5-Methyl-phenanthro[2,3-b]thio-phene.

The title compound, C(17)H(12)S, which crystallises with two molecules in the asymmetric unit, features four fused rings forming an essentially planar mol-ecule, with maximum deviations from the mean plane of 0.078 (2) and 0.080 (2) Å for C atoms of the thio-phene and phenanthrene groups in both the mol-ecules. The crystal packing features weak C-H⋯π inter-actions.

Related literature

For a related structure, see: Gunasekaran et al. (2010 ▶).

Experimental

Crystal data

C17H12S

M = 248.33

Monoclinic,

a = 18.7011 (10) Å

b = 5.8199 (3) Å

c = 23.4546 (14) Å

β = 105.158 (2)°

V = 2463.9 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.985

31917 measured reflections

6983 independent reflections

4446 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.195

S = 1.06

6983 reflections

327 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014838/bt5506sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014838/bt5506Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811014838/bt5506Isup3.cml

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

C17H12S	F(000) = 1040
Mr = 248.33	Dx = 1.339 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6983 reflections
a = 18.7011 (10) Å	θ = 1.3–29.7°
b = 5.8199 (3) Å	µ = 0.24 mm−1
c = 23.4546 (14) Å	T = 293 K
β = 105.158 (2)°	Block, colourless
V = 2463.9 (2) Å3	0.25 × 0.22 × 0.19 mm
Z = 8

Bruker APEXII CCD area-detector diffractometer	6983 independent reflections
Radiation source: fine-focus sealed tube	4446 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω and φ scans	θmax = 29.7°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→26
Tmin = 0.981, Tmax = 0.985	k = −8→8
31917 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.195	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.1022P)2 + 0.5162P] where P = (Fo2 + 2Fc2)/3
6983 reflections	(Δ/σ)max = 0.001
327 parameters	Δρmax = 0.47 e Å−3
2 restraints	Δρmin = −0.30 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
C1'	0.33522 (15)	0.2874 (5)	0.07093 (11)	0.0702 (7)
H1'	0.3227	0.3551	0.0337	0.084*
C1	0.55737 (13)	0.7887 (4)	0.06335 (10)	0.0601 (6)
H1	0.5490	0.8546	0.0261	0.072*
C2	0.60214 (13)	0.8818 (4)	0.11144 (10)	0.0516 (5)
H2	0.6274	1.0193	0.1114	0.062*
C2'	0.31625 (12)	0.3776 (4)	0.11600 (10)	0.0538 (5)
