(1E,4E)-1,5-Bis(2,4,6-trimeth-oxy-phen-yl)penta-1,4-dien-3-one.

There are two crystallographically independent mol-ecules in the asymmetric unit of the title bis-chalcone derivative, C(23)H(26)O(7). The mol-ecules are unsymmetrical and almost planar: the dihedral angle between two benzene rings is 1.04 (7)° in one mol-ecule and 2.31 (7)° in the other. The central penta-1,4-dien-3-one fragment makes dihedral angles of 7.61 (7) and 6.82 (7)° with the two adjacent benzene rings in one mol-ecule, while the corresponding values are 7.85 (7) and 9.42 (6)° in the other. In both mol-ecules, the three meth-oxy groups of the two 2,4,6-trimeth-oxy-phenyl units are coplanar with the attached benzene rings [C-O-C-C- torsion angles of -1.5 (2), -7.2 (2) and 4.1 (2)° in one mol-ecule and -0.7 (2), -5.5 (2) and -0.6 (2)° in the other]. The mol-ecular conformations are stabilized by weak intra-molecular C-H⋯O inter-actions generating two S(6) ring motifs. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O inter-actions into zigzag chains parallel to the c axis. The crystal structure is further stabilized by C-H⋯π inter-actions and π-π inter-actions with centroid-centroid distances of 3.6433 (8) Å.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Fun et al. (2010 ▶); Harrison et al. (2006 ▶). For background to and applications of bis­chalcones, see: Gomes et al. (2009 ▶); Lee et al. (2009 ▶); Quincoces et al. (2008 ▶); Uchida et al. (1998 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C23H26O7

M = 414.44

Monoclinic,

a = 15.7417 (2) Å

b = 15.1192 (2) Å

c = 19.4803 (3) Å

β = 117.827 (1)°

V = 4100.21 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.39 × 0.32 × 0.17 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.963, T max = 0.983

50384 measured reflections

10908 independent reflections

7903 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.139

S = 1.04

10908 reflections

553 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.24 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/S1600536810049299/rz2523sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049299/rz2523Isup2.hkl

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

C23H26O7	F(000) = 1760
Mr = 414.44	Dx = 1.343 Mg m−3
Monoclinic, P21/c	Melting point = 494–495 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.7417 (2) Å	Cell parameters from 10908 reflections
b = 15.1192 (2) Å	θ = 2.1–29.0°
c = 19.4803 (3) Å	µ = 0.10 mm−1
β = 117.827 (1)°	T = 100 K
V = 4100.21 (11) Å3	Block, pale yellow
Z = 8	0.39 × 0.32 × 0.17 mm

Bruker APEXII DUO CCD area-detector diffractometer	10908 independent reflections
Radiation source: sealed tube	7903 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 29.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −20→21
Tmin = 0.963, Tmax = 0.983	k = −20→18
50384 measured reflections	l = −26→26

