(E)-1-(4-Decyl-oxyphen-yl)-3-(4-hydroxy-phen-yl)prop-2-en-1-one.

In the title compound, C(25)H(32)O(3), the asymmetric unit contains two crystallographically independent mol-ecules: both enone groups adopt an s-cis configuration. In the crystal, O-H⋯O and C-H⋯O inter-molecular inter-actions form bifurcated hydrogen bonds, which generate R(1) (2)(6) ring motifs. These inter-molecular inter-actions link the mol-ecules into one-dimensional chains along the [10] direction. The crystal structure is further stabilized by C-H⋯π inter-actions.

Related literature

For general background to the biological properties of chalcone derivatives, see: Bhat et al. (2005 ▶); Xue et al. (2004 ▶); Satyanarayana et al. (2004 ▶); Zhao et al. (2005 ▶); Yayli et al. (2006 ▶). For related structures, see: Ng, Razak et al. (2006 ▶); Ng, Patil et al. (2006 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C25H32O3

M = 380.51

Monoclinic,

a = 12.4437 (2) Å

b = 35.5191 (6) Å

c = 9.8004 (2) Å

β = 99.284 (1)°

V = 4274.93 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.52 × 0.44 × 0.35 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.962, T max = 0.974

62626 measured reflections

16928 independent reflections

12634 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.153

S = 1.04

16928 reflections

515 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.54 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901054X/at2746sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901054X/at2746Isup2.hkl

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

C25H32O3	F(000) = 1648
Mr = 380.51	Dx = 1.182 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9788 reflections
a = 12.4437 (2) Å	θ = 2.4–33.6°
b = 35.5191 (6) Å	µ = 0.08 mm−1
c = 9.8004 (2) Å	T = 100 K
β = 99.284 (1)°	Block, colourless
V = 4274.93 (13) Å3	0.52 × 0.44 × 0.35 mm
Z = 8

Bruker APEXII CCD area-detector diffractometer	16928 independent reflections
Radiation source: sealed tube	12634 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 33.6°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −19→12
Tmin = 0.962, Tmax = 0.974	k = −47→55
62626 measured reflections	l = −15→15

