0.0214 (11)	0.0194 (9)	0.0151 (8)
C3A	0.1022 (15)	0.0667 (12)	0.0617 (11)	0.0232 (11)	0.0262 (10)	0.0313 (9)
C4A	0.0986 (14)	0.0498 (10)	0.0734 (12)	0.0122 (9)	0.0245 (11)	0.0219 (9)
C5A	0.0776 (12)	0.0507 (9)	0.0545 (10)	0.0029 (8)	0.0117 (8)	0.0118 (7)
C6A	0.0506 (8)	0.0481 (8)	0.0485 (8)	0.0096 (7)	0.0106 (7)	0.0149 (7)
C7A	0.0479 (8)	0.0472 (8)	0.0441 (8)	0.0081 (6)	0.0054 (6)	0.0104 (6)
C8A	0.0442 (7)	0.0427 (7)	0.0391 (7)	0.0130 (6)	0.0067 (6)	0.0074 (6)
C9A	0.0438 (7)	0.0449 (8)	0.0411 (7)	0.0132 (6)	0.0061 (6)	0.0054 (6)
C10A	0.0431 (8)	0.0487 (8)	0.0427 (8)	0.0122 (6)	0.0059 (6)	−0.0020 (6)
C11A	0.0519 (9)	0.0473 (8)	0.0529 (9)	0.0099 (7)	0.0128 (7)	−0.0013 (7)
C12A	0.0603 (10)	0.0566 (10)	0.0731 (12)	0.0009 (8)	0.0139 (9)	−0.0068 (9)
C13A	0.0512 (10)	0.0788 (13)	0.0739 (13)	0.0029 (9)	0.0000 (9)	−0.0163 (10)
C14A	0.0551 (10)	0.0851 (13)	0.0510 (10)	0.0198 (9)	−0.0040 (8)	−0.0066 (9)
C15A	0.0522 (9)	0.0604 (10)	0.0436 (8)	0.0167 (7)	0.0061 (7)	0.0009 (7)
C16A	0.0868 (14)	0.0971 (15)	0.0559 (11)	0.0384 (12)	0.0037 (9)	0.0244 (10)
C17A	0.0712 (11)	0.0468 (9)	0.0646 (10)	0.0111 (8)	0.0141 (8)	0.0083 (8)
C18A	0.0457 (8)	0.0426 (8)	0.0414 (7)	0.0092 (6)	0.0074 (6)	0.0064 (6)
C19A	0.0722 (11)	0.0837 (13)	0.0488 (10)	0.0002 (10)	−0.0074 (8)	0.0276 (9)
O1B	0.1041 (10)	0.0693 (8)	0.0423 (7)	0.0151 (7)	0.0101 (6)	0.0163 (6)
O2B	0.1318 (12)	0.0456 (7)	0.0557 (7)	0.0084 (7)	0.0048 (7)	0.0166 (6)
O3B	0.0734 (8)	0.0593 (7)	0.0506 (6)	−0.0068 (6)	0.0032 (5)	0.0218 (5)
O4B	0.0458 (5)	0.0503 (6)	0.0354 (5)	0.0058 (4)	0.0065 (4)	0.0019 (4)
O5B	0.1163 (12)	0.0733 (9)	0.0750 (9)	−0.0361 (9)	0.0218 (8)	0.0103 (7)
C1B	0.0493 (8)	0.0524 (9)	0.0559 (9)	0.0090 (7)	0.0073 (7)	0.0111 (7)
C2B	0.0691 (11)	0.0580 (10)	0.0648 (11)	0.0171 (9)	0.0088 (8)	0.0191 (8)
C3B	0.0824 (13)	0.0489 (9)	0.0659 (11)	0.0053 (9)	0.0204 (10)	0.0124 (8)
C4B	0.0652 (11)	0.0587 (10)	0.0677 (11)	−0.0079 (8)	0.0091 (9)	0.0045 (9)
C5B	0.0558 (9)	0.0584 (10)	0.0522 (9)	0.0038 (8)	0.0000 (7)	0.0042 (7)
C6B	0.0498 (8)	0.0465 (8)	0.0391 (7)	0.0085 (6)	0.0078 (6)	0.0030 (6)
C7B	0.0476 (8)	0.0534 (9)	0.0385 (7)	0.0113 (7)	0.0031 (6)	0.0067 (6)
