3-[(4-Fluoro­phen­yl)sulfon­yl]-5-iodo-2-methyl-1-benzofuran

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

doi:10.1107/S1600536810034069

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2424

https://doi.org/10.1107/S1600536810034069

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3-[(4-Fluorophenyl)sulfonyl]-5-iodo-2-methyl-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 19 August 2010; accepted 24 August 2010; online 28 August 2010)

In the title compound, C₁₅H₁₀FIO₃S, the 4-fluorophenyl ring makes a dihedral angle of 72.27 (6)° with the mean plane of the benzofuran fragment [mean deviation of 0.014 (2) Å from the plane defined by the nine constituent atoms]. In the crystal, pairs of weak intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers, which are further linked via an aromatic π–π interactions between the iodobenzene rings of neighbouring molecules [centroid–centroid distance = 3.569 (3) Å].

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 the structures of related 3-(4-fluorophenylsulfonyl)-5-halo-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a ,b ,c ).

Experimental

Crystal data

C₁₅H₁₀FIO₃S
M_r = 416.19
Triclinic, $[P \overline 1]$
a = 7.5324 (3) Å
b = 9.4289 (3) Å
c = 11.6460 (4) Å
α = 69.687 (1)°
β = 77.639 (2)°
γ = 67.410 (2)°
V = 713.06 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.41 mm⁻¹
T = 179 K
0.32 × 0.31 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.516, T_max = 0.715
12406 measured reflections
3286 independent reflections
3117 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.067
S = 1.12
3286 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.74 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2ⁱ	0.95	2.56	3.399 (3)	148
Symmetry code: (i) -x+1, -y+1, -z+1.

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/S1600536810034069/nk2056sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810034069/nk2056Isup2.hkl

checkCIF report

Comment top

Many compounds containing a benzofuran ring system show diverse pharmacological properties such as antifungal, antitumor, antiviral, and antimicrobial activities (Aslam et al., 2006, Galal et al., 2009, Khan et al., 2005). 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-fluorophenylsulfonyl)-5-halo-2-methyl-1-benzofuran analogues (Choi et al., 2010a,b,c), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.014 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the benzofuran plane and the 4-fluorophenyl ring is 72.27 (6)° . The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds between the 4–fluorophenyl H atom and the oxygen of the O═S═O unit, with C11—H11···O2ⁱ (Table 1). The crystal packing (Fig. 2) is further stabilized by an aromatic π..π interaction between the benzene rings of adjacent molecules, with a Cg···Cgⁱⁱ distance of 3.569 (3) Å (Cg 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 the structures of related 3-(4-fluorophenylsulfonyl)-5-halo-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a,b,c).

Experimental top

77% 3-chloroperoxybenzoic acid (381 mg, 1.7 mmol) was added in small portions to a stirred solution of 3-(4-fluorophenylsulfanyl)-5-iodo-2-methyl-1-benzofuran (307 mg, 0.8 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 8h, 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 colorless solid [yield 81%, m.p. 438–439 K; R_f = 0.71 (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 chloroform 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 the structures of related 3-(4-fluorophenylsulfonyl)-5-halo-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a,b,c).

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 and π–π interactions (dotted lines) in the crystal structure of the title compound. Cg denotes the ring centroid. [Symmetry codes: (i) - x + 1, - y + 1, - z + 1; (ii) - x + 2, - y, - z + 1.]

3-[(4-Fluorophenyl)sulfonyl]-5-iodo-2-methyl-1-benzofuran top

Crystal data top

C₁₅H₁₀FIO₃S	Z = 2
M_r = 416.19	F(000) = 404
Triclinic, P1	D_x = 1.938 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5324 (3) Å	Cell parameters from 9807 reflections
b = 9.4289 (3) Å	θ = 2.5–27.5°
c = 11.6460 (4) Å	µ = 2.41 mm⁻¹
α = 69.687 (1)°	T = 179 K
β = 77.639 (2)°	Block, colourless
γ = 67.410 (2)°	0.32 × 0.31 × 0.15 mm
V = 713.06 (4) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3286 independent reflections
Radiation source: rotating anode	3117 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.032
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 1.9°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
T_min = 0.516, T_max = 0.715	l = −15→14
12406 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)] = 0.026	Hydrogen site location: difference Fourier map
wR(F²) = 0.067	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0304P)² + 0.3949P] where P = (F_o² + 2F_c²)/3
3286 reflections	(Δ/σ)_max = 0.001
192 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.74 e Å⁻³

