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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2-(4-Bromo­phen­yl)-5,6-methyl­enedi­­oxy-3-phenyl­sulfinyl-1-benzo­furan benzene solvate

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 7 September 2009; accepted 15 September 2009; online 19 September 2009)

In the title compound, C21H13BrO4S·C6H6, the O atom and the phenyl group of the phenyl­sulfinyl substituent are located on opposite sides of the mean plane of the 5,6-methyl­enedioxy­benzofuran fragment; the phenyl ring is almost perpendicular to this plane [83.66 (6)°]. The 4-bromo­phenyl ring is rotated slightly out of the 5,6-methyl­enedioxy­benzo­furan plane, making a dihedral angle of 2.9 (1)°. The crystal structure is stabilized by inter­molecular C—H⋯O hydrogen bonds and inter­molecular C—H⋯π inter­actions. The crystal structure also exhibits ππ inter­actions between the benzene ring and the 4-bromo­phenyl ring of an adjacent mol­ecule [centroid–centroid distance = 3.586 (3) Å].

Related literature

For the crystal structures of similar 5,6-methyl­enedi­oxy-1-benzofuran derivatives, see: Choi et al. (2007[Choi, H. D., Seo, P. J., Lee, H. K., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o519-o520.], 2008[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o849.]). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999[Howlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283-289.]); Twyman & Allsop (1999[Twyman, L. J. & Allsop, D. (1999). Tetrahedron Lett. 40, 9383-9384.]). For natural products with benzofuran rings, see: Akgul & Anil (2003[Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939-943.]); von Reuss & König (2004[Reuss, S. H. von & König, W. A. (2004). Phytochemistry, 65, 3113-3118.]).

[Scheme 1]

Experimental

Crystal data
  • C21H13BrO4S·C6H6

  • Mr = 519.39

  • Monoclinic, P 21 /c

  • a = 13.8967 (7) Å

  • b = 12.6640 (7) Å

  • c = 13.0469 (7) Å

  • β = 102.418 (1)°

  • V = 2242.4 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.96 mm−1

  • T = 173 K

  • 0.40 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000[Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.]) Tmin = 0.629, Tmax = 0.679

  • 13417 measured reflections

  • 4886 independent reflections

  • 3946 reflections with I > 2σ(I)

  • Rint = 0.075

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.102

  • S = 1.02

  • 4886 reflections

  • 298 parameters

  • 6 restraints

  • H-atom parameters constrained

  • Δρmax = 0.64 e Å−3

  • Δρmin = −0.65 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C4—H4⋯O4i 0.93 2.43 3.290 (3) 154
C14—H14⋯Cg1ii 0.93 2.72 3.531 (3) 147
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]. Cg1 is the centroid of the C1/C2/O1/C3/C9 furan ring.

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT and SMART. 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

Benzofuran systems have been received particular attention in the view of their pharmacological properties (Howlett et al., 1999; Twyman & Allsop, 1999). These compounds occur in natural products (Akgul & Anil, 2003; von Reuss & König, 2004). As a part of our ongoing studies of the effect of side chain substituents on the solid state structures of 5,6-methylenedioxy-1-benzofuran analogues (Choi et al., 2007, 2008) we report the crystal structure of the title compound (I) co-crystallized with benzene. The 5,6-methylenedioxybenzofuran unit is planar with a mean deviation of 0.030 (2) Å from the least-squares plane defined by the twelve constituent atoms. The dihedral angle formed by the planes of the 5,6-methylenedioxybenzofuran ring and 4-bromophenyl ring is 2.9 (1)°. The phenyl ring (C16-C21) is almost perpendicular to the plane of 5,6-methylenedioxybenzofuran [83.66 (6)°]. The crystal packing (Fig. 2) is stabilized by intermolecular C–H···O hydrogen bonds between a benzene H atom of the 5,6-methylenedioxybenzofuran ring and the oxygen of the SO unit, with a C4–H4···O4i (Table 1). The molecular packing (Fig. 3) is further stabilized by intermolecular C–H···π interactions between an H atom of the 4-bromophenyl ring and the furan ring, with a C14–H14···Cg1ii (Table 1; Cg1 is the centroid of the C1/C2/O1/C3/C9 furan ring). The crystal structure (Fig. 3) also exhibits ππ interactions between the benzene ring and the 4-bromophenyl ring of the neighbouring molecules. The Cg2···Cg3v distance is 3.586 (3) Å (Cg2 and Cg3 is the centroids of the C3/C4/C5/C7/C8/C9 benzene ring and the C10-C15 phenyl ring, respectively).

