The crystal and molecular structures of three isoquinoline derivatives: 1-chloro-3-hydroxyisoquinoline, 1-phenyl-2-methyl-3-isoquinolone and 2-(2',6'-dichlorobenzyl)-1-isoquinolone

H. L. Ammon, G. L. Wheeler
1974 Acta Crystallographica Section B  
1-Chloro-3-hydroxyisoquinoline, C9H6CINO, crystallizes in space group P21/c, with a= 9.962 (1), b= 5-685 (1), c=14.671 (2) A, fl=106.360 (9) °, Z=4. 1-Phenyl-2-methyl-3-iso~uinolone, Ct6H13NO, crystallizes in space group P2a/m, with a = 12.580 (2), b = 6.869 (2), c = 14.247 (2)A,/~= 97-14 (1) °, Z= 4. There are two independent molecules on the crystallographic mirror plane. 2-(2',6'-Dichlorobenzyl)-lisoquinolone, Cx6HlINOCI2, crystallizes in space group P2~/n, with a=9.494 (2), b= 11.012 (2),
more » ... ), b= 11.012 (2), c= 14"409 (5)A, ,8= 111.02 (1) °, Z=4. The cell constants and intensity data were collected with a Picker FACS-I diffractometer, Mo K~ radiation (2=0.71069 .~), and a graphite monochromator. The structures were solved by Patterson and direct methods and refined by the full-matrix least-squares technique with anisotropic temperature factors for C, N, O, CI and isotropic terms for H. The structure of lchloro-3-hydroxyisoquinoline (R=0.045) confirms the lactim tautomeric form of this compound in the solid state and provides an accurate set of bond lengths for the isoquinoline ring. Bond distances in the nitrogen-containing 6-ring of the 1-isoquinolone (R= 0.038) correspond more closely to the lengths in a 2-pyridone than do the 3-isoquinolone (R = 0.084) distances. The structure of homophthalimide, which is isostructural with 1-chloro-3-hydroxyisoquinoline, is reported in the Appendix. The compound, C9HvNO2, crystallizes in space group P2~/c with cell constants a= 10.040 (6), b= 5.814 (3), c= 13.256 (5) A"/~= 104.23 ° (5), Z=4. The structure refinement used anisotropic temperature factors for C, N and O. The H atoms were included at calculated positions, and the H parameters were not refined. The final R index was 0.114.
doi:10.1107/s056774087400447x fatcat:fu5s65m2cndnxicxlxboditoye