6-(4-Meth-oxy-phen-yl)naphtho[2,3-b][1]benzothio-phene.

The asymmetric unit of the title compound, C23H16OS, contains two independent mol-ecules with opposite orientations of the meth-oxy groups bonded to the benzene rings. The napthobenzothiophene group in the two molecules is separated by an average distance of 3.912 Å. In both mol-ecules, the napthobenzothio-phene unit is almost planar, with r.m.s deviations of 0.0522 and 0.0143 Å. The meth-oxy-phenyl ring makes dihedral angles of 67.0 (6)° and 70.4 (6)° with respect to the napthobenzothio-phene ring system in the two mol-ecules. The crystal packing features C-H⋯S, π-π [centroid-centroid distances = 3.666 (10) and 3.658 (10) Å] and C-H⋯π inter-actions, forming a sheet running along the b-axis direction.

Related literature

For the biological activity of thio­phene derivatives, see: Bonini et al. (2005 ▶); Brault et al. (2005 ▶); Isloora et al. (2010 ▶); Xia et al. (2010 ▶). For a related structure, see: Gunasekaran et al. (2010 ▶).

Experimental

Crystal data

C23H16OS

M = 340.42

Triclinic,

a = 6.2019 (3) Å

b = 11.2124 (6) Å

c = 24.4724 (13) Å

α = 95.759 (3)°

β = 91.762 (3)°

γ = 95.617 (3)°

V = 1683.63 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.981, T max = 0.985

30236 measured reflections

8440 independent reflections

6029 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.140

S = 1.03

8440 reflections

451 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812047137/pv2598sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047137/pv2598Isup2.hkl

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

C23H16OS	Z = 4
Mr = 340.42	F(000) = 712
Triclinic, P1	Dx = 1.343 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.2019 (3) Å	Cell parameters from 8440 reflections
b = 11.2124 (6) Å	θ = 0.8–28.5°
c = 24.4724 (13) Å	µ = 0.20 mm−1
α = 95.759 (3)°	T = 293 K
β = 91.762 (3)°	Block, colourless
γ = 95.617 (3)°	0.20 × 0.20 × 0.20 mm
V = 1683.63 (15) Å3

Bruker SMART APEXII area-detector diffractometer	8440 independent reflections
Radiation source: fine-focus sealed tube	6029 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ω and φ scans	θmax = 28.5°, θmin = 0.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −8→8
Tmin = 0.981, Tmax = 0.985	k = −14→15
30236 measured reflections	l = −32→32