Related literature top

For the crystal structures of similar 5,6-methylenedioxy-1-benzofuran derivatives, see: Choi et al. (2007, 2008). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999); Twyman & Allsop (1999). For natural products with benzofuran rings, see: Akgul & Anil (2003); von Reuss & König (2004). Cg1 is the centroid of the C1/C2/O1/C3/C9 furan ring.

Experimental top

77% 3-Chloroperoxybenzoic acid (123 mg, 0.55 mmol) was added in small portions to a stirred solution of 2-(4-bromophenyl)-5, 6-methylenedioxy-3-phenylsulfanyl-1-benzofuran (213 mg, 0.5 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 3 h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (hexane-ethyl acetate, 1:2 v/v) to afford the title compound as a colourless solid [yield 73%, m.p. 462-463 K; Rf = 0.71 (hexane-ethyl acetate, 1:2 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C–H = 0.93 Å for the aryl and 0.97 Å for the methylene H atoms. Uiso(H) = 1.2Ueq(C) for the aryl and the methylene H atoms. The distances of C–C in the solvated benzene ring were restrained to 1.39 (1) Å using command DFIX.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 cycles of arbitrary radius.
[Figure 2] Fig. 2. The C–H···O hydrogen bonds (dotted lines) in the crystal packing of (I). [Symmetry codes: (i) - x + 1, y + 0.5, - z + 3/2; (iii) - x + 1, y - 0.5, - z + 3/2.]
[Figure 3] Fig. 3. The C–H···π and ππ interactions (dotted lines) in (I). Cg denotes the ring centroids. [Symmetry codes: (ii) x, -y + 1/2, z - 1/2; (iv) x, - y + 1/2, z + 1/2; (v) - x + 1, - y + 1, - z + 1; (vi) - x + 1, y + 1/2, - z + 1/2.]
2-(4-Bromophenyl)-5,6-methylenedioxy-3-phenylsulfinyl-1-benzofuran benzene solvate top
Crystal data top
C21H13BrO4S·C6H6F(000) = 1056
Mr = 519.39Dx = 1.538 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6564 reflections
a = 13.8967 (7) Åθ = 2.2–27.5°
b = 12.6640 (7) ŵ = 1.96 mm1
c = 13.0469 (7) ÅT = 173 K
β = 102.418 (1)°Block, colorless
V = 2242.4 (2) Å30.40 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
4886 independent reflections
Radiation source: fine-focus sealed tube3946 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
Detector resolution: 10.0 pixels mm-1θmax = 27.0°, θmin = 1.5°
ϕ and ω scansh = 1717
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
k = 168
Tmin = 0.629, Tmax = 0.679l = 1516
13417 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)] = 0.036Hydrogen site location: difference Fourier map
wR(F2) = 0.102H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0572P)2 + 0.3212P]
where P = (Fo2 + 2Fc2)/3
4886 reflections(Δ/σ)max = 0.001
298 parametersΔρmax = 0.64 e Å3
6 restraintsΔρmin = 0.65 e Å3
Crystal data top
C21H13BrO4S·C6H6V = 2242.4 (2) Å3