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0694P)2 + 1.5875P] where P = (Fo2 + 2Fc2)/3
16928 reflections	(Δ/σ)max = 0.001
515 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.25 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	0.19648 (7)	−0.12225 (2)	0.96568 (9)	0.02036 (16)
O2A	0.68305 (7)	−0.08504 (2)	0.48100 (9)	0.02114 (16)
O3A	0.86470 (6)	0.07913 (2)	0.43003 (8)	0.01776 (15)
C1A	0.39100 (9)	−0.06947 (3)	0.80269 (10)	0.01565 (18)
H1AA	0.4143	−0.0447	0.7989	0.019*
C2A	0.31110 (9)	−0.07833 (3)	0.88043 (11)	0.01666 (18)
H2AA	0.2810	−0.0595	0.9282	0.020*
C3A	0.27532 (8)	−0.11552 (3)	0.88759 (10)	0.01508 (17)
C4A	0.32006 (9)	−0.14375 (3)	0.81526 (11)	0.01803 (19)
H4AA	0.2966	−0.1685	0.8192	0.022*
C5A	0.39998 (9)	−0.13443 (3)	0.73730 (11)	0.01765 (19)
H5AA	0.4295	−0.1533	0.6890	0.021*
C6A	0.43747 (8)	−0.09747 (3)	0.72928 (10)	0.01372 (17)
C7A	0.52133 (8)	−0.09029 (3)	0.64537 (10)	0.01487 (17)
H7AA	0.5451	−0.1111	0.6011	0.018*
C8A	0.56916 (8)	−0.05727 (3)	0.62344 (10)	0.01469 (17)
H8AA	0.5488	−0.0353	0.6644	0.018*
C9A	0.65358 (8)	−0.05601 (3)	0.53460 (10)	0.01421 (17)
C10A	0.70600 (8)	−0.01986 (3)	0.50805 (10)	0.01370 (17)
C11A	0.79143 (9)	−0.02091 (3)	0.43098 (11)	0.01715 (19)
H11A	0.8116	−0.0439	0.3977	0.021*
C12A	0.84675 (9)	0.01122 (3)	0.40270 (11)	0.01749 (19)
H12A	0.9038	0.0097	0.3522	0.021*
C13A	0.81582 (8)	0.04600 (3)	0.45113 (10)	0.01456 (17)
C14A	0.72985 (8)	0.04794 (3)	0.52714 (11)	0.01556 (18)
H14A	0.7089	0.0711	0.5588	0.019*
C15A	0.67605 (8)	0.01542 (3)	0.55516 (10)	0.01479 (17)
H15A	0.6192	0.0169	0.6059	0.018*
C16A	0.95178 (9)	0.07828 (3)	0.34939 (11)	0.01798 (19)
H16A	0.9254	0.0681	0.2583	0.022*
H16B	1.0102	0.0623	0.3940	0.022*
C17A	0.99332 (9)	0.11775 (3)	0.33678 (11)	0.01747 (19)
H17A	1.0190	0.1279	0.4281	0.021*
H17B	0.9347	0.1337	0.2921	0.021*
C18A	1.08613 (9)	0.11765 (3)	0.25216 (12)	0.0205 (2)
H18A	1.1456	0.1027	0.3004	0.025*
H18B	1.0610	0.1056	0.1640	0.025*
C19A	1.12904 (9)	0.15667 (3)	0.22545 (11)	0.01802 (19)
H19A	1.1530	0.1691	0.3132	0.022*
H19B	1.0705	0.1715	0.1744	0.022*
C20A	1.22377 (9)	0.15512 (3)	0.14381 (12)	0.0193 (2)
H20A	1.2836	0.1415	0.1975	0.023*
H20B	1.2009	0.1412	0.0588	0.023*
C21A	1.26404 (9)	0.19380 (3)	0.10818 (11)	0.01678 (18)
H21A	1.2887	0.2074	0.1932	0.020*
H21B	1.2037	0.2077	0.0565	0.020*
C22A	1.35682 (9)	0.19220 (3)	0.02342 (11)	0.01782 (19)
H22A	1.4177	0.1788	0.0759	0.021*
H22B	1.3327	0.1781	−0.0607	0.021*
C23A	1.39557 (9)	0.23103 (3)	−0.01474 (11)	0.01709 (18)
H23A	1.3347	0.2443	−0.0680	0.021*
H23B	1.4185	0.2452	0.0695	0.021*
C24A	1.48909 (10)	0.23004 (3)	−0.09762 (13)	0.0224 (2)
H24A	1.4664	0.2162	−0.1827	0.027*
H24B	1.5503	0.2168	−0.0449	0.027*
C25A	1.52534 (10)	0.26954 (3)	−0.13242 (13)	0.0231 (2)
H25A	1.5845	0.2677	−0.1840	0.035*
H25B	1.5488	0.2832	−0.0484	0.035*
H25C	1.4655	0.2825	−0.1867	0.035*
O1B	1.31221 (7)	0.33893 (2)	0.04708 (9)	0.02207 (17)
O2B	0.84313 (8)	0.30275 (2)	0.55634 (10)	0.0293 (2)
O3B	0.68508 (7)	0.13810 (2)	0.65982 (8)	0.01930 (16)
C1B	1.12915 (9)	0.28531 (3)	0.22651 (12)	0.0189 (2)
H1BA	1.1138	0.2602	0.2417	0.023*
C2B	1.20746 (10)	0.29428 (3)	0.14624 (12)	0.0208 (2)
H2BA	1.2436	0.2752	0.1071	0.025*
C3B	1.23247 (9)	0.33191 (3)	0.12373 (11)	0.01589 (18)
C4B	1.17622 (9)	0.36043 (3)	0.17965 (11)	0.01771 (19)
H4BA	1.1914	0.3856	0.1640	0.021*
C5B	1.09736 (9)	0.35102 (3)	0.25890 (11)	0.01814 (19)
H5BA	1.0598	0.3702	0.2956	0.022*
C6B	1.07262 (8)	0.31357 (3)	0.28527 (11)	0.01511 (18)
C7B	0.99147 (9)	0.30651 (3)	0.37343 (11)	0.01700 (19)
H7BA	0.9566	0.3278	0.4005	0.020*
C8B	0.95974 (9)	0.27355 (3)	0.42135 (11)	0.01687 (18)
H8BA	0.9904	0.2511	0.3971	0.020*
C9B	0.87663 (9)	0.27302 (3)	0.51200 (11)	0.01733 (19)
C10B	0.83094 (8)	0.23694 (3)	0.55219 (11)	0.01535 (18)
C11B	0.75851 (9)	0.23806 (3)	0.64765 (11)	0.01700 (19)
H11B	0.7433	0.2611	0.6854	0.020*
C12B	0.70886 (9)	0.20588 (3)	0.68738 (11)	0.01700 (19)
H12B	0.6610	0.2073	0.7509	0.020*
C13B	0.73143 (8)	0.17123 (3)	0.63101 (10)	0.01518 (17)
C14B	0.80510 (9)	0.16922 (3)	0.53728 (12)	0.0188 (2)
H14B	0.8212	0.1461	0.5011	0.023*
C15B	0.85396 (9)	0.20172 (3)	0.49851 (11)	0.01832 (19)
H15B	0.9027	0.2002	0.4361	0.022*
C16B	0.60126 (9)	0.13979 (3)	0.74562 (11)	0.01719 (19)
H16C	0.5419	0.1556	0.7026	0.021*
H16D	0.6305	0.1504	0.8351	0.021*
C17B	0.56056 (9)	0.10029 (3)	0.76309 (11)	0.01687 (18)
H17C	0.6200	0.0848	0.8081	0.020*
H17D	0.5342	0.0895	0.6730	0.020*
C18B	0.46876 (9)	0.10052 (3)	0.84962 (11)	0.01672 (18)
H18C	0.4952	0.1120	0.9384	0.020*
H18D	0.4094	0.1159	0.8033	0.020*
C19B	0.42533 (9)	0.06142 (3)	0.87367 (11)	0.01718 (19)
H19C	0.4847	0.0459	0.9189	0.021*
H19D	0.3977	0.0500	0.7850	0.021*
C20B	0.33482 (9)	0.06196 (3)	0.96191 (11)	0.01738 (19)
H20C	0.3617	0.0742	1.0492	0.021*
H20D	0.2745	0.0768	0.9151	0.021*
C21B	0.29339 (9)	0.02284 (3)	0.99067 (11)	0.01762 (19)
H21C	0.3540	0.0080	1.0364	0.021*
H21D	0.2660	0.0108	0.9032	0.021*
C22B	0.20355 (8)	0.02275 (3)	1.08003 (11)	0.01643 (18)
H22C	0.2313	0.0342	1.1686	0.020*
H22D	0.1434	0.0381	1.0356	0.020*
C23B	0.16144 (8)	−0.01652 (3)	1.10443 (11)	0.01573 (18)
H23C	0.2216	−0.0317	1.1498	0.019*
H23D	0.1349	−0.0280	1.0156	0.019*
C24B	0.07056 (9)	−0.01719 (3)	1.19178 (11)	0.01754 (19)
H24C	0.0101	−0.0020	1.1471	0.021*
H24D	0.0969	−0.0061	1.2814	0.021*
C25B	0.03045 (10)	−0.05710 (3)	1.21225 (13)	0.0231 (2)
H25D	−0.0276	−0.0562	1.2659	0.035*
H25E	0.0893	−0.0719	1.2599	0.035*
H25F	0.0044	−0.0682	1.1238	0.035*
H1OB	1.3164 (14)	0.3643 (6)	0.0362 (19)	0.044 (5)*
H1OA	0.1825 (15)	−0.1475 (6)	0.9592 (19)	0.046 (5)*