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0631P)2 + 1.5299P] where P = (Fo2 + 2Fc2)/3
10908 reflections	(Δ/σ)max = 0.001
553 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.24 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	0.17578 (9)	0.23957 (10)	−0.12657 (6)	0.0395 (3)
O2A	0.45629 (7)	0.37966 (7)	−0.07200 (6)	0.0219 (2)
O3A	0.72990 (7)	0.41499 (7)	0.18177 (6)	0.0257 (2)
O4A	0.43772 (7)	0.29181 (7)	0.15211 (5)	0.0209 (2)
O5A	−0.05667 (7)	0.12267 (7)	−0.05942 (6)	0.0218 (2)
O6A	−0.07167 (8)	0.03212 (8)	0.17332 (6)	0.0287 (3)
O7A	0.20935 (7)	0.16050 (7)	0.18551 (6)	0.0233 (2)
C1A	0.50181 (11)	0.37297 (9)	0.00690 (8)	0.0176 (3)
C2A	0.59599 (11)	0.40105 (9)	0.05208 (9)	0.0196 (3)
H2AA	0.6305	0.4261	0.0292	0.023*
C3A	0.63756 (10)	0.39085 (10)	0.13221 (9)	0.0199 (3)
C4A	0.58625 (10)	0.35517 (10)	0.16765 (8)	0.0200 (3)
H4AA	0.6148	0.3497	0.2214	0.024*
C5A	0.49247 (10)	0.32789 (9)	0.12218 (8)	0.0180 (3)
C6A	0.44650 (10)	0.33541 (9)	0.03973 (8)	0.0169 (3)
C7A	0.35023 (10)	0.30407 (9)	−0.01164 (8)	0.0180 (3)
H7AA	0.3314	0.3105	−0.0643	0.022*
C8A	0.28416 (10)	0.26743 (10)	0.00458 (8)	0.0191 (3)
H8AA	0.2963	0.2625	0.0559	0.023*
C9A	0.19240 (11)	0.23482 (10)	−0.05818 (8)	0.0209 (3)
C10A	0.12089 (11)	0.19400 (10)	−0.04001 (8)	0.0204 (3)
H10A	0.0631	0.1753	−0.0809	0.024*
C11A	0.13474 (10)	0.18232 (9)	0.03281 (8)	0.0175 (3)
H11A	0.1931	0.2040	0.0708	0.021*
C12A	0.07555 (10)	0.14215 (9)	0.06315 (8)	0.0177 (3)
C13A	−0.01944 (10)	0.11210 (9)	0.01869 (8)	0.0183 (3)
C14A	−0.07145 (11)	0.07451 (10)	0.05295 (8)	0.0202 (3)
H14A	−0.1340	0.0547	0.0226	0.024*
C15A	−0.02790 (11)	0.06729 (10)	0.13332 (9)	0.0221 (3)
C16A	0.06571 (11)	0.09625 (10)	0.17972 (9)	0.0224 (3)
H16A	0.0937	0.0912	0.2334	0.027*
C17A	0.11655 (10)	0.13254 (10)	0.14487 (8)	0.0193 (3)
C18A	0.50745 (11)	0.41912 (10)	−0.10866 (9)	0.0235 (3)
H18A	0.4664	0.4221	−0.1637	0.035*
H18B	0.5630	0.3840	−0.0983	0.035*
H18C	0.5273	0.4777	−0.0886	0.035*
C19A	0.78857 (12)	0.44273 (12)	0.14764 (10)	0.0325 (4)
H19A	0.8528	0.4535	0.1878	0.049*
H19B	0.7627	0.4961	0.1185	0.049*
H19C	0.7896	0.3973	0.1136	0.049*
C20A	0.47734 (12)	0.28718 (12)	0.23484 (8)	0.0264 (3)
H20A	0.4308	0.2620	0.2480	0.040*
H20B	0.4938	0.3456	0.2564	0.040*
H20C	0.5339	0.2509	0.2556	0.040*
C21A	−0.15303 (11)	0.09395 (10)	−0.10841 (9)	0.0229 (3)
H21A	−0.1695	0.1054	−0.1616	0.034*
H21B	−0.1962	0.1255	−0.0951	0.034*
H21C	−0.1580	0.0317	−0.1013	0.034*
C22A	−0.16834 (11)	0.00175 (11)	0.13032 (10)	0.0271 (3)
H22A	−0.1905	−0.0197	0.1655	0.041*
H22B	−0.1710	−0.0451	0.0962	0.041*
H22C	−0.2085	0.0497	0.1004	0.041*
C23A	0.25648 (12)	0.15076 (12)	0.26804 (8)	0.0272 (4)
H23A	0.3190	0.1774	0.2894	0.041*
H23B	0.2629	0.0890	0.2811	0.041*
H23C	0.2192	0.1793	0.2890	0.041*
O1B	0.68800 (7)	0.20303 (8)	0.36386 (6)	0.0241 (2)
O2B	0.99141 (7)	0.09844 (7)	0.41753 (6)	0.0225 (2)
O3B	1.26319 (8)	0.06825 (8)	0.67341 (6)	0.0287 (3)
O4B	0.96545 (7)	0.18131 (7)	0.63905 (6)	0.0223 (2)
O5B	0.48221 (7)	0.36335 (7)	0.43616 (6)	0.0209 (2)
O6B	0.47137 (8)	0.44271 (8)	0.67297 (6)	0.0260 (2)
O7B	0.75115 (7)	0.31918 (7)	0.67890 (6)	0.0211 (2)
C1B	1.03565 (10)	0.10545 (10)	0.49647 (8)	0.0185 (3)
C2B	1.13074 (10)	0.07922 (10)	0.54267 (9)	0.0206 (3)
H2BA	1.1665	0.0549	0.5205	0.025*
C3B	1.17063 (10)	0.09028 (10)	0.62243 (9)	0.0213 (3)
C4B	1.11777 (11)	0.12564 (10)	0.65642 (8)	0.0220 (3)
H4BA	1.1457	0.1329	0.7100	0.026*
C5B	1.02313 (10)	0.14997 (9)	0.60976 (8)	0.0184 (3)
C6B	0.97838 (10)	0.14116 (9)	0.52777 (8)	0.0172 (3)
C7B	0.87935 (10)	0.16500 (9)	0.47616 (8)	0.0169 (3)
H7BA	0.8555	0.1456	0.4252	0.020*
C8B	0.81720 (10)	0.21120 (9)	0.49162 (8)	0.0174 (3)
H8BA	0.8372	0.2320	0.5418	0.021*
C9B	0.71850 (10)	0.22977 (9)	0.43148 (8)	0.0164 (3)
C10B	0.65299 (10)	0.28005 (9)	0.45157 (8)	0.0174 (3)
H10B	0.5947	0.2990	0.4115	0.021*
C11B	0.67345 (10)	0.29988 (9)	0.52518 (8)	0.0163 (3)
H11B	0.7353	0.2846	0.5620	0.020*
C12B	0.61648 (10)	0.34076 (9)	0.55742 (8)	0.0162 (3)
C13B	0.52085 (10)	0.37092 (9)	0.51463 (8)	0.0169 (3)
C14B	0.46987 (10)	0.40590 (9)	0.55087 (8)	0.0190 (3)
H14B	0.4072	0.4259	0.5217	0.023*
C15B	0.51478 (11)	0.41016 (9)	0.63141 (9)	0.0195 (3)
C16B	0.60879 (11)	0.38162 (10)	0.67653 (8)	0.0194 (3)
H16B	0.6376	0.3849	0.7304	0.023*
C17B	0.65853 (10)	0.34824 (9)	0.63965 (8)	0.0171 (3)
C18B	1.04507 (11)	0.06389 (11)	0.38133 (9)	0.0248 (3)
H18D	1.0042	0.0593	0.3264	0.037*
H18E	1.0694	0.0064	0.4021	0.037*
H18F	1.0978	0.1027	0.3911	0.037*
C19B	1.31903 (11)	0.02436 (11)	0.64289 (10)	0.0280 (4)
H19D	1.3822	0.0125	0.6843	0.042*
H19E	1.3238	0.0615	0.6049	0.042*
H19F	1.2885	−0.0303	0.6191	0.042*
C20B	1.00518 (12)	0.18825 (12)	0.72165 (8)	0.0293 (4)
H20D	0.9576	0.2116	0.7344	0.044*
H20E	1.0597	0.2271	0.7413	0.044*
H20F	1.0249	0.1308	0.7446	0.044*
C21B	0.38459 (10)	0.39154 (10)	0.38923 (8)	0.0226 (3)
H21D	0.3672	0.3838	0.3354	0.034*
H21E	0.3787	0.4528	0.3992	0.034*
H21G	0.3427	0.3568	0.4018	0.034*
C22B	0.37374 (12)	0.47159 (12)	0.63068 (10)	0.0315 (4)
H22D	0.3517	0.4916	0.6664	0.047*
H22G	0.3344	0.4233	0.6006	0.047*
H22E	0.3697	0.5192	0.5967	0.047*
C23B	0.80039 (12)	0.33050 (12)	0.76164 (8)	0.0273 (4)
H23G	0.8652	0.3097	0.7818	0.041*
H23D	0.7680	0.2974	0.7845	0.041*
H23E	0.8009	0.3920	0.7740	0.041*

