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Acta Cryst. (2009). E65, o703    [ doi:10.1107/S1600536809007685 ]

N-(Pyrimidin-2-yl)aniline

E. Badaruddin, N. Shah Bakhtiar, Z. Aiyub, Z. Abdullah and S. W. Ng

Abstract top

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 top

For 4-chloro-N-(pyrimidin-2-yl)aniline, see: Maizathul Akmam et al. (2009).

Experimental top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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).

Figures top
[Figure 1] Fig. 1. 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.
N-(Pyrimidin-2-yl)aniline top
Crystal data top
C10H9N3Z = 4
Mr = 171.20F(000) = 360
Triclinic, P1Dx = 1.317 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8792 (2) ÅCell parameters from 3015 reflections
b = 9.9382 (2) Åθ = 2.7–28.3°
c = 10.2038 (2) ŵ = 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
Data collection top
Bruker SMART APEX
diffractometer		3144 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
graphiteθmax = 27.5°, θmin = 2.1°
ω scansh = −11→11
8238 measured reflectionsk = −12→12
3950 independent reflectionsl = −13→12
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H 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 parametersΔρmax = 0.20 e Å−3
2 restraintsΔρmin = −0.22 e Å−3
Crystal data top
C10H9N3γ = 97.780 (1)°
Mr = 171.20V = 863.28 (3) Å3
Triclinic, P1Z = 4
a = 8.8792 (2) ÅMo Kα radiation
b = 9.9382 (2) ŵ = 0.08 mm−1
c = 10.2038 (2) ÅT = 123 K
α = 93.186 (1)°0.35 × 0.20 × 0.10 mm
β = 103.665 (1)°
Data collection top
Bruker SMART APEX
diffractometer		3144 reflections with I > 2σ(I)
8238 measured reflectionsRint = 0.020
3950 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108Δρmax = 0.20 e Å−3
S = 1.03Δρmin = −0.22 e Å−3
3950 reflectionsAbsolute structure: ?
243 parametersFlack parameter: ?
2 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.63241 (11)0.69760 (10)0.39973 (10)0.0229 (2)
H10.5458 (13)0.7328 (15)0.4021 (15)0.042 (4)*
N20.60532 (11)0.62876 (10)0.60461 (10)0.0235 (2)
N30.82465 (11)0.58169 (10)0.51919 (10)0.0257 (2)
N40.33475 (12)0.78540 (10)0.59499 (10)0.0256 (2)
H40.4034 (15)0.7306 (13)0.5833 (14)0.038 (4)*
N50.37902 (11)0.86480 (10)0.39948 (10)0.0256 (2)
N60.18856 (11)0.94997 (10)0.50126 (10)0.0245 (2)
C10.69680 (13)0.72230 (11)0.28811 (11)0.0212 (2)
C20.59235 (14)0.72964 (12)0.16374 (12)0.0259 (3)
H20.48270.71630.15710.031*
C30.64691 (15)0.75616 (13)0.04969 (12)0.0305 (3)
H30.57480.7621−0.03420.037*
C40.80703 (15)0.77406 (13)0.05803 (13)0.0304 (3)
H4A0.84490.7896−0.02030.036*
C50.91044 (14)0.76895 (12)0.18192 (12)0.0273 (3)
H51.02000.78240.18820.033*
C60.85757 (13)0.74464 (11)0.29708 (12)0.0234 (2)
H60.93040.74320.38160.028*
C70.69174 (13)0.63447 (11)0.51132 (11)0.0208 (2)
C80.66215 (14)0.56772 (12)0.71431 (12)0.0269 (3)
H80.60550.56180.78250.032*
C90.79969 (15)0.51238 (14)0.73406 (13)0.0321 (3)
