Ethyl (E)-3-(anthracen-9-yl)prop-2-enoate.

In the asymmetric unit of the title compound, C19H16O2, there are two symmetry-independent mol-ecules (A and B) that differ in the conformation of the ester eth-oxy group. In the crystal, the mol-ecules form inversion dimers via pairs of C-H⋯O inter-actions. Within the dimers, the anthracenyl units have inter-planar distances of 0.528 (2) and 0.479 (2) Å for dimers of mol-ecules A and B, respectively. Another short C-H⋯O contact between symmetry-independent dimers links them into columns parallel to [10-1]. These columns are arranged into (111) layers and there are π-π stacking inter-actions [centroid-centroid distances = 3.6446 (15) and 3.6531 (15) Å] between the anthracenyl units from the neighbouring columns. In addition, there are C-H⋯π inter-actions between the anthracenyl unit of dimers A and dimers B within the same column.

Related literature

For an analogous preparation of the title compound, see: Nguyen & Weizman (2007 ▶). For modeling of the title compound at the B3LYP/6–31G* level, see: Coleman (2007 ▶). For crystal structures of photodimerizable aryl­enes, see: Vishnumurthy et al. (2002 ▶); Mascitti & Corey (2006 ▶); Sonoda (2011 ▶); Schmidt (1964 ▶). For the photodimerization of anthracenes in the crystal, see: Schmidt (1971 ▶); Ihmels et al. (2000 ▶).

Experimental

Crystal data

C19H16O2

M = 276.32

Triclinic,

a = 8.8700 (5) Å

b = 12.8918 (7) Å

c = 13.1062 (7) Å

α = 84.389 (4)°

β = 84.620 (4)°

γ = 70.771 (5)°

V = 1405.28 (13) Å3

Z = 4

Cu Kα radiation

μ = 0.66 mm−1

T = 291 K

0.22 × 0.11 × 0.09 mm

Data collection

Agilent SuperNova Dual Atlas diffractometer

Absorption correction: Gaussian (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.889, T max = 0.942

11350 measured reflections

4901 independent reflections

4250 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.171

S = 1.10

4901 reflections

381 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) within OLEX2 (Dolomanov et al., 2009 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812051033/gk2545sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051033/gk2545Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051033/gk2545Isup3.cml

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

C19H16O2	F(000) = 584
Mr = 276.32	Dx = 1.306 Mg m−3
Triclinic, P1	Melting point: 353.6 K
a = 8.8700 (5) Å	Cu Kα radiation, λ = 1.5418 Å
b = 12.8918 (7) Å	Cell parameters from 4999 reflections
c = 13.1062 (7) Å	θ = 3.6–76.1°
α = 84.389 (4)°	µ = 0.66 mm−1
β = 84.620 (4)°	T = 291 K
γ = 70.771 (5)°	Block, translucent intense yellow
V = 1405.28 (13) Å3	0.22 × 0.11 × 0.09 mm
Z = 4

Agilent SuperNova Dual Atlas diffractometer	4901 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	4250 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.025
Detector resolution: 10.4127 pixels mm-1	θmax = 66.0°, θmin = 3.6°
ω scans	h = −10→10
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2012)	k = −10→15
Tmin = 0.889, Tmax = 0.942	l = −15→15
11350 measured reflections

