Literature DB >> 22064822

1-(2,4,6-Triisopropyl-phen-yl)ethanone.

Amber D Blair1, Arthur D Hendsbee, Jason D Masuda.   

Abstract

The title compound, C(17)H(26)O, is a di-ortho-alkyl substituted phenyl ethanone that exhibits a significant twisting of the ketone fragment relative to the aromatic ring [O-C-C-C torsion angle = 89.32 (17)°] due to steric pressure from the ortho-isopropyl groups. One ortho- and the para-isopropyl group exhibit orientational disorder with a refined site occupancy factor of 0.562 (3):0.438 (3).

Entities:  

Year:  2011        PMID： 22064822      PMCID： PMC3201453          DOI： 10.1107/S1600536811038293

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

There are two examples in the literature of crystallo­graph­ically characterized ortho-substituted phenyl ethano­nes, see: van Koningsveld et al. (1987 ▶); Padmanabhan et al. (1986 ▶); De Ridder & Schenk (1995 ▶). For the preparation, see: Delair et al. (1996 ▶). For the use of the title mol­ecule in the preparation of 2-ethynyl-1,3,5-triisopropyl­benzene, see: Tani et al. (1963 ▶). For some related ligands containing ortho-isopropyl groups, see: Boeré & Masuda (2002 ▶); Boeré et al. (2008 ▶); Giffin et al. (2010a ▶,b ▶, 2011 ▶).

