(2E,4E,6E)-3-Methyl-7-(pyren-1-yl)octa-2,4,6-trienoic acid.

The title compound, C(25)H(20)O(2), was synthesized by a Wittig reaction between triphen-yl[1-(pyren-1-yl)eth-yl]phospho-nium bromide and ethyl (2E,4E)-3-methyl-6-oxohexa-2,4-dienoate, in the presence of n-butyl lithium, followed by saponification. It was obtained pure in the all-trans configuration following crystallization from ethyl acetate. The asymmetric unit contains two independent mol-ecules (A and B), which are arranged almost parallel to each other within the crystal structure. The triene chain is not coplanar with the pyrene ring system, forming dihedral angles of 52.8 (1) and 42.2 (1)° for mol-ecules A and B, respectively. Inter-molecular hydrogen bonds between the carboxyl groups of the mol-ecules link them into centrosymmetric pairs, AA and BB, each with the R(2) (2)(8) graph-set motif.

Related literature

For general background on retinoids, see: Meyer et al. (1978 ▶); Sporn et al. (1994 ▶); Tian et al. (1997 ▶); Chaudhuri et al. (1999 ▶); Malpezzi et al. (2005 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C25H20O2

M = 352.41

Triclinic,

a = 7.5751 (7) Å

b = 8.5466 (7) Å

c = 28.458 (3) Å

α = 97.086 (7)°

β = 93.003 (8)°

γ = 97.574 (7)°

V = 1808.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.21 × 0.17 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur-3 with Sapphire CCD diffractometer

Absorption correction: none

22799 measured reflections

6284 independent reflections

3448 reflections with I > 2σ(I)

R int = 0.109

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.160

S = 1.00

6284 reflections

497 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038409/fj2242sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038409/fj2242Isup2.hkl

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

C25H20O2	Z = 4
Mr = 352.41	F(000) = 744
Triclinic, P1	Dx = 1.295 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5751 (7) Å	Cell parameters from 4369 reflections
b = 8.5466 (7) Å	θ = 3.0–30.3°
c = 28.458 (3) Å	µ = 0.08 mm−1
α = 97.086 (7)°	T = 100 K
β = 93.003 (8)°	Prism, colourless
γ = 97.574 (7)°	0.21 × 0.17 × 0.14 mm
V = 1808.0 (3) Å3

Oxford Diffraction Xcalibur-3 with Sapphire CCD diffractometer	3448 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray source	Rint = 0.109
graphite	θmax = 25.0°, θmin = 3.0°
Detector resolution: 16.0288 pixels mm-1	h = −9→9
ω and φ scans	k = −9→10
22799 measured reflections	l = −33→33
6284 independent reflections

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0717P)2] where P = (Fo2 + 2Fc2)/3
6284 reflections	(Δ/σ)max < 0.001
497 parameters	Δρmax = 0.33 e Å−3
2 restraints	Δρmin = −0.35 e Å−3

Experimental. IR (KBr, cm-1): 3200–2610, 2937, 2849, 1674; HPLC (40% MeCN/H2O to 100% MeCN, C18, 3.5 µm, 150x4.6 mm): tR = 21.073 min; 1H–NMR (400 MHz, d6-DMSO): δ 12.12 (br. s, 1H), 8.30 (d, J = 7.2 Hz, 1H), 8.28 (d, J = 7.2 Hz, 2H), 8.18 (m, 4H) , 8.08 (t, J = 7.2 Hz, 1H), 7.95 (d, J = 8 Hz, 1H), 7.23 (dd, J = 11.2 and 15.2 Hz, 1H), 6.53 (d, J = 15.2 Hz, 1H), 6.39 (d, J = 11.2 Hz, 1H), 5.83 (s, 1H), 2.47 (s, 3H), 2.39 (s, 3H) p.p.m.; ESI-MS (30 eV): m/z 704.21 (2M), 353.37 (MH), 335.36 (MH—H2O).

