2-Methyl-1-(4-methyl­phenyl­sulfinyl)naphtho­[2,1-b]furan

Choi, H.D.; Seo, P.J.; Lee, U.

doi:10.1107/S1600536812003121

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o549

doi:10.1107/S1600536812003121

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2-Methyl-1-(4-methylphenylsulfinyl)naphtho[2,1-b]furan

Hong Dae Choi,^a Pil Ja Seo ^a 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 20 January 2012; accepted 25 January 2012; online 31 January 2012)

In the title compound, C₂₀H₁₆O₂S, the 4-methylphenyl ring makes a dihedral angle of 82.60 (4)° with the mean plane [r.m.s. deviation = 0.007 (1) Å] of the naphthofuran fragment. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds, and by a slipped π–π interaction between the central naphthofuran benzene rings of neighbouring molecules [centroid-to-centroid distance = 3.671 (2) Å, interplanar distance = 3.349 (2) Å and slippage = 1.503 (2)°].

Related literature

For the pharmacological activity of naphthofuran compounds, see: Goel & Dixit (2004 ); Hagiwara et al. (1999 ); Piloto et al. (2005 ). For the crystal structures of related compounds, see: Choi et al. (2007 , 2008 ).

Experimental

Crystal data

C₂₀H₁₆O₂S
M_r = 320.39
Monoclinic, P 2₁ /c
a = 6.5052 (1) Å
b = 16.7418 (3) Å
c = 14.4935 (2) Å
β = 97.883 (1)°
V = 1563.55 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 173 K
0.28 × 0.28 × 0.26 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.677, T_max = 0.746
15390 measured reflections
3896 independent reflections
3271 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.107
S = 1.03
3896 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.29 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
C6—H6⋯O2ⁱ	0.95	2.48	3.3211 (19)	147
C10—H10⋯O1ⁱⁱ	0.95	2.59	3.4579 (19)	152
C13—H13C⋯O2ⁱⁱⁱ	0.98	2.35	3.2538 (19)	153
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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/S1600536812003121/lr2049sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003121/lr2049Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812003121/lr2049Isup3.cml

checkCIF report

Comment top

Naphthofuran analogues have drawn much attention owing to their valuable biological activities (Goel & Dixit, 2004; Hagiwara et al., 1999; Piloto et al., 2005). As a part of our continuing study of 2-methylnaphthofuran derivatives containing either 1-phenylsulfinyl (Choi et al., 2007) or 1-phenylsulfonyl (Choi et al., 2008) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the naphthofuran unit is essentially planar, with a mean deviation of 0.007 (1) Å from the least-squares plane defined by the thirteen constituent atoms. The dihedral angle between the 4-methylphenyl ring and the mean plane of the naphthofuran fragment is 82.60 (4)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds (Table 1). The crystal packing (Fig. 2) is further stabilized by a weak slipped π–π interaction between adjacent central benzene rings of the naphthofuran moiety, with a Cg···Cg^iv distance of 3.671 (2) Å, and an interplanar distance of 3.349 (2) Å, resulting in a slippage of 1.503 (2) Å, Cg is the centroid of the C2,C3,C8,C9,C10,C11 benzene ring and (iv) is the -x + 1, -y + 1, -z symmetry code.

Related literature top

For the pharmacological activity of naphthofuran compounds, see: Goel & Dixit (2004); Hagiwara et al. (1999); Piloto et al. (2005). For the crystal structures of related compounds, see: Choi et al. (2007, 2008).

Experimental top

77% 3-Chloroperoxybenzoic acid (269 mg, 1.2 mmol) was added in small portions to a stirred solution of 2-methyl-1-(4-methylphenylsulfanyl) naphtho[2,1-b]furan (334 mg, 1.1 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 5 h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 433–448 K; R_f = 0.51 (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 ethyl acetate at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view of the C—H···O and π–π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) -x + 2, y + 1/2, -z + 1/2; (ii) -x, -y + 1, -z; (iii) x - 1, y, z; (iv) -x + 1, -y + 1, -z; (v) -x + 2, y - 1/2, -z + 1/2; (vi) x + 1, y, z.]