H90.83930.47060.81400.039*
C100.87631 (14)0.52129 (13)0.63096 (13)0.0309 (3)
H100.97000.48260.64020.037*
C110.27870 (12)0.77031 (12)0.71236 (11)0.0219 (2)
C120.28250 (13)0.64404 (12)0.76560 (12)0.0245 (3)
H120.31710.57280.71990.029*
C130.23654 (14)0.62121 (13)0.88390 (12)0.0281 (3)
H130.23990.53490.91910.034*
C140.18554 (15)0.72450 (14)0.95093 (13)0.0322 (3)
H140.15320.70931.03190.039*
C150.18214 (16)0.84974 (14)0.89877 (13)0.0336 (3)
H150.14700.92040.94470.040*
C160.22895 (14)0.87466 (12)0.78070 (12)0.0274 (3)
H160.22710.96170.74690.033*
C170.29837 (13)0.87077 (11)0.49672 (11)0.0220 (2)
C180.34955 (14)0.95120 (12)0.30445 (12)0.0277 (3)
H180.40520.95200.23560.033*
C190.24158 (14)1.03965 (12)0.30177 (12)0.0281 (3)
H190.22331.10160.23420.034*
C200.16165 (14)1.03296 (12)0.40278 (12)0.0271 (3)
H200.08401.09010.40200.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0200 (5)0.0288 (5)0.0229 (5)0.0082 (4)0.0084 (4)0.0053 (4)
N20.0250 (5)0.0245 (5)0.0232 (5)0.0057 (4)0.0090 (4)0.0032 (4)
N30.0237 (5)0.0303 (5)0.0251 (5)0.0093 (4)0.0068 (4)0.0043 (4)
N40.0280 (5)0.0276 (5)0.0273 (5)0.0120 (4)0.0134 (4)0.0068 (4)
N50.0250 (5)0.0288 (5)0.0260 (5)0.0065 (4)0.0102 (4)0.0052 (4)
N60.0223 (5)0.0262 (5)0.0260 (5)0.0066 (4)0.0062 (4)0.0031 (4)
C10.0246 (5)0.0192 (5)0.0215 (5)0.0043 (4)0.0086 (4)0.0019 (4)
C20.0239 (6)0.0279 (6)0.0260 (6)0.0052 (5)0.0055 (5)0.0043 (5)
C30.0364 (7)0.0325 (7)0.0221 (6)0.0062 (5)0.0054 (5)0.0046 (5)
C40.0393 (7)0.0294 (6)0.0262 (6)0.0035 (5)0.0159 (5)0.0041 (5)
C50.0273 (6)0.0255 (6)0.0319 (7)0.0025 (5)0.0140 (5)0.0014 (5)
C60.0230 (5)0.0241 (6)0.0232 (6)0.0032 (4)0.0063 (4)0.0007 (4)
C70.0208 (5)0.0207 (5)0.0206 (5)0.0022 (4)0.0055 (4)−0.0003 (4)
C80.0319 (6)0.0291 (6)0.0220 (6)0.0050 (5)0.0107 (5)0.0036 (5)
C90.0345 (7)0.0394 (7)0.0246 (6)0.0114 (6)0.0061 (5)0.0114 (5)
C100.0263 (6)0.0364 (7)0.0317 (7)0.0122 (5)0.0055 (5)0.0073 (5)
C110.0182 (5)0.0257 (6)0.0228 (6)0.0043 (4)0.0060 (4)0.0035 (4)
C120.0245 (6)0.0243 (6)0.0259 (6)0.0054 (4)0.0080 (5)0.0010 (5)
C130.0299 (6)0.0269 (6)0.0294 (6)0.0042 (5)0.0096 (5)0.0075 (5)
C140.0363 (7)0.0406 (7)0.0259 (6)0.0105 (6)0.0160 (5)0.0087 (5)
C150.0417 (7)0.0368 (7)0.0295 (7)0.0172 (6)0.0166 (6)0.0036 (5)
C160.0328 (6)0.0253 (6)0.0275 (6)0.0097 (5)0.0104 (5)0.0048 (5)
C170.0199 (5)0.0228 (6)0.0232 (6)0.0025 (4)0.0060 (4)0.0017 (4)
C180.0291 (6)0.0300 (6)0.0254 (6)0.0028 (5)0.0102 (5)0.0049 (5)
C190.0329 (6)0.0254 (6)0.0257 (6)0.0047 (5)0.0054 (5)0.0074 (5)
C200.0268 (6)0.0257 (6)0.0287 (6)0.0082 (5)0.0042 (5)0.0019 (5)
Geometric parameters (Å, °) top
N1—C71.3613 (14)C5—H50.9500
N1—C11.4090 (14)C6—H60.9500
N1—H10.892 (9)C8—C91.3829 (17)
N2—C81.3294 (15)C8—H80.9500
N2—C71.3555 (14)C9—C101.3819 (17)
N3—C101.3322 (15)C9—H90.9500
N3—C71.3423 (14)C10—H100.9500
N4—C171.3584 (15)C11—C161.3950 (16)
N4—C111.4093 (14)C11—C121.3963 (16)
