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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o2721
https://doi.org/10.1107/S1600536810038870

5-Bromo-3-(4-chloro­phenyl­sulfin­yl)-2-methyl-1-benzo­furan

Hong Dae Choi,a Pil Ja Seo,a Byeng Wha Sonb and Uk Leeb*

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 28 September 2010; accepted 29 September 2010; online 9 October 2010)

In the title compound, C15H10BrClO2S, the 4-chloro­phenyl ring is oriented approximately perpendicular to the mean plane of the benzofuran ring [dihedral angle = 89.55 (9)°]. In the crystal, mol­ecules are linked through weak inter­molecular C—H⋯O hydrogen bonds and and a Br⋯Br contact [3.783 (3) Å].

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2006[Aslam, S. N., Stevenson, P. C., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214-4226.]); 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 structures of related 3-(4-chloro­phenyl­sulfin­yl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o2325.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o2551.]).

[Scheme 1]

Experimental

Crystal data

  • C15H10BrClO2S

  • Mr = 369.65

  • Monoclinic, P 21 /c

  • a = 11.530 (6) Å

  • b = 5.834 (3) Å

  • c = 22.045 (13) Å

  • β = 100.602 (16)°

  • V = 1457.6 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 3.14 mm−1

  • T = 173 K

  • 0.20 × 0.16 × 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 = 0.625, Tmax = 0.746

  • 12344 measured reflections

  • 3169 independent reflections

  • 2505 reflections with I > 2σ(I)

  • Rint = 0.054
Refinement

  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.125

  • S = 1.08

  • 3169 reflections

  • 182 parameters

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.61 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C9—H9C⋯O2i 0.98 2.51 3.473 (5) 166
C14—H14⋯O2ii 0.95 2.56 3.376 (4) 145
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x+2, -y+2, -z+1.

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

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810038870/hg2719sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810038870/hg2719Isup2.hkl

checkCIF report


Comment top

Many compounds involving a benzofuran skeleton have received much attention owing to their important pharmacological properties such as antifungal, antimicrobial, antitumor and antiviral 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-chlorophenylsulfinyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010a,b), we report herein on the crystal structure of the title compound.

In the title molecule (Fig. 1). the benzofuran unit is essentially planar, with a mean deviation of 0.090 (2) Å from the least-squares plane defined by the nine constituent atoms. The 4-chlorophenyl ring makes a dihedral angle of 89.55 (9)° with the mean plane of the benzofuran fragment. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a methyl H atom and the oxygen of the S═O unit [C9—H9C···O2i; see Table 1], and the second one between the 4-chlorophenyl H atom and the oxygen of the S═O unit [C14—H14···O2ii; see Table 1], respectively. The crystal packing (Fig. 2) is further stabilized by an intermolecular a Br—Briii interaction at 3.783 (3) Å.

Related literature top

For the biological 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-chlorophenylsulfinyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a,b).

Experimental top

77% 3-chloroperoxybenzoic acid (202 mg, 0.9 mmol) was added in small portions to a stirred solution of 5-bromo-3-(4-chlorophenylsulfanyl)-2-methyl-1-benzofuran (289 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 5h, 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 (silica gel, hexane–ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 83%, m.p. 404–405 K; Rf = 0.64 (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 acetone at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 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.

Structure description top

Many compounds involving a benzofuran skeleton have received much attention owing to their important pharmacological properties such as antifungal, antimicrobial, antitumor and antiviral 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-chlorophenylsulfinyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010a,b), we report herein on the crystal structure of the title compound.

In the title molecule (Fig. 1). the benzofuran unit is essentially planar, with a mean deviation of 0.090 (2) Å from the least-squares plane defined by the nine constituent atoms. The 4-chlorophenyl ring makes a dihedral angle of 89.55 (9)° with the mean plane of the benzofuran fragment. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a methyl H atom and the oxygen of the S═O unit [C9—H9C···O2i; see Table 1], and the second one between the 4-chlorophenyl H atom and the oxygen of the S═O unit [C14—H14···O2ii; see Table 1], respectively. The crystal packing (Fig. 2) is further stabilized by an intermolecular a Br—Briii interaction at 3.783 (3) Å.