2-Methyl-1-(4-methylphenylsulfinyl)naphtho[2,1-b]furan top

Crystal data top

C₂₀H₁₆O₂S	F(000) = 672
M_r = 320.39	D_x = 1.361 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5690 reflections
a = 6.5052 (1) Å	θ = 2.8–28.1°
b = 16.7418 (3) Å	µ = 0.21 mm⁻¹
c = 14.4935 (2) Å	T = 173 K
β = 97.883 (1)°	Block, colourless
V = 1563.55 (4) Å³	0.28 × 0.28 × 0.26 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3896 independent reflections
Radiation source: rotating anode	3271 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.028
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 1.9°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −19→22
T_min = 0.677, T_max = 0.746	l = −19→19
15390 measured 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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F²) = 0.107	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0548P)² + 0.534P] where P = (F_o² + 2F_c²)/3
3896 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₀H₁₆O₂S	V = 1563.55 (4) Å³
M_r = 320.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.5052 (1) Å	µ = 0.21 mm⁻¹
b = 16.7418 (3) Å	T = 173 K
c = 14.4935 (2) Å	0.28 × 0.28 × 0.26 mm
β = 97.883 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3896 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3271 reflections with I > 2σ(I)
T_min = 0.677, T_max = 0.746	R_int = 0.028
15390 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.03	Δρ_max = 0.29 e Å⁻³
3896 reflections	Δρ_min = −0.39 e Å⁻³
210 parameters

Special details top

Geometry. Cg···Cg^iv distance = 3.671 (2) Å; (iv) -x + 1, -y + 1, -z

Cg is the centroid of the C2/C3/C8–C11 benzene ring.

