N-(4-Methyl-2-pyrid-yl)-p-toluidine.

In the title compound, C(13)H(14)N(2), the dihedral angle between the aromatic rings is 48.1 (1)° and the bridging C-N-C bond angle is 127.24 (12)°. In the crystal, intermolecular N-H⋯N hydrogen bonding about a center of inversion generates a hydrogen-bonded dimer.

Related literature

For the structure of N-(2-pyrid­yl)-4-toluidine, see: Fairuz et al. (2008 ▶).

Experimental

Crystal data

C13H14N2

M = 198.26

Monoclinic,

a = 10.9385 (11) Å

b = 7.5708 (8) Å

c = 13.4372 (14) Å

β = 95.246 (2)°

V = 1108.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 295 K

0.45 × 0.40 × 0.30 mm

Data collection

Bruker SMART APEX diffractometer

6758 measured reflections

2528 independent reflections

1797 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.142

S = 1.05

2528 reflections

143 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680905586X/xu2710sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905586X/xu2710Isup2.hkl

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

C13H14N2	F(000) = 424
Mr = 198.26	Dx = 1.188 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2289 reflections
a = 10.9385 (11) Å	θ = 2.5–28.1°
b = 7.5708 (8) Å	µ = 0.07 mm−1
c = 13.4372 (14) Å	T = 295 K
β = 95.246 (2)°	Irregular block, colorless
V = 1108.1 (2) Å3	0.45 × 0.40 × 0.30 mm
Z = 4

Bruker SMART APEX diffractometer	1797 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 27.5°, θmin = 2.3°
ω scans	h = −14→13
6758 measured reflections	k = −9→9
2528 independent reflections	l = −14→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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0692P)2 + 0.1529P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2528 reflections	Δρmax = 0.17 e Å−3
143 parameters	Δρmin = −0.13 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.044 (6)

	x	y	z	Uiso*/Ueq
N1	0.51269 (11)	0.54344 (19)	0.64065 (9)	0.0571 (4)
H1	0.4682 (13)	0.546 (2)	0.5832 (8)	0.063 (5)*
N2	0.66732 (12)	0.46482 (18)	0.54571 (9)	0.0554 (4)
C1	0.78715 (15)	0.4383 (2)	0.53779 (12)	0.0642 (5)
H1A	0.8107	0.4072	0.4754	0.077*
C2	0.87740 (14)	0.4535 (2)	0.61487 (13)	0.0619 (4)
H2	0.9588	0.4288	0.6052	0.074*
C3	0.84502 (13)	0.50645 (19)	0.70755 (11)	0.0490 (4)
C4	0.72299 (13)	0.53940 (19)	0.71698 (11)	0.0471 (3)
H4	0.6985	0.5788	0.7776	0.056*
C5	0.63566 (13)	0.51384 (18)	0.63552 (10)	0.0458 (3)
C6	0.93890 (14)	0.5264 (2)	0.79563 (12)	0.0607 (4)
H6A	0.9168	0.6239	0.8360	0.091*
H6B	1.0180	0.5479	0.7725	0.091*
H6C	0.9418	0.4201	0.8347	0.091*
C7	0.45006 (12)	0.55349 (19)	0.72722 (10)	0.0447 (3)
C8	0.35038 (12)	0.6665 (2)	0.72803 (11)	0.0516 (4)
H8	0.3294	0.7385	0.6731	0.062*
C9	0.28208 (13)	0.6735 (2)	0.80914 (11)	0.0547 (4)
H9	0.2153	0.7498	0.8077	0.066*
C10	0.31070 (13)	0.5694 (2)	0.89293 (11)	0.0526 (4)
C11	0.41089 (13)	0.4573 (2)	0.89151 (11)	0.0502 (4)
H11	0.4322	0.3860	0.9467	0.060*
C12	0.47974 (13)	0.44843 (19)	0.81091 (10)	0.0477 (4)
H12	0.5464	0.3719	0.8124	0.057*
C13	0.23520 (17)	0.5750 (3)	0.98106 (13)	0.0757 (5)
H13A	0.1631	0.6452	0.9646	0.113*
H13B	0.2829	0.6262	1.0373	0.113*
H13C	0.2115	0.4572	0.9974	0.113*

	U11	U22	U33	U12	U13	U23
N1	0.0418 (7)	0.0866 (10)	0.0424 (7)	0.0084 (6)	0.0001 (5)	0.0006 (6)
N2	0.0492 (7)	0.0675 (8)	0.0496 (7)	0.0037 (6)	0.0048 (5)	−0.0037 (6)
C1	0.0536 (9)	0.0824 (12)	0.0583 (9)	0.0073 (8)	0.0136 (7)	−0.0093 (8)
C2	0.0426 (8)	0.0744 (11)	0.0698 (10)	0.0060 (7)	0.0104 (7)	−0.0040 (8)
C3	0.0433 (8)	0.0435 (8)	0.0599 (9)	−0.0004 (6)	0.0025 (6)	0.0045 (6)
C4	0.0439 (7)	0.0494 (8)	0.0479 (7)	0.0008 (6)	0.0049 (6)	−0.0010 (6)
C5	0.0427 (7)	0.0476 (8)	0.0471 (7)	0.0022 (6)	0.0049 (6)	0.0029 (6)
C6	0.0435 (8)	0.0664 (10)	0.0706 (10)	−0.0005 (7)	−0.0032 (7)	0.0044 (8)
C7	0.0363 (7)	0.0533 (8)	0.0434 (7)	−0.0015 (6)	−0.0023 (5)	−0.0024 (6)
C8	0.0424 (7)	0.0570 (9)	0.0542 (8)	0.0033 (6)	−0.0022 (6)	0.0070 (7)
C9	0.0411 (7)	0.0585 (9)	0.0643 (9)	0.0052 (6)	0.0031 (6)	−0.0040 (7)
C10	0.0452 (8)	0.0625 (9)	0.0500 (8)	−0.0080 (7)	0.0034 (6)	−0.0102 (7)
C11	0.0479 (8)	0.0559 (9)	0.0450 (7)	−0.0082 (6)	−0.0047 (6)	0.0031 (6)
C12	0.0408 (7)	0.0497 (8)	0.0512 (8)	0.0021 (6)	−0.0036 (6)	−0.0022 (6)
C13	0.0698 (11)	0.0969 (14)	0.0623 (10)	−0.0047 (10)	0.0172 (8)	−0.0109 (10)

N1—C5	1.3716 (18)	C6—H6C	0.9600
N1—C7	1.4051 (18)	C7—C8	1.3867 (19)
N1—H1	0.875 (9)	C7—C12	1.391 (2)
N2—C1	1.340 (2)	C8—C9	1.378 (2)
N2—C5	1.3380 (18)	C8—H8	0.9300
C1—C2	1.369 (2)	C9—C10	1.386 (2)
C1—H1A	0.9300	C9—H9	0.9300
C2—C3	1.385 (2)	C10—C11	1.388 (2)
C2—H2	0.9300	C10—C13	1.505 (2)
C3—C4	1.375 (2)	C11—C12	1.376 (2)
C3—C6	1.502 (2)	C11—H11	0.9300
C4—C5	1.399 (2)	C12—H12	0.9300
C4—H4	0.9300	C13—H13A	0.9600
C6—H6A	0.9600	C13—H13B	0.9600
C6—H6B	0.9600	C13—H13C	0.9600
C5—N1—C7	127.24 (12)	C8—C7—C12	118.16 (13)
C5—N1—H1	115.4 (11)	C8—C7—N1	118.89 (13)
C7—N1—H1	117.1 (11)	C12—C7—N1	122.87 (13)
C1—N2—C5	116.68 (13)	C9—C8—C7	120.90 (13)
N2—C1—C2	124.77 (15)	C9—C8—H8	119.5
N2—C1—H1A	117.6	C7—C8—H8	119.5
C2—C1—H1A	117.6	C8—C9—C10	121.47 (14)
C1—C2—C3	118.61 (14)	C8—C9—H9	119.3
C1—C2—H2	120.7	C10—C9—H9	119.3
C3—C2—H2	120.7	C9—C10—C11	117.16 (14)
C4—C3—C2	117.75 (14)	C9—C10—C13	121.57 (15)
C4—C3—C6	120.58 (14)	C11—C10—C13	121.26 (15)
C2—C3—C6	121.67 (14)	C12—C11—C10	122.03 (14)
C3—C4—C5	120.13 (13)	C12—C11—H11	119.0
C3—C4—H4	119.9	C10—C11—H11	119.0
C5—C4—H4	119.9	C11—C12—C7	120.27 (13)
N2—C5—N1	115.25 (12)	C11—C12—H12	119.9
N2—C5—C4	121.97 (13)	C7—C12—H12	119.9
N1—C5—C4	122.73 (13)	C10—C13—H13A	109.5
C3—C6—H6A	109.5	C10—C13—H13B	109.5
C3—C6—H6B	109.5	H13A—C13—H13B	109.5
H6A—C6—H6B	109.5	C10—C13—H13C	109.5
C3—C6—H6C	109.5	H13A—C13—H13C	109.5
H6A—C6—H6C	109.5	H13B—C13—H13C	109.5
H6B—C6—H6C	109.5
C5—N2—C1—C2	1.7 (3)	C5—N1—C7—C8	146.94 (15)
N2—C1—C2—C3	−2.5 (3)	C5—N1—C7—C12	−36.3 (2)
C1—C2—C3—C4	0.6 (2)	C12—C7—C8—C9	−0.5 (2)
C1—C2—C3—C6	−179.91 (16)	N1—C7—C8—C9	176.39 (13)
C2—C3—C4—C5	2.0 (2)	C7—C8—C9—C10	0.5 (2)
C6—C3—C4—C5	−177.51 (13)	C8—C9—C10—C11	−0.2 (2)
C1—N2—C5—N1	178.72 (14)	C8—C9—C10—C13	−179.16 (15)
C1—N2—C5—C4	1.1 (2)	C9—C10—C11—C12	0.0 (2)
C7—N1—C5—N2	163.28 (14)	C13—C10—C11—C12	178.95 (14)
C7—N1—C5—C4	−19.1 (2)	C10—C11—C12—C7	0.0 (2)
C3—C4—C5—N2	−3.0 (2)	C8—C7—C12—C11	0.3 (2)
C3—C4—C5—N1	179.59 (14)	N1—C7—C12—C11	−176.47 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.87 (1)	2.18 (1)	3.041 (2)	170 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.87 (1)	2.18 (1)	3.041 (2)	170 (2)

Symmetry code: (i) .