2-Methyl-3-(phenyl­sulfon­yl)naphtho[1,2-b]furan

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

doi:10.1107/S1600536808000895

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o452

doi:10.1107/S1600536808000895

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2-Methyl-3-(phenylsulfonyl)naphtho[1,2-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 24 December 2007; accepted 10 January 2008; online 16 January 2008)

In the title molecule, C₁₉H₁₄O₃S, the phenyl ring forms a dihedral angle of 69.13 (6)° with the plane of the naphthofuran fragment, being slightly tilted towards it. The crystal packing exhibits π–π interactions between the benzene rings from neighbouring molecules [centroid–centroid distance = 3.616 (4) Å] and weak C—H⋯O and C—H⋯π interactions.

Related literature

The crystal structure of 2-methyl-3-(methylsulfinyl)naphtho[1,2-b]furan has been reported by Choi et al. (2006 ).

Experimental

Crystal data

C₁₉H₁₄O₃S
M_r = 322.36
Orthorhombic, P n a 2₁
a = 8.198 (4) Å
b = 18.589 (8) Å
c = 10.049 (4) Å
V = 1531.4 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 (2) K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
8102 measured reflections
2714 independent reflections
2538 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.083
S = 1.05
2714 reflections
208 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1125 Friedel pairs
Flack parameter: 0.04 (7)

Table 1
Selected interatomic distances (Å)

Cg2 and Cg3 are the centroids of the C2–C5/C10/C11 benzene ring and the C5–C10 benzene ring, respectively.

Cg2⋯Cg3ⁱ	3.616 (4)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the O1/C12/C1/C2/C11 furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯Cg1ⁱ	0.98	2.64	3.483 (3)	144
C8—H8⋯O3ⁱⁱ	0.95	2.51	3.406 (3)	157
C16—H16⋯O3ⁱⁱⁱ	0.95	2.51	3.430 (3)	164
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x-1, y, z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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/S1600536808000895/cv2379sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808000895/cv2379Isup2.hkl

checkCIF report

Comment top

As part of our ongoing study of 2-methylnaphtho[1,2-b]furan derivatives, the crystal structure of 2-methyl-3-(methylsulfinyl)naphtho[1,2-b]furan has been recently reported (Choi et al., 2006). Herein we present the molecular and crystal structure of the title compound, (I).

In (I) (Fig. 1), the naphthofuran unit is essentially planar, with a mean deviation of 0.007 Å from the least-squares plane defined by the thirteen constituent atoms. The crystal packing (Fig. 2) is stabilized by aromatic π—π stacking interactions between adjacent benzene rings. The Cg2···Cg3ⁱ distance is 3.616 (4) Å (Table 1; Cg2 and Cg3 are the centroids of the C2—C5/C10/C11 benzene ring and the C5—C10 benzene ring, respectively, symmetry code as in Fig. 2). The molecular packing is further stabilized by CH₂—H···π interactions between the methyl group and the furan ring of the naphthofuran unit, with a C13—H13A···Cg1ⁱ separation of 2.64 Å (Fig. 2 and Table 2; Cg1 is the centroid of the O1/C12/C1/C2/C11 furan ring; symmetry code as in Fig. 2). Additionally, the weak hydrogen bonds were observed; one between the benzene H atom of naphthofuran unit and the O atom of sulfonyl group, with a C8—H8···O3ⁱⁱ, a second between the benzene H atom of phenylsulfonyl group and adjacent O atom of sulfonyl group, with a C16—H16···O3ⁱⁱⁱ (Fig. 2 and Table 2; symmetry code as in Fig. 2).

Related literature top

The crystal structure of 2-methyl-3-(methylsulfinyl)naphtho[1,2-b]furan has been reported by Choi et al. (2006).

Experimental top

3-Chloroperbenzoic acid (77%, 560 mg, 2.5 mmol) was added in small portions to a stirred solution of 2-methyl-3-(phenylsulfanyl)naphtho[1,2-b] furan (348 mg, 1.2 mmol) in dichloromethane (40 ml) at 273 K. After being stirred at room temperature for 4 h, 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 pale yellow solid [yield 84%, m.p. 412–413 K; R_f = 0.64 (hexane-ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a dilute solution of the title compound in acetone at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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, showing displacement ellipsoides drawn at the 50% probability level.
	Fig. 2. π—π, C—H···π and C—H···O interactions (dotted lines) in the title compound [symmetry codes: (i) x - 1/2, -y + 1/2, z; (ii) -x + 3/2, y + 1/2, z - 1/2; (iii) x - 1, y, z; (iv) x + 1/2, -y + 1/2, z; (v) x + 1, y, z; (vi) -x + 3/2, y - 1/2, z + 1/2.]