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
S1	0.54869 (6)	0.29240 (2)	0.22725 (3)	0.02964 (11)
O1	0.18369 (15)	0.42901 (7)	0.06023 (7)	0.0332 (2)
O2	0.77697 (17)	0.28641 (6)	0.22477 (8)	0.0391 (3)
C1	0.4389 (2)	0.37111 (8)	0.15685 (9)	0.0268 (3)
C2	0.4942 (2)	0.45457 (8)	0.14760 (9)	0.0251 (3)
C3	0.6672 (2)	0.50427 (8)	0.17904 (9)	0.0253 (3)
C4	0.8502 (2)	0.47737 (9)	0.23408 (10)	0.0301 (3)
H4	0.8619	0.4230	0.2528	0.036*
C5	1.0110 (2)	0.52903 (9)	0.26072 (12)	0.0368 (3)
H5	1.1337	0.5100	0.2972	0.044*
C6	0.9958 (2)	0.60987 (9)	0.23450 (12)	0.0375 (4)
H6	1.1067	0.6455	0.2544	0.045*
C7	0.8224 (2)	0.63704 (9)	0.18063 (11)	0.0339 (3)
H7	0.8146	0.6917	0.1629	0.041*
C8	0.6534 (2)	0.58600 (8)	0.15034 (10)	0.0282 (3)
C9	0.4756 (2)	0.61434 (9)	0.09111 (10)	0.0338 (3)
H9	0.4694	0.6691	0.0736	0.041*
C10	0.3145 (2)	0.56566 (10)	0.05886 (10)	0.0346 (3)
H10	0.1974	0.5847	0.0185	0.042*
C11	0.3302 (2)	0.48621 (9)	0.08821 (10)	0.0289 (3)
C12	0.2541 (2)	0.35928 (9)	0.10221 (10)	0.0309 (3)
C13	0.1180 (3)	0.28882 (10)	0.08024 (12)	0.0399 (4)
H13A	0.1879	0.2409	0.1079	0.060*
H13B	0.0887	0.2822	0.0125	0.060*
H13C	−0.0124	0.2967	0.1058	0.060*
C14	0.5188 (2)	0.33407 (8)	0.33886 (9)	0.0254 (3)
C15	0.6874 (2)	0.33510 (9)	0.40837 (11)	0.0330 (3)
H15	0.8197	0.3177	0.3958	0.040*
C16	0.6611 (2)	0.36179 (10)	0.49654 (11)	0.0367 (3)
H16	0.7769	0.3626	0.5442	0.044*
C17	0.4692 (2)	0.38742 (9)	0.51671 (10)	0.0318 (3)
C18	0.3013 (2)	0.38436 (9)	0.44579 (10)	0.0316 (3)
H18	0.1685	0.4011	0.4585	0.038*
C19	0.3236 (2)	0.35751 (8)	0.35733 (10)	0.0289 (3)
H19	0.2072	0.3551	0.3100	0.035*
C20	0.4422 (3)	0.41837 (11)	0.61182 (11)	0.0416 (4)
H20A	0.5394	0.3909	0.6590	0.062*
H20B	0.2997	0.4084	0.6236	0.062*
H20C	0.4700	0.4759	0.6147	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0360 (2)	0.02007 (18)	0.0343 (2)	0.00179 (13)	0.00981 (14)	−0.00098 (13)
O1	0.0290 (5)	0.0398 (6)	0.0299 (5)	0.0007 (4)	0.0012 (4)	−0.0028 (4)
O2	0.0378 (6)	0.0329 (6)	0.0494 (7)	0.0121 (5)	0.0161 (5)	0.0032 (5)
C1	0.0293 (7)	0.0260 (7)	0.0259 (7)	−0.0002 (5)	0.0068 (5)	−0.0021 (5)
C2	0.0282 (6)	0.0246 (7)	0.0232 (6)	0.0036 (5)	0.0066 (5)	−0.0009 (5)
C3	0.0295 (7)	0.0231 (7)	0.0245 (6)	0.0023 (5)	0.0079 (5)	−0.0015 (5)
C4	0.0299 (7)	0.0235 (7)	0.0372 (8)	0.0009 (5)	0.0058 (6)	0.0014 (6)
C5	0.0304 (7)	0.0335 (8)	0.0458 (9)	−0.0007 (6)	0.0027 (6)	0.0006 (7)
C6	0.0354 (8)	0.0310 (8)	0.0475 (9)	−0.0082 (6)	0.0110 (7)	−0.0053 (7)
C7	0.0440 (8)	0.0223 (7)	0.0384 (8)	−0.0018 (6)	0.0158 (7)	−0.0008 (6)
C8	0.0362 (7)	0.0237 (7)	0.0265 (7)	0.0023 (5)	0.0114 (6)	−0.0009 (5)
C9	0.0449 (8)	0.0266 (7)	0.0312 (7)	0.0101 (6)	0.0101 (6)	0.0046 (6)
C10	0.0372 (8)	0.0365 (8)	0.0295 (7)	0.0117 (6)	0.0023 (6)	0.0039 (6)
C11	0.0285 (7)	0.0326 (7)	0.0259 (7)	0.0027 (6)	0.0049 (5)	−0.0023 (6)
C12	0.0322 (7)	0.0336 (8)	0.0281 (7)	−0.0011 (6)	0.0086 (6)	−0.0044 (6)
C13	0.0371 (8)	0.0427 (9)	0.0402 (9)	−0.0106 (7)	0.0061 (7)	−0.0088 (7)
C14	0.0293 (7)	0.0188 (6)	0.0285 (7)	0.0001 (5)	0.0054 (5)	0.0029 (5)
C15	0.0266 (7)	0.0340 (8)	0.0383 (8)	0.0012 (6)	0.0041 (6)	0.0032 (6)
C16	0.0325 (7)	0.0423 (9)	0.0338 (8)	−0.0025 (6)	−0.0016 (6)	0.0031 (7)
C17	0.0374 (8)	0.0288 (7)	0.0299 (7)	−0.0075 (6)	0.0070 (6)	0.0017 (6)
C18	0.0291 (7)	0.0315 (8)	0.0354 (8)	0.0003 (6)	0.0090 (6)	0.0010 (6)
C19	0.0267 (7)	0.0285 (7)	0.0311 (7)	0.0007 (5)	0.0029 (5)	0.0020 (6)
C20	0.0502 (9)	0.0444 (9)	0.0318 (8)	−0.0107 (8)	0.0111 (7)	−0.0035 (7)

