Abstract
C19H16N2, orthorhombic, P212121 (no. 19), a = 7.5177(10) Å, b = 12.4761(16) Å, c = 16.118(2) Å, V = 1511.7(3) Å3, Z = 4, Rgt(F) = 0.0424, wRref(F2) = 0.0967, T = 293(2) K.
The 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.
Data collection and handling.
| Crystal: | Colourless block |
| Size: | 0.25 × 0.20 × 0.18 mm |
| Wavelength: | Mo Kα radiation (0.71073 Å) |
| μ: | 0.07 mm−1 |
| Diffractometer, scan mode: | Bruker APEX-II, φ and ω |
| θmax, completeness: | 26.0°, >99% |
| N(hkl)measured, N(hkl)unique, Rint: | 9396, 2961, 0.024 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 2480 |
| N(param)refined: | 190 |
| Programs: | Bruker [1], SHELX [2], [3] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | x | y | z | Uiso*/Ueq |
|---|---|---|---|---|
| C1 | 0.4955(3) | 0.3905(2) | 0.67032(15) | 0.0460(6) |
| C2 | 0.3887(4) | 0.3378(3) | 0.7272(2) | 0.0645(8) |
| H2 | 0.3774 | 0.3645 | 0.7808 | 0.077* |
| C3 | 0.2992(5) | 0.2462(3) | 0.7048(3) | 0.0833(11) |
| H3 | 0.2265 | 0.2121 | 0.7433 | 0.100* |
| C4 | 0.3153(5) | 0.2049(3) | 0.6274(3) | 0.0839(12) |
| H4 | 0.2546 | 0.1427 | 0.6130 | 0.101* |
| C5 | 0.4211(4) | 0.2551(3) | 0.5709(2) | 0.0710(9) |
| H5 | 0.4326 | 0.2267 | 0.5178 | 0.085* |
| C6 | 0.5119(4) | 0.3482(2) | 0.59167(17) | 0.0539(7) |
| H6 | 0.5837 | 0.3820 | 0.5526 | 0.065* |
| C7 | 0.5836(4) | 0.4947(2) | 0.69547(18) | 0.0573(7) |
| H7A | 0.4974 | 0.5523 | 0.6912 | 0.069* |
| H7B | 0.6200 | 0.4897 | 0.7531 | 0.069* |
| C8 | 0.7268(4) | 0.5986(2) | 0.58754(18) | 0.0537(7) |
| H8 | 0.6280 | 0.6434 | 0.5871 | 0.064* |
| C9 | 0.8543(4) | 0.6140(2) | 0.53020(17) | 0.0566(7) |
| C10 | 1.0007(4) | 0.5388(2) | 0.52736(17) | 0.0594(7) |
| H10 | 1.0825 | 0.5427 | 0.4842 | 0.071* |
| C11 | 1.0196(4) | 0.4646(2) | 0.58515(16) | 0.0562(7) |
| H11 | 1.1095 | 0.4140 | 0.5791 | 0.067* |
| C12 | 0.9021(3) | 0.4587(2) | 0.66022(16) | 0.0487(6) |
| H12 | 0.8688 | 0.3835 | 0.6683 | 0.058* |
| C13 | 0.8407(4) | 0.6955(3) | 0.4693(2) | 0.0726(9) |
| C14 | 0.9961(3) | 0.4968(2) | 0.73890(15) | 0.0460(6) |
| C15 | 0.9761(4) | 0.4442(3) | 0.81351(18) | 0.0650(8) |
| H15 | 0.9055 | 0.3831 | 0.8167 | 0.078* |
| C16 | 1.0619(5) | 0.4825(4) | 0.88418(19) | 0.0827(11) |
| H16 | 1.0483 | 0.4470 | 0.9345 | 0.099* |
| C17 | 1.1660(5) | 0.5721(3) | 0.8799(2) | 0.0781(10) |
| H17 | 1.2212 | 0.5978 | 0.9276 | 0.094* |
| C18 | 1.1894(4) | 0.6241(3) | 0.8064(2) | 0.0656(8) |
| H18 | 1.2619 | 0.6844 | 0.8038 | 0.079* |
| C19 | 1.1055(3) | 0.5874(2) | 0.73565(17) | 0.0509(6) |
| H19 | 1.1218 | 0.6231 | 0.6856 | 0.061* |
| N1 | 0.7358(3) | 0.52085(16) | 0.64567(14) | 0.0488(5) |
| N2 | 0.8327(5) | 0.7609(3) | 0.4197(2) | 0.1090(12) |
Source of material
Phenylmagnesium bromide (3.77 g, 24 mmol), bromobenzene (0.56 g, 3.5 mmol), and magnesium (0.55 g, 23 mmol) were added to 1-benzyl-3-cyanopyridine bromide (5.50 g, 20 mmol) [4], [5], [6]. Stirring was continued for 20 min with cooling to room temperature. The solution was washed three times with water to obtain a mixture. After drying of the organic layer over sodium sulfate the solution was filtered and evaporated to dryness. The resulting oil was purified by silica gel column chromatography using a mixture of petroleum ether and ethyl acetate. Finally, the resulting solution was evaporated to dryness in vacuo to give the title compound as colorless crystals.
Experimental details
All hydrogen atoms were placed in the calculated positions and all the non-hydrogen atoms were refined anisotropically.
Comment
In recent years, it was reported that the title compound is a estrogen receptor [7]. Estrogen receptors are more abundant in the cells of the target organs, and can specifically bind to hormones to form hormone-receptor complexes, allowing hormones to exert their biological effects. This may be important in the treatment of cancer, cardiovascular disease, inflammatory disease, immune and reproductive systems [8], [9], [10].
The title compound crystalize in the orthorhombic crystal system with the space group of P212121. When a pyridine has one electron-withdrawing substituent at the 3 position or two such substituents at the 3 and 5 positions the reaction proceeds faster, forming a cyanopyridine salt which is then reacted with phenylmagnesium bromide to give the title product. However, due to the steric hidrance effect, the phenyl groups are arranged side by side. In the crystal structure, several important bond angles are as follows C8—N1—C7 = 120.7(2)°, C8—N1—C12 = 121.7(2)°, C7—N1—C12 = 117.6(2)°, C11—C12—C14 = 112.6(2)°. Generally all bond lengths and angles are in the expected ranges.
Acknowledgements
We gratefully acknowledge support by the Graduate Student Innovation Fund of North China University of Science and Technology and Science Research Foundation of North China University of Science and Technology.
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©2019 Shi-Jun Chen et al., published by De Gruyter, Berlin/Boston
This work is licensed under the Creative Commons Attribution 4.0 Public License.
