(Z)-4-(2,5-Di-tert-butyl-anilino)pent-3-en-2-one.

In the crystal structure of the title ketoamine, C(19)H(29)NO, 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 steric hindrance exerted by the tert-butyl groups. The mol-ecule has a Z-configured alkene function, which is facilitated by an intra-molecular N-H⋯O hydrogen bond between the amine and ketone groups. The mol-ecules are linked into extended chains, which run parallel to the [010] direction, by a very weak C-H⋯O inter-action between the methyl substituent of the alkene group and the ketone O atom of a neighbouring mol-ecule.

Related literature

For the conformations of β-pan class="Chemical">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 class="Gene">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

C19H29NO

M = 287.44

Monoclinic,

a = 23.7759 (5) Å

b = 9.0517 (2) Å

c = 19.3760 (4) Å

β = 120.6308 (11)°

V = 3588.11 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.06 mm−1

T = 160 K

0.32 × 0.25 × 0.20 mm

Data collection

Nonius KappaCCD area-detector diffractometer

24643 measured reflections

3153 independent reflections

2769 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.118

S = 1.04

3152 reflections

203 parameters

pan class="Disease">H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DEn class="Chemical">NZO-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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017296/lh5243sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017296/lh5243Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811017296/lh5243Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811017296/lh5243Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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	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)

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

Table 1

Hydrogen-bond geometry (Å, °)

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) .