C8B	0.0459 (8)	0.0479 (8)	0.0391 (7)	0.0161 (6)	0.0069 (6)	0.0094 (6)
C9B	0.0483 (8)	0.0472 (8)	0.0402 (7)	0.0143 (6)	0.0090 (6)	0.0073 (6)
C10B	0.0460 (8)	0.0438 (8)	0.0370 (7)	0.0107 (6)	0.0069 (6)	0.0023 (6)
C11B	0.0524 (8)	0.0428 (8)	0.0442 (8)	0.0069 (6)	0.0101 (6)	0.0000 (6)
C12B	0.0619 (10)	0.0513 (9)	0.0534 (9)	0.0012 (8)	0.0027 (8)	−0.0037 (7)
C13B	0.0735 (11)	0.0591 (10)	0.0464 (9)	0.0120 (9)	−0.0062 (8)	−0.0026 (8)
C14B	0.0725 (11)	0.0590 (10)	0.0410 (8)	0.0179 (8)	0.0052 (7)	0.0110 (7)
C15B	0.0550 (9)	0.0439 (8)	0.0443 (8)	0.0094 (7)	0.0074 (7)	0.0091 (6)
C16B	0.0915 (15)	0.0893 (15)	0.0724 (13)	−0.0126 (12)	0.0048 (11)	0.0455 (11)
C17B	0.0712 (11)	0.0522 (9)	0.0531 (9)	−0.0027 (8)	0.0161 (8)	0.0046 (7)
C18B	0.0608 (9)	0.0489 (9)	0.0441 (9)	0.0178 (7)	0.0068 (7)	0.0106 (7)
C19B	0.199 (3)	0.0553 (12)	0.0878 (16)	0.0041 (15)	0.0135 (17)	0.0348 (11)

O1A—C18A	1.3360 (17)	O1B—C18B	1.1971 (18)
O1A—C19A	1.4400 (18)	O2B—C18B	1.327 (2)
O2A—C18A	1.2019 (17)	O2B—C19B	1.449 (2)
O3A—C15A	1.358 (2)	O3B—C15B	1.3620 (18)
O3A—C16A	1.417 (2)	O3B—C16B	1.419 (2)
O4A—C10A	1.3808 (17)	O4B—C10B	1.3785 (16)
O4A—C9A	1.4488 (17)	O4B—C9B	1.4481 (17)
O5A—C17A	1.202 (2)	O5B—C17B	1.1993 (19)
C1A—C6A	1.382 (2)	C1B—C2B	1.376 (2)
C1A—C2A	1.382 (2)	C1B—C6B	1.393 (2)
C1A—H1A	0.9300	C1B—H1B	0.9300
C2A—C3A	1.372 (3)	C2B—C3B	1.378 (3)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.364 (3)	C3B—C4B	1.371 (3)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.381 (2)	C4B—C5B	1.376 (2)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.392 (2)	C5B—C6B	1.391 (2)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.470 (2)	C6B—C7B	1.463 (2)
C7A—C8A	1.339 (2)	C7B—C8B	1.334 (2)
C7A—H7A	0.9300	C7B—H7B	0.9300
C8A—C18A	1.4844 (19)	C8B—C18B	1.488 (2)
C8A—C9A	1.4902 (19)	C8B—C9B	1.5002 (19)
C9A—H9A1	0.9700	C9B—H9B1	0.9700
C9A—H9A2	0.9700	C9B—H9B2	0.9700
C10A—C11A	1.385 (2)	C10B—C11B	1.389 (2)
C10A—C15A	1.403 (2)	C10B—C15B	1.403 (2)
C11A—C12A	1.403 (2)	C11B—C12B	1.400 (2)
C11A—C17A	1.470 (2)	C11B—C17B	1.469 (2)
C12A—C13A	1.362 (3)	C12B—C13B	1.359 (2)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.384 (3)	C13B—C14B	1.383 (2)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C15A	1.382 (2)	C14B—C15B	1.382 (2)
