3-(4-Chloro­phenyl­sulfin­yl)-2,5,7-tri­methyl-1-benzofuran

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

doi:10.1107/S1600536810032228

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2325

https://doi.org/10.1107/S1600536810032228

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3-(4-Chlorophenylsulfinyl)-2,5,7-trimethyl-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 10 August 2010; accepted 11 August 2010; online 18 August 2010)

In the title compound, C₁₇H₁₅ClO₂S, the O atom and the 4-chlorophenyl group of the 4-chlorophenylsulfinyl substituent are located on opposite sides of the plane through the benzofuran fragment; the 4-chlorophenyl ring is approximately perpendicular to this plane [dihedral angle = 87.12 (3)°]. In the crystal structure, molecules are linked through a weak intermolecular C—H⋯O hydrogen bond, and by weak C—S⋯π [3.394 (2) Å] and C—Cl⋯π [3.800 (2) Å] interactions.

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006 ); Galal et al. (2009 ); Khan et al. (2005 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For related structures, see: Choi et al. (2010a ,b ).

Experimental

Crystal data

C₁₇H₁₅ClO₂S
M_r = 318.80
Triclinic, $[P \overline 1]$
a = 6.0790 (12) Å
b = 10.2232 (19) Å
c = 12.514 (2) Å
α = 84.474 (9)°
β = 80.121 (9)°
γ = 85.991 (9)°
V = 761.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 173 K
0.33 × 0.29 × 0.29 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.883, T_max = 0.897
13813 measured reflections
3789 independent reflections
3381 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.100
S = 1.06
3789 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	0.93	2.52	3.2548 (17)	136
Symmetry code: (i) -x, -y+1, -z+2.

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: https://doi.org/10.1107/S1600536810032228/ng5016sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810032228/ng5016Isup2.hkl

checkCIF report

Comment top

A series of benzofuran ring system show remarkable pharmacological properties such as antimicrobial (Khan et al., 2005), antifungal (Aslam et al., 2006), antitumour and antiviral (Galal et al., 2009) activities. These compounds widely occur in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our study of the substituent effect on the solid state structures of 3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010a,b), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.005 (1) Å from the least-squares plane defined by the nine constituent atoms. The 4-chlorophenyl ring is nearly perpendicular to the benzofuran plane with a dihedral angle of 87.12 (3)° and is tilted slightly towards it. The molecular packing (Fig. 2) is stabilized by a weak intermolecular C—H···O hydrogen bond between the 4-chlorophenyl H atom and the oxygen of the S═O unit, with a C13—H13···O2ⁱ (Table 1). The crystal packing (Fig. 2) is further stabilized by a weak intermolecular C—S···π interaction between the sulfur and 4-chlorophenyl ring of an adjacent molecule, with a C1—S···Cg1ⁱⁱ [3.394 (2) Å] (Cg1 is the centroid of the C12–C17 4-chlorophenyl ring), and by an intermolecular C—Cl···π interaction between the chlorine and the benzene ring of a neighbouring benzofuran system, with a C15—Cl···Cg2ⁱⁱⁱ [3.800 (2) Å] (Cg2 is the centroid of the C2–C7 benzene ring).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For related structures, see: Choi et al. (2010a,b).

Experimental top

77% 3-chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of 3-(4-chlorophenylsulfanyl)-2,5,7-trimethyl-1-benzofuran (303 mg, 1.0 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 at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 1:1 v/v) to afford the title compound as a colourless solid [yield 79%, m.p. 419–420 K; R_f = 0.69 (hexane–ethyl acetate, 1:1 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.

Structure description top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For related structures, see: Choi et al. (2010a,b).

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 with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. C—H···O, C—S···π, and C—Cl···π interactions (dotted lines) in the crystal structure of the title compound. Cg1 and Cg2 denote the ring centroids. [Symmetry codes: (i) -x, -y + 1, -z + 2; (ii) -x + 1, -y + 1 , -z + 2; (iii) -x + 1, -y, -z + 2.]

3-(4-Chlorophenylsulfinyl)-2,5,7-trimethyl-1-benzofuran top

Crystal data top

C₁₇H₁₅ClO₂S	Z = 2
M_r = 318.80	F(000) = 332
Triclinic, P1	D_x = 1.390 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0790 (12) Å	Cell parameters from 8051 reflections
b = 10.2232 (19) Å	θ = 2.5–28.5°
c = 12.514 (2) Å	µ = 0.39 mm⁻¹
α = 84.474 (9)°	T = 173 K
β = 80.121 (9)°	Block, colourless
γ = 85.991 (9)°	0.33 × 0.29 × 0.29 mm
V = 761.5 (3) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3789 independent reflections
Radiation source: rotating anode	3381 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.027
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.5°, θ_min = 1.7°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
T_min = 0.883, T_max = 0.897	l = −16→16
13813 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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F²) = 0.100	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0527P)² + 0.253P] where P = (F_o² + 2F_c²)/3
3789 reflections	(Δ/σ)_max = 0.001
193 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₇H₁₅ClO₂S	γ = 85.991 (9)°
M_r = 318.80	V = 761.5 (3) Å³
Triclinic, P1	Z = 2
a = 6.0790 (12) Å	Mo Kα radiation
b = 10.2232 (19) Å	µ = 0.39 mm⁻¹
c = 12.514 (2) Å	T = 173 K
α = 84.474 (9)°	0.33 × 0.29 × 0.29 mm
β = 80.121 (9)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3789 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3381 reflections with I > 2σ(I)
T_min = 0.883, T_max = 0.897	R_int = 0.027
13813 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.06	Δρ_max = 0.29 e Å⁻³
3789 reflections	Δρ_min = −0.37 e Å⁻³
193 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
Cl	0.59001 (8)	0.01403 (4)	1.15921 (3)	0.04476 (12)
S	0.39442 (5)	0.50713 (3)	0.84174 (2)	0.02515 (10)
O1	0.70564 (15)	0.39917 (9)	0.55824 (7)	0.0275 (2)
O2	0.14556 (16)	0.52738 (11)	0.85326 (8)	0.0345 (2)
C1	0.4919 (2)	0.43493 (12)	0.71941 (10)	0.0238 (2)
C2	0.3922 (2)	0.33367 (12)	0.67424 (10)	0.0233 (2)
C3	0.2051 (2)	0.25904 (13)	0.70614 (11)	0.0268 (3)
H3	0.1112	0.2693	0.7721	0.032*
C4	0.1625 (2)	0.16917 (13)	0.63714 (12)	0.0298 (3)
C5	0.3092 (3)	0.15433 (13)	0.53838 (12)	0.0323 (3)
H5	0.2783	0.0928	0.4937	0.039*
C6	0.4978 (2)	0.22683 (13)	0.50407 (10)	0.0299 (3)
C7	0.5302 (2)	0.31615 (12)	0.57516 (10)	0.0249 (3)
C8	0.6769 (2)	0.47050 (13)	0.64733 (10)	0.0255 (3)
C9	−0.0407 (3)	0.08820 (16)	0.66938 (15)	0.0409 (4)
