4-Chloro-N-(2-pyrid-yl)aniline.

There are two mol-ecules in the asymmetric unit of the title compound, C(11)H(9)ClN(2), with dihedral angles of 41.84 (12) and 49.24 (12)° between the aromatic ring planes. The two mol-ecules form a dimer via a pair of N-H⋯N hydrogen bonds.

Related literature

For the structures of the two modifications of N-(pyrazin-2-yl)aniline, see: Abdullah & Ng (2008 ▶); Wan Saffiee et al. (2008 ▶).

Experimental

Crystal data

C11H9ClN2

M = 204.65

Monoclinic,

a = 15.5096 (4) Å

b = 7.5519 (2) Å

c = 17.6846 (4) Å

β = 106.284 (2)°

V = 1988.25 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.34 mm−1

T = 296 (2) K

0.42 × 0.06 × 0.03 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.870, T max = 0.990

18472 measured reflections

4565 independent reflections

2369 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.137

S = 1.00

4565 reflections

261 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.24 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/S1600536808038658/hb2855sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038658/hb2855Isup2.hkl

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

C11H9ClN2	F000 = 848
Mr = 204.65	Dx = 1.367 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2114 reflections
a = 15.5096 (4) Å	θ = 2.4–21.4º
b = 7.5519 (2) Å	µ = 0.34 mm−1
c = 17.6846 (4) Å	T = 296 (2) K
β = 106.284 (2)º	Rod, colourless
V = 1988.25 (9) Å3	0.42 × 0.06 × 0.03 mm
Z = 8

Bruker SMART APEX CCD diffractometer	4565 independent reflections
Radiation source: fine-focus sealed tube	2369 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.041
T = 100(2) K	θmax = 27.5º
ω scans	θmin = 1.6º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)	h = −20→20
Tmin = 0.870, Tmax = 0.990	k = −9→9
18472 measured reflections	l = −22→22

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.3184P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
4565 reflections	Δρmax = 0.15 e Å−3
261 parameters	Δρmin = −0.24 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
Cl1	0.67109 (6)	0.86166 (11)	0.13818 (4)	0.0915 (3)
Cl2	0.52605 (6)	0.65436 (13)	0.94056 (4)	0.1027 (3)
N1	0.67429 (13)	0.7765 (3)	0.47124 (11)	0.0625 (5)
H1	0.6219 (9)	0.782 (3)	0.4794 (14)	0.074 (8)*
N2	0.72018 (12)	0.7057 (3)	0.60159 (11)	0.0625 (5)
N3	0.52408 (13)	0.6934 (3)	0.60693 (11)	0.0651 (6)
H3	0.5772 (9)	0.691 (3)	0.6004 (13)	0.064 (7)*
N4	0.48220 (12)	0.7816 (3)	0.47849 (11)	0.0634 (5)
C1	0.78370 (17)	0.6465 (4)	0.66437 (14)	0.0710 (7)
H1A	0.7688	0.6375	0.7116	0.085*
C2	0.86856 (17)	0.5984 (4)	0.66472 (15)	0.0743 (8)
H2	0.9099	0.5571	0.7102	0.089*
C3	0.89013 (16)	0.6137 (3)	0.59455 (15)	0.0693 (7)
H3A	0.9473	0.5828	0.5921	0.083*
C4	0.82822 (15)	0.6738 (3)	0.52878 (14)	0.0614 (6)
H4	0.8425	0.6842	0.4813	0.074*
C5	0.74264 (14)	0.7197 (3)	0.53411 (13)	0.0528 (6)
C6	0.67699 (14)	0.7960 (3)	0.39292 (12)	0.0517 (5)
C7	0.74402 (15)	0.8895 (3)	0.37290 (14)	0.0626 (6)
H7	0.7902	0.9407	0.4122	0.075*
C8	0.74268 (16)	0.9074 (3)	0.29468 (15)	0.0648 (7)
H8	0.7889	0.9670	0.2815	0.078*
C9	0.67292 (17)	0.8368 (3)	0.23664 (14)	0.0590 (6)
C10	0.60499 (15)	0.7467 (3)	0.25551 (13)	0.0571 (6)
H10	0.5576	0.7003	0.2160	0.069*
C11	0.60754 (14)	0.7255 (3)	0.33346 (13)	0.0532 (6)
H11	0.5619	0.6630	0.3463	0.064*
C12	0.41850 (17)	0.8195 (4)	0.41237 (14)	0.0756 (8)
H12	0.4368	0.8569	0.3692	0.091*
C13	0.32900 (18)	0.8074 (4)	0.40351 (15)	0.0787 (8)
H13	0.2873	0.8389	0.3565	0.094*
C14	0.30224 (16)	0.7468 (4)	0.46686 (15)	0.0747 (8)
H14	0.2415	0.7335	0.4628	0.090*
C15	0.36502 (15)	0.7066 (3)	0.53537 (14)	0.0654 (7)
H15	0.3478	0.6647	0.5784	0.078*
C16	0.45526 (14)	0.7290 (3)	0.54015 (13)	0.0546 (6)
C17	0.52001 (13)	0.6854 (3)	0.68456 (12)	0.0504 (5)
C18	0.45807 (15)	0.7767 (3)	0.71257 (13)	0.0573 (6)
H18	0.4151	0.8470	0.6784	0.069*
C19	0.45919 (16)	0.7647 (3)	0.79053 (14)	0.0614 (6)
H19	0.4161	0.8238	0.8084	0.074*
C20	0.52424 (16)	0.6652 (3)	0.84200 (13)	0.0601 (6)
C21	0.58698 (15)	0.5743 (3)	0.81581 (13)	0.0592 (6)
H21	0.6308	0.5071	0.8507	0.071*
C22	0.58459 (14)	0.5833 (3)	0.73756 (13)	0.0559 (6)
H22	0.6266	0.5205	0.7197	0.067*

	U11	U22	U33	U12	U13	U23
Cl1	0.1128 (6)	0.1099 (6)	0.0642 (4)	0.0274 (5)	0.0455 (4)	0.0168 (4)
Cl2	0.1127 (6)	0.1427 (8)	0.0617 (4)	0.0110 (5)	0.0395 (4)	0.0276 (4)
N1	0.0442 (11)	0.0929 (16)	0.0500 (11)	0.0058 (11)	0.0123 (10)	0.0067 (10)
N2	0.0496 (11)	0.0902 (15)	0.0470 (11)	−0.0002 (10)	0.0125 (9)	−0.0015 (10)
N3	0.0437 (11)	0.1038 (17)	0.0470 (11)	0.0070 (11)	0.0112 (9)	0.0061 (10)
N4	0.0528 (11)	0.0867 (15)	0.0499 (12)	0.0078 (10)	0.0132 (10)	0.0019 (10)
C1	0.0581 (15)	0.104 (2)	0.0467 (14)	−0.0025 (15)	0.0082 (12)	0.0000 (13)
C2	0.0530 (15)	0.101 (2)	0.0594 (16)	0.0018 (14)	0.0003 (12)	0.0038 (14)
C3	0.0453 (13)	0.0847 (19)	0.0717 (17)	0.0065 (13)	0.0062 (13)	−0.0064 (14)
C4	0.0501 (13)	0.0802 (18)	0.0535 (14)	0.0011 (12)	0.0136 (11)	−0.0050 (12)
C5	0.0437 (12)	0.0622 (14)	0.0499 (13)	−0.0034 (11)	0.0086 (11)	−0.0051 (11)
C6	0.0444 (12)	0.0614 (14)	0.0502 (13)	0.0000 (11)	0.0146 (10)	0.0030 (11)
C7	0.0509 (14)	0.0699 (16)	0.0649 (15)	−0.0099 (12)	0.0126 (12)	0.0014 (12)
C8	0.0565 (14)	0.0664 (16)	0.0782 (17)	−0.0024 (12)	0.0301 (13)	0.0124 (13)
C9	0.0627 (15)	0.0628 (16)	0.0556 (14)	0.0137 (12)	0.0231 (12)	0.0072 (11)
C10	0.0489 (13)	0.0655 (16)	0.0547 (14)	0.0020 (11)	0.0107 (11)	−0.0056 (11)
C11	0.0438 (12)	0.0596 (14)	0.0575 (14)	−0.0017 (11)	0.0162 (11)	0.0015 (11)
C12	0.0645 (17)	0.111 (2)	0.0505 (15)	0.0178 (15)	0.0148 (13)	0.0093 (14)
C13	0.0578 (16)	0.119 (2)	0.0516 (15)	0.0208 (16)	0.0031 (13)	0.0020 (15)
C14	0.0464 (14)	0.102 (2)	0.0685 (17)	0.0002 (14)	0.0049 (13)	−0.0065 (15)
C15	0.0488 (13)	0.0883 (18)	0.0560 (14)	−0.0067 (13)	0.0097 (11)	0.0019 (13)
C16	0.0478 (13)	0.0647 (15)	0.0496 (13)	0.0051 (11)	0.0106 (11)	−0.0018 (11)
C17	0.0384 (11)	0.0631 (14)	0.0489 (13)	−0.0045 (10)	0.0108 (10)	0.0009 (10)
C18	0.0499 (13)	0.0631 (15)	0.0555 (14)	0.0051 (11)	0.0094 (11)	0.0066 (11)
C19	0.0562 (14)	0.0704 (17)	0.0622 (15)	0.0023 (12)	0.0244 (12)	0.0011 (12)
C20	0.0603 (15)	0.0692 (16)	0.0526 (14)	−0.0064 (13)	0.0186 (12)	0.0107 (12)
C21	0.0486 (13)	0.0677 (16)	0.0586 (14)	−0.0023 (12)	0.0104 (11)	0.0153 (12)
C22	0.0420 (12)	0.0654 (15)	0.0585 (14)	0.0008 (11)	0.0114 (11)	0.0029 (11)

Cl1—C9	1.744 (2)	C8—C9	1.373 (3)
Cl2—C20	1.737 (2)	C8—H8	0.9300
N1—C5	1.372 (3)	C9—C10	1.371 (3)
N1—C6	1.405 (3)	C10—C11	1.377 (3)
N1—H1	0.865 (10)	C10—H10	0.9300
N2—C1	1.338 (3)	C11—H11	0.9300
N2—C5	1.338 (3)	C12—C13	1.356 (3)
N3—C16	1.378 (3)	C12—H12	0.9300
N3—C17	1.393 (3)	C13—C14	1.378 (3)
N3—H3	0.863 (9)	C13—H13	0.9300
N4—C12	1.333 (3)	C14—C15	1.359 (3)
N4—C16	1.333 (3)	C14—H14	0.9300
C1—C2	1.364 (3)	C15—C16	1.389 (3)
C1—H1A	0.9300	C15—H15	0.9300
C2—C3	1.378 (3)	C17—C18	1.382 (3)
C2—H2	0.9300	C17—C22	1.396 (3)
C3—C4	1.362 (3)	C18—C19	1.377 (3)
C3—H3A	0.9300	C18—H18	0.9300
C4—C5	1.400 (3)	C19—C20	1.377 (3)
C4—H4	0.9300	C19—H19	0.9300
C6—C7	1.382 (3)	C20—C21	1.373 (3)
C6—C11	1.383 (3)	C21—C22	1.376 (3)
C7—C8	1.384 (3)	C21—H21	0.9300
C7—H7	0.9300	C22—H22	0.9300
C5—N1—C6	127.0 (2)	C11—C10—H10	120.2
C5—N1—H1	115.4 (16)	C10—C11—C6	120.9 (2)
C6—N1—H1	116.6 (16)	C10—C11—H11	119.5
C1—N2—C5	116.8 (2)	C6—C11—H11	119.5
C16—N3—C17	127.9 (2)	N4—C12—C13	124.7 (2)
C16—N3—H3	115.4 (15)	N4—C12—H12	117.6
C17—N3—H3	116.0 (15)	C13—C12—H12	117.6
C12—N4—C16	117.2 (2)	C12—C13—C14	117.4 (2)
N2—C1—C2	125.3 (2)	C12—C13—H13	121.3
N2—C1—H1A	117.3	C14—C13—H13	121.3
C2—C1—H1A	117.3	C15—C14—C13	119.7 (2)
C1—C2—C3	116.8 (2)	C15—C14—H14	120.2
C1—C2—H2	121.6	C13—C14—H14	120.2
C3—C2—H2	121.6	C14—C15—C16	119.0 (2)
C4—C3—C2	120.4 (2)	C14—C15—H15	120.5
C4—C3—H3A	119.8	C16—C15—H15	120.5
C2—C3—H3A	119.8	N4—C16—N3	114.45 (19)
C3—C4—C5	118.7 (2)	N4—C16—C15	121.9 (2)
C3—C4—H4	120.7	N3—C16—C15	123.6 (2)
C5—C4—H4	120.7	C18—C17—N3	124.0 (2)
N2—C5—N1	114.34 (19)	C18—C17—C22	118.3 (2)
N2—C5—C4	122.0 (2)	N3—C17—C22	117.6 (2)
N1—C5—C4	123.7 (2)	C19—C18—C17	120.7 (2)
C7—C6—C11	118.9 (2)	C19—C18—H18	119.6
C7—C6—N1	122.6 (2)	C17—C18—H18	119.6
C11—C6—N1	118.5 (2)	C18—C19—C20	119.9 (2)
C6—C7—C8	120.3 (2)	C18—C19—H19	120.0
C6—C7—H7	119.9	C20—C19—H19	120.0
C8—C7—H7	119.9	C21—C20—C19	120.5 (2)
C9—C8—C7	119.8 (2)	C21—C20—Cl2	120.07 (18)
C9—C8—H8	120.1	C19—C20—Cl2	119.5 (2)
C7—C8—H8	120.1	C20—C21—C22	119.5 (2)
C10—C9—C8	120.6 (2)	C20—C21—H21	120.2
C10—C9—Cl1	119.87 (19)	C22—C21—H21	120.2
C8—C9—Cl1	119.55 (19)	C21—C22—C17	121.0 (2)
C9—C10—C11	119.5 (2)	C21—C22—H22	119.5
C9—C10—H10	120.2	C17—C22—H22	119.5
C5—N2—C1—C2	−0.6 (4)	C16—N4—C12—C13	−0.4 (4)
N2—C1—C2—C3	0.5 (4)	N4—C12—C13—C14	−1.9 (5)
C1—C2—C3—C4	−0.3 (4)	C12—C13—C14—C15	1.8 (4)
C2—C3—C4—C5	0.1 (4)	C13—C14—C15—C16	0.5 (4)
C1—N2—C5—N1	178.4 (2)	C12—N4—C16—N3	−179.4 (2)
C1—N2—C5—C4	0.3 (3)	C12—N4—C16—C15	2.8 (4)
C6—N1—C5—N2	−177.0 (2)	C17—N3—C16—N4	160.2 (2)
C6—N1—C5—C4	0.9 (4)	C17—N3—C16—C15	−22.0 (4)
C3—C4—C5—N2	−0.1 (4)	C14—C15—C16—N4	−2.9 (4)
C3—C4—C5—N1	−177.9 (2)	C14—C15—C16—N3	179.5 (2)
C5—N1—C6—C7	−51.1 (4)	C16—N3—C17—C18	−26.8 (4)
C5—N1—C6—C11	131.9 (3)	C16—N3—C17—C22	155.4 (2)
C11—C6—C7—C8	−1.9 (3)	N3—C17—C18—C19	−178.8 (2)
N1—C6—C7—C8	−178.9 (2)	C22—C17—C18—C19	−1.1 (3)
C6—C7—C8—C9	2.1 (4)	C17—C18—C19—C20	2.0 (4)
C7—C8—C9—C10	−0.8 (4)	C18—C19—C20—C21	−1.5 (4)
C7—C8—C9—Cl1	179.35 (19)	C18—C19—C20—Cl2	178.90 (18)
C8—C9—C10—C11	−0.7 (3)	C19—C20—C21—C22	0.1 (3)
Cl1—C9—C10—C11	179.13 (17)	Cl2—C20—C21—C22	179.70 (18)
C9—C10—C11—C6	0.9 (3)	C20—C21—C22—C17	0.8 (3)
C7—C6—C11—C10	0.4 (3)	C18—C17—C22—C21	−0.4 (3)
N1—C6—C11—C10	177.5 (2)	N3—C17—C22—C21	177.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4	0.87 (1)	2.16 (1)	3.018 (3)	170 (2)
N3—H3···N2	0.86 (1)	2.22 (1)	3.071 (3)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N4	0.87 (1)	2.16 (1)	3.018 (3)	170 (2)
N3—H3⋯N2	0.86 (1)	2.22 (1)	3.071 (3)	171 (2)