![](/logos/buttonlogos/cross.png)
![](/logos/buttonlogos/cross.png)
organic compounds
(Z)-4-(2,5-Di-tert-butylanilino)pent-3-en-2-one
aDepartamento de Química, Universidad Simón Bolívar, Caracas 1080A, Venezuela, and bInstitute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland
*Correspondence e-mail: alinden@oci.uzh.ch, rdorta@usb.ve
In the 19H29NO, the bond lengths from the N atom through the alkene group to the ketone O atom show the presence of an extensively delocalized π-system. The dihedral angle between the plane of the phenyl ring and that of the alkene component is 63.45 (7)° due to exerted by the tert-butyl groups. The molecule has a Z-configured alkene function, which is facilitated by an intramolecular N—H⋯O hydrogen bond between the amine and ketone groups. The molecules are linked into extended chains, which run parallel to the [010] direction, by a very weak C—H⋯O interaction between the methyl substituent of the alkene group and the ketone O atom of a neighbouring molecule.
of the title ketoamine, CRelated literature
For the conformations of β-ketoamines, see: Pastrán et al. (2011); Zharkova et al. (2009
). For reactions involving aminoketonate complexes, see: He et al. (2003
); Hsu, Chang et al. (2004
); Lai et al. (2005
); Li et al. (2005
); Tang et al. (2005
); Hsu, Li et al. (2007
); Pan et al. (2008
). For the preparation and coordination chemistry of aminoketonate ligands, see: Jones et al. (1998
); Shukla et al. (2005
); Lesikar et al. (2008
); Sedai et al. (2008
).
Experimental
Crystal data
|
Data collection
|
Refinement
|
|
Data collection: COLLECT (Nonius, 2000); cell DENZO-SMN (Otwinowski & Minor, 1997
); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997
); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: ORTEPII (Johnson, 1976
); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009
).
Supporting information
10.1107/S1600536811017296/lh5243sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811017296/lh5243Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811017296/lh5243Isup3.cdx
Supporting information file. DOI: 10.1107/S1600536811017296/lh5243Isup4.cml
The title compound was prepared by refluxing 2,5-di-tert-butyl-aniline (1.14 g, 5.56 mmol) with 4-[(-)1-phenyl-ethylamino]-pent-3-en-2-one (Lai, et al., 2005) (1.14 g, 5.60 mmol) in dry ethanol (30 ml) and HCl (12M, 0.5 ml) for 24 h. The cooled reaction mixture was treated with 1M K2CO3 and extracted with CH2Cl2 (3 × 10 ml). The extracts were dried over MgSO4, filtered, and the volatiles evaporated in vacuo to afford an orange oil. Methanol (2.0 ml) was added and the resulting solution was cooled to 273 K for two days to yield 0.50 g (37%) of colorless crystals (m.p. 325–327 K). 1H-NMR (400 MHz, CDCl3): δ 1.28 (s, 9H), 1.35 (s, 9H), 1.79 (s, 3H), 2.10 (s, 3H), 5.22 (s, 1H), 7.35–6.97 (m, 3H), 12.48 (s, 1H).
The amine H atom was located in a difference Fourier map and its position and isotropic displacement parameter were refined freely. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H = 0.95 and 0.98 Å for aromatic and methyl H atoms, respectively, and with Uiso(H) = 1.2Ueq(C) for aromatic H atoms or 1.5Ueq(C) for methyl groups. Twelve low angle reflections were excluded from the data set because they were obscured by the beam stop.
