(Z)-Ethyl 2-hy-droxy-4-oxo-4-(1,4,5,6,8-penta-meth-oxy-naphthalen-2-yl)but-2-enoate.

The title compound, C21H24O9, crystallizes with two independent mol-ecules in the asymmetric unit which are almost centrosymmetrically related to each other. The ethano-ate group in one of the two mol-ecules is disordered over two positions with a site-occupation factor of 0.880 (7) for the major occupied site. In the crystal, the 1,3-diketone group exists in the keto-enol isomeric form due to the stabilizing effect of the intra-molecular O-H⋯O hydrogen bond present in this form. The compound packs as a layered structure in which C-H⋯π and C-H⋯O inter-actions are present within and between the layers.

Related literature

For the synthesis of the title compound, see: de Koning et al. (1991 ▶). This forms part of our research programme directed towards the synthesis of the natural phytotoxic naphtho­quinone, marticin, see: Pillay et al. (2012 ▶).

Experimental

Crystal data

C21H24O9

M = 420.40

Triclinic,

a = 6.8019 (4) Å

b = 12.3042 (6) Å

c = 24.3971 (12) Å

α = 100.002 (4)°

β = 93.080 (4)°

γ = 98.748 (4)°

V = 1980.67 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 173 K

0.39 × 0.16 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

19594 measured reflections

7793 independent reflections

3172 reflections with I > 2σ(I)

R int = 0.083

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.118

S = 0.84

7793 reflections

572 parameters

54 restraints

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-NT (Bruker, 2005 ▶); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and SCHAKAL99 (Keller, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812049203/bt6876sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049203/bt6876Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049203/bt6876Isup3.cml

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

C21H24O9	Z = 4
Mr = 420.40	F(000) = 888
Triclinic, P1	Dx = 1.410 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8019 (4) Å	Cell parameters from 1943 reflections
b = 12.3042 (6) Å	θ = 2.6–25.0°
c = 24.3971 (12) Å	µ = 0.11 mm−1
α = 100.002 (4)°	T = 173 K
β = 93.080 (4)°	Needle, red
γ = 98.748 (4)°	0.39 × 0.16 × 0.07 mm
V = 1980.67 (18) Å3

Bruker APEXII CCD diffractometer	3172 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.083
Graphite monochromator	θmax = 26.0°, θmin = 1.7°
φ and ω scans	h = −8→8
19594 measured reflections	k = −15→15
7793 independent reflections	l = −30→30

