(E)-3-[4-(Dodec-yloxy)phen-yl]-1-(2-hydroxy-phen-yl)prop-2-en-1-one.

In the title compound, C(27)H(36)O(3), the asymmetric unit consists of two crystallographically independent mol-ecules. The aromatic rings form dihedral angles of 17.1 (2) and 17.6 (2)° in the two molecules. In both mol-ecules, the enone groups adopt an s-cis conformation and the alkoxyl chains are in trans conformations curving out of the zigzag plane. Intra-molecular O-H⋯O hydrogen bonds involving the keto and hydr-oxy groups generate S(6) ring motifs. The mol-ecules are stacked alternately in a head-to-tail fashion along the a axis and the crystal structure is stabilized by weak C-H⋯π inter-actions. The crystal studied was a non-merohedral twin, the ratio of components being 0.788 (2):0.212 (2).

Related literature

For general background to the biological activity of chalcone derivatives, see: Bhat et al. (2005 ▶); Xue et al. (2004 ▶); Satyanarayana et al. (2004 ▶); Zhao et al. (2005 ▶); Lee et al. (2006 ▶). For related structures, see: Ng et al. (2006 ▶); Razak et al. (2009 ▶); Ngaini, Fadzillah et al. (2009 ▶); Ngaini, Rahman et al. (2009 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C27H36O3

M = 408.56

Triclinic,

a = 7.4953 (6) Å

b = 13.4714 (9) Å

c = 23.7874 (18) Å

α = 75.116 (4)°

β = 83.876 (5)°

γ = 84.669 (5)°

V = 2302.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.55 × 0.13 × 0.06 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.960, T max = 0.996

8571 measured reflections

8571 independent reflections

4737 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.206

S = 1.03

8571 reflections

546 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014925/lh2802sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014925/lh2802Isup2.hkl

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

C27H36O3	Z = 4
Mr = 408.56	F(000) = 888
Triclinic, P1	Dx = 1.179 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4953 (6) Å	Cell parameters from 3668 reflections
b = 13.4714 (9) Å	θ = 2.7–28.0°
c = 23.7874 (18) Å	µ = 0.08 mm−1
α = 75.116 (4)°	T = 100 K
β = 83.876 (5)°	Needle, yellow
γ = 84.669 (5)°	0.55 × 0.13 × 0.06 mm
V = 2302.7 (3) Å3

Bruker APEXII diffractometer	8571 independent reflections
Radiation source: sealed tube	4737 reflections with I > 2σ(I)
graphite	Rint = 0.0000
π and ω scans	θmax = 25.5°, θmin = 0.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→9
Tmin = 0.960, Tmax = 0.996	k = −16→16
8571 measured reflections	l = −28→28

