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

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

doi:10.1107/S1600536808007046

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o727

doi:10.1107/S1600536808007046

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2-Methyl-1-(phenylsulfonyl)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 24 January 2008; accepted 13 March 2008; online 20 March 2008)

The title compound, C₁₉H₁₄O₃S, was prepared by the oxidation of 2-methyl-1-(phenylsulfanyl)naphtho[2,1-b]furan with 3-chloroperoxybenzoic acid. The phenyl ring makes a dihedral angle of 87.13 (4)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by π–π interactions between the furan and benzene rings of neighbouring molecules [centroid–centroid distance = 3.850 (2) Å] and weak C—H⋯π interactions. In addition, there are also intramolecular C—H⋯O interactions.

Related literature

For the crystal structures of similar 2-methylnaphtho[2,1-b]furan compounds, see: Choi et al. (2006 , 2007 ).

Experimental

Crystal data

C₁₉H₁₄O₃S
M_r = 322.36
Monoclinic, P 2₁ /n
a = 10.7175 (4) Å
b = 7.7972 (3) Å
c = 18.0488 (7) Å
β = 97.797 (1)°
V = 1494.33 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 (2) K
0.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
8784 measured reflections
3222 independent reflections
2785 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.098
S = 1.05
3222 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2	0.95	2.35	3.190 (2)	147
C18—H18⋯O2	0.95	2.46	2.869 (2)	106
C19—H19B⋯O3	0.98	2.55	2.926 (2)	103
C19—H19C⋯Cg3ⁱ	0.98	3.03	3.735 (3)	130
C16—H16⋯Cg3ⁱⁱ	0.95	2.88	3.761 (3)	155
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+2, -y+1, -z. Cg3 is the centroid of the benzene ring of the naphthofuran unit.

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/S1600536808007046/fb2090sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808007046/fb2090Isup2.hkl

checkCIF report

Comment top

As a part of our ongoing studies on the synthesis and structure of 2-methylnaphtho[2,1-b]furan derivatives, the crystal structures of 2-methyl-1-(methylsulfinyl)naphtho[2,1-b]furan (Choi et al., 2006) and 2-methyl-1-(phenylsulfinyl)naphtho[2,1-b]furan (Choi et al., 2007) have already been described. Herein we report the molecular and the crystal structure of the title compound, 2-methyl-1-(phenylsulfonyl)naphtho[2,1-b]furan (Fig. 1).

The naphthofuran unit is essentially planar, with a mean deviation equal to 0.040 Å from the least-squares plane defined by thirteen constituent atoms. The crystal packing (Fig. 2) is stabilized by aromatic π—π stacking interactions between the furan and the benzene rings from the adjacent naphthofuran fragments. The Cg1···Cg2ⁱ distance is 3.850 (2) Å (Cg1 and Cg2 are the centroids of the O1/C12/C1/C2/C11 furan and the C2/C3/C8/C9/C10/C11 benzene rings, respectively, the symmetry code as in Fig. 2). The crystal packing (Fig. 2) is further stabilized by the C—H···π interactions; in both cases the benzene ring of the naphthofuran unit (Cg3) is involved. There are also intramolecular C—H···O interactions present in the structure.

Related literature top

For the crystal structures of similar 2-methylnaphtho[2,1-b]furan compounds, see: Choi et al. (2006, 2007).

Experimental top

3-Chloroperoxybenzoic acid (77%, 471 mg, 2.10 mmol) was added in small portions to a stirred solution of 2-methyl-1-(phenylsulfanyl)naphtho[2,1-b]furan (290 mg, 1.0 mmol) in dichloromethane (20 ml) at 273 K. After having been stirred for 4 h at room temperature, the mixture was washed with saturated sodium hydrogencarbonate 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 colourless solid [yield 84%, m.p. 431–432 K; R_f = 0.63 (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 acetone at room temperature. The average crystal size was approximately 1.0 × 1.0 × 0.5 mm. The crystals are colourless and soluble in polar solvents.

