(E)-3-Dimethyl­amino-1-(4-pyrid­yl)prop-2-en-1-one

Abstract

The title compound, C₁₀H₁₂N₂O, is approximately planar, the r.m.s. deviation of the non-H atoms from the mean plane being 0.099 Å.

Related literature

For an isomer of the title compound with the same space group and similar unit-cell parameters, see: Ni et al. (2009 ▶).

Experimental

Crystal data

• C₁₀H₁₂N₂O

• M _r = 176.22

• Monoclinic,

• a = 5.6300 (11) Å

• b = 22.850 (5) Å

• c = 7.8400 (16) Å

• β = 107.57 (3)°

• V = 961.5 (3) ų

• Z = 4

• Mo Kα radiation

• μ = 0.08 mm⁻¹

• T = 294 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

• 5177 measured reflections

• 1784 independent reflections

• 1503 reflections with I > 2σ(I)

• R _int = 0.022

Refinement

• R[F ² > 2σ(F ²)] = 0.040

• wR(F ²) = 0.137

• S = 1.00

• 1784 reflections

• 121 parameters

• H-atom parameters not refined

• Δρ_max = 0.20 e Å⁻³

• Δρ_min = −0.13 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.

Supplementary Material

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

supplementary crystallographic information

Comment

As part of our ongoing studies of heteroaromatic compounds (Ni et al., 2009), we now report the synthesis and structure of the title compound, (I).

As shown in Fig. 1, non-hydrogen atoms including the pyridine ring, N,N-Dimethylamino, and prop-2-en-1-one are coplanar with the r.m.s deviation of the fitted atoms being 0.099 Å.

Experimental

A mixture of 4-acetylpyridine(10 mmol) and N,N-dimethylformamide-dimethyl acetal(40 ml) was refluxed for four hours. After concentration invacuo, recrystallization of the orange residue from ethanol afforded yellow blocks of (I). Anal. Calc. for C₁₀H₁₂N₂O: C 68.10, H 6.81, N 15.89%; Found: C 68.05, H 6.69, N 15.81%.

Refinement

All H atoms were geometrically positioned (C—H = 0.93–0.97Å) and refined as riding with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C).

Figures

Fig. 1.

The molecular structure of (I), drawn with 30% probability displacement ellipsoids for the non-hydrogen atoms.

Crystal data

C10H12N2O	F(000) = 376
Mr = 176.22	Dx = 1.217 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1784 reflections
a = 5.6300 (11) Å	θ = 1.8–25.5°
b = 22.850 (5) Å	µ = 0.08 mm−1
c = 7.8400 (16) Å	T = 294 K
β = 107.57 (3)°	Block, yellow
V = 961.5 (3) Å3	0.12 × 0.10 × 0.08 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer	1784 independent reflections
Radiation source: fine-focus sealed tube	1503 reflections with I > 2σ(I)
graphite	Rint = 0.022
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→26
5177 measured reflections	l = −7→9

Refinement

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters not refined
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.092P)2 + 0.1151P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
1784 reflections	Δρmax = 0.20 e Å−3
121 parameters	Δρmin = −0.12 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: 0.016 (6)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.8254 (2)	0.15312 (5)	0.68372 (16)	0.0403 (3)
C2	0.6652 (3)	0.20055 (6)	0.65592 (17)	0.0451 (4)
H2	0.5490	0.2036	0.7183	0.054*
C3	0.6795 (3)	0.24329 (7)	0.5346 (2)	0.0541 (4)
H3	0.5698	0.2747	0.5180	0.065*
C4	0.9907 (3)	0.19670 (8)	0.4672 (2)	0.0634 (5)
H4	1.1040	0.1947	0.4022	0.076*
C5	0.9919 (3)	0.15168 (7)	0.5851 (2)	0.0533 (4)
H5	1.1034	0.1208	0.5980	0.064*
C6	0.8303 (2)	0.10391 (6)	0.81421 (18)	0.0441 (4)
C7	0.6972 (2)	0.11110 (6)	0.94016 (18)	0.0452 (4)
H7	0.6012	0.1444	0.9377	0.054*
C8	0.7118 (3)	0.06832 (6)	1.06560 (18)	0.0453 (4)
H8	0.8147	0.0367	1.0632	0.054*
C9	0.4227 (3)	0.11224 (8)	1.2011 (2)	0.0668 (5)
H9A	0.5085	0.1490	1.2271	0.100*
H9B	0.3519	0.1028	1.2948	0.100*
H9C	0.2924	0.1150	1.0894	0.100*
C10	0.6374 (3)	0.01980 (7)	1.3199 (2)	0.0641 (5)
H10A	0.7505	−0.0083	1.2966	0.096*
H10B	0.4815	0.0011	1.3112	0.096*
H10C	0.7069	0.0355	1.4380	0.096*
N1	0.8397 (3)	0.24245 (6)	0.44017 (18)	0.0617 (4)
N2	0.5966 (2)	0.06690 (5)	1.18924 (16)	0.0494 (4)
O1	0.9520 (2)	0.05981 (5)	0.80351 (16)	0.0677 (4)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
C1	0.0414 (7)	0.0407 (7)	0.0388 (7)	−0.0052 (5)	0.0120 (5)	−0.0024 (5)
C2	0.0477 (7)	0.0453 (8)	0.0433 (7)	−0.0010 (6)	0.0153 (6)	−0.0018 (6)
C3	0.0581 (9)	0.0476 (8)	0.0541 (9)	0.0035 (6)	0.0131 (7)	0.0068 (6)
C4	0.0583 (9)	0.0715 (11)	0.0699 (10)	0.0001 (8)	0.0337 (8)	0.0178 (8)
C5	0.0500 (8)	0.0541 (9)	0.0623 (9)	0.0035 (6)	0.0268 (7)	0.0092 (7)
C6	0.0480 (7)	0.0410 (7)	0.0460 (7)	0.0005 (5)	0.0184 (6)	0.0004 (6)
C7	0.0498 (7)	0.0429 (7)	0.0467 (7)	0.0020 (6)	0.0202 (6)	0.0009 (5)
C8	0.0499 (8)	0.0442 (8)	0.0460 (8)	−0.0016 (6)	0.0210 (6)	−0.0037 (6)
C9	0.0651 (10)	0.0810 (12)	0.0631 (10)	0.0146 (8)	0.0326 (8)	0.0008 (8)
C10	0.0914 (12)	0.0553 (9)	0.0583 (9)	−0.0050 (8)	0.0415 (9)	0.0036 (7)
N1	0.0633 (8)	0.0598 (8)	0.0646 (8)	−0.0018 (6)	0.0232 (7)	0.0176 (6)
N2	0.0576 (7)	0.0507 (7)	0.0476 (7)	0.0002 (5)	0.0274 (6)	0.0012 (5)
O1	0.0928 (9)	0.0519 (7)	0.0772 (8)	0.0237 (6)	0.0538 (7)	0.0171 (5)

Geometric parameters (Å, °)

C1—C2	1.3846 (18)	C7—C8	1.3713 (19)
C1—C5	1.3842 (19)	C7—H7	0.9300
C1—C6	1.5148 (18)	C8—N2	1.3193 (17)
C2—C3	1.382 (2)	C8—H8	0.9300
C2—H2	0.9300	C9—N2	1.4476 (19)
C3—N1	1.329 (2)	C9—H9A	0.9600
C3—H3	0.9300	C9—H9B	0.9600
C4—N1	1.323 (2)	C9—H9C	0.9600
C4—C5	1.382 (2)	C10—N2	1.4555 (19)
C4—H4	0.9300	C10—H10A	0.9600
C5—H5	0.9300	C10—H10B	0.9600
C6—O1	1.2357 (16)	C10—H10C	0.9600
C6—C7	1.4180 (18)
C2—C1—C5	116.72 (12)	C6—C7—H7	120.4
C2—C1—C6	124.44 (12)	N2—C8—C7	127.45 (13)
C5—C1—C6	118.84 (12)	N2—C8—H8	116.3
C1—C2—C3	119.39 (13)	C7—C8—H8	116.3
C1—C2—H2	120.3	N2—C9—H9A	109.5
C3—C2—H2	120.3	N2—C9—H9B	109.5
N1—C3—C2	124.31 (14)	H9A—C9—H9B	109.5
N1—C3—H3	117.8	N2—C9—H9C	109.5
C2—C3—H3	117.8	H9A—C9—H9C	109.5
N1—C4—C5	124.67 (14)	H9B—C9—H9C	109.5
N1—C4—H4	117.7	N2—C10—H10A	109.5
C5—C4—H4	117.7	N2—C10—H10B	109.5
C4—C5—C1	119.24 (14)	H10A—C10—H10B	109.5
C4—C5—H5	120.4	N2—C10—H10C	109.5
C1—C5—H5	120.4	H10A—C10—H10C	109.5
O1—C6—C7	124.21 (12)	H10B—C10—H10C	109.5
O1—C6—C1	117.19 (12)	C4—N1—C3	115.67 (13)
C7—C6—C1	118.60 (11)	C8—N2—C9	121.45 (12)
C8—C7—C6	119.15 (12)	C8—N2—C10	121.81 (13)
C8—C7—H7	120.4	C9—N2—C10	116.74 (12)