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organic compounds
3-(4-Bromophenylsulfinyl)-5-chloro-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
In the title compound, C15H10BrClO2S, the 4-bromophenyl ring makes a dihedral angle of 86.85 (6)° with the mean plane [mean deviation = 0.009 (2) Å] of the benzofuran fragment. In the crystal, molecules are linked by slipped π–π interactions between the benzene and the furan rings of adjacent molecules [centroid–centroid distance = 3.884 (2), interplanar distance = 3.369 (2) and slippage = 1.945 (2) Å], and between the 4-bromophenyl rings of adjacent molecules [centroid–centroid distance = 3.882 (2), interplanar distance = 3.552 (2) and slippage = 1.566 (2) Å]. A Br⋯Br [3.6446 (4) Å] halogen interaction is also observed.
Related literature
For background information and the crystal structures of related compounds, see: Choi et al. (2008, 2010
).
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009
); 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
https://doi.org/10.1107/S1600536812025846/ds2198sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025846/ds2198Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812025846/ds2198Isup3.cml
3-Chloroperoxybenzoic acid (77%, 202 mg, 0.9 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-5-chloro-2-methyl-1-benzofuran (283 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
(hexane/ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 73%, m.p. 395–396 K; Rf = 0.44 (hexane/ethyl acetate, 2:1 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.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. The positions of methyl hydrogens were optimized rotationally.
As a part of our ongoing study of 5-chloro-2-methyl-1-benzofuran derivatives containing 3-phenylsulfonyl (Choi et al., 2008) and 3-(4-fluorophenylsulfonyl) (Choi et al., 2010) substituents, we report herein the
of the title compound.In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.009 (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 fragment is 86.85 (6)°. In the π···π interactions; the first one between the benzene and the furan rings of adjacent molecules, with a Cg1···Cg2i distance of 3.884 (2) Å and an interplanar distance of 3.369 (2) Å resulting in a slippage of 1.945 (2) Å (Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively), and the second one between the 4-bromophenyl rings of adjacent molecules, with a Cg3···Cg3ii distance of 3.882 (2) Å and an interplanar distance of 3.552 (2) Å resulting in a slippage of 1.566 (2) Å (Cg3 is the centroid of the C10–C15 benzene ring). The crystal packing (Fig. 2) also exhibits a Br···Br contact at [3.6446 (4) Å].
(Fig. 2), molecules are connected by slippedFor background information and the crystal structures of related compounds, see: Choi et al. (2008, 2010).
Data collection: APEX2 (Bruker, 2009); cell
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).C15H10BrClO2S | Z = 2 |
Mr = 369.65 | F(000) = 368 |
Triclinic, P1 | Dx = 1.725 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.4192 (1) Å | Cell parameters from 7922 reflections |
b = 9.9185 (2) Å | θ = 2.5–28.3° |
c = 11.7755 (2) Å | µ = 3.22 mm−1 |
α = 100.681 (1)° | T = 173 K |
β = 92.113 (1)° | Block, colourless |
γ = 104.168 (1)° | 0.38 × 0.31 × 0.27 mm |
V = 711.67 (2) Å3 |
