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BY-NC-ND 4.0 license Open Access Published by De Gruyter (O) July 12, 2018

Crystal structure of methyl 4-(4-bromophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C20H22BrNO3

Tao-Wen Ren , Xing-Peng Xiao , Bai-Yu Li , Yu-Mei Zhao and Shao-Peng Peng EMAIL logo

Abstract

C20H22BrNO3, monoclinic, P21/n (no. 14), a = 9.597(2) Å, b = 18.236(5) Å, c = 11.640(3) Å, β = 111.355(5)°, V = 1897.3(8) Å3, Z = 4, Rgt(F) = 0.0497, wRref(F2) = 0.1240, T = 296(2) K.

CCDC no.: 1851670

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:Yellow block
Size:0.26 × 0.21 × 0.17 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:2.18 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:25.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:9434, 3337, 0.056
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1913
N(param)refined:226
Programs:Olex2 [1], SHELX [2], Bruker [3]
Table 2:

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

AtomxyzUiso*/Ueq
N10.2178(3)0.31642(16)0.4445(3)0.0437(8)
H10.1566820.3260720.3711370.052*
Br1−0.04573(7)0.05860(3)0.85548(5)0.0885(3)
O10.3753(4)0.36240(15)0.8710(3)0.0718(9)
O20.2494(3)0.45084(13)0.7455(2)0.0586(8)
O30.5493(3)0.14298(14)0.6953(2)0.0617(8)
C10.2667(6)0.4951(2)0.8529(4)0.0731(14)
H1A0.2190890.5417090.8272880.110*
H1B0.2212280.4704870.9033320.110*
H1C0.3711730.5023910.8995290.110*
C20.3101(4)0.3845(2)0.7672(4)0.0434(9)
C30.2908(4)0.34053(18)0.6568(3)0.0373(9)
C40.2202(4)0.36267(19)0.5398(3)0.0407(9)
C50.1398(5)0.43307(19)0.4947(4)0.0587(12)
H5A0.1005530.4333720.4061070.088*
H5B0.0591530.4378880.5243580.088*
H5C0.2080620.4732920.5244770.088*
C60.3070(4)0.25692(19)0.4613(3)0.0381(9)
C70.3819(4)0.23108(18)0.5767(3)0.0366(9)
C80.3544(4)0.26328(18)0.6859(3)0.0364(9)
H80.4512020.2668700.7540870.044*
C90.3177(4)0.2239(2)0.3471(3)0.0484(10)
H9A0.3877640.2522570.3226410.058*
H9B0.2205770.2269780.2809850.058*
C100.3677(5)0.1446(2)0.3633(3)0.0517(11)
C110.4040(6)0.1193(3)0.2525(4)0.0877(17)
H11A0.3164590.1237510.1789720.132*
H11B0.4826490.1491930.2451460.132*
H11C0.4357730.0690100.2636790.132*
C120.2409(5)0.0966(2)0.3705(4)0.0712(13)
H12A0.1556980.1009870.2951500.107*
H12B0.2731150.0463600.3822220.107*
H12C0.2141540.1121410.4384680.107*
C130.5030(5)0.1383(2)0.4811(3)0.0644(13)
H13A0.5296200.0869760.4963570.077*
H13B0.5863540.1632920.4698290.077*
C140.4811(4)0.1699(2)0.5933(4)0.0475(10)
C150.2546(4)0.21449(18)0.7278(3)0.0359(9)
C160.1152(4)0.1928(2)0.6472(3)0.0445(10)
H160.0821180.2094360.5661560.053*
C170.0239(5)0.1476(2)0.6831(4)0.0502(10)
H17−0.0692570.1335390.6271180.060*
C180.0726(5)0.1236(2)0.8025(4)0.0512(11)
C190.2088(6)0.1441(2)0.8854(4)0.0642(13)
H190.2410860.1274510.9664550.077*
C200.2981(5)0.1901(2)0.8473(3)0.0539(11)
H200.3901030.2048560.9041470.065*

Source of material

The title compound was synthesized according to a reported procedure [4]. A mixture of 5,5-dimethyl-cyclohexane-1,3-dione (10 mmol), 4-bromobenzaldehyde (10 mmol), 3-amino-2-butenoic acid methyl ester (10 mmol) in ethanol (100 mL) was refluxed for 2–3 h and then cooled to room temperature. After filtering precipitates were sequentially washed with ice-cooled water and ethanol and dried under vacuum.

Experimental details

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å/0.96 Å and N—H = 0.86 Å with Uiso(H) = 1.2 times Ueq(C) and 1.2 times Ueq(N).

Comment

Neuro-oncology is the study of brain and spinal cord neoplasms, many of which are (at least eventually) very dangerous and life-threatening [5]. Among the malignant brain cancers, gliomas of the brainstem and pons, glioblastoma multiforme, and high-grade (highly anaplastic) astrocytoma are among the worst [6]. Some 4-arylpolyhydroquinoline derivatives exhibit antimicrobial activity, growth stimulating effects, antifungal and plant growth regulation effects, antitumor activity, central nervous system (CNS) activity and hypotensive effect [7]. Others are known for antihistaminic activity, platelet anti-aggregating activity and local anaesthetic activity, antiallergenic effect, antidepressant effect and as anti-glioma agents [8].

In the crystal structure of the title compound (Figure), the six-membered ring containing nitrogen atom is nearly planar and the adjacent ring with the keto group adopts a flattened chair conformation. The bond distances and the bond angles in the title compound are comparable with those of known complexes [9], [10], [11], which show a slightly modified substituation scheme. The Br atom in the title compound was replaced by one -NO2 group, one -OCH3 group and one Cl atom in the complexes reported in reference [9], [10], [11], respectively.

References

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Received: 2018-04-11
Accepted: 2018-06-26
Published Online: 2018-07-12
Published in Print: 2018-08-28

©2018 Tao-Wen Ren 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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