H2'	0.2897	0.5136	0.1144	0.065*
C3	0.60700 (11)	0.7451 (3)	0.16387 (9)	0.0431 (4)
C3'	0.34245 (11)	0.2359 (3)	0.16957 (9)	0.0449 (4)
C4	0.56138 (11)	0.5470 (3)	0.15084 (9)	0.0457 (4)
C4'	0.38181 (11)	0.0412 (3)	0.15862 (9)	0.0451 (4)
C5	0.55612 (11)	0.3950 (3)	0.19459 (10)	0.0487 (5)
H5	0.5255	0.2669	0.1856	0.058*
C5'	0.41350 (11)	−0.1131 (4)	0.20223 (10)	0.0496 (5)
H5'	0.4394	−0.2397	0.1939	0.059*
C6'	0.40615 (10)	−0.0763 (3)	0.25924 (9)	0.0438 (4)
C6	0.59727 (11)	0.4349 (3)	0.25262 (9)	0.0446 (4)
C7	0.64532 (10)	0.6288 (3)	0.26671 (9)	0.0411 (4)
C7'	0.36605 (10)	0.1153 (3)	0.27204 (8)	0.0406 (4)
C8'	0.33449 (11)	0.2692 (3)	0.22664 (9)	0.0461 (4)
H8'	0.3079	0.3951	0.2345	0.055*
C8	0.64871 (11)	0.7820 (3)	0.22128 (9)	0.0437 (4)
H8	0.6794	0.9101	0.2298	0.052*
C9'	0.35973 (10)	0.1459 (3)	0.33238 (9)	0.0431 (4)
C9	0.68848 (11)	0.6597 (3)	0.32765 (8)	0.0416 (4)
C10'	0.31838 (11)	0.3236 (4)	0.34787 (10)	0.0517 (5)
H10'	0.2927	0.4236	0.3187	0.062*
C10	0.74001 (12)	0.8395 (4)	0.34412 (9)	0.0489 (5)
H10	0.7475	0.9395	0.3153	0.059*
C11'	0.31458 (12)	0.3548 (5)	0.40558 (11)	0.0601 (6)
H11'	0.2870	0.4754	0.4149	0.072*
C11	0.77956 (13)	0.8707 (4)	0.40190 (10)	0.0567 (5)
H11	0.8128	0.9921	0.4119	0.068*
C12'	0.35180 (13)	0.2064 (5)	0.44909 (10)	0.0620 (6)
H12'	0.3492	0.2269	0.4878	0.074*
C12	0.76975 (13)	0.7205 (4)	0.44519 (10)	0.0597 (6)
H12	0.7965	0.7414	0.4843	0.072*
C13'	0.39265 (13)	0.0289 (4)	0.43557 (10)	0.0573 (6)
H13'	0.4176	−0.0697	0.4653	0.069*
C13	0.72101 (13)	0.5424 (4)	0.43057 (10)	0.0561 (6)
H13	0.7153	0.4424	0.4600	0.067*
C14'	0.39736 (10)	−0.0063 (3)	0.37744 (9)	0.0444 (4)
C14	0.67910 (12)	0.5061 (3)	0.37200 (9)	0.0459 (5)
C15'	0.44026 (11)	−0.1964 (4)	0.36283 (10)	0.0502 (5)
C15	0.62704 (12)	0.3163 (4)	0.35639 (10)	0.0503 (5)
C16	0.59013 (12)	0.2845 (4)	0.29960 (10)	0.0516 (5)
H16	0.5584	0.1591	0.2901	0.062*
C16'	0.44238 (12)	−0.2279 (4)	0.30675 (10)	0.0517 (5)
H16'	0.4684	−0.3534	0.2980	0.062*
C17'	0.48297 (13)	−0.3532 (4)	0.41088 (11)	0.0644 (6)
H17A	0.5035	−0.4779	0.3935	0.097*
H17B	0.4503	−0.4131	0.4328	0.097*
H17C	0.5223	−0.2686	0.4369	0.097*
C17	0.61402 (14)	0.1585 (4)	0.40359 (12)	0.0658 (7)
H17D	0.5801	0.0392	0.3856	0.099*
H17E	0.5935	0.2445	0.4304	0.099*
H17F	0.6602	0.0911	0.4248	0.099*
S1	0.51607 (4)	0.53496 (12)	0.07611 (3)	0.0620 (2)
S1'	0.38490 (4)	0.03471 (13)	0.08505 (3)	0.0655 (2)