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0665P)2 + 2.0996P] where P = (Fo2 + 2Fc2)/3
4901 reflections	(Δ/σ)max = 0.001
381 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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
C10A	1.2110 (3)	0.6510 (2)	1.14911 (19)	0.0233 (6)
C10B	0.5292 (3)	0.5977 (2)	0.65022 (19)	0.0226 (5)
C11A	1.2162 (3)	0.7552 (2)	1.1299 (2)	0.0248 (6)
C11B	0.6625 (3)	0.6286 (2)	0.6358 (2)	0.0252 (6)
C12A	1.0823 (3)	0.8399 (2)	1.0900 (2)	0.0247 (6)
C12B	0.8112 (3)	0.5498 (2)	0.60494 (19)	0.0232 (5)
C13A	0.9467 (3)	0.8181 (2)	1.07279 (19)	0.0217 (5)
C13B	0.8205 (3)	0.4465 (2)	0.58699 (18)	0.0211 (5)
C14A	0.9348 (3)	0.7097 (2)	1.09399 (18)	0.0185 (5)
C14B	0.6822 (3)	0.4108 (2)	0.59782 (18)	0.0188 (5)
C15A	0.6563 (3)	0.7738 (2)	1.03919 (19)	0.0189 (5)
C15B	0.8340 (3)	0.2220 (2)	0.53924 (19)	0.0192 (5)
C16A	0.5756 (3)	0.7705 (2)	0.95986 (19)	0.0195 (5)
C16B	0.9259 (3)	0.2403 (2)	0.45797 (19)	0.0192 (5)
C17A	0.4367 (3)	0.8650 (2)	0.92781 (19)	0.0187 (5)
C17B	1.0714 (3)	0.1530 (2)	0.42227 (19)	0.0186 (5)
C18A	0.2639 (3)	0.9408 (2)	0.7928 (2)	0.0241 (6)
C18B	1.2700 (3)	0.1079 (2)	0.2833 (2)	0.0253 (6)
C19A	0.2370 (3)	0.9096 (2)	0.6907 (2)	0.0287 (6)
C19B	1.2224 (4)	0.0354 (3)	0.2187 (2)	0.0381 (7)
C1A	0.7963 (3)	0.6843 (2)	1.07686 (18)	0.0179 (5)
C1B	0.6856 (3)	0.3039 (2)	0.57936 (18)	0.0192 (5)
C2A	0.7926 (3)	0.5751 (2)	1.09581 (18)	0.0182 (5)
C2B	0.5461 (3)	0.2731 (2)	0.59795 (18)	0.0187 (5)
C3A	0.6545 (3)	0.5437 (2)	1.08596 (18)	0.0205 (5)
C3B	0.5413 (3)	0.1676 (2)	0.57712 (19)	0.0218 (5)
C4A	0.6582 (3)	0.4370 (2)	1.10317 (19)	0.0238 (5)
C4B	0.4033 (3)	0.1420 (2)	0.5929 (2)	0.0242 (5)
C5A	0.7991 (3)	0.3526 (2)	1.1330 (2)	0.0257 (6)
C5B	0.2589 (3)	0.2189 (2)	0.6321 (2)	0.0234 (5)
C6A	0.9315 (3)	0.3792 (2)	1.14713 (19)	0.0234 (5)
C6B	0.2578 (3)	0.3206 (2)	0.65261 (19)	0.0218 (5)
C7A	0.9337 (3)	0.4898 (2)	1.13063 (18)	0.0208 (5)
C7B	0.3988 (3)	0.3521 (2)	0.63505 (18)	0.0191 (5)
C8A	1.0680 (3)	0.5168 (2)	1.14721 (18)	0.0213 (5)
C8B	0.3970 (3)	0.4574 (2)	0.65117 (19)	0.0213 (5)
C9A	1.0724 (3)	0.6240 (2)	1.13095 (18)	0.0195 (5)
C9B	0.5332 (3)	0.4892 (2)	0.63321 (18)	0.0197 (5)
H10A	1.2994	0.5960	1.1746	0.028*
H10B	0.4327	0.6487	0.6717	0.027*
H11A	1.3071	0.7713	1.1428	0.030*
H11B	0.6569	0.7002	0.6460	0.030*
H12A	1.0872	0.9109	1.0755	0.030*
H12B	0.9033	0.5700	0.5970	0.028*
H13A	0.8604	0.8746	1.0468	0.026*
H13B	0.9193	0.3970	0.5670	0.025*
H15A	0.6218	0.8380	1.0739	0.023*
H15B	0.8655	0.1523	0.5735	0.023*
H16A	0.6070	0.7074	0.9237	0.023*
H16B	0.8981	0.3095	0.4229	0.023*
H18A	1.3367	0.0627	0.3362	0.030*
H18B	1.3320	0.1471	0.2407	0.030*
H18C	0.2929	1.0076	0.7845	0.029*
H18D	0.1673	0.9538	0.8379	0.029*
H19A	1.1467	0.0803	0.1714	0.057*
H19B	1.1747	−0.0112	0.2622	0.057*
H19C	1.3155	−0.0092	0.1811	0.057*
H19D	0.3357	0.8908	0.6489	0.043*
H19E	0.1588	0.9705	0.6572	0.043*
H19F	0.1991	0.8474	0.7005	0.043*
H3A	0.5599	0.5974	1.0674	0.025*
H3B	0.6342	0.1153	0.5523	0.026*
H4A	0.5668	0.4192	1.0952	0.029*
H4B	0.4034	0.0730	0.5777	0.029*
H5A	0.8009	0.2798	1.1428	0.031*
H5B	0.1661	0.1997	0.6436	0.028*
H6A	1.0229	0.3239	1.1681	0.028*
H6B	0.1635	0.3706	0.6785	0.026*
H8A	1.1580	0.4614	1.1700	0.026*
H8B	0.3018	0.5082	0.6747	0.026*
O1A	0.3710 (2)	0.94528 (14)	0.97524 (14)	0.0244 (4)
O1B	1.1304 (2)	0.06439 (14)	0.46678 (14)	0.0241 (4)
O2A	0.3930 (2)	0.84993 (14)	0.83614 (13)	0.0209 (4)
O2B	1.1301 (2)	0.18662 (14)	0.33104 (13)	0.0225 (4)