Data collection: COLLECT (Nonius, 2000); cell
DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009). ![]() | Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary size. |
C19H29NO | F(000) = 1264 |
Mr = 287.44 | Dx = 1.064 Mg m−3 |
Monoclinic, C2/c | Melting point: 326 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 23.7759 (5) Å | Cell parameters from 3360 reflections |
b = 9.0517 (2) Å | θ = 2.0–25.0° |
c = 19.3760 (4) Å | µ = 0.06 mm−1 |
β = 120.6308 (11)° | T = 160 K |
V = 3588.11 (13) Å3 | Prism, colourless |
Z = 8 | 0.32 × 0.25 × 0.20 mm |
Nonius KappaCCD area-detector diffractometer | 2769 reflections with I > 2σ(I) |
Radiation source: Nonius FR590 sealed tube generator | Rint = 0.035 |
Horizontally mounted graphite crystal monochromator | θmax = 25.0°, θmin = 3.0° |
Detector resolution: 9 pixels mm-1 | h = 0→28 |
ω scans with κ offsets | k = 0→10 |
24643 measured reflections | l = −23→19 |
3153 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.056P)2 + 2.1259P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3152 reflections | Δρmax = 0.19 e Å−3 |
203 parameters | Δρmin = −0.17 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: 0.0053 (10) |
C19H29NO | V = 3588.11 (13) Å3 |
Mr = 287.44 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 23.7759 (5) Å | µ = 0.06 mm−1 |
b = 9.0517 (2) Å | T = 160 K |
c = 19.3760 (4) Å | 0.32 × 0.25 × 0.20 mm |
β = 120.6308 (11)° |
Nonius KappaCCD area-detector diffractometer | 2769 reflections with I > 2σ(I) |
24643 measured reflections | Rint = 0.035 |
3153 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.19 e Å−3 |
3152 reflections | Δρmin = −0.17 e Å−3 |
203 parameters |
Experimental. Solvent used: MeOH Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.811 (1) Frames collected: 1331 Seconds exposure per frame: 60 Degrees rotation per frame: 0.3 Crystal-Detector distance (mm): 30.0 |
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. |
x | y | z | Uiso*/Ueq | ||
O18 | 0.19853 (5) | 0.78576 (13) | 0.11732 (6) | 0.0523 (3) | |
N15 | 0.30334 (6) | 0.85624 (13) | 0.25496 (6) | 0.0337 (3) | |
H15 | 0.2706 (8) | 0.7964 (19) | 0.2197 (10) | 0.048 (4)* | |
C1 | 0.35235 (6) | 0.80923 (15) | 0.33326 (7) | 0.0310 (3) | |
C2 | 0.39376 (6) | 0.68963 (14) | 0.34376 (7) | 0.0313 (3) | |
C3 | 0.43787 (7) | 0.65278 (16) | 0.42337 (8) | 0.0391 (3) | |
H3 | 0.4668 | 0.5722 | 0.4339 | 0.047* | |
