2-Methyl-3-phenyl­sulfonyl-5-propyl-1-benzofuran

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

doi:10.1107/S1600536808025786

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1761

doi:10.1107/S1600536808025786

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2-Methyl-3-phenylsulfonyl-5-propyl-1-benzofuran

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 13 July 2008; accepted 10 August 2008; online 16 August 2008)

The title compound, C₁₈H₁₈O₃S, was prepared by the oxidation of 2-methyl-3-phenylsulfanyl-5-propyl-1-benzofuran with 3-chloroperoxybenzoic acid. The phenyl ring makes a dihedral angle of 81.74 (6)° with the plane of the benzofuran fragment. The crystal structure is stabilized by C—H⋯π interactions between a methyl H atom and the phenyl ring of the phenylsulfonyl substituent from a neighbouring molecule, and by intermolecular C—H⋯O interactions.

Related literature

For the crystal structures of similar 2-methyl-3-phenylsulfonyl-1-benzofuran compounds, see: Choi et al. (2008a ,b ).

Experimental

Crystal data

C₁₈H₁₈O₃S
M_r = 314.38
Monoclinic, P 2₁ /n
a = 7.2712 (9) Å
b = 17.583 (2) Å
c = 12.788 (2) Å
β = 102.669 (2)°
V = 1595.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 173 (2) K
0.40 × 0.40 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
8966 measured reflections
3125 independent reflections
2606 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.135
S = 1.12
3125 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C9–C14 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O3ⁱ	0.95	2.60	3.355 (3)	137
C18—H18C⋯Cgⁱⁱ	0.98	3.29	3.947 (4)	126
Symmetry codes: (i) x+1, y, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536808025786/gw2046sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025786/gw2046Isup2.hkl

checkCIF report

Comment top

This work is related to our communications on the synthesis and structure of 2-methyl-3-phenylsulfonyl-1-benzofuran analogues, viz. 5-ethyl-2-methyl-3-phenylsulfonyl-1-benzofuran (Choi et al., 2008a) and 5-isopropyl-2-methyl-3-phenylsulfonyl-1-benzofuran (Choi et al., 2008b). Here we report the crystal structure of the title compound, 2-methyl-3-phenylsulfonyl-5-propyl-1-benzofuran (Fig. 1).

The benzofuran unit is almost planar, with a mean deviation of 0.018 (2) Å from the least-squares plane defined by the nine constituent atoms. The phenyl ring (C9–C14) makes a dihedral angle of 81.74 (6)° with the plane of the benzofuran fragment. The crystal packing (Fig. 2) is stabilized by intermolecular C—H···π interactions between a methyl H atom and the phenyl ring of the phenylsulfonyl substituent, with a C18—H18C···Cgⁱⁱ separation of 3.291 (4) Å (Fig. 2 and Table 1; Cg is the centroid of the C9–C14 phenyl ring, symmetry code as in Fig. 2). The molecular packing is further stabilized by intermolecular C—H···O interactions (Fig. 2 and Table 1; symmetry code as in Fig. 2).

Related literature top

For the crystal structures of similar 2-methyl-3-phenylsulfonyl-1-benzofuran compounds, see: Choi et al. (2008a,b).

Experimental top

77% 3-Chloroperoxybenzoic acid (471 mg, 2.1 mmol) was added in small portions to a stirred solution of 2-methyl-3-phenylsulfanyl-5-propyl-1-benzofuran (282 mg, 1.0 mmol) in dichloromethane (30 ml) at 273 K. After being stirred for 4 h at room temperature, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated under 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 83%, m.p. 388–389 K; R_f = 0.75 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in acetone at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 0.94 (t, J = 7.32 Hz, 3H), 1.62–1.69 (m, 2H), 2,68 (t,J = 7.32 Hz, 2H), 2.79 (s, 3H), 7.12 (d, J = 8.44 Hz, 1H), 7.31 (d, J = 8.44 Hz, 1H), 7.48–7.60 (m, 3H), 7.67 (s, 1H), 8.01 (d, J = 8.44 Hz, 2H); EI-MS 314 [M⁺].