	U11	U22	U33	U12	U13	U23
C10A	0.0158 (12)	0.0318 (14)	0.0185 (12)	−0.0022 (10)	−0.0003 (9)	−0.0036 (10)
C10B	0.0230 (13)	0.0200 (12)	0.0203 (12)	−0.0012 (10)	−0.0014 (10)	−0.0012 (10)
C11A	0.0168 (12)	0.0328 (14)	0.0258 (13)	−0.0079 (11)	0.0003 (10)	−0.0077 (11)
C11B	0.0307 (14)	0.0218 (13)	0.0236 (13)	−0.0092 (11)	−0.0030 (11)	−0.0001 (10)
C12A	0.0240 (13)	0.0235 (13)	0.0272 (13)	−0.0084 (11)	0.0023 (11)	−0.0064 (10)
C12B	0.0239 (13)	0.0269 (13)	0.0207 (12)	−0.0110 (11)	−0.0018 (10)	−0.0005 (10)
C13A	0.0178 (12)	0.0215 (12)	0.0227 (12)	−0.0022 (10)	0.0005 (10)	−0.0030 (10)
C13B	0.0191 (12)	0.0263 (13)	0.0164 (12)	−0.0057 (10)	−0.0007 (9)	0.0000 (10)
C14A	0.0174 (12)	0.0194 (12)	0.0155 (11)	−0.0019 (9)	0.0009 (9)	−0.0027 (9)
C14B	0.0185 (12)	0.0202 (12)	0.0149 (11)	−0.0022 (10)	−0.0020 (9)	−0.0010 (9)
C15A	0.0156 (11)	0.0167 (11)	0.0228 (12)	−0.0040 (9)	0.0015 (9)	−0.0005 (9)
C15B	0.0170 (12)	0.0186 (12)	0.0214 (12)	−0.0048 (9)	−0.0025 (9)	−0.0007 (9)
C16A	0.0166 (11)	0.0178 (12)	0.0231 (12)	−0.0049 (9)	0.0019 (9)	−0.0025 (9)
C16B	0.0170 (12)	0.0176 (12)	0.0214 (12)	−0.0035 (9)	−0.0024 (9)	−0.0005 (9)
C17A	0.0167 (11)	0.0187 (12)	0.0214 (12)	−0.0079 (10)	0.0006 (9)	0.0003 (10)
C17B	0.0162 (11)	0.0204 (12)	0.0202 (12)	−0.0068 (10)	−0.0007 (9)	−0.0031 (10)
C18A	0.0193 (12)	0.0204 (13)	0.0289 (14)	−0.0016 (10)	−0.0061 (10)	0.0026 (10)
C18B	0.0190 (12)	0.0261 (13)	0.0265 (13)	−0.0037 (10)	0.0081 (10)	−0.0042 (11)
C19A	0.0302 (14)	0.0285 (14)	0.0266 (14)	−0.0084 (12)	−0.0083 (11)	0.0044 (11)
C19B	0.0404 (17)	0.0382 (17)	0.0340 (16)	−0.0102 (14)	0.0088 (13)	−0.0137 (13)
C1A	0.0163 (11)	0.0180 (12)	0.0161 (11)	−0.0013 (9)	0.0014 (9)	−0.0028 (9)