C14A—H14A	0.9300	C14B—H14B	0.9300
C16A—H16A	0.9600	C16B—H16D	0.9600
C16A—H16B	0.9600	C16B—H16E	0.9600
C16A—H16C	0.9600	C16B—H16F	0.9600
C17A—H17A	0.9300	C17B—H17B	0.9300
C19A—H19A	0.9600	C19B—H19D	0.9600
C19A—H19B	0.9600	C19B—H19E	0.9600
C19A—H19C	0.9600	C19B—H19F	0.9600
C18A—O1A—C19A	115.45 (12)	C18B—O2B—C19B	115.86 (15)
C15A—O3A—C16A	118.01 (14)	C15B—O3B—C16B	118.03 (13)
C10A—O4A—C9A	112.60 (10)	C10B—O4B—C9B	116.89 (10)
C6A—C1A—C2A	120.38 (16)	C2B—C1B—C6B	120.19 (15)
C6A—C1A—H1A	119.8	C2B—C1B—H1B	119.9
C2A—C1A—H1A	119.8	C6B—C1B—H1B	119.9
C3A—C2A—C1A	120.54 (17)	C1B—C2B—C3B	120.84 (17)
C3A—C2A—H2A	119.7	C1B—C2B—H2B	119.6
C1A—C2A—H2A	119.7	C3B—C2B—H2B	119.6
C4A—C3A—C2A	119.68 (17)	C4B—C3B—C2B	119.44 (17)
C4A—C3A—H3A	120.2	C4B—C3B—H3B	120.3
C2A—C3A—H3A	120.2	C2B—C3B—H3B	120.3
C3A—C4A—C5A	120.48 (17)	C3B—C4B—C5B	120.37 (17)
C3A—C4A—H4A	119.8	C3B—C4B—H4B	119.8
C5A—C4A—H4A	119.8	C5B—C4B—H4B	119.8
C4A—C5A—C6A	120.41 (17)	C4B—C5B—C6B	120.89 (16)
C4A—C5A—H5A	119.8	C4B—C5B—H5B	119.6
C6A—C5A—H5A	119.8	C6B—C5B—H5B	119.6
C1A—C6A—C5A	118.48 (14)	C5B—C6B—C1B	118.27 (14)
C1A—C6A—C7A	122.41 (14)	C5B—C6B—C7B	119.47 (14)
C5A—C6A—C7A	119.08 (14)	C1B—C6B—C7B	122.19 (13)
C8A—C7A—C6A	128.24 (14)	C8B—C7B—C6B	128.96 (13)
C8A—C7A—H7A	115.9	C8B—C7B—H7B	115.5
C6A—C7A—H7A	115.9	C6B—C7B—H7B	115.5
C7A—C8A—C18A	120.49 (13)	C7B—C8B—C18B	116.47 (13)
C7A—C8A—C9A	124.49 (13)	C7B—C8B—C9B	123.79 (13)
C18A—C8A—C9A	114.79 (12)	C18B—C8B—C9B	119.68 (13)
O4A—C9A—C8A	110.18 (11)	O4B—C9B—C8B	108.60 (11)
O4A—C9A—H9A1	109.6	O4B—C9B—H9B1	110.0
C8A—C9A—H9A1	109.6	C8B—C9B—H9B1	110.0
O4A—C9A—H9A2	109.6	O4B—C9B—H9B2	110.0
C8A—C9A—H9A2	109.6	C8B—C9B—H9B2	110.0
H9A1—C9A—H9A2	108.1	H9B1—C9B—H9B2	108.4
O4A—C10A—C11A	119.70 (13)	O4B—C10B—C11B	118.40 (12)
O4A—C10A—C15A	120.06 (13)	O4B—C10B—C15B	121.71 (13)
C11A—C10A—C15A	120.19 (14)	C11B—C10B—C15B	119.66 (13)
C10A—C11A—C12A	119.64 (16)	C10B—C11B—C12B	119.55 (14)
C10A—C11A—C17A	120.45 (14)	C10B—C11B—C17B	120.62 (13)
C12A—C11A—C17A	119.90 (15)	C12B—C11B—C17B	119.82 (14)
