Bis(4-meth-oxy-pyridin-3-yl)diazene.

The asymmetric unit of the title compound, C(12)H(12)N(4)O(2), consists of one half-mol-ecule, which is located on a center of inversion. The molecule has a step-like shape; the azo group adopting a trans configuration, with the pyridine rings being parallel-displace.

Related literature

For background to this work, see: Thies et al. (2010 ▶, 2011 ▶); Venkataramani et al. (2011 ▶).

Experimental

Crystal data

C12H12N4O2

M = 244.26

Orthorhombic,

a = 13.3976 (8) Å

b = 6.2101 (6) Å

c = 13.6079 (9) Å

V = 1132.18 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 220 K

0.3 × 0.2 × 0.2 mm

Data collection

Stoe IPDS-1 diffractometer

5829 measured reflections

1235 independent reflections

1002 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.105

S = 1.04

1235 reflections

84 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.19 e Å−3

Data collection: X-AREA (Stoe & Cie, 2008 ▶); cell refinement: X-AREA; data reduction: X-RED32; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812018326/bt5885sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018326/bt5885Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018326/bt5885Isup3.cml

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

C12H12N4O2	Dx = 1.433 Mg m−3
Mr = 244.26	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 4972 reflections
a = 13.3976 (8) Å	θ = 4.7–28.8°
b = 6.2101 (6) Å	µ = 0.10 mm−1
c = 13.6079 (9) Å	T = 220 K
V = 1132.18 (15) Å3	Block, colourless
Z = 4	0.3 × 0.2 × 0.2 mm
F(000) = 512

Stoe IPDS-1 diffractometer	1002 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
Graphite monochromator	θmax = 27.1°, θmin = 3.0°
Phi scans	h = −17→12
5829 measured reflections	k = −7→7
1235 independent reflections	l = −17→17

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0625P)2 + 0.204P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1235 reflections	Δρmax = 0.26 e Å−3
84 parameters	Δρmin = −0.19 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: 0.030 (8)

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	0.66974 (9)	0.6358 (2)	0.34371 (9)	0.0314 (3)
C1	0.62249 (10)	0.7907 (2)	0.39360 (9)	0.0263 (3)
H1	0.6591	0.9134	0.4119	0.032*
C2	0.52211 (9)	0.7811 (2)	0.42010 (8)	0.0211 (3)
C3	0.46546 (10)	0.60269 (19)	0.38987 (8)	0.0205 (3)
C4	0.51423 (10)	0.4414 (2)	0.33786 (9)	0.0250 (3)
H4	0.4794	0.3190	0.3161	0.030*
C5	0.61506 (11)	0.4644 (2)	0.31870 (10)	0.0301 (3)
H5	0.6475	0.3513	0.2857	0.036*
N2	0.47208 (8)	0.94965 (17)	0.47068 (7)	0.0228 (3)
O1	0.36924 (7)	0.60036 (15)	0.41627 (7)	0.0277 (3)
C6	0.30947 (11)	0.4230 (2)	0.38338 (11)	0.0321 (4)
H6A	0.3032	0.4284	0.3124	0.048*
H6B	0.2438	0.4320	0.4130	0.048*
H6C	0.3410	0.2888	0.4024	0.048*

	U11	U22	U33	U12	U13	U23
N1	0.0230 (6)	0.0348 (6)	0.0364 (7)	−0.0008 (5)	0.0067 (5)	−0.0042 (5)
C1	0.0237 (7)	0.0271 (7)	0.0280 (6)	−0.0044 (5)	0.0010 (5)	−0.0020 (5)
C2	0.0227 (6)	0.0202 (6)	0.0203 (5)	0.0000 (5)	−0.0014 (4)	−0.0006 (4)
C3	0.0200 (6)	0.0208 (6)	0.0205 (6)	0.0011 (5)	−0.0014 (4)	0.0011 (4)
C4	0.0273 (7)	0.0216 (6)	0.0261 (6)	−0.0009 (5)	−0.0004 (5)	−0.0045 (5)
C5	0.0292 (7)	0.0283 (7)	0.0329 (7)	0.0039 (6)	0.0052 (5)	−0.0058 (5)
N2	0.0231 (5)	0.0202 (5)	0.0251 (5)	−0.0017 (4)	−0.0012 (4)	−0.0022 (4)
O1	0.0193 (5)	0.0241 (5)	0.0396 (6)	−0.0030 (4)	0.0020 (4)	−0.0086 (4)
C6	0.0230 (7)	0.0288 (7)	0.0444 (8)	−0.0068 (6)	−0.0037 (6)	−0.0068 (6)

N1—C5	1.3360 (19)	C4—C5	1.3832 (19)
N1—C1	1.3369 (18)	C4—H4	0.9400
C1—C2	1.3936 (18)	C5—H5	0.9400
C1—H1	0.9400	N2—N2i	1.260 (2)
C2—C3	1.4044 (17)	O1—C6	1.4333 (16)
C2—N2	1.4209 (16)	C6—H6A	0.9700
C3—O1	1.3384 (16)	C6—H6B	0.9700
C3—C4	1.3897 (17)	C6—H6C	0.9700
C5—N1—C1	116.29 (12)	C3—C4—H4	120.6
N1—C1—C2	123.89 (12)	N1—C5—C4	124.74 (13)
N1—C1—H1	118.1	N1—C5—H5	117.6
C2—C1—H1	118.1	C4—C5—H5	117.6
C1—C2—C3	118.65 (11)	N2i—N2—C2	113.10 (14)
C1—C2—N2	123.30 (11)	C3—O1—C6	117.56 (10)
C3—C2—N2	117.91 (11)	O1—C6—H6A	109.5
O1—C3—C4	125.58 (11)	O1—C6—H6B	109.5
O1—C3—C2	116.77 (11)	H6A—C6—H6B	109.5
C4—C3—C2	117.62 (12)	O1—C6—H6C	109.5
C5—C4—C3	118.73 (12)	H6A—C6—H6C	109.5
C5—C4—H4	120.6	H6B—C6—H6C	109.5