C4 | 0.44166 (7) | 0.72794 (17) | 0.48796 (8) | 0.0423 (4) | |
H4 | 0.4732 | 0.6982 | 0.5409 | 0.051* | |
C5 | 0.40051 (7) | 0.84563 (15) | 0.47720 (8) | 0.0361 (3) | |
C6 | 0.35575 (6) | 0.88316 (15) | 0.39810 (8) | 0.0347 (3) | |
H6 | 0.3264 | 0.9625 | 0.3880 | 0.042* | |
C7 | 0.39271 (6) | 0.60546 (15) | 0.27398 (7) | 0.0341 (3) | |
C8 | 0.40461 (8) | 0.71202 (17) | 0.22106 (9) | 0.0430 (4) | |
H81 | 0.4100 | 0.6554 | 0.1817 | 0.065* | |
H82 | 0.4442 | 0.7699 | 0.2547 | 0.065* | |
H83 | 0.3672 | 0.7788 | 0.1930 | 0.065* | |
C9 | 0.32752 (7) | 0.52365 (16) | 0.22340 (9) | 0.0435 (4) | |
H91 | 0.3193 | 0.4603 | 0.2583 | 0.065* | |
H92 | 0.3297 | 0.4628 | 0.1830 | 0.065* | |
H93 | 0.2920 | 0.5957 | 0.1966 | 0.065* | |
C10 | 0.44656 (7) | 0.48728 (17) | 0.30488 (9) | 0.0445 (4) | |
H101 | 0.4396 | 0.4153 | 0.3376 | 0.067* | |
H102 | 0.4893 | 0.5344 | 0.3375 | 0.067* | |
H103 | 0.4451 | 0.4368 | 0.2592 | 0.067* | |
C11 | 0.40414 (7) | 0.93389 (17) | 0.54685 (8) | 0.0424 (4) | |
C12 | 0.43769 (11) | 0.8466 (2) | 0.62528 (9) | 0.0662 (5) | |
H121 | 0.4138 | 0.7544 | 0.6185 | 0.099* | |
H122 | 0.4382 | 0.9056 | 0.6680 | 0.099* | |
H123 | 0.4827 | 0.8237 | 0.6397 | 0.099* | |
C13 | 0.44427 (9) | 1.0737 (2) | 0.55784 (11) | 0.0596 (5) | |
H131 | 0.4880 | 1.0459 | 0.5692 | 0.089* | |
H132 | 0.4480 | 1.1316 | 0.6027 | 0.089* | |
H133 | 0.4225 | 1.1330 | 0.5087 | 0.089* | |
C14 | 0.33608 (8) | 0.9797 (2) | 0.52823 (10) | 0.0636 (5) | |
H141 | 0.3165 | 1.0458 | 0.4817 | 0.095* | |
H142 | 0.3394 | 1.0310 | 0.5747 | 0.095* | |
H143 | 0.3087 | 0.8916 | 0.5164 | 0.095* | |
C16 | 0.30034 (7) | 0.98782 (15) | 0.22102 (8) | 0.0352 (3) | |
C17 | 0.25166 (7) | 1.01571 (16) | 0.14306 (8) | 0.0400 (4) | |
H17 | 0.2498 | 1.1113 | 0.1217 | 0.048* | |
C18 | 0.20430 (7) | 0.91006 (18) | 0.09300 (8) | 0.0445 (4) | |
C19 | 0.16057 (9) | 0.9464 (2) | 0.00524 (9) | 0.0620 (5) | |
H191 | 0.1762 | 0.8945 | −0.0262 | 0.093* | |
H192 | 0.1614 | 1.0532 | −0.0026 | 0.093* | |
H193 | 0.1158 | 0.9152 | −0.0125 | 0.093* | |
C20 | 0.35276 (8) | 1.09906 (17) | 0.26778 (9) | 0.0468 (4) | |
H201 | 0.3460 | 1.1426 | 0.3093 | 0.070* | |
H202 | 0.3511 | 1.1769 | 0.2316 | 0.070* | |
H203 | 0.3955 | 1.0505 | 0.2931 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O18 | 0.0518 (7) | 0.0519 (7) | 0.0380 (6) | −0.0019 (5) | 0.0118 (5) | 0.0034 (5) |
