A chalcone showing positional disorder, two related diarylcyclohexenones showing enantiomeric disorder and a related hydroxyterphenyl, all derived from simple carbonyl precursors
Four compounds are reported, all of which lie along a versatile reaction pathway which leads from simple carbonyl compounds to terphenyls. (2E)‐1‐(2,4‐Dichlorophenyl)‐3‐ [4‐(prop‐1‐en‐2‐yl)phenyl]prop‐2‐en‐1‐one, C18H14Cl2O, (I), prepared from 4‐(prop‐1‐en‐2‐yl)benzaldehyde and 2,4‐dichloroacetophen...
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| Veröffentlicht in: | Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2015-07, Vol.71 (7), p.610-617 |
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| container_title | Acta crystallographica. Section C, Crystal structure communications |
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| creator | Salian, Vinutha V. Narayana, Badiadka Yathirajan, Hemmige S. Akkurt, Mehmet Çelik, Ömer Ersanlı, Cem Cüneyt Glidewell, Christopher |
| description | Four compounds are reported, all of which lie along a versatile reaction pathway which leads from simple carbonyl compounds to terphenyls. (2E)‐1‐(2,4‐Dichlorophenyl)‐3‐ [4‐(prop‐1‐en‐2‐yl)phenyl]prop‐2‐en‐1‐one, C18H14Cl2O, (I), prepared from 4‐(prop‐1‐en‐2‐yl)benzaldehyde and 2,4‐dichloroacetophenone, exhibits disorder over two sets of atomic sites having occupancies of 0.664 (6) and 0.336 (6). The related chalcone (2E)‐3‐(4‐chlorophenyl)‐1‐(4‐fluorophenyl)prop‐2‐en‐1‐one reacts with acetone to produce (5RS)‐3‐(4‐chlorophenyl)‐5‐[4‐(propan‐2‐yl)phenyl]cyclohex‐2‐en‐1‐one, C21H21ClO, (II), which exhibits enantiomeric disorder with occupancies at the reference site of 0.662 (4) and 0.338 (4) for the (5R) and (5S) forms; the same chalcone reacts with methyl 3‐oxobutanoate to give methyl (1RS,6SR)‐4‐(4‐chlorophenyl)‐6‐[4‐(propan‐2‐yl)phenyl]‐2‐oxocyclohex‐3‐ene‐1‐carboxylate, C23H23ClO3, (III), where the reference site contains both (1R,6S) and (1S,6R) forms with occupancies of 0.923 (3) and 0.077 (3), respectively. Oxidation, using 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone, of ethyl (1RS,6SR)‐6‐(4‐bromophenyl)‐4‐(4‐fluorophenyl)‐2‐oxocyclohex‐3‐ene‐1‐carboxylate, prepared in a similar manner to (II) and (III), produces ethyl 4′′‐bromo‐4‐fluoro‐5′‐hydroxy‐1,1′:3′,1′′‐terphenyl‐4′‐carboxylate, C21H16BrFO3, (IV), which crystallizes with Z′ = 2 in the space group P. There are no significant intermolecular interactions in the structures of compounds (I) and (II), but for the major disorder component of compound (III), the molecules are linked into sheets by a combination of C—H...O and C—H...π(arene) hydrogen bonds. The two independent molecules of compound (IV) form two different centrosymmetric dimers, one built from inversion‐related pairs of C—H...O hydrogen bonds and the other from inversion‐related pairs of C—H...π(arene) hydrogen bonds. Comparisons are made with related compounds. |
| doi_str_mv | 10.1107/S2053229615011961 |
| format | Article |
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(2E)‐1‐(2,4‐Dichlorophenyl)‐3‐ [4‐(prop‐1‐en‐2‐yl)phenyl]prop‐2‐en‐1‐one, C18H14Cl2O, (I), prepared from 4‐(prop‐1‐en‐2‐yl)benzaldehyde and 2,4‐dichloroacetophenone, exhibits disorder over two sets of atomic sites having occupancies of 0.664 (6) and 0.336 (6). The related chalcone (2E)‐3‐(4‐chlorophenyl)‐1‐(4‐fluorophenyl)prop‐2‐en‐1‐one reacts with acetone to produce (5RS)‐3‐(4‐chlorophenyl)‐5‐[4‐(propan‐2‐yl)phenyl]cyclohex‐2‐en‐1‐one, C21H21ClO, (II), which exhibits enantiomeric disorder with occupancies at the reference site of 0.662 (4) and 0.338 (4) for the (5R) and (5S) forms; the same chalcone reacts with methyl 3‐oxobutanoate to give methyl (1RS,6SR)‐4‐(4‐chlorophenyl)‐6‐[4‐(propan‐2‐yl)phenyl]‐2‐oxocyclohex‐3‐ene‐1‐carboxylate, C23H23ClO3, (III), where the reference site contains both (1R,6S) and (1S,6R) forms with occupancies of 0.923 (3) and 0.077 (3), respectively. Oxidation, using 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone, of ethyl (1RS,6SR)‐6‐(4‐bromophenyl)‐4‐(4‐fluorophenyl)‐2‐oxocyclohex‐3‐ene‐1‐carboxylate, prepared in a similar manner to (II) and (III), produces ethyl 4′′‐bromo‐4‐fluoro‐5′‐hydroxy‐1,1′:3′,1′′‐terphenyl‐4′‐carboxylate, C21H16BrFO3, (IV), which crystallizes with Z′ = 2 in the space group P. There are no significant intermolecular interactions in the structures of compounds (I) and (II), but for the major disorder component of compound (III), the molecules are linked into sheets by a combination of C—H...O and C—H...π(arene) hydrogen bonds. The two independent molecules of compound (IV) form two different centrosymmetric dimers, one built from inversion‐related pairs of C—H...O hydrogen bonds and the other from inversion‐related pairs of C—H...π(arene) hydrogen bonds. Comparisons are made with related compounds.</description><identifier>ISSN: 2053-2296</identifier><identifier>ISSN: 0108-2701</identifier><identifier>EISSN: 2053-2296</identifier><identifier>EISSN: 1600-5759</identifier><identifier>DOI: 10.1107/S2053229615011961</identifier><identifier>PMID: 26146401</identifier><language>eng</language><publisher>5 Abbey Square, Chester, Cheshire CH1 2HU, England: International Union of Crystallography</publisher><subject>Acetone ; Benzaldehydes - chemistry ; Carbonyl compounds ; Chalcone - analogs & derivatives ; Chalcone - chemical synthesis ; Chalcone - chemistry ; chalcones ; Crystal structure ; Crystallization ; Crystallography ; Crystallography, X-Ray ; Cyclohexanones - chemistry ; diarylcyclohexenones ; Dimers ; Disorders ; enantiomeric disorder ; Hydrocarbons, Chlorinated - chemical synthesis ; Hydrocarbons, Chlorinated - chemistry ; Hydrogen Bonding ; Hydrogen bonds ; Molecular chemistry ; Molecular Structure ; Pathways ; Precursors ; Propane - analogs & derivatives ; Propane - chemical synthesis ; Propane - chemistry ; Stereoisomerism ; supramolecular aggregation ; Terphenyls</subject><ispartof>Acta crystallographica. Section C, Crystal structure communications, 2015-07, Vol.71 (7), p.610-617</ispartof><rights>International Union of Crystallography, 2015</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4553-f8a516d9a8312650f9d32a7d55011cafb765cfba75e7b8028ba2ef4cac113f3</citedby><cites>FETCH-LOGICAL-c4553-f8a516d9a8312650f9d32a7d55011cafb765cfba75e7b8028ba2ef4cac113f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1107%2FS2053229615011961$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1107%2FS2053229615011961$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26146401$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Salian, Vinutha V.</creatorcontrib><creatorcontrib>Narayana, Badiadka</creatorcontrib><creatorcontrib>Yathirajan, Hemmige S.