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) = 0.140	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0729P)2 + 0.216P] where P = (Fo2 + 2Fc2)/3
8440 reflections	(Δ/σ)max = 0.001
451 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.28 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
S1	0.18748 (7)	0.11396 (4)	0.544498 (16)	0.04374 (13)
S1'	0.32902 (7)	0.37462 (4)	0.961647 (16)	0.04379 (13)
O1	0.4892 (2)	0.28907 (12)	0.32371 (5)	0.0549 (3)
O1'	−0.0436 (2)	0.23774 (13)	1.18636 (5)	0.0575 (3)
C17	0.4236 (2)	0.19074 (14)	0.57740 (6)	0.0373 (3)
C8'	−0.0574 (2)	0.22460 (14)	0.95470 (6)	0.0366 (3)
C18	0.2493 (3)	0.09979 (14)	0.65053 (6)	0.0400 (4)
C16'	0.1203 (2)	0.27619 (14)	0.87037 (6)	0.0379 (3)
C9	0.7591 (2)	0.31808 (14)	0.58557 (7)	0.0403 (4)
C5'	−0.0552 (2)	0.23189 (14)	1.01597 (6)	0.0365 (3)
C17'	0.1090 (2)	0.28311 (14)	0.92850 (6)	0.0363 (3)
C8	0.5807 (2)	0.25893 (14)	0.55212 (6)	0.0385 (3)
C18'	0.3128 (3)	0.34510 (14)	0.85358 (6)	0.0396 (4)
C16	0.4363 (2)	0.17469 (14)	0.63429 (6)	0.0391 (3)
C19	0.1000 (3)	0.06293 (14)	0.60615 (6)	0.0405 (4)
C14'	−0.2168 (3)	0.14796 (14)	0.86256 (6)	0.0396 (4)
C2	0.5044 (3)	0.28681 (15)	0.37968 (7)	0.0409 (4)
C15'	−0.0416 (3)	0.20851 (15)	0.83843 (6)	0.0416 (4)
H15'	−0.0352	0.2027	0.8003	0.050*
C15	0.6110 (3)	0.22988 (15)	0.66590 (7)	0.0443 (4)
H15	0.6216	0.2192	0.7031	0.053*
C4'	0.0925 (3)	0.17389 (16)	1.04479 (6)	0.0449 (4)
H4'	0.1928	0.1314	1.0256	0.054*
C5	0.5587 (2)	0.27062 (14)	0.49206 (6)	0.0376 (3)
C19'	0.4407 (3)	0.40253 (15)	0.89885 (7)	0.0417 (4)
C4	0.3946 (3)	0.33000 (17)	0.47121 (7)	0.0495 (4)
H4	0.3005	0.3652	0.4953	0.059*
C9'	−0.2270 (2)	0.15599 (14)	0.92128 (6)	0.0377 (3)
C7	0.6709 (3)	0.22705 (16)	0.39932 (7)	0.0467 (4)
H7	0.7643	0.1920	0.3750	0.056*
C14	0.7746 (3)	0.30247 (15)	0.64273 (7)	0.0426 (4)
C20	−0.0950 (3)	−0.00424 (15)	0.61356 (7)	0.0482 (4)
H20	−0.1941	−0.0273	0.5842	0.058*
C13	0.9558 (3)	0.36222 (18)	0.67486 (8)	0.0549 (5)
H13	0.9679	0.3520	0.7120	0.066*
C23'	0.3812 (3)	0.35939 (16)	0.80082 (7)	0.0490 (4)
H23'	0.2976	0.3228	0.7704	0.059*
C3'	0.0937 (3)	0.17794 (17)	1.10136 (7)	0.0475 (4)
H3'	0.1941	0.1386	1.1199	0.057*
C6	0.6984 (3)	0.21946 (16)	0.45486 (7)	0.0459 (4)
H6	0.8114	0.1798	0.4678	0.055*
C2'	−0.0545 (3)	0.24060 (15)	1.13040 (6)	0.0418 (4)
C7'	−0.2004 (3)	0.30002 (17)	1.10305 (7)	0.0508 (4)
H7'	−0.2990	0.3433	1.1225	0.061*
C6'	−0.1999 (3)	0.29510 (17)	1.04629 (7)	0.0505 (4)
H6'	−0.2996	0.3354	1.0280	0.061*
C3	0.3662 (3)	0.33868 (17)	0.41563 (7)	0.0496 (4)
H3	0.2545	0.3793	0.4026	0.060*
C23	0.2027 (3)	0.06416 (16)	0.70203 (7)	0.0496 (4)
H23	0.3013	0.0861	0.7316	0.059*
C10	0.9248 (3)	0.39496 (16)	0.56390 (8)	0.0479 (4)
H10	0.9171	0.4069	0.5269	0.057*
C22	0.0102 (3)	−0.00373 (17)	0.70930 (8)	0.0565 (5)
H22	−0.0203	−0.0280	0.7437	0.068*
C13'	−0.3877 (3)	0.07889 (16)	0.83011 (7)	0.0481 (4)
H13'	−0.3815	0.0722	0.7920	0.058*
C11'	−0.5702 (3)	0.03041 (17)	0.91091 (8)	0.0504 (4)
H11'	−0.6884	−0.0084	0.9267	0.060*
C12'	−0.5596 (3)	0.02260 (17)	0.85331 (7)	0.0520 (4)
H12'	−0.6705	−0.0212	0.8312	0.062*
C10'	−0.4088 (3)	0.09435 (15)	0.94365 (7)	0.0433 (4)
H10'	−0.4180	0.0977	0.9816	0.052*
C11	1.0943 (3)	0.45122 (17)	0.59649 (9)	0.0580 (5)
H11	1.1999	0.5017	0.5816	0.070*
C21	−0.1387 (3)	−0.03607 (17)	0.66532 (8)	0.0543 (5)
H21	−0.2699	−0.0799	0.6710	0.065*
C20'	0.6349 (3)	0.47103 (17)	0.89157 (8)	0.0534 (4)
H20'	0.7200	0.5079	0.9217	0.064*
C21'	0.6986 (3)	0.48325 (18)	0.83907 (8)	0.0613 (5)
H21'	0.8278	0.5292	0.8337	0.074*
C12	1.1107 (3)	0.43343 (19)	0.65267 (9)	0.0609 (5)
H12	1.2284	0.4708	0.6745	0.073*
C1	0.3082 (4)	0.3402 (2)	0.30222 (8)	0.0734 (6)
H1A	0.3146	0.3370	0.2630	0.110*
H1B	0.3109	0.4226	0.3176	0.110*
H1C	0.1767	0.2957	0.3116	0.110*
C22'	0.5729 (3)	0.42791 (17)	0.79378 (8)	0.0575 (5)
H22'	0.6188	0.4373	0.7585	0.069*
C1'	−0.2057 (4)	0.2910 (2)	1.21743 (8)	0.0775 (7)
H1D	−0.1800	0.2827	1.2557	0.116*
H1E	−0.3458	0.2513	1.2054	0.116*
H1F	−0.2008	0.3749	1.2121	0.116*