Experimental

Crystal data

C17H26O M = 246.38 Monoclinic, a = 5.8590 (12) Å b = 20.248 (4) Å c = 13.148 (3) Å β = 92.568 (2)° V = 1558.2 (6) Å3 Z = 4 Mo Kα radiation μ = 0.06 mm−1 T = 129 K 0.45 × 0.41 × 0.35 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.972, T max = 0.978 10949 measured reflections 3047 independent reflections 2460 reflections with I > 2σ(I) R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.048 wR(F 2) = 0.120 S = 1.05 3047 reflections 214 parameters 21 restraints H-atom parameters constrained Δρmax = 0.19 e Å−3 Δρmin = −0.27 e Å−3 Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL (Bruker, 2008 ▶) and publCIF (Westrip, 2010 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811038293/nr2011sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038293/nr2011Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811038293/nr2011Isup3.mol Supplementary material file. DOI: 10.1107/S1600536811038293/nr2011Isup4.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H26OF(000) = 544
Mr = 246.38Dx = 1.051 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3864 reflections
a = 5.8590 (12) Åθ = 2.5–27.8°
b = 20.248 (4) ŵ = 0.06 mm−1
c = 13.148 (3) ÅT = 129 K
β = 92.568 (2)°Block, colourless
V = 1558.2 (6) Å30.45 × 0.41 × 0.35 mm
Z = 4
Bruker APEXII CCD diffractometer3047 independent reflections
Radiation source: fine-focus sealed tube2460 reflections with I > 2σ(I)
graphiteRint = 0.030
φ and ω scansθmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −7→7
Tmin = 0.972, Tmax = 0.978k = −24→24
10949 measured reflectionsl = −16→13
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0417P)2 + 0.6687P] where P = (Fo2 + 2Fc2)/3
3047 reflections(Δ/σ)max < 0.001
214 parametersΔρmax = 0.19 e Å−3
21 restraintsΔρmin = −0.27 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.
xyzUiso*/UeqOcc. (<1)
O10.01390 (17)0.19352 (5)0.46376 (7)0.0360 (3)
C1−0.0742 (2)0.17979 (7)0.38182 (10)0.0274 (3)
C2−0.3278 (3)0.17911 (13)0.36357 (14)0.0645 (7)
H2A−0.40110.19370.42530.097*
H2B−0.37830.13420.34620.097*
H2C−0.37050.20900.30730.097*
C30.0664 (2)0.16216 (7)0.29222 (10)0.0250 (3)
C40.1265 (2)0.09627 (7)0.27715 (11)0.0298 (3)
C50.2545 (2)0.08078 (8)0.19350 (11)0.0337 (4)
H5A0.29630.03610.18270.040*
C60.3226 (2)0.12825 (9)0.12577 (11)0.0340 (4)
C70.2595 (2)0.19336 (8)0.14225 (11)0.0345 (4)
H7A0.30450.22650.09600.041*
C80.1318 (2)0.21148 (7)0.22491 (10)0.0284 (3)
C90.0604 (3)0.04223 (8)0.35037 (14)0.0458 (5)
H9A−0.03780.06270.40210.055*
C100.2720 (4)0.01420 (11)0.40679 (19)0.0743 (7)
H10A0.34800.04920.44710.111*
H10B0.3773−0.00320.35740.111*
H10C0.2268−0.02150.45210.111*
C11−0.0781 (4)−0.01245 (10)0.2970 (2)0.0781 (8)
H11A−0.21560.00650.26340.117*
H11B−0.1222−0.04530.34730.117*
H11C0.0146−0.03370.24610.117*
