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ISSN: 2056-9890

3-(4-Bromo­phenyl­sulfon­yl)-5-ethyl-2-methyl-1-benzo­furan

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 8 November 2012; accepted 25 November 2012; online 30 November 2012)

In the title compound, C17H15BrO3S, the 4-bromo­phenyl ring makes a dihedral angle of 76.58 (9)° with the mean plane [r.m.s. deviation = 0.006 (2) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯π inter­actions.

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009[Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191-195.]); Galal et al. (2009[Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420-2428.]); Khan et al. (2005[Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796-4805.]). For the crystal structures of related compounds, see: Choi et al. (2010[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o2575.], 2011[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o1278.]).

[Scheme 1]

Experimental

Crystal data
  • C17H15BrO3S

  • Mr = 379.26

  • Tetragonal, P 43

  • a = 10.2785 (3) Å

  • c = 15.2899 (6) Å

  • V = 1615.34 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.68 mm−1

  • T = 173 K

  • 0.31 × 0.17 × 0.15 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.450, Tmax = 0.746

  • 8518 measured reflections

  • 3085 independent reflections

  • 2558 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.067

  • S = 1.03

  • 3085 reflections

  • 201 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.29 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1000 Friedel pairs

  • Flack parameter: 0.001 (7)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C6—H6⋯O3i 0.95 2.53 3.238 (4) 131
C11—H11A⋯O3ii 0.98 2.58 3.321 (4) 132
C14—H14⋯Cgiii 0.95 2.70 3.495 (4) 142
Symmetry codes: (i) [-x, -y+1, z-{\script{1\over 2}}]; (ii) [-y+1, x, z-{\script{1\over 4}}]; (iii) [y, -x+1, z+{\script{1\over 4}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Many compounds containing the benzofuran skeleton have attracted much interest owing to their biological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009; Galal et al., 2009; Khan et al., 2005). As a part of our ongoing study of 5-ethyl-2-methyl-1-benzofuran derivatives containing 4-fluorophenylsulfonyl (Choi et al., 2010) or 3-fluorophenylsulfonyl (Choi et al., 2011) substituents in the 3-position, we report herein the crystal structure of the title compound.

The title compound crystallizes as the non-centrosymmetric space group P43 in spite of having no asymmetric C atoms.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.006 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 4-bromophenyl ring and the mean plane of the benzofuran ring is 76.58 (9)°. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O and C—H···π interactions (Table 1, Cg is the centroid of the C2–C7 benzene ring).

Related literature top

For the biological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For the crystal structures of related compounds, see: Choi et al. (2010, 2011).

Experimental top

3-Chloroperoxybenzoic acid (77%, 448 mg, 2.0 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-5-ethyl-2-methyl-1-benzofuran (312 mg, 0.9 mmol) in dichloromethane (50 mL) at 273 K. After being stirred at room temperature for 10h, 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 (benzene) to afford the title compound as a colorless solid [yield 68%, m.p. 404–405 K; Rf = 0.61 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in diisopropyl ether at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C–H = 0.95 Å for aryl, 0.99 Å for methylene and 0.98 Å for methyl H atoms, respectively. Uiso(H) = 1.2Ueq(C) for aryl, methylene, and 1.5Ueq(C) for methyl H atoms. The positions of methyl hydrogens were optimized rotationally.

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, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Bruker, 2009).

Figures top
[Figure 1] 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 small spheres of arbitrary radius.
[Figure 2] Fig. 2. A view of the C—H···O and C—H···π interactions (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen-bonding were omitted for clarity. [Symmetry code: (i) - x, - y + 1, z - 1/2 (ii) - y + 1, x, z - 1/4 (iii) y, - x + 1, z + 1/4 (iv) - x, - y + 1, z + 1/2
3-(4-Bromophenylsulfonyl)-5-ethyl-2-methyl-1-benzofuran top
Crystal data top
C17H15BrO3SDx = 1.559 Mg m3
Mr = 379.26Melting point = 404–405 K
Tetragonal, P43Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 4cwCell parameters from 2851 reflections
a = 10.2785 (3) Åθ = 2.4–23.1°
c = 15.2899 (6) ŵ = 2.68 mm1
V = 1615.34 (9) Å3T = 173 K
Z = 4Block, colourless
F(000) = 7680.31 × 0.17 × 0.15 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
3085 independent reflections
Radiation source: rotating anode2558 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.035
Detector resolution: 10.0 pixels mm-1θmax = 28.3°, θmin = 2.0°
ϕ and ω scansh = 1213
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1312
Tmin = 0.450, Tmax = 0.746l = 2013
8518 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.067 w = 1/[σ2(Fo2) + (0.0094P)2 + 0.1451P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3085 reflectionsΔρmax = 0.35 e Å3
201 parametersΔρmin = 0.29 e Å3
1 restraintAbsolute structure: Flack (1983), 1000 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.001 (7)
Crystal data top
C17H15BrO3SZ = 4
Mr = 379.26Mo Kα radiation
Tetragonal, P43µ = 2.68 mm1
a = 10.2785 (3) ÅT = 173 K
c = 15.2899 (6) Å0.31 × 0.17 × 0.15 mm
V = 1615.34 (9) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer
3085 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
2558 reflections with I > 2σ(I)
Tmin = 0.450, Tmax = 0.746Rint = 0.035
8518 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.067Δρmax = 0.35 e Å3
S = 1.03Δρmin = 0.29 e Å3
3085 reflectionsAbsolute structure: Flack (1983), 1000 Friedel pairs
201 parametersAbsolute structure parameter: 0.001 (7)
1 restraint
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
xyzUiso*/Ueq
Br10.83341 (3)0.52123 (5)0.64403 (3)0.06379 (15)
S10.22891 (7)0.40370 (7)0.69506 (5)0.02917 (17)
O10.1117 (2)0.2989 (2)0.46167 (13)0.0331 (5)
O20.2142 (2)0.2825 (2)0.73957 (15)0.0401 (6)
O30.1697 (2)0.5188 (2)0.73023 (15)0.0372 (5)
C120.3955 (3)0.4357 (3)0.68213 (18)0.0248 (6)
C20.1292 (3)0.4919 (3)0.5329 (2)0.0250 (6)
C170.4835 (3)0.3333 (3)0.6829 (2)0.0357 (7)
H170.45460.24640.69120.043*
C130.4374 (3)0.5626 (3)0.6707 (2)0.0346 (8)
H130.37630.63190.67050.042*
C160.6140 (3)0.3604 (3)0.6713 (2)0.0394 (8)
H160.67570.29160.67120.047*
C150.6542 (3)0.4857 (4)0.66010 (19)0.0390 (8)
C60.0458 (3)0.4963 (3)0.3844 (2)0.0370 (7)
H60.02230.45250.33200.044*
C70.0933 (3)0.4311 (3)0.4558 (2)0.0287 (7)
C50.0339 (3)0.6299 (3)0.3931 (3)0.0382 (7)
H50.00080.67870.34520.046*
C30.1165 (3)0.6262 (3)0.5399 (2)0.0299 (7)
H30.14030.66960.59230.036*
C80.1590 (3)0.2747 (3)0.5441 (2)0.0295 (7)
C90.0514 (4)0.8410 (3)0.4760 (3)0.0454 (9)