	U11	U22	U33	U12	U13	U23
C1'	0.0742 (16)	0.0787 (17)	0.0525 (13)	−0.0132 (14)	0.0075 (12)	0.0174 (12)
C1	0.0656 (14)	0.0640 (14)	0.0512 (12)	0.0067 (11)	0.0162 (10)	0.0135 (11)
C2	0.0656 (13)	0.0447 (11)	0.0494 (12)	−0.0016 (10)	0.0235 (10)	0.0059 (9)
C2'	0.0551 (12)	0.0461 (11)	0.0569 (13)	0.0003 (9)	0.0087 (10)	0.0039 (10)
C3	0.0492 (10)	0.0382 (9)	0.0471 (10)	0.0007 (8)	0.0218 (8)	0.0017 (8)
C3'	0.0431 (10)	0.0442 (10)	0.0451 (10)	−0.0050 (8)	0.0073 (8)	−0.0005 (8)
C4	0.0462 (10)	0.0438 (10)	0.0495 (11)	−0.0004 (8)	0.0171 (9)	−0.0004 (9)
C4'	0.0434 (10)	0.0489 (11)	0.0426 (10)	−0.0073 (8)	0.0103 (8)	−0.0040 (9)
C5	0.0506 (11)	0.0390 (10)	0.0594 (13)	−0.0073 (8)	0.0193 (10)	−0.0007 (9)
C5'	0.0480 (11)	0.0456 (11)	0.0548 (12)	0.0030 (9)	0.0130 (9)	−0.0045 (9)
C6'	0.0407 (10)	0.0410 (10)	0.0475 (11)	0.0008 (8)	0.0077 (8)	−0.0011 (8)
C6	0.0484 (10)	0.0378 (10)	0.0541 (12)	0.0000 (8)	0.0248 (9)	0.0038 (8)
C7	0.0473 (10)	0.0356 (9)	0.0466 (10)	0.0028 (8)	0.0232 (8)	0.0019 (8)
C7'	0.0368 (9)	0.0419 (10)	0.0416 (10)	−0.0029 (7)	0.0075 (7)	−0.0029 (8)
C8'	0.0467 (10)	0.0422 (10)	0.0483 (11)	0.0028 (8)	0.0105 (8)	−0.0032 (9)
C8	0.0555 (11)	0.0358 (9)	0.0447 (10)	−0.0065 (8)	0.0219 (9)	−0.0012 (8)
C9'	0.0379 (9)	0.0459 (10)	0.0449 (10)	−0.0017 (8)	0.0098 (8)	−0.0009 (8)
C9	0.0482 (10)	0.0391 (10)	0.0434 (10)	0.0057 (8)	0.0225 (8)	0.0021 (8)
C10'	0.0453 (10)	0.0554 (12)	0.0540 (12)	0.0048 (9)	0.0124 (9)	−0.0041 (10)
C10	0.0553 (11)	0.0482 (11)	0.0473 (11)	−0.0019 (9)	0.0208 (9)	0.0000 (9)
C11'	0.0498 (12)	0.0714 (15)	0.0624 (14)	0.0064 (11)	0.0205 (10)	−0.0104 (12)
C11	0.0562 (12)	0.0620 (13)	0.0537 (13)	0.0018 (11)	0.0178 (10)	−0.0061 (11)
C12'	0.0543 (12)	0.0867 (18)	0.0479 (12)	−0.0021 (12)	0.0187 (10)	−0.0068 (12)
C12	0.0649 (14)	0.0696 (15)	0.0446 (12)	0.0140 (12)	0.0145 (10)	−0.0021 (11)
C13'	0.0513 (12)	0.0740 (15)	0.0457 (12)	−0.0044 (11)	0.0113 (9)	0.0064 (11)
C13	0.0670 (14)	0.0600 (13)	0.0466 (12)	0.0194 (11)	0.0244 (10)	0.0099 (10)
C14'	0.0374 (9)	0.0502 (11)	0.0436 (10)	−0.0045 (8)	0.0072 (8)	0.0029 (9)
C14	0.0542 (11)	0.0428 (10)	0.0483 (11)	0.0135 (8)	0.0272 (9)	0.0082 (8)
C15'	0.0454 (10)	0.0468 (11)	0.0546 (12)	−0.0005 (9)	0.0060 (9)	0.0073 (9)
C15	0.0589 (12)	0.0428 (11)	0.0599 (13)	0.0107 (9)	0.0346 (10)	0.0149 (9)
C16	0.0565 (12)	0.0402 (10)	0.0648 (14)	−0.0026 (9)	0.0280 (10)	0.0101 (9)
C16'	0.0501 (11)	0.0443 (11)	0.0591 (13)	0.0091 (9)	0.0113 (9)	0.0001 (10)
C17'	0.0607 (14)	0.0607 (14)	0.0667 (15)	0.0089 (11)	0.0077 (11)	0.0168 (12)
C17	0.0743 (15)	0.0596 (14)	0.0740 (16)	0.0110 (12)	0.0380 (13)	0.0299 (12)
S1	0.0603 (4)	0.0672 (4)	0.0536 (4)	−0.0073 (3)	0.0061 (3)	0.0019 (3)
S1'	0.0684 (4)	0.0788 (4)	0.0530 (4)	−0.0042 (3)	0.0223 (3)	−0.0040 (3)

