organic compounds
1,4-Bis(benzyloxy)-2-tert-butylbenzene
aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
*Correspondence e-mail: wjt@njut.edu.cn
The title compound, C24H26O2, was obtained unintentionally as the product of an attempted synthesis of a new chiral cobalt salen catalyst. There are no classical hydrogen bonds; intermolecular C—H⋯π stacking interactions between aromatic rings help to establish the molecular conformation.
Related literature
For related literature, see: Annis & Jacobsen (1999); Kwon & Kim (2003); Ready & Jacobsen (2001). For bond-length data, see: Allen et al. (1987).
Experimental
Crystal data
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Refinement
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Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536808003383/rk2077sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808003383/rk2077Isup2.hkl
Under N2 atmosphere, a mixture of 5.5 g (33 mmol) of 2–tert–butyl–hydroquinone, 2.25 g anhydrous potassium carbonate (16.0 mmol) in 75 ml dry acetonitrile were stirred for half an hour at room temperature. Subsequently 8.2 g (66 mmol) of benzyl chloride and 600 mg (3.6 mmol) of potassium iodide were added to the reaction mixture and was refluxed for 3 h in inert atmosphere. The mixture was cooled to room temperature and was filtrated and the solvent was removed under reduced pressure. The crude product was purified with n–hexane solution. Crystals of (I) suitable for X–ray diffraction were further recrystallized by slow evaporation of acetone. 1H NMR (CDCl3, δ, p.p.m.) 7.45 (q, 10H), 7.00 (s, 1H), 6.89 (d, 1H), 6.74 (d, 1H), 5.05 (s, 2H), 4.99 (S, 2H), 1.38 (s, 9H).
During the
the phenyl rings were treated as rigid hexagons with C–C bond lengths of 1.39 Å. H atoms were positioned geometrically (C—H = 0.930, 0.970 and 0.960Å for aromatic, methylene and methyl H atoms respectively) and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl and x = 1.2 for all other H atoms.Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell
CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C24H26O2 | F(000) = 744 |
Mr = 346.45 | Dx = 1.144 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 6.5570 (13) Å | θ = 9–13° |
b = 23.772 (5) Å | µ = 0.07 mm−1 |
c = 12.924 (3) Å | T = 293 K |
β = 93.21 (3)° | Block, colourless |
V = 2011.3 (7) Å3 | 0.40 × 0.30 × 0.20 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 2336 reflections with I > 2σ(I) |
Radiation source: fine–focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 26.0°, θmin = 1.7° |
ω/2θ scans | h = 0→8 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→29 |
Tmin = 0.969, Tmax = 0.986 | l = −15→15 |
4285 measured reflections | 3 standard reflections every 200 reflections |
3935 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.072 | H-atom parameters constrained |
wR(F2) = 0.162 | w = 1/[σ2(Fo2) + (0.0054P)2 + 4.1075P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3935 reflections | Δρmax = 0.35 e Å−3 |
188 parameters | Δρmin = −0.33 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0384 (15) |
C24H26O2 | V = 2011.3 (7) Å3 |
Mr = 346.45 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.5570 (13) Å | µ = 0.07 mm−1 |
b = 23.772 (5) Å | T = 293 K |
c = 12.924 (3) Å | 0.40 × 0.30 × 0.20 mm |
β = 93.21 (3)° |
Enraf–Nonius CAD-4 diffractometer | 2336 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.027 |
Tmin = 0.969, Tmax = 0.986 | 3 standard reflections every 200 reflections |
4285 measured reflections | intensity decay: none |
3935 independent reflections |
R[F2 > 2σ(F2)] = 0.072 | 0 restraints |
wR(F2) = 0.162 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.35 e Å−3 |
3935 reflections | Δρmin = −0.33 e Å−3 |
188 parameters |
Geometry. All s.u.'s (except the s.u.'s in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | ||
C1 | 1.0565 (4) | 0.27733 (12) | 0.5023 (3) | 0.0843 (15) | |
H1 | 1.1645 | 0.2523 | 0.5133 | 0.101* | |
C2 | 1.0574 (4) | 0.31573 (15) | 0.4212 (3) | 0.0931 (17) | |
H2 | 1.1661 | 0.3164 | 0.3780 | 0.112* | |
C3 | 0.8960 (4) | 0.35314 (12) | 0.4048 (2) | 0.0765 (13) | |
H3 | 0.8966 | 0.3788 | 0.3505 | 0.092* | |
C4 | 0.7335 (4) | 0.35215 (11) | 0.4694 (2) | 0.0582 (11) | |
C5 | 0.7326 (4) | 0.31375 (13) | 0.55046 (19) | 0.0719 (13) | |
H5 | 0.6239 | 0.3131 | 0.5937 | 0.086* | |
C6 | 0.8941 (5) | 0.27634 (11) | 0.5669 (2) | 0.0777 (14) | |
H6 | 0.8934 | 0.2506 | 0.6212 | 0.093* | |
C7 | 0.5631 (7) | 0.3943 (2) | 0.4568 (3) | 0.0746 (14) | |
H7A | 0.4514 | 0.3831 | 0.4984 | 0.090* | |
H7B | 0.6112 | 0.4309 | 0.4806 | 0.090* | |
C8 | 0.3396 (3) | 0.43592 (8) | 0.32489 (12) | 0.0461 (9) | |
C9 | 0.2627 (2) | 0.43853 (6) | 0.22256 (11) | 0.0447 (8) | |
C10 | 0.1057 (2) | 0.47575 (8) | 0.19454 (11) | 0.0475 (9) | |
H10 | 0.0543 | 0.4775 | 0.1261 | 0.057* | |
C11 | 0.0255 (3) | 0.51035 (8) | 0.26886 (14) | 0.0486 (9) | |
C12 | 0.1024 (3) | 0.50774 (8) | 0.37119 (13) | 0.0530 (10) | |
H12 | 0.0487 | 0.5309 | 0.4209 | 0.064* | |
C13 | 0.2594 (3) | 0.47053 (9) | 0.39920 (10) | 0.0547 (10) | |