	U11	U22	U33	U12	U13	U23
O1A	0.0300 (7)	0.0677 (9)	0.0156 (5)	−0.0216 (6)	0.0063 (5)	0.0002 (6)
O2A	0.0209 (6)	0.0262 (6)	0.0191 (5)	−0.0032 (4)	0.0099 (4)	0.0011 (4)
O3A	0.0156 (5)	0.0298 (6)	0.0281 (6)	−0.0049 (4)	0.0072 (5)	−0.0042 (5)
O4A	0.0176 (5)	0.0289 (6)	0.0148 (5)	−0.0008 (4)	0.0064 (4)	0.0027 (4)
O5A	0.0171 (5)	0.0276 (6)	0.0170 (5)	−0.0012 (4)	0.0049 (4)	−0.0006 (4)
O6A	0.0247 (6)	0.0382 (7)	0.0270 (6)	−0.0021 (5)	0.0151 (5)	0.0055 (5)
O7A	0.0178 (5)	0.0333 (6)	0.0154 (5)	−0.0011 (4)	0.0049 (4)	0.0006 (4)
C1A	0.0195 (7)	0.0141 (7)	0.0196 (7)	0.0018 (5)	0.0094 (6)	−0.0001 (5)
C2A	0.0194 (7)	0.0167 (7)	0.0258 (7)	0.0003 (6)	0.0133 (6)	−0.0008 (6)
C3A	0.0143 (7)	0.0175 (7)	0.0252 (7)	0.0003 (6)	0.0069 (6)	−0.0035 (6)
C4A	0.0179 (7)	0.0214 (7)	0.0174 (7)	0.0017 (6)	0.0055 (6)	−0.0003 (5)
C5A	0.0173 (7)	0.0162 (7)	0.0197 (7)	0.0024 (5)	0.0080 (6)	0.0006 (5)
C6A	0.0155 (7)	0.0161 (7)	0.0175 (7)	0.0012 (5)	0.0065 (6)	−0.0002 (5)
C7A	0.0185 (7)	0.0174 (7)	0.0153 (6)	0.0021 (6)	0.0056 (6)	0.0005 (5)
C8A	0.0183 (7)	0.0208 (7)	0.0147 (6)	−0.0002 (6)	0.0047 (6)	−0.0002 (5)
C9A	0.0208 (8)	0.0220 (7)	0.0164 (7)	−0.0005 (6)	0.0058 (6)	0.0019 (6)
C10A	0.0166 (7)	0.0217 (7)	0.0202 (7)	−0.0015 (6)	0.0064 (6)	−0.0011 (6)
C11A	0.0162 (7)	0.0155 (7)	0.0185 (7)	0.0015 (5)	0.0061 (6)	−0.0007 (5)
C12A	0.0171 (7)	0.0157 (7)	0.0193 (7)	0.0023 (5)	0.0078 (6)	0.0000 (5)
C13A	0.0190 (7)	0.0160 (7)	0.0185 (7)	0.0042 (6)	0.0076 (6)	−0.0001 (5)
C14A	0.0172 (7)	0.0190 (7)	0.0236 (7)	0.0002 (6)	0.0088 (6)	−0.0010 (6)
C15A	0.0226 (8)	0.0208 (8)	0.0264 (8)	0.0029 (6)	0.0145 (7)	0.0024 (6)
C16A	0.0235 (8)	0.0252 (8)	0.0184 (7)	0.0038 (6)	0.0099 (6)	0.0014 (6)
C17A	0.0177 (7)	0.0184 (7)	0.0200 (7)	0.0027 (6)	0.0074 (6)	−0.0008 (5)
C18A	0.0253 (8)	0.0243 (8)	0.0257 (8)	0.0001 (6)	0.0158 (7)	0.0025 (6)
C19A	0.0198 (8)	0.0420 (10)	0.0378 (9)	−0.0093 (7)	0.0152 (7)	−0.0138 (8)
C20A	0.0226 (8)	0.0380 (9)	0.0156 (7)	−0.0009 (7)	0.0064 (6)	0.0028 (6)
C21A	0.0188 (8)	0.0230 (8)	0.0218 (7)	−0.0007 (6)	0.0052 (6)	−0.0039 (6)
C22A	0.0235 (8)	0.0286 (8)	0.0330 (8)	−0.0006 (7)	0.0162 (7)	0.0025 (7)
C23A	0.0224 (8)	0.0403 (10)	0.0166 (7)	−0.0001 (7)	0.0072 (6)	0.0002 (6)
O1B	0.0171 (5)	0.0371 (6)	0.0154 (5)	0.0035 (5)	0.0053 (4)	−0.0032 (4)
O2B	0.0181 (5)	0.0317 (6)	0.0179 (5)	0.0030 (4)	0.0085 (4)	−0.0004 (4)
O3B	0.0161 (5)	0.0345 (7)	0.0276 (6)	0.0042 (5)	0.0036 (5)	0.0039 (5)
O4B	0.0188 (5)	0.0312 (6)	0.0133 (5)	0.0019 (4)	0.0044 (4)	−0.0025 (4)
O5B	0.0158 (5)	0.0258 (6)	0.0169 (5)	0.0038 (4)	0.0042 (4)	0.0001 (4)
O6B	0.0224 (6)	0.0326 (6)	0.0266 (6)	0.0046 (5)	0.0144 (5)	−0.0028 (5)
O7B	0.0169 (5)	0.0304 (6)	0.0142 (5)	0.0040 (4)	0.0059 (4)	0.0000 (4)
C1B	0.0180 (7)	0.0176 (7)	0.0190 (7)	−0.0025 (6)	0.0081 (6)	0.0008 (5)
C2B	0.0165 (7)	0.0186 (7)	0.0267 (8)	−0.0001 (6)	0.0101 (6)	0.0022 (6)
C3B	0.0137 (7)	0.0190 (7)	0.0259 (8)	−0.0006 (6)	0.0046 (6)	0.0042 (6)
C4B	0.0190 (8)	0.0229 (8)	0.0172 (7)	−0.0018 (6)	0.0026 (6)	0.0009 (6)
C5B	0.0171 (7)	0.0170 (7)	0.0191 (7)	−0.0017 (6)	0.0070 (6)	−0.0001 (5)
C6B	0.0153 (7)	0.0158 (7)	0.0179 (7)	−0.0023 (5)	0.0057 (6)	0.0007 (5)
C7B	0.0155 (7)	0.0194 (7)	0.0141 (6)	−0.0038 (5)	0.0054 (5)	0.0006 (5)
C8B	0.0176 (7)	0.0185 (7)	0.0138 (6)	−0.0021 (6)	0.0054 (6)	−0.0005 (5)
C9B	0.0170 (7)	0.0174 (7)	0.0151 (6)	−0.0026 (5)	0.0079 (6)	0.0008 (5)
C10B	0.0144 (7)	0.0186 (7)	0.0170 (6)	0.0006 (5)	0.0055 (6)	0.0015 (5)
C11B	0.0150 (7)	0.0147 (7)	0.0183 (7)	0.0000 (5)	0.0070 (6)	0.0015 (5)
C12B	0.0178 (7)	0.0145 (7)	0.0172 (6)	−0.0008 (5)	0.0089 (6)	−0.0001 (5)
C13B	0.0180 (7)	0.0143 (7)	0.0167 (6)	−0.0014 (5)	0.0066 (6)	−0.0005 (5)
C14B	0.0151 (7)	0.0168 (7)	0.0245 (7)	0.0006 (5)	0.0089 (6)	−0.0006 (6)
C15B	0.0218 (8)	0.0167 (7)	0.0258 (7)	−0.0012 (6)	0.0159 (6)	−0.0017 (6)
C16B	0.0212 (8)	0.0206 (7)	0.0175 (7)	−0.0001 (6)	0.0098 (6)	−0.0006 (5)
C17B	0.0169 (7)	0.0166 (7)	0.0173 (6)	−0.0006 (5)	0.0076 (6)	0.0006 (5)
C18B	0.0238 (8)	0.0286 (8)	0.0273 (8)	0.0000 (6)	0.0164 (7)	−0.0014 (6)
C19B	0.0163 (8)	0.0273 (9)	0.0360 (9)	0.0032 (6)	0.0084 (7)	0.0064 (7)
C20B	0.0307 (9)	0.0356 (9)	0.0151 (7)	0.0042 (7)	0.0053 (7)	−0.0030 (6)
C21B	0.0168 (7)	0.0251 (8)	0.0208 (7)	0.0016 (6)	0.0045 (6)	0.0028 (6)
C22B	0.0232 (9)	0.0388 (10)	0.0357 (9)	0.0053 (7)	0.0165 (7)	−0.0035 (7)
C23B	0.0224 (8)	0.0412 (10)	0.0152 (7)	0.0045 (7)	0.0063 (6)	−0.0010 (6)