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.206	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0924P)2 + 0.763P] where P = (Fo2 + 2Fc2)/3
8571 reflections	(Δ/σ)max < 0.001
546 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.6765 (4)	0.69790 (18)	0.78918 (11)	0.0307 (6)
H1A	0.6609	0.6985	0.7555	0.046*
O2A	0.6335 (3)	0.62359 (18)	0.70527 (11)	0.0290 (6)
O3A	0.6291 (3)	0.19687 (18)	0.50595 (10)	0.0255 (6)
C1A	0.6917 (5)	0.5994 (3)	0.82144 (16)	0.0249 (8)
C2A	0.7137 (5)	0.5837 (3)	0.88068 (16)	0.0273 (9)
H2AA	0.7158	0.6397	0.8966	0.033*
C3A	0.7324 (5)	0.4852 (3)	0.91544 (16)	0.0294 (9)
H3AA	0.7456	0.4751	0.9550	0.035*
C4A	0.7320 (5)	0.4007 (3)	0.89221 (15)	0.0288 (9)
H4AA	0.7469	0.3344	0.9159	0.035*
C5A	0.7094 (5)	0.4154 (3)	0.83407 (15)	0.0256 (8)
H5AA	0.7088	0.3585	0.8187	0.031*
C6A	0.6871 (4)	0.5145 (3)	0.79750 (15)	0.0210 (8)
C7A	0.6563 (4)	0.5329 (3)	0.73494 (15)	0.0220 (8)
C8A	0.6552 (5)	0.4480 (3)	0.70683 (15)	0.0235 (8)
H8AA	0.6597	0.3802	0.7291	0.028*
C9A	0.6477 (4)	0.4687 (3)	0.64905 (15)	0.0231 (8)
H9AA	0.6432	0.5381	0.6297	0.028*
C10A	0.6455 (4)	0.3974 (3)	0.61220 (15)	0.0214 (8)
C11A	0.6156 (5)	0.2928 (3)	0.63470 (15)	0.0230 (8)
H11A	0.5988	0.2660	0.6749	0.028*
C12A	0.6109 (4)	0.2297 (3)	0.59822 (15)	0.0221 (8)
H12A	0.5905	0.1606	0.6139	0.027*
C13A	0.6362 (4)	0.2674 (3)	0.53777 (15)	0.0203 (8)
C14A	0.6673 (5)	0.3704 (3)	0.51432 (15)	0.0229 (8)
H14A	0.6862	0.3961	0.4741	0.028*
C15A	0.6698 (5)	0.4344 (3)	0.55132 (15)	0.0233 (8)
H15A	0.6882	0.5037	0.5354	0.028*
C16A	0.6352 (5)	0.2302 (3)	0.44325 (15)	0.0236 (8)
H16A	0.7410	0.2680	0.4277	0.028*
H16B	0.5292	0.2746	0.4313	0.028*
C17A	0.6417 (5)	0.1341 (3)	0.42151 (15)	0.0252 (8)
H17A	0.5401	0.0951	0.4406	0.030*
H17B	0.7502	0.0923	0.4334	0.030*
C18A	0.6386 (5)	0.1513 (3)	0.35641 (15)	0.0233 (8)
H18A	0.7441	0.1861	0.3368	0.028*
H18B	0.5331	0.1953	0.3437	0.028*
C19A	0.6354 (5)	0.0500 (3)	0.33918 (15)	0.0240 (8)
H19A	0.7360	0.0046	0.3550	0.029*
H19B	0.5261	0.0178	0.3575	0.029*
C20A	0.6443 (5)	0.0575 (3)	0.27412 (15)	0.0255 (8)
H20A	0.7542	0.0885	0.2554	0.031*
H20B	0.5437	0.1023	0.2578	0.031*
C21A	0.6396 (5)	−0.0469 (3)	0.26067 (15)	0.0252 (8)
H21A	0.7325	−0.0935	0.2806	0.030*
H21B	0.5246	−0.0746	0.2764	0.030*
C22A	0.6664 (5)	−0.0442 (3)	0.19601 (15)	0.0246 (8)
H22A	0.7767	−0.0116	0.1794	0.029*
H22B	0.5678	−0.0025	0.1765	0.029*
C23A	0.6765 (5)	−0.1509 (3)	0.18409 (15)	0.0251 (8)
H23A	0.7717	−0.1936	0.2051	0.030*
H23B	0.5641	−0.1823	0.1992	0.030*
C24A	0.7112 (5)	−0.1494 (3)	0.11987 (15)	0.0265 (9)
H24A	0.8193	−0.1139	0.1041	0.032*
H24B	0.6119	−0.1105	0.0993	0.032*
C25A	0.7332 (5)	−0.2558 (3)	0.10808 (15)	0.0276 (9)
H25A	0.8331	−0.2946	0.1284	0.033*
H25B	0.6254	−0.2915	0.1240	0.033*
C26A	0.7664 (5)	−0.2538 (3)	0.04410 (15)	0.0288 (9)
H26A	0.8748	−0.2187	0.0282	0.035*
H26B	0.6671	−0.2145	0.0237	0.035*
C27A	0.7868 (6)	−0.3608 (3)	0.03238 (16)	0.0336 (10)
H27A	0.8210	−0.3548	−0.0084	0.050*
H27B	0.6745	−0.3925	0.0431	0.050*
H27C	0.8778	−0.4023	0.0551	0.050*
O1B	0.1478 (4)	−0.19486 (18)	0.21550 (11)	0.0324 (7)
H1B	0.1245	−0.1949	0.2500	0.049*
O2B	0.0945 (3)	−0.11900 (18)	0.30324 (11)	0.0290 (6)
O3B	0.1502 (3)	0.30711 (17)	0.50023 (10)	0.0251 (6)
C1B	0.1699 (5)	−0.0980 (3)	0.18370 (16)	0.0248 (8)
C2B	0.2029 (5)	−0.0831 (3)	0.12353 (17)	0.0296 (9)
H2BA	0.2081	−0.1390	0.1071	0.036*
C3B	0.2280 (5)	0.0137 (3)	0.08821 (17)	0.0328 (10)
H3BA	0.2487	0.0230	0.0480	0.039*
C4B	0.2224 (5)	0.0976 (3)	0.11249 (16)	0.0310 (9)
H4BA	0.2395	0.1631	0.0886	0.037*
C5B	0.1917 (5)	0.0837 (3)	0.17155 (16)	0.0252 (8)
H5BA	0.1892	0.1402	0.1874	0.030*
C6B	0.1638 (4)	−0.0137 (3)	0.20895 (16)	0.0224 (8)
C7B	0.1286 (4)	−0.0313 (3)	0.27275 (15)	0.0224 (8)
C8B	0.1362 (4)	0.0522 (3)	0.30173 (15)	0.0230 (8)
H8BA	0.1448	0.1195	0.2794	0.028*
C9B	0.1308 (4)	0.0320 (3)	0.35977 (15)	0.0217 (8)
H9BA	0.1227	−0.0367	0.3796	0.026*
C10B	0.1359 (5)	0.1032 (3)	0.39596 (15)	0.0231 (8)
C11B	0.1184 (5)	0.2102 (3)	0.37436 (15)	0.0234 (8)
H11B	0.1037	0.2379	0.3350	0.028*
C12B	0.1225 (5)	0.2748 (3)	0.41016 (16)	0.0258 (9)
H12B	0.1100	0.3457	0.3949	0.031*
C13B	0.1452 (5)	0.2351 (3)	0.46948 (16)	0.0230 (8)
C14B	0.1622 (5)	0.1297 (3)	0.49237 (16)	0.0249 (8)
H14B	0.1760	0.1024	0.5319	0.030*
C15B	0.1585 (5)	0.0651 (3)	0.45546 (16)	0.0259 (9)
H15B	0.1713	−0.0057	0.4708	0.031*
C16B	0.1390 (5)	0.2755 (3)	0.56305 (15)	0.0237 (8)
H16C	0.2351	0.2240	0.5761	0.028*
H16D	0.0247	0.2466	0.5783	0.028*
C17B	0.1564 (5)	0.3710 (3)	0.58335 (15)	0.0247 (8)
H17C	0.0658	0.4232	0.5666	0.030*
H17D	0.2732	0.3969	0.5684	0.030*
C18B	0.1366 (5)	0.3554 (3)	0.64911 (15)	0.0245 (8)
H18C	0.2292	0.3050	0.6663	0.029*
H18D	0.0206	0.3289	0.6646	0.029*
C19B	0.1520 (5)	0.4559 (3)	0.66580 (15)	0.0249 (8)
H19C	0.2613	0.4858	0.6457	0.030*
H19D	0.0517	0.5031	0.6515	0.030*
C20B	0.1549 (5)	0.4484 (3)	0.73017 (15)	0.0231 (8)
H20C	0.2600	0.4055	0.7444	0.028*
H20D	0.0492	0.4153	0.7510	0.028*
C21B	0.1587 (5)	0.5525 (3)	0.74315 (15)	0.0248 (8)
H21C	0.0480	0.5927	0.7321	0.030*
H21D	0.2572	0.5882	0.7189	0.030*
C22B	0.1799 (5)	0.5491 (3)	0.80653 (15)	0.0255 (8)
H22C	0.0780	0.5170	0.8307	0.031*
H22D	0.2875	0.5063	0.8184	0.031*
C23B	0.1928 (5)	0.6542 (3)	0.81750 (15)	0.0262 (8)
H23C	0.0837	0.6963	0.8067	0.031*
H23D	0.2924	0.6871	0.7924	0.031*
C24B	0.2195 (5)	0.6512 (3)	0.88035 (15)	0.0262 (8)
H24C	0.3210	0.6032	0.8925	0.031*
H24D	0.1137	0.6252	0.9049	0.031*
C25B	0.2525 (5)	0.7555 (3)	0.89035 (15)	0.0276 (9)
H25C	0.3601	0.7808	0.8666	0.033*
H25D	0.1524	0.8041	0.8774	0.033*
C26B	0.2743 (5)	0.7519 (3)	0.95361 (15)	0.0281 (9)
H26C	0.3818	0.7090	0.9654	0.034*
H26D	0.1724	0.7200	0.9779	0.034*
C27B	0.2879 (6)	0.8576 (3)	0.96430 (17)	0.0361 (10)
H27D	0.3122	0.8498	1.0041	0.054*
H27E	0.1764	0.8979	0.9570	0.054*
H27F	0.3835	0.8915	0.9386	0.054*

