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

Ni, L.; Zhu, G.-W.; Wei, H.

doi:10.1107/S1600536809030542

organic compounds

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Volume 65| Part 9| September 2009| Page o2104

doi:10.1107/S1600536809030542

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

Lei Ni,^a ^* Guo-Wei Zhu ^a and Hong Wei ^a

^aCollege of Chemistry and Biology, Beihua University, Jilin 132013, People's Republic of China
^*Correspondence e-mail: nilei_bh@163.com

(Received 9 July 2009; accepted 31 July 2009; online 8 August 2009)

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, P 2₁ /n
a = 5.6300 (11) Å
b = 22.850 (5) Å
c = 7.8400 (16) Å
β = 107.57 (3)°
V = 961.5 (3) Å³
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[F² > 2σ(F²)] = 0.040
wR(F²) = 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030542/hb5024sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809030542/hb5024Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), drawn with 30% probability displacement ellipsoids for the non-hydrogen atoms.

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

Crystal data top

C₁₀H₁₂N₂O	F(000) = 376
M_r = 176.22	D_x = 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 top

Bruker APEXII CCD diffractometer	1784 independent reflections
Radiation source: fine-focus sealed tube	1503 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 25.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −6→6
T_min = 0.990, T_max = 0.994	k = −27→26
5177 measured reflections	l = −7→9

Refinement top

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(F_o²) + (0.092P)² + 0.1151P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
1784 reflections	Δρ_max = 0.20 e Å⁻³
121 parameters	Δρ_min = −0.13 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)

Crystal data top

C₁₀H₁₂N₂O	V = 961.5 (3) Å³
M_r = 176.22	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.6300 (11) Å	µ = 0.08 mm⁻¹
b = 22.850 (5) Å	T = 294 K
c = 7.8400 (16) Å	0.12 × 0.10 × 0.08 mm
β = 107.57 (3)°

Data collection top

Bruker APEXII CCD diffractometer	1784 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1503 reflections with I > 2σ(I)
T_min = 0.990, T_max = 0.994	R_int = 0.022
5177 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.137	H-atom parameters not refined
S = 1.00	Δρ_max = 0.20 e Å⁻³
1784 reflections	Δρ_min = −0.13 e Å⁻³
121 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂N₂O
M_r	176.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	5.6300 (11), 22.850 (5), 7.8400 (16)
β (°)	107.57 (3)
V (Å³)	961.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.990, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	5177, 1784, 1503
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.137, 1.00
No. of reflections	1784
No. of parameters	121
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.13

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors acknowledge financial support from the Science Foundation of Beihua University.

References

Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ni, L., Zhao, J.-L. & Wei, H. (2009). Acta Cryst. E65, o2103. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar