Redetermination of (E)-3-(anthracen-9-yl)-1-(2-hy-droxy-phen-yl)prop-2-en-1-one.

The redetermined structure of title chalcone derivative, C(23)H(16)O(2), corrects errors in the title, scheme and synthesis in the previous report of the same structure [Jasinski et al. (2011 ▶). Acta Cryst. E67, o795]. There are two independent mol-ecules in the asymmetric unit with slight differences in bond lengths and angles. The dihedral angle between the benzene ring and the anthracene ring system is 73.30 (4)° in one mol-ecule and 73.18 (4)° in the other. Both mol-ecules feature an intra-molecular O-H⋯O hydrogen bond, which generates an S(6) ring. In the crystal, mol-ecules are arranged into sheets lying parallel to the ac plane and further stacked along the b axis by π-π inter-actions with centroid-centroid distances in the range 3.6421 (6)-3.7607 (6) Å. The crystal structure is further stabilized by C-H⋯π inter-actions. There are also C⋯O [3.2159 (15) Å] short contacts.

Related literature

For the previous structure determination, see: Jasinski et al. (2011 ▶). For a related structure and background references, see: Joothamongkhon et al. (2010 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C23H16O2

M = 324.36

Monoclinic,

a = 14.0843 (2) Å

b = 13.7224 (2) Å

c = 16.9615 (3) Å

β = 101.411 (1)°

V = 3213.36 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.50 × 0.39 × 0.37 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.959, T max = 0.969

40230 measured reflections

9368 independent reflections

7868 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.132

S = 1.02

9368 reflections

459 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.54 e Å−3

Δρmin = −0.21 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 datablock(s) global, I. DOI: 10.1107/S1600536811034994/hb5945sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034994/hb5945Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034994/hb5945Isup3.cml

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

C23H16O2	F(000) = 1360
Mr = 324.36	Dx = 1.341 Mg m−3
Monoclinic, P21/c	Melting point = 431–432 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.0843 (2) Å	Cell parameters from 9368 reflections
b = 13.7224 (2) Å	θ = 1.9–30.0°
c = 16.9615 (3) Å	µ = 0.09 mm−1
β = 101.411 (1)°	T = 100 K
V = 3213.36 (9) Å3	Block, yellow
Z = 8	0.50 × 0.39 × 0.37 mm

