A second monoclinic polymorph of N-(pyrazin-2-yl)aniline.

The two aromatic rings in the title compound, C(10)H(9)N(3), are aligned at 23.4 (1)° and the bridging C-N-C angle is 128.9 (1)°. In the crystal structure, intermolecular N-H⋯N hydrogen bonds result in a chain motif, the repeat distance of which is half the b axial length of 8.8851 (3) Å.

Related literature

In the P21/c modification, the aromatic rings are aligned at 15.2 (1)°, and the repeat distance of the helical chain is half the b-axial length of 7.8423 (3) Å; see: Wan Saffiee et al. (2008 ▶).

Experimental

Crystal data

C10H9N3

M = 171.20

Monoclinic,

a = 8.2194 (3) Å

b = 8.8851 (3) Å

c = 11.8395 (4) Å

β = 104.643 (2)°

V = 836.56 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 (2) K

0.25 × 0.05 × 0.03 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

7621 measured reflections

1922 independent reflections

1389 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.113

S = 1.03

1922 reflections

122 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 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/S1600536808031954/pk2124sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031954/pk2124Isup2.hkl

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

C10H9N3	F(000) = 360
Mr = 171.20	Dx = 1.359 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1282 reflections
a = 8.2194 (3) Å	θ = 2.7–26.1°
b = 8.8851 (3) Å	µ = 0.09 mm−1
c = 11.8395 (4) Å	T = 100 K
β = 104.643 (2)°	Prism, pale yellow
V = 836.56 (5) Å3	0.25 × 0.05 × 0.03 mm
Z = 4

Bruker SMART APEX diffractometer	1389 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
graphite	θmax = 27.5°, θmin = 2.7°
ω scans	h = −10→10
7621 measured reflections	k = −11→11
1922 independent reflections	l = −15→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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0547P)2 + 0.1331P] where P = (Fo2 + 2Fc2)/3
1922 reflections	(Δ/σ)max = 0.001
122 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

	x	y	z	Uiso*/Ueq
N1	1.00115 (16)	0.42084 (14)	0.63143 (11)	0.0216 (3)
H1	1.103 (2)	0.377 (2)	0.6527 (15)	0.035 (5)*
N2	0.84988 (15)	0.63197 (14)	0.66840 (11)	0.0230 (3)
N3	1.15770 (16)	0.76478 (14)	0.78284 (11)	0.0228 (3)
C1	0.86787 (18)	0.33136 (16)	0.56827 (12)	0.0193 (3)
C2	0.89595 (19)	0.17682 (17)	0.56499 (13)	0.0254 (4)
H2	1.0021	0.1367	0.6049	0.030*
C3	0.7717 (2)	0.08147 (17)	0.50462 (14)	0.0264 (4)
H3	0.7933	−0.0235	0.5030	0.032*
C4	0.61582 (19)	0.13750 (17)	0.44633 (13)	0.0232 (3)
H4	0.5296	0.0717	0.4058	0.028*
C5	0.58777 (19)	0.29106 (17)	0.44814 (13)	0.0222 (3)
H5	0.4815	0.3305	0.4079	0.027*
C6	0.71238 (18)	0.38836 (16)	0.50783 (13)	0.0211 (3)
H6	0.6916	0.4936	0.5074	0.025*
C7	0.99583 (18)	0.56191 (16)	0.67668 (13)	0.0192 (3)
C8	1.14967 (18)	0.63040 (16)	0.73478 (13)	0.0213 (3)
H8	1.2514	0.5772	0.7393	0.026*
C9	1.00948 (18)	0.83515 (18)	0.77382 (13)	0.0248 (4)
H9	1.0085	0.9325	0.8069	0.030*
C10	0.8604 (2)	0.76892 (17)	0.71788 (14)	0.0254 (4)
H10	0.7592	0.8226	0.7139	0.030*