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, showing displacement ellipsoides drawn at the 50% probability level.
	Fig. 2. π—π, C—H···π and intramolecular C—H···O interactions (dotted lines) in the title compound. Cg denotes the ring centroids. [Symmetry code: (i) 1 - x, -y, -z; (ii) 2 - x, 1 - y, -z; (iii) x + 1, y + 1, z.]

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

Crystal data top

C₁₉H₁₄O₃S	F(000) = 672
M_r = 322.36	D_x = 1.433 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 431–432 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.7175 (4) Å	Cell parameters from 5468 reflections
b = 7.7972 (3) Å	θ = 2.3–28.2°
c = 18.0488 (7) Å	µ = 0.23 mm⁻¹
β = 97.797 (1)°	T = 173 K
V = 1494.33 (10) Å³	Block, colourless
Z = 4	0.40 × 0.40 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	2785 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 27.0°, θ_min = 2.9°
Detector resolution: 10.0 pixels mm^-1	h = −13→11
ϕ and ω scans	k = −9→9
8784 measured reflections	l = −23→23
3222 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0464P)² + 0.7406P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3222 reflections	Δρ_max = 0.33 e Å⁻³
210 parameters	Δρ_min = −0.39 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
54 constraints	Extinction coefficient: 0.015 (2)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₉H₁₄O₃S	V = 1494.33 (10) Å³
M_r = 322.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.7175 (4) Å	µ = 0.23 mm⁻¹
b = 7.7972 (3) Å	T = 173 K
c = 18.0488 (7) Å	0.40 × 0.40 × 0.20 mm
β = 97.797 (1)°

Data collection top

Bruker SMART CCD diffractometer	2785 reflections with I > 2σ(I)
8784 measured reflections	R_int = 0.023
3222 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.05	Δρ_max = 0.33 e Å⁻³
3222 reflections	Δρ_min = −0.39 e Å⁻³
210 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