	U11	U22	U33	U12	U13	U23
O1A	0.0346 (16)	0.0267 (14)	0.0343 (16)	−0.0020 (11)	−0.0117 (13)	−0.0102 (12)
O2A	0.0320 (15)	0.0243 (14)	0.0325 (15)	−0.0041 (11)	−0.0084 (12)	−0.0074 (11)
O3A	0.0314 (15)	0.0256 (14)	0.0220 (14)	−0.0052 (11)	−0.0045 (11)	−0.0081 (11)
C1A	0.0151 (19)	0.027 (2)	0.033 (2)	−0.0025 (15)	−0.0031 (16)	−0.0072 (17)
C2A	0.022 (2)	0.031 (2)	0.034 (2)	−0.0024 (16)	−0.0058 (17)	−0.0160 (17)
C3A	0.025 (2)	0.043 (2)	0.023 (2)	−0.0046 (17)	−0.0076 (17)	−0.0121 (18)
C4A	0.032 (2)	0.029 (2)	0.025 (2)	−0.0052 (17)	−0.0047 (17)	−0.0054 (16)
C5A	0.025 (2)	0.027 (2)	0.027 (2)	−0.0053 (16)	−0.0017 (16)	−0.0102 (16)
C6A	0.0143 (18)	0.027 (2)	0.024 (2)	−0.0053 (15)	−0.0010 (15)	−0.0078 (16)
C7A	0.0136 (18)	0.025 (2)	0.027 (2)	−0.0029 (14)	−0.0030 (15)	−0.0055 (16)
C8A	0.020 (2)	0.024 (2)	0.027 (2)	−0.0006 (15)	−0.0037 (16)	−0.0048 (16)
C9A	0.0148 (19)	0.025 (2)	0.029 (2)	−0.0038 (14)	−0.0057 (16)	−0.0032 (16)
C10A	0.0111 (18)	0.028 (2)	0.028 (2)	−0.0022 (14)	−0.0037 (15)	−0.0102 (16)
C11A	0.0179 (19)	0.029 (2)	0.023 (2)	−0.0024 (15)	−0.0054 (15)	−0.0049 (16)
C12A	0.0167 (19)	0.0210 (19)	0.028 (2)	−0.0016 (14)	−0.0059 (15)	−0.0042 (16)
C13A	0.0132 (18)	0.0224 (19)	0.029 (2)	0.0012 (14)	−0.0062 (15)	−0.0130 (16)
C14A	0.022 (2)	0.027 (2)	0.021 (2)	−0.0014 (15)	−0.0082 (16)	−0.0062 (16)
C15A	0.0210 (19)	0.0197 (19)	0.029 (2)	−0.0052 (15)	−0.0059 (16)	−0.0035 (15)
C16A	0.022 (2)	0.026 (2)	0.025 (2)	−0.0033 (15)	−0.0034 (16)	−0.0098 (16)
C17A	0.022 (2)	0.030 (2)	0.025 (2)	−0.0019 (16)	−0.0032 (16)	−0.0084 (16)
C18A	0.021 (2)	0.025 (2)	0.026 (2)	−0.0010 (15)	−0.0059 (16)	−0.0073 (16)
C19A	0.021 (2)	0.026 (2)	0.025 (2)	−0.0035 (15)	−0.0063 (16)	−0.0045 (16)
C20A	0.020 (2)	0.030 (2)	0.028 (2)	−0.0011 (16)	−0.0066 (16)	−0.0077 (16)
C21A	0.024 (2)	0.0225 (19)	0.031 (2)	−0.0004 (15)	−0.0100 (17)	−0.0057 (16)
C22A	0.022 (2)	0.028 (2)	0.026 (2)	−0.0028 (15)	−0.0058 (16)	−0.0092 (16)
C23A	0.021 (2)	0.027 (2)	0.027 (2)	0.0012 (15)	−0.0087 (16)	−0.0061 (16)
C24A	0.026 (2)	0.029 (2)	0.025 (2)	−0.0020 (16)	−0.0028 (16)	−0.0075 (16)
C25A	0.026 (2)	0.030 (2)	0.028 (2)	−0.0037 (16)	−0.0076 (17)	−0.0067 (16)
C26A	0.032 (2)	0.029 (2)	0.026 (2)	−0.0017 (17)	−0.0053 (17)	−0.0075 (16)
C27A	0.040 (3)	0.036 (2)	0.028 (2)	−0.0003 (18)	−0.0104 (19)	−0.0130 (18)
O1B	0.0386 (17)	0.0279 (15)	0.0329 (16)	−0.0060 (12)	−0.0052 (14)	−0.0094 (12)
O2B	0.0291 (15)	0.0265 (14)	0.0324 (15)	−0.0084 (11)	−0.0100 (12)	−0.0040 (12)
O3B	0.0280 (15)	0.0236 (13)	0.0250 (14)	−0.0037 (11)	−0.0058 (11)	−0.0064 (11)
C1B	0.0171 (19)	0.027 (2)	0.032 (2)	−0.0024 (15)	−0.0081 (16)	−0.0070 (17)
C2B	0.029 (2)	0.029 (2)	0.036 (2)	−0.0018 (17)	−0.0062 (18)	−0.0156 (18)
C3B	0.034 (2)	0.040 (2)	0.026 (2)	0.0029 (18)	−0.0060 (18)	−0.0129 (18)
C4B	0.034 (2)	0.027 (2)	0.030 (2)	−0.0030 (17)	−0.0050 (18)	−0.0033 (17)
C5B	0.025 (2)	0.023 (2)	0.030 (2)	0.0008 (15)	−0.0060 (17)	−0.0105 (16)
C6B	0.0127 (18)	0.0245 (19)	0.032 (2)	0.0008 (14)	−0.0059 (16)	−0.0104 (16)
C7B	0.0121 (18)	0.027 (2)	0.029 (2)	−0.0004 (14)	−0.0098 (15)	−0.0060 (16)
C8B	0.0172 (19)	0.0221 (19)	0.031 (2)	−0.0010 (15)	−0.0056 (16)	−0.0068 (16)
C9B	0.0161 (19)	0.0212 (19)	0.028 (2)	−0.0028 (14)	−0.0046 (15)	−0.0053 (15)
C10B	0.0159 (19)	0.025 (2)	0.030 (2)	−0.0054 (15)	−0.0028 (16)	−0.0078 (16)
C11B	0.0180 (19)	0.030 (2)	0.022 (2)	−0.0036 (15)	−0.0038 (15)	−0.0049 (16)
C12B	0.019 (2)	0.026 (2)	0.033 (2)	−0.0031 (15)	−0.0057 (16)	−0.0059 (17)
C13B	0.0152 (19)	0.027 (2)	0.028 (2)	−0.0052 (15)	−0.0021 (15)	−0.0082 (16)
C14B	0.025 (2)	0.029 (2)	0.021 (2)	−0.0026 (16)	−0.0044 (16)	−0.0067 (16)
C15B	0.023 (2)	0.024 (2)	0.030 (2)	−0.0020 (15)	−0.0055 (17)	−0.0046 (16)
C16B	0.0204 (19)	0.026 (2)	0.024 (2)	−0.0050 (15)	−0.0049 (15)	−0.0031 (16)
C17B	0.0174 (19)	0.028 (2)	0.029 (2)	−0.0025 (15)	−0.0041 (16)	−0.0058 (16)
C18B	0.020 (2)	0.027 (2)	0.026 (2)	−0.0006 (15)	−0.0043 (16)	−0.0061 (16)
C19B	0.022 (2)	0.025 (2)	0.027 (2)	−0.0014 (15)	−0.0054 (16)	−0.0034 (16)
C20B	0.0196 (19)	0.025 (2)	0.024 (2)	−0.0023 (15)	−0.0044 (15)	−0.0046 (15)
C21B	0.019 (2)	0.027 (2)	0.028 (2)	−0.0025 (15)	−0.0023 (16)	−0.0061 (16)
C22B	0.021 (2)	0.028 (2)	0.028 (2)	0.0007 (15)	−0.0052 (16)	−0.0069 (16)
C23B	0.024 (2)	0.025 (2)	0.030 (2)	−0.0040 (16)	−0.0052 (17)	−0.0072 (16)
C24B	0.025 (2)	0.027 (2)	0.028 (2)	−0.0034 (16)	−0.0079 (17)	−0.0068 (16)
C25B	0.027 (2)	0.029 (2)	0.028 (2)	−0.0027 (16)	−0.0070 (17)	−0.0079 (16)
C26B	0.030 (2)	0.031 (2)	0.024 (2)	−0.0031 (17)	−0.0047 (17)	−0.0084 (16)
C27B	0.044 (3)	0.035 (2)	0.033 (2)	−0.0091 (19)	−0.006 (2)	−0.0123 (18)

