Structure of (±)-(1R,6S)-1-benzyloxy-8,11,11-trimethyl-6-phenylthiobicyclo[5.3.1]undec-7-en-3-one
C27H32O2S, Mr = 420.61, monoclinic, P2(1)/c, a = 8.4756(13), b = 14.710(2), c = 18.425(3) A, beta = 99.575(13) degrees, V = 2265.2(6) A3, Z = 4, Dx = 1.23 g cm-3, mu = 1.5567 cm-1, Mo K alpha, lambda = 0.7107 A, F(000) = 904, T = 298 K, R = 0.0630 for 2942 reflections [Fo greater than or equal to 6...
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| Veröffentlicht in: | Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 1991-02, Vol.47 (2), p.468-470 |
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| container_title | Acta crystallographica. Section C, Crystal structure communications |
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| creator | Lynch, V. M. Fishpaugh, J. R. Martin, S. F. Davis, B. E. |
| description | C27H32O2S, Mr = 420.61, monoclinic, P2(1)/c, a = 8.4756(13), b = 14.710(2), c = 18.425(3) A, beta = 99.575(13) degrees, V = 2265.2(6) A3, Z = 4, Dx = 1.23 g cm-3, mu = 1.5567 cm-1, Mo K alpha, lambda = 0.7107 A, F(000) = 904, T = 298 K, R = 0.0630 for 2942 reflections [Fo greater than or equal to 6 sigma (Fo)]. The cyclooctane portion of the [5.3.1] ring system assumes the boat-chair conformation while the cyclohexene portion has the boat conformation. As has been observed in other [5.3.1]undecene systems, ring strain appears to cause a distortion of the geometry of the bridgehead alkene. The bond length C7--C8 [1.343(5) A] is long for an isolated C--C double bond. The Csp2--Csp3 bond lengths at C7 are asymmetric with C7--C6 being 1.498(5) A while C7--C11 is 1.535(5) A. The maximum deviation from ideality for the torsion angles around the double bond is 16.2(4) degrees (absolute value). This twist in the alkene group is reflected in the non-planarity of the group [max. deviation 0.193(6) A for C9] and in the dihedral angle between the nearly planar portions (C6, C7, C8, C11 and C7, C8, C9, C15), which is 9.4(2) degrees. |
| doi_str_mv | 10.1107/S0108270190008320 |
| format | Article |
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M. ; Fishpaugh, J. R. ; Martin, S. F. ; Davis, B. E.</creator><creatorcontrib>Lynch, V. M. ; Fishpaugh, J. R. ; Martin, S. F. ; Davis, B. E.</creatorcontrib><description>C27H32O2S, Mr = 420.61, monoclinic, P2(1)/c, a = 8.4756(13), b = 14.710(2), c = 18.425(3) A, beta = 99.575(13) degrees, V = 2265.2(6) A3, Z = 4, Dx = 1.23 g cm-3, mu = 1.5567 cm-1, Mo K alpha, lambda = 0.7107 A, F(000) = 904, T = 298 K, R = 0.0630 for 2942 reflections [Fo greater than or equal to 6 sigma (Fo)]. The cyclooctane portion of the [5.3.1] ring system assumes the boat-chair conformation while the cyclohexene portion has the boat conformation. As has been observed in other [5.3.1]undecene systems, ring strain appears to cause a distortion of the geometry of the bridgehead alkene. The bond length C7--C8 [1.343(5) A] is long for an isolated C--C double bond. The Csp2--Csp3 bond lengths at C7 are asymmetric with C7--C6 being 1.498(5) A while C7--C11 is 1.535(5) A. The maximum deviation from ideality for the torsion angles around the double bond is 16.2(4) degrees (absolute value). This twist in the alkene group is reflected in the non-planarity of the group [max. deviation 0.193(6) A for C9] and in the dihedral angle between the nearly planar portions (C6, C7, C8, C11 and C7, C8, C9, C15), which is 9.4(2) degrees.</description><identifier>ISSN: 0108-2701</identifier><identifier>EISSN: 1600-5759</identifier><identifier>DOI: 10.1107/S0108270190008320</identifier><identifier>PMID: 2025408</identifier><identifier>CODEN: ACSCEE</identifier><language>eng</language><publisher>5 Abbey Square, Chester, Cheshire CH1 2HU, England: International Union of Crystallography</publisher><subject>Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds ; Bridged Bicyclo Compounds - chemistry ; Condensed matter: structure, mechanical and thermal properties ; Exact sciences and technology ; Molecular Structure ; Organic compounds ; Physics ; Stereoisomerism ; Structure of solids and liquids; crystallography ; Structure of specific crystalline solids ; X-Ray Diffraction</subject><ispartof>Acta crystallographica. 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E.