2-[(E)-4-Meth-oxy-benzyl-idene]-1,2,3,4-tetra-hydro-naphthalen-1-one.

Two independent mol-ecules (A and B) comprise the asymmetric unit of the title compound, C(18)H(16)O(2). Mol-ecule B is virtually superimposable upon A. Minor differences are noted in the dihedral angles between the terminal benzene rings of 56.03 (10) and 54.62 (10)°, and in the orientations of meth-oxy groups with respect to the benzene rings to which they are attached [C-O-C-C torsion angles = 169.11 (19) and -172.37 (18)°]. The cyclo-hexene ring of each fused ring system has a screw-boat conformation. In the crystal, C-H⋯π inter-actions assemble mol-ecules into a supra-molecular array in the ab plane.

Related literature

For the activity of related species developed for the treatment of Chagas disease, see: Vera-DiVaio et al. (2009 ▶). For the structure of the 2-meth­oxy derivative, see: Dimmock et al. (2002 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C18H16O2

M = 264.31

Monoclinic,

a = 6.8289 (4) Å

b = 14.7444 (8) Å

c = 26.7258 (14) Å

β = 93.757 (5)°

V = 2685.2 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.40 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.766, T max = 1.000

18691 measured reflections

6195 independent reflections

3813 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.187

S = 0.99

6195 reflections

361 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.25 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 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681202805X/bt5948sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202805X/bt5948Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202805X/bt5948Isup3.cml

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

C18H16O2	F(000) = 1120
Mr = 264.31	Dx = 1.308 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3418 reflections
a = 6.8289 (4) Å	θ = 2.7–27.5°
b = 14.7444 (8) Å	µ = 0.08 mm−1
c = 26.7258 (14) Å	T = 100 K
β = 93.757 (5)°	Prism, light-yellow
V = 2685.2 (3) Å3	0.40 × 0.20 × 0.10 mm
Z = 8