O1A—C1A	1.353 (4)	O1B—C1B	1.345 (4)
O1A—H1A	0.8200	O1B—H1B	0.8200
O2A—C7A	1.251 (4)	O2B—C7B	1.251 (4)
O3A—C13A	1.366 (4)	O3B—C13B	1.361 (4)
O3A—C16A	1.440 (4)	O3B—C16B	1.440 (4)
C1A—C2A	1.396 (5)	C1B—C2B	1.392 (5)
C1A—C6A	1.407 (5)	C1B—C6B	1.410 (5)
C2A—C3A	1.374 (5)	C2B—C3B	1.375 (5)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.388 (5)	C3B—C4B	1.392 (5)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.372 (5)	C4B—C5B	1.366 (5)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.400 (5)	C5B—C6B	1.403 (5)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.484 (5)	C6B—C7B	1.473 (5)
C7A—C8A	1.467 (5)	C7B—C8B	1.470 (5)
C8A—C9A	1.337 (5)	C8B—C9B	1.334 (5)
C8A—H8AA	0.9300	C8B—H8BA	0.9300
C9A—C10A	1.459 (5)	C9B—C10B	1.449 (5)
C9A—H9AA	0.9300	C9B—H9BA	0.9300
C10A—C15A	1.403 (5)	C10B—C15B	1.399 (5)
C10A—C11A	1.404 (5)	C10B—C11B	1.399 (5)
C11A—C12A	1.366 (5)	C11B—C12B	1.370 (5)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.395 (5)	C12B—C13B	1.397 (5)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.387 (5)	C13B—C14B	1.384 (5)
C14A—C15A	1.384 (5)	C14B—C15B	1.389 (5)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—C17A	1.508 (5)	C16B—C17B	1.507 (5)
C16A—H16A	0.9700	C16B—H16C	0.9700
C16A—H16B	0.9700	C16B—H16D	0.9700
C17A—C18A	1.508 (5)	C17B—C18B	1.517 (5)
C17A—H17A	0.9700	C17B—H17C	0.9700
C17A—H17B	0.9700	C17B—H17D	0.9700
C18A—C19A	1.525 (5)	C18B—C19B	1.522 (5)
C18A—H18A	0.9700	C18B—H18C	0.9700
C18A—H18B	0.9700	C18B—H18D	0.9700
C19A—C20A	1.519 (5)	C19B—C20B	1.511 (5)
C19A—H19A	0.9700	C19B—H19C	0.9700
C19A—H19B	0.9700	C19B—H19D	0.9700
C20A—C21A	1.525 (5)	C20B—C21B	1.515 (5)
C20A—H20A	0.9700	C20B—H20C	0.9700
C20A—H20B	0.9700	C20B—H20D	0.9700
C21A—C22A	1.522 (5)	C21B—C22B	1.521 (5)
C21A—H21A	0.9700	C21B—H21C	0.9700
C21A—H21B	0.9700	C21B—H21D	0.9700
C22A—C23A	1.529 (5)	C22B—C23B	1.518 (5)
C22A—H22A	0.9700	C22B—H22C	0.9700
C22A—H22B	0.9700	C22B—H22D	0.9700
C23A—C24A	1.517 (5)	C23B—C24B	1.519 (5)
C23A—H23A	0.9700	C23B—H23C	0.9700
C23A—H23B	0.9700	C23B—H23D	0.9700
C24A—C25A	1.520 (5)	C24B—C25B	1.531 (5)
C24A—H24A	0.9700	C24B—H24C	0.9700
C24A—H24B	0.9700	C24B—H24D	0.9700
C25A—C26A	1.510 (5)	C25B—C26B	1.519 (5)
C25A—H25A	0.9700	C25B—H25C	0.9700
C25A—H25B	0.9700	C25B—H25D	0.9700
C26A—C27A	1.528 (5)	C26B—C27B	1.523 (5)
C26A—H26A	0.9700	C26B—H26C	0.9700
C26A—H26B	0.9700	C26B—H26D	0.9700
C27A—H27A	0.9600	C27B—H27D	0.9600
C27A—H27B	0.9600	C27B—H27E	0.9600
C27A—H27C	0.9600	C27B—H27F	0.9600
C1A—O1A—H1A	109.5	C1B—O1B—H1B	109.5
C13A—O3A—C16A	119.7 (3)	C13B—O3B—C16B	119.3 (3)
O1A—C1A—C2A	117.3 (3)	O1B—C1B—C2B	117.2 (3)
O1A—C1A—C6A	122.7 (3)	O1B—C1B—C6B	122.8 (3)
C2A—C1A—C6A	120.0 (3)	C2B—C1B—C6B	120.0 (3)
