(E)-1-(Pyridin-2-yl)ethanone O-acryloyloxime.

The title compound, C(10)H(10)N(2)O(2), was synthesized by the reaction of the oxime of 2-acetyl-pyridine and 3-bromo-propanoyl chloride in the presence of triethyl-amine. The mol-ecule adopts a nearly planar chain-extended conformation with the oxime group in a trans and the acryloyl group in an s-cis conformation. This conformation is stabilized by an intra-molecular C-H⋯N hydrogen bond. The screw-related mol-ecules are linked into C(9) chains by C-H⋯O hydrogen bonds.

Related literature

For general background, see: Robertson, (1995 ▶). For the biological activity of oximes, see: Van Helden et al. (1996 ▶). For related structures, see: Mojzych et al. (2007 ▶). For the graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H10N2O2

M = 190.20

Monoclinic,

a = 7.0240 (5) Å

b = 18.4054 (14) Å

c = 7.8642 (6) Å

β = 114.043 (1)°

V = 928.47 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 (2) K

0.75 × 0.13 × 0.07 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.924, T max = 0.993

15216 measured reflections

2209 independent reflections

1951 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.098

S = 1.02

2209 reflections

167 parameters

All H-atom parameters refined

Δρmax = 0.40 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶), PLATON (Spek, 2003 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808005436/ci2565sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005436/ci2565Isup2.hkl

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

C10H10N2O2	F000 = 400
Mr = 190.20	Dx = 1.361 Mg m−3
Monoclinic, P21/n	Melting point: 338 K
Hall symbol: -P 2yn	Mo Kα radiation λ = 0.71073 Å
a = 7.0240 (5) Å	Cell parameters from 166 reflections
b = 18.4054 (14) Å	θ = 3.8–28.0º
c = 7.8642 (6) Å	µ = 0.10 mm−1
β = 114.043 (1)º	T = 100 (2) K
V = 928.47 (12) Å3	Prism, colourless
Z = 4	0.75 × 0.13 × 0.07 mm

Bruker SMART APEXII CCD diffractometer	1951 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
T = 100(2) K	θmax = 28.4º
ω scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Sheldrick, 2002)	h = −9→9
Tmin = 0.924, Tmax = 0.993	k = −24→24
15216 measured reflections	l = −10→10
2209 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033	All H-atom parameters refined
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0531P)2 + 0.3208P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
2209 reflections	Δρmax = 0.40 e Å−3
167 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
O1	0.29133 (11)	−0.01660 (4)	0.63817 (9)	0.01600 (18)
O2	0.12879 (12)	−0.12207 (4)	0.50393 (10)	0.02091 (19)
N1	0.27586 (13)	0.17974 (5)	0.26737 (12)	0.0168 (2)
N2	0.23265 (12)	0.01032 (5)	0.45236 (11)	0.0149 (2)
C1	0.22032 (15)	0.21070 (6)	0.09936 (15)	0.0189 (2)
C2	0.14439 (15)	0.17215 (6)	−0.06672 (15)	0.0189 (2)
C3	0.13150 (15)	0.09699 (6)	−0.06045 (14)	0.0176 (2)
C4	0.19186 (15)	0.06379 (6)	0.11195 (14)	0.0157 (2)
C5	0.25793 (14)	0.10712 (5)	0.27155 (14)	0.0139 (2)
C6	0.30844 (14)	0.07431 (5)	0.45895 (13)	0.0137 (2)
C7	0.22368 (15)	−0.08629 (5)	0.63995 (14)	0.0148 (2)
C8	0.28945 (16)	−0.10972 (6)	0.83633 (15)	0.0184 (2)
C9	0.25144 (17)	−0.17670 (6)	0.87484 (16)	0.0212 (2)
C10	0.43601 (17)	0.11625 (6)	0.63073 (14)	0.0179 (2)
H1	0.234 (2)	0.2626 (8)	0.0980 (19)	0.023 (3)*
H2	0.106 (2)	0.1958 (8)	−0.180 (2)	0.026 (3)*
H3	0.081 (2)	0.0693 (8)	−0.173 (2)	0.027 (3)*
H4	0.185 (2)	0.0111 (7)	0.1226 (18)	0.021 (3)*
H8	0.363 (2)	−0.0726 (8)	0.931 (2)	0.030 (4)*
H9A	0.293 (2)	−0.1938 (7)	1.002 (2)	0.025 (3)*
H9B	0.180 (2)	−0.2100 (7)	0.776 (2)	0.025 (3)*
H10A	0.389 (2)	0.1079 (8)	0.726 (2)	0.038 (4)*
H10B	0.429 (2)	0.1661 (9)	0.605 (2)	0.039 (4)*
H10C	0.581 (3)	0.1023 (8)	0.673 (2)	0.039 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0177 (4)	0.0178 (4)	0.0120 (3)	−0.0008 (3)	0.0056 (3)	0.0015 (3)
O2	0.0281 (4)	0.0172 (4)	0.0168 (4)	−0.0010 (3)	0.0085 (3)	−0.0012 (3)
N1	0.0150 (4)	0.0154 (4)	0.0200 (4)	0.0006 (3)	0.0072 (3)	0.0004 (3)
N2	0.0158 (4)	0.0173 (4)	0.0119 (4)	0.0022 (3)	0.0059 (3)	0.0022 (3)
C1	0.0168 (5)	0.0153 (5)	0.0244 (5)	0.0010 (4)	0.0081 (4)	0.0033 (4)
C2	0.0154 (5)	0.0227 (5)	0.0181 (5)	0.0023 (4)	0.0064 (4)	0.0067 (4)
C3	0.0152 (5)	0.0220 (5)	0.0154 (5)	−0.0014 (4)	0.0060 (4)	−0.0011 (4)
C4	0.0147 (4)	0.0154 (5)	0.0176 (5)	0.0000 (3)	0.0072 (4)	0.0004 (4)
C5	0.0104 (4)	0.0162 (5)	0.0155 (5)	0.0013 (3)	0.0058 (3)	0.0005 (4)
C6	0.0115 (4)	0.0160 (5)	0.0149 (5)	0.0024 (3)	0.0067 (3)	−0.0007 (4)
C7	0.0131 (4)	0.0163 (5)	0.0169 (5)	0.0031 (3)	0.0080 (4)	0.0013 (4)
C8	0.0167 (5)	0.0237 (5)	0.0156 (5)	0.0008 (4)	0.0073 (4)	0.0013 (4)
C9	0.0212 (5)	0.0241 (6)	0.0208 (5)	0.0039 (4)	0.0110 (4)	0.0051 (4)
C10	0.0205 (5)	0.0181 (5)	0.0154 (5)	−0.0027 (4)	0.0077 (4)	−0.0025 (4)

O1—C7	1.3698 (12)	C4—C5	1.3971 (14)
O1—N2	1.4352 (10)	C4—H4	0.976 (13)
O2—C7	1.2005 (13)	C5—C6	1.4954 (13)
N1—C1	1.3426 (14)	C6—C10	1.4957 (13)
N1—C5	1.3442 (13)	C7—C8	1.4843 (14)
N2—C6	1.2849 (13)	C8—C9	1.3224 (15)
C1—C2	1.3879 (15)	C8—H8	0.989 (15)
C1—H1	0.962 (14)	C9—H9A	0.972 (15)
C2—C3	1.3884 (15)	C9—H9B	0.954 (14)
C2—H2	0.929 (15)	C10—H10A	0.947 (17)
C3—C4	1.3868 (14)	C10—H10B	0.937 (16)
C3—H3	0.954 (15)	C10—H10C	0.969 (16)
C7—O1—N2	112.13 (7)	N2—C6—C5	113.73 (8)
C1—N1—C5	116.97 (9)	N2—C6—C10	126.54 (9)
C6—N2—O1	109.45 (8)	C5—C6—C10	119.74 (8)
N1—C1—C2	123.73 (10)	O2—C7—O1	125.00 (9)
N1—C1—H1	116.3 (8)	O2—C7—C8	126.30 (9)
C2—C1—H1	120.0 (8)	O1—C7—C8	108.69 (8)
C3—C2—C1	118.79 (9)	C9—C8—C7	120.19 (10)
C3—C2—H2	120.2 (9)	C9—C8—H8	124.2 (9)
C1—C2—H2	121.0 (9)	C7—C8—H8	115.5 (9)
C4—C3—C2	118.38 (9)	C8—C9—H9A	122.2 (8)
C4—C3—H3	121.3 (8)	C8—C9—H9B	120.1 (8)
C2—C3—H3	120.3 (8)	H9A—C9—H9B	117.7 (11)
C3—C4—C5	118.96 (9)	C6—C10—H10A	111.0 (10)
C3—C4—H4	121.0 (8)	C6—C10—H10B	110.3 (10)
C5—C4—H4	120.0 (8)	H10A—C10—H10B	109.1 (13)
N1—C5—C4	123.07 (9)	C6—C10—H10C	109.4 (9)
N1—C5—C6	116.01 (8)	H10A—C10—H10C	109.9 (13)
C4—C5—C6	120.90 (9)	H10B—C10—H10C	107.0 (13)
C7—O1—N2—C6	−176.92 (7)	O1—N2—C6—C10	−0.77 (13)
C5—N1—C1—C2	0.84 (14)	N1—C5—C6—N2	160.49 (8)
N1—C1—C2—C3	−2.47 (15)	C4—C5—C6—N2	−18.13 (12)
C1—C2—C3—C4	1.12 (14)	N1—C5—C6—C10	−19.37 (12)
C2—C3—C4—C5	1.61 (14)	C4—C5—C6—C10	162.02 (9)
C1—N1—C5—C4	2.13 (14)	N2—O1—C7—O2	0.98 (13)
C1—N1—C5—C6	−176.46 (8)	N2—O1—C7—C8	−179.69 (7)
C3—C4—C5—N1	−3.38 (14)	O2—C7—C8—C9	2.73 (16)
C3—C4—C5—C6	175.14 (8)	O1—C7—C8—C9	−176.58 (9)
O1—N2—C6—C5	179.39 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···N1	0.94 (2)	2.438 (14)	2.8596 (14)	107 (1)
C1—H1···O2i	0.96 (2)	2.588 (15)	3.4581 (14)	150 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯N1	0.94 (2)	2.438 (14)	2.8596 (14)	107 (1)
C1—H1⋯O2i	0.96 (2)	2.588 (15)	3.4581 (14)	150 (1)

Symmetry code: (i) .