2-(Naphthalen-2-yl)azulene.

In the title compound, C(20)H(14), a naphthalene ring system is linked at the 2-position to the 2-C atom of the five-membered ring of an azulene unit. The compound crystallizes with two reasonably similar mol-ecules in the asymmetric unit. Neither mol-ecule is perfectly planar: the r.m.s. deviations from the best fit planes through all non-H atoms are 0.092 and 0.091 Å for the two mol-ecules. The dihedral angle between the mol-ecular planes is 49.60 (4)°. The naphthalene and azulene ring systems are inclined at dihedral angles of 6.54 (12) and 5.68 (12)° in the two mol-ecules. The crystal structure exhibits two sets of parallel layers, a typical edge-to-face herringbone packing arrangement. The structure is stabilized by an extensive series of weak C-H⋯π inter-actions.

Related literature

For the structure and properties of azulene, see: Zhang & Petoud (2008 ▶); Dewar (1969 ▶); Wang et al. (1999 ▶). For applications of azulene derivatives, see: Ito et al. (2005 ▶); Lambert et al. (2003 ▶); Porsch et al. (1997 ▶); Schmitt et al. (1998 ▶). For the crystal structures of some organic semiconductors, see: Tan et al. (2009 ▶); Ando et al. (2005 ▶).

Experimental

Crystal data

C20H14

M = 254.31

Triclinic,

a = 6.0754 (8) Å

b = 7.6324 (11) Å

c = 14.5662 (19) Å

α = 97.997 (7)°

β = 97.179 (6)°

γ = 90.526 (7)°

V = 663.38 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.35 × 0.32 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.975, T max = 0.991

3762 measured reflections

2573 independent reflections

2039 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.130

S = 1.04

2573 reflections

361 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker 1997 ▶); cell refinement: SAINT (Bruker 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536810004897/sj2726sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004897/sj2726Isup2.hkl

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

C20H14	Z = 2
Mr = 254.31	F(000) = 268
Triclinic, P1	Dx = 1.273 Mg m−3
Hall symbol: P 1	Melting point = 547–549 K
a = 6.0754 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6324 (11) Å	Cell parameters from 1303 reflections
c = 14.5662 (19) Å	θ = 2.9–24.7°
α = 97.997 (7)°	µ = 0.07 mm−1
β = 97.179 (6)°	T = 293 K
γ = 90.526 (7)°	Block, blue
V = 663.38 (16) Å3	0.35 × 0.32 × 0.13 mm

Bruker SMART CCD area-detector diffractometer	2573 independent reflections
Radiation source: fine-focus sealed tube	2039 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 26.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −7→7
Tmin = 0.975, Tmax = 0.991	k = −9→8
3762 measured reflections	l = −17→16

