(E)-1-[4-(Hex-yloxy)phen-yl]-3-(3-hy-droxy-phen-yl)prop-2-en-1-one.

There are two mol-ecules in the asymmetric unit of the title compound, C(21)H(24)O(3), in which the dihedral angles between the aromatic rings are 6.4 (1) and 7.0 (1)°. The enone moiety of both mol-ecules adopts an s-cis configuration. In the crystal, inter-molecular O-H⋯O and C-H⋯O inter-actions to the same acceptor O atom generate R(2) (1)(6) ring motifs and further C-H⋯O inter-actions generate R(2) (2)(8) ring motifs. Topologically, the R(2) (1)(6) and R(2) (2)(8) ring motifs are arranged alternately, forming [001] chains of mol-ecules. 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: Razak, Fun, Ngaini, Rahman et al. (2009 ▶); Razak, Fun, Ngaini, Fadzillah et al. (2009a ▶,b ▶); Ngaini, Fadzillah et al. (2009 ▶); Ngaini, Rahman et al. (2009 ▶); Razak et al. (2009a ▶,b ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987) ▶.

Experimental

Crystal data

C21H24O3

M = 324.40

Triclinic,

a = 7.6053 (3) Å

b = 13.7328 (5) Å

c = 17.3769 (7) Å

α = 105.226 (2)°

β = 93.740 (2)°

γ = 93.038 (2)°

V = 1742.80 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.77 × 0.44 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.940, T max = 0.990

36519 measured reflections

10044 independent reflections

6371 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.188

S = 1.04

10044 reflections

443 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.66 e Å−3

Δρmin = −0.28 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810047768/hb5741sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047768/hb5741Isup2.hkl

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

C21H24O3	Z = 4
Mr = 324.40	F(000) = 696
Triclinic, P1	Dx = 1.236 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6053 (3) Å	Cell parameters from 9989 reflections
b = 13.7328 (5) Å	θ = 2.7–31.5°
c = 17.3769 (7) Å	µ = 0.08 mm−1
α = 105.226 (2)°	T = 100 K
β = 93.740 (2)°	Plate, colourless
γ = 93.038 (2)°	0.77 × 0.44 × 0.12 mm
V = 1742.80 (12) Å3

Bruker SMART APEXII CCD diffractometer	10044 independent reflections
Radiation source: sealed tube	6371 reflections with I > 2σ(I)
graphite	Rint = 0.036
π and ω scans	θmax = 30.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.940, Tmax = 0.990	k = −19→19
36519 measured reflections	l = −24→23

