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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2106.
Published online 2008 October 11. doi:  10.1107/S1600536808031954
PMCID: PMC2959673

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

Abstract

The two aromatic rings in the title compound, C10H9N3, 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 [triangle]).

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Object name is e-64-o2106-scheme1.jpg

Experimental

Crystal data

  • C10H9N3
  • M r = 171.20
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2106-efi1.jpg
  • 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 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

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

supplementary crystallographic information

Comment

The cell dimensions of the reported monoclinic P21/c modification are: a = 10.0644 (3), b = 7.8423 (3), c = 10.8907 (3) Å; β = 116.439 (2)° (Wan Saffiee et al., 2008). The cell dimensions of the present modification (Scheme I, Fig. 1), after transformation to the standard P21/c setting, are: a = 8.2194 (3), b = 8.8851 (3), c = 12.5909 (4) Å, β = 114.525 (2)°.

Experimental

The P21/c modification of 2-pyrazinyl-N-aniline (0.10 g, 0.4 mmol), zinc acetate (0.09 g, 0.4 mmol) and water (18 ml) were heated in a 23-ml Teflon-lined Parr bomb at 403 K for 2 days. The bomb was cooled to room temperature at 5 K min-1. Several faint yellow prisms were picked out manually from the cool solution.

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 freely refined.

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

C10H9N3F(000) = 360
Mr = 171.20Dx = 1.359 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1282 reflections
a = 8.2194 (3) Åθ = 2.7–26.1°
b = 8.8851 (3) ŵ = 0.09 mm1
c = 11.8395 (4) ÅT = 100 K
β = 104.643 (2)°Prism, pale yellow
V = 836.56 (5) Å30.25 × 0.05 × 0.03 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer1389 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.045
graphiteθmax = 27.5°, θmin = 2.7°
ω scansh = −10→10
7621 measured reflectionsk = −11→11
1922 independent reflectionsl = −15→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0547P)2 + 0.1331P] where P = (Fo2 + 2Fc2)/3
1922 reflections(Δ/σ)max = 0.001
122 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = −0.22 e Å3

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

xyzUiso*/Ueq
N11.00115 (16)0.42084 (14)0.63143 (11)0.0216 (3)
H11.103 (2)0.377 (2)0.6527 (15)0.035 (5)*
N20.84988 (15)0.63197 (14)0.66840 (11)0.0230 (3)
N31.15770 (16)0.76478 (14)0.78284 (11)0.0228 (3)
C10.86787 (18)0.33136 (16)0.56827 (12)0.0193 (3)
C20.89595 (19)0.17682 (17)0.56499 (13)0.0254 (4)
H21.00210.13670.60490.030*
C30.7717 (2)0.08147 (17)0.50462 (14)0.0264 (4)
H30.7933−0.02350.50300.032*
C40.61582 (19)0.13750 (17)0.44633 (13)0.0232 (3)
H40.52960.07170.40580.028*
C50.58777 (19)0.29106 (17)0.44814 (13)0.0222 (3)
H50.48150.33050.40790.027*
C60.71238 (18)0.38836 (16)0.50783 (13)0.0211 (3)
H60.69160.49360.50740.025*
C70.99583 (18)0.56191 (16)0.67668 (13)0.0192 (3)
C81.14967 (18)0.63040 (16)0.73478 (13)0.0213 (3)
H81.25140.57720.73930.026*
C91.00948 (18)0.83515 (18)0.77382 (13)0.0248 (4)
H91.00850.93250.80690.030*
C100.8604 (2)0.76892 (17)0.71788 (14)0.0254 (4)
H100.75920.82260.71390.030*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0144 (7)0.0200 (7)0.0276 (7)0.0019 (5)0.0003 (5)−0.0014 (5)
N20.0173 (6)0.0230 (7)0.0272 (7)0.0004 (5)0.0027 (5)−0.0036 (5)
N30.0195 (7)0.0228 (7)0.0251 (7)−0.0033 (5)0.0037 (5)−0.0011 (5)
C10.0180 (7)0.0205 (7)0.0193 (7)−0.0010 (6)0.0048 (6)−0.0009 (6)
C20.0217 (8)0.0227 (8)0.0289 (8)0.0040 (6)0.0012 (6)0.0000 (6)
C30.0293 (9)0.0176 (8)0.0307 (9)0.0005 (6)0.0043 (7)−0.0019 (6)
C40.0217 (8)0.0233 (8)0.0244 (8)−0.0059 (6)0.0053 (6)−0.0035 (6)
C50.0173 (7)0.0251 (8)0.0229 (8)0.0005 (6)0.0026 (6)−0.0006 (6)
C60.0195 (8)0.0190 (7)0.0237 (8)0.0005 (6)0.0031 (6)−0.0011 (6)
C70.0175 (7)0.0198 (7)0.0194 (7)0.0004 (6)0.0030 (6)0.0020 (6)
C80.0177 (7)0.0224 (8)0.0233 (8)−0.0001 (6)0.0041 (6)0.0015 (6)
C90.0228 (8)0.0220 (8)0.0284 (8)−0.0016 (6)0.0047 (6)−0.0049 (6)
C100.0202 (8)0.0241 (8)0.0307 (9)0.0032 (6)0.0043 (6)−0.0041 (7)

