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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 7| July 2013| Page o1165
https://doi.org/10.1107/S1600536813017285

8-Phenyl-16-thia­penta­cyclo­[6.6.5.01,18.02,7.09,14]nona­deca-2,4,6,9,11,13,18-hepta­ene

Eason M. Mathew,a M. Sithambaresan,b* P. A. Unnikrishnana and M. R. Prathapachandra Kurupa

aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India, and bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka
*Correspondence e-mail: eesans@yahoo.com

(Received 17 June 2013; accepted 22 June 2013; online 29 June 2013)

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 inter­actions, which facilitate the packing of the mol­ecules.

Related literature

For background to dibenzobarrelene dervatives and their applications, see: Khalil et al. (2010[Khalil, A. M., Berghot, M. A., Gouda, M. A. & Bialy, S. A. E. (2010). Monatsh. Chem. 141, 1353-1360.]); Cox et al. (2013[Cox, J. R., Simpson, J. H. & Swager, T. M. (2013). J. Am. Chem. Soc. 135, 640-643.]). For the synthesis of related compounds, see: Ciganek (1980[Ciganek, E. (1980). J. Org. Chem. 45, 1497-1505.]); Vetter (1998[Vetter, S. (1998). Synth. Commun. 28, 3219-3223.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data

  • C24H18S

  • Mr = 338.44

  • Orthorhombic, P b c a

  • 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[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.945, Tmax = 0.963

  • 22858 measured reflections

  • 3757 independent reflections

  • 2765 reflections with I > 2σ(I)

  • Rint = 0.032
Refinement

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 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

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) [-x+{\script{3\over 2}}, -y-1, z+{\script{3\over 2}}]; (ii) -x+1, -y+2, -z+2; (iii) [x+1, -y-{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813017285/zl2554sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813017285/zl2554Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813017285/zl2554Isup3.cml

checkCIF report


Comment top

Thiazoles, thiophenes and their derivatives have attracted continuing interest over the years since they often exhibit various biological activities and have been investigated for the treatment of various diseases (Khalil et al., 2010). Dibenzobarrelene derivatives find application in the alignment of nematic liquid crystals. The strong coupling of the liquid crystal directors to dibenzobarrelene groups is responsible for the alignment mechanism (Cox et al., 2013).

The compound (Fig. 1) crystallizes in the monoclinic space group Pbca. The dihedral angles between the phenyl ring and the other two benzene rings of the anthracene moiety are 51.92 (9) and 68.24 (9)°. The two aromatic rings of the anthracene moiety form a dihedral angle of 120.13 (9)° between themselves.

The five-membered heterocyclic ring C14–17/S1 is in an envelope conformation on S1 [φ = 3.9 (3)°] (Cremer & Pople, 1975). The ring C7/C8/C13/C14/C19/C24 of the three fused six-membered rings is in a boat conformation [φ = 180.31 (13)° and θ = 89.60 (12)°] with a total puckering amplitude QT of 0.8317 (18) Å. The second six-membered ring C7/C8/C13/C14/C17/C18 is also in a boat conformation [φ = 359.90 (13)° and θ = 89.16 (13)°] having a total puckering amplitude QT of 0.8160 (18) Å. The third six-membered ring C7/C14/C17/C18/C19/C24 also has the same conformation [φ = 358.83 (13)° and θ = 89.80 (13)°] and has a total puckering amplitude QT of 0.7856 (18) Å.

There are three weak C–H···π interactions (Fig. 2) between the H atoms attached at the C2, C5 and C15 atoms and neighboring aromatic rings. The hydrogen atoms from the C2 and C5 atoms form C–H···π interactions with the C19—C24 ring of two adjacent molecules from opposite sides of the main molecule and the hydrogen attached at C15 atom has an interaction with the C8—C13 ring of a neighbouring molecule with H···π distances of 2.80, 2.76 and 2.98 Å, respectively (Table 1). The packing of molecules is dominated by these C–H···π interactions. Fig. 3 shows the packing diagram of the title compound along b axis.