Mr = 519.39Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.8967 (7) ŵ = 1.96 mm1
b = 12.6640 (7) ÅT = 173 K
c = 13.0469 (7) Å0.40 × 0.20 × 0.20 mm
β = 102.418 (1)°
Data collection top
Bruker SMART CCD
diffractometer
4886 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
3946 reflections with I > 2σ(I)
Tmin = 0.629, Tmax = 0.679Rint = 0.075
13417 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0366 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 1.02Δρmax = 0.64 e Å3
4886 reflectionsΔρmin = 0.65 e Å3
298 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
Br0.201403 (18)0.26805 (2)0.115664 (18)0.03840 (10)
S0.63758 (4)0.22232 (4)0.56951 (4)0.02291 (13)
O10.43951 (10)0.44110 (11)0.59753 (11)0.0246 (3)
O20.57823 (12)0.58271 (13)0.94388 (13)0.0359 (4)
O30.71273 (11)0.47027 (13)0.96114 (12)0.0311 (3)
O40.68316 (11)0.16954 (12)0.67099 (11)0.0302 (3)
C10.56264 (14)0.32535 (16)0.60145 (15)0.0224 (4)
C20.47437 (14)0.36076 (16)0.54372 (16)0.0226 (4)
C30.50610 (14)0.45414 (16)0.69083 (16)0.0230 (4)
C40.49371 (15)0.52551 (17)0.76854 (17)0.0267 (4)
H40.44000.57080.76190.032*
C50.56899 (16)0.52172 (16)0.85561 (17)0.0261 (4)
C60.66481 (17)0.54604 (19)1.01496 (17)0.0324 (5)
H6A0.64720.51361.07570.039*
H6B0.70880.60481.03870.039*
C70.64952 (15)0.45403 (17)0.86521 (16)0.0250 (4)
C80.66125 (15)0.38315 (16)0.78944 (16)0.0245 (4)
H80.71520.33810.79720.029*
C90.58448 (15)0.38419 (16)0.69831 (16)0.0227 (4)
C100.41034 (15)0.33635 (16)0.44190 (16)0.0234 (4)
C110.32404 (16)0.39505 (18)0.40747 (18)0.0296 (5)
H110.30820.44820.45020.036*
C120.26182 (16)0.37585 (19)0.31148 (18)0.0319 (5)
H120.20510.41600.28950.038*
C130.28519 (16)0.29598 (18)0.24839 (17)0.0277 (5)
C140.36932 (17)0.23670 (18)0.28017 (18)0.0300 (5)
H140.38420.18330.23720.036*
C150.43210 (17)0.25665 (17)0.37660 (19)0.0291 (5)
H150.48900.21660.39770.035*
C160.73086 (15)0.30455 (17)0.53476 (16)0.0243 (4)
C170.81941 (17)0.3206 (2)0.60380 (19)0.0423 (6)
H170.83250.28860.66950.051*
C180.8888 (2)0.3853 (3)0.5735 (2)0.0584 (9)
H180.94900.39710.61930.070*
C190.8689 (2)0.4326 (3)0.4751 (2)0.0530 (8)
H190.91530.47720.45610.064*
C200.78115 (18)0.4138 (2)0.40579 (19)0.0381 (6)
H200.76880.44430.33940.046*
C210.71121 (16)0.34943 (18)0.43497 (16)0.0284 (5)
H210.65170.33630.38840.034*
C220.0616 (2)0.5412 (3)0.1216 (2)0.0578 (8)
H220.11800.51660.10170.069*
C230.0017 (2)0.4709 (3)0.1512 (2)0.0629 (9)
H230.01240.39910.15160.076*
C240.0846 (2)0.5040 (5)0.1801 (3)0.0906 (16)
H240.12780.45510.19870.109*
C250.1041 (3)0.6067 (6)0.1817 (4)0.114 (2)
H250.16080.62790.20280.137*
C260.0441 (5)0.6831 (4)0.1536 (4)0.129 (3)
H260.05920.75450.15570.155*
C270.0434 (3)0.6476 (4)0.1207 (3)0.0869 (13)