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0764P)2] where P = (Fo2 + 2Fc2)/3
2573 reflections	(Δ/σ)max < 0.001
361 parameters	Δρmax = 0.16 e Å−3
3 restraints	Δρmin = −0.16 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	0.3852 (6)	0.1216 (5)	0.5454 (3)	0.0531 (10)
H1	0.4727	0.0839	0.4988	0.064*
C2	0.4630 (7)	0.1084 (5)	0.6353 (3)	0.0576 (11)
H2	0.6020	0.0617	0.6493	0.069*
C3	0.3356 (7)	0.1650 (5)	0.7080 (3)	0.0526 (10)
C4	0.4094 (7)	0.1490 (6)	0.8036 (3)	0.0630 (12)
H4	0.5453	0.0992	0.8199	0.076*
C5	0.2791 (9)	0.2075 (7)	0.8705 (3)	0.0711 (13)
H5	0.3277	0.1972	0.9326	0.085*
C6	0.0742 (8)	0.2825 (6)	0.8480 (3)	0.0653 (12)
H6	−0.0116	0.3220	0.8949	0.078*
C7	0.0002 (7)	0.2978 (5)	0.7577 (3)	0.0545 (10)
H7	−0.1365	0.3482	0.7437	0.065*
C8	0.1255 (6)	0.2393 (5)	0.6846 (3)	0.0471 (9)
C9	0.0509 (6)	0.2508 (5)	0.5908 (3)	0.0480 (9)
H9	−0.0859	0.3003	0.5759	0.058*
C10	0.1729 (6)	0.1915 (4)	0.5200 (2)	0.0428 (9)
C11	0.0910 (6)	0.1919 (5)	0.4208 (3)	0.0436 (9)
C12	−0.1122 (6)	0.2601 (5)	0.3858 (3)	0.0479 (9)
H12	−0.2134	0.3157	0.4223	0.057*
C13	−0.1395 (6)	0.2324 (4)	0.2889 (3)	0.0443 (9)
C14	−0.3185 (6)	0.2829 (5)	0.2301 (3)	0.0496 (9)
H14	−0.4308	0.3389	0.2599	0.060*
C15	−0.3528 (7)	0.2615 (6)	0.1338 (3)	0.0574 (11)
H15	−0.4841	0.3057	0.1072	0.069*
C16	−0.2149 (7)	0.1818 (6)	0.0712 (3)	0.0584 (11)
H16	−0.2676	0.1809	0.0084	0.070*
C17	−0.0131 (7)	0.1044 (6)	0.0883 (3)	0.0591 (11)
H17	0.0498	0.0587	0.0354	0.071*
C18	0.1091 (7)	0.0848 (5)	0.1718 (3)	0.0540 (10)
H18	0.2418	0.0263	0.1675	0.065*
C19	0.0620 (6)	0.1398 (5)	0.2616 (3)	0.0470 (9)
C20	0.1931 (6)	0.1178 (5)	0.3448 (3)	0.0500 (9)
H20	0.3286	0.0619	0.3488	0.060*
C1'	0.5370 (6)	0.6436 (5)	0.5553 (3)	0.0456 (9)
H1'	0.3975	0.5908	0.5352	0.055*
C2'	0.6193 (6)	0.6635 (4)	0.6506 (3)	0.0440 (9)
C3'	0.4909 (7)	0.6150 (5)	0.7189 (3)	0.0522 (10)
H3'	0.3505	0.5633	0.6997	0.063*
C4'	0.5691 (7)	0.6425 (6)	0.8116 (3)	0.0607 (11)
H4'	0.4830	0.6079	0.8548	0.073*
C5'	0.7779 (7)	0.7226 (6)	0.8422 (3)	0.0622 (11)
H5'	0.8277	0.7446	0.9059	0.075*
C6'	0.9095 (7)	0.7690 (5)	0.7797 (3)	0.0569 (10)
H6'	1.0496	0.8198	0.8008	0.068*
C7'	0.8332 (6)	0.7400 (5)	0.6821 (3)	0.0487 (9)
C8'	0.9599 (6)	0.7907 (5)	0.6147 (3)	0.0536 (10)
H8'	1.1029	0.8374	0.6333	0.064*
C9'	0.8756 (6)	0.7720 (5)	0.5237 (3)	0.0486 (9)
H9'	0.9626	0.8070	0.4809	0.058*
C10'	0.6590 (6)	0.7009 (4)	0.4907 (2)	0.0420 (8)
C11'	0.5689 (6)	0.6949 (4)	0.3917 (3)	0.0432 (9)
C12'	0.6771 (6)	0.7610 (5)	0.3238 (3)	0.0467 (9)
H12'	0.8171	0.8159	0.3342	0.056*
C13'	0.5428 (6)	0.7320 (5)	0.2383 (3)	0.0456 (9)
C14'	0.5962 (7)	0.7764 (5)	0.1547 (3)	0.0526 (10)
H14'	0.7334	0.8335	0.1577	0.063*
C15'	0.4729 (7)	0.7471 (6)	0.0676 (3)	0.0574 (11)
H15'	0.5391	0.7871	0.0198	0.069*
C16'	0.2669 (7)	0.6676 (6)	0.0410 (3)	0.0569 (10)
H16'	0.2159	0.6595	−0.0224	0.068*
C17'	0.1225 (7)	0.5972 (5)	0.0944 (3)	0.0549 (10)
H17'	−0.0119	0.5511	0.0620	0.066*
C18'	0.1523 (6)	0.5867 (5)	0.1894 (3)	0.0482 (9)
H18'	0.0357	0.5345	0.2124	0.058*
C19'	0.3336 (6)	0.6442 (4)	0.2542 (3)	0.0435 (8)
C20'	0.3596 (6)	0.6260 (5)	0.3491 (3)	0.0459 (9)
H20'	0.2543	0.5758	0.3795	0.055*