Agilent SuperNova Dual diffractometer with an Atlas detector	6195 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3813 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.054
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.7°
ω scan	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −19→15
Tmin = 0.766, Tmax = 1.000	l = −34→27
18691 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
6195 reflections	(Δ/σ)max < 0.001
361 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.25 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
O1	0.6701 (2)	0.77015 (11)	0.24286 (5)	0.0275 (4)
O2	−0.2580 (2)	0.79768 (10)	0.02451 (5)	0.0278 (4)
O3	1.2130 (2)	0.55355 (11)	0.26086 (6)	0.0292 (4)
O4	0.2783 (2)	0.52827 (10)	0.04328 (5)	0.0268 (4)
C1	0.5156 (3)	0.78348 (13)	0.26276 (8)	0.0191 (5)
C2	0.5128 (3)	0.78434 (13)	0.31863 (7)	0.0192 (5)
C3	0.6731 (3)	0.74880 (14)	0.34768 (8)	0.0255 (5)
H3	0.7842	0.7269	0.3318	0.031*
C4	0.6701 (4)	0.74553 (15)	0.39950 (8)	0.0293 (5)
H4	0.7778	0.7204	0.4191	0.035*
C5	0.5088 (4)	0.77917 (15)	0.42253 (8)	0.0289 (5)
H5	0.5069	0.7775	0.4580	0.035*
C6	0.3502 (3)	0.81528 (14)	0.39402 (8)	0.0246 (5)
H6	0.2412	0.8386	0.4103	0.029*
C7	0.3488 (3)	0.81776 (13)	0.34180 (8)	0.0205 (5)
C8	0.1784 (3)	0.85520 (14)	0.30966 (7)	0.0207 (5)
H8A	0.2059	0.9189	0.3008	0.025*
H8B	0.0590	0.8545	0.3288	0.025*
C9	0.1421 (3)	0.79936 (14)	0.26173 (8)	0.0203 (5)
H9A	0.1016	0.7372	0.2705	0.024*
H9B	0.0343	0.8271	0.2404	0.024*
C10	0.3253 (3)	0.79488 (13)	0.23293 (8)	0.0186 (4)
C11	0.3302 (3)	0.80015 (13)	0.18286 (7)	0.0188 (5)
H11	0.4575	0.8033	0.1706	0.023*
C12	0.1669 (3)	0.80180 (13)	0.14431 (7)	0.0191 (5)
C13	0.1890 (3)	0.84882 (14)	0.09931 (7)	0.0208 (5)
H13	0.3059	0.8822	0.0953	0.025*
C14	0.0440 (3)	0.84745 (14)	0.06078 (8)	0.0216 (5)
H14	0.0606	0.8809	0.0310	0.026*
C15	−0.1261 (3)	0.79728 (14)	0.06547 (7)	0.0209 (5)
C16	−0.1524 (3)	0.74988 (14)	0.10958 (7)	0.0205 (5)
H16	−0.2689	0.7159	0.1131	0.025*
C17	−0.0066 (3)	0.75278 (13)	0.14846 (7)	0.0192 (5)
H17	−0.0254	0.7206	0.1786	0.023*
C18	−0.4166 (3)	0.73482 (16)	0.02424 (9)	0.0307 (5)
H18A	−0.5007	0.7424	−0.0066	0.046*
H18B	−0.4935	0.7460	0.0533	0.046*
H18C	−0.3647	0.6728	0.0258	0.046*
C19	1.0573 (3)	0.54246 (13)	0.28040 (8)	0.0193 (5)
C20	1.0499 (3)	0.54485 (13)	0.33611 (8)	0.0191 (5)
C21	1.2083 (3)	0.58197 (14)	0.36510 (8)	0.0245 (5)
H21	1.3201	0.6033	0.3493	0.029*
C22	1.2022 (3)	0.58761 (14)	0.41678 (8)	0.0274 (5)
H22	1.3095	0.6130	0.4365	0.033*
C23	1.0381 (3)	0.55593 (14)	0.43966 (8)	0.0268 (5)
H23	1.0329	0.5605	0.4750	0.032*
C24	0.8820 (3)	0.51760 (14)	0.41117 (8)	0.0234 (5)
H24	0.7722	0.4949	0.4273	0.028*
C25	0.8846 (3)	0.51211 (14)	0.35905 (8)	0.0199 (5)
C26	0.7168 (3)	0.47224 (14)	0.32696 (8)	0.0225 (5)
H26A	0.5962	0.4737	0.3456	0.027*
H26B	0.7462	0.4081	0.3194	0.027*
C27	0.6822 (3)	0.52514 (14)	0.27784 (7)	0.0201 (5)
H27A	0.5783	0.4948	0.2564	0.024*
H27B	0.6365	0.5871	0.2852	0.024*
C28	0.8670 (3)	0.53087 (13)	0.25012 (7)	0.0184 (5)
C29	0.8732 (3)	0.52698 (13)	0.19981 (8)	0.0197 (5)
H29	1.0006	0.5245	0.1876	0.024*
C30	0.7102 (3)	0.52606 (13)	0.16160 (7)	0.0185 (4)
C31	0.7301 (3)	0.47902 (14)	0.11619 (8)	0.0214 (5)
H31	0.8470	0.4458	0.1118	0.026*
C32	0.5845 (3)	0.48000 (14)	0.07810 (8)	0.0221 (5)
H32	0.6005	0.4471	0.0481	0.027*
C33	0.4132 (3)	0.52956 (14)	0.08374 (8)	0.0214 (5)
C34	0.3894 (3)	0.57657 (14)	0.12784 (7)	0.0207 (5)
H34	0.2727	0.6102	0.1317	0.025*
C35	0.5359 (3)	0.57460 (14)	0.16638 (7)	0.0203 (5)
H35	0.5176	0.6067	0.1965	0.024*
C36	0.1135 (3)	0.58699 (15)	0.04526 (8)	0.0268 (5)
H36A	0.0275	0.5796	0.0147	0.040*
H36B	0.1586	0.6500	0.0479	0.040*
H36C	0.0408	0.5718	0.0746	0.040*