For the biological 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-chlorophenylsulfinyl)-2-methyl-1-benzofuran derivatives, 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
[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 a small spheres of arbitrary radius.
[Figure 2] Fig. 2. A view of the C—H···O and Br···Br interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x +2, y - 1/2, - z + 3/2; (ii) - x + 2, - y + 2, - z + 1; (iii) - x + 1, - y + 3, - z + 1.]
5-Bromo-3-(4-chlorophenylsulfinyl)-2-methyl-1-benzofuran top
Crystal data top
C15H10BrClO2SF(000) = 736
Mr = 369.65Dx = 1.684 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4598 reflections
a = 11.530 (6) Åθ = 2.4–27.8°
b = 5.834 (3) ŵ = 3.14 mm−1
c = 22.045 (13) ÅT = 173 K
β = 100.602 (16)°Block, colourless
V = 1457.6 (15) Å30.20 × 0.16 × 0.15 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD
diffractometer		3169 independent reflections
Radiation source: rotating anode2505 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.054
Detector resolution: 10.0 pixels mm-1θmax = 27.0°, θmin = 1.8°
φ and ω scansh = −14→14
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −7→7
Tmin = 0.625, Tmax = 0.746l = −28→28
12344 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)] = 0.040Hydrogen site location: difference Fourier map
wR(F2) = 0.125H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0713P)2]
where P = (Fo2 + 2Fc2)/3
3169 reflections(Δ/σ)max = 0.001
182 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −0.61 e Å−3
Crystal data top
C15H10BrClO2SV = 1457.6 (15) Å3
Mr = 369.65Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.530 (6) ŵ = 3.14 mm−1
b = 5.834 (3) ÅT = 173 K
c = 22.045 (13) Å0.20 × 0.16 × 0.15 mm
β = 100.602 (16)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3169 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		2505 reflections with I > 2σ(I)
Tmin = 0.625, Tmax = 0.746Rint = 0.054
12344 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.125H-atom parameters constrained
S = 1.08Δρmax = 0.37 e Å−3
3169 reflectionsΔρmin = −0.61 e Å−3
182 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
Br0.49545 (3)1.26359 (6)0.558213 (16)0.05190 (16)
Cl0.73989 (8)0.5654 (2)0.33164 (3)0.0649 (3)
S0.93528 (6)0.61437 (15)0.61528 (3)0.0386 (2)
O10.69728 (19)0.4763 (4)0.71682 (8)0.0423 (5)
O20.9809 (2)0.8550 (5)0.62575 (10)0.0516 (6)
C10.8083 (3)0.5913 (5)0.64826 (12)0.0345 (6)
C20.7048 (3)0.7367 (5)0.64045 (12)0.0328 (6)
C30.6625 (2)0.9187 (5)0.60174 (12)0.0344 (6)
H30.70390.97310.57110.041*
C40.5576 (3)1.0161 (5)0.61011 (12)0.0371 (6)
C50.4941 (3)0.9380 (6)0.65489 (13)0.0433 (7)
H50.42211.01040.65900.052*
C60.5362 (3)0.7563 (6)0.69289 (13)0.0453 (8)
H60.49500.70110.72350.054*
C70.6407 (3)0.6592 (6)0.68429 (12)0.0368 (6)
C80.7994 (3)0.4395 (5)0.69429 (12)0.0371 (7)
C90.8777 (4)0.2533 (6)0.72349 (16)0.0533 (9)
H9A0.94660.24210.70350.080*
H9B0.83460.10770.71890.080*
H9C0.90370.28700.76740.080*