Bruker SMART APEXII CCD diffractometer | 3529 independent reflections |
Radiation source: rotating anode | 3236 reflections with I > 2σ(I) |
Graphite multilayer monochromator | Rint = 0.034 |
Detector resolution: 10.0 pixels mm-1 | θmax = 28.3°, θmin = 1.8° |
φ and ω scans | h = −8→8 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −13→13 |
Tmin = 0.374, Tmax = 0.475 | l = −15→15 |
13131 measured reflections |
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)] = 0.031 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0418P)2 + 0.3308P] where P = (Fo2 + 2Fc2)/3 |
3529 reflections | (Δ/σ)max = 0.001 |
182 parameters | Δρmax = 0.55 e Å−3 |
0 restraints | Δρmin = −0.76 e Å−3 |
C15H10BrClO2S | γ = 104.168 (1)° |
Mr = 369.65 | V = 711.67 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.4192 (1) Å | Mo Kα radiation |
b = 9.9185 (2) Å | µ = 3.22 mm−1 |
c = 11.7755 (2) Å | T = 173 K |
α = 100.681 (1)° | 0.38 × 0.31 × 0.27 mm |
β = 92.113 (1)° |
Bruker SMART APEXII CCD diffractometer | 3529 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3236 reflections with I > 2σ(I) |
Tmin = 0.374, Tmax = 0.475 | Rint = 0.034 |
13131 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.55 e Å−3 |
3529 reflections | Δρmin = −0.76 e Å−3 |
182 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.73945 (4) | 0.92053 (2) | 0.917091 (18) | 0.03412 (8) | |
Cl1 | −0.34796 (9) | 0.39254 (7) | 0.44410 (7) | 0.05267 (19) | |
S1 | 0.18432 (8) | 0.27154 (5) | 0.84285 (4) | 0.02666 (11) | |
O1 | 0.3068 (2) | 0.10245 (15) | 0.53223 (12) | 0.0280 (3) | |
O2 | −0.0436 (3) | 0.27377 (19) | 0.86385 (15) | 0.0408 (4) | |
C1 | 0.1970 (3) | 0.21347 (19) | 0.69398 (16) | 0.0221 (3) | |
C2 | 0.0811 (3) | 0.23994 (19) | 0.59651 (16) | 0.0218 (3) | |
C3 | −0.0758 (3) | 0.3123 (2) | 0.58146 (19) | 0.0273 (4) | |
H3 | −0.1307 | 0.3616 | 0.6456 | 0.033* | |
C4 | −0.1474 (3) | 0.3084 (2) | 0.4682 (2) | 0.0329 (5) | |
C5 | −0.0676 (4) | 0.2384 (3) | 0.3725 (2) | 0.0381 (5) | |
H5 | −0.1203 | 0.2402 | 0.2965 | 0.046* | |
C6 | 0.0869 (4) | 0.1664 (3) | 0.38686 (19) | 0.0353 (5) | |
H6 | 0.1427 | 0.1179 | 0.3225 | 0.042* | |
C7 | 0.1560 (3) | 0.1686 (2) | 0.49963 (17) | 0.0254 (4) | |
C8 | 0.3276 (3) | 0.1306 (2) | 0.65100 (18) | 0.0253 (4) | |
C9 | 0.4833 (4) | 0.0697 (2) | 0.7071 (2) | 0.0357 (5) | |
H9A | 0.6304 | 0.1255 | 0.7026 | 0.054* | |
H9B | 0.4668 | −0.0287 | 0.6672 | 0.054* | |
H9C | 0.4555 | 0.0720 | 0.7886 | 0.054* | |
C10 | 0.3331 (3) | 0.4532 (2) | 0.85442 (15) | 0.0222 (3) | |
C11 | 0.2396 (3) | 0.5607 (2) | 0.89910 (18) | 0.0283 (4) | |
H11 | 0.0936 | 0.5387 | 0.9172 | 0.034* | |
C12 | 0.3588 (3) | 0.7010 (2) | 0.91761 (18) | 0.0296 (4) | |
H12 | 0.2961 | 0.7758 | 0.9486 | 0.036* | |
C13 | 0.5709 (3) | 0.7301 (2) | 0.89001 (16) | 0.0247 (4) | |
C14 | 0.6662 (3) | 0.6227 (2) | 0.84636 (19) | 0.0294 (4) | |
H14 | 0.8119 | 0.6448 | 0.8279 | 0.035* | |
C15 | 0.5474 (3) | 0.4829 (2) | 0.82977 (19) | 0.0292 (4) | |
H15 | 0.6119 | 0.4080 | 0.8018 | 0.035* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.04322 (14) | 0.02544 (12) | 0.02911 (12) | 0.00304 (9) | 0.00126 (9) | 0.00208 (8) |
Cl1 | 0.0273 (3) | 0.0545 (4) | 0.0839 (5) | 0.0083 (2) | −0.0072 (3) | 0.0384 (4) |
S1 | 0.0281 (2) | 0.0293 (2) | 0.0188 (2) | 0.00123 (18) | 0.00349 (17) | 0.00343 (18) |
O1 | 0.0258 (7) | 0.0302 (7) | 0.0268 (7) | 0.0092 (6) | 0.0044 (5) | −0.0010 (6) |
