Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029028/sg6031sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029028/sg6031Isup2.hkl |
CCDC reference: 287726
The synthesis of 4-isopropyl-para-anisyl-phenylidene-2 tetralone-1 was achieved using the method reported by Kerbal et al. (1988). That means a condensation of para-anisaldahyde with 4-isopropyl-tetralone-1 in an alcaline medium in methanol.
All H atoms were located in a difference map and were refined with fixed individual displacement parameters [Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(Cmethyl)] using a riding model, with C—H ranging from 0.95 to 1.00 Å. In addition, the CH3 group attached to the O atom was allowed to rotate but not to tip.
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level. |
C21H22O2 | F(000) = 656 |
Mr = 306.39 | Dx = 1.215 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25892 reflections |
a = 7.9380 (5) Å | θ = 3.4–25.8° |
b = 9.3745 (4) Å | µ = 0.08 mm−1 |
c = 22.7340 (16) Å | T = 173 K |
β = 98.219 (5)° | Block, colourless |
V = 1674.37 (17) Å3 | 0.35 × 0.33 × 0.29 mm |
Z = 4 |
Stoe IPDS-II two-circle diffractometer | 2800 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.040 |
Graphite monochromator | θmax = 25.6°, θmin = 3.4° |
ω scans | h = −9→9 |
26652 measured reflections | k = −11→11 |
3147 independent reflections | l = −27→25 |
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)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0595P)2 + 0.4741P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
3147 reflections | Δρmax = 0.25 e Å−3 |
210 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.024 (3) |
C21H22O2 | V = 1674.37 (17) Å3 |
Mr = 306.39 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.9380 (5) Å | µ = 0.08 mm−1 |
b = 9.3745 (4) Å | T = 173 K |
c = 22.7340 (16) Å | 0.35 × 0.33 × 0.29 mm |
β = 98.219 (5)° |
Stoe IPDS-II two-circle diffractometer | 2800 reflections with I > 2σ(I) |
26652 measured reflections | Rint = 0.040 |
3147 independent reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.25 e Å−3 |
3147 reflections | Δρmin = −0.17 e Å−3 |
210 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 | 0.97679 (11) | 0.54685 (11) | 0.20869 (4) | 0.0364 (3) | |
C1 | 0.82768 (14) | 0.58779 (12) | 0.20260 (6) | 0.0249 (3) | |
C2 | 0.73578 (15) | 0.61684 (12) | 0.25442 (5) | 0.0235 (3) | |
C3 | 0.55489 (15) | 0.67181 (13) | 0.23986 (5) | 0.0248 (3) | |
H3A | 0.5567 | 0.7748 | 0.2303 | 0.030* | |
H3B | 0.4947 | 0.6597 | 0.2748 | 0.030* | |