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0965P)2 + 0.6952P] where P = (Fo2 + 2Fc2)/3
10044 reflections	(Δ/σ)max < 0.001
443 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −0.28 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	−0.04558 (17)	−0.32446 (10)	0.74767 (8)	0.0222 (3)
O2A	0.17874 (17)	0.08611 (9)	0.57096 (7)	0.0229 (3)
O3A	0.49336 (16)	0.12151 (8)	0.24926 (7)	0.0193 (3)
C1A	0.0626 (2)	−0.22051 (13)	0.66575 (10)	0.0177 (3)
H1AA	0.0344	−0.1623	0.7027	0.021*
C2A	0.0299 (2)	−0.31450 (13)	0.68046 (10)	0.0181 (3)
C3A	0.0749 (2)	−0.40150 (13)	0.62610 (11)	0.0214 (4)
H3AA	0.0551	−0.4644	0.6360	0.026*
C4A	0.1498 (2)	−0.39383 (13)	0.55681 (11)	0.0226 (4)
H4AA	0.1800	−0.4521	0.5204	0.027*
C5A	0.1801 (2)	−0.30062 (13)	0.54114 (11)	0.0204 (4)
H5AA	0.2286	−0.2967	0.4942	0.025*
C6A	0.1373 (2)	−0.21258 (12)	0.59617 (10)	0.0173 (3)
C7A	0.1628 (2)	−0.11143 (13)	0.58357 (10)	0.0185 (3)
H7AA	0.1380	−0.0577	0.6257	0.022*
C8A	0.2170 (2)	−0.08706 (12)	0.51938 (11)	0.0177 (3)
H8AA	0.2481	−0.1376	0.4763	0.021*
C9A	0.2285 (2)	0.01929 (12)	0.51567 (10)	0.0161 (3)
C10A	0.2985 (2)	0.04561 (12)	0.44537 (10)	0.0157 (3)
C11A	0.3666 (2)	−0.02568 (12)	0.38269 (10)	0.0170 (3)
H11A	0.3692	−0.0926	0.3847	0.020*
C12A	0.4293 (2)	0.00219 (12)	0.31843 (10)	0.0178 (3)
H12A	0.4733	−0.0459	0.2773	0.021*
C13A	0.4270 (2)	0.10263 (12)	0.31485 (10)	0.0160 (3)
C14A	0.3598 (2)	0.17511 (12)	0.37613 (10)	0.0174 (3)
H14A	0.3576	0.2420	0.3739	0.021*
C15A	0.2965 (2)	0.14575 (12)	0.44015 (10)	0.0177 (3)
H15A	0.2513	0.1938	0.4809	0.021*
C16A	0.5117 (2)	0.22438 (12)	0.24321 (11)	0.0180 (3)
H16A	0.5771	0.2680	0.2906	0.022*
H16B	0.3967	0.2500	0.2370	0.022*
C17A	0.6112 (2)	0.21984 (12)	0.17017 (10)	0.0176 (3)
H17A	0.5423	0.1760	0.1239	0.021*
H17B	0.7215	0.1893	0.1765	0.021*
C18A	0.6523 (2)	0.32204 (13)	0.15368 (11)	0.0205 (4)
H18A	0.7172	0.3677	0.2003	0.025*
H18B	0.5429	0.3514	0.1433	0.025*
C19A	0.7623 (2)	0.30938 (13)	0.08122 (11)	0.0212 (4)
H19A	0.8531	0.2637	0.0855	0.025*
H19B	0.6862	0.2780	0.0331	0.025*
C20A	0.8507 (3)	0.40815 (13)	0.07228 (12)	0.0250 (4)
H20A	0.9201	0.4423	0.1218	0.030*
H20B	0.9308	0.3924	0.0302	0.030*
C21A	0.7195 (3)	0.47918 (15)	0.05250 (15)	0.0370 (5)
H21A	0.7821	0.5388	0.0463	0.056*
