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

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

doi:10.1107/S1600536809037283

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2503

doi:10.1107/S1600536809037283

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

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 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 π–π 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 , 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 ).

Experimental

Crystal data

C₂₁H₁₃BrO₄S·C₆H₆
M_r = 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 ) T_min = 0.629, T_max = 0.679
13417 measured reflections
4886 independent reflections
3946 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 2001); 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: 10.1107/S1600536809037283/kp2232sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037283/kp2232Isup2.hkl

checkCIF report

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 S═O 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 π–π interactions between the benzene ring and the 4-bromophenyl ring of the neighbouring molecules. The Cg2···Cg3^v 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; R_f = 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.

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

	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.
	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.]
	Fig. 3. The C–H···π and π–π 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·C₆H₆	F(000) = 1056
M_r = 519.39	D_x = 1.538 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6564 reflections
a = 13.8967 (7) Å	θ = 2.2–27.5°
b = 12.6640 (7) Å	µ = 1.96 mm⁻¹
c = 13.0469 (7) Å	T = 173 K
β = 102.418 (1)°	Block, colorless
V = 2242.4 (2) Å³	0.40 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	4886 independent reflections
Radiation source: fine-focus sealed tube	3946 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 1.5°
ϕ and ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −16→8
T_min = 0.629, T_max = 0.679	l = −15→16
13417 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)] = 0.036	Hydrogen site location: difference Fourier map
wR(F²) = 0.102	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0572P)² + 0.3212P] where P = (F_o² + 2F_c²)/3
4886 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 0.64 e Å⁻³
6 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

