2,3,6,7-Tetra­hydro­benzo[1,2-b;4,5-b']difuran

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.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.039
• wR factor = 0.113
• Data-to-parameter ratio = 15.9

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Computing details

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

Crystal data

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) Å^3	Block, colourless
Z = 4	0.36 × 0.30 × 0.20 mm

Data collection

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 F^2 > 2σ(F^2)

Refinement

Refinement on F^2	w = 1/[0.0012Fo^2 + σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.039	(Δ/σ)max < 0.001
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

O1—C1	1.4453 (17)	C4—C5^i	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···C1^ii	3.600 (2)	H2···O1^v	3.253
O1···C1^iii	3.4355 (19)	H2···C1^v	3.388
C1···O1^iv	3.600 (2)	H2···C1^ix	3.473
C1···O1^v	3.4355 (19)	H2···H1^v	2.696
O1···H1^iii	2.878	H2···H1^ix	2.645
O1···H2^ii	2.801	H2···H2^iv	3.451
O1···H2^iii	3.253	H2···H2^ii	3.451
O1···H3^vi	2.823	H2···H3^ix	2.966
O1···H4^vii	3.010	H2···H4^ii	3.517
O1···H4^ii	3.392	H2···H4^iii	3.358
O1···H5^viii	3.460	H3···O1^xi	2.823
C1···H1^v	3.146	H3···C1^xi	3.219
C1···H1^iii	3.486	H3···C2^xi	3.386
C1···H1^ix	3.456	H3···C2^vi	3.495
C1···H2^iii	3.388	H3···C3^xi	3.318
C1···H2^x	3.473	H3···C4^xi	2.987
C1···H3^vi	3.219	H3···H1^xi	2.992
C1···H4^iii	3.355	H3···H1^v	3.403
C2···H1^v	3.174	H3···H2^x	2.966
C2···H3^xi	3.495	H3···H3^xi	3.079
C2···H3^vi	3.386	H3···H3^vi	3.079
C2···H5^xii	3.391	H3···H4^vi	3.012
C3···H3^vi	3.318	H4···O1^xiii	3.010
C3···H5^vi	3.329	H4···O1^iv	3.392
C3···H5^xii	3.359	H4···C1^v	3.355
C3···H5^viii	3.085	H4···C4^xiii	3.372
C4···H3^vi	2.987	H4···C5^xii	3.179
C4···H4^vii	3.372	H4···H1^v	2.636
C4···H5^vi	3.489	H4···H2^iv	3.517
C4···H5^viii	2.879	H4···H2^v	3.358
C5···H4^xii	3.179	H4···H3^xi	3.012
C5···H5^vi	3.032	H4···H5^xii	2.659
C5···H5^xii	3.171	H5···O1^xiv	3.460
C5···H5^viii	3.410	H5···C2^xii	3.391
H1···O1^v	2.878	H5···C3^xi	3.329
H1···C1^v	3.486	H5···C3^xii	3.359
H1···C1^iii	3.146	H5···C3^xiv	3.085
H1···C1^x	3.456	H5···C4^xi	3.489
H1···C2^iii	3.174	H5···C4^xiv	2.879
H1···H1^v	3.161	H5···C5^xi	3.032
H1···H1^iii	3.161	H5···C5^xii	3.171
H1···H2^iii	2.696	H5···C5^xiv	3.410
H1···H2^x	2.645	H5···H4^xii	2.659
H1···H3^vi	2.992	H5···H5^xi	3.442
H1···H3^iii	3.403	H5···H5^vi	3.442
H1···H4^iii	2.636	H5···H5^xii	2.854
H2···O1^iv	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—C5^i	124.27 (10)	C3—C2—H4	111.1
C3—C4—C5^i	122.91 (11)	H3—C2—H4	109.5
C3—C5—C4^i	116.71 (10)	C3—C5—H5	121.7
O1—C1—H1	109.8	C4^i—C5—H5	121.6
C1—O1—C4—C3	7.77 (15)	C2—C3—C4—C5^i	−179.67 (12)
C1—O1—C4—C5^i	−172.39 (12)	C2—C3—C5—C4^i	179.54 (13)
C4—O1—C1—C2	−12.47 (15)	C4—C3—C5—C4^i	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—C5^i	−0.15 (19)
C1—C2—C3—C5	173.03 (13)	O1—C4—C5^i—C3^i	−179.68 (11)
C2—C3—C4—O1	0.17 (15)	C3—C4—C5^i—C3^i	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.