H9A	−0.0003	0.0065	0.7076	0.061*
H9B	−0.0967	0.0707	0.6052	0.061*
H9C	−0.1544	0.1359	0.7157	0.061*
C10	0.6554 (3)	0.21158 (16)	0.39876 (12)	0.0418 (4)
H10A	0.6553	0.2929	0.3535	0.063*
H10B	0.6078	0.1432	0.3619	0.063*
H10C	0.8037	0.1888	0.4137	0.063*
C11	0.8487 (2)	0.56565 (14)	0.64818 (12)	0.0322 (3)
H11A	0.7992	0.6222	0.7056	0.048*
H11B	0.8723	0.6177	0.5795	0.048*
H11C	0.9862	0.5189	0.6600	0.048*
C12	0.4487 (2)	0.36497 (13)	0.93215 (10)	0.0238 (2)
C13	0.2739 (2)	0.31452 (14)	1.00741 (11)	0.0284 (3)
H13	0.1297	0.3526	1.0104	0.034*
C14	0.3172 (2)	0.20634 (15)	1.07826 (12)	0.0332 (3)
H14	0.2020	0.1708	1.1290	0.040*
C15	0.5339 (3)	0.15185 (14)	1.07258 (11)	0.0307 (3)
C16	0.7104 (2)	0.20486 (15)	0.99957 (12)	0.0328 (3)
H16	0.8551	0.1680	0.9976	0.039*
C17	0.6671 (2)	0.31354 (14)	0.92966 (11)	0.0302 (3)
H17	0.7835	0.3518	0.8814	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0623 (3)	0.0352 (2)	0.0401 (2)	−0.00630 (17)	−0.02155 (19)	0.00593 (15)
S	0.02602 (17)	0.02658 (17)	0.02290 (16)	0.00133 (12)	−0.00348 (12)	−0.00547 (11)
O1	0.0279 (5)	0.0294 (5)	0.0231 (4)	−0.0013 (4)	0.0010 (3)	−0.0016 (3)
O2	0.0269 (5)	0.0442 (6)	0.0312 (5)	0.0108 (4)	−0.0041 (4)	−0.0072 (4)
C1	0.0238 (6)	0.0255 (6)	0.0217 (6)	0.0002 (5)	−0.0033 (4)	−0.0025 (4)
C2	0.0238 (6)	0.0231 (6)	0.0226 (6)	0.0028 (4)	−0.0047 (4)	−0.0018 (4)
C3	0.0236 (6)	0.0266 (6)	0.0292 (6)	0.0008 (5)	−0.0024 (5)	−0.0016 (5)
C4	0.0287 (6)	0.0242 (6)	0.0382 (7)	0.0010 (5)	−0.0121 (5)	−0.0008 (5)
C5	0.0425 (8)	0.0256 (6)	0.0319 (7)	0.0012 (5)	−0.0144 (6)	−0.0049 (5)
C6	0.0398 (7)	0.0266 (6)	0.0229 (6)	0.0054 (5)	−0.0071 (5)	−0.0028 (5)
C7	0.0270 (6)	0.0240 (6)	0.0231 (6)	0.0011 (5)	−0.0038 (5)	−0.0005 (4)
C8	0.0256 (6)	0.0272 (6)	0.0230 (6)	0.0010 (5)	−0.0040 (5)	−0.0011 (5)
C9	0.0332 (7)	0.0346 (8)	0.0575 (10)	−0.0058 (6)	−0.0121 (7)	−0.0059 (7)
C10	0.0617 (10)	0.0356 (8)	0.0258 (7)	0.0021 (7)	0.0004 (7)	−0.0076 (6)
C11	0.0278 (6)	0.0340 (7)	0.0341 (7)	−0.0053 (5)	−0.0042 (5)	0.0010 (5)
C12	0.0229 (6)	0.0281 (6)	0.0210 (6)	−0.0017 (5)	−0.0039 (4)	−0.0044 (5)
C13	0.0215 (6)	0.0352 (7)	0.0285 (6)	−0.0037 (5)	−0.0023 (5)	−0.0051 (5)
C14	0.0323 (7)	0.0382 (8)	0.0287 (7)	−0.0107 (6)	−0.0018 (5)	−0.0009 (6)
C15	0.0396 (7)	0.0290 (6)	0.0261 (6)	−0.0051 (5)	−0.0120 (5)	−0.0017 (5)
C16	0.0263 (6)	0.0370 (7)	0.0359 (7)	0.0023 (5)	−0.0091 (5)	−0.0028 (6)
C17	0.0229 (6)	0.0374 (7)	0.0286 (7)	−0.0006 (5)	−0.0006 (5)	−0.0009 (5)

