N-(2-Pyrid-yl)-4-toluidine.

There are two mol-ecules in the asymmetric unit of the title compound, C(12)H(12)N(2), with dihedral angles between the aromatic rings of 48.35 (12) and 51.02 (12)°. In the crystal structure, both mol-ecules form inversion dimers, linked by pairs of N-H⋯N hydrogen bonds.

Related literature

For the crystal structure of N-(2-pyrid­yl)aniline, see: Polamo et al. (1997 ▶)

Experimental

Crystal data

C12H12N2

M = 184.24

Monoclinic,

a = 18.2260 (7) Å

b = 10.5680 (3) Å

c = 10.6005 (3) Å

β = 95.364 (2)°

V = 2032.9 (1) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 100 (2) K

0.30 × 0.10 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

18430 measured reflections

4676 independent reflections

2774 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.206

S = 1.01

4676 reflections

263 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.64 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (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: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037306/sg2278sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037306/sg2278Isup2.hkl

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

C12H12N2	F000 = 784
Mr = 184.24	Dx = 1.204 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1819 reflections
a = 18.2260 (7) Å	θ = 2.2–24.4º
b = 10.5680 (3) Å	µ = 0.07 mm−1
c = 10.6005 (3) Å	T = 100 (2) K
β = 95.364 (2)º	Prism, colorless
V = 2032.9 (1) Å3	0.30 × 0.10 × 0.05 mm
Z = 8

Bruker SMART APEX diffractometer	2774 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.066
Monochromator: graphite	θmax = 27.5º
T = 100(2) K	θmin = 1.1º
ω scans	h = −23→23
Absorption correction: None	k = −13→13
18430 measured reflections	l = −13→13
4676 independent reflections

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)] = 0.070	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.206	w = 1/[σ2(Fo2) + (0.0922P)2 + 1.1608P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
4676 reflections	Δρmax = 0.64 e Å−3
263 parameters	Δρmin = −0.31 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
N1	0.09908 (12)	0.46043 (18)	0.0668 (2)	0.0267 (5)
N2	−0.01070 (12)	0.37392 (18)	0.11163 (19)	0.0279 (5)
N3	0.40746 (13)	0.5526 (2)	0.5578 (2)	0.0350 (6)
N4	0.52478 (13)	0.60957 (18)	0.62565 (19)	0.0317 (5)
C1	0.17505 (14)	0.4657 (2)	0.0530 (2)	0.0258 (5)
C2	0.21791 (14)	0.3582 (2)	0.0393 (2)	0.0293 (6)
H2	0.1962	0.2766	0.0418	0.035*
C3	0.29141 (14)	0.3698 (3)	0.0221 (3)	0.0337 (6)
H3	0.3198	0.2954	0.0138	0.040*
C4	0.32560 (15)	0.4877 (3)	0.0164 (3)	0.0334 (6)
C5	0.28179 (15)	0.5943 (2)	0.0269 (3)	0.0340 (6)
H5	0.3031	0.6759	0.0208	0.041*
C6	0.20817 (15)	0.5841 (2)	0.0460 (2)	0.0312 (6)
H0	0.1798	0.6585	0.0543	0.037*
C7	0.40666 (16)	0.4993 (3)	0.0012 (3)	0.0419 (7)
H7A	0.4166	0.5822	−0.0350	0.063*
H7B	0.4213	0.4325	−0.0555	0.063*
H7C	0.4348	0.4907	0.0841	0.063*
C8	0.06324 (14)	0.3732 (2)	0.1354 (2)	0.0269 (6)
C9	0.09904 (15)	0.2931 (2)	0.2268 (2)	0.0311 (6)
H9	0.1512	0.2944	0.2431	0.037*
C10	0.05715 (17)	0.2127 (2)	0.2923 (3)	0.0371 (7)
H10	0.0804	0.1573	0.3544	0.045*
C11	−0.01855 (16)	0.2121 (2)	0.2684 (3)	0.0377 (7)
H11	−0.0482	0.1566	0.3126	0.045*
C12	−0.04948 (16)	0.2946 (2)	0.1783 (3)	0.0340 (6)
H12	−0.1016	0.2955	0.1624	0.041*
C13	0.32986 (15)	0.5449 (2)	0.5522 (3)	0.0324 (6)
C14	0.29295 (16)	0.5298 (3)	0.6599 (3)	0.0377 (7)
H14	0.3199	0.5265	0.7410	0.045*
C15	0.21749 (16)	0.5196 (3)	0.6495 (3)	0.0379 (7)
H15	0.1931	0.5108	0.7244	0.045*
C16	0.17531 (15)	0.5217 (2)	0.5326 (3)	0.0342 (6)
C17	0.21226 (16)	0.5333 (2)	0.4247 (3)	0.0343 (6)
H17	0.1853	0.5331	0.3436	0.041*
C18	0.28849 (16)	0.5451 (2)	0.4344 (3)	0.0357 (7)
H18	0.3129	0.5536	0.3595	0.043*
C19	0.09289 (16)	0.5105 (3)	0.5244 (3)	0.0446 (7)
H19A	0.0753	0.4663	0.4461	0.067*
H19B	0.0710	0.5951	0.5244	0.067*
H19C	0.0786	0.4626	0.5975	0.067*
C20	0.45389 (16)	0.6270 (2)	0.6362 (2)	0.0318 (6)
C21	0.42898 (18)	0.7175 (2)	0.7187 (3)	0.0388 (7)
H21	0.3779	0.7288	0.7261	0.047*
C22	0.48103 (17)	0.7898 (2)	0.7891 (3)	0.0391 (7)
H22	0.4653	0.8516	0.8458	0.047*
C23	0.55493 (18)	0.7741 (2)	0.7787 (3)	0.0412 (7)
H23	0.5908	0.8242	0.8264	0.049*
C24	0.57493 (18)	0.6821 (2)	0.6957 (3)	0.0404 (7)
H24	0.6258	0.6690	0.6874	0.049*
H1N	0.0699 (14)	0.510 (2)	0.017 (2)	0.047 (9)*
H3N	0.4165 (16)	0.495 (2)	0.498 (2)	0.045 (9)*

	U11	U22	U33	U12	U13	U23
N1	0.0326 (12)	0.0186 (10)	0.0293 (12)	0.0017 (9)	0.0053 (9)	0.0041 (8)
N2	0.0344 (12)	0.0213 (10)	0.0291 (12)	0.0011 (9)	0.0080 (9)	0.0022 (8)
N3	0.0438 (14)	0.0293 (12)	0.0327 (13)	−0.0009 (10)	0.0075 (11)	−0.0068 (10)
N4	0.0537 (15)	0.0173 (10)	0.0240 (11)	−0.0013 (10)	0.0032 (10)	−0.0002 (8)
C1	0.0341 (14)	0.0227 (12)	0.0206 (12)	−0.0018 (10)	0.0022 (10)	−0.0012 (9)
C2	0.0361 (15)	0.0211 (12)	0.0302 (14)	−0.0005 (11)	0.0012 (11)	−0.0006 (10)
C3	0.0340 (15)	0.0325 (14)	0.0342 (15)	0.0038 (12)	0.0006 (12)	0.0000 (11)
C4	0.0347 (15)	0.0372 (15)	0.0279 (14)	−0.0031 (12)	0.0015 (11)	0.0026 (11)
C5	0.0437 (17)	0.0266 (13)	0.0316 (15)	−0.0074 (12)	0.0022 (12)	0.0034 (11)
C6	0.0413 (16)	0.0220 (12)	0.0306 (14)	−0.0002 (11)	0.0043 (12)	0.0015 (10)
C7	0.0378 (17)	0.0472 (17)	0.0410 (17)	−0.0038 (13)	0.0053 (13)	0.0045 (13)
C8	0.0414 (15)	0.0165 (11)	0.0237 (13)	−0.0001 (10)	0.0077 (11)	−0.0019 (9)
C9	0.0399 (16)	0.0256 (13)	0.0273 (14)	−0.0003 (11)	0.0009 (11)	0.0009 (10)
C10	0.0548 (19)	0.0287 (14)	0.0280 (15)	−0.0006 (13)	0.0046 (13)	0.0070 (11)
C11	0.0512 (18)	0.0289 (14)	0.0342 (16)	−0.0050 (13)	0.0112 (13)	0.0072 (11)
C12	0.0413 (16)	0.0302 (14)	0.0320 (15)	−0.0034 (12)	0.0103 (12)	0.0034 (11)
C13	0.0402 (16)	0.0240 (13)	0.0331 (15)	0.0023 (11)	0.0033 (12)	−0.0010 (11)
C14	0.0434 (17)	0.0361 (15)	0.0338 (15)	0.0017 (13)	0.0043 (13)	0.0060 (12)
C15	0.0438 (17)	0.0321 (14)	0.0383 (16)	0.0028 (12)	0.0069 (13)	0.0044 (12)
C16	0.0366 (16)	0.0218 (12)	0.0449 (17)	0.0031 (11)	0.0083 (13)	−0.0004 (11)
C17	0.0455 (17)	0.0228 (13)	0.0350 (15)	0.0008 (12)	0.0056 (12)	0.0003 (11)
C18	0.0477 (17)	0.0266 (14)	0.0343 (15)	−0.0010 (12)	0.0112 (13)	−0.0005 (11)
C19	0.0379 (17)	0.0482 (18)	0.0481 (19)	0.0053 (14)	0.0067 (14)	0.0015 (14)
C20	0.0491 (17)	0.0213 (12)	0.0253 (14)	−0.0014 (11)	0.0044 (12)	0.0031 (10)
C21	0.0591 (19)	0.0267 (14)	0.0309 (15)	−0.0007 (13)	0.0052 (13)	−0.0021 (11)
C22	0.065 (2)	0.0221 (13)	0.0298 (15)	0.0027 (13)	0.0000 (14)	−0.0040 (11)
C23	0.069 (2)	0.0218 (13)	0.0313 (16)	0.0038 (13)	−0.0040 (14)	−0.0044 (11)
C24	0.0553 (19)	0.0253 (13)	0.0404 (17)	0.0010 (13)	0.0025 (14)	−0.0005 (12)

N1—C8	1.376 (3)	C10—C11	1.379 (4)
N1—C1	1.407 (3)	C10—H10	0.9500
N1—H1N	0.884 (10)	C11—C12	1.375 (4)
N2—C12	1.340 (3)	C11—H11	0.9500
N2—C8	1.348 (3)	C12—H12	0.9500
N3—C20	1.376 (3)	C13—C14	1.388 (4)
N3—C13	1.412 (3)	C13—C18	1.398 (4)
N3—H3N	0.911 (10)	C14—C15	1.374 (4)
N4—C20	1.320 (3)	C14—H14	0.9500
N4—C24	1.359 (3)	C15—C16	1.396 (4)
C1—C2	1.393 (3)	C15—H15	0.9500
C1—C6	1.395 (3)	C16—C17	1.385 (4)
C2—C3	1.374 (4)	C16—C19	1.501 (4)
C2—H2	0.9500	C17—C18	1.389 (4)
C3—C4	1.397 (4)	C17—H17	0.9500
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.391 (4)	C19—H19A	0.9800
C4—C7	1.506 (4)	C19—H19B	0.9800
C5—C6	1.380 (4)	C19—H19C	0.9800
C5—H5	0.9500	C20—C21	1.400 (4)
C6—H0	0.9500	C21—C22	1.381 (4)
C7—H7A	0.9800	C21—H21	0.9500
C7—H7B	0.9800	C22—C23	1.372 (4)
C7—H7C	0.9800	C22—H22	0.9500
C8—C9	1.400 (3)	C23—C24	1.382 (4)
C9—C10	1.374 (4)	C23—H23	0.9500
C9—H9	0.9500	C24—H24	0.9500
C8—N1—C1	127.0 (2)	C10—C11—H11	121.2
C8—N1—H1N	115 (2)	N2—C12—C11	124.1 (3)
C1—N1—H1N	117 (2)	N2—C12—H12	117.9
C12—N2—C8	117.7 (2)	C11—C12—H12	117.9
C20—N3—C13	128.0 (2)	C14—C13—C18	118.2 (3)
C20—N3—H3N	131.8 (19)	C14—C13—N3	122.2 (3)
C13—N3—H3N	100.2 (19)	C18—C13—N3	119.5 (2)
C20—N4—C24	119.2 (2)	C15—C14—C13	120.1 (3)
C2—C1—C6	118.4 (2)	C15—C14—H14	119.9
C2—C1—N1	123.1 (2)	C13—C14—H14	119.9
C6—C1—N1	118.4 (2)	C14—C15—C16	122.3 (3)
C3—C2—C1	120.3 (2)	C14—C15—H15	118.8
C3—C2—H2	119.9	C16—C15—H15	118.8
C1—C2—H2	119.9	C17—C16—C15	117.7 (3)
C2—C3—C4	122.0 (2)	C17—C16—C19	121.4 (3)
C2—C3—H3	119.0	C15—C16—C19	121.0 (3)
C4—C3—H3	119.0	C16—C17—C18	120.5 (3)
C5—C4—C3	117.2 (2)	C16—C17—H17	119.8
C5—C4—C7	121.3 (2)	C18—C17—H17	119.8
C3—C4—C7	121.5 (3)	C17—C18—C13	121.2 (3)
C6—C5—C4	121.5 (2)	C17—C18—H18	119.4
C6—C5—H5	119.3	C13—C18—H18	119.4
C4—C5—H5	119.3	C16—C19—H19A	109.5
C5—C6—C1	120.6 (2)	C16—C19—H19B	109.5
C5—C6—H0	119.7	H19A—C19—H19B	109.5
C1—C6—H0	119.7	C16—C19—H19C	109.5
C4—C7—H7A	109.5	H19A—C19—H19C	109.5
C4—C7—H7B	109.5	H19B—C19—H19C	109.5
H7A—C7—H7B	109.5	N4—C20—N3	114.9 (2)
C4—C7—H7C	109.5	N4—C20—C21	121.7 (3)
H7A—C7—H7C	109.5	N3—C20—C21	123.4 (3)
H7B—C7—H7C	109.5	C22—C21—C20	118.0 (3)
N2—C8—N1	114.4 (2)	C22—C21—H21	121.0
N2—C8—C9	121.7 (2)	C20—C21—H21	121.0
N1—C8—C9	123.8 (2)	C23—C22—C21	121.3 (3)
C10—C9—C8	118.6 (3)	C23—C22—H22	119.4
C10—C9—H9	120.7	C21—C22—H22	119.4
C8—C9—H9	120.7	C22—C23—C24	117.1 (3)
C9—C10—C11	120.3 (3)	C22—C23—H23	121.4
C9—C10—H10	119.9	C24—C23—H23	121.4
C11—C10—H10	119.9	N4—C24—C23	122.7 (3)
C12—C11—C10	117.6 (2)	N4—C24—H24	118.7
C12—C11—H11	121.2	C23—C24—H24	118.7
C8—N1—C1—C2	39.0 (4)	C20—N3—C13—C14	−48.6 (4)
C8—N1—C1—C6	−144.6 (2)	C20—N3—C13—C18	135.1 (3)
C6—C1—C2—C3	1.5 (4)	C18—C13—C14—C15	−2.0 (4)
N1—C1—C2—C3	177.9 (2)	N3—C13—C14—C15	−178.4 (2)
C1—C2—C3—C4	−0.7 (4)	C13—C14—C15—C16	1.1 (4)
C2—C3—C4—C5	−1.0 (4)	C14—C15—C16—C17	0.7 (4)
C2—C3—C4—C7	178.3 (2)	C14—C15—C16—C19	−179.9 (3)
C3—C4—C5—C6	1.9 (4)	C15—C16—C17—C18	−1.4 (4)
C7—C4—C5—C6	−177.4 (2)	C19—C16—C17—C18	179.2 (2)
C4—C5—C6—C1	−1.1 (4)	C16—C17—C18—C13	0.4 (4)
C2—C1—C6—C5	−0.6 (4)	C14—C13—C18—C17	1.3 (4)
N1—C1—C6—C5	−177.2 (2)	N3—C13—C18—C17	177.8 (2)
C12—N2—C8—N1	−177.6 (2)	C24—N4—C20—N3	177.5 (2)
C12—N2—C8—C9	−0.2 (3)	C24—N4—C20—C21	−0.7 (4)
C1—N1—C8—N2	−166.9 (2)	C13—N3—C20—N4	176.3 (2)
C1—N1—C8—C9	15.8 (4)	C13—N3—C20—C21	−5.5 (4)
N2—C8—C9—C10	0.7 (4)	N4—C20—C21—C22	0.5 (4)
N1—C8—C9—C10	177.8 (2)	N3—C20—C21—C22	−177.5 (2)
C8—C9—C10—C11	−0.3 (4)	C20—C21—C22—C23	0.1 (4)
C9—C10—C11—C12	−0.4 (4)	C21—C22—C23—C24	−0.6 (4)
C8—N2—C12—C11	−0.6 (4)	C20—N4—C24—C23	0.2 (4)
C10—C11—C12—N2	0.9 (4)	C22—C23—C24—N4	0.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···N2i	0.88 (1)	2.06 (1)	2.944 (3)	174 (3)
N3—H3n···N4ii	0.91 (1)	2.08 (2)	2.949 (3)	159 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯N2i	0.88 (1)	2.06 (1)	2.944 (3)	174 (3)
N3—H3n⋯N4ii	0.91 (1)	2.08 (2)	2.949 (3)	159 (3)

Symmetry codes: (i) ; (ii) .