</creatorcontrib><creatorcontrib>Akkurt, Mehmet</creatorcontrib><creatorcontrib>Çelik, Ömer</creatorcontrib><creatorcontrib>Ersanlı, Cem Cüneyt</creatorcontrib><creatorcontrib>Glidewell, Christopher</creatorcontrib><title>A chalcone showing positional disorder, two related diarylcyclohexenones showing enantiomeric disorder and a related hydroxyterphenyl, all derived from simple carbonyl precursors</title><title>Acta crystallographica. Section C, Crystal structure communications</title><addtitle>Acta Crystallogr C Struct Chem</addtitle><description>Four compounds are reported, all of which lie along a versatile reaction pathway which leads from simple carbonyl compounds to terphenyls. (2E)‐1‐(2,4‐Dichlorophenyl)‐3‐ [4‐(prop‐1‐en‐2‐yl)phenyl]prop‐2‐en‐1‐one, C18H14Cl2O, (I), prepared from 4‐(prop‐1‐en‐2‐yl)benzaldehyde and 2,4‐dichloroacetophenone, exhibits disorder over two sets of atomic sites having occupancies of 0.664 (6) and 0.336 (6). The related chalcone (2E)‐3‐(4‐chlorophenyl)‐1‐(4‐fluorophenyl)prop‐2‐en‐1‐one reacts with acetone to produce (5RS)‐3‐(4‐chlorophenyl)‐5‐[4‐(propan‐2‐yl)phenyl]cyclohex‐2‐en‐1‐one, C21H21ClO, (II), which exhibits enantiomeric disorder with occupancies at the reference site of 0.662 (4) and 0.338 (4) for the (5R) and (5S) forms; the same chalcone reacts with methyl 3‐oxobutanoate to give methyl (1RS,6SR)‐4‐(4‐chlorophenyl)‐6‐[4‐(propan‐2‐yl)phenyl]‐2‐oxocyclohex‐3‐ene‐1‐carboxylate, C23H23ClO3, (III), where the reference site contains both (1R,6S) and (1S,6R) forms with occupancies of 0.923 (3) and 0.077 (3), respectively. Oxidation, using 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone, of ethyl (1RS,6SR)‐6‐(4‐bromophenyl)‐4‐(4‐fluorophenyl)‐2‐oxocyclohex‐3‐ene‐1‐carboxylate, prepared in a similar manner to (II) and (III), produces ethyl 4′′‐bromo‐4‐fluoro‐5′‐hydroxy‐1,1′:3′,1′′‐terphenyl‐4′‐carboxylate, C21H16BrFO3, (IV), which crystallizes with Z′ = 2 in the space group P. There are no significant intermolecular interactions in the structures of compounds (I) and (II), but for the major disorder component of compound (III), the molecules are linked into sheets by a combination of C—H...O and C—H...π(arene) hydrogen bonds. The two independent molecules of compound (IV) form two different centrosymmetric dimers, one built from inversion‐related pairs of C—H...O hydrogen bonds and the other from inversion‐related pairs of C—H...π(arene) hydrogen bonds. Comparisons are made with related compounds.</description><subject>Acetone</subject><subject>Benzaldehydes - chemistry</subject><subject>Carbonyl compounds</subject><subject>Chalcone - analogs & derivatives</subject><subject>Chalcone - chemical synthesis</subject><subject>Chalcone - chemistry</subject><subject>chalcones</subject><subject>Crystal structure</subject><subject>Crystallization</subject><subject>Crystallography</subject><subject>Crystallography, X-Ray</subject><subject>Cyclohexanones - chemistry</subject><subject>diarylcyclohexenones</subject><subject>Dimers</subject><subject>Disorders</subject><subject>enantiomeric disorder</subject><subject>Hydrocarbons, Chlorinated - chemical synthesis</subject><subject>Hydrocarbons, Chlorinated - chemistry</subject><subject>Hydrogen Bonding</subject><subject>Hydrogen bonds</subject><subject>Molecular chemistry</subject><subject>Molecular Structure</subject><subject>Pathways</subject><subject>Precursors</subject><subject>Propane - analogs & derivatives</subject><subject>Propane - chemical synthesis</subject><subject>Propane - chemistry</subject><subject>Stereoisomerism</subject><subject>supramolecular