C12A0.4554 (7)0.09901 (19)0.0358 (4)0.0262 (8)0.562 (3)
H12A0.48830.05120.04870.031*0.562 (3)
C13A0.3133 (6)0.1066 (2)−0.0634 (3)0.0268 (7)0.562 (3)
H13A0.40340.0925−0.12050.040*0.562 (3)
H13B0.26930.1530−0.07260.040*0.562 (3)
H13C0.17560.0793−0.06090.040*0.562 (3)
C14A0.6817 (4)0.13736 (14)0.0294 (2)0.0299 (7)0.562 (3)
H14A0.76950.1193−0.02590.045*0.562 (3)
H14B0.77060.13310.09400.045*0.562 (3)
H14C0.64880.18410.01600.045*0.562 (3)
C12B0.4652 (9)0.1237 (2)0.0327 (5)0.0238 (10)0.438 (3)
H12B0.50660.16890.00900.029*0.438 (3)
C14B0.6776 (5)0.08476 (18)0.0610 (3)0.0307 (9)0.438 (3)
H14D0.77300.10980.11050.046*0.438 (3)
H14E0.76330.0766−0.00010.046*0.438 (3)
H14F0.63470.04250.09100.046*0.438 (3)
C13B0.3143 (10)0.0881 (3)−0.0497 (4)0.0287 (14)*0.438 (3)
H13D0.40460.0791−0.10900.043*0.438 (3)
H13E0.18410.1163−0.07000.043*0.438 (3)
H13F0.25840.0465−0.02220.043*0.438 (3)
C15A0.0614 (13)0.2804 (4)0.2368 (7)0.0403 (10)0.562 (3)
H15A−0.00940.28580.30410.048*0.562 (3)
C16A−0.1203 (7)0.2960 (2)0.1501 (3)0.0578 (10)0.562 (3)
H16A−0.17520.34140.15760.087*0.562 (3)
H16B−0.24880.26530.15410.087*0.562 (3)
H16C−0.05110.29120.08400.087*0.562 (3)
C17A0.2662 (6)0.32461 (14)0.2330 (3)0.0495 (9)0.562 (3)
H17A0.38180.31060.28470.074*0.562 (3)
H17B0.22080.37030.24620.074*0.562 (3)
H17C0.32980.32180.16540.074*0.562 (3)
C15B0.0787 (18)0.2866 (5)0.2488 (10)0.044 (2)0.438 (3)
H15B−0.05080.28640.29580.053*0.438 (3)
C16B0.0019 (8)0.3298 (2)0.1582 (3)0.0445 (10)0.438 (3)
H16D−0.12750.30880.12110.067*0.438 (3)
H16E0.12860.33500.11260.067*0.438 (3)
H16F−0.04450.37320.18270.067*0.438 (3)
C17B0.2869 (6)0.32093 (18)0.3094 (4)0.0402 (10)0.438 (3)
H17D0.32280.29640.37230.060*0.438 (3)
H17E0.24590.36650.32600.060*0.438 (3)
H17F0.42060.32110.26710.060*0.438 (3)
U11U22U33U12U13U23
O10.0370 (6)0.0477 (7)0.0232 (5)−0.0009 (5)−0.0008 (4)−0.0086 (5)
C10.0263 (7)0.0320 (7)0.0240 (7)−0.0024 (6)0.0019 (5)−0.0061 (6)
C20.0251 (8)0.131 (2)0.0382 (10)−0.0011 (10)0.0074 (7)−0.0324 (11)
C30.0169 (6)0.0364 (8)0.0215 (7)−0.0047 (5)−0.0007 (5)−0.0064 (6)
C40.0251 (7)0.0345 (8)0.0302 (8)−0.0103 (6)0.0061 (6)−0.0112 (6)
C50.0268 (7)0.0419 (8)0.0330 (8)−0.0057 (6)0.0067 (6)−0.0162 (7)
C60.0176 (6)0.0633 (10)0.0212 (7)−0.0002 (6)0.0001 (5)−0.0076 (7)
C70.0210 (7)0.0589 (10)0.0235 (7)0.0008 (6)−0.0013 (5)0.0088 (7)
C80.0197 (6)0.0397 (7)0.0253 (7)0.0006 (5)−0.0048 (5)0.0021 (6)
C90.0527 (10)0.0298 (8)0.0574 (11)−0.0150 (7)0.0299 (9)−0.0112 (7)
C100.0848 (16)0.0629 (14)0.0770 (16)−0.0128 (12)0.0222 (13)0.0352 (12)
C110.0690 (14)0.0466 (11)0.123 (2)−0.0340 (10)0.0532 (14)−0.0408 (12)
C12A0.0276 (14)0.027 (2)0.0246 (13)−0.0014 (14)0.0059 (10)−0.002 (2)
C13A0.0273 (14)0.032 (2)0.0215 (12)−0.0052 (15)0.0069 (10)−0.0046 (15)
C14A0.0219 (11)0.0399 (17)0.0283 (13)0.0005 (10)0.0048 (9)−0.0030 (12)