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 ellipsoids drawn at the 50% probability level.
	Fig. 2. C—H···π and C—H···O interactions (dotted lines) in the title compound. Cg denotes the ring centroid. [Symmetry code: (i) x + 1, y, z; (ii) x + 1/2, -y + 3/2, 1/2 + z+1/2; (iii) x - 1, y, z; (iv) x - 1/2, -y + 3/2, z + 1/2.]

2-Methyl-3-phenylsulfonyl-5-propyl-1-benzofuran top

Crystal data top

C₁₈H₁₈O₃S	F(000) = 664
M_r = 314.38	D_x = 1.309 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P_2yn	Cell parameters from 3769 reflections
a = 7.2712 (9) Å	θ = 2.4–28.3°
b = 17.583 (2) Å	µ = 0.21 mm⁻¹
c = 12.788 (2) Å	T = 173 K
β = 102.669 (2)°	Block, colourless
V = 1595.1 (4) Å³	0.40 × 0.40 × 0.30 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2606 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.053
Graphite monochromator	θ_max = 26.0°, θ_min = 2.0°
Detector resolution: 10.0 pixels mm^-1	h = −8→5
ϕ and ω scans	k = −21→21
8966 measured reflections	l = −13→15
3125 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0731P)² + 0.5558P] where P = (F_o² + 2F_c²)/3
3125 reflections	(Δ/σ)_max = 0.001
200 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₈H₁₈O₃S	V = 1595.1 (4) Å³
M_r = 314.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.2712 (9) Å	µ = 0.21 mm⁻¹
b = 17.583 (2) Å	T = 173 K
c = 12.788 (2) Å	0.40 × 0.40 × 0.30 mm
β = 102.669 (2)°

