8-Phenyl-16-thia-penta-cyclo-[6.6.5.0(1,18).0(2,7).0(9,14)]nona-deca-2,4,6,9,11,13,18-hepta-ene.

In the title compound, C24H18S, the dihedral angles between the phenyl ring and the two benzene rings of the anthracene moiety are 51.92 (9) and 68.24 (9)°, whereas the dihedral angle between the two anthracene benzene rings is 120.13 (9)°. The three non-aromatic six-membered rings are in boat conformations, while the five-membered ring has an envelope conformation on the S atom. In the crystal, there are three C-H⋯π inter-actions, which facilitate the packing of the mol-ecules.

Related literature

For background to dibenzobarrelene dervatives and their applications, see: Khalil et al. (2010 ▶); Cox et al. (2013 ▶). For the synthesis of related compounds, see: Ciganek (1980 ▶); Vetter (1998 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C24H18S

M = 338.44

Orthorhombic,

a = 18.8842 (11) Å

b = 9.5339 (4) Å

c = 19.1140 (9) Å

V = 3441.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.19 mm−1

T = 296 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.945, T max = 0.963

22858 measured reflections

3757 independent reflections

2765 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.138

S = 1.02

3757 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813017285/zl2554sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017285/zl2554Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813017285/zl2554Isup3.cml

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

C24H18S	F(000) = 1424
Mr = 338.44	Dx = 1.306 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5274 reflections
a = 18.8842 (11) Å	θ = 2.4–27.6°
b = 9.5339 (4) Å	µ = 0.19 mm−1
c = 19.1140 (9) Å	T = 296 K
V = 3441.3 (3) Å3	Block, colorless
Z = 8	0.30 × 0.25 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	3757 independent reflections
Radiation source: fine-focus sealed tube	2765 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 8.33 pixels mm-1	θmax = 27.0°, θmin = 2.6°
ω and φ scan	h = −24→20
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −11→12
Tmin = 0.945, Tmax = 0.963	l = −24→24
22858 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0791P)2 + 0.6172P] where P = (Fo2 + 2Fc2)/3
3757 reflections	(Δ/σ)max = 0.006
226 parameters	Δρmax = 0.18 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
S1	0.77988 (3)	1.09442 (6)	1.01400 (3)	0.0562 (2)
C21	0.47261 (12)	1.2996 (2)	0.87474 (10)	0.0488 (5)
H21	0.4282	1.3379	0.8657	0.059*
C22	0.52896 (12)	1.3863 (2)	0.88829 (10)	0.0506 (5)
H22	0.5226	1.4830	0.8876	0.061*
C23	0.59526 (11)	1.33134 (19)	0.90300 (10)	0.0432 (4)
H23	0.6334	1.3905	0.9118	0.052*
C3	0.38780 (12)	0.6768 (2)	0.83907 (12)	0.0552 (6)
H3	0.3499	0.6193	0.8271	0.066*
C2	0.41860 (12)	0.7624 (3)	0.78966 (11)	0.0562 (6)
H2	0.4012	0.7629	0.7441	0.067*
C1	0.47491 (11)	0.8473 (2)	0.80711 (10)	0.0476 (5)
H1	0.4941	0.9065	0.7734	0.057*
C6	0.50367 (10)	0.84613 (18)	0.87452 (8)	0.0352 (4)
C7	0.56618 (9)	0.94019 (17)	0.89155 (8)	0.0325 (4)
C19	0.54721 (9)	1.09806 (17)	0.88904 (8)	0.0324 (4)
C20	0.48144 (10)	1.1551 (2)	0.87441 (8)	0.0394 (4)
H20	0.4433	1.0967	0.8644	0.047*
C16	0.69820 (11)	1.0122 (2)	1.04320 (10)	0.0460 (5)
H16A	0.7075	0.9194	1.0619	0.055*
H16B	0.6757	1.0682	1.0792	0.055*
C17	0.65229 (10)	1.00336 (17)	0.97976 (8)	0.0338 (4)
C14	0.67205 (10)	1.10848 (17)	0.92219 (9)	0.0358 (4)
C24	0.60395 (9)	1.18688 (18)	0.90446 (8)	0.0341 (4)
C4	0.41364 (11)	0.6773 (2)	0.90609 (12)	0.0495 (5)
H4	0.3923	0.6216	0.9400	0.059*
C5	0.47154 (10)	0.76063 (19)	0.92374 (9)	0.0398 (4)
H5	0.4889	0.7588	0.9693	0.048*
C18	0.59965 (9)	0.91744 (17)	0.96419 (8)	0.0336 (4)
H18	0.5840	0.8483	0.9948	0.040*
C8	0.63048 (10)	0.92721 (17)	0.84115 (8)	0.0342 (4)
C13	0.68638 (10)	1.01795 (18)	0.85762 (9)	0.0367 (4)
C12	0.74681 (11)	1.0184 (2)	0.81727 (11)	0.0492 (5)
H12	0.7839	1.0787	0.8282	0.059*
C11	0.75247 (13)	0.9291 (2)	0.76038 (11)	0.0578 (6)
H11	0.7929	0.9312	0.7326	0.069*
C10	0.69867 (13)	0.8378 (2)	0.74485 (10)	0.0564 (6)
H10	0.7032	0.7770	0.7071	0.068*
C9	0.63726 (11)	0.8355 (2)	0.78527 (9)	0.0437 (5)
H9	0.6010	0.7728	0.7748	0.052*
C15	0.73314 (11)	1.1988 (2)	0.94933 (11)	0.0493 (5)
H15A	0.7151	1.2841	0.9704	0.059*
H15B	0.7647	1.2240	0.9113	0.059*

	U11	U22	U33	U12	U13	U23
S1	0.0443 (3)	0.0488 (3)	0.0754 (4)	0.0006 (2)	−0.0213 (3)	−0.0014 (2)
C21	0.0489 (12)	0.0560 (12)	0.0415 (10)	0.0226 (10)	−0.0013 (9)	0.0015 (8)
C22	0.0640 (14)	0.0391 (10)	0.0487 (11)	0.0181 (10)	−0.0023 (10)	0.0013 (8)
C23	0.0525 (12)	0.0339 (9)	0.0432 (10)	0.0031 (8)	−0.0014 (9)	0.0015 (7)
C3	0.0416 (12)	0.0508 (12)	0.0732 (14)	−0.0032 (9)	−0.0068 (10)	−0.0229 (11)
C2	0.0496 (13)	0.0706 (14)	0.0483 (11)	0.0040 (11)	−0.0110 (10)	−0.0191 (10)
C1	0.0459 (12)	0.0600 (12)	0.0370 (9)	0.0002 (10)	−0.0026 (8)	−0.0058 (8)
C6	0.0364 (10)	0.0358 (9)	0.0335 (8)	0.0028 (7)	0.0006 (7)	−0.0054 (7)
C7	0.0353 (9)	0.0361 (9)	0.0261 (8)	0.0015 (7)	0.0006 (6)	0.0000 (6)
C19	0.0368 (9)	0.0366 (9)	0.0237 (7)	0.0056 (7)	0.0029 (6)	0.0011 (6)
C20	0.0385 (10)	0.0484 (10)	0.0315 (8)	0.0065 (8)	0.0000 (7)	−0.0006 (7)
C16	0.0518 (12)	0.0429 (10)	0.0433 (10)	0.0047 (9)	−0.0123 (9)	−0.0045 (8)
C17	0.0386 (10)	0.0306 (8)	0.0321 (8)	0.0069 (7)	−0.0042 (7)	0.0003 (6)
C14	0.0341 (9)	0.0302 (8)	0.0430 (9)	0.0024 (7)	−0.0021 (7)	0.0024 (7)
C24	0.0371 (10)	0.0335 (9)	0.0316 (8)	0.0055 (7)	0.0007 (7)	0.0025 (6)
C4	0.0443 (12)	0.0400 (10)	0.0641 (13)	−0.0044 (9)	0.0030 (10)	−0.0043 (9)
C5	0.0415 (11)	0.0364 (9)	0.0415 (9)	−0.0004 (8)	−0.0001 (8)	−0.0038 (7)
C18	0.0392 (10)	0.0326 (9)	0.0290 (8)	0.0021 (7)	−0.0001 (7)	0.0023 (6)
C8	0.0381 (10)	0.0342 (9)	0.0303 (8)	0.0076 (7)	0.0021 (7)	0.0050 (7)
C13	0.0375 (10)	0.0344 (9)	0.0384 (9)	0.0078 (7)	0.0020 (7)	0.0090 (7)
C12	0.0396 (11)	0.0506 (12)	0.0576 (12)	0.0073 (9)	0.0084 (9)	0.0158 (9)
C11	0.0531 (14)	0.0686 (15)	0.0518 (12)	0.0231 (12)	0.0216 (10)	0.0156 (11)
C10	0.0692 (16)	0.0607 (13)	0.0394 (10)	0.0273 (12)	0.0119 (10)	−0.0001 (9)
C9	0.0518 (12)	0.0446 (10)	0.0349 (9)	0.0134 (9)	−0.0005 (8)	−0.0005 (7)
C15	0.0429 (12)	0.0375 (10)	0.0675 (13)	−0.0027 (8)	−0.0104 (10)	0.0032 (9)