	U11	U22	U33	U12	U13	U23
S1	0.0432 (2)	0.0465 (3)	0.0395 (2)	−0.00126 (18)	−0.00526 (17)	0.00235 (18)
S1'	0.0431 (2)	0.0492 (3)	0.0362 (2)	−0.00239 (18)	−0.00513 (16)	−0.00047 (17)
O1	0.0586 (8)	0.0671 (9)	0.0408 (7)	0.0062 (6)	0.0047 (5)	0.0143 (6)
O1'	0.0621 (8)	0.0789 (9)	0.0316 (6)	0.0090 (7)	0.0024 (5)	0.0037 (6)
C17	0.0372 (8)	0.0355 (8)	0.0382 (8)	0.0045 (6)	−0.0021 (6)	−0.0011 (6)
C8'	0.0397 (8)	0.0376 (8)	0.0327 (8)	0.0067 (6)	−0.0027 (6)	0.0041 (6)
C18	0.0427 (8)	0.0362 (8)	0.0401 (9)	0.0034 (7)	0.0015 (7)	−0.0002 (7)
C16'	0.0409 (8)	0.0374 (8)	0.0352 (8)	0.0036 (7)	−0.0021 (6)	0.0048 (6)
C9	0.0374 (8)	0.0370 (8)	0.0456 (9)	0.0069 (7)	0.0031 (7)	−0.0035 (7)
C5'	0.0387 (8)	0.0381 (8)	0.0322 (7)	0.0020 (7)	−0.0019 (6)	0.0034 (6)
C17'	0.0386 (8)	0.0354 (8)	0.0343 (8)	0.0037 (6)	−0.0055 (6)	0.0025 (6)
C8	0.0390 (8)	0.0360 (8)	0.0399 (8)	0.0070 (7)	0.0018 (6)	−0.0015 (6)
C18'	0.0424 (8)	0.0377 (8)	0.0383 (8)	0.0026 (7)	−0.0006 (6)	0.0043 (7)
C16	0.0405 (8)	0.0380 (9)	0.0380 (8)	0.0048 (7)	−0.0007 (6)	−0.0001 (6)
C19	0.0445 (9)	0.0352 (8)	0.0411 (9)	0.0059 (7)	0.0004 (7)	−0.0013 (7)
C14'	0.0418 (8)	0.0401 (9)	0.0362 (8)	0.0027 (7)	−0.0050 (6)	0.0038 (7)
C2	0.0430 (9)	0.0386 (9)	0.0406 (9)	−0.0018 (7)	0.0042 (7)	0.0064 (7)
C15'	0.0463 (9)	0.0460 (9)	0.0314 (8)	0.0005 (7)	−0.0043 (6)	0.0038 (7)
C15	0.0469 (9)	0.0473 (10)	0.0373 (8)	0.0038 (7)	−0.0034 (7)	0.0002 (7)
C4'	0.0432 (9)	0.0561 (10)	0.0381 (9)	0.0164 (8)	0.0033 (7)	0.0070 (7)
C5	0.0390 (8)	0.0347 (8)	0.0386 (8)	0.0033 (6)	0.0036 (6)	0.0015 (6)
C19'	0.0444 (9)	0.0380 (9)	0.0420 (9)	0.0037 (7)	0.0008 (7)	0.0017 (7)
C4	0.0477 (10)	0.0571 (11)	0.0468 (10)	0.0209 (8)	0.0104 (7)	0.0035 (8)
C9'	0.0391 (8)	0.0374 (8)	0.0365 (8)	0.0046 (7)	−0.0023 (6)	0.0045 (6)
C7	0.0491 (10)	0.0481 (10)	0.0445 (9)	0.0137 (8)	0.0104 (7)	0.0016 (7)