H270.08600.69550.09950.104*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.04220 (16)0.04233 (17)0.02635 (14)0.00182 (10)0.00222 (10)0.00305 (10)
S0.0252 (3)0.0199 (3)0.0232 (3)0.00213 (19)0.0043 (2)0.0001 (2)
O10.0278 (7)0.0209 (7)0.0245 (7)0.0025 (6)0.0041 (6)0.0012 (6)
O20.0408 (9)0.0339 (9)0.0302 (8)0.0055 (7)0.0016 (7)0.0113 (7)
O30.0329 (8)0.0324 (8)0.0263 (8)0.0004 (7)0.0024 (6)0.0055 (7)
O40.0356 (8)0.0263 (8)0.0274 (8)0.0057 (6)0.0041 (6)0.0055 (6)
C10.0247 (10)0.0209 (10)0.0223 (10)0.0000 (8)0.0065 (8)0.0010 (8)
C20.0260 (10)0.0184 (10)0.0251 (10)0.0003 (8)0.0092 (8)0.0006 (8)
C30.0261 (10)0.0200 (10)0.0229 (10)0.0009 (8)0.0054 (8)0.0027 (8)
C40.0286 (11)0.0225 (11)0.0299 (11)0.0027 (8)0.0083 (9)0.0001 (9)
C50.0338 (11)0.0195 (10)0.0263 (11)0.0016 (8)0.0096 (9)0.0020 (8)
C60.0406 (12)0.0290 (12)0.0265 (11)0.0005 (10)0.0047 (9)0.0036 (9)
C70.0279 (10)0.0234 (10)0.0232 (10)0.0047 (8)0.0044 (8)0.0008 (8)
C80.0258 (10)0.0218 (10)0.0265 (10)0.0007 (8)0.0072 (8)0.0017 (9)
C90.0259 (10)0.0195 (10)0.0244 (10)0.0005 (8)0.0090 (8)0.0007 (8)
C100.0270 (10)0.0199 (10)0.0238 (10)0.0021 (8)0.0064 (8)0.0038 (8)
C110.0315 (11)0.0254 (11)0.0311 (11)0.0044 (9)0.0046 (9)0.0049 (9)
C120.0307 (11)0.0292 (12)0.0333 (12)0.0064 (9)0.0013 (9)0.0007 (10)
C130.0314 (11)0.0269 (11)0.0228 (10)0.0042 (9)0.0015 (8)0.0020 (9)
C140.0358 (12)0.0266 (11)0.0273 (11)0.0034 (9)0.0064 (9)0.0054 (9)
C150.0307 (11)0.0276 (11)0.0282 (11)0.0062 (9)0.0043 (9)0.0006 (9)
C160.0246 (10)0.0245 (10)0.0245 (10)0.0007 (8)0.0065 (8)0.0028 (9)
C170.0326 (12)0.0649 (18)0.0269 (12)0.0063 (12)0.0007 (10)0.0041 (12)
C180.0341 (14)0.095 (3)0.0395 (15)0.0256 (15)0.0062 (12)0.0027 (16)
C190.0452 (15)0.070 (2)0.0439 (15)0.0286 (14)0.0111 (12)0.0008 (15)
C200.0414 (13)0.0430 (15)0.0304 (12)0.0073 (11)0.0090 (10)0.0042 (11)
C210.0284 (10)0.0296 (11)0.0256 (10)0.0001 (9)0.0022 (9)0.0010 (9)
C220.0416 (15)0.085 (2)0.0443 (16)0.0091 (15)0.0035 (13)0.0037 (16)
C230.0460 (16)0.092 (3)0.0480 (17)0.0026 (17)0.0039 (14)0.0090 (18)
C240.0445 (18)0.177 (5)0.0487 (19)0.003 (2)0.0070 (15)0.038 (3)
C250.072 (3)0.176 (6)0.076 (3)0.057 (3)0.025 (2)0.081 (4)
C260.148 (5)0.089 (4)0.102 (4)0.060 (4)0.080 (4)0.049 (3)
C270.093 (3)0.076 (3)0.067 (2)0.003 (2)0.036 (2)0.000 (2)
Geometric parameters (Å, º) top
Br—C131.901 (2)C12—H120.9300
S—O41.4968 (15)C13—C141.376 (3)
S—C11.774 (2)C14—C151.391 (3)
S—C161.795 (2)C14—H140.9300
O1—C31.371 (2)C15—H150.9300
O1—C21.382 (2)C16—C171.375 (3)
O2—C51.370 (3)C16—C211.393 (3)
O2—C61.429 (3)C17—C181.387 (4)
O3—C71.381 (2)C17—H170.9300
O3—C61.435 (3)C18—C191.389 (4)
C1—C21.370 (3)C18—H180.9300
C1—C91.442 (3)C19—C201.374 (4)
C2—C101.464 (3)C19—H190.9300
C3—C91.391 (3)C20—C211.383 (3)
C3—C41.396 (3)C20—H200.9300