2-Methyl-3-(phenylsulfonyl)naphtho[1,2-b]furan top

Crystal data top

C₁₉H₁₄O₃S	F(000) = 672
M_r = 322.36	D_x = 1.398 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5173 reflections
a = 8.198 (4) Å	θ = 2.2–28.1°
b = 18.589 (8) Å	µ = 0.22 mm⁻¹
c = 10.049 (4) Å	T = 173 K
V = 1531.4 (11) Å³	Block, yellow
Z = 4	0.40 × 0.30 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	2538 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
Graphite monochromator	θ_max = 26.0°, θ_min = 2.2°
Detector resolution: 10.0 pixels mm^-1	h = −7→10
ϕ and ω scans	k = −22→22
8102 measured reflections	l = −12→11
2714 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.083	w = 1/[σ²(F_o²) + (0.0507P)² + 0.1234P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2714 reflections	Δρ_max = 0.26 e Å⁻³
208 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1125 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (7)

Crystal data top

C₁₉H₁₄O₃S	V = 1531.4 (11) Å³
M_r = 322.36	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 8.198 (4) Å	µ = 0.22 mm⁻¹
b = 18.589 (8) Å	T = 173 K
c = 10.049 (4) Å	0.40 × 0.30 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	2538 reflections with I > 2σ(I)
8102 measured reflections	R_int = 0.048
2714 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.083	Δρ_max = 0.26 e Å⁻³
S = 1.05	Δρ_min = −0.21 e Å⁻³
2714 reflections	Absolute structure: Flack (1983), 1125 Friedel pairs
208 parameters	Absolute structure parameter: 0.04 (7)
1 restraint