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
C1A	0.0508 (4)	0.8362 (4)	0.45141 (12)	0.0247 (8)
C1B	0.4808 (4)	1.3280 (4)	0.44843 (11)	0.0243 (8)
C2A	0.0917 (4)	0.7231 (4)	0.41240 (11)	0.0247 (8)
H2A	0.1673	0.7649	0.3909	0.030*
C2B	0.4635 (4)	1.2089 (4)	0.40651 (11)	0.0259 (8)
H2B	0.4067	1.2354	0.3794	0.031*
C3A	0.0344 (4)	0.5659 (4)	0.40331 (11)	0.0225 (8)
C3B	0.5198 (4)	1.0650 (4)	0.40221 (11)	0.0241 (8)
C4A	0.0898 (4)	0.4799 (4)	0.36041 (11)	0.0233 (8)
H4A	0.1564	0.5400	0.3407	0.028*
C4B	0.4895 (4)	0.9708 (4)	0.35600 (11)	0.0249 (8)
H4B	0.4385	1.0179	0.3319	0.030*
C5A	0.0542 (4)	0.3227 (4)	0.34658 (11)	0.0225 (8)
H5A	−0.0107	0.2600	0.3660	0.027*
C5B	0.5275 (4)	0.8214 (4)	0.34422 (11)	0.0239 (8)
H5B	0.5766	0.7701	0.3677	0.029*
C6A	0.1115 (4)	0.2460 (4)	0.30317 (11)	0.0243 (8)
H6A	0.1718	0.3113	0.2836	0.029*
C6B	0.4949 (4)	0.7392 (4)	0.29682 (11)	0.0254 (8)
H6B	0.4503	0.7952	0.2739	0.030*
C7A	0.0858 (4)	0.0887 (4)	0.28832 (11)	0.0210 (7)
C7B	0.5226 (4)	0.5888 (4)	0.28218 (11)	0.0231 (8)
C8A	−0.0034 (5)	−0.0307 (4)	0.31727 (11)	0.0316 (9)
H8A1	0.0530	−0.0133	0.3488	0.047*
H8A2	0.0071	−0.1363	0.3028	0.047*
H8A3	−0.1274	−0.0186	0.3186	0.047*
C8B	0.5888 (4)	0.4862 (4)	0.31719 (11)	0.0275 (8)
H8B1	0.7114	0.5246	0.3273	0.041*
H8B2	0.5788	0.3781	0.3023	0.041*
H8B3	0.5180	0.4909	0.3442	0.041*
C9A	−0.0803 (5)	0.4746 (4)	0.43400 (12)	0.0331 (9)
H9A1	−0.0110	0.4082	0.4500	0.050*
H9A2	−0.1771	0.4092	0.4149	0.050*
H9A3	−0.1272	0.5471	0.4570	0.050*
C9B	0.6137 (5)	0.9991 (4)	0.44129 (12)	0.0375 (10)
H9B1	0.6380	1.0790	0.4685	0.056*
H9B2	0.7240	0.9680	0.4309	0.056*
H9B3	0.5394	0.9081	0.4496	0.056*
C10A	0.1586 (4)	0.0308 (4)	0.24283 (10)	0.0202 (7)
C10B	0.4752 (4)	0.5222 (4)	0.23171 (11)	0.0209 (7)
C11A	0.0509 (4)	−0.0710 (4)	0.20581 (11)	0.0195 (7)
C11B	0.5854 (4)	0.4329 (4)	0.20344 (11)	0.0190 (7)
C12A	−0.1353 (4)	−0.1213 (4)	0.20822 (11)	0.0216 (8)
H12A	−0.1895	−0.0907	0.2358	0.026*
C12B	0.7587 (4)	0.4024 (4)	0.22032 (11)	0.0230 (8)
H12B	0.8021	0.4440	0.2511	0.028*
C13A	−0.2351 (4)	−0.2122 (4)	0.17156 (11)	0.0230 (8)
H13A	−0.3552	−0.2448	0.1750	0.028*
