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Crystal structures of three co-crystals of 4,4'-bipyridyl with 4-alk-oxy-benzoic acids: 4-eth-oxy-benzoic acid-4,4'-bipyridyl (2/1), 4-n-propoxybenzoic acid-4,4'-bipyridyl (2/1) and 4-n-but-oxy-benzoic acid-4,4'-bipyridyl (2/1).

Tabuchi Y, Gotoh K, Ishida H - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: Struct.Chem. 49, 1137-1140], the present study shows that the space group is P21/n with Z = 4.The 2:1 units of (I), (II) and (III) are linked via C-H⋯O hydrogen bonds, forming sheet, double-tape and tape structures, respectively.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Faculty of Science, Okayama University, Okayama 700-8530, Japan.

ABSTRACT
The crystal structures of three hydrogen-bonded co-crystals of 4-alk-oxy-benzoic acid-4,4'-bipyridyl (2/1), namely, 2C9H10O3·C10H8N2, (I), 2C10H12O3·C10H8N2, (II) and 2C11H14O3·C10H8N2, (III), have been determined at 93 K. Although the structure of (I) has been determined in the space group P21 with Z = 4 [Lai et al. (2008 ▸). J. Struct. Chem. 49, 1137-1140], the present study shows that the space group is P21/n with Z = 4. In each crystal, the components are linked by O-H⋯N hydrogen bonds, forming a linear hydrogen-bonded 2:1 unit of the acid and the base. The 2:1 unit of (I) adopts nearly pseudo-C 2 symmetry, viz. twofold rotation around an axis passing through the mid-point of the central C-C bond of 4,4'-bipyridyl, while the units of (II) and (III), except for the terminal alkyl chains, have pseudo-inversion symmetry. The 2:1 units of (I), (II) and (III) are linked via C-H⋯O hydrogen bonds, forming sheet, double-tape and tape structures, respectively.

No MeSH data available.


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The mol­ecular structure of compound (III), showing the atom-numbering scheme. Displacement ellipsoids of non-H atoms are drawn at the 50% probability level and H atoms are drawn as circles of arbitrary size. The O—H⋯N hydrogen bonds are indicated by dashed lines.
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fig3: The mol­ecular structure of compound (III), showing the atom-numbering scheme. Displacement ellipsoids of non-H atoms are drawn at the 50% probability level and H atoms are drawn as circles of arbitrary size. The O—H⋯N hydrogen bonds are indicated by dashed lines.

Mentions: The mol­ecular structure of (I) is shown in Fig. 1 ▸. Compound (I) crystallizes in the space group P21/n with Z = 4. For the structure (space group P21) previously determined by Lai et al. (2008 ▸), ADDSYM in PLATON (Spek, 2009 ▸) detected missed symmetry elements, viz. a centre of inversion and a glide plane. The mol­ecular structures of (II) and (III) are shown in Figs. 2 ▸ and 3 ▸, respectively. The asymmetric units each comprise two crystallographically independent 4-alk­oxy­benzoic acid mol­ecules and one 4,4′-bipyridyl mol­ecule, and the two acids and the base are held together by O—H⋯N hydrogen bonds (Tables 1 ▸, 2 ▸ and 3 ▸), forming a linear hydrogen-bonded 2:1 aggregate. Similar to the reported structure of the 2:1 unit of 4-meth­oxy­benzoic acid–4,4′-bipyridyl (2/1) (Mukherjee & Desiraju, 2014 ▸; Ramon et al., 2014 ▸), the 2:1 unit of (I) also adopts nearly pseudo-C2 symmetry, viz. twofold rotation around an axis passing through the mid-point of the central C21—C26 bond of the 4,4′-bipyridyl mol­ecule. On the other hand, the 2:1 units of (II) and (III), except for the terminal alkyl chains, have pseudo-inversion symmetry.