	U11	U22	U33	U12	U13	U23
O1A	0.0220 (4)	0.0178 (4)	0.0250 (4)	−0.0022 (3)	0.0151 (3)	0.0001 (3)
O2A	0.0248 (4)	0.0131 (3)	0.0295 (4)	−0.0007 (3)	0.0166 (3)	−0.0028 (3)
O3A	0.0201 (4)	0.0131 (3)	0.0229 (4)	−0.0027 (3)	0.0118 (3)	0.0005 (3)
C1A	0.0186 (5)	0.0123 (4)	0.0176 (4)	−0.0009 (3)	0.0077 (3)	−0.0004 (3)
C2A	0.0197 (5)	0.0134 (4)	0.0190 (4)	−0.0003 (3)	0.0092 (4)	−0.0017 (3)
C3A	0.0146 (4)	0.0154 (4)	0.0167 (4)	−0.0003 (3)	0.0069 (3)	0.0011 (3)
C4A	0.0206 (5)	0.0126 (4)	0.0236 (5)	−0.0017 (4)	0.0117 (4)	−0.0001 (3)
C5A	0.0205 (5)	0.0129 (4)	0.0220 (5)	−0.0003 (3)	0.0110 (4)	−0.0012 (3)
C6A	0.0145 (4)	0.0126 (4)	0.0153 (4)	−0.0003 (3)	0.0060 (3)	0.0004 (3)
C7A	0.0152 (4)	0.0143 (4)	0.0164 (4)	0.0003 (3)	0.0065 (3)	0.0003 (3)
C8A	0.0154 (4)	0.0138 (4)	0.0163 (4)	−0.0005 (3)	0.0068 (3)	−0.0009 (3)
C9A	0.0143 (4)	0.0133 (4)	0.0161 (4)	−0.0003 (3)	0.0055 (3)	0.0004 (3)
C10A	0.0147 (4)	0.0124 (4)	0.0152 (4)	−0.0002 (3)	0.0059 (3)	0.0001 (3)
C11A	0.0191 (5)	0.0135 (4)	0.0212 (5)	−0.0007 (3)	0.0102 (4)	−0.0018 (3)
C12A	0.0187 (5)	0.0148 (4)	0.0217 (5)	−0.0015 (4)	0.0116 (4)	−0.0006 (3)
C13A	0.0154 (4)	0.0133 (4)	0.0159 (4)	−0.0012 (3)	0.0055 (3)	0.0012 (3)
C14A	0.0166 (5)	0.0132 (4)	0.0183 (4)	0.0004 (3)	0.0068 (3)	−0.0004 (3)
C15A	0.0144 (4)	0.0148 (4)	0.0168 (4)	0.0001 (3)	0.0073 (3)	0.0005 (3)
C16A	0.0175 (5)	0.0161 (5)	0.0226 (5)	−0.0013 (4)	0.0103 (4)	0.0016 (4)
C17A	0.0176 (5)	0.0155 (4)	0.0208 (5)	−0.0024 (3)	0.0075 (4)	0.0011 (3)
C18A	0.0191 (5)	0.0165 (5)	0.0284 (5)	−0.0011 (4)	0.0117 (4)	0.0028 (4)
C19A	0.0189 (5)	0.0161 (5)	0.0207 (5)	−0.0016 (4)	0.0082 (4)	0.0020 (3)
C20A	0.0199 (5)	0.0159 (5)	0.0242 (5)	−0.0016 (4)	0.0098 (4)	0.0026 (4)
C21A	0.0163 (5)	0.0162 (4)	0.0192 (4)	−0.0021 (3)	0.0070 (4)	0.0004 (3)
C22A	0.0181 (5)	0.0165 (5)	0.0208 (5)	−0.0016 (4)	0.0087 (4)	0.0004 (3)
C23A	0.0176 (5)	0.0163 (4)	0.0192 (4)	−0.0012 (3)	0.0087 (4)	0.0000 (3)
C24A	0.0220 (5)	0.0189 (5)	0.0300 (6)	0.0005 (4)	0.0152 (4)	0.0025 (4)
C25A	0.0214 (5)	0.0216 (5)	0.0282 (5)	−0.0036 (4)	0.0100 (4)	0.0036 (4)
O1B	0.0255 (4)	0.0154 (4)	0.0301 (4)	−0.0002 (3)	0.0187 (3)	0.0018 (3)
O2B	0.0372 (5)	0.0137 (4)	0.0445 (5)	−0.0007 (3)	0.0292 (4)	−0.0017 (3)
O3B	0.0230 (4)	0.0129 (3)	0.0256 (4)	−0.0035 (3)	0.0146 (3)	−0.0003 (3)
C1B	0.0219 (5)	0.0120 (4)	0.0257 (5)	−0.0013 (4)	0.0129 (4)	−0.0010 (4)
C2B	0.0260 (6)	0.0131 (4)	0.0271 (5)	0.0005 (4)	0.0161 (4)	−0.0015 (4)
C3B	0.0169 (5)	0.0143 (4)	0.0185 (4)	−0.0004 (3)	0.0089 (3)	0.0005 (3)
C4B	0.0208 (5)	0.0118 (4)	0.0230 (5)	0.0006 (3)	0.0109 (4)	0.0015 (3)
C5B	0.0205 (5)	0.0123 (4)	0.0243 (5)	0.0012 (3)	0.0116 (4)	0.0011 (3)
C6B	0.0143 (4)	0.0137 (4)	0.0187 (4)	0.0002 (3)	0.0070 (3)	0.0008 (3)
C7B	0.0168 (5)	0.0149 (4)	0.0211 (5)	0.0001 (3)	0.0087 (4)	0.0001 (3)
C8B	0.0163 (5)	0.0143 (4)	0.0220 (5)	−0.0012 (3)	0.0090 (4)	−0.0010 (3)
C9B	0.0176 (5)	0.0147 (4)	0.0219 (5)	−0.0008 (3)	0.0099 (4)	−0.0003 (3)
C10B	0.0149 (4)	0.0137 (4)	0.0191 (4)	−0.0014 (3)	0.0076 (3)	−0.0001 (3)
C11B	0.0184 (5)	0.0137 (4)	0.0213 (5)	−0.0017 (3)	0.0103 (4)	−0.0019 (3)
C12B	0.0183 (5)	0.0154 (4)	0.0199 (4)	−0.0022 (3)	0.0108 (4)	−0.0008 (3)
C13B	0.0158 (4)	0.0131 (4)	0.0180 (4)	−0.0017 (3)	0.0066 (3)	0.0008 (3)
C14B	0.0214 (5)	0.0132 (4)	0.0248 (5)	−0.0012 (4)	0.0122 (4)	−0.0022 (4)
C15B	0.0199 (5)	0.0148 (4)	0.0233 (5)	−0.0014 (4)	0.0126 (4)	−0.0009 (4)
C16B	0.0186 (5)	0.0155 (4)	0.0198 (4)	−0.0022 (4)	0.0101 (4)	0.0006 (3)
C17B	0.0191 (5)	0.0141 (4)	0.0193 (4)	−0.0024 (3)	0.0087 (4)	0.0013 (3)
C18B	0.0179 (5)	0.0144 (4)	0.0190 (4)	−0.0015 (3)	0.0065 (4)	0.0015 (3)
C19B	0.0195 (5)	0.0152 (4)	0.0183 (4)	−0.0030 (4)	0.0075 (4)	−0.0003 (3)
C20B	0.0191 (5)	0.0147 (4)	0.0199 (4)	−0.0017 (4)	0.0080 (4)	0.0011 (3)
C21B	0.0200 (5)	0.0148 (4)	0.0199 (4)	−0.0023 (4)	0.0086 (4)	0.0008 (3)
C22B	0.0164 (5)	0.0157 (4)	0.0185 (4)	−0.0017 (3)	0.0067 (3)	0.0008 (3)
C23B	0.0166 (4)	0.0143 (4)	0.0178 (4)	−0.0006 (3)	0.0070 (3)	0.0004 (3)
C24B	0.0174 (5)	0.0171 (5)	0.0199 (5)	−0.0013 (4)	0.0083 (4)	0.0011 (3)
C25B	0.0227 (5)	0.0211 (5)	0.0273 (5)	−0.0056 (4)	0.0094 (4)	0.0019 (4)