Related literature top

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 top

The title compound was prepared by adapting a reported procedure (Ciganek, 1980; Vetter, 1998). 10-phenyl-9-anthracenemethanol (1 mmol) obtained by reduction of the corresponding aldehyde (1 mmol) using sodium borohydride (3 mmol) and thiourea (2 mmol) were dissolved in acetone and stirred overnight with 10 ml of 5 N HCl to obtain10-phenyl-9-anthracenemethanethiol which was converted into 10-phenyl-9-anthracenemethyl propargyl sulfide through treatment with propargyl bromide. 10-Phenyl-9-anthracenemethyl propargyl sulfide was refluxed in p-xylene for 7 h (intramolecular Diels-Alder reaction) to get the title compound. Colourless crystals suitable for X-ray structure determination were recrystallized from acetonitrile by slow evaporation over a few days (m.p: 218 °C).

Refinement top

All H atoms on C were placed in calculated positions, guided by difference maps, with C–H bond distances of 0.93–0.97 Å. H atoms were assigned Uiso=1.2Ueq. Omitted owing to bad disagreement were the reflections (0 0 2), (2 0 0), and (1 0 2).

Structure description top

Thiazoles, thiophenes and their derivatives have attracted continuing interest over the years since they often exhibit various biological activities and have been investigated for the treatment of various diseases (Khalil et al., 2010). Dibenzobarrelene derivatives find application in the alignment of nematic liquid crystals. The strong coupling of the liquid crystal directors to dibenzobarrelene groups is responsible for the alignment mechanism (Cox et al., 2013).

The compound (Fig. 1) crystallizes in the monoclinic space group Pbca. The dihedral angles between the phenyl ring and the other two benzene rings of the anthracene moiety are 51.92 (9) and 68.24 (9)°. The two aromatic rings of the anthracene moiety form a dihedral angle of 120.13 (9)° between themselves.

The five-membered heterocyclic ring C14–17/S1 is in an envelope conformation on S1 [φ = 3.9 (3)°] (Cremer & Pople, 1975). The ring C7/C8/C13/C14/C19/C24 of the three fused six-membered rings is in a boat conformation [φ = 180.31 (13)° and θ = 89.60 (12)°] with a total puckering amplitude QT of 0.8317 (18) Å. The second six-membered ring C7/C8/C13/C14/C17/C18 is also in a boat conformation [φ = 359.90 (13)° and θ = 89.16 (13)°] having a total puckering amplitude QT of 0.8160 (18) Å. The third six-membered ring C7/C14/C17/C18/C19/C24 also has the same conformation [φ = 358.83 (13)° and θ = 89.80 (13)°] and has a total puckering amplitude QT of 0.7856 (18) Å.

There are three weak C–H···π interactions (Fig. 2) between the H atoms attached at the C2, C5 and C15 atoms and neighboring aromatic rings. The hydrogen atoms from the C2 and C5 atoms form C–H···π interactions with the C19—C24 ring of two adjacent molecules from opposite sides of the main molecule and the hydrogen attached at C15 atom has an interaction with the C8—C13 ring of a neighbouring molecule with H···π distances of 2.80, 2.76 and 2.98 Å, respectively (Table 1). The packing of molecules is dominated by these C–H···π interactions. Fig. 3 shows the packing diagram of the title compound along b axis.

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).

