Abstract
C21H24ClNO3, orthorhombic, Pbcn (no. 60), a = 17.215(11) Å, b = 15.749(11) Å, c = 14.136(9) Å, V = 3832(4) Å3, Z = 8, Rgt(F) = 0.058, wRref(F2) = 0.177, T = 296(2) K.
Data collection and handling.
| Crystal: | Block, yellow |
| Size: | 0.32 × 0.28 × 0.25 mm |
| Wavelength: | Mo Kα radiation (λ =0.71073 Å) |
| μ: | 0.220 mm−1 |
| Diffractometer, scan mode: | CCD area detector, Φ and ω-scans |
| 2θmax, completeness: | 25.0°, >99% |
| N(hkl)measured, N(hkl)unique, Rint: | 18525, 3380, 0.0541 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2σ(Iobs), 2176 |
| N(param)refined: | 237 |
| Programs: | Bruker programs [1], OLEX2 [2], SHELX [3] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | x | y | z | Uiso*/Ueq |
|---|---|---|---|---|
| N1 | 0.38417(14) | 0.07907(15) | 0.67038(16) | 0.0480(6) |
| H1 | 0.382670 | 0.069075 | 0.730163 | 0.058 |
| Cl1 | 0.07594(6) | 0.03553(7) | 0.64578(8) | 0.0899(4) |
| O1 | 0.34465(15) | 0.26977(15) | 0.42352(19) | 0.0750(8) |
| O2 | 0.39095(18) | 0.32592(16) | 0.5537(2) | 0.0915(9) |
| O3 | 0.38800(14) | −0.03147(13) | 0.36612(13) | 0.0575(6) |
| C1 | 0.1287(2) | 0.0655(2) | 0.5469(3) | 0.0605(9) |
| C2 | 0.0902(2) | 0.0811(2) | 0.4651(3) | 0.0760(11) |
| H2 | 0.036355 | 0.076576 | 0.462149 | 0.091 |
| C3 | 0.1322(3) | 0.1035(3) | 0.3872(3) | 0.0866(13) |
| H3 | 0.106708 | 0.113216 | 0.330203 | 0.104 |
| C4 | 0.2129(2) | 0.1120(2) | 0.3916(3) | 0.0724(11) |
| H4 | 0.240465 | 0.127766 | 0.337859 | 0.087 |
| C5 | 0.25177(18) | 0.09724(17) | 0.4751(2) | 0.0484(7) |
| C6 | 0.20789(17) | 0.07292(19) | 0.5530(2) | 0.0529(8) |
| H6 | 0.232581 | 0.061488 | 0.610167 | 0.063 |
| C7 | 0.33959(17) | 0.10569(18) | 0.4830(2) | 0.0446(7) |
| H7 | 0.360218 | 0.118024 | 0.419830 | 0.053 |
| C8 | 0.36302(17) | 0.17781(18) | 0.5485(2) | 0.0451(7) |
| C9 | 0.36804(19) | 0.2649(2) | 0.5126(3) | 0.0558(8) |
| C10 | 0.3490(3) | 0.3533(3) | 0.3802(4) | 0.1065(17) |
| H10A | 0.348447 | 0.396490 | 0.429080 | 0.128 |
| H10B | 0.397441 | 0.358476 | 0.345519 | 0.128 |
| C11 | 0.2884(3) | 0.3660(3) | 0.3203(4) | 0.1195(18) |
| H11A | 0.292420 | 0.421430 | 0.292463 | 0.179 |
| H11B | 0.289423 | 0.323771 | 0.271296 | 0.179 |
| H11C | 0.240503 | 0.361728 | 0.354732 | 0.179 |
| C12 | 0.37905(17) | 0.16208(18) | 0.6394(2) | 0.0467(7) |
| C13 | 0.3931(2) | 0.2265(2) | 0.7154(3) | 0.0688(10) |
| H13A | 0.397010 | 0.198357 | 0.775466 | 0.103 |
| H13B | 0.350662 | 0.266055 | 0.716945 | 0.103 |
| H13C | 0.440521 | 0.256363 | 0.702563 | 0.103 |
| C14 | 0.39150(15) | 0.01270(17) | 0.60964(18) | 0.0403(7) |
| C15 | 0.37588(16) | 0.02432(17) | 0.51714(18) | 0.0391(6) |
| C16 | 0.39399(16) | −0.04244(18) | 0.45158(19) | 0.0412(7) |
| C17 | 0.42347(18) | −0.12548(18) | 0.4897(2) | 0.0487(7) |
| H17A | 0.479701 | −0.125556 | 0.485240 | 0.058 |
| H17B | 0.404362 | −0.170761 | 0.449382 | 0.058 |
| C18 | 0.40105(17) | −0.14539(18) | 0.5907(2) | 0.0459(7) |
| C19 | 0.42054(17) | −0.06797(18) | 0.65033(19) | 0.0452(7) |