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 0.84	w = 1/[σ2(Fo2) + (0.0343P)2] where P = (Fo2 + 2Fc2)/3
7793 reflections	(Δ/σ)max = 0.001
572 parameters	Δρmax = 0.21 e Å−3
54 restraints	Δρmin = −0.25 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	Occ. (<1)
C1A	0.7086 (4)	0.6467 (2)	0.10802 (12)	0.0245 (8)
C2A	0.7846 (4)	0.6053 (2)	0.15505 (12)	0.0247 (8)
C3A	0.9780 (5)	0.6484 (2)	0.18382 (13)	0.0274 (8)
C4A	1.0511 (5)	0.6025 (2)	0.22628 (12)	0.0293 (8)
H4A	1.1805	0.6317	0.2441	0.035*
C5A	0.9352 (5)	0.5130 (3)	0.24321 (13)	0.0282 (8)
C6A	0.7459 (5)	0.4692 (2)	0.21838 (12)	0.0259 (8)
C7A	0.6673 (4)	0.5137 (2)	0.17411 (12)	0.0244 (8)
C8A	0.4709 (5)	0.4721 (3)	0.14548 (13)	0.0284 (8)
C9A	0.4045 (5)	0.5152 (2)	0.10176 (12)	0.0274 (8)
H9A	0.2747	0.4859	0.0842	0.033*
C10A	0.5233 (4)	0.6030 (2)	0.08142 (12)	0.0244 (8)
C11A	0.4404 (5)	0.6341 (3)	0.03013 (13)	0.0269 (8)
C12A	0.5123 (5)	0.7360 (3)	0.01041 (12)	0.0320 (9)
H12A	0.6240	0.7863	0.0299	0.038*
C13A	0.4219 (5)	0.7599 (3)	−0.03533 (14)	0.0363 (9)
C14A	0.4888 (6)	0.8667 (3)	−0.05716 (15)	0.0437 (9)	0.880 (7)
C15A	0.7626 (7)	1.0144 (3)	−0.0550 (2)	0.0586 (16)	0.880 (7)
H15A	0.8505	1.0631	−0.0238	0.070*	0.880 (7)
H15B	0.6543	1.0549	−0.0648	0.070*	0.880 (7)
C16A	0.8787 (8)	0.9900 (4)	−0.1037 (2)	0.0657 (18)	0.880 (7)
H16A	0.9349	1.0602	−0.1150	0.099*	0.880 (7)
H16B	0.7912	0.9425	−0.1347	0.099*	0.880 (7)
H16C	0.9871	0.9510	−0.0938	0.099*	0.880 (7)
O8A	0.6766 (4)	0.9106 (3)	−0.03759 (16)	0.0469 (10)	0.880 (7)
O9A	0.3818 (5)	0.9035 (3)	−0.08750 (19)	0.0591 (13)	0.880 (7)
C14C	0.4888 (6)	0.8667 (3)	−0.05716 (15)	0.0437 (9)	0.120 (7)
C15C	0.750 (2)	0.971 (2)	−0.0955 (11)	0.035 (7)*	0.120 (7)
H15E	0.6642	1.0293	−0.0880	0.042*	0.120 (7)
H15F	0.7428	0.9443	−0.1363	0.042*	0.120 (7)
C16C	0.958 (4)	1.018 (3)	−0.0738 (15)	0.069 (13)*	0.120 (7)
H16G	1.0093	1.0779	−0.0934	0.103*	0.120 (7)
H16H	1.0407	0.9587	−0.0799	0.103*	0.120 (7)
H16I	0.9627	1.0477	−0.0338	0.103*	0.120 (7)
O8C	0.6804 (13)	0.8774 (15)	−0.0674 (10)	0.046 (5)*	0.120 (7)
O9C	0.371 (3)	0.924 (2)	−0.0690 (15)	0.059 (11)*	0.120 (7)
C17A	0.9644 (5)	0.6896 (3)	0.05027 (13)	0.0385 (9)
H17A	1.0490	0.6468	0.0688	0.058*
H17B	1.0480	0.7528	0.0390	0.058*
H17C	0.8902	0.6411	0.0171	0.058*
C18A	1.2844 (4)	0.7789 (3)	0.19191 (13)	0.0377 (9)
H18A	1.2816	0.8059	0.2320	0.057*
H18B	1.3455	0.8403	0.1744	0.057*
H18C	1.3626	0.7179	0.1861	0.057*
C19A	1.1951 (5)	0.5070 (3)	0.31297 (14)	0.0445 (10)
H19A	1.2947	0.4988	0.2856	0.067*
H19B	1.2208	0.4648	0.3424	0.067*
H19C	1.2034	0.5862	0.3295	0.067*
C20A	0.6807 (5)	0.2757 (3)	0.21377 (14)	0.0409 (9)
H20A	0.6351	0.2610	0.1740	0.061*
H20B	0.6098	0.2179	0.2318	0.061*
H20C	0.8245	0.2748	0.2180	0.061*
C21A	0.1682 (4)	0.3393 (3)	0.13505 (13)	0.0371 (9)
H21A	0.0842	0.3976	0.1362	0.056*