H21B	0.6432	0.4978	0.0951	0.056*
H21C	0.6500	0.4459	0.0036	0.056*
O1B	1.03690 (18)	1.26874 (10)	−0.36389 (8)	0.0221 (3)
O2B	0.92123 (17)	0.87058 (9)	−0.16144 (8)	0.0234 (3)
O3B	0.58649 (17)	0.83300 (9)	0.15508 (7)	0.0211 (3)
C1B	0.9824 (2)	1.17003 (12)	−0.27030 (10)	0.0167 (3)
H1BA	1.0148	1.1119	−0.3061	0.020*
C2B	0.9882 (2)	1.26135 (12)	−0.29143 (10)	0.0167 (3)
C3B	0.9418 (2)	1.34888 (12)	−0.23752 (11)	0.0183 (3)
H3BA	0.9450	1.4101	−0.2511	0.022*
C4B	0.8907 (2)	1.34372 (13)	−0.16302 (11)	0.0192 (4)
H4BA	0.8612	1.4022	−0.1268	0.023*
C5B	0.8830 (2)	1.25322 (13)	−0.14194 (10)	0.0182 (3)
H5BA	0.8477	1.2511	−0.0921	0.022*
C6B	0.9286 (2)	1.16495 (12)	−0.19592 (10)	0.0164 (3)
C7B	0.9226 (2)	1.06597 (12)	−0.17862 (10)	0.0182 (3)
H7BA	0.9728	1.0146	−0.2148	0.022*
C8B	0.8539 (2)	1.04076 (12)	−0.11739 (10)	0.0175 (3)
H8BA	0.8028	1.0893	−0.0792	0.021*
C9B	0.8582 (2)	0.93598 (12)	−0.10954 (10)	0.0165 (3)
C10B	0.7870 (2)	0.90971 (12)	−0.03963 (10)	0.0156 (3)
C11B	0.7199 (2)	0.98105 (12)	0.02337 (11)	0.0176 (3)
H11B	0.7202	1.0483	0.0221	0.021*
C12B	0.6538 (2)	0.95274 (12)	0.08697 (11)	0.0184 (3)
H12B	0.6102	1.0008	0.1282	0.022*
C13B	0.6525 (2)	0.85191 (12)	0.08946 (10)	0.0168 (3)
C14B	0.7172 (2)	0.77927 (12)	0.02725 (10)	0.0169 (3)
H14B	0.7155	0.7119	0.0284	0.020*
C15B	0.7835 (2)	0.80879 (12)	−0.03580 (10)	0.0170 (3)
H15B	0.8270	0.7605	−0.0769	0.020*
C16B	0.5958 (2)	0.73389 (12)	0.16826 (10)	0.0171 (3)
H16C	0.7150	0.7123	0.1638	0.020*
H16D	0.5163	0.6847	0.1294	0.020*
C17B	0.5415 (2)	0.74426 (12)	0.25178 (10)	0.0169 (3)
H17C	0.4226	0.7665	0.2545	0.020*
H17D	0.6192	0.7965	0.2888	0.020*
C18B	0.5463 (2)	0.64715 (12)	0.27882 (10)	0.0178 (3)
H18C	0.6643	0.6236	0.2758	0.021*
H18D	0.4655	0.5950	0.2435	0.021*
C19B	0.4938 (2)	0.66626 (13)	0.36472 (11)	0.0203 (4)
H19C	0.5558	0.7288	0.3968	0.024*
H19D	0.3683	0.6756	0.3647	0.024*
C20B	0.5329 (3)	0.58199 (14)	0.40434 (12)	0.0244 (4)
H20C	0.6577	0.5709	0.4029	0.029*
H20D	0.5080	0.6038	0.4601	0.029*
C21B	0.4270 (3)	0.48291 (15)	0.36512 (14)	0.0372 (5)
H21D	0.4515	0.4347	0.3950	0.056*
H21E	0.4590	0.4574	0.3114	0.056*
H21F	0.3032	0.4937	0.3642	0.056*
H1OB	1.074 (3)	1.212 (2)	−0.3885 (16)	0.045 (7)*
H1OA	−0.063 (4)	−0.261 (2)	0.7782 (18)	0.062 (9)*

