Home Physical Sciences Crystal structure of 1,3-dimethyl-2-phenyl-1H-perimidin-3-ium iodide, C19H17IN2
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Crystal structure of 1,3-dimethyl-2-phenyl-1H-perimidin-3-ium iodide, C19H17IN2

  • Lin Yuan , Zhong-Yan Li EMAIL logo , Xian-You Yuan , Min Zhang and Fang Liu
Published/Copyright: May 8, 2017

Abstract

C19H17IN2, monoclinic, C2/c, a = 18.701(4) Å, b = 7.9230(16) Å, c = 24.069(6) Å, β = 111.168(2)°, V = 3325.6(13) Å3, Z = 8, Rgt(F) = 0.0201, wRref(F2) = 0.0462, T = 296(2) K.

CCDC no.:: 1470938

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.

Table 1

Data collection and handling.

Crystal:Yellow block
Size:0.38 × 0.36 × 0.32 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:19.2 cm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
2θmax, completeness:50°, 98.6%
N(hkl)measured, N(hkl)unique, Rint:14906, 2887, 0.015
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2763
N(param)refined:203
Programs:Bruker programs [1], SHELX [2, 3] , PLATON [17]
Table 2

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

AtomxyzUiso*/Ueq
N10.02337(10)0.0880(2)0.10919(7)0.0404(4)
N20.00485(9)0.3438(2)0.14921(7)0.0412(4)
C2−0.05664(12)0.0579(3)0.08300(9)0.0415(4)
C140.13526(12)0.2481(3)0.16972(10)0.0430(5)
C110.05110(11)0.2267(2)0.14101(9)0.0392(4)
C1−0.10546(11)0.1761(2)0.09493(8)0.0396(4)
C6−0.18568(12)0.1482(3)0.07256(9)0.0483(5)
C10−0.07554(11)0.3222(3)0.12880(9)0.0410(4)
C9−0.12331(14)0.4357(3)0.14080(11)0.0569(6)
H9−0.10350.53290.16260.068*
C160.25785(14)0.3241(3)0.16719(13)0.0608(6)
H160.28760.36600.14660.073*
C3−0.08599(14)−0.0823(3)0.04876(11)0.0569(6)
H3−0.0537−0.16050.04100.068*
C170.29231(13)0.2778(3)0.22568(12)0.0583(6)
H170.34520.28700.24450.070*
C120.07474(14)−0.0462(3)0.10397(12)0.0593(6)
H12A0.0642−0.14850.12100.089*
H12B0.1270−0.01340.12480.089*
H12C0.0666−0.06460.06270.089*
C150.17931(13)0.3095(3)0.13828(11)0.0539(5)
H150.15630.34020.09850.065*
C8−0.20211(15)0.4040(4)0.11994(12)0.0677(7)
H8−0.23420.47960.12920.081*
C190.17027(13)0.2034(3)0.22913(10)0.0535(6)
H190.14090.16380.25040.064*
C130.03612(15)0.5060(3)0.17746(13)0.0628(7)
H13A0.03100.51310.21570.094*
H13B0.00840.59700.15270.094*
H13C0.08930.51360.18250.094*
C180.24860(13)0.2178(3)0.25649(12)0.0599(6)
H180.27210.18650.29620.072*
C5−0.21444(14)0.0039(3)0.03718(11)0.0607(6)
H5−0.2670−0.01640.02170.073*
C7−0.23314(14)0.2659(4)0.08657(11)0.0615(6)
H7−0.28590.24880.07290.074*
C4−0.16575(16)−0.1051(3)0.02568(12)0.0677(7)
H4−0.1859−0.19830.00160.081*
I2a0.00000.92943(3)0.25000.04629(7)
I1a0.00000.50000.00000.08320(11)
  1. aOccupancy: 0.5.

Source of material

  1. Iodomethane (3.02 g, 0.021 mol) was added in one portion to a solution of 2-phenyl-1H-perimidine (2.44 g, 0.01 mol) in dimethylformamide (15 mL) at 373 K. The mixture was heated for 8 h, giving a yellow precipitate. After cooling, the yellow solid was filtered and dried under vacuum to give 1-methyl-2-phenyl-1H-perimidine (1.83 g, 71%).

  2. Iodomethane (3.02 g, 0.021 mol) was added dropwise to a solution of 1-methyl-2-phenyl-1H-perimidine (2.58 g, 0.01 mol) in dimethylformamide (20 mL) at 373 K. The mixture was heated for 8 h, giving a yellow precipitate. After cooling, the yellow solid was filtered, washed with anhydrous ethanol and dried under vacuum to give the desired salt 1,3-dimethyl-2-phenyl-1H-perimidin-3-ium iodide (3.04 g, 76%). A light yellow crystal was obtained by recrystallization from anhydrous ethanol.

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 [2], [3]). The Uiso values of the hydrogen atoms of the methyl groups were set to 1.5Ueq(C) and the Uiso values of all other hydrogen atoms were set to 1.2 Ueq(C).

Comment

Perimidines have long attracted the attention of researchers because they exhibit a diverse range of biological activities [4], [5], [6], [7]. Perimidines can also be used as dyes and have a wide application in industrial field with solvent black 3 being a notable example 3 [8]. There are several preparative methods available for the synthesis of perimidine derivatives [9], [10], [11], [12], [13]. The most common method is the condensation reaction of 1,8-diaminonaphthalene with a carbonyl group [14], [15], [16]. Herein, a perimidine iodate was synthesized and characterized by single-crystal X-ray diffraction [14, 15] . In the structure of the title compound, the bond angles N(1)—C(11)—N(2), N(1)—C(11)—C(14) and N(2)—C(11)—C(14) are 121.40(18), 119.33(18) and 119.23(17)°, respectively, indicative of the sp2 hybridization state of the C(11) atom. The newly-formed three-membered heterocyclic ring is essentially planar, as demonstrated by the fact that the angle between the naphthalene and N-heterocyclic rings is 4.065°. As revelaed by PLATON analysis [17], the maximum deviation from the least-squares plane through the 13 atoms of the perimidine ring is 0.060(2) Å. Two half-occupied iodide anions are present in the asymmetric unit and sit on special positions.