	U11	U22	U33	U12	U13	U23
O1	0.0184 (8)	0.0352 (9)	0.0293 (9)	0.0018 (7)	0.0038 (7)	−0.0026 (7)
O2	0.0298 (9)	0.0303 (9)	0.0224 (8)	−0.0040 (7)	−0.0051 (7)	0.0049 (6)
O3	0.0190 (8)	0.0375 (10)	0.0316 (9)	−0.0025 (7)	0.0057 (7)	−0.0020 (7)
O4	0.0313 (9)	0.0285 (9)	0.0200 (8)	0.0075 (7)	−0.0034 (7)	−0.0018 (6)
C1	0.0190 (11)	0.0134 (10)	0.0248 (11)	0.0002 (8)	0.0009 (9)	−0.0007 (8)
C2	0.0211 (11)	0.0151 (10)	0.0209 (11)	−0.0019 (8)	−0.0016 (9)	0.0001 (8)
C3	0.0256 (12)	0.0184 (11)	0.0320 (13)	−0.0009 (9)	−0.0017 (10)	−0.0032 (9)
C4	0.0392 (14)	0.0192 (12)	0.0275 (12)	−0.0014 (10)	−0.0125 (11)	0.0008 (9)
C5	0.0428 (15)	0.0212 (12)	0.0222 (12)	−0.0095 (10)	−0.0032 (11)	0.0017 (9)
C6	0.0301 (13)	0.0182 (11)	0.0258 (12)	−0.0049 (9)	0.0057 (10)	−0.0001 (9)
C7	0.0228 (12)	0.0161 (11)	0.0227 (11)	−0.0065 (8)	0.0022 (9)	−0.0016 (8)
C8	0.0188 (11)	0.0207 (11)	0.0230 (11)	0.0024 (8)	0.0034 (9)	−0.0009 (8)
C9	0.0163 (11)	0.0214 (11)	0.0231 (11)	0.0001 (8)	0.0007 (9)	−0.0002 (8)
C10	0.0163 (11)	0.0155 (10)	0.0240 (11)	0.0015 (8)	0.0019 (9)	−0.0009 (8)
C11	0.0163 (11)	0.0173 (11)	0.0231 (11)	0.0010 (8)	0.0031 (9)	−0.0018 (8)
C12	0.0186 (11)	0.0162 (11)	0.0227 (11)	0.0024 (8)	0.0035 (9)	−0.0023 (8)
C13	0.0229 (12)	0.0174 (11)	0.0226 (11)	−0.0006 (9)	0.0044 (9)	−0.0019 (8)
C14	0.0273 (12)	0.0191 (11)	0.0185 (11)	0.0019 (9)	0.0028 (9)	0.0023 (8)
C15	0.0239 (12)	0.0201 (11)	0.0186 (11)	0.0036 (9)	0.0006 (9)	−0.0010 (8)
C16	0.0204 (11)	0.0176 (11)	0.0237 (12)	−0.0002 (8)	0.0024 (9)	−0.0017 (8)
C17	0.0229 (11)	0.0176 (11)	0.0175 (11)	0.0028 (8)	0.0039 (9)	0.0003 (8)
C18	0.0262 (13)	0.0367 (14)	0.0280 (13)	−0.0040 (10)	−0.0058 (10)	0.0001 (10)
C19	0.0167 (11)	0.0141 (10)	0.0270 (12)	−0.0012 (8)	0.0019 (9)	−0.0009 (8)
C20	0.0211 (11)	0.0144 (10)	0.0218 (11)	0.0017 (8)	0.0013 (9)	0.0021 (8)
C21	0.0209 (12)	0.0193 (12)	0.0328 (13)	−0.0026 (9)	−0.0023 (10)	0.0012 (9)
C22	0.0332 (13)	0.0192 (12)	0.0288 (13)	−0.0052 (10)	−0.0054 (10)	0.0012 (9)
C23	0.0388 (14)	0.0186 (12)	0.0226 (12)	−0.0022 (10)	−0.0003 (10)	−0.0003 (9)
C24	0.0284 (12)	0.0177 (11)	0.0244 (12)	−0.0012 (9)	0.0043 (10)	0.0001 (8)
C25	0.0211 (11)	0.0158 (10)	0.0228 (11)	0.0032 (8)	0.0011 (9)	0.0009 (8)
C26	0.0208 (11)	0.0224 (12)	0.0246 (11)	−0.0017 (9)	0.0039 (9)	0.0003 (9)
C27	0.0186 (11)	0.0202 (11)	0.0217 (11)	−0.0009 (9)	0.0028 (9)	0.0003 (8)
C28	0.0171 (11)	0.0148 (10)	0.0233 (11)	−0.0012 (8)	0.0023 (9)	0.0009 (8)
C29	0.0201 (11)	0.0148 (11)	0.0246 (11)	−0.0008 (8)	0.0047 (9)	0.0007 (8)
C30	0.0209 (11)	0.0161 (10)	0.0190 (11)	−0.0016 (8)	0.0048 (9)	0.0028 (8)
C31	0.0233 (12)	0.0190 (11)	0.0226 (11)	0.0045 (9)	0.0070 (9)	0.0035 (8)
C32	0.0299 (12)	0.0197 (11)	0.0169 (11)	0.0030 (9)	0.0040 (9)	−0.0010 (8)
C33	0.0261 (12)	0.0190 (11)	0.0191 (11)	−0.0007 (9)	0.0002 (9)	0.0035 (8)
C34	0.0219 (11)	0.0181 (11)	0.0226 (11)	0.0041 (9)	0.0049 (9)	0.0017 (8)
C35	0.0255 (12)	0.0177 (11)	0.0183 (11)	0.0009 (9)	0.0044 (9)	0.0009 (8)
C36	0.0251 (12)	0.0270 (12)	0.0279 (12)	0.0031 (10)	−0.0026 (10)	0.0032 (9)

