4,6-Di-tert-butyl-2,8-dimeth-oxy-dibenzo[b,d]furan.

In the title compound, C(22)H(28)O(3), the dihedral angle between the benzene rings is 3.47 (13)° and the five-membered furan ring is essentially planar with a largest deviation of 0.0052 (14) Å. The Csp(2)-Csp(2) bond length between the two benzene rings [1.443 (3) Å] is considerably shorter than those between the benzene and tertiary C atoms [1.538 (3) and 1.530 (3) Å], which are sp(2)-sp(3) hybridized. C-H⋯π inter-actions involving the furan and benzene rings are found in the crystal structure.

Related literature

For the synthesis of the title compound, see: Hewgill & Hewitt (1967 ▶); Butsgan et al. (1989 ▶); Malkowsky et al. (2006 ▶). For a related structure, see: Du & Wang (2009 ▶).

Experimental

Crystal data

C22H28O3

M = 340.44

Monoclinic,

a = 15.631 (3) Å

b = 8.2487 (14) Å

c = 16.000 (3) Å

β = 105.438 (5)°

V = 1988.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 100 K

0.5 × 0.4 × 0.2 mm

Data collection

Rigaku R-AXIS RAPID II-S diffractometer

Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 2008 ▶) T min = 0.965, T max = 0.985

18260 measured reflections

4563 independent reflections

2123 reflections with I > 2σ(I)

R int = 0.107

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.229

S = 0.99

4563 reflections

227 parameters

H-atom parameters not refined

Δρmax = 0.24 e Å−3

Δρmin = −0.21 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2008 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811048379/bq2314sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048379/bq2314Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048379/bq2314Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H28O3	F(000) = 736
Mr = 340.44	Dx = 1.137 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 15.631 (3) Å	Cell parameters from 18260 reflections
b = 8.2487 (14) Å	θ = 3.2–27.5°
c = 16.000 (3) Å	µ = 0.07 mm−1
β = 105.438 (5)°	T = 100 K
V = 1988.5 (6) Å3	Block, brown
Z = 4	0.5 × 0.4 × 0.2 mm

Rigaku R-AXIS RAPID II-S diffractometer	4563 independent reflections
Radiation source: fine-focus sealed tube	2123 reflections with I > 2σ(I)
graphite	Rint = 0.107
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 2008)	h = −20→20
Tmin = 0.965, Tmax = 0.985	k = −9→10
18260 measured reflections	l = −20→20