Computing details top

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 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. ORTEP view of the title compound drawn with 50% probability displacement ellipsoids for the non-H atoms.
[Figure 2] Fig. 2. C—H···π interactions found in the title compound.
[Figure 3] Fig. 3. Packing diagram of the compound along b axis.
8-Phenyl-16-thiapentacyclo[6.6.5.01,18.02,7.09,14]nonadeca-2,4,6,9,11,13,18-heptaene top
Crystal data top
C24H18SF(000) = 1424
Mr = 338.44Dx = 1.306 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 5274 reflections
a = 18.8842 (11) Åθ = 2.4–27.6°
b = 9.5339 (4) ŵ = 0.19 mm−1
c = 19.1140 (9) ÅT = 296 K
V = 3441.3 (3) Å3Block, colorless
Z = 80.30 × 0.25 × 0.20 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer		3757 independent reflections
Radiation source: fine-focus sealed tube2765 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 8.33 pixels mm-1θmax = 27.0°, θmin = 2.6°
ω and φ scanh = −24→20
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		k = −11→12
Tmin = 0.945, Tmax = 0.963l = −24→24
22858 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-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 parametersΔρmax = 0.18 e Å−3
0 restraintsΔρmin = −0.26 e Å−3
Crystal data top
C24H18SV = 3441.3 (3) Å3
Mr = 338.44Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 18.8842 (11) ŵ = 0.19 mm−1
b = 9.5339 (4) ÅT = 296 K
c = 19.1140 (9) Å0.30 × 0.25 × 0.20 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer		3757 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		2765 reflections with I > 2σ(I)
Tmin = 0.945, Tmax = 0.963Rint = 0.032
22858 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.138H-atom parameters constrained
S = 1.02Δρmax = 0.18 e Å−3
3757 reflectionsΔρmin = −0.26 e Å−3
226 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.77988 (3)1.09442 (6)1.01400 (3)0.0562 (2)
C210.47261 (12)1.2996 (2)0.87474 (10)0.0488 (5)
H210.42821.33790.86570.059*
C220.52896 (12)1.3863 (2)0.88829 (10)0.0506 (5)
H220.52261.48300.88760.061*
C230.59526 (11)1.33134 (19)0.90300 (10)0.0432 (4)
H230.63341.39050.91180.052*
C30.38780 (12)0.6768 (2)0.83907 (12)0.0552 (6)
H30.34990.61930.82710.066*
C20.41860 (12)0.7624 (3)0.78966 (11)0.0562 (6)
H20.40120.76290.74410.067*
C10.47491 (11)0.8473 (2)0.80711 (10)0.0476 (5)
H10.49410.90650.77340.057*
C60.50367 (10)0.84613 (18)0.87452 (8)0.0352 (4)
C70.56618 (9)0.94019 (17)0.89155 (8)0.0325 (4)
C190.54721 (9)1.09806 (17)0.88904 (8)0.0324 (4)
C200.48144 (10)1.1551 (2)0.87441 (8)0.0394 (4)
H200.44331.09670.86440.047*
C160.69820 (11)1.0122 (2)1.04320 (10)0.0460 (5)
H16A0.70750.91941.06190.055*
H16B0.67571.06821.07920.055*
C170.65229 (10)1.00336 (17)0.97976 (8)0.0338 (4)
C140.67205 (10)1.10848 (17)0.92219 (9)0.0358 (4)
C240.60395 (9)1.18688 (18)0.90446 (8)0.0341 (4)
C40.41364 (11)0.6773 (2)0.90609 (12)0.0495 (5)
H40.39230.62160.94000.059*
C50.47154 (10)0.76063 (19)0.92374 (9)0.0398 (4)
H50.48890.75880.96930.048*
C180.59965 (9)0.91744 (17)0.96419 (8)0.0336 (4)
H180.58400.84830.99480.040*
C80.63048 (10)0.92721 (17)0.84115 (8)0.0342 (4)
C130.68638 (10)1.01795 (18)0.85762 (9)0.0367 (4)
C120.74681 (11)1.0184 (2)0.81727 (11)0.0492 (5)
H120.78391.07870.82820.059*
C110.75247 (13)0.9291 (2)0.76038 (11)0.0578 (6)
H110.79290.93120.73260.069*
C100.69867 (13)0.8378 (2)0.74485 (10)0.0564 (6)
H100.70320.77700.70710.068*
C90.63726 (11)0.8355 (2)0.78527 (9)0.0437 (5)