H13 | 0.3108 | 0.4688 | 0.4677 | 0.066* | |
C14 | 0.3591 (3) | 0.40301 (9) | 0.13571 (14) | 0.0655 (10) | |
C15 | 0.2469 (4) | 0.41208 (13) | 0.02966 (13) | 0.0934 (18) | |
H15A | 0.2507 | 0.4512 | 0.0118 | 0.140* | |
H15B | 0.1074 | 0.4002 | 0.0326 | 0.140* | |
H15C | 0.3123 | 0.3905 | −0.0218 | 0.140* | |
C16 | 0.3501 (8) | 0.34034 (19) | 0.1595 (4) | 0.0885 (16) | |
H16A | 0.4201 | 0.3331 | 0.2254 | 0.133* | |
H16B | 0.4145 | 0.3197 | 0.1065 | 0.133* | |
H16C | 0.2101 | 0.3288 | 0.1616 | 0.133* | |
C17 | 0.5827 (6) | 0.4212 (2) | 0.1272 (4) | 0.0834 (15) | |
H17A | 0.6565 | 0.4156 | 0.1927 | 0.125* | |
H17B | 0.5875 | 0.4602 | 0.1085 | 0.125* | |
H17C | 0.6439 | 0.3990 | 0.0751 | 0.125* | |
C18 | −0.2037 (6) | 0.58533 (19) | 0.3026 (3) | 0.0689 (13) | |
H18A | −0.0948 | 0.6094 | 0.3307 | 0.083* | |
H18B | −0.2610 | 0.5653 | 0.3596 | 0.083* | |
C19 | −0.3651 (2) | 0.61998 (7) | 0.24720 (11) | 0.0528 (10) | |
C20 | −0.3295 (3) | 0.67607 (6) | 0.2238 (2) | 0.0705 (12) | |
H20 | −0.2036 | 0.6923 | 0.2422 | 0.085* | |
C21 | −0.4821 (3) | 0.70793 (7) | 0.1730 (2) | 0.0846 (15) | |
H21 | −0.4583 | 0.7455 | 0.1574 | 0.102* | |
C22 | −0.6703 (3) | 0.68368 (9) | 0.14560 (14) | 0.0824 (15) | |
H22 | −0.7724 | 0.7050 | 0.1116 | 0.099* | |
C23 | −0.7060 (2) | 0.62759 (9) | 0.1690 (2) | 0.0797 (14) | |
H23 | −0.8319 | 0.6114 | 0.1506 | 0.096* | |
C24 | −0.5534 (2) | 0.59573 (8) | 0.21979 (18) | 0.0636 (11) | |
H24 | −0.5772 | 0.5582 | 0.2354 | 0.076* | |
O1 | 0.4937 (3) | 0.39766 (9) | 0.35168 (17) | 0.0581 (7) | |
O2 | −0.1255 (2) | 0.54656 (6) | 0.23203 (9) | 0.0577 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.061 (3) | 0.083 (4) | 0.107 (4) | 0.019 (3) | −0.014 (3) | 0.000 (3) |
C2 | 0.056 (3) | 0.102 (4) | 0.123 (5) | 0.014 (3) | 0.013 (3) | 0.024 (4) |
C3 | 0.061 (3) | 0.078 (3) | 0.089 (3) | 0.009 (2) | 0.002 (2) | 0.021 (3) |
C4 | 0.058 (2) | 0.070 (2) | 0.055 (2) | 0.013 (2) | −0.0180 (19) | −0.015 (2) |
C5 | 0.076 (3) | 0.084 (3) | 0.056 (3) | 0.013 (3) | −0.001 (2) | −0.003 (2) |
C6 | 0.096 (4) | 0.070 (3) | 0.065 (3) | 0.014 (3) | −0.014 (3) | 0.008 (2) |
C7 | 0.081 (3) | 0.082 (3) | 0.058 (3) | 0.032 (3) | −0.023 (2) | −0.013 (2) |
C8 | 0.0405 (19) | 0.051 (2) | 0.046 (2) | −0.0003 (17) | −0.0038 (15) | −0.0029 (17) |
C9 | 0.0414 (19) | 0.049 (2) | 0.0437 (19) | −0.0036 (17) | 0.0049 (15) | −0.0008 (16) |
C10 | 0.0413 (19) | 0.061 (2) | 0.0397 (19) | −0.0004 (18) | −0.0004 (15) | −0.0006 (17) |
C11 | 0.0343 (18) | 0.058 (2) | 0.053 (2) | −0.0001 (17) | 0.0006 (16) | 0.0002 (18) |
C12 | 0.057 (2) | 0.057 (2) | 0.044 (2) | 0.0122 (19) | 0.0000 (17) | −0.0064 (18) |
C13 | 0.055 (2) | 0.066 (3) | 0.041 (2) | 0.015 (2) | −0.0061 (17) | −0.0015 (18) |
C14 | 0.065 (2) | 0.075 (3) | 0.057 (2) | 0.002 (2) | 0.0035 (17) | −0.0086 (19) |
C15 | 0.100 (4) | 0.131 (5) | 0.049 (3) | 0.039 (3) | −0.004 (2) | −0.020 (3) |
C16 | 0.114 (4) | 0.071 (3) | 0.081 (3) | 0.001 (3) | 0.009 (3) | −0.021 (3) |
C17 | 0.065 (3) | 0.112 (4) | 0.076 (3) | 0.001 (3) | 0.028 (2) | −0.009 (3) |
C18 | 0.066 (3) | 0.090 (3) | 0.051 (2) | 0.032 (2) | −0.001 (2) | −0.004 (2) |
C19 | 0.051 (2) | 0.063 (3) | 0.045 (2) | 0.0094 (19) | 0.0053 (17) | −0.0049 (18) |
C20 | 0.069 (3) | 0.066 (3) | 0.076 (3) | −0.012 (2) | 0.000 (2) | −0.012 (2) |
C21 | 0.109 (4) | 0.054 (3) | 0.091 (4) | 0.011 (3) | 0.005 (3) | 0.008 (3) |
C22 | 0.077 (3) | 0.096 (4) | 0.073 (3) | 0.032 (3) | 0.000 (3) | 0.010 (3) |
C23 | 0.050 (3) | 0.107 (4) | 0.082 (3) | 0.002 (3) | 0.003 (2) | 0.004 (3) |
C24 | 0.054 (2) | 0.066 (3) | 0.072 (3) | 0.002 (2) | 0.008 (2) | 0.007 (2) |
O1 | 0.0566 (16) | 0.0708 (18) | 0.0461 (14) | 0.0190 (14) | −0.0045 (12) | −0.0035 (13) |
O2 | 0.0476 (15) | 0.0733 (18) | 0.0516 (15) | 0.0168 (13) | −0.0015 (12) | −0.0063 (13) |
C1—C2 | 1.3900 | C14—C16 | 1.523 (5) |
C1—C6 | 1.3900 | C14—C15 | 1.5341 |
C1—H1 | 0.9300 | C14—C17 | 1.539 (5) |
C2—C3 | 1.3900 | C15—H15A | 0.9600 |
C2—H2 | 0.9300 | C15—H15B | 0.9600 |
C3—C4 | 1.3900 | C15—H15C | 0.9600 |
C3—H3 | 0.9300 | C16—H16A | 0.9600 |
C4—C5 | 1.3900 | C16—H16B | 0.9600 |
C4—C7 | 1.503 (4) | C16—H16C | 0.9600 |
C5—C6 | 1.3900 | C17—H17A | 0.9600 |
C5—H5 | 0.9300 | C17—H17B | 0.9600 |
C6—H6 | 0.9300 | C17—H17C | 0.9600 |
C7—O1 | 1.411 (4) | C18—O2 | 1.413 (4) |
C7—H7A | 0.9700 | C18—C19 | 1.492 (4) |
C7—H7B | 0.9700 | C18—H18A | 0.9700 |
C8—O1 | 1.3888 | C18—H18B | 0.9700 |
C8—C9 | 1.3900 | C19—C20 | 1.3900 |
C8—C13 | 1.3900 | C19—C24 | 1.3900 |
C9—C10 | 1.3900 | C20—C21 | 1.3900 |
C9—C14 | 1.5657 | C20—H20 | 0.9300 |
C10—C11 | 1.3900 | C21—C22 | 1.3900 |
C10—H10 | 0.9300 | C21—H21 | 0.9300 |
C11—O2 | 1.3766 | C22—C23 | 1.3900 |
C11—C12 | 1.3900 | C22—H22 | 0.9300 |
C12—C13 | 1.3900 | C23—C24 | 1.3900 |
C12—H12 | 0.9300 | C23—H23 | 0.9300 |
C13—H13 | 0.9300 | C24—H24 | 0.9300 |
C2—C1—C6 | 120.0 | C15—C14—C9 | 111.8 |
C2—C1—H1 | 120.0 | C17—C14—C9 | 108.9 (2) |
C6—C1—H1 | 120.0 | C14—C15—H15A | 109.5 |
C1—C2—C3 | 120.0 | C14—C15—H15B | 109.5 |
C1—C2—H2 | 120.0 | H15A—C15—H15B | 109.5 |
C3—C2—H2 | 120.0 | C14—C15—H15C | 109.5 |