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.229	H-atom parameters not refined
S = 0.99	w = 1/[σ2(Fo2) + (0.1073P)2] where P = (Fo2 + 2Fc2)/3
4563 reflections	(Δ/σ)max = 0.009
227 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
O1	0.90422 (11)	0.83006 (19)	0.11113 (11)	0.0570 (5)
O2	0.87127 (14)	1.1093 (2)	0.41186 (12)	0.0787 (6)
C11	0.81556 (16)	1.0573 (3)	0.08804 (16)	0.0515 (6)
C10	0.84681 (16)	1.0295 (3)	0.18023 (17)	0.0524 (6)
C12	0.85219 (16)	0.9345 (3)	0.04927 (17)	0.0528 (6)
O3	0.68536 (15)	1.2535 (2)	−0.11118 (13)	0.0805 (6)
C5	0.75816 (17)	1.1710 (3)	0.03733 (17)	0.0585 (7)
H5	0.7323	1.2532	0.0621	0.070*
C4	0.83376 (17)	1.1096 (3)	0.25353 (17)	0.0560 (6)
H4	0.7990	1.2024	0.2483	0.067*
C3	0.87496 (17)	1.0440 (3)	0.33359 (17)	0.0592 (7)
C1	0.93919 (17)	0.8188 (3)	0.27084 (18)	0.0589 (7)
C7	0.78180 (18)	1.0324 (3)	−0.08857 (18)	0.0633 (7)
H7	0.7697	1.0287	−0.1487	0.076*
C9	0.89907 (17)	0.8908 (3)	0.19084 (17)	0.0551 (6)
C6	0.74191 (18)	1.1549 (3)	−0.05084 (18)	0.0610 (7)
C8	0.83866 (17)	0.9163 (3)	−0.03992 (17)	0.0563 (6)
C14	0.87778 (18)	0.7790 (3)	−0.08242 (18)	0.0617 (7)
C2	0.92504 (17)	0.9010 (3)	0.34121 (18)	0.0633 (7)
H2	0.9499	0.8595	0.3964	0.076*
C13	0.9922 (2)	0.6597 (3)	0.2794 (2)	0.0734 (8)
C15	0.8178 (2)	1.2486 (4)	0.4088 (2)	0.0791 (9)
H15A	0.8197	1.2819	0.4668	0.119*
H15B	0.7577	1.2238	0.3779	0.119*
H15C	0.8397	1.3345	0.3797	0.119*
C18	0.9331 (2)	0.5255 (3)	0.2286 (2)	0.0874 (10)
H18A	0.9123	0.5566	0.1688	0.131*
H18B	0.8834	0.5088	0.2521	0.131*
H18C	0.9667	0.4269	0.2330	0.131*
C22	0.9777 (2)	0.7683 (5)	−0.0432 (3)	0.1029 (13)
H22A	1.0051	0.8670	−0.0547	0.154*
H22B	1.0010	0.6787	−0.0686	0.154*
H22C	0.9900	0.7524	0.0183	0.154*
C16	0.6289 (2)	1.3589 (4)	−0.0816 (2)	0.0826 (9)
H16A	0.5937	1.4200	−0.1295	0.124*
H16B	0.6639	1.4317	−0.0392	0.124*
H16C	0.5907	1.2968	−0.0558	0.124*
C19	1.0732 (2)	0.6880 (4)	0.2426 (3)	0.1032 (12)
H19A	1.0531	0.7258	0.1838	0.155*
H19B	1.1050	0.5881	0.2439	0.155*
H19C	1.1116	0.7676	0.2771	0.155*
C20	0.8357 (2)	0.6196 (4)	−0.0658 (2)	0.0952 (11)
H20A	0.8430	0.6067	−0.0047	0.143*
H20B	0.8640	0.5312	−0.0870	0.143*
H20C	0.7736	0.6207	−0.0954	0.143*
C21	0.8591 (3)	0.8028 (5)	−0.1807 (2)	0.1160 (14)
H21A	0.8840	0.9041	−0.1923	0.174*
H21B	0.7962	0.8035	−0.2063	0.174*
H21C	0.8855	0.7157	−0.2049	0.174*
C17	1.0251 (3)	0.6062 (4)	0.3745 (2)	0.1147 (14)
H17A	1.0570	0.5060	0.3778	0.172*
H17B	0.9752	0.5913	0.3981	0.172*
H17C	1.0636	0.6880	0.4071	0.172*