C14	0.0372 (8)	0.0418 (9)	0.0470 (9)	0.0044 (7)	−0.0011 (7)	−0.0044 (7)
C20	0.0467 (9)	0.0414 (9)	0.0533 (10)	−0.0001 (7)	−0.0016 (8)	−0.0039 (8)
C13	0.0462 (10)	0.0618 (12)	0.0528 (11)	0.0027 (9)	−0.0070 (8)	−0.0079 (9)
C23'	0.0589 (11)	0.0468 (10)	0.0402 (9)	−0.0012 (8)	0.0021 (8)	0.0055 (7)
C3'	0.0473 (9)	0.0592 (11)	0.0393 (9)	0.0156 (8)	−0.0016 (7)	0.0116 (8)
C6	0.0454 (9)	0.0477 (10)	0.0464 (10)	0.0150 (8)	0.0044 (7)	0.0036 (7)
C2'	0.0444 (9)	0.0470 (10)	0.0323 (8)	−0.0013 (7)	−0.0008 (6)	0.0022 (7)
C7'	0.0535 (10)	0.0595 (11)	0.0403 (9)	0.0213 (9)	0.0029 (7)	−0.0054 (8)
C6'	0.0556 (10)	0.0567 (11)	0.0417 (9)	0.0230 (9)	−0.0063 (8)	0.0023 (8)
C3	0.0461 (9)	0.0562 (11)	0.0504 (10)	0.0171 (8)	0.0031 (8)	0.0123 (8)
C23	0.0557 (10)	0.0489 (10)	0.0424 (9)	−0.0005 (8)	−0.0003 (8)	0.0028 (8)
C10	0.0443 (9)	0.0425 (10)	0.0548 (10)	0.0016 (7)	0.0081 (8)	−0.0041 (8)
C22	0.0700 (13)	0.0509 (11)	0.0473 (10)	−0.0030 (9)	0.0104 (9)	0.0056 (8)
C13'	0.0527 (10)	0.0498 (10)	0.0394 (9)	0.0000 (8)	−0.0094 (7)	0.0017 (7)
C11'	0.0430 (9)	0.0490 (10)	0.0577 (11)	−0.0039 (8)	0.0012 (8)	0.0069 (8)
C12'	0.0479 (10)	0.0497 (10)	0.0546 (11)	−0.0049 (8)	−0.0120 (8)	0.0007 (8)
C10'	0.0456 (9)	0.0434 (9)	0.0405 (9)	0.0020 (7)	0.0022 (7)	0.0047 (7)
C11	0.0439 (10)	0.0475 (11)	0.0772 (14)	−0.0067 (8)	0.0115 (9)	−0.0115 (9)
C21	0.0525 (10)	0.0458 (10)	0.0617 (12)	−0.0067 (8)	0.0103 (9)	0.0003 (9)
C20'	0.0503 (10)	0.0515 (11)	0.0536 (11)	−0.0071 (8)	0.0015 (8)	−0.0051 (8)
C21'	0.0619 (12)	0.0534 (12)	0.0642 (13)	−0.0136 (9)	0.0148 (10)	−0.0004 (9)
C12	0.0405 (10)	0.0631 (13)	0.0722 (14)	−0.0043 (9)	−0.0046 (9)	−0.0160 (10)
C1	0.0792 (15)	0.0909 (17)	0.0565 (12)	0.0178 (13)	−0.0037 (11)	0.0322 (11)
C22'	0.0682 (13)	0.0526 (11)	0.0505 (11)	−0.0058 (9)	0.0151 (9)	0.0076 (9)
C1'	0.0793 (15)	0.112 (2)	0.0405 (11)	0.0155 (14)	0.0159 (10)	−0.0067 (11)