Geometric parameters (Å, º) top

Cl—C15	1.7443 (15)	C9—H9A	0.9600
S—O2	1.4964 (10)	C9—H9B	0.9600
S—C1	1.7563 (13)	C9—H9C	0.9600
S—C12	1.8015 (13)	C10—H10A	0.9600
O1—C8	1.3700 (16)	C10—H10B	0.9600
O1—C7	1.3846 (16)	C10—H10C	0.9600
C1—C8	1.3627 (17)	C11—H11A	0.9600
C1—C2	1.4408 (17)	C11—H11B	0.9600
C2—C7	1.3920 (17)	C11—H11C	0.9600
C2—C3	1.3937 (18)	C12—C13	1.3863 (18)
C3—C4	1.3854 (19)	C12—C17	1.3900 (18)
C3—H3	0.9300	C13—C14	1.389 (2)
C4—C5	1.409 (2)	C13—H13	0.9300
C4—C9	1.511 (2)	C14—C15	1.387 (2)
C5—C6	1.392 (2)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.389 (2)
C6—C7	1.3805 (18)	C16—C17	1.386 (2)
C6—C10	1.5048 (19)	C16—H16	0.9300
C8—C11	1.4780 (19)	C17—H17	0.9300

O2—S—C1	108.00 (6)	H9A—C9—H9C	109.5
O2—S—C12	106.40 (6)	H9B—C9—H9C	109.5
C1—S—C12	96.87 (6)	C6—C10—H10A	109.5
C8—O1—C7	106.14 (10)	C6—C10—H10B	109.5
C8—C1—C2	107.49 (11)	H10A—C10—H10B	109.5
C8—C1—S	124.61 (10)	C6—C10—H10C	109.5
C2—C1—S	127.86 (10)	H10A—C10—H10C	109.5
C7—C2—C3	119.63 (12)	H10B—C10—H10C	109.5
C7—C2—C1	104.61 (11)	C8—C11—H11A	109.5
C3—C2—C1	135.75 (12)	C8—C11—H11B	109.5
C4—C3—C2	118.34 (12)	H11A—C11—H11B	109.5
C4—C3—H3	120.8	C8—C11—H11C	109.5
C2—C3—H3	120.8	H11A—C11—H11C	109.5
C3—C4—C5	119.66 (13)	H11B—C11—H11C	109.5
C3—C4—C9	119.32 (13)	C13—C12—C17	121.40 (12)
C5—C4—C9	121.02 (13)	C13—C12—S	119.24 (10)
C6—C5—C4	123.56 (13)	C17—C12—S	119.23 (10)
C6—C5—H5	118.2	C12—C13—C14	119.03 (12)
C4—C5—H5	118.2	C12—C13—H13	120.5
C7—C6—C5	114.29 (12)	C14—C13—H13	120.5
C7—C6—C10	121.78 (14)	C15—C14—C13	119.40 (13)
C5—C6—C10	123.92 (13)	C15—C14—H14	120.3
C6—C7—O1	124.64 (12)	C13—C14—H14	120.3
C6—C7—C2	124.50 (12)	C14—C15—C16	121.63 (13)
O1—C7—C2	110.86 (11)	C14—C15—Cl	119.93 (11)
C1—C8—O1	110.89 (11)	C16—C15—Cl	118.45 (11)
C1—C8—C11	133.18 (12)	C17—C16—C15	118.88 (13)
O1—C8—C11	115.91 (11)	C17—C16—H16	120.6
C4—C9—H9A	109.5	C15—C16—H16	120.6
C4—C9—H9B	109.5	C16—C17—C12	119.56 (13)
H9A—C9—H9B	109.5	C16—C17—H17	120.2
C4—C9—H9C	109.5	C12—C17—H17	120.2

O2—S—C1—C8	137.22 (11)	C1—C2—C7—C6	179.56 (12)
C12—S—C1—C8	−113.01 (12)	C3—C2—C7—O1	179.84 (11)
O2—S—C1—C2	−40.20 (13)	C1—C2—C7—O1	0.32 (14)
C12—S—C1—C2	69.57 (12)	C2—C1—C8—O1	−0.20 (14)
C8—C1—C2—C7	−0.07 (14)	S—C1—C8—O1	−178.07 (9)
S—C1—C2—C7	177.71 (10)	C2—C1—C8—C11	−178.62 (14)
C8—C1—C2—C3	−179.47 (14)	S—C1—C8—C11	3.5 (2)
S—C1—C2—C3	−1.7 (2)	C7—O1—C8—C1	0.40 (14)
C7—C2—C3—C4	−0.10 (18)	C7—O1—C8—C11	179.11 (11)
C1—C2—C3—C4	179.23 (13)	O2—S—C12—C13	−11.33 (12)
C2—C3—C4—C5	0.85 (19)	C1—S—C12—C13	−122.43 (11)
C2—C3—C4—C9	−179.33 (12)	O2—S—C12—C17	172.79 (11)
C3—C4—C5—C6	−0.7 (2)	C1—S—C12—C17	61.69 (12)
C9—C4—C5—C6	179.49 (13)	C17—C12—C13—C14	−3.1 (2)
C4—C5—C6—C7	−0.2 (2)	S—C12—C13—C14	−178.86 (10)
C4—C5—C6—C10	179.96 (13)	C12—C13—C14—C15	0.4 (2)
C5—C6—C7—O1	−179.80 (12)	C13—C14—C15—C16	1.7 (2)
C10—C6—C7—O1	0.0 (2)	C13—C14—C15—Cl	−178.75 (11)
C5—C6—C7—C2	1.05 (19)	C14—C15—C16—C17	−1.1 (2)
C10—C6—C7—C2	−179.14 (13)	Cl—C15—C16—C17	179.36 (11)
C8—O1—C7—C6	−179.69 (12)	C15—C16—C17—C12	−1.6 (2)
C8—O1—C7—C2	−0.44 (14)	C13—C12—C17—C16	3.7 (2)
C3—C2—C7—C6	−0.92 (19)	S—C12—C17—C16	179.48 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.93	2.52	3.2548 (17)	136

Symmetry code: (i) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅ClO₂S
M_r	318.80
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	6.0790 (12), 10.2232 (19), 12.514 (2)
α, β, γ (°)	84.474 (9), 80.121 (9), 85.991 (9)
V (Å³)	761.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.33 × 0.29 × 0.29

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.883, 0.897
No. of measured, independent and observed [I > 2σ(I)] reflections	13813, 3789, 3381
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.100, 1.06
No. of reflections	3789
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.37

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
C13—H13···O2ⁱ	0.93	2.52	3.2548 (17)	136.1

Symmetry code: (i) −x, −y+1, −z+2.

Acknowledgements

This work was supported by Blue-Bio Industry RIC at Dongeui University as an RIC programme under the Ministry of Knowledge Economy and Busan city.

References

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