Crystal structures of three co-crystals of 4,4'-bipyridyl with 4-alk-oxy-benzoic acids: 4-eth-oxy-benzoic acid-4,4'-bipyridyl (2/1), 4-n-propoxybenzoic acid-4,4'-bipyridyl (2/1) and 4-n-but-oxy-benzoic acid-4,4'-bipyridyl (2/1).

Tabuchi Y, Gotoh K, Ishida H - Acta Crystallogr E Crystallogr Commun (2015)

The mol­ecular structure of compound (III), showing the atom-numbering scheme. Displacement ellipsoids of non-H atoms are drawn at the 50% probability level and H atoms are drawn as circles of arbitrary size. The O—H⋯N hydrogen bonds are indicated by dashed lines.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4645087&req=5

fig3: The mol­ecular structure of compound (III), showing the atom-numbering scheme. Displacement ellipsoids of non-H atoms are drawn at the 50% probability level and H atoms are drawn as circles of arbitrary size. The O—H⋯N hydrogen bonds are indicated by dashed lines.
Mentions: The mol­ecular structure of (I) is shown in Fig. 1 ▸. Compound (I) crystallizes in the space group P21/n with Z = 4. For the structure (space group P21) previously determined by Lai et al. (2008 ▸), ADDSYM in PLATON (Spek, 2009 ▸) detected missed symmetry elements, viz. a centre of inversion and a glide plane. The mol­ecular structures of (II) and (III) are shown in Figs. 2 ▸ and 3 ▸, respectively. The asymmetric units each comprise two crystallographically independent 4-alk­oxy­benzoic acid mol­ecules and one 4,4′-bipyridyl mol­ecule, and the two acids and the base are held together by O—H⋯N hydrogen bonds (Tables 1 ▸, 2 ▸ and 3 ▸), forming a linear hydrogen-bonded 2:1 aggregate. Similar to the reported structure of the 2:1 unit of 4-meth­oxy­benzoic acid–4,4′-bipyridyl (2/1) (Mukherjee & Desiraju, 2014 ▸; Ramon et al., 2014 ▸), the 2:1 unit of (I) also adopts nearly pseudo-C2 symmetry, viz. twofold rotation around an axis passing through the mid-point of the central C21—C26 bond of the 4,4′-bipyridyl mol­ecule. On the other hand, the 2:1 units of (II) and (III), except for the terminal alkyl chains, have pseudo-inversion symmetry.

Bottom Line: Struct.Chem. 49, 1137-1140], the present study shows that the space group is P21/n with Z = 4.The 2:1 units of (I), (II) and (III) are linked via C-H⋯O hydrogen bonds, forming sheet, double-tape and tape structures, respectively.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Faculty of Science, Okayama University, Okayama 700-8530, Japan.

ABSTRACT
The crystal structures of three hydrogen-bonded co-crystals of 4-alk-oxy-benzoic acid-4,4'-bipyridyl (2/1), namely, 2C9H10O3·C10H8N2, (I), 2C10H12O3·C10H8N2, (II) and 2C11H14O3·C10H8N2, (III), have been determined at 93 K. Although the structure of (I) has been determined in the space group P21 with Z = 4 [Lai et al. (2008 ▸). J. Struct. Chem. 49, 1137-1140], the present study shows that the space group is P21/n with Z = 4. In each crystal, the components are linked by O-H⋯N hydrogen bonds, forming a linear hydrogen-bonded 2:1 unit of the acid and the base. The 2:1 unit of (I) adopts nearly pseudo-C 2 symmetry, viz. twofold rotation around an axis passing through the mid-point of the central C-C bond of 4,4'-bipyridyl, while the units of (II) and (III), except for the terminal alkyl chains, have pseudo-inversion symmetry. The 2:1 units of (I), (II) and (III) are linked via C-H⋯O hydrogen bonds, forming sheet, double-tape and tape structures, respectively.

No MeSH data available.


Related in: MedlinePlus