aggregation</subject><subject>Terphenyls</subject><issn>2053-2296</issn><issn>0108-2701</issn><issn>2053-2296</issn><issn>1600-5759</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc9u1DAQhyMEolXpA3BBlrhw6Lb-EyfxcbUCWrUSh-XCKZrYE5LKsYOdsM1r8YR4u2WF4NDTWOPv-1meybK3jF4yRsurLadScK4KJiljqbzITvet1b738q_zSXYe4z2lieKyLNnr7IQXLC9yyk6zX2uiO7DaOySx87vefSejj_3UeweWmD76YDBckGnnSUALE5rUhbBYvWjrO3xAl-R4tNGBS_aAoddHn4AzBI4B3WKCf1gmDGOHbrEXBGx6LCk_020b_EBiP4wWiYbQ-ESQMaCeQ0qLb7JXLdiI50_1LNt--vh1c726-_L5ZrO-W-lcpq-3FUhWGAWVYLyQtFVGcCiN3I9LQ9uUhdRtA6XEsqkorxrg2OYaNGOiFWfZh0PqGPyPGeNUD33UaC049HOsWSmFzKko2PNooSSrCqmqhL7_B733c0iTfqSEUkpynih2oHTwMQZs6zH0Q5p5zWi9X3793_KT8-4peW4GNEfjz6oToA7Arre4PJ9Yr79t-PZWSCXEb19kvkQ</recordid><startdate>201507</startdate><enddate>201507</enddate><creator>Salian, Vinutha V.</creator><creator>Narayana, Badiadka</creator><creator>Yathirajan, Hemmige S.</creator><creator>Akkurt, Mehmet</creator><creator>Çelik, Ömer</creator><creator>Ersanlı, Cem Cüneyt</creator><creator>Glidewell, Christopher</creator><general>International Union of Crystallography</general><general>Wiley Subscription Services, Inc</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope></search><sort><creationdate>201507</creationdate><title>A chalcone showing positional disorder, two related diarylcyclohexenones showing enantiomeric disorder and a related hydroxyterphenyl, all derived from simple carbonyl precursors</title><author>Salian, Vinutha V. ; Narayana, Badiadka ; Yathirajan, Hemmige S. ; Akkurt, Mehmet ; Çelik, Ömer ; Ersanlı, Cem Cüneyt ; Glidewell, Christopher</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4553-f8a516d9a8312650f9d32a7d55011cafb765cfba75e7b8028ba2ef4cac113f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Acetone</topic><topic>Benzaldehydes - chemistry</topic><topic>Carbonyl compounds</topic><topic>Chalcone - analogs & derivatives</topic><topic>Chalcone - chemical synthesis</topic><topic>Chalcone - chemistry</topic><topic>chalcones</topic><topic>Crystal structure</topic><topic>Crystallization</topic><topic>Crystallography</topic><topic>Crystallography, X-Ray</topic><topic>Cyclohexanones - chemistry</topic><topic>diarylcyclohexenones</topic><topic>Dimers</topic><topic>Disorders</topic><topic>enantiomeric disorder</topic><topic>Hydrocarbons, Chlorinated - chemical synthesis</topic><topic>Hydrocarbons, Chlorinated - chemistry</topic><topic>Hydrogen Bonding</topic><topic>Hydrogen bonds</topic><topic>Molecular chemistry</topic><topic>Molecular Structure</topic><topic>Pathways</topic><topic>Precursors</topic><topic>Propane - analogs & derivatives</topic><topic>Propane - chemical synthesis</topic><topic>Propane - chemistry</topic><topic>Stereoisomerism</topic><topic>supramolecular aggregation</topic><topic>Terphenyls</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Salian, Vinutha V.</creatorcontrib><creatorcontrib>Narayana, Badiadka</creatorcontrib><creatorcontrib>Yathirajan, Hemmige S.</creatorcontrib><creatorcontrib>Akkurt, Mehmet</creatorcontrib><creatorcontrib>Çelik, Ömer</creatorcontrib><creatorcontrib>Ersanlı, Cem Cüneyt</creatorcontrib><creatorcontrib>Glidewell, Christopher</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Acta crystallographica. Section C, Crystal structure communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Salian, Vinutha V.</au><au>Narayana, Badiadka</au><au>Yathirajan, Hemmige S.