S1—C19	1.7494 (17)	C7—C6	1.377 (2)
S1—C17	1.7540 (15)	C7—H7	0.9300
S1'—C19'	1.7488 (17)	C14—C13	1.422 (2)
S1'—C17'	1.7504 (15)	C20—C21	1.378 (3)
O1—C2	1.3729 (19)	C20—H20	0.9300
O1—C1	1.420 (2)	C13—C12	1.351 (3)
O1'—C2'	1.3727 (18)	C13—H13	0.9300
O1'—C1'	1.421 (2)	C23'—C22'	1.377 (3)
C17—C8	1.379 (2)	C23'—H23'	0.9300
C17—C16	1.422 (2)	C3'—C2'	1.382 (2)
C8'—C17'	1.378 (2)	C3'—H3'	0.9300
C8'—C9'	1.425 (2)	C6—H6	0.9300
C8'—C5'	1.493 (2)	C2'—C7'	1.371 (2)
C18—C23	1.390 (2)	C7'—C6'	1.385 (2)
C18—C19	1.407 (2)	C7'—H7'	0.9300
C18—C16	1.454 (2)	C6'—H6'	0.9300
C16'—C15'	1.371 (2)	C3—H3	0.9300
C16'—C17'	1.421 (2)	C23—C22	1.378 (3)
C16'—C18'	1.451 (2)	C23—H23	0.9300
C9—C8	1.423 (2)	C10—C11	1.363 (2)
C9—C10	1.426 (2)	C10—H10	0.9300
C9—C14	1.428 (2)	C22—C21	1.392 (3)
C5'—C6'	1.385 (2)	C22—H22	0.9300
C5'—C4'	1.389 (2)	C13'—C12'	1.354 (3)
C8—C5	1.492 (2)	C13'—H13'	0.9300
C18'—C23'	1.391 (2)	C11'—C10'	1.361 (2)
C18'—C19'	1.405 (2)	C11'—C12'	1.408 (2)
C16—C15	1.370 (2)	C11'—H11'	0.9300
C19—C20	1.388 (2)	C12'—H12'	0.9300
C14'—C15'	1.402 (2)	C10'—H10'	0.9300
C14'—C13'	1.421 (2)	C11—C12	1.411 (3)
C14'—C9'	1.434 (2)	C11—H11	0.9300
C2—C3	1.374 (2)	C21—H21	0.9300
C2—C7	1.384 (2)	C20'—C21'	1.372 (3)
C15'—H15'	0.9300	C20'—H20'	0.9300
C15—C14	1.407 (2)	C21'—C22'	1.391 (3)
C15—H15	0.9300	C21'—H21'	0.9300
C4'—C3'	1.380 (2)	C12—H12	0.9300
C4'—H4'	0.9300	C1—H1A	0.9600
C5—C4	1.381 (2)	C1—H1B	0.9600
C5—C6	1.396 (2)	C1—H1C	0.9600
C19'—C20'	1.390 (2)	C22'—H22'	0.9300
C4—C3	1.381 (2)	C1'—H1D	0.9600
C4—H4	0.9300	C1'—H1E	0.9600
C9'—C10'	1.418 (2)	C1'—H1F	0.9600
C19—S1—C17	91.55 (7)	C12—C13—H13	119.2
C19'—S1'—C17'	91.64 (7)	C14—C13—H13	119.2
C2—O1—C1	116.84 (14)	C22'—C23'—C18'	119.79 (17)
C2'—O1'—C1'	117.75 (15)	C22'—C23'—H23'	120.1
C8—C17—C16	123.04 (14)	C18'—C23'—H23'	120.1
C8—C17—S1	125.08 (12)	C4'—C3'—C2'	119.88 (14)
C16—C17—S1	111.88 (12)	C4'—C3'—H3'	120.1
C17'—C8'—C9'	117.64 (13)	C2'—C3'—H3'	120.1
C17'—C8'—C5'	120.48 (13)	C7—C6—C5	120.82 (15)
C9'—C8'—C5'	121.87 (14)	C7—C6—H6	119.6
C23—C18—C19	119.04 (16)	C5—C6—H6	119.6
C23—C18—C16	129.04 (15)	C7'—C2'—O1'	124.30 (15)
C19—C18—C16	111.91 (14)	C7'—C2'—C3'	119.98 (15)
C15'—C16'—C17'	118.90 (15)	O1'—C2'—C3'	115.73 (14)