	U11	U22	U33	U12	U13	U23
C1	0.047 (2)	0.048 (2)	0.063 (3)	0.0042 (18)	0.0056 (19)	0.0059 (19)
C2	0.049 (2)	0.047 (2)	0.075 (3)	0.0051 (19)	0.003 (2)	0.007 (2)
C3	0.048 (2)	0.041 (2)	0.066 (3)	−0.0037 (18)	0.0014 (19)	0.0053 (18)
C4	0.055 (3)	0.061 (3)	0.070 (3)	−0.003 (2)	−0.007 (2)	0.011 (2)
C5	0.075 (3)	0.085 (3)	0.049 (3)	−0.009 (3)	−0.008 (2)	0.010 (2)
C6	0.062 (3)	0.077 (3)	0.054 (3)	−0.005 (2)	0.010 (2)	−0.001 (2)
C7	0.049 (2)	0.055 (2)	0.057 (3)	0.0003 (19)	0.0057 (18)	−0.0010 (19)
C8	0.049 (2)	0.036 (2)	0.053 (2)	−0.0037 (17)	0.0015 (17)	0.0011 (17)
C9	0.044 (2)	0.041 (2)	0.059 (2)	0.0024 (17)	0.0063 (17)	0.0077 (17)
C10	0.0410 (19)	0.0329 (19)	0.054 (2)	−0.0020 (16)	0.0063 (16)	0.0046 (16)
C11	0.038 (2)	0.0348 (19)	0.058 (2)	0.0015 (16)	0.0054 (16)	0.0067 (17)
C12	0.044 (2)	0.045 (2)	0.054 (3)	0.0057 (17)	0.0066 (17)	0.0051 (17)
C13	0.0359 (19)	0.0331 (18)	0.065 (3)	0.0057 (14)	0.0081 (16)	0.0081 (17)
C14	0.043 (2)	0.047 (2)	0.059 (3)	0.0061 (17)	0.0087 (17)	0.0080 (18)
C15	0.050 (2)	0.060 (3)	0.064 (3)	0.006 (2)	0.0025 (19)	0.016 (2)
C16	0.057 (3)	0.066 (3)	0.053 (2)	−0.003 (2)	0.0024 (19)	0.013 (2)
C17	0.059 (3)	0.059 (3)	0.063 (3)	0.001 (2)	0.018 (2)	0.012 (2)
C18	0.049 (2)	0.051 (2)	0.064 (3)	0.0026 (18)	0.0158 (19)	0.0096 (19)
C19	0.042 (2)	0.0363 (19)	0.065 (2)	0.0021 (15)	0.0154 (17)	0.0079 (17)
C20	0.046 (2)	0.046 (2)	0.059 (2)	0.0073 (18)	0.0093 (18)	0.0084 (18)
C1'	0.038 (2)	0.039 (2)	0.060 (2)	−0.0012 (16)	0.0065 (17)	0.0073 (17)
C2'	0.045 (2)	0.0330 (19)	0.055 (2)	0.0021 (16)	0.0100 (17)	0.0065 (16)
C3'	0.045 (2)	0.053 (2)	0.061 (3)	−0.0004 (18)	0.0114 (18)	0.0114 (19)
C4'	0.059 (3)	0.072 (3)	0.054 (3)	0.007 (2)	0.013 (2)	0.013 (2)
C5'	0.063 (3)	0.072 (3)	0.049 (2)	0.013 (2)	0.003 (2)	0.003 (2)
C6'	0.049 (2)	0.058 (3)	0.062 (3)	0.0041 (19)	0.0021 (19)	0.0034 (19)
C7'	0.043 (2)	0.041 (2)	0.062 (3)	0.0055 (17)	0.0073 (17)	0.0083 (17)
C8'	0.042 (2)	0.051 (2)	0.067 (3)	−0.0062 (18)	0.0022 (19)	0.0087 (19)
C9'	0.043 (2)	0.045 (2)	0.058 (2)	0.0000 (17)	0.0106 (17)	0.0067 (18)
C10'	0.045 (2)	0.0319 (18)	0.050 (2)	0.0036 (16)	0.0103 (16)	0.0042 (16)
C11'	0.042 (2)	0.0345 (19)	0.054 (2)	0.0047 (16)	0.0098 (16)	0.0065 (16)
C12'	0.041 (2)	0.044 (2)	0.056 (2)	−0.0016 (17)	0.0085 (17)	0.0050 (17)
C13'	0.044 (2)	0.0386 (19)	0.055 (2)	0.0039 (16)	0.0121 (17)	0.0044 (16)
C14'	0.053 (2)	0.050 (2)	0.057 (3)	0.0013 (18)	0.0178 (19)	0.0058 (18)
C15'	0.056 (3)	0.063 (3)	0.055 (3)	0.005 (2)	0.017 (2)	0.0069 (19)
C16'	0.059 (3)	0.068 (3)	0.042 (2)	0.008 (2)	0.0062 (18)	0.0022 (19)
C17'	0.047 (2)	0.059 (3)	0.056 (3)	0.0019 (19)	0.0024 (18)	0.0024 (19)
C18'	0.040 (2)	0.041 (2)	0.064 (3)	−0.0002 (16)	0.0087 (17)	0.0077 (17)
C19'	0.0365 (19)	0.0377 (19)	0.057 (2)	0.0035 (15)	0.0105 (16)	0.0057 (16)
C20'	0.038 (2)	0.043 (2)	0.058 (2)	0.0019 (16)	0.0082 (17)	0.0098 (17)