C4—C51.370 (3)C21—H210.9300
C4—H40.9300C22—C231.365 (5)
C5—C71.394 (3)C22—C271.370 (5)
C6—H6A0.9700C22—H220.9300
C6—H6B0.9700C23—C241.354 (4)
C7—C81.371 (3)C23—H230.9300
C8—C91.416 (3)C24—C251.330 (7)
C8—H80.9300C24—H240.9300
C10—C151.395 (3)C25—C261.377 (8)
C10—C111.400 (3)C25—H250.9300
C11—C121.382 (3)C26—C271.445 (8)
C11—H110.9300C26—H260.9300
C12—C131.386 (3)C27—H270.9300
O4—S—C1106.19 (9)C14—C13—C12120.8 (2)
O4—S—C16106.93 (9)C14—C13—Br119.17 (17)
C1—S—C1697.18 (10)C12—C13—Br120.07 (17)
C3—O1—C2107.24 (15)C13—C14—C15120.0 (2)
C5—O2—C6106.02 (17)C13—C14—H14120.0
C7—O3—C6105.75 (16)C15—C14—H14120.0
C2—C1—C9107.91 (17)C14—C15—C10120.5 (2)
C2—C1—S127.83 (16)C14—C15—H15119.8
C9—C1—S124.22 (15)C10—C15—H15119.8
C1—C2—O1109.40 (17)C17—C16—C21121.3 (2)
C1—C2—C10136.67 (19)C17—C16—S120.88 (17)
O1—C2—C10113.92 (17)C21—C16—S117.76 (16)
O1—C3—C9110.75 (17)C16—C17—C18118.7 (2)
O1—C3—C4123.88 (18)C16—C17—H17120.7
C9—C3—C4125.33 (19)C18—C17—H17120.7
C5—C4—C3112.83 (19)C17—C18—C19120.4 (2)
C5—C4—H4123.6C17—C18—H18119.8
C3—C4—H4123.6C19—C18—H18119.8
C4—C5—O2126.47 (19)C20—C19—C18120.3 (2)
C4—C5—C7123.47 (19)C20—C19—H19119.8
O2—C5—C7110.06 (19)C18—C19—H19119.8
O2—C6—O3108.32 (17)C19—C20—C21119.9 (2)
O2—C6—H6A110.0C19—C20—H20120.1
O3—C6—H6A110.0C21—C20—H20120.1
O2—C6—H6B110.0C20—C21—C16119.3 (2)
O3—C6—H6B110.0C20—C21—H21120.3
H6A—C6—H6B108.4C16—C21—H21120.3
C8—C7—O3126.87 (19)C23—C22—C27121.0 (4)
C8—C7—C5123.75 (19)C23—C22—H22119.5
O3—C7—C5109.38 (18)C27—C22—H22119.5
C7—C8—C9114.48 (18)C24—C23—C22121.0 (4)
C7—C8—H8122.8C24—C23—H23119.5
C9—C8—H8122.8C22—C23—H23119.5
C3—C9—C8120.13 (18)C25—C24—C23119.7 (5)
C3—C9—C1104.69 (17)C25—C24—H24120.2
C8—C9—C1135.18 (19)C23—C24—H24120.2
C15—C10—C11118.1 (2)C24—C25—C26123.1 (4)
C15—C10—C2122.52 (19)C24—C25—H25118.4
C11—C10—C2119.36 (18)C26—C25—H25118.4
C12—C11—C10121.5 (2)C25—C26—C27117.2 (4)
C12—C11—H11119.2C25—C26—H26121.4
C10—C11—H11119.2C27—C26—H26121.4
C11—C12—C13119.1 (2)C22—C27—C26118.0 (5)
C11—C12—H12120.5C22—C27—H27121.0
C13—C12—H12120.5C26—C27—H27121.0
O4—S—C1—C2144.86 (18)S—C1—C9—C3178.71 (15)
C16—S—C1—C2105.13 (19)C2—C1—C9—C8178.1 (2)
O4—S—C1—C932.39 (19)S—C1—C9—C80.4 (3)
C16—S—C1—C977.62 (18)C1—C2—C10—C151.9 (4)
C9—C1—C2—O11.4 (2)O1—C2—C10—C15179.02 (18)
S—C1—C2—O1179.01 (14)C1—C2—C10—C11177.7 (2)
C9—C1—C2—C10179.5 (2)O1—C2—C10—C111.4 (3)
S—C1—C2—C101.9 (4)C15—C10—C11—C120.4 (3)
C3—O1—C2—C11.2 (2)C2—C10—C11—C12179.2 (2)
C3—O1—C2—C10179.43 (16)C10—C11—C12—C130.6 (3)
C2—O1—C3—C90.6 (2)C11—C12—C13—C140.3 (3)
C2—O1—C3—C4177.09 (19)C11—C12—C13—Br179.72 (17)
O1—C3—C4—C5178.27 (18)C12—C13—C14—C150.0 (3)
C9—C3—C4—C50.9 (3)Br—C13—C14—C15179.35 (17)
C3—C4—C5—O2179.17 (19)C13—C14—C15—C100.2 (3)
C3—C4—C5—C70.2 (3)C11—C10—C15—C140.0 (3)