| H19A | 0.398411 | −0.075298 | 0.712900 | 0.054 |
| H19B | 0.476498 | −0.064294 | 0.657312 | 0.054 |
| C20 | 0.3145(2) | −0.1664(2) | 0.5974(3) | 0.0685(10) |
| H20A | 0.301358 | −0.178886 | 0.661964 | 0.103 |
| H20B | 0.284591 | −0.118732 | 0.575994 | 0.103 |
| H20C | 0.303248 | −0.214905 | 0.558603 | 0.103 |
| C21 | 0.4485(2) | −0.2213(2) | 0.6259(3) | 0.0715(10) |
| H21A | 0.434279 | −0.234022 | 0.690008 | 0.107 |
| H21B | 0.438095 | −0.269768 | 0.586607 | 0.107 |
| H21C | 0.502821 | −0.207860 | 0.623059 | 0.107 |
Source of materials
The title compound was synthesized according to reported procedures. A mixture of 1,1-dimethyl-3,5-cyclohexanedione (10 mmol), 3-chlorobenzaldehyde (10 mmol), ammonium acetate (10 mmol) and ethyl acetoacetate (10 mmol) in ethanol (100 mL) was refluxed for 2–3 h and then cooled to room temperature. After filtering the precipitates, they were sequentially washed with ice-cooled water and ethanol and then dried under vacuum.
Experimental details
H atoms were positioned geometrically and refined using a riding model, with C—H = 0.96 Å and N—H = 0.86 Å with Uiso(H) = 1.2 times Ueq(C) and 1.2 times Ueq(N).
Comment
4-Arylpolyhydroquinolines possess diverse pharmacological and biological activities such as antitumor, analgesic and ulcerogenic, anti-inflammatory, anticoagulant, phototriggering, and fungicidal properties, and can act as anticoagulants in the production of pesticides [4]. Neurofibromatosis type I(NF-1) is a complex multi-system human disorder caused by the mutation of ageneonchromosome 17 that is responsible for production of a protein called neurofibromin which is needed for normal function in many human cell types [5]. NF-1 causes tumors along the nervous system which can grow anywhere on the body. NF-1 is one of the most common genetic disorders and is not limited to any person’s race or sex [6]. Recent research has also indicated that these heterocycles is an effective treatment to shrink NF-1 and control symptoms [7].
In the crystal structure of the title compound (Figure), the six-membered ring containing nitrogen atom is slightly folded and the adjacent ring containing the keto group adopts a flattened chair conformation. The nitrogenous heterocyclic is almost perpendicular to the chlorophenyl moiety and is almost coplanar with the mean plane of the ketone ring. The bond distances and the bond angles in the title compound are comparable with those in known compounds [8], [9], [10]. Compared with the known similar structures [8], [9], [10], the main difference is that they have different functional groups. The Cl atom in the title compound was replaced by one Br atom, one -OCH3 group and one H atom in the compounds reported in reference 5, 6 and 7, respectively.
References
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©2018 Wei Gou et al., published by De Gruyter, Berlin/Boston
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