2-Phenyl-3-(phenyl­sulfin­yl)naphtho[1,2-b]furan

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

doi:10.1107/S1600536809023101

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1641

doi:10.1107/S1600536809023101

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2-Phenyl-3-(phenylsulfinyl)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 5 June 2009; accepted 16 June 2009; online 20 June 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 [81.54 (5)°]. The 2-phenyl ring is rotated out of the naphthofuran plane, making a dihedral angle of 18.2 (1)°.

Related literature

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

Experimental

Crystal data

C₂₄H₁₆O₂S
M_r = 368.44
Monoclinic, P 2₁ /n
a = 10.123 (1) Å
b = 14.109 (2) Å
c = 12.410 (2) Å
β = 99.743 (2)°
V = 1746.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 K
0.20 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
10523 measured reflections
3804 independent reflections
2555 reflections with I > 2σ(I)
R_int = 0.079

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.137
S = 1.05
3804 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.41 e Å⁻³

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 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023101/hg2520sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809023101/hg2520Isup2.hkl

checkCIF report

Comment top

The naphthofuran compounds have attracted widespread interest in view of their biological and pharmacological activities (Goel & Dixit, 2004; Piloto et al., 2005). This work is related to our communications on the synthesis and structures of naphtho[1,2-b]furan analogues, viz. 2-methyl-3-(phenylsulfonyl)naphtho[1,2-b]furan (Choi et al., 2008a) and 3-(4-chlorophenylsulfonyl)-2-methylnaphtho[1,2-b]furan (Choi et al., 2008b). We report the crystal structure of the title compound (I), 2-phenyl-3-(phenylsulfinyl)naphtho[1,2-b]furan (Fig. 1).

The naphthofuran unit is essentially planar, with a mean deviation of 0.023 (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 18.2 (1)°, and the phenyl ring (C19-C24) with 81.54 (5)° lies toward the naphthofuran plane.

Related literature top

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

Experimental top

The 77% 3-chloroperoxybenzoic acid (77%, 179 mg, 0.8 mmol) was added in small portions to a stirred solution of 2-phenyl-3-(phenylsulfanyl)naphtho[1,2-b]furan (282 mg, 0.8 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 80%, m.p. 472-473 K; R_f = 0.52 (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 compound 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); 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 cycles of arbitrary radius.

2-Phenyl-3-(phenylsulfinyl)naphtho[1,2-b]furan top

Crystal data top

C₂₄H₁₆O₂S	F(000) = 768
M_r = 368.44	D_x = 1.401 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2794 reflections
a = 10.123 (1) Å	θ = 2.4–28.0°
b = 14.109 (2) Å	µ = 0.20 mm⁻¹
c = 12.410 (2) Å	T = 173 K
β = 99.743 (2)°	Block, colorless
V = 1746.9 (4) Å³	0.20 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2555 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.079
Graphite monochromator	θ_max = 27.0°, θ_min = 2.2°
Detector resolution: 10.0 pixels mm^-1	h = −12→12
ϕ and ω scans	k = −18→17
10523 measured reflections	l = −15→10
3804 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)] = 0.053	Hydrogen site location: difference Fourier map
wR(F²) = 0.137	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0554P)² + 0.5717P] where P = (F_o² + 2F_c²)/3
3804 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₂₄H₁₆O₂S	V = 1746.9 (4) Å³
M_r = 368.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.123 (1) Å	µ = 0.20 mm⁻¹
b = 14.109 (2) Å	T = 173 K
c = 12.410 (2) Å	0.20 × 0.20 × 0.15 mm
β = 99.743 (2)°