	U11	U22	U33	U12	U13	U23
O1A	0.0294 (7)	0.0205 (6)	0.0194 (7)	0.0003 (5)	0.0103 (5)	0.0085 (5)
O2A	0.0319 (7)	0.0226 (6)	0.0166 (6)	0.0068 (5)	0.0104 (5)	0.0066 (5)
O3A	0.0281 (6)	0.0133 (5)	0.0186 (6)	0.0005 (5)	0.0095 (5)	0.0064 (5)
C1A	0.0193 (8)	0.0183 (8)	0.0157 (8)	0.0027 (6)	0.0036 (7)	0.0042 (6)
C2A	0.0165 (8)	0.0234 (8)	0.0166 (8)	0.0005 (6)	0.0046 (7)	0.0084 (7)
C3A	0.0251 (9)	0.0183 (8)	0.0226 (9)	0.0005 (7)	0.0050 (7)	0.0082 (7)
C4A	0.0278 (9)	0.0188 (8)	0.0213 (9)	0.0044 (7)	0.0076 (7)	0.0036 (7)
C5A	0.0248 (9)	0.0226 (8)	0.0161 (8)	0.0035 (7)	0.0071 (7)	0.0074 (7)
C6A	0.0177 (8)	0.0205 (8)	0.0149 (8)	0.0013 (6)	0.0016 (6)	0.0069 (6)
C7A	0.0208 (8)	0.0200 (8)	0.0162 (8)	0.0035 (6)	0.0044 (7)	0.0063 (6)
C8A	0.0181 (8)	0.0178 (8)	0.0174 (8)	0.0023 (6)	0.0047 (7)	0.0041 (6)
C9A	0.0145 (7)	0.0189 (8)	0.0153 (8)	0.0018 (6)	0.0012 (6)	0.0050 (6)
C10A	0.0146 (7)	0.0183 (8)	0.0148 (8)	0.0011 (6)	0.0018 (6)	0.0055 (6)
C11A	0.0196 (8)	0.0142 (7)	0.0175 (8)	0.0016 (6)	0.0027 (7)	0.0044 (6)
C12A	0.0218 (8)	0.0147 (7)	0.0163 (8)	0.0022 (6)	0.0051 (7)	0.0020 (6)
C13A	0.0150 (7)	0.0181 (8)	0.0154 (8)	−0.0005 (6)	0.0024 (6)	0.0052 (6)
C14A	0.0188 (8)	0.0153 (7)	0.0191 (9)	0.0009 (6)	0.0040 (7)	0.0060 (6)
C15A	0.0189 (8)	0.0164 (8)	0.0170 (8)	0.0023 (6)	0.0030 (7)	0.0026 (6)
C16A	0.0211 (8)	0.0141 (7)	0.0202 (9)	0.0004 (6)	0.0040 (7)	0.0069 (6)
C17A	0.0205 (8)	0.0166 (8)	0.0174 (8)	−0.0009 (6)	0.0031 (7)	0.0074 (6)
C18A	0.0257 (9)	0.0183 (8)	0.0197 (9)	−0.0003 (7)	0.0049 (7)	0.0084 (7)
C19A	0.0253 (9)	0.0193 (8)	0.0206 (9)	−0.0003 (7)	0.0061 (7)	0.0072 (7)
C20A	0.0312 (10)	0.0228 (9)	0.0217 (9)	−0.0054 (7)	0.0058 (8)	0.0076 (7)
C21A	0.0494 (13)	0.0252 (10)	0.0437 (13)	0.0081 (9)	0.0132 (11)	0.0185 (9)
O1B	0.0327 (7)	0.0212 (6)	0.0153 (6)	0.0026 (5)	0.0076 (5)	0.0087 (5)
O2B	0.0343 (7)	0.0193 (6)	0.0187 (7)	0.0042 (5)	0.0120 (6)	0.0062 (5)
O3B	0.0329 (7)	0.0158 (6)	0.0195 (6)	0.0054 (5)	0.0142 (5)	0.0096 (5)
C1B	0.0182 (8)	0.0162 (7)	0.0160 (8)	0.0008 (6)	0.0042 (6)	0.0042 (6)
C2B	0.0177 (8)	0.0202 (8)	0.0138 (8)	−0.0003 (6)	0.0023 (6)	0.0073 (6)
C3B	0.0213 (8)	0.0156 (8)	0.0200 (9)	−0.0007 (6)	0.0032 (7)	0.0082 (6)
C4B	0.0210 (8)	0.0167 (8)	0.0198 (9)	0.0007 (6)	0.0047 (7)	0.0040 (6)
C5B	0.0202 (8)	0.0208 (8)	0.0149 (8)	0.0003 (6)	0.0058 (7)	0.0065 (6)
C6B	0.0155 (7)	0.0189 (8)	0.0163 (8)	−0.0001 (6)	0.0028 (6)	0.0074 (6)
C7B	0.0219 (8)	0.0171 (8)	0.0167 (8)	0.0013 (6)	0.0052 (7)	0.0057 (6)
C8B	0.0213 (8)	0.0169 (8)	0.0159 (8)	0.0013 (6)	0.0052 (7)	0.0062 (6)
C9B	0.0171 (8)	0.0186 (8)	0.0148 (8)	−0.0002 (6)	0.0027 (6)	0.0058 (6)
C10B	0.0152 (7)	0.0181 (8)	0.0152 (8)	−0.0002 (6)	0.0025 (6)	0.0072 (6)
C11B	0.0207 (8)	0.0150 (7)	0.0188 (8)	0.0028 (6)	0.0040 (7)	0.0067 (6)
C12B	0.0231 (8)	0.0158 (8)	0.0181 (9)	0.0045 (6)	0.0073 (7)	0.0056 (6)
C13B	0.0164 (8)	0.0191 (8)	0.0170 (8)	0.0009 (6)	0.0048 (6)	0.0075 (6)
C14B	0.0192 (8)	0.0144 (7)	0.0193 (8)	0.0022 (6)	0.0061 (7)	0.0071 (6)
C15B	0.0184 (8)	0.0171 (8)	0.0163 (8)	0.0024 (6)	0.0040 (6)	0.0053 (6)
C16B	0.0208 (8)	0.0149 (7)	0.0179 (8)	0.0021 (6)	0.0053 (7)	0.0077 (6)
C17B	0.0196 (8)	0.0162 (8)	0.0162 (8)	0.0008 (6)	0.0054 (6)	0.0060 (6)
C18B	0.0224 (8)	0.0172 (8)	0.0166 (8)	0.0018 (6)	0.0066 (7)	0.0080 (6)
C19B	0.0261 (9)	0.0193 (8)	0.0175 (9)	0.0018 (7)	0.0054 (7)	0.0076 (7)
C20B	0.0301 (10)	0.0255 (9)	0.0228 (9)	0.0053 (7)	0.0081 (8)	0.0137 (7)
C21B	0.0598 (15)	0.0233 (10)	0.0336 (12)	−0.0012 (9)	0.0109 (11)	0.0155 (9)