C13B	0.8592 (4)	0.3159 (4)	0.19311 (11)	0.0243 (8)
H13B	0.9677	0.2951	0.2061	0.029*
C14A	−0.1619 (4)	−0.2593 (4)	0.12809 (11)	0.0214 (8)
C14B	0.8048 (4)	0.2547 (4)	0.14485 (11)	0.0228 (8)
C15A	−0.2625 (4)	−0.3479 (4)	0.08916 (11)	0.0235 (8)
H15A	−0.3826	−0.3830	0.0918	0.028*
C15B	0.9078 (4)	0.1650 (4)	0.11602 (11)	0.0258 (8)
H15B	1.0170	0.1434	0.1282	0.031*
C16A	−0.1880 (4)	−0.3848 (4)	0.04670 (11)	0.0276 (8)
H16A	−0.2586	−0.4422	0.0209	0.033*
C16B	0.8500 (4)	0.1080 (4)	0.06972 (12)	0.0300 (9)
H16B	0.9202	0.0480	0.0510	0.036*
C17A	−0.0082 (4)	−0.3366 (4)	0.04229 (11)	0.0268 (8)
H17A	0.0408	−0.3618	0.0135	0.032*
C17B	0.6881 (5)	0.1392 (4)	0.05074 (12)	0.0293 (8)
H17B	0.6503	0.0989	0.0195	0.035*
C18A	0.0999 (4)	−0.2508 (4)	0.08053 (11)	0.0220 (8)
C18B	0.5813 (4)	0.2301 (4)	0.07801 (11)	0.0232 (8)
C19A	0.2858 (4)	−0.2031 (4)	0.07779 (11)	0.0255 (8)
H19A	0.3387	−0.2341	0.0500	0.031*
C19B	0.4127 (4)	0.2657 (4)	0.05942 (12)	0.0270 (8)
H19B	0.3738	0.2283	0.0280	0.032*
C20A	0.3873 (4)	−0.1144 (4)	0.11424 (11)	0.0254 (8)
H20A	0.5081	−0.0840	0.1110	0.030*
C20B	0.3109 (4)	0.3511 (4)	0.08627 (11)	0.0246 (8)
H20B	0.2038	0.3735	0.0730	0.030*
C21A	0.3126 (4)	−0.0664 (4)	0.15760 (11)	0.0209 (7)
C21B	0.3634 (4)	0.4090 (4)	0.13516 (11)	0.0218 (8)
C22A	0.4134 (4)	0.0312 (4)	0.19507 (11)	0.0222 (7)
H22A	0.5341	0.0638	0.1924	0.027*
C22B	0.2594 (4)	0.4966 (4)	0.16391 (11)	0.0238 (8)
H22B	0.1513	0.5194	0.1513	0.029*
C23A	0.3358 (4)	0.0796 (4)	0.23598 (11)	0.0214 (8)
H23A	0.4052	0.1477	0.2600	0.026*
C23B	0.3125 (4)	0.5504 (4)	0.21052 (11)	0.0230 (8)
H23B	0.2384	0.6075	0.2288	0.028*
C24A	0.1296 (4)	−0.1163 (4)	0.16294 (11)	0.0194 (7)
C24B	0.5297 (4)	0.3771 (4)	0.15525 (11)	0.0189 (7)
C25A	0.0224 (4)	−0.2094 (4)	0.12396 (11)	0.0195 (7)
C25B	0.6370 (4)	0.2868 (4)	0.12604 (11)	0.0210 (7)
O1A	−0.0314 (3)	0.8043 (3)	0.48587 (8)	0.0293 (6)
O1B	0.5355 (3)	1.3133 (3)	0.48846 (8)	0.0316 (6)
O2A	0.1129 (3)	0.9852 (3)	0.44623 (8)	0.0320 (6)
H2A1	0.092 (5)	1.054 (4)	0.4701 (10)	0.048*
O2B	0.4270 (3)	1.4636 (3)	0.43819 (8)	0.0342 (6)
H2B1	0.443 (5)	1.520 (4)	0.4655 (8)	0.051*