C1B	0.0186 (12)	0.0218 (12)	0.0144 (11)	−0.0033 (10)	−0.0017 (9)	0.0010 (9)
C2A	0.0181 (12)	0.0191 (12)	0.0137 (11)	−0.0016 (10)	0.0008 (9)	−0.0006 (9)
C2B	0.0176 (12)	0.0210 (12)	0.0149 (11)	−0.0027 (10)	−0.0016 (9)	0.0001 (9)
C3A	0.0194 (12)	0.0221 (13)	0.0176 (12)	−0.0037 (10)	0.0002 (9)	−0.0011 (9)
C3B	0.0189 (12)	0.0218 (13)	0.0219 (12)	−0.0035 (10)	0.0012 (10)	−0.0017 (10)
C4A	0.0279 (13)	0.0266 (13)	0.0187 (12)	−0.0119 (11)	0.0018 (10)	−0.0026 (10)
C4B	0.0252 (13)	0.0214 (13)	0.0257 (13)	−0.0080 (11)	−0.0005 (10)	−0.0005 (10)
C5A	0.0322 (14)	0.0194 (12)	0.0239 (13)	−0.0075 (11)	0.0039 (11)	−0.0021 (10)
C5B	0.0178 (12)	0.0277 (13)	0.0246 (13)	−0.0081 (10)	−0.0006 (10)	0.0005 (10)
C6A	0.0253 (13)	0.0190 (12)	0.0198 (12)	−0.0002 (10)	0.0013 (10)	0.0009 (10)
C6B	0.0168 (12)	0.0252 (13)	0.0198 (12)	−0.0027 (10)	−0.0003 (9)	−0.0004 (10)
C7A	0.0213 (12)	0.0213 (12)	0.0150 (11)	−0.0017 (10)	0.0029 (9)	−0.0008 (9)
C7B	0.0170 (12)	0.0226 (12)	0.0145 (11)	−0.0025 (10)	−0.0005 (9)	−0.0003 (9)
C8A	0.0175 (12)	0.0223 (12)	0.0174 (12)	0.0020 (10)	0.0005 (9)	−0.0004 (9)
C8B	0.0182 (12)	0.0215 (12)	0.0179 (12)	0.0023 (10)	−0.0003 (9)	−0.0024 (9)
C9A	0.0169 (12)	0.0228 (12)	0.0158 (11)	−0.0026 (10)	0.0012 (9)	−0.0022 (9)
C9B	0.0200 (12)	0.0220 (12)	0.0143 (11)	−0.0028 (10)	−0.0034 (9)	0.0001 (9)
O1A	0.0202 (9)	0.0223 (9)	0.0282 (10)	−0.0021 (7)	−0.0034 (7)	−0.0047 (7)
O1B	0.0199 (9)	0.0215 (9)	0.0264 (9)	−0.0022 (7)	0.0016 (7)	0.0017 (7)
O2A	0.0182 (8)	0.0202 (9)	0.0213 (9)	−0.0021 (7)	−0.0036 (7)	0.0004 (7)
O2B	0.0188 (9)	0.0225 (9)	0.0222 (9)	−0.0033 (7)	0.0046 (7)	−0.0006 (7)