C1'—C2'	1.310 (3)	C9'—C14'	1.417 (3)
C1'—S1'	1.725 (3)	C9—C10	1.407 (3)
C1'—H1'	0.9300	C9—C14	1.417 (3)
C1—C2	1.331 (3)	C10'—C11'	1.386 (3)
C1—S1	1.729 (3)	C10'—H10'	0.9300
C1—H1	0.9300	C10—C11	1.376 (3)
C2—C3	1.447 (3)	C10—H10	0.9300
C2—H2	0.9300	C11'—C12'	1.379 (3)
C2'—C3'	1.476 (3)	C11'—H11'	0.9300
C2'—H2'	0.9300	C11—C12	1.387 (3)
C3—C8	1.385 (3)	C11—H11	0.9300
C3—C4	1.419 (3)	C12'—C13'	1.371 (3)
C3'—C8'	1.398 (3)	C12'—H12'	0.9300
C3'—C4'	1.411 (3)	C12—C13	1.364 (4)
C4—C5	1.378 (3)	C12—H12	0.9300
C4—S1	1.737 (2)	C13'—C14'	1.404 (3)
C4'—C5'	1.373 (3)	C13'—H13'	0.9300
C4'—S1'	1.742 (2)	C13—C14	1.408 (3)
C5—C6	1.397 (3)	C13—H13	0.9300
C5—H5	0.9300	C14'—C15'	1.459 (3)
C5'—C6'	1.396 (3)	C14—C15	1.455 (3)
C5'—H5'	0.9300	C15'—C16'	1.339 (3)
C6'—C7'	1.419 (3)	C15'—C17'	1.507 (3)
C6'—C16'	1.444 (3)	C15—C16	1.343 (3)
C6—C7	1.426 (3)	C15—C17	1.507 (3)
C6—C16	1.441 (3)	C16—H16	0.9300
C7—C8	1.404 (3)	C16'—H16'	0.9300
C7—C9	1.457 (3)	C17'—H17A	0.9600
C7'—C8'	1.399 (3)	C17'—H17B	0.9600
C7'—C9'	1.461 (3)	C17'—H17C	0.9600
C8'—H8'	0.9300	C17—H17D	0.9600
C8—H8	0.9300	C17—H17E	0.9600
C9'—C10'	1.395 (3)	C17—H17F	0.9600
C2'—C1'—S1'	115.65 (19)	C11'—C10'—H10'	119.2
C2'—C1'—H1'	122.2	C9'—C10'—H10'	119.2
S1'—C1'—H1'	122.2	C11—C10—C9	121.5 (2)
C2—C1—S1	114.30 (17)	C11—C10—H10	119.3
C2—C1—H1	122.9	C9—C10—H10	119.3
S1—C1—H1	122.9	C12'—C11'—C10'	119.7 (2)
C1—C2—C3	112.4 (2)	C12'—C11'—H11'	120.1
C1—C2—H2	123.8	C10'—C11'—H11'	120.1
C3—C2—H2	123.8	C10—C11—C12	119.9 (2)
C1'—C2'—C3'	111.3 (2)	C10—C11—H11	120.1
C1'—C2'—H2'	124.3	C12—C11—H11	120.1
C3'—C2'—H2'	124.3	C13'—C12'—C11'	120.3 (2)
C8—C3—C4	119.30 (18)	C13'—C12'—H12'	119.8
C8—C3—C2	129.41 (19)	C11'—C12'—H12'	119.8
C4—C3—C2	111.29 (19)	C13—C12—C11	120.2 (2)
C8'—C3'—C4'	118.48 (18)	C13—C12—H12	119.9
C8'—C3'—C2'	130.0 (2)	C11—C12—H12	119.9
C4'—C3'—C2'	111.52 (19)	C12'—C13'—C14'	121.0 (2)
C5—C4—C3	121.2 (2)	C12'—C13'—H13'	119.5
C5—C4—S1	127.90 (17)	C14'—C13'—H13'	119.5
C3—C4—S1	110.93 (15)	C12—C13—C14	121.6 (2)
C5'—C4'—C3'	122.2 (2)	C12—C13—H13	119.2
C5'—C4'—S1'	127.17 (17)	C14—C13—H13	119.2
C3'—C4'—S1'	110.59 (15)	C13'—C14'—C9'	119.2 (2)
C4—C5—C6	119.36 (19)	C13'—C14'—C15'	121.09 (19)
C4—C5—H5	120.3	C9'—C14'—C15'	119.68 (19)
C6—C5—H5	120.3	C13—C14—C9	118.5 (2)
C4'—C5'—C6'	118.82 (19)	C13—C14—C15	121.65 (19)
C4'—C5'—H5'	120.6	C9—C14—C15	119.8 (2)
C6'—C5'—H5'	120.6	C16'—C15'—C14'	119.61 (19)
C5'—C6'—C7'	120.86 (18)	C16'—C15'—C17'	120.4 (2)
C5'—C6'—C16'	120.13 (18)	C14'—C15'—C17'	120.0 (2)
C7'—C6'—C16'	118.95 (18)	C16—C15—C14	119.40 (18)
C5—C6—C7	120.71 (18)	C16—C15—C17	120.3 (2)
C5—C6—C16	120.42 (19)	C14—C15—C17	120.3 (2)
C7—C6—C16	118.84 (19)	C15—C16—C6	123.3 (2)
C8—C7—C6	118.51 (19)	C15—C16—H16	118.4
C8—C7—C9	122.88 (18)	C6—C16—H16	118.4
C6—C7—C9	118.61 (17)	C15'—C16'—C6'	123.1 (2)
C8'—C7'—C6'	118.90 (18)	C15'—C16'—H16'	118.5
C8'—C7'—C9'	122.30 (18)	C6'—C16'—H16'	118.5
C6'—C7'—C9'	118.80 (17)	C15'—C17'—H17A	109.5
C3'—C8'—C7'	120.70 (19)	C15'—C17'—H17B	109.5
C3'—C8'—H8'	119.7	H17A—C17'—H17B	109.5
C7'—C8'—H8'	119.7	C15'—C17'—H17C	109.5
C3—C8—C7	120.92 (18)	H17A—C17'—H17C	109.5
C3—C8—H8	119.5	H17B—C17'—H17C	109.5
C7—C8—H8	119.5	C15—C17—H17D	109.5
C10'—C9'—C14'	118.04 (19)	C15—C17—H17E	109.5
C10'—C9'—C7'	122.22 (18)	H17D—C17—H17E	109.5
C14'—C9'—C7'	119.73 (18)	C15—C17—H17F	109.5
C10—C9—C14	118.38 (19)	H17D—C17—H17F	109.5
C10—C9—C7	121.69 (17)	H17E—C17—H17F	109.5
C14—C9—C7	119.93 (18)	C1—S1—C4	91.03 (11)
C11'—C10'—C9'	121.7 (2)	C1'—S1'—C4'	90.93 (12)
S1—C1—C2—C3	1.1 (3)	C6—C7—C9—C14	−3.5 (3)
S1'—C1'—C2'—C3'	−0.4 (3)	C14'—C9'—C10'—C11'	1.0 (3)
C1—C2—C3—C8	178.3 (2)	C7'—C9'—C10'—C11'	−178.1 (2)
C1—C2—C3—C4	−1.1 (3)	C14—C9—C10—C11	−1.4 (3)
C1'—C2'—C3'—C8'	179.8 (2)	C7—C9—C10—C11	178.70 (19)
C1'—C2'—C3'—C4'	0.6 (3)	C9'—C10'—C11'—C12'	−0.6 (4)
C8—C3—C4—C5	2.0 (3)	C9—C10—C11—C12	1.0 (3)
C2—C3—C4—C5	−178.43 (19)	C10'—C11'—C12'—C13'	0.2 (4)
C8—C3—C4—S1	−178.83 (15)	C10—C11—C12—C13	0.0 (3)
C2—C3—C4—S1	0.7 (2)	C11'—C12'—C13'—C14'	−0.2 (4)
C8'—C3'—C4'—C5'	−1.2 (3)	C11—C12—C13—C14	−0.5 (3)
C2'—C3'—C4'—C5'	178.05 (19)	C12'—C13'—C14'—C9'	0.6 (3)
C8'—C3'—C4'—S1'	−179.91 (15)	C12'—C13'—C14'—C15'	−179.4 (2)
C2'—C3'—C4'—S1'	−0.6 (2)	C10'—C9'—C14'—C13'	−0.9 (3)
C3—C4—C5—C6	−0.9 (3)	C7'—C9'—C14'—C13'	178.15 (18)
S1—C4—C5—C6	−179.89 (16)	C10'—C9'—C14'—C15'	179.06 (18)
C3'—C4'—C5'—C6'	0.3 (3)	C7'—C9'—C14'—C15'	−1.9 (3)