Data collection top

Bruker SMART CCD diffractometer	2555 reflections with I > 2σ(I)
10523 measured reflections	R_int = 0.079
3804 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.05	Δρ_max = 0.41 e Å⁻³
3804 reflections	Δρ_min = −0.41 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	0.28091 (6)	0.00804 (5)	0.16729 (5)	0.02695 (19)
O1	0.40566 (16)	0.15573 (12)	0.43697 (13)	0.0242 (4)
O2	0.20908 (19)	0.07138 (13)	0.08044 (15)	0.0371 (5)
C1	0.3042 (2)	0.07384 (17)	0.2906 (2)	0.0237 (5)
C2	0.2072 (2)	0.13705 (17)	0.3244 (2)	0.0245 (5)
C3	0.0698 (2)	0.15748 (18)	0.2865 (2)	0.0287 (6)
H3	0.0206	0.1244	0.2261	0.034*
C4	0.0109 (2)	0.22564 (19)	0.3393 (2)	0.0296 (6)
H4	−0.0810	0.2396	0.3146	0.035*
C5	0.0812 (2)	0.27738 (18)	0.4303 (2)	0.0257 (6)
C6	0.0202 (3)	0.34960 (19)	0.4835 (2)	0.0306 (6)
H6	−0.0720	0.3636	0.4600	0.037*
C7	0.0913 (3)	0.39968 (19)	0.5680 (2)	0.0331 (6)
H7	0.0481	0.4480	0.6025	0.040*
C8	0.2281 (3)	0.38060 (19)	0.6046 (2)	0.0322 (6)
H8	0.2768	0.4163	0.6631	0.039*
C9	0.2907 (3)	0.31082 (18)	0.5560 (2)	0.0287 (6)
H9	0.3829	0.2980	0.5812	0.034*
C19	0.1603 (2)	−0.07478 (17)	0.2024 (2)	0.0247 (5)
C10	0.2198 (2)	0.25777 (17)	0.4690 (2)	0.0234 (5)
C11	0.2748 (2)	0.18564 (17)	0.4126 (2)	0.0236 (5)
C12	0.4218 (2)	0.08750 (17)	0.3604 (2)	0.0238 (5)
C13	0.5573 (2)	0.04856 (18)	0.3710 (2)	0.0245 (6)
C14	0.5820 (3)	−0.03834 (18)	0.3242 (2)	0.0291 (6)
H14	0.5092	−0.0741	0.2861	0.035*
C15	0.7112 (3)	−0.07276 (19)	0.3326 (2)	0.0335 (6)
H15	0.7268	−0.1318	0.3001	0.040*
C16	0.8175 (3)	−0.0217 (2)	0.3881 (2)	0.0359 (7)
H16	0.9064	−0.0449	0.3927	0.043*
C17	0.7944 (3)	0.0634 (2)	0.4371 (2)	0.0372 (7)
H17	0.8673	0.0976	0.4773	0.045*
C18	0.6658 (3)	0.0989 (2)	0.4279 (2)	0.0311 (6)
H18	0.6512	0.1580	0.4605	0.037*
C20	0.0331 (3)	−0.07786 (19)	0.1411 (2)	0.0308 (6)
H20	0.0073	−0.0336	0.0837	0.037*
C21	−0.0565 (3)	−0.1460 (2)	0.1641 (2)	0.0349 (7)
H21	−0.1441	−0.1486	0.1222	0.042*
C22	−0.0190 (3)	−0.21003 (19)	0.2474 (2)	0.0351 (7)
H22	−0.0813	−0.2560	0.2636	0.042*
C23	0.1093 (3)	−0.20754 (19)	0.3078 (2)	0.0318 (6)
H23	0.1350	−0.2521	0.3649	0.038*
C24	0.1998 (3)	−0.14042 (18)	0.2852 (2)	0.0290 (6)