</au><au>Akkurt, Mehmet</au><au>Çelik, Ömer</au><au>Ersanlı, Cem Cüneyt</au><au>Glidewell, Christopher</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A chalcone showing positional disorder, two related diarylcyclohexenones showing enantiomeric disorder and a related hydroxyterphenyl, all derived from simple carbonyl precursors</atitle><jtitle>Acta crystallographica. Section C, Crystal structure communications</jtitle><addtitle>Acta Crystallogr C Struct Chem</addtitle><date>2015-07</date><risdate>2015</risdate><volume>71</volume><issue>7</issue><spage>610</spage><epage>617</epage><pages>610-617</pages><issn>2053-2296</issn><issn>0108-2701</issn><eissn>2053-2296</eissn><eissn>1600-5759</eissn><abstract>Four compounds are reported, all of which lie along a versatile reaction pathway which leads from simple carbonyl compounds to terphenyls. (2E)‐1‐(2,4‐Dichlorophenyl)‐3‐ [4‐(prop‐1‐en‐2‐yl)phenyl]prop‐2‐en‐1‐one, C18H14Cl2O, (I), prepared from 4‐(prop‐1‐en‐2‐yl)benzaldehyde and 2,4‐dichloroacetophenone, exhibits disorder over two sets of atomic sites having occupancies of 0.664 (6) and 0.336 (6). The related chalcone (2E)‐3‐(4‐chlorophenyl)‐1‐(4‐fluorophenyl)prop‐2‐en‐1‐one reacts with acetone to produce (5RS)‐3‐(4‐chlorophenyl)‐5‐[4‐(propan‐2‐yl)phenyl]cyclohex‐2‐en‐1‐one, C21H21ClO, (II), which exhibits enantiomeric disorder with occupancies at the reference site of 0.662 (4) and 0.338 (4) for the (5R) and (5S) forms; the same chalcone reacts with methyl 3‐oxobutanoate to give methyl (1RS,6SR)‐4‐(4‐chlorophenyl)‐6‐[4‐(propan‐2‐yl)phenyl]‐2‐oxocyclohex‐3‐ene‐1‐carboxylate, C23H23ClO3, (III), where the reference site contains both (1R,6S) and (1S,6R) forms with occupancies of 0.923 (3) and 0.077 (3), respectively. Oxidation, using 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone, of ethyl (1RS,6SR)‐6‐(4‐bromophenyl)‐4‐(4‐fluorophenyl)‐2‐oxocyclohex‐3‐ene‐1‐carboxylate, prepared in a similar manner to (II) and (III), produces ethyl 4′′‐bromo‐4‐fluoro‐5′‐hydroxy‐1,1′:3′,1′′‐terphenyl‐4′‐carboxylate, C21H16BrFO3, (IV), which crystallizes with Z′ = 2 in the space group P. There are no significant intermolecular interactions in the structures of compounds (I) and (II), but for the major disorder component of compound (III), the molecules are linked into sheets by a combination of C—H...O and C—H...π(arene) hydrogen bonds. The two independent molecules of compound (IV) form two different centrosymmetric dimers, one built from inversion‐related pairs of C—H...O hydrogen bonds and the other from inversion‐related pairs of C—H...π(arene) hydrogen bonds. Comparisons are made with related compounds.</abstract><cop>5 Abbey Square, Chester, Cheshire CH1 2HU, England</cop><pub>International Union of Crystallography</pub><pmid>26146401</pmid><doi>10.1107/S2053229615011961</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Acetone Benzaldehydes - chemistry Carbonyl compounds Chalcone - analogs & derivatives Chalcone - chemical synthesis Chalcone - chemistry chalcones Crystal structure Crystallization Crystallography Crystallography, X-Ray Cyclohexanones - chemistry diarylcyclohexenones Dimers Disorders enantiomeric disorder Hydrocarbons, Chlorinated - chemical synthesis Hydrocarbons, Chlorinated - chemistry Hydrogen Bonding Hydrogen bonds Molecular chemistry Molecular Structure Pathways Precursors Propane - analogs & derivatives Propane - chemical synthesis Propane - chemistry Stereoisomerism supramolecular aggregation Terphenyls |
| title | A chalcone showing positional disorder, two related diarylcyclohexenones showing enantiomeric disorder and a related hydroxyterphenyl, all derived from simple carbonyl precursors |
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