(E)-3-Dimethyl-amino-1-(4-pyrid-yl)prop-2-en-1-one.

The title compound, C(10)H(12)N(2)O, 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 = 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) 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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.137

S = 1.00

1784 reflections

121 parameters

H-atom parameters not refined

Δρmax = 0.20 e Å−3

Δρmin = −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.

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

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

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

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

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 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)

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	0.8254 (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)

	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)

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)