O1A—C2A	1.369 (2)	O1B—C2B	1.363 (2)
O1A—H1OA	0.92 (3)	O1B—H1OB	0.85 (3)
O2A—C9A	1.237 (2)	O2B—C9B	1.235 (2)
O3A—C13A	1.355 (2)	O3B—C13B	1.355 (2)
O3A—C16A	1.4440 (19)	O3B—C16B	1.4428 (19)
C1A—C2A	1.393 (2)	C1B—C2B	1.395 (2)
C1A—C6A	1.396 (2)	C1B—C6B	1.399 (2)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.389 (2)	C2B—C3B	1.394 (2)
C3A—C4A	1.391 (3)	C3B—C4B	1.394 (2)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.388 (2)	C4B—C5B	1.384 (2)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.399 (2)	C5B—C6B	1.400 (2)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.467 (2)	C6B—C7B	1.466 (2)
C7A—C8A	1.330 (2)	C7B—C8B	1.331 (2)
C7A—H7AA	0.9300	C7B—H7BA	0.9300
C8A—C9A	1.477 (2)	C8B—C9B	1.482 (2)
C8A—H8AA	0.9300	C8B—H8BA	0.9300
C9A—C10A	1.484 (2)	C9B—C10B	1.481 (2)
C10A—C15A	1.403 (2)	C10B—C15B	1.404 (2)
C10A—C11A	1.407 (2)	C10B—C11B	1.408 (2)
C11A—C12A	1.377 (2)	C11B—C12B	1.379 (2)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.398 (2)	C12B—C13B	1.396 (2)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.398 (2)	C13B—C14B	1.400 (2)
C14A—C15A	1.384 (2)	C14B—C15B	1.379 (2)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—C17A	1.509 (2)	C16B—C17B	1.508 (2)
C16A—H16A	0.9700	C16B—H16C	0.9700
C16A—H16B	0.9700	C16B—H16D	0.9700
C17A—C18A	1.525 (2)	C17B—C18B	1.527 (2)
C17A—H17A	0.9700	C17B—H17C	0.9700
C17A—H17B	0.9700	C17B—H17D	0.9700
C18A—C19A	1.534 (2)	C18B—C19B	1.529 (2)
C18A—H18A	0.9700	C18B—H18C	0.9700
C18A—H18B	0.9700	C18B—H18D	0.9700
C19A—C20A	1.531 (2)	C19B—C20B	1.526 (2)
C19A—H19A	0.9700	C19B—H19C	0.9700
C19A—H19B	0.9700	C19B—H19D	0.9700
C20A—C21A	1.517 (3)	C20B—C21B	1.513 (3)
C20A—H20A	0.9700	C20B—H20C	0.9700
C20A—H20B	0.9700	C20B—H20D	0.9700
C21A—H21A	0.9600	C21B—H21D	0.9600
C21A—H21B	0.9600	C21B—H21E	0.9600
C21A—H21C	0.9600	C21B—H21F	0.9600
C2A—O1A—H1OA	107.6 (18)	C2B—O1B—H1OB	108.3 (18)
C13A—O3A—C16A	119.39 (13)	C13B—O3B—C16B	119.73 (13)
C2A—C1A—C6A	120.84 (16)	C2B—C1B—C6B	120.76 (15)
C2A—C1A—H1AA	119.6	C2B—C1B—H1BA	119.6
C6A—C1A—H1AA	119.6	C6B—C1B—H1BA	119.6
O1A—C2A—C3A	118.21 (15)	O1B—C2B—C3B	117.90 (15)
O1A—C2A—C1A	121.99 (15)	O1B—C2B—C1B	122.35 (15)
C3A—C2A—C1A	119.80 (16)	C3B—C2B—C1B	119.75 (15)
C2A—C3A—C4A	119.48 (16)	C4B—C3B—C2B	119.28 (15)
C2A—C3A—H3AA	120.3	C4B—C3B—H3BA	120.4
C4A—C3A—H3AA	120.3	C2B—C3B—H3BA	120.4
C5A—C4A—C3A	121.01 (16)	C5B—C4B—C3B	121.31 (16)
C5A—C4A—H4AA	119.5	C5B—C4B—H4BA	119.3
C3A—C4A—H4AA	119.5	C3B—C4B—H4BA	119.3
C4A—C5A—C6A	119.79 (16)	C4B—C5B—C6B	119.71 (16)
C4A—C5A—H5AA	120.1	C4B—C5B—H5BA	120.1
C6A—C5A—H5AA	120.1	C6B—C5B—H5BA	120.1
