2-Phenyl-1-(phenyl­sulfin­yl)naphtho[2,1-b]furan

Choi, H.D.; Seo, P.J.; Son, B.W.; Lee, U.

doi:10.1107/S1600536809019977

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1443

doi:10.1107/S1600536809019977

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2-Phenyl-1-(phenylsulfinyl)naphtho[2,1-b]furan

Hong Dae Choi,^a Pil Ja Seo,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry Pukyong National University 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 25 May 2009; accepted 26 May 2009; online 29 May 2009)

In the title compound, C₂₄H₁₆O₂S, the O atom and the phenyl group of the phenylsulfinyl substituent lie on opposite sides of the plane of the naphthofuran fragment; the phenyl ring is almost perpendicular to this plane [82.34 (5)°]. The 2-phenyl ring is rotated out of the naphthofuran plane making a dihedral angle of 48.21 (6)°. The crystal structure shows π–π interactions between the central benzene rings of adjacent molecules [centroid–centroid distance = 3.516 (3) Å], as well as non-classical C—H⋯O hydrogen bonds.

Related literature

For the crystal structures of similar naphtho[2,1-b]furan derivatives, see: Choi et al. (2007 , 2008 ). For the biological and pharmacological activity of naphthofuran compounds, see: Goel & Dixit (2004 ); Hagiwara et al. (1999 ); Piloto et al. (2005 ).

Experimental

Crystal data

C₂₄H₁₆O₂S
M_r = 368.43
Triclinic, $[P \overline 1]$
a = 9.2262 (7) Å
b = 10.3430 (8) Å
c = 10.4296 (8) Å
α = 78.298 (1)°
β = 86.849 (1)°
γ = 67.506 (1)°
V = 900.15 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
6736 measured reflections
3140 independent reflections
2602 reflections with I > 2σ(I)
R_int = 0.076

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.106
S = 1.06
3140 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O2ⁱ	0.95	2.59	3.488 (3)	158
C18—H18⋯O2ⁱⁱ	0.95	2.57	3.323 (3)	137
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y+1, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019977/ng2587sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019977/ng2587Isup2.hkl

checkCIF report

Comment top

The naphthofuran ring system has attracted widespread interest in view of their biological and pharmacological activities (Goel & Dixit, 2004; Hagiwara et al., 1999; Piloto et al., 2005). This work is related to our communications on the synthesis and structures of naphtho[2,1-b]furan analogues, viz. 2-methyl-1-(phenylsulfinyl)naphtho[2,1-b]furan (Choi et al., 2007) and 2-methyl-1-(phenylsulfonyl)naphtho[2,1-b]furan (Choi et al., 2008). We present the crystal structure of the title compound (I), 2-phenyl-1-(phenylsulfinyl)naphtho[2,1-b]furan (Fig. 1).

The naphthofuran unit is essentially planar, with a mean deviation of 0.015 (2) Å from the least-squares plane defined by the thirteen constituent atoms. The dihedral angle in (I) formed by the plane of the naphthofuran ring and the plane of 2-phenyl ring is 48.21 (6)°, and the phenyl ring (C19-C24) with 82.34 (5)° lies toward the naphthofuran plane. The crystal packing (Fig. 2) is stabilized by aromatic π–π interactions between the central benzene rings from the adjacent molecules. The Cg···Cgⁱⁱⁱ distance is 3.516 (3) Å (Cg is the centroide of the C2/C3/C8/C9/C10/C11 benzene ring, symmetry code as in Fig. 2). The molecular packing is further stabilized by weak non-classical intermolecular C–H···O hydrogen bonds, the first between an aromatic H atom of the naphthofuran fragment and the S═O unit, the second between an aromatic H atom of 2-phenyl ring and the S═O unit, respectively (Table 1 and Fig. 2; symmetry code as in Fig. 2).