C4—C3—C2 | 120.0 | H15A—C15—H15C | 109.5 |
C4—C3—H3 | 120.0 | H15B—C15—H15C | 109.5 |
C2—C3—H3 | 120.0 | C14—C16—H16A | 109.5 |
C5—C4—C3 | 120.0 | C14—C16—H16B | 109.5 |
C5—C4—C7 | 119.0 (3) | H16A—C16—H16B | 109.5 |
C3—C4—C7 | 120.9 (3) | C14—C16—H16C | 109.5 |
C4—C5—C6 | 120.0 | H16A—C16—H16C | 109.5 |
C4—C5—H5 | 120.0 | H16B—C16—H16C | 109.5 |
C6—C5—H5 | 120.0 | C14—C17—H17A | 109.5 |
C5—C6—C1 | 120.0 | C14—C17—H17B | 109.5 |
C5—C6—H6 | 120.0 | H17A—C17—H17B | 109.5 |
C1—C6—H6 | 120.0 | C14—C17—H17C | 109.5 |
O1—C7—C4 | 109.9 (3) | H17A—C17—H17C | 109.5 |
O1—C7—H7A | 109.7 | H17B—C17—H17C | 109.5 |
C4—C7—H7A | 109.7 | O2—C18—C19 | 108.9 (3) |
O1—C7—H7B | 109.7 | O2—C18—H18A | 109.9 |
C4—C7—H7B | 109.7 | C19—C18—H18A | 109.9 |
H7A—C7—H7B | 108.2 | O2—C18—H18B | 109.9 |
O1—C8—C9 | 119.10 | C19—C18—H18B | 109.9 |
O1—C8—C13 | 120.88 | H18A—C18—H18B | 108.3 |
C9—C8—C13 | 120.0 | C20—C19—C24 | 120.0 |
C10—C9—C8 | 120.0 | C20—C19—C18 | 120.7 (2) |
C10—C9—C14 | 118.6 | C24—C19—C18 | 119.3 (2) |
C8—C9—C14 | 121.2 | C21—C20—C19 | 120.0 |
C11—C10—C9 | 120.0 | C21—C20—H20 | 120.0 |
C11—C10—H10 | 120.0 | C19—C20—H20 | 120.0 |
C9—C10—H10 | 120.0 | C20—C21—C22 | 120.0 |
O2—C11—C10 | 115.07 | C20—C21—H21 | 120.0 |
O2—C11—C12 | 124.91 | C22—C21—H21 | 120.0 |
C10—C11—C12 | 120.0 | C21—C22—C23 | 120.0 |
C13—C12—C11 | 120.0 | C21—C22—H22 | 120.0 |
C13—C12—H12 | 120.0 | C23—C22—H22 | 120.0 |
C11—C12—H12 | 120.0 | C24—C23—C22 | 120.0 |
C12—C13—C8 | 120.0 | C24—C23—H23 | 120.0 |
C12—C13—H13 | 120.0 | C22—C23—H23 | 120.0 |
C8—C13—H13 | 120.0 | C23—C24—C19 | 120.0 |
C16—C14—C15 | 107.2 (2) | C23—C24—H24 | 120.0 |
C16—C14—C17 | 109.7 (3) | C19—C24—H24 | 120.0 |
C15—C14—C17 | 108.0 (2) | C8—O1—C7 | 117.9 (2) |
C16—C14—C9 | 111.2 (2) | C11—O2—C18 | 117.68 (19) |
C6—C1—C2—C3 | 0.0 | C10—C9—C14—C16 | −124.7 (3) |
C1—C2—C3—C4 | 0.0 | C8—C9—C14—C16 | 59.3 (3) |
C2—C3—C4—C5 | 0.0 | C10—C9—C14—C15 | −4.9 |
C2—C3—C4—C7 | 176.5 (3) | C8—C9—C14—C15 | 179.1 |
C3—C4—C5—C6 | 0.0 | C10—C9—C14—C17 | 114.4 (2) |
C7—C4—C5—C6 | −176.6 (3) | C8—C9—C14—C17 | −61.6 (2) |
C4—C5—C6—C1 | 0.0 | O2—C18—C19—C20 | −107.8 (3) |
C2—C1—C6—C5 | 0.0 | O2—C18—C19—C24 | 72.8 (3) |
C5—C4—C7—O1 | −135.2 (3) | C24—C19—C20—C21 | 0.0 |
C3—C4—C7—O1 | 48.2 (4) | C18—C19—C20—C21 | −179.40 (18) |
O1—C8—C9—C10 | 178.7 | C19—C20—C21—C22 | 0.0 |
C13—C8—C9—C10 | 0.0 | C20—C21—C22—C23 | 0.0 |
O1—C8—C9—C14 | −5.3 | C21—C22—C23—C24 | 0.0 |
C13—C8—C9—C14 | 176.0 | C22—C23—C24—C19 | 0.0 |
C8—C9—C10—C11 | 0.0 | C20—C19—C24—C23 | 0.0 |
