organic compounds
5-Bromo-3-(4-fluorophenylsulfonyl)-2,7-dimethyl-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, C16H12BrFO3S, the 4-fluorophenyl ring makes a dihedral angle of 72.35 (5)° with the mean plane [r.m.s. deviation = 0.008 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked into [010] chains via two different inversion-generated pairs of C—H⋯O hydrogen bonds. The also exhibits slipped π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.667 (2) Å and slippage = 1.341 (2) Å], and between the benzene and the furan rings of neighbouring molecules [centroid–centroid distance = 3.759 (2) Å and slippage = 0.757 (2) Å].
Related literature
For background information and the crystal structures of related compounds, see: Choi et al. (2010, 2012).
Experimental
Crystal data
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Refinement
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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
10.1107/S1600536812043607/hb6977sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812043607/hb6977Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812043607/hb6977Isup3.cml
3-Chloroperoxybenzoic acid (77%, 381 mg, 1.7 mmol) was added in small portions to a stirred solution of 5-bromo-3-(4-fluorophenylsulfanyl)-2,7-dimethyl-1-benzofuran (281 mg, 0.8 mmol) in dichloromethane (40 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
(hexane–ethyl acetate, 4:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 472–473 K; Rf = 0.57 (hexane–ethyl acetate, 4:1 v/v)]. Colourless blocks 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.
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).C16H12BrFO3S | Z = 2 |
Mr = 383.23 | F(000) = 384 |
Triclinic, P1 | Dx = 1.719 Mg m−3 |
Hall symbol: -P 1 | Melting point = 472–473 K |
a = 8.0789 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.2754 (2) Å | Cell parameters from 6655 reflections |
c = 11.3555 (2) Å | θ = 2.7–28.3° |
α = 71.283 (1)° | µ = 2.94 mm−1 |
β = 72.645 (1)° | T = 173 K |
γ = 70.042 (1)° | Block, colourless |
V = 740.30 (2) Å3 | 0.29 × 0.21 × 0.18 mm |
Bruker SMART APEXII CCD diffractometer | 3680 independent reflections |
Radiation source: rotating anode | 3259 reflections with I > 2σ(I) |
Graphite multilayer monochromator | Rint = 0.031 |
Detector resolution: 10.0 pixels mm-1 | θmax = 28.3°, θmin = 1.9° |
ϕ and ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −12→12 |
Tmin = 0.527, Tmax = 0.746 | l = −15→15 |
14090 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)] = 0.028 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.074 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0417P)2 + 0.237P] where P = (Fo2 + 2Fc2)/3 |