Bruker APEXII CCD diffractometer	9368 independent reflections
Radiation source: sealed tube	7868 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 30.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −19→19
Tmin = 0.959, Tmax = 0.969	k = −17→19
40230 measured reflections	l = −23→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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0739P)2 + 1.125P] where P = (Fo2 + 2Fc2)/3
9368 reflections	(Δ/σ)max = 0.001
459 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.21 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 120.0 (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	0.23244 (6)	0.20731 (6)	0.25499 (5)	0.02242 (17)
O2A	0.12311 (6)	0.12104 (6)	0.13834 (5)	0.02449 (18)
C1A	0.44611 (8)	0.49417 (8)	0.37297 (6)	0.0174 (2)
C2A	0.50222 (8)	0.44622 (9)	0.32283 (6)	0.0227 (2)
H2AA	0.4773	0.3914	0.2936	0.027*
C3A	0.59212 (9)	0.48005 (11)	0.31737 (7)	0.0271 (3)
H3AA	0.6279	0.4475	0.2850	0.033*
C4A	0.63149 (9)	0.56412 (11)	0.36045 (7)	0.0279 (3)
H4AA	0.6923	0.5867	0.3556	0.033*
C5A	0.58036 (8)	0.61172 (9)	0.40878 (7)	0.0239 (2)
H5AA	0.6069	0.6666	0.4371	0.029*
C6A	0.48658 (8)	0.57869 (8)	0.41671 (6)	0.0185 (2)
C7A	0.43416 (8)	0.62652 (8)	0.46690 (7)	0.0194 (2)
H7AA	0.4608	0.6811	0.4955	0.023*
C8A	0.34265 (8)	0.59435 (8)	0.47522 (6)	0.0173 (2)
C9A	0.29196 (9)	0.64164 (8)	0.52973 (7)	0.0210 (2)
H9AA	0.3197	0.6953	0.5590	0.025*
C10A	0.20378 (9)	0.60920 (9)	0.53942 (7)	0.0231 (2)
H10A	0.1713	0.6412	0.5746	0.028*
C11A	0.16130 (8)	0.52659 (9)	0.49592 (7)	0.0217 (2)
H11A	0.1012	0.5045	0.5032	0.026*
C12A	0.20734 (8)	0.47903 (8)	0.44350 (6)	0.0188 (2)
H12A	0.1782	0.4248	0.4159	0.023*
C13A	0.29970 (8)	0.51123 (8)	0.43031 (6)	0.01584 (19)
C14A	0.35199 (8)	0.46226 (8)	0.37893 (6)	0.01602 (19)
C15A	0.31128 (8)	0.37739 (8)	0.33147 (6)	0.0184 (2)
H15A	0.3487	0.3211	0.3358	0.022*
C16A	0.22424 (8)	0.37492 (8)	0.28239 (6)	0.0199 (2)
H16A	0.1840	0.4292	0.2782	0.024*
C17A	0.19193 (8)	0.28682 (8)	0.23504 (6)	0.0179 (2)
C18A	0.11383 (8)	0.29411 (8)	0.16329 (6)	0.0172 (2)
C19A	0.08536 (8)	0.20943 (9)	0.11699 (6)	0.0193 (2)
C20A	0.01483 (9)	0.21635 (10)	0.04625 (7)	0.0242 (2)
H20A	−0.0024	0.1613	0.0147	0.029*
C21A	−0.02897 (9)	0.30437 (10)	0.02334 (7)	0.0252 (2)
H21A	−0.0761	0.3080	−0.0234	0.030*
C22A	−0.00370 (9)	0.38831 (9)	0.06921 (7)	0.0240 (2)
H22A	−0.0346	0.4472	0.0538	0.029*
C23A	0.06780 (8)	0.38290 (9)	0.13788 (7)	0.0209 (2)
H23A	0.0858	0.4390	0.1679	0.025*
O1B	0.18383 (6)	0.94230 (6)	0.26687 (5)	0.02468 (18)
O2B	0.03389 (7)	0.89265 (7)	0.16165 (5)	0.02348 (18)
C1B	0.50277 (8)	0.87960 (7)	0.47232 (6)	0.01604 (19)
C2B	0.53592 (8)	0.88359 (8)	0.39761 (6)	0.0194 (2)
H2BA	0.4912	0.8925	0.3499	0.023*
C3B	0.63166 (9)	0.87455 (9)	0.39523 (7)	0.0221 (2)
H3BA	0.6512	0.8783	0.3461	0.026*
C4B	0.70218 (9)	0.85953 (9)	0.46673 (7)	0.0223 (2)
H4BA	0.7673	0.8534	0.4641	0.027*
C5B	0.67406 (8)	0.85419 (8)	0.53925 (7)	0.0198 (2)
H5BA	0.7203	0.8442	0.5859	0.024*
C6B	0.57425 (8)	0.86375 (8)	0.54417 (6)	0.0166 (2)
C7B	0.54489 (8)	0.85640 (8)	0.61815 (6)	0.0173 (2)
H7BA	0.5912	0.8461	0.6647	0.021*
C8B	0.44772 (8)	0.86415 (8)	0.62337 (6)	0.0175 (2)
C9B	0.41872 (9)	0.85451 (9)	0.69944 (6)	0.0220 (2)
H9BA	0.4652	0.8414	0.7453	0.026*
C10B	0.32440 (9)	0.86416 (10)	0.70549 (7)	0.0253 (2)
H10B	0.3065	0.8564	0.7550	0.030*
C11B	0.25298 (9)	0.88619 (9)	0.63594 (7)	0.0233 (2)
H11B	0.1888	0.8945	0.6407	0.028*
C12B	0.27755 (8)	0.89535 (8)	0.56208 (7)	0.0196 (2)
H12B	0.2298	0.9104	0.5175	0.024*
C13B	0.37537 (8)	0.88220 (8)	0.55225 (6)	0.0165 (2)
C14B	0.40387 (8)	0.88795 (7)	0.47662 (6)	0.01590 (19)
C15B	0.33125 (8)	0.90127 (8)	0.40140 (6)	0.0180 (2)
H15B	0.3405	0.9525	0.3679	0.022*
C16B	0.25332 (8)	0.84486 (8)	0.37825 (6)	0.0189 (2)
H16B	0.2422	0.7934	0.4110	0.023*
C17B	0.18418 (8)	0.86241 (8)	0.30157 (6)	0.0181 (2)
C18B	0.11590 (8)	0.78474 (8)	0.26706 (6)	0.0167 (2)
C19B	0.04372 (8)	0.80431 (8)	0.19787 (6)	0.0184 (2)
C20B	−0.02191 (8)	0.73166 (9)	0.16524 (6)	0.0215 (2)
H20B	−0.0693	0.7450	0.1200	0.026*
C21B	−0.01681 (8)	0.64008 (9)	0.19984 (7)	0.0229 (2)
H21B	−0.0609	0.5922	0.1778	0.027*
C22B	0.05418 (9)	0.61899 (9)	0.26782 (7)	0.0217 (2)
H22B	0.0578	0.5572	0.2907	0.026*
C23B	0.11898 (8)	0.69067 (8)	0.30083 (6)	0.0190 (2)
H23B	0.1656	0.6765	0.3463	0.023*
H1OA	0.1696 (15)	0.1326 (15)	0.1845 (13)	0.052 (6)*
H1OB	0.0847 (15)	0.9246 (15)	0.1878 (12)	0.052 (6)*

	U11	U22	U33	U12	U13	U23
O1A	0.0194 (4)	0.0219 (4)	0.0243 (4)	0.0023 (3)	0.0002 (3)	−0.0037 (3)
O2A	0.0203 (4)	0.0243 (4)	0.0272 (4)	0.0028 (3)	0.0006 (3)	−0.0089 (3)
C1A	0.0145 (5)	0.0220 (5)	0.0147 (4)	−0.0008 (4)	0.0008 (3)	0.0034 (4)
C2A	0.0185 (5)	0.0334 (6)	0.0157 (4)	0.0012 (4)	0.0021 (4)	0.0007 (4)
C3A	0.0182 (5)	0.0450 (8)	0.0187 (5)	0.0036 (5)	0.0048 (4)	0.0056 (5)
C4A	0.0159 (5)	0.0417 (7)	0.0254 (5)	−0.0036 (5)	0.0026 (4)	0.0124 (5)
C5A	0.0177 (5)	0.0273 (6)	0.0247 (5)	−0.0061 (4)	−0.0005 (4)	0.0094 (4)
C6A	0.0166 (5)	0.0195 (5)	0.0181 (4)	−0.0027 (4)	0.0004 (4)	0.0062 (4)
C7A	0.0206 (5)	0.0150 (5)	0.0209 (5)	−0.0032 (4)	−0.0001 (4)	0.0028 (4)
C8A	0.0187 (5)	0.0149 (5)	0.0173 (4)	0.0000 (4)	0.0011 (4)	0.0024 (3)
C9A	0.0255 (6)	0.0155 (5)	0.0210 (5)	0.0025 (4)	0.0023 (4)	−0.0006 (4)
C10A	0.0257 (6)	0.0226 (6)	0.0216 (5)	0.0057 (4)	0.0065 (4)	0.0009 (4)
C11A	0.0182 (5)	0.0245 (6)	0.0232 (5)	0.0006 (4)	0.0062 (4)	0.0034 (4)
C12A	0.0171 (5)	0.0193 (5)	0.0199 (5)	−0.0025 (4)	0.0030 (4)	0.0013 (4)
C13A	0.0159 (5)	0.0155 (5)	0.0154 (4)	−0.0003 (4)	0.0015 (3)	0.0019 (3)
C14A	0.0148 (5)	0.0178 (5)	0.0148 (4)	−0.0014 (4)	0.0013 (3)	0.0010 (3)
C15A	0.0176 (5)	0.0193 (5)	0.0182 (5)	−0.0005 (4)	0.0034 (4)	−0.0013 (4)
C16A	0.0194 (5)	0.0200 (5)	0.0192 (5)	0.0001 (4)	0.0016 (4)	−0.0035 (4)
C17A	0.0142 (5)	0.0221 (5)	0.0175 (4)	−0.0013 (4)	0.0037 (4)	−0.0028 (4)
C18A	0.0139 (5)	0.0222 (5)	0.0156 (4)	−0.0021 (4)	0.0036 (3)	−0.0017 (4)
C19A	0.0148 (5)	0.0242 (5)	0.0197 (5)	−0.0007 (4)	0.0055 (4)	−0.0046 (4)
C20A	0.0194 (5)	0.0319 (6)	0.0201 (5)	−0.0018 (5)	0.0012 (4)	−0.0084 (4)
C21A	0.0207 (5)	0.0365 (7)	0.0172 (5)	−0.0010 (5)	0.0010 (4)	−0.0010 (4)
C22A	0.0230 (6)	0.0274 (6)	0.0207 (5)	0.0000 (5)	0.0024 (4)	0.0045 (4)
C23A	0.0216 (5)	0.0221 (5)	0.0188 (5)	−0.0030 (4)	0.0032 (4)	0.0010 (4)
