3-Dimethyl-amino-1-(4-methyl-phen-yl)prop-2-en-1-one.

In the title compound, C(12)H(15)NO, the C=C and C=O functional groups and the benzene ring are involved in an extended conjugated system. The mol-ecules are essentially planar with a maximal deviation from planarity for the non-H atoms of 0.062 (2) Å.

Related literature

For the pharmaceutical activity of enamino­nes, see: Edafiogh et al. (2003 ▶); Eddington et al. (2003 ▶). For the use of enamino­nes as chelating ligands for main group metals and transition metals in coordination chemistry, see: Cindrić et al. (2004 ▶); Shi et al. (2008 ▶). For the chemical synthesis of enamino­nes, see: Kantevari et al. (2007 ▶); Ke et al. (2009 ▶). For the crystal structures of enamino­nes, see: Lemmerer et al. (2007 ▶); Bertolasi et al. (1999 ▶); Blake et al. (1996 ▶).

Experimental

Crystal data

C12H15NO

M = 189.25

Monoclinic,

a = 8.7918 (17) Å

b = 5.9506 (12) Å

c = 20.789 (4) Å

β = 99.300 (3)°

V = 1073.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 173 K

0.08 × 0.06 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.994, T max = 0.998

5180 measured reflections

2290 independent reflections

1731 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.150

S = 1.02

2290 reflections

130 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809048879/vm2013sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048879/vm2013Isup2.hkl

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

C12H15NO	F(000) = 408
Mr = 189.25	Dx = 1.171 Mg m−3
Monoclinic, P21/c	Melting point: 367 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.7918 (17) Å	Cell parameters from 1291 reflections
b = 5.9506 (12) Å	θ = 3.1–28.6°
c = 20.789 (4) Å	µ = 0.07 mm−1
β = 99.300 (3)°	T = 173 K
V = 1073.3 (4) Å3	Plate, colourless
Z = 4	0.08 × 0.06 × 0.03 mm

Bruker APEX CCD diffractometer	2290 independent reflections
Radiation source: fine-focus sealed tube	1731 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω and phi scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→10
Tmin = 0.994, Tmax = 0.998	k = −7→7
5180 measured reflections	l = −11→26

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0918P)2 + 0.1894P] where P = (Fo2 + 2Fc2)/3
2290 reflections	(Δ/σ)max < 0.001
130 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.23 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.

	x	y	z	Uiso*/Ueq
O1	0.19626 (13)	0.51500 (19)	0.07917 (6)	0.0490 (4)
N1	−0.15817 (14)	0.0530 (2)	0.05528 (6)	0.0327 (3)
C1	0.84154 (18)	0.1518 (3)	0.24118 (8)	0.0439 (4)
H1A	0.8475	−0.0002	0.2596	0.066*
H1B	0.8626	0.2619	0.2765	0.066*
H1C	0.9179	0.1680	0.2120	0.066*
C2	0.68222 (16)	0.1912 (2)	0.20336 (7)	0.0308 (3)
C3	0.64246 (17)	0.3950 (3)	0.17274 (7)	0.0346 (4)
H3A	0.7179	0.5101	0.1744	0.042*
C4	0.49477 (17)	0.4341 (2)	0.13971 (7)	0.0318 (3)
H4A	0.4705	0.5753	0.1193	0.038*
C5	0.38156 (16)	0.2684 (2)	0.13621 (6)	0.0271 (3)
C6	0.42232 (16)	0.0632 (2)	0.16573 (7)	0.0302 (3)
H6A	0.3478	−0.0535	0.1632	0.036*
C7	0.57032 (17)	0.0256 (3)	0.19896 (7)	0.0328 (4)
H7A	0.5952	−0.1161	0.2190	0.039*
C8	0.22148 (16)	0.3234 (2)	0.10167 (7)	0.0301 (3)
C9	0.10551 (16)	0.1520 (2)	0.09670 (7)	0.0291 (3)
H9A	0.1299	0.0087	0.1157	0.035*
C10	−0.03947 (16)	0.1940 (2)	0.06473 (7)	0.0296 (3)
H10A	−0.0578	0.3408	0.0472	0.036*
C11	−0.1441 (2)	−0.1751 (3)	0.07988 (9)	0.0442 (4)
H11A	−0.0440	−0.2368	0.0739	0.066*
H11B	−0.2268	−0.2675	0.0560	0.066*
H11C	−0.1520	−0.1752	0.1264	0.066*
C12	−0.30880 (17)	0.1211 (3)	0.02142 (8)	0.0411 (4)
H12A	−0.3026	0.2740	0.0045	0.062*
H12B	−0.3833	0.1175	0.0518	0.062*
H12C	−0.3421	0.0178	−0.0148	0.062*

	U11	U22	U33	U12	U13	U23
O1	0.0387 (7)	0.0328 (6)	0.0712 (9)	−0.0016 (5)	−0.0038 (6)	0.0170 (6)
N1	0.0276 (6)	0.0359 (7)	0.0341 (7)	−0.0024 (5)	0.0035 (5)	−0.0010 (5)
C1	0.0330 (9)	0.0542 (10)	0.0421 (9)	0.0026 (7)	−0.0008 (7)	−0.0023 (8)
C2	0.0276 (7)	0.0373 (8)	0.0274 (7)	0.0008 (6)	0.0047 (5)	−0.0040 (6)
C3	0.0325 (8)	0.0346 (8)	0.0367 (8)	−0.0090 (6)	0.0056 (6)	−0.0041 (6)
C4	0.0360 (8)	0.0261 (7)	0.0335 (8)	−0.0030 (6)	0.0065 (6)	0.0026 (6)
C5	0.0283 (7)	0.0286 (7)	0.0250 (7)	−0.0013 (5)	0.0062 (5)	−0.0018 (5)
C6	0.0299 (7)	0.0280 (7)	0.0326 (8)	−0.0030 (6)	0.0050 (6)	0.0013 (6)
C7	0.0356 (8)	0.0318 (8)	0.0309 (7)	0.0028 (6)	0.0048 (6)	0.0031 (6)
C8	0.0321 (8)	0.0280 (7)	0.0305 (7)	0.0006 (6)	0.0056 (6)	0.0015 (6)
C9	0.0286 (8)	0.0282 (7)	0.0307 (7)	0.0004 (6)	0.0055 (6)	0.0019 (6)
C10	0.0316 (8)	0.0288 (7)	0.0296 (7)	−0.0003 (6)	0.0083 (6)	−0.0007 (6)
C11	0.0457 (10)	0.0360 (9)	0.0512 (10)	−0.0103 (7)	0.0090 (8)	−0.0011 (7)
C12	0.0285 (8)	0.0562 (11)	0.0377 (8)	−0.0011 (7)	0.0031 (6)	−0.0056 (7)

O1—C8	1.2388 (18)	C5—C8	1.509 (2)
N1—C10	1.3288 (18)	C6—C7	1.389 (2)
N1—C11	1.448 (2)	C6—H6A	0.9500
N1—C12	1.453 (2)	C7—H7A	0.9500
C1—C2	1.510 (2)	C8—C9	1.434 (2)
C1—H1A	0.9800	C9—C10	1.362 (2)
C1—H1B	0.9800	C9—H9A	0.9500
C1—H1C	0.9800	C10—H10A	0.9500
C2—C7	1.385 (2)	C11—H11A	0.9800
C2—C3	1.388 (2)	C11—H11B	0.9800
C3—C4	1.387 (2)	C11—H11C	0.9800
C3—H3A	0.9500	C12—H12A	0.9800
C4—C5	1.395 (2)	C12—H12B	0.9800
C4—H4A	0.9500	C12—H12C	0.9800
C5—C6	1.387 (2)
C10—N1—C11	121.29 (13)	C2—C7—C6	121.09 (13)
C10—N1—C12	121.85 (13)	C2—C7—H7A	119.5
C11—N1—C12	116.84 (13)	C6—C7—H7A	119.5
C2—C1—H1A	109.5	O1—C8—C9	123.07 (13)
C2—C1—H1B	109.5	O1—C8—C5	118.41 (13)
H1A—C1—H1B	109.5	C9—C8—C5	118.52 (12)
C2—C1—H1C	109.5	C10—C9—C8	120.19 (13)
H1A—C1—H1C	109.5	C10—C9—H9A	119.9
H1B—C1—H1C	109.5	C8—C9—H9A	119.9
C7—C2—C3	117.91 (13)	N1—C10—C9	127.35 (14)
C7—C2—C1	120.88 (14)	N1—C10—H10A	116.3
C3—C2—C1	121.21 (14)	C9—C10—H10A	116.3
C4—C3—C2	121.32 (13)	N1—C11—H11A	109.5
C4—C3—H3A	119.3	N1—C11—H11B	109.5
C2—C3—H3A	119.3	H11A—C11—H11B	109.5
C3—C4—C5	120.69 (14)	N1—C11—H11C	109.5
C3—C4—H4A	119.7	H11A—C11—H11C	109.5
C5—C4—H4A	119.7	H11B—C11—H11C	109.5
C6—C5—C4	117.92 (13)	N1—C12—H12A	109.5
C6—C5—C8	123.77 (13)	N1—C12—H12B	109.5
C4—C5—C8	118.31 (13)	H12A—C12—H12B	109.5
C5—C6—C7	121.06 (13)	N1—C12—H12C	109.5
C5—C6—H6A	119.5	H12A—C12—H12C	109.5
C7—C6—H6A	119.5	H12B—C12—H12C	109.5