C1—C2	1.353 (5)	C1'—C10'	1.382 (5)
C1—C10	1.426 (5)	C1'—C2'	1.402 (5)
C1—H1	0.9300	C1'—H1'	0.9300
C2—C3	1.411 (6)	C2'—C7'	1.415 (5)
C2—H2	0.9300	C2'—C3'	1.423 (5)
C3—C8	1.423 (5)	C3'—C4'	1.361 (6)
C3—C4	1.431 (6)	C3'—H3'	0.9300
C4—C5	1.362 (7)	C4'—C5'	1.397 (6)
C4—H4	0.9300	C4'—H4'	0.9300
C5—C6	1.395 (7)	C5'—C6'	1.365 (6)
C5—H5	0.9300	C5'—H5'	0.9300
C6—C7	1.357 (5)	C6'—C7'	1.425 (5)
C6—H6	0.9300	C6'—H6'	0.9300
C7—C8	1.410 (5)	C7'—C8'	1.412 (5)
C7—H7	0.9300	C8'—C9'	1.348 (5)
C8—C9	1.400 (5)	C8'—H8'	0.9300
C9—C10	1.373 (5)	C9'—C10'	1.418 (5)
C9—H9	0.9300	C9'—H9'	0.9300
C10—C11	1.469 (5)	C10'—C11'	1.471 (5)
C11—C20	1.391 (5)	C11'—C12'	1.401 (5)
C11—C12	1.408 (5)	C11'—C20'	1.407 (5)
C12—C13	1.386 (5)	C12'—C13'	1.390 (5)
C12—H12	0.9300	C12'—H12'	0.9300
C13—C14	1.389 (5)	C13'—C14'	1.384 (5)
C13—C19	1.488 (5)	C13'—C19'	1.490 (5)
C14—C15	1.379 (5)	C14'—C15'	1.379 (5)
C14—H14	0.9300	C14'—H14'	0.9300
C15—C16	1.395 (6)	C15'—C16'	1.372 (6)
C15—H15	0.9300	C15'—H15'	0.9300
C16—C17	1.376 (6)	C16'—C17'	1.394 (6)
C16—H16	0.9300	C16'—H16'	0.9300
C17—C18	1.371 (6)	C17'—C18'	1.386 (5)
C17—H17	0.9300	C17'—H17'	0.9300
C18—C19	1.383 (5)	C18'—C19'	1.383 (5)
C18—H18	0.9300	C18'—H18'	0.9300
C19—C20	1.396 (5)	C19'—C20'	1.398 (5)
C20—H20	0.9300	C20'—H20'	0.9300
C2—C1—C10	122.0 (4)	C10'—C1'—C2'	121.3 (3)
C2—C1—H1	119.0	C10'—C1'—H1'	119.3
C10—C1—H1	119.0	C2'—C1'—H1'	119.3
C1—C2—C3	120.7 (4)	C1'—C2'—C7'	120.0 (3)
C1—C2—H2	119.7	C1'—C2'—C3'	122.1 (3)
C3—C2—H2	119.7	C7'—C2'—C3'	117.8 (4)
C2—C3—C8	118.4 (4)	C4'—C3'—C2'	121.4 (4)
C2—C3—C4	122.4 (4)	C4'—C3'—H3'	119.3
C8—C3—C4	119.2 (4)	C2'—C3'—H3'	119.3
C5—C4—C3	119.4 (4)	C3'—C4'—C5'	120.3 (4)
C5—C4—H4	120.3	C3'—C4'—H4'	119.8
C3—C4—H4	120.3	C5'—C4'—H4'	119.8
C4—C5—C6	121.5 (4)	C6'—C5'—C4'	120.6 (4)
C4—C5—H5	119.2	C6'—C5'—H5'	119.7
C6—C5—H5	119.2	C4'—C5'—H5'	119.7
C7—C6—C5	120.1 (4)	C5'—C6'—C7'	120.3 (4)
C7—C6—H6	120.0	C5'—C6'—H6'	119.9
C5—C6—H6	120.0	C7'—C6'—H6'	119.9
C6—C7—C8	121.6 (4)	C8'—C7'—C2'	118.0 (4)
C6—C7—H7	119.2	C8'—C7'—C6'	122.5 (4)