O1B	0.0254 (4)	0.0208 (4)	0.0249 (4)	−0.0021 (3)	−0.0021 (3)	0.0047 (3)
O2B	0.0221 (4)	0.0248 (4)	0.0214 (4)	0.0002 (3)	−0.0009 (3)	0.0023 (3)
C1B	0.0177 (5)	0.0129 (5)	0.0173 (4)	−0.0021 (4)	0.0028 (4)	−0.0009 (3)
C2B	0.0223 (5)	0.0185 (5)	0.0173 (5)	−0.0008 (4)	0.0038 (4)	0.0005 (4)
C3B	0.0242 (6)	0.0221 (5)	0.0217 (5)	−0.0015 (4)	0.0088 (4)	−0.0001 (4)
C4B	0.0179 (5)	0.0230 (6)	0.0273 (5)	−0.0004 (4)	0.0074 (4)	−0.0004 (4)
C5B	0.0165 (5)	0.0194 (5)	0.0228 (5)	−0.0003 (4)	0.0023 (4)	−0.0002 (4)
C6B	0.0173 (5)	0.0136 (5)	0.0186 (5)	−0.0009 (4)	0.0027 (4)	−0.0010 (3)
C7B	0.0179 (5)	0.0162 (5)	0.0169 (4)	−0.0013 (4)	0.0011 (4)	−0.0011 (3)
C8B	0.0195 (5)	0.0159 (5)	0.0169 (4)	−0.0029 (4)	0.0033 (4)	−0.0027 (3)
C9B	0.0234 (6)	0.0260 (6)	0.0163 (5)	−0.0046 (4)	0.0031 (4)	−0.0032 (4)
C10B	0.0254 (6)	0.0324 (6)	0.0193 (5)	−0.0059 (5)	0.0078 (4)	−0.0065 (4)
C11B	0.0183 (5)	0.0278 (6)	0.0249 (5)	−0.0035 (4)	0.0067 (4)	−0.0079 (4)
C12B	0.0177 (5)	0.0189 (5)	0.0219 (5)	−0.0018 (4)	0.0031 (4)	−0.0042 (4)
C13B	0.0172 (5)	0.0139 (5)	0.0180 (4)	−0.0020 (4)	0.0026 (4)	−0.0028 (3)
C14B	0.0170 (5)	0.0129 (5)	0.0171 (4)	−0.0015 (4)	0.0018 (4)	−0.0006 (3)
C15B	0.0193 (5)	0.0171 (5)	0.0172 (4)	0.0005 (4)	0.0023 (4)	0.0003 (4)
C16B	0.0188 (5)	0.0186 (5)	0.0182 (5)	−0.0012 (4)	0.0010 (4)	0.0013 (4)
C17B	0.0162 (5)	0.0194 (5)	0.0183 (4)	−0.0002 (4)	0.0026 (4)	−0.0006 (4)
C18B	0.0144 (5)	0.0203 (5)	0.0155 (4)	0.0000 (4)	0.0035 (3)	−0.0020 (4)
C19B	0.0164 (5)	0.0231 (5)	0.0164 (4)	0.0019 (4)	0.0046 (4)	−0.0015 (4)
C20B	0.0163 (5)	0.0305 (6)	0.0173 (5)	−0.0011 (4)	0.0028 (4)	−0.0052 (4)
C21B	0.0191 (5)	0.0264 (6)	0.0237 (5)	−0.0049 (4)	0.0057 (4)	−0.0081 (4)
C22B	0.0212 (5)	0.0208 (5)	0.0241 (5)	−0.0019 (4)	0.0069 (4)	−0.0028 (4)
C23B	0.0172 (5)	0.0216 (5)	0.0184 (5)	0.0002 (4)	0.0042 (4)	−0.0014 (4)

