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

The two aromatic rings in the title compound, C(10)H(8)ClN(3), open the angle at the planar N atom to 128.00 (12)°. The amino N atom of one mol-ecule forms a hydrogen bond to the 1-N atom of an adjacent pyrimidyl ring, generating a hydrogen-bonded dimer.

Related literature

For other 4-chloro­anilino substituted N-heterocycles, see: Fairuz et al. (2008 ▶); Idris et al. (2008 ▶).

Experimental

Crystal data

C10H8ClN3

M = 205.64

Triclinic,

a = 3.7750 (1) Å

b = 10.0589 (3) Å

c = 12.0116 (3) Å

α = 89.237 (1)°

β = 89.037 (1)°

γ = 89.399 (2)°

V = 455.98 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 100 (2) K

0.35 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.880, T max = 0.982

3625 measured reflections

2032 independent reflections

1757 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.080

S = 1.02

2032 reflections

131 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041184/tk2341sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041184/tk2341Isup2.hkl

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

C10H8ClN3	Z = 2
Mr = 205.64	F(000) = 212
Triclinic, P1	Dx = 1.498 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 3.7750 (1) Å	Cell parameters from 2160 reflections
b = 10.0589 (3) Å	θ = 2.6–28.2°
c = 12.0116 (3) Å	µ = 0.38 mm−1
α = 89.237 (1)°	T = 100 K
β = 89.037 (1)°	Plate, yellow
γ = 89.399 (2)°	0.35 × 0.15 × 0.05 mm
V = 455.98 (2) Å3

Bruker SMART APEX diffractometer	2032 independent reflections
Radiation source: fine-focus sealed tube	1757 reflections with I > 2σ(I)
graphite	Rint = 0.014
ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→4
Tmin = 0.880, Tmax = 0.982	k = −13→13
3625 measured reflections	l = −14→15

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0319P)2 + 0.3201P] where P = (Fo2 + 2Fc2)/3
2032 reflections	(Δ/σ)max = 0.001
131 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	1.12780 (11)	0.77439 (4)	1.04792 (3)	0.02641 (13)
N1	0.6990 (3)	0.63747 (13)	0.59185 (10)	0.0156 (3)
H1	0.642 (5)	0.556 (2)	0.5875 (16)	0.028 (5)*
N2	0.5390 (3)	0.64905 (12)	0.40908 (10)	0.0150 (3)
N3	0.7907 (3)	0.83808 (12)	0.49717 (10)	0.0156 (3)
C1	0.8101 (4)	0.67719 (14)	0.69743 (11)	0.0136 (3)
C2	0.7505 (4)	0.80454 (15)	0.73923 (11)	0.0156 (3)
H2	0.6416	0.8710	0.6941	0.019*
C3	0.8504 (4)	0.83405 (15)	0.84683 (12)	0.0178 (3)
H3	0.8117	0.9208	0.8752	0.021*
C4	1.0064 (4)	0.73655 (16)	0.91245 (11)	0.0172 (3)
C5	1.0687 (4)	0.60984 (15)	0.87278 (12)	0.0175 (3)
H5	1.1767	0.5436	0.9184	0.021*
C6	0.9703 (4)	0.58131 (15)	0.76498 (12)	0.0156 (3)
H6	1.0131	0.4947	0.7368	0.019*
C7	0.6752 (4)	0.71254 (14)	0.49723 (11)	0.0132 (3)
C8	0.7695 (4)	0.90471 (14)	0.40058 (12)	0.0156 (3)
H8	0.8469	0.9943	0.3975	0.019*
C9	0.6401 (4)	0.84960 (15)	0.30478 (12)	0.0165 (3)
H9	0.6296	0.8981	0.2365	0.020*
C10	0.5268 (4)	0.71961 (15)	0.31431 (11)	0.0159 (3)
H10	0.4358	0.6785	0.2502	0.019*

	U11	U22	U33	U12	U13	U23
Cl1	0.0288 (2)	0.0384 (2)	0.01228 (18)	−0.00173 (17)	−0.00450 (14)	−0.00490 (15)
N1	0.0213 (7)	0.0124 (6)	0.0133 (6)	−0.0040 (5)	−0.0022 (5)	−0.0008 (5)
N2	0.0171 (6)	0.0139 (6)	0.0141 (6)	−0.0007 (5)	−0.0017 (5)	−0.0020 (4)
N3	0.0169 (6)	0.0151 (6)	0.0146 (6)	−0.0028 (5)	0.0002 (5)	−0.0010 (5)
C1	0.0129 (6)	0.0158 (7)	0.0121 (6)	−0.0037 (5)	0.0005 (5)	−0.0004 (5)
C2	0.0173 (7)	0.0159 (7)	0.0136 (6)	−0.0006 (5)	0.0002 (5)	0.0005 (5)
C3	0.0184 (7)	0.0185 (7)	0.0164 (7)	−0.0019 (6)	0.0022 (5)	−0.0043 (5)
C4	0.0152 (7)	0.0260 (8)	0.0103 (6)	−0.0035 (6)	0.0003 (5)	−0.0020 (5)
C5	0.0141 (7)	0.0224 (8)	0.0158 (7)	−0.0005 (6)	0.0003 (5)	0.0030 (6)
C6	0.0153 (7)	0.0154 (7)	0.0162 (7)	−0.0012 (5)	0.0016 (5)	−0.0009 (5)
C7	0.0118 (6)	0.0145 (7)	0.0133 (6)	0.0001 (5)	0.0007 (5)	−0.0018 (5)
C8	0.0159 (7)	0.0138 (7)	0.0170 (7)	−0.0013 (5)	0.0017 (5)	−0.0001 (5)
C9	0.0182 (7)	0.0177 (7)	0.0135 (6)	0.0008 (6)	0.0004 (5)	0.0012 (5)
C10	0.0161 (7)	0.0180 (7)	0.0136 (6)	0.0010 (5)	−0.0019 (5)	−0.0030 (5)

Cl1—C4	1.7458 (14)	C3—C4	1.383 (2)
N1—C7	1.3599 (18)	C3—H3	0.9500
N1—C1	1.4067 (17)	C4—C5	1.383 (2)
N1—H1	0.85 (2)	C5—C6	1.3875 (19)
N2—C10	1.3346 (18)	C5—H5	0.9500
N2—C7	1.3552 (17)	C6—H6	0.9500
N3—C8	1.3353 (18)	C8—C9	1.383 (2)
N3—C7	1.3404 (18)	C8—H8	0.9500
C1—C6	1.392 (2)	C9—C10	1.383 (2)
C1—C2	1.397 (2)	C9—H9	0.9500
C2—C3	1.3890 (19)	C10—H10	0.9500
C2—H2	0.9500
C7—N1—C1	128.00 (12)	C4—C5—H5	120.7
C7—N1—H1	116.9 (14)	C6—C5—H5	120.7
C1—N1—H1	115.1 (14)	C5—C6—C1	121.22 (13)
C10—N2—C7	115.63 (12)	C5—C6—H6	119.4
C8—N3—C7	116.05 (12)	C1—C6—H6	119.4
C6—C1—C2	119.06 (13)	N3—C7—N2	125.91 (13)
C6—C1—N1	117.44 (13)	N3—C7—N1	119.22 (12)
C2—C1—N1	123.41 (13)	N2—C7—N1	114.85 (12)
C3—C2—C1	120.03 (14)	N3—C8—C9	123.14 (13)
C3—C2—H2	120.0	N3—C8—H8	118.4
C1—C2—H2	120.0	C9—C8—H8	118.4
C4—C3—C2	119.69 (14)	C10—C9—C8	115.99 (13)
C4—C3—H3	120.2	C10—C9—H9	122.0
C2—C3—H3	120.2	C8—C9—H9	122.0
C5—C4—C3	121.30 (13)	N2—C10—C9	123.27 (13)
C5—C4—Cl1	119.40 (12)	N2—C10—H10	118.4
C3—C4—Cl1	119.31 (12)	C9—C10—H10	118.4
C4—C5—C6	118.70 (14)
C7—N1—C1—C6	−150.50 (14)	N1—C1—C6—C5	−176.11 (13)
C7—N1—C1—C2	33.1 (2)	C8—N3—C7—N2	−0.4 (2)
C6—C1—C2—C3	−0.1 (2)	C8—N3—C7—N1	178.01 (13)
N1—C1—C2—C3	176.32 (13)	C10—N2—C7—N3	1.0 (2)
C1—C2—C3—C4	−0.5 (2)	C10—N2—C7—N1	−177.43 (13)
C2—C3—C4—C5	0.6 (2)	C1—N1—C7—N3	5.1 (2)
C2—C3—C4—Cl1	−179.51 (11)	C1—N1—C7—N2	−176.27 (13)
C3—C4—C5—C6	−0.2 (2)	C7—N3—C8—C9	−0.6 (2)
Cl1—C4—C5—C6	179.93 (11)	N3—C8—C9—C10	0.8 (2)
C4—C5—C6—C1	−0.4 (2)	C7—N2—C10—C9	−0.7 (2)
C2—C1—C6—C5	0.5 (2)	C8—C9—C10—N2	−0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.85 (2)	2.18 (2)	3.028 (2)	174 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.85 (2)	2.18 (2)	3.028 (2)	174 (2)

Symmetry code: (i) .