C₂₁H₁₃BrO₄S·C₆H₆	V = 2242.4 (2) Å³
M_r = 519.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.8967 (7) Å	µ = 1.96 mm⁻¹
b = 12.6640 (7) Å	T = 173 K
c = 13.0469 (7) Å	0.40 × 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)
T_min = 0.629, T_max = 0.679	R_int = 0.075
13417 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	6 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.02	Δρ_max = 0.64 e Å⁻³
4886 reflections	Δρ_min = −0.65 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Br	0.201403 (18)	0.26805 (2)	0.115664 (18)	0.03840 (10)
S	0.63758 (4)	0.22232 (4)	0.56951 (4)	0.02291 (13)
O1	0.43951 (10)	0.44110 (11)	0.59753 (11)	0.0246 (3)
O2	0.57823 (12)	0.58271 (13)	0.94388 (13)	0.0359 (4)
O3	0.71273 (11)	0.47027 (13)	0.96114 (12)	0.0311 (3)
O4	0.68316 (11)	0.16954 (12)	0.67099 (11)	0.0302 (3)
C1	0.56264 (14)	0.32535 (16)	0.60145 (15)	0.0224 (4)
C2	0.47437 (14)	0.36076 (16)	0.54372 (16)	0.0226 (4)
C3	0.50610 (14)	0.45414 (16)	0.69083 (16)	0.0230 (4)
C4	0.49371 (15)	0.52551 (17)	0.76854 (17)	0.0267 (4)
H4	0.4400	0.5708	0.7619	0.032*
C5	0.56899 (16)	0.52172 (16)	0.85561 (17)	0.0261 (4)
C6	0.66481 (17)	0.54604 (19)	1.01496 (17)	0.0324 (5)
H6A	0.6472	0.5136	1.0757	0.039*
H6B	0.7088	0.6048	1.0387	0.039*
C7	0.64952 (15)	0.45403 (17)	0.86521 (16)	0.0250 (4)
C8	0.66125 (15)	0.38315 (16)	0.78944 (16)	0.0245 (4)
H8	0.7152	0.3381	0.7972	0.029*
C9	0.58448 (15)	0.38419 (16)	0.69831 (16)	0.0227 (4)
C10	0.41034 (15)	0.33635 (16)	0.44190 (16)	0.0234 (4)
C11	0.32404 (16)	0.39505 (18)	0.40747 (18)	0.0296 (5)
H11	0.3082	0.4482	0.4502	0.036*
C12	0.26182 (16)	0.37585 (19)	0.31148 (18)	0.0319 (5)
H12	0.2051	0.4160	0.2895	0.038*
C13	0.28519 (16)	0.29598 (18)	0.24839 (17)	0.0277 (5)
C14	0.36932 (17)	0.23670 (18)	0.28017 (18)	0.0300 (5)
H14	0.3842	0.1833	0.2372	0.036*
C15	0.43210 (17)	0.25665 (17)	0.37660 (19)	0.0291 (5)
H15	0.4890	0.2166	0.3977	0.035*
C16	0.73086 (15)	0.30455 (17)	0.53476 (16)	0.0243 (4)
C17	0.81941 (17)	0.3206 (2)	0.60380 (19)	0.0423 (6)
H17	0.8325	0.2886	0.6695	0.051*
C18	0.8888 (2)	0.3853 (3)	0.5735 (2)	0.0584 (9)
H18	0.9490	0.3971	0.6193	0.070*
C19	0.8689 (2)	0.4326 (3)	0.4751 (2)	0.0530 (8)
H19	0.9153	0.4772	0.4561	0.064*
C20	0.78115 (18)	0.4138 (2)	0.40579 (19)	0.0381 (6)
H20	0.7688	0.4443	0.3394	0.046*
C21	0.71121 (16)	0.34943 (18)	0.43497 (16)	0.0284 (5)
H21	0.6517	0.3363	0.3884	0.034*
C22	0.0616 (2)	0.5412 (3)	0.1216 (2)	0.0578 (8)
H22	0.1180	0.5166	0.1017	0.069*
C23	−0.0017 (2)	0.4709 (3)	0.1512 (2)	0.0629 (9)
H23	0.0124	0.3991	0.1516	0.076*
C24	−0.0846 (2)	0.5040 (5)	0.1801 (3)	0.0906 (16)
H24	−0.1278	0.4551	0.1987	0.109*
C25	−0.1041 (3)	0.6067 (6)	0.1817 (4)	0.114 (2)
H25	−0.1608	0.6279	0.2028	0.137*
C26	−0.0441 (5)	0.6831 (4)	0.1536 (4)	0.129 (3)
H26	−0.0592	0.7545	0.1557	0.155*
C27	0.0434 (3)	0.6476 (4)	0.1207 (3)	0.0869 (13)
H27	0.0860	0.6955	0.0995	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.04220 (16)	0.04233 (17)	0.02635 (14)	−0.00182 (10)	−0.00222 (10)	−0.00305 (10)
S	0.0252 (3)	0.0199 (3)	0.0232 (3)	0.00213 (19)	0.0043 (2)	−0.0001 (2)
O1	0.0278 (7)	0.0209 (7)	0.0245 (7)	0.0025 (6)	0.0041 (6)	−0.0012 (6)
O2	0.0408 (9)	0.0339 (9)	0.0302 (8)	0.0055 (7)	0.0016 (7)	−0.0113 (7)
O3	0.0329 (8)	0.0324 (8)	0.0263 (8)	0.0004 (7)	0.0024 (6)	−0.0055 (7)
O4	0.0356 (8)	0.0263 (8)	0.0274 (8)	0.0057 (6)	0.0041 (6)	0.0055 (6)
C1	0.0247 (10)	0.0209 (10)	0.0223 (10)	0.0000 (8)	0.0065 (8)	0.0010 (8)
C2	0.0260 (10)	0.0184 (10)	0.0251 (10)	0.0003 (8)	0.0092 (8)	0.0006 (8)
C3	0.0261 (10)	0.0200 (10)	0.0229 (10)	−0.0009 (8)	0.0054 (8)	0.0027 (8)
C4	0.0286 (11)	0.0225 (11)	0.0299 (11)	0.0027 (8)	0.0083 (9)	−0.0001 (9)
C5	0.0338 (11)	0.0195 (10)	0.0263 (11)	−0.0016 (8)	0.0096 (9)	−0.0020 (8)
C6	0.0406 (12)	0.0290 (12)	0.0265 (11)	−0.0005 (10)	0.0047 (9)	−0.0036 (9)
C7	0.0279 (10)	0.0234 (10)	0.0232 (10)	−0.0047 (8)	0.0044 (8)	0.0008 (8)
C8	0.0258 (10)	0.0218 (10)	0.0265 (10)	0.0007 (8)	0.0072 (8)	0.0017 (9)
C9	0.0259 (10)	0.0195 (10)	0.0244 (10)	−0.0005 (8)	0.0090 (8)	0.0007 (8)
C10	0.0270 (10)	0.0199 (10)	0.0238 (10)	−0.0021 (8)	0.0064 (8)	0.0038 (8)
C11	0.0315 (11)	0.0254 (11)	0.0311 (11)	0.0044 (9)	0.0046 (9)	−0.0049 (9)
C12	0.0307 (11)	0.0292 (12)	0.0333 (12)	0.0064 (9)	0.0013 (9)	−0.0007 (10)
C13	0.0314 (11)	0.0269 (11)	0.0228 (10)	−0.0042 (9)	0.0015 (8)	0.0020 (9)
C14	0.0358 (12)	0.0266 (11)	0.0273 (11)	0.0034 (9)	0.0064 (9)	−0.0054 (9)
C15	0.0307 (11)	0.0276 (11)	0.0282 (11)	0.0062 (9)	0.0043 (9)	0.0006 (9)
C16	0.0246 (10)	0.0245 (10)	0.0245 (10)	−0.0007 (8)	0.0065 (8)	−0.0028 (9)
C17	0.0326 (12)	0.0649 (18)	0.0269 (12)	−0.0063 (12)	0.0007 (10)	0.0041 (12)
C18	0.0341 (14)	0.095 (3)	0.0395 (15)	−0.0256 (15)	−0.0062 (12)	0.0027 (16)
C19	0.0452 (15)	0.070 (2)	0.0439 (15)	−0.0286 (14)	0.0111 (12)	0.0008 (15)
C20	0.0414 (13)	0.0430 (15)	0.0304 (12)	−0.0073 (11)	0.0090 (10)	0.0042 (11)
C21	0.0284 (10)	0.0296 (11)	0.0256 (10)	0.0001 (9)	0.0022 (9)	−0.0010 (9)
C22	0.0416 (15)	0.085 (2)	0.0443 (16)	0.0091 (15)	0.0035 (13)	−0.0037 (16)
C23	0.0460 (16)	0.092 (3)	0.0480 (17)	0.0026 (17)	0.0039 (14)	−0.0090 (18)
C24	0.0445 (18)	0.177 (5)	0.0487 (19)	−0.003 (2)	0.0070 (15)	−0.038 (3)
C25	0.072 (3)	0.176 (6)	0.076 (3)	0.057 (3)	−0.025 (2)	−0.081 (4)
C26	0.148 (5)	0.089 (4)	0.102 (4)	0.060 (4)	−0.080 (4)	−0.049 (3)
C27	0.093 (3)	0.076 (3)	0.067 (2)	0.003 (2)	−0.036 (2)	0.000 (2)