H24	0.2882	−0.1390	0.3257	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0311 (3)	0.0275 (4)	0.0222 (3)	−0.0035 (3)	0.0044 (3)	−0.0006 (3)
O1	0.0217 (8)	0.0279 (10)	0.0219 (9)	0.0022 (7)	0.0003 (7)	−0.0001 (7)
O2	0.0493 (12)	0.0350 (11)	0.0250 (10)	−0.0060 (9)	0.0006 (9)	0.0065 (8)
C1	0.0273 (13)	0.0217 (13)	0.0215 (13)	−0.0017 (10)	0.0021 (10)	0.0016 (10)
C2	0.0269 (13)	0.0220 (13)	0.0238 (13)	−0.0018 (10)	0.0025 (11)	0.0047 (11)
C3	0.0259 (13)	0.0286 (14)	0.0291 (14)	−0.0024 (11)	−0.0027 (11)	0.0000 (12)
C4	0.0203 (12)	0.0316 (15)	0.0350 (15)	0.0024 (11)	−0.0007 (11)	0.0048 (12)
C5	0.0274 (13)	0.0259 (14)	0.0242 (13)	0.0018 (11)	0.0056 (11)	0.0062 (11)
C6	0.0280 (13)	0.0300 (15)	0.0350 (16)	0.0059 (11)	0.0087 (12)	0.0084 (12)
C7	0.0413 (15)	0.0288 (15)	0.0320 (15)	0.0071 (12)	0.0144 (13)	0.0011 (12)
C8	0.0397 (15)	0.0289 (15)	0.0278 (14)	0.0013 (12)	0.0056 (12)	−0.0007 (12)
C9	0.0290 (13)	0.0302 (15)	0.0264 (14)	0.0015 (11)	0.0038 (11)	0.0019 (11)
C19	0.0303 (13)	0.0212 (13)	0.0233 (13)	−0.0026 (11)	0.0061 (11)	−0.0048 (10)
C10	0.0253 (13)	0.0239 (13)	0.0216 (13)	−0.0006 (10)	0.0053 (10)	0.0046 (10)
C11	0.0221 (12)	0.0231 (13)	0.0246 (13)	0.0001 (10)	0.0011 (10)	0.0048 (10)
C12	0.0299 (13)	0.0209 (13)	0.0210 (13)	−0.0023 (11)	0.0056 (10)	0.0008 (10)
C13	0.0254 (12)	0.0293 (14)	0.0188 (12)	0.0019 (10)	0.0032 (10)	0.0054 (11)
C14	0.0288 (13)	0.0268 (14)	0.0313 (15)	−0.0017 (11)	0.0041 (12)	0.0022 (12)
C15	0.0359 (15)	0.0286 (15)	0.0365 (16)	0.0080 (12)	0.0077 (13)	0.0038 (13)
C16	0.0273 (14)	0.0436 (17)	0.0366 (16)	0.0120 (13)	0.0048 (12)	0.0081 (14)
C17	0.0300 (14)	0.0487 (19)	0.0302 (15)	0.0029 (13)	−0.0024 (12)	−0.0006 (13)
C18	0.0313 (14)	0.0335 (16)	0.0266 (14)	0.0035 (12)	−0.0006 (11)	−0.0020 (12)
C20	0.0333 (14)	0.0303 (15)	0.0277 (14)	0.0002 (12)	0.0017 (12)	−0.0001 (12)
C21	0.0285 (14)	0.0397 (17)	0.0363 (16)	−0.0065 (12)	0.0048 (12)	−0.0060 (13)
C22	0.0410 (16)	0.0260 (15)	0.0417 (17)	−0.0080 (12)	0.0167 (14)	−0.0075 (13)
C23	0.0446 (16)	0.0229 (14)	0.0294 (15)	0.0025 (12)	0.0103 (13)	0.0031 (11)
C24	0.0317 (14)	0.0298 (14)	0.0243 (13)	−0.0015 (11)	0.0011 (11)	−0.0007 (11)

