In the crystal structure of the title compound, C10H10O2, the molecule has crystallographic inversion symmetry. Each dihydrofuran ring adopts an envelope conformation and, excluding the flap C atom, is essentially coplanar with the benzene ring.
Supporting information
CCDC reference: 289687
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C)= 0.002 Å
- R factor = 0.039
- wR factor = 0.113
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
2,3,6,7-Tetrahydrobenzo[1,2 - b;4,5 - b']difuran
top
Crystal data top
C10H10O2 | F(000) = 344.00 |
Mr = 162.19 | Dx = 1.378 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 5940 reflections |
a = 7.434 (4) Å | θ = 3.4–27.5° |
b = 5.972 (2) Å | µ = 0.10 mm−1 |
c = 17.603 (9) Å | T = 296 K |
V = 781.4 (6) Å3 | Block, colourless |
Z = 4 | 0.36 × 0.30 × 0.20 mm |
Data collection top
Rigaku R-AXIS RAPID diffractometer | Rint = 0.026 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.5° |
ω scans | h = −9→9 |
6952 measured reflections | k = −7→7 |
891 independent reflections | l = −22→22 |
656 reflections with F2 > 2σ(F2) | |
Refinement top
Refinement on F2 | w = 1/[0.0012Fo2 + σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.039 | (Δ/σ)max < 0.001 |
wR(F2) = 0.113 | Δρmax = 0.24 e Å−3 |
S = 1.02 | Δρmin = −0.14 e Å−3 |
891 reflections | Extinction correction: Larson (1970) |
56 parameters | Extinction coefficient: 268 (37) |
H-atom parameters constrained | |
Special details top
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and
goodness of fit (S) are based on F2. R-factor (gt) are
based on F. The threshold expression of F2 > 2.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.43530 (14) | 0.60188 (13) | 0.35156 (5) | 0.0570 (3) | |
C1 | 0.4768 (2) | 0.3963 (2) | 0.31195 (10) | 0.0624 (4) | |
C2 | 0.5722 (2) | 0.2415 (2) | 0.36674 (8) | 0.0566 (4) | |
C3 | 0.54239 (16) | 0.3559 (2) | 0.44151 (6) | 0.0413 (3) | |
C4 | 0.46343 (17) | 0.5623 (2) | 0.42769 (6) | 0.0412 (3) | |
C5 | 0.58094 (17) | 0.28956 (19) | 0.51517 (6) | 0.0435 (3) | |
H1 | 0.5538 | 0.4279 | 0.2688 | 0.075* | |
H2 | 0.3663 | 0.3269 | 0.2944 | 0.076* | |
H3 | 0.6995 | 0.2310 | 0.3552 | 0.069* | |
H4 | 0.5196 | 0.0929 | 0.3666 | 0.069* | |
H5 | 0.6349 | 0.1524 | 0.5256 | 0.052* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0763 (7) | 0.0530 (5) | 0.0416 (6) | 0.0093 (4) | −0.0051 (4) | 0.0055 (4) |
C1 | 0.0759 (10) | 0.0645 (8) | 0.0466 (9) | 0.0056 (7) | −0.0039 (7) | −0.0070 (6) |
C2 | 0.0710 (10) | 0.0486 (7) | 0.0501 (8) | 0.0056 (7) | 0.0043 (6) | −0.0042 (6) |
C3 | 0.0392 (6) | 0.0373 (6) | 0.0475 (7) | 0.0007 (4) | 0.0027 (5) | 0.0014 (5) |
C4 | 0.0413 (6) | 0.0405 (6) | 0.0418 (7) | −0.0004 (4) | −0.0008 (5) | 0.0072 (5) |
C5 | 0.0455 (7) | 0.0353 (5) | 0.0496 (7) | 0.0060 (5) | −0.0008 (5) | 0.0047 (5) |
Geometric parameters (Å, º) top
O1—C1 | 1.4453 (17) | C4—C5i | 1.3797 (17) |
O1—C4 | 1.3768 (15) | C1—H1 | 0.970 |
C1—C2 | 1.512 (2) | C1—H2 | 0.970 |
C2—C3 | 1.4992 (18) | C2—H3 | 0.970 |
C3—C4 | 1.3868 (16) | C2—H4 | 0.970 |
C3—C5 | 1.3857 (17) | C5—H5 | 0.930 |
| | | |
O1···C1ii | 3.600 (2) | H2···O1v | 3.253 |