O1—C1	1.229 (2)	C18—H18A	0.9800
O2—C15	1.371 (2)	C18—H18B	0.9800
O2—C18	1.426 (3)	C18—H18C	0.9800
O3—C19	1.226 (2)	C19—C20	1.494 (3)
O4—C33	1.374 (2)	C19—C28	1.495 (3)
O4—C36	1.424 (2)	C20—C21	1.400 (3)
C1—C10	1.489 (3)	C20—C25	1.405 (3)
C1—C2	1.494 (3)	C21—C22	1.387 (3)
C2—C3	1.401 (3)	C21—H21	0.9500
C2—C7	1.404 (3)	C22—C23	1.392 (3)
C3—C4	1.387 (3)	C22—H22	0.9500
C3—H3	0.9500	C23—C24	1.389 (3)
C4—C5	1.388 (3)	C23—H23	0.9500
C4—H4	0.9500	C24—C25	1.396 (3)
C5—C6	1.389 (3)	C24—H24	0.9500
C5—H5	0.9500	C25—C26	1.505 (3)
C6—C7	1.395 (3)	C26—C27	1.532 (3)
C6—H6	0.9500	C26—H26A	0.9900
C7—C8	1.506 (3)	C26—H26B	0.9900
C8—C9	1.529 (3)	C27—C28	1.507 (3)
C8—H8A	0.9900	C27—H27A	0.9900
C8—H8B	0.9900	C27—H27B	0.9900
C9—C10	1.512 (3)	C28—C29	1.349 (3)
C9—H9A	0.9900	C29—C30	1.460 (3)
C9—H9B	0.9900	C29—H29	0.9500
C10—C11	1.343 (3)	C30—C35	1.402 (3)
C11—C12	1.468 (3)	C30—C31	1.412 (3)
C11—H11	0.9500	C31—C32	1.375 (3)
C12—C17	1.398 (3)	C31—H31	0.9500
C12—C13	1.405 (3)	C32—C33	1.396 (3)
C13—C14	1.381 (3)	C32—H32	0.9500
C13—H13	0.9500	C33—C34	1.386 (3)
C14—C15	1.389 (3)	C34—C35	1.388 (3)
C14—H14	0.9500	C34—H34	0.9500
C15—C16	1.392 (3)	C35—H35	0.9500
C16—C17	1.392 (3)	C36—H36A	0.9800
C16—H16	0.9500	C36—H36B	0.9800
C17—H17	0.9500	C36—H36C	0.9800
C15—O2—C18	117.43 (16)	H18B—C18—H18C	109.5
C33—O4—C36	116.96 (16)	O3—C19—C20	120.56 (19)
O1—C1—C10	122.05 (18)	O3—C19—C28	122.16 (19)
O1—C1—C2	120.08 (19)	C20—C19—C28	117.21 (17)
C10—C1—C2	117.80 (17)	C21—C20—C25	120.44 (19)
C3—C2—C7	120.22 (19)	C21—C20—C19	119.04 (18)
C3—C2—C1	119.34 (18)	C25—C20—C19	120.51 (18)
C7—C2—C1	120.41 (18)	C22—C21—C20	120.1 (2)
C4—C3—C2	120.3 (2)	C22—C21—H21	119.9
C4—C3—H3	119.9	C20—C21—H21	119.9
C2—C3—H3	119.9	C21—C22—C23	119.7 (2)
C5—C4—C3	119.6 (2)	C21—C22—H22	120.2
C5—C4—H4	120.2	C23—C22—H22	120.2
C3—C4—H4	120.2	C24—C23—C22	120.5 (2)
C4—C5—C6	120.5 (2)	C24—C23—H23	119.8
C4—C5—H5	119.8	C22—C23—H23	119.8
C6—C5—H5	119.8	C23—C24—C25	120.7 (2)
C5—C6—C7	120.8 (2)	C23—C24—H24	119.6
C5—C6—H6	119.6	C25—C24—H24	119.6
C7—C6—H6	119.6	C24—C25—C20	118.59 (19)
C6—C7—C2	118.61 (19)	C24—C25—C26	122.15 (18)
C6—C7—C8	122.30 (18)	C20—C25—C26	119.27 (18)