N4—H40.894 (8)C12—C131.3831 (16)
N5—C181.3339 (15)C12—H120.9500
N5—C171.3570 (14)C13—C141.3859 (17)
N6—C201.3338 (15)C13—H130.9500
N6—C171.3407 (14)C14—C151.3818 (18)
C1—C61.3949 (15)C14—H140.9500
C1—C21.3958 (16)C15—C161.3883 (17)
C2—C31.3873 (16)C15—H150.9500
C2—H20.9500C16—H160.9500
C3—C41.3903 (18)C18—C191.3824 (17)
C3—H30.9500C18—H180.9500
C4—C51.3839 (18)C19—C201.3824 (17)
C4—H4A0.9500C19—H190.9500
C5—C61.3860 (16)C20—H200.9500
C7—N1—C1128.19 (9)C10—C9—H9121.9
C7—N1—H1114.6 (10)C8—C9—H9121.9
C1—N1—H1117.0 (10)N3—C10—C9122.94 (11)
C8—N2—C7115.61 (10)N3—C10—H10118.5
C10—N3—C7116.06 (10)C9—C10—H10118.5
C17—N4—C11129.13 (10)C16—C11—C12119.15 (10)
C17—N4—H4115.5 (9)C16—C11—N4124.17 (10)
C11—N4—H4115.4 (9)C12—C11—N4116.58 (10)
C18—N5—C17115.71 (10)C13—C12—C11120.91 (11)
C20—N6—C17115.97 (10)C13—C12—H12119.5
C6—C1—C2119.10 (10)C11—C12—H12119.5
C6—C1—N1123.56 (10)C12—C13—C14119.88 (11)
C2—C1—N1117.30 (10)C12—C13—H13120.1
C3—C2—C1120.70 (11)C14—C13—H13120.1
C3—C2—H2119.7C15—C14—C13119.35 (11)
C1—C2—H2119.7C15—C14—H14120.3
C2—C3—C4120.04 (11)C13—C14—H14120.3
C2—C3—H3120.0C14—C15—C16121.49 (11)
C4—C3—H3120.0C14—C15—H15119.3
C5—C4—C3119.13 (11)C16—C15—H15119.3
C5—C4—H4A120.4C15—C16—C11119.20 (11)
C3—C4—H4A120.4C15—C16—H16120.4
C4—C5—C6121.39 (11)C11—C16—H16120.4
C4—C5—H5119.3N6—C17—N5125.94 (11)
C6—C5—H5119.3N6—C17—N4119.51 (10)
C5—C6—C1119.59 (11)N5—C17—N4114.55 (10)
C5—C6—H6120.2N5—C18—C19122.92 (11)
C1—C6—H6120.2N5—C18—H18118.5
N3—C7—N2125.92 (10)C19—C18—H18118.5
N3—C7—N1119.10 (10)C18—C19—C20116.34 (11)
N2—C7—N1114.96 (10)C18—C19—H19121.8
N2—C8—C9123.22 (11)C20—C19—H19121.8
N2—C8—H8118.4N6—C20—C19123.03 (11)
C9—C8—H8118.4N6—C20—H20118.5
C10—C9—C8116.22 (11)C19—C20—H20118.5
C7—N1—C1—C6−31.08 (18)C17—N4—C11—C16−28.92 (18)
C7—N1—C1—C2151.47 (11)C17—N4—C11—C12154.69 (11)
C6—C1—C2—C31.23 (17)C16—C11—C12—C130.54 (17)
N1—C1—C2—C3178.80 (10)N4—C11—C12—C13177.12 (10)
C1—C2—C3—C40.81 (18)C11—C12—C13—C140.15 (18)
C2—C3—C4—C5−1.85 (18)C12—C13—C14—C15−0.37 (19)
C3—C4—C5—C60.85 (18)C13—C14—C15—C16−0.1 (2)
C4—C5—C6—C11.19 (17)C14—C15—C16—C110.8 (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—N4178.70 (10)
C8—N2—C7—N31.75 (16)C18—N5—C17—N63.36 (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—N2178.23 (10)C11—N4—C17—N5176.99 (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—N31.3 (2)C18—C19—C20—N62.18 (18)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N50.89 (1)2.10 (1)2.972 (1)164 (1)
N4—H4···N20.89 (1)2.15 (1)3.020 (1)165 (1)
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N50.89 (1)2.10 (1)2.972 (1)164 (1)
N4—H4···N20.89 (1)2.15 (1)3.020 (1)165 (1)
Acknowledgements top

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

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Maizathul Akmam, A. B., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o94.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.