O1A—C3A	1.3592 (12)	O1B—C3B	1.3607 (12)
O1A—H1OA	0.92 (2)	O1B—H1OB	0.91 (2)
O2A—C9A	1.2396 (12)	O2B—C9B	1.2396 (13)
O3A—C13A	1.3559 (12)	O3B—C13B	1.3600 (12)
O3A—C16A	1.4407 (12)	O3B—C16B	1.4427 (12)
C1A—C2A	1.3829 (14)	C1B—C2B	1.3848 (14)
C1A—C6A	1.4054 (14)	C1B—C6B	1.4016 (14)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.3995 (14)	C2B—C3B	1.3980 (14)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.3946 (14)	C3B—C4B	1.3928 (14)
C4A—C5A	1.3884 (14)	C4B—C5B	1.3871 (14)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.3998 (14)	C5B—C6B	1.3989 (14)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.4516 (13)	C6B—C7B	1.4527 (14)
C7A—C8A	1.3480 (14)	C7B—C8B	1.3445 (14)
C7A—H7AA	0.9300	C7B—H7BA	0.9300
C8A—C9A	1.4693 (13)	C8B—C9B	1.4681 (14)
C8A—H8AA	0.9300	C8B—H8BA	0.9300
C9A—C10A	1.4821 (14)	C9B—C10B	1.4810 (14)
C10A—C11A	1.4004 (13)	C10B—C11B	1.4005 (14)
C10A—C15A	1.4062 (14)	C10B—C15B	1.4044 (14)
C11A—C12A	1.3837 (14)	C11B—C12B	1.3848 (14)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.3994 (14)	C12B—C13B	1.3958 (14)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.4005 (14)	C13B—C14B	1.4004 (14)
C14A—C15A	1.3846 (14)	C14B—C15B	1.3860 (15)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—C17A	1.5060 (14)	C16B—C17B	1.5106 (14)
C16A—H16A	0.9700	C16B—H16C	0.9700
C16A—H16B	0.9700	C16B—H16D	0.9700
C17A—C18A	1.5266 (15)	C17B—C18B	1.5286 (14)
C17A—H17A	0.9700	C17B—H17C	0.9700
C17A—H17B	0.9700	C17B—H17D	0.9700
C18A—C19A	1.5231 (15)	C18B—C19B	1.5224 (14)
C18A—H18A	0.9700	C18B—H18C	0.9700
C18A—H18B	0.9700	C18B—H18D	0.9700
C19A—C20A	1.5287 (15)	C19B—C20B	1.5267 (14)
C19A—H19A	0.9700	C19B—H19C	0.9700
C19A—H19B	0.9700	C19B—H19D	0.9700
C20A—C21A	1.5223 (14)	C20B—C21B	1.5239 (14)
C20A—H20A	0.9700	C20B—H20C	0.9700
C20A—H20B	0.9700	C20B—H20D	0.9700
C21A—C22A	1.5282 (14)	C21B—C22B	1.5272 (14)
C21A—H21A	0.9700	C21B—H21C	0.9700
C21A—H21B	0.9700	C21B—H21D	0.9700
C22A—C23A	1.5272 (15)	C22B—C23B	1.5223 (14)
C22A—H22A	0.9700	C22B—H22C	0.9700
C22A—H22B	0.9700	C22B—H22D	0.9700
C23A—C24A	1.5232 (14)	C23B—C24B	1.5247 (14)
C23A—H23A	0.9700	C23B—H23C	0.9700
C23A—H23B	0.9700	C23B—H23D	0.9700
C24A—C25A	1.5291 (16)	C24B—C25B	1.5269 (15)
C24A—H24A	0.9700	C24B—H24C	0.9700
C24A—H24B	0.9700	C24B—H24D	0.9700
C25A—H25A	0.9600	C25B—H25D	0.9600
C25A—H25B	0.9600	C25B—H25E	0.9600
C25A—H25C	0.9600	C25B—H25F	0.9600
C3A—O1A—H1OA	106.3 (11)	C3B—O1B—H1OB	107.9 (11)
C13A—O3A—C16A	117.46 (8)	C13B—O3B—C16B	117.12 (8)
C2A—C1A—C6A	120.85 (9)	C2B—C1B—C6B	120.96 (10)
C2A—C1A—H1AA	119.6	C2B—C1B—H1BA	119.5
C6A—C1A—H1AA	119.6	C6B—C1B—H1BA	119.5