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

	x	y	z	U_iso*/U_eq
S1	0.44268 (6)	0.07870 (2)	0.60161 (6)	0.02617 (13)
O1	0.51082 (18)	0.27348 (7)	0.46110 (15)	0.0291 (3)
O2	0.3904 (2)	0.09804 (9)	0.73361 (15)	0.0373 (4)
O3	0.58124 (17)	0.03221 (8)	0.58544 (17)	0.0369 (4)
C1	0.4858 (2)	0.15710 (10)	0.5141 (2)	0.0253 (4)
C2	0.5822 (2)	0.16115 (11)	0.3939 (2)	0.0260 (4)
C3	0.6620 (3)	0.11149 (11)	0.3089 (2)	0.0293 (4)
H3	0.6565	0.0612	0.3254	0.035*
C4	0.7466 (3)	0.13772 (11)	0.2031 (2)	0.0314 (5)
H4	0.8012	0.1048	0.1460	0.038*
C5	0.7564 (3)	0.21297 (11)	0.1745 (2)	0.0296 (4)
C6	0.8432 (3)	0.23949 (14)	0.0629 (2)	0.0379 (5)
H6	0.8960	0.2067	0.0045	0.045*
C7	0.8521 (3)	0.31235 (14)	0.0381 (3)	0.0448 (6)
H7	0.9111	0.3293	−0.0370	0.054*
C8	0.7749 (3)	0.36149 (12)	0.1225 (3)	0.0421 (6)
H8	0.7828	0.4115	0.1042	0.051*
C9	0.6884 (3)	0.33880 (11)	0.2309 (2)	0.0342 (5)
H9	0.6355	0.3726	0.2872	0.041*
C10	0.6786 (3)	0.26389 (11)	0.2582 (2)	0.0276 (4)
C11	0.5932 (2)	0.23396 (10)	0.3665 (2)	0.0270 (4)
C12	0.4468 (2)	0.22595 (11)	0.5500 (2)	0.0282 (4)
C13	0.3579 (3)	0.25867 (13)	0.6634 (2)	0.0375 (5)
H13A	0.2672	0.2878	0.6297	0.045*
H13B	0.4325	0.2893	0.7143	0.045*
H13C	0.3154	0.2206	0.7211	0.045*
C14	0.2753 (2)	0.03853 (10)	0.51984 (19)	0.0249 (4)
C15	0.1181 (3)	0.05753 (12)	0.5593 (2)	0.0312 (5)
H15	0.1021	0.0928	0.6265	0.037*
C16	−0.0141 (3)	0.02474 (14)	0.5000 (2)	0.0404 (5)
H16	−0.1217	0.0368	0.5272	0.048*
C17	0.0105 (3)	−0.02571 (14)	0.4009 (3)	0.0469 (6)
H17	−0.0805	−0.0486	0.3604	0.056*
C18	0.1664 (3)	−0.04291 (13)	0.3605 (3)	0.0447 (6)
H18	0.1818	−0.0767	0.2908	0.054*
C19	0.3008 (3)	−0.01150 (11)	0.4204 (2)	0.0327 (5)
H19	0.4082	−0.0241	0.3937	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0274 (2)	0.0262 (2)	0.0250 (2)	−0.00075 (19)	−0.0024 (2)	0.0041 (2)
O1	0.0359 (8)	0.0213 (6)	0.0301 (8)	0.0009 (6)	0.0004 (6)	−0.0021 (6)
O2	0.0459 (9)	0.0419 (8)	0.0241 (8)	−0.0059 (8)	−0.0011 (7)	0.0014 (7)
O3	0.0300 (8)	0.0329 (7)	0.0477 (11)	0.0043 (6)	−0.0026 (7)	0.0125 (8)
C1	0.0254 (9)	0.0224 (9)	0.0282 (11)	−0.0009 (8)	−0.0043 (8)	0.0008 (8)
C2	0.0254 (10)	0.0265 (10)	0.0261 (10)	−0.0022 (8)	−0.0030 (8)	0.0021 (8)
C3	0.0337 (11)	0.0226 (9)	0.0317 (11)	−0.0016 (9)	−0.0024 (9)	−0.0003 (8)
C4	0.0356 (12)	0.0298 (10)	0.0290 (11)	0.0004 (9)	0.0012 (9)	−0.0030 (9)
C5	0.0321 (11)	0.0337 (11)	0.0229 (10)	−0.0027 (9)	−0.0040 (8)	0.0025 (9)
C6	0.0411 (13)	0.0454 (14)	0.0271 (12)	−0.0046 (11)	−0.0001 (9)	0.0043 (9)
C7	0.0469 (14)	0.0538 (15)	0.0337 (13)	−0.0117 (12)	−0.0025 (11)	0.0163 (11)
C8	0.0503 (14)	0.0320 (11)	0.0441 (15)	−0.0122 (10)	−0.0105 (11)	0.0122 (11)
C9	0.0381 (12)	0.0278 (10)	0.0366 (13)	−0.0050 (9)	−0.0084 (9)	0.0021 (9)
C10	0.0295 (11)	0.0272 (10)	0.0260 (10)	−0.0050 (8)	−0.0080 (8)	0.0046 (8)
C11	0.0287 (10)	0.0237 (10)	0.0286 (11)	−0.0013 (8)	−0.0042 (8)	−0.0021 (9)
C12	0.0280 (10)	0.0273 (10)	0.0294 (10)	−0.0001 (9)	−0.0032 (8)	−0.0012 (8)
C13	0.0426 (14)	0.0349 (12)	0.0349 (12)	0.0055 (10)	0.0026 (10)	−0.0042 (10)
C14	0.0282 (10)	0.0235 (9)	0.0229 (11)	−0.0014 (8)	0.0004 (8)	0.0052 (8)
C15	0.0327 (11)	0.0338 (10)	0.0271 (11)	0.0014 (10)	0.0036 (8)	0.0036 (8)
C16	0.0297 (11)	0.0534 (14)	0.0380 (14)	−0.0038 (11)	0.0007 (10)	0.0068 (11)
C17	0.0412 (14)	0.0608 (16)	0.0386 (14)	−0.0207 (13)	−0.0045 (11)	0.0009 (12)
C18	0.0576 (15)	0.0430 (13)	0.0335 (13)	−0.0117 (12)	0.0037 (11)	−0.0098 (11)
C19	0.0354 (12)	0.0311 (11)	0.0316 (11)	−0.0021 (9)	0.0058 (9)	−0.0032 (9)