C8—C7—H7	119.2	C2'—C7'—C6'	119.4 (4)
C9—C8—C7	122.7 (3)	C9'—C8'—C7'	120.7 (4)
C9—C8—C3	119.2 (4)	C9'—C8'—H8'	119.7
C7—C8—C3	118.1 (4)	C7'—C8'—H8'	119.7
C10—C9—C8	122.3 (3)	C8'—C9'—C10'	122.5 (3)
C10—C9—H9	118.9	C8'—C9'—H9'	118.8
C8—C9—H9	118.9	C10'—C9'—H9'	118.8
C9—C10—C1	117.5 (3)	C1'—C10'—C9'	117.4 (3)
C9—C10—C11	122.9 (3)	C1'—C10'—C11'	122.2 (3)
C1—C10—C11	119.5 (3)	C9'—C10'—C11'	120.3 (3)
C20—C11—C12	107.7 (3)	C12'—C11'—C20'	108.1 (3)
C20—C11—C10	126.5 (3)	C12'—C11'—C10'	125.3 (3)
C12—C11—C10	125.7 (3)	C20'—C11'—C10'	126.5 (3)
C13—C12—C11	110.1 (3)	C13'—C12'—C11'	109.4 (3)
C13—C12—H12	124.9	C13'—C12'—H12'	125.3
C11—C12—H12	124.9	C11'—C12'—H12'	125.3
C12—C13—C14	126.5 (3)	C14'—C13'—C12'	125.9 (4)
C12—C13—C19	105.9 (3)	C14'—C13'—C19'	127.1 (4)
C14—C13—C19	127.6 (4)	C12'—C13'—C19'	107.0 (3)
C15—C14—C13	129.0 (4)	C15'—C14'—C13'	128.5 (4)
C15—C14—H14	115.5	C15'—C14'—H14'	115.7
C13—C14—H14	115.5	C13'—C14'—H14'	115.7
C14—C15—C16	128.1 (4)	C16'—C15'—C14'	129.5 (4)
C14—C15—H15	116.0	C16'—C15'—H15'	115.3
C16—C15—H15	116.0	C14'—C15'—H15'	115.3
C17—C16—C15	129.9 (4)	C15'—C16'—C17'	130.0 (4)
C17—C16—H16	115.1	C15'—C16'—H16'	115.0
C15—C16—H16	115.1	C17'—C16'—H16'	115.0
C18—C17—C16	129.6 (4)	C18'—C17'—C16'	128.7 (4)
C18—C17—H17	115.2	C18'—C17'—H17'	115.7
C16—C17—H17	115.2	C16'—C17'—H17'	115.7
C17—C18—C19	128.9 (4)	C19'—C18'—C17'	128.2 (4)
C17—C18—H18	115.6	C19'—C18'—H18'	115.9
C19—C18—H18	115.6	C17'—C18'—H18'	115.9
C18—C19—C20	126.8 (4)	C18'—C19'—C20'	126.2 (3)
C18—C19—C13	126.9 (4)	C18'—C19'—C13'	128.1 (3)
C20—C19—C13	106.3 (3)	C20'—C19'—C13'	105.6 (3)
C11—C20—C19	109.9 (3)	C19'—C20'—C11'	109.8 (3)
C11—C20—H20	125.0	C19'—C20'—H20'	125.1
C19—C20—H20	125.0	C11'—C20'—H20'	125.1
C10—C1—C2—C3	−0.3 (6)	C10'—C1'—C2'—C7'	−1.4 (5)
C1—C2—C3—C8	−1.2 (6)	C10'—C1'—C2'—C3'	176.2 (3)
C1—C2—C3—C4	178.3 (4)	C1'—C2'—C3'—C4'	−176.9 (4)
C2—C3—C4—C5	179.5 (4)	C7'—C2'—C3'—C4'	0.7 (5)
C8—C3—C4—C5	−1.0 (6)	C2'—C3'—C4'—C5'	1.1 (6)
C3—C4—C5—C6	0.2 (7)	C3'—C4'—C5'—C6'	−2.2 (7)
C4—C5—C6—C7	0.3 (8)	C4'—C5'—C6'—C7'	1.5 (7)
C5—C6—C7—C8	0.1 (7)	C1'—C2'—C7'—C8'	−1.4 (5)
C6—C7—C8—C9	178.9 (4)	C3'—C2'—C7'—C8'	−179.1 (3)
C6—C7—C8—C3	−0.9 (6)	C1'—C2'—C7'—C6'	176.3 (3)
C2—C3—C8—C9	1.1 (5)	C3'—C2'—C7'—C6'	−1.4 (5)
C4—C3—C8—C9	−178.4 (4)	C5'—C6'—C7'—C8'	177.9 (4)
C2—C3—C8—C7	−179.1 (4)	C5'—C6'—C7'—C2'	0.3 (6)
C4—C3—C8—C7	1.3 (5)	C2'—C7'—C8'—C9'	2.3 (5)
C7—C8—C9—C10	−179.2 (4)	C6'—C7'—C8'—C9'	−175.4 (3)
C3—C8—C9—C10	0.5 (5)	C7'—C8'—C9'—C10'	−0.3 (6)
C8—C9—C10—C1	−2.0 (5)	C2'—C1'—C10'—C9'	3.3 (5)
C8—C9—C10—C11	175.9 (3)	C2'—C1'—C10'—C11'	−174.8 (3)
C2—C1—C10—C9	1.9 (5)	C8'—C9'—C10'—C1'	−2.5 (5)
C2—C1—C10—C11	−176.0 (3)	C8'—C9'—C10'—C11'	175.7 (3)
C9—C10—C11—C20	−172.8 (4)	C1'—C10'—C11'—C12'	175.6 (4)
C1—C10—C11—C20	5.0 (5)	C9'—C10'—C11'—C12'	−2.4 (5)
C9—C10—C11—C12	3.7 (5)	C1'—C10'—C11'—C20'	−3.0 (5)
C1—C10—C11—C12	−178.5 (4)	C9'—C10'—C11'—C20'	178.9 (4)
C20—C11—C12—C13	−0.7 (4)	C20'—C11'—C12'—C13'	−1.3 (4)
C10—C11—C12—C13	−177.7 (3)	C10'—C11'—C12'—C13'	179.8 (3)
C11—C12—C13—C14	−179.4 (3)	C11'—C12'—C13'—C14'	−178.7 (4)
C11—C12—C13—C19	0.0 (4)	C11'—C12'—C13'—C19'	1.1 (4)
C12—C13—C14—C15	178.8 (4)	C12'—C13'—C14'—C15'	178.2 (4)
C19—C13—C14—C15	−0.5 (6)	C19'—C13'—C14'—C15'	−1.5 (7)
C13—C14—C15—C16	0.5 (7)	C13'—C14'—C15'—C16'	0.2 (8)
C14—C15—C16—C17	0.3 (8)	C14'—C15'—C16'—C17'	1.4 (8)
C15—C16—C17—C18	−0.3 (8)	C15'—C16'—C17'—C18'	−1.2 (8)
C16—C17—C18—C19	−0.8 (7)	C16'—C17'—C18'—C19'	0.1 (7)
C17—C18—C19—C20	−179.4 (4)	C17'—C18'—C19'—C20'	−177.9 (4)
C17—C18—C19—C13	1.3 (7)	C17'—C18'—C19'—C13'	0.0 (6)
C12—C13—C19—C18	180.0 (4)	C14'—C13'—C19'—C18'	1.1 (6)
C14—C13—C19—C18	−0.6 (6)	C12'—C13'—C19'—C18'	−178.7 (3)
C12—C13—C19—C20	0.6 (4)	C14'—C13'—C19'—C20'	179.3 (4)
C14—C13—C19—C20	−179.9 (3)	C12'—C13'—C19'—C20'	−0.4 (4)
C12—C11—C20—C19	1.1 (4)	C18'—C19'—C20'—C11'	177.9 (3)
C10—C11—C20—C19	178.1 (3)	C13'—C19'—C20'—C11'	−0.4 (4)
C18—C19—C20—C11	179.6 (4)	C12'—C11'—C20'—C19'	1.0 (4)
C13—C19—C20—C11	−1.1 (4)	C10'—C11'—C20'—C19'	179.9 (3)