O2 | 0.0277 (8) | 0.0484 (9) | 0.0358 (8) | −0.0032 (7) | 0.0136 (6) | −0.0022 (7) |
C1 | 0.0210 (8) | 0.0223 (8) | 0.0210 (8) | 0.0032 (7) | 0.0012 (7) | 0.0024 (7) |
C2 | 0.0194 (8) | 0.0224 (8) | 0.0214 (8) | 0.0020 (7) | 0.0022 (7) | 0.0032 (7) |
C3 | 0.0207 (9) | 0.0270 (9) | 0.0344 (10) | 0.0038 (7) | 0.0034 (7) | 0.0090 (8) |
C4 | 0.0203 (9) | 0.0330 (10) | 0.0460 (12) | 0.0002 (8) | −0.0024 (8) | 0.0195 (9) |
C5 | 0.0302 (11) | 0.0500 (13) | 0.0286 (10) | −0.0052 (9) | −0.0063 (8) | 0.0165 (10) |
C6 | 0.0338 (11) | 0.0448 (12) | 0.0215 (9) | 0.0014 (9) | 0.0033 (8) | 0.0035 (9) |
C7 | 0.0208 (8) | 0.0290 (9) | 0.0233 (9) | 0.0024 (7) | 0.0026 (7) | 0.0025 (7) |
C8 | 0.0220 (9) | 0.0233 (8) | 0.0283 (9) | 0.0030 (7) | 0.0014 (7) | 0.0032 (7) |
C9 | 0.0286 (10) | 0.0325 (11) | 0.0471 (13) | 0.0110 (8) | −0.0020 (9) | 0.0075 (10) |
C10 | 0.0216 (8) | 0.0264 (9) | 0.0160 (8) | 0.0043 (7) | 0.0001 (6) | 0.0002 (7) |
C11 | 0.0218 (9) | 0.0363 (10) | 0.0279 (10) | 0.0105 (8) | 0.0053 (7) | 0.0042 (8) |
C12 | 0.0308 (10) | 0.0311 (10) | 0.0290 (10) | 0.0150 (8) | 0.0053 (8) | 0.0014 (8) |
C13 | 0.0287 (9) | 0.0246 (9) | 0.0189 (8) | 0.0057 (7) | −0.0013 (7) | 0.0022 (7) |
C14 | 0.0215 (9) | 0.0316 (10) | 0.0337 (10) | 0.0067 (8) | 0.0054 (8) | 0.0026 (8) |
C15 | 0.0251 (9) | 0.0290 (10) | 0.0323 (10) | 0.0090 (8) | 0.0087 (8) | −0.0005 (8) |
Br1—C13 | 1.895 (2) | C5—H5 | 0.9500 |
Br1—Br1i | 3.6446 (4) | C6—C7 | 1.379 (3) |
Cl1—C4 | 1.738 (2) | C6—H6 | 0.9500 |
Cl1—Cl1ii | 3.3576 (15) | C8—C9 | 1.482 (3) |
S1—O2 | 1.4973 (16) | C9—H9A | 0.9800 |
S1—C1 | 1.7522 (19) | C9—H9B | 0.9800 |
S1—C10 | 1.798 (2) | C9—H9C | 0.9800 |
O1—C8 | 1.369 (2) | C10—C11 | 1.380 (3) |
O1—C7 | 1.375 (2) | C10—C15 | 1.388 (3) |
C1—C8 | 1.360 (3) | C11—C12 | 1.387 (3) |
C1—C2 | 1.444 (3) | C11—H11 | 0.9500 |
C2—C7 | 1.393 (3) | C12—C13 | 1.385 (3) |
C2—C3 | 1.396 (3) | C12—H12 | 0.9500 |
C3—C4 | 1.386 (3) | C13—C14 | 1.383 (3) |
C3—H3 | 0.9500 | C14—C15 | 1.383 (3) |
C4—C5 | 1.392 (3) | C14—H14 | 0.9500 |
C5—C6 | 1.378 (4) | C15—H15 | 0.9500 |
C13—Br1—Br1i | 129.17 (6) | C1—C8—O1 | 110.68 (17) |
C4—Cl1—Cl1ii | 147.84 (10) | C1—C8—C9 | 132.7 (2) |
O2—S1—C1 | 108.52 (9) | O1—C8—C9 | 116.58 (17) |
O2—S1—C10 | 106.57 (9) | C8—C9—H9A | 109.5 |
C1—S1—C10 | 98.01 (9) | C8—C9—H9B | 109.5 |
C8—O1—C7 | 106.55 (14) | H9A—C9—H9B | 109.5 |
C8—C1—C2 | 107.50 (16) | C8—C9—H9C | 109.5 |
C8—C1—S1 | 123.01 (15) | H9A—C9—H9C | 109.5 |
C2—C1—S1 | 129.49 (14) | H9B—C9—H9C | 109.5 |
C7—C2—C3 | 119.56 (18) | C11—C10—C15 | 120.93 (18) |
C7—C2—C1 | 104.41 (16) | C11—C10—S1 | 119.38 (15) |
C3—C2—C1 | 136.02 (18) | C15—C10—S1 | 119.34 (15) |
C4—C3—C2 | 116.62 (19) | C10—C11—C12 | 119.95 (18) |
C4—C3—H3 | 121.7 | C10—C11—H11 | 120.0 |
C2—C3—H3 | 121.7 | C12—C11—H11 | 120.0 |
C3—C4—C5 | 122.8 (2) | C13—C12—C11 | 118.80 (18) |
C3—C4—Cl1 | 118.67 (18) | C13—C12—H12 | 120.6 |
C5—C4—Cl1 | 118.47 (17) | C11—C12—H12 | 120.6 |
C6—C5—C4 | 120.8 (2) | C14—C13—C12 | 121.50 (19) |
C6—C5—H5 | 119.6 | C14—C13—Br1 | 118.71 (15) |
C4—C5—H5 | 119.6 | C12—C13—Br1 | 119.75 (15) |
C5—C6—C7 | 116.4 (2) | C13—C14—C15 | 119.41 (18) |
C5—C6—H6 | 121.8 | C13—C14—H14 | 120.3 |
C7—C6—H6 | 121.8 | C15—C14—H14 | 120.3 |
O1—C7—C6 | 125.35 (18) | C14—C15—C10 | 119.37 (18) |
O1—C7—C2 | 110.85 (17) | C14—C15—H15 | 120.3 |