C3A—C2A—C1A	119.9 (3)	C3B—C2B—C1B	120.5 (3)
C3A—C2A—H2AA	120.0	C3B—C2B—H2BA	119.7
C1A—C2A—H2AA	120.0	C1B—C2B—H2BA	119.7
C2A—C3A—C4A	120.8 (3)	C2B—C3B—C4B	120.1 (4)
C2A—C3A—H3AA	119.6	C2B—C3B—H3BA	119.9
C4A—C3A—H3AA	119.6	C4B—C3B—H3BA	119.9
C5A—C4A—C3A	119.7 (3)	C5B—C4B—C3B	119.8 (3)
C5A—C4A—H4AA	120.1	C5B—C4B—H4BA	120.1
C3A—C4A—H4AA	120.1	C3B—C4B—H4BA	120.1
C4A—C5A—C6A	121.1 (3)	C4B—C5B—C6B	121.7 (3)
C4A—C5A—H5AA	119.5	C4B—C5B—H5BA	119.2
C6A—C5A—H5AA	119.5	C6B—C5B—H5BA	119.2
C5A—C6A—C1A	118.5 (3)	C5B—C6B—C1B	117.8 (3)
C5A—C6A—C7A	122.4 (3)	C5B—C6B—C7B	123.1 (3)
C1A—C6A—C7A	119.1 (3)	C1B—C6B—C7B	119.1 (3)
O2A—C7A—C8A	119.3 (3)	O2B—C7B—C8B	119.0 (3)
O2A—C7A—C6A	118.8 (3)	O2B—C7B—C6B	119.8 (3)
C8A—C7A—C6A	121.9 (3)	C8B—C7B—C6B	121.2 (3)
C9A—C8A—C7A	119.6 (3)	C9B—C8B—C7B	120.5 (3)
C9A—C8A—H8AA	120.2	C9B—C8B—H8BA	119.7
C7A—C8A—H8AA	120.2	C7B—C8B—H8BA	119.7
C8A—C9A—C10A	129.0 (3)	C8B—C9B—C10B	128.6 (3)
C8A—C9A—H9AA	115.5	C8B—C9B—H9BA	115.7
C10A—C9A—H9AA	115.5	C10B—C9B—H9BA	115.7
C15A—C10A—C11A	117.7 (3)	C15B—C10B—C11B	117.3 (3)
C15A—C10A—C9A	119.3 (3)	C15B—C10B—C9B	119.7 (3)
C11A—C10A—C9A	123.0 (3)	C11B—C10B—C9B	123.0 (3)
C12A—C11A—C10A	120.7 (3)	C12B—C11B—C10B	121.3 (3)
C12A—C11A—H11A	119.6	C12B—C11B—H11B	119.4
C10A—C11A—H11A	119.6	C10B—C11B—H11B	119.4
C11A—C12A—C13A	121.0 (3)	C11B—C12B—C13B	120.5 (3)
C11A—C12A—H12A	119.5	C11B—C12B—H12B	119.8
C13A—C12A—H12A	119.5	C13B—C12B—H12B	119.8
O3A—C13A—C14A	124.9 (3)	O3B—C13B—C14B	125.2 (3)
O3A—C13A—C12A	115.5 (3)	O3B—C13B—C12B	115.0 (3)
C14A—C13A—C12A	119.6 (3)	C14B—C13B—C12B	119.8 (3)
C15A—C14A—C13A	119.4 (3)	C13B—C14B—C15B	119.0 (3)
C15A—C14A—H14A	120.3	C13B—C14B—H14B	120.5
C13A—C14A—H14A	120.3	C15B—C14B—H14B	120.5
C14A—C15A—C10A	121.7 (3)	C14B—C15B—C10B	122.2 (3)
C14A—C15A—H15A	119.1	C14B—C15B—H15B	118.9
C10A—C15A—H15A	119.1	C10B—C15B—H15B	118.9
O3A—C16A—C17A	106.4 (3)	O3B—C16B—C17B	106.2 (3)
O3A—C16A—H16A	110.4	O3B—C16B—H16C	110.5
C17A—C16A—H16A	110.4	C17B—C16B—H16C	110.5
O3A—C16A—H16B	110.4	O3B—C16B—H16D	110.5
C17A—C16A—H16B	110.4	C17B—C16B—H16D	110.5
H16A—C16A—H16B	108.6	H16C—C16B—H16D	108.7
C16A—C17A—C18A	115.6 (3)	C16B—C17B—C18B	114.6 (3)
C16A—C17A—H17A	108.4	C16B—C17B—H17C	108.6
C18A—C17A—H17A	108.4	C18B—C17B—H17C	108.6
C16A—C17A—H17B	108.4	C16B—C17B—H17D	108.6
C18A—C17A—H17B	108.4	C18B—C17B—H17D	108.6
H17A—C17A—H17B	107.4	H17C—C17B—H17D	107.6
C17A—C18A—C19A	111.6 (3)	C17B—C18B—C19B	111.2 (3)
C17A—C18A—H18A	109.3	C17B—C18B—H18C	109.4
C19A—C18A—H18A	109.3	C19B—C18B—H18C	109.4
C17A—C18A—H18B	109.3	C17B—C18B—H18D	109.4
C19A—C18A—H18B	109.3	C19B—C18B—H18D	109.4
H18A—C18A—H18B	108.0	H18C—C18B—H18D	108.0
C20A—C19A—C18A	116.1 (3)	C20B—C19B—C18B	116.2 (3)