Geometric parameters (Å, º) top

S1—O2	1.4938 (11)	C9—H9	0.9500
S1—C1	1.7573 (15)	C10—C11	1.396 (2)
S1—C14	1.7964 (14)	C10—H10	0.9500
O1—C12	1.3662 (18)	C12—C13	1.483 (2)
O1—C11	1.3727 (17)	C13—H13A	0.9800
C1—C12	1.360 (2)	C13—H13B	0.9800
C1—C2	1.4537 (19)	C13—H13C	0.9800
C2—C11	1.3813 (19)	C14—C15	1.384 (2)
C2—C3	1.4232 (19)	C14—C19	1.3901 (18)
C3—C4	1.413 (2)	C15—C16	1.386 (2)
C3—C8	1.4293 (19)	C15—H15	0.9500
C4—C5	1.371 (2)	C16—C17	1.389 (2)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.406 (2)	C17—C18	1.394 (2)
C5—H5	0.9500	C17—C20	1.505 (2)
C6—C7	1.359 (2)	C18—C19	1.385 (2)
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.414 (2)	C19—H19	0.9500
C7—H7	0.9500	C20—H20A	0.9800
C8—C9	1.424 (2)	C20—H20B	0.9800
C9—C10	1.359 (2)	C20—H20C	0.9800

O2—S1—C1	111.27 (6)	O1—C11—C10	123.78 (13)
O2—S1—C14	106.16 (7)	C2—C11—C10	124.97 (14)
C1—S1—C14	98.40 (6)	C1—C12—O1	110.52 (13)
C12—O1—C11	106.72 (11)	C1—C12—C13	134.00 (15)
C12—C1—C2	107.26 (13)	O1—C12—C13	115.48 (13)
C12—C1—S1	119.03 (11)	C12—C13—H13A	109.5
C2—C1—S1	133.49 (11)	C12—C13—H13B	109.5
C11—C2—C3	118.98 (13)	H13A—C13—H13B	109.5
C11—C2—C1	104.24 (12)	C12—C13—H13C	109.5
C3—C2—C1	136.67 (13)	H13A—C13—H13C	109.5
C4—C3—C2	124.22 (13)	H13B—C13—H13C	109.5
C4—C3—C8	118.95 (13)	C15—C14—C19	120.66 (13)
C2—C3—C8	116.82 (13)	C15—C14—S1	119.20 (10)
C5—C4—C3	120.60 (14)	C19—C14—S1	119.84 (11)
C5—C4—H4	119.7	C14—C15—C16	119.32 (13)
C3—C4—H4	119.7	C14—C15—H15	120.3
C4—C5—C6	120.57 (15)	C16—C15—H15	120.3
C4—C5—H5	119.7	C15—C16—C17	121.45 (14)
C6—C5—H5	119.7	C15—C16—H16	119.3
C7—C6—C5	119.97 (14)	C17—C16—H16	119.3
C7—C6—H6	120.0	C16—C17—C18	117.99 (14)
C5—C6—H6	120.0	C16—C17—C20	121.35 (14)
C6—C7—C8	121.65 (14)	C18—C17—C20	120.66 (14)
C6—C7—H7	119.2	C19—C18—C17	121.58 (13)
C8—C7—H7	119.2	C19—C18—H18	119.2
C7—C8—C9	121.24 (13)	C17—C18—H18	119.2
C7—C8—C3	118.23 (13)	C18—C19—C14	118.97 (13)
C9—C8—C3	120.51 (13)	C18—C19—H19	120.5
C10—C9—C8	122.13 (14)	C14—C19—H19	120.5
C10—C9—H9	118.9	C17—C20—H20A	109.5
C8—C9—H9	118.9	C17—C20—H20B	109.5
C9—C10—C11	116.49 (14)	H20A—C20—H20B	109.5
C9—C10—H10	121.8	C17—C20—H20C	109.5
C11—C10—H10	121.8	H20A—C20—H20C	109.5
O1—C11—C2	111.24 (12)	H20B—C20—H20C	109.5