C1A—C2A—C3A	120.35 (9)	C1B—C2B—C3B	120.31 (10)
C1A—C2A—H2AA	119.8	C1B—C2B—H2BA	119.8
C3A—C2A—H2AA	119.8	C3B—C2B—H2BA	119.8
O1A—C3A—C4A	122.92 (9)	O1B—C3B—C4B	122.79 (9)
O1A—C3A—C2A	117.29 (9)	O1B—C3B—C2B	117.58 (9)
C4A—C3A—C2A	119.79 (9)	C4B—C3B—C2B	119.64 (9)
C5A—C4A—C3A	119.24 (9)	C5B—C4B—C3B	119.39 (9)
C5A—C4A—H4AA	120.4	C5B—C4B—H4BA	120.3
C3A—C4A—H4AA	120.4	C3B—C4B—H4BA	120.3
C4A—C5A—C6A	121.95 (9)	C4B—C5B—C6B	121.96 (9)
C4A—C5A—H5AA	119.0	C4B—C5B—H5BA	119.0
C6A—C5A—H5AA	119.0	C6B—C5B—H5BA	119.0
C5A—C6A—C1A	117.82 (9)	C5B—C6B—C1B	117.72 (9)
C5A—C6A—C7A	118.24 (9)	C5B—C6B—C7B	117.95 (9)
C1A—C6A—C7A	123.94 (9)	C1B—C6B—C7B	124.33 (9)
C8A—C7A—C6A	128.28 (9)	C8B—C7B—C6B	129.01 (10)
C8A—C7A—H7AA	115.9	C8B—C7B—H7BA	115.5
C6A—C7A—H7AA	115.9	C6B—C7B—H7BA	115.5
C7A—C8A—C9A	119.82 (9)	C7B—C8B—C9B	119.85 (9)
C7A—C8A—H8AA	120.1	C7B—C8B—H8BA	120.1
C9A—C8A—H8AA	120.1	C9B—C8B—H8BA	120.1
O2A—C9A—C8A	120.96 (9)	O2B—C9B—C8B	120.72 (9)
O2A—C9A—C10A	118.54 (9)	O2B—C9B—C10B	118.61 (9)
C8A—C9A—C10A	120.49 (8)	C8B—C9B—C10B	120.67 (9)
C11A—C10A—C15A	117.73 (9)	C11B—C10B—C15B	117.89 (9)
C11A—C10A—C9A	117.74 (9)	C11B—C10B—C9B	117.97 (9)
C15A—C10A—C9A	124.53 (9)	C15B—C10B—C9B	124.13 (9)
C12A—C11A—C10A	122.10 (9)	C12B—C11B—C10B	121.92 (9)
C12A—C11A—H11A	118.9	C12B—C11B—H11B	119.0
C10A—C11A—H11A	118.9	C10B—C11B—H11B	119.0
C11A—C12A—C13A	119.16 (9)	C11B—C12B—C13B	119.28 (9)
C11A—C12A—H12A	120.4	C11B—C12B—H12B	120.4
C13A—C12A—H12A	120.4	C13B—C12B—H12B	120.4
O3A—C13A—C12A	124.04 (9)	O3B—C13B—C12B	124.16 (9)
O3A—C13A—C14A	116.00 (9)	O3B—C13B—C14B	115.87 (9)
C12A—C13A—C14A	119.96 (9)	C12B—C13B—C14B	119.97 (9)
C15A—C14A—C13A	119.97 (9)	C15B—C14B—C13B	119.99 (9)
C15A—C14A—H14A	120.0	C15B—C14B—H14B	120.0
C13A—C14A—H14A	120.0	C13B—C14B—H14B	120.0
C14A—C15A—C10A	121.07 (9)	C14B—C15B—C10B	120.94 (9)
C14A—C15A—H15A	119.5	C14B—C15B—H15B	119.5
C10A—C15A—H15A	119.5	C10B—C15B—H15B	119.5
O3A—C16A—C17A	108.91 (8)	O3B—C16B—C17B	108.34 (8)
O3A—C16A—H16A	109.9	O3B—C16B—H16C	110.0
C17A—C16A—H16A	109.9	C17B—C16B—H16C	110.0
O3A—C16A—H16B	109.9	O3B—C16B—H16D	110.0
C17A—C16A—H16B	109.9	C17B—C16B—H16D	110.0
H16A—C16A—H16B	108.3	H16C—C16B—H16D	108.4
C16A—C17A—C18A	110.01 (9)	C16B—C17B—C18B	110.62 (8)
C16A—C17A—H17A	109.7	C16B—C17B—H17C	109.5
C18A—C17A—H17A	109.7	C18B—C17B—H17C	109.5
C16A—C17A—H17B	109.7	C16B—C17B—H17D	109.5
C18A—C17A—H17B	109.7	C18B—C17B—H17D	109.5
H17A—C17A—H17B	108.2	H17C—C17B—H17D	108.1
C19A—C18A—C17A	114.09 (9)	C19B—C18B—C17B	113.38 (9)
C19A—C18A—H18A	108.7	C19B—C18B—H18C	108.9
C17A—C18A—H18A	108.7	C17B—C18B—H18C	108.9
C19A—C18A—H18B	108.7	C19B—C18B—H18D	108.9
C17A—C18A—H18B	108.7	C17B—C18B—H18D	108.9