Related literature top

For the crystal structures of similar naphtho[2,1-b]furan derivatives, see: Choi et al. (2007, 2008). For the biological and pharmacological activity of naphthofuran compounds, see: Goel & Dixit (2004); Hagiwara et al. (1999); Piloto et al. (2005).

Experimental top

The 77% 3-chloroperoxybenzoic acid (77%, 247 mg, 1.1 mmol) was added in small portions to a stirred solution of 2-phenyl-1-(phenylsulfanyl)naphtho[2,1-b]furan (352 mg, 1.0 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 3h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (hexane-ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 81%, m.p. 462-463 K; R_f = 0.54 (hexane-ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title χompound in benzene at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The π–π and C–H···O interactions (dotted lines) in the title compound. Cg denotes the ring centroids. [Symmetry code: (i) x - 1, y, z; (ii) -x + 2, -y + 1, -z + 1; (iii) -x + 1, -y + 1, -z + 1.]

2-Phenyl-1-(phenylsulfinyl)naphtho[2,1-b]furan top

Crystal data top

C₂₄H₁₆O₂S	Z = 2
M_r = 368.43	F(000) = 384
Triclinic, P1	D_x = 1.359 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2262 (7) Å	Cell parameters from 3903 reflections
b = 10.3430 (8) Å	θ = 2.2–28.1°
c = 10.4296 (8) Å	µ = 0.20 mm⁻¹
α = 78.298 (1)°	T = 173 K
β = 86.849 (1)°	Block, colorless
γ = 67.506 (1)°	0.30 × 0.20 × 0.10 mm
V = 900.15 (12) Å³

Data collection top

Bruker SMART CCD diffractometer	2602 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.076
Graphite monochromator	θ_max = 25.0°, θ_min = 2.6°
Detector resolution: 10.0 pixels mm^-1	h = −10→10
ϕ and ω scans	k = −12→12
6736 measured reflections	l = −12→12
3140 independent reflections

Refinement top

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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F²) = 0.106	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0292P)² + 0.4516P] where P = (F_o² + 2F_c²)/3
3140 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₄H₁₆O₂S	γ = 67.506 (1)°
M_r = 368.43	V = 900.15 (12) Å³
Triclinic, P1	Z = 2
a = 9.2262 (7) Å	Mo Kα radiation
b = 10.3430 (8) Å	µ = 0.20 mm⁻¹
c = 10.4296 (8) Å	T = 173 K
α = 78.298 (1)°	0.30 × 0.20 × 0.10 mm
β = 86.849 (1)°

Data collection top

Bruker SMART CCD diffractometer	2602 reflections with I > 2σ(I)
6736 measured reflections	R_int = 0.076
3140 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.06	Δρ_max = 0.30 e Å⁻³
3140 reflections	Δρ_min = −0.36 e Å⁻³
244 parameters

Special details top

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 > 2sigma(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