H21B	0.1033	0.2790	0.1526	0.056*
H21C	0.1871	0.3094	0.0961	0.056*
O1A	0.8265 (3)	0.73063 (16)	0.08806 (8)	0.0274 (5)
O2A	1.0851 (3)	0.73912 (17)	0.16741 (8)	0.0352 (6)
O3A	0.9989 (3)	0.46456 (17)	0.28566 (9)	0.0378 (6)
O4A	0.6406 (3)	0.38328 (17)	0.23943 (8)	0.0311 (6)
O5A	0.3595 (3)	0.38650 (17)	0.16480 (8)	0.0360 (6)
O6A	0.2923 (3)	0.56832 (17)	0.00277 (8)	0.0317 (6)
O7A	0.2659 (3)	0.6961 (2)	−0.06553 (9)	0.0450 (7)
H7A	0.2301	0.6399	−0.0510	0.068*
C1B	0.3209 (5)	0.8636 (2)	0.39125 (12)	0.0268 (8)
C2B	0.2118 (4)	0.9010 (3)	0.34798 (12)	0.0260 (8)
C3B	0.0137 (5)	0.8495 (2)	0.32514 (13)	0.0276 (8)
C4B	−0.0842 (4)	0.8891 (2)	0.28420 (12)	0.0282 (8)
H4B	−0.2163	0.8545	0.2704	0.034*
C5B	0.0082 (5)	0.9796 (3)	0.26257 (13)	0.0285 (8)
C6B	0.2003 (4)	1.0317 (2)	0.28214 (12)	0.0250 (8)
C7B	0.3025 (4)	0.9964 (2)	0.32591 (12)	0.0246 (8)
C8B	0.4976 (4)	1.0515 (3)	0.35055 (12)	0.0274 (8)
C9B	0.5930 (4)	1.0143 (2)	0.39183 (12)	0.0265 (8)
H9B	0.7211	1.0531	0.4071	0.032*
C10B	0.5082 (4)	0.9193 (3)	0.41316 (12)	0.0266 (8)
C11B	0.6317 (5)	0.8932 (3)	0.45984 (13)	0.0318 (8)
C12B	0.5872 (5)	0.7955 (3)	0.48512 (12)	0.0317 (8)
H12B	0.4773	0.7389	0.4701	0.038*
C13B	0.7032 (5)	0.7848 (3)	0.53055 (13)	0.0315 (8)
C14B	0.6633 (5)	0.6875 (3)	0.55955 (14)	0.0348 (9)
C15B	0.4164 (5)	0.5460 (3)	0.57949 (14)	0.0468 (10)
H15C	0.4399	0.5735	0.6203	0.056*
H15D	0.4960	0.4857	0.5691	0.056*
C16B	0.1988 (5)	0.5027 (3)	0.56370 (15)	0.0514 (11)
H16D	0.1224	0.5640	0.5725	0.077*
H16E	0.1535	0.4439	0.5847	0.077*
H16F	0.1785	0.4720	0.5236	0.077*
C17B	0.1232 (5)	0.7820 (3)	0.45533 (13)	0.0405 (9)
H17D	0.1955	0.8402	0.4853	0.061*
H17E	0.0933	0.7116	0.4692	0.061*
H17F	−0.0018	0.8046	0.4432	0.061*
C18B	−0.2757 (4)	0.7101 (3)	0.32455 (13)	0.0366 (9)
H18D	−0.3620	0.7670	0.3323	0.055*
H18E	−0.3215	0.6473	0.3430	0.055*
H18F	−0.2813	0.6834	0.2842	0.055*
C19B	−0.2761 (4)	0.9696 (3)	0.19809 (14)	0.0422 (10)
H19D	−0.2764	0.8902	0.1833	0.063*
H19E	−0.3183	1.0064	0.1680	0.063*
H19F	−0.3686	0.9765	0.2275	0.063*
C20B	0.2339 (5)	1.2213 (2)	0.27309 (13)	0.0403 (9)
H20D	0.0885	1.2153	0.2680	0.060*
H20E	0.2968	1.2743	0.2510	0.060*
H20F	0.2788	1.2479	0.3127	0.060*
C21B	0.7722 (4)	1.2003 (3)	0.35457 (13)	0.0387 (9)
H21D	0.7672	1.2272	0.3946	0.058*
H21E	0.8154	1.2638	0.3363	0.058*
H21F	0.8670	1.1476	0.3491	0.058*
O1B	0.2440 (3)	0.76673 (16)	0.40899 (8)	0.0307 (6)
O2B	−0.0734 (3)	0.75818 (17)	0.34535 (8)	0.0358 (6)
O3B	−0.0784 (3)	1.02174 (18)	0.22093 (9)	0.0380 (6)
O4B	0.2889 (3)	1.11377 (17)	0.25499 (8)	0.0293 (5)
O5B	0.5775 (3)	1.14496 (18)	0.33067 (9)	0.0376 (6)
O6B	0.7876 (3)	0.96174 (18)	0.47859 (9)	0.0434 (7)
O7B	0.8649 (3)	0.85584 (19)	0.55340 (9)	0.0433 (6)
H7B	0.8847	0.9086	0.5356	0.065*
O8B	0.4734 (3)	0.63665 (18)	0.54955 (9)	0.0403 (6)
O9B	0.7878 (4)	0.6589 (2)	0.58861 (10)	0.0492 (7)