3680 reflections | (Δ/σ)max = 0.002 |
201 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
C16H12BrFO3S | γ = 70.042 (1)° |
Mr = 383.23 | V = 740.30 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.0789 (1) Å | Mo Kα radiation |
b = 9.2754 (2) Å | µ = 2.94 mm−1 |
c = 11.3555 (2) Å | T = 173 K |
α = 71.283 (1)° | 0.29 × 0.21 × 0.18 mm |
β = 72.645 (1)° |
Bruker SMART APEXII CCD diffractometer | 3680 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3259 reflections with I > 2σ(I) |
Tmin = 0.527, Tmax = 0.746 | Rint = 0.031 |
14090 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.074 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.36 e Å−3 |
3680 reflections | Δρmin = −0.47 e Å−3 |
201 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 | 0.75349 (3) | 0.10966 (3) | 0.797351 (17) | 0.03912 (8) | |
S1 | 0.48725 (5) | 0.40486 (5) | 0.29104 (4) | 0.02342 (10) | |
F1 | 1.00247 (19) | 0.77090 (18) | 0.00357 (14) | 0.0571 (4) | |
O1 | 0.75109 (17) | −0.04433 (15) | 0.32764 (12) | 0.0274 (3) | |
O2 | 0.40458 (16) | 0.45572 (16) | 0.40738 (11) | 0.0286 (3) | |
O3 | 0.37705 (17) | 0.41993 (16) | 0.20642 (12) | 0.0315 (3) | |
C1 | 0.6075 (2) | 0.2081 (2) | 0.33360 (16) | 0.0242 (3) | |
C2 | 0.6733 (2) | 0.1303 (2) | 0.45008 (15) | 0.0227 (3) | |
C3 | 0.6674 (2) | 0.1745 (2) | 0.55829 (16) | 0.0251 (3) | |
H3 | 0.6078 | 0.2785 | 0.5692 | 0.030* | |
C4 | 0.7538 (2) | 0.0574 (2) | 0.64843 (16) | 0.0271 (3) | |
C5 | 0.8430 (2) | −0.0963 (2) | 0.63592 (17) | 0.0285 (4) | |
H5 | 0.9010 | −0.1707 | 0.7011 | 0.034* | |
C6 | 0.8486 (2) | −0.1426 (2) | 0.52969 (17) | 0.0268 (3) | |
C7 | 0.7611 (2) | −0.0248 (2) | 0.44028 (16) | 0.0243 (3) | |
C8 | 0.6581 (2) | 0.0987 (2) | 0.26428 (16) | 0.0265 (3) | |
C9 | 0.9424 (3) | −0.3065 (2) | 0.51205 (19) | 0.0331 (4) | |
H9A | 0.8612 | −0.3460 | 0.4891 | 0.050* | |
H9B | 0.9767 | −0.3761 | 0.5915 | 0.050* | |
H9C | 1.0506 | −0.3045 | 0.4440 | 0.050* | |
C10 | 0.6362 (3) | 0.1018 (3) | 0.13857 (18) | 0.0346 (4) | |
H10A | 0.5784 | 0.2103 | 0.0967 | 0.052* | |
H10B | 0.5610 | 0.0329 | 0.1499 | 0.052* | |
H10C | 0.7547 | 0.0644 | 0.0858 | 0.052* | |
C11 | 0.6478 (2) | 0.5107 (2) | 0.20442 (16) | 0.0244 (3) | |
C12 | 0.6821 (3) | 0.5500 (2) | 0.07255 (17) | 0.0321 (4) | |
H12 | 0.6237 | 0.5157 | 0.0295 | 0.038* | |
C13 | 0.8014 (3) | 0.6392 (3) | 0.00442 (19) | 0.0394 (5) | |
H13 | 0.8256 | 0.6685 | −0.0859 | 0.047* | |
C14 | 0.8840 (3) | 0.6845 (2) | 0.0705 (2) | 0.0376 (4) | |
C15 | 0.8550 (3) | 0.6459 (3) | 0.2007 (2) | 0.0370 (4) | |
H15 | 0.9169 | 0.6782 | 0.2427 | 0.044* | |
C16 | 0.7330 (2) | 0.5585 (2) | 0.26933 (17) | 0.0300 (4) | |