C10A—C11A	1.358 (4)	C1A—C15A	1.476 (3)
C10A—H10A	0.9300	C1A—C14A	1.414 (4)
C10B—H10B	0.9300	C1A—C2A	1.415 (4)
C11A—H11A	0.9300	C1B—C15B	1.479 (3)
C11B—C10B	1.359 (4)	C2A—C3A	1.432 (4)
C11B—H11B	0.9300	C2A—C7A	1.445 (3)
C12A—C11A	1.424 (4)	C2B—C3B	1.429 (4)
C12A—H12A	0.9300	C2B—C7B	1.443 (3)
C12B—C11B	1.426 (4)	C2B—C1B	1.413 (4)
C12B—C13B	1.350 (4)	C3A—H3A	0.9300
C12B—H12B	0.9300	C3B—H3B	0.9300
C13A—C12A	1.364 (4)	C4A—C5A	1.418 (4)
C13A—H13A	0.9300	C4A—C3A	1.362 (4)
C13B—H13B	0.9300	C4A—H4A	0.9300
C14A—C13A	1.434 (4)	C4B—C3B	1.362 (4)
C14A—C9A	1.436 (3)	C4B—C5B	1.424 (4)
C14B—C13B	1.436 (4)	C4B—H4B	0.9300
C14B—C9B	1.442 (3)	C5A—H5A	0.9300
C14B—C1B	1.412 (4)	C5B—H5B	0.9300
C15A—C16A	1.328 (4)	C6A—C5A	1.360 (4)
C15A—H15A	0.9300	C6A—H6A	0.9300
C15B—H15B	0.9300	C6B—C5B	1.361 (4)
C16A—C17A	1.478 (3)	C6B—H6B	0.9300
C16A—H16A	0.9300	C7A—C6A	1.427 (4)
C16B—C17B	1.478 (3)	C7B—C8B	1.389 (4)
C16B—C15B	1.330 (4)	C7B—C6B	1.429 (4)
C16B—H16B	0.9300	C8A—C7A	1.387 (4)
C18A—C19A	1.497 (4)	C8A—H8A	0.9300
C18A—H18D	0.9700	C8B—H8B	0.9300
C18A—H18C	0.9700	C9A—C10A	1.428 (4)
C18B—C19B	1.500 (4)	C9A—C8A	1.391 (4)
C18B—H18B	0.9700	C9B—C10B	1.427 (4)
C18B—H18A	0.9700	C9B—C8B	1.392 (4)
C19A—H19F	0.9600	O1A—C17A	1.207 (3)
C19A—H19E	0.9600	O1B—C17B	1.205 (3)
C19A—H19D	0.9600	O2A—C18A	1.454 (3)
C19B—H19C	0.9600	O2A—C17A	1.347 (3)
C19B—H19B	0.9600	O2B—C18B	1.453 (3)
C19B—H19A	0.9600	O2B—C17B	1.349 (3)
C10A—C11A—H11A	120.0	C2B—C3B—H3B	119.4
C10A—C11A—C12A	120.0 (2)	C2B—C1B—C15B	118.4 (2)
C10A—C9A—C14A	119.1 (2)	C3A—C4A—C5A	121.2 (3)
C10B—C11B—H11B	120.4	C3A—C4A—H4A	119.4
C10B—C11B—C12B	119.1 (2)	C3A—C2A—C7A	117.1 (2)
C10B—C9B—C14B	119.0 (2)	C3B—C4B—C5B	121.3 (2)
C11A—C12A—H12A	119.7	C3B—C4B—H4B	119.4
C11A—C10A—H10A	119.4	C3B—C2B—C7B	117.5 (2)
C11A—C10A—C9A	121.3 (2)	C4A—C5A—H5A	120.3
C11B—C10B—H10B	119.1	C4A—C3A—H3A	119.2
