N-(Pyrazin-2-yl)aniline

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

doi:10.1107/S1600536808031942

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2105

doi:10.1107/S1600536808031942

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N-(Pyrazin-2-yl)aniline

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

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

(Received 10 September 2008; accepted 4 October 2008; online 11 October 2008)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.041
wR(F²) = 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

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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/S1600536808031942/pk2121sup1.cif

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

checkCIF report

Comment top

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.

Related literature top

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 top

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.

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

N-(pyrazin-2-yl)aniline top

Crystal data top

C₁₀H₉N₃	F(000) = 360
M_r = 171.20	D_x = 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 top

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

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)] = 0.041	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(F_o²) + (0.0421P)² + 0.247P] where P = (F_o² + 2F_c²)/3
1934 reflections	(Δ/σ)_max = 0.001
122 parameters	Δρ_max = 0.23 e Å⁻³
1 restraint	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₀H₉N₃	V = 846.15 (5) Å³
M_r = 171.20	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.0644 (3) Å	µ = 0.09 mm⁻¹
b = 7.8423 (3) Å	T = 100 K
c = 10.8907 (3) Å	0.20 × 0.10 × 0.05 mm
β = 116.439 (2)°

Data collection top

Bruker SMART APEX diffractometer	1463 reflections with I > 2σ(I)
5664 measured reflections	R_int = 0.033
1934 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.23 e Å⁻³
1934 reflections	Δρ_min = −0.23 e Å⁻³
122 parameters

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

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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, º) top

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) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₉N₃
M_r	171.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.0644 (3), 7.8423 (3), 10.8907 (3)
β (°)	116.439 (2)
V (Å³)	846.15 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.10 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5664, 1934, 1463
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.101, 1.03
No. of reflections	1934
No. of parameters	122
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.23

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···N2ⁱ	0.89 (1)	2.12 (1)	2.977 (2)	162 (1)

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

Acknowledgements

The authors thank the University of Malaya for supporting this study (grant Nos. FS 358/2008A and FA 067/2006A).

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chao, M., Schempp, E. & Rosenstein, R. D. (1976). Acta Cryst. B32, 288–290. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Parsons, S., Wharton, S., McNab, H., Parkin, A. & Johnstone, R. (2006). Private communication (Deposition No. 610410). CCDC, Union Road, Cambridge, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar