(E)-3-[4-(Hexyloxy)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one

Abstract

Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.003 Å; R factor = 0.070; wR factor = 0.190; data-to-parameter ratio = 22.6.In the title compound, C 21 H 24 O 3 , the conformation of the enone group is s-cis. The benzene rings are inclined at an angle of 7.9 (1) . The alkoxy tail is planar, with a maximum deviation from the least-squares plane of 0.009 (2) Å , and adopts a trans conformation throughout. An intramolecular O-HÁ Á ÁO interaction between the keto and hydroxy groups forms S(6) ring motifs. In the crystal, molecules are arranged in a head-to-tail manner down the a axis and are subsequently stacked along the b axis, forming molecular sheets parallel to the ab plane. The crystal structure is further stabilized by weak C-HÁ Á Á interactions and short CÁ Á ÁO [3.376 (2) Å ] contacts. Related literature

(2E)-3-(3,4-Dimethoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one

“…The mean plane of the prop-2-en-1-one group, the active site in this molecule, makes angles of 7.40 (8) ° and 13.25 (8) °, respectively, with the hydroxyphenyl and dimethoxyphenyl rings. Bond lengths and angles are normal and correspond to those observed in related compounds (Butcher et al, 2006;Cao et al, 2005;Harrison et al, 2007;Jasinski et al, 2010Jasinski et al, , 2011aJasinski et al, , 2011bNgaini et al, 2009;Radha Krishna et al, 2005;Sharma et al, 1997;Wu et al, 2005). Crystal packing is stabilized by O-H (Table 2) and π-π stacking interactions (Table 3); see Fig.…”

“…For related chalcone structures, see: Butcher et al (2006); Cao et al (2005); Harrison et al (2007); Jasinski et al (2010Jasinski et al ( , 2011a; Ngaini et al (2009); Radha Krishna et al (2005); Sharma et al (1997); Wu et al (2005) Experimental (16) 147Symmetry codes: (i) x À 1 2 ; Ày þ 1 2 ; Àz þ 1; (ii) Àx þ 1; y À 1 2 ; Àz þ 1 2 .…”

(E)-3-(3,4-Dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one

“…The mean plane of the prop-2-en-1-one group, the active site in this molecule, makes angles of 3.6 (0)° and 2.6 (7)°, respectively, with the hydroxyphenyl and dimethoxyphenyl rings. Bond lengths and angles are normal (Allen et al, 1987) and corespond to those observed in related compounds (Butcher et al, 2006;Cao et al, 2005;Harrison et al, 2007;Jasinski et al, 2010Jasinski et al, , 2011aJasinski et al, , 2011bNgaini et al, 2009;Radha Krishna et al, 2005;Sharma et al, 1997;Wu et al, 2005). (Table 1) and π-π stacking interactions (Table 2, Fig.…”

“…For related structures, see: Butcher et al (2006); Cao et al (2005); Harrison et al (2007); Jasinski et al (2010Jasinski et al ( , 2011a; Ngaini et al (2009); Radha Krishna et al (2005); Sharma et al (1997); Wu et al (2005). For standard bond lengths, see: Allen et al (1987).…”