C15'—C16'—C18'	129.10 (14)	C2'—C7'—C6'	119.51 (16)
C17'—C16'—C18'	112.00 (13)	C2'—C7'—H7'	120.2
C8—C9—C10	121.87 (16)	C6'—C7'—H7'	120.2
C8—C9—C14	120.09 (15)	C7'—C6'—C5'	121.90 (15)
C10—C9—C14	118.04 (15)	C7'—C6'—H6'	119.0
C6'—C5'—C4'	117.34 (14)	C5'—C6'—H6'	119.0
C6'—C5'—C8'	121.91 (13)	C2—C3—C4	119.38 (15)
C4'—C5'—C8'	120.75 (14)	C2—C3—H3	120.3
C8'—C17'—C16'	123.19 (14)	C4—C3—H3	120.3
C8'—C17'—S1'	125.00 (11)	C22—C23—C18	119.95 (16)
C16'—C17'—S1'	111.81 (12)	C22—C23—H23	120.0
C17—C8—C9	117.52 (14)	C18—C23—H23	120.0
C17—C8—C5	120.25 (14)	C11—C10—C9	121.17 (18)
C9—C8—C5	122.22 (14)	C11—C10—H10	119.4
C23'—C18'—C19'	119.03 (16)	C9—C10—H10	119.4
C23'—C18'—C16'	128.98 (15)	C23—C22—C21	120.23 (17)
C19'—C18'—C16'	112.00 (14)	C23—C22—H22	119.9
C15—C16—C17	118.98 (15)	C21—C22—H22	119.9
C15—C16—C18	129.06 (15)	C12'—C13'—C14'	121.58 (16)
C17—C16—C18	111.94 (13)	C12'—C13'—H13'	119.2
C20—C19—C18	121.03 (16)	C14'—C13'—H13'	119.2
C20—C19—S1	126.27 (13)	C10'—C11'—C12'	120.47 (17)
C18—C19—S1	112.68 (13)	C10'—C11'—H11'	119.8
C15'—C14'—C13'	121.48 (14)	C12'—C11'—H11'	119.8
C15'—C14'—C9'	119.94 (14)	C13'—C12'—C11'	119.97 (16)
C13'—C14'—C9'	118.58 (15)	C13'—C12'—H12'	120.0
O1—C2—C3	124.11 (15)	C11'—C12'—H12'	120.0
O1—C2—C7	115.89 (15)	C11'—C10'—C9'	121.62 (16)
C3—C2—C7	120.00 (15)	C11'—C10'—H10'	119.2
C16'—C15'—C14'	120.69 (14)	C9'—C10'—H10'	119.2
C16'—C15'—H15'	119.7	C10—C11—C12	120.43 (18)
C14'—C15'—H15'	119.7	C10—C11—H11	119.8
C16—C15—C14	120.67 (15)	C12—C11—H11	119.8
C16—C15—H15	119.7	C20—C21—C22	121.10 (17)
C14—C15—H15	119.7	C20—C21—H21	119.5
C3'—C4'—C5'	121.38 (15)	C22—C21—H21	119.5
C3'—C4'—H4'	119.3	C21'—C20'—C19'	118.71 (17)
C5'—C4'—H4'	119.3	C21'—C20'—H20'	120.6
C4—C5—C6	117.68 (15)	C19'—C20'—H20'	120.6
C4—C5—C8	120.80 (14)	C20'—C21'—C22'	121.02 (18)
C6—C5—C8	121.50 (14)	C20'—C21'—H21'	119.5
C20'—C19'—C18'	121.00 (16)	C22'—C21'—H21'	119.5
C20'—C19'—S1'	126.44 (13)	C13—C12—C11	120.16 (17)
C18'—C19'—S1'	112.55 (13)	C13—C12—H12	119.9
C3—C4—C5	122.00 (15)	C11—C12—H12	119.9
C3—C4—H4	119.0	O1—C1—H1A	109.5
C5—C4—H4	119.0	O1—C1—H1B	109.5
C10'—C9'—C8'	122.62 (14)	H1A—C1—H1B	109.5
C10'—C9'—C14'	117.76 (14)	O1—C1—H1C	109.5