C4 | 0.45933 (14) | 0.58946 (13) | 0.18629 (5) | 0.0231 (3) | |
H4 | 0.3423 | 0.6305 | 0.1769 | 0.028* | |
C5 | 0.55189 (15) | 0.61442 (12) | 0.13337 (5) | 0.0226 (3) | |
C6 | 0.46723 (16) | 0.63647 (13) | 0.07599 (6) | 0.0271 (3) | |
H6 | 0.3463 | 0.6376 | 0.0692 | 0.033* | |
C7 | 0.55750 (18) | 0.65682 (13) | 0.02842 (6) | 0.0302 (3) | |
H7 | 0.4979 | 0.6728 | −0.0103 | 0.036* | |
C8 | 0.73464 (18) | 0.65375 (14) | 0.03742 (6) | 0.0319 (3) | |
H8 | 0.7959 | 0.6672 | 0.0049 | 0.038* | |
C9 | 0.82135 (16) | 0.63094 (13) | 0.09404 (6) | 0.0287 (3) | |
H9 | 0.9422 | 0.6284 | 0.1002 | 0.034* | |
C10 | 0.73164 (15) | 0.61173 (12) | 0.14208 (5) | 0.0235 (3) | |
C11 | 0.81825 (15) | 0.58691 (12) | 0.30893 (6) | 0.0247 (3) | |
H11 | 0.9270 | 0.5440 | 0.3099 | 0.030* | |
C12 | 0.76367 (15) | 0.61130 (12) | 0.36725 (5) | 0.0241 (3) | |
C13 | 0.81472 (15) | 0.51513 (13) | 0.41354 (6) | 0.0280 (3) | |
H13 | 0.8830 | 0.4356 | 0.4062 | 0.034* | |
C14 | 0.76859 (16) | 0.53246 (13) | 0.46977 (6) | 0.0287 (3) | |
H14 | 0.8035 | 0.4650 | 0.5003 | 0.034* | |
C15 | 0.67039 (15) | 0.65011 (13) | 0.48102 (5) | 0.0254 (3) | |
C16 | 0.62228 (15) | 0.75000 (13) | 0.43603 (6) | 0.0268 (3) | |
H16 | 0.5585 | 0.8317 | 0.4440 | 0.032* | |
C17 | 0.66704 (15) | 0.73050 (13) | 0.37999 (5) | 0.0258 (3) | |
H17 | 0.6322 | 0.7984 | 0.3497 | 0.031* | |
O2 | 0.61530 (11) | 0.67818 (11) | 0.53422 (4) | 0.0336 (2) | |
C18 | 0.66685 (19) | 0.58251 (17) | 0.58261 (6) | 0.0397 (3) | |
H18A | 0.6272 | 0.4859 | 0.5714 | 0.060* | |
H18B | 0.6173 | 0.6135 | 0.6176 | 0.060* | |
H18C | 0.7913 | 0.5826 | 0.5919 | 0.060* | |
C41 | 0.44219 (15) | 0.42722 (13) | 0.19868 (6) | 0.0260 (3) | |
H41 | 0.5581 | 0.3838 | 0.2012 | 0.031* | |
C42 | 0.37636 (18) | 0.39845 (17) | 0.25752 (6) | 0.0372 (3) | |
H42A | 0.4503 | 0.4461 | 0.2899 | 0.056* | |
H42B | 0.3765 | 0.2955 | 0.2650 | 0.056* | |
H42C | 0.2602 | 0.4353 | 0.2555 | 0.056* | |
C43 | 0.32687 (19) | 0.35340 (16) | 0.14796 (7) | 0.0390 (3) | |
H43A | 0.3693 | 0.3723 | 0.1103 | 0.059* | |
H43B | 0.2107 | 0.3903 | 0.1459 | 0.059* | |
H43C | 0.3269 | 0.2503 | 0.1552 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0234 (5) | 0.0488 (6) | 0.0371 (5) | 0.0083 (4) | 0.0043 (4) | −0.0031 (4) |
C1 | 0.0223 (6) | 0.0208 (6) | 0.0316 (7) | −0.0002 (4) | 0.0042 (5) | −0.0022 (5) |
C2 | 0.0233 (6) | 0.0198 (6) | 0.0271 (6) | −0.0004 (4) | 0.0023 (5) | −0.0023 (4) |
C3 | 0.0256 (6) | 0.0248 (6) | 0.0239 (6) | 0.0052 (5) | 0.0037 (5) | −0.0009 (5) |