	U11	U22	U33	U12	U13	U23
C1A	0.027 (2)	0.0197 (18)	0.0280 (19)	0.0018 (15)	0.0058 (16)	0.0087 (15)
C2A	0.0191 (18)	0.0271 (19)	0.0273 (19)	0.0021 (15)	−0.0025 (15)	0.0064 (15)
C3A	0.0266 (19)	0.0256 (19)	0.0281 (19)	−0.0021 (15)	−0.0009 (16)	0.0067 (15)
C4A	0.0240 (19)	0.031 (2)	0.0302 (19)	−0.0008 (15)	−0.0084 (16)	0.0073 (16)
C5A	0.031 (2)	0.0256 (19)	0.029 (2)	0.0068 (16)	−0.0031 (17)	0.0074 (16)
C6A	0.0255 (19)	0.0254 (19)	0.0271 (19)	0.0006 (15)	0.0037 (16)	0.0081 (15)
C7A	0.0235 (19)	0.0233 (18)	0.0247 (19)	−0.0003 (15)	0.0004 (16)	0.0035 (15)
C8A	0.026 (2)	0.0273 (19)	0.032 (2)	0.0008 (15)	0.0077 (17)	0.0085 (16)
C9A	0.0216 (19)	0.0292 (19)	0.030 (2)	−0.0001 (15)	0.0008 (16)	0.0064 (16)
C10A	0.0205 (18)	0.0267 (18)	0.0245 (19)	0.0005 (15)	−0.0021 (15)	0.0048 (15)
C11A	0.0246 (19)	0.031 (2)	0.0271 (19)	0.0096 (15)	0.0051 (16)	0.0048 (16)
C12A	0.036 (2)	0.034 (2)	0.027 (2)	0.0022 (16)	0.0009 (17)	0.0113 (16)
C13A	0.038 (2)	0.042 (2)	0.031 (2)	0.0115 (18)	0.0047 (19)	0.0093 (18)
C14A	0.062 (2)	0.041 (2)	0.035 (2)	0.0180 (18)	0.008 (2)	0.0186 (19)
C15A	0.079 (4)	0.039 (3)	0.066 (4)	0.007 (2)	0.023 (3)	0.028 (3)
C16A	0.092 (5)	0.041 (3)	0.066 (4)	0.000 (3)	0.029 (3)	0.018 (3)
O8A	0.0502 (18)	0.0399 (18)	0.058 (2)	0.0060 (14)	0.0111 (15)	0.0283 (17)
O9A	0.086 (3)	0.056 (2)	0.045 (3)	0.0240 (19)	−0.0081 (18)	0.029 (2)
C14C	0.062 (2)	0.041 (2)	0.035 (2)	0.0180 (18)	0.008 (2)	0.0186 (19)
C17A	0.031 (2)	0.045 (2)	0.037 (2)	−0.0028 (17)	0.0083 (18)	0.0103 (17)
C18A	0.0237 (19)	0.039 (2)	0.045 (2)	−0.0125 (16)	−0.0058 (17)	0.0109 (17)
C19A	0.048 (2)	0.040 (2)	0.045 (2)	0.0006 (18)	−0.0187 (19)	0.0182 (18)
C20A	0.040 (2)	0.031 (2)	0.053 (2)	0.0025 (17)	0.0037 (19)	0.0159 (18)
C21A	0.028 (2)	0.037 (2)	0.042 (2)	−0.0104 (16)	−0.0031 (18)	0.0116 (17)
O1A	0.0235 (13)	0.0267 (13)	0.0322 (13)	−0.0008 (10)	0.0002 (11)	0.0111 (10)
O2A	0.0262 (13)	0.0358 (14)	0.0401 (14)	−0.0113 (11)	−0.0106 (11)	0.0162 (11)
O3A	0.0353 (14)	0.0366 (14)	0.0402 (14)	−0.0039 (11)	−0.0151 (12)	0.0174 (11)
O4A	0.0312 (13)	0.0305 (13)	0.0328 (13)	0.0010 (11)	0.0014 (11)	0.0129 (11)
O5A	0.0242 (13)	0.0392 (14)	0.0430 (14)	−0.0094 (11)	−0.0072 (11)	0.0190 (12)
O6A	0.0270 (13)	0.0345 (14)	0.0308 (13)	−0.0001 (11)	−0.0059 (11)	0.0056 (11)
O7A	0.0474 (17)	0.0515 (17)	0.0362 (15)	0.0041 (13)	−0.0091 (13)	0.0152 (12)
C1B	0.031 (2)	0.0235 (18)	0.0268 (19)	0.0050 (15)	0.0044 (16)	0.0065 (15)
C2B	0.0217 (19)	0.0299 (19)	0.0254 (19)	0.0014 (15)	−0.0025 (15)	0.0064 (15)
C3B	0.027 (2)	0.0275 (19)	0.0281 (19)	−0.0012 (16)	0.0026 (16)	0.0098 (16)
C4B	0.0201 (19)	0.032 (2)	0.030 (2)	−0.0015 (15)	−0.0035 (16)	0.0046 (16)
C5B	0.025 (2)	0.033 (2)	0.0269 (19)	0.0029 (16)	−0.0060 (16)	0.0098 (16)
C6B	0.0258 (19)	0.0270 (19)	0.0212 (18)	0.0006 (15)	−0.0004 (15)	0.0053 (15)
C7B	0.0218 (19)	0.0243 (19)	0.0255 (19)	−0.0010 (15)	0.0015 (16)	0.0032 (15)
C8B	0.0250 (19)	0.030 (2)	0.0271 (19)	0.0028 (16)	−0.0025 (16)	0.0072 (16)
C9B	0.0215 (18)	0.0274 (19)	0.0268 (19)	−0.0036 (15)	−0.0034 (15)	0.0030 (15)
C10B	0.0207 (18)	0.032 (2)	0.0267 (19)	0.0052 (15)	−0.0044 (16)	0.0043 (15)
C11B	0.033 (2)	0.031 (2)	0.030 (2)	0.0091 (17)	−0.0041 (17)	0.0023 (16)
C12B	0.034 (2)	0.032 (2)	0.028 (2)	0.0053 (16)	−0.0066 (17)	0.0047 (16)
C13B	0.028 (2)	0.037 (2)	0.030 (2)	0.0044 (17)	0.0003 (17)	0.0112 (17)
C14B	0.030 (2)	0.042 (2)	0.030 (2)	0.0056 (18)	−0.0031 (18)	0.0050 (17)
C15B	0.052 (3)	0.042 (2)	0.050 (2)	0.0017 (19)	−0.004 (2)	0.024 (2)
C16B	0.046 (2)	0.045 (2)	0.060 (3)	−0.0077 (19)	−0.008 (2)	0.017 (2)
C17B	0.036 (2)	0.046 (2)	0.039 (2)	−0.0042 (17)	0.0026 (18)	0.0185 (18)
C18B	0.026 (2)	0.036 (2)	0.044 (2)	−0.0084 (16)	−0.0021 (18)	0.0121 (17)
C19B	0.029 (2)	0.049 (2)	0.047 (2)	−0.0016 (18)	−0.0154 (18)	0.0145 (19)
C20B	0.039 (2)	0.033 (2)	0.052 (2)	0.0032 (17)	0.0028 (19)	0.0205 (18)
C21B	0.0222 (19)	0.045 (2)	0.044 (2)	−0.0104 (17)	−0.0054 (17)	0.0095 (18)
O1B	0.0335 (14)	0.0268 (13)	0.0306 (13)	−0.0009 (11)	−0.0029 (11)	0.0090 (10)
O2B	0.0297 (14)	0.0345 (14)	0.0398 (14)	−0.0104 (11)	−0.0100 (11)	0.0155 (11)
O3B	0.0272 (13)	0.0440 (15)	0.0410 (15)	−0.0067 (11)	−0.0127 (11)	0.0188 (12)
O4B	0.0267 (13)	0.0292 (13)	0.0319 (13)	−0.0029 (10)	0.0003 (11)	0.0125 (11)
O5B	0.0281 (14)	0.0398 (14)	0.0428 (14)	−0.0120 (11)	−0.0098 (11)	0.0210 (12)
O6B	0.0365 (15)	0.0402 (15)	0.0485 (15)	−0.0080 (12)	−0.0234 (12)	0.0146 (12)
O7B	0.0422 (16)	0.0465 (17)	0.0394 (15)	−0.0008 (12)	−0.0118 (13)	0.0148 (12)
O8B	0.0370 (15)	0.0413 (15)	0.0463 (15)	0.0024 (12)	−0.0026 (12)	0.0242 (12)
O9B	0.0420 (16)	0.0589 (17)	0.0525 (17)	0.0091 (13)	−0.0066 (14)	0.0289 (14)