C11B—C10B—C9B	121.8 (2)	C4A—C3A—C2A	121.5 (2)
C11B—C12B—H12B	119.4	C4B—C3B—H3B	119.4
C12A—C11A—H11A	120.0	C4B—C3B—C2B	121.2 (2)
C12A—C13A—H13A	119.4	C4B—C5B—H5B	120.3
C12A—C13A—C14A	121.2 (2)	C5A—C6A—H6A	119.1
C12B—C11B—H11B	120.4	C5A—C6A—C7A	121.7 (2)
C12B—C13B—H13B	119.1	C5A—C4A—H4A	119.4
C12B—C13B—C14B	121.9 (2)	C5B—C4B—H4B	119.4
C13A—C12A—C11A	120.7 (2)	C5B—C6B—H6B	119.4
C13A—C12A—H12A	119.7	C5B—C6B—C7B	121.2 (2)
C13A—C14A—C9A	117.7 (2)	C6A—C5A—H5A	120.3
C13B—C12B—C11B	121.1 (2)	C6A—C5A—C4A	119.4 (2)
C13B—C12B—H12B	119.4	C6A—C7A—C2A	119.0 (2)
C13B—C14B—C9B	116.9 (2)	C6B—C5B—H5B	120.3
C14A—C13A—H13A	119.4	C6B—C5B—C4B	119.5 (2)
C14A—C1A—C15A	118.6 (2)	C6B—C7B—C2B	119.3 (2)
C14A—C1A—C2A	120.5 (2)	C7A—C6A—H6A	119.1
C14B—C13B—H13B	119.1	C7A—C8A—H8A	118.9
C14B—C1B—C15B	121.1 (2)	C7A—C8A—C9A	122.2 (2)
C14B—C1B—C2B	120.5 (2)	C7B—C8B—H8B	118.9
C15A—C16A—C17A	121.4 (2)	C7B—C8B—C9B	122.1 (2)
C15A—C16A—H16A	119.3	C7B—C6B—H6B	119.4
C15B—C16B—C17B	121.4 (2)	C8A—C7A—C6A	121.5 (2)
C15B—C16B—H16B	119.3	C8A—C7A—C2A	119.5 (2)
C16A—C15A—H15A	117.3	C8A—C9A—C10A	121.7 (2)
C16A—C15A—C1A	125.5 (2)	C8A—C9A—C14A	119.2 (2)
C16B—C15B—H15B	117.5	C8B—C9B—C10B	121.4 (2)
C16B—C15B—C1B	125.0 (2)	C8B—C9B—C14B	119.6 (2)
C17A—C16A—H16A	119.3	C8B—C7B—C6B	121.7 (2)
C17A—O2A—C18A	115.54 (19)	C8B—C7B—C2B	119.1 (2)
C17B—C16B—H16B	119.3	C9A—C10A—H10A	119.4
C17B—O2B—C18B	116.66 (19)	C9A—C8A—H8A	118.9
C18A—C19A—H19F	109.5	C9B—C10B—H10B	119.1
C18A—C19A—H19E	109.5	C9B—C8B—H8B	118.9
C18A—C19A—H19D	109.5	H18A—C18B—H18B	108.0
C18B—C19B—H19C	109.5	H18C—C18A—H18D	108.5
C18B—C19B—H19B	109.5	H19A—C19B—H19C	109.5
C18B—C19B—H19A	109.5	H19A—C19B—H19B	109.5
C19A—C18A—H18D	110.3	H19B—C19B—H19C	109.5
C19A—C18A—H18C	110.3	H19D—C19A—H19F	109.5
C19B—C18B—H18B	109.4	H19D—C19A—H19E	109.5
C19B—C18B—H18A	109.4	H19E—C19A—H19F	109.5
C1A—C15A—H15A	117.3	O1A—C17A—C16A	125.9 (2)
C1A—C14A—C13A	122.7 (2)	O1A—C17A—O2A	123.9 (2)
C1A—C14A—C9A	119.6 (2)	O1B—C17B—C16B	125.9 (2)
C1A—C2A—C3A	123.9 (2)	O1B—C17B—O2B	124.2 (2)
C1A—C2A—C7A	119.0 (2)	O2A—C18A—C19A	107.3 (2)
C1B—C15B—H15B	117.5	O2A—C18A—H18D	110.3
C1B—C2B—C3B	122.9 (2)	O2A—C18A—H18C	110.3
C1B—C2B—C7B	119.6 (2)	O2A—C17A—C16A	110.2 (2)
C1B—C14B—C13B	124.0 (2)	O2B—C18B—C19B	111.0 (2)
C1B—C14B—C9B	119.1 (2)	O2B—C18B—H18B	109.4
C2A—C3A—H3A	119.2	O2B—C18B—H18A	109.4
C2A—C1A—C15A	121.0 (2)	O2B—C17B—C16B	109.9 (2)
C10A—C9A—C8A—C7A	179.5 (2)	C1A—C2A—C7A—C8A	1.6 (3)
C10B—C9B—C8B—C7B	−180.0 (2)	C1B—C2B—C3B—C4B	−177.8 (2)
C11B—C12B—C13B—C14B	0.1 (4)	C1B—C2B—C7B—C8B	0.4 (3)
C12B—C11B—C10B—C9B	−1.3 (4)	C1B—C2B—C7B—C6B	179.3 (2)
C13A—C12A—C11A—C10A	1.4 (4)	C1B—C14B—C13B—C12B	179.6 (2)
C13A—C14A—C9A—C10A	2.7 (3)	C1B—C14B—C9B—C10B	−179.0 (2)
C13A—C14A—C9A—C8A	−176.7 (2)	C1B—C14B—C9B—C8B	1.8 (3)
C13B—C12B—C11B—C10B	1.9 (4)	C2A—C7A—C6A—C5A	−1.4 (4)
C13B—C14B—C9B—C10B	3.1 (3)	C2A—C1A—C15A—C16A	−49.8 (4)
C13B—C14B—C9B—C8B	−176.1 (2)	C2A—C1A—C14A—C13A	177.9 (2)
C13B—C14B—C1B—C15B	−4.6 (4)	C2A—C1A—C14A—C9A	0.0 (3)
C13B—C14B—C1B—C2B	176.0 (2)	C2B—C7B—C8B—C9B	−0.3 (4)
C14A—C13A—C12A—C11A	−0.1 (4)	C2B—C7B—C6B—C5B	−2.0 (4)
C14A—C9A—C10A—C11A	−1.5 (4)	C2B—C1B—C15B—C16B	129.6 (3)
C14A—C9A—C8A—C7A	−1.1 (4)	C3A—C4A—C5A—C6A	1.6 (4)
C14A—C1A—C15A—C16A	130.4 (3)	C3A—C2A—C7A—C6A	3.7 (3)
C14A—C1A—C2A—C3A	176.4 (2)	C3A—C2A—C7A—C8A	−176.3 (2)
C14A—C1A—C2A—C7A	−1.4 (3)	C3B—C4B—C5B—C6B	1.1 (4)
C14B—C9B—C10B—C11B	−1.2 (4)	C3B—C2B—C7B—C8B	−176.8 (2)
C14B—C9B—C8B—C7B	−0.7 (4)	C3B—C2B—C7B—C6B	2.2 (3)
C14B—C1B—C15B—C16B	−49.8 (4)	C3B—C2B—C1B—C15B	−1.7 (4)
C15A—C16A—C17A—O2A	169.2 (2)	C3B—C2B—C1B—C14B	177.7 (2)
C15A—C16A—C17A—O1A	−10.2 (4)	C5A—C4A—C3A—C2A	0.9 (4)
C15A—C1A—C14A—C13A	−2.3 (4)	C5B—C4B—C3B—C2B	−0.9 (4)