C1A—C6A—C5A	119.05 (15)	C1B—C6B—C5B	119.19 (15)
C1A—C6A—C7A	117.76 (15)	C1B—C6B—C7B	117.64 (15)
C5A—C6A—C7A	123.17 (16)	C5B—C6B—C7B	123.17 (15)
C8A—C7A—C6A	128.02 (16)	C8B—C7B—C6B	127.82 (16)
C8A—C7A—H7AA	116.0	C8B—C7B—H7BA	116.1
C6A—C7A—H7AA	116.0	C6B—C7B—H7BA	116.1
C7A—C8A—C9A	120.77 (16)	C7B—C8B—C9B	120.59 (16)
C7A—C8A—H8AA	119.6	C7B—C8B—H8BA	119.7
C9A—C8A—H8AA	119.6	C9B—C8B—H8BA	119.7
O2A—C9A—C8A	119.90 (16)	O2B—C9B—C10B	120.05 (15)
O2A—C9A—C10A	120.17 (15)	O2B—C9B—C8B	119.86 (15)
C8A—C9A—C10A	119.93 (14)	C10B—C9B—C8B	120.09 (14)
C15A—C10A—C11A	117.86 (16)	C15B—C10B—C11B	117.80 (15)
C15A—C10A—C9A	119.11 (15)	C15B—C10B—C9B	119.00 (15)
C11A—C10A—C9A	123.03 (15)	C11B—C10B—C9B	123.19 (15)
C12A—C11A—C10A	120.96 (15)	C12B—C11B—C10B	121.04 (15)
C12A—C11A—H11A	119.5	C12B—C11B—H11B	119.5
C10A—C11A—H11A	119.5	C10B—C11B—H11B	119.5
C11A—C12A—C13A	120.12 (15)	C11B—C12B—C13B	119.99 (15)
C11A—C12A—H12A	119.9	C11B—C12B—H12B	120.0
C13A—C12A—H12A	119.9	C13B—C12B—H12B	120.0
O3A—C13A—C12A	115.01 (14)	O3B—C13B—C12B	114.92 (14)
O3A—C13A—C14A	124.78 (15)	O3B—C13B—C14B	124.96 (15)
C12A—C13A—C14A	120.21 (16)	C12B—C13B—C14B	120.11 (16)
C15A—C14A—C13A	118.93 (15)	C15B—C14B—C13B	119.23 (15)
C15A—C14A—H14A	120.5	C15B—C14B—H14B	120.4
C13A—C14A—H14A	120.5	C13B—C14B—H14B	120.4
C14A—C15A—C10A	121.91 (15)	C14B—C15B—C10B	121.81 (15)
C14A—C15A—H15A	119.0	C14B—C15B—H15B	119.1
C10A—C15A—H15A	119.0	C10B—C15B—H15B	119.1
O3A—C16A—C17A	105.46 (13)	O3B—C16B—C17B	105.71 (13)
O3A—C16A—H16A	110.6	O3B—C16B—H16C	110.6
C17A—C16A—H16A	110.6	C17B—C16B—H16C	110.6
O3A—C16A—H16B	110.6	O3B—C16B—H16D	110.6
C17A—C16A—H16B	110.6	C17B—C16B—H16D	110.6
H16A—C16A—H16B	108.8	H16C—C16B—H16D	108.7
C16A—C17A—C18A	114.68 (14)	C16B—C17B—C18B	114.30 (14)
C16A—C17A—H17A	108.6	C16B—C17B—H17C	108.7
C18A—C17A—H17A	108.6	C18B—C17B—H17C	108.7
C16A—C17A—H17B	108.6	C16B—C17B—H17D	108.7
C18A—C17A—H17B	108.6	C18B—C17B—H17D	108.7
H17A—C17A—H17B	107.6	H17C—C17B—H17D	107.6
C17A—C18A—C19A	110.30 (14)	C17B—C18B—C19B	110.22 (14)
C17A—C18A—H18A	109.6	C17B—C18B—H18C	109.6
C19A—C18A—H18A	109.6	C19B—C18B—H18C	109.6
C17A—C18A—H18B	109.6	C17B—C18B—H18D	109.6
C19A—C18A—H18B	109.6	C19B—C18B—H18D	109.6
H18A—C18A—H18B	108.1	H18C—C18B—H18D	108.1
C20A—C19A—C18A	114.49 (15)	C20B—C19B—C18B	114.61 (14)
C20A—C19A—H19A	108.6	C20B—C19B—H19C	108.6
C18A—C19A—H19A	108.6	C18B—C19B—H19C	108.6
C20A—C19A—H19B	108.6	C20B—C19B—H19D	108.6
C18A—C19A—H19B	108.6	C18B—C19B—H19D	108.6
H19A—C19A—H19B	107.6	H19C—C19B—H19D	107.6
C21A—C20A—C19A	113.07 (16)	C21B—C20B—C19B	113.65 (16)
