Pyridine-4-carb­aldehyde azine

In the crystal structure of the title compound, C₁₂H₁₀N₄, the pyridine ring makes a dihedral angle of 1.12 (9)° with the mean plane of the complete almost planar and crystallographically centrosymmetric mol­ecule. There are stacks of parallel mol­ecules along the a-axis direction, with alternate stacks having a herring-bone arrangement relative to each other and an interplanar spacing of 3.551 Å.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).

(I)

Crystal data

C12H10N4	F(000) = 220
Mr = 210.24	Dx = 1.293 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 3.8515 (3) Å	Cell parameters from 2605 reflections
b = 11.0201 (8) Å	θ = 2.5–28.3°
c = 12.7303 (9) Å	µ = 0.08 mm^−1
β = 92.312 (2)°	T = 293 K
V = 539.88 (7) Å^3	Block, orange
Z = 2	0.38 × 0.36 × 0.32 mm

Data collection

Siemens SMART CCD area-detector diffractometer	1065 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 28.4°, θmin = 2.5°
Detector resolution: 8.33 pixels mm^-1	h = −5→5
ω scans	k = −14→7
3584 measured reflections	l = −16→16
1325 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	All H-atom parameters refined
S = 1.25	w = 1/[σ^2(Fo^2) + (0.0958P)^2 + 0.1438P] where P = (Fo^2 + 2Fc^2)/3
1325 reflections	(Δ/σ)max < 0.001
93 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.0922 (6)	0.8462 (2)	0.08500 (15)	0.0580 (6)
N2	0.4664 (5)	1.00082 (15)	0.44528 (12)	0.0453 (5)
C1	0.2637 (5)	0.88327 (16)	0.29857 (14)	0.0380 (5)
C2	0.3255 (6)	0.97260 (19)	0.22425 (15)	0.0429 (5)
C3	0.2348 (6)	0.9499 (2)	0.12006 (17)	0.0524 (6)
C4	0.0341 (7)	0.7614 (2)	0.15670 (19)	0.0547 (6)
C5	0.1144 (6)	0.77541 (19)	0.26308 (17)	0.0473 (5)
C6	0.3510 (5)	0.90013 (18)	0.41100 (15)	0.0416 (5)
H2	0.436 (7)	1.049 (3)	0.244 (2)	0.064 (8)*
H3	0.276 (7)	1.011 (3)	0.067 (2)	0.061 (7)*
H4	−0.077 (8)	0.687 (3)	0.129 (2)	0.073 (8)*
H5	0.062 (7)	0.708 (3)	0.312 (2)	0.063 (7)*
H6	0.318 (6)	0.833 (2)	0.457 (2)	0.056 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0709 (13)	0.0645 (13)	0.0383 (9)	0.0023 (10)	−0.0024 (8)	−0.0116 (8)
N2	0.0617 (11)	0.0423 (9)	0.0312 (9)	−0.0022 (7)	−0.0073 (7)	0.0017 (6)
C1	0.0408 (10)	0.0379 (9)	0.0352 (9)	0.0026 (7)	0.0002 (7)	−0.0025 (7)
C2	0.0510 (11)	0.0404 (10)	0.0373 (10)	−0.0011 (8)	−0.0003 (8)	−0.0008 (7)
C3	0.0658 (14)	0.0554 (13)	0.0362 (10)	0.0042 (10)	0.0020 (9)	0.0025 (9)
C4	0.0627 (14)	0.0516 (12)	0.0497 (12)	−0.0048 (10)	−0.0007 (10)	−0.0166 (10)
C5	0.0575 (13)	0.0392 (10)	0.0453 (11)	−0.0029 (8)	0.0028 (9)	−0.0051 (8)
C6	0.0522 (11)	0.0375 (9)	0.0350 (9)	−0.0016 (8)	−0.0009 (7)	0.0021 (7)

Geometric parameters (Å, º)

N1—C4	1.332 (3)	C2—C3	1.381 (3)
N1—C3	1.337 (3)	C2—H2	0.97 (3)
N2—C6	1.266 (3)	C3—H3	0.97 (3)
N2—N2^i	1.407 (3)	C4—C5	1.386 (3)
C1—C5	1.388 (3)	C4—H4	0.98 (3)
C1—C2	1.393 (3)	C5—H5	0.99 (3)
C1—C6	1.469 (3)	C6—H6	0.95 (3)
C4—N1—C3	116.7 (2)	C2—C3—H3	119.9 (17)
C6—N2—N2^i	112.2 (2)	N1—C4—C5	123.7 (2)
C5—C1—C2	117.64 (18)	N1—C4—H4	114.9 (18)
C5—C1—C6	120.08 (17)	C5—C4—H4	121.4 (18)
C2—C1—C6	122.28 (17)	C4—C5—C1	119.2 (2)
C3—C2—C1	118.75 (19)	C4—C5—H5	119.0 (16)
C3—C2—H2	119.9 (17)	C1—C5—H5	121.8 (16)
C1—C2—H2	121.3 (17)	N2—C6—C1	120.67 (17)
N1—C3—C2	124.1 (2)	N2—C6—H6	121.4 (16)
N1—C3—H3	116.1 (17)	C1—C6—H6	117.9 (16)
C5—C1—C2—C3	0.3 (3)	C2—C1—C5—C4	0.0 (3)
C6—C1—C2—C3	−179.78 (19)	C6—C1—C5—C4	−179.98 (19)
C4—N1—C3—C2	0.5 (4)	N2^i—N2—C6—C1	179.84 (19)
C1—C2—C3—N1	−0.5 (4)	C5—C1—C6—N2	−175.41 (19)
C3—N1—C4—C5	−0.3 (4)	C2—C1—C6—N2	4.6 (3)
N1—C4—C5—C1	0.0 (4)

Symmetry code: (i) −x+1, −y+2, −z+1.