Geometric parameters (Å, º) top

S—O2	1.4912 (19)	C19—C24	1.390 (3)
S—C1	1.771 (3)	C10—C11	1.403 (3)
S—C19	1.796 (3)	C12—C13	1.463 (3)
O1—C11	1.375 (3)	C13—C18	1.395 (3)
O1—C12	1.381 (3)	C13—C14	1.397 (4)
C1—C12	1.363 (3)	C14—C15	1.383 (4)
C1—C2	1.440 (3)	C14—H14	0.9500
C2—C11	1.372 (3)	C15—C16	1.378 (4)
C2—C3	1.420 (3)	C15—H15	0.9500
C3—C4	1.356 (4)	C16—C17	1.384 (4)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.429 (4)	C17—C18	1.381 (4)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.412 (4)	C18—H18	0.9500
C5—C10	1.431 (3)	C20—C21	1.384 (4)
C6—C7	1.365 (4)	C20—H20	0.9500
C6—H6	0.9500	C21—C22	1.377 (4)
C7—C8	1.408 (4)	C21—H21	0.9500
C7—H7	0.9500	C22—C23	1.386 (4)
C8—C9	1.365 (4)	C22—H22	0.9500
C8—H8	0.9500	C23—C24	1.379 (4)
C9—C10	1.407 (3)	C23—H23	0.9500
C9—H9	0.9500	C24—H24	0.9500
C19—C20	1.381 (3)

O2—S—C1	106.72 (11)	C2—C11—C10	125.0 (2)
O2—S—C19	107.27 (11)	O1—C11—C10	124.2 (2)
C1—S—C19	97.33 (11)	C1—C12—O1	110.1 (2)
C11—O1—C12	106.53 (18)	C1—C12—C13	135.2 (2)
C12—C1—C2	107.0 (2)	O1—C12—C13	114.7 (2)
C12—C1—S	126.7 (2)	C18—C13—C14	118.4 (2)
C2—C1—S	125.37 (18)	C18—C13—C12	120.0 (2)
C11—C2—C3	119.4 (2)	C14—C13—C12	121.5 (2)
C11—C2—C1	105.6 (2)	C15—C14—C13	120.7 (2)
C3—C2—C1	135.0 (2)	C15—C14—H14	119.7
C4—C3—C2	118.0 (2)	C13—C14—H14	119.7
C4—C3—H3	121.0	C16—C15—C14	120.2 (3)
C2—C3—H3	121.0	C16—C15—H15	119.9
C3—C4—C5	122.9 (2)	C14—C15—H15	119.9
C3—C4—H4	118.6	C15—C16—C17	119.8 (2)
C5—C4—H4	118.6	C15—C16—H16	120.1
C6—C5—C4	122.7 (2)	C17—C16—H16	120.1
C6—C5—C10	117.6 (2)	C18—C17—C16	120.3 (3)
C4—C5—C10	119.7 (2)	C18—C17—H17	119.8
C7—C6—C5	121.1 (2)	C16—C17—H17	119.8
C7—C6—H6	119.4	C17—C18—C13	120.5 (3)
C5—C6—H6	119.4	C17—C18—H18	119.7
C6—C7—C8	120.7 (3)	C13—C18—H18	119.7
C6—C7—H7	119.6	C19—C20—C21	119.4 (3)
C8—C7—H7	119.6	C19—C20—H20	120.3
C9—C8—C7	120.0 (3)	C21—C20—H20	120.3
C9—C8—H8	120.0	C22—C21—C20	120.2 (3)
C7—C8—H8	120.0	C22—C21—H21	119.9
C8—C9—C10	120.5 (2)	C20—C21—H21	119.9
C8—C9—H9	119.8	C21—C22—C23	120.2 (3)
C10—C9—H9	119.8	C21—C22—H22	119.9
C20—C19—C24	120.7 (2)	C23—C22—H22	119.9
C20—C19—S	119.7 (2)	C24—C23—C22	120.1 (3)
C24—C19—S	119.35 (19)	C24—C23—H23	120.0
C11—C10—C9	125.1 (2)	C22—C23—H23	120.0
C11—C10—C5	115.0 (2)	C23—C24—C19	119.3 (2)
C9—C10—C5	120.0 (2)	C23—C24—H24	120.3
C2—C11—O1	110.7 (2)	C19—C24—H24	120.3