O1A—C17A	1.2466 (14)	O1B—C17B	1.2438 (14)
O2A—C19A	1.3449 (14)	O2B—C19B	1.3537 (14)
O2A—H1OA	0.93 (2)	O2B—H1OB	0.88 (2)
C1A—C14A	1.4186 (14)	C1B—C14B	1.4138 (15)
C1A—C2A	1.4306 (15)	C1B—C6B	1.4354 (14)
C1A—C6A	1.4329 (16)	C1B—C2B	1.4356 (14)
C2A—C3A	1.3688 (17)	C2B—C3B	1.3627 (16)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.418 (2)	C3B—C4B	1.4224 (17)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.3606 (19)	C4B—C5B	1.3668 (15)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.4277 (15)	C5B—C6B	1.4307 (15)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.3962 (16)	C6B—C7B	1.4003 (14)
C7A—C8A	1.3957 (15)	C7B—C8B	1.3930 (15)
C7A—H7AA	0.9300	C7B—H7BA	0.9300
C8A—C9A	1.4306 (15)	C8B—C9B	1.4344 (14)
C8A—C13A	1.4371 (15)	C8B—C13B	1.4383 (15)
C9A—C10A	1.3595 (17)	C9B—C10B	1.3590 (17)
C9A—H9AA	0.9300	C9B—H9BA	0.9300
C10A—C11A	1.4187 (17)	C10B—C11B	1.4231 (17)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.3657 (15)	C11B—C12B	1.3699 (15)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.4327 (15)	C12B—C13B	1.4315 (15)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.4167 (14)	C13B—C14B	1.4200 (14)
C14A—C15A	1.4664 (15)	C14B—C15B	1.4802 (14)
C15A—C16A	1.3392 (15)	C15B—C16B	1.3370 (15)
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—C17A	1.4728 (15)	C16B—C17B	1.4821 (14)
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—C18A	1.4736 (14)	C17B—C18B	1.4767 (15)
C18A—C23A	1.4072 (16)	C18B—C23B	1.4095 (15)
C18A—C19A	1.4153 (15)	C18B—C19B	1.4179 (14)
C19A—C20A	1.4014 (15)	C19B—C20B	1.3972 (16)
C20A—C21A	1.3768 (18)	C20B—C21B	1.3828 (18)
C20A—H20A	0.9300	C20B—H20B	0.9300
C21A—C22A	1.3962 (17)	C21B—C22B	1.3989 (17)
C21A—H21A	0.9300	C21B—H21B	0.9300
C22A—C23A	1.3828 (16)	C22B—C23B	1.3827 (16)
C22A—H22A	0.9300	C22B—H22B	0.9300
C23A—H23A	0.9300	C23B—H23B	0.9300
C19A—O2A—H1OA	104.3 (13)	C19B—O2B—H1OB	102.6 (13)
C14A—C1A—C2A	122.30 (10)	C14B—C1B—C6B	120.07 (9)
C14A—C1A—C6A	119.63 (10)	C14B—C1B—C2B	122.56 (10)
C2A—C1A—C6A	118.04 (10)	C6B—C1B—C2B	117.34 (10)
C3A—C2A—C1A	120.75 (12)	C3B—C2B—C1B	121.28 (10)
C3A—C2A—H2AA	119.6	C3B—C2B—H2BA	119.4
C1A—C2A—H2AA	119.6	C1B—C2B—H2BA	119.4
C2A—C3A—C4A	120.91 (11)	C2B—C3B—C4B	121.07 (10)
C2A—C3A—H3AA	119.5	C2B—C3B—H3BA	119.5
C4A—C3A—H3AA	119.5	C4B—C3B—H3BA	119.5
C5A—C4A—C3A	120.09 (11)	C5B—C4B—C3B	119.82 (11)
C5A—C4A—H4AA	120.0	C5B—C4B—H4BA	120.1
C3A—C4A—H4AA	120.0	C3B—C4B—H4BA	120.1
C4A—C5A—C6A	120.94 (12)	C4B—C5B—C6B	120.71 (10)
C4A—C5A—H5AA	119.5	C4B—C5B—H5BA	119.6
C6A—C5A—H5AA	119.5	C6B—C5B—H5BA	119.6
C7A—C6A—C5A	121.26 (11)	C7B—C6B—C5B	120.89 (10)
C7A—C6A—C1A	119.48 (10)	C7B—C6B—C1B	119.33 (10)
C5A—C6A—C1A	119.26 (10)	C5B—C6B—C1B	119.77 (9)
C8A—C7A—C6A	121.55 (10)	C8B—C7B—C6B	121.30 (10)
C8A—C7A—H7AA	119.2	C8B—C7B—H7BA	119.4
C6A—C7A—H7AA	119.2	C6B—C7B—H7BA	119.4