C21A—C20A—H20A	109.0	C21B—C20B—H20C	108.8
C19A—C20A—H20A	109.0	C19B—C20B—H20C	108.8
C21A—C20A—H20B	109.0	C21B—C20B—H20D	108.8
C19A—C20A—H20B	109.0	C19B—C20B—H20D	108.8
H20A—C20A—H20B	107.8	H20C—C20B—H20D	107.7
C20A—C21A—H21A	109.5	C20B—C21B—H21D	109.5
C20A—C21A—H21B	109.5	C20B—C21B—H21E	109.5
H21A—C21A—H21B	109.5	H21D—C21B—H21E	109.5
C20A—C21A—H21C	109.5	C20B—C21B—H21F	109.5
H21A—C21A—H21C	109.5	H21D—C21B—H21F	109.5
H21B—C21A—H21C	109.5	H21E—C21B—H21F	109.5
C6A—C1A—C2A—O1A	−179.04 (15)	C6B—C1B—C2B—O1B	−178.82 (15)
C6A—C1A—C2A—C3A	1.2 (3)	C6B—C1B—C2B—C3B	0.8 (2)
O1A—C2A—C3A—C4A	179.22 (15)	O1B—C2B—C3B—C4B	179.76 (15)
C1A—C2A—C3A—C4A	−1.0 (3)	C1B—C2B—C3B—C4B	0.1 (2)
C2A—C3A—C4A—C5A	−0.1 (3)	C2B—C3B—C4B—C5B	−0.8 (3)
C3A—C4A—C5A—C6A	1.0 (3)	C3B—C4B—C5B—C6B	0.5 (3)
C2A—C1A—C6A—C5A	−0.3 (2)	C2B—C1B—C6B—C5B	−1.1 (2)
C2A—C1A—C6A—C7A	178.12 (15)	C2B—C1B—C6B—C7B	178.81 (15)
C4A—C5A—C6A—C1A	−0.8 (3)	C4B—C5B—C6B—C1B	0.4 (2)
C4A—C5A—C6A—C7A	−179.09 (16)	C4B—C5B—C6B—C7B	−179.44 (16)
C1A—C6A—C7A—C8A	−173.88 (17)	C1B—C6B—C7B—C8B	−170.15 (17)
C5A—C6A—C7A—C8A	4.5 (3)	C5B—C6B—C7B—C8B	9.7 (3)
C6A—C7A—C8A—C9A	177.51 (16)	C6B—C7B—C8B—C9B	179.51 (16)
C7A—C8A—C9A—O2A	−3.7 (2)	C7B—C8B—C9B—O2B	−2.2 (3)
C7A—C8A—C9A—C10A	176.67 (15)	C7B—C8B—C9B—C10B	177.85 (15)
O2A—C9A—C10A—C15A	−4.2 (2)	O2B—C9B—C10B—C15B	−3.5 (2)
C8A—C9A—C10A—C15A	175.42 (14)	C8B—C9B—C10B—C15B	176.44 (15)
O2A—C9A—C10A—C11A	176.26 (16)	O2B—C9B—C10B—C11B	177.33 (16)
C8A—C9A—C10A—C11A	−4.1 (2)	C8B—C9B—C10B—C11B	−2.7 (2)
C15A—C10A—C11A—C12A	0.1 (2)	C15B—C10B—C11B—C12B	0.4 (2)
C9A—C10A—C11A—C12A	179.65 (15)	C9B—C10B—C11B—C12B	179.52 (15)
C10A—C11A—C12A—C13A	0.3 (2)	C10B—C11B—C12B—C13B	−0.1 (3)
C16A—O3A—C13A—C12A	−174.49 (14)	C16B—O3B—C13B—C12B	−173.44 (14)
C16A—O3A—C13A—C14A	5.5 (2)	C16B—O3B—C13B—C14B	6.2 (2)
C11A—C12A—C13A—O3A	179.47 (14)	C11B—C12B—C13B—O3B	179.27 (15)
C11A—C12A—C13A—C14A	−0.5 (2)	C11B—C12B—C13B—C14B	−0.4 (3)
O3A—C13A—C14A—C15A	−179.74 (15)	O3B—C13B—C14B—C15B	−179.00 (15)
C12A—C13A—C14A—C15A	0.2 (2)	C12B—C13B—C14B—C15B	0.6 (2)
C13A—C14A—C15A—C10A	0.2 (2)	C13B—C14B—C15B—C10B	−0.3 (2)
C11A—C10A—C15A—C14A	−0.4 (2)	C11B—C10B—C15B—C14B	−0.1 (2)
C9A—C10A—C15A—C14A	−179.95 (15)	C9B—C10B—C15B—C14B	−179.32 (15)
C13A—O3A—C16A—C17A	172.30 (13)	C13B—O3B—C16B—C17B	170.35 (14)
O3A—C16A—C17A—C18A	−177.78 (14)	O3B—C16B—C17B—C18B	−178.70 (13)
C16A—C17A—C18A—C19A	176.80 (15)	C16B—C17B—C18B—C19B	178.55 (14)
C17A—C18A—C19A—C20A	−165.05 (15)	C17B—C18B—C19B—C20B	−167.08 (15)
C18A—C19A—C20A—C21A	−67.1 (2)	C18B—C19B—C20B—C21B	−64.9 (2)

