Abstract
C17H13BrN2, orthorhombic, Pbca (no. 61), a = 9.995(4) Å, b = 13.845(5) Å, c = 20.213(7) Å, V = 2797.2(18) Å3, Z = 8, Rgt(F) = 0.0304, wRref(F2) = 0.0784, T = 296(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.
Source of material
A mixture of naphthalene-1,8-diamine (1.58 g, 10 mmol) and 4-bromobenzaldehyde (1.85 g, 10 mmol), in anhydrous ethanol (50 mL) was refluxed at 353 K for about 2 h. Then the solvent was removed under reduced presure. The resulting residue was purified by recrystallization from ethanol to obtain a crystal (yield 2.86 g, 88%).
Data collection and handling.
| Crystal: | Yellow block |
| Size: | 0.36 × 0.33 × 0.30 mm |
| Wavelength: | Mo Kα radiation (0.71073 Å) |
| μ: | 2.9 mm−1 |
| Diffractometer, scan mode: | Bruker APEXII, φ and ω |
| θmax, completeness: | 25.0°, >99% |
| N(hkl)measured, N(hkl)unique, Rint: | 24886, 2461, 0.022 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 2105 |
| N(param)refined: | 181 |
| Programs: | Bruker programs [9], SHELX [10], [11] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | x | y | z | Uiso*/Ueq |
|---|---|---|---|---|
| Br1 | 0.18042(3) | 0.35089(2) | 0.33392(2) | 0.06296(13) |
| N1 | 0.2936(2) | 0.68189(15) | 0.57191(10) | 0.0421(5) |
| H1 | 0.3410 | 0.6309 | 0.5783 | 0.051* |
| N2 | 0.09235(19) | 0.74946(14) | 0.53505(10) | 0.0437(5) |
| H2 | 0.0534 | 0.7572 | 0.4975 | 0.052* |
| C1 | 0.2059(2) | 0.82136(17) | 0.62753(11) | 0.0380(5) |
| C2 | 0.3044(2) | 0.74847(17) | 0.62398(11) | 0.0375(5) |
| C3 | 0.4092(3) | 0.74798(19) | 0.66788(12) | 0.0468(6) |
| H3 | 0.4737 | 0.6997 | 0.6658 | 0.056* |
| C4 | 0.4185(3) | 0.8209(2) | 0.71593(13) | 0.0521(7) |
| H4 | 0.4884 | 0.8193 | 0.7462 | 0.062* |
| C5 | 0.3274(3) | 0.8936(2) | 0.71913(12) | 0.0500(7) |
| H5 | 0.3371 | 0.9419 | 0.7508 | 0.060* |
| C6 | 0.2183(3) | 0.89664(18) | 0.67493(11) | 0.0427(6) |
| C7 | 0.1232(3) | 0.97190(19) | 0.67458(13) | 0.0510(7) |
| H7 | 0.1298 | 1.0219 | 0.7051 | 0.061* |
| C8 | 0.0222(3) | 0.9715(2) | 0.62974(14) | 0.0541(7) |
| H8 | −0.0393 | 1.0220 | 0.6300 | 0.065* |
| C9 | 0.0075(3) | 0.89749(19) | 0.58307(14) | 0.0503(6) |
| H9 | −0.0631 | 0.8989 | 0.5531 | 0.060* |
| C10 | 0.0979(2) | 0.82290(17) | 0.58178(12) | 0.0408(5) |
| C11 | 0.1555(2) | 0.65951(17) | 0.55290(12) | 0.0408(5) |
| H11 | 0.1087 | 0.6318 | 0.5911 | 0.049* |
| C12 | 0.1564(2) | 0.58674(17) | 0.49761(12) | 0.0380(5) |
| C13 | 0.1791(2) | 0.49116(18) | 0.51340(12) | 0.0447(6) |
| H13 | 0.1886 | 0.4737 | 0.5576 | 0.054* |
| C14 | 0.1880(3) | 0.42121(18) | 0.46551(13) | 0.0458(6) |
| H14 | 0.2054 | 0.3573 | 0.4768 | 0.055* |
| C15 | 0.1706(2) | 0.44749(18) | 0.40048(12) | 0.0423(6) |
| C16 | 0.1458(3) | 0.54151(19) | 0.38309(12) | 0.0492(6) |
| H16 | 0.1326 | 0.5581 | 0.3390 | 0.059* |
| C17 | 0.1405(3) | 0.61125(19) | 0.43183(12) | 0.0458(6) |
| H17 | 0.1260 | 0.6754 | 0.4203 | 0.055* |
Experimental details
All hydrogen atoms were identified in difference Fourier syntheses. The Uiso values of the hydrogen atoms were set to 1.2 Ueq(C).
Comment
Perimidines have drawn extensive examinations of many researchers for a long time, because they exhibit a diverse range of biological activities [1], [2], [3]. There are several preparative methods for the synthesis of perimidine derivatives [4], [5], [6], [7]. Herein, we report on a novel perimidine compound which was synthesized and characterized by single-crystal X-ray diffraction.
In the structure, the bond angles of N(1)—C(11)—N(2), N(1)—C(11)—C(12) and N(2)—C(11)—C(12) are 107.17(19), 109.31(19) and 113.3(2) in turn, which indicates the sp3 hybridization state of C(11) atom and the new-formed three-membered heterocyclic ring is nonplanar. All bond lengths and angles are in the expected ranges [8].
Acknowledgements
This work was financially supported by the Natural Science Foundation of Hunan Province of China (2017JJ3093).
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