C2—C7—C8	119.09 (18)	C25—C26—C27	111.00 (17)
C7—C8—C9	110.93 (17)	C25—C26—H26A	109.4
C7—C8—H8A	109.5	C27—C26—H26A	109.4
C9—C8—H8A	109.5	C25—C26—H26B	109.4
C7—C8—H8B	109.5	C27—C26—H26B	109.4
C9—C8—H8B	109.5	H26A—C26—H26B	108.0
H8A—C8—H8B	108.0	C28—C27—C26	111.27 (17)
C10—C9—C8	110.85 (17)	C28—C27—H27A	109.4
C10—C9—H9A	109.5	C26—C27—H27A	109.4
C8—C9—H9A	109.5	C28—C27—H27B	109.4
C10—C9—H9B	109.5	C26—C27—H27B	109.4
C8—C9—H9B	109.5	H27A—C27—H27B	108.0
H9A—C9—H9B	108.1	C29—C28—C19	117.47 (18)
C11—C10—C1	117.53 (18)	C29—C28—C27	124.72 (19)
C11—C10—C9	125.45 (19)	C19—C28—C27	117.81 (17)
C1—C10—C9	117.02 (17)	C28—C29—C30	128.69 (19)
C10—C11—C12	129.27 (19)	C28—C29—H29	115.7
C10—C11—H11	115.4	C30—C29—H29	115.7
C12—C11—H11	115.4	C35—C30—C31	117.31 (19)
C17—C12—C13	117.51 (19)	C35—C30—C29	122.98 (18)
C17—C12—C11	122.97 (18)	C31—C30—C29	119.60 (18)
C13—C12—C11	119.34 (18)	C32—C31—C30	121.70 (19)
C14—C13—C12	121.27 (19)	C32—C31—H31	119.1
C14—C13—H13	119.4	C30—C31—H31	119.1
C12—C13—H13	119.4	C31—C32—C33	119.71 (19)
C13—C14—C15	120.21 (19)	C31—C32—H32	120.1
C13—C14—H14	119.9	C33—C32—H32	120.1
C15—C14—H14	119.9	O4—C33—C34	124.49 (19)
O2—C15—C14	115.78 (18)	O4—C33—C32	115.54 (18)
O2—C15—C16	124.29 (19)	C34—C33—C32	120.0 (2)
C14—C15—C16	119.9 (2)	C33—C34—C35	120.11 (19)
C15—C16—C17	119.39 (19)	C33—C34—H34	119.9
C15—C16—H16	120.3	C35—C34—H34	119.9
C17—C16—H16	120.3	C34—C35—C30	121.19 (19)
C16—C17—C12	121.67 (19)	C34—C35—H35	119.4
C16—C17—H17	119.2	C30—C35—H35	119.4
C12—C17—H17	119.2	O4—C36—H36A	109.5
O2—C18—H18A	109.5	O4—C36—H36B	109.5
O2—C18—H18B	109.5	H36A—C36—H36B	109.5
H18A—C18—H18B	109.5	O4—C36—H36C	109.5
O2—C18—H18C	109.5	H36A—C36—H36C	109.5
H18A—C18—H18C	109.5	H36B—C36—H36C	109.5
O1—C1—C2—C3	−15.4 (3)	O3—C19—C20—C21	16.0 (3)
C10—C1—C2—C3	161.88 (18)	C28—C19—C20—C21	−160.95 (18)
O1—C1—C2—C7	166.67 (19)	O3—C19—C20—C25	−165.3 (2)
C10—C1—C2—C7	−16.1 (3)	C28—C19—C20—C25	17.7 (3)
C7—C2—C3—C4	0.6 (3)	C25—C20—C21—C22	−0.7 (3)
C1—C2—C3—C4	−177.35 (18)	C19—C20—C21—C22	177.95 (19)
C2—C3—C4—C5	−1.1 (3)	C20—C21—C22—C23	0.2 (3)
C3—C4—C5—C6	0.6 (3)	C21—C22—C23—C24	0.9 (3)
C4—C5—C6—C7	0.6 (3)	C22—C23—C24—C25	−1.5 (3)
