N-{1,2-Bis(pyridin-3-yl)-2-[(E)-(pyridin-3-yl)methyl-idene-amino]-eth-yl}nicotinamide.

In the title compound, C24H20N6O, the pyridin-3-yl groups on the ethyl-ene fragment are found in a trans conformation with a C(py)-C(e)-C(e)-C(py) (py = pyridine, e = ethylene) torsion angle of 179.2 (3)°. The dihedral angle between the pyridine rings is 3.5 (1)°. In the crystal, N-H⋯N and C-H⋯O=C inter-actions form a layer arrangement parallel to the bc plane. The compound displays disorder of the ethyl-ene fragment over two positions with an occupancy ratio of 0.676 (7) to 0.324 (7) that extends into the amide section of the nicotinamide moiety.

Related literature

For supra­molecular structures, see: Nyburg & Wood (1964 ▶); House & Sadler (1973 ▶); Koçak (2000 ▶). For a related enanti­oselective catalyst, see: Jacobsen et al. (1990 ▶); Corey & Kühnle (1997 ▶); Corey et al. (1989 ▶). For coordination compounds with polypyridine ligands related to the title compound, see: Parra-Hake et al. (2000 ▶); Cruz Enríquez et al. (2012 ▶). For the synthesis of analogous compounds, see: Proskurnina et al. (2002 ▶); Tu et al. (2009 ▶); Irving & Parkins (1965 ▶).

Experimental

Crystal data

C24H20N6O

M = 408.46

Monoclinic,

a = 11.4868 (17) Å

b = 8.7275 (13) Å

c = 21.105 (3) Å

β = 99.857 (3)°

V = 2084.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.28 × 0.26 × 0.14 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶ T min = 0.984, T max = 0.992

17508 measured reflections

3821 independent reflections

2371 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.198

S = 1.02

3821 reflections

312 parameters

48 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813008544/zl2533sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008544/zl2533Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008544/zl2533Isup3.cml

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

C24H20N6O	F(000) = 856
Mr = 408.46	Dx = 1.301 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3500 reflections
a = 11.4868 (17) Å	θ = 2.4–23.6°
b = 8.7275 (13) Å	µ = 0.08 mm−1
c = 21.105 (3) Å	T = 298 K
β = 99.857 (3)°	Prism, colourless
V = 2084.6 (5) Å3	0.28 × 0.26 × 0.14 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3821 independent reflections
Radiation source: fine-focus sealed tube	2371 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
Detector resolution: 0.661 pixels mm-1	θmax = 25.4°, θmin = 1.8°
ω–scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2007	k = −10→10
Tmin = 0.984, Tmax = 0.992	l = −25→25
17508 measured reflections

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0806P)2 + 0.8743P] where P = (Fo2 + 2Fc2)/3
3821 reflections	(Δ/σ)max < 0.001
312 parameters	Δρmax = 0.34 e Å−3
48 restraints	Δρmin = −0.25 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	Occ. (<1)
O1	0.3921 (12)	0.342 (4)	0.0332 (5)	0.109 (5)	0.61 (6)
O1B	0.388 (2)	0.408 (5)	0.0340 (9)	0.121 (7)	0.39 (6)
N1	0.1399 (3)	0.3383 (5)	0.18544 (14)	0.1025 (11)
C2	0.2412 (3)	0.3745 (4)	0.16651 (14)	0.0731 (9)
H2	0.2921	0.4413	0.1921	0.088*
C3	0.2751 (2)	0.3191 (3)	0.11162 (12)	0.0571 (7)
C4	0.2000 (3)	0.2207 (4)	0.07388 (16)	0.0878 (10)
H4	0.2195	0.1815	0.0361	0.105*
C5	0.0947 (3)	0.1806 (5)	0.0931 (2)	0.1138 (14)
H5	0.0424	0.1127	0.0691	0.137*
C6	0.0703 (3)	0.2443 (6)	0.1484 (2)	0.1124 (15)
H6	−0.0012	0.2188	0.1607	0.135*
C7	0.3861 (3)	0.3661 (4)	0.08965 (13)	0.0665 (8)
N8	0.4788 (2)	0.4040 (3)	0.13361 (11)	0.0601 (6)
H8	0.479 (3)	0.397 (3)	0.1736 (15)	0.072*
C9	0.5966 (4)	0.4277 (5)	0.1140 (2)	0.0568 (12)	0.676 (7)
H9	0.5824	0.4637	0.0694	0.068*	0.676 (7)
C10	0.6602 (4)	0.5549 (6)	0.1553 (2)	0.0574 (12)	0.676 (7)
H10	0.6793	0.5219	0.2003	0.069*	0.676 (7)
C9B	0.5658 (7)	0.5179 (11)	0.1168 (4)	0.057 (2)	0.324 (7)
H9B	0.5616	0.5235	0.0701	0.068*	0.324 (7)
C10B	0.6859 (6)	0.4612 (10)	0.1491 (4)	0.059 (2)	0.324 (7)
H10B	0.6920	0.4578	0.1960	0.071*	0.324 (7)
N11	0.7701 (2)	0.5794 (3)	0.12864 (11)	0.0712 (7)
N12	1.1564 (3)	0.7923 (6)	0.1683 (2)	0.1422 (16)
C13	1.0551 (4)	0.7403 (5)	0.18534 (19)	0.1078 (13)
H13	1.0438	0.7562	0.2274	0.129*
C14	0.9677 (3)	0.6652 (4)	0.14390 (16)	0.0712 (8)
C15	0.9841 (3)	0.6467 (4)	0.08213 (18)	0.0862 (10)
H15	0.9262	0.5988	0.0525	0.103*
C16	1.0847 (4)	0.6976 (6)	0.0634 (2)	0.1156 (15)
H16	1.0960	0.6850	0.0211	0.139*
C17	1.1665 (4)	0.7655 (7)	0.1062 (3)	0.1348 (19)
H17	1.2356	0.7970	0.0926	0.162*
C18	0.8618 (3)	0.6101 (4)	0.16693 (14)	0.0697 (8)
H18	0.8634	0.5979	0.2108	0.084*
N19	0.7524 (3)	0.1072 (3)	0.04909 (13)	0.0848 (8)
C20	0.7026 (3)	0.2381 (4)	0.05998 (15)	0.0755 (9)
H20	0.6810	0.3032	0.0251	0.091*
C21	0.6799 (3)	0.2862 (3)	0.11762 (17)	0.0752 (9)
C22	0.7164 (3)	0.1917 (4)	0.16992 (16)	0.0744 (9)
H22	0.7054	0.2208	0.2109	0.089*
C23	0.7687 (3)	0.0550 (4)	0.16045 (16)	0.0746 (9)
H23	0.7932	−0.0112	0.1947	0.090*
C24	0.7842 (3)	0.0183 (4)	0.10042 (18)	0.0846 (10)
H24	0.8195	−0.0754	0.0944	0.102*
N25	0.4976 (3)	0.8743 (3)	0.21511 (13)	0.0795 (8)
C26	0.5503 (3)	0.7463 (4)	0.20567 (17)	0.0863 (10)
H26	0.5746	0.6851	0.2416	0.104*
C27	0.5731 (3)	0.6934 (4)	0.14883 (18)	0.0860 (11)
C28	0.5332 (3)	0.7813 (4)	0.09498 (16)	0.0772 (9)
H28	0.5458	0.7502	0.0546	0.093*
C29	0.4749 (3)	0.9150 (4)	0.10240 (15)	0.0778 (9)
H29	0.4467	0.9769	0.0673	0.093*
C30	0.4591 (3)	0.9551 (4)	0.16320 (17)	0.0842 (10)
H30	0.4185	1.0454	0.1680	0.101*

	U11	U22	U33	U12	U13	U23
O1	0.089 (4)	0.189 (14)	0.055 (3)	−0.054 (6)	0.026 (3)	−0.040 (4)
O1B	0.144 (10)	0.172 (17)	0.049 (6)	−0.066 (10)	0.022 (5)	0.009 (7)
N1	0.0616 (17)	0.170 (3)	0.0795 (19)	−0.006 (2)	0.0214 (15)	0.001 (2)
C2	0.0564 (17)	0.103 (2)	0.0609 (18)	0.0009 (16)	0.0132 (14)	0.0014 (16)
C3	0.0552 (15)	0.0628 (17)	0.0527 (15)	−0.0015 (13)	0.0074 (12)	0.0027 (13)
C4	0.074 (2)	0.111 (3)	0.078 (2)	−0.016 (2)	0.0106 (17)	−0.018 (2)
C5	0.076 (3)	0.149 (4)	0.113 (3)	−0.046 (3)	0.004 (2)	−0.012 (3)
C6	0.062 (2)	0.179 (4)	0.097 (3)	−0.026 (3)	0.017 (2)	0.020 (3)
C7	0.0663 (18)	0.090 (2)	0.0447 (16)	−0.0137 (16)	0.0145 (14)	−0.0084 (15)
N8	0.0593 (14)	0.0737 (16)	0.0497 (13)	−0.0127 (12)	0.0164 (12)	0.0006 (12)
C9	0.060 (3)	0.061 (3)	0.052 (2)	−0.004 (2)	0.0180 (19)	0.001 (2)
C10	0.062 (3)	0.062 (3)	0.050 (2)	−0.002 (2)	0.0136 (18)	−0.001 (2)
C9B	0.065 (4)	0.056 (5)	0.051 (4)	−0.003 (4)	0.016 (3)	−0.001 (4)
C10B	0.062 (4)	0.063 (5)	0.053 (4)	−0.007 (4)	0.012 (3)	−0.004 (4)
N11	0.0568 (14)	0.0999 (19)	0.0586 (14)	−0.0186 (14)	0.0144 (12)	0.0066 (13)
N12	0.085 (2)	0.204 (4)	0.131 (3)	−0.063 (3)	−0.001 (2)	0.024 (3)
C13	0.089 (3)	0.149 (4)	0.083 (2)	−0.028 (3)	0.006 (2)	0.015 (2)
C14	0.0514 (16)	0.084 (2)	0.078 (2)	0.0023 (16)	0.0122 (15)	0.0171 (17)
C15	0.072 (2)	0.100 (3)	0.088 (2)	−0.0076 (19)	0.0172 (18)	0.002 (2)
C16	0.089 (3)	0.166 (4)	0.100 (3)	−0.010 (3)	0.038 (3)	0.018 (3)
C17	0.081 (3)	0.187 (5)	0.142 (4)	−0.027 (3)	0.036 (3)	0.050 (4)
C18	0.0616 (18)	0.087 (2)	0.0602 (18)	−0.0030 (16)	0.0107 (15)	0.0063 (16)
N19	0.108 (2)	0.0748 (18)	0.0763 (18)	0.0132 (16)	0.0290 (16)	−0.0048 (15)
C20	0.078 (2)	0.076 (2)	0.077 (2)	0.0063 (18)	0.0268 (17)	0.0182 (17)
C21	0.092 (2)	0.0555 (17)	0.093 (2)	0.0013 (16)	0.0553 (19)	0.0079 (17)
C22	0.082 (2)	0.073 (2)	0.075 (2)	−0.0111 (17)	0.0341 (17)	−0.0086 (17)
C23	0.0673 (19)	0.081 (2)	0.076 (2)	0.0040 (17)	0.0114 (16)	0.0153 (17)
C24	0.098 (3)	0.069 (2)	0.093 (3)	0.0172 (19)	0.033 (2)	0.0021 (19)
N25	0.101 (2)	0.0716 (18)	0.0682 (17)	0.0071 (16)	0.0199 (15)	−0.0082 (14)
C26	0.109 (3)	0.071 (2)	0.090 (2)	0.010 (2)	0.046 (2)	0.0196 (18)
C27	0.116 (3)	0.0551 (18)	0.107 (3)	0.0028 (18)	0.075 (2)	0.0085 (18)
C28	0.094 (2)	0.071 (2)	0.075 (2)	−0.0136 (18)	0.0402 (18)	−0.0158 (17)
C29	0.082 (2)	0.082 (2)	0.0651 (19)	0.0154 (18)	0.0010 (16)	−0.0035 (17)
C30	0.100 (3)	0.076 (2)	0.075 (2)	0.0219 (19)	0.0088 (19)	−0.0157 (18)

O1—C7	1.223 (8)	N12—C17	1.357 (6)
O1B—C7	1.234 (12)	C13—C14	1.379 (5)
N1—C6	1.307 (5)	C13—H13	0.9300
N1—C2	1.332 (4)	C14—C15	1.359 (5)
C2—C3	1.371 (4)	C14—C18	1.465 (4)
C2—H2	0.9300	C15—C16	1.358 (5)
C3—C4	1.372 (4)	C15—H15	0.9300
C3—C7	1.487 (4)	C16—C17	1.326 (6)
C4—C5	1.385 (5)	C16—H16	0.9300
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.365 (6)	C18—H18	0.9300
C5—H5	0.9300	N19—C20	1.316 (4)
C6—H6	0.9300	N19—C24	1.332 (4)
C7—N8	1.329 (4)	C20—C21	1.353 (4)
N8—C9B	1.495 (9)	C20—H20	0.9300
N8—C9	1.495 (5)	C21—C22	1.384 (5)
N8—H8	0.84 (3)	C22—C23	1.366 (4)
C9—C10	1.520 (5)	C22—H22	0.9300
C9—C21	1.556 (6)	C23—C24	1.348 (4)
C9—H9	0.9800	C23—H23	0.9300
C10—N11	1.483 (4)	C24—H24	0.9300
C10—C27	1.561 (6)	N25—C26	1.302 (4)
C10—H10	0.9800	N25—C30	1.314 (4)
C9B—C10B	1.514 (8)	C26—C27	1.352 (4)
C9B—C27	1.671 (11)	C26—H26	0.9300
C9B—H9B	0.9800	C27—C28	1.382 (5)
C10B—N11	1.526 (7)	C28—C29	1.368 (4)
C10B—C21	1.662 (10)	C28—H28	0.9300
C10B—H10B	0.9800	C29—C30	1.372 (4)
N11—C18	1.242 (3)	C29—H29	0.9300
N12—C13	1.354 (5)	C30—H30	0.9300
C6—N1—C2	116.5 (3)	N12—C13—H13	118.1
N1—C2—C3	124.0 (3)	C14—C13—H13	118.1
N1—C2—H2	118.0	C15—C14—C13	117.3 (3)
C3—C2—H2	118.0	C15—C14—C18	122.6 (3)
C2—C3—C4	118.0 (3)	C13—C14—C18	120.1 (3)
C2—C3—C7	123.3 (3)	C16—C15—C14	120.4 (4)
C4—C3—C7	118.6 (3)	C16—C15—H15	119.8
C3—C4—C5	118.8 (3)	C14—C15—H15	119.8
C3—C4—H4	120.6	C17—C16—C15	119.2 (4)
C5—C4—H4	120.6	C17—C16—H16	120.4
C6—C5—C4	117.7 (4)	C15—C16—H16	120.4
C6—C5—H5	121.1	C16—C17—N12	124.5 (4)
C4—C5—H5	121.1	C16—C17—H17	117.7
N1—C6—C5	125.0 (3)	N12—C17—H17	117.7
N1—C6—H6	117.5	N11—C18—C14	121.0 (3)
C5—C6—H6	117.5	N11—C18—H18	119.5
O1—C7—N8	123.4 (7)	C14—C18—H18	119.5
O1B—C7—N8	116.5 (13)	C20—N19—C24	115.5 (3)
O1—C7—C3	116.8 (8)	N19—C20—C21	125.7 (3)
O1B—C7—C3	122.5 (12)	N19—C20—H20	117.2
N8—C7—C3	118.6 (2)	C21—C20—H20	117.2
C7—N8—C9B	119.2 (4)	C20—C21—C22	117.0 (3)
C7—N8—C9	119.7 (3)	C20—C21—C9	114.4 (3)
C7—N8—H8	123 (2)	C22—C21—C9	127.7 (3)
C9B—N8—H8	113 (2)	C20—C21—C10B	130.0 (4)
C9—N8—H8	116 (2)	C22—C21—C10B	104.0 (4)
N8—C9—C10	108.1 (3)	C23—C22—C21	119.0 (3)
N8—C9—C21	117.0 (3)	C23—C22—H22	120.5
C10—C9—C21	108.7 (4)	C21—C22—H22	120.5
N8—C9—H9	107.6	C24—C23—C22	118.5 (3)
C10—C9—H9	107.6	C24—C23—H23	120.7
C21—C9—H9	107.6	C22—C23—H23	120.7
N11—C10—C9	104.1 (3)	N19—C24—C23	124.3 (3)
N11—C10—C27	115.5 (3)	N19—C24—H24	117.8
C9—C10—C27	106.1 (4)	C23—C24—H24	117.8
N11—C10—H10	110.3	C26—N25—C30	115.6 (3)
C9—C10—H10	110.3	N25—C26—C27	126.5 (3)
C27—C10—H10	110.3	N25—C26—H26	116.8
N8—C9B—C10B	105.6 (6)	C27—C26—H26	116.8
N8—C9B—C27	120.2 (6)	C26—C27—C28	117.0 (3)
C10B—C9B—C27	98.0 (7)	C26—C27—C10	113.9 (3)
N8—C9B—H9B	110.7	C28—C27—C10	128.2 (3)
C10B—C9B—H9B	110.7	C26—C27—C9B	131.9 (4)
C27—C9B—H9B	110.7	C28—C27—C9B	100.9 (4)
C9B—C10B—N11	103.0 (6)	C10—C27—C9B	46.6 (3)
C9B—C10B—C21	98.5 (7)	C29—C28—C27	118.6 (3)
N11—C10B—C21	119.5 (6)	C29—C28—H28	120.7
C9B—C10B—H10B	111.5	C27—C28—H28	120.7
N11—C10B—H10B	111.5	C28—C29—C30	118.1 (3)
C21—C10B—H10B	111.5	C28—C29—H29	121.0
C18—N11—C10	117.8 (3)	C30—C29—H29	121.0
C18—N11—C10B	118.0 (4)	N25—C30—C29	124.3 (3)
C13—N12—C17	114.7 (4)	N25—C30—H30	117.9
N12—C13—C14	123.8 (4)	C29—C30—H30	117.9

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···N25i	0.84 (3)	2.33 (3)	3.168 (4)	174 (3)
C28—H28···O1ii	0.93	2.25	3.163 (16)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8⋯N25i	0.84 (3)	2.33 (3)	3.168 (4)	174 (3)
C28—H28⋯O1ii	0.93	2.25	3.163 (16)	169

Symmetry codes: (i) ; (ii) .