C15A—C1A—C14A—C9A	179.8 (2)	C6B—C7B—C8B—C9B	−179.3 (2)
C15A—C1A—C2A—C3A	−3.5 (4)	C7A—C6A—C5A—C4A	−1.3 (4)
C15A—C1A—C2A—C7A	178.7 (2)	C7A—C2A—C3A—C4A	−3.5 (3)
C15B—C16B—C17B—O2B	171.2 (2)	C7B—C6B—C5B—C4B	0.3 (4)
C15B—C16B—C17B—O1B	−8.7 (4)	C7B—C2B—C3B—C4B	−0.8 (4)
C17A—O2A—C18A—C19A	178.4 (2)	C7B—C2B—C1B—C15B	−178.7 (2)
C17B—C16B—C15B—C1B	−179.1 (2)	C7B—C2B—C1B—C14B	0.7 (4)
C17B—O2B—C18B—C19B	87.3 (3)	C8A—C7A—C6A—C5A	178.6 (2)
C18A—O2A—C17A—C16A	−176.1 (2)	C8A—C9A—C10A—C11A	177.9 (2)
C18A—O2A—C17A—O1A	3.3 (3)	C8B—C9B—C10B—C11B	178.0 (2)
C18B—O2B—C17B—C16B	−177.5 (2)	C8B—C7B—C6B—C5B	176.9 (2)
C18B—O2B—C17B—O1B	2.4 (4)	C9A—C10A—C11A—C12A	−0.6 (4)
C1A—C15A—C16A—C17A	−179.8 (2)	C9A—C8A—C7A—C6A	179.6 (2)
C1A—C14A—C13A—C12A	−179.9 (2)	C9A—C8A—C7A—C2A	−0.3 (4)
C1A—C14A—C9A—C10A	−179.3 (2)	C9A—C14A—C13A—C12A	−1.9 (4)
C1A—C14A—C9A—C8A	1.3 (3)	C9B—C14B—C13B—C12B	−2.6 (4)
C1A—C2A—C3A—C4A	178.7 (2)	C9B—C14B—C1B—C15B	177.6 (2)
C1A—C2A—C7A—C6A	−178.4 (2)	C9B—C14B—C1B—C2B	−1.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13A—H13A···O1Ai	0.93	2.56	3.455 (3)	163
C18B—H18B···O2Aii	0.97	2.56	3.422 (3)	148
C3B—H3B···O1Biii	0.93	2.57	3.470 (3)	162
C6A—H6A···O2Biv	0.93	2.67	3.438 (3)	140
C19A—H19E···O1Bv	0.96	2.66	3.409 (3)	135
C6B—H6B···Cg1vi	0.93	2.81	3.447 (3)	126
C8B—H8B···Cg2vi	0.93	2.82	3.439 (3)	124

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1A/C2A/C7A–C9A/C14A and C2A—C7A rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13A—H13A⋯O1A i	0.93	2.56	3.455 (3)	163
C18B—H18B⋯O2A ii	0.97	2.56	3.422 (3)	148
C3B—H3B⋯O1B iii	0.93	2.57	3.470 (3)	162
C6A—H6A⋯O2B iv	0.93	2.67	3.438 (3)	140
C19A—H19E⋯O1B v	0.96	2.66	3.409 (3)	135
C6B—H6B⋯Cg1vi	0.93	2.81	3.447 (3)	126
C8B—H8B⋯Cg2vi	0.93	2.82	3.439 (3)	124

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