	U11	U22	U33	U12	U13	U23
C1A	0.032 (2)	0.019 (2)	0.0256 (19)	0.0097 (16)	0.0007 (15)	0.0053 (16)
C1B	0.0243 (18)	0.026 (2)	0.0222 (19)	0.0010 (16)	0.0056 (14)	0.0036 (16)
C2A	0.0261 (18)	0.024 (2)	0.0265 (19)	0.0080 (16)	0.0072 (14)	0.0059 (16)
C2B	0.0264 (19)	0.028 (2)	0.0233 (18)	0.0018 (16)	0.0009 (14)	0.0070 (16)
C3A	0.0234 (18)	0.019 (2)	0.0263 (19)	0.0057 (15)	0.0008 (14)	0.0034 (16)
C3B	0.0202 (18)	0.028 (2)	0.0245 (18)	−0.0003 (15)	0.0030 (14)	0.0066 (16)
C4A	0.0213 (18)	0.026 (2)	0.0245 (18)	0.0070 (15)	0.0061 (13)	0.0064 (16)
C4B	0.0233 (18)	0.028 (2)	0.0246 (18)	0.0052 (16)	0.0005 (14)	0.0068 (16)
C5A	0.0236 (18)	0.020 (2)	0.0232 (18)	0.0024 (15)	0.0013 (13)	0.0013 (15)
C5B	0.0217 (18)	0.028 (2)	0.0235 (18)	0.0035 (16)	0.0037 (13)	0.0086 (16)
C6A	0.0230 (18)	0.029 (2)	0.0230 (18)	0.0053 (16)	0.0030 (14)	0.0065 (16)
C6B	0.0232 (18)	0.027 (2)	0.0270 (19)	0.0063 (16)	0.0012 (14)	0.0061 (16)
C7A	0.0216 (18)	0.020 (2)	0.0232 (18)	0.0058 (15)	0.0032 (13)	0.0058 (15)
C7B	0.0204 (18)	0.022 (2)	0.0284 (19)	0.0025 (15)	0.0036 (14)	0.0071 (16)
C8A	0.039 (2)	0.031 (2)	0.0238 (19)	0.0009 (18)	0.0032 (15)	0.0039 (17)
C8B	0.034 (2)	0.022 (2)	0.0266 (19)	0.0045 (16)	0.0013 (15)	0.0047 (16)
C9A	0.038 (2)	0.034 (2)	0.0271 (19)	0.0027 (18)	0.0068 (16)	0.0025 (17)
C9B	0.047 (2)	0.035 (2)	0.031 (2)	0.0151 (19)	−0.0033 (17)	−0.0005 (18)
C10A	0.0211 (18)	0.0209 (19)	0.0197 (17)	0.0050 (15)	0.0022 (13)	0.0047 (15)
C10B	0.0226 (18)	0.0126 (18)	0.0274 (19)	0.0003 (14)	0.0008 (14)	0.0054 (15)
C11A	0.0235 (18)	0.0146 (18)	0.0222 (18)	0.0061 (15)	0.0023 (13)	0.0054 (14)
C11B	0.0196 (17)	0.0115 (18)	0.0261 (18)	−0.0002 (14)	0.0041 (13)	0.0054 (14)
C12A	0.0225 (18)	0.023 (2)	0.0219 (18)	0.0086 (15)	0.0061 (14)	0.0055 (15)
C12B	0.0250 (18)	0.020 (2)	0.0225 (18)	0.0004 (15)	−0.0018 (14)	0.0031 (15)
C13A	0.0198 (17)	0.024 (2)	0.0272 (19)	0.0036 (15)	0.0039 (14)	0.0082 (16)
C13B	0.0185 (18)	0.024 (2)	0.033 (2)	0.0057 (15)	−0.0005 (14)	0.0095 (16)
C14A	0.0252 (19)	0.0176 (19)	0.0230 (18)	0.0067 (15)	0.0013 (14)	0.0051 (15)
C14B	0.0243 (18)	0.0164 (19)	0.0290 (19)	0.0022 (15)	0.0042 (14)	0.0078 (15)
C15A	0.0220 (18)	0.0181 (19)	0.0304 (19)	−0.0004 (15)	0.0012 (14)	0.0065 (15)
C15B	0.0265 (19)	0.022 (2)	0.031 (2)	0.0061 (16)	0.0046 (15)	0.0095 (16)
C16A	0.031 (2)	0.023 (2)	0.027 (2)	0.0039 (16)	−0.0041 (15)	0.0002 (16)
C16B	0.036 (2)	0.023 (2)	0.034 (2)	0.0096 (17)	0.0126 (16)	0.0063 (17)
C17A	0.035 (2)	0.024 (2)	0.0223 (19)	0.0089 (17)	0.0054 (15)	0.0011 (15)
C17B	0.041 (2)	0.020 (2)	0.0261 (19)	0.0025 (17)	0.0035 (16)	0.0016 (16)
C18A	0.0287 (19)	0.0161 (19)	0.0232 (18)	0.0075 (15)	0.0033 (14)	0.0055 (15)
C18B	0.0280 (19)	0.0159 (19)	0.0265 (19)	−0.0014 (15)	0.0048 (14)	0.0094 (15)
C19A	0.0272 (19)	0.027 (2)	0.0260 (19)	0.0119 (16)	0.0093 (14)	0.0081 (16)
C19B	0.030 (2)	0.023 (2)	0.0264 (19)	−0.0019 (16)	−0.0045 (15)	0.0058 (16)
C20A	0.0243 (18)	0.024 (2)	0.031 (2)	0.0096 (16)	0.0095 (15)	0.0082 (16)
C20B	0.0233 (18)	0.024 (2)	0.0276 (19)	0.0026 (16)	−0.0025 (14)	0.0098 (16)
C21A	0.0213 (18)	0.0156 (18)	0.0270 (18)	0.0066 (15)	0.0024 (14)	0.0039 (15)
C21B	0.0199 (18)	0.0172 (19)	0.0290 (19)	0.0014 (15)	0.0028 (14)	0.0069 (15)
C22A	0.0210 (17)	0.0177 (19)	0.0288 (19)	0.0021 (15)	0.0042 (14)	0.0065 (15)
C22B	0.0197 (18)	0.020 (2)	0.033 (2)	0.0044 (15)	−0.0021 (14)	0.0090 (16)
C23A	0.0244 (19)	0.0125 (18)	0.0265 (18)	0.0000 (15)	−0.0014 (14)	0.0033 (15)
C23B	0.0218 (18)	0.0185 (19)	0.0298 (19)	0.0048 (15)	0.0058 (14)	0.0043 (15)
C24A	0.0214 (18)	0.0129 (18)	0.0252 (18)	0.0048 (14)	0.0019 (14)	0.0054 (14)
C24B	0.0193 (17)	0.0132 (18)	0.0234 (18)	−0.0029 (14)	0.0020 (13)	0.0053 (14)
C25A	0.0191 (17)	0.0175 (19)	0.0237 (18)	0.0078 (14)	0.0022 (13)	0.0039 (14)
C25B	0.0228 (18)	0.0172 (19)	0.0241 (18)	0.0020 (15)	0.0034 (14)	0.0069 (15)
O1A	0.0414 (15)	0.0224 (14)	0.0251 (13)	0.0043 (11)	0.0091 (11)	0.0046 (11)
O1B	0.0459 (15)	0.0258 (15)	0.0243 (13)	0.0077 (12)	0.0023 (11)	0.0046 (11)
O2A	0.0435 (15)	0.0201 (15)	0.0322 (15)	0.0027 (12)	0.0114 (11)	0.0006 (11)
O2B	0.0466 (15)	0.0243 (15)	0.0321 (14)	0.0122 (12)	−0.0023 (12)	−0.0007 (11)

