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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2009 Mar 6;65(Pt 4):o703. doi: 10.1107/S1600536809007685

N-(Pyrimidin-2-yl)aniline

Edura Badaruddin a, Nasir Shah Bakhtiar a, Zaharah Aiyub a, Zanariah Abdullah a, Seik Weng Ng a,*
PMCID: PMC2969043  PMID: 21582441

Abstract

There are two molecules in the asymmetric unit of the title compound, C10H9N3, with inter-ring dihedral angles of 31.1 (1) and 35.3 (1)°. The bridging C—N—C bond angles are 128.2 (1) and 129.1 (1)°. In the crystal, the two independent mol­ecules are linked into a dimer by two N—H⋯N hydrogen bonds.

Related literature

For the structure of 4-chloro-N-(pyrimidin-2-yl)aniline, see: Maizathul Akmam et al. (2009 ▶).graphic file with name e-65-0o703-scheme1.jpg

Experimental

Crystal data

  • C10H9N3

  • M r = 171.20

  • Triclinic, Inline graphic

  • a = 8.8792 (2) Å

  • b = 9.9382 (2) Å

  • c = 10.2038 (2) Å

  • α = 93.186 (1)°

  • β = 103.665 (1)°

  • γ = 97.780 (1)°

  • V = 863.28 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 123 K

  • 0.35 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer

  • Absorption correction: none

  • 8238 measured reflections

  • 3950 independent reflections

  • 3144 reflections with I > 2σ(I)

  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039

  • wR(F 2) = 0.108

  • S = 1.03

  • 3950 reflections

  • 243 parameters

  • 2 restraints

  • 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, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007685/xu2492sup1.cif

e-65-0o703-sup1.cif (18.7KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007685/xu2492Isup2.hkl

e-65-0o703-Isup2.hkl (193.6KB, hkl)

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⋯N5 0.89 (1) 2.10 (1) 2.972 (1) 164 (1)
N4—H4⋯N2 0.89 (1) 2.15 (1) 3.020 (1) 165 (1)
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Acknowledgments

The authors thank the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

2-Chloropyrimidine (0.05 mol), aniline (0.05 mol) and ethanol (5 ml) were heated at 423–433 K for 3 h. The product was dissolved in water and the solution extracted with ether. The ether phase was dried over sodium sulfate; the evaporation of the solvent gave well shaped colorless crystals along with some unidentified brown material.

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 Uiso(H) set to 1.2Ueq(C). The amino H-atoms were located in a difference Fourier map, and were refined with a distance restraint of N–H 0.88±0.01 Å; their isotropic temperature factors were refined.

Figures

Fig. 1.

Fig. 1.

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Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C10H9N3 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Dashed lines denote hydrogen bonds.

Crystal data

C10H9N3 Z = 4
Mr = 171.20 F(000) = 360
Triclinic, P1 Dx = 1.317 Mg m−3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å
a = 8.8792 (2) Å Cell parameters from 3015 reflections
b = 9.9382 (2) Å θ = 2.7–28.3°
c = 10.2038 (2) Å µ = 0.08 mm−1
α = 93.186 (1)° T = 123 K
β = 103.665 (1)° Prism, colorless
γ = 97.780 (1)° 0.35 × 0.20 × 0.10 mm
V = 863.28 (3) Å3
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Data collection