	x	y	z	U_iso*/U_eq
S	0.78568 (4)	0.07420 (5)	0.11326 (2)	0.02579 (13)
O1	0.44773 (10)	0.27156 (15)	0.07186 (6)	0.0317 (3)
O2	0.81955 (11)	−0.07018 (14)	0.07052 (7)	0.0327 (3)
O3	0.78345 (12)	0.05031 (17)	0.19220 (6)	0.0376 (3)
C1	0.63938 (14)	0.1558 (2)	0.07427 (8)	0.0251 (3)
C2	0.59348 (14)	0.19921 (19)	−0.00332 (8)	0.0239 (3)
C3	0.63656 (14)	0.18767 (19)	−0.07498 (8)	0.0246 (3)
C4	0.74995 (16)	0.1091 (2)	−0.08857 (9)	0.0294 (3)
H4	0.8031	0.0575	−0.0483	0.035*
C5	0.78480 (18)	0.1059 (2)	−0.15919 (9)	0.0360 (4)
H5	0.8612	0.0516	−0.1671	0.043*
C6	0.70826 (19)	0.1822 (3)	−0.21959 (9)	0.0407 (4)
H6	0.7339	0.1820	−0.2680	0.049*
C7	0.59747 (18)	0.2564 (2)	−0.20867 (9)	0.0383 (4)
H7	0.5460	0.3066	−0.2500	0.046*
C8	0.55669 (15)	0.2608 (2)	−0.13718 (9)	0.0297 (4)
C9	0.43790 (16)	0.3342 (2)	−0.12790 (10)	0.0355 (4)
H9	0.3867	0.3809	−0.1702	0.043*
C10	0.39621 (15)	0.3389 (2)	−0.06035 (10)	0.0335 (4)
H10	0.3164	0.3859	−0.0543	0.040*
C11	0.47661 (14)	0.2710 (2)	0.00014 (9)	0.0273 (3)
C12	0.54835 (15)	0.2028 (2)	0.11655 (9)	0.0294 (3)
C13	0.89432 (14)	0.24061 (19)	0.10214 (8)	0.0247 (3)
C14	0.87639 (16)	0.4045 (2)	0.12958 (9)	0.0299 (4)
H14	0.8035	0.4308	0.1520	0.036*
C15	0.96700 (17)	0.5283 (2)	0.12344 (9)	0.0351 (4)
H15	0.9550	0.6417	0.1403	0.042*
C16	1.07529 (17)	0.4877 (2)	0.09275 (9)	0.0367 (4)
H16	1.1377	0.5730	0.0897	0.044*
C17	1.09280 (16)	0.3244 (2)	0.06666 (10)	0.0360 (4)
H17	1.1675	0.2969	0.0463	0.043*
C18	1.00096 (15)	0.2003 (2)	0.07027 (9)	0.0301 (4)
H18	1.0112	0.0886	0.0510	0.036*
C19	0.53353 (18)	0.1975 (3)	0.19698 (10)	0.0414 (4)
H19A	0.4597	0.2651	0.2054	0.062*
H19B	0.6089	0.2455	0.2266	0.062*
H19C	0.5222	0.0784	0.2121	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0269 (2)	0.0252 (2)	0.0241 (2)	0.00073 (15)	−0.00082 (14)	0.00240 (14)
O1	0.0246 (6)	0.0341 (6)	0.0373 (6)	−0.0007 (5)	0.0076 (5)	0.0014 (5)
O2	0.0342 (6)	0.0231 (6)	0.0394 (6)	0.0013 (5)	0.0005 (5)	−0.0007 (5)
O3	0.0411 (7)	0.0446 (7)	0.0259 (6)	−0.0008 (6)	−0.0007 (5)	0.0089 (5)
C1	0.0243 (7)	0.0255 (8)	0.0250 (7)	−0.0014 (6)	0.0017 (6)	0.0009 (6)
C2	0.0226 (7)	0.0204 (7)	0.0276 (8)	−0.0032 (6)	−0.0001 (6)	0.0003 (6)
C3	0.0267 (7)	0.0214 (7)	0.0245 (7)	−0.0049 (6)	−0.0012 (6)	−0.0004 (6)
C4	0.0317 (8)	0.0298 (8)	0.0261 (8)	−0.0004 (6)	0.0017 (6)	−0.0011 (6)
C5	0.0386 (9)	0.0395 (10)	0.0307 (8)	−0.0018 (7)	0.0074 (7)	−0.0055 (7)
C6	0.0503 (11)	0.0482 (11)	0.0236 (8)	−0.0117 (9)	0.0056 (7)	−0.0026 (8)
C7	0.0438 (10)	0.0421 (10)	0.0262 (8)	−0.0096 (8)	−0.0061 (7)	0.0056 (7)
C8	0.0308 (8)	0.0282 (8)	0.0278 (8)	−0.0075 (7)	−0.0046 (6)	0.0032 (6)
C9	0.0304 (9)	0.0335 (9)	0.0386 (9)	−0.0035 (7)	−0.0093 (7)	0.0097 (7)
C10	0.0220 (8)	0.0305 (9)	0.0463 (10)	−0.0009 (6)	−0.0017 (7)	0.0061 (7)
C11	0.0240 (8)	0.0245 (8)	0.0331 (8)	−0.0040 (6)	0.0030 (6)	0.0009 (6)
C12	0.0271 (8)	0.0302 (8)	0.0311 (8)	−0.0032 (6)	0.0043 (6)	0.0011 (7)
C13	0.0249 (7)	0.0249 (8)	0.0228 (7)	0.0008 (6)	−0.0024 (6)	0.0007 (6)
C14	0.0316 (8)	0.0280 (8)	0.0293 (8)	0.0053 (6)	0.0015 (6)	−0.0006 (6)
C15	0.0471 (10)	0.0254 (8)	0.0311 (8)	−0.0008 (7)	−0.0009 (7)	−0.0016 (7)
C16	0.0410 (10)	0.0359 (10)	0.0318 (8)	−0.0107 (8)	0.0003 (7)	0.0023 (7)
C17	0.0304 (9)	0.0425 (10)	0.0355 (9)	−0.0028 (7)	0.0065 (7)	−0.0031 (8)
C18	0.0290 (8)	0.0297 (8)	0.0309 (8)	0.0021 (6)	0.0015 (6)	−0.0058 (7)
C19	0.0415 (10)	0.0521 (12)	0.0335 (9)	−0.0013 (9)	0.0154 (8)	0.0001 (8)

