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ISSN: 2056-9890

3-(3-Chloro­phenyl­sulfin­yl)-2,4,6,7-tetra­methyl-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 12 January 2012; accepted 23 January 2012; online 31 January 2012)

In the title compound, C18H17ClO2S, the 3-chloro­phenyl ring makes a dihedral angle of 72.62 (4)° with the mean plane of the benzofuran fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O and C—H⋯π inter­actions. The crystal structure also exhibits a slipped ππ inter­action between the 3-chloro­phenyl rings of adjacent mol­ecules [centroid–centroid distance = 3.751 (2) Å, inter­planar distance = 3.450 (2) Å and slippage = 1.472 (2) Å].

Related literature

For the pharmacological 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 natural products with benzofuran rings, see: Akgul & Anil (2003[Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939-943.]); Soekamto et al. (2003[Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831-834.]). 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, o3087.], 2011[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o1323.]).

[Scheme 1]

Experimental

Crystal data
  • C18H17ClO2S

  • Mr = 332.83

  • Triclinic, [P \overline 1]

  • a = 7.4198 (1) Å

  • b = 7.9792 (1) Å

  • c = 14.5014 (2) Å

  • α = 105.965 (1)°

  • β = 95.732 (1)°

  • γ = 103.965 (1)°

  • V = 788.21 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.38 mm−1

  • T = 173 K

  • 0.26 × 0.25 × 0.25 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 = 0.908, Tmax = 0.911

  • 14786 measured reflections

  • 3897 independent reflections

  • 3622 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.099

  • S = 0.95

  • 3897 reflections

  • 203 parameters

  • H-atom parameters constrained

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.39 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C11—H11B⋯O2i 0.98 2.60 3.5786 (16) 175
C12—H12A⋯O2ii 0.98 2.40 3.3159 (17) 155
C10—H10CCg1iii 0.98 2.79 3.615 (16) 142
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x+1, y, z; (iii) -x+1, -y, -z.

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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) 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

Substituted benzofuran analogues have drawn much attention owing to their valuable 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). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our continuing study of 2,4,6,7-tetramethyl-1-benzofuran derivatives containing either 3-(4-chlorophenylsulfinyl) (Choi et al., 2010) or 3-(3-fluorophenylsulfinyl) (Choi et al., 2011) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.018 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 3-chlorophenyl ring and the mean plane of the benzofurn fragment is 72.62 (4)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C– H···O and C–H···π interactions (Table 1, Cg1 is the centroid of the C2-C7 benzene ring). The crystal packing (Fig. 2) is further stabilized by a weak slipped ππ interaction between the 3-chlorophenyl rings of adjacent molecules, with a Cg2···Cg2iv distance of 3.751 (2) Å and an interplanar distance of 3.450 (2) Å resulting in a slippage of 1.472 (2) Å (Cg2 is the centroid of the C13-C18 3-chlorophenyl ring).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For the crystal structures of related compounds, see: Choi et al. (2010, 2011).

Experimental top

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 3-(3-chlorophenylsulfanyl)-2,4,6,7-tetramethyl-1-benzofuran (285 mg, 0.9 mmol) in dichloromethane (30 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 (hexane-ethyl acetate, 4:1 v/v) to afford the title compound as a colorless solid [yield 76%, m.p. 447-448 K; Rf = 0.52 (hexane-ethyl acetate, 4:1 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

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C–H = 0.95 Å for aryl and 0.98 Å for methyl H atoms. Uiso(H) =1.2Ueq(C) for aryl and 1.5Ueq(C)for methyl H atoms.