C13A—C12A—C11A	119.87 (17)	C13B—C12B—C11B	120.21 (15)
C13A—C12A—H12A	120.1	C13B—C12B—H12B	119.9
C11A—C12A—H12A	120.1	C11B—C12B—H12B	119.9
C12A—C13A—C14A	120.74 (17)	C12B—C13B—C14B	120.83 (15)
C12A—C13A—H13A	119.6	C12B—C13B—H13B	119.6
C14A—C13A—H13A	119.6	C14B—C13B—H13B	119.6
C15A—C14A—C13A	120.63 (17)	C15B—C14B—C13B	120.14 (15)
C15A—C14A—H14A	119.7	C15B—C14B—H14B	119.9
C13A—C14A—H14A	119.7	C13B—C14B—H14B	119.9
O3A—C15A—C14A	125.62 (15)	O3B—C15B—C14B	124.42 (14)
O3A—C15A—C10A	115.46 (13)	O3B—C15B—C10B	116.01 (13)
C14A—C15A—C10A	118.91 (16)	C14B—C15B—C10B	119.55 (14)
O3A—C16A—H16A	109.5	O3B—C16B—H16D	109.5
O3A—C16A—H16B	109.5	O3B—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
O3A—C16A—H16C	109.5	O3B—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16C	109.5	H16E—C16B—H16F	109.5
O5A—C17A—C11A	124.33 (17)	O5B—C17B—C11B	124.08 (16)
O5A—C17A—H17A	117.8	O5B—C17B—H17B	118.0
C11A—C17A—H17A	117.8	C11B—C17B—H17B	118.0
O2A—C18A—O1A	122.83 (13)	O1B—C18B—O2B	123.09 (15)
O2A—C18A—C8A	123.97 (13)	O1B—C18B—C8B	125.27 (15)
O1A—C18A—C8A	113.20 (12)	O2B—C18B—C8B	111.64 (13)
O1A—C19A—H19A	109.5	O2B—C19B—H19D	109.5
O1A—C19A—H19B	109.5	O2B—C19B—H19E	109.5
H19A—C19A—H19B	109.5	H19D—C19B—H19E	109.5
O1A—C19A—H19C	109.5	O2B—C19B—H19F	109.5
H19A—C19A—H19C	109.5	H19D—C19B—H19F	109.5
H19B—C19A—H19C	109.5	H19E—C19B—H19F	109.5
C6A—C1A—C2A—C3A	−0.5 (3)	C6B—C1B—C2B—C3B	0.9 (3)
C1A—C2A—C3A—C4A	0.4 (3)	C1B—C2B—C3B—C4B	−0.1 (3)
C2A—C3A—C4A—C5A	0.5 (3)	C2B—C3B—C4B—C5B	−0.8 (3)
C3A—C4A—C5A—C6A	−1.4 (3)	C3B—C4B—C5B—C6B	1.0 (3)
C2A—C1A—C6A—C5A	−0.4 (3)	C4B—C5B—C6B—C1B	−0.3 (2)
C2A—C1A—C6A—C7A	−178.36 (16)	C4B—C5B—C6B—C7B	−177.33 (15)
C4A—C5A—C6A—C1A	1.3 (3)	C2B—C1B—C6B—C5B	−0.7 (2)
C4A—C5A—C6A—C7A	179.34 (16)	C2B—C1B—C6B—C7B	176.33 (15)
C1A—C6A—C7A—C8A	−40.2 (2)	C5B—C6B—C7B—C8B	−141.00 (17)
C5A—C6A—C7A—C8A	141.79 (17)	C1B—C6B—C7B—C8B	42.0 (2)
C6A—C7A—C8A—C18A	178.94 (14)	C6B—C7B—C8B—C18B	−175.41 (14)
C6A—C7A—C8A—C9A	−6.8 (2)	C6B—C7B—C8B—C9B	7.3 (2)
C10A—O4A—C9A—C8A	168.47 (11)	C10B—O4B—C9B—C8B	−174.31 (11)
C7A—C8A—C9A—O4A	104.79 (16)	C7B—C8B—C9B—O4B	−105.02 (16)
C18A—C8A—C9A—O4A	−80.66 (14)	C18B—C8B—C9B—O4B	77.76 (16)