H16 | 0.7078 | 0.5316 | 0.3597 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.05355 (14) | 0.04150 (14) | 0.02493 (11) | −0.01030 (10) | −0.01583 (8) | −0.00744 (8) |
S1 | 0.02474 (19) | 0.0241 (2) | 0.02165 (19) | −0.00430 (16) | −0.00808 (15) | −0.00546 (16) |
F1 | 0.0558 (8) | 0.0497 (9) | 0.0620 (9) | −0.0322 (7) | −0.0040 (7) | 0.0026 (7) |
O1 | 0.0325 (6) | 0.0237 (6) | 0.0290 (6) | −0.0070 (5) | −0.0088 (5) | −0.0090 (5) |
O2 | 0.0296 (6) | 0.0290 (7) | 0.0250 (6) | −0.0048 (5) | −0.0041 (5) | −0.0089 (5) |
O3 | 0.0325 (6) | 0.0346 (7) | 0.0306 (6) | −0.0073 (6) | −0.0154 (5) | −0.0061 (6) |
C1 | 0.0276 (8) | 0.0232 (8) | 0.0228 (7) | −0.0067 (7) | −0.0077 (6) | −0.0049 (7) |
C2 | 0.0230 (7) | 0.0222 (8) | 0.0226 (7) | −0.0064 (6) | −0.0058 (6) | −0.0041 (6) |
C3 | 0.0285 (8) | 0.0234 (9) | 0.0237 (8) | −0.0065 (7) | −0.0063 (6) | −0.0059 (7) |
C4 | 0.0319 (8) | 0.0303 (9) | 0.0201 (7) | −0.0097 (7) | −0.0074 (6) | −0.0045 (7) |
C5 | 0.0305 (8) | 0.0260 (9) | 0.0265 (8) | −0.0090 (7) | −0.0089 (7) | 0.0009 (7) |
C6 | 0.0271 (8) | 0.0224 (9) | 0.0294 (8) | −0.0091 (7) | −0.0058 (7) | −0.0020 (7) |
C7 | 0.0262 (8) | 0.0226 (9) | 0.0253 (8) | −0.0075 (7) | −0.0055 (6) | −0.0061 (7) |
C8 | 0.0277 (8) | 0.0264 (9) | 0.0267 (8) | −0.0077 (7) | −0.0062 (6) | −0.0075 (7) |
C9 | 0.0357 (9) | 0.0217 (9) | 0.0397 (10) | −0.0056 (8) | −0.0106 (8) | −0.0047 (8) |
C10 | 0.0431 (10) | 0.0364 (11) | 0.0302 (9) | −0.0093 (9) | −0.0125 (8) | −0.0132 (8) |
C11 | 0.0267 (8) | 0.0208 (8) | 0.0235 (8) | −0.0034 (7) | −0.0072 (6) | −0.0041 (7) |
C12 | 0.0360 (9) | 0.0344 (10) | 0.0253 (8) | −0.0077 (8) | −0.0113 (7) | −0.0041 (8) |
C13 | 0.0435 (11) | 0.0415 (12) | 0.0254 (9) | −0.0122 (9) | −0.0071 (8) | 0.0027 (8) |
C14 | 0.0367 (10) | 0.0264 (10) | 0.0437 (11) | −0.0116 (8) | −0.0042 (8) | −0.0013 (9) |
C15 | 0.0387 (10) | 0.0345 (11) | 0.0445 (11) | −0.0135 (9) | −0.0100 (8) | −0.0135 (9) |
C16 | 0.0343 (9) | 0.0305 (10) | 0.0268 (8) | −0.0077 (8) | −0.0078 (7) | −0.0089 (8) |
Br1—C4 | 1.9019 (16) | C6—C9 | 1.498 (3) |
S1—O2 | 1.4396 (12) | C8—C10 | 1.480 (2) |
S1—O3 | 1.4403 (12) | C9—H9A | 0.9800 |
S1—C1 | 1.7354 (18) | C9—H9B | 0.9800 |
S1—C11 | 1.7612 (17) | C9—H9C | 0.9800 |
F1—C14 | 1.354 (2) | C10—H10A | 0.9800 |
O1—C8 | 1.368 (2) | C10—H10B | 0.9800 |
O1—C7 | 1.377 (2) | C10—H10C | 0.9800 |
C1—C8 | 1.362 (2) | C11—C12 | 1.387 (2) |
C1—C2 | 1.448 (2) | C11—C16 | 1.391 (2) |
C2—C7 | 1.395 (2) | C12—C13 | 1.379 (3) |
C2—C3 | 1.398 (2) | C12—H12 | 0.9500 |
C3—C4 | 1.382 (3) | C13—C14 | 1.371 (3) |
C3—H3 | 0.9500 | C13—H13 | 0.9500 |
C4—C5 | 1.392 (3) | C14—C15 | 1.371 (3) |