Geometric parameters (Å, º) top

S1—O3	1.437 (2)	C8—C9	1.367 (3)
S1—O2	1.440 (2)	C8—H8	0.9500
S1—C1	1.738 (2)	C9—C10	1.422 (3)
S1—C14	1.765 (2)	C9—H9	0.9500
O1—C12	1.361 (3)	C10—C11	1.409 (3)
O1—C11	1.378 (2)	C12—C13	1.483 (3)
C1—C12	1.368 (3)	C13—H13A	0.9800
C1—C2	1.446 (3)	C13—H13B	0.9800
C2—C11	1.384 (3)	C13—H13C	0.9800
C2—C3	1.418 (3)	C14—C19	1.381 (3)
C3—C4	1.360 (3)	C14—C15	1.394 (3)
C3—H3	0.9500	C15—C16	1.378 (3)
C4—C5	1.430 (3)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.383 (4)
C5—C6	1.417 (3)	C16—H16	0.9500
C5—C10	1.417 (3)	C17—C18	1.379 (4)
C6—C7	1.379 (4)	C17—H17	0.9500
C6—H6	0.9500	C18—C19	1.384 (3)
C7—C8	1.398 (4)	C18—H18	0.9500
C7—H7	0.9500	C19—H19	0.9500

Cg2···Cg3ⁱ	3.616 (4)

O3—S1—O2	119.3 (1)	C11—C10—C5	114.7 (2)
O3—S1—C1	106.6 (1)	C11—C10—C9	124.3 (2)
O2—S1—C1	108.5 (1)	C5—C10—C9	121.0 (2)
O3—S1—C14	107.9 (1)	O1—C11—C2	110.6 (2)
O2—S1—C14	107.7 (1)	O1—C11—C10	124.5 (2)
C1—S1—C14	106.1 (1)	C2—C11—C10	124.9 (2)
C12—O1—C11	107.2 (2)	O1—C12—C1	110.2 (2)
C12—C1—C2	107.4 (2)	O1—C12—C13	115.3 (2)
C12—C1—S1	127.1 (2)	C1—C12—C13	134.5 (2)
C2—C1—S1	125.3 (2)	C12—C13—H13A	109.5
C11—C2—C3	119.1 (2)	C12—C13—H13B	109.5
C11—C2—C1	104.6 (2)	H13A—C13—H13B	109.5
C3—C2—C1	136.2 (2)	C12—C13—H13C	109.5
C4—C3—C2	118.2 (2)	H13A—C13—H13C	109.5
C4—C3—H3	120.9	H13B—C13—H13C	109.5
C2—C3—H3	120.9	C19—C14—C15	121.1 (2)
C3—C4—C5	122.4 (2)	C19—C14—S1	120.3 (2)
C3—C4—H4	118.8	C15—C14—S1	118.6 (2)
C5—C4—H4	118.8	C16—C15—C14	119.4 (2)
C6—C5—C10	117.6 (2)	C16—C15—H15	120.3
C6—C5—C4	121.8 (2)	C14—C15—H15	120.3
C10—C5—C4	120.6 (2)	C15—C16—C17	119.8 (2)
C7—C6—C5	120.8 (2)	C15—C16—H16	120.1
C7—C6—H6	119.6	C17—C16—H16	120.1
C5—C6—H6	119.6	C18—C17—C16	120.3 (2)
C6—C7—C8	120.5 (2)	C18—C17—H17	119.9
C6—C7—H7	119.7	C16—C17—H17	119.9
C8—C7—H7	119.7	C17—C18—C19	120.8 (2)
C9—C8—C7	121.1 (2)	C17—C18—H18	119.6
C9—C8—H8	119.4	C19—C18—H18	119.6
C7—C8—H8	119.4	C14—C19—C18	118.5 (2)
C8—C9—C10	119.0 (2)	C14—C19—H19	120.7
C8—C9—H9	120.5	C18—C19—H19	120.7
C10—C9—H9	120.5