C20A—C19A—H19A	108.3	C20B—C19B—H19C	108.2
C18A—C19A—H19A	108.3	C18B—C19B—H19C	108.2
C20A—C19A—H19B	108.3	C20B—C19B—H19D	108.2
C18A—C19A—H19B	108.3	C18B—C19B—H19D	108.2
H19A—C19A—H19B	107.4	H19C—C19B—H19D	107.4
C19A—C20A—C21A	112.7 (3)	C19B—C20B—C21B	112.7 (3)
C19A—C20A—H20A	109.0	C19B—C20B—H20C	109.1
C21A—C20A—H20A	109.0	C21B—C20B—H20C	109.1
C19A—C20A—H20B	109.0	C19B—C20B—H20D	109.1
C21A—C20A—H20B	109.0	C21B—C20B—H20D	109.1
H20A—C20A—H20B	107.8	H20C—C20B—H20D	107.8
C22A—C21A—C20A	114.4 (3)	C20B—C21B—C22B	115.0 (3)
C22A—C21A—H21A	108.6	C20B—C21B—H21C	108.5
C20A—C21A—H21A	108.6	C22B—C21B—H21C	108.5
C22A—C21A—H21B	108.6	C20B—C21B—H21D	108.5
C20A—C21A—H21B	108.6	C22B—C21B—H21D	108.5
H21A—C21A—H21B	107.6	H21C—C21B—H21D	107.5
C21A—C22A—C23A	113.3 (3)	C23B—C22B—C21B	113.7 (3)
C21A—C22A—H22A	108.9	C23B—C22B—H22C	108.8
C23A—C22A—H22A	108.9	C21B—C22B—H22C	108.8
C21A—C22A—H22B	108.9	C23B—C22B—H22D	108.8
C23A—C22A—H22B	108.9	C21B—C22B—H22D	108.8
H22A—C22A—H22B	107.7	H22C—C22B—H22D	107.7
C24A—C23A—C22A	113.7 (3)	C22B—C23B—C24B	114.0 (3)
C24A—C23A—H23A	108.8	C22B—C23B—H23C	108.7
C22A—C23A—H23A	108.8	C24B—C23B—H23C	108.7
C24A—C23A—H23B	108.8	C22B—C23B—H23D	108.7
C22A—C23A—H23B	108.8	C24B—C23B—H23D	108.7
H23A—C23A—H23B	107.7	H23C—C23B—H23D	107.6
C23A—C24A—C25A	113.9 (3)	C23B—C24B—C25B	114.2 (3)
C23A—C24A—H24A	108.8	C23B—C24B—H24C	108.7
C25A—C24A—H24A	108.8	C25B—C24B—H24C	108.7
C23A—C24A—H24B	108.8	C23B—C24B—H24D	108.7
C25A—C24A—H24B	108.8	C25B—C24B—H24D	108.7
H24A—C24A—H24B	107.7	H24C—C24B—H24D	107.6
C26A—C25A—C24A	113.7 (3)	C26B—C25B—C24B	113.7 (3)
C26A—C25A—H25A	108.8	C26B—C25B—H25C	108.8
C24A—C25A—H25A	108.8	C24B—C25B—H25C	108.8
C26A—C25A—H25B	108.8	C26B—C25B—H25D	108.8
C24A—C25A—H25B	108.8	C24B—C25B—H25D	108.8
H25A—C25A—H25B	107.7	H25C—C25B—H25D	107.7
C25A—C26A—C27A	113.5 (3)	C25B—C26B—C27B	113.4 (3)
C25A—C26A—H26A	108.9	C25B—C26B—H26C	108.9
C27A—C26A—H26A	108.9	C27B—C26B—H26C	108.9
C25A—C26A—H26B	108.9	C25B—C26B—H26D	108.9
C27A—C26A—H26B	108.9	C27B—C26B—H26D	108.9
H26A—C26A—H26B	107.7	H26C—C26B—H26D	107.7
C26A—C27A—H27A	109.5	C26B—C27B—H27D	109.5
C26A—C27A—H27B	109.5	C26B—C27B—H27E	109.5
H27A—C27A—H27B	109.5	H27D—C27B—H27E	109.5
C26A—C27A—H27C	109.5	C26B—C27B—H27F	109.5
H27A—C27A—H27C	109.5	H27D—C27B—H27F	109.5
H27B—C27A—H27C	109.5	H27E—C27B—H27F	109.5
O1A—C1A—C2A—C3A	−179.1 (3)	O1B—C1B—C2B—C3B	−179.6 (3)
C6A—C1A—C2A—C3A	0.6 (5)	C6B—C1B—C2B—C3B	−0.7 (5)
C1A—C2A—C3A—C4A	0.8 (6)	C1B—C2B—C3B—C4B	0.7 (6)
C2A—C3A—C4A—C5A	−1.2 (6)	C2B—C3B—C4B—C5B	−0.1 (6)
C3A—C4A—C5A—C6A	0.2 (6)	C3B—C4B—C5B—C6B	−0.6 (6)
C4A—C5A—C6A—C1A	1.2 (5)	C4B—C5B—C6B—C1B	0.6 (5)
C4A—C5A—C6A—C7A	−177.9 (3)	C4B—C5B—C6B—C7B	−179.4 (3)