O1A—C9A	1.2341 (17)	O1B—C9B	1.2404 (16)
O2A—C1A	1.3631 (17)	O2B—C1B	1.3643 (17)
O2A—C18A	1.4324 (17)	O2B—C18B	1.4282 (18)
O3A—C3A	1.3668 (17)	O3B—C3B	1.3672 (18)
O3A—C19A	1.430 (2)	O3B—C19B	1.433 (2)
O4A—C5A	1.3600 (17)	O4B—C5B	1.3631 (18)
O4A—C20A	1.4327 (16)	O4B—C20B	1.4324 (17)
O5A—C13A	1.3607 (16)	O5B—C13B	1.3607 (16)
O5A—C21A	1.4314 (17)	O5B—C21B	1.4379 (17)
O6A—C15A	1.3661 (18)	O6B—C15B	1.3716 (17)
O6A—C22A	1.4277 (19)	O6B—C22B	1.4316 (19)
O7A—C17A	1.3637 (17)	O7B—C17B	1.3648 (17)
O7A—C23A	1.4294 (17)	O7B—C23B	1.4357 (17)
C1A—C2A	1.391 (2)	C1B—C2B	1.396 (2)
C1A—C6A	1.418 (2)	C1B—C6B	1.410 (2)
C2A—C3A	1.391 (2)	C2B—C3B	1.388 (2)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.393 (2)	C3B—C4B	1.390 (2)
C4A—C5A	1.383 (2)	C4B—C5B	1.384 (2)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.4250 (19)	C5B—C6B	1.4194 (19)
C6A—C7A	1.451 (2)	C6B—C7B	1.4518 (19)
C7A—C8A	1.340 (2)	C7B—C8B	1.346 (2)
C7A—H7AA	0.9300	C7B—H7BA	0.9300
C8A—C9A	1.475 (2)	C8B—C9B	1.4717 (19)
C8A—H8AA	0.9300	C8B—H8BA	0.9300
C9A—C10A	1.465 (2)	C9B—C10B	1.474 (2)
C10A—C11A	1.342 (2)	C10B—C11B	1.3484 (19)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.449 (2)	C11B—C12B	1.4514 (19)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.408 (2)	C12B—C13B	1.413 (2)
C12A—C17A	1.4186 (19)	C12B—C17B	1.4238 (19)
C13A—C14A	1.396 (2)	C13B—C14B	1.397 (2)
C14A—C15A	1.390 (2)	C14B—C15B	1.389 (2)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—C16A	1.392 (2)	C15B—C16B	1.391 (2)
C16A—C17A	1.382 (2)	C16B—C17B	1.382 (2)
C16A—H16A	0.9300	C16B—H16B	0.9300
C18A—H18A	0.9600	C18B—H18D	0.9600
C18A—H18B	0.9600	C18B—H18E	0.9600
C18A—H18C	0.9600	C18B—H18F	0.9600
C19A—H19A	0.9600	C19B—H19D	0.9600
C19A—H19B	0.9600	C19B—H19E	0.9600
C19A—H19C	0.9600	C19B—H19F	0.9600
C20A—H20A	0.9600	C20B—H20D	0.9600
C20A—H20B	0.9600	C20B—H20E	0.9600
C20A—H20C	0.9600	C20B—H20F	0.9600
C21A—H21A	0.9600	C21B—H21D	0.9600
C21A—H21B	0.9600	C21B—H21E	0.9600
C21A—H21C	0.9600	C21B—H21G	0.9600
C22A—H22A	0.9600	C22B—H22D	0.9600
C22A—H22B	0.9600	C22B—H22G	0.9600
C22A—H22C	0.9600	C22B—H22E	0.9600
C23A—H23A	0.9600	C23B—H23G	0.9600
C23A—H23B	0.9600	C23B—H23D	0.9600
C23A—H23C	0.9600	C23B—H23E	0.9600
C1A—O2A—C18A	118.11 (11)	C1B—O2B—C18B	118.46 (12)
C3A—O3A—C19A	117.06 (12)	C3B—O3B—C19B	117.61 (12)
C5A—O4A—C20A	118.13 (11)	C5B—O4B—C20B	117.96 (12)
C13A—O5A—C21A	118.64 (11)	C13B—O5B—C21B	118.29 (11)
C15A—O6A—C22A	118.28 (12)	C15B—O6B—C22B	117.81 (12)
C17A—O7A—C23A	118.30 (12)	C17B—O7B—C23B	117.80 (11)
O2A—C1A—C2A	122.34 (13)	O2B—C1B—C2B	122.27 (13)
O2A—C1A—C6A	115.35 (12)	O2B—C1B—C6B	115.09 (12)
C2A—C1A—C6A	122.31 (13)	C2B—C1B—C6B	122.64 (13)
C1A—C2A—C3A	118.70 (13)	C3B—C2B—C1B	118.43 (14)
C1A—C2A—H2AA	120.6	C3B—C2B—H2BA	120.8
C3A—C2A—H2AA	120.6	C1B—C2B—H2BA	120.8
O3A—C3A—C2A	123.44 (13)	O3B—C3B—C2B	123.77 (14)
O3A—C3A—C4A	115.15 (13)	O3B—C3B—C4B	114.82 (13)
C2A—C3A—C4A	121.41 (13)	C2B—C3B—C4B	121.41 (13)
C5A—C4A—C3A	119.37 (13)	C5B—C4B—C3B	119.32 (13)
C5A—C4A—H4AA	120.3	C5B—C4B—H4BA	120.3
C3A—C4A—H4AA	120.3	C3B—C4B—H4BA	120.3
O4A—C5A—C4A	123.06 (13)	O4B—C5B—C4B	122.72 (13)
O4A—C5A—C6A	115.16 (12)	O4B—C5B—C6B	115.21 (12)
C4A—C5A—C6A	121.78 (13)	C4B—C5B—C6B	122.04 (13)