C7A—C8A—C9A	120.72 (10)	C7B—C8B—C9B	120.55 (10)
C7A—C8A—C13A	119.85 (10)	C7B—C8B—C13B	120.12 (9)
C9A—C8A—C13A	119.41 (10)	C9B—C8B—C13B	119.33 (10)
C10A—C9A—C8A	120.95 (11)	C10B—C9B—C8B	121.02 (11)
C10A—C9A—H9AA	119.5	C10B—C9B—H9BA	119.5
C8A—C9A—H9AA	119.5	C8B—C9B—H9BA	119.5
C9A—C10A—C11A	120.00 (10)	C9B—C10B—C11B	119.96 (10)
C9A—C10A—H10A	120.0	C9B—C10B—H10B	120.0
C11A—C10A—H10A	120.0	C11B—C10B—H10B	120.0
C12A—C11A—C10A	120.98 (11)	C12B—C11B—C10B	120.83 (11)
C12A—C11A—H11A	119.5	C12B—C11B—H11B	119.6
C10A—C11A—H11A	119.5	C10B—C11B—H11B	119.6
C11A—C12A—C13A	121.14 (10)	C11B—C12B—C13B	121.21 (11)
C11A—C12A—H12A	119.4	C11B—C12B—H12B	119.4
C13A—C12A—H12A	119.4	C13B—C12B—H12B	119.4
C14A—C13A—C12A	123.25 (10)	C14B—C13B—C12B	123.29 (10)
C14A—C13A—C8A	119.15 (9)	C14B—C13B—C8B	119.16 (10)
C12A—C13A—C8A	117.51 (9)	C12B—C13B—C8B	117.54 (9)
C13A—C14A—C1A	120.29 (10)	C1B—C14B—C13B	119.97 (9)
C13A—C14A—C15A	121.33 (9)	C1B—C14B—C15B	119.04 (9)
C1A—C14A—C15A	118.38 (9)	C13B—C14B—C15B	120.98 (10)
C16A—C15A—C14A	124.87 (10)	C16B—C15B—C14B	124.67 (10)
C16A—C15A—H15A	117.6	C16B—C15B—H15B	117.7
C14A—C15A—H15A	117.6	C14B—C15B—H15B	117.7
C15A—C16A—C17A	120.39 (10)	C15B—C16B—C17B	121.49 (10)
C15A—C16A—H16A	119.8	C15B—C16B—H16B	119.3
C17A—C16A—H16A	119.8	C17B—C16B—H16B	119.3
O1A—C17A—C16A	119.67 (10)	O1B—C17B—C18B	120.49 (10)
O1A—C17A—C18A	120.69 (10)	O1B—C17B—C16B	119.92 (10)
C16A—C17A—C18A	119.62 (10)	C18B—C17B—C16B	119.59 (10)
C23A—C18A—C19A	118.57 (10)	C23B—C18B—C19B	117.98 (10)
C23A—C18A—C17A	122.35 (10)	C23B—C18B—C17B	122.32 (10)
C19A—C18A—C17A	119.07 (10)	C19B—C18B—C17B	119.70 (10)
O2A—C19A—C20A	117.85 (10)	O2B—C19B—C20B	117.32 (10)
O2A—C19A—C18A	122.52 (10)	O2B—C19B—C18B	122.50 (10)
C20A—C19A—C18A	119.63 (11)	C20B—C19B—C18B	120.17 (10)
C21A—C20A—C19A	120.22 (11)	C21B—C20B—C19B	120.36 (10)
C21A—C20A—H20A	119.9	C21B—C20B—H20B	119.8
C19A—C20A—H20A	119.9	C19B—C20B—H20B	119.8
C20A—C21A—C22A	121.06 (11)	C20B—C21B—C22B	120.44 (11)
C20A—C21A—H21A	119.5	C20B—C21B—H21B	119.8
C22A—C21A—H21A	119.5	C22B—C21B—H21B	119.8
C23A—C22A—C21A	119.21 (11)	C23B—C22B—C21B	119.57 (11)
C23A—C22A—H22A	120.4	C23B—C22B—H22B	120.2
C21A—C22A—H22A	120.4	C21B—C22B—H22B	120.2
C22A—C23A—C18A	121.27 (11)	C22B—C23B—C18B	121.48 (10)
C22A—C23A—H23A	119.4	C22B—C23B—H23B	119.3
C18A—C23A—H23A	119.4	C18B—C23B—H23B	119.3
C14A—C1A—C2A—C3A	178.79 (11)	C14B—C1B—C2B—C3B	−179.47 (10)
C6A—C1A—C2A—C3A	0.37 (16)	C6B—C1B—C2B—C3B	−1.22 (16)
C1A—C2A—C3A—C4A	−0.77 (18)	C1B—C2B—C3B—C4B	0.83 (18)
C2A—C3A—C4A—C5A	0.78 (18)	C2B—C3B—C4B—C5B	−0.13 (18)
C3A—C4A—C5A—C6A	−0.38 (17)	C3B—C4B—C5B—C6B	−0.13 (18)
C4A—C5A—C6A—C7A	179.27 (11)	C4B—C5B—C6B—C7B	178.72 (11)
C4A—C5A—C6A—C1A	−0.01 (16)	C4B—C5B—C6B—C1B	−0.31 (16)
C14A—C1A—C6A—C7A	2.27 (15)	C14B—C1B—C6B—C7B	0.20 (15)