C8'—C9'—C14'	119.62 (14)	H1A—C1—H1C	109.5
C6—C7—C2	120.11 (15)	H1B—C1—H1C	109.5
C6—C7—H7	119.9	C23'—C22'—C21'	120.46 (18)
C2—C7—H7	119.9	C23'—C22'—H22'	119.8
C15—C14—C13	121.72 (16)	C21'—C22'—H22'	119.8
C15—C14—C9	119.66 (14)	O1'—C1'—H1D	109.5
C13—C14—C9	118.61 (16)	O1'—C1'—H1E	109.5
C21—C20—C19	118.60 (16)	H1D—C1'—H1E	109.5
C21—C20—H20	120.7	O1'—C1'—H1F	109.5
C19—C20—H20	120.7	H1D—C1'—H1F	109.5
C12—C13—C14	121.57 (18)	H1E—C1'—H1F	109.5
C19—S1—C17—C8	−178.68 (14)	C6—C5—C4—C3	0.5 (3)
C19—S1—C17—C16	1.36 (12)	C8—C5—C4—C3	−177.81 (16)
C17'—C8'—C5'—C6'	110.27 (19)	C17'—C8'—C9'—C10'	−178.49 (14)
C9'—C8'—C5'—C6'	−70.9 (2)	C5'—C8'—C9'—C10'	2.7 (2)
C17'—C8'—C5'—C4'	−70.3 (2)	C17'—C8'—C9'—C14'	1.4 (2)
C9'—C8'—C5'—C4'	108.46 (18)	C5'—C8'—C9'—C14'	−177.45 (13)
C9'—C8'—C17'—C16'	−1.2 (2)	C15'—C14'—C9'—C10'	179.21 (15)
C5'—C8'—C17'—C16'	177.68 (14)	C13'—C14'—C9'—C10'	−0.2 (2)
C9'—C8'—C17'—S1'	178.44 (11)	C15'—C14'—C9'—C8'	−0.7 (2)
C5'—C8'—C17'—S1'	−2.7 (2)	C13'—C14'—C9'—C8'	179.93 (14)
C15'—C16'—C17'—C8'	0.2 (2)	O1—C2—C7—C6	−179.65 (15)
C18'—C16'—C17'—C8'	−179.42 (14)	C3—C2—C7—C6	0.0 (3)
C15'—C16'—C17'—S1'	−179.48 (12)	C16—C15—C14—C13	178.99 (16)
C18'—C16'—C17'—S1'	0.93 (17)	C16—C15—C14—C9	−0.5 (2)
C19'—S1'—C17'—C8'	179.39 (14)	C8—C9—C14—C15	−1.0 (2)
C19'—S1'—C17'—C16'	−0.96 (12)	C10—C9—C14—C15	178.29 (15)
C16—C17—C8—C9	−1.9 (2)	C8—C9—C14—C13	179.57 (15)
S1—C17—C8—C9	178.17 (11)	C10—C9—C14—C13	−1.2 (2)
C16—C17—C8—C5	179.16 (13)	C18—C19—C20—C21	−1.0 (2)
S1—C17—C8—C5	−0.8 (2)	S1—C19—C20—C21	−179.45 (13)
C10—C9—C8—C17	−177.15 (14)	C15—C14—C13—C12	−178.89 (17)
C14—C9—C8—C17	2.1 (2)	C9—C14—C13—C12	0.6 (3)
C10—C9—C8—C5	1.8 (2)	C19'—C18'—C23'—C22'	0.8 (3)
C14—C9—C8—C5	−178.99 (14)	C16'—C18'—C23'—C22'	−178.97 (17)
C15'—C16'—C18'—C23'	−0.2 (3)	C5'—C4'—C3'—C2'	0.1 (3)
C17'—C16'—C18'—C23'	179.39 (16)	C2—C7—C6—C5	0.6 (3)
C15'—C16'—C18'—C19'	−179.90 (16)	C4—C5—C6—C7	−0.8 (3)
C17'—C16'—C18'—C19'	−0.36 (19)	C8—C5—C6—C7	177.49 (16)
C8—C17—C16—C15	0.5 (2)	C1'—O1'—C2'—C7'	5.7 (3)
S1—C17—C16—C15	−179.53 (12)	C1'—O1'—C2'—C3'	−174.10 (18)
C8—C17—C16—C18	179.50 (14)	C4'—C3'—C2'—C7'	−0.9 (3)
S1—C17—C16—C18	−0.55 (16)	C4'—C3'—C2'—O1'	178.84 (16)
C23—C18—C16—C15	−1.0 (3)	O1'—C2'—C7'—C6'	−178.77 (17)