C1A—C10A	1.373 (4)	C21A—H21B	0.9800
C1A—O1A	1.382 (3)	C21A—H21C	0.9800
C1A—C2A	1.436 (4)	O7A—H7A	0.8400
C2A—C3A	1.437 (4)	C1B—O1B	1.377 (3)
C2A—C7A	1.439 (4)	C1B—C10B	1.383 (4)
C3A—C4A	1.368 (4)	C1B—C2B	1.437 (4)
C3A—O2A	1.369 (3)	C2B—C3B	1.436 (4)
C4A—C5A	1.391 (4)	C2B—C7B	1.444 (4)
C4A—H4A	0.9500	C3B—C4B	1.369 (4)
C5A—O3A	1.364 (3)	C3B—O2B	1.370 (3)
C5A—C6A	1.381 (4)	C4B—C5B	1.393 (4)
C6A—O4A	1.376 (3)	C4B—H4B	0.9500
C6A—C7A	1.408 (4)	C5B—O3B	1.364 (3)
C7A—C8A	1.450 (4)	C5B—C6B	1.385 (4)
C8A—C9A	1.356 (4)	C6B—O4B	1.383 (3)
C8A—O5A	1.369 (3)	C6B—C7B	1.409 (4)
C9A—C10A	1.425 (4)	C7B—C8B	1.443 (4)
C9A—H9A	0.9500	C8B—C9B	1.350 (4)
C10A—C11A	1.479 (4)	C8B—O5B	1.373 (3)
C11A—O6A	1.268 (3)	C9B—C10B	1.417 (4)
C11A—C12A	1.446 (4)	C9B—H9B	0.9500
C12A—C13A	1.343 (4)	C10B—C11B	1.488 (4)
C12A—H12A	0.9500	C11B—O6B	1.260 (3)
C13A—O7A	1.321 (4)	C11B—C12B	1.443 (4)
C13A—C14A	1.518 (4)	C12B—C13B	1.362 (4)
C14A—O9A	1.200 (4)	C12B—H12B	0.9500
C14A—O8A	1.337 (4)	C13B—O7B	1.326 (4)
C15A—O8A	1.465 (4)	C13B—C14B	1.492 (4)
C15A—C16A	1.474 (5)	C14B—O9B	1.207 (4)
C15A—H15A	0.9900	C14B—O8B	1.337 (4)
C15A—H15B	0.9900	C15B—O8B	1.453 (3)
C16A—H16A	0.9800	C15B—C16B	1.500 (4)
C16A—H16B	0.9800	C15B—H15C	0.9900
C16A—H16C	0.9800	C15B—H15D	0.9900
C15C—O8C	1.470 (6)	C16B—H16D	0.9800
C15C—C16C	1.478 (7)	C16B—H16E	0.9800
C15C—H15E	0.9900	C16B—H16F	0.9800
C15C—H15F	0.9900	C17B—O1B	1.436 (3)
C16C—H16G	0.9800	C17B—H17D	0.9800
C16C—H16H	0.9800	C17B—H17E	0.9800
C16C—H16I	0.9800	C17B—H17F	0.9800
C17A—O1A	1.435 (3)	C18B—O2B	1.440 (3)
C17A—H17A	0.9800	C18B—H18D	0.9800
C17A—H17B	0.9800	C18B—H18E	0.9800
C17A—H17C	0.9800	C18B—H18F	0.9800
C18A—O2A	1.429 (3)	C19B—O3B	1.437 (3)
C18A—H18A	0.9800	C19B—H19D	0.9800
C18A—H18B	0.9800	C19B—H19E	0.9800
C18A—H18C	0.9800	C19B—H19F	0.9800
C19A—O3A	1.438 (3)	C20B—O4B	1.432 (3)
C19A—H19A	0.9800	C20B—H20D	0.9800
C19A—H19B	0.9800	C20B—H20E	0.9800
C19A—H19C	0.9800	C20B—H20F	0.9800
C20A—O4A	1.435 (3)	C21B—O5B	1.436 (3)
C20A—H20A	0.9800	C21B—H21D	0.9800
C20A—H20B	0.9800	C21B—H21E	0.9800
C20A—H20C	0.9800	C21B—H21F	0.9800
C21A—O5A	1.442 (3)	O7B—H7B	0.8400
C21A—H21A	0.9800
C10A—C1A—O1A	119.0 (3)	C1A—O1A—C17A	113.2 (2)
C10A—C1A—C2A	121.5 (3)	C3A—O2A—C18A	118.5 (2)
O1A—C1A—C2A	119.4 (3)	C5A—O3A—C19A	118.3 (2)
C1A—C2A—C3A	123.2 (3)	C6A—O4A—C20A	112.5 (2)
C1A—C2A—C7A	119.7 (3)	C8A—O5A—C21A	117.1 (2)
C3A—C2A—C7A	117.0 (3)	C13A—O7A—H7A	109.5
C4A—C3A—O2A	121.4 (3)	O1B—C1B—C10B	118.9 (3)
C4A—C3A—C2A	121.8 (3)	O1B—C1B—C2B	119.7 (3)
O2A—C3A—C2A	116.9 (3)	C10B—C1B—C2B	121.2 (3)
C3A—C4A—C5A	119.8 (3)	C3B—C2B—C1B	123.8 (3)
C3A—C4A—H4A	120.1	C3B—C2B—C7B	117.0 (3)
C5A—C4A—H4A	120.1	C1B—C2B—C7B	119.2 (3)
O3A—C5A—C6A	116.0 (3)	C4B—C3B—O2B	121.0 (3)
O3A—C5A—C4A	122.5 (3)	C4B—C3B—C2B	121.5 (3)