Crystal data top

C₁₅H₁₀FIO₃S	γ = 67.410 (2)°
M_r = 416.19	V = 713.06 (4) Å³
Triclinic, P1	Z = 2
a = 7.5324 (3) Å	Mo Kα radiation
b = 9.4289 (3) Å	µ = 2.41 mm⁻¹
c = 11.6460 (4) Å	T = 179 K
α = 69.687 (1)°	0.32 × 0.31 × 0.15 mm
β = 77.639 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3286 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3117 reflections with I > 2σ(I)
T_min = 0.516, T_max = 0.715	R_int = 0.032
12406 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.067	H-atom parameters constrained
S = 1.12	Δρ_max = 0.46 e Å⁻³
3286 reflections	Δρ_min = −0.74 e Å⁻³
192 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
I	0.74536 (3)	0.07895 (2)	0.834688 (14)	0.03858 (8)
S	0.46135 (8)	0.39074 (6)	0.29783 (5)	0.02623 (12)
F	1.0151 (3)	0.7277 (2)	0.0740 (2)	0.0570 (5)
O1	0.7819 (2)	−0.06398 (19)	0.35078 (15)	0.0287 (3)
O2	0.3608 (3)	0.4405 (2)	0.40446 (17)	0.0371 (4)
O3	0.3545 (3)	0.4119 (2)	0.20121 (16)	0.0342 (4)
C1	0.6012 (3)	0.1889 (3)	0.3496 (2)	0.0253 (4)
C2	0.6714 (3)	0.1055 (2)	0.4696 (2)	0.0229 (4)
C3	0.6569 (3)	0.1441 (3)	0.5777 (2)	0.0259 (5)
H3	0.5818	0.2481	0.5853	0.031*
C4	0.7570 (3)	0.0235 (3)	0.6732 (2)	0.0261 (5)
C5	0.8659 (3)	−0.1312 (3)	0.6658 (2)	0.0292 (5)
H5	0.9309	−0.2100	0.7342	0.035*
C6	0.8799 (3)	−0.1707 (3)	0.5599 (2)	0.0281 (5)
H6	0.9530	−0.2755	0.5532	0.034*
C7	0.7821 (3)	−0.0502 (3)	0.4643 (2)	0.0243 (4)
C8	0.6729 (3)	0.0833 (3)	0.2820 (2)	0.0273 (5)
C9	0.6640 (4)	0.0959 (3)	0.1531 (2)	0.0368 (6)
H9A	0.6471	−0.0008	0.1502	0.055*
H9B	0.7842	0.1063	0.1045	0.055*
H9C	0.5547	0.1906	0.1192	0.055*
C10	0.6315 (3)	0.4907 (2)	0.2315 (2)	0.0253 (4)
C11	0.7203 (4)	0.5247 (3)	0.3064 (2)	0.0323 (5)
H11	0.6913	0.4938	0.3931	0.039*
C12	0.8523 (4)	0.6048 (3)	0.2529 (3)	0.0398 (6)
H12	0.9165	0.6284	0.3022	0.048*
C13	0.8877 (4)	0.6489 (3)	0.1269 (3)	0.0376 (6)