C1A—C6A—C5A	116.41 (13)	C1B—C6B—C5B	116.16 (13)
C1A—C6A—C7A	118.89 (12)	C1B—C6B—C7B	119.47 (13)
C5A—C6A—C7A	124.64 (13)	C5B—C6B—C7B	124.37 (13)
C8A—C7A—C6A	130.38 (13)	C8B—C7B—C6B	129.17 (13)
C8A—C7A—H7AA	114.8	C8B—C7B—H7BA	115.4
C6A—C7A—H7AA	114.8	C6B—C7B—H7BA	115.4
C7A—C8A—C9A	120.69 (13)	C7B—C8B—C9B	121.91 (13)
C7A—C8A—H8AA	119.7	C7B—C8B—H8BA	119.0
C9A—C8A—H8AA	119.7	C9B—C8B—H8BA	119.0
O1A—C9A—C10A	119.07 (13)	O1B—C9B—C8B	121.64 (13)
O1A—C9A—C8A	120.49 (14)	O1B—C9B—C10B	118.57 (12)
C10A—C9A—C8A	120.42 (12)	C8B—C9B—C10B	119.77 (12)
C11A—C10A—C9A	123.14 (13)	C11B—C10B—C9B	123.21 (13)
C11A—C10A—H10A	118.4	C11B—C10B—H10B	118.4
C9A—C10A—H10A	118.4	C9B—C10B—H10B	118.4
C10A—C11A—C12A	131.90 (14)	C10B—C11B—C12B	131.73 (13)
C10A—C11A—H11A	114.0	C10B—C11B—H11B	114.1
C12A—C11A—H11A	114.0	C12B—C11B—H11B	114.1
C13A—C12A—C17A	116.96 (13)	C13B—C12B—C17B	116.47 (12)
C13A—C12A—C11A	125.77 (13)	C13B—C12B—C11B	125.83 (12)
C17A—C12A—C11A	117.27 (13)	C17B—C12B—C11B	117.65 (12)
O5A—C13A—C14A	122.67 (13)	O5B—C13B—C14B	122.59 (13)
O5A—C13A—C12A	115.42 (13)	O5B—C13B—C12B	115.46 (12)
C14A—C13A—C12A	121.91 (13)	C14B—C13B—C12B	121.95 (13)
C15A—C14A—C13A	118.66 (14)	C15B—C14B—C13B	118.61 (13)
C15A—C14A—H14A	120.7	C15B—C14B—H14B	120.7
C13A—C14A—H14A	120.7	C13B—C14B—H14B	120.7
O6A—C15A—C14A	123.94 (14)	O6B—C15B—C14B	123.52 (13)
O6A—C15A—C16A	114.52 (13)	O6B—C15B—C16B	114.49 (13)
C14A—C15A—C16A	121.54 (14)	C14B—C15B—C16B	121.99 (13)
C17A—C16A—C15A	119.10 (14)	C17B—C16B—C15B	118.61 (13)
C17A—C16A—H16A	120.5	C17B—C16B—H16B	120.7
C15A—C16A—H16A	120.5	C15B—C16B—H16B	120.7
O7A—C17A—C16A	123.15 (13)	O7B—C17B—C16B	122.87 (12)
O7A—C17A—C12A	115.01 (13)	O7B—C17B—C12B	114.76 (12)
C16A—C17A—C12A	121.83 (14)	C16B—C17B—C12B	122.37 (13)
O2A—C18A—H18A	109.5	O2B—C18B—H18D	109.5
O2A—C18A—H18B	109.5	O2B—C18B—H18E	109.5
H18A—C18A—H18B	109.5	H18D—C18B—H18E	109.5
O2A—C18A—H18C	109.5	O2B—C18B—H18F	109.5
H18A—C18A—H18C	109.5	H18D—C18B—H18F	109.5
H18B—C18A—H18C	109.5	H18E—C18B—H18F	109.5
O3A—C19A—H19A	109.5	O3B—C19B—H19D	109.5
O3A—C19A—H19B	109.5	O3B—C19B—H19E	109.5
H19A—C19A—H19B	109.5	H19D—C19B—H19E	109.5
O3A—C19A—H19C	109.5	O3B—C19B—H19F	109.5
H19A—C19A—H19C	109.5	H19D—C19B—H19F	109.5
H19B—C19A—H19C	109.5	H19E—C19B—H19F	109.5
O4A—C20A—H20A	109.5	O4B—C20B—H20D	109.5
O4A—C20A—H20B	109.5	O4B—C20B—H20E	109.5
H20A—C20A—H20B	109.5	H20D—C20B—H20E	109.5
O4A—C20A—H20C	109.5	O4B—C20B—H20F	109.5
H20A—C20A—H20C	109.5	H20D—C20B—H20F	109.5
H20B—C20A—H20C	109.5	H20E—C20B—H20F	109.5
O5A—C21A—H21A	109.5	O5B—C21B—H21D	109.5
O5A—C21A—H21B	109.5	O5B—C21B—H21E	109.5
H21A—C21A—H21B	109.5	H21D—C21B—H21E	109.5
O5A—C21A—H21C	109.5	O5B—C21B—H21G	109.5
H21A—C21A—H21C	109.5	H21D—C21B—H21G	109.5
H21B—C21A—H21C	109.5	H21E—C21B—H21G	109.5
O6A—C22A—H22A	109.5	O6B—C22B—H22D	109.5
O6A—C22A—H22B	109.5	O6B—C22B—H22G	109.5
H22A—C22A—H22B	109.5	H22D—C22B—H22G	109.5
O6A—C22A—H22C	109.5	O6B—C22B—H22E	109.5
H22A—C22A—H22C	109.5	H22D—C22B—H22E	109.5
H22B—C22A—H22C	109.5	H22G—C22B—H22E	109.5
O7A—C23A—H23A	109.5	O7B—C23B—H23G	109.5
O7A—C23A—H23B	109.5	O7B—C23B—H23D	109.5
H23A—C23A—H23B	109.5	H23G—C23B—H23D	109.5
O7A—C23A—H23C	109.5	O7B—C23B—H23E	109.5
