Do C—H...O and C—H...π interactions help to stabilize a non-centrosymmetric structure for racemic 2,3-dibromo-1,3-diphenylpropan-1-one?

Harrison, William T. A.; Yathirajan, H. S.; Sarojini, B. K.; Narayana, B.; Anilkumar, H. G.

doi:10.1107/s0108270105036942

Cited by 23 publications

(20 citation statements)

References 10 publications

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“…Chalcone dibromides usually have higher melting points and are thermally stable. Only a few structures of these compounds have been reported (Butcher, Yathirajan, Anilkumar et al, 2006;Harrison et al, 2005;Yathirajan, Mayekar et al, 2007;Yathirajan, Vijesh et al, 2007). In continuation to our studies on crystal structures of chalcones, we report the synthesis and crystal structure of the title compound.…”

Section: S1 Commentmentioning

confidence: 79%

“…For applications of chalcone compounds, see: Liu et al (2003); Nielson et al (1998); Rajas et al (2002); Dinkova-Kostova et al (1998); Goto et al (1991); Uchida et al (1998); Tam et al (1989); Indira et al (2002); Sarojini et al (2006). For related structures, see: Butcher, Yathirajan, Anilkumar et al (2006); ; Harrison et al (2005); Yathirajan, Mayekar et al (2007); Yathirajan, Vijesh et al (2007). For hydrogen-bond motifs, see: Bernstein et al (1995).…”

Section: Related Literaturementioning

confidence: 99%

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2,3-Dibromo-3-(4-chlorophenyl)-1-(2-hydroxyphenyl)propan-1-one

Fun

Loh

Sarojini³

et al. 2011

Acta Cryst E

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Section: S1 Commentmentioning

confidence: 79%

Section: Related Literaturementioning

confidence: 99%

2,3-Dibromo-3-(4-chlorophenyl)-1-(2-hydroxyphenyl)propan-1-one

Fun

Loh

Sarojini³

et al. 2011

Acta Cryst E

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“…18b). In addition, weak C-HÁ Á Á interactions {C8A-H8A3Á Á Á Cg3 viii = 2.95 Å and 123 ; C8C-H8C1Á Á ÁCg4 = 2.99 Å and 127 [symmetry code: (viii) x À 1, y + 1, z]; C7C-H7C2Á Á Á Cg8 vi = 2.98 Å and 134 [symmetry code: (Harrison et al, 2005) further stabilize the crystal structure (Cg1 is the centroid of the N1A/C2A/N3A/C4A/ C5A/C6A ring, Cg2 that of the C9A/C10A/C11A/C12A/C13A/ C14A ring, Cg3 that of the N1B/C2B/N3B/C4B/C5B/C6B ring, Cg4 that of the C9B/C10B/C11B/C12B/C13B/C14B ring, Cg5 that of the N1C/C2C/N3C/C4C/C5C/C6C ring and Cg8 that of the C19A/C20A/C21A/C22A/C23A/C24A ring).…”

Section: Table 13mentioning

confidence: 99%

Supramolecular hydrogen-bonding patterns in salts of the antifolate drugs trimethoprim and pyrimethamine

Darious

Muthiah

Perdih

2018

Acta Crystallogr C Struct Chem

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Nine salts of the antifolate drugs trimethoprim and pyrimethamine, namely, trimethoprimium [or 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium] 2,5-dichlorothiophene-3-carboxylate monohydrate (TMPDCTPC, 1:1), CHNO·CHClOS, (I), trimethoprimium 3-bromothiophene-2-carboxylate monohydrate, (TMPBTPC, 1:1:1), CHNO·CHBrOS·HO, (II), trimethoprimium 3-chlorothiophene-2-carboxylate monohydrate (TMPCTPC, 1:1:1), CHNO·CHClOS·HO, (III), trimethoprimium 5-methylthiophene-2-carboxylate monohydrate (TMPMTPC, 1:1:1), CHNO·CHOS·HO, (IV), trimethoprimium anthracene-9-carboxylate sesquihydrate (TMPAC, 2:2:3), CHNO·CHO·1.5HO, (V), pyrimethaminium [or 2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium] 2,5-dichlorothiophene-3-carboxylate (PMNDCTPC, 1:1), CHClN·CHClOS, (VI), pyrimethaminium 5-bromothiophene-2-carboxylate (PMNBTPC, 1:1), CHClN·CHBrOS, (VII), pyrimethaminium anthracene-9-carboxylate ethanol monosolvate monohydrate (PMNAC, 1:1:1:1), CHClN·CHO·CHOH·HO, (VIII), and bis(pyrimethaminium) naphthalene-1,5-disulfonate (PMNNSA, 2:1), 2CHClN·CHOS, (IX), have been prepared and characterized by single-crystal X-ray diffraction. In all the crystal structures, the pyrimidine N1 atom is protonated. In salts (I)-(III) and (VI)-(IX), the 2-aminopyrimidinium cation interacts with the corresponding anion via a pair of N-H...O hydrogen bonds, generating the robust R(8) supramolecular heterosynthon. In salt (IV), instead of forming the R(8) heterosynthon, the carboxylate group bridges two pyrimidinium cations via N-H...O hydrogen bonds. In salt (V), one of the carboxylate O atoms bridges the N1-H group and a 2-amino H atom of the pyrimidinium cation to form a smaller R(6) ring instead of the R(8) ring. In salt (IX), the sulfonate O atoms mimic the role of carboxylate O atoms in forming an R(8) ring motif. In salts (II)-(IX), the pyrimidinium cation forms base pairs via a pair of N-H...N hydrogen bonds, generating a ring motif [R(8) homosynthon]. Compounds (II) and (III) are isomorphous. The quadruple DDAA (D = hydrogen-bond donor and A = hydrogen-bond acceptor) array is observed in (I). In salts (II)-(IV) and (VI)-(IX), quadruple DADA arrays are present. In salts (VI) and (VII), both DADA and DDAA arrays co-exist. The crystal structures are further stabilized by π-π stacking interactions [in (I), (V) and (VII)-(IX)], C-H...π interactions [in (IV)-(V) and (VII)-(IX)], C-Br...π interactions [in (II)] and C-Cl...π interactions [in (I), (III) and (VI)]. Cl...O and Cl...Cl halogen-bond interactions are present in (I) and (VI), with distances and angles of 3.0020 (18) and 3.5159 (16) Å, and 165.56 (10) and 154.81 (11)°, respectively.

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“…It has been shown that extended p systems with terminal donor-acceptor substituents exhibit large b values [3,4]. In these categories, chalcone derivatives are attracting a great deal of attention due to their high NLO coefficients [5][6][7][8][9], and good crystallizability [10][11][12]. As observed in our laboratory [13,14], single crystal structures of two such NLO crystals of chalcone, 1-(4-bromophenyl)-3-(2,4-dichlorophenyl) prop-2-en-1-one (2,4-DiCL-4 0 -bromochalcone), and 3-(2,4-dichlorophenyl)-1-(4-methylphenyl) prop-2-en-1-one (2,4-DiCL-4 0 -methylchalcone), possess a second harmonic generation (SHG) conversion efficiency of about 1.5 and 1.2 times that of urea, respectively.…”

Section: Introductionmentioning

confidence: 99%