C6—C7—C2 | 123.8 (2) | C10—C15—H15 | 120.3 |
O2—S1—C1—C8 | −144.10 (17) | C1—C2—C7—C6 | −179.82 (19) |
C10—S1—C1—C8 | 105.36 (17) | C2—C1—C8—O1 | 0.7 (2) |
O2—S1—C1—C2 | 35.8 (2) | S1—C1—C8—O1 | −179.37 (13) |
C10—S1—C1—C2 | −74.70 (18) | C2—C1—C8—C9 | 179.8 (2) |
C8—C1—C2—C7 | −0.4 (2) | S1—C1—C8—C9 | −0.3 (3) |
S1—C1—C2—C7 | 179.69 (15) | C7—O1—C8—C1 | −0.7 (2) |
C8—C1—C2—C3 | 178.4 (2) | C7—O1—C8—C9 | −179.98 (17) |
S1—C1—C2—C3 | −1.6 (3) | O2—S1—C10—C11 | 11.79 (19) |
C7—C2—C3—C4 | −0.2 (3) | C1—S1—C10—C11 | 123.91 (16) |
C1—C2—C3—C4 | −178.8 (2) | O2—S1—C10—C15 | −174.93 (16) |
C2—C3—C4—C5 | −0.9 (3) | C1—S1—C10—C15 | −62.81 (18) |
C2—C3—C4—Cl1 | 178.31 (14) | C15—C10—C11—C12 | 1.4 (3) |
Cl1ii—Cl1—C4—C3 | 8.9 (3) | S1—C10—C11—C12 | 174.58 (16) |
Cl1ii—Cl1—C4—C5 | −171.87 (13) | C10—C11—C12—C13 | 0.3 (3) |
C3—C4—C5—C6 | 1.1 (3) | C11—C12—C13—C14 | −1.0 (3) |
Cl1—C4—C5—C6 | −178.09 (17) | C11—C12—C13—Br1 | −178.79 (15) |
C4—C5—C6—C7 | −0.2 (3) | Br1i—Br1—C13—C14 | −52.56 (18) |
C8—O1—C7—C6 | −179.8 (2) | Br1i—Br1—C13—C12 | 125.32 (15) |
C8—O1—C7—C2 | 0.5 (2) | C12—C13—C14—C15 | 0.0 (3) |
C5—C6—C7—O1 | 179.31 (19) | Br1—C13—C14—C15 | 177.84 (16) |
C5—C6—C7—C2 | −1.0 (3) | C13—C14—C15—C10 | 1.7 (3) |
C3—C2—C7—O1 | −179.05 (16) | C11—C10—C15—C14 | −2.4 (3) |
C1—C2—C7—O1 | −0.1 (2) | S1—C10—C15—C14 | −175.55 (16) |
C3—C2—C7—C6 | 1.2 (3) |
Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) −x−1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C15H10BrClO2S |
Mr | 369.65 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 6.4192 (1), 9.9185 (2), 11.7755 (2) |
α, β, γ (°) | 100.681 (1), 92.113 (1), 104.168 (1) |
V (Å3) | 711.67 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 3.22 |
Crystal size (mm) | 0.38 × 0.31 × 0.27 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.374, 0.475 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13131, 3529, 3236 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.081, 1.12 |
No. of reflections | 3529 |
No. of parameters | 182 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.55, −0.76 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).
References
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o1190. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o2350. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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As a part of our ongoing study of 5-chloro-2-methyl-1-benzofuran derivatives containing 3-phenylsulfonyl (Choi et al., 2008) and 3-(4-fluorophenylsulfonyl) (Choi et al., 2010) 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 0.009 (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 fragment is 86.85 (6)°. In the crystal structure (Fig. 2), molecules are connected by slipped π···π interactions; the first one between the benzene and the furan rings of adjacent molecules, with a Cg1···Cg2i distance of 3.884 (2) Å and an interplanar distance of 3.369 (2) Å resulting in a slippage of 1.945 (2) Å (Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively), and the second one between the 4-bromophenyl rings of adjacent molecules, with a Cg3···Cg3ii distance of 3.882 (2) Å and an interplanar distance of 3.552 (2) Å resulting in a slippage of 1.566 (2) Å (Cg3 is the centroid of the C10–C15 benzene ring). The crystal packing (Fig. 2) also exhibits a Br···Br contact at [3.6446 (4) Å].