H23A—C23A—H23C	109.5	H23G—C23B—H23E	109.5
H23B—C23A—H23C	109.5	H23D—C23B—H23E	109.5
C18A—O2A—C1A—C2A	−1.5 (2)	C18B—O2B—C1B—C2B	−0.7 (2)
C18A—O2A—C1A—C6A	178.45 (12)	C18B—O2B—C1B—C6B	179.23 (13)
O2A—C1A—C2A—C3A	−179.22 (13)	O2B—C1B—C2B—C3B	178.78 (13)
C6A—C1A—C2A—C3A	0.8 (2)	C6B—C1B—C2B—C3B	−1.1 (2)
C19A—O3A—C3A—C2A	−7.2 (2)	C19B—O3B—C3B—C2B	−5.5 (2)
C19A—O3A—C3A—C4A	173.26 (13)	C19B—O3B—C3B—C4B	174.68 (13)
C1A—C2A—C3A—O3A	179.02 (13)	C1B—C2B—C3B—O3B	−179.09 (14)
C1A—C2A—C3A—C4A	−1.4 (2)	C1B—C2B—C3B—C4B	0.7 (2)
O3A—C3A—C4A—C5A	−179.30 (13)	O3B—C3B—C4B—C5B	−179.89 (13)
C2A—C3A—C4A—C5A	1.1 (2)	C2B—C3B—C4B—C5B	0.3 (2)
C20A—O4A—C5A—C4A	4.1 (2)	C20B—O4B—C5B—C4B	−0.6 (2)
C20A—O4A—C5A—C6A	−176.28 (13)	C20B—O4B—C5B—C6B	177.44 (13)
C3A—C4A—C5A—O4A	179.50 (13)	C3B—C4B—C5B—O4B	176.94 (13)
C3A—C4A—C5A—C6A	−0.1 (2)	C3B—C4B—C5B—C6B	−0.9 (2)
O2A—C1A—C6A—C5A	−179.87 (12)	O2B—C1B—C6B—C5B	−179.37 (12)
C2A—C1A—C6A—C5A	0.1 (2)	C2B—C1B—C6B—C5B	0.5 (2)
O2A—C1A—C6A—C7A	2.78 (19)	O2B—C1B—C6B—C7B	1.53 (19)
C2A—C1A—C6A—C7A	−177.23 (13)	C2B—C1B—C6B—C7B	−178.56 (13)
O4A—C5A—C6A—C1A	179.88 (12)	O4B—C5B—C6B—C1B	−177.51 (12)
C4A—C5A—C6A—C1A	−0.5 (2)	C4B—C5B—C6B—C1B	0.5 (2)
O4A—C5A—C6A—C7A	−2.9 (2)	O4B—C5B—C6B—C7B	1.5 (2)
C4A—C5A—C6A—C7A	176.72 (14)	C4B—C5B—C6B—C7B	179.55 (14)
C1A—C6A—C7A—C8A	−179.23 (15)	C1B—C6B—C7B—C8B	−169.16 (14)
C5A—C6A—C7A—C8A	3.7 (2)	C5B—C6B—C7B—C8B	11.8 (2)
C6A—C7A—C8A—C9A	−175.78 (14)	C6B—C7B—C8B—C9B	179.71 (13)
C7A—C8A—C9A—O1A	1.1 (2)	C7B—C8B—C9B—O1B	0.5 (2)
C7A—C8A—C9A—C10A	179.37 (14)	C7B—C8B—C9B—C10B	179.49 (13)
O1A—C9A—C10A—C11A	176.83 (15)	O1B—C9B—C10B—C11B	169.13 (14)
C8A—C9A—C10A—C11A	−1.4 (2)	C8B—C9B—C10B—C11B	−9.9 (2)
C9A—C10A—C11A—C12A	−178.22 (15)	C9B—C10B—C11B—C12B	−173.57 (14)
C10A—C11A—C12A—C13A	−6.6 (3)	C10B—C11B—C12B—C13B	−0.5 (3)
C10A—C11A—C12A—C17A	173.70 (15)	C10B—C11B—C12B—C17B	176.71 (15)
C21A—O5A—C13A—C14A	−0.1 (2)	C21B—O5B—C13B—C14B	−0.9 (2)
C21A—O5A—C13A—C12A	−179.80 (12)	C21B—O5B—C13B—C12B	179.03 (12)
C17A—C12A—C13A—O5A	179.72 (12)	C17B—C12B—C13B—O5B	179.84 (12)
C11A—C12A—C13A—O5A	0.1 (2)	C11B—C12B—C13B—O5B	−2.9 (2)
C17A—C12A—C13A—C14A	0.0 (2)	C17B—C12B—C13B—C14B	−0.3 (2)
C11A—C12A—C13A—C14A	−179.66 (14)	C11B—C12B—C13B—C14B	177.01 (13)
O5A—C13A—C14A—C15A	−179.28 (13)	O5B—C13B—C14B—C15B	179.29 (13)
C12A—C13A—C14A—C15A	0.4 (2)	C12B—C13B—C14B—C15B	−0.6 (2)
C22A—O6A—C15A—C14A	−0.7 (2)	C22B—O6B—C15B—C14B	1.6 (2)
C22A—O6A—C15A—C16A	179.22 (13)	C22B—O6B—C15B—C16B	−178.63 (14)
C13A—C14A—C15A—O6A	179.70 (14)	C13B—C14B—C15B—O6B	−179.60 (13)
C13A—C14A—C15A—C16A	−0.2 (2)	C13B—C14B—C15B—C16B	0.7 (2)
O6A—C15A—C16A—C17A	179.69 (13)	O6B—C15B—C16B—C17B	−179.62 (13)
C14A—C15A—C16A—C17A	−0.4 (2)	C14B—C15B—C16B—C17B	0.1 (2)
C23A—O7A—C17A—C16A	0.8 (2)	C23B—O7B—C17B—C16B	−4.9 (2)
C23A—O7A—C17A—C12A	−178.34 (13)	C23B—O7B—C17B—C12B	175.67 (13)
C15A—C16A—C17A—O7A	−178.23 (14)	C15B—C16B—C17B—O7B	179.56 (13)
C15A—C16A—C17A—C12A	0.8 (2)	C15B—C16B—C17B—C12B	−1.0 (2)
C13A—C12A—C17A—O7A	178.48 (12)	C13B—C12B—C17B—O7B	−179.45 (12)
C11A—C12A—C17A—O7A	−1.82 (19)	C11B—C12B—C17B—O7B	3.04 (18)
C13A—C12A—C17A—C16A	−0.6 (2)	C13B—C12B—C17B—C16B	1.1 (2)
C11A—C12A—C17A—C16A	179.06 (13)	C11B—C12B—C17B—C16B	−176.40 (13)

Cg1, Cg2 and Cg3 are the centroids of the C1A–C6A, C12A–C17A and C12B–C17B rings, respectively

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7AA···O1A	0.93	2.42	2.787 (2)	104
C7A—H7AA···O2A	0.93	2.29	2.704 (2)	106
C8A—H8AA···O4A	0.93	2.18	2.7844 (17)	121
C7B—H7BA···O1B	0.93	2.49	2.8351 (19)	102
C7B—H7BA···O2B	0.93	2.33	2.704 (2)	104
C8B—H8BA···O4B	0.93	2.16	2.7643 (18)	121
C10A—H10A···O5A	0.93	2.26	2.852 (2)	121
C10B—H10B···O5B	0.93	2.26	2.855 (2)	121
C11A—H11A···O7A	0.93	2.23	2.6599 (17)	108
C11B—H11B···O7B	0.93	2.23	2.6700 (17)	108
C20A—H20C···O1B	0.96	2.47	3.339 (2)	151
C20B—H20E···O1Ai	0.96	2.37	3.0238 (19)	125
C23A—H23C···O1Aii	0.96	2.39	3.319 (2)	162
C23B—H23D···O1Bii	0.96	2.41	3.262 (2)	148
C18A—H18C···Cg1iii	0.96	2.65	3.4503 (17)	141
C21A—H21C···Cg2iv	0.96	2.94	3.5813 (18)	126
C21B—H21E···Cg3v	0.96	2.72	3.5809 (16)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1A–C6A, C12A–C17A and C12B–C17B rings, respectively