	x	y	z	U_iso*/U_eq
S	0.92526 (5)	0.67298 (6)	0.63521 (5)	0.02249 (16)
O1	0.55628 (15)	0.80588 (16)	0.40427 (15)	0.0287 (4)
O2	1.01571 (15)	0.51840 (16)	0.68794 (15)	0.0304 (4)
C1	0.7484 (2)	0.6976 (2)	0.5575 (2)	0.0217 (4)
C2	0.6230 (2)	0.6466 (2)	0.5980 (2)	0.0225 (5)
C3	0.5963 (2)	0.5480 (2)	0.7043 (2)	0.0247 (5)
C4	0.7034 (2)	0.4667 (2)	0.8087 (2)	0.0288 (5)
H4	0.8013	0.4767	0.8114	0.035*
C5	0.6685 (3)	0.3735 (3)	0.9063 (2)	0.0369 (6)
H5	0.7423	0.3195	0.9760	0.044*
C6	0.5244 (3)	0.3568 (3)	0.9045 (3)	0.0409 (6)
H6	0.5006	0.2928	0.9733	0.049*
C7	0.4196 (3)	0.4323 (3)	0.8042 (3)	0.0367 (6)
H7	0.3231	0.4194	0.8033	0.044*
C8	0.4506 (2)	0.5296 (2)	0.7011 (2)	0.0304 (5)
C9	0.3413 (2)	0.6054 (3)	0.5950 (3)	0.0350 (6)
H9	0.2462	0.5900	0.5946	0.042*
C10	0.3676 (2)	0.6990 (3)	0.4943 (2)	0.0341 (6)
H10	0.2936	0.7499	0.4242	0.041*
C11	0.5109 (2)	0.7163 (2)	0.4998 (2)	0.0265 (5)
C12	0.7040 (2)	0.7901 (2)	0.4412 (2)	0.0240 (5)
C13	0.7758 (2)	0.8777 (2)	0.3541 (2)	0.0245 (5)
C14	0.6902 (3)	1.0219 (2)	0.3089 (2)	0.0310 (5)
H14	0.5843	1.0632	0.3339	0.037*
C15	0.7568 (3)	1.1061 (2)	0.2284 (2)	0.0355 (6)
H15	0.6975	1.2049	0.1987	0.043*
C16	0.9113 (3)	1.0456 (3)	0.1907 (2)	0.0362 (6)
H16	0.9579	1.1031	0.1350	0.043*
C17	0.9966 (3)	0.9026 (3)	0.2340 (2)	0.0332 (5)
H17	1.1020	0.8618	0.2076	0.040*
C18	0.9314 (2)	0.8173 (2)	0.3153 (2)	0.0280 (5)
H18	0.9914	0.7185	0.3448	0.034*
C19	0.8432 (2)	0.7532 (2)	0.7740 (2)	0.0233 (5)
C20	0.7332 (2)	0.8915 (2)	0.7556 (2)	0.0296 (5)
H20	0.6946	0.9429	0.6700	0.036*
C21	0.6802 (3)	0.9539 (3)	0.8632 (3)	0.0376 (6)
H21	0.6040	1.0485	0.8519	0.045*
C22	0.7381 (3)	0.8787 (3)	0.9879 (2)	0.0369 (6)
H22	0.7005	0.9218	1.0617	0.044*
C23	0.8501 (3)	0.7414 (3)	1.0049 (2)	0.0344 (5)
H23	0.8901	0.6904	1.0901	0.041*
C24	0.9038 (2)	0.6785 (2)	0.8972 (2)	0.0286 (5)
H24	0.9817	0.5846	0.9080	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0174 (2)	0.0248 (3)	0.0242 (3)	−0.0081 (2)	−0.00033 (18)	−0.0022 (2)
O1	0.0238 (7)	0.0305 (9)	0.0299 (9)	−0.0084 (6)	−0.0053 (6)	−0.0044 (7)
O2	0.0223 (7)	0.0265 (9)	0.0369 (10)	−0.0036 (6)	−0.0003 (6)	−0.0050 (7)
C1	0.0188 (9)	0.0223 (11)	0.0238 (11)	−0.0064 (8)	0.0017 (8)	−0.0074 (9)
C2	0.0193 (9)	0.0216 (11)	0.0274 (12)	−0.0063 (8)	0.0018 (8)	−0.0095 (9)
C3	0.0232 (10)	0.0224 (11)	0.0308 (12)	−0.0091 (8)	0.0083 (8)	−0.0112 (9)
C4	0.0261 (11)	0.0277 (12)	0.0332 (13)	−0.0113 (9)	0.0050 (9)	−0.0062 (10)
C5	0.0389 (12)	0.0335 (14)	0.0367 (14)	−0.0142 (10)	0.0070 (10)	−0.0046 (11)
C6	0.0474 (14)	0.0377 (15)	0.0431 (16)	−0.0235 (12)	0.0206 (12)	−0.0106 (12)
C7	0.0319 (12)	0.0411 (15)	0.0481 (16)	−0.0229 (11)	0.0184 (11)	−0.0193 (12)
C8	0.0244 (10)	0.0321 (13)	0.0389 (14)	−0.0115 (9)	0.0105 (9)	−0.0172 (11)
C9	0.0197 (10)	0.0421 (15)	0.0493 (16)	−0.0135 (10)	0.0068 (10)	−0.0207 (12)
C10	0.0211 (10)	0.0397 (14)	0.0417 (15)	−0.0075 (10)	−0.0035 (9)	−0.0158 (11)
C11	0.0225 (10)	0.0256 (12)	0.0316 (13)	−0.0071 (9)	0.0020 (8)	−0.0104 (9)
C12	0.0207 (9)	0.0244 (11)	0.0257 (12)	−0.0053 (8)	−0.0019 (8)	−0.0085 (9)
C13	0.0281 (10)	0.0268 (12)	0.0196 (11)	−0.0105 (9)	−0.0003 (8)	−0.0064 (9)
C14	0.0325 (11)	0.0265 (13)	0.0302 (13)	−0.0064 (9)	0.0002 (9)	−0.0072 (10)
C15	0.0466 (13)	0.0213 (12)	0.0367 (14)	−0.0115 (10)	−0.0019 (10)	−0.0036 (10)
C16	0.0468 (13)	0.0354 (14)	0.0331 (14)	−0.0249 (11)	0.0010 (10)	−0.0027 (11)
C17	0.0305 (11)	0.0376 (14)	0.0325 (13)	−0.0144 (10)	0.0019 (9)	−0.0064 (11)
C18	0.0290 (11)	0.0247 (12)	0.0282 (12)	−0.0075 (9)	−0.0010 (9)	−0.0051 (9)
C19	0.0208 (10)	0.0268 (12)	0.0257 (12)	−0.0128 (9)	0.0000 (8)	−0.0045 (9)
C20	0.0261 (10)	0.0292 (13)	0.0314 (13)	−0.0080 (9)	−0.0063 (9)	−0.0045 (10)
C21	0.0298 (12)	0.0363 (14)	0.0453 (16)	−0.0060 (10)	−0.0018 (10)	−0.0173 (12)
C22	0.0374 (13)	0.0480 (16)	0.0337 (14)	−0.0202 (11)	0.0059 (10)	−0.0199 (12)
C23	0.0453 (13)	0.0397 (14)	0.0251 (13)	−0.0252 (11)	−0.0016 (10)	−0.0027 (10)
C24	0.0335 (11)	0.0244 (12)	0.0288 (13)	−0.0137 (9)	−0.0030 (9)	−0.0009 (9)