C6A—C5A—C4A	121.5 (3)	O2B—C3B—C2B	117.6 (3)
O4A—C6A—C5A	117.1 (3)	C3B—C4B—C5B	120.5 (3)
O4A—C6A—C7A	122.8 (3)	C3B—C4B—H4B	119.7
C5A—C6A—C7A	120.1 (3)	C5B—C4B—H4B	119.7
C6A—C7A—C2A	119.8 (3)	O3B—C5B—C6B	115.5 (3)
C6A—C7A—C8A	123.7 (3)	O3B—C5B—C4B	123.7 (3)
C2A—C7A—C8A	116.6 (3)	C6B—C5B—C4B	120.8 (3)
C9A—C8A—O5A	122.6 (3)	O4B—C6B—C5B	117.4 (3)
C9A—C8A—C7A	121.5 (3)	O4B—C6B—C7B	122.3 (3)
O5A—C8A—C7A	115.9 (3)	C5B—C6B—C7B	120.3 (3)
C8A—C9A—C10A	122.1 (3)	C6B—C7B—C8B	123.0 (3)
C8A—C9A—H9A	119.0	C6B—C7B—C2B	119.8 (3)
C10A—C9A—H9A	119.0	C8B—C7B—C2B	117.1 (3)
C1A—C10A—C9A	118.5 (3)	C9B—C8B—O5B	122.3 (3)
C1A—C10A—C11A	125.1 (3)	C9B—C8B—C7B	121.5 (3)
C9A—C10A—C11A	116.3 (3)	O5B—C8B—C7B	116.2 (3)
O6A—C11A—C12A	118.2 (3)	C8B—C9B—C10B	122.2 (3)
O6A—C11A—C10A	117.4 (3)	C8B—C9B—H9B	118.9
C12A—C11A—C10A	124.4 (3)	C10B—C9B—H9B	118.9
C13A—C12A—C11A	120.3 (3)	C1B—C10B—C9B	118.8 (3)
C13A—C12A—H12A	119.8	C1B—C10B—C11B	126.6 (3)
C11A—C12A—H12A	119.8	C9B—C10B—C11B	114.6 (3)
O7A—C13A—C12A	124.9 (3)	O6B—C11B—C12B	117.6 (3)
O7A—C13A—C14A	112.6 (3)	O6B—C11B—C10B	117.2 (3)
C12A—C13A—C14A	122.5 (3)	C12B—C11B—C10B	125.2 (3)
O9A—C14A—O8A	127.0 (4)	C13B—C12B—C11B	119.9 (3)
O9A—C14A—C13A	122.6 (4)	C13B—C12B—H12B	120.1
O8A—C14A—C13A	110.4 (3)	C11B—C12B—H12B	120.1
O8A—C15A—C16A	110.4 (3)	O7B—C13B—C12B	125.3 (3)
O8A—C15A—H15A	109.6	O7B—C13B—C14B	112.0 (3)
C16A—C15A—H15A	109.6	C12B—C13B—C14B	122.8 (3)
O8A—C15A—H15B	109.6	O9B—C14B—O8B	124.5 (3)
C16A—C15A—H15B	109.6	O9B—C14B—C13B	123.8 (3)
H15A—C15A—H15B	108.1	O8B—C14B—C13B	111.7 (3)
C15A—C16A—H16A	109.5	O8B—C15B—C16B	107.3 (3)
C15A—C16A—H16B	109.5	O8B—C15B—H15C	110.3
H16A—C16A—H16B	109.5	C16B—C15B—H15C	110.3
C15A—C16A—H16C	109.5	O8B—C15B—H15D	110.3
H16A—C16A—H16C	109.5	C16B—C15B—H15D	110.3
H16B—C16A—H16C	109.5	H15C—C15B—H15D	108.5
C14A—O8A—C15A	116.9 (3)	C15B—C16B—H16D	109.5
O8C—C15C—C16C	108.3 (8)	C15B—C16B—H16E	109.5
O8C—C15C—H15E	110.0	H16D—C16B—H16E	109.5
C16C—C15C—H15E	110.0	C15B—C16B—H16F	109.5
O8C—C15C—H15F	110.0	H16D—C16B—H16F	109.5
C16C—C15C—H15F	110.0	H16E—C16B—H16F	109.5
H15E—C15C—H15F	108.4	O1B—C17B—H17D	109.5
C15C—C16C—H16G	109.5	O1B—C17B—H17E	109.5
C15C—C16C—H16H	109.5	H17D—C17B—H17E	109.5
H16G—C16C—H16H	109.5	O1B—C17B—H17F	109.5
C15C—C16C—H16I	109.5	H17D—C17B—H17F	109.5
H16G—C16C—H16I	109.5	H17E—C17B—H17F	109.5
H16H—C16C—H16I	109.5	O2B—C18B—H18D	109.5
O1A—C17A—H17A	109.5	O2B—C18B—H18E	109.5
O1A—C17A—H17B	109.5	H18D—C18B—H18E	109.5
H17A—C17A—H17B	109.5	O2B—C18B—H18F	109.5
O1A—C17A—H17C	109.5	H18D—C18B—H18F	109.5
H17A—C17A—H17C	109.5	H18E—C18B—H18F	109.5
H17B—C17A—H17C	109.5	O3B—C19B—H19D	109.5
O2A—C18A—H18A	109.5	O3B—C19B—H19E	109.5
O2A—C18A—H18B	109.5	H19D—C19B—H19E	109.5