C4 | 0.0195 (5) | 0.0251 (6) | 0.0244 (6) | 0.0049 (4) | 0.0021 (4) | 0.0011 (5) |
C5 | 0.0277 (6) | 0.0155 (5) | 0.0249 (6) | 0.0023 (4) | 0.0049 (5) | −0.0007 (4) |
C6 | 0.0306 (6) | 0.0220 (6) | 0.0281 (6) | 0.0027 (5) | 0.0019 (5) | −0.0007 (5) |
C7 | 0.0446 (7) | 0.0224 (6) | 0.0231 (6) | 0.0015 (5) | 0.0028 (5) | −0.0002 (5) |
C8 | 0.0455 (8) | 0.0253 (6) | 0.0279 (6) | −0.0010 (5) | 0.0153 (6) | −0.0007 (5) |
C9 | 0.0303 (6) | 0.0233 (6) | 0.0341 (7) | −0.0006 (5) | 0.0107 (5) | −0.0013 (5) |
C10 | 0.0271 (6) | 0.0168 (5) | 0.0272 (6) | 0.0012 (4) | 0.0058 (5) | −0.0009 (4) |
C11 | 0.0222 (5) | 0.0207 (6) | 0.0305 (6) | 0.0004 (4) | 0.0014 (5) | −0.0015 (5) |
C12 | 0.0230 (5) | 0.0214 (6) | 0.0262 (6) | −0.0020 (4) | −0.0021 (4) | −0.0012 (5) |
C13 | 0.0272 (6) | 0.0243 (6) | 0.0307 (6) | 0.0037 (5) | −0.0027 (5) | −0.0002 (5) |
C14 | 0.0306 (6) | 0.0260 (6) | 0.0273 (6) | −0.0004 (5) | −0.0035 (5) | 0.0052 (5) |
C15 | 0.0236 (6) | 0.0277 (6) | 0.0240 (6) | −0.0065 (5) | 0.0001 (4) | −0.0009 (5) |
C16 | 0.0279 (6) | 0.0221 (6) | 0.0299 (6) | 0.0012 (5) | 0.0020 (5) | −0.0020 (5) |
C17 | 0.0296 (6) | 0.0202 (6) | 0.0261 (6) | −0.0001 (5) | −0.0008 (5) | 0.0024 (5) |
O2 | 0.0359 (5) | 0.0407 (5) | 0.0247 (5) | −0.0007 (4) | 0.0059 (4) | 0.0022 (4) |
C18 | 0.0422 (8) | 0.0494 (9) | 0.0270 (7) | −0.0083 (6) | 0.0031 (6) | 0.0083 (6) |
C41 | 0.0201 (5) | 0.0265 (6) | 0.0314 (7) | 0.0007 (5) | 0.0038 (5) | 0.0036 (5) |
C42 | 0.0340 (7) | 0.0434 (8) | 0.0344 (7) | −0.0036 (6) | 0.0061 (6) | 0.0118 (6) |
C43 | 0.0405 (8) | 0.0357 (7) | 0.0400 (8) | −0.0106 (6) | 0.0031 (6) | −0.0013 (6) |
O1—C1 | 1.2332 (15) | C12—C17 | 1.4087 (17) |
C1—C10 | 1.4915 (17) | C13—C14 | 1.3887 (18) |
C1—C2 | 1.4967 (17) | C13—H13 | 0.9500 |
C2—C11 | 1.3458 (17) | C14—C15 | 1.3951 (18) |
C2—C3 | 1.5169 (16) | C14—H14 | 0.9500 |
C3—C4 | 1.5461 (16) | C15—O2 | 1.3691 (15) |
C3—H3A | 0.9900 | C15—C16 | 1.3988 (17) |
C3—H3B | 0.9900 | C16—C17 | 1.3829 (18) |
C4—C5 | 1.5147 (16) | C16—H16 | 0.9500 |
C4—C41 | 1.5563 (16) | C17—H17 | 0.9500 |
C4—H4 | 1.0000 | O2—C18 | 1.4331 (17) |
C5—C6 | 1.3949 (17) | C18—H18A | 0.9800 |
C5—C10 | 1.4124 (17) | C18—H18B | 0.9800 |
C6—C7 | 1.3931 (18) | C18—H18C | 0.9800 |
C6—H6 | 0.9500 | C41—C42 | 1.5281 (17) |
C7—C8 | 1.3920 (19) | C41—C43 | 1.5311 (18) |
C7—H7 | 0.9500 | C41—H41 | 1.0000 |
C8—C9 | 1.3868 (19) | C42—H42A | 0.9800 |
C8—H8 | 0.9500 | C42—H42B | 0.9800 |
C9—C10 | 1.3980 (17) | C42—H42C | 0.9800 |
C9—H9 | 0.9500 | C43—H43A | 0.9800 |
C11—C12 | 1.4703 (17) | C43—H43B | 0.9800 |
