(E)-2-(4-Methoxy-phen-yl)-N-(2-pyrid-yl)-3-(2-pyridylamino)acrylamide.

In the title compound, C(20)H(18)N(4)O(2), the amino-acrylamide group makes a dihedral angles of 4.0 (1)° with the amino-bound pyridyl ring and 15.66 (12)° with the amide-bound pyridyl ring. The dihedral angle between the amino-acrylamide group and the pendant 4-methoxy-phenyl group is 71.22 (9)°. In the crystal structure, N-H⋯N hydrogen bonds and C-H⋯O and C-H⋯N inter-actions help to establish the packing. Intra-molecular C-H⋯O and C-H⋯(N,O) contacts also occur.

Related literature

For background to the anti­bacteriological activity of enamines, see: Xiao et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C20H18N4O2

M = 346.38

Monoclinic,

a = 11.546 (2) Å

b = 12.148 (2) Å

c = 14.006 (3) Å

β = 113.74 (3)°

V = 1798.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.975, T max = 0.992

3523 measured reflections

3523 independent reflections

1452 reflections with I > 2σ(I)

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.083

wR(F 2) = 0.200

S = 1.04

3523 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007089/hb2919sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007089/hb2919Isup2.hkl

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

C20H18N4O2	F(000) = 728
Mr = 346.38	Dx = 1.279 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.546 (2) Å	θ = 9–12°
b = 12.148 (2) Å	µ = 0.09 mm−1
c = 14.006 (3) Å	T = 293 K
β = 113.74 (3)°	Block, colorless
V = 1798.3 (6) Å3	0.30 × 0.10 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1452 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.0000
graphite	θmax = 26.0°, θmin = 1.9°
ω/2θ scans	h = −14→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→14
Tmin = 0.975, Tmax = 0.992	l = 0→17
3523 measured reflections	3 standard reflections every 200 reflections
3523 independent reflections	intensity decay: none

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)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.200	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0712P)2] where P = (Fo2 + 2Fc2)/3
3523 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.16 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
N1	0.8670 (3)	0.3253 (3)	0.3474 (3)	0.0628 (10)
H1A	0.9483	0.3244	0.3725	0.075*
O1	1.3868 (3)	0.5123 (3)	0.3652 (3)	0.1153 (14)
C1	1.4551 (5)	0.4266 (5)	0.3437 (5)	0.137 (3)
H1B	1.5434	0.4450	0.3718	0.206*
H1C	1.4251	0.4168	0.2696	0.206*
H1D	1.4432	0.3596	0.3750	0.206*
O2	0.6560 (2)	0.5617 (3)	0.1480 (2)	0.0756 (9)
N2	0.6813 (3)	0.2469 (3)	0.3418 (3)	0.0752 (11)
C2	1.2592 (4)	0.5024 (5)	0.3320 (4)	0.0820 (15)
N3	0.8252 (3)	0.6425 (3)	0.1344 (2)	0.0591 (9)
H3A	0.9063	0.6471	0.1648	0.071*
C3	1.1876 (4)	0.4216 (4)	0.2676 (4)	0.0764 (13)
H3B	1.2254	0.3682	0.2420	0.092*
N4	0.8483 (3)	0.7805 (3)	0.0328 (3)	0.0635 (9)
C4	1.0576 (4)	0.4195 (3)	0.2404 (3)	0.0648 (11)
H4B	1.0096	0.3645	0.1958	0.078*
C5	0.9974 (4)	0.4961 (3)	0.2771 (3)	0.0568 (11)
C6	1.0728 (4)	0.5774 (4)	0.3409 (3)	0.0743 (13)
H6A	1.0356	0.6313	0.3665	0.089*
C7	1.2003 (4)	0.5811 (4)	0.3678 (4)	0.0874 (15)
H7A	1.2479	0.6373	0.4107	0.105*
C8	0.8599 (3)	0.4900 (3)	0.2477 (3)	0.0545 (10)
C9	0.8061 (4)	0.4077 (3)	0.2814 (3)	0.0583 (11)
H9A	0.7183	0.4081	0.2566	0.070*
C10	0.8054 (4)	0.2412 (3)	0.3773 (3)	0.0602 (11)
C11	0.8757 (4)	0.1591 (4)	0.4414 (4)	0.0797 (15)
H11A	0.9634	0.1585	0.4652	0.096*
C12	0.8136 (5)	0.0787 (4)	0.4691 (4)	0.1026 (18)
H12A	0.8588	0.0216	0.5122	0.123*
C13	0.6855 (5)	0.0816 (4)	0.4340 (4)	0.0955 (17)
H13A	0.6416	0.0268	0.4518	0.115*
C14	0.6240 (5)	0.1666 (4)	0.3725 (4)	0.0884 (16)
H14A	0.5365	0.1697	0.3499	0.106*
C15	0.7711 (4)	0.5672 (3)	0.1737 (3)	0.0537 (10)
C16	0.7672 (4)	0.7143 (3)	0.0506 (3)	0.0559 (10)
C17	0.6370 (4)	0.7165 (4)	−0.0105 (3)	0.0671 (12)
H17A	0.5812	0.6716	0.0045	0.080*
C18	0.5952 (5)	0.7878 (4)	−0.0932 (4)	0.0870 (15)
H18A	0.5094	0.7909	−0.1362	0.104*
C19	0.6782 (5)	0.8542 (4)	−0.1129 (4)	0.0860 (16)
H19A	0.6505	0.9018	−0.1697	0.103*
C20	0.8027 (4)	0.8489 (4)	−0.0471 (4)	0.0811 (14)
H20A	0.8588	0.8961	−0.0591	0.097*

	U11	U22	U33	U12	U13	U23
N1	0.0472 (19)	0.066 (2)	0.072 (2)	0.0045 (18)	0.0203 (17)	0.011 (2)
O1	0.056 (2)	0.122 (3)	0.161 (4)	0.003 (2)	0.036 (2)	0.026 (3)
C1	0.066 (3)	0.138 (6)	0.215 (7)	0.023 (4)	0.064 (4)	0.051 (5)
O2	0.0566 (18)	0.090 (2)	0.082 (2)	0.0110 (16)	0.0303 (16)	0.0173 (18)
N2	0.055 (2)	0.079 (3)	0.086 (3)	−0.011 (2)	0.023 (2)	0.018 (2)
C2	0.046 (3)	0.091 (4)	0.100 (4)	0.005 (3)	0.020 (3)	0.032 (3)
N3	0.0523 (19)	0.056 (2)	0.059 (2)	0.0026 (17)	0.0119 (17)	0.0122 (18)
C3	0.070 (3)	0.073 (3)	0.092 (4)	0.011 (3)	0.038 (3)	0.015 (3)
N4	0.062 (2)	0.070 (2)	0.056 (2)	0.000 (2)	0.0210 (18)	0.009 (2)
C4	0.065 (3)	0.056 (3)	0.067 (3)	0.000 (2)	0.020 (2)	0.002 (2)
C5	0.059 (2)	0.051 (3)	0.054 (3)	0.005 (2)	0.015 (2)	0.005 (2)
C6	0.064 (3)	0.077 (3)	0.075 (3)	0.009 (3)	0.021 (2)	−0.004 (3)
C7	0.066 (3)	0.083 (4)	0.094 (4)	−0.007 (3)	0.013 (3)	−0.008 (3)
C8	0.052 (2)	0.050 (3)	0.057 (3)	0.006 (2)	0.0169 (19)	0.003 (2)
C9	0.056 (2)	0.050 (2)	0.059 (3)	0.007 (2)	0.012 (2)	0.000 (2)
C10	0.057 (3)	0.063 (3)	0.057 (3)	−0.015 (2)	0.019 (2)	0.004 (2)
C11	0.066 (3)	0.080 (3)	0.084 (3)	−0.001 (3)	0.021 (3)	0.034 (3)
C12	0.093 (4)	0.098 (4)	0.101 (4)	−0.008 (3)	0.023 (3)	0.040 (4)
C13	0.095 (4)	0.081 (4)	0.095 (4)	−0.022 (3)	0.023 (3)	0.031 (3)
C14	0.067 (3)	0.096 (4)	0.098 (4)	−0.021 (3)	0.030 (3)	0.014 (3)
C15	0.055 (2)	0.059 (3)	0.047 (2)	0.004 (2)	0.021 (2)	−0.003 (2)
C16	0.057 (2)	0.056 (3)	0.054 (3)	0.010 (2)	0.022 (2)	0.003 (2)
C17	0.060 (3)	0.073 (3)	0.062 (3)	0.003 (2)	0.017 (2)	0.009 (3)
C18	0.066 (3)	0.106 (4)	0.068 (3)	0.016 (3)	0.005 (3)	0.017 (3)
C19	0.074 (3)	0.103 (4)	0.077 (4)	0.017 (3)	0.025 (3)	0.039 (3)
C20	0.075 (3)	0.097 (4)	0.071 (3)	0.006 (3)	0.029 (3)	0.023 (3)

N1—C9	1.352 (4)	C5—C8	1.472 (5)
N1—C10	1.402 (5)	C6—C7	1.366 (6)
N1—H1A	0.8600	C6—H6A	0.9300
O1—C2	1.360 (5)	C7—H7A	0.9300
O1—C1	1.409 (6)	C8—C9	1.359 (5)
C1—H1B	0.9600	C8—C15	1.466 (5)
C1—H1C	0.9600	C9—H9A	0.9300
C1—H1D	0.9600	C10—C11	1.368 (5)
O2—C15	1.231 (4)	C11—C12	1.358 (6)
N2—C10	1.315 (5)	C11—H11A	0.9300
N2—C14	1.343 (5)	C12—C13	1.358 (6)
C2—C3	1.365 (6)	C12—H12A	0.9300
C2—C7	1.379 (6)	C13—C14	1.348 (6)
N3—C15	1.344 (5)	C13—H13A	0.9300
N3—C16	1.398 (5)	C14—H14A	0.9300
N3—H3A	0.8600	C16—C17	1.400 (5)
C3—C4	1.393 (5)	C17—C18	1.368 (6)
C3—H3B	0.9300	C17—H17A	0.9300
N4—C20	1.321 (5)	C18—C19	1.364 (6)
N4—C16	1.332 (5)	C18—H18A	0.9300
C4—C5	1.379 (5)	C19—C20	1.361 (6)
C4—H4B	0.9300	C19—H19A	0.9300
C5—C6	1.380 (5)	C20—H20A	0.9300
C9—N1—C10	123.8 (3)	N1—C9—C8	126.7 (4)
C9—N1—H1A	118.1	N1—C9—H9A	116.7
C10—N1—H1A	118.1	C8—C9—H9A	116.7
C2—O1—C1	119.0 (5)	N2—C10—C11	123.7 (4)
O1—C1—H1B	109.5	N2—C10—N1	117.1 (4)
O1—C1—H1C	109.5	C11—C10—N1	119.2 (4)
H1B—C1—H1C	109.5	C12—C11—C10	118.0 (4)
O1—C1—H1D	109.5	C12—C11—H11A	121.0
H1B—C1—H1D	109.5	C10—C11—H11A	121.0
H1C—C1—H1D	109.5	C11—C12—C13	120.1 (5)
C10—N2—C14	116.3 (4)	C11—C12—H12A	120.0
O1—C2—C3	125.0 (5)	C13—C12—H12A	120.0
O1—C2—C7	116.1 (5)	C14—C13—C12	117.9 (5)
C3—C2—C7	118.8 (4)	C14—C13—H13A	121.0
C15—N3—C16	128.6 (4)	C12—C13—H13A	121.0
C15—N3—H3A	115.7	N2—C14—C13	124.0 (5)
C16—N3—H3A	115.7	N2—C14—H14A	118.0
C2—C3—C4	119.6 (5)	C13—C14—H14A	118.0
C2—C3—H3B	120.2	O2—C15—N3	122.9 (4)
C4—C3—H3B	120.2	O2—C15—C8	122.5 (4)
C20—N4—C16	117.9 (4)	N3—C15—C8	114.6 (4)
C5—C4—C3	122.4 (4)	N4—C16—N3	113.5 (3)
C5—C4—H4B	118.8	N4—C16—C17	122.5 (4)
C3—C4—H4B	118.8	N3—C16—C17	124.0 (4)
C4—C5—C6	116.3 (4)	C18—C17—C16	117.1 (4)
C4—C5—C8	120.7 (4)	C18—C17—H17A	121.4
C6—C5—C8	123.0 (4)	C16—C17—H17A	121.4
C7—C6—C5	122.0 (4)	C19—C18—C17	120.6 (4)
C7—C6—H6A	119.0	C19—C18—H18A	119.7
C5—C6—H6A	119.0	C17—C18—H18A	119.7
C6—C7—C2	120.8 (5)	C20—C19—C18	118.2 (5)
C6—C7—H7A	119.6	C20—C19—H19A	120.9
C2—C7—H7A	119.6	C18—C19—H19A	120.9
C9—C8—C15	115.4 (4)	N4—C20—C19	123.7 (5)
C9—C8—C5	122.2 (4)	N4—C20—H20A	118.1
C15—C8—C5	122.3 (4)	C19—C20—H20A	118.1
C1—O1—C2—C3	−8.5 (8)	N2—C10—C11—C12	0.5 (7)
C1—O1—C2—C7	171.2 (5)	N1—C10—C11—C12	−180.0 (4)
O1—C2—C3—C4	179.1 (4)	C10—C11—C12—C13	−0.4 (8)
C7—C2—C3—C4	−0.6 (7)	C11—C12—C13—C14	−0.6 (9)
C2—C3—C4—C5	−0.7 (7)	C10—N2—C14—C13	−1.6 (7)
C3—C4—C5—C6	1.5 (6)	C12—C13—C14—N2	1.7 (9)
C3—C4—C5—C8	−179.1 (4)	C16—N3—C15—O2	−10.3 (6)
C4—C5—C6—C7	−1.0 (6)	C16—N3—C15—C8	168.0 (4)
C8—C5—C6—C7	179.6 (4)	C9—C8—C15—O2	3.7 (6)
C5—C6—C7—C2	−0.3 (7)	C5—C8—C15—O2	179.2 (4)
O1—C2—C7—C6	−178.6 (4)	C9—C8—C15—N3	−174.7 (3)
C3—C2—C7—C6	1.2 (7)	C5—C8—C15—N3	0.8 (5)
C4—C5—C8—C9	68.4 (5)	C20—N4—C16—N3	177.8 (4)
C6—C5—C8—C9	−112.2 (5)	C20—N4—C16—C17	−1.4 (6)
C4—C5—C8—C15	−106.8 (4)	C15—N3—C16—N4	178.7 (4)
C6—C5—C8—C15	72.6 (5)	C15—N3—C16—C17	−2.1 (6)
C10—N1—C9—C8	−178.4 (4)	N4—C16—C17—C18	2.4 (6)
C15—C8—C9—N1	178.4 (4)	N3—C16—C17—C18	−176.8 (4)
C5—C8—C9—N1	2.9 (6)	C16—C17—C18—C19	−1.0 (7)
C14—N2—C10—C11	0.5 (7)	C17—C18—C19—C20	−1.2 (8)
C14—N2—C10—N1	−179.0 (4)	C16—N4—C20—C19	−1.0 (7)
C9—N1—C10—N2	−3.0 (6)	C18—C19—C20—N4	2.3 (8)
C9—N1—C10—C11	177.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N4i	0.86	2.25	3.079 (5)	163
C9—H9A···O2	0.93	2.33	2.718 (5)	104
C9—H9A···N2	0.93	2.42	2.754 (6)	101
C17—H17A···O2	0.93	2.27	2.850 (5)	120
C11—H11A···N4i	0.93	2.62	3.396 (6)	141
C14—H14A···O2ii	0.93	2.59	3.378 (5)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N4i	0.86	2.25	3.079 (5)	163
C9—H9A⋯O2	0.93	2.33	2.718 (5)	104
C9—H9A⋯N2	0.93	2.42	2.754 (6)	101
C17—H17A⋯O2	0.93	2.27	2.850 (5)	120
C11—H11A⋯N4i	0.93	2.62	3.396 (6)	141
C14—H14A⋯O2ii	0.93	2.59	3.378 (5)	143

Symmetry codes: (i) ; (ii) .