Home Physical Sciences Crystal structure of 2-(4-fluorophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16ClIN2
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Crystal structure of 2-(4-fluorophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16ClIN2

  • Zhong-Yan Li , Lin Yuan EMAIL logo , Xian-You Yuan and Min Zhang
Published/Copyright: August 1, 2017

Abstract

C19H16ClIN2, monoclinic, P21/c (no. 14), a = 7.3359(11) Å, b = 18.424(3) Å, c = 12.8968(19) Å, β = 93.230(2)°, V = 1740.3(4) Å3, Z = 4, Rgt(F) = 0.0213, wRref(F2) = 0.0562, T = 296(2) K.

CCDC no.:: 1534966

Table 1

Data collection and handling.

Crystal:Yellow needle
Size:0.38 × 0.35 × 0.32 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:19.9 cm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
2θmax, completeness:50°, >99%
N(hkl)measured, N(hkl)unique, Rint:16222, 3066, 0.016
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2859
N(param)refined:210
Programs:SHELX [1, 2] , Bruker programs [3]
Table 2

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

AtomxyzUiso*/Ueq
I10.64951(2)0.681046(9)0.366570(13)0.05085(8)
Cl10.26776(13)0.51968(4)0.58110(7)0.0728(2)
C130.2264(3)0.84342(12)0.57358(16)0.0356(4)
C170.2538(4)0.61389(13)0.57756(18)0.0478(6)
C160.1024(4)0.64697(14)0.5296(2)0.0499(6)
H160.00760.61920.49950.060*
N10.2568(2)0.87952(9)0.48649(13)0.0367(4)
C150.0938(3)0.72168(13)0.52721(19)0.0472(5)
H15−0.00650.74460.49430.057*
C180.3953(4)0.65397(15)0.62298(19)0.0521(6)
H180.49670.63080.65420.063*
N20.1909(2)0.87785(10)0.66080(14)0.0386(4)
C140.2343(3)0.76274(12)0.57368(17)0.0388(5)
C190.3855(3)0.72889(14)0.62181(18)0.0471(5)
H190.47960.75640.65310.057*
C100.1961(3)0.95470(12)0.66810(17)0.0404(5)
C10.2236(3)0.99353(12)0.57629(17)0.0383(5)
C120.3040(4)0.84112(14)0.39152(18)0.0485(5)
H12A0.33000.79120.40760.073*
H12B0.40960.86330.36420.073*
H12C0.20340.84390.34080.073*
C60.2246(3)1.07044(13)0.5779(2)0.0487(6)
C70.1982(4)1.10570(15)0.6740(3)0.0634(8)
H70.19701.15610.67720.076*
C110.1372(4)0.83751(15)0.75354(19)0.0533(6)
H11A0.11360.78780.73520.080*
H11B0.02900.85880.77900.080*
H11C0.23430.83980.80660.080*
C50.2544(3)1.10802(14)0.4853(2)0.0591(7)
H50.25711.15850.48510.071*
C30.2776(3)0.99470(14)0.3931(2)0.0504(6)
H30.29370.97040.33110.060*
C20.2520(3)0.95667(12)0.48235(17)0.0373(4)
C90.1737(4)0.99058(16)0.7599(2)0.0587(7)
H90.15790.96480.82070.070*
C40.2792(4)1.07100(15)0.3965(2)0.0616(7)
H40.29781.09680.33590.074*
C80.1750(4)1.06634(17)0.7606(3)0.0697(8)
H80.15931.09050.82280.084*

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Source of materials

Iodomethane (3.02 g, 0.021 mol) was added dropwise to a solution of 2-(4-chlorophenyl)-1-methyl-1H-perimidine (2.92 g, 0.01 mol) in dimethylformamide (20 mL) at 373.15 K. The mixture was heated for 6 h, giving a yellow precipitate. After cooling, the yellow solid was filtered, washed with a little ethanol and dried under vacuum to give the product 2-(4-chlorophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide (2.73 g, 63%). Yellow needle crystals were obtained by recrystallization from ethyl acetate.

Experimental details

All hydrogen atoms were identified in difference Fourier syntheses. The methyl groups were idealized and refined using rigid groups allowed to rotate about the N—C bond (AFIX 137 option of the SHELXL-2013 program). The Uiso values of the hydrogen atoms of methyl groups were set to 1.5Ueq(C) and the Uiso values of all other hydrogen atons were set to 1.2Ueq(C).

Comment

Perimidines have drawn extensive examinations of many researchers recently [4], [5], [6]. There are several preparative methods for the synthesis of perimidine derivatives [7, 8] . But the characters of their corresponding salts have not been fully studied. Here, we present the crystal structure of a new perimidinium iodide, which is part of our ongoing study on perimidinium salts [9]. In its structure, the bond angles of N(1)—C(13)—N(2), N(1)—C(13)—C(14) and N(2)—C(13)—C(14) are 121.6(2)°, 119.35(18)° and 119.04(19)° in turn, which indicates the sp2 hybridization state of C(13) atom and the triheterocyclic moiety is essentially planar. All bond lengths and angles are in the expected ranges.

Acknowledgement

This work was financially supported by the Scientific Research Fund of Hunan Provincial Education Department (No. 16B104), Natural Science Foundation of Hunan Province of China (2017JJ3093), the Opening Project of Key Laboratory of Comprehensive Utilization of Advantage Plants Resources in Hunan South (No. XNZW16C01) and the Scientific Research Fund of Hunan University of Science and Engineering (No. 16XKY063).

References

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Received: 2017-3-3
Accepted: 2017-7-7
Published Online: 2017-8-1
Published in Print: 2017-9-26

©2017 Zhong-Yan Li et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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