Bruker SMART APEX diffractometer 3144 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Rint = 0.020
graphite θmax = 27.5°, θmin = 2.1°
ω scans h = −11→11
8238 measured reflections k = −12→12
3950 independent reflections l = −13→12
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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)] = 0.039 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108 H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.056P)2 + 0.1316P] where P = (Fo2 + 2Fc2)/3
3950 reflections (Δ/σ)max = 0.001
243 parameters Δρmax = 0.20 e Å−3
2 restraints Δρmin = −0.22 e Å−3
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
N1 0.63241 (11) 0.69760 (10) 0.39973 (10) 0.0229 (2)
H1 0.5458 (13) 0.7328 (15) 0.4021 (15) 0.042 (4)*
N2 0.60532 (11) 0.62876 (10) 0.60461 (10) 0.0235 (2)
N3 0.82465 (11) 0.58169 (10) 0.51919 (10) 0.0257 (2)
N4 0.33475 (12) 0.78540 (10) 0.59499 (10) 0.0256 (2)
H4 0.4034 (15) 0.7306 (13) 0.5833 (14) 0.038 (4)*
N5 0.37902 (11) 0.86480 (10) 0.39948 (10) 0.0256 (2)
N6 0.18856 (11) 0.94997 (10) 0.50126 (10) 0.0245 (2)
C1 0.69680 (13) 0.72230 (11) 0.28811 (11) 0.0212 (2)
C2 0.59235 (14) 0.72964 (12) 0.16374 (12) 0.0259 (3)
H2 0.4827 0.7163 0.1571 0.031*
C3 0.64691 (15) 0.75616 (13) 0.04969 (12) 0.0305 (3)
H3 0.5748 0.7621 −0.0342 0.037*
C4 0.80703 (15) 0.77406 (13) 0.05803 (13) 0.0304 (3)
H4A 0.8449 0.7896 −0.0203 0.036*
C5 0.91044 (14) 0.76895 (12) 0.18192 (12) 0.0273 (3)
H5 1.0200 0.7824 0.1882 0.033*
C6 0.85757 (13) 0.74464 (11) 0.29708 (12) 0.0234 (2)
H6 0.9304 0.7432 0.3816 0.028*
C7 0.69174 (13) 0.63447 (11) 0.51132 (11) 0.0208 (2)
C8 0.66215 (14) 0.56772 (12) 0.71431 (12) 0.0269 (3)
H8 0.6055 0.5618 0.7825 0.032*
C9 0.79969 (15) 0.51238 (14) 0.73406 (13) 0.0321 (3)
H9 0.8393 0.4706 0.8140 0.039*
C10 0.87631 (14) 0.52129 (13) 0.63096 (13) 0.0309 (3)
H10 0.9700 0.4826 0.6402 0.037*
C11 0.27870 (12) 0.77031 (12) 0.71236 (11) 0.0219 (2)
C12 0.28250 (13) 0.64404 (12) 0.76560 (12) 0.0245 (3)
H12 0.3171 0.5728 0.7199 0.029*
C13 0.23654 (14) 0.62121 (13) 0.88390 (12) 0.0281 (3)
H13 0.2399 0.5349 0.9191 0.034*
C14 0.18554 (15) 0.72450 (14) 0.95093 (13) 0.0322 (3)
H14 0.1532 0.7093 1.0319 0.039*
C15 0.18214 (16) 0.84974 (14) 0.89877 (13) 0.0336 (3)
H15 0.1470 0.9204 0.9447 0.040*
C16 0.22895 (14) 0.87466 (12) 0.78070 (12) 0.0274 (3)