C100.8689 (2)0.6021 (5)0.53503 (12)0.0300 (6)
C110.8105 (3)0.4075 (5)0.50999 (14)0.0451 (8)
H110.79870.28280.53590.054*
C120.7695 (3)0.3952 (6)0.44718 (15)0.0488 (8)
H120.72800.26390.42930.059*
C130.7902 (2)0.5784 (6)0.41089 (13)0.0390 (7)
C140.8486 (3)0.7708 (5)0.43509 (15)0.0434 (8)
H140.86160.89440.40910.052*
C150.8881 (3)0.7822 (5)0.49797 (14)0.0395 (7)
H150.92860.91480.51570.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.0453 (2)0.0542 (3)0.0552 (2)0.01571 (15)0.00677 (17)0.00300 (14)
Cl0.0517 (5)0.1073 (8)0.0349 (4)0.0106 (5)0.0053 (4)−0.0076 (4)
S0.0285 (4)0.0529 (5)0.0344 (4)0.0028 (3)0.0059 (3)0.0022 (3)
O10.0496 (13)0.0516 (13)0.0274 (9)−0.0036 (11)0.0116 (9)0.0057 (8)
O20.0441 (13)0.0659 (15)0.0450 (12)−0.0217 (13)0.0090 (10)−0.0112 (11)
C10.0330 (15)0.0442 (17)0.0269 (12)0.0012 (13)0.0067 (11)0.0009 (11)
C20.0307 (15)0.0414 (17)0.0263 (12)−0.0052 (12)0.0054 (11)−0.0035 (10)
C30.0310 (14)0.0427 (17)0.0312 (13)−0.0006 (13)0.0099 (11)0.0014 (11)
C40.0320 (14)0.0464 (17)0.0323 (13)0.0004 (14)0.0040 (12)−0.0075 (12)
C50.0300 (15)0.064 (2)0.0374 (14)0.0020 (15)0.0105 (12)−0.0127 (14)
C60.0412 (18)0.068 (2)0.0301 (15)−0.0078 (15)0.0159 (14)−0.0050 (13)
C70.0394 (16)0.0462 (17)0.0252 (12)−0.0063 (14)0.0067 (12)−0.0033 (12)
C80.0436 (16)0.0414 (16)0.0257 (12)−0.0029 (14)0.0046 (12)−0.0003 (11)
C90.068 (3)0.051 (2)0.0385 (16)0.0065 (16)0.0032 (17)0.0119 (13)
C100.0256 (13)0.0325 (14)0.0334 (13)0.0047 (11)0.0096 (11)0.0010 (10)
C110.054 (2)0.0348 (16)0.0470 (16)−0.0054 (15)0.0095 (15)0.0040 (13)
C120.052 (2)0.0419 (18)0.0496 (17)−0.0068 (16)0.0025 (15)−0.0083 (14)
C130.0278 (14)0.058 (2)0.0336 (14)0.0102 (14)0.0110 (12)−0.0027 (13)
C140.0409 (18)0.052 (2)0.0395 (15)0.0005 (15)0.0137 (14)0.0109 (13)
C150.0374 (17)0.0410 (17)0.0424 (15)−0.0088 (13)0.0132 (14)−0.0017 (12)
Geometric parameters (Å, º) top
Br—C41.899 (3)C6—C71.376 (5)
Br—Bri3.7826 (17)C6—H60.9500
Cl—C131.738 (3)C8—C91.482 (4)
S—O21.502 (3)C9—H9A0.9800
S—C11.756 (3)C9—H9B0.9800
S—C101.795 (3)C9—H9C0.9800
O1—C81.376 (4)C10—C151.373 (4)
O1—C71.381 (4)C10—C111.382 (4)
C1—C81.365 (4)C11—C121.380 (4)
C1—C21.448 (4)C11—H110.9500
C2—C31.393 (4)C12—C131.382 (5)
C2—C71.395 (4)C12—H120.9500
C3—C41.379 (4)C13—C141.366 (5)
C3—H30.9500C14—C151.379 (4)
C4—C51.409 (4)C14—H140.9500
C5—C61.383 (5)C15—H150.9500
C5—H50.9500
C4—Br—Bri155.35 (9)C1—C8—C9132.5 (3)
O2—S—C1107.65 (14)O1—C8—C9116.8 (3)
O2—S—C10105.22 (13)C8—C9—H9A109.5
C1—S—C1099.69 (13)C8—C9—H9B109.5
C8—O1—C7106.7 (2)H9A—C9—H9B109.5
C8—C1—C2107.2 (3)C8—C9—H9C109.5
C8—C1—S122.7 (2)H9A—C9—H9C109.5
C2—C1—S129.6 (2)H9B—C9—H9C109.5
C3—C2—C7120.1 (3)C15—C10—C11120.7 (3)
C3—C2—C1135.0 (3)C15—C10—S118.0 (2)
C7—C2—C1104.9 (2)C11—C10—S120.9 (2)
C4—C3—C2116.6 (3)C12—C11—C10119.7 (3)
C4—C3—H3121.7C12—C11—H11120.2
C2—C3—H3121.7C10—C11—H11120.2
C3—C4—C5122.9 (3)C11—C12—C13118.5 (3)
C3—C4—Br118.4 (2)C11—C12—H12120.8
C5—C4—Br118.7 (2)C13—C12—H12120.8
C6—C5—C4120.1 (3)C14—C13—C12122.3 (3)