Cg1, Cg4, Cg5, Cg6, Cg7 and Cg8 are the centroids of the C1–C3,C8–C10, C13–C19, C1'-C2',C7'–C10', C2'–C7', C11'–C13',C19',C20' and C13'–C19' rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg5i	0.93	2.84	3.488 (4)	128
C7—H7···Cg6ii	0.93	2.81	3.544 (4)	137
C8'—H8'···Cg1iii	0.93	2.82	3.456 (4)	126
C14—H14···Cg7ii	0.93	2.75	3.430 (4)	131
C14'—H14'···Cg4iii	0.93	2.77	3.485 (4)	135
C18—H18···Cg8i	0.93	2.73	3.446 (4)	134
C18'—H18'···Cg4	0.93	2.79	3.463 (4)	130

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg4, Cg5, Cg6, Cg7 and Cg8 are the centroids of the C1–C3/C8–C10, C13–C19, C1′–C2′/C7′–C10′, C2′–C7′, C11′–C13′/C19′,C20′ and C13′–C19′ rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg5i	0.93	2.84	3.488 (4)	128
C7—H7⋯Cg6ii	0.93	2.81	3.544 (4)	137
C8′—H8′⋯Cg1iii	0.93	2.82	3.456 (4)	126
C14—H14⋯Cg7ii	0.93	2.75	3.430 (4)	131
C14′—H14′⋯Cg4iii	0.93	2.77	3.485 (4)	135
C18—H18⋯Cg8i	0.93	2.73	3.446 (4)	134
C18′—H18′⋯Cg4	0.93	2.79	3.463 (4)	130

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