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Intermolecular head-to-head interaction of carbonyl groups in bicyclic hydrogen-bonded synthon based on β-hydroxy ketones
In this study, we report a counterintuitive carbonyl–carbonyl interaction explored for crystalline (2 RS ,3 RS )-1-aryl-2-bromo-3-hydroxy-3-(2-nitrophenyl)-propan-1-ones. The mentioned β-hydroxyketones display an ability to form dimensionally different crystal formative motifs ranging from 1D to 3D....
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| Published in: | CrystEngComm 2019, Vol.21 (10), p.1587-1599 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c259t-4534200e390ecccae481f3195280556de4eaa1ed884d5b15f3f15232b2a2ec733 |
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| cites | cdi_FETCH-LOGICAL-c259t-4534200e390ecccae481f3195280556de4eaa1ed884d5b15f3f15232b2a2ec733 |
| container_end_page | 1599 |
| container_issue | 10 |
| container_start_page | 1587 |
| container_title | CrystEngComm |
| container_volume | 21 |
| creator | Fayzullin, Robert R. Shteingolts, Sergey A. Lodochnikova, Olga A. Mamedova, Vera L. Korshin, Dmitry E. Mamedov, Vakhid A. |
| description | In this study, we report a counterintuitive carbonyl–carbonyl interaction explored for crystalline (2
RS
,3
RS
)-1-aryl-2-bromo-3-hydroxy-3-(2-nitrophenyl)-propan-1-ones. The mentioned β-hydroxyketones display an ability to form dimensionally different crystal formative motifs ranging from 1D to 3D. Despite the structural differences, primarily in intermolecular interactions, all the studied compounds are arranged by the same bicyclic hydrogen-bonded twelve-membered supramolecular synthon
R
22(12), with the essential feature being an
attractive
interaction between two oxygen atoms of the
head-to-head
-arranged carbonyl groups CO⋯OC. This unusual interaction along with all the other interactions that are present in the crystal structures, for instance, H-bonds and hydrogen–hydrogen and carbonyl–halogen contacts, were investigated by means of quantum-topological analysis of the calculated electron density. |
| doi_str_mv | 10.1039/C8CE02132E |
| format | article |
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RS
,3
RS
)-1-aryl-2-bromo-3-hydroxy-3-(2-nitrophenyl)-propan-1-ones. The mentioned β-hydroxyketones display an ability to form dimensionally different crystal formative motifs ranging from 1D to 3D. Despite the structural differences, primarily in intermolecular interactions, all the studied compounds are arranged by the same bicyclic hydrogen-bonded twelve-membered supramolecular synthon
R
22(12), with the essential feature being an
attractive
interaction between two oxygen atoms of the
head-to-head
-arranged carbonyl groups CO⋯OC. This unusual interaction along with all the other interactions that are present in the crystal structures, for instance, H-bonds and hydrogen–hydrogen and carbonyl–halogen contacts, were investigated by means of quantum-topological analysis of the calculated electron density.</description><identifier>ISSN: 1466-8033</identifier><identifier>EISSN: 1466-8033</identifier><identifier>DOI: 10.1039/C8CE02132E</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Aromatic compounds ; Carbonyl groups ; Carbonyls ; Crystal structure ; Crystallography ; Electron density ; Hydrogen ; Hydrogen bonding ; Ketones ; Oxygen atoms</subject><ispartof>CrystEngComm, 2019, Vol.21 (10), p.1587-1599</ispartof><rights>Copyright Royal Society of Chemistry 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c259t-4534200e390ecccae481f3195280556de4eaa1ed884d5b15f3f15232b2a2ec733</citedby><cites>FETCH-LOGICAL-c259t-4534200e390ecccae481f3195280556de4eaa1ed884d5b15f3f15232b2a2ec733</cites><orcidid>0000-0001-6265-5684 ; 0000-0001-9614-5092 ; 0000-0002-3740-9833</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,4024,27923,27924,27925</link.rule.ids></links><search><creatorcontrib>Fayzullin, Robert R.</creatorcontrib><creatorcontrib>Shteingolts, Sergey A.</creatorcontrib><creatorcontrib>Lodochnikova, Olga A.</creatorcontrib><creatorcontrib>Mamedova, Vera L.</creatorcontrib><creatorcontrib>Korshin, Dmitry E.</creatorcontrib><creatorcontrib>Mamedov, Vakhid A.</creatorcontrib><title>Intermolecular head-to-head interaction of carbonyl groups in bicyclic hydrogen-bonded synthon based on β-hydroxy ketones</title><title>CrystEngComm</title><description>In this study, we report a counterintuitive carbonyl–carbonyl interaction explored for crystalline (2
RS
,3
RS
)-1-aryl-2-bromo-3-hydroxy-3-(2-nitrophenyl)-propan-1-ones. The mentioned β-hydroxyketones display an ability to form dimensionally different crystal formative motifs ranging from 1D to 3D. Despite the structural differences, primarily in intermolecular interactions, all the studied compounds are arranged by the same bicyclic hydrogen-bonded twelve-membered supramolecular synthon
R
22(12), with the essential feature being an
attractive
interaction between two oxygen atoms of the
head-to-head