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
[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, C–H···π, and ππ interactions (dottedlines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) - x + 1, - y + 1, - z; (ii) x + 1, y, z; (iii) -x + 1, -y, -z (iv) - -x + 1, - -y + 1, - z + 1; (v) -x - 1, -y, z.]
3-(3-Chlorophenylsulfinyl)-2,4,6,7-tetramethyl-1-benzofuran top
Crystal data top
C18H17ClO2SZ = 2
Mr = 332.83F(000) = 348
Triclinic, P1Dx = 1.402 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4198 (1) ÅCell parameters from 9057 reflections
b = 7.9792 (1) Åθ = 2.7–28.3°
c = 14.5014 (2) ŵ = 0.38 mm1
α = 105.965 (1)°T = 173 K
β = 95.732 (1)°Block, colourless
γ = 103.965 (1)°0.26 × 0.25 × 0.25 mm
V = 788.21 (2) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer
3897 independent reflections
Radiation source: rotating anode3622 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.025
Detector resolution: 10.0 pixels mm-1θmax = 28.3°, θmin = 1.5°
ϕ and ω scansh = 99
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1010
Tmin = 0.908, Tmax = 0.911l = 1919
14786 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: difference Fourier map
wR(F2) = 0.099H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.0638P)2 + 0.3249P]
where P = (Fo2 + 2Fc2)/3
3897 reflections(Δ/σ)max = 0.001
203 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.39 e Å3
Crystal data top
C18H17ClO2Sγ = 103.965 (1)°
Mr = 332.83V = 788.21 (2) Å3
Triclinic, P1Z = 2
a = 7.4198 (1) ÅMo Kα radiation
b = 7.9792 (1) ŵ = 0.38 mm1
c = 14.5014 (2) ÅT = 173 K
α = 105.965 (1)°0.26 × 0.25 × 0.25 mm
β = 95.732 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3897 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3622 reflections with I > 2σ(I)
Tmin = 0.908, Tmax = 0.911Rint = 0.025
14786 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.099H-atom parameters constrained
S = 0.95Δρmax = 0.36 e Å3
3897 reflectionsΔρmin = 0.39 e Å3
203 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
xyzUiso*/Ueq
S10.53130 (4)0.65049 (4)0.33172 (2)0.02082 (9)
Cl10.00317 (6)0.23558 (6)0.46616 (3)0.04572 (13)
O10.79660 (12)0.52179 (12)0.11618 (6)0.02335 (19)
O20.36498 (14)0.72242 (13)0.32004 (7)0.0282 (2)
C10.59030 (17)0.55512 (16)0.21874 (8)0.0202 (2)
C20.48969 (16)0.40937 (15)0.13006 (8)0.0191 (2)
C30.30551 (17)0.29506 (16)0.09430 (9)0.0212 (2)
C40.27547 (18)0.17027 (17)0.00165 (9)0.0236 (2)
H40.15180.09150.02470.028*
C50.41627 (19)0.15371 (17)0.05513 (9)0.0232 (2)
C60.59915 (18)0.26984 (17)0.02096 (9)0.0220 (2)
C70.62560 (17)0.39462 (16)0.07062 (8)0.0204 (2)
C80.77070 (17)0.61729 (17)0.20508 (9)0.0227 (2)
C90.14666 (18)0.30115 (19)0.15074 (9)0.0270 (3)
H9A0.02650.26120.10530.040*
H9B0.16540.42570.19260.040*
H9C0.14450.22050.19110.040*
C100.3716 (2)0.00812 (19)0.15260 (9)0.0297 (3)
H10A0.40410.06400.20330.045*
H10B0.23660.05610.16740.045*
H10C0.44500.07810.15040.045*
C110.7563 (2)0.26059 (19)0.07831 (10)0.0285 (3)
H11A0.86810.36180.04420.043*
H11B0.71660.26850.14310.043*
H11C0.78660.14540.08500.043*
C120.93714 (19)0.7651 (2)0.26499 (10)0.0317 (3)
H12A1.04090.71400.27810.048*
H12B0.90460.82650.32680.048*
H12C0.97610.85260.22980.048*
C130.44562 (18)0.44638 (16)0.36349 (8)0.0211 (2)
C140.55149 (19)0.32357 (18)0.35979 (9)0.0264 (3)
H140.66950.34380.33840.032*
C150.4822 (2)0.17083 (18)0.38788 (10)0.0305 (3)
H150.55280.08540.38510.037*
C160.3106 (2)0.14177 (18)0.42004 (10)0.0298 (3)
H160.26250.03650.43850.036*
C170.21090 (19)0.26868 (19)0.42478 (9)0.0276 (3)
C180.27641 (18)0.42257 (18)0.39725 (9)0.0246 (3)
H180.20690.50920.40150.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02414 (16)0.01806 (15)0.01927 (15)0.00564 (11)0.00480 (11)0.00411 (11)
Cl10.0391 (2)0.0496 (2)0.0587 (3)0.01101 (18)0.02486 (18)0.0286 (2)
O10.0202 (4)0.0255 (4)0.0230 (4)0.0046 (3)0.0058 (3)0.0062 (3)
O20.0326 (5)0.0247 (5)0.0331 (5)0.0151 (4)0.0106 (4)0.0104 (4)
C10.0211 (5)0.0205 (5)0.0193 (5)0.0056 (4)0.0043 (4)0.0063 (4)
C20.0224 (6)0.0177 (5)0.0187 (5)0.0062 (4)0.0044 (4)0.0074 (4)
C30.0224 (6)0.0204 (5)0.0217 (5)0.0056 (4)0.0054 (4)0.0080 (4)
C40.0243 (6)0.0204 (6)0.0228 (6)0.0022 (5)0.0025 (4)0.0055 (5)
C50.0306 (6)0.0207 (6)0.0190 (5)0.0080 (5)0.0049 (4)0.0064 (4)
C60.0274 (6)0.0222 (6)0.0205 (5)0.0093 (5)0.0077 (4)0.0096 (4)
C70.0207 (5)0.0205 (5)0.0214 (5)0.0057 (4)0.0040 (4)0.0087 (4)
C80.0232 (6)0.0231 (6)0.0220 (5)0.0069 (5)0.0046 (4)0.0068 (5)
C90.0215 (6)0.0293 (6)0.0255 (6)0.0021 (5)0.0064 (5)0.0046 (5)
C100.0387 (7)0.0249 (6)0.0219 (6)0.0073 (5)0.0064 (5)0.0027 (5)
C110.0311 (7)0.0330 (7)0.0247 (6)0.0115 (5)0.0118 (5)0.0097 (5)
C120.0217 (6)0.0333 (7)0.0315 (7)0.0010 (5)0.0034 (5)0.0027 (6)
C130.0265 (6)0.0195 (5)0.0163 (5)0.0066 (4)0.0034 (4)0.0039 (4)
C140.0307 (6)0.0254 (6)0.0246 (6)0.0113 (5)0.0069 (5)0.0066 (5)
C150.0421 (8)0.0235 (6)0.0288 (6)0.0147 (6)0.0068 (6)0.0075 (5)
C160.0403 (7)0.0216 (6)0.0247 (6)0.0040 (5)0.0042 (5)0.0075 (5)
C170.0294 (6)0.0285 (6)0.0228 (6)0.0036 (5)0.0064 (5)0.0078 (5)
C180.0282 (6)0.0258 (6)0.0207 (6)0.0088 (5)0.0057 (5)0.0070 (5)
Geometric parameters (Å, º) top
S1—O21.4949 (9)C9—H9C0.9800
S1—C11.7531 (12)C10—H10A0.9800
S1—C131.8001 (13)C10—H10B0.9800
Cl1—C171.7401 (14)C10—H10C0.9800
O1—C81.3635 (14)C11—H11A0.9800
O1—C71.3851 (14)C11—H11B0.9800
C1—C81.3651 (17)C11—H11C0.9800
C1—C21.4594 (16)C12—H12A0.9800
C2—C71.3960 (16)C12—H12B0.9800
C2—C31.4018 (17)C12—H12C0.9800
C3—C41.3941 (17)C13—C181.3823 (17)
C3—C91.5032 (16)C13—C141.3897 (17)
C4—C51.4020 (17)C14—C151.3886 (19)
C4—H40.9500C14—H140.9500
C5—C61.3970 (18)C15—C161.388 (2)
C5—C101.5081 (17)C15—H150.9500
C6—C71.3856 (17)C16—C171.382 (2)
C6—C111.5025 (17)C16—H160.9500
C8—C121.4797 (18)C17—C181.3870 (19)
C9—H9A0.9800C18—H180.9500
C9—H9B0.9800
O2—S1—C1111.44 (6)C5—C10—H10B109.5
O2—S1—C13105.69 (6)H10A—C10—H10B109.5
C1—S1—C1399.12 (5)C5—C10—H10C109.5
C8—O1—C7106.80 (9)H10A—C10—H10C109.5
C8—C1—C2107.14 (10)H10B—C10—H10C109.5
C8—C1—S1118.34 (9)C6—C11—H11A109.5
C2—C1—S1134.45 (9)C6—C11—H11B109.5
C7—C2—C3118.68 (11)H11A—C11—H11B109.5
C7—C2—C1104.27 (10)C6—C11—H11C109.5
C3—C2—C1137.04 (11)H11A—C11—H11C109.5
C4—C3—C2116.04 (11)H11B—C11—H11C109.5
C4—C3—C9120.50 (11)C8—C12—H12A109.5
C2—C3—C9123.45 (11)C8—C12—H12B109.5
C3—C4—C5124.13 (12)H12A—C12—H12B109.5
C3—C4—H4117.9C8—C12—H12C109.5