Data collection top

Bruker SMART CCD diffractometer	2606 reflections with I > 2σ(I)
8966 measured reflections	R_int = 0.053
3125 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.12	Δρ_max = 0.36 e Å⁻³
3125 reflections	Δρ_min = −0.37 e Å⁻³
200 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	0.61553 (7)	0.71791 (3)	0.30885 (4)	0.02750 (18)
O1	0.7452 (2)	0.52071 (8)	0.44838 (12)	0.0335 (4)
O2	0.7324 (2)	0.76700 (8)	0.38556 (12)	0.0367 (4)
O3	0.4196 (2)	0.73668 (9)	0.27128 (12)	0.0359 (4)
C1	0.6276 (3)	0.62641 (11)	0.36076 (15)	0.0258 (4)
C2	0.4937 (3)	0.56569 (11)	0.32516 (16)	0.0266 (4)
C3	0.3214 (3)	0.55783 (13)	0.25182 (16)	0.0310 (5)
H3	0.2625	0.6007	0.2131	0.037*
C4	0.2374 (3)	0.48657 (13)	0.23632 (17)	0.0347 (5)
C5	0.3257 (3)	0.42403 (13)	0.29533 (19)	0.0403 (6)
H5	0.2669	0.3756	0.2839	0.048*
C6	0.4948 (3)	0.43051 (12)	0.36937 (19)	0.0380 (5)
H6	0.5528	0.3880	0.4094	0.046*
C7	0.5749 (3)	0.50211 (12)	0.38205 (16)	0.0300 (5)
C8	0.7750 (3)	0.59641 (12)	0.43314 (16)	0.0304 (5)
C9	0.7172 (3)	0.71003 (11)	0.19608 (16)	0.0276 (4)
C10	0.6070 (3)	0.68438 (12)	0.09947 (17)	0.0327 (5)
H10	0.4781	0.6717	0.0939	0.039*
C11	0.6880 (4)	0.67762 (13)	0.01194 (18)	0.0403 (6)
H11	0.6144	0.6603	−0.0546	0.048*
C12	0.8757 (4)	0.69593 (13)	0.0204 (2)	0.0407 (6)
H12	0.9304	0.6910	−0.0402	0.049*
C13	0.9842 (3)	0.72143 (13)	0.1167 (2)	0.0393 (5)
H13	1.1129	0.7341	0.1218	0.047*
C14	0.9063 (3)	0.72851 (12)	0.20576 (18)	0.0339 (5)
H14	0.9804	0.7457	0.2722	0.041*
C15	0.0537 (3)	0.47675 (16)	0.1550 (2)	0.0445 (6)
H15A	0.0473	0.5158	0.0986	0.053*
H15B	0.0549	0.4264	0.1205	0.053*
C16	−0.1198 (4)	0.4823 (2)	0.1979 (2)	0.0575 (8)
H16A	−0.1251	0.5334	0.2296	0.069*
H16B	−0.1129	0.4444	0.2558	0.069*
C17	−0.2983 (3)	0.46938 (15)	0.1141 (2)	0.0463 (6)
H17A	−0.2957	0.4185	0.0833	0.056*
H17B	−0.3080	0.5076	0.0573	0.056*
H17C	−0.4074	0.4737	0.1472	0.056*
C18	0.9566 (3)	0.62697 (14)	0.4949 (2)	0.0458 (6)
H18A	1.0596	0.6087	0.4633	0.069*
H18B	0.9770	0.6097	0.5695	0.069*
H18C	0.9532	0.6827	0.4929	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0294 (3)	0.0218 (3)	0.0307 (3)	0.00328 (19)	0.0053 (2)	−0.00131 (19)
O1	0.0344 (8)	0.0271 (7)	0.0364 (8)	0.0002 (6)	0.0022 (6)	0.0050 (6)
O2	0.0446 (9)	0.0263 (7)	0.0377 (8)	−0.0017 (7)	0.0059 (7)	−0.0062 (6)
O3	0.0323 (9)	0.0338 (8)	0.0409 (9)	0.0094 (7)	0.0069 (7)	0.0003 (7)
C1	0.0277 (10)	0.0236 (9)	0.0264 (10)	0.0004 (8)	0.0063 (8)	−0.0003 (8)
C2	0.0277 (10)	0.0266 (10)	0.0274 (10)	−0.0005 (8)	0.0099 (8)	−0.0029 (8)
C3	0.0278 (11)	0.0360 (11)	0.0302 (11)	0.0009 (9)	0.0088 (8)	−0.0021 (9)
C4	0.0314 (12)	0.0418 (12)	0.0340 (11)	−0.0063 (9)	0.0143 (9)	−0.0110 (9)
C5	0.0435 (14)	0.0326 (11)	0.0490 (14)	−0.0125 (10)	0.0193 (11)	−0.0104 (10)
C6	0.0452 (14)	0.0271 (11)	0.0440 (13)	−0.0023 (10)	0.0148 (11)	0.0019 (9)
C7	0.0314 (11)	0.0293 (10)	0.0302 (10)	−0.0010 (8)	0.0088 (9)	−0.0002 (8)
C8	0.0327 (11)	0.0259 (10)	0.0312 (10)	0.0002 (9)	0.0042 (9)	0.0008 (8)
C9	0.0314 (11)	0.0202 (9)	0.0309 (11)	0.0037 (8)	0.0065 (8)	0.0043 (8)
C10	0.0315 (11)	0.0325 (11)	0.0327 (11)	−0.0003 (9)	0.0040 (9)	0.0041 (9)
C11	0.0518 (15)	0.0368 (12)	0.0314 (11)	−0.0026 (11)	0.0074 (10)	0.0025 (9)
C12	0.0534 (15)	0.0316 (11)	0.0427 (13)	0.0031 (11)	0.0228 (11)	0.0062 (10)
C13	0.0343 (12)	0.0323 (11)	0.0545 (14)	0.0007 (9)	0.0165 (11)	0.0067 (10)
C14	0.0324 (12)	0.0280 (10)	0.0399 (12)	−0.0006 (9)	0.0045 (9)	0.0018 (9)
C15	0.0374 (13)	0.0589 (15)	0.0392 (13)	−0.0113 (11)	0.0130 (10)	−0.0187 (11)
C16	0.0352 (14)	0.096 (2)	0.0409 (14)	0.0089 (14)	0.0068 (11)	−0.0107 (14)
C17	0.0322 (13)	0.0517 (15)	0.0532 (15)	0.0029 (11)	0.0057 (11)	−0.0032 (12)
C18	0.0391 (13)	0.0368 (12)	0.0523 (14)	−0.0034 (10)	−0.0103 (11)	0.0062 (11)