Geometric parameters (Å, °)

N1—C71.3681 (19)C3—H30.9500
N1—C11.4061 (19)C4—C51.385 (2)
N1—H10.897 (18)C4—H40.9500
N2—C71.3330 (18)C5—C61.389 (2)
N2—C101.3438 (19)C5—H50.9500
N3—C81.3171 (19)C6—H60.9500
N3—C91.3494 (19)C7—C81.415 (2)
C1—C61.393 (2)C8—H80.9500
C1—C21.395 (2)C9—C101.370 (2)
C2—C31.379 (2)C9—H90.9500
C2—H20.9500C10—H100.9500
C3—C41.385 (2)
C7—N1—C1128.94 (13)C4—C5—H5119.4
C7—N1—H1114.0 (12)C6—C5—H5119.4
C1—N1—H1116.7 (11)C5—C6—C1119.86 (14)
C7—N2—C10115.67 (13)C5—C6—H6120.1
C8—N3—C9116.12 (13)C1—C6—H6120.1
C6—C1—C2118.72 (13)N2—C7—N1121.09 (13)
C6—C1—N1123.92 (13)N2—C7—C8120.79 (13)
C2—C1—N1117.35 (13)N1—C7—C8118.11 (13)
C3—C2—C1120.88 (14)N3—C8—C7122.74 (13)
C3—C2—H2119.6N3—C8—H8118.6
C1—C2—H2119.6C7—C8—H8118.6
C2—C3—C4120.52 (14)N3—C9—C10121.23 (14)
C2—C3—H3119.7N3—C9—H9119.4
C4—C3—H3119.7C10—C9—H9119.4
C5—C4—C3118.88 (14)N2—C10—C9123.44 (14)
C5—C4—H4120.6N2—C10—H10118.3
C3—C4—H4120.6C9—C10—H10118.3
C4—C5—C6121.11 (14)
C7—N1—C1—C621.9 (2)C10—N2—C7—N1178.88 (14)
C7—N1—C1—C2−159.27 (15)C10—N2—C7—C80.2 (2)
C6—C1—C2—C3−1.0 (2)C1—N1—C7—N22.9 (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—C70.0 (2)
C2—C3—C4—C51.0 (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—C100.1 (2)
C2—C1—C6—C51.5 (2)C7—N2—C10—C90.0 (2)
N1—C1—C6—C5−179.75 (13)N3—C9—C10—N2−0.1 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···N3i0.90 (2)2.17 (2)3.062 (2)175 (2)

Symmetry codes: (i) −x+5/2, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2124).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wan Saffiee, W. A. M., Idris, A., Abdullah, Z., Aiyub, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2105. [PMC free article] [PubMed]
  • Westrip, S. P. (2008). publCIF In preparation.

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