H90.60100.77280.77480.052*
C150.73314 (11)1.1988 (2)0.94933 (11)0.0493 (5)
H15A0.71511.28410.97040.059*
H15B0.76471.22400.91130.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0443 (3)0.0488 (3)0.0754 (4)0.0006 (2)−0.0213 (3)−0.0014 (2)
C210.0489 (12)0.0560 (12)0.0415 (10)0.0226 (10)−0.0013 (9)0.0015 (8)
C220.0640 (14)0.0391 (10)0.0487 (11)0.0181 (10)−0.0023 (10)0.0013 (8)
C230.0525 (12)0.0339 (9)0.0432 (10)0.0031 (8)−0.0014 (9)0.0015 (7)
C30.0416 (12)0.0508 (12)0.0732 (14)−0.0032 (9)−0.0068 (10)−0.0229 (11)
C20.0496 (13)0.0706 (14)0.0483 (11)0.0040 (11)−0.0110 (10)−0.0191 (10)
C10.0459 (12)0.0600 (12)0.0370 (9)0.0002 (10)−0.0026 (8)−0.0058 (8)
C60.0364 (10)0.0358 (9)0.0335 (8)0.0028 (7)0.0006 (7)−0.0054 (7)
C70.0353 (9)0.0361 (9)0.0261 (8)0.0015 (7)0.0006 (6)0.0000 (6)
C190.0368 (9)0.0366 (9)0.0237 (7)0.0056 (7)0.0029 (6)0.0011 (6)
C200.0385 (10)0.0484 (10)0.0315 (8)0.0065 (8)0.0000 (7)−0.0006 (7)
C160.0518 (12)0.0429 (10)0.0433 (10)0.0047 (9)−0.0123 (9)−0.0045 (8)
C170.0386 (10)0.0306 (8)0.0321 (8)0.0069 (7)−0.0042 (7)0.0003 (6)
C140.0341 (9)0.0302 (8)0.0430 (9)0.0024 (7)−0.0021 (7)0.0024 (7)
C240.0371 (10)0.0335 (9)0.0316 (8)0.0055 (7)0.0007 (7)0.0025 (6)
C40.0443 (12)0.0400 (10)0.0641 (13)−0.0044 (9)0.0030 (10)−0.0043 (9)
C50.0415 (11)0.0364 (9)0.0415 (9)−0.0004 (8)−0.0001 (8)−0.0038 (7)
C180.0392 (10)0.0326 (9)0.0290 (8)0.0021 (7)−0.0001 (7)0.0023 (6)
C80.0381 (10)0.0342 (9)0.0303 (8)0.0076 (7)0.0021 (7)0.0050 (7)
C130.0375 (10)0.0344 (9)0.0384 (9)0.0078 (7)0.0020 (7)0.0090 (7)
C120.0396 (11)0.0506 (12)0.0576 (12)0.0073 (9)0.0084 (9)0.0158 (9)
C110.0531 (14)0.0686 (15)0.0518 (12)0.0231 (12)0.0216 (10)0.0156 (11)
C100.0692 (16)0.0607 (13)0.0394 (10)0.0273 (12)0.0119 (10)−0.0001 (9)
C90.0518 (12)0.0446 (10)0.0349 (9)0.0134 (9)−0.0005 (8)−0.0005 (7)
C150.0429 (12)0.0375 (10)0.0675 (13)−0.0027 (8)−0.0104 (10)0.0032 (9)
Geometric parameters (Å, º) top
S1—C151.816 (2)C16—C171.493 (2)
S1—C161.818 (2)C16—H16A0.9700
C21—C221.372 (3)C16—H16B0.9700
C21—C201.388 (3)C17—C181.322 (2)
C21—H210.9300C17—C141.534 (2)
C22—C231.386 (3)C14—C241.526 (2)
C22—H220.9300C14—C151.530 (3)
C23—C241.387 (2)C14—C131.530 (2)
C23—H230.9300C4—C51.393 (3)
C3—C41.371 (3)C4—H40.9300
C3—C21.377 (3)C5—H50.9300
C3—H30.9300C18—H180.9300
C2—C11.377 (3)C8—C91.386 (2)
C2—H20.9300C8—C131.401 (3)
C1—C61.398 (2)C13—C121.377 (3)
C1—H10.9300C12—C111.385 (3)
C6—C51.385 (3)C12—H120.9300
C6—C71.518 (2)C11—C101.370 (3)
C7—C181.541 (2)C11—H110.9300
C7—C191.548 (2)C10—C91.394 (3)
C7—C81.555 (2)C10—H100.9300
C19—C201.384 (2)C9—H90.9300
C19—C241.397 (2)C15—H15A0.9700
C20—H200.9300C15—H15B0.9700
C15—S1—C1691.89 (9)C24—C14—C15115.81 (14)
C22—C21—C20120.39 (18)C24—C14—C13104.26 (14)
C22—C21—H21119.8C15—C14—C13117.22 (16)
C20—C21—H21119.8C24—C14—C17105.92 (14)
C21—C22—C23120.73 (18)C15—C14—C17107.92 (15)
C21—C22—H22119.6C13—C14—C17104.65 (13)
C23—C22—H22119.6C23—C24—C19120.46 (17)
C24—C23—C22119.09 (19)C23—C24—C14126.19 (16)
C24—C23—H23120.5C19—C24—C14113.35 (14)
C22—C23—H23120.5C3—C4—C5120.5 (2)
C4—C3—C2119.25 (19)C3—C4—H4119.7
C4—C3—H3120.4C5—C4—H4119.7
C2—C3—H3120.4C6—C5—C4121.00 (18)
C3—C2—C1120.55 (19)C6—C5—H5119.5
C3—C2—H2119.7C4—C5—H5119.5
C1—C2—H2119.7C17—C18—C7115.09 (15)
C2—C1—C6121.21 (19)C17—C18—H18122.5
C2—C1—H1119.4C7—C18—H18122.5
C6—C1—H1119.4C9—C8—C13119.54 (17)
C5—C6—C1117.42 (17)C9—C8—C7126.85 (17)
C5—C6—C7122.88 (15)C13—C8—C7113.58 (14)
C1—C6—C7119.66 (16)C12—C13—C8120.02 (17)