Geometric parameters (Å, º) top

S—O2	1.4387 (12)	C8—C9	1.426 (2)
S—O3	1.4403 (12)	C9—C10	1.355 (2)
S—C1	1.7492 (15)	C9—H9	0.9500
S—C13	1.7729 (16)	C10—C11	1.400 (2)
O1—C12	1.366 (2)	C10—H10	0.9500
O1—C11	1.3713 (19)	C12—C19	1.482 (2)
C1—C12	1.367 (2)	C13—C18	1.383 (2)
C1—C2	1.460 (2)	C13—C14	1.393 (2)
C2—C11	1.381 (2)	C14—C15	1.384 (2)
C2—C3	1.434 (2)	C14—H14	0.9500
C3—C4	1.412 (2)	C15—C16	1.389 (3)
C3—C8	1.434 (2)	C15—H15	0.9500
C4—C5	1.376 (2)	C16—C17	1.379 (3)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.405 (3)	C17—C18	1.388 (2)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.359 (3)	C18—H18	0.9500
C6—H6	0.9500	C19—H19A	0.9800
C7—C8	1.418 (2)	C19—H19B	0.9800
C7—H7	0.9500	C19—H19C	0.9800

Cg1···Cg2ⁱ	3.850 (2)

O2—S—O3	117.93 (7)	C9—C10—C11	116.63 (15)
O2—S—C1	110.28 (7)	C9—C10—H10	121.7
O3—S—C1	108.10 (7)	C11—C10—H10	121.7
O2—S—C13	107.14 (7)	O1—C11—C2	111.47 (13)
O3—S—C13	107.81 (7)	O1—C11—C10	122.77 (14)
C1—S—C13	104.76 (7)	C2—C11—C10	125.75 (15)
C12—O1—C11	107.16 (12)	O1—C12—C1	109.97 (14)
C12—C1—C2	107.47 (14)	O1—C12—C19	114.10 (14)
C12—C1—S	122.78 (12)	C1—C12—C19	135.93 (16)
C2—C1—S	129.59 (11)	C18—C13—C14	121.17 (15)
C11—C2—C3	118.11 (14)	C18—C13—S	118.24 (12)
C11—C2—C1	103.91 (13)	C14—C13—S	120.44 (12)
C3—C2—C1	137.99 (14)	C15—C14—C13	118.61 (15)
C4—C3—C2	125.03 (14)	C15—C14—H14	120.7
C4—C3—C8	118.22 (14)	C13—C14—H14	120.7
C2—C3—C8	116.75 (14)	C14—C15—C16	120.44 (16)
C5—C4—C3	121.14 (15)	C14—C15—H15	119.8
C5—C4—H4	119.4	C16—C15—H15	119.8
C3—C4—H4	119.4	C17—C16—C15	120.42 (16)
C4—C5—C6	120.51 (17)	C17—C16—H16	119.8
C4—C5—H5	119.7	C15—C16—H16	119.8
C6—C5—H5	119.7	C16—C17—C18	119.82 (16)
C7—C6—C5	119.84 (16)	C16—C17—H17	120.1
C7—C6—H6	120.1	C18—C17—H17	120.1
C5—C6—H6	120.1	C13—C18—C17	119.50 (16)
C6—C7—C8	121.71 (16)	C13—C18—H18	120.2
C6—C7—H7	119.1	C17—C18—H18	120.2
C8—C7—H7	119.1	C12—C19—H19A	109.5
C7—C8—C9	120.46 (15)	C12—C19—H19B	109.5
C7—C8—C3	118.54 (16)	H19A—C19—H19B	109.5
C9—C8—C3	120.99 (15)	C12—C19—H19C	109.5
C10—C9—C8	121.70 (15)	H19A—C19—H19C	109.5
C10—C9—H9	119.2	H19B—C19—H19C	109.5
C8—C9—H9	119.2

