(E)-3-(Anthracen-9-yl)-1-(4-bromophenyl)prop-2-en-1-one

Abstract

In the title mol­ecule, C23H15BrO, the prop-2-en-1-one unit is planar and it makes dihedral angles of 20.9 (1) and 45.8 (1)°, respectively, with the 4-bromo­phenyl ring and the anthracene ring system. The interplanar angle between the 4-bromophenyl ring and the anthracene ring system is 35.52 (7)°. In the crystal structure, mol­ecules are linked into dimers by C—H⋯Br hydrogen bonds, and the dimers are linked into a zigzag network parallel to the bc plane by weak C—H⋯O hydrogen bonds and C—H⋯π inter­actions involving the central benzene ring of the anthracene ring system.

(2E)-3-(2-Anthracen-2-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one

“…The dihedral angles between the mean planes of the 2-anthryl and benzene rings are 73.0 (9)° and 73.3 (3)° in A and B, respectively. Bond lengths and angles are normal and correspond to those observed in the related compounds ((Z)-3-(9-anthryl)-1-(4-methoxyphenyl) prop-2-en-1-one (Chantrapromma et al, 2009), (E)-3-(anthracen-9-yl)-1-(4-bromophenyl)prop-2-en-1-one (Suwunwong et al, 2009), (Z)-3-(9-anthryl)-1-(4-bromophenyl)-2-(4-nitro-1H-imidazol-1-yl) prop-2-en-1-one (Lu et al, 2009), (Z)-3-(9-anthryl)-2-(4-nitro-1H-imidazol-1-yl)-1-p-tolylprop-2-en-1-one (Wang et al, 2009) and (E)-3-(9anthryl)-1-(4-fluorophenyl)-2-(4-nitro-1H-imidazol-1-yl) prop-2-en-1-one (Wang et al, 2010).…”

(Z)-3-(Anthracen-9-yl)-1-(2-ethoxyphenyl)prop-2-en-1-one

“…For bond-length data, see: Allen et al (1987). For related structures, see: Chantrapromma et al (2009Chantrapromma et al ( , 2010; Suwunwong et al (2009). For background to and applications of chalcones, see: Kobkeatthawin et al (2010); Nowakowska (2007); Oliveira et al (2007); Patil & Dharmaprakash (2008); Saydam et al (2003); Svetlichny et al (2007); Tewtrakul et al (2003).…”

“…They have been studied for non-linear optical (Patil & Dharmaprakash, 2008), biological activities including anti-inflammatory, antileishmanial, antimicrobial, antioxidant (Nowakowska, 2007;Oliveira et al, 2007;Saydam et al, 2003) and HIV-1 protease inhibitory (Tewtrakul et al, 2003) as well as fluorescence properties (Kobkeatthawin et al, 2010;Svetlichny et al, 2007). We have previously reported the crystal structures of several chalcone derivatives containing the anthracene moiety which show interesting fluorescence properties (Suwunwong et al, 2009;Chantrapromma et al, 2009Chantrapromma et al, , 2010.…”

A second orthorhombic polymorph of (Z)-3-(9-anthryl)-1-(2-thienyl)prop-2-en-1-one

“…Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009). In continuation of our study of chalcone derivatives (Chantrapromma et al, 2009;Fun et al, 2009;Suwunwong et al, 2009) which can be used for non-linear optical (NLO) materials (Patil & Dharmaprakash, 2008), fluorescent materials (Svetlichny et al, 2007) and bioactive compounds (Saydam et al, 2003), the title heteroaryl chalcone (I) was synthesized and its crystal structure was previously reported in the orthorhombic space group Pna2 1 (Fun et al, 2009). In the present work, the compound crystallized in the orthorhombic space group P2 1 2 1 2 1 from an ethanol/acetone (1:1) solvent mixture, while the crystal of the Pna2 1 form crystallized from hot ethanol.…”

“…For the structure of the first polymorph, see: Fun et al (2009). For background to and applications of chalcones, see: Chantrapromma et al (2009); Patil & Dharmaprakash (2008); Saydam et al (2003); Suwunwong et al (2009); Svetlichny et al (2007). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986).…”