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7A—H7AA⋯O1A	0.93	2.42	2.787 (2)	104
C7A—H7AA⋯O2A	0.93	2.29	2.704 (2)	106
C8A—H8AA⋯O4A	0.93	2.18	2.7844 (17)	121
C7B—H7BA⋯O1B	0.93	2.49	2.8351 (19)	102
C7B—H7BA⋯O2B	0.93	2.33	2.704 (2)	104
C8B—H8BA⋯O4B	0.93	2.16	2.7643 (18)	121
C10A—H10A⋯O5A	0.93	2.26	2.852 (2)	121
C10B—H10B⋯O5B	0.93	2.26	2.855 (2)	121
C11A—H11A⋯O7A	0.93	2.23	2.6599 (17)	108
C11B—H11B⋯O7B	0.93	2.23	2.6700 (17)	108
C20A—H20C⋯O1B	0.96	2.47	3.339 (2)	151
C20B—H20E⋯O1Ai	0.96	2.37	3.0238 (19)	125
C23A—H23C⋯O1Aii	0.96	2.39	3.319 (2)	162
C23B—H23D⋯O1Bii	0.96	2.41	3.262 (2)	148
C18A—H18C⋯Cg1iii	0.96	2.65	3.4503 (17)	141
C21A—H21C⋯Cg2iv	0.96	2.94	3.5813 (18)	126
C21B—H21E⋯Cg3v	0.96	2.72	3.5809 (16)	150

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