H18A—C18A—H18B	109.5	O3B—C19B—H19F	109.5
O2A—C18A—H18C	109.5	H19D—C19B—H19F	109.5
H18A—C18A—H18C	109.5	H19E—C19B—H19F	109.5
H18B—C18A—H18C	109.5	O4B—C20B—H20D	109.5
O3A—C19A—H19A	109.5	O4B—C20B—H20E	109.5
O3A—C19A—H19B	109.5	H20D—C20B—H20E	109.5
H19A—C19A—H19B	109.5	O4B—C20B—H20F	109.5
O3A—C19A—H19C	109.5	H20D—C20B—H20F	109.5
H19A—C19A—H19C	109.5	H20E—C20B—H20F	109.5
H19B—C19A—H19C	109.5	O5B—C21B—H21D	109.5
O4A—C20A—H20A	109.5	O5B—C21B—H21E	109.5
O4A—C20A—H20B	109.5	H21D—C21B—H21E	109.5
H20A—C20A—H20B	109.5	O5B—C21B—H21F	109.5
O4A—C20A—H20C	109.5	H21D—C21B—H21F	109.5
H20A—C20A—H20C	109.5	H21E—C21B—H21F	109.5
H20B—C20A—H20C	109.5	C1B—O1B—C17B	114.9 (2)
O5A—C21A—H21A	109.5	C3B—O2B—C18B	117.6 (2)
O5A—C21A—H21B	109.5	C5B—O3B—C19B	118.0 (2)
H21A—C21A—H21B	109.5	C6B—O4B—C20B	113.9 (2)
O5A—C21A—H21C	109.5	C8B—O5B—C21B	116.8 (2)
H21A—C21A—H21C	109.5	C13B—O7B—H7B	109.5
H21B—C21A—H21C	109.5	C14B—O8B—C15B	115.7 (3)
C10A—C1A—C2A—C3A	179.7 (3)	O1B—C1B—C2B—C3B	6.8 (5)
O1A—C1A—C2A—C3A	1.4 (5)	C10B—C1B—C2B—C3B	−177.4 (3)
C10A—C1A—C2A—C7A	1.8 (4)	O1B—C1B—C2B—C7B	−174.0 (3)
O1A—C1A—C2A—C7A	−176.5 (3)	C10B—C1B—C2B—C7B	1.9 (4)
C1A—C2A—C3A—C4A	−175.9 (3)	C1B—C2B—C3B—C4B	179.5 (3)
C7A—C2A—C3A—C4A	2.1 (5)	C7B—C2B—C3B—C4B	0.2 (5)
C1A—C2A—C3A—O2A	5.2 (4)	C1B—C2B—C3B—O2B	−1.3 (5)
C7A—C2A—C3A—O2A	−176.8 (3)	C7B—C2B—C3B—O2B	179.4 (3)
O2A—C3A—C4A—C5A	177.6 (3)	O2B—C3B—C4B—C5B	−177.8 (3)
C2A—C3A—C4A—C5A	−1.2 (5)	C2B—C3B—C4B—C5B	1.4 (5)
C3A—C4A—C5A—O3A	−179.3 (3)	C3B—C4B—C5B—O3B	178.5 (3)
C3A—C4A—C5A—C6A	−0.5 (5)	C3B—C4B—C5B—C6B	−0.3 (5)
O3A—C5A—C6A—O4A	1.1 (4)	O3B—C5B—C6B—O4B	−4.9 (4)
C4A—C5A—C6A—O4A	−177.8 (3)	C4B—C5B—C6B—O4B	173.9 (3)
O3A—C5A—C6A—C7A	−179.9 (3)	O3B—C5B—C6B—C7B	178.7 (3)
C4A—C5A—C6A—C7A	1.3 (5)	C4B—C5B—C6B—C7B	−2.5 (5)
O4A—C6A—C7A—C2A	178.7 (3)	O4B—C6B—C7B—C8B	7.8 (5)
C5A—C6A—C7A—C2A	−0.3 (5)	C5B—C6B—C7B—C8B	−176.0 (3)
O4A—C6A—C7A—C8A	−1.5 (5)	O4B—C6B—C7B—C2B	−172.2 (3)
C5A—C6A—C7A—C8A	179.5 (3)	C5B—C6B—C7B—C2B	4.0 (4)
C1A—C2A—C7A—C6A	176.7 (3)	C3B—C2B—C7B—C6B	−2.9 (4)
C3A—C2A—C7A—C6A	−1.3 (4)	C1B—C2B—C7B—C6B	177.8 (3)
C1A—C2A—C7A—C8A	−3.1 (4)	C3B—C2B—C7B—C8B	177.2 (3)
C3A—C2A—C7A—C8A	178.9 (3)	C1B—C2B—C7B—C8B	−2.1 (4)
C6A—C7A—C8A—C9A	−177.7 (3)	C6B—C7B—C8B—C9B	−178.8 (3)
C2A—C7A—C8A—C9A	2.1 (4)	C2B—C7B—C8B—C9B	1.1 (4)
C6A—C7A—C8A—O5A	1.5 (4)	C6B—C7B—C8B—O5B	2.8 (4)
C2A—C7A—C8A—O5A	−178.7 (3)	C2B—C7B—C8B—O5B	−177.2 (3)
O5A—C8A—C9A—C10A	−178.9 (3)	O5B—C8B—C9B—C10B	178.5 (3)
C7A—C8A—C9A—C10A	0.2 (5)	C7B—C8B—C9B—C10B	0.3 (5)
O1A—C1A—C10A—C9A	178.9 (3)	O1B—C1B—C10B—C9B	175.4 (3)
C2A—C1A—C10A—C9A	0.6 (4)	C2B—C1B—C10B—C9B	−0.5 (5)
O1A—C1A—C10A—C11A	3.6 (5)	O1B—C1B—C10B—C11B	−7.6 (5)
C2A—C1A—C10A—C11A	−174.8 (3)	C2B—C1B—C10B—C11B	176.5 (3)