C19—C18—C16—C15	178.00 (16)	C3'—C2'—C7'—C6'	1.0 (3)
C23—C18—C16—C17	−179.85 (16)	C2'—C7'—C6'—C5'	−0.2 (3)
C19—C18—C16—C17	−0.85 (19)	C4'—C5'—C6'—C7'	−0.6 (3)
C23—C18—C19—C20	2.4 (2)	C8'—C5'—C6'—C7'	178.79 (17)
C16—C18—C19—C20	−176.73 (14)	O1—C2—C3—C4	179.32 (16)
C23—C18—C19—S1	−179.00 (13)	C7—C2—C3—C4	−0.3 (3)
C16—C18—C19—S1	1.89 (17)	C5—C4—C3—C2	0.1 (3)
C17—S1—C19—C20	176.66 (15)	C19—C18—C23—C22	−1.6 (3)
C17—S1—C19—C18	−1.87 (12)	C16—C18—C23—C22	177.35 (17)
C1—O1—C2—C3	−5.2 (3)	C8—C9—C10—C11	179.81 (15)
C1—O1—C2—C7	174.46 (17)	C14—C9—C10—C11	0.6 (2)
C17'—C16'—C15'—C14'	0.6 (2)	C18—C23—C22—C21	−0.5 (3)
C18'—C16'—C15'—C14'	−179.88 (15)	C15'—C14'—C13'—C12'	−178.44 (16)
C13'—C14'—C15'—C16'	179.04 (15)	C9'—C14'—C13'—C12'	1.0 (3)
C9'—C14'—C15'—C16'	−0.4 (2)	C14'—C13'—C12'—C11'	−0.9 (3)
C17—C16—C15—C14	0.7 (2)	C10'—C11'—C12'—C13'	0.1 (3)
C18—C16—C15—C14	−178.09 (15)	C12'—C11'—C10'—C9'	0.7 (3)
C6'—C5'—C4'—C3'	0.7 (3)	C8'—C9'—C10'—C11'	179.25 (15)
C8'—C5'—C4'—C3'	−178.74 (16)	C14'—C9'—C10'—C11'	−0.6 (2)
C17—C8—C5—C4	66.3 (2)	C9—C10—C11—C12	0.7 (3)
C9—C8—C5—C4	−112.60 (19)	C19—C20—C21—C22	−1.1 (3)
C17—C8—C5—C6	−111.91 (18)	C23—C22—C21—C20	1.9 (3)
C9—C8—C5—C6	69.2 (2)	C18'—C19'—C20'—C21'	1.0 (3)
C23'—C18'—C19'—C20'	−1.2 (2)	S1'—C19'—C20'—C21'	179.79 (15)
C16'—C18'—C19'—C20'	178.60 (15)	C19'—C20'—C21'—C22'	−0.4 (3)
C23'—C18'—C19'—S1'	179.85 (13)	C14—C13—C12—C11	0.7 (3)
C16'—C18'—C19'—S1'	−0.37 (18)	C10—C11—C12—C13	−1.3 (3)
C17'—S1'—C19'—C20'	−178.14 (16)	C18'—C23'—C22'—C21'	−0.2 (3)
C17'—S1'—C19'—C18'	0.76 (13)	C20'—C21'—C22'—C23'	0.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6′—H6′···S1′i	0.93	2.87	3.7591 (17)	160
C3′—H3′···Cg15ii	0.93	2.93	3.704 (2)	141
C7—H7···Cg5iii	0.93	2.89	3.672 (2)	143
C11—H11···Cg2iv	0.93	2.91	3.789 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

Cg2, Cg5 and Cg15 are the centroids of the C2–C7, C18–C23 and C9′–C14′ rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6′—H6′⋯S1′i	0.93	2.87	3.7591 (17)	160
C3′—H3′⋯Cg15ii	0.93	2.93	3.704 (2)	141
C7—H7⋯Cg5iii	0.93	2.89	3.672 (2)	143
C11—H11⋯Cg2iv	0.93	2.91	3.789 (2)	159

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