C5—C6 | 1.389 (2) | C15—C16 | 1.385 (3) |
C5—H5 | 0.9500 | C15—H15 | 0.9500 |
C6—C7 | 1.383 (2) | C16—H16 | 0.9500 |
O2—S1—O3 | 119.77 (8) | C6—C9—H9A | 109.5 |
O2—S1—C1 | 106.57 (8) | C6—C9—H9B | 109.5 |
O3—S1—C1 | 108.82 (8) | H9A—C9—H9B | 109.5 |
O2—S1—C11 | 107.04 (8) | C6—C9—H9C | 109.5 |
O3—S1—C11 | 107.58 (8) | H9A—C9—H9C | 109.5 |
C1—S1—C11 | 106.33 (8) | H9B—C9—H9C | 109.5 |
C8—O1—C7 | 107.04 (13) | C8—C10—H10A | 109.5 |
C8—C1—C2 | 107.36 (15) | C8—C10—H10B | 109.5 |
C8—C1—S1 | 126.67 (13) | H10A—C10—H10B | 109.5 |
C2—C1—S1 | 125.96 (13) | C8—C10—H10C | 109.5 |
C7—C2—C3 | 119.41 (15) | H10A—C10—H10C | 109.5 |
C7—C2—C1 | 104.63 (14) | H10B—C10—H10C | 109.5 |
C3—C2—C1 | 135.96 (16) | C12—C11—C16 | 121.12 (16) |
C4—C3—C2 | 115.86 (16) | C12—C11—S1 | 119.34 (13) |
C4—C3—H3 | 122.1 | C16—C11—S1 | 119.49 (13) |
C2—C3—H3 | 122.1 | C13—C12—C11 | 119.55 (17) |
C3—C4—C5 | 123.81 (16) | C13—C12—H12 | 120.2 |
C3—C4—Br1 | 118.15 (14) | C11—C12—H12 | 120.2 |
C5—C4—Br1 | 118.04 (13) | C14—C13—C12 | 118.25 (18) |
C6—C5—C4 | 121.09 (17) | C14—C13—H13 | 120.9 |
C6—C5—H5 | 119.5 | C12—C13—H13 | 120.9 |
C4—C5—H5 | 119.5 | F1—C14—C13 | 118.26 (19) |
C7—C6—C5 | 114.69 (16) | F1—C14—C15 | 118.05 (19) |
C7—C6—C9 | 122.24 (16) | C13—C14—C15 | 123.68 (18) |
C5—C6—C9 | 123.06 (17) | C14—C15—C16 | 118.15 (18) |
O1—C7—C6 | 124.43 (16) | C14—C15—H15 | 120.9 |
O1—C7—C2 | 110.43 (14) | C16—C15—H15 | 120.9 |
C6—C7—C2 | 125.14 (15) | C15—C16—C11 | 119.24 (17) |
C1—C8—O1 | 110.54 (15) | C15—C16—H16 | 120.4 |
C1—C8—C10 | 134.51 (18) | C11—C16—H16 | 120.4 |
O1—C8—C10 | 114.95 (15) | ||
O2—S1—C1—C8 | 157.48 (15) | C1—C2—C7—O1 | −0.36 (18) |
O3—S1—C1—C8 | 27.03 (18) | C3—C2—C7—C6 | −1.2 (3) |
C11—S1—C1—C8 | −88.59 (17) | C1—C2—C7—C6 | 178.73 (16) |
O2—S1—C1—C2 | −22.76 (17) | C2—C1—C8—O1 | 0.24 (19) |
O3—S1—C1—C2 | −153.21 (14) | S1—C1—C8—O1 | −179.96 (12) |
C11—S1—C1—C2 | 91.18 (15) | C2—C1—C8—C10 | −179.02 (19) |
C8—C1—C2—C7 | 0.08 (18) | S1—C1—C8—C10 | 0.8 (3) |
S1—C1—C2—C7 | −179.73 (13) | C7—O1—C8—C1 | −0.46 (19) |
C8—C1—C2—C3 | 179.94 (19) | C7—O1—C8—C10 | 178.96 (15) |
S1—C1—C2—C3 | 0.1 (3) | O2—S1—C11—C12 | −147.79 (15) |
C7—C2—C3—C4 | 0.8 (2) | O3—S1—C11—C12 | −17.86 (17) |
C1—C2—C3—C4 | −179.07 (18) | C1—S1—C11—C12 | 98.59 (16) |
C2—C3—C4—C5 | 0.1 (3) | O2—S1—C11—C16 | 29.83 (17) |
C2—C3—C4—Br1 | 179.36 (12) | O3—S1—C11—C16 | 159.77 (14) |
C3—C4—C5—C6 | −0.8 (3) | C1—S1—C11—C16 | −83.78 (16) |
Br1—C4—C5—C6 | 179.98 (13) | C16—C11—C12—C13 | −0.6 (3) |
C4—C5—C6—C7 | 0.5 (2) | S1—C11—C12—C13 | 176.99 (16) |
C4—C5—C6—C9 | −179.85 (16) | C11—C12—C13—C14 | 0.8 (3) |
C8—O1—C7—C6 | −178.59 (16) | C12—C13—C14—F1 | 179.41 (19) |
