4-Chloro-N-(2-pyrid­yl)aniline

Wan Saffiee, W.A.M.; Idris, A.; Aiyub, Z.; Abdullah, Z.; Ng, S.W.

doi:10.1107/S1600536808038658

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2437

doi:10.1107/S1600536808038658

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4-Chloro-N-(2-pyridyl)aniline

Wan Ainna Mardhiah Wan Saffiee,^a Azila Idris,^a Zaharah Aiyub,^a Zanariah Abdullah ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 18 November 2008; accepted 19 November 2008; online 26 November 2008)

There are two molecules in the asymmetric unit of the title compound, C₁₁H₉ClN₂, with dihedral angles of 41.84 (12) and 49.24 (12)° between the aromatic ring planes. The two molecules 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_r = 204.65
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.137
S = 1.00
4565 reflections
261 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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)

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038658/hb2855sup1.cif

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

checkCIF report

Comment top

For related structures, see: Abdullah & Ng (2008); Wan Saffiee et al. (2008). For the molecular structure of the title compound, (I), see Fig. 1. For hydrogen bond data, see Table 1.

Related literature top

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

Experimental top

2-Chloropyrazine (0.11 g, 0.1 mmol) and 4-chloroaniline (0.13 g, 0.1 mmol) were heated at 423–433 K for 5 h. The mixture was cooled and dissolved in water. The solution was extracted with ether. The ether extract was dried over sodium sulfate and the solvent evaporated to yield a dark brown compound. Colourless rods of (I) were separated manually.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

Fig. 1. The molecular structure of (I) drawn at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

4-Chloro-N-(2-pyridyl)aniline top

Crystal data top

C₁₁H₉ClN₂	F(000) = 848
M_r = 204.65	D_x = 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 = 2.4–21.4°
b = 7.5519 (2) Å	µ = 0.34 mm⁻¹
c = 17.6846 (4) Å	T = 296 K
β = 106.284 (2)°	Rod, colourless
V = 1988.25 (9) Å³	0.42 × 0.06 × 0.03 mm
Z = 8

Data collection top

Bruker SMART APEX CCD diffractometer	4565 independent reflections
Radiation source: fine-focus sealed tube	2369 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
T_min = 0.870, T_max = 0.990	k = −9→9
18472 measured reflections	l = −22→22

Refinement top

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0544P)² + 0.3184P] where P = (F_o² + 2F_c²)/3
4565 reflections	(Δ/σ)_max = 0.001
261 parameters	Δρ_max = 0.15 e Å⁻³
2 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₁H₉ClN₂	V = 1988.25 (9) Å³
M_r = 204.65	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.5096 (4) Å	µ = 0.34 mm⁻¹
b = 7.5519 (2) Å	T = 296 K
c = 17.6846 (4) Å	0.42 × 0.06 × 0.03 mm
β = 106.284 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	4565 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2369 reflections with I > 2σ(I)
T_min = 0.870, T_max = 0.990	R_int = 0.041
18472 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	2 restraints
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.15 e Å⁻³
4565 reflections	Δρ_min = −0.24 e Å⁻³
261 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₁H₉ClN₂
M_r	204.65
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	15.5096 (4), 7.5519 (2), 17.6846 (4)
β (°)	106.284 (2)
V (Å³)	1988.25 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.42 × 0.06 × 0.03

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.870, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	18472, 4565, 2369
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.137, 1.00
No. of reflections	4565
No. of parameters	261
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.24

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

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)

Acknowledgements

We thank the University of Malaya for supporting this study (grant No. PS205/2008 A).

References

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