C14—C9—C10—C11 | −176.1 | C18—C19—C24—C23 | 179.41 (18) |
C9—C10—C11—O2 | 178.3 | C9—C8—O1—C7 | −177.5 (3) |
C9—C10—C11—C12 | 0.0 | C13—C8—O1—C7 | 1.2 (4) |
O2—C11—C12—C13 | −178.2 | C4—C7—O1—C8 | −178.2 (3) |
C10—C11—C12—C13 | 0.0 | C10—C11—O2—C18 | −176.0 (2) |
C11—C12—C13—C8 | 0.0 | C12—C11—O2—C18 | 2.3 (3) |
O1—C8—C13—C12 | −178.7 | C19—C18—O2—C11 | −179.7 (2) |
C9—C8—C13—C12 | 0.0 |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cg3i | 0.93 | 2.96 | 3.725 | 141 |
C15—H15C···Cg3ii | 0.96 | 2.87 | 3.818 | 168 |
C24—H24···Cg2iii | 0.93 | 2.71 | 3.560 | 153 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+1, −z; (iii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C24H26O2 |
Mr | 346.45 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 6.5570 (13), 23.772 (5), 12.924 (3) |
β (°) | 93.21 (3) |
V (Å3) | 2011.3 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.40 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.969, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4285, 3935, 2336 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.072, 0.162, 1.03 |
No. of reflections | 3935 |
No. of parameters | 188 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.33 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cg3i | 0.93 | 2.96 | 3.725 | 141 |
C15—H15C···Cg3ii | 0.96 | 2.87 | 3.818 | 168 |
C24—H24···Cg2iii | 0.93 | 2.71 | 3.560 | 153 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+1, −z; (iii) x−1, y, z. |
Acknowledgements
The authors thank the Center of Testing and Analysis, Nanjing University, for support.
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.
Chiral Co(salen) complexes are widely used in the Hydrolytic Kinetic Resolution of terminal epoxides, such as epichlorohydrin (Annis & Jacobsen, 1999). Bis–phenols, such as 2–tert–butyl–hydroquinone, are useful as starting materials for the synthesis of salicylaldehyde (Ready & Jacobsen, 2001), especially in the synthesis of polymeric salen complexes (Kwon & Kim, 2003). We here report the molecular and crystal structure of the title compound (I).
The atom–numbering scheme of (I) is shown in Fig. 1. A l l bond lengths and angles are within normal ranges (Allen et al., 1987). The molecule contains three phenyl rings - ring 1 (C1–C6), ring 2 (C8–C13), ring 3 (C19—C24), which are planar. The dihedral angle between ring 1 and ring 2 is 48.5 (4)°. There are no typical hydrogen bonds, while intermolecular C—H···π stacking interactions between aromatic rings help to stabilize the molecular conformation of compound (I).