C2A—C1A—C6A—C7A	−179.27 (10)	C2B—C1B—C6B—C7B	−178.10 (10)
C14A—C1A—C6A—C5A	−178.44 (10)	C14B—C1B—C6B—C5B	179.24 (10)
C2A—C1A—C6A—C5A	0.03 (15)	C2B—C1B—C6B—C5B	0.95 (15)
C5A—C6A—C7A—C8A	−179.69 (10)	C5B—C6B—C7B—C8B	−179.03 (10)
C1A—C6A—C7A—C8A	−0.41 (16)	C1B—C6B—C7B—C8B	0.01 (16)
C6A—C7A—C8A—C9A	177.12 (10)	C6B—C7B—C8B—C9B	178.75 (10)
C6A—C7A—C8A—C13A	−1.18 (16)	C6B—C7B—C8B—C13B	−1.40 (16)
C7A—C8A—C9A—C10A	−178.48 (10)	C7B—C8B—C9B—C10B	178.48 (11)
C13A—C8A—C9A—C10A	−0.17 (16)	C13B—C8B—C9B—C10B	−1.37 (17)
C8A—C9A—C10A—C11A	0.81 (17)	C8B—C9B—C10B—C11B	−1.32 (19)
C9A—C10A—C11A—C12A	−0.55 (17)	C9B—C10B—C11B—C12B	1.74 (19)
C10A—C11A—C12A—C13A	−0.37 (17)	C10B—C11B—C12B—C13B	0.62 (18)
C11A—C12A—C13A—C14A	177.54 (10)	C11B—C12B—C13B—C14B	177.98 (10)
C11A—C12A—C13A—C8A	0.98 (16)	C11B—C12B—C13B—C8B	−3.23 (16)
C7A—C8A—C13A—C14A	0.91 (15)	C7B—C8B—C13B—C14B	2.56 (15)
C9A—C8A—C13A—C14A	−177.41 (10)	C9B—C8B—C13B—C14B	−177.58 (10)
C7A—C8A—C13A—C12A	177.61 (10)	C7B—C8B—C13B—C12B	−176.28 (10)
C9A—C8A—C13A—C12A	−0.71 (15)	C9B—C8B—C13B—C12B	3.57 (15)
C12A—C13A—C14A—C1A	−175.56 (10)	C6B—C1B—C14B—C13B	1.00 (15)
C8A—C13A—C14A—C1A	0.95 (15)	C2B—C1B—C14B—C13B	179.20 (10)
C12A—C13A—C14A—C15A	3.81 (16)	C6B—C1B—C14B—C15B	−178.15 (9)
C8A—C13A—C14A—C15A	−179.68 (9)	C2B—C1B—C14B—C15B	0.05 (16)
C2A—C1A—C14A—C13A	179.07 (10)	C12B—C13B—C14B—C1B	176.41 (10)
C6A—C1A—C14A—C13A	−2.53 (15)	C8B—C13B—C14B—C1B	−2.36 (15)
C2A—C1A—C14A—C15A	−0.31 (15)	C12B—C13B—C14B—C15B	−4.45 (16)
C6A—C1A—C14A—C15A	178.08 (9)	C8B—C13B—C14B—C15B	176.78 (10)
C13A—C14A—C15A—C16A	52.54 (15)	C1B—C14B—C15B—C16B	125.91 (12)
C1A—C14A—C15A—C16A	−128.08 (12)	C13B—C14B—C15B—C16B	−53.23 (16)
C14A—C15A—C16A—C17A	177.64 (10)	C14B—C15B—C16B—C17B	−179.49 (10)
C15A—C16A—C17A—O1A	18.56 (16)	C15B—C16B—C17B—O1B	−17.28 (17)
C15A—C16A—C17A—C18A	−159.78 (10)	C15B—C16B—C17B—C18B	162.91 (10)
O1A—C17A—C18A—C23A	−178.62 (10)	O1B—C17B—C18B—C23B	174.78 (10)
C16A—C17A—C18A—C23A	−0.30 (15)	C16B—C17B—C18B—C23B	−5.41 (15)
O1A—C17A—C18A—C19A	−0.13 (15)	O1B—C17B—C18B—C19B	−5.71 (16)
C16A—C17A—C18A—C19A	178.20 (9)	C16B—C17B—C18B—C19B	174.10 (9)
C23A—C18A—C19A—O2A	−177.65 (10)	C23B—C18B—C19B—O2B	179.06 (9)
C17A—C18A—C19A—O2A	3.80 (15)	C17B—C18B—C19B—O2B	−0.47 (15)
C23A—C18A—C19A—C20A	1.96 (15)	C23B—C18B—C19B—C20B	0.22 (15)
C17A—C18A—C19A—C20A	−176.59 (10)	C17B—C18B—C19B—C20B	−179.31 (10)
O2A—C19A—C20A—C21A	177.39 (11)	O2B—C19B—C20B—C21B	−179.19 (10)
C18A—C19A—C20A—C21A	−2.24 (17)	C18B—C19B—C20B—C21B	−0.28 (16)
C19A—C20A—C21A—C22A	0.64 (18)	C19B—C20B—C21B—C22B	−0.11 (17)
C20A—C21A—C22A—C23A	1.23 (18)	C20B—C21B—C22B—C23B	0.56 (17)
C21A—C22A—C23A—C18A	−1.48 (17)	C21B—C22B—C23B—C18B	−0.63 (16)
C19A—C18A—C23A—C22A	−0.11 (16)	C19B—C18B—C23B—C22B	0.24 (15)
C17A—C18A—C23A—C22A	178.39 (10)	C17B—C18B—C23B—C22B	179.76 (10)