O2—S—C1—C12	−127.7 (2)	C12—O1—C11—C2	1.2 (3)
C19—S—C1—C12	121.7 (2)	C12—O1—C11—C10	−177.3 (2)
O2—S—C1—C2	39.8 (2)	C9—C10—C11—C2	−176.7 (2)
C19—S—C1—C2	−70.8 (2)	C5—C10—C11—C2	1.9 (4)
C12—C1—C2—C11	0.7 (3)	C9—C10—C11—O1	1.6 (4)
S—C1—C2—C11	−168.88 (19)	C5—C10—C11—O1	−179.8 (2)
C12—C1—C2—C3	179.5 (3)	C2—C1—C12—O1	0.0 (3)
S—C1—C2—C3	10.0 (4)	S—C1—C12—O1	169.41 (17)
C11—C2—C3—C4	0.6 (4)	C2—C1—C12—C13	−178.7 (3)
C1—C2—C3—C4	−178.1 (3)	S—C1—C12—C13	−9.4 (4)
C2—C3—C4—C5	0.2 (4)	C11—O1—C12—C1	−0.7 (3)
C3—C4—C5—C6	178.7 (2)	C11—O1—C12—C13	178.3 (2)
C3—C4—C5—C10	0.0 (4)	C1—C12—C13—C18	158.3 (3)
C4—C5—C6—C7	−177.9 (2)	O1—C12—C13—C18	−20.4 (3)
C10—C5—C6—C7	0.8 (4)	C1—C12—C13—C14	−20.9 (4)
C5—C6—C7—C8	0.0 (4)	O1—C12—C13—C14	160.3 (2)
C6—C7—C8—C9	−0.5 (4)	C18—C13—C14—C15	−1.0 (4)
C7—C8—C9—C10	0.3 (4)	C12—C13—C14—C15	178.3 (2)
O2—S—C19—C20	7.9 (2)	C13—C14—C15—C16	0.3 (4)
C1—S—C19—C20	118.0 (2)	C14—C15—C16—C17	1.2 (4)
O2—S—C19—C24	−177.6 (2)	C15—C16—C17—C18	−2.0 (4)
C1—S—C19—C24	−67.5 (2)	C16—C17—C18—C13	1.3 (4)
C8—C9—C10—C11	179.1 (2)	C14—C13—C18—C17	0.2 (4)
C8—C9—C10—C5	0.5 (4)	C12—C13—C18—C17	−179.1 (2)
C6—C5—C10—C11	−179.7 (2)	C24—C19—C20—C21	1.3 (4)
C4—C5—C10—C11	−1.0 (3)	S—C19—C20—C21	175.7 (2)
C6—C5—C10—C9	−1.0 (4)	C19—C20—C21—C22	0.1 (4)
C4—C5—C10—C9	177.7 (2)	C20—C21—C22—C23	−1.0 (4)
C3—C2—C11—O1	179.8 (2)	C21—C22—C23—C24	0.5 (4)
C1—C2—C11—O1	−1.2 (3)	C22—C23—C24—C19	0.9 (4)
C3—C2—C11—C10	−1.8 (4)	C20—C19—C24—C23	−1.8 (4)
C1—C2—C11—C10	177.3 (2)	S—C19—C24—C23	−176.2 (2)

Experimental details

Crystal data
Chemical formula	C₂₄H₁₆O₂S
M_r	368.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	10.123 (1), 14.109 (2), 12.410 (2)
β (°)	99.743 (2)
V (Å³)	1746.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.20 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10523, 3804, 2555
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.137, 1.05
No. of reflections	3804
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.41

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

References

Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008a). Acta Cryst. E64, o452. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o837. 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
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