-arranged carbonyl groups CO⋯OC. This unusual interaction along with all the other interactions that are present in the crystal structures, for instance, H-bonds and hydrogen–hydrogen and carbonyl–halogen contacts, were investigated by means of quantum-topological analysis of the calculated electron density.</description><subject>Aromatic compounds</subject><subject>Carbonyl groups</subject><subject>Carbonyls</subject><subject>Crystal structure</subject><subject>Crystallography</subject><subject>Electron density</subject><subject>Hydrogen</subject><subject>Hydrogen bonding</subject><subject>Ketones</subject><subject>Oxygen atoms</subject><issn>1466-8033</issn><issn>1466-8033</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpNkM1Kw0AUhQdRsFY3PsGAO2F0ftPJUkLVQsGNrsNk5qZNTTN1JgHjY_kgPpNTK-jqnMv57r1wELpk9IZRkd8WuphTzgSfH6EJk1lGNBXi-J8_RWcxbihlkjE6QR-Lroew9S3YoTUBr8E40nuyV9zsM2P7xnfY19iaUPlubPEq-GEXU4yrxo62bSxejy74FXQkEQ4cjmPXr9NaZWKakvn6JD_M-4hfofcdxHN0Ups2wsWvTtHL_fy5eCTLp4dFcbcklqu8J1IJySkFkVOw1hqQmtWC5YprqlTmQIIxDJzW0qmKqVrUTHHBK2442JkQU3R1uLsL_m2A2JcbP4QuvSw507NMzLTKE3V9oGzwMQaoy11otiaMJaPlvtvyr1vxDVXzbj4</recordid><startdate>2019</startdate><enddate>2019</enddate><creator>Fayzullin, Robert R.</creator><creator>Shteingolts, Sergey A.</creator><creator>Lodochnikova, Olga A.</creator><creator>Mamedova, Vera L.</creator><creator>Korshin, Dmitry E.</creator><creator>Mamedov, Vakhid A.</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-6265-5684</orcidid><orcidid>https://orcid.org/0000-0001-9614-5092</orcidid><orcidid>https://orcid.org/0000-0002-3740-9833</orcidid></search><sort><creationdate>2019</creationdate><title>Intermolecular head-to-head interaction of carbonyl groups in bicyclic hydrogen-bonded synthon based on β-hydroxy ketones</title><author>Fayzullin, Robert R. ; Shteingolts, Sergey A. ; Lodochnikova, Olga A. ; Mamedova, Vera L. ; Korshin, Dmitry E. ; Mamedov, Vakhid A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c259t-4534200e390ecccae481f3195280556de4eaa1ed884d5b15f3f15232b2a2ec733</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Aromatic compounds</topic><topic>Carbonyl groups</topic><topic>Carbonyls</topic><topic>Crystal structure</topic><topic>Crystallography</topic><topic>Electron density</topic><topic>Hydrogen</topic><topic>Hydrogen bonding</topic><topic>Ketones</topic><topic>Oxygen atoms</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fayzullin, Robert R.</creatorcontrib><creatorcontrib>Shteingolts, Sergey A.</creatorcontrib><creatorcontrib>Lodochnikova, Olga A.</creatorcontrib><creatorcontrib>Mamedova, Vera L.</creatorcontrib><creatorcontrib>Korshin, Dmitry E.</creatorcontrib><creatorcontrib>Mamedov, Vakhid A.</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>CrystEngComm</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fayzullin, Robert R.</au><au>Shteingolts, Sergey A.</au><au>Lodochnikova, Olga A.</au><au>Mamedova, Vera L.</au><au>Korshin, Dmitry E.</au><au>Mamedov, Vakhid A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Intermolecular head-to-head interaction of carbonyl groups in bicyclic hydrogen-bonded synthon based on β-hydroxy ketones</atitle><jtitle>CrystEngComm</jtitle><date>2019</date><risdate>2019</risdate><volume>21</volume><issue>10</issue><spage>1587</spage><epage>1599</epage><pages>1587-1599</pages><issn>1466-8033</issn><eissn>1466-8033</eissn><abstract>In this study, we report a counterintuitive carbonyl–carbonyl interaction explored for crystalline (2
RS
,3
RS
)-1-aryl-2-bromo-3-hydroxy-3-(2-nitrophenyl)-propan-1-ones. The mentioned β-hydroxyketones display an ability to form dimensionally different crystal formative motifs ranging from 1D to 3D. Despite the structural differences, primarily in intermolecular interactions, all the studied compounds are arranged by the same bicyclic hydrogen-bonded twelve-membered supramolecular synthon
R
22(12), with the essential feature being an
attractive
interaction between two oxygen atoms of the
head-to-head
-arranged carbonyl groups CO⋯OC. This unusual interaction along with all the other interactions that are present in the crystal structures, for instance, H-bonds and hydrogen–hydrogen and carbonyl–halogen contacts, were investigated by means of quantum-topological analysis of the calculated electron density.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/C8CE02132E</doi><tpages>13</tpages><orcidid>https://orcid.org/0000-0001-6265-5684</orcidid><orcidid>https://orcid.org/0000-0001-9614-5092</orcidid><orcidid>https://orcid.org/0000-0002-3740-9833</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1466-8033 |
| ispartof | CrystEngComm, 2019, Vol.21 (10), p.1587-1599 |
| issn | 1466-8033 1466-8033 |
| language | eng |
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| source | Royal Society of Chemistry Journals |
| subjects | Aromatic compounds Carbonyl groups Carbonyls Crystal structure Crystallography Electron density Hydrogen Hydrogen bonding Ketones Oxygen atoms |
| title | Intermolecular head-to-head interaction of carbonyl groups in bicyclic hydrogen-bonded synthon based on β-hydroxy ketones |
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