Geometric parameters (Å, º) top

S—O2	1.4926 (15)	C12—C13	1.464 (3)
S—C1	1.7690 (19)	C13—C14	1.388 (3)
S—C19	1.801 (2)	C13—C18	1.402 (3)
O1—C12	1.376 (2)	C14—C15	1.377 (3)
O1—C11	1.380 (3)	C14—H14	0.9500
C1—C12	1.356 (3)	C15—C16	1.391 (3)
C1—C2	1.455 (3)	C15—H15	0.9500
C2—C11	1.373 (3)	C16—C17	1.375 (3)
C2—C3	1.426 (3)	C16—H16	0.9500
C3—C4	1.407 (3)	C17—C18	1.381 (3)
C3—C8	1.431 (3)	C17—H17	0.9500
C4—C5	1.369 (3)	C18—H18	0.9500
C4—H4	0.9500	C19—C24	1.380 (3)
C5—C6	1.406 (3)	C19—C20	1.383 (3)
C5—H5	0.9500	C20—C21	1.381 (3)
C6—C7	1.357 (4)	C20—H20	0.9500
C6—H6	0.9500	C21—C22	1.389 (4)
C7—C8	1.414 (3)	C21—H21	0.9500
C7—H7	0.9500	C22—C23	1.382 (3)
C8—C9	1.423 (3)	C22—H22	0.9500
C9—C10	1.355 (4)	C23—C24	1.386 (3)
C9—H9	0.9500	C23—H23	0.9500
C10—C11	1.406 (3)	C24—H24	0.9500
C10—H10	0.9500