S1—C15	1.816 (2)	C16—C17	1.493 (2)
S1—C16	1.818 (2)	C16—H16A	0.9700
C21—C22	1.372 (3)	C16—H16B	0.9700
C21—C20	1.388 (3)	C17—C18	1.322 (2)
C21—H21	0.9300	C17—C14	1.534 (2)
C22—C23	1.386 (3)	C14—C24	1.526 (2)
C22—H22	0.9300	C14—C15	1.530 (3)
C23—C24	1.387 (2)	C14—C13	1.530 (2)
C23—H23	0.9300	C4—C5	1.393 (3)
C3—C4	1.371 (3)	C4—H4	0.9300
C3—C2	1.377 (3)	C5—H5	0.9300
C3—H3	0.9300	C18—H18	0.9300
C2—C1	1.377 (3)	C8—C9	1.386 (2)
C2—H2	0.9300	C8—C13	1.401 (3)
C1—C6	1.398 (2)	C13—C12	1.377 (3)
C1—H1	0.9300	C12—C11	1.385 (3)
C6—C5	1.385 (3)	C12—H12	0.9300
C6—C7	1.518 (2)	C11—C10	1.370 (3)
C7—C18	1.541 (2)	C11—H11	0.9300
C7—C19	1.548 (2)	C10—C9	1.394 (3)
C7—C8	1.555 (2)	C10—H10	0.9300
C19—C20	1.384 (2)	C9—H9	0.9300
C19—C24	1.397 (2)	C15—H15A	0.9700
C20—H20	0.9300	C15—H15B	0.9700
C15—S1—C16	91.89 (9)	C24—C14—C15	115.81 (14)
C22—C21—C20	120.39 (18)	C24—C14—C13	104.26 (14)
C22—C21—H21	119.8	C15—C14—C13	117.22 (16)
C20—C21—H21	119.8	C24—C14—C17	105.92 (14)
C21—C22—C23	120.73 (18)	C15—C14—C17	107.92 (15)
C21—C22—H22	119.6	C13—C14—C17	104.65 (13)
C23—C22—H22	119.6	C23—C24—C19	120.46 (17)
C24—C23—C22	119.09 (19)	C23—C24—C14	126.19 (16)
C24—C23—H23	120.5	C19—C24—C14	113.35 (14)
C22—C23—H23	120.5	C3—C4—C5	120.5 (2)
C4—C3—C2	119.25 (19)	C3—C4—H4	119.7
C4—C3—H3	120.4	C5—C4—H4	119.7
C2—C3—H3	120.4	C6—C5—C4	121.00 (18)
C3—C2—C1	120.55 (19)	C6—C5—H5	119.5
C3—C2—H2	119.7	C4—C5—H5	119.5
C1—C2—H2	119.7	C17—C18—C7	115.09 (15)
C2—C1—C6	121.21 (19)	C17—C18—H18	122.5
C2—C1—H1	119.4	C7—C18—H18	122.5
C6—C1—H1	119.4	C9—C8—C13	119.54 (17)
C5—C6—C1	117.42 (17)	C9—C8—C7	126.85 (17)
C5—C6—C7	122.88 (15)	C13—C8—C7	113.58 (14)
C1—C6—C7	119.66 (16)	C12—C13—C8	120.02 (17)
C6—C7—C18	115.41 (14)	C12—C13—C14	126.63 (18)
C6—C7—C19	112.82 (14)	C8—C13—C14	113.35 (15)
C18—C7—C19	105.06 (13)	C13—C12—C11	120.1 (2)
C6—C7—C8	115.31 (13)	C13—C12—H12	119.9
C18—C7—C8	103.10 (13)	C11—C12—H12	119.9
C19—C7—C8	103.83 (13)	C10—C11—C12	120.2 (2)
C20—C19—C24	119.52 (16)	C10—C11—H11	119.9
C20—C19—C7	126.56 (16)	C12—C11—H11	119.9
C24—C19—C7	113.91 (15)	C11—C10—C9	120.46 (19)
C19—C20—C21	119.77 (19)	C11—C10—H10	119.8
C19—C20—H20	120.1	C9—C10—H10	119.8
C21—C20—H20	120.1	C8—C9—C10	119.6 (2)
C17—C16—S1	105.52 (13)	C8—C9—H9	120.2
C17—C16—H16A	110.6	C10—C9—H9	120.2
S1—C16—H16A	110.6	C14—C15—S1	106.81 (13)
C17—C16—H16B	110.6	C14—C15—H15A	110.4
S1—C16—H16B	110.6	S1—C15—H15A	110.4
H16A—C16—H16B	108.8	C14—C15—H15B	110.4
C18—C17—C16	130.86 (16)	S1—C15—H15B	110.4