O1A—C1A—C6A—C5A	178.1 (3)	O1B—C1B—C6B—C5B	178.9 (3)
C2A—C1A—C6A—C5A	−1.5 (5)	C2B—C1B—C6B—C5B	0.1 (5)
O1A—C1A—C6A—C7A	−2.8 (5)	O1B—C1B—C6B—C7B	−1.1 (5)
C2A—C1A—C6A—C7A	177.6 (3)	C2B—C1B—C6B—C7B	180.0 (3)
C5A—C6A—C7A—O2A	178.4 (3)	C5B—C6B—C7B—O2B	175.9 (3)
C1A—C6A—C7A—O2A	−0.7 (5)	C1B—C6B—C7B—O2B	−4.1 (5)
C5A—C6A—C7A—C8A	−2.7 (5)	C5B—C6B—C7B—C8B	−5.4 (5)
C1A—C6A—C7A—C8A	178.2 (3)	C1B—C6B—C7B—C8B	174.7 (3)
O2A—C7A—C8A—C9A	6.5 (5)	O2B—C7B—C8B—C9B	8.8 (5)
C6A—C7A—C8A—C9A	−172.3 (3)	C6B—C7B—C8B—C9B	−169.9 (3)
C7A—C8A—C9A—C10A	179.9 (3)	C7B—C8B—C9B—C10B	−179.7 (3)
C8A—C9A—C10A—C15A	−168.6 (4)	C8B—C9B—C10B—C15B	−169.5 (4)
C8A—C9A—C10A—C11A	13.0 (6)	C8B—C9B—C10B—C11B	10.8 (6)
C15A—C10A—C11A—C12A	0.1 (5)	C15B—C10B—C11B—C12B	−0.2 (5)
C9A—C10A—C11A—C12A	178.5 (3)	C9B—C10B—C11B—C12B	179.5 (3)
C10A—C11A—C12A—C13A	0.2 (5)	C10B—C11B—C12B—C13B	0.3 (5)
C16A—O3A—C13A—C14A	−6.8 (5)	C16B—O3B—C13B—C14B	−12.2 (5)
C16A—O3A—C13A—C12A	173.7 (3)	C16B—O3B—C13B—C12B	168.4 (3)
C11A—C12A—C13A—O3A	179.8 (3)	C11B—C12B—C13B—O3B	178.9 (3)
C11A—C12A—C13A—C14A	0.3 (5)	C11B—C12B—C13B—C14B	−0.5 (5)
O3A—C13A—C14A—C15A	179.5 (3)	O3B—C13B—C14B—C15B	−178.6 (3)
C12A—C13A—C14A—C15A	−1.0 (5)	C12B—C13B—C14B—C15B	0.8 (5)
C13A—C14A—C15A—C10A	1.4 (5)	C13B—C14B—C15B—C10B	−0.7 (5)
C11A—C10A—C15A—C14A	−0.9 (5)	C11B—C10B—C15B—C14B	0.5 (5)
C9A—C10A—C15A—C14A	−179.4 (3)	C9B—C10B—C15B—C14B	−179.2 (3)
C13A—O3A—C16A—C17A	175.0 (3)	C13B—O3B—C16B—C17B	177.5 (3)
O3A—C16A—C17A—C18A	176.8 (3)	O3B—C16B—C17B—C18B	176.5 (3)
C16A—C17A—C18A—C19A	−176.9 (3)	C16B—C17B—C18B—C19B	−178.8 (3)
C17A—C18A—C19A—C20A	−176.2 (3)	C17B—C18B—C19B—C20B	−173.5 (3)
C18A—C19A—C20A—C21A	−179.7 (3)	C18B—C19B—C20B—C21B	−176.4 (3)
C19A—C20A—C21A—C22A	−174.4 (3)	C19B—C20B—C21B—C22B	−174.4 (3)
C20A—C21A—C22A—C23A	175.3 (3)	C20B—C21B—C22B—C23B	177.0 (3)
C21A—C22A—C23A—C24A	−177.5 (3)	C21B—C22B—C23B—C24B	−178.3 (3)
C22A—C23A—C24A—C25A	176.3 (3)	C22B—C23B—C24B—C25B	173.9 (3)
C23A—C24A—C25A—C26A	179.6 (3)	C23B—C24B—C25B—C26B	178.6 (3)
C24A—C25A—C26A—C27A	−179.5 (3)	C24B—C25B—C26B—C27B	−174.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2A	0.82	1.79	2.513 (4)	146
O1B—H1B···O2B	0.82	1.81	2.530 (4)	146
C22B—H22C···Cg1i	0.97	2.77	3.654 (4)	151
C16B—H16D···Cg2i	0.97	3.00	3.736 (4)	134
C17B—H17D···Cg2	0.97	2.82	3.612 (4)	139
C22A—H22B···Cg3	0.97	2.93	3.765 (4)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯O2A	0.82	1.79	2.513 (4)	146
O1B—H1B⋯O2B	0.82	1.81	2.530 (4)	146
C22B—H22C⋯Cg1i	0.97	2.77	3.654 (4)	151
C17B—H17D⋯Cg2	0.97	2.82	3.612 (4)	139
C22A—H22B⋯Cg3	0.97	2.93	3.765 (4)	145

Symmetry code: (i) . Cg1, Cg2 and Cg3 are the centroids of the C1A--C6A, C10A–C15A and C1B–C6B rings, respectively.