H18A—C18A—H18B	107.6	H18C—C18B—H18D	107.7
C18A—C19A—C20A	112.24 (9)	C18B—C19B—C20B	112.89 (9)
C18A—C19A—H19A	109.2	C18B—C19B—H19C	109.0
C20A—C19A—H19A	109.2	C20B—C19B—H19C	109.0
C18A—C19A—H19B	109.2	C18B—C19B—H19D	109.0
C20A—C19A—H19B	109.2	C20B—C19B—H19D	109.0
H19A—C19A—H19B	107.9	H19C—C19B—H19D	107.8
C21A—C20A—C19A	113.43 (9)	C21B—C20B—C19B	113.32 (9)
C21A—C20A—H20A	108.9	C21B—C20B—H20C	108.9
C19A—C20A—H20A	108.9	C19B—C20B—H20C	108.9
C21A—C20A—H20B	108.9	C21B—C20B—H20D	108.9
C19A—C20A—H20B	108.9	C19B—C20B—H20D	108.9
H20A—C20A—H20B	107.7	H20C—C20B—H20D	107.7
C20A—C21A—C22A	113.37 (9)	C20B—C21B—C22B	114.14 (9)
C20A—C21A—H21A	108.9	C20B—C21B—H21C	108.7
C22A—C21A—H21A	108.9	C22B—C21B—H21C	108.7
C20A—C21A—H21B	108.9	C20B—C21B—H21D	108.7
C22A—C21A—H21B	108.9	C22B—C21B—H21D	108.7
H21A—C21A—H21B	107.7	H21C—C21B—H21D	107.6
C23A—C22A—C21A	113.31 (9)	C23B—C22B—C21B	113.23 (8)
C23A—C22A—H22A	108.9	C23B—C22B—H22C	108.9
C21A—C22A—H22A	108.9	C21B—C22B—H22C	108.9
C23A—C22A—H22B	108.9	C23B—C22B—H22D	108.9
C21A—C22A—H22B	108.9	C21B—C22B—H22D	108.9
H22A—C22A—H22B	107.7	H22C—C22B—H22D	107.7
C24A—C23A—C22A	114.10 (9)	C22B—C23B—C24B	114.07 (8)
C24A—C23A—H23A	108.7	C22B—C23B—H23C	108.7
C22A—C23A—H23A	108.7	C24B—C23B—H23C	108.7
C24A—C23A—H23B	108.7	C22B—C23B—H23D	108.7
C22A—C23A—H23B	108.7	C24B—C23B—H23D	108.7
H23A—C23A—H23B	107.6	H23C—C23B—H23D	107.6
C23A—C24A—C25A	112.09 (9)	C23B—C24B—C25B	112.09 (9)
C23A—C24A—H24A	109.2	C23B—C24B—H24C	109.2
C25A—C24A—H24A	109.2	C25B—C24B—H24C	109.2
C23A—C24A—H24B	109.2	C23B—C24B—H24D	109.2
C25A—C24A—H24B	109.2	C25B—C24B—H24D	109.2
H24A—C24A—H24B	107.9	H24C—C24B—H24D	107.9
C24A—C25A—H25A	109.5	C24B—C25B—H25D	109.5
C24A—C25A—H25B	109.5	C24B—C25B—H25E	109.5
H25A—C25A—H25B	109.5	H25D—C25B—H25E	109.5
C24A—C25A—H25C	109.5	C24B—C25B—H25F	109.5
H25A—C25A—H25C	109.5	H25D—C25B—H25F	109.5
H25B—C25A—H25C	109.5	H25E—C25B—H25F	109.5
C6A—C1A—C2A—C3A	0.19 (16)	C6B—C1B—C2B—C3B	0.77 (18)
C1A—C2A—C3A—O1A	−179.91 (10)	C1B—C2B—C3B—O1B	178.25 (11)
C1A—C2A—C3A—C4A	−0.38 (16)	C1B—C2B—C3B—C4B	−1.61 (17)
O1A—C3A—C4A—C5A	179.69 (10)	O1B—C3B—C4B—C5B	−178.78 (10)
C2A—C3A—C4A—C5A	0.18 (16)	C2B—C3B—C4B—C5B	1.07 (17)
C3A—C4A—C5A—C6A	0.20 (17)	C3B—C4B—C5B—C6B	0.31 (17)
C4A—C5A—C6A—C1A	−0.38 (16)	C4B—C5B—C6B—C1B	−1.13 (17)
C4A—C5A—C6A—C7A	179.95 (10)	C4B—C5B—C6B—C7B	177.88 (10)
C2A—C1A—C6A—C5A	0.18 (15)	C2B—C1B—C6B—C5B	0.58 (17)
C2A—C1A—C6A—C7A	179.83 (10)	C2B—C1B—C6B—C7B	−178.35 (11)
C5A—C6A—C7A—C8A	−179.76 (11)	C5B—C6B—C7B—C8B	−174.80 (11)
C1A—C6A—C7A—C8A	0.58 (17)	C1B—C6B—C7B—C8B	4.13 (19)
C6A—C7A—C8A—C9A	179.70 (10)	C6B—C7B—C8B—C9B	178.96 (10)
