Concomitant polymorphism in the stereoselective synthesis of a β-benzyl-β-hydroxyaspartate analogue
Two concomitant polymorphs, (I) and (II), of a β‐benzyl‐β‐hydroxyaspartate analogue [systematic name: dibenzyl 2‐benzyl‐2‐hydroxy‐3‐(4‐methylphenylsulfonamido)succinate], C32H31NO7S, crystallize from a mixture of ethyl acetate and cyclohexane at ambient temperature. The structure of (I) has triclini...
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| Veröffentlicht in: | Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2011-08, Vol.67 (8), p.o301-o305 |
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| creator | Mekki, Sofiane Rolland, Valérie Bellahouel, Salima Lee, Arie van der Rolland, Marc |
| description | Two concomitant polymorphs, (I) and (II), of a β‐benzyl‐β‐hydroxyaspartate analogue [systematic name: dibenzyl 2‐benzyl‐2‐hydroxy‐3‐(4‐methylphenylsulfonamido)succinate], C32H31NO7S, crystallize from a mixture of ethyl acetate and cyclohexane at ambient temperature. The structure of (I) has triclinic (P) symmetry and that of (II) monoclinic (P21/c) symmetry. Both crystal structures are made up of a stacking of homochiral racemic dimers (2S,3S and 2R,3R) which are internally connected by a similar R22(9) hydrogen‐bonding pattern consisting of intermolecular N—H...O and O—H...O hydrogen bonds. The centroid of the racemic dimer lies on an inversion centre. The main structural difference between the two polymorphs is the conformational orientation of two of the four aromatic rings present in the molecule. Polymorph (II) is found to be twinned by reticular merohedry with twin index 3 and twin fractions 0.854 (1) and 0.146 (1). |
| doi_str_mv | 10.1107/S0108270111024632 |
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The structure of (I) has triclinic (P) symmetry and that of (II) monoclinic (P21/c) symmetry. Both crystal structures are made up of a stacking of homochiral racemic dimers (2S,3S and 2R,3R) which are internally connected by a similar R22(9) hydrogen‐bonding pattern consisting of intermolecular N—H...O and O—H...O hydrogen bonds. The centroid of the racemic dimer lies on an inversion centre. The main structural difference between the two polymorphs is the conformational orientation of two of the four aromatic rings present in the molecule. Polymorph (II) is found to be twinned by reticular merohedry with twin index 3 and twin fractions 0.854 (1) and 0.146 (1).</description><identifier>ISSN: 0108-2701</identifier><identifier>EISSN: 1600-5759</identifier><identifier>DOI: 10.1107/S0108270111024632</identifier><identifier>PMID: 21817797</identifier><language>eng</language><publisher>5 Abbey Square, Chester, Cheshire CH1 2HU, England: International Union of Crystallography</publisher><subject>Analogue ; Aspartic Acid - analogs & derivatives ; Aspartic Acid - chemistry ; Chemical Sciences ; Crystal structure ; Crystallization ; Crystallography, X-Ray ; Dimers ; Hydrogen Bonding ; Inversions ; Medicinal Chemistry ; Molecular Conformation ; Molecular Structure ; Organic chemistry ; Other ; Stacking ; Symmetry</subject><ispartof>Acta crystallographica. 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Section C, Crystal structure communications</title><addtitle>Acta Cryst. C</addtitle><description>Two concomitant polymorphs, (I) and (II), of a β‐benzyl‐β‐hydroxyaspartate analogue [systematic name: dibenzyl 2‐benzyl‐2‐hydroxy‐3‐(4‐methylphenylsulfonamido)succinate], C32H31NO7S, crystallize from a mixture of ethyl acetate and cyclohexane at ambient temperature. The structure of (I) has triclinic (P) symmetry and that of (II) monoclinic (P21/c) symmetry. Both crystal structures are made up of a stacking of homochiral racemic dimers (2S,3S and 2R,3R) which are internally connected by a similar R22(9) hydrogen‐bonding pattern consisting of intermolecular N—H...O and O—H...O hydrogen bonds. The centroid of the racemic dimer lies on an inversion centre. The main structural difference between the two polymorphs is the conformational orientation of two of the four aromatic rings present in the molecule. Polymorph (II) is found to be twinned by reticular merohedry with twin index 3 and twin fractions 0.854 (1) and 0.146 (1).