C12B0.0224 (18)0.027 (3)0.0221 (16)−0.0016 (17)0.0031 (11)−0.003 (3)
C14B0.0245 (15)0.038 (2)0.0303 (18)0.0031 (12)0.0035 (12)−0.0010 (14)
C15A0.039 (3)0.0478 (17)0.035 (2)0.0202 (17)0.0160 (19)0.017 (2)
C16A0.059 (2)0.072 (3)0.0433 (19)0.0391 (18)0.0063 (15)0.0148 (18)
C17A0.077 (2)0.0236 (12)0.049 (2)0.0030 (13)0.0153 (17)−0.0030 (14)
C15B0.036 (4)0.0340 (19)0.061 (5)0.006 (2)−0.013 (3)0.011 (2)
C16B0.049 (2)0.0377 (19)0.047 (2)0.0158 (19)0.0026 (18)0.0073 (17)
C17B0.044 (2)0.0297 (17)0.047 (3)−0.0006 (14)0.0028 (16)−0.0076 (16)
O1—C11.2060 (17)C13A—H13B0.9800
C1—C21.495 (2)C13A—H13C0.9800
C1—C31.5102 (19)C14A—H14A0.9800
C2—H2A0.9800C14A—H14B0.9800
C2—H2B0.9800C14A—H14C0.9800
C2—H2C0.9800C12B—C14B1.506 (6)
C3—C41.396 (2)C12B—C13B1.546 (8)
C3—C81.399 (2)C12B—H12B1.0000
C4—C51.3942 (19)C14B—H14D0.9800
C4—C91.519 (2)C14B—H14E0.9800
C5—C61.381 (2)C14B—H14F0.9800
C5—H5A0.9500C13B—H13D0.9800
C6—C71.389 (2)C13B—H13E0.9800
C6—C12B1.515 (7)C13B—H13F0.9800
C6—C12A1.561 (5)C15A—C17A1.500 (8)
C7—C81.396 (2)C15A—C16A1.557 (8)
C7—H7A0.9500C15A—H15A1.0000
C8—C15A1.466 (8)C16A—H16A0.9800
C8—C15B1.587 (11)C16A—H16B0.9800
C9—C111.525 (2)C16A—H16C0.9800
C9—C101.526 (3)C17A—H17A0.9800
C9—H9A1.0000C17A—H17B0.9800
C10—H10A0.9800C17A—H17C0.9800
C10—H10B0.9800C15B—C16B1.528 (11)
C10—H10C0.9800C15B—C17B1.587 (10)
C11—H11A0.9800C15B—H15B1.0000
C11—H11B0.9800C16B—H16D0.9800
C11—H11C0.9800C16B—H16E0.9800
C12A—C13A1.524 (7)C16B—H16F0.9800
C12A—C14A1.542 (5)C17B—H17D0.9800
C12A—H12A1.0000C17B—H17E0.9800
C13A—H13A0.9800C17B—H17F0.9800
O1—C1—C2121.88 (13)C12A—C14A—H14A109.5
O1—C1—C3121.65 (12)C12A—C14A—H14B109.5
C2—C1—C3116.47 (12)H14A—C14A—H14B109.5
C1—C2—H2A109.5C12A—C14A—H14C109.5
C1—C2—H2B109.5H14A—C14A—H14C109.5
H2A—C2—H2B109.5H14B—C14A—H14C109.5
C1—C2—H2C109.5C6—C12B—C14B108.1 (4)
H2A—C2—H2C109.5C6—C12B—C13B106.0 (4)
H2B—C2—H2C109.5C14B—C12B—C13B111.7 (4)
C4—C3—C8120.95 (13)C6—C12B—H12B110.3
C4—C3—C1119.11 (12)C14B—C12B—H12B110.3
C8—C3—C1119.94 (13)C13B—C12B—H12B110.3
C5—C4—C3118.35 (14)C12B—C14B—H14D109.5
C5—C4—C9119.96 (14)C12B—C14B—H14E109.5
C3—C4—C9121.68 (13)H14D—C14B—H14E109.5
C6—C5—C4122.21 (14)C12B—C14B—H14F109.5
C6—C5—H5A118.9H14D—C14B—H14F109.5
C4—C5—H5A118.9H14E—C14B—H14F109.5
C5—C6—C7118.26 (13)C12B—C13B—H13D109.5
C5—C6—C12B131.6 (2)C12B—C13B—H13E109.5
C7—C6—C12B110.1 (2)H13D—C13B—H13E109.5
C5—C6—C12A113.13 (19)C12B—C13B—H13F109.5
C7—C6—C12A128.56 (19)H13D—C13B—H13F109.5
C6—C7—C8121.78 (14)H13E—C13B—H13F109.5
C6—C7—H7A119.1C8—C15A—C17A109.6 (5)
C8—C7—H7A119.1C8—C15A—C16A107.6 (5)
C7—C8—C3118.45 (14)C17A—C15A—C16A112.1 (5)
C7—C8—C15A119.8 (3)C8—C15A—H15A109.2
C3—C8—C15A121.7 (3)C17A—C15A—H15A109.2
C7—C8—C15B121.5 (5)C16A—C15A—H15A109.2
C3—C8—C15B119.8 (5)C15A—C16A—H16A109.5
C4—C9—C11112.16 (17)C15A—C16A—H16B109.5
C4—C9—C10110.56 (13)H16A—C16A—H16B109.5