Geometric parameters (Å, º) top

Br—C13	1.901 (2)	C12—H12	0.9300
S—O4	1.4968 (15)	C13—C14	1.376 (3)
S—C1	1.774 (2)	C14—C15	1.391 (3)
S—C16	1.795 (2)	C14—H14	0.9300
O1—C3	1.371 (2)	C15—H15	0.9300
O1—C2	1.382 (2)	C16—C17	1.375 (3)
O2—C5	1.370 (3)	C16—C21	1.393 (3)
O2—C6	1.429 (3)	C17—C18	1.387 (4)
O3—C7	1.381 (2)	C17—H17	0.9300
O3—C6	1.435 (3)	C18—C19	1.389 (4)
C1—C2	1.370 (3)	C18—H18	0.9300
C1—C9	1.442 (3)	C19—C20	1.374 (4)
C2—C10	1.464 (3)	C19—H19	0.9300
C3—C9	1.391 (3)	C20—C21	1.383 (3)
C3—C4	1.396 (3)	C20—H20	0.9300
C4—C5	1.370 (3)	C21—H21	0.9300
C4—H4	0.9300	C22—C23	1.365 (5)
C5—C7	1.394 (3)	C22—C27	1.370 (5)
C6—H6A	0.9700	C22—H22	0.9300
C6—H6B	0.9700	C23—C24	1.354 (4)
C7—C8	1.371 (3)	C23—H23	0.9300
C8—C9	1.416 (3)	C24—C25	1.330 (7)
C8—H8	0.9300	C24—H24	0.9300
C10—C15	1.395 (3)	C25—C26	1.377 (8)
C10—C11	1.400 (3)	C25—H25	0.9300
C11—C12	1.382 (3)	C26—C27	1.445 (8)
C11—H11	0.9300	C26—H26	0.9300
C12—C13	1.386 (3)	C27—H27	0.9300