C1A—O1A	1.228 (4)	C12A—C13A	1.351 (4)
C1A—O2A	1.327 (4)	C12A—H12A	0.9300
C1A—C2A	1.454 (4)	C12B—C13B	1.340 (4)
C1B—O1B	1.218 (4)	C12B—H12B	0.9300
C1B—O2B	1.338 (4)	C13A—C14A	1.417 (4)
C1B—C2B	1.458 (4)	C13A—H13A	0.9300
C2A—C3A	1.345 (4)	C13B—C14B	1.427 (4)
C2A—H2A	0.9300	C13B—H13B	0.9300
C2B—C3B	1.347 (4)	C14A—C15A	1.390 (4)
C2B—H2B	0.9300	C14A—C25A	1.421 (4)
C3A—C4A	1.456 (4)	C14B—C15B	1.392 (4)
C3A—C9A	1.482 (5)	C14B—C25B	1.426 (4)
C3B—C4B	1.445 (4)	C15A—C16A	1.379 (4)
C3B—C9B	1.496 (4)	C15A—H15A	0.9300
C4A—C5A	1.340 (4)	C15B—C16B	1.375 (4)
C4A—H4A	0.9300	C15B—H15B	0.9300
C4B—C5B	1.352 (4)	C16A—C17A	1.387 (4)
C4B—H4B	0.9300	C16A—H16A	0.9300
C5A—C6A	1.441 (4)	C16B—C17B	1.385 (4)
C5A—H5A	0.9300	C16B—H16B	0.9300
C5B—C6B	1.435 (4)	C17A—C18A	1.395 (4)
C5B—H5B	0.9300	C17A—H17A	0.9300
C6A—C7A	1.344 (4)	C17B—C18B	1.395 (4)
C6A—H6A	0.9300	C17B—H17B	0.9300
C6B—C7B	1.348 (4)	C18A—C25A	1.421 (4)
C6B—H6B	0.9300	C18A—C19A	1.423 (4)
C7A—C10A	1.488 (4)	C18B—C25B	1.415 (4)
C7A—C8A	1.504 (4)	C18B—C19B	1.441 (4)
C7B—C10B	1.485 (4)	C19A—C20A	1.346 (4)
C7B—C8B	1.514 (4)	C19A—H19A	0.9300
C8A—H8A1	0.9600	C19B—C20B	1.335 (4)
C8A—H8A2	0.9600	C19B—H19B	0.9300
C8A—H8A3	0.9600	C20A—C21A	1.422 (4)
C8B—H8B1	0.9600	C20A—H20A	0.9300
C8B—H8B2	0.9600	C20B—C21B	1.435 (4)
C8B—H8B3	0.9600	C20B—H20B	0.9300
C9A—H9A1	0.9600	C21A—C22A	1.394 (4)
C9A—H9A2	0.9600	C21A—C24A	1.418 (4)
C9A—H9A3	0.9600	C21B—C22B	1.387 (4)
C9B—H9B1	0.9600	C21B—C24B	1.429 (4)
C9B—H9B2	0.9600	C22A—C23A	1.374 (4)
C9B—H9B3	0.9600	C22A—H22A	0.9300
C10A—C23A	1.384 (4)	C22B—C23B	1.370 (4)
C10A—C11A	1.424 (4)	C22B—H22B	0.9300
C10B—C23B	1.406 (4)	C23A—H23A	0.9300
C10B—C11B	1.419 (4)	C23B—H23B	0.9300
C11A—C24A	1.419 (4)	C24A—C25A	1.429 (4)
C11A—C12A	1.427 (4)	C24B—C25B	1.423 (4)
C11B—C24B	1.418 (4)	O2A—H2A1	0.876 (18)
C11B—C12B	1.442 (4)	O2B—H2B1	0.858 (18)
O1A—C1A—O2A	121.5 (3)	C13B—C12B—H12B	118.9
O1A—C1A—C2A	126.4 (3)	C11B—C12B—H12B	118.9
O2A—C1A—C2A	112.1 (3)	C12A—C13A—C14A	121.9 (3)
O1B—C1B—O2B	121.5 (3)	C12A—C13A—H13A	119.0
O1B—C1B—C2B	127.2 (3)	C14A—C13A—H13A	119.0
O2B—C1B—C2B	111.2 (3)	C12B—C13B—C14B	121.9 (3)
C3A—C2A—C1A	128.4 (3)	C12B—C13B—H13B	119.0
C3A—C2A—H2A	115.8	C14B—C13B—H13B	119.0
C1A—C2A—H2A	115.8	C15A—C14A—C13A	123.3 (3)
C3B—C2B—C1B	127.9 (3)	C15A—C14A—C25A	118.8 (3)
C3B—C2B—H2B	116.0	C13A—C14A—C25A	118.0 (3)