N15 | 0.0348 (6) | 0.0330 (6) | 0.0282 (6) | 0.0030 (5) | 0.0123 (5) | 0.0014 (5) |
C1 | 0.0304 (7) | 0.0321 (7) | 0.0287 (6) | −0.0007 (5) | 0.0138 (5) | 0.0030 (5) |
C2 | 0.0322 (7) | 0.0309 (7) | 0.0314 (7) | −0.0005 (5) | 0.0168 (6) | 0.0022 (5) |
C3 | 0.0427 (8) | 0.0388 (8) | 0.0343 (7) | 0.0104 (6) | 0.0185 (6) | 0.0048 (6) |
C4 | 0.0438 (8) | 0.0483 (9) | 0.0290 (7) | 0.0087 (7) | 0.0143 (6) | 0.0062 (6) |
C5 | 0.0404 (7) | 0.0380 (8) | 0.0312 (7) | −0.0021 (6) | 0.0192 (6) | 0.0000 (6) |
C6 | 0.0357 (7) | 0.0347 (7) | 0.0345 (7) | 0.0027 (6) | 0.0184 (6) | 0.0008 (6) |
C7 | 0.0368 (7) | 0.0338 (7) | 0.0314 (7) | 0.0033 (6) | 0.0172 (6) | 0.0009 (5) |
C8 | 0.0534 (9) | 0.0438 (8) | 0.0408 (8) | 0.0013 (7) | 0.0304 (7) | 0.0013 (6) |
C9 | 0.0437 (8) | 0.0367 (8) | 0.0464 (8) | −0.0017 (6) | 0.0202 (7) | −0.0079 (6) |
C10 | 0.0462 (8) | 0.0463 (9) | 0.0406 (8) | 0.0115 (7) | 0.0218 (7) | 0.0004 (6) |
C11 | 0.0484 (8) | 0.0472 (9) | 0.0322 (7) | 0.0013 (7) | 0.0211 (7) | −0.0024 (6) |
C12 | 0.0964 (14) | 0.0672 (12) | 0.0355 (9) | 0.0107 (11) | 0.0340 (9) | 0.0006 (8) |
C13 | 0.0714 (11) | 0.0555 (11) | 0.0541 (10) | −0.0118 (9) | 0.0336 (9) | −0.0184 (8) |
C14 | 0.0579 (10) | 0.0914 (14) | 0.0497 (9) | 0.0034 (10) | 0.0334 (8) | −0.0173 (9) |
C16 | 0.0418 (7) | 0.0337 (7) | 0.0352 (7) | 0.0071 (6) | 0.0233 (6) | 0.0017 (6) |
C17 | 0.0472 (8) | 0.0397 (8) | 0.0350 (7) | 0.0123 (6) | 0.0223 (6) | 0.0079 (6) |
C18 | 0.0437 (8) | 0.0530 (10) | 0.0339 (8) | 0.0131 (7) | 0.0177 (7) | 0.0047 (7) |
C19 | 0.0629 (11) | 0.0701 (12) | 0.0359 (8) | 0.0130 (9) | 0.0126 (8) | 0.0070 (8) |
C20 | 0.0573 (9) | 0.0379 (8) | 0.0450 (8) | −0.0018 (7) | 0.0258 (7) | 0.0025 (6) |
O18—C18 | 1.2541 (19) | C10—H102 | 0.9800 |
N15—C16 | 1.3447 (18) | C10—H103 | 0.9800 |
N15—C1 | 1.4280 (16) | C11—C14 | 1.525 (2) |
N15—H15 | 0.908 (17) | C11—C12 | 1.528 (2) |
C1—C6 | 1.3888 (18) | C11—C13 | 1.533 (2) |
C1—C2 | 1.4066 (18) | C12—H121 | 0.9800 |
C2—C3 | 1.3935 (18) | C12—H122 | 0.9800 |
C2—C7 | 1.5411 (17) | C12—H123 | 0.9800 |
C3—C4 | 1.387 (2) | C13—H131 | 0.9800 |
C3—H3 | 0.9500 | C13—H132 | 0.9800 |
C4—C5 | 1.388 (2) | C13—H133 | 0.9800 |
C4—H4 | 0.9500 | C14—H141 | 0.9800 |
C5—C6 | 1.3911 (18) | C14—H142 | 0.9800 |
C5—C11 | 1.5324 (19) | C14—H143 | 0.9800 |
C6—H6 | 0.9500 | C16—C17 | 1.3797 (19) |
C7—C8 | 1.5354 (19) | C16—C20 | 1.496 (2) |
C7—C10 | 1.5365 (18) | C17—C18 | 1.418 (2) |