C6—C7—C18115.41 (14)C12—C13—C14126.63 (18)
C6—C7—C19112.82 (14)C8—C13—C14113.35 (15)
C18—C7—C19105.06 (13)C13—C12—C11120.1 (2)
C6—C7—C8115.31 (13)C13—C12—H12119.9
C18—C7—C8103.10 (13)C11—C12—H12119.9
C19—C7—C8103.83 (13)C10—C11—C12120.2 (2)
C20—C19—C24119.52 (16)C10—C11—H11119.9
C20—C19—C7126.56 (16)C12—C11—H11119.9
C24—C19—C7113.91 (15)C11—C10—C9120.46 (19)
C19—C20—C21119.77 (19)C11—C10—H10119.8
C19—C20—H20120.1C9—C10—H10119.8
C21—C20—H20120.1C8—C9—C10119.6 (2)
C17—C16—S1105.52 (13)C8—C9—H9120.2
C17—C16—H16A110.6C10—C9—H9120.2
S1—C16—H16A110.6C14—C15—S1106.81 (13)
C17—C16—H16B110.6C14—C15—H15A110.4
S1—C16—H16B110.6S1—C15—H15A110.4
H16A—C16—H16B108.8C14—C15—H15B110.4
C18—C17—C16130.86 (16)S1—C15—H15B110.4
C18—C17—C14115.23 (15)H15A—C15—H15B108.6
C16—C17—C14113.86 (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—C1957.81 (17)
C4—C3—C2—C10.2 (3)C17—C14—C24—C19−52.30 (18)
C3—C2—C1—C61.9 (3)C2—C3—C4—C5−1.6 (3)
C2—C1—C6—C5−2.6 (3)C1—C6—C5—C41.2 (3)
C2—C1—C6—C7179.40 (18)C7—C6—C5—C4179.12 (17)
C5—C6—C7—C189.5 (2)C3—C4—C5—C60.9 (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—C1966.6 (2)C6—C7—C18—C17−177.47 (15)
C5—C6—C7—C8129.62 (17)C19—C7—C18—C17−52.56 (19)
C1—C6—C7—C8−52.5 (2)C8—C7—C18—C1755.91 (18)
C6—C7—C19—C201.0 (2)C6—C7—C8—C9−3.1 (2)
C18—C7—C19—C20−125.52 (17)C18—C7—C8—C9123.63 (17)
C8—C7—C19—C20126.54 (17)C19—C7—C8—C9−126.98 (17)
C6—C7—C19—C24−179.93 (13)C6—C7—C8—C13178.59 (14)
C18—C7—C19—C2453.54 (17)C18—C7—C8—C13−54.73 (17)
C8—C7—C19—C24−54.39 (17)C19—C7—C8—C1354.66 (17)
C24—C19—C20—C210.4 (2)C9—C8—C13—C121.7 (2)
C7—C19—C20—C21179.44 (16)C7—C8—C13—C12−179.77 (15)
C22—C21—C20—C191.1 (3)C9—C8—C13—C14−177.77 (15)
C15—S1—C16—C1732.38 (13)C7—C8—C13—C140.72 (19)
S1—C16—C17—C18155.10 (17)C24—C14—C13—C12123.19 (18)
S1—C16—C17—C14−22.11 (18)C15—C14—C13—C12−6.3 (3)
C18—C17—C14—C2455.15 (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—C15179.77 (16)C15—C14—C13—C8173.18 (15)
C16—C17—C14—C15−2.6 (2)C17—C14—C13—C853.70 (18)
C18—C17—C14—C13−54.68 (19)C8—C13—C12—C110.0 (3)
C16—C17—C14—C13122.99 (16)C14—C13—C12—C11179.43 (17)
C22—C23—C24—C192.1 (3)C13—C12—C11—C10−1.4 (3)
C22—C23—C24—C14−177.67 (17)C12—C11—C10—C91.2 (3)
C20—C19—C24—C23−2.0 (2)C13—C8—C9—C10−2.0 (3)
C7—C19—C24—C23178.83 (15)C7—C8—C9—C10179.71 (16)
C20—C19—C24—C14177.74 (14)C11—C10—C9—C80.6 (3)
C7—C19—C24—C14−1.39 (19)C24—C14—C15—S1144.72 (13)
C15—C14—C24—C237.9 (3)C13—C14—C15—S1−91.47 (17)
C13—C14—C24—C23−122.42 (18)C17—C14—C15—S126.26 (18)
C17—C14—C24—C23127.46 (18)C16—S1—C15—C14−34.57 (15)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C19–C2 and C8–C13 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C2—H2···Cg1i0.932.803.516 (2)135
C5—H5···Cg1ii0.932.763.5844 (19)149
C15—H15B···Cg2iii0.972.983.845 (2)149
Symmetry codes: (i) −x+3/2, −y−1, z+3/2; (ii) −x+1, −y+2, −z+2; (iii) x+1, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC24H18S
Mr338.44
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)296
a, b, c (Å)18.8842 (11), 9.5339 (4), 19.1140 (9)
V (Å3)3441.3 (3)
Z8
Radiation typeMo Kα
µ (mm−1)0.19
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerBruker Kappa APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.945, 0.963
No. of measured, independent and
observed [I > 2σ(I)] reflections		22858, 3757, 2765
Rint0.032
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.138, 1.02
No. of reflections3757
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.18, −0.26