	U11	U22	U33	U12	U13	U23
O1	0.0590 (10)	0.0531 (10)	0.0617 (12)	0.0046 (8)	0.0209 (9)	−0.0053 (8)
O2	0.0938 (15)	0.0840 (13)	0.0594 (12)	0.0314 (11)	0.0220 (11)	−0.0055 (10)
C11	0.0529 (13)	0.0463 (12)	0.0617 (16)	−0.0036 (10)	0.0262 (12)	−0.0047 (11)
C10	0.0525 (14)	0.0471 (12)	0.0619 (16)	−0.0012 (10)	0.0225 (12)	−0.0034 (11)
C12	0.0525 (13)	0.0456 (12)	0.0644 (16)	−0.0011 (10)	0.0230 (12)	0.0009 (12)
O3	0.0993 (15)	0.0751 (13)	0.0708 (13)	0.0233 (12)	0.0293 (12)	0.0033 (10)
C5	0.0650 (16)	0.0509 (13)	0.0654 (17)	0.0050 (12)	0.0275 (13)	−0.0009 (12)
C4	0.0599 (15)	0.0498 (13)	0.0628 (16)	0.0045 (11)	0.0240 (13)	−0.0023 (12)
C3	0.0636 (16)	0.0601 (15)	0.0578 (16)	0.0047 (12)	0.0226 (13)	−0.0073 (13)
C1	0.0559 (14)	0.0522 (14)	0.0683 (18)	0.0053 (11)	0.0159 (13)	−0.0020 (13)
C7	0.0722 (17)	0.0631 (16)	0.0608 (16)	−0.0004 (14)	0.0286 (14)	−0.0035 (13)
C9	0.0559 (14)	0.0493 (13)	0.0631 (16)	−0.0016 (11)	0.0209 (12)	−0.0076 (12)
C6	0.0662 (16)	0.0562 (14)	0.0654 (17)	0.0056 (12)	0.0258 (14)	0.0056 (13)
C8	0.0588 (15)	0.0542 (14)	0.0615 (16)	−0.0036 (12)	0.0261 (13)	−0.0076 (12)
C14	0.0662 (16)	0.0605 (15)	0.0666 (18)	−0.0005 (13)	0.0317 (14)	−0.0107 (13)
C2	0.0664 (16)	0.0594 (15)	0.0632 (16)	0.0100 (13)	0.0158 (13)	−0.0003 (13)
C13	0.079 (2)	0.0594 (16)	0.078 (2)	0.0187 (14)	0.0146 (16)	−0.0048 (15)
C15	0.085 (2)	0.084 (2)	0.0688 (19)	0.0247 (16)	0.0222 (16)	−0.0115 (16)
C18	0.105 (2)	0.0525 (16)	0.101 (3)	0.0133 (16)	0.022 (2)	0.0001 (16)
C22	0.069 (2)	0.124 (3)	0.125 (3)	0.0018 (19)	0.041 (2)	−0.056 (2)
C16	0.092 (2)	0.0692 (18)	0.087 (2)	0.0197 (16)	0.0261 (18)	0.0021 (17)
C19	0.069 (2)	0.095 (2)	0.143 (4)	0.0249 (18)	0.024 (2)	−0.020 (2)
C20	0.110 (3)	0.0655 (19)	0.121 (3)	−0.0122 (18)	0.051 (2)	−0.0273 (19)
C21	0.176 (4)	0.109 (3)	0.078 (2)	0.046 (3)	0.059 (3)	−0.009 (2)
C17	0.151 (4)	0.086 (2)	0.086 (2)	0.054 (2)	−0.004 (2)	0.002 (2)

O1—C9	1.393 (3)	C13—C18	1.529 (4)
O1—C12	1.398 (3)	C13—C17	1.536 (4)
O2—C3	1.378 (3)	C13—C19	1.549 (5)
O2—C15	1.413 (3)	C15—H15A	0.9600
C11—C12	1.389 (3)	C15—H15B	0.9600
C11—C5	1.398 (3)	C15—H15C	0.9600
C11—C10	1.443 (3)	C18—H18A	0.9600
C10—C9	1.390 (3)	C18—H18B	0.9600
C10—C4	1.407 (3)	C18—H18C	0.9600
C12—C8	1.394 (3)	C22—H22A	0.9600
O3—C6	1.386 (3)	C22—H22B	0.9600
O3—C16	1.408 (3)	C22—H22C	0.9600
C5—C6	1.372 (4)	C16—H16A	0.9600
C5—H5	0.9300	C16—H16B	0.9600
C4—C3	1.382 (4)	C16—H16C	0.9600
C4—H4	0.9300	C19—H19A	0.9600
C3—C2	1.403 (3)	C19—H19B	0.9600
C1—C2	1.382 (4)	C19—H19C	0.9600
C1—C9	1.399 (4)	C20—H20A	0.9600
C1—C13	1.538 (3)	C20—H20B	0.9600
C7—C8	1.395 (4)	C20—H20C	0.9600
C7—C6	1.405 (4)	C21—H21A	0.9600
C7—H7	0.9300	C21—H21B	0.9600
C8—C14	1.530 (3)	C21—H21C	0.9600
C14—C22	1.523 (4)	C17—H17A	0.9600
C14—C20	1.524 (4)	C17—H17B	0.9600
C14—C21	1.533 (4)	C17—H17C	0.9600
C2—H2	0.9300
C9—O1—C12	105.20 (18)	C1—C13—C19	108.2 (2)
C3—O2—C15	117.0 (2)	O2—C15—H15A	109.5
C12—C11—C5	120.5 (2)	O2—C15—H15B	109.5
C12—C11—C10	105.8 (2)	H15A—C15—H15B	109.5
C5—C11—C10	133.6 (2)	O2—C15—H15C	109.5
C9—C10—C4	119.7 (2)	H15A—C15—H15C	109.5
C9—C10—C11	106.5 (2)	H15B—C15—H15C	109.5
C4—C10—C11	133.8 (2)	C13—C18—H18A	109.5
C11—C12—C8	124.6 (2)	C13—C18—H18B	109.5
C11—C12—O1	111.4 (2)	H18A—C18—H18B	109.5
C8—C12—O1	124.0 (2)	C13—C18—H18C	109.5
C6—O3—C16	117.9 (2)	H18A—C18—H18C	109.5
C6—C5—C11	116.5 (2)	H18B—C18—H18C	109.5
C6—C5—H5	121.7	C14—C22—H22A	109.5
C11—C5—H5	121.7	C14—C22—H22B	109.5
C3—C4—C10	117.0 (2)	H22A—C22—H22B	109.5
C3—C4—H4	121.5	C14—C22—H22C	109.5
C10—C4—H4	121.5	H22A—C22—H22C	109.5
O2—C3—C4	124.6 (2)	H22B—C22—H22C	109.5
O2—C3—C2	114.0 (2)	O3—C16—H16A	109.5
C4—C3—C2	121.4 (2)	O3—C16—H16B	109.5
C2—C1—C9	114.0 (2)	H16A—C16—H16B	109.5
C2—C1—C13	123.1 (2)	O3—C16—H16C	109.5
C9—C1—C13	122.9 (2)	H16A—C16—H16C	109.5
C8—C7—C6	123.0 (3)	H16B—C16—H16C	109.5
C8—C7—H7	118.5	C13—C19—H19A	109.5
C6—C7—H7	118.5	C13—C19—H19B	109.5
C10—C9—O1	111.1 (2)	H19A—C19—H19B	109.5
C10—C9—C1	124.6 (2)	C13—C19—H19C	109.5
O1—C9—C1	124.3 (2)	H19A—C19—H19C	109.5
C5—C6—O3	124.7 (2)	H19B—C19—H19C	109.5
C5—C6—C7	122.0 (3)	C14—C20—H20A	109.5
O3—C6—C7	113.3 (2)	C14—C20—H20B	109.5
C12—C8—C7	113.4 (2)	H20A—C20—H20B	109.5
C12—C8—C14	124.4 (2)	C14—C20—H20C	109.5
C7—C8—C14	122.1 (2)	H20A—C20—H20C	109.5
C22—C14—C20	108.7 (3)	H20B—C20—H20C	109.5
C22—C14—C8	110.3 (2)	C14—C21—H21A	109.5
C20—C14—C8	108.6 (2)	C14—C21—H21B	109.5
C22—C14—C21	108.9 (3)	H21A—C21—H21B	109.5
C20—C14—C21	108.4 (3)	C14—C21—H21C	109.5
C8—C14—C21	111.8 (2)	H21A—C21—H21C	109.5
C1—C2—C3	123.3 (3)	H21B—C21—H21C	109.5
C1—C2—H2	118.4	C13—C17—H17A	109.5
C3—C2—H2	118.4	C13—C17—H17B	109.5
C18—C13—C17	108.3 (3)	H17A—C17—H17B	109.5
C18—C13—C1	109.6 (2)	C13—C17—H17C	109.5
C17—C13—C1	111.3 (2)	H17A—C17—H17C	109.5
C18—C13—C19	110.2 (3)	H17B—C17—H17C	109.5
C17—C13—C19	109.2 (3)

Cg1 and Cg2 are the centroids of the C5–C8/C11/C12 and O1/C9–C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···Cg1i	0.96	2.98	3.580 (3)	121
C15—H15B···Cg2i	0.96	2.65	3.200 (3)	117
C22—H15A···Cg2iiii	0.96	2.99	3.872 (4)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C5–C8/C11/C12 and O1/C9–C12 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯Cg1i	0.96	2.98	3.580 (3)	121
C15—H15B⋯Cg2i	0.96	2.65	3.200 (3)	117
C22—H15A⋯Cg2ii	0.96	2.99	3.872 (4)	152

Symmetry codes: (i) ; (ii) .