O4—S—C1	106.19 (9)	C14—C13—C12	120.8 (2)
O4—S—C16	106.93 (9)	C14—C13—Br	119.17 (17)
C1—S—C16	97.18 (10)	C12—C13—Br	120.07 (17)
C3—O1—C2	107.24 (15)	C13—C14—C15	120.0 (2)
C5—O2—C6	106.02 (17)	C13—C14—H14	120.0
C7—O3—C6	105.75 (16)	C15—C14—H14	120.0
C2—C1—C9	107.91 (17)	C14—C15—C10	120.5 (2)
C2—C1—S	127.83 (16)	C14—C15—H15	119.8
C9—C1—S	124.22 (15)	C10—C15—H15	119.8
C1—C2—O1	109.40 (17)	C17—C16—C21	121.3 (2)
C1—C2—C10	136.67 (19)	C17—C16—S	120.88 (17)
O1—C2—C10	113.92 (17)	C21—C16—S	117.76 (16)
O1—C3—C9	110.75 (17)	C16—C17—C18	118.7 (2)
O1—C3—C4	123.88 (18)	C16—C17—H17	120.7
C9—C3—C4	125.33 (19)	C18—C17—H17	120.7
C5—C4—C3	112.83 (19)	C17—C18—C19	120.4 (2)
C5—C4—H4	123.6	C17—C18—H18	119.8
C3—C4—H4	123.6	C19—C18—H18	119.8
C4—C5—O2	126.47 (19)	C20—C19—C18	120.3 (2)
C4—C5—C7	123.47 (19)	C20—C19—H19	119.8
O2—C5—C7	110.06 (19)	C18—C19—H19	119.8
O2—C6—O3	108.32 (17)	C19—C20—C21	119.9 (2)
O2—C6—H6A	110.0	C19—C20—H20	120.1
O3—C6—H6A	110.0	C21—C20—H20	120.1
O2—C6—H6B	110.0	C20—C21—C16	119.3 (2)
O3—C6—H6B	110.0	C20—C21—H21	120.3
H6A—C6—H6B	108.4	C16—C21—H21	120.3
C8—C7—O3	126.87 (19)	C23—C22—C27	121.0 (4)
C8—C7—C5	123.75 (19)	C23—C22—H22	119.5
O3—C7—C5	109.38 (18)	C27—C22—H22	119.5
C7—C8—C9	114.48 (18)	C24—C23—C22	121.0 (4)
C7—C8—H8	122.8	C24—C23—H23	119.5
C9—C8—H8	122.8	C22—C23—H23	119.5
C3—C9—C8	120.13 (18)	C25—C24—C23	119.7 (5)
C3—C9—C1	104.69 (17)	C25—C24—H24	120.2
C8—C9—C1	135.18 (19)	C23—C24—H24	120.2
C15—C10—C11	118.1 (2)	C24—C25—C26	123.1 (4)
C15—C10—C2	122.52 (19)	C24—C25—H25	118.4
C11—C10—C2	119.36 (18)	C26—C25—H25	118.4
C12—C11—C10	121.5 (2)	C25—C26—C27	117.2 (4)
C12—C11—H11	119.2	C25—C26—H26	121.4
C10—C11—H11	119.2	C27—C26—H26	121.4
C11—C12—C13	119.1 (2)	C22—C27—C26	118.0 (5)
C11—C12—H12	120.5	C22—C27—H27	121.0
C13—C12—H12	120.5	C26—C27—H27	121.0