C7—C9 | 1.5374 (19) | C17—H17 | 0.9500 |
C8—H81 | 0.9800 | C18—C19 | 1.510 (2) |
C8—H82 | 0.9800 | C19—H191 | 0.9800 |
C8—H83 | 0.9800 | C19—H192 | 0.9800 |
C9—H91 | 0.9800 | C19—H193 | 0.9800 |
C9—H92 | 0.9800 | C20—H201 | 0.9800 |
C9—H93 | 0.9800 | C20—H202 | 0.9800 |
C10—H101 | 0.9800 | C20—H203 | 0.9800 |
C16—N15—C1 | 126.49 (12) | C14—C11—C12 | 109.23 (14) |
C16—N15—H15 | 110.4 (10) | C14—C11—C5 | 110.88 (12) |
C1—N15—H15 | 123.0 (10) | C12—C11—C5 | 111.88 (13) |
C6—C1—C2 | 121.74 (12) | C14—C11—C13 | 108.59 (15) |
C6—C1—N15 | 117.22 (12) | C12—C11—C13 | 108.44 (14) |
C2—C1—N15 | 121.01 (11) | C5—C11—C13 | 107.73 (12) |
C3—C2—C1 | 114.89 (12) | C11—C12—H121 | 109.5 |
C3—C2—C7 | 121.29 (12) | C11—C12—H122 | 109.5 |
C1—C2—C7 | 123.81 (11) | H121—C12—H122 | 109.5 |
C4—C3—C2 | 123.21 (13) | C11—C12—H123 | 109.5 |
C4—C3—H3 | 118.4 | H121—C12—H123 | 109.5 |
C2—C3—H3 | 118.4 | H122—C12—H123 | 109.5 |
C3—C4—C5 | 121.62 (13) | C11—C13—H131 | 109.5 |
C3—C4—H4 | 119.2 | C11—C13—H132 | 109.5 |
C5—C4—H4 | 119.2 | H131—C13—H132 | 109.5 |
C4—C5—C6 | 115.96 (12) | C11—C13—H133 | 109.5 |
C4—C5—C11 | 123.27 (12) | H131—C13—H133 | 109.5 |
C6—C5—C11 | 120.75 (12) | H132—C13—H133 | 109.5 |
C1—C6—C5 | 122.57 (13) | C11—C14—H141 | 109.5 |
C1—C6—H6 | 118.7 | C11—C14—H142 | 109.5 |
C5—C6—H6 | 118.7 | H141—C14—H142 | 109.5 |
C8—C7—C10 | 107.28 (11) | C11—C14—H143 | 109.5 |
C8—C7—C9 | 110.23 (11) | H141—C14—H143 | 109.5 |
C10—C7—C9 | 106.40 (11) | H142—C14—H143 | 109.5 |
C8—C7—C2 | 110.44 (11) | N15—C16—C17 | 120.22 (13) |
C10—C7—C2 | 111.39 (11) | N15—C16—C20 | 118.68 (12) |
C9—C7—C2 | 110.96 (11) | C17—C16—C20 | 121.02 (13) |
C7—C8—H81 | 109.5 | C16—C17—C18 | 123.81 (14) |
C7—C8—H82 | 109.5 | C16—C17—H17 | 118.1 |
H81—C8—H82 | 109.5 | C18—C17—H17 | 118.1 |
C7—C8—H83 | 109.5 | O18—C18—C17 | 123.28 (13) |
H81—C8—H83 | 109.5 | O18—C18—C19 | 118.33 (15) |
H82—C8—H83 | 109.5 | C17—C18—C19 | 118.33 (15) |
C7—C9—H91 | 109.5 | C18—C19—H191 | 109.5 |
C7—C9—H92 | 109.5 | C18—C19—H192 | 109.5 |
H91—C9—H92 | 109.5 | H191—C19—H192 | 109.5 |
C7—C9—H93 | 109.5 | C18—C19—H193 | 109.5 |
H91—C9—H93 | 109.5 | H191—C19—H193 | 109.5 |
H92—C9—H93 | 109.5 | H192—C19—H193 | 109.5 |
C7—C10—H101 | 109.5 | C16—C20—H201 | 109.5 |
C7—C10—H102 | 109.5 | C16—C20—H202 | 109.5 |
H101—C10—H102 | 109.5 | H201—C20—H202 | 109.5 |
C7—C10—H103 | 109.5 | C16—C20—H203 | 109.5 |