C11—H11 | 0.9500 | C43—H43C | 0.9800 |
C12—C13 | 1.4009 (17) | ||
O1—C1—C10 | 120.42 (11) | C17—C12—C11 | 123.23 (11) |
O1—C1—C2 | 122.43 (11) | C14—C13—C12 | 122.02 (11) |
C10—C1—C2 | 117.15 (10) | C14—C13—H13 | 119.0 |
C11—C2—C1 | 117.34 (10) | C12—C13—H13 | 119.0 |
C11—C2—C3 | 126.33 (11) | C13—C14—C15 | 119.27 (11) |
C1—C2—C3 | 116.28 (10) | C13—C14—H14 | 120.4 |
C2—C3—C4 | 110.17 (9) | C15—C14—H14 | 120.4 |
C2—C3—H3A | 109.6 | O2—C15—C14 | 124.83 (11) |
C4—C3—H3A | 109.6 | O2—C15—C16 | 115.39 (11) |
C2—C3—H3B | 109.6 | C14—C15—C16 | 119.77 (11) |
C4—C3—H3B | 109.6 | C17—C16—C15 | 120.39 (11) |
H3A—C3—H3B | 108.1 | C17—C16—H16 | 119.8 |
C5—C4—C3 | 108.02 (9) | C15—C16—H16 | 119.8 |
C5—C4—C41 | 111.08 (9) | C16—C17—C12 | 120.89 (11) |
C3—C4—C41 | 113.03 (10) | C16—C17—H17 | 119.6 |
C5—C4—H4 | 108.2 | C12—C17—H17 | 119.6 |
C3—C4—H4 | 108.2 | C15—O2—C18 | 117.76 (11) |
C41—C4—H4 | 108.2 | O2—C18—H18A | 109.5 |
C6—C5—C10 | 118.40 (11) | O2—C18—H18B | 109.5 |
C6—C5—C4 | 122.83 (11) | H18A—C18—H18B | 109.5 |
C10—C5—C4 | 118.75 (10) | O2—C18—H18C | 109.5 |
C7—C6—C5 | 120.92 (12) | H18A—C18—H18C | 109.5 |
C7—C6—H6 | 119.5 | H18B—C18—H18C | 109.5 |
C5—C6—H6 | 119.5 | C42—C41—C43 | 109.69 (11) |
C8—C7—C6 | 120.26 (12) | C42—C41—C4 | 112.37 (11) |
C8—C7—H7 | 119.9 | C43—C41—C4 | 111.33 (10) |
C6—C7—H7 | 119.9 | C42—C41—H41 | 107.8 |
C9—C8—C7 | 119.77 (12) | C43—C41—H41 | 107.8 |
C9—C8—H8 | 120.1 | C4—C41—H41 | 107.8 |
C7—C8—H8 | 120.1 | C41—C42—H42A | 109.5 |
C8—C9—C10 | 120.28 (12) | C41—C42—H42B | 109.5 |
C8—C9—H9 | 119.9 | H42A—C42—H42B | 109.5 |
C10—C9—H9 | 119.9 | C41—C42—H42C | 109.5 |
C9—C10—C5 | 120.36 (11) | H42A—C42—H42C | 109.5 |
C9—C10—C1 | 119.32 (11) | H42B—C42—H42C | 109.5 |
C5—C10—C1 | 120.32 (11) | C41—C43—H43A | 109.5 |
C2—C11—C12 | 129.10 (11) | C41—C43—H43B | 109.5 |
C2—C11—H11 | 115.5 | H43A—C43—H43B | 109.5 |
C12—C11—H11 | 115.5 | C41—C43—H43C | 109.5 |
C13—C12—C17 | 117.62 (11) | H43A—C43—H43C | 109.5 |
C13—C12—C11 | 119.10 (11) | H43B—C43—H43C | 109.5 |
O1—C1—C2—C11 | −4.61 (18) | C2—C1—C10—C9 | 159.78 (11) |
C10—C1—C2—C11 | 175.95 (10) | O1—C1—C10—C5 | 160.09 (11) |
O1—C1—C2—C3 | 177.82 (11) | C2—C1—C10—C5 | −20.46 (15) |
C10—C1—C2—C3 | −1.62 (15) | C1—C2—C11—C12 | 176.42 (11) |
C11—C2—C3—C4 | −135.17 (12) | C3—C2—C11—C12 | −6.3 (2) |
C1—C2—C3—C4 | 42.14 (14) | C2—C11—C12—C13 | 147.14 (13) |
C2—C3—C4—C5 | −61.03 (12) | C2—C11—C12—C17 | −35.39 (19) |
C2—C3—C4—C41 | 62.28 (13) | C17—C12—C13—C14 | 1.95 (18) |