O2—S1—C1—C12	137.65 (11)	C12—O1—C11—C10	179.24 (13)
C14—S1—C1—C12	−111.29 (12)	C3—C2—C11—O1	176.11 (11)
O2—S1—C1—C2	−48.61 (15)	C1—C2—C11—O1	−0.85 (14)
C14—S1—C1—C2	62.45 (14)	C3—C2—C11—C10	−3.1 (2)
C12—C1—C2—C11	1.38 (14)	C1—C2—C11—C10	179.93 (13)
S1—C1—C2—C11	−172.89 (11)	C9—C10—C11—O1	−178.33 (13)
C12—C1—C2—C3	−174.74 (15)	C9—C10—C11—C2	0.8 (2)
S1—C1—C2—C3	11.0 (2)	C2—C1—C12—O1	−1.46 (15)
C11—C2—C3—C4	−175.09 (12)	S1—C1—C12—O1	173.79 (9)
C1—C2—C3—C4	0.6 (2)	C2—C1—C12—C13	179.00 (15)
C11—C2—C3—C8	3.32 (18)	S1—C1—C12—C13	−5.8 (2)
C1—C2—C3—C8	179.02 (14)	C11—O1—C12—C1	0.93 (15)
C2—C3—C4—C5	179.31 (13)	C11—O1—C12—C13	−179.43 (12)
C8—C3—C4—C5	0.9 (2)	O2—S1—C14—C15	−15.36 (13)
C3—C4—C5—C6	0.6 (2)	C1—S1—C14—C15	−130.48 (12)
C4—C5—C6—C7	−1.4 (2)	O2—S1—C14—C19	170.95 (11)
C5—C6—C7—C8	0.6 (2)	C1—S1—C14—C19	55.83 (12)
C6—C7—C8—C9	−177.67 (14)	C19—C14—C15—C16	−1.7 (2)
C6—C7—C8—C3	1.0 (2)	S1—C14—C15—C16	−175.29 (12)
C4—C3—C8—C7	−1.69 (19)	C14—C15—C16—C17	0.1 (2)
C2—C3—C8—C7	179.81 (12)	C15—C16—C17—C18	1.0 (2)
C4—C3—C8—C9	176.95 (12)	C15—C16—C17—C20	−178.40 (15)
C2—C3—C8—C9	−1.56 (18)	C16—C17—C18—C19	−0.7 (2)
C7—C8—C9—C10	177.87 (14)	C20—C17—C18—C19	178.78 (14)
C3—C8—C9—C10	−0.7 (2)	C17—C18—C19—C14	−0.8 (2)
C8—C9—C10—C11	1.2 (2)	C15—C14—C19—C18	2.0 (2)
C12—O1—C11—C2	0.01 (15)	S1—C14—C19—C18	175.61 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.95	2.48	3.3211 (19)	147
C10—H10···O1ⁱⁱ	0.95	2.59	3.4579 (19)	152
C13—H13C···O2ⁱⁱⁱ	0.98	2.35	3.2538 (19)	153

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆O₂S
M_r	320.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	6.5052 (1), 16.7418 (3), 14.4935 (2)
β (°)	97.883 (1)
V (Å³)	1563.55 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.28 × 0.28 × 0.26

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.677, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	15390, 3896, 3271
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.107, 1.03
No. of reflections	3896
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.39

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
C6—H6···O2ⁱ	0.95	2.48	3.3211 (19)	147.1
C10—H10···O1ⁱⁱ	0.95	2.59	3.4579 (19)	151.5
C13—H13C···O2ⁱⁱⁱ	0.98	2.35	3.2538 (19)	152.7

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

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Centre (grant No. RIC08-06-07) at Dongeui University as an RIC programme under the Ministry of Knowledge Economy and Busan city.

References

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