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2010), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C19–C2 and C8–C13 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C2—H2···Cg1i0.932.803.516 (2)135
C5—H5···Cg1ii0.932.763.5844 (19)149
C15—H15B···Cg2iii0.972.983.845 (2)149
Symmetry codes: (i) −x+3/2, −y−1, z+3/2; (ii) −x+1, −y+2, −z+2; (iii) x+1, −y−1/2, z−1/2.
 

Acknowledgements

EMM is thankful to the Council of Scientific and Industrial Research, New Delhi, India, for financial support in the form of a Senior Research Fellowship. The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India, for the single-crystal X-ray diffraction measurements.

References

First citationBrandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCiganek, E. (1980). J. Org. Chem. 45, 1497–1505.  CrossRef CAS Web of Science Google Scholar
 First citationCox, J. R., Simpson, J. H. & Swager, T. M. (2013). J. Am. Chem. Soc. 135, 640–643.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
 First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationKhalil, A. M., Berghot, M. A., Gouda, M. A. & Bialy, S. A. E. (2010). Monatsh. Chem. 141, 1353–1360.  Web of Science CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationVetter, S. (1998). Synth. Commun. 28, 3219–3223.  Web of Science CrossRef CAS Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 69| Part 7| July 2013| Page o1165
https://doi.org/10.1107/S1600536813017285
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