C6—O2—C5—C4176.6 (2)C2—C10—C15—C14179.6 (2)
C6—O2—C5—C74.3 (2)O4—S—C16—C178.5 (2)
C5—O2—C6—O36.8 (2)C1—S—C16—C17100.9 (2)
C7—O3—C6—O26.7 (2)O4—S—C16—C21170.16 (16)
C6—O3—C7—C8175.7 (2)C1—S—C16—C2180.45 (18)
C6—O3—C7—C54.1 (2)C21—C16—C17—C181.8 (4)
C4—C5—C7—C81.0 (3)S—C16—C17—C18179.6 (2)
O2—C5—C7—C8179.93 (19)C16—C17—C18—C190.2 (5)
C4—C5—C7—O3179.20 (19)C17—C18—C19—C201.5 (5)
O2—C5—C7—O30.1 (2)C18—C19—C20—C211.5 (5)
O3—C7—C8—C9179.72 (18)C19—C20—C21—C160.1 (4)
C5—C7—C8—C90.5 (3)C17—C16—C21—C201.8 (3)
O1—C3—C9—C8179.05 (17)S—C16—C21—C20179.57 (18)
C4—C3—C9—C81.4 (3)C27—C22—C23—C240.4 (5)
O1—C3—C9—C10.2 (2)C22—C23—C24—C251.3 (5)
C4—C3—C9—C1177.88 (19)C23—C24—C25—C261.0 (7)
C7—C8—C9—C30.6 (3)C24—C25—C26—C270.3 (7)
C7—C8—C9—C1178.4 (2)C23—C22—C27—C260.9 (5)
C2—C1—C9—C31.0 (2)C25—C26—C27—C221.2 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O4i0.932.433.290 (3)154
C14—H14···Cg1ii0.932.723.531 (3)147
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC21H13BrO4S·C6H6
Mr519.39
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)13.8967 (7), 12.6640 (7), 13.0469 (7)
β (°) 102.418 (1)
V3)2242.4 (2)
Z4
Radiation typeMo Kα
µ (mm1)1.96
Crystal size (mm)0.40 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2000)
Tmin, Tmax0.629, 0.679
No. of measured, independent and
observed [I > 2σ(I)] reflections
13417, 4886, 3946
Rint0.075
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.102, 1.02
No. of reflections4886
No. of parameters298
No. of restraints6
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.64, 0.65

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
C4—H4···O4i0.932.433.290 (3)153.7
C14—H14···Cg1ii0.932.723.531 (3)147.0
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x, y+1/2, z1/2.
 

References

First citationAkgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943.  Web of Science CrossRef PubMed CAS
First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationBruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationChoi, H. D., Seo, P. J., Lee, H. K., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o519–o520.  Web of Science CSD CrossRef IUCr Journals
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o849.  Web of Science CSD CrossRef IUCr Journals
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationHowlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283–289.  Web of Science CrossRef PubMed CAS
First citationReuss, S. H. von & König, W. A. (2004). Phytochemistry, 65, 3113–3118.  Web of Science PubMed
First citationSheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationTwyman, L. J. & Allsop, D. (1999). Tetrahedron Lett. 40, 9383–9384.  Web of Science CrossRef CAS

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