C3—C4—C5—C6 | −139.93 (11) | C11—C12—C13—C14 | 179.56 (11) |
C41—C4—C5—C6 | 95.58 (13) | C12—C13—C14—C15 | −0.91 (18) |
C3—C4—C5—C10 | 41.72 (13) | C13—C14—C15—O2 | 179.24 (11) |
C41—C4—C5—C10 | −82.76 (12) | C13—C14—C15—C16 | −1.09 (18) |
C10—C5—C6—C7 | −0.64 (17) | O2—C15—C16—C17 | −178.30 (10) |
C4—C5—C6—C7 | −178.99 (11) | C14—C15—C16—C17 | 2.00 (18) |
C5—C6—C7—C8 | 0.76 (18) | C15—C16—C17—C12 | −0.92 (18) |
C6—C7—C8—C9 | −0.28 (18) | C13—C12—C17—C16 | −1.02 (17) |
C7—C8—C9—C10 | −0.30 (19) | C11—C12—C17—C16 | −178.53 (11) |
C8—C9—C10—C5 | 0.41 (18) | C14—C15—O2—C18 | 2.22 (17) |
C8—C9—C10—C1 | −179.82 (11) | C16—C15—O2—C18 | −177.46 (11) |
C6—C5—C10—C9 | 0.05 (16) | C5—C4—C41—C42 | 170.49 (10) |
C4—C5—C10—C9 | 178.47 (10) | C3—C4—C41—C42 | 48.88 (13) |
C6—C5—C10—C1 | −179.71 (10) | C5—C4—C41—C43 | −66.01 (13) |
C4—C5—C10—C1 | −1.29 (16) | C3—C4—C41—C43 | 172.38 (10) |
O1—C1—C10—C9 | −19.67 (17) |
Experimental details
Crystal data | |
Chemical formula | C21H22O2 |
Mr | 306.39 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 7.9380 (5), 9.3745 (4), 22.7340 (16) |
β (°) | 98.219 (5) |
V (Å3) | 1674.37 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.35 × 0.33 × 0.29 |
Data collection | |
Diffractometer | Stoe IPDS-II two-circle diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26652, 3147, 2800 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.608 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.105, 1.02 |
No. of reflections | 3147 |
No. of parameters | 210 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.17 |
Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97 and PLATON (Spek, 2003).
Knowledge of the configuration and conformation of the title compound, (I), is necessary to understand its behaviour in dipolar-1,3 cycloaddition reactions (Badri et al., 1999; Bennani et al., 2002). To confirm the E configuration of the acyclic C═C double bond and the axial position of the isopropyl group an X-ray structure determination was carried out.
A perspective view of the title compound is shown in Fig. 1. Bond lengths and angles can be regarded as normal (Cambridge Crystallographic Database, Version 1.7; Mogul Version 1.0.1; Allen, 2002). The acyclic C═C double bond shows an E configuration. The carbonyl group is almost coplanar with this double bond [O1—C1—C2—C11 = − 4.61 (18)°], but the phenyl ring attached to it is twisted out of the plane of the double bond [C2—C11—C12—C17 − 35.39 (19)°]. The isopropyl group is attached in an axial position to the cyclohexenone ring.