Abstract
C20H22IN2O1.5, monoclinic, C2/c (no. 15), a = 38.828(4) Å, b = 9.5689(9) Å, c = 26.186(2) Å, β = 127.719(1)°, Z = 8, V = 7696.0(12) Å3, Rgt(F) = 0.0379, wRref(F2) = 0.1058, T = 296(2) K.
The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.
Data collection and handling.
| Crystal: | Block, colorless |
| Wavelength: | Mo Kα radiation (0.71073 Å) |
| μ: | 1.68 mm−1 |
| Diffractometer, scan mode: | Bruker APEX-II, φ and ω-scans |
| θmax, completeness: | 25°, >99% |
| N(hkl)measured, N(hkl)unique, Rint: | 35774, 6781, 0.018 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 5614 |
| N(param)refined: | 448 |
| Programs: | Bruker programs [1], SHELX [2, 3] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | x | y | z | Uiso*/Ueq |
|---|---|---|---|---|
| I2 | −0.079488(9) | 0.98965(3) | 0.020967(15) | 0.07124(12) |
| I1 | 0.164420(10) | 0.36573(4) | 0.309302(15) | 0.07974(13) |
| O2 | −0.03783(19) | 0.2095(5) | 0.1576(2) | 0.1342(17) |
| H2A | −0.0136 | 0.2091 | 0.1953 | 0.201* |
| H2B | −0.0363 | 0.1559 | 0.1332 | 0.201* |
| N1 | 0.01707(9) | 0.7558(3) | 0.07866(14) | 0.0492(7) |
| N2 | −0.02088(11) | 0.6172(4) | 0.10198(16) | 0.0590(8) |
| N3 | −0.18228(9) | 0.8937(3) | −0.15015(14) | 0.0463(7) |
| C5 | −0.06228(15) | 0.6206(6) | −0.1137(2) | 0.0773(14) |
| H5 | −0.0798 | 0.5913 | −0.1566 | 0.093* |
| C6 | −0.06783(12) | 0.5627(5) | −0.0705(2) | 0.0662(12) |
| C1 | −0.04127(11) | 0.6118(4) | −0.00493(18) | 0.0519(9) |
| C2 | −0.00965(11) | 0.7131(4) | 0.01290(17) | 0.0509(8) |
| C12 | 0.01034(11) | 0.7107(4) | 0.11965(18) | 0.0515(8) |
| C14 | 0.03907(12) | 0.7594(4) | 0.18777(18) | 0.0542(9) |
| C15 | 0.03324(17) | 0.8884(6) | 0.2047(2) | 0.0874(16) |
| H15 | 0.0107 | 0.9463 | 0.1737 | 0.105* |
| C16 | 0.06129(18) | 0.9309(6) | 0.2685(2) | 0.0947(18) |
| H16 | 0.0568 | 1.0169 | 0.2801 | 0.114* |
| C17 | 0.09582(14) | 0.8488(5) | 0.3153(2) | 0.0687(12) |
| C20 | 0.12821(18) | 0.9053(8) | 0.3836(2) | 0.0993(19) |
| H20A | 0.1424 | 0.9864 | 0.3828 | 0.149* |
| H20B | 0.1495 | 0.8349 | 0.4105 | 0.149* |
| H20C | 0.1131 | 0.9302 | 0.4006 | 0.149* |
| C13 | 0.05114(14) | 0.8595(5) | 0.0980(2) | 0.0667(11) |
| H13A | 0.0683 | 0.8273 | 0.0853 | 0.100* |
| H13B | 0.0695 | 0.8717 | 0.1439 | 0.100* |
| H13C | 0.0378 | 0.9471 | 0.0772 | 0.100* |
| C11 | −0.03097(19) | 0.5807(7) | 0.1463(3) | 0.0955(17) |
| H11A | −0.0206 | 0.4881 | 0.1628 | 0.143* |
| H11B | −0.0619 | 0.5843 | 0.1234 | 0.143* |
| H11C | −0.0170 | 0.6460 | 0.1815 | 0.143* |
| C10 | −0.04721(12) | 0.5593(4) | 0.0390(2) | 0.0585(10) |
| C9 | −0.07704(15) | 0.4560(5) | 0.0215(3) | 0.0837(15) |
| H9 | −0.0807 | 0.4198 | 0.0509 | 0.100* |
| C8 | −0.10241(15) | 0.4057(6) | −0.0435(3) | 0.0947(19) |
| H8 | −0.1223 | 0.3342 | −0.0559 | 0.114* |
| C7 | −0.09848(15) | 0.4576(6) | −0.0869(3) | 0.0870(16) |
| H7 | −0.1164 | 0.4238 | −0.1289 | 0.104* |
| C18 | 0.10090(14) | 0.7214(5) | 0.2975(2) | 0.0663(11) |
| H18 | 0.1238 | 0.6641 | 0.3285 | 0.080* |
| C19 | 0.07292(14) | 0.6756(5) | 0.23470(19) | 0.0615(10) |
| H19 | 0.0768 | 0.5877 | 0.2238 | 0.074* |
| C3 | −0.00445(14) | 0.7657(5) | −0.0302(2) | 0.0659(11) |
| H3 | 0.0169 | 0.8321 | −0.0174 | 0.079* |
| C4 | −0.03175(17) | 0.7183(6) | −0.0940(2) | 0.0821(14) |
| H4 | −0.0286 | 0.7559 | −0.1237 | 0.099* |
| C25 | −0.17093(13) | 1.2183(5) | −0.24712(19) | 0.0614(10) |
| H25 | −0.1688 | 1.2895 | −0.2692 | 0.074* |
| C24 | −0.15646(14) | 1.0879(5) | −0.2457(2) | 0.0651(11) |
| H24 | −0.1445 | 1.0717 | −0.2669 | 0.078* |
| C23 | −0.15906(13) | 0.9769(4) | −0.21310(19) | 0.0570(9) |
| H23 | −0.1496 | 0.8880 | −0.2136 | 0.068* |
| C22 | −0.17574(11) | 1.0019(4) | −0.18056(17) | 0.0462(8) |