C1B—C2B—H2B	116.0	C15B—C14B—C25B	119.4 (3)
C2A—C3A—C4A	117.5 (3)	C15B—C14B—C13B	122.7 (3)
C2A—C3A—C9A	124.5 (3)	C25B—C14B—C13B	117.9 (3)
C4A—C3A—C9A	118.0 (3)	C16A—C15A—C14A	121.5 (3)
C2B—C3B—C4B	116.8 (3)	C16A—C15A—H15A	119.3
C2B—C3B—C9B	124.7 (3)	C14A—C15A—H15A	119.3
C4B—C3B—C9B	118.5 (3)	C16B—C15B—C14B	120.8 (3)
C5A—C4A—C3A	126.3 (3)	C16B—C15B—H15B	119.6
C5A—C4A—H4A	116.8	C14B—C15B—H15B	119.6
C3A—C4A—H4A	116.8	C15A—C16A—C17A	120.2 (3)
C5B—C4B—C3B	126.8 (3)	C15A—C16A—H16A	119.9
C5B—C4B—H4B	116.6	C17A—C16A—H16A	119.9
C3B—C4B—H4B	116.6	C15B—C16B—C17B	120.6 (3)
C4A—C5A—C6A	123.2 (3)	C15B—C16B—H16B	119.7
C4A—C5A—H5A	118.4	C17B—C16B—H16B	119.7
C6A—C5A—H5A	118.4	C16A—C17A—C18A	120.8 (3)
C4B—C5B—C6B	122.3 (3)	C16A—C17A—H17A	119.6
C4B—C5B—H5B	118.8	C18A—C17A—H17A	119.6
C6B—C5B—H5B	118.8	C16B—C17B—C18B	120.8 (3)
C7A—C6A—C5A	126.0 (3)	C16B—C17B—H17B	119.6
C7A—C6A—H6A	117.0	C18B—C17B—H17B	119.6
C5A—C6A—H6A	117.0	C17A—C18A—C25A	119.1 (3)
C7B—C6B—C5B	126.5 (3)	C17A—C18A—C19A	122.4 (3)
C7B—C6B—H6B	116.8	C25A—C18A—C19A	118.5 (3)
C5B—C6B—H6B	116.8	C17B—C18B—C25B	119.3 (3)
C6A—C7A—C10A	118.3 (3)	C17B—C18B—C19B	122.3 (3)
C6A—C7A—C8A	122.5 (3)	C25B—C18B—C19B	118.3 (3)
C10A—C7A—C8A	119.1 (3)	C20A—C19A—C18A	121.9 (3)
C6B—C7B—C10B	118.7 (3)	C20A—C19A—H19A	119.1
C6B—C7B—C8B	120.6 (3)	C18A—C19A—H19A	119.1
C10B—C7B—C8B	120.6 (3)	C20B—C19B—C18B	121.5 (3)
C7A—C8A—H8A1	109.5	C20B—C19B—H19B	119.3
C7A—C8A—H8A2	109.5	C18B—C19B—H19B	119.3
H8A1—C8A—H8A2	109.5	C19A—C20A—C21A	121.0 (3)
C7A—C8A—H8A3	109.5	C19A—C20A—H20A	119.5
H8A1—C8A—H8A3	109.5	C21A—C20A—H20A	119.5
H8A2—C8A—H8A3	109.5	C19B—C20B—C21B	121.4 (3)
C7B—C8B—H8B1	109.5	C19B—C20B—H20B	119.3
C7B—C8B—H8B2	109.5	C21B—C20B—H20B	119.3
H8B1—C8B—H8B2	109.5	C22A—C21A—C24A	118.6 (3)
C7B—C8B—H8B3	109.5	C22A—C21A—C20A	121.9 (3)
H8B1—C8B—H8B3	109.5	C24A—C21A—C20A	119.5 (3)
H8B2—C8B—H8B3	109.5	C22B—C21B—C24B	118.2 (3)
C3A—C9A—H9A1	109.5	C22B—C21B—C20B	122.5 (3)
C3A—C9A—H9A2	109.5	C24B—C21B—C20B	119.2 (3)
H9A1—C9A—H9A2	109.5	C23A—C22A—C21A	120.5 (3)
C3A—C9A—H9A3	109.5	C23A—C22A—H22A	119.7
H9A1—C9A—H9A3	109.5	C21A—C22A—H22A	119.7
H9A2—C9A—H9A3	109.5	C23B—C22B—C21B	121.3 (3)
C3B—C9B—H9B1	109.5	C23B—C22B—H22B	119.3
C3B—C9B—H9B2	109.5	C21B—C22B—H22B	119.3
H9B1—C9B—H9B2	109.5	C22A—C23A—C10A	122.5 (3)
C3B—C9B—H9B3	109.5	C22A—C23A—H23A	118.7