C8A—C9A—C10A—C1A	−1.6 (5)	C8B—C9B—C10B—C1B	−0.6 (5)
C8A—C9A—C10A—C11A	174.2 (3)	C8B—C9B—C10B—C11B	−178.0 (3)
C1A—C10A—C11A—O6A	162.6 (3)	C1B—C10B—C11B—O6B	−171.3 (3)
C9A—C10A—C11A—O6A	−12.9 (4)	C9B—C10B—C11B—O6B	5.8 (4)
C1A—C10A—C11A—C12A	−19.7 (5)	C1B—C10B—C11B—C12B	8.8 (5)
C9A—C10A—C11A—C12A	164.8 (3)	C9B—C10B—C11B—C12B	−174.0 (3)
O6A—C11A—C12A—C13A	0.7 (5)	O6B—C11B—C12B—C13B	5.3 (5)
C10A—C11A—C12A—C13A	−177.0 (3)	C10B—C11B—C12B—C13B	−174.9 (3)
C11A—C12A—C13A—O7A	0.0 (5)	C11B—C12B—C13B—O7B	−3.2 (5)
C11A—C12A—C13A—C14A	178.8 (3)	C11B—C12B—C13B—C14B	178.6 (3)
O7A—C13A—C14A—O9A	19.6 (6)	O7B—C13B—C14B—O9B	−20.1 (5)
C12A—C13A—C14A—O9A	−159.3 (4)	C12B—C13B—C14B—O9B	158.3 (3)
O7A—C13A—C14A—O8A	−160.7 (3)	O7B—C13B—C14B—O8B	159.6 (3)
C12A—C13A—C14A—O8A	20.4 (5)	C12B—C13B—C14B—O8B	−21.9 (4)
O9A—C14A—O8A—C15A	−0.3 (7)	C10B—C1B—O1B—C17B	92.4 (3)
C13A—C14A—O8A—C15A	−180.0 (3)	C2B—C1B—O1B—C17B	−91.6 (3)
C16A—C15A—O8A—C14A	−95.6 (5)	C4B—C3B—O2B—C18B	−3.9 (4)
C10A—C1A—O1A—C17A	−94.7 (3)	C2B—C3B—O2B—C18B	176.9 (3)
C2A—C1A—O1A—C17A	83.7 (3)	C6B—C5B—O3B—C19B	178.7 (3)
C4A—C3A—O2A—C18A	6.0 (4)	C4B—C5B—O3B—C19B	−0.1 (5)
C2A—C3A—O2A—C18A	−175.1 (3)	C5B—C6B—O4B—C20B	82.7 (3)
C6A—C5A—O3A—C19A	180.0 (3)	C7B—C6B—O4B—C20B	−101.0 (3)
C4A—C5A—O3A—C19A	−1.2 (4)	C9B—C8B—O5B—C21B	2.1 (4)
C5A—C6A—O4A—C20A	−87.5 (3)	C7B—C8B—O5B—C21B	−179.6 (3)
C7A—C6A—O4A—C20A	93.5 (3)	O9B—C14B—O8B—C15B	4.2 (5)
C9A—C8A—O5A—C21A	2.6 (4)	C13B—C14B—O8B—C15B	−175.5 (3)
C7A—C8A—O5A—C21A	−176.6 (3)	C16B—C15B—O8B—C14B	178.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O7A—H7A···O6A	0.84	1.77	2.499 (3)	144
O7B—H7B···O6B	0.84	1.77	2.497 (3)	143
C17B—H17D···O6Bi	0.98	2.43	3.234 (4)	139
C19A—H19B···O9Bii	0.98	2.45	3.419 (4)	168
C19B—H19E···O9Aiii	0.98	2.47	3.440 (5)	172
C20A—H20B···O4Biv	0.98	2.50	3.384 (4)	150
C20B—H20E···O4Av	0.98	2.57	3.382 (4)	140
C20B—H20F···O9Bi	0.98	2.58	3.460 (4)	150
C18A—H18A···Cg3vi	0.98	2.66	3.486 (3)	142
C18A—H18C···Cg1vi	0.98	2.92	3.844 (3)	158
C18B—H18F···Cg2vii	0.98	2.66	3.522 (3)	147
C21A—H21A···Cg2vii	0.98	2.96	3.845 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1A/C2A/C7A–C10A, C2A–C7A and C2B–C7B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7A—H7A⋯O6A	0.84	1.77	2.499 (3)	144
O7B—H7B⋯O6B	0.84	1.77	2.497 (3)	143
C17B—H17D⋯O6B i	0.98	2.43	3.234 (4)	139
C19A—H19B⋯O9B ii	0.98	2.45	3.419 (4)	168
C19B—H19E⋯O9A iii	0.98	2.47	3.440 (5)	172
C20A—H20B⋯O4B iv	0.98	2.50	3.384 (4)	150
C20B—H20E⋯O4A v	0.98	2.57	3.382 (4)	140
C20B—H20F⋯O9B i	0.98	2.58	3.460 (4)	150
C18A—H18A⋯Cg3vi	0.98	2.66	3.486 (3)	142
C18A—H18C⋯Cg1vi	0.98	2.92	3.844 (3)	158
C18B—H18F⋯Cg2vii	0.98	2.66	3.522 (3)	147
C21A—H21A⋯Cg2vii	0.98	2.96	3.845 (3)	150

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .