4-(2,3-Dimethyl-anilino)pent-3-en-2-one.

In the title compound, C(13)H(17)NO, the dihedral angle between the aryl ring and the amino-acryl-aldehyde mean plane [N-C=C-C=O; maximum deviation = 0.0144 (9) Å] is 53.43 (4)°. There is an intra-molecular N-H⋯O hydrogen bond involving the amine and carbonyl groups. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming chains propagating along [001].

Related literature

For background to the synthesis of the title compound, see: Shaheen et al. (2006 ▶); Venter et al. (2010 ▶). For applications of rhodium compounds containing bidentate ligand systems, see: Pyżuk et al. (1993 ▶); Tan et al. (2008 ▶); Xia et al. (2008 ▶). For related rhodium enamino­ketonato complexes, see: Brink et al. (2010 ▶); Damoense et al. (1994 ▶); Roodt & Steyn (2000 ▶); Venter et al. (2009a ▶,b ▶; 2012 ▶).

Experimental

Crystal data

C13H17NO

M = 203.28

Monoclinic,

a = 7.526 (3) Å

b = 12.450 (5) Å

c = 12.040 (4) Å

β = 90.243 (4)°

V = 1128.1 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.18 × 0.16 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.987, T max = 0.994

20265 measured reflections

2817 independent reflections

2528 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.103

S = 1.05

2817 reflections

144 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SIR92 (Altomare et al., 1992) ▶; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812038779/su2465sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038779/su2465Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812038779/su2465Isup3.cml

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

C13H17NO	F(000) = 440
Mr = 203.28	Dx = 1.197 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9978 reflections
a = 7.526 (3) Å	θ = 2.7–28.4°
b = 12.450 (5) Å	µ = 0.08 mm−1
c = 12.040 (4) Å	T = 100 K
β = 90.243 (4)°	Cuboid, colourless
V = 1128.1 (7) Å3	0.18 × 0.16 × 0.08 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2817 independent reflections
Radiation source: fine-focus sealed tube	2528 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
phi and ω scans	θmax = 28.4°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→10
Tmin = 0.987, Tmax = 0.994	k = −16→16
20265 measured reflections	l = −15→16

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0535P)2 + 0.3712P] where P = (Fo2 + 2Fc2)/3
2817 reflections	(Δ/σ)max < 0.001
144 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.06673 (13)	0.30089 (8)	0.27466 (8)	0.0206 (2)
H1A	0.1442	0.3069	0.34	0.031*
H1B	−0.0323	0.2525	0.2913	0.031*
H1C	0.0202	0.372	0.2552	0.031*
C2	0.17093 (11)	0.25693 (7)	0.17890 (7)	0.01569 (19)
C3	0.15832 (12)	0.14919 (7)	0.15135 (7)	0.01678 (19)
H3	0.083	0.1047	0.1946	0.02*
C4	0.25242 (12)	0.10152 (7)	0.06148 (7)	0.01660 (19)
C5	0.23616 (14)	−0.01799 (8)	0.04301 (9)	0.0233 (2)
H5A	0.1841	−0.0315	−0.0304	0.035*
H5B	0.1597	−0.0491	0.1003	0.035*
H5C	0.3542	−0.051	0.0472	0.035*
C11	0.29955 (12)	0.43578 (7)	0.13435 (7)	0.01577 (19)
C12	0.27101 (11)	0.50391 (7)	0.04322 (7)	0.01532 (19)
C13	0.30377 (12)	0.61452 (7)	0.05608 (8)	0.01670 (19)
C14	0.36216 (12)	0.65366 (8)	0.15862 (8)	0.0192 (2)
H14	0.385	0.7283	0.167	0.023*
C15	0.38734 (12)	0.58538 (8)	0.24843 (8)	0.0199 (2)
H15	0.4246	0.6136	0.318	0.024*
C16	0.35811 (13)	0.47587 (8)	0.23660 (8)	0.0185 (2)
H16	0.3777	0.4286	0.2974	0.022*
C17	0.20554 (13)	0.46041 (8)	−0.06639 (8)	0.0190 (2)
H17A	0.3054	0.4546	−0.118	0.028*
H17B	0.1158	0.5091	−0.0974	0.028*
H17C	0.1529	0.3893	−0.055	0.028*
C18	0.27215 (14)	0.69111 (8)	−0.03884 (9)	0.0223 (2)
H18A	0.1441	0.6989	−0.0515	0.034*
H18B	0.3282	0.6629	−0.1061	0.034*
H18C	0.3235	0.7613	−0.0206	0.034*
N1	0.27422 (11)	0.32320 (6)	0.11920 (7)	0.01722 (18)
O1	0.35012 (9)	0.15398 (5)	−0.00317 (6)	0.01903 (16)
H1	0.3236 (19)	0.2906 (12)	0.0590 (12)	0.033 (4)*

	U11	U22	U33	U12	U13	U23
C1	0.0210 (4)	0.0217 (5)	0.0193 (4)	−0.0008 (4)	0.0040 (3)	−0.0023 (3)
C2	0.0148 (4)	0.0177 (4)	0.0146 (4)	0.0006 (3)	−0.0018 (3)	0.0005 (3)
C3	0.0176 (4)	0.0159 (4)	0.0169 (4)	−0.0007 (3)	0.0001 (3)	0.0017 (3)
C4	0.0167 (4)	0.0155 (4)	0.0176 (4)	0.0002 (3)	−0.0033 (3)	0.0006 (3)
C5	0.0264 (5)	0.0150 (4)	0.0285 (5)	−0.0019 (4)	0.0046 (4)	−0.0016 (4)
C11	0.0155 (4)	0.0138 (4)	0.0181 (4)	0.0003 (3)	0.0018 (3)	−0.0018 (3)
C12	0.0125 (4)	0.0166 (4)	0.0168 (4)	0.0006 (3)	0.0009 (3)	−0.0014 (3)
C13	0.0135 (4)	0.0154 (4)	0.0212 (4)	0.0012 (3)	0.0011 (3)	0.0002 (3)
C14	0.0166 (4)	0.0153 (4)	0.0258 (5)	0.0000 (3)	0.0005 (3)	−0.0041 (3)
C15	0.0183 (4)	0.0221 (5)	0.0192 (4)	0.0002 (3)	−0.0010 (3)	−0.0063 (4)
C16	0.0190 (4)	0.0197 (4)	0.0170 (4)	0.0009 (3)	−0.0003 (3)	−0.0005 (3)
C17	0.0207 (4)	0.0194 (4)	0.0168 (4)	−0.0008 (3)	−0.0012 (3)	−0.0009 (3)
C18	0.0227 (5)	0.0171 (4)	0.0272 (5)	0.0002 (4)	−0.0018 (4)	0.0039 (4)
N1	0.0209 (4)	0.0139 (4)	0.0169 (4)	−0.0001 (3)	0.0031 (3)	−0.0015 (3)
O1	0.0223 (3)	0.0165 (3)	0.0183 (3)	−0.0011 (3)	0.0025 (3)	−0.0004 (2)

C1—C2	1.5005 (13)	C12—C13	1.4074 (14)
C1—H1A	0.98	C12—C17	1.5074 (13)
C1—H1B	0.98	C13—C14	1.3964 (14)
C1—H1C	0.98	C13—C18	1.5066 (14)
C2—N1	1.3441 (12)	C14—C15	1.3878 (14)
C2—C3	1.3849 (14)	C14—H14	0.95
C3—C4	1.4251 (13)	C15—C16	1.3883 (14)
C3—H3	0.95	C15—H15	0.95
C4—O1	1.2562 (12)	C16—H16	0.95
C4—C5	1.5093 (14)	C17—H17A	0.98
C5—H5A	0.98	C17—H17B	0.98
C5—H5B	0.98	C17—H17C	0.98
C5—H5C	0.98	C18—H18A	0.98
C11—C16	1.3979 (13)	C18—H18B	0.98
C11—C12	1.4027 (13)	C18—H18C	0.98
C11—N1	1.4262 (13)	N1—H1	0.911 (15)
C2—C1—H1A	109.5	C14—C13—C12	119.54 (8)
C2—C1—H1B	109.5	C14—C13—C18	119.86 (9)
H1A—C1—H1B	109.5	C12—C13—C18	120.58 (9)
C2—C1—H1C	109.5	C15—C14—C13	121.10 (9)
H1A—C1—H1C	109.5	C15—C14—H14	119.4
H1B—C1—H1C	109.5	C13—C14—H14	119.5
N1—C2—C3	120.37 (8)	C14—C15—C16	120.03 (9)
N1—C2—C1	119.50 (8)	C14—C15—H15	120
C3—C2—C1	120.12 (8)	C16—C15—H15	120
C2—C3—C4	123.46 (8)	C15—C16—C11	119.35 (9)
C2—C3—H3	118.3	C15—C16—H16	120.3
C4—C3—H3	118.3	C11—C16—H16	120.3
O1—C4—C3	123.23 (9)	C12—C17—H17A	109.5
O1—C4—C5	117.94 (8)	C12—C17—H17B	109.5
C3—C4—C5	118.82 (8)	H17A—C17—H17B	109.5
C4—C5—H5A	109.5	C12—C17—H17C	109.5
C4—C5—H5B	109.5	H17A—C17—H17C	109.5
H5A—C5—H5B	109.5	H17B—C17—H17C	109.5
C4—C5—H5C	109.5	C13—C18—H18A	109.5
H5A—C5—H5C	109.5	C13—C18—H18B	109.5
H5B—C5—H5C	109.5	H18A—C18—H18B	109.5
C16—C11—C12	121.31 (9)	C13—C18—H18C	109.5
C16—C11—N1	120.33 (8)	H18A—C18—H18C	109.5
C12—C11—N1	118.32 (8)	H18B—C18—H18C	109.5
C11—C12—C13	118.65 (9)	C2—N1—C11	127.75 (8)
C11—C12—C17	121.06 (8)	C2—N1—H1	113.0 (9)
C13—C12—C17	120.29 (8)	C11—N1—H1	119.0 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.911 (15)	1.869 (15)	2.6348 (13)	140.2 (13)
C1—H1A···O1i	0.98	2.49	3.4599 (15)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.911 (15)	1.869 (15)	2.6348 (13)	140.2 (13)
C1—H1A⋯O1i	0.98	2.49	3.4599 (15)	173

Symmetry code: (i) .