C7A—C8A—C9A—O2A	−1.22 (16)	C7B—C8B—C9B—O2B	−7.31 (17)
C7A—C8A—C9A—C10A	179.25 (9)	C7B—C8B—C9B—C10B	172.58 (10)
O2A—C9A—C10A—C11A	−4.18 (15)	O2B—C9B—C10B—C11B	−5.15 (16)
C8A—C9A—C10A—C11A	175.37 (9)	C8B—C9B—C10B—C11B	174.95 (10)
O2A—C9A—C10A—C15A	175.97 (10)	O2B—C9B—C10B—C15B	173.51 (11)
C8A—C9A—C10A—C15A	−4.49 (15)	C8B—C9B—C10B—C15B	−6.39 (17)
C15A—C10A—C11A—C12A	0.99 (16)	C15B—C10B—C11B—C12B	−1.09 (16)
C9A—C10A—C11A—C12A	−178.88 (10)	C9B—C10B—C11B—C12B	177.65 (10)
C10A—C11A—C12A—C13A	−0.74 (17)	C10B—C11B—C12B—C13B	0.02 (17)
C16A—O3A—C13A—C12A	1.79 (15)	C16B—O3B—C13B—C12B	5.06 (15)
C16A—O3A—C13A—C14A	−178.55 (9)	C16B—O3B—C13B—C14B	−174.26 (9)
C11A—C12A—C13A—O3A	179.64 (10)	C11B—C12B—C13B—O3B	−178.14 (10)
C11A—C12A—C13A—C14A	0.00 (16)	C11B—C12B—C13B—C14B	1.16 (16)
O3A—C13A—C14A—C15A	−179.21 (9)	O3B—C13B—C14B—C15B	178.11 (10)
C12A—C13A—C14A—C15A	0.47 (16)	C12B—C13B—C14B—C15B	−1.24 (17)
C13A—C14A—C15A—C10A	−0.21 (16)	C13B—C14B—C15B—C10B	0.14 (17)
C11A—C10A—C15A—C14A	−0.50 (15)	C11B—C10B—C15B—C14B	1.00 (16)
C9A—C10A—C15A—C14A	179.35 (10)	C9B—C10B—C15B—C14B	−177.66 (11)
C13A—O3A—C16A—C17A	179.19 (9)	C13B—O3B—C16B—C17B	179.40 (9)
O3A—C16A—C17A—C18A	179.77 (9)	O3B—C16B—C17B—C18B	−178.19 (8)
C16A—C17A—C18A—C19A	176.24 (10)	C16B—C17B—C18B—C19B	−178.88 (9)
C17A—C18A—C19A—C20A	178.47 (9)	C17B—C18B—C19B—C20B	179.18 (9)
C18A—C19A—C20A—C21A	176.60 (9)	C18B—C19B—C20B—C21B	−178.06 (9)
C19A—C20A—C21A—C22A	−178.54 (9)	C19B—C20B—C21B—C22B	179.42 (9)
C20A—C21A—C22A—C23A	178.83 (9)	C20B—C21B—C22B—C23B	178.56 (9)
C21A—C22A—C23A—C24A	179.22 (9)	C21B—C22B—C23B—C24B	−179.19 (9)
C22A—C23A—C24A—C25A	−179.64 (10)	C22B—C23B—C24B—C25B	179.50 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1OA···O2Bi	0.91 (2)	1.80 (2)	2.711 (1)	179 (3)
O1B—H1OB···O2Aii	0.91 (2)	1.81 (2)	2.716 (1)	176 (2)
C4A—H4AA···O2Bi	0.93	2.50	3.185 (1)	131
C4B—H4BA···O2Aii	0.93	2.50	3.192 (1)	131
C14B—H14B···O3A	0.93	2.56	3.485 (1)	173
C18B—H18C···Cg1iii	0.97	2.85	3.696 (1)	146
C24B—H24D···Cg2iii	0.97	2.71	3.554 (1)	145
C22A—H22B···Cg3iv	0.97	2.95	3.743 (1)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1OA⋯O2Bi	0.91 (2)	1.80 (2)	2.711 (1)	179 (3)
O1B—H1OB⋯O2Aii	0.91 (2)	1.81 (2)	2.716 (1)	176 (2)
C4A—H4AA⋯O2Bi	0.93	2.50	3.185 (1)	131
C4B—H4BA⋯O2Aii	0.93	2.50	3.192 (1)	131
C14B—H14B⋯O3A	0.93	2.56	3.485 (1)	173
C18B—H18C⋯Cg1iii	0.97	2.85	3.696 (1)	146
C24B—H24D⋯Cg2iii	0.97	2.71	3.554 (1)	145
C22A—H22B⋯Cg3iv	0.97	2.95	3.743 (1)	140

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1, Cg2 and Cg3 are the centroids of the C1A–C6A, C10B–C15B and C1B–C6B rings, respectively.