4-(4-Chlorobenzyloxy)-3-methoxybenzaldehyde

Abstract

Key indicators: single-crystal X-ray study; T = 294 K; mean (C-C) = 0.005 Å; R factor = 0.054; wR factor = 0.157; data-to-parameter ratio = 13.8.In the title compound, C 15 H 13 ClO 3 , the vanillin group makes a dihedral angle of 72.79 (9) with the chlorobenzene ring. The crystal structure is stabilized by weak non-classical intermolecular C-HÁ Á ÁO hydrogen bonds that form centrosymmetric dimers. Related literatureFor general background, see: Allen et al. (1987); Jones et al. (1979); Larson & Pecoraro (1991); Santos et al. (2001). Experimental Crystal data C 15 H 13 ClO 3 M r = 276.70 Monoclinic, P2 1 =c a = 9.054 (3) Å b = 8.535 (2) Å c = 17.828 (5) Å = 90.10 (2) V = 1377.7 (7) Å 3 Z = 4 Mo K radiation = 0.28 mm À1 T = 294 (2) K 0.28 Â 0.22 Â 0.20 mm Data collection Bruker SMART APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T min = 0.912, T max = 0.946 6675 measured reflections 2383 independent reflections 1124 reflections with I > 2(I) R int = 0.048

4-(Benzyloxy)benzaldehyde

“…In common with three other derivatives (Li & Chen (2008); Liu et al (2006); Zhen et al (2006)), the two aromatic rings of 4-(benzyloxy)benzaldehyde approach coplanarity (C13C8C2C7 = -9.2 (3)°), whilst the similarly substituted species described by Gerkin (1999), Allwood et al (1985) and Liu et al (2007) are very twisted (torsion angle range 31.7 to 99.1 °).…”

“…For discussion of C-HÁ Á ÁO contacts in a related methoxy derivative, see: Gerkin (1999). For other related structures, see: Allwood et al (1985); Li & Chen (2008); Liu et al (2006Liu et al ( , 2007; Zhen et al (2006). For background to the antiretroviral treatment programme of AIDS, see: UNAIDS/WHO (2009).…”

Crystal structures and Hirshfeld surface analyses of 4,4′-{[1,3-phenylenebis(methylene)]bis(oxy)}bis(3-methoxybenzaldehyde) and 4,4′-{[(1,4-phenylenebis(methylene)]bis(oxy)}bis(3-methoxybenzaldehyde)

“…A search for 4-benzyloxy-3-methoxybenzaldehydes gave eight hits. Apart from 4-benzyloxy-3-methoxybenzaldehyde itself (vanillin benzyl ether: COBNUC; Gerkin, 1999), the other hits include the 4-nitrobenzyloxy derivative (VOHYUN; Li & Chen, 2008), the 4-fluorobenzyloxy derivative (POMQIT; Bernard-Gauthier & Schirrmacher, 2014) and the 4-chlorobenzyloxy derivative (WINROB; Liu et al, 2007). In VOHYUN, the 3-methoxybenzaldehyde ring is inclined to the 4-benzyloxy ring by 5.00 (11) , while in COBNUC this dihedral angle is 78.11 (9) .…”