H101—C10—H103 | 109.5 | H201—C20—H203 | 109.5 |
H102—C10—H103 | 109.5 | H202—C20—H203 | 109.5 |
C16—N15—C1—C6 | 65.87 (17) | C3—C2—C7—C10 | −2.30 (18) |
C16—N15—C1—C2 | −116.26 (15) | C1—C2—C7—C10 | 176.39 (12) |
C6—C1—C2—C3 | −0.26 (19) | C3—C2—C7—C9 | 116.04 (14) |
N15—C1—C2—C3 | −178.03 (12) | C1—C2—C7—C9 | −65.27 (16) |
C6—C1—C2—C7 | −179.02 (12) | C4—C5—C11—C14 | −143.77 (16) |
N15—C1—C2—C7 | 3.21 (19) | C6—C5—C11—C14 | 37.95 (19) |
C1—C2—C3—C4 | −0.5 (2) | C4—C5—C11—C12 | −21.6 (2) |
C7—C2—C3—C4 | 178.27 (13) | C6—C5—C11—C12 | 160.16 (14) |
C2—C3—C4—C5 | 0.8 (2) | C4—C5—C11—C13 | 97.53 (17) |
C3—C4—C5—C6 | −0.2 (2) | C6—C5—C11—C13 | −80.74 (17) |
C3—C4—C5—C11 | −178.53 (14) | C1—N15—C16—C17 | 176.87 (12) |
C2—C1—C6—C5 | 0.8 (2) | C1—N15—C16—C20 | 0.26 (19) |
N15—C1—C6—C5 | 178.71 (12) | N15—C16—C17—C18 | −2.8 (2) |
C4—C5—C6—C1 | −0.6 (2) | C20—C16—C17—C18 | 173.76 (13) |
C11—C5—C6—C1 | 177.79 (13) | C16—C17—C18—O18 | 6.9 (2) |
C3—C2—C7—C8 | −121.41 (14) | C16—C17—C18—C19 | −170.40 (14) |
C1—C2—C7—C8 | 57.28 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N15—H15···O18 | 0.908 (17) | 1.848 (17) | 2.6376 (15) | 144.1 (15) |
C20—H201···O18i | 0.98 | 2.52 | 3.474 (2) | 164 |
Symmetry code: (i) −x+1/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H29NO |
Mr | 287.44 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 160 |
a, b, c (Å) | 23.7759 (5), 9.0517 (2), 19.3760 (4) |
β (°) | 120.6308 (11) |
V (Å3) | 3588.11 (13) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.06 |
Crystal size (mm) | 0.32 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Nonius KappaCCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24643, 3153, 2769 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.118, 1.04 |
No. of reflections | 3152 |
No. of parameters | 203 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.19, −0.17 |
Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), ORTEPII (Johnson, 1976), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
O18—C18 | 1.2541 (19) | C16—C17 | 1.3797 (19) |
N15—C16 | 1.3447 (18) | C17—C18 | 1.418 (2) |
N15—C1 | 1.4280 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N15—H15···O18 | 0.908 (17) | 1.848 (17) | 2.6376 (15) | 144.1 (15) |
C20—H201···O18i | 0.98 | 2.52 | 3.474 (2) | 164 |
Symmetry code: (i) −x+1/2, y+1/2, −z+1/2. |
Acknowledgements
This work was financed by FONACIT (project S1–2001000851).
