Structure of 4-hydroxy-4-androstene-3,17-dione

Abstract

C19H2603, P21212j, a = 18.540 (1), b = 24.348 (4), c = 7.3237 (6) A, V 3306.1 A 3, M r 302.41, Z = 8, D c = 1.22 Mg m-a; 3843 observations, 3114 > 2o¥. 4-Hydroxy-4-androstene-3,17-dione (4OH-A) is an effective inhibitor of estrogen synthetase and has been shown to be effective in controlling estrogen-dependent reproductive and neoplastic processes [Brodie, Schwarzel, Shaikh & Brodie (1977). Endocrinology, 100, 1684-1685]. The structure determination was undertaken as part of a study on the structural requirements for the aromatase system. The structure contains hydrogen-bonded dimers. Introduction. Crystals of 4-hydroxy-4-androstene-3,17dione were grown from ethyl acetate. A crystal approximately 0.20 × 0.22 × 0.80 mm was used for the collection of 3843 reflections on an Enraf-Nonius CAD-4 diffractometer. Cell constants were determined by least-squares analysis of the 20 values for 22 independent reflections in the interval 72.36 ° 2 a F and 0.066 for all 3843 data.~ The function minimized in the least-squares * Author to whom correspondence should be addressed. 5-Lists of structure factors and anisotropic thermal parameters have been deposited with the British Library Lending Division as Supplementary Publication No. SUP 34747 (20 pp.). Copies may be obtained through The Executive Secretary, International Union of Crystallography, 5 Abbey Square, Chester CH 1 2HU, England. 0567-7408/80/010201-03501.00 procedure was Y~ w(IFol -IFcl) 2 where w = 1/a~o and aro is defined in Stout & Jensen (1968, equation H14) with an instability factor of 0.06. The scattering factors O17 'r II s°l l ~,~ 11.529(5) I h-~ 1.538(4) . , , ~ ' ~ 11541(4).~L 1.53o(6) 1.9 l l .532(41 11.545(5) 11.528(5) I 11-548(4) 11-528(5) I 1.577(6) I1 540(4) I L. .= I 1 h : 5 3 2 ~ ~ f~ l J ' 1.532(4) '~ 1.523(4) 153315) 11.506(5) 11.525(4) 11.521(4) 1.207(4) .,,,,~'~,,~ }'J~44~}4~/..,7~., 1 -4~14 ~ . , ~ 1.216 ( 4 ) / _ _ _ _ / ~ 34Z~4 }~,,f ~ 4 'J 4 I' 4 J . ~ ~ _ . . . . U ~ ~ :26.., [I o ~ ~ ; ~ , ~:~,11 1.363(3) ~ 125.7 1 367(4) 124 7 I 11z,1 L . . . . . . . I ~ g ~ o . , ~.~ ,20:8, ' 1 2 3 , 4 1 1 ~ 1 ) C ( l O ) C ( 9 ) a , 107.7 108.6 ° 1 2 1 ~ 0 C ( 1 0 ) C(19) = 108.1 107.8 ~ ~ 2 ) C ( 1 3 ) (C 17 ) 116.4 117.7 ~ 4 ) C ( 1 3 ) C(18) I 11 3.5 113.3 0 / , z,J.:~ !! 4.3_~121.9 . . . . v 114.8 1~:~.8 N