O2—S—C1	110.64 (9)	C1—C12—C13	133.87 (18)
O2—S—C19	106.60 (9)	O1—C12—C13	115.97 (18)
C1—S—C19	98.59 (9)	C14—C13—C18	119.2 (2)
C12—O1—C11	106.29 (16)	C14—C13—C12	120.17 (18)
C12—C1—C2	107.88 (17)	C18—C13—C12	120.62 (19)
C12—C1—S	119.06 (15)	C15—C14—C13	120.8 (2)
C2—C1—S	132.80 (16)	C15—C14—H14	119.6
C11—C2—C3	119.15 (18)	C13—C14—H14	119.6
C11—C2—C1	104.07 (19)	C14—C15—C16	119.7 (2)
C3—C2—C1	136.75 (18)	C14—C15—H15	120.2
C4—C3—C2	124.79 (18)	C16—C15—H15	120.2
C4—C3—C8	118.6 (2)	C17—C16—C15	119.9 (2)
C2—C3—C8	116.6 (2)	C17—C16—H16	120.1
C5—C4—C3	120.9 (2)	C15—C16—H16	120.1
C5—C4—H4	119.5	C16—C17—C18	121.0 (2)
C3—C4—H4	119.5	C16—C17—H17	119.5
C4—C5—C6	120.6 (2)	C18—C17—H17	119.5
C4—C5—H5	119.7	C17—C18—C13	119.4 (2)
C6—C5—H5	119.7	C17—C18—H18	120.3
C7—C6—C5	119.8 (2)	C13—C18—H18	120.3
C7—C6—H6	120.1	C24—C19—C20	121.2 (2)
C5—C6—H6	120.1	C24—C19—S	118.22 (16)
C6—C7—C8	121.5 (2)	C20—C19—S	120.25 (17)
C6—C7—H7	119.2	C21—C20—C19	119.0 (2)
C8—C7—H7	119.2	C21—C20—H20	120.5
C7—C8—C9	121.0 (2)	C19—C20—H20	120.5
C7—C8—C3	118.5 (2)	C20—C21—C22	120.2 (2)
C9—C8—C3	120.5 (2)	C20—C21—H21	119.9
C10—C9—C8	122.5 (2)	C22—C21—H21	119.9
C10—C9—H9	118.8	C23—C22—C21	120.2 (2)
C8—C9—H9	118.8	C23—C22—H22	119.9
C9—C10—C11	116.1 (2)	C21—C22—H22	119.9
C9—C10—H10	122.0	C22—C23—C24	119.8 (2)
C11—C10—H10	122.0	C22—C23—H23	120.1
C2—C11—O1	111.62 (17)	C24—C23—H23	120.1
C2—C11—C10	125.1 (2)	C19—C24—C23	119.5 (2)
O1—C11—C10	123.3 (2)	C19—C24—H24	120.3
C1—C12—O1	110.10 (18)	C23—C24—H24	120.3

