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BY-NC-ND 4.0 license Open Access Published by De Gruyter (O) June 21, 2018

Crystal structure of ethyl 4-(3-chlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C21H24ClNO3

Wei Gou , Yan Zhou , Wei Zhong EMAIL logo , Yang Wang , Bai-Yuan Yang and An-Rong Zhao

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.

CCDC no.: 1847962

Table 1:

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]
Table 2:

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

AtomxyzUiso*/Ueq
N10.38417(14)0.07907(15)0.67038(16)0.0480(6)
H10.3826700.0690750.7301630.058
Cl10.07594(6)0.03553(7)0.64578(8)0.0899(4)
O10.34465(15)0.26977(15)0.42352(19)0.0750(8)
O20.39095(18)0.32592(16)0.5537(2)0.0915(9)
O30.38800(14)−0.03147(13)0.36612(13)0.0575(6)
C10.1287(2)0.0655(2)0.5469(3)0.0605(9)
C20.0902(2)0.0811(2)0.4651(3)0.0760(11)
H20.0363550.0765760.4621490.091
C30.1322(3)0.1035(3)0.3872(3)0.0866(13)
H30.1067080.1132160.3302030.104
C40.2129(2)0.1120(2)0.3916(3)0.0724(11)
H40.2404650.1277660.3378590.087
C50.25177(18)0.09724(17)0.4751(2)0.0484(7)
C60.20789(17)0.07292(19)0.5530(2)0.0529(8)
H60.2325810.0614880.6101670.063
C70.33959(17)0.10569(18)0.4830(2)0.0446(7)
H70.3602180.1180240.4198300.053
C80.36302(17)0.17781(18)0.5485(2)0.0451(7)
C90.36804(19)0.2649(2)0.5126(3)0.0558(8)
C100.3490(3)0.3533(3)0.3802(4)0.1065(17)
H10A0.3484470.3964900.4290800.128
H10B0.3974410.3584760.3455190.128
C110.2884(3)0.3660(3)0.3203(4)0.1195(18)
H11A0.2924200.4214300.2924630.179
H11B0.2894230.3237710.2712960.179
H11C0.2405030.3617280.3547320.179
C120.37905(17)0.16208(18)0.6394(2)0.0467(7)
C130.3931(2)0.2265(2)0.7154(3)0.0688(10)
H13A0.3970100.1983570.7754660.103
H13B0.3506620.2660550.7169450.103
H13C0.4405210.2563630.7025630.103
C140.39150(15)0.01270(17)0.60964(18)0.0403(7)
C150.37588(16)0.02432(17)0.51714(18)0.0391(6)
C160.39399(16)−0.04244(18)0.45158(19)0.0412(7)
C170.42347(18)−0.12548(18)0.4897(2)0.0487(7)
H17A0.479701−0.1255560.4852400.058
H17B0.404362−0.1707610.4493820.058
C180.40105(17)−0.14539(18)0.5907(2)0.0459(7)
C190.42054(17)−0.06797(18)0.65033(19)0.0452(7)
H19A0.398411−0.0752980.7129000.054
H19B0.476498−0.0642940.6573120.054
C200.3145(2)−0.1664(2)0.5974(3)0.0685(10)
H20A0.301358−0.1788860.6619640.103
H20B0.284591−0.1187320.5759940.103
H20C0.303248−0.2149050.5586030.103
C210.4485(2)−0.2213(2)0.6259(3)0.0715(10)
H21A0.434279−0.2340220.6900080.107
H21B0.438095−0.2697680.5866070.107
H21C0.502821−0.2078600.6230590.107

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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Received: 2018-04-10
Accepted: 2018-06-07
Published Online: 2018-06-21
Published in Print: 2018-08-28

©2018 Wei Gou 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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