(E)-3-Dimethyl-amino-1-(2-pyrid-yl)prop-2-en-1-one.

The mol-ecule of the title compound, C(10)H(12)N(2)O, is approximately planar, with an r.m.s. deviation of 0.072 Å from the mean plane for the non-H atoms. It was synthesized from 2-acetyl-pyridine and N,N-dimethyl-formamide dimethyl acetal in a one-step reaction.

Related literature

For background to related heteroaromatic compounds, see: Zhang et al. (2009 ▶); Liu et al. (2009 ▶); Kida et al. (2009 ▶).

Experimental

Crystal data

C10H12N2O

M = 176.22

Monoclinic,

a = 5.6670 (11) Å

b = 23.117 (5) Å

c = 7.6880 (15) Å

β = 108.17 (3)°

V = 956.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.990, T max = 0.994

7131 measured reflections

1775 independent reflections

1403 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.143

S = 1.00

1775 reflections

121 parameters

H-atom parameters not refined

Δρmax = 0.18 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); 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/S1600536809030530/hb5023sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030530/hb5023Isup2.hkl

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

C10H12N2O	F(000) = 376
Mr = 176.22	Dx = 1.223 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1775 reflections
a = 5.6670 (11) Å	θ = 1.8–25.5°
b = 23.117 (5) Å	µ = 0.08 mm−1
c = 7.6880 (15) Å	T = 295 K
β = 108.17 (3)°	Block, yellow
V = 956.9 (3) Å3	0.12 × 0.10 × 0.08 mm
Z = 4

Bruker APEXII CCD diffractometer	1775 independent reflections
Radiation source: fine-focus sealed tube	1403 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −6→6
Tmin = 0.990, Tmax = 0.994	k = −27→28
7131 measured reflections	l = −9→9

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters not refined
S = 1.00	w = 1/[σ2(Fo2) + (0.087P)2 + 0.1213P] where P = (Fo2 + 2Fc2)/3
1775 reflections	(Δ/σ)max < 0.001
121 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.15 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
C1	0.3675 (4)	0.01987 (8)	−0.3188 (3)	0.0664 (6)
H1A	0.2562	−0.0080	−0.2945	0.100*
H1B	0.5232	0.0016	−0.3092	0.100*
H1C	0.2964	0.0351	−0.4401	0.100*
C2	0.5845 (4)	0.11075 (9)	−0.1969 (3)	0.0674 (6)
H2A	0.5072	0.1481	−0.2079	0.101*
H2B	0.6385	0.1038	−0.3017	0.101*
H2C	0.7251	0.1096	−0.0879	0.101*
C3	0.2893 (3)	0.06861 (7)	−0.0630 (2)	0.0456 (4)
H3	0.1843	0.0377	−0.0633	0.055*
C4	0.3024 (3)	0.11046 (7)	0.0648 (2)	0.0464 (4)
H4	0.4006	0.1430	0.0703	0.056*
C5	0.1648 (3)	0.10380 (7)	0.1890 (2)	0.0445 (4)
C6	0.1719 (3)	0.15207 (6)	0.3237 (2)	0.0423 (4)
C7	0.0089 (3)	0.15063 (8)	0.4258 (2)	0.0533 (5)
H7	−0.1038	0.1204	0.4118	0.064*
C8	0.0165 (4)	0.19467 (9)	0.5484 (2)	0.0615 (5)
H8	−0.0916	0.1947	0.6179	0.074*
C9	0.1851 (4)	0.23816 (8)	0.5661 (2)	0.0608 (5)
H9	0.1951	0.2682	0.6484	0.073*
C10	0.3406 (4)	0.23655 (8)	0.4592 (2)	0.0584 (5)
H10	0.4549	0.2664	0.4720	0.070*
N1	0.4076 (3)	0.06659 (6)	−0.18682 (18)	0.0500 (4)
N2	0.3368 (3)	0.19482 (6)	0.33867 (18)	0.0505 (4)
O1	0.0370 (3)	0.06092 (5)	0.19576 (18)	0.0657 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0977 (16)	0.0551 (11)	0.0587 (11)	0.0089 (10)	0.0423 (11)	−0.0012 (9)
C2	0.0611 (12)	0.0857 (14)	0.0628 (12)	−0.0074 (10)	0.0303 (10)	0.0026 (10)
C3	0.0508 (9)	0.0462 (9)	0.0432 (9)	0.0036 (7)	0.0197 (7)	0.0052 (7)
C4	0.0487 (9)	0.0464 (9)	0.0466 (9)	−0.0007 (7)	0.0185 (7)	−0.0010 (7)
C5	0.0491 (9)	0.0431 (9)	0.0427 (9)	0.0008 (7)	0.0164 (7)	0.0007 (7)
C6	0.0457 (9)	0.0423 (9)	0.0387 (8)	0.0060 (7)	0.0128 (7)	0.0034 (6)
C7	0.0541 (10)	0.0571 (11)	0.0531 (10)	0.0016 (8)	0.0232 (8)	−0.0037 (8)
C8	0.0649 (12)	0.0701 (13)	0.0560 (11)	0.0110 (10)	0.0284 (9)	−0.0077 (9)
C9	0.0763 (13)	0.0555 (11)	0.0482 (10)	0.0122 (9)	0.0161 (9)	−0.0103 (8)
C10	0.0730 (12)	0.0476 (10)	0.0519 (10)	−0.0048 (9)	0.0158 (9)	−0.0051 (8)
N1	0.0591 (9)	0.0520 (8)	0.0462 (8)	0.0031 (6)	0.0271 (7)	0.0023 (6)
N2	0.0581 (9)	0.0476 (8)	0.0466 (8)	−0.0037 (7)	0.0178 (7)	−0.0031 (6)
O1	0.0896 (10)	0.0554 (8)	0.0676 (9)	−0.0208 (7)	0.0472 (8)	−0.0144 (6)

