Crystal structure of 2-chloro-3-(dimethoxymethyl)-6-methoxyquinoline
The title compound, C13H14ClNO3, crystallizes with Z′ = 2 in the space group Pca21, but a search for possible additional crystallographic symmetry found none. However, the crystal structure exhibits pseudosymmetry as the two independent molecules are related by an approximate but non-crystallograph...
| Main Authors: | , , , , , |
|---|---|
| Format: | Online |
| Language: | English |
| Published: |
International Union of Crystallography
2015
|
| Online Access: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4420130/ |
| id |
pubmed-4420130 |
|---|---|
| recordtype |
oai_dc |
| spelling |
pubmed-44201302015-05-20 Crystal structure of 2-chloro-3-(dimethoxymethyl)-6-methoxyquinoline Chandrika, Nanjappa Suresha Kumara, Tholappanavara H. Jasinski, Jerry P. Millikan, Sean P. Yathirajan, Hemmige S. Glidewell, Christopher Data Reports The title compound, C13H14ClNO3, crystallizes with Z′ = 2 in the space group Pca21, but a search for possible additional crystallographic symmetry found none. However, the crystal structure exhibits pseudosymmetry as the two independent molecules are related by an approximate but non-crystallographic inversion located close to (0.38, 0.26, 1/2) in the selected asymmetric unit, and the structure exhibits partial inversion twinning. The approximate inversion relationship between the two molecules in the selected asymmetric unit is clearly shown by comparison of the relevant torsion angle in the two molecules; the corresponding torsion angles have similar, although not identical magnitudes but with opposite signs. The mean planes of the quinoline rings in the two independent molecules are almost parallel, with a dihedral angle of only 0.16 (3)° between them, and the mutual orientation of these rings permits significant π–π stacking interactions between them [centroid–centroid distances = 3.7579 (15) and 3.7923 (15) Å]. In addition, the bimolecular aggregates which are related by translation along [010] are linked by a further π–π stacking interaction [centroid–centroid distance = 3.7898 (15) Å], so forming a π-stacked chain running parallel to [010]. However, there are no C—H⋯N hydrogen bonds in the structure nor, despite the number of independent aromatic rings, are there any C—H⋯π hydrogen bonds; hence there are no direction-specific interactions between adjacent π-stacked chains. International Union of Crystallography 2015-04-30 /pmc/articles/PMC4420130/ /pubmed/25995951 http://dx.doi.org/10.1107/S205698901500804X Text en © Chandrika et al. 2015 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
| repository_type |
Open Access Journal |
| institution_category |
Foreign Institution |
| institution |
US National Center for Biotechnology Information |
| building |
NCBI PubMed |
| collection |
Online Access |
| language |
English |
| format |
Online |
| author |
Chandrika, Nanjappa Suresha Kumara, Tholappanavara H. Jasinski, Jerry P. Millikan, Sean P. Yathirajan, Hemmige S. Glidewell, Christopher |
| spellingShingle |
Chandrika, Nanjappa Suresha Kumara, Tholappanavara H. Jasinski, Jerry P. Millikan, Sean P. Yathirajan, Hemmige S. Glidewell, Christopher Crystal structure of 2-chloro-3-(dimethoxymethyl)-6-methoxyquinoline |
| author_facet |
Chandrika, Nanjappa Suresha Kumara, Tholappanavara H. Jasinski, Jerry P. Millikan, Sean P. Yathirajan, Hemmige S. Glidewell, Christopher |
| author_sort |
Chandrika, Nanjappa |
| title |
Crystal structure of 2-chloro-3-(dimethoxymethyl)-6-methoxyquinoline |
| title_short |
Crystal structure of 2-chloro-3-(dimethoxymethyl)-6-methoxyquinoline |
| title_full |
Crystal structure of 2-chloro-3-(dimethoxymethyl)-6-methoxyquinoline |
| title_fullStr |
Crystal structure of 2-chloro-3-(dimethoxymethyl)-6-methoxyquinoline |
| title_full_unstemmed |
Crystal structure of 2-chloro-3-(dimethoxymethyl)-6-methoxyquinoline |
| title_sort |
crystal structure of 2-chloro-3-(dimethoxymethyl)-6-methoxyquinoline |
| description |
The title compound, C13H14ClNO3, crystallizes with Z′ = 2 in the space group Pca21, but a search for possible additional crystallographic symmetry found none. However, the crystal structure exhibits pseudosymmetry as the two independent molecules are related by an approximate but non-crystallographic inversion located close to (0.38, 0.26, 1/2) in the selected asymmetric unit, and the structure exhibits partial inversion twinning. The approximate inversion relationship between the two molecules in the selected asymmetric unit is clearly shown by comparison of the relevant torsion angle in the two molecules; the corresponding torsion angles have similar, although not identical magnitudes but with opposite signs. The mean planes of the quinoline rings in the two independent molecules are almost parallel, with a dihedral angle of only 0.16 (3)° between them, and the mutual orientation of these rings permits significant π–π stacking interactions between them [centroid–centroid distances = 3.7579 (15) and 3.7923 (15) Å]. In addition, the bimolecular aggregates which are related by translation along [010] are linked by a further π–π stacking interaction [centroid–centroid distance = 3.7898 (15) Å], so forming a π-stacked chain running parallel to [010]. However, there are no C—H⋯N hydrogen bonds in the structure nor, despite the number of independent aromatic rings, are there any C—H⋯π hydrogen bonds; hence there are no direction-specific interactions between adjacent π-stacked chains. |
| publisher |
International Union of Crystallography |
| publishDate |
2015 |
| url |
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4420130/ |
| _version_ |
1613219290975043584 |