S1'—C4'—C5'—C6'	178.75 (16)	C12—C13—C14—C9	0.1 (3)
C4'—C5'—C6'—C7'	0.7 (3)	C12—C13—C14—C15	−179.93 (19)
C4'—C5'—C6'—C16'	−176.45 (19)	C10—C9—C14—C13	0.9 (3)
C4—C5—C6—C7	−1.0 (3)	C7—C9—C14—C13	−179.26 (17)
C4—C5—C6—C16	177.11 (19)	C10—C9—C14—C15	−179.12 (17)
C5—C6—C7—C8	1.8 (3)	C7—C9—C14—C15	0.8 (3)
C16—C6—C7—C8	−176.34 (18)	C13'—C14'—C15'—C16'	178.6 (2)
C5—C6—C7—C9	−178.46 (17)	C9'—C14'—C15'—C16'	−1.4 (3)
C16—C6—C7—C9	3.4 (3)	C13'—C14'—C15'—C17'	−2.5 (3)
C5'—C6'—C7'—C8'	−0.7 (3)	C9'—C14'—C15'—C17'	177.52 (19)
C16'—C6'—C7'—C8'	176.44 (18)	C13—C14—C15—C16	−177.8 (2)
C5'—C6'—C7'—C9'	179.81 (18)	C9—C14—C15—C16	2.2 (3)
C16'—C6'—C7'—C9'	−3.0 (3)	C13—C14—C15—C17	2.9 (3)
C4'—C3'—C8'—C7'	1.2 (3)	C9—C14—C15—C17	−177.15 (18)
C2'—C3'—C8'—C7'	−177.96 (19)	C14—C15—C16—C6	−2.3 (3)
C6'—C7'—C8'—C3'	−0.2 (3)	C17—C15—C16—C6	177.00 (19)
C9'—C7'—C8'—C3'	179.21 (17)	C5—C6—C16—C15	−178.7 (2)
C4—C3—C8—C7	−1.2 (3)	C7—C6—C16—C15	−0.5 (3)
C2—C3—C8—C7	179.37 (19)	C14'—C15'—C16'—C6'	2.4 (3)
C6—C7—C8—C3	−0.7 (3)	C17'—C15'—C16'—C6'	−176.44 (19)
C9—C7—C8—C3	179.61 (17)	C5'—C6'—C16'—C15'	177.0 (2)
C8'—C7'—C9'—C10'	3.6 (3)	C7'—C6'—C16'—C15'	−0.2 (3)
C6'—C7'—C9'—C10'	−176.94 (18)	C2—C1—S1—C4	−0.56 (19)
C8'—C7'—C9'—C14'	−175.43 (18)	C5—C4—S1—C1	178.9 (2)
C6'—C7'—C9'—C14'	4.0 (3)	C3—C4—S1—C1	−0.11 (16)
C8—C7—C9—C10	−3.9 (3)	C2'—C1'—S1'—C4'	0.0 (2)
C6—C7—C9—C10	176.38 (17)	C5'—C4'—S1'—C1'	−178.2 (2)
C8—C7—C9—C14	176.23 (17)	C3'—C4'—S1'—C1'	0.36 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg4i	0.93	2.84	3.612 (3)	141
C2'—H2'···Cg14ii	0.93	2.85	3.619 (3)	141
C11—H11···Cg1i	0.93	2.72	3.515 (3)	144
C11'—H11'···Cg11ii	0.93	2.82	3.610 (3)	143
C17'—H17B···Cg14iii	0.96	2.98	3.581 (3)	121
C17—H17F···Cg4iii	0.96	2.92	3.565 (3)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg4i	0.93	2.84	3.612 (3)	141
C2′—H2′⋯Cg14ii	0.93	2.85	3.619 (3)	141
C11—H11⋯Cg1i	0.93	2.72	3.515 (3)	144
C11′—H11′⋯Cg11ii	0.93	2.82	3.610 (3)	143
C17′—H17B⋯Cg14iii	0.96	2.98	3.581 (3)	121
C17—H17F⋯Cg4iii	0.96	2.92	3.565 (3)	125

Symmetry codes: (i) ; (ii) ; (iii) . Cg1, Cg4, Cg11 and Cg14 are the centroids of the S1/C1–C4, C9–C14, S1′/C1′–C4′ and C9′–C14′ rings, respectively.