C5—C4—H4117.9H12A—C12—H12C109.5
C6—C5—C4120.18 (11)H12B—C12—H12C109.5
C6—C5—C10119.76 (11)C18—C13—C14121.49 (12)
C4—C5—C10120.05 (12)C18—C13—S1117.34 (9)
C7—C6—C5114.84 (11)C14—C13—S1121.06 (10)
C7—C6—C11122.20 (12)C15—C14—C13118.97 (12)
C5—C6—C11122.96 (11)C15—C14—H14120.5
O1—C7—C6123.21 (11)C13—C14—H14120.5
O1—C7—C2110.72 (10)C16—C15—C14120.63 (12)
C6—C7—C2126.06 (11)C16—C15—H15119.7
O1—C8—C1111.04 (11)C14—C15—H15119.7
O1—C8—C12115.43 (11)C17—C16—C15118.86 (13)
C1—C8—C12133.53 (12)C17—C16—H16120.6
C3—C9—H9A109.5C15—C16—H16120.6
C3—C9—H9B109.5C16—C17—C18121.86 (13)
H9A—C9—H9B109.5C16—C17—Cl1119.46 (11)
C3—C9—H9C109.5C18—C17—Cl1118.68 (11)
H9A—C9—H9C109.5C13—C18—C17118.15 (12)
H9B—C9—H9C109.5C13—C18—H18120.9
C5—C10—H10A109.5C17—C18—H18120.9
O2—S1—C1—C8125.23 (10)C11—C6—C7—C2178.00 (11)
C13—S1—C1—C8123.83 (10)C3—C2—C7—O1177.83 (10)
O2—S1—C1—C258.15 (13)C1—C2—C7—O11.15 (12)
C13—S1—C1—C252.78 (13)C3—C2—C7—C63.17 (18)
C8—C1—C2—C71.49 (13)C1—C2—C7—C6177.85 (11)
S1—C1—C2—C7175.39 (10)C7—O1—C8—C10.63 (13)
C8—C1—C2—C3177.20 (13)C7—O1—C8—C12178.36 (11)
S1—C1—C2—C35.9 (2)C2—C1—C8—O11.34 (14)
C7—C2—C3—C41.96 (16)S1—C1—C8—O1176.13 (8)
C1—C2—C3—C4179.49 (13)C2—C1—C8—C12177.39 (14)
C7—C2—C3—C9178.71 (11)S1—C1—C8—C125.1 (2)
C1—C2—C3—C90.2 (2)O2—S1—C13—C1817.61 (11)
C2—C3—C4—C50.39 (18)C1—S1—C13—C18133.06 (10)
C9—C3—C4—C5178.96 (12)O2—S1—C13—C14166.23 (10)
C3—C4—C5—C61.86 (19)C1—S1—C13—C1450.79 (11)
C3—C4—C5—C10177.04 (12)C18—C13—C14—C152.02 (19)
C4—C5—C6—C70.82 (17)S1—C13—C14—C15178.01 (10)
C10—C5—C6—C7178.09 (11)C13—C14—C15—C160.6 (2)
C4—C5—C6—C11179.50 (11)C14—C15—C16—C170.8 (2)
C10—C5—C6—C111.59 (18)C15—C16—C17—C180.8 (2)
C8—O1—C7—C6178.65 (11)C15—C16—C17—Cl1179.31 (10)
C8—O1—C7—C20.39 (13)C14—C13—C18—C172.01 (18)
C5—C6—C7—O1179.43 (10)S1—C13—C18—C17178.15 (9)
C11—C6—C7—O10.88 (18)C16—C17—C18—C130.59 (19)
C5—C6—C7—C21.68 (18)Cl1—C17—C18—C13179.31 (9)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C11—H11B···O2i0.982.603.5786 (16)175
C12—H12A···O2ii0.982.403.3159 (17)155
C10—H10C···Cg1iii0.982.793.615 (16)142
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC18H17ClO2S
Mr332.83
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)7.4198 (1), 7.9792 (1), 14.5014 (2)
α, β, γ (°)105.965 (1), 95.732 (1), 103.965 (1)
V3)788.21 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.38
Crystal size (mm)0.26 × 0.25 × 0.25
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.908, 0.911
No. of measured, independent and
observed [I > 2σ(I)] reflections
14786, 3897, 3622
Rint0.025
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.099, 0.95
No. of reflections3897
No. of parameters203
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.36, 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
Cg1 is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C11—H11B···O2i0.982.603.5786 (16)175.0
C12—H12A···O2ii0.982.403.3159 (17)155.2
C10—H10C···Cg1iii0.982.793.615 (16)142.4
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z; (iii) x+1, y, z.
 

Acknowledgements

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

References

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