</description><subject>Analogue</subject><subject>Aspartic Acid - analogs & derivatives</subject><subject>Aspartic Acid - chemistry</subject><subject>Chemical Sciences</subject><subject>Crystal structure</subject><subject>Crystallization</subject><subject>Crystallography, X-Ray</subject><subject>Dimers</subject><subject>Hydrogen Bonding</subject><subject>Inversions</subject><subject>Medicinal Chemistry</subject><subject>Molecular Conformation</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Other</subject><subject>Stacking</subject><subject>Symmetry</subject><issn>0108-2701</issn><issn>1600-5759</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc9u1DAQhy0EokvhAbig3IBDwGPHf3LcrugWaQVCBSG4WLOJwxqSOLWzpeGxeBCeCa9S9oIEJ3tmvm800o-Qx0BfAFD18pIC1UxRSBUrJGd3yAIkpblQorxLFodxfpifkAcxfqWUMsb4fXLCQINSpVoQu_J95Ts3Yj9mg2-nzodh52KXuT4bdzaLow3WR9vaanTXqZ761I4uZr7JMPv1M9_a_sfU5um3m-rgbyaMA4YRR5thj63_srcPyb0G22gf3b6n5MP5q_eri3zzdv16tdzkVSEKkYtSVqpBywAKiZVkQnNGpVRKgZS0ELSRsNVYWlFXnDFEymuqy61tGOqa81PyfN67w9YMwXUYJuPRmYvlxhx6tFAgoNTXkNinMzsEf7W3cTSdi5VtW-yt30ejNRSKU0UT-eyfJEgFTMpSqITCjFbBxxhsc7wCqDlkZv7KLDlPbtfvt52tj8afkBKgZ-C7a-30_41m-Wm1_syhFEnNZ9WlHG-OKoZvRiquhPn4Zm2S_e7s_EyYS_4bNaqxMA</recordid><startdate>201108</startdate><enddate>201108</enddate><creator>Mekki, Sofiane</creator><creator>Rolland, Valérie</creator><creator>Bellahouel, Salima</creator><creator>Lee, Arie van der</creator><creator>Rolland, Marc</creator><general>International Union of Crystallography</general><scope>BSCLL</scope><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><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0003-4503-3554</orcidid><orcidid>https://orcid.org/0000-0001-6493-8442</orcidid><orcidid>https://orcid.org/0000-0002-4567-1831</orcidid></search><sort><creationdate>201108</creationdate><title>Concomitant polymorphism in the stereoselective synthesis of a β-benzyl-β-hydroxyaspartate analogue</title><author>Mekki, Sofiane ; Rolland, Valérie ; Bellahouel, Salima ; Lee, Arie van der ; Rolland, Marc</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4545-596c7fae21146ac6258320667771660450f61b8a9e5dc322aa03d089bef2a8d33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Analogue</topic><topic>Aspartic Acid - analogs & derivatives</topic><topic>Aspartic Acid - chemistry</topic><topic>Chemical Sciences</topic><topic>Crystal structure</topic><topic>Crystallization</topic><topic>Crystallography, X-Ray</topic><topic>Dimers</topic><topic>Hydrogen Bonding</topic><topic>Inversions</topic><topic>Medicinal Chemistry</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Other</topic><topic>Stacking</topic><topic>Symmetry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mekki, Sofiane</creatorcontrib><creatorcontrib>Rolland, Valérie</creatorcontrib><creatorcontrib>Bellahouel, Salima</creatorcontrib><creatorcontrib>Lee, Arie van der</creatorcontrib><creatorcontrib>Rolland, Marc</creatorcontrib><collection>Istex</collection><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><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>Acta crystallographica. Section C, Crystal structure communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mekki, Sofiane</au><au>Rolland, Valérie</au><au>Bellahouel, Salima</au><au>Lee, Arie van der</au><au>Rolland, Marc</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Concomitant polymorphism in the stereoselective synthesis of a β-benzyl-β-hydroxyaspartate analogue</atitle><jtitle>Acta crystallographica. Section C, Crystal structure communications</jtitle><addtitle>Acta Cryst. C</addtitle><date>2011-08</date><risdate>2011</risdate><volume>67</volume><issue>8</issue><spage>o301</spage><epage>o305</epage><pages>o301-o305</pages><issn>0108-2701</issn><eissn>1600-5759</eissn><abstract>Two concomitant polymorphs, (I) and (II), of a β‐benzyl‐β‐hydroxyaspartate analogue [systematic name: dibenzyl 2‐benzyl‐2‐hydroxy‐3‐(4‐methylphenylsulfonamido)succinate], C32H31NO7S, crystallize from a mixture of ethyl acetate and cyclohexane at ambient temperature. The structure of (I) has triclinic (P) symmetry and that of (II) monoclinic (P21/c) symmetry. Both crystal structures are made up of a stacking of homochiral racemic dimers (2S,3S and 2R,3R) which are internally connected by a similar R22(9) hydrogen‐bonding pattern consisting of intermolecular N—H...O and O—H...O hydrogen bonds. The centroid of the racemic dimer lies on an inversion centre. The main structural difference between the two polymorphs is the conformational orientation of two of the four aromatic rings present in the molecule. Polymorph (II) is found to be twinned by reticular merohedry with twin index 3 and twin fractions 0.854 (1) and 0.146 (1).</abstract><cop>5 Abbey Square, Chester, Cheshire CH1 2HU, England</cop><pub>International Union of Crystallography</pub><pmid>21817797</pmid><doi>10.1107/S0108270111024632</doi><orcidid>https://orcid.org/0000-0003-4503-3554</orcidid><orcidid>https://orcid.org/0000-0001-6493-8442</orcidid><orcidid>https://orcid.org/0000-0002-4567-1831</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Analogue Aspartic Acid - analogs & derivatives Aspartic Acid - chemistry Chemical Sciences Crystal structure Crystallization Crystallography, X-Ray Dimers Hydrogen Bonding Inversions Medicinal Chemistry Molecular Conformation Molecular Structure Organic chemistry Other Stacking Symmetry |
| title | Concomitant polymorphism in the stereoselective synthesis of a β-benzyl-β-hydroxyaspartate analogue |
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