C8—O1—C7—C2 | 0.51 (18) | C12—C13—C14—C15 | 0.1 (3) |
C5—C6—C7—O1 | 179.48 (15) | F1—C14—C15—C16 | 179.55 (18) |
C9—C6—C7—O1 | −0.2 (3) | C13—C14—C15—C16 | −1.1 (3) |
C5—C6—C7—C2 | 0.5 (2) | C14—C15—C16—C11 | 1.3 (3) |
C9—C6—C7—C2 | −179.19 (16) | C12—C11—C16—C15 | −0.5 (3) |
C3—C2—C7—O1 | 179.75 (14) | S1—C11—C16—C15 | −178.04 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2i | 0.95 | 2.53 | 3.408 (2) | 154 |
C9—H9A···O2ii | 0.98 | 2.50 | 3.304 (2) | 139 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C16H12BrFO3S |
Mr | 383.23 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 8.0789 (1), 9.2754 (2), 11.3555 (2) |
α, β, γ (°) | 71.283 (1), 72.645 (1), 70.042 (1) |
V (Å3) | 740.30 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.94 |
Crystal size (mm) | 0.29 × 0.21 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.527, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14090, 3680, 3259 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.074, 1.02 |
No. of reflections | 3680 |
No. of parameters | 201 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.36, −0.47 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2i | 0.95 | 2.53 | 3.408 (2) | 154 |
C9—H9A···O2ii | 0.98 | 2.50 | 3.304 (2) | 139 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1. |
Acknowledgements
This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan City.
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. & Lee, U. (2012). Acta Cryst. E68, o2143. CSD CrossRef IUCr Journals Google Scholar
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As a part of our continuing study of 5-bromo-2-methyl-1-benzofuran derivatives containing 4-fluorophenylsulfonyl (Choi et al., 2010) and 4-methylphenylsulfonyl (Choi et al., 2012) substituents in 3-position, 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 0.008 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 4-fluorophenyl ring and the mean plane of the benzofuran ring is 72.35 (5). In the crystal structure (Fig. 2), molecules are linked via pairs of C—H···O hydrogen bonds (Table 1), forming inversion dimers. The crystal packing (Fig. 2) also exhibits slipped π–π interactions; the first one between the benzene rings of neighbouring molecules, with a Cg1···Cg1iii distance of 3.667 (2) Å and an interplanar distance of 3.413 (2) Å resulting in a slippage of 1.341 (2) Å (Cg1 is the centroid of the C2–C7 benzene ring), and the second one between the benzene and the furan rings of neighbouring molecules, with a Cg1···Cg2ii distance of 3.759 (2) Å and an interplanar distance of 3.682 (2) Å resulting in a slippage of 0.757 (2) Å (Cg2 is the C1/C2/C7/O1/C8 furan ring).