C5—C6—C7—C2	−1.1 (3)	C23—C24—C25—C20	1.0 (3)
C5—C6—C7—C8	179.15 (19)	C23—C24—C25—C26	−179.12 (19)
C3—C2—C7—C6	0.5 (3)	C21—C20—C25—C24	0.1 (3)
C1—C2—C7—C6	178.42 (18)	C19—C20—C25—C24	−178.53 (18)
C3—C2—C7—C8	−179.74 (18)	C21—C20—C25—C26	−179.76 (18)
C1—C2—C7—C8	−1.8 (3)	C19—C20—C25—C26	1.6 (3)
C6—C7—C8—C9	−142.08 (19)	C24—C25—C26—C27	142.0 (2)
C2—C7—C8—C9	38.1 (2)	C20—C25—C26—C27	−38.1 (3)
C7—C8—C9—C10	−56.1 (2)	C25—C26—C27—C28	54.7 (2)
O1—C1—C10—C11	−7.2 (3)	O3—C19—C28—C29	4.3 (3)
C2—C1—C10—C11	175.64 (17)	C20—C19—C28—C29	−178.81 (17)
O1—C1—C10—C9	172.68 (19)	O3—C19—C28—C27	−175.23 (19)
C2—C1—C10—C9	−4.5 (3)	C20—C19—C28—C27	1.7 (3)
C8—C9—C10—C11	−140.1 (2)	C26—C27—C28—C29	143.1 (2)
C8—C9—C10—C1	40.1 (2)	C26—C27—C28—C19	−37.4 (2)
C1—C10—C11—C12	172.93 (19)	C19—C28—C29—C30	−172.60 (19)
C9—C10—C11—C12	−6.9 (3)	C27—C28—C29—C30	6.9 (3)
C10—C11—C12—C17	−35.3 (3)	C28—C29—C30—C35	35.2 (3)
C10—C11—C12—C13	149.7 (2)	C28—C29—C30—C31	−148.7 (2)
C17—C12—C13—C14	0.6 (3)	C35—C30—C31—C32	−0.4 (3)
C11—C12—C13—C14	175.92 (18)	C29—C30—C31—C32	−176.69 (18)
C12—C13—C14—C15	−1.5 (3)	C30—C31—C32—C33	0.9 (3)
C18—O2—C15—C14	169.11 (19)	C36—O4—C33—C34	6.9 (3)
C18—O2—C15—C16	−10.1 (3)	C36—O4—C33—C32	−172.37 (18)
C13—C14—C15—O2	−177.76 (18)	C31—C32—C33—O4	178.49 (17)
C13—C14—C15—C16	1.5 (3)	C31—C32—C33—C34	−0.8 (3)
O2—C15—C16—C17	178.62 (18)	O4—C33—C34—C35	−179.09 (18)
C14—C15—C16—C17	−0.5 (3)	C32—C33—C34—C35	0.1 (3)
C15—C16—C17—C12	−0.4 (3)	C33—C34—C35—C30	0.5 (3)
C13—C12—C17—C16	0.3 (3)	C31—C30—C35—C34	−0.3 (3)
C11—C12—C17—C16	−174.79 (18)	C29—C30—C35—C34	175.87 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···Cg1i	0.95	2.70	3.486 (2)	140
C21—H21···Cg2ii	0.95	2.97	3.595 (2)	124
C31—H31···Cg2iii	0.95	2.64	3.411 (2)	139
C36—H36B···Cg3	0.98	2.88	3.592 (2)	131

Table 1

Hydrogen-bond geometry (Å, °)

Cg1–Cg3 are the centroids of the C20–C25, C2–C7 and C12–C17 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯Cg1i	0.95	2.70	3.486 (2)	140
C21—H21⋯Cg2ii	0.95	2.97	3.595 (2)	124
C31—H31⋯Cg2iii	0.95	2.64	3.411 (2)	139
C36—H36B⋯Cg3	0.98	2.88	3.592 (2)	131

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