Geometric parameters (Å, º) top

S—O2	1.437 (2)	C10—C11	1.380 (3)
S—O3	1.438 (2)	C10—H10	0.9500
S—C1	1.735 (2)	C11—C12	1.384 (4)
S—C9	1.765 (2)	C11—H11	0.9500
O1—C8	1.369 (2)	C12—C13	1.384 (4)
O1—C7	1.378 (3)	C12—H12	0.9500
C1—C8	1.360 (3)	C13—C14	1.384 (3)
C1—C2	1.449 (3)	C13—H13	0.9500
C2—C7	1.392 (3)	C14—H14	0.9500
C2—C3	1.398 (3)	C15—C16	1.485 (4)
C3—C4	1.389 (3)	C15—H15A	0.9900
C3—H3	0.9500	C15—H15B	0.9900
C4—C5	1.407 (3)	C16—C17	1.508 (3)
C4—C15	1.512 (3)	C16—H16A	0.9900
C5—C6	1.382 (3)	C16—H16B	0.9900
C5—H5	0.9500	C17—H17A	0.9800
C6—C7	1.382 (3)	C17—H17B	0.9800
C6—H6	0.9500	C17—H17C	0.9800
C8—C18	1.483 (3)	C18—H18A	0.9800
C9—C14	1.391 (3)	C18—H18B	0.9800
C9—C10	1.392 (3)	C18—H18C	0.9800

O2—S—O3	118.98 (9)	C10—C11—C12	120.4 (2)
O2—S—C1	108.86 (9)	C10—C11—H11	119.8
O3—S—C1	107.68 (10)	C12—C11—H11	119.8
O2—S—C9	108.30 (10)	C13—C12—C11	120.4 (2)
O3—S—C9	107.87 (9)	C13—C12—H12	119.8
C1—S—C9	104.17 (9)	C11—C12—H12	119.8
C8—O1—C7	106.97 (15)	C12—C13—C14	120.3 (2)
C8—C1—C2	107.64 (18)	C12—C13—H13	119.8
C8—C1—S	125.89 (16)	C14—C13—H13	119.8
C2—C1—S	126.07 (15)	C13—C14—C9	118.7 (2)
C7—C2—C3	119.09 (19)	C13—C14—H14	120.6
C7—C2—C1	104.40 (18)	C9—C14—H14	120.6
C3—C2—C1	136.49 (19)	C16—C15—C4	115.6 (2)
C4—C3—C2	119.1 (2)	C16—C15—H15A	108.4
C4—C3—H3	120.4	C4—C15—H15A	108.4
C2—C3—H3	120.4	C16—C15—H15B	108.4
C3—C4—C5	119.6 (2)	C4—C15—H15B	108.4
C3—C4—C15	119.7 (2)	H15A—C15—H15B	107.4
C5—C4—C15	120.7 (2)	C15—C16—C17	113.4 (2)
C6—C5—C4	122.4 (2)	C15—C16—H16A	108.9
C6—C5—H5	118.8	C17—C16—H16A	108.9
C4—C5—H5	118.8	C15—C16—H16B	108.9
C7—C6—C5	116.4 (2)	C17—C16—H16B	108.9
C7—C6—H6	121.8	H16A—C16—H16B	107.7
C5—C6—H6	121.8	C16—C17—H17A	109.5
O1—C7—C6	126.0 (2)	C16—C17—H17B	109.5
O1—C7—C2	110.60 (18)	H17A—C17—H17B	109.5
C6—C7—C2	123.4 (2)	C16—C17—H17C	109.5
C1—C8—O1	110.39 (18)	H17A—C17—H17C	109.5
C1—C8—C18	134.4 (2)	H17B—C17—H17C	109.5
O1—C8—C18	115.24 (18)	C8—C18—H18A	109.5
C14—C9—C10	121.3 (2)	C8—C18—H18B	109.5
C14—C9—S	119.47 (16)	H18A—C18—H18B	109.5
C10—C9—S	119.19 (17)	C8—C18—H18C	109.5
C11—C10—C9	118.9 (2)	H18A—C18—H18C	109.5
C11—C10—H10	120.6	H18B—C18—H18C	109.5
C9—C10—H10	120.6