| C32 | −0.19358(10) | 0.9213(4) | −0.11245(16) | 0.0453(8) |
| C34 | −0.20099(12) | 0.8063(4) | −0.08252(17) | 0.0502(8) |
| C39 | −0.24237(13) | 0.7961(5) | −0.0990(2) | 0.0643(11) |
| H39 | −0.2634 | 0.8627 | −0.1259 | 0.077* |
| C38 | −0.25224(15) | 0.6872(5) | −0.0756(2) | 0.0739(12) |
| H38 | −0.2801 | 0.6809 | −0.0871 | 0.089* |
| C37 | −0.22143(16) | 0.5866(5) | −0.0351(2) | 0.0670(11) |
| C40 | −0.2330(2) | 0.4671(6) | −0.0103(3) | 0.0951(17) |
| H40A | −0.2295 | 0.4964 | 0.0277 | 0.143* |
| H40B | −0.2142 | 0.3892 | 0.0000 | 0.143* |
| H40C | −0.2627 | 0.4399 | −0.0429 | 0.143* |
| C27 | −0.20642(12) | 1.3776(4) | −0.21622(19) | 0.0599(10) |
| H27 | −0.2063 | 1.4512 | −0.2393 | 0.072* |
| C26 | −0.18931(11) | 1.2466(4) | −0.21521(17) | 0.0521(9) |
| C33 | −0.17779(17) | 0.7502(4) | −0.1652(2) | 0.0686(11) |
| H33A | −0.1918 | 0.7425 | −0.2105 | 0.103* |
| H33B | −0.1912 | 0.6866 | −0.1537 | 0.103* |
| H33C | −0.1475 | 0.7277 | −0.1411 | 0.103* |
| C35 | −0.16969(13) | 0.7085(4) | −0.0410(2) | 0.0604(10) |
| H35 | −0.1417 | 0.7155 | −0.0289 | 0.072* |
| C36 | −0.18009(15) | 0.6008(5) | −0.0176(2) | 0.0663(11) |
| H36 | −0.1587 | 0.5362 | 0.0106 | 0.080* |
| N4 | −0.20240(9) | 1.0517(3) | −0.10570(14) | 0.0473(7) |
| C31 | −0.20382(15) | 1.0908(5) | −0.05240(19) | 0.0626(10) |
| H31A | −0.2334 | 1.1090 | −0.0694 | 0.094* |
| H31B | −0.1866 | 1.1732 | −0.0314 | 0.094* |
| H31C | −0.1924 | 1.0156 | −0.0218 | 0.094* |
| C30 | −0.20565(10) | 1.1629(4) | −0.14404(16) | 0.0454(8) |
| C21 | −0.19002(10) | 1.1365(4) | −0.17953(16) | 0.0446(8) |
| C29 | −0.22229(12) | 1.2903(4) | −0.1464(2) | 0.0565(9) |
| H29 | −0.2330 | 1.3063 | −0.1235 | 0.068* |
| C28 | −0.22303(13) | 1.3972(4) | −0.1839(2) | 0.0629(11) |
| H28 | −0.2352 | 1.4832 | −0.1866 | 0.076* |
| O1 | 0.04859(19) | 0.3069(7) | 0.2480(3) | 0.158(2) |
| H1A | 0.0758 | 0.3422 | 0.2917 | 0.236* |
| H1B | 0.0526 | 0.2371 | 0.2735 | 0.236* |
| O3 | −0.1282(3) | 0.3201(10) | 0.0871(4) | 0.251(4) |
| H3A | −0.1082 | 0.2597 | 0.1011 | 0.376* |
| H3B | −0.1444 | 0.2960 | 0.0973 | 0.376* |
Source of material
Iodomethane (3.02 g, 0.021 mol) was added dropwise to a solution of 1-methyl-2-(p-tolyl)-1H-perimidine (2.72 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 ethanol and dried under vacuum to give the title compound (3.11 g, 75%). Yellow needle crystals were obtained by recrystallization from ethyl acetate.
Experimental details
The methyl groups refined using rigid groups allowed to rotate about the N—C bond (AFIX 137 option of the SHELX program). The Uiso values of the hydrogen atoms of methyl groups were set to 1.5Ueq(C) and the Uiso values of other hydrogen atons were set to 1.2Ueq(C).
Discussion
Perimidines have drawn extensive examinations [4], [5]. There are several preparative methods for the synthesis of perimidine derivatives [6], [7].
There are two cations, two anions and three water molecules in the asymmetric unit. In its structure, the bond angles of N(1)—C(12)—N(2), N(1)—C(12)—C(14) and N(2)—C(12)—C(14) are 121.5(3), 119.7(3) and 118.7(3) in turn, which indicates the sp2 hybridization state of C(12) atom and the new-formed three-membered heterocyclic ring is essentially planar. Geometric parameteres are in accord with those of other compounds of this class reported by us [8].
Acknowledgements
This work was financially supported by the Natural Science Foundation of Hunan Province of China (2017JJ3093).
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©2018 Lin Yuan et al., published by De Gruyter, Berlin/Boston
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