H9A0.08460.87050.53350.054*
H9B0.10460.88320.43010.054*
C140.5674 (3)0.5881 (3)0.6595 (2)0.0392 (8)
H140.59710.67480.65150.047*
C40.0687 (3)0.6956 (3)0.4694 (2)0.0359 (8)
C10.1709 (3)0.3870 (3)0.58850 (19)0.0275 (7)
C110.1847 (3)0.1373 (3)0.5637 (2)0.0399 (8)
H11A0.24690.10250.52120.060*
H11B0.10330.08800.56030.060*
H11C0.22100.12970.62280.060*
C100.0874 (4)0.8851 (4)0.4663 (3)0.0598 (11)
H10A0.12020.85950.40860.090*
H10B0.09170.97990.47210.090*
H10C0.14090.84460.51190.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02640 (18)0.1092 (4)0.0558 (2)0.00760 (19)0.00298 (19)0.0095 (3)
S10.0271 (4)0.0358 (4)0.0246 (3)0.0022 (3)0.0028 (3)0.0006 (4)
O10.0342 (12)0.0308 (12)0.0344 (12)0.0039 (9)0.0097 (10)0.0053 (10)
O20.0447 (14)0.0415 (14)0.0340 (12)0.0079 (10)0.0037 (11)0.0077 (11)
O30.0330 (13)0.0478 (14)0.0308 (12)0.0037 (10)0.0048 (10)0.0083 (11)
C120.0189 (14)0.0371 (17)0.0183 (13)0.0009 (12)0.0012 (12)0.0052 (13)
C20.0176 (14)0.0285 (16)0.0288 (16)0.0047 (12)0.0025 (13)0.0043 (13)
C170.0399 (19)0.0355 (18)0.0316 (16)0.0026 (13)0.0022 (15)0.0029 (15)
C130.0315 (17)0.0337 (18)0.0387 (19)0.0036 (13)0.0008 (14)0.0074 (14)
C160.0329 (18)0.052 (2)0.0330 (18)0.0134 (15)0.0038 (14)0.0043 (16)
C150.0219 (15)0.071 (3)0.0243 (17)0.0017 (15)0.0011 (14)0.0056 (17)
C60.0384 (18)0.0387 (17)0.0338 (17)0.0044 (14)0.0098 (16)0.0033 (16)
C70.0233 (15)0.0279 (16)0.0348 (17)0.0020 (12)0.0040 (13)0.0018 (14)
C50.0345 (18)0.0388 (18)0.0414 (17)0.0023 (14)0.0121 (17)0.006 (2)
C30.0296 (17)0.0273 (17)0.0329 (17)0.0052 (13)0.0018 (14)0.0028 (14)
C80.0272 (17)0.0302 (17)0.0312 (17)0.0024 (13)0.0016 (14)0.0012 (14)
C90.058 (2)0.0264 (18)0.052 (2)0.0003 (16)0.0081 (19)0.0021 (16)
C140.0355 (18)0.0398 (19)0.042 (2)0.0093 (14)0.0031 (16)0.0073 (16)
C40.0341 (18)0.0313 (18)0.0423 (19)0.0045 (13)0.0024 (15)0.0010 (15)
C10.0221 (16)0.0302 (17)0.0302 (16)0.0048 (12)0.0000 (13)0.0004 (14)
C110.043 (2)0.0305 (18)0.047 (2)0.0022 (15)0.0034 (17)0.0018 (16)
C100.072 (3)0.034 (2)0.074 (3)0.0137 (18)0.004 (2)0.000 (2)
Geometric parameters (Å, º) top
Br1—C151.894 (3)C6—C51.384 (4)
S1—O21.427 (2)C6—H60.9500
S1—O31.435 (2)C5—C41.395 (5)
S1—C11.743 (3)C5—H50.9500
S1—C121.754 (3)C3—C41.382 (4)
O1—C81.374 (4)C3—H30.9500
O1—C71.376 (3)C8—C11.345 (4)
C12—C131.385 (4)C8—C111.467 (4)
C12—C171.388 (4)C9—C101.505 (5)
C2—C71.384 (4)C9—C41.509 (4)
C2—C31.391 (4)C9—H9A0.9900
C2—C11.438 (4)C9—H9B0.9900
C17—C161.381 (4)C14—H140.9500
C17—H170.9500C11—H11A0.9800
C13—C141.372 (4)C11—H11B0.9800
C13—H130.9500C11—H11C0.9800
C16—C151.364 (5)C10—H10A0.9800
C16—H160.9500C10—H10B0.9800
C15—C141.381 (5)C10—H10C0.9800
C6—C71.371 (4)
O2—S1—O3119.73 (14)C4—C3—C2119.0 (3)
O2—S1—C1108.87 (14)C4—C3—H3120.5
O3—S1—C1106.63 (14)C2—C3—H3120.5
O2—S1—C12108.70 (14)C1—C8—O1109.9 (3)
O3—S1—C12107.56 (13)C1—C8—C11134.9 (3)
C1—S1—C12104.29 (13)O1—C8—C11115.2 (3)
C8—O1—C7106.7 (2)C10—C9—C4113.8 (3)
C13—C12—C17120.8 (3)C10—C9—H9A108.8
C13—C12—S1119.7 (2)C4—C9—H9A108.8
C17—C12—S1119.6 (2)C10—C9—H9B108.8
C7—C2—C3119.2 (3)C4—C9—H9B108.8
C7—C2—C1104.2 (2)H9A—C9—H9B107.7
C3—C2—C1136.6 (3)C13—C14—C15118.9 (3)