O4—S—C1—C2	−144.86 (18)	S—C1—C9—C3	−178.71 (15)
C16—S—C1—C2	105.13 (19)	C2—C1—C9—C8	178.1 (2)
O4—S—C1—C9	32.39 (19)	S—C1—C9—C8	0.4 (3)
C16—S—C1—C9	−77.62 (18)	C1—C2—C10—C15	1.9 (4)
C9—C1—C2—O1	1.4 (2)	O1—C2—C10—C15	−179.02 (18)
S—C1—C2—O1	179.01 (14)	C1—C2—C10—C11	−177.7 (2)
C9—C1—C2—C10	−179.5 (2)	O1—C2—C10—C11	1.4 (3)
S—C1—C2—C10	−1.9 (4)	C15—C10—C11—C12	−0.4 (3)
C3—O1—C2—C1	−1.2 (2)	C2—C10—C11—C12	179.2 (2)
C3—O1—C2—C10	179.43 (16)	C10—C11—C12—C13	0.6 (3)
C2—O1—C3—C9	0.6 (2)	C11—C12—C13—C14	−0.3 (3)
C2—O1—C3—C4	−177.09 (19)	C11—C12—C13—Br	−179.72 (17)
O1—C3—C4—C5	178.27 (18)	C12—C13—C14—C15	0.0 (3)
C9—C3—C4—C5	0.9 (3)	Br—C13—C14—C15	179.35 (17)
C3—C4—C5—O2	179.17 (19)	C13—C14—C15—C10	0.2 (3)
C3—C4—C5—C7	0.2 (3)	C11—C10—C15—C14	0.0 (3)
C6—O2—C5—C4	176.6 (2)	C2—C10—C15—C14	−179.6 (2)
C6—O2—C5—C7	−4.3 (2)	O4—S—C16—C17	−8.5 (2)
C5—O2—C6—O3	6.8 (2)	C1—S—C16—C17	100.9 (2)
C7—O3—C6—O2	−6.7 (2)	O4—S—C16—C21	170.16 (16)
C6—O3—C7—C8	−175.7 (2)	C1—S—C16—C21	−80.45 (18)
C6—O3—C7—C5	4.1 (2)	C21—C16—C17—C18	1.8 (4)
C4—C5—C7—C8	−1.0 (3)	S—C16—C17—C18	−179.6 (2)
O2—C5—C7—C8	179.93 (19)	C16—C17—C18—C19	−0.2 (5)
C4—C5—C7—O3	179.20 (19)	C17—C18—C19—C20	−1.5 (5)
O2—C5—C7—O3	0.1 (2)	C18—C19—C20—C21	1.5 (5)
O3—C7—C8—C9	−179.72 (18)	C19—C20—C21—C16	0.1 (4)
C5—C7—C8—C9	0.5 (3)	C17—C16—C21—C20	−1.8 (3)
O1—C3—C9—C8	−179.05 (17)	S—C16—C21—C20	179.57 (18)
C4—C3—C9—C8	−1.4 (3)	C27—C22—C23—C24	0.4 (5)
O1—C3—C9—C1	0.2 (2)	C22—C23—C24—C25	−1.3 (5)
C4—C3—C9—C1	177.88 (19)	C23—C24—C25—C26	1.0 (7)
C7—C8—C9—C3	0.6 (3)	C24—C25—C26—C27	0.3 (7)
C7—C8—C9—C1	−178.4 (2)	C23—C22—C27—C26	0.9 (5)
C2—C1—C9—C3	−1.0 (2)	C25—C26—C27—C22	−1.2 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+1/2, −z+3/2; (ii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₃BrO₄S·C₆H₆
M_r	519.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	13.8967 (7), 12.6640 (7), 13.0469 (7)
β (°)	102.418 (1)
V (Å³)	2242.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.96
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.629, 0.679
No. of measured, independent and observed [I > 2σ(I)] reflections	13417, 4886, 3946
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.102, 1.02
No. of reflections	4886
No. of parameters	298
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
C4—H4···O4ⁱ	0.93	2.43	3.290 (3)	153.7
C14—H14···Cg1ⁱⁱ	0.93	2.72	3.531 (3)	147.0

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, −y+1/2, z−1/2.

References

Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943. Web of Science CrossRef PubMed CAS Google Scholar
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, 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 Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o849. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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. Web of Science CrossRef PubMed CAS Google Scholar
Reuss, S. H. von & König, W. A. (2004). Phytochemistry, 65, 3113–3118. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Twyman, L. J. & Allsop, D. (1999). Tetrahedron Lett. 40, 9383–9384. Web of Science CrossRef CAS Google Scholar

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Volume 65| Part 10| October 2009| Page o2503

doi:10.1107/S1600536809037283

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

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