C6—C5—H5119.9C14—C13—Cl118.5 (2)
C4—C5—H5119.9C12—C13—Cl119.1 (2)
C7—C6—C5116.8 (3)C13—C14—C15118.7 (3)
C7—C6—H6121.6C13—C14—H14120.7
C5—C6—H6121.6C15—C14—H14120.7
C6—C7—O1126.1 (3)C10—C15—C14120.1 (3)
C6—C7—C2123.4 (3)C10—C15—H15120.0
O1—C7—C2110.5 (3)C14—C15—H15120.0
C1—C8—O1110.7 (3)
O2—S—C1—C8−120.0 (3)C1—C2—C7—O1−1.0 (3)
C10—S—C1—C8130.5 (2)C2—C1—C8—O10.0 (3)
O2—S—C1—C250.7 (3)S—C1—C8—O1172.54 (19)
C10—S—C1—C2−58.8 (3)C2—C1—C8—C9−178.9 (3)
C8—C1—C2—C3−179.5 (3)S—C1—C8—C9−6.4 (5)
S—C1—C2—C38.7 (5)C7—O1—C8—C1−0.7 (3)
C8—C1—C2—C70.6 (3)C7—O1—C8—C9178.4 (3)
S—C1—C2—C7−171.2 (2)O2—S—C10—C1510.8 (3)
C7—C2—C3—C41.0 (4)C1—S—C10—C15122.2 (2)
C1—C2—C3—C4−178.9 (3)O2—S—C10—C11−175.8 (2)
C2—C3—C4—C5−0.4 (4)C1—S—C10—C11−64.3 (3)
C2—C3—C4—Br−179.6 (2)C15—C10—C11—C12−0.9 (5)
C3—C4—C5—C60.0 (5)S—C10—C11—C12−174.2 (3)
Br—C4—C5—C6179.2 (2)C10—C11—C12—C131.1 (5)
C4—C5—C6—C7−0.2 (4)C11—C12—C13—C14−0.7 (5)
C5—C6—C7—O1−179.5 (3)C11—C12—C13—Cl179.7 (3)
C5—C6—C7—C20.8 (5)C12—C13—C14—C150.0 (5)
C8—O1—C7—C6−178.6 (3)Cl—C13—C14—C15179.7 (3)
C8—O1—C7—C21.1 (3)C11—C10—C15—C140.3 (5)
C3—C2—C7—C6−1.3 (4)S—C10—C15—C14173.8 (3)
C1—C2—C7—C6178.7 (3)C13—C14—C15—C100.2 (5)
C3—C2—C7—O1179.0 (2)
Symmetry code: (i) −x+1, −y+3, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9C···O2ii0.982.513.473 (5)166
C14—H14···O2iii0.952.563.376 (4)145
Symmetry codes: (ii) −x+2, y−1/2, −z+3/2; (iii) −x+2, −y+2, −z+1.

Experimental details

Crystal data
Chemical formulaC15H10BrClO2S
Mr369.65
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)11.530 (6), 5.834 (3), 22.045 (13)
β (°) 100.602 (16)
V (Å3)1457.6 (15)
Z4
Radiation typeMo Kα
µ (mm−1)3.14
Crystal size (mm)0.20 × 0.16 × 0.15
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.625, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections		12344, 3169, 2505
Rint0.054
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.125, 1.08
No. of reflections3169
No. of parameters182
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.37, −0.61

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···AD—HH···AD···AD—H···A
C9—H9C···O2i0.982.513.473 (5)166.1
C14—H14···O2ii0.952.563.376 (4)144.6
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+2, −y+2, −z+1.
 

References

First citationAkgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943.  Web of Science CrossRef PubMed CAS Google Scholar
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 First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
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 First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o2325.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSoekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831–834.  Web of Science CrossRef PubMed CAS Google Scholar

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ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o2721
https://doi.org/10.1107/S1600536810038870
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