O2—S—C1—C12	136.48 (14)	C12—O1—C11—C2	1.42 (17)
O3—S—C1—C12	6.22 (17)	C12—O1—C11—C10	−177.49 (15)
C13—S—C1—C12	−108.55 (14)	C3—C2—C11—O1	179.31 (12)
O2—S—C1—C2	−48.68 (16)	C1—C2—C11—O1	−1.14 (17)
O3—S—C1—C2	−178.93 (14)	C3—C2—C11—C10	−1.8 (2)
C13—S—C1—C2	66.30 (16)	C1—C2—C11—C10	177.73 (15)
C12—C1—C2—C11	0.43 (17)	C9—C10—C11—O1	178.28 (15)
S—C1—C2—C11	−175.02 (12)	C9—C10—C11—C2	−0.5 (3)
C12—C1—C2—C3	179.84 (17)	C11—O1—C12—C1	−1.10 (18)
S—C1—C2—C3	4.4 (3)	C11—O1—C12—C19	178.68 (14)
C11—C2—C3—C4	−176.13 (15)	C2—C1—C12—O1	0.41 (18)
C1—C2—C3—C4	4.5 (3)	S—C1—C12—O1	176.24 (11)
C11—C2—C3—C8	3.3 (2)	C2—C1—C12—C19	−179.31 (19)
C1—C2—C3—C8	−176.09 (17)	S—C1—C12—C19	−3.5 (3)
C2—C3—C4—C5	−179.13 (15)	O2—S—C13—C18	−12.25 (14)
C8—C3—C4—C5	1.5 (2)	O3—S—C13—C18	115.62 (13)
C3—C4—C5—C6	0.5 (3)	C1—S—C13—C18	−129.41 (12)
C4—C5—C6—C7	−1.6 (3)	O2—S—C13—C14	172.06 (12)
C5—C6—C7—C8	0.7 (3)	O3—S—C13—C14	−60.06 (14)
C6—C7—C8—C9	−177.78 (17)	C1—S—C13—C14	54.91 (14)
C6—C7—C8—C3	1.3 (3)	C18—C13—C14—C15	0.9 (2)
C4—C3—C8—C7	−2.3 (2)	S—C13—C14—C15	176.46 (12)
C2—C3—C8—C7	178.25 (14)	C13—C14—C15—C16	−2.1 (2)
C4—C3—C8—C9	176.74 (15)	C14—C15—C16—C17	1.3 (3)
C2—C3—C8—C9	−2.7 (2)	C15—C16—C17—C18	0.8 (3)
C7—C8—C9—C10	179.50 (16)	C14—C13—C18—C17	1.1 (2)
C3—C8—C9—C10	0.5 (3)	S—C13—C18—C17	−174.55 (13)
C8—C9—C10—C11	1.1 (2)	C16—C17—C18—C13	−1.9 (3)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2	0.95	2.35	3.190 (2)	147
C18—H18···O2	0.95	2.46	2.869 (2)	106
C19—H19B···O3	0.98	2.55	2.926 (2)	103
C19—H19C···Cg3ⁱ	0.98	3.03	3.735 (3)	130
C16—H16···Cg3ⁱⁱ	0.95	2.88	3.761 (3)	155

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₄O₃S
M_r	322.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	10.7175 (4), 7.7972 (3), 18.0488 (7)
β (°)	97.797 (1)
V (Å³)	1494.33 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.40 × 0.40 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8784, 3222, 2785
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.098, 1.05
No. of reflections	3222
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.39

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

Selected interatomic distances (Å) top

Cg1···Cg2ⁱ

3.850 (2)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2	0.95	2.35	3.190 (2)	147
C18—H18···O2	0.95	2.46	2.869 (2)	106
C19—H19B···O3	0.98	2.55	2.926 (2)	103
C19—H19C···Cg3ⁱ	0.98	3.03	3.735 (3)	129.6
C16—H16···Cg3ⁱⁱ	0.95	2.88	3.761 (3)	155.4

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

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., Woo, H. M., Seo, P. J., Son, B. W. & Lee, U. (2006). Acta Cryst. E62, o3881–o3882. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef 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 4| April 2008| Page o727

doi:10.1107/S1600536808007046

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