C16—C17—C12118.7 (3)C13—C14—H14120.6
C16—C17—H17120.7C15—C14—H14120.6
C12—C17—H17120.7C3—C4—C5119.6 (3)
C14—C13—C12120.0 (3)C3—C4—C9120.1 (3)
C14—C13—H13120.0C5—C4—C9120.3 (3)
C12—C13—H13120.0C8—C1—C2108.5 (3)
C15—C16—C17120.1 (3)C8—C1—S1126.0 (2)
C15—C16—H16120.0C2—C1—S1125.5 (2)
C17—C16—H16120.0C8—C11—H11A109.5
C16—C15—C14121.7 (3)C8—C11—H11B109.5
C16—C15—Br1119.6 (3)H11A—C11—H11B109.5
C14—C15—Br1118.7 (3)C8—C11—H11C109.5
C7—C6—C5116.1 (3)H11A—C11—H11C109.5
C7—C6—H6122.0H11B—C11—H11C109.5
C5—C6—H6122.0C9—C10—H10A109.5
C6—C7—O1125.7 (3)C9—C10—H10B109.5
C6—C7—C2123.6 (3)H10A—C10—H10B109.5
O1—C7—C2110.7 (3)C9—C10—H10C109.5
C6—C5—C4122.5 (3)H10A—C10—H10C109.5
C6—C5—H5118.7H10B—C10—H10C109.5
C4—C5—H5118.7
O2—S1—C12—C13156.8 (2)C7—O1—C8—C11179.7 (3)
O3—S1—C12—C1325.8 (3)C12—C13—C14—C150.1 (5)
C1—S1—C12—C1387.2 (3)C16—C15—C14—C130.1 (5)
O2—S1—C12—C1723.7 (3)Br1—C15—C14—C13179.6 (2)
O3—S1—C12—C17154.7 (2)C2—C3—C4—C50.2 (5)
C1—S1—C12—C1792.3 (3)C2—C3—C4—C9178.8 (3)
C13—C12—C17—C160.5 (4)C6—C5—C4—C30.3 (5)
S1—C12—C17—C16179.1 (2)C6—C5—C4—C9178.8 (3)
C17—C12—C13—C140.3 (4)C10—C9—C4—C3117.6 (4)
S1—C12—C13—C14179.3 (3)C10—C9—C4—C560.9 (5)
C12—C17—C16—C150.5 (5)O1—C8—C1—C20.1 (3)
C17—C16—C15—C140.3 (5)C11—C8—C1—C2180.0 (3)
C17—C16—C15—Br1179.8 (2)O1—C8—C1—S1179.2 (2)
C5—C6—C7—O1179.4 (3)C11—C8—C1—S10.7 (5)
C5—C6—C7—C20.4 (5)C7—C2—C1—C80.2 (3)
C8—O1—C7—C6179.2 (3)C3—C2—C1—C8178.9 (3)
C8—O1—C7—C20.6 (3)C7—C2—C1—S1179.5 (2)
C3—C2—C7—C60.4 (5)C3—C2—C1—S11.8 (5)
C1—C2—C7—C6179.3 (3)O2—S1—C1—C822.4 (3)
C3—C2—C7—O1179.4 (3)O3—S1—C1—C8152.8 (3)
C1—C2—C7—O10.5 (3)C12—S1—C1—C893.5 (3)
C7—C6—C5—C40.4 (5)O2—S1—C1—C2158.4 (2)
C7—C2—C3—C40.2 (4)O3—S1—C1—C228.0 (3)
C1—C2—C3—C4178.8 (3)C12—S1—C1—C285.7 (3)
C7—O1—C8—C10.4 (3)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C6—H6···O3i0.952.533.238 (4)131
C11—H11A···O3ii0.982.583.321 (4)132
C14—H14···Cgiii0.952.703.495 (4)142
Symmetry codes: (i) x, y+1, z1/2; (ii) y+1, x, z1/4; (iii) y, x+1, z+1/4.

Experimental details

Crystal data
Chemical formulaC17H15BrO3S
Mr379.26
Crystal system, space groupTetragonal, P43
Temperature (K)173
a, c (Å)10.2785 (3), 15.2899 (6)
V3)1615.34 (9)
Z4
Radiation typeMo Kα
µ (mm1)2.68
Crystal size (mm)0.31 × 0.17 × 0.15
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.450, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
8518, 3085, 2558
Rint0.035
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.067, 1.03
No. of reflections3085
No. of parameters201
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.29
Absolute structureFlack (1983), 1000 Friedel pairs
Absolute structure parameter0.001 (7)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 1998), SHELXL97 (Bruker, 2009).

Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C6—H6···O3i0.952.533.238 (4)131.3
C11—H11A···O3ii0.982.583.321 (4)132.3
C14—H14···Cgiii0.952.703.495 (4)141.6
Symmetry codes: (i) x, y+1, z1/2; (ii) y+1, x, z1/4; (iii) y, x+1, z+1/4.
 

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan City.

References

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