Acknowledgement

This work was financially supported by the Scientific Research Fund of Hunan Provincial Education Department (16B104), the Opening Project of Key Laboratory of Comprehensive Utilization of Advantage Plants Resources in Hunan South (XNZW16C01), the Natural Science Foundation of Hunan Province of China (2017JJ3093), the Scientific Research Fund of Hunan University of Science and Engineering (16XKY063), and the Construct Program of the Key Discipline in Hunan University of Science and Engineering (2016).

References

1 Bruker: APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, WI, USA (2013).Search in Google Scholar

2 Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Search in Google Scholar

3 Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar

4 Bu, X.; Deady, L. W.; Finlay, G. J.; Baguley, B. C.; Denny, W. A.: Synthesis and cytotoxic activity of 7-oxo-7H-dibenz[f,ij]isoquinoline and 7-oxo-7H-benzo[e]perimidine derivatives. J. Med. Chem. 44 (2001) 2004–2014.10.1021/jm010041lSearch in Google Scholar

5 Gong, X. W.; Li, X.; Li, W. L.; Gao, X.; Xu, W. F.; Zhai, H. M.: Synthesis and crystal structure of (E)-4-(benzyloxy)-2-(cinnamoyl-oxy)-N,N,N-trimethyl-4-oxobutan-1-aminium chloride as a double-prodrug. Chin. J. Struct. Chem. 27 (2008) 177–182.Search in Google Scholar

6 Ye, J.; Sun, X. X.; Qiu, S. Y.; Hu, A. X.: Synthesis, crystal structure and fungicidal activity of N-(4-tert-buty)-5-(1,2,4-triazol-1-yl)thiazol-2-yl) propionamide. Chin. J. Struct. Chem. 3 (2014)3 429–433.Search in Google Scholar

7 Fu, C. R.; Pei, J.; Ning, Y.; Liu, M.; Shan, P. C.; Liu, J.; Li, Y. Q.; Hu, F. Z.; Zhu, Y. Q.; Yang, H. Z.; Zou, X. M.: Synthesis and insecticidal activities of novel pyrazole oxime ether derivatives with different substituted pyridyl rings. Pest Manag. Sci. 70 (2013) 1207–1214.10.1002/ps.3672Search in Google Scholar

8 Hashim, J. A.; Kezhal, M. S.: Synthesis, characterization and biological activity of 2-aryl-2,3-dihydro-1H-perimidine. Res. Pharm. Biotech. 5 (2014) 1–6.Search in Google Scholar

9 Vanden, E. J. J.; Delfosse, F.; Mayence, A.; Haverbeke, Y. V.: Old reagents, new results-aromatization of Hantzsch 1,4-dihydropyridines with manganese-dioxide and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Tetrahedron 51 (1995) 5813–5818.10.1016/0040-4020(95)00318-3Search in Google Scholar

10 Hendrickson, J. B.; Hussoin, M. S.: Seeking the ideal dehydrating reagent. J. Org. Chem. 52 (1987) 4137–4139.10.1021/jo00227a041Search in Google Scholar

11 Deady, L. W.; Rodemann, T. J.: Synthesis of perimidine and fused perimidine derivatives from reaction of 1,8-naphthalenediamine with an iminoisocoumarin. Heterocycl. Chem. 35 (1998) 1417–1419.10.1002/jhet.5570350633Search in Google Scholar

12 Mueller-Westerhoff, U. T.; Vance, B.; Dong. I. Y.: The synthesis of dithiolene dyes with strong near-IR absorption. Tetrahedron 47 (1991) 909–932.10.1016/S0040-4020(01)80932-7Search in Google Scholar

13 Starshikov, M.; Pozharskii, F. T.: Synthesis of 2-(5-halogeno-2-f uryl)-2,3-dihydroperimidines. Chem. Heterocycl. Compd. 9 (1973) 922–924.10.1007/BF00471584Search in Google Scholar

14 Maslak, P.; Chopra, A.; Moylan, C. R.; Wortmann, R.; Lebus, S.; Rheingold, A. L.; Yap, G. P. A.: Optical properties of spiroconjugated charge-transfer dyes. J. Am. Chem. Soc. 118 (1996) 1471–1481.10.1021/ja9533003Search in Google Scholar

15 Starshikov, N. M.; Pozharskii, A. F.: Heterocyclic analogs of pleiadiene. Chem. Heterocycl. Compd. 10 (1978) 1413–1417.10.1007/BF00469962Search in Google Scholar

16 Sokolov, V. I.; Pozharskii, A. F.; Kashparov, I. S.; Ivanov, A. G.: Heterocyclic analogs of pleiadiene. Chem. Heterocycl. Compd. 4 (1974) 558–561.10.1007/BF00945648Search in Google Scholar

17 Spek, A. L.: Structure validation in chemical crystallography. Acta Crystallogr. D65 (2009) 148–155.10.1107/S090744490804362XSearch in Google Scholar PubMed PubMed Central

Received: 2016-10-5
Accepted: 2017-4-5
Published Online: 2017-5-8
Published in Print: 2017-7-26

©2017 Lin Yuan et al., published by De Gruyter.

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

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