	U11	U22	U33	U12	U13	U23
N1	0.0144 (7)	0.0200 (7)	0.0276 (7)	0.0019 (5)	0.0003 (5)	−0.0014 (5)
N2	0.0173 (6)	0.0230 (7)	0.0272 (7)	0.0004 (5)	0.0027 (5)	−0.0036 (5)
N3	0.0195 (7)	0.0228 (7)	0.0251 (7)	−0.0033 (5)	0.0037 (5)	−0.0011 (5)
C1	0.0180 (7)	0.0205 (7)	0.0193 (7)	−0.0010 (6)	0.0048 (6)	−0.0009 (6)
C2	0.0217 (8)	0.0227 (8)	0.0289 (8)	0.0040 (6)	0.0012 (6)	0.0000 (6)
C3	0.0293 (9)	0.0176 (8)	0.0307 (9)	0.0005 (6)	0.0043 (7)	−0.0019 (6)
C4	0.0217 (8)	0.0233 (8)	0.0244 (8)	−0.0059 (6)	0.0053 (6)	−0.0035 (6)
C5	0.0173 (7)	0.0251 (8)	0.0229 (8)	0.0005 (6)	0.0026 (6)	−0.0006 (6)
C6	0.0195 (8)	0.0190 (7)	0.0237 (8)	0.0005 (6)	0.0031 (6)	−0.0011 (6)
C7	0.0175 (7)	0.0198 (7)	0.0194 (7)	0.0004 (6)	0.0030 (6)	0.0020 (6)
C8	0.0177 (7)	0.0224 (8)	0.0233 (8)	−0.0001 (6)	0.0041 (6)	0.0015 (6)
C9	0.0228 (8)	0.0220 (8)	0.0284 (8)	−0.0016 (6)	0.0047 (6)	−0.0049 (6)
C10	0.0202 (8)	0.0241 (8)	0.0307 (9)	0.0032 (6)	0.0043 (6)	−0.0041 (7)

N1—C7	1.3681 (19)	C3—H3	0.9500
N1—C1	1.4061 (19)	C4—C5	1.385 (2)
N1—H1	0.897 (18)	C4—H4	0.9500
N2—C7	1.3330 (18)	C5—C6	1.389 (2)
N2—C10	1.3438 (19)	C5—H5	0.9500
N3—C8	1.3171 (19)	C6—H6	0.9500
N3—C9	1.3494 (19)	C7—C8	1.415 (2)
C1—C6	1.393 (2)	C8—H8	0.9500
C1—C2	1.395 (2)	C9—C10	1.370 (2)
C2—C3	1.379 (2)	C9—H9	0.9500
C2—H2	0.9500	C10—H10	0.9500
C3—C4	1.385 (2)
C7—N1—C1	128.94 (13)	C4—C5—H5	119.4
C7—N1—H1	114.0 (12)	C6—C5—H5	119.4
C1—N1—H1	116.7 (11)	C5—C6—C1	119.86 (14)
C7—N2—C10	115.67 (13)	C5—C6—H6	120.1
C8—N3—C9	116.12 (13)	C1—C6—H6	120.1
C6—C1—C2	118.72 (13)	N2—C7—N1	121.09 (13)
C6—C1—N1	123.92 (13)	N2—C7—C8	120.79 (13)
C2—C1—N1	117.35 (13)	N1—C7—C8	118.11 (13)
C3—C2—C1	120.88 (14)	N3—C8—C7	122.74 (13)
C3—C2—H2	119.6	N3—C8—H8	118.6
C1—C2—H2	119.6	C7—C8—H8	118.6
C2—C3—C4	120.52 (14)	N3—C9—C10	121.23 (14)
C2—C3—H3	119.7	N3—C9—H9	119.4
C4—C3—H3	119.7	C10—C9—H9	119.4
C5—C4—C3	118.88 (14)	N2—C10—C9	123.44 (14)
C5—C4—H4	120.6	N2—C10—H10	118.3
C3—C4—H4	120.6	C9—C10—H10	118.3
C4—C5—C6	121.11 (14)
C7—N1—C1—C6	21.9 (2)	C10—N2—C7—N1	178.88 (14)
C7—N1—C1—C2	−159.27 (15)	C10—N2—C7—C8	0.2 (2)
C6—C1—C2—C3	−1.0 (2)	C1—N1—C7—N2	2.9 (2)
N1—C1—C2—C3	−179.81 (14)	C1—N1—C7—C8	−178.36 (14)
C1—C2—C3—C4	−0.3 (2)	C9—N3—C8—C7	0.0 (2)
C2—C3—C4—C5	1.0 (2)	N2—C7—C8—N3	−0.2 (2)
C3—C4—C5—C6	−0.5 (2)	N1—C7—C8—N3	−178.92 (13)
C4—C5—C6—C1	−0.8 (2)	C8—N3—C9—C10	0.1 (2)
C2—C1—C6—C5	1.5 (2)	C7—N2—C10—C9	0.0 (2)
N1—C1—C6—C5	−179.75 (13)	N3—C9—C10—N2	−0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3i	0.90 (2)	2.17 (2)	3.062 (2)	175 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3i	0.90 (2)	2.17 (2)	3.062 (2)	175 (2)

Symmetry code: (i) .