N-(Pyrazin-2-yl)aniline.

The two aromatic rings in the title compound, C(10)H(9)N(3), 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 mol-ecule 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 = 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) Å3

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

Δρmax = 0.23 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808031942/pk2121sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031942/pk2121Isup2.hkl

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

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

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 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

	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*

	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)

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)

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)

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) .