O2—S—C1—C12	−136.67 (16)	C9—C10—C11—C2	−0.1 (3)
C19—S—C1—C12	111.89 (17)	C9—C10—C11—O1	179.1 (2)
O2—S—C1—C2	50.0 (2)	C2—C1—C12—O1	1.4 (2)
C19—S—C1—C2	−61.5 (2)	S—C1—C12—O1	−173.45 (13)
C12—C1—C2—C11	−0.5 (2)	C2—C1—C12—C13	178.2 (2)
S—C1—C2—C11	173.40 (17)	S—C1—C12—C13	3.3 (3)
C12—C1—C2—C3	177.6 (2)	C11—O1—C12—C1	−1.8 (2)
S—C1—C2—C3	−8.5 (4)	C11—O1—C12—C13	−179.21 (17)
C11—C2—C3—C4	178.0 (2)	C1—C12—C13—C14	−129.7 (3)
C1—C2—C3—C4	0.1 (4)	O1—C12—C13—C14	47.0 (3)
C11—C2—C3—C8	−0.6 (3)	C1—C12—C13—C18	50.2 (3)
C1—C2—C3—C8	−178.5 (2)	O1—C12—C13—C18	−133.2 (2)
C2—C3—C4—C5	−179.5 (2)	C18—C13—C14—C15	−0.8 (3)
C8—C3—C4—C5	−0.9 (3)	C12—C13—C14—C15	179.1 (2)
C3—C4—C5—C6	0.0 (3)	C13—C14—C15—C16	0.6 (4)
C4—C5—C6—C7	0.9 (4)	C14—C15—C16—C17	−0.1 (4)
C5—C6—C7—C8	−0.8 (4)	C15—C16—C17—C18	−0.3 (4)
C6—C7—C8—C9	178.5 (2)	C16—C17—C18—C13	0.1 (3)
C6—C7—C8—C3	−0.2 (3)	C14—C13—C18—C17	0.5 (3)
C4—C3—C8—C7	1.1 (3)	C12—C13—C18—C17	−179.4 (2)
C2—C3—C8—C7	179.70 (19)	O2—S—C19—C24	16.08 (18)
C4—C3—C8—C9	−177.6 (2)	C1—S—C19—C24	130.73 (17)
C2—C3—C8—C9	1.0 (3)	O2—S—C19—C20	−170.04 (16)
C7—C8—C9—C10	−179.7 (2)	C1—S—C19—C20	−55.39 (18)
C3—C8—C9—C10	−1.1 (3)	C24—C19—C20—C21	−1.9 (3)
C8—C9—C10—C11	0.6 (3)	S—C19—C20—C21	−175.57 (17)
C3—C2—C11—O1	−179.15 (17)	C19—C20—C21—C22	0.6 (3)
C1—C2—C11—O1	−0.6 (2)	C20—C21—C22—C23	0.6 (4)
C3—C2—C11—C10	0.1 (3)	C21—C22—C23—C24	−0.5 (3)
C1—C2—C11—C10	178.7 (2)	C20—C19—C24—C23	2.0 (3)
C12—O1—C11—C2	1.5 (2)	S—C19—C24—C23	175.80 (15)
C12—O1—C11—C10	−177.8 (2)	C22—C23—C24—C19	−0.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2ⁱ	0.95	2.59	3.488 (3)	158
C18—H18···O2ⁱⁱ	0.95	2.57	3.323 (3)	137

Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₆O₂S
M_r	368.43
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	9.2262 (7), 10.3430 (8), 10.4296 (8)
α, β, γ (°)	78.298 (1), 86.849 (1), 67.506 (1)
V (Å³)	900.15 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6736, 3140, 2602
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.106, 1.06
No. of reflections	3140
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.36

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2ⁱ	0.95	2.59	3.488 (3)	158.0
C18—H18···O2ⁱⁱ	0.95	2.57	3.323 (3)	136.7

Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z+1.

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o1731–o1732. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o727. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Goel, A. & Dixit, M. (2004). Tetrahedron Lett. 45, 8819-8821. Web of Science CrossRef CAS Google Scholar
Hagiwara, H., Sato, K., Suzuki, T. & Ando, M. (1999). Heterocycles, 51, 497-500. CrossRef CAS Google Scholar
Piloto, A. M., Costa, S. P. G. & Goncalves, M. S. T. (2005). Tetrahedron Lett. 46, 4757–4760. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 6| June 2009| Page o1443

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