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organic compounds
4,6-Di-tert-butyl-2,8-dimethoxydibenzo[b,d]furan
aGwangju Science High School, Gwangju 500-480, Republic of Korea, bDepartment of Chemistry, Sunchon National University, Sunchon 540-742, Republic of Korea, and cDepartment of Chemical Engineering, Sunchon National University, Sunchon 540-742, Republic of Korea
*Correspondence e-mail: chkwak@sunchon.ac.kr
In the title compound, C22H28O3, 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 Csp2—Csp2 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 sp2–sp3 hybridized. C—H⋯π interactions 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
|
Refinement
|
|
Data collection: RAPID-AUTO (Rigaku, 2008); cell 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
).
Supporting information
https://doi.org/10.1107/S1600536811048379/bq2314sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048379/bq2314Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811048379/bq2314Isup3.cml
A mixture of BHA (1.20 g, 6.65 mmol) and iron (0.95 g) and copper (0.89 g) powder in a Schlenk tube was heated under argon gas until BHA was melt and this mixture keep ca 170°C for 24 h. Dissolving the product with 30 ml CH2Cl2 for 3 times, the solution was chromatographed on Al2O3 eluting with CH2Cl2/n-hexane(1:1) to afford the title compound. Single crystals of the compound for X-ray analysis were obtained by recrystallization from CH2Cl2/n-hexane (1:1) at -20°C. 13C-NMR (THF-d5) δ 29.245 (C(CH3)3), 32.843 ((O-CH3), 54.707 (C(CH3)3), 11.825, 113.253, 128.572, 139.625, 145.875, 153.619 (Phenyl). ESI-MS (M/z) C22H28O3; Observed (cal'd): [M+H]+ = 341.2186 (340.46).
The H atoms were positioned geometrically and ride on their respective parent atoms. C—H Distance is 0.93 Å (CH, sp2) with Uiso = 1.2Ueq(C) and 0.96 Å (CH3) with Uiso = 1.5Ueq(C).
Oxidative coupling of phenyl is a useful synthetic route for the synthesis of natural products (Malkowsky et al., 2006). 2-tert-Butyl-4-methoxyphenol (BHA) is well kwon as an antioxidant and
of it produces di-BHA and benzofuran derivative by the various method of preparation (Hewgill & Hewitt, 1967; Butsgan et al., 1989). The single-crystal structure of di-BHA was reported but that of benzofuran derived from BHA has not been investigated. Here we describe the structure of title compound obtained from method.The title compound, C22H29O3, forms tricycle adjoined two benzene skeleton in C10 and C11, and C9 and C12 through O1 (Fig. 1). All atoms lies in almost a plane, the dihedral angle between two benzene skeletons is 3.47 (13)° and 5-membered furan ring is a plane with the largest deviation of 0.0052 (14) Å. The bond distance of C10—C11 [1.443 (3) Å] in sp2 –sp2 π (3/2 - x, 1/2 + y, 1/2 - z) interaction involving the benzene ring (C5-C8/C11-C12) and, C15—H15B···π and C22—H22A···π (2 - x, 2 - y, -z) interactions involing furan ring (O1/C9—C12) are found in the (Fig. 2 and Table 1). No classical hydrogen bond is found in the crystal structure.
which connects two benzene skeleton, is considerably shorter than that of C1—C13 [1.538 (3) Å] or C8—C14 [1.530 (3) Å] in sp2-sp3 C15—H15A···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).
Data collection: RAPID-AUTO (Rigaku, 2008); cell
RAPID-AUTO (Rigaku, 2008); data reduction: RAPID-AUTO (Rigaku, 2008); 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). ![]() | Fig. 1. The structure of the title compound with displacement ellipsoids drawn at 50% probability level. |
![]() | Fig. 2. A packing diagram of the title compound. Dashed lines represent C—H···π interactions. |
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 monochromator | 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 |
C22H28O3 | V = 1988.5 (6) Å3 |
Mr = 340.44 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.631 (3) Å | µ = 0.07 mm−1 |
b = 8.2487 (14) Å | T = 100 K |
c = 16.000 (3) Å | 0.5 × 0.4 × 0.2 mm |
β = 105.438 (5)° |
Rigaku R-AXIS RAPID II-S diffractometer | 4563 independent reflections |
Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 2008) | 2123 reflections with I > 2σ(I) |
Tmin = 0.965, Tmax = 0.985 | Rint = 0.107 |
18260 measured reflections |
R[F2 > 2σ(F2)] = 0.076 | 0 restraints |
wR(F2) = 0.229 | H-atom parameters not refined |
S = 0.99 | Δρmax = 0.24 e Å−3 |
4563 reflections | Δρmin = −0.21 e Å−3 |
227 parameters |
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 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+2, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C22H28O3 |
Mr | 340.44 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 15.631 (3), 8.2487 (14), 16.000 (3) |
β (°) | 105.438 (5) |
V (Å3) | 1988.5 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.5 × 0.4 × 0.2 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID II-S |
Absorption correction | Multi-scan (RAPID-AUTO; Rigaku, 2008) |
Tmin, Tmax | 0.965, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18260, 4563, 2123 |
Rint | 0.107 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.076, 0.229, 0.99 |
No. of reflections | 4563 |
No. of parameters | 227 |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.24, −0.21 |
Computer programs: RAPID-AUTO (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).
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 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+2, −y+2, −z. |
Acknowledgements
This work was supported financially by the RIC, 2011, and the Non-Directional Fund of Sunchon National University, 2005.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Oxidative coupling of phenyl is a useful synthetic route for the synthesis of natural products (Malkowsky et al., 2006). 2-tert-Butyl-4-methoxyphenol (BHA) is well kwon as an antioxidant and oxidative coupling of it produces di-BHA and benzofuran derivative by the various method of preparation (Hewgill & Hewitt, 1967; Butsgan et al., 1989). The single-crystal structure of di-BHA was reported but that of benzofuran derived from BHA has not been investigated. Here we describe the structure of title compound obtained from pyrolysis method.
The title compound, C22H29O3, forms tricycle adjoined two benzene skeleton in C10 and C11, and C9 and C12 through O1 (Fig. 1). All atoms lies in almost a plane, the dihedral angle between two benzene skeletons is 3.47 (13)° and 5-membered furan ring is a plane with the largest deviation of 0.0052 (14) Å. The bond distance of C10—C11 [1.443 (3) Å] in sp2 –sp2 hybridization, which connects two benzene skeleton, is considerably shorter than that of C1—C13 [1.538 (3) Å] or C8—C14 [1.530 (3) Å] in sp2-sp3 hybridization. C15—H15A···π (3/2 - x, 1/2 + y, 1/2 - z) interaction involving the benzene ring (C5-C8/C11-C12) and, C15—H15B···π and C22—H22A···π (2 - x, 2 - y, -z) interactions involing furan ring (O1/C9—C12) are found in the crystal structure (Fig. 2 and Table 1). No classical hydrogen bond is found in the crystal structure.