H9B1—C9B—H9B3	109.5	C10A—C23A—H23A	118.7
H9B2—C9B—H9B3	109.5	C22B—C23B—C10B	122.3 (3)
C23A—C10A—C11A	119.0 (3)	C22B—C23B—H23B	118.8
C23A—C10A—C7A	118.9 (3)	C10B—C23B—H23B	118.8
C11A—C10A—C7A	122.1 (3)	C21A—C24A—C11A	120.9 (3)
C23B—C10B—C11B	118.0 (3)	C21A—C24A—C25A	119.2 (3)
C23B—C10B—C7B	118.2 (3)	C11A—C24A—C25A	119.9 (3)
C11B—C10B—C7B	123.8 (3)	C11B—C24B—C25B	120.8 (3)
C24A—C11A—C10A	118.4 (3)	C11B—C24B—C21B	120.6 (3)
C24A—C11A—C12A	118.0 (3)	C25B—C24B—C21B	118.6 (3)
C10A—C11A—C12A	123.5 (3)	C14A—C25A—C18A	119.7 (3)
C24B—C11B—C10B	119.5 (3)	C14A—C25A—C24A	120.4 (3)
C24B—C11B—C12B	117.1 (3)	C18A—C25A—C24A	119.9 (3)
C10B—C11B—C12B	123.3 (3)	C18B—C25B—C24B	121.0 (3)
C13A—C12A—C11A	121.9 (3)	C18B—C25B—C14B	119.1 (3)
C13A—C12A—H12A	119.1	C24B—C25B—C14B	120.0 (3)
C11A—C12A—H12A	119.1	C1A—O2A—H2A1	113 (2)
C13B—C12B—C11B	122.2 (3)	C1B—O2B—H2B1	101 (3)
O1A—C1A—C2A—C3A	7.5 (5)	C25A—C18A—C19A—C20A	−3.1 (5)
O2A—C1A—C2A—C3A	−172.4 (3)	C17B—C18B—C19B—C20B	179.0 (3)
O1B—C1B—C2B—C3B	−7.0 (6)	C25B—C18B—C19B—C20B	0.7 (5)
O2B—C1B—C2B—C3B	173.2 (3)	C18A—C19A—C20A—C21A	1.0 (5)
C1A—C2A—C3A—C4A	177.5 (3)	C18B—C19B—C20B—C21B	−1.2 (5)
C1A—C2A—C3A—C9A	−2.7 (5)	C19A—C20A—C21A—C22A	−177.2 (3)
C1B—C2B—C3B—C4B	−178.5 (3)	C19A—C20A—C21A—C24A	1.7 (5)
C1B—C2B—C3B—C9B	0.1 (6)	C19B—C20B—C21B—C22B	−179.4 (3)
C2A—C3A—C4A—C5A	176.4 (3)	C19B—C20B—C21B—C24B	1.2 (5)
C9A—C3A—C4A—C5A	−3.4 (5)	C24A—C21A—C22A—C23A	−0.9 (4)
C2B—C3B—C4B—C5B	−176.9 (3)	C20A—C21A—C22A—C23A	178.0 (3)
C9B—C3B—C4B—C5B	4.4 (5)	C24B—C21B—C22B—C23B	−0.7 (5)
C3A—C4A—C5A—C6A	179.1 (3)	C20B—C21B—C22B—C23B	179.9 (3)
C3B—C4B—C5B—C6B	−178.8 (3)	C21A—C22A—C23A—C10A	2.2 (5)
C4A—C5A—C6A—C7A	177.3 (3)	C11A—C10A—C23A—C22A	−1.2 (5)
C4B—C5B—C6B—C7B	−177.5 (3)	C7A—C10A—C23A—C22A	179.8 (3)
C5A—C6A—C7A—C10A	−178.6 (3)	C21B—C22B—C23B—C10B	0.9 (5)
C5A—C6A—C7A—C8A	−2.3 (5)	C11B—C10B—C23B—C22B	−0.9 (5)
C5B—C6B—C7B—C10B	178.1 (3)	C7B—C10B—C23B—C22B	178.6 (3)
C5B—C6B—C7B—C8B	2.2 (5)	C22A—C21A—C24A—C11A	−1.3 (4)
C6A—C7A—C10A—C23A	51.1 (4)	C20A—C21A—C24A—C11A	179.8 (3)
C8A—C7A—C10A—C23A	−125.3 (3)	C22A—C21A—C24A—C25A	176.8 (3)
C6A—C7A—C10A—C11A	−127.8 (3)	C20A—C21A—C24A—C25A	−2.1 (4)
C8A—C7A—C10A—C11A	55.8 (4)	C10A—C11A—C24A—C21A	2.3 (4)
C6B—C7B—C10B—C23B	−43.4 (4)	C12A—C11A—C24A—C21A	178.1 (3)
C8B—C7B—C10B—C23B	132.5 (3)	C10A—C11A—C24A—C25A	−175.8 (3)