Cg1 and Cg3 are the centroids of the C1A–C6A and C1B–C6B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1B—H1OB···O2Ai	0.86 (3)	1.92 (3)	2.773 (2)	171 (2)
C1B—H1BA···O2Ai	0.93	2.50	3.196 (2)	132
O1A—H1OA···O2Bii	0.92 (3)	1.85 (3)	2.763 (2)	175 (3)
C1A—H1AA···O2Bii	0.93	2.50	3.214 (2)	133
C12B—H12B···O3Aiii	0.93	2.56	3.483 (2)	175
C12A—H12A···O3Biv	0.93	2.56	3.487 (2)	174
C16A—H16A···Cg1v	0.97	2.80	3.653 (2)	147
C16B—H16C···Cg3vi	0.97	2.73	3.595 (2)	149
C17B—H17C···Cg3vii	0.97	2.74	3.640 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg3 are the centroids of the C1A–C6A and C1B–C6B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1B—H1OB⋯O2Ai	0.86 (3)	1.92 (3)	2.773 (2)	171 (2)
C1B—H1BA⋯O2Ai	0.93	2.50	3.196 (2)	132
O1A—H1OA⋯O2Bii	0.92 (3)	1.85 (3)	2.763 (2)	175 (3)
C1A—H1AA⋯O2Bii	0.93	2.50	3.214 (2)	133
C12B—H12B⋯O3Aiii	0.93	2.56	3.483 (2)	175
C12A—H12A⋯O3Biv	0.93	2.56	3.487 (2)	174
C16A—H16A⋯Cg1v	0.97	2.80	3.653 (2)	147
C16B—H16C⋯Cg3vi	0.97	2.73	3.595 (2)	149
C17B—H17C⋯Cg3vii	0.97	2.74	3.640 (2)	154

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