C11—C9—C10110.95 (17)C15A—C16A—H16C109.5
C4—C9—H9A107.7H16A—C16A—H16C109.5
C11—C9—H9A107.7H16B—C16A—H16C109.5
C10—C9—H9A107.7C15A—C17A—H17A109.5
C9—C10—H10A109.5C15A—C17A—H17B109.5
C9—C10—H10B109.5H17A—C17A—H17B109.5
H10A—C10—H10B109.5C15A—C17A—H17C109.5
C9—C10—H10C109.5H17A—C17A—H17C109.5
H10A—C10—H10C109.5H17B—C17A—H17C109.5
H10B—C10—H10C109.5C16B—C15B—C17B109.5 (7)
C9—C11—H11A109.5C16B—C15B—C8116.6 (8)
C9—C11—H11B109.5C17B—C15B—C8111.5 (6)
H11A—C11—H11B109.5C16B—C15B—H15B106.2
C9—C11—H11C109.5C17B—C15B—H15B106.2
H11A—C11—H11C109.5C8—C15B—H15B106.2
H11B—C11—H11C109.5C15B—C16B—H16D109.5
C13A—C12A—C14A109.9 (4)C15B—C16B—H16E109.5
C13A—C12A—C6109.8 (3)H16D—C16B—H16E109.5
C14A—C12A—C6108.0 (3)C15B—C16B—H16F109.5
C13A—C12A—H12A109.7H16D—C16B—H16F109.5
C14A—C12A—H12A109.7H16E—C16B—H16F109.5
C6—C12A—H12A109.7C15B—C17B—H17D109.5
C12A—C13A—H13A109.5C15B—C17B—H17E109.5
C12A—C13A—H13B109.5H17D—C17B—H17E109.5
H13A—C13A—H13B109.5C15B—C17B—H17F109.5
C12A—C13A—H13C109.5H17D—C17B—H17F109.5
H13A—C13A—H13C109.5H17E—C17B—H17F109.5
H13B—C13A—H13C109.5
O1—C1—C3—C489.32 (17)C5—C4—C9—C1066.0 (2)
C2—C1—C3—C4−90.50 (18)C3—C4—C9—C10−112.65 (17)
O1—C1—C3—C8−91.58 (17)C5—C6—C12A—C13A112.2 (3)
C2—C1—C3—C888.60 (18)C7—C6—C12A—C13A−64.9 (4)
C8—C3—C4—C50.3 (2)C12B—C6—C12A—C13A−77.6 (11)
C1—C3—C4—C5179.40 (12)C5—C6—C12A—C14A−128.0 (2)
C8—C3—C4—C9178.99 (13)C7—C6—C12A—C14A55.0 (4)
C1—C3—C4—C9−1.9 (2)C12B—C6—C12A—C14A42.2 (10)
C3—C4—C5—C6−0.1 (2)C5—C6—C12B—C14B−48.4 (4)
C9—C4—C5—C6−178.78 (14)C7—C6—C12B—C14B130.1 (3)
C4—C5—C6—C7−0.3 (2)C12A—C6—C12B—C14B−60.5 (11)
C4—C5—C6—C12B178.1 (3)C5—C6—C12B—C13B71.5 (5)
C4—C5—C6—C12A−177.6 (2)C7—C6—C12B—C13B−110.1 (3)
C5—C6—C7—C80.4 (2)C12A—C6—C12B—C13B59.3 (10)
C12B—C6—C7—C8−178.4 (3)C7—C8—C15A—C17A−52.9 (6)
C12A—C6—C7—C8177.3 (3)C3—C8—C15A—C17A129.8 (4)
C6—C7—C8—C3−0.1 (2)C15B—C8—C15A—C17A53 (6)
C6—C7—C8—C15A−177.5 (4)C7—C8—C15A—C16A69.2 (5)
C6—C7—C8—C15B174.6 (4)C3—C8—C15A—C16A−108.1 (5)
C4—C3—C8—C7−0.21 (19)C15B—C8—C15A—C16A175 (7)
C1—C3—C8—C7−179.30 (12)C7—C8—C15B—C16B44.8 (8)
C4—C3—C8—C15A177.1 (4)C3—C8—C15B—C16B−140.5 (6)
C1—C3—C8—C15A−1.9 (4)C15A—C8—C15B—C16B−33 (6)
C4—C3—C8—C15B−175.0 (4)C7—C8—C15B—C17B−81.9 (8)
C1—C3—C8—C15B5.9 (4)C3—C8—C15B—C17B92.8 (8)
C5—C4—C9—C11−58.4 (2)C15A—C8—C15B—C17B−160 (7)
C3—C4—C9—C11122.94 (16)
  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  1,3-Bis(2,6-diisopropyl-phen-yl)imidazolidin-2-yl-idene.

Authors:  Nick A Giffin; Arthur D Hendsbee; Jason D Masuda
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-08-04

3.  1,3-Bis(2,6-diisopropyl-phen-yl)imidazolidinium tetra-phenyl-borate dichloro-methane disolvate.

Authors:  Nick A Giffin; Arthur D Hendsbee; Jason D Masuda
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-07-24
  3 in total

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