C14	0.7985 (4)	0.6179 (3)	0.0512 (3)	0.0357 (6)
H14	0.8248	0.6520	−0.0356	0.043*
C15	0.6704 (4)	0.5361 (3)	0.1045 (2)	0.0288 (5)
H15	0.6089	0.5110	0.0547	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I	0.04426 (12)	0.04278 (11)	0.02458 (10)	−0.00531 (8)	−0.00975 (7)	−0.01169 (7)
S	0.0244 (3)	0.0270 (2)	0.0210 (3)	−0.0027 (2)	−0.0043 (2)	−0.0050 (2)
F	0.0535 (11)	0.0454 (9)	0.0756 (14)	−0.0303 (8)	−0.0174 (10)	0.0000 (9)
O1	0.0308 (9)	0.0273 (7)	0.0271 (8)	−0.0070 (7)	−0.0022 (7)	−0.0106 (6)
O2	0.0353 (10)	0.0354 (9)	0.0273 (9)	0.0005 (7)	0.0014 (8)	−0.0097 (7)
O3	0.0306 (9)	0.0384 (9)	0.0295 (9)	−0.0098 (7)	−0.0113 (7)	−0.0022 (7)
C1	0.0234 (11)	0.0277 (10)	0.0209 (10)	−0.0061 (8)	−0.0016 (9)	−0.0057 (8)
C2	0.0193 (10)	0.0251 (9)	0.0202 (10)	−0.0054 (8)	−0.0003 (8)	−0.0051 (8)
C3	0.0241 (11)	0.0268 (10)	0.0222 (11)	−0.0043 (8)	−0.0002 (9)	−0.0075 (8)
C4	0.0241 (11)	0.0313 (10)	0.0212 (10)	−0.0091 (9)	−0.0003 (9)	−0.0069 (8)
C5	0.0260 (12)	0.0283 (10)	0.0260 (11)	−0.0062 (9)	−0.0053 (9)	−0.0011 (9)
C6	0.0257 (11)	0.0231 (9)	0.0313 (12)	−0.0057 (8)	−0.0014 (9)	−0.0065 (9)
C7	0.0231 (11)	0.0270 (10)	0.0225 (10)	−0.0091 (8)	0.0020 (9)	−0.0085 (8)
C8	0.0258 (11)	0.0298 (10)	0.0248 (11)	−0.0083 (9)	−0.0026 (9)	−0.0074 (9)
C9	0.0393 (14)	0.0442 (13)	0.0278 (13)	−0.0091 (11)	−0.0035 (11)	−0.0174 (11)
C10	0.0252 (11)	0.0212 (9)	0.0269 (11)	−0.0014 (8)	−0.0070 (9)	−0.0086 (8)
C11	0.0374 (13)	0.0260 (10)	0.0301 (12)	0.0005 (9)	−0.0125 (10)	−0.0115 (9)
C12	0.0428 (15)	0.0287 (11)	0.0528 (17)	−0.0065 (11)	−0.0202 (13)	−0.0147 (11)
C13	0.0367 (14)	0.0226 (10)	0.0504 (16)	−0.0089 (10)	−0.0097 (12)	−0.0049 (10)
C14	0.0371 (14)	0.0310 (11)	0.0327 (13)	−0.0091 (10)	−0.0047 (11)	−0.0038 (10)
C15	0.0317 (12)	0.0290 (10)	0.0253 (11)	−0.0085 (9)	−0.0064 (9)	−0.0072 (9)