O2—S—C1—C8	−27.3 (2)	C1—C2—C7—C6	−177.9 (2)
O3—S—C1—C8	−157.57 (18)	C2—C1—C8—O1	−0.9 (2)
C9—S—C1—C8	88.1 (2)	S—C1—C8—O1	−173.94 (14)
O2—S—C1—C2	160.91 (17)	C2—C1—C8—C18	177.5 (2)
O3—S—C1—C2	30.7 (2)	S—C1—C8—C18	4.4 (4)
C9—S—C1—C2	−83.72 (19)	C7—O1—C8—C1	1.0 (2)
C8—C1—C2—C7	0.4 (2)	C7—O1—C8—C18	−177.68 (19)
S—C1—C2—C7	173.44 (15)	O2—S—C9—C14	19.23 (19)
C8—C1—C2—C3	−177.8 (2)	O3—S—C9—C14	149.23 (16)
S—C1—C2—C3	−4.7 (3)	C1—S—C9—C14	−96.53 (17)
C7—C2—C3—C4	−1.1 (3)	O2—S—C9—C10	−161.66 (16)
C1—C2—C3—C4	176.9 (2)	O3—S—C9—C10	−31.66 (18)
C2—C3—C4—C5	0.7 (3)	C1—S—C9—C10	82.58 (17)
C2—C3—C4—C15	−178.30 (18)	C14—C9—C10—C11	−0.2 (3)
C3—C4—C5—C6	0.1 (3)	S—C9—C10—C11	−179.34 (16)
C15—C4—C5—C6	179.2 (2)	C9—C10—C11—C12	0.1 (3)
C4—C5—C6—C7	−0.6 (3)	C10—C11—C12—C13	−0.2 (3)
C8—O1—C7—C6	177.3 (2)	C11—C12—C13—C14	0.3 (3)
C8—O1—C7—C2	−0.7 (2)	C12—C13—C14—C9	−0.4 (3)
C5—C6—C7—O1	−177.6 (2)	C10—C9—C14—C13	0.4 (3)
C5—C6—C7—C2	0.2 (3)	S—C9—C14—C13	179.49 (16)
C3—C2—C7—O1	178.77 (17)	C3—C4—C15—C16	−94.1 (3)
C1—C2—C7—O1	0.2 (2)	C5—C4—C15—C16	86.9 (3)
C3—C2—C7—C6	0.6 (3)	C4—C15—C16—C17	−178.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3ⁱ	0.95	2.60	3.355 (3)	137
C18—H18C···Cgⁱⁱ	0.98	3.29	3.947 (4)	126

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈O₃S
M_r	314.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	7.2712 (9), 17.583 (2), 12.788 (2)
β (°)	102.669 (2)
V (Å³)	1595.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.40 × 0.40 × 0.30

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8966, 3125, 2606
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.135, 1.12
No. of reflections	3125
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.37

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
C13—H13···O3ⁱ	0.95	2.60	3.355 (3)	136.6
C18—H18C···Cgⁱⁱ	0.98	3.29	3.947 (4)	125.9

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

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. (2008a). Acta Cryst. E64, o1016. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o1257. 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 9| September 2008| Page o1761

doi:10.1107/S1600536808025786

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