References
He, X., Yao, Y., Luo, X., Zhang, J., Liu, Y., Zhang, L. & Wu, Q. (2003). Organometallics, 22, 4952–4957. Web of Science CSD CrossRef CAS Google Scholar
Hsu, S., Chang, J., Lai, C., Hu, C., Lee, H., Lee, G., Peng, S. & Huang, J. (2004). Inorg. Chem. 43, 6786–6792. Web of Science CSD CrossRef PubMed CAS Google Scholar
Hsu, S., Li, C., Chiu, Y., Chiu, M., Lien, Y., Kuo, P., Lee, H., Cheng, C. & Huang, J. (2007). J. Organomet. Chem. 692, 5421–5428. Web of Science CSD CrossRef CAS Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Jones, D., Roberts, A., Cavell, K., Keim, W., Englert, U., Skelton, B. W. & White, A. H. (1998). J. Chem. Soc. Dalton Trans. 2, pp. 255–262. CrossRef Google Scholar
Lai, Y., Chen, H., Hung, W., Lin, C. & Hong, F. (2005). Tetrahedron, 61, 9484–9489. Web of Science CSD CrossRef CAS Google Scholar
Lesikar, L., Gushwa, A. F. & Richards, A. F. (2008). J. Organomet. Chem. 693, 3245–3255. Web of Science CSD CrossRef CAS Google Scholar
Li, X., Li, Y.-G., Li, Y.-S., Che, Y.-X. & Hu, N. (2005). Organometallics, 24, 2502–2510. CrossRef CAS Google Scholar
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Pan, L., Ye, W., Liu, J., Hong, M. & Li, Y. (2008). Macromolecules, 41, 2981–2983. Web of Science CrossRef CAS Google Scholar
Pastrán, J., Ineichen, E., Agrifoglio, G., Linden, A. & Dorta, R. (2011). Acta Cryst. E67, o188–o189. Web of Science CrossRef IUCr Journals Google Scholar
Sedai, B., Heeg, M. J. & Winter, C. H. (2008). J. Organomet. Chem. 693, 3495–3503. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shukla, P., Gordon, J. C., Cowley, A. H. & Jones, J. N. (2005). J. Organomet. Chem. 690, 1366–1371. CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tang, L., Hu, T., Bo, Y., Li, Y. & Hu, N. (2005). J. Organomet. Chem. 690, 3125–3133. CrossRef CAS Google Scholar
Zharkova, G., Stabnikov, P., Baidina, I., Smolentsev, A. & Tkachey, S. (2009). Polyhedron, 28, 2307–2312. Web of Science CSD CrossRef CAS Google Scholar
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.
Anions of β-amino-α-enones are potentially useful bidentate ligands (Jones, et al., 1998; Shukla, et al., 2005; Hsu, Li et al., 2007; Lesikar, et al., 2008; Sedai, et al., 2008) in stoichiometric (Hsu, Chang et al., 2004) and catalytic processes (He, et al., 2003; Lai, et al., 2005; Li, et al., 2005; Tang, et al., 2005; Pan, et al., 2008). Generally, β-amino-α-enones have Z conformations that are stabilized by intramolecular hydrogen bonds (Zharkova, et al., 2009; Pastrán et al., 2011). The title β-amino-α-enone was derived from 2,5-di-tert-butyl-aniline and acetylacetone, via the 4-[(-)1-phenyl-ethylamino]-pent-3-en-2-one intermediate (Lai, et al., 2005). In its crystal structure, the plane of the aryl ring is twisted out of the plane spanned by the C═C double bond (defined by atoms N15, C16, C17, C18 and C20) by 63.45 (7)° due to the steric pressure exerted by the tert-butyl groups (Fig. 1). The bond lengths from N15 through the alkene group to the ketone O atom, O18, show the presence of an extensively delocalized π-system (Table 1). Even the C1—N15 bond is shorter than a normal single bond, despite the twist about this bond. The Z-configuration of the molecule facilitates the formation of an intramolecular N—H···O hydrogen bond between the amine group and the carbonyl O-atom (Table 2). The molecules are linked into extended 21-symmetrical chains, which run parallel to the [010] direction, by a very weak C—H···O interaction between the methyl substituent of the alkene group and the ketone O atom of a neighbouring molecule. There are no other significant intermolecular interactions in the structure.