N-(4-Chloro-phen-yl)-4-methyl-pyridin-2-amine.

In the title compound, C(12)H(11)ClN(2), the dihedral angle between the benzene and pyridyl rings is 48.03 (8)°. Twists are also evident in the mol-ecule, in particular about the N(a)-C(b) (a = amine and b = benzene) bond [C-N-C-C = -144.79 (18)°]. In the crystal, inversion dimers linked by pairs of N-H⋯N hydrogen bonds result in the formation of eight-membered {⋯NCNH}(2) synthons [or R(2) (2)(8) loops].

Related literature

For background to the fluorescence properties of compounds related to the title compound, see: Kawai et al. (2001 ▶); Abdullah (2005 ▶).

Experimental

Crystal data

C12H11ClN2

M = 218.68

Monoclinic,

a = 15.9335 (15) Å

b = 4.0651 (4) Å

c = 17.0153 (16) Å

β = 98.755 (1)°

V = 1089.26 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 293 K

0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.776, T max = 0.862

9785 measured reflections

2509 independent reflections

1886 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.132

S = 1.04

2509 reflections

141 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810030138/hb5582sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030138/hb5582Isup2.hkl

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

C12H11ClN2	F(000) = 456
Mr = 218.68	Dx = 1.333 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2763 reflections
a = 15.9335 (15) Å	θ = 2.4–25.7°
b = 4.0651 (4) Å	µ = 0.32 mm−1
c = 17.0153 (16) Å	T = 293 K
β = 98.755 (1)°	Block, colourless
V = 1089.26 (18) Å3	0.30 × 0.30 × 0.20 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2509 independent reflections
Radiation source: fine-focus sealed tube	1886 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→19
Tmin = 0.776, Tmax = 0.862	k = −5→5
9785 measured reflections	l = −22→20

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0689P)2 + 0.1992P] where P = (Fo2 + 2Fc2)/3
2509 reflections	(Δ/σ)max < 0.001
141 parameters	Δρmax = 0.22 e Å−3
1 restraint	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
Cl1	0.59502 (4)	1.02913 (16)	0.10424 (3)	0.0834 (2)
N1	0.60831 (9)	0.5290 (4)	0.56614 (8)	0.0495 (4)
N2	0.57324 (9)	0.6997 (4)	0.43820 (9)	0.0552 (4)
H2n	0.5222 (7)	0.653 (5)	0.4444 (11)	0.061 (6)*
C1	0.63451 (10)	0.6751 (4)	0.50365 (9)	0.0439 (4)
C2	0.66466 (12)	0.5088 (5)	0.63260 (11)	0.0578 (5)
H2	0.6472	0.4101	0.6767	0.069*
C3	0.74612 (12)	0.6230 (5)	0.64035 (10)	0.0570 (5)
H3	0.7827	0.5985	0.6881	0.068*
C4	0.77369 (11)	0.7769 (4)	0.57556 (10)	0.0498 (4)
C5	0.71648 (10)	0.8019 (4)	0.50667 (10)	0.0461 (4)
H5	0.7323	0.9030	0.4621	0.055*
C6	0.86175 (12)	0.9137 (6)	0.58031 (13)	0.0661 (5)
H6A	0.8620	1.0847	0.5414	0.099*
H6B	0.8999	0.7416	0.5701	0.099*
H6C	0.8797	1.0023	0.6325	0.099*
C7	0.58319 (10)	0.7850 (4)	0.36041 (9)	0.0428 (4)
C8	0.51945 (11)	0.9664 (4)	0.31600 (11)	0.0496 (4)
H8	0.4740	1.0406	0.3396	0.059*
C9	0.52239 (12)	1.0389 (4)	0.23723 (11)	0.0544 (4)
H9	0.4789	1.1588	0.2077	0.065*
C10	0.59014 (12)	0.9323 (4)	0.20290 (10)	0.0493 (4)
C11	0.65418 (11)	0.7545 (4)	0.24569 (10)	0.0481 (4)
H11	0.6998	0.6843	0.2219	0.058*
C12	0.65108 (10)	0.6791 (4)	0.32428 (10)	0.0462 (4)
H12	0.6946	0.5570	0.3532	0.055*

	U11	U22	U33	U12	U13	U23
Cl1	0.1035 (5)	0.0997 (5)	0.0472 (3)	−0.0123 (3)	0.0123 (3)	0.0172 (3)
N1	0.0440 (8)	0.0626 (9)	0.0425 (8)	0.0058 (6)	0.0082 (6)	0.0026 (6)
N2	0.0364 (8)	0.0858 (12)	0.0428 (8)	−0.0052 (7)	0.0048 (6)	0.0083 (7)
C1	0.0414 (8)	0.0494 (9)	0.0409 (8)	0.0059 (7)	0.0061 (6)	−0.0034 (7)
C2	0.0582 (11)	0.0722 (13)	0.0430 (9)	0.0070 (9)	0.0072 (8)	0.0058 (8)
C3	0.0574 (11)	0.0673 (11)	0.0424 (9)	0.0083 (9)	−0.0051 (8)	−0.0042 (8)
C4	0.0481 (9)	0.0476 (9)	0.0515 (10)	0.0039 (7)	0.0006 (7)	−0.0127 (7)
C5	0.0452 (9)	0.0486 (9)	0.0439 (9)	−0.0008 (7)	0.0049 (7)	−0.0019 (7)
C6	0.0535 (11)	0.0693 (12)	0.0705 (13)	−0.0074 (9)	−0.0066 (9)	−0.0119 (10)
C7	0.0379 (8)	0.0485 (9)	0.0409 (8)	−0.0039 (7)	0.0027 (6)	−0.0004 (7)
C8	0.0436 (9)	0.0535 (10)	0.0512 (10)	0.0057 (7)	0.0059 (7)	−0.0012 (7)
C9	0.0539 (10)	0.0521 (10)	0.0541 (10)	0.0051 (8)	−0.0019 (8)	0.0089 (8)
C10	0.0572 (10)	0.0488 (9)	0.0411 (8)	−0.0110 (8)	0.0052 (7)	0.0025 (7)
C11	0.0440 (9)	0.0518 (10)	0.0495 (9)	−0.0053 (7)	0.0101 (7)	−0.0027 (7)
C12	0.0373 (8)	0.0517 (9)	0.0486 (9)	0.0024 (7)	0.0032 (7)	0.0034 (7)

Cl1—C10	1.7376 (18)	C6—H6A	0.9600
N1—C2	1.335 (2)	C6—H6B	0.9600
N1—C1	1.339 (2)	C6—H6C	0.9600
N2—C1	1.368 (2)	C7—C8	1.383 (2)
N2—C7	1.400 (2)	C7—C12	1.391 (2)
N2—H2n	0.857 (9)	C8—C9	1.380 (2)
C1—C5	1.398 (2)	C8—H8	0.9300
C2—C3	1.366 (3)	C9—C10	1.373 (3)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.396 (3)	C10—C11	1.367 (2)
C3—H3	0.9300	C11—C12	1.380 (2)
C4—C5	1.375 (2)	C11—H11	0.9300
C4—C6	1.500 (3)	C12—H12	0.9300
C5—H5	0.9300
C2—N1—C1	116.69 (15)	C4—C6—H6C	109.5
C1—N2—C7	128.17 (14)	H6A—C6—H6C	109.5
C1—N2—H2n	117.2 (13)	H6B—C6—H6C	109.5
C7—N2—H2n	114.6 (13)	C8—C7—C12	118.64 (15)
N1—C1—N2	114.12 (15)	C8—C7—N2	117.97 (15)
N1—C1—C5	122.47 (15)	C12—C7—N2	123.27 (15)
N2—C1—C5	123.36 (15)	C9—C8—C7	120.91 (16)
N1—C2—C3	124.59 (18)	C9—C8—H8	119.5
N1—C2—H2	117.7	C7—C8—H8	119.5
C3—C2—H2	117.7	C10—C9—C8	119.40 (16)
C2—C3—C4	119.00 (16)	C10—C9—H9	120.3
C2—C3—H3	120.5	C8—C9—H9	120.3
C4—C3—H3	120.5	C11—C10—C9	120.77 (16)
C5—C4—C3	117.32 (16)	C11—C10—Cl1	119.67 (14)
C5—C4—C6	120.81 (17)	C9—C10—Cl1	119.55 (14)
C3—C4—C6	121.87 (16)	C10—C11—C12	119.99 (16)
C4—C5—C1	119.92 (16)	C10—C11—H11	120.0
C4—C5—H5	120.0	C12—C11—H11	120.0
C1—C5—H5	120.0	C11—C12—C7	120.28 (15)
C4—C6—H6A	109.5	C11—C12—H12	119.9
C4—C6—H6B	109.5	C7—C12—H12	119.9
H6A—C6—H6B	109.5
C2—N1—C1—N2	−177.70 (15)	C1—N2—C7—C8	−144.79 (18)
C2—N1—C1—C5	0.0 (2)	C1—N2—C7—C12	39.4 (3)
C7—N2—C1—N1	−167.92 (17)	C12—C7—C8—C9	0.6 (3)
C7—N2—C1—C5	14.4 (3)	N2—C7—C8—C9	−175.42 (16)
C1—N1—C2—C3	−0.7 (3)	C7—C8—C9—C10	−0.8 (3)
N1—C2—C3—C4	1.0 (3)	C8—C9—C10—C11	0.3 (3)
C2—C3—C4—C5	−0.6 (3)	C8—C9—C10—Cl1	−178.88 (14)
C2—C3—C4—C6	178.85 (18)	C9—C10—C11—C12	0.2 (3)
C3—C4—C5—C1	−0.1 (2)	Cl1—C10—C11—C12	179.44 (13)
C6—C4—C5—C1	−179.50 (17)	C10—C11—C12—C7	−0.4 (3)
N1—C1—C5—C4	0.4 (3)	C8—C7—C12—C11	−0.1 (2)
N2—C1—C5—C4	177.85 (16)	N2—C7—C12—C11	175.77 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···N1i	0.86 (1)	2.19 (1)	3.029 (2)	167 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯N1i	0.86 (1)	2.19 (1)	3.029 (2)	167 (2)

Symmetry code: (i) .