C18—C17—C14	115.23 (15)	H15A—C15—H15B	108.6
C16—C17—C14	113.86 (15)
C20—C21—C22—C23	−1.1 (3)	C15—C14—C24—C19	−171.86 (15)
C21—C22—C23—C24	−0.5 (3)	C13—C14—C24—C19	57.81 (17)
C4—C3—C2—C1	0.2 (3)	C17—C14—C24—C19	−52.30 (18)
C3—C2—C1—C6	1.9 (3)	C2—C3—C4—C5	−1.6 (3)
C2—C1—C6—C5	−2.6 (3)	C1—C6—C5—C4	1.2 (3)
C2—C1—C6—C7	179.40 (18)	C7—C6—C5—C4	179.12 (17)
C5—C6—C7—C18	9.5 (2)	C3—C4—C5—C6	0.9 (3)
C1—C6—C7—C18	−172.62 (16)	C16—C17—C18—C7	−178.55 (17)
C5—C6—C7—C19	−111.32 (18)	C14—C17—C18—C7	−1.4 (2)
C1—C6—C7—C19	66.6 (2)	C6—C7—C18—C17	−177.47 (15)
C5—C6—C7—C8	129.62 (17)	C19—C7—C18—C17	−52.56 (19)
C1—C6—C7—C8	−52.5 (2)	C8—C7—C18—C17	55.91 (18)
C6—C7—C19—C20	1.0 (2)	C6—C7—C8—C9	−3.1 (2)
C18—C7—C19—C20	−125.52 (17)	C18—C7—C8—C9	123.63 (17)
C8—C7—C19—C20	126.54 (17)	C19—C7—C8—C9	−126.98 (17)
C6—C7—C19—C24	−179.93 (13)	C6—C7—C8—C13	178.59 (14)
C18—C7—C19—C24	53.54 (17)	C18—C7—C8—C13	−54.73 (17)
C8—C7—C19—C24	−54.39 (17)	C19—C7—C8—C13	54.66 (17)
C24—C19—C20—C21	0.4 (2)	C9—C8—C13—C12	1.7 (2)
C7—C19—C20—C21	179.44 (16)	C7—C8—C13—C12	−179.77 (15)
C22—C21—C20—C19	1.1 (3)	C9—C8—C13—C14	−177.77 (15)
C15—S1—C16—C17	32.38 (13)	C7—C8—C13—C14	0.72 (19)
S1—C16—C17—C18	155.10 (17)	C24—C14—C13—C12	123.19 (18)
S1—C16—C17—C14	−22.11 (18)	C15—C14—C13—C12	−6.3 (3)
C18—C17—C14—C24	55.15 (19)	C17—C14—C13—C12	−125.78 (18)
C16—C17—C14—C24	−127.18 (15)	C24—C14—C13—C8	−57.34 (17)
C18—C17—C14—C15	179.77 (16)	C15—C14—C13—C8	173.18 (15)
C16—C17—C14—C15	−2.6 (2)	C17—C14—C13—C8	53.70 (18)
C18—C17—C14—C13	−54.68 (19)	C8—C13—C12—C11	0.0 (3)
C16—C17—C14—C13	122.99 (16)	C14—C13—C12—C11	179.43 (17)
C22—C23—C24—C19	2.1 (3)	C13—C12—C11—C10	−1.4 (3)
C22—C23—C24—C14	−177.67 (17)	C12—C11—C10—C9	1.2 (3)
C20—C19—C24—C23	−2.0 (2)	C13—C8—C9—C10	−2.0 (3)
C7—C19—C24—C23	178.83 (15)	C7—C8—C9—C10	179.71 (16)
C20—C19—C24—C14	177.74 (14)	C11—C10—C9—C8	0.6 (3)
C7—C19—C24—C14	−1.39 (19)	C24—C14—C15—S1	144.72 (13)
C15—C14—C24—C23	7.9 (3)	C13—C14—C15—S1	−91.47 (17)
C13—C14—C24—C23	−122.42 (18)	C17—C14—C15—S1	26.26 (18)
C17—C14—C24—C23	127.46 (18)	C16—S1—C15—C14	−34.57 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg1i	0.93	2.80	3.516 (2)	135
C5—H5···Cg1ii	0.93	2.76	3.5844 (19)	149
C15—H15B···Cg2iii	0.97	2.98	3.845 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C19–C2 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg1i	0.93	2.80	3.516 (2)	135
C5—H5⋯Cg1ii	0.93	2.76	3.5844 (19)	149
C15—H15B⋯Cg2iii	0.97	2.98	3.845 (2)	149

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