C1—N1	1.451 (2)	C5—O1	1.2384 (18)
C1—H1A	0.9600	C5—C6	1.514 (2)
C1—H1B	0.9600	C6—N2	1.340 (2)
C1—H1C	0.9600	C6—C7	1.386 (2)
C2—N1	1.450 (2)	C7—C8	1.379 (2)
C2—H2A	0.9600	C7—H7	0.9300
C2—H2B	0.9600	C8—C9	1.364 (3)
C2—H2C	0.9600	C8—H8	0.9300
C3—N1	1.325 (2)	C9—C10	1.380 (3)
C3—C4	1.364 (2)	C9—H9	0.9300
C3—H3	0.9300	C10—N2	1.333 (2)
C4—C5	1.417 (2)	C10—H10	0.9300
C4—H4	0.9300
N1—C1—H1A	109.5	C4—C5—C6	118.57 (14)
N1—C1—H1B	109.5	N2—C6—C7	122.61 (15)
H1A—C1—H1B	109.5	N2—C6—C5	118.10 (14)
N1—C1—H1C	109.5	C7—C6—C5	119.29 (15)
H1A—C1—H1C	109.5	C8—C7—C6	119.01 (17)
H1B—C1—H1C	109.5	C8—C7—H7	120.5
N1—C2—H2A	109.5	C6—C7—H7	120.5
N1—C2—H2B	109.5	C9—C8—C7	118.94 (17)
H2A—C2—H2B	109.5	C9—C8—H8	120.5
N1—C2—H2C	109.5	C7—C8—H8	120.5
H2A—C2—H2C	109.5	C8—C9—C10	118.55 (16)
H2B—C2—H2C	109.5	C8—C9—H9	120.7
N1—C3—C4	128.04 (15)	C10—C9—H9	120.7
N1—C3—H3	116.0	N2—C10—C9	123.96 (17)
C4—C3—H3	116.0	N2—C10—H10	118.0
C3—C4—C5	119.39 (15)	C9—C10—H10	118.0
C3—C4—H4	120.3	C3—N1—C2	121.81 (14)
C5—C4—H4	120.3	C3—N1—C1	121.65 (15)
O1—C5—C4	124.55 (15)	C2—N1—C1	116.54 (14)
O1—C5—C6	116.87 (14)	C10—N2—C6	116.93 (15)