Geometric parameters (Å, º) top

I—C4	2.096 (2)	C6—C7	1.380 (3)
S—O3	1.4362 (19)	C6—H6	0.9500
S—O2	1.4369 (18)	C8—C9	1.478 (3)
S—C1	1.741 (2)	C9—H9A	0.9800
S—C10	1.768 (2)	C9—H9B	0.9800
F—C13	1.352 (3)	C9—H9C	0.9800
O1—C8	1.370 (3)	C10—C11	1.385 (3)
O1—C7	1.373 (3)	C10—C15	1.388 (3)
C1—C8	1.361 (3)	C11—C12	1.390 (4)
C1—C2	1.444 (3)	C11—H11	0.9500
C2—C7	1.398 (3)	C12—C13	1.375 (4)
C2—C3	1.399 (3)	C12—H12	0.9500
C3—C4	1.386 (3)	C13—C14	1.378 (4)
C3—H3	0.9500	C14—C15	1.376 (4)
C4—C5	1.396 (3)	C14—H14	0.9500
C5—C6	1.379 (4)	C15—H15	0.9500
C5—H5	0.9500

O3—S—O2	119.80 (12)	C1—C8—O1	110.4 (2)
O3—S—C1	108.88 (11)	C1—C8—C9	134.2 (2)
O2—S—C1	107.18 (11)	O1—C8—C9	115.4 (2)
O3—S—C10	107.53 (11)	C8—C9—H9A	109.5
O2—S—C10	108.01 (12)	C8—C9—H9B	109.5
C1—S—C10	104.41 (11)	H9A—C9—H9B	109.5
C8—O1—C7	107.05 (17)	C8—C9—H9C	109.5
C8—C1—C2	107.58 (19)	H9A—C9—H9C	109.5
C8—C1—S	126.09 (18)	H9B—C9—H9C	109.5
C2—C1—S	126.25 (18)	C11—C10—C15	121.4 (2)
C7—C2—C3	119.0 (2)	C11—C10—S	119.71 (19)
C7—C2—C1	104.5 (2)	C15—C10—S	118.90 (19)
C3—C2—C1	136.5 (2)	C10—C11—C12	119.1 (2)
C4—C3—C2	116.9 (2)	C10—C11—H11	120.4
C4—C3—H3	121.5	C12—C11—H11	120.4
C2—C3—H3	121.5	C13—C12—C11	118.3 (3)
C3—C4—C5	123.0 (2)	C13—C12—H12	120.8
C3—C4—I	118.01 (17)	C11—C12—H12	120.8
C5—C4—I	119.02 (17)	F—C13—C12	118.8 (3)
C6—C5—C4	120.5 (2)	F—C13—C14	118.0 (3)
C6—C5—H5	119.8	C12—C13—C14	123.2 (3)
C4—C5—H5	119.8	C15—C14—C13	118.3 (2)
C5—C6—C7	116.6 (2)	C15—C14—H14	120.8
C5—C6—H6	121.7	C13—C14—H14	120.8
C7—C6—H6	121.7	C14—C15—C10	119.6 (2)
O1—C7—C6	125.5 (2)	C14—C15—H15	120.2
O1—C7—C2	110.46 (19)	C10—C15—H15	120.2
C6—C7—C2	124.1 (2)

O3—S—C1—C8	28.4 (2)	C1—C2—C7—C6	178.9 (2)
O2—S—C1—C8	159.4 (2)	C2—C1—C8—O1	1.2 (3)
C10—S—C1—C8	−86.2 (2)	S—C1—C8—O1	177.96 (17)
O3—S—C1—C2	−155.4 (2)	C2—C1—C8—C9	−176.1 (3)
O2—S—C1—C2	−24.4 (2)	S—C1—C8—C9	0.7 (4)
C10—S—C1—C2	90.0 (2)	C7—O1—C8—C1	−1.2 (3)
C8—C1—C2—C7	−0.7 (3)	C7—O1—C8—C9	176.7 (2)
S—C1—C2—C7	−177.47 (17)	O3—S—C10—C11	163.83 (18)
C8—C1—C2—C3	177.9 (3)	O2—S—C10—C11	33.2 (2)
S—C1—C2—C3	1.1 (4)	C1—S—C10—C11	−80.6 (2)
C7—C2—C3—C4	0.8 (3)	O3—S—C10—C15	−14.9 (2)
C1—C2—C3—C4	−177.6 (3)	O2—S—C10—C15	−145.54 (18)
C2—C3—C4—C5	−1.1 (4)	C1—S—C10—C15	100.62 (19)
C2—C3—C4—I	178.21 (16)	C15—C10—C11—C12	−0.6 (3)
C3—C4—C5—C6	0.6 (4)	S—C10—C11—C12	−179.36 (18)
I—C4—C5—C6	−178.65 (18)	C10—C11—C12—C13	0.8 (3)
C4—C5—C6—C7	0.2 (3)	C11—C12—C13—F	179.6 (2)
C8—O1—C7—C6	−178.1 (2)	C11—C12—C13—C14	0.1 (4)
C8—O1—C7—C2	0.7 (2)	F—C13—C14—C15	179.3 (2)
C5—C6—C7—O1	178.2 (2)	C12—C13—C14—C15	−1.2 (4)
C5—C6—C7—C2	−0.5 (4)	C13—C14—C15—C10	1.4 (4)
C3—C2—C7—O1	−178.9 (2)	C11—C10—C15—C14	−0.5 (3)
C1—C2—C7—O1	0.0 (2)	S—C10—C15—C14	178.25 (18)
C3—C2—C7—C6	0.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2ⁱ	0.95	2.56	3.399 (3)	148

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀FIO₃S
M_r	416.19
Crystal system, space group	Triclinic, P1
Temperature (K)	179
a, b, c (Å)	7.5324 (3), 9.4289 (3), 11.6460 (4)
α, β, γ (°)	69.687 (1), 77.639 (2), 67.410 (2)
V (Å³)	713.06 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.41
Crystal size (mm)	0.32 × 0.31 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.516, 0.715
No. of measured, independent and observed [I > 2σ(I)] reflections	12406, 3286, 3117
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.067, 1.12
No. of reflections	3286
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.74

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
C11—H11···O2ⁱ	0.95	2.56	3.399 (3)	148.1

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

This work was supported by Blue–Bio Industry RIC at Dongeui University as a RIC program under the Ministry of Knowledge Economy and Busan City.

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