C6B—C7B—C10B—C11B	136.0 (3)	C12A—C11A—C24A—C25A	0.0 (4)
C8B—C7B—C10B—C11B	−48.1 (4)	C10B—C11B—C24B—C25B	−179.8 (3)
C23A—C10A—C11A—C24A	−1.0 (4)	C12B—C11B—C24B—C25B	3.6 (4)
C7A—C10A—C11A—C24A	177.9 (3)	C10B—C11B—C24B—C21B	−0.5 (5)
C23A—C10A—C11A—C12A	−176.6 (3)	C12B—C11B—C24B—C21B	−177.1 (3)
C7A—C10A—C11A—C12A	2.3 (5)	C22B—C21B—C24B—C11B	0.5 (5)
C23B—C10B—C11B—C24B	0.7 (5)	C20B—C21B—C24B—C11B	179.9 (3)
C7B—C10B—C11B—C24B	−178.8 (3)	C22B—C21B—C24B—C25B	179.8 (3)
C23B—C10B—C11B—C12B	177.0 (3)	C20B—C21B—C24B—C25B	−0.8 (5)
C7B—C10B—C11B—C12B	−2.4 (5)	C15A—C14A—C25A—C18A	−0.1 (4)
C24A—C11A—C12A—C13A	1.4 (4)	C13A—C14A—C25A—C18A	−178.4 (3)
C10A—C11A—C12A—C13A	177.0 (3)	C15A—C14A—C25A—C24A	179.1 (3)
C24B—C11B—C12B—C13B	−4.5 (5)	C13A—C14A—C25A—C24A	0.8 (4)
C10B—C11B—C12B—C13B	179.1 (3)	C17A—C18A—C25A—C14A	1.6 (4)
C11A—C12A—C13A—C14A	−1.8 (5)	C19A—C18A—C25A—C14A	−178.3 (3)
C11B—C12B—C13B—C14B	3.0 (5)	C17A—C18A—C25A—C24A	−177.6 (3)
C12A—C13A—C14A—C15A	−177.6 (3)	C19A—C18A—C25A—C24A	2.5 (4)
C12A—C13A—C14A—C25A	0.7 (4)	C21A—C24A—C25A—C14A	−179.2 (3)
C12B—C13B—C14B—C15B	179.8 (3)	C11A—C24A—C25A—C14A	−1.1 (4)
C12B—C13B—C14B—C25B	−0.7 (5)	C21A—C24A—C25A—C18A	0.0 (4)
C13A—C14A—C15A—C16A	176.8 (3)	C11A—C24A—C25A—C18A	178.1 (3)
C25A—C14A—C15A—C16A	−1.4 (5)	C17B—C18B—C25B—C24B	−178.7 (3)
C25B—C14B—C15B—C16B	0.3 (5)	C19B—C18B—C25B—C24B	−0.2 (5)
C13B—C14B—C15B—C16B	179.8 (3)	C17B—C18B—C25B—C14B	2.5 (5)
C14A—C15A—C16A—C17A	1.4 (5)	C19B—C18B—C25B—C14B	−179.1 (3)
C14B—C15B—C16B—C17B	0.2 (5)	C11B—C24B—C25B—C18B	179.6 (3)
C15A—C16A—C17A—C18A	0.2 (5)	C21B—C24B—C25B—C18B	0.3 (5)
C15B—C16B—C17B—C18B	0.6 (5)	C11B—C24B—C25B—C14B	−1.5 (5)
C16A—C17A—C18A—C25A	−1.7 (5)	C21B—C24B—C25B—C14B	179.2 (3)
C16A—C17A—C18A—C19A	178.2 (3)	C15B—C14B—C25B—C18B	−1.7 (5)
C16B—C17B—C18B—C25B	−2.0 (5)	C13B—C14B—C25B—C18B	178.8 (3)
C16B—C17B—C18B—C19B	179.7 (3)	C15B—C14B—C25B—C24B	179.5 (3)
C17A—C18A—C19A—C20A	177.0 (3)	C13B—C14B—C25B—C24B	−0.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2A1···O1Ai	0.88 (2)	1.76 (2)	2.629 (3)	174 (4)
O2B—H2B1···O1Bii	0.86 (2)	1.79 (2)	2.624 (3)	162 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2A—H2A1⋯O1Ai	0.876 (18)	1.756 (19)	2.629 (3)	174 (4)
O2B—H2B1⋯O1Bii	0.858 (18)	1.79 (2)	2.624 (3)	162 (4)

Symmetry codes: (i) ; (ii) .