Cg1, Cg3, Cg5, Cg6 and Cg7 are the centroids of the C1A–C6A, C8A–C13A, C1B–C6B, C1B/C6B–C8B/C13B–C14B and C8B–C13B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H1OA···O1A	0.93 (2)	1.69 (2)	2.5459 (12)	152.2 (19)
O2B—H1OB···O1B	0.88 (2)	1.75 (2)	2.5725 (13)	154.2 (19)
C5A—H5AA···Cg5	0.93	2.84	3.6754 (13)	151
C7A—H7AA···Cg6	0.93	2.76	3.6440 (12)	158
C9A—H9AA···Cg7	0.93	2.73	3.6325 (12)	164
C9B—H9BA···Cg1i	0.93	2.76	3.4023 (12)	127
C23B—H23B···Cg3	0.93	2.91	3.7661 (11)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg3, Cg5, Cg6 and Cg7 are the centroids of the C1A–C6A, C8A–C13A, C1B–C6B, C1B/C6B–C8B/C13B–C14B and C8B–C13B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2A—H1OA⋯O1A	0.93 (2)	1.69 (2)	2.5459 (12)	152.2 (19)
O2B—H1OB⋯O1B	0.88 (2)	1.75 (2)	2.5725 (13)	154.2 (19)
C5A—H5AA⋯Cg5	0.93	2.84	3.6754 (13)	151
C7A—H7AA⋯Cg6	0.93	2.76	3.6440 (12)	158
C9A—H9AA⋯Cg7	0.93	2.73	3.6325 (12)	164
C9B—H9BA⋯Cg1i	0.93	2.76	3.4023 (12)	127
C23B—H23B⋯Cg3	0.93	2.91	3.7661 (11)	154

Symmetry code: (i) .