C9A—O4A—C10A—C11A	−106.93 (14)	C9B—O4B—C10B—C11B	119.51 (14)
C9A—O4A—C10A—C15A	75.55 (16)	C9B—O4B—C10B—C15B	−66.03 (18)
O4A—C10A—C11A—C12A	−176.58 (13)	O4B—C10B—C11B—C12B	172.24 (14)
C15A—C10A—C11A—C12A	0.9 (2)	C15B—C10B—C11B—C12B	−2.3 (2)
O4A—C10A—C11A—C17A	4.4 (2)	O4B—C10B—C11B—C17B	−9.1 (2)
C15A—C10A—C11A—C17A	−178.09 (14)	C15B—C10B—C11B—C17B	176.36 (14)
C10A—C11A—C12A—C13A	−0.7 (3)	C10B—C11B—C12B—C13B	2.4 (2)
C17A—C11A—C12A—C13A	178.30 (17)	C17B—C11B—C12B—C13B	−176.30 (16)
C11A—C12A—C13A—C14A	−0.1 (3)	C11B—C12B—C13B—C14B	−0.5 (3)
C12A—C13A—C14A—C15A	0.8 (3)	C12B—C13B—C14B—C15B	−1.6 (3)
C16A—O3A—C15A—C14A	10.6 (2)	C16B—O3B—C15B—C14B	−0.2 (3)
C16A—O3A—C15A—C10A	−170.80 (15)	C16B—O3B—C15B—C10B	−179.14 (17)
C13A—C14A—C15A—O3A	177.99 (16)	C13B—C14B—C15B—O3B	−177.30 (16)
C13A—C14A—C15A—C10A	−0.6 (2)	C13B—C14B—C15B—C10B	1.6 (2)
O4A—C10A—C15A—O3A	−1.5 (2)	O4B—C10B—C15B—O3B	4.9 (2)
C11A—C10A—C15A—O3A	−179.01 (13)	C11B—C10B—C15B—O3B	179.35 (13)
O4A—C10A—C15A—C14A	177.22 (14)	O4B—C10B—C15B—C14B	−174.06 (14)
C11A—C10A—C15A—C14A	−0.3 (2)	C11B—C10B—C15B—C14B	0.3 (2)
C10A—C11A—C17A—O5A	−170.69 (17)	C10B—C11B—C17B—O5B	178.61 (18)
C12A—C11A—C17A—O5A	10.3 (3)	C12B—C11B—C17B—O5B	−2.7 (3)
C19A—O1A—C18A—O2A	−2.1 (2)	C19B—O2B—C18B—O1B	0.6 (3)
C19A—O1A—C18A—C8A	177.28 (14)	C19B—O2B—C18B—C8B	−178.78 (19)
C7A—C8A—C18A—O2A	177.55 (15)	C7B—C8B—C18B—O1B	5.9 (2)
C9A—C8A—C18A—O2A	2.8 (2)	C9B—C8B—C18B—O1B	−176.72 (15)
C7A—C8A—C18A—O1A	−1.85 (19)	C7B—C8B—C18B—O2B	−174.76 (15)
C9A—C8A—C18A—O1A	−176.63 (12)	C9B—C8B—C18B—O2B	2.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C17A—H17A···O2A	0.93	2.48	3.354 (2)	156.
C17A—H17A···O4A	0.93	2.50	2.8164 (19)	100.
C17B—H17B···O4B	0.93	2.47	2.8004 (19)	101.
C9A—H9A2···O3A	0.97	2.49	3.0167 (18)	114.
C9B—H9B1···O3B	0.97	2.36	2.9416 (17)	118.
C7B—H7B···O1B	0.93	2.41	2.7847 (18)	104.
C7A—H7A···O1A	0.93	2.29	2.6914 (17)	106.
C9A—H9A1···O4Bi	0.97	2.55	3.2215 (16)	126.
C19B—H19D···O5Aii	0.96	2.43	3.275 (3)	147.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17A—H17A⋯O2A	0.93	2.48	3.354 (2)	156
C9A—H9A1⋯O4Bi	0.97	2.55	3.2215 (16)	126
C19B—H19D⋯O5Aii	0.96	2.43	3.275 (3)	147

Symmetry codes: (i) ; (ii) .