O3—S1—C1—C12	−142.38 (19)	C3—C2—C11—O1	−178.86 (17)
O2—S1—C1—C12	−12.7 (2)	C1—C2—C11—O1	0.0 (2)
C14—S1—C1—C12	102.8 (2)	C3—C2—C11—C10	0.2 (3)
O3—S1—C1—C2	32.34 (19)	C1—C2—C11—C10	179.12 (19)
O2—S1—C1—C2	162.06 (16)	C5—C10—C11—O1	179.07 (18)
C14—S1—C1—C2	−82.51 (18)	C9—C10—C11—O1	−1.2 (3)
C12—C1—C2—C11	−0.1 (2)	C5—C10—C11—C2	0.1 (3)
S1—C1—C2—C11	−175.74 (15)	C9—C10—C11—C2	179.8 (2)
C12—C1—C2—C3	178.5 (2)	C11—O1—C12—C1	−0.2 (2)
S1—C1—C2—C3	2.9 (3)	C11—O1—C12—C13	177.78 (17)
C11—C2—C3—C4	0.0 (3)	C2—C1—C12—O1	0.2 (2)
C1—C2—C3—C4	−178.5 (2)	S1—C1—C12—O1	175.70 (14)
C2—C3—C4—C5	−0.5 (3)	C2—C1—C12—C13	−177.2 (2)
C3—C4—C5—C6	−179.2 (2)	S1—C1—C12—C13	−1.7 (4)
C3—C4—C5—C10	0.9 (3)	O3—S1—C14—C19	−22.04 (19)
C10—C5—C6—C7	0.5 (3)	O2—S1—C14—C19	−152.05 (17)
C4—C5—C6—C7	−179.5 (2)	C1—S1—C14—C19	91.94 (18)
C5—C6—C7—C8	−0.2 (4)	O3—S1—C14—C15	156.92 (16)
C6—C7—C8—C9	−0.4 (4)	O2—S1—C14—C15	26.90 (19)
C7—C8—C9—C10	0.6 (3)	C1—S1—C14—C15	−89.10 (18)
C6—C5—C10—C11	179.43 (18)	C19—C14—C15—C16	1.4 (3)
C4—C5—C10—C11	−0.6 (3)	S1—C14—C15—C16	−177.59 (17)
C6—C5—C10—C9	−0.3 (3)	C14—C15—C16—C17	−1.0 (3)
C4—C5—C10—C9	179.69 (19)	C15—C16—C17—C18	−0.5 (4)
C8—C9—C10—C11	−179.9 (2)	C16—C17—C18—C19	1.6 (4)
C8—C9—C10—C5	−0.3 (3)	C15—C14—C19—C18	−0.2 (3)
C12—O1—C11—C2	0.1 (2)	S1—C14—C19—C18	178.69 (18)
C12—O1—C11—C10	−178.99 (19)	C17—C18—C19—C14	−1.2 (4)

Symmetry code: (i) x−1/2, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Cg1ⁱ	0.98	2.64	3.483 (3)	144
C8—H8···O3ⁱⁱ	0.95	2.51	3.406 (3)	157
C16—H16···O3ⁱⁱⁱ	0.95	2.51	3.430 (3)	164

Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) −x+3/2, y+1/2, z−1/2; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₄O₃S
M_r	322.36
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	173
a, b, c (Å)	8.198 (4), 18.589 (8), 10.049 (4)
V (Å³)	1531.4 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8102, 2714, 2538
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.083, 1.05
No. of reflections	2714
No. of parameters	208
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.21
Absolute structure	Flack (1983), 1125 Friedel pairs
Absolute structure parameter	0.04 (7)

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

Selected interatomic distances (Å) top

Cg2···Cg3ⁱ

3.616 (4)

Symmetry code: (i) x−1/2, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Cg1ⁱ	0.98	2.64	3.483 (3)	143.8
C8—H8···O3ⁱⁱ	0.95	2.51	3.406 (3)	156.7
C16—H16···O3ⁱⁱⁱ	0.95	2.51	3.430 (3)	164.0

Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) −x+3/2, y+1/2, z−1/2; (iii) x−1, y, z.

References

Brandenburg, K. (1998). DIAMOND. Version 2.1. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (1997). SMART (Version 5.631) and SAINT (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Woo, H. M., Seo, P. J., Son, B. W. & Lee, U. (2006). Acta Cryst. E62, o3883–o3884. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals 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 64| Part 2| February 2008| Page o452

doi:10.1107/S1600536808000895

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