H16 0.2271 0.9617 0.7469 0.033*
C17 0.29837 (13) 0.87077 (11) 0.49672 (11) 0.0220 (2)
C18 0.34955 (14) 0.95120 (12) 0.30445 (12) 0.0277 (3)
H18 0.4052 0.9520 0.2356 0.033*
C19 0.24158 (14) 1.03965 (12) 0.30177 (12) 0.0281 (3)
H19 0.2233 1.1016 0.2342 0.034*
C20 0.16165 (14) 1.03296 (12) 0.40278 (12) 0.0271 (3)
H20 0.0840 1.0901 0.4020 0.033*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
N1 0.0200 (5) 0.0288 (5) 0.0229 (5) 0.0082 (4) 0.0084 (4) 0.0053 (4)
N2 0.0250 (5) 0.0245 (5) 0.0232 (5) 0.0057 (4) 0.0090 (4) 0.0032 (4)
N3 0.0237 (5) 0.0303 (5) 0.0251 (5) 0.0093 (4) 0.0068 (4) 0.0043 (4)
N4 0.0280 (5) 0.0276 (5) 0.0273 (5) 0.0120 (4) 0.0134 (4) 0.0068 (4)
N5 0.0250 (5) 0.0288 (5) 0.0260 (5) 0.0065 (4) 0.0102 (4) 0.0052 (4)
N6 0.0223 (5) 0.0262 (5) 0.0260 (5) 0.0066 (4) 0.0062 (4) 0.0031 (4)
C1 0.0246 (5) 0.0192 (5) 0.0215 (5) 0.0043 (4) 0.0086 (4) 0.0019 (4)
C2 0.0239 (6) 0.0279 (6) 0.0260 (6) 0.0052 (5) 0.0055 (5) 0.0043 (5)
C3 0.0364 (7) 0.0325 (7) 0.0221 (6) 0.0062 (5) 0.0054 (5) 0.0046 (5)
C4 0.0393 (7) 0.0294 (6) 0.0262 (6) 0.0035 (5) 0.0159 (5) 0.0041 (5)
C5 0.0273 (6) 0.0255 (6) 0.0319 (7) 0.0025 (5) 0.0140 (5) 0.0014 (5)
C6 0.0230 (5) 0.0241 (6) 0.0232 (6) 0.0032 (4) 0.0063 (4) 0.0007 (4)
C7 0.0208 (5) 0.0207 (5) 0.0206 (5) 0.0022 (4) 0.0055 (4) −0.0003 (4)
C8 0.0319 (6) 0.0291 (6) 0.0220 (6) 0.0050 (5) 0.0107 (5) 0.0036 (5)
C9 0.0345 (7) 0.0394 (7) 0.0246 (6) 0.0114 (6) 0.0061 (5) 0.0114 (5)
C10 0.0263 (6) 0.0364 (7) 0.0317 (7) 0.0122 (5) 0.0055 (5) 0.0073 (5)
C11 0.0182 (5) 0.0257 (6) 0.0228 (6) 0.0043 (4) 0.0060 (4) 0.0035 (4)
C12 0.0245 (6) 0.0243 (6) 0.0259 (6) 0.0054 (4) 0.0080 (5) 0.0010 (5)
C13 0.0299 (6) 0.0269 (6) 0.0294 (6) 0.0042 (5) 0.0096 (5) 0.0075 (5)
C14 0.0363 (7) 0.0406 (7) 0.0259 (6) 0.0105 (6) 0.0160 (5) 0.0087 (5)
C15 0.0417 (7) 0.0368 (7) 0.0295 (7) 0.0172 (6) 0.0166 (6) 0.0036 (5)
C16 0.0328 (6) 0.0253 (6) 0.0275 (6) 0.0097 (5) 0.0104 (5) 0.0048 (5)
C17 0.0199 (5) 0.0228 (6) 0.0232 (6) 0.0025 (4) 0.0060 (4) 0.0017 (4)
C18 0.0291 (6) 0.0300 (6) 0.0254 (6) 0.0028 (5) 0.0102 (5) 0.0049 (5)
C19 0.0329 (6) 0.0254 (6) 0.0257 (6) 0.0047 (5) 0.0054 (5) 0.0074 (5)
C20 0.0268 (6) 0.0257 (6) 0.0287 (6) 0.0082 (5) 0.0042 (5) 0.0019 (5)
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Geometric parameters (Å, °)