O1···C1iii | 3.4355 (19) | H2···C1v | 3.388 |
C1···O1iv | 3.600 (2) | H2···C1ix | 3.473 |
C1···O1v | 3.4355 (19) | H2···H1v | 2.696 |
O1···H1iii | 2.878 | H2···H1ix | 2.645 |
O1···H2ii | 2.801 | H2···H2iv | 3.451 |
O1···H2iii | 3.253 | H2···H2ii | 3.451 |
O1···H3vi | 2.823 | H2···H3ix | 2.966 |
O1···H4vii | 3.010 | H2···H4ii | 3.517 |
O1···H4ii | 3.392 | H2···H4iii | 3.358 |
O1···H5viii | 3.460 | H3···O1xi | 2.823 |
C1···H1v | 3.146 | H3···C1xi | 3.219 |
C1···H1iii | 3.486 | H3···C2xi | 3.386 |
C1···H1ix | 3.456 | H3···C2vi | 3.495 |
C1···H2iii | 3.388 | H3···C3xi | 3.318 |
C1···H2x | 3.473 | H3···C4xi | 2.987 |
C1···H3vi | 3.219 | H3···H1xi | 2.992 |
C1···H4iii | 3.355 | H3···H1v | 3.403 |
C2···H1v | 3.174 | H3···H2x | 2.966 |
C2···H3xi | 3.495 | H3···H3xi | 3.079 |
C2···H3vi | 3.386 | H3···H3vi | 3.079 |
C2···H5xii | 3.391 | H3···H4vi | 3.012 |
C3···H3vi | 3.318 | H4···O1xiii | 3.010 |
C3···H5vi | 3.329 | H4···O1iv | 3.392 |
C3···H5xii | 3.359 | H4···C1v | 3.355 |
C3···H5viii | 3.085 | H4···C4xiii | 3.372 |
C4···H3vi | 2.987 | H4···C5xii | 3.179 |
C4···H4vii | 3.372 | H4···H1v | 2.636 |
C4···H5vi | 3.489 | H4···H2iv | 3.517 |
C4···H5viii | 2.879 | H4···H2v | 3.358 |
C5···H4xii | 3.179 | H4···H3xi | 3.012 |
C5···H5vi | 3.032 | H4···H5xii | 2.659 |
C5···H5xii | 3.171 | H5···O1xiv | 3.460 |
C5···H5viii | 3.410 | H5···C2xii | 3.391 |
H1···O1v | 2.878 | H5···C3xi | 3.329 |
H1···C1v | 3.486 | H5···C3xii | 3.359 |
H1···C1iii | 3.146 | H5···C3xiv | 3.085 |
H1···C1x | 3.456 | H5···C4xi | 3.489 |
H1···C2iii | 3.174 | H5···C4xiv | 2.879 |
H1···H1v | 3.161 | H5···C5xi | 3.032 |
H1···H1iii | 3.161 | H5···C5xii | 3.171 |
H1···H2iii | 2.696 | H5···C5xiv | 3.410 |
H1···H2x | 2.645 | H5···H4xii | 2.659 |
H1···H3vi | 2.992 | H5···H5xi | 3.442 |
H1···H3iii | 3.403 | H5···H5vi | 3.442 |
H1···H4iii | 2.636 | H5···H5xii | 2.854 |
H2···O1iv | 2.801 | | |
| | | |
C1—O1—C4 | 106.93 (10) | O1—C1—H2 | 109.6 |
O1—C1—C2 | 108.15 (12) | C2—C1—H1 | 110.0 |
C1—C2—C3 | 102.25 (11) | C2—C1—H2 | 109.8 |
C2—C3—C4 | 108.26 (10) | H1—C1—H2 | 109.5 |
C2—C3—C5 | 131.36 (11) | C1—C2—H3 | 111.3 |
C4—C3—C5 | 120.37 (11) | C1—C2—H4 | 111.6 |
O1—C4—C3 | 112.81 (10) | C3—C2—H3 | 111.0 |
O1—C4—C5i | 124.27 (10) | C3—C2—H4 | 111.1 |
C3—C4—C5i | 122.91 (11) | H3—C2—H4 | 109.5 |
C3—C5—C4i | 116.71 (10) | C3—C5—H5 | 121.7 |
O1—C1—H1 | 109.8 | C4i—C5—H5 | 121.6 |
| | | |
C1—O1—C4—C3 | 7.77 (15) | C2—C3—C4—C5i | −179.67 (12) |
C1—O1—C4—C5i | −172.39 (12) | C2—C3—C5—C4i | 179.54 (13) |
C4—O1—C1—C2 | −12.47 (15) | C4—C3—C5—C4i | 0.15 (17) |
O1—C1—C2—C3 | 12.07 (15) | C5—C3—C4—O1 | 179.69 (11) |
C1—C2—C3—C4 | −7.52 (14) | C5—C3—C4—C5i | −0.15 (19) |
C1—C2—C3—C5 | 173.03 (13) | O1—C4—C5i—C3i | −179.68 (11) |
C2—C3—C4—O1 | 0.17 (15) | C3—C4—C5i—C3i | 0.15 (18) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y+1/2, z; (iii) −x+1, y+1/2, −z+1/2; (iv) −x+1/2, y−1/2, z; (v) −x+1, y−1/2, −z+1/2; (vi) −x+3/2, y+1/2, z; (vii) x, y+1, z; (viii) x−1/2, −y+1/2, −z+1; (ix) x−1/2, y, −z+1/2; (x) x+1/2, y, −z+1/2; (xi) −x+3/2, y−1/2, z; (xii) −x+1, −y, −z+1; (xiii) x, y−1, z; (xiv) x+1/2, −y+1/2, −z+1. |