Home Crystal structure of 5-bromo-2-(naphthalen-6-yl)pyridine, C15H10BrN
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Crystal structure of 5-bromo-2-(naphthalen-6-yl)pyridine, C15H10BrN

  • Hong-Mei Li EMAIL logo , Hao-Feng Wang , Bei-Jing Sun and Xin-Hua Lou
Published/Copyright: September 27, 2018

Abstract

C15H10BrN, monoclinic, P21/c (no. 14), a = 14.6998(9) Å, b = 5.9337(4) Å, c = 14.6275(11) Å, β = 113.542(8)°, V = 1169.67(15) Å3, Z = 4, Rgt(F) = 0.0396, wRref(F2) = 0.1103, T = 293(2) K.

CCDC no.: 1848649

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless prism
Size:0.20 × 0.18 × 0.15 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:4.56 mm−1
Diffractometer, scan mode:Xcalibur, ω
θmax, completeness:67.1°, >99%
N(hkl)measured, N(hkl)unique, Rint:4263, 2078, 0.026
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1651
N(param)refined:154
Programs:SHELX [1], CrysAlisPRO [2]
Table 2:

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

AtomxyzUiso*/Ueq
Br10.55224(3)0.57982(9)0.68324(3)0.0684(2)
C11.3067(2)0.2805(6)1.0306(2)0.0460(8)
H11.32780.14601.06530.055*
C21.3753(2)0.4336(7)1.0287(3)0.0498(9)
H21.44270.40241.06170.060*
C31.3449(3)0.6360(6)0.9776(3)0.0497(9)
H31.39230.73850.97640.060*
C41.2463(2)0.6867(6)0.9288(3)0.0439(8)
H41.22740.82350.89550.053*
C51.1730(2)0.5323(5)0.9289(2)0.0369(7)
C61.2036(2)0.3242(6)0.9803(2)0.0373(7)
C71.1299(2)0.1704(6)0.9792(2)0.0414(8)
H71.14860.03401.01290.050*
C81.0318(2)0.2190(5)0.9296(2)0.0391(7)
H80.98490.11360.92940.047*
C90.9991(2)0.4255(5)0.8784(2)0.0333(7)
C101.0703(2)0.5777(5)0.8789(2)0.0364(7)
H101.05020.71400.84560.044*
C110.8910(2)0.4740(5)0.8288(2)0.0350(7)
C120.8538(2)0.6739(6)0.7784(3)0.0436(8)
H120.89710.78360.77410.052*
C130.7527(2)0.7101(6)0.7346(3)0.0451(8)
H130.72670.84300.70050.054*
C140.6917(2)0.5428(6)0.7432(2)0.0435(8)
C150.7324(2)0.3472(6)0.7938(3)0.0476(9)
H150.69000.23570.79860.057*
N10.8298(2)0.3115(5)0.8360(2)0.0440(7)

Source of material

The title compound was obtained from the palladium-catalyzed Suzuki coupling of naphthalen-2-yl-2-boronic acid and 2,5-dibromopyridine, which were prepared according to the published procedures [3]. The product was recrystallized from dichloromethane/petroleum ether at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.

Experimental details

Hydrogen atoms were added using the riding models implemented in the SHELX system.

Comment

Pyridines are an important class of N-containing heterocyclic compounds for natural products, pharmaceuticals [4]. Moreover, some aryl-pyridines are used in functional materials, supramolecular chemistry and organometallic catalysis [5], [6], [7], [8]. Among several methods for their synthesis, the Suzuki coupling has become an extremely useful method for the formation of carbon-carbon [9], [10], [11], [12]. It is known that the 2-pyridyl boronic acid was not stable [10]. Thus we prepared the title compound from the Suzuki coupling of naphthalen-2-yl-2-boronic acid and 2,5-dibromopyridine (the ratio of 1:1).

A view of the molecular structure of the title compound is given in the figure. The pyridine ring and naphthaline ring are coplanar, which is similar to those of related aryl-N-heterocyclic derivatives [13, 14] . The bromine and nitrogen atom in pyrimidine ring do not participate in hydrogen bonds.

Acknowledgements

This work was supported by the Innovation Scientists and Technicians Troop Construction Projects of Henan Province (154100510015), the tackle key problem of science and technology Project of Henan Province (162102210125).

References

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Received: 2018-06-17
Accepted: 2018-09-05
Published Online: 2018-09-27
Published in Print: 2018-12-19

©2018 Hong-Mei Li et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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