V. Sourdon, G. Boyer, J. Galy
Apr 1, 2001
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Zeitschrift für Kristallographie - New Crystal Structures
Abstract
C15H15N, monoclinic, C l e l (No. 9), a = 10.7295(6) Ä, b = 15.1279(8)Ä, c = 7.7526(3)Ä, β = 108.8390)°, V= 1191.0Ä, Ζ=4, Rp(F) = 0.037, wR^F) = 0.062, Τ = 298 Κ. Source of material This compound was prepared by addition of methyllithium to 4-methylacridine in T H F with a modified procedure [1]. In this case the recovered 4,9-dimethyl-9,10-dihydroacridine was recrystallised in chloroform/ether (3/7) to yield 55 % of the title compound. Experimental details All the hydrogen atoms were located from a difference Fourier map, but their positions were not refined. Discussion Acridine derivatives have a wide range of biological applications, especially as antitumor agents [2]. Because of its planar structure, the acridine chromophore has shown excellent DNA binding properties [3]. Since bis-intercalation would theoretically increase DNA binding, the synthesis of polyacridines as potential bis-intercalating agents has been extensively studied [4], and we have recently prepared new acridine dimers and tetramers [5,6], We report now the molecular structure of 4,9-dimethyl-9,10-dihydroacridine which is an intermediary used in the preparation of polyacridines. Since the first crystallographic study of acridine [7], no structure of dimethyl acridane was reported. The examination of these distances and angles shows no surprising values, all distances are normal; the bond distances between the methyl substituants and the heterocycle are 1.539 Ä in the case of C7—C15 bond, and 1.497 Ä for C2—CI4 . The whole molecule is not flat with two aromatic planes (C1-C6 and C8-C13) linked by sp atoms (C7 and Ν1). The angle between C 6 C 7 C 8 is only 110.8(1)° while the angle C 1 N 1 C 1 3 is 120.2(1)°. Moreover the methyl carbon C15 is out of the molecule with an angle close to 110.1(1)° Table 1. Data collection and handling. colourless block, size 0.2 χ 0.1 χ 0.1 mm Mo K a radiation (0.71073 Ä) 0.7 cm" Nonius Kappa CCD, φ 52.68° 1132, 1094 /obs > 3 a(Iobs), 1048 143 SIR92 [8], maXus [9], ORTEP-II [10] Table 2. Atomic coordinates and displacement parameters (in A). Atom Site X y ζ i/iso H(l) 4a 0.1902 0.2567 0.3013 0.080 H(9) 4a 0.0405 0.5257 0.6329 0.087 H(7) 4a 0.2822 0.5006 0.7143 0.077 H(12) 4a -0.0386 0.2769 0.2115 0.083 H(15A) 4a 0.1986 0.3892 0.9117 0.092 H(5) 4a 0.5262 0.4873 0.7541 0.085 H( l l ) 4a -0.2212 0.3698 0.2171 0.089 H(10) 4a -0.1875 0.4805 0.4634 0.092 H(15B) 4a 0.3670 0.3909 0.9447 0.092 H(15C) 4a 0.2557 0.3121 0.8211 0.092 H(14A) 4a 0.4957 0.2132 0.2405 0.099 H(3) 4a 0.6273 0.3228 0.3833 0.088 H(4) 4a 0.6861 0.4378 0.6326 0.096 H(14B) 4a 0.3454 0.2369 0.1459 0.099 H(14C) 4a 0.3963 0.1641 0.3796 0.099 Crystal: Wavelength: μ: Diffractometer, scan mode: N(hkl)measured, N(hkl)umqlx: Criterion for /obs, N(hkl)gc. N(param)KflTKä\ Programs: * Correspondence author (e-mail: gerard.boyer@mvcf.u-3mrs.fr) 646 4,9-Dimethyl-9,10-dihydroacridine Table 3. Atomic coordinates and displacement parameters (in A). Atom Site X ζ U\\ C/22 t/33 U12 Un Uu N(l) 4a 0.21400° 0.29960(3) 0.4100° 0.0485(3) 0.0431(3) 0.0582(4) -0.0026(2) 0.0191(3) -0.0135(2) C(8) 4a 0.12870(7) 0.41880(4) 0.5450(1) 0.0480(3) 0.0398(3) 0.0443(3) 0.0014(2) 0.0188(3) 0.0007(2) CO) 4a 0.34110(7) 0.33620(4) 0.4674(1) 0.0417(3) 0.0416(3) 0.0421(3) 0.0020(3) 0.0118(2) 0.0039(2) C(13) 4a 0.10660(7) 0.34920(4) 0.4201(1) 0.0475(3) 0.0405(3) 0.0421(3) -0.0012(3) 0.0206(3) -0.0002(2) C(7) 4a 0.26480(7) 0.43160(4) 0.6790(1) 0.0561(3) 0.0418(3) 0.0434(3) -0.0006(3) 0.0142(3) -0.0056(2) C(6) 4a 0.36850(7) 0.40390(3) 0.5967(1) 0.0510(3) 0.0402(3) 0.0433(4) -0.0010(3) 0.0131(3) 0.0007(2) C(12) 4a -0.01980(7) 0.33040(4) 0.3069(1) 0.0494(3) 0.0533(4) 0.0560(4) -0.0096(3) 0.0220(3) -0.0013(3) C(9) 4a 0.02200(7) 0.47030(4) 0.5476(1) 0.0620(4) 0.0510(4) 0.0570(5) 0.0072(3) 0.0309(3) -0.0020(3) C(2) 4a 0.43810(7) 0.30310(4) 0.3998(1) 0.0512(4) 0.0519(4) 0.0447(4) 0.0076(3) 0.0186(3) 0.0066(3) C(5) 4a 0.49390(7) 0.43980(4) 0.6555(1) 0.0510(4) 0.0606(4) 0.0532(4) -0.0077(3) 0.0072(3) -0.0036(3) C(3) 4a 0.56240(7) 0.34060(5) 0.4644(1) 0.0484(4) 0.0697(4) 0.0562(4) 0.0066(3) 0.0195(3) 0.0099(3) C(14) 4a 0.41030(8) 0.22780(5) 0.2677(1) 0.0663(4) 0.0815(5) 0.0592(5) 0.0142(3) 0.0243(3) -0.0133(3) C(10) 4a -0.10390(8) 0.45260(5) 0.4320(1) 0.0516(4) 0.0682(4) 0.0671(5) 0.0088(3) 0.0299(3) 0.0091(3) C( l l ) 4a -0.12460(7) 0.38240(5) 0.3141(1) 0.0450(3) 0.0721(5) 0.0615(5) -0.0058(3) 0.0217(3) 0.0088(3) C(15) 4a 0.28000(8) 0.37870(4) 0.8542(1) 0.0719(4) 0.0694(4) 0.0463(4) -0.0007(3) 0.0191(3) -0.0015(3) C(4) 4a 0.59120(8) 0.40850(5) 0.5889(1) 0.0498(4) 0.0790(5) 0.0698(5) -0.0093(3) 0.0147(3) -0.0003(4) a: arbitrarily fixed for definition of origin.