N-(Pyrazin-2-yl)aniline

Abstract

The two aromatic rings in the title compound, C₁₀H₉N₃, are inclined at 15.2 (1)° to each other; this opens up the angle at the amino N atom to 130.4 (1)°. The amino N atom forms a hydrogen bond to the 4-N atom of an adjacent mol­ecule to create a chain motif.

Related literature

For the structure of amino­pyrazine, see: Chao et al. (1976 ▶). For the structure of 2-pyrazinyl-N-2-nitro­phenyl­aniline; see: Parsons et al. (2006 ▶).

Experimental

Crystal data

• C₁₀H₉N₃

• M _r = 171.20

• Monoclinic,

• a = 11.0644 (3) Å

• b = 7.8423 (3) Å

• c = 10.8907 (3) Å

• β = 116.439 (2)°

• V = 846.15 (5) ų

• Z = 4

• Mo Kα radiation

• μ = 0.09 mm⁻¹

• T = 100 (2) K

• 0.20 × 0.10 × 0.05 mm

Data collection

• Bruker SMART APEX diffractometer

• Absorption correction: none

• 5664 measured reflections

• 1934 independent reflections

• 1463 reflections with I > 2σ(I)

• R _int = 0.033

Refinement

• R[F ² > 2σ(F ²)] = 0.041

• wR(F ²) = 0.101

• S = 1.03

• 1934 reflections

• 122 parameters

• 1 restraint

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.23 e Å⁻³

• Δρ_min = −0.23 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 ▶).

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.89 (1)	2.12 (1)	2.977 (2)	162 (1)

Symmetry code: (i) .

supplementary crystallographic information

Comment

There are few structural examples of pyrazine compounds having an amino substituent; these are limited to, for example, aminopyrazine (Chao et al., 1976) and pyrazinyl-N-2-nitrophenylaniline (Parsons et al., 2006). In the title compound (Scheme I, Fig. 1), the two aromatic rings are aligned at 15.2 (1)°; these open up the angle at the amino nitrogen to 130.4 (1) °. The amino nitrogen forms a hydrogen bond to the 4-nitrogen atom of an adjacent molecule to furnish a chain motif.

Experimental

Chloropyrazine (1 ml, 1.1 mmol) and aniline (1 ml, 1.1 mmol) were heated at 423–433 K for 3 h. The solid was dissolved in water. The compound was extracted with ether. The ether extract was dried over sodium sulfate; evaporation of the solvent gave a colorless crystals among some unidentified dark brown materials.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) fixed at 1.2U(C). The amino H-atom was located in a difference Fourier map, and was refined with a distance restraint of N—H 0.88 (1) Å.

Figures

Fig. 1.

Thermal ellipsoid plot (Barbour, 2001) of C10H9N3 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C10H9N3	F(000) = 360
Mr = 171.20	Dx = 1.344 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3723 reflections
a = 11.0644 (3) Å	θ = 3.3–26.4°
b = 7.8423 (3) Å	µ = 0.09 mm−1
c = 10.8907 (3) Å	T = 100 K
β = 116.439 (2)°	Prism, colourless
V = 846.15 (5) Å3	0.20 × 0.10 × 0.05 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer	1463 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
graphite	θmax = 27.5°, θmin = 3.3°
ω scans	h = −14→14
5664 measured reflections	k = −10→10
1934 independent reflections	l = −14→14

Refinement

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0421P)2 + 0.247P] where P = (Fo2 + 2Fc2)/3
1934 reflections	(Δ/σ)max = 0.001
122 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.23 e Å−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.36080 (11)	0.49391 (15)	0.56127 (12)	0.0188 (3)
H1	0.4485 (9)	0.479 (2)	0.6153 (13)	0.024 (4)*
N2	0.36741 (11)	0.89784 (15)	0.72193 (11)	0.0205 (3)
N3	0.18404 (11)	0.69151 (16)	0.51024 (12)	0.0221 (3)
C1	0.29407 (14)	0.36077 (18)	0.46992 (13)	0.0181 (3)
C2	0.37632 (14)	0.23785 (18)	0.45198 (14)	0.0201 (3)
H2	0.4717	0.2479	0.5007	0.024*
C3	0.32046 (15)	0.1019 (2)	0.36410 (15)	0.0246 (3)
H3	0.3775	0.0188	0.3534	0.029*
C4	0.18124 (15)	0.0862 (2)	0.29138 (15)	0.0255 (3)
H4	0.1427	−0.0058	0.2293	0.031*
C5	0.09930 (14)	0.20604 (19)	0.31037 (14)	0.0235 (3)
H5	0.0040	0.1948	0.2617	0.028*
C6	0.15425 (14)	0.34292 (18)	0.39962 (14)	0.0204 (3)
H6	0.0969	0.4236	0.4125	0.025*
C7	0.31216 (13)	0.64466 (17)	0.58462 (13)	0.0174 (3)
C8	0.40342 (13)	0.74982 (17)	0.69058 (14)	0.0184 (3)
H8	0.4941	0.7127	0.7412	0.022*
C9	0.23812 (14)	0.94629 (19)	0.64641 (14)	0.0232 (3)
H9	0.2078	1.0522	0.6649	0.028*
C10	0.14961 (14)	0.84350 (19)	0.54274 (15)	0.0245 (3)
H10	0.0594	0.8820	0.4914	0.029*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
N1	0.0140 (6)	0.0182 (6)	0.0186 (6)	0.0013 (5)	0.0023 (5)	−0.0019 (5)
N2	0.0201 (6)	0.0197 (6)	0.0210 (6)	−0.0006 (5)	0.0085 (5)	−0.0008 (5)
N3	0.0182 (6)	0.0214 (7)	0.0220 (6)	0.0020 (5)	0.0048 (5)	−0.0008 (5)
C1	0.0201 (7)	0.0171 (7)	0.0147 (6)	−0.0012 (5)	0.0057 (5)	0.0009 (5)
C2	0.0176 (7)	0.0223 (8)	0.0194 (7)	−0.0005 (6)	0.0074 (6)	0.0000 (6)
C3	0.0285 (8)	0.0227 (8)	0.0257 (8)	−0.0008 (6)	0.0150 (6)	−0.0045 (6)
C4	0.0286 (8)	0.0236 (8)	0.0233 (7)	−0.0072 (6)	0.0108 (6)	−0.0075 (6)
C5	0.0197 (7)	0.0251 (8)	0.0214 (7)	−0.0047 (6)	0.0051 (6)	−0.0003 (6)
C6	0.0189 (7)	0.0197 (7)	0.0194 (7)	−0.0005 (6)	0.0056 (6)	0.0008 (6)
C7	0.0180 (7)	0.0175 (7)	0.0164 (7)	−0.0003 (5)	0.0073 (5)	0.0019 (5)
C8	0.0155 (6)	0.0193 (7)	0.0187 (7)	0.0006 (5)	0.0060 (5)	0.0019 (5)
C9	0.0215 (7)	0.0211 (7)	0.0250 (7)	0.0039 (6)	0.0087 (6)	−0.0015 (6)
C10	0.0191 (7)	0.0237 (8)	0.0266 (8)	0.0058 (6)	0.0065 (6)	−0.0001 (6)

Geometric parameters (Å, °)

N1—C7	1.3689 (17)	C3—H3	0.9500
N1—C1	1.4039 (17)	C4—C5	1.384 (2)
N1—H1	0.891 (9)	C4—H4	0.9500
N2—C8	1.3207 (18)	C5—C6	1.393 (2)
N2—C9	1.3488 (17)	C5—H5	0.9500
N3—C7	1.3335 (17)	C6—H6	0.9500
N3—C10	1.3458 (19)	C7—C8	1.4120 (19)
C1—C6	1.3944 (18)	C8—H8	0.9500
C1—C2	1.3978 (19)	C9—C10	1.378 (2)
C2—C3	1.381 (2)	C9—H9	0.9500
C2—H2	0.9500	C10—H10	0.9500
C3—C4	1.389 (2)
C7—N1—C1	130.38 (12)	C4—C5—H5	119.5
C7—N1—H1	113.3 (10)	C6—C5—H5	119.5
C1—N1—H1	116.3 (10)	C5—C6—C1	119.56 (13)
C8—N2—C9	116.75 (12)	C5—C6—H6	120.2
C7—N3—C10	115.67 (12)	C1—C6—H6	120.2
C6—C1—C2	119.09 (13)	N3—C7—N1	121.64 (12)
C6—C1—N1	124.65 (13)	N3—C7—C8	121.03 (12)
C2—C1—N1	116.25 (12)	N1—C7—C8	117.32 (12)
C3—C2—C1	120.72 (13)	N2—C8—C7	122.44 (12)
C3—C2—H2	119.6	N2—C8—H8	118.8
C1—C2—H2	119.6	C7—C8—H8	118.8
C2—C3—C4	120.26 (14)	N2—C9—C10	120.58 (13)
C2—C3—H3	119.9	N2—C9—H9	119.7
C4—C3—H3	119.9	C10—C9—H9	119.7
C5—C4—C3	119.26 (14)	N3—C10—C9	123.53 (13)
C5—C4—H4	120.4	N3—C10—H10	118.2
C3—C4—H4	120.4	C9—C10—H10	118.2
C4—C5—C6	121.08 (13)
C7—N1—C1—C6	−12.7 (2)	C10—N3—C7—N1	−179.30 (12)
C7—N1—C1—C2	168.41 (13)	C10—N3—C7—C8	0.36 (19)
C6—C1—C2—C3	1.1 (2)	C1—N1—C7—N3	−4.2 (2)
N1—C1—C2—C3	−179.89 (12)	C1—N1—C7—C8	176.09 (13)
C1—C2—C3—C4	0.5 (2)	C9—N2—C8—C7	−0.73 (19)
C2—C3—C4—C5	−1.5 (2)	N3—C7—C8—N2	0.3 (2)
C3—C4—C5—C6	0.9 (2)	N1—C7—C8—N2	−179.99 (12)
C4—C5—C6—C1	0.7 (2)	C8—N2—C9—C10	0.4 (2)
C2—C1—C6—C5	−1.7 (2)	C7—N3—C10—C9	−0.7 (2)
N1—C1—C6—C5	179.40 (13)	N2—C9—C10—N3	0.3 (2)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.89 (1)	2.12 (1)	2.977 (2)	162 (1)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2.