N,N-Dimethyl-4-[(2-pyrid-yl)diazen-yl]aniline.

The title compound, C(13)H(14)N(4), adopts a trans configuration about the azo bond. There is a dihedral angle of 12.18 (7)° between the pyridine and benzene rings and the mean plane of the dimethyl-amino substituent is twisted by 6.1 (2)° relative to the benzene ring. In the crystal, weak inter-molecular C-H⋯N hydrogen bonds result in a zigzag arrangement along [010].

Related literature

For applications of azo compounds in textile coloring and photovoltaic frameworks, see: Millington et al. (2007 ▶). For the synthesis of similar compounds, see: Krause & Krause (1980 ▶). For the X-ray structures of protonated n class="Chemical">2-(phenylazo)pyridine (azpy), a similar compound, and chelating complexes, see: Panneerselvam et al. (2000 ▶); Peacock et al. (2007 ▶); Ohashi et al. (2003 ▶). For the X-ray structures of complexes with the title compound, see: Dougan et al. (2006 ▶); Li et al. (2001 ▶);

Experimental

Crystal data

C13H14N4

M = 226.28

Monoclinic,

a = 6.2322 (4) Å

b = 19.9353 (11) Å

c = 9.6404 (6) Å

β = 96.003 (1)°

V = 1191.16 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.28 × 0.26 × 0.06 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.918, T max = 1.000

12811 measured reflections

2101 independent reflections

1754 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.108

S = 1.04

2101 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: n class="Chemical">Mercury and SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810025754/fj2313sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025754/fj2313Isup2.hkl

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

C13H14N4	F(000) = 480
Mr = 226.28	Dx = 1.262 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3335 reflections
a = 6.2322 (4) Å	θ = 2.4–25.4°
b = 19.9353 (11) Å	µ = 0.08 mm−1
c = 9.6404 (6) Å	T = 293 K
β = 96.003 (1)°	Block, colorless
V = 1191.16 (13) Å3	0.28 × 0.26 × 0.06 mm
Z = 4

Bruker APEX CCD area-detector diffractometer	2101 independent reflections
Radiation source: fine-focus sealed tube	1754 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −7→7
Tmin = 0.918, Tmax = 1.000	k = −23→23
12811 measured reflections	l = −11→11

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.057P)2 + 0.1546P] where P = (Fo2 + 2Fc2)/3
2101 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.18 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	0.26625 (18)	0.22136 (6)	0.68133 (12)	0.0540 (3)
C1	0.2173 (3)	0.27093 (7)	0.76510 (16)	0.0609 (4)
H1	0.3306	0.2956	0.8102	0.073*
C2	0.0116 (3)	0.28823 (7)	0.78947 (16)	0.0622 (4)
H2	−0.0136	0.3234	0.8490	0.075*
C3	−0.1564 (2)	0.25173 (8)	0.72277 (15)	0.0619 (4)
H3	−0.2983	0.2620	0.7363	0.074*
C4	−0.1119 (2)	0.20013 (7)	0.63609 (15)	0.0547 (4)
H4	−0.2227	0.1746	0.5906	0.066*
C5	0.1016 (2)	0.18679 (6)	0.61771 (13)	0.0449 (3)
N2	0.16987 (18)	0.13418 (5)	0.53090 (11)	0.0498 (3)
N3	0.01419 (17)	0.10823 (5)	0.45640 (11)	0.0487 (3)
C6	0.0660 (2)	0.05591 (6)	0.36836 (13)	0.0450 (3)
C7	−0.1052 (2)	0.02897 (7)	0.28271 (15)	0.0516 (3)
H7	−0.2431	0.0459	0.2879	0.062*
C8	−0.0770 (2)	−0.02177 (7)	0.19098 (14)	0.0508 (3)
H8	−0.1955	−0.0386	0.1352	0.061*
C9	0.1288 (2)	−0.04879 (6)	0.17993 (13)	0.0456 (3)
C10	0.3025 (2)	−0.02146 (7)	0.26841 (15)	0.0530 (4)
H10	0.4408	−0.0383	0.2644	0.064*
C11	0.2711 (2)	0.02924 (7)	0.35976 (14)	0.0511 (3)
H11	0.3881	0.0462	0.4169	0.061*
N4	0.15861 (18)	−0.09932 (6)	0.08935 (12)	0.0542 (3)
C12	−0.0229 (2)	−0.13009 (7)	0.00681 (16)	0.0597 (4)
H12A	−0.1279	−0.1441	0.0670	0.090*
H12B	0.0260	−0.1684	−0.0415	0.090*
H12C	−0.0871	−0.0982	−0.0597	0.090*
C13	0.3730 (2)	−0.12209 (9)	0.06728 (19)	0.0733 (5)
H13A	0.4497	−0.0864	0.0272	0.110*
H13B	0.3624	−0.1598	0.0051	0.110*
H13C	0.4490	−0.1351	0.1549	0.110*

	U11	U22	U33	U12	U13	U23
N1	0.0499 (7)	0.0566 (7)	0.0556 (7)	−0.0048 (5)	0.0061 (5)	−0.0065 (6)
C1	0.0631 (9)	0.0583 (9)	0.0613 (9)	−0.0094 (7)	0.0064 (7)	−0.0099 (7)
C2	0.0747 (10)	0.0535 (8)	0.0597 (9)	0.0077 (8)	0.0127 (8)	−0.0043 (7)
C3	0.0532 (8)	0.0707 (10)	0.0621 (9)	0.0137 (7)	0.0086 (7)	0.0022 (8)
C4	0.0480 (8)	0.0636 (9)	0.0516 (8)	−0.0012 (6)	0.0009 (6)	0.0009 (7)
C5	0.0477 (7)	0.0448 (7)	0.0419 (7)	0.0004 (6)	0.0029 (6)	0.0048 (5)
N2	0.0488 (6)	0.0510 (6)	0.0492 (6)	−0.0023 (5)	0.0038 (5)	−0.0007 (5)
N3	0.0507 (7)	0.0462 (6)	0.0484 (6)	−0.0008 (5)	0.0017 (5)	0.0041 (5)
C6	0.0483 (7)	0.0421 (7)	0.0447 (7)	−0.0007 (5)	0.0049 (6)	0.0049 (5)
C7	0.0416 (7)	0.0521 (8)	0.0612 (8)	0.0003 (6)	0.0052 (6)	0.0004 (7)
C8	0.0420 (7)	0.0517 (8)	0.0574 (8)	−0.0063 (6)	−0.0003 (6)	−0.0019 (6)
C9	0.0453 (7)	0.0444 (7)	0.0473 (7)	−0.0048 (6)	0.0054 (6)	0.0034 (5)
C10	0.0408 (7)	0.0558 (8)	0.0619 (8)	0.0011 (6)	0.0028 (6)	−0.0051 (7)
C11	0.0464 (8)	0.0528 (8)	0.0524 (8)	−0.0038 (6)	−0.0032 (6)	−0.0016 (6)
N4	0.0472 (7)	0.0551 (7)	0.0601 (7)	−0.0034 (5)	0.0048 (5)	−0.0105 (6)
C12	0.0590 (9)	0.0583 (9)	0.0612 (9)	−0.0100 (7)	0.0036 (7)	−0.0086 (7)
C13	0.0571 (9)	0.0797 (11)	0.0834 (11)	0.0040 (8)	0.0089 (8)	−0.0265 (9)

N1—C5	1.3311 (16)	C7—H7	0.9300
N1—C1	1.3316 (18)	C8—C9	1.4052 (18)
C1—C2	1.371 (2)	C8—H8	0.9300
C1—H1	0.9300	C9—N4	1.3586 (17)
C2—C3	1.378 (2)	C9—C10	1.4156 (18)
C2—H2	0.9300	C10—C11	1.3678 (19)
C3—C4	1.372 (2)	C10—H10	0.9300
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.3863 (19)	N4—C13	1.4477 (18)
C4—H4	0.9300	N4—C12	1.4494 (17)
C5—N2	1.4337 (16)	C12—H12A	0.9600
N2—N3	1.2566 (15)	C12—H12B	0.9600
N3—C6	1.4035 (16)	C12—H12C	0.9600
C6—C7	1.3870 (18)	C13—H13A	0.9600
C6—C11	1.3951 (19)	C13—H13B	0.9600
C7—C8	1.3668 (19)	C13—H13C	0.9600
C5—N1—C1	116.70 (12)	C9—C8—H8	119.6
N1—C1—C2	124.61 (14)	N4—C9—C8	121.36 (12)
N1—C1—H1	117.7	N4—C9—C10	121.68 (12)
C2—C1—H1	117.7	C8—C9—C10	116.95 (12)
C1—C2—C3	117.76 (14)	C11—C10—C9	121.37 (12)
C1—C2—H2	121.1	C11—C10—H10	119.3
C3—C2—H2	121.1	C9—C10—H10	119.3
C4—C3—C2	119.19 (14)	C10—C11—C6	120.90 (12)
C4—C3—H3	120.4	C10—C11—H11	119.6
C2—C3—H3	120.4	C6—C11—H11	119.6
C3—C4—C5	118.67 (13)	C9—N4—C13	121.16 (11)
C3—C4—H4	120.7	C9—N4—C12	121.01 (11)
C5—C4—H4	120.7	C13—N4—C12	117.77 (12)
N1—C5—C4	123.06 (12)	N4—C12—H12A	109.5
N1—C5—N2	112.72 (11)	N4—C12—H12B	109.5
C4—C5—N2	124.21 (12)	H12A—C12—H12B	109.5
N3—N2—C5	112.11 (11)	N4—C12—H12C	109.5
N2—N3—C6	116.04 (11)	H12A—C12—H12C	109.5
C7—C6—C11	118.00 (12)	H12B—C12—H12C	109.5
C7—C6—N3	115.89 (12)	N4—C13—H13A	109.5
C11—C6—N3	126.11 (12)	N4—C13—H13B	109.5
C8—C7—C6	121.93 (13)	H13A—C13—H13B	109.5
C8—C7—H7	119.0	N4—C13—H13C	109.5
C6—C7—H7	119.0	H13A—C13—H13C	109.5
C7—C8—C9	120.85 (12)	H13B—C13—H13C	109.5
C7—C8—H8	119.6
C5—N1—C1—C2	0.0 (2)	N3—C6—C7—C8	179.35 (12)
N1—C1—C2—C3	0.1 (2)	C6—C7—C8—C9	0.0 (2)
C1—C2—C3—C4	0.2 (2)	C7—C8—C9—N4	179.85 (12)
C2—C3—C4—C5	−0.5 (2)	C7—C8—C9—C10	0.5 (2)
C1—N1—C5—C4	−0.41 (19)	N4—C9—C10—C11	−179.74 (12)
C1—N1—C5—N2	−179.47 (11)	C8—C9—C10—C11	−0.4 (2)
C3—C4—C5—N1	0.7 (2)	C9—C10—C11—C6	−0.2 (2)
C3—C4—C5—N2	179.60 (12)	C7—C6—C11—C10	0.7 (2)
N1—C5—N2—N3	−170.52 (11)	N3—C6—C11—C10	−179.24 (12)
C4—C5—N2—N3	10.44 (17)	C8—C9—N4—C13	173.23 (14)
C5—N2—N3—C6	−179.68 (10)	C10—C9—N4—C13	−7.5 (2)
N2—N3—C6—C7	−177.82 (11)	C8—C9—N4—C12	−3.9 (2)
N2—N3—C6—C11	2.14 (18)	C10—C9—N4—C12	175.44 (12)
C11—C6—C7—C8	−0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N3i	0.93	2.58	3.4516 (18)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N3i	0.93	2.58	3.4516 (18)	157

Symmetry code: (i) .