N1—C7 1.3613 (14) C5—H5 0.9500
N1—C1 1.4090 (14) C6—H6 0.9500
N1—H1 0.892 (9) C8—C9 1.3829 (17)
N2—C8 1.3294 (15) C8—H8 0.9500
N2—C7 1.3555 (14) C9—C10 1.3819 (17)
N3—C10 1.3322 (15) C9—H9 0.9500
N3—C7 1.3423 (14) C10—H10 0.9500
N4—C17 1.3584 (15) C11—C16 1.3950 (16)
N4—C11 1.4093 (14) C11—C12 1.3963 (16)
N4—H4 0.894 (8) C12—C13 1.3831 (16)
N5—C18 1.3339 (15) C12—H12 0.9500
N5—C17 1.3570 (14) C13—C14 1.3859 (17)
N6—C20 1.3338 (15) C13—H13 0.9500
N6—C17 1.3407 (14) C14—C15 1.3818 (18)
C1—C6 1.3949 (15) C14—H14 0.9500
C1—C2 1.3958 (16) C15—C16 1.3883 (17)
C2—C3 1.3873 (16) C15—H15 0.9500
C2—H2 0.9500 C16—H16 0.9500
C3—C4 1.3903 (18) C18—C19 1.3824 (17)
C3—H3 0.9500 C18—H18 0.9500
C4—C5 1.3839 (18) C19—C20 1.3824 (17)
C4—H4A 0.9500 C19—H19 0.9500
C5—C6 1.3860 (16) C20—H20 0.9500
C7—N1—C1 128.19 (9) C10—C9—H9 121.9
C7—N1—H1 114.6 (10) C8—C9—H9 121.9
C1—N1—H1 117.0 (10) N3—C10—C9 122.94 (11)
C8—N2—C7 115.61 (10) N3—C10—H10 118.5
C10—N3—C7 116.06 (10) C9—C10—H10 118.5
C17—N4—C11 129.13 (10) C16—C11—C12 119.15 (10)
C17—N4—H4 115.5 (9) C16—C11—N4 124.17 (10)
C11—N4—H4 115.4 (9) C12—C11—N4 116.58 (10)
C18—N5—C17 115.71 (10) C13—C12—C11 120.91 (11)
C20—N6—C17 115.97 (10) C13—C12—H12 119.5
C6—C1—C2 119.10 (10) C11—C12—H12 119.5
C6—C1—N1 123.56 (10) C12—C13—C14 119.88 (11)
C2—C1—N1 117.30 (10) C12—C13—H13 120.1
C3—C2—C1 120.70 (11) C14—C13—H13 120.1
C3—C2—H2 119.7 C15—C14—C13 119.35 (11)
C1—C2—H2 119.7 C15—C14—H14 120.3
C2—C3—C4 120.04 (11) C13—C14—H14 120.3
C2—C3—H3 120.0 C14—C15—C16 121.49 (11)
C4—C3—H3 120.0 C14—C15—H15 119.3
C5—C4—C3 119.13 (11) C16—C15—H15 119.3
C5—C4—H4A 120.4 C15—C16—C11 119.20 (11)
C3—C4—H4A 120.4 C15—C16—H16 120.4
C4—C5—C6 121.39 (11) C11—C16—H16 120.4
C4—C5—H5 119.3 N6—C17—N5 125.94 (11)
C6—C5—H5 119.3 N6—C17—N4 119.51 (10)
C5—C6—C1 119.59 (11) N5—C17—N4 114.55 (10)
C5—C6—H6 120.2 N5—C18—C19 122.92 (11)
C1—C6—H6 120.2 N5—C18—H18 118.5
N3—C7—N2 125.92 (10) C19—C18—H18 118.5
N3—C7—N1 119.10 (10) C18—C19—C20 116.34 (11)
N2—C7—N1 114.96 (10) C18—C19—H19 121.8
N2—C8—C9 123.22 (11) C20—C19—H19 121.8
N2—C8—H8 118.4 N6—C20—C19 123.03 (11)
C9—C8—H8 118.4 N6—C20—H20 118.5
C10—C9—C8 116.22 (11) C19—C20—H20 118.5
C7—N1—C1—C6 −31.08 (18) C17—N4—C11—C16 −28.92 (18)
C7—N1—C1—C2 151.47 (11) C17—N4—C11—C12 154.69 (11)
C6—C1—C2—C3 1.23 (17) C16—C11—C12—C13 0.54 (17)
N1—C1—C2—C3 178.80 (10) N4—C11—C12—C13 177.12 (10)
C1—C2—C3—C4 0.81 (18) C11—C12—C13—C14 0.15 (18)
C2—C3—C4—C5 −1.85 (18) C12—C13—C14—C15 −0.37 (19)
C3—C4—C5—C6 0.85 (18) C13—C14—C15—C16 −0.1 (2)
C4—C5—C6—C1 1.19 (17) C14—C15—C16—C11 0.8 (2)
C2—C1—C6—C5 −2.21 (17) C12—C11—C16—C15 −1.00 (18)
N1—C1—C6—C5 −179.62 (10) N4—C11—C16—C15 −177.30 (11)
C10—N3—C7—N2 −1.59 (17) C20—N6—C17—N5 −2.37 (17)
C10—N3—C7—N1 −179.97 (10) C20—N6—C17—N4 178.70 (10)
C8—N2—C7—N3 1.75 (16) C18—N5—C17—N6 3.36 (17)
C8—N2—C7—N1 −179.81 (10) C18—N5—C17—N4 −177.67 (10)
C1—N1—C7—N3 −3.22 (17) C11—N4—C17—N6 −3.96 (18)
C1—N1—C7—N2 178.23 (10) C11—N4—C17—N5 176.99 (11)
C7—N2—C8—C9 −0.28 (17) C17—N5—C18—C19 −1.45 (17)
N2—C8—C9—C10 −1.14 (19) N5—C18—C19—C20 −1.09 (18)
C7—N3—C10—C9 −0.06 (18) C17—N6—C20—C19 −0.57 (17)
C8—C9—C10—N3 1.3 (2) C18—C19—C20—N6 2.18 (18)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
N1—H1···N5 0.89 (1) 2.10 (1) 2.972 (1) 164 (1)
N4—H4···N2 0.89 (1) 2.15 (1) 3.020 (1) 165 (1)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2492).

References

  1. Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  2. Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Maizathul Akmam, A. B., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o94. [DOI] [PMC free article] [PubMed]
  4. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  5. Westrip, S. P. (2009). publCIF In preparation.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007685/xu2492sup1.cif

e-65-0o703-sup1.cif (18.7KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007685/xu2492Isup2.hkl

e-65-0o703-Isup2.hkl (193.6KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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