</creatorcontrib><title>Structure of (±)-(1R,6S)-1-benzyloxy-8,11,11-trimethyl-6-phenylthiobicyclo[5.3.1]undec-7-en-3-one</title><title>Acta crystallographica. Section C, Crystal structure communications</title><addtitle>Acta Cryst. C</addtitle><description>C27H32O2S, Mr = 420.61, monoclinic, P2(1)/c, a = 8.4756(13), b = 14.710(2), c = 18.425(3) A, beta = 99.575(13) degrees, V = 2265.2(6) A3, Z = 4, Dx = 1.23 g cm-3, mu = 1.5567 cm-1, Mo K alpha, lambda = 0.7107 A, F(000) = 904, T = 298 K, R = 0.0630 for 2942 reflections [Fo greater than or equal to 6 sigma (Fo)]. The cyclooctane portion of the [5.3.1] ring system assumes the boat-chair conformation while the cyclohexene portion has the boat conformation. As has been observed in other [5.3.1]undecene systems, ring strain appears to cause a distortion of the geometry of the bridgehead alkene. The bond length C7--C8 [1.343(5) A] is long for an isolated C--C double bond. The Csp2--Csp3 bond lengths at C7 are asymmetric with C7--C6 being 1.498(5) A while C7--C11 is 1.535(5) A. The maximum deviation from ideality for the torsion angles around the double bond is 16.2(4) degrees (absolute value). This twist in the alkene group is reflected in the non-planarity of the group [max. deviation 0.193(6) A for C9] and in the dihedral angle between the nearly planar portions (C6, C7, C8, C11 and C7, C8, C9, C15), which is 9.4(2) degrees.</description><subject>Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds</subject><subject>Bridged Bicyclo Compounds - chemistry</subject><subject>Condensed matter: structure, mechanical and thermal properties</subject><subject>Exact sciences and technology</subject><subject>Molecular Structure</subject><subject>Organic compounds</subject><subject>Physics</subject><subject>Stereoisomerism</subject><subject>Structure of solids and liquids; crystallography</subject><subject>Structure of specific crystalline solids</subject><subject>X-Ray Diffraction</subject><issn>0108-2701</issn><issn>1600-5759</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1991</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkN1qFDEYhoNY6rZ6AR4IPVFaaNYvyeRnDutS20JRdFdFRUKS-YadOjuzTmaw07vyFrwys-xSDzwQAjl4n-cNeQl5ymDKGOiXc2BguAaWA4ARHB6QCVMAVGqZPySTTUw3-SNyEONNgjjnYp_sc-AyAzMhft53Q-iHDo_a8uj4968Teszen6r5CWXUY3M31u3tSM0pY-nQvqtW2C_Hmiq6XmIz1v2yan0VxlC3X-VUTNm3oSkwUE2xoYK2DT4me6WrIz7Z3Yfkw-vzxeySXr-9uJqdXdOQGZFw5TCTRpUiDyCkyAUob5jSXEmpuPdOZB4dR-M9mGASK4AbiaoooMilOCQvtr3rrv0xYOztqooB69o12A7RGpCZZpAnkG3B0LUxdljadfqW60bLwG52tf_smpxnu_LBr7C4N3ZDpvz5LncxuLrsXBOq-Lc4N5JJzRJnttzPqsbx_w_bs8-z-QKyTCeVbtUq9nh7r7ruu1VaaGk_vbmwrz6yL_BOL6wRfwB6KJqB</recordid><startdate>19910215</startdate><enddate>19910215</enddate><creator>Lynch, V. M.</creator><creator>Fishpaugh, J. R.</creator><creator>Martin, S. F.</creator><creator>Davis, B. E.</creator><general>International Union of Crystallography</general><general>Blackwell</general><scope>BSCLL</scope><scope>IQODW</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>7X8</scope></search><sort><creationdate>19910215</creationdate><title>Structure of (±)-(1R,6S)-1-benzyloxy-8,11,11-trimethyl-6-phenylthiobicyclo[5.3.1]undec-7-en-3-one</title><author>Lynch, V. M. ; Fishpaugh, J. R. ; Martin, S. F. ; Davis, B. E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4837-e6ae4586f39c03539306b8167265562bba34bea2e8bb08c845830285e6dd0d953</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1991</creationdate><topic>Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds</topic><topic>Bridged Bicyclo Compounds - chemistry</topic><topic>Condensed matter: structure, mechanical and thermal properties</topic><topic>Exact sciences and technology</topic><topic>Molecular Structure</topic><topic>Organic compounds</topic><topic>Physics</topic><topic>Stereoisomerism</topic><topic>Structure of solids and liquids; crystallography</topic><topic>Structure of specific crystalline solids</topic><topic>X-Ray Diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lynch, V. M.</creatorcontrib><creatorcontrib>Fishpaugh, J. R.</creatorcontrib><creatorcontrib>Martin, S. F.</creatorcontrib><creatorcontrib>Davis, B. E.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</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>Lynch, V. M.</au><au>Fishpaugh, J. R.</au><au>Martin, S. F.</au><au>Davis, B. E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structure of (±)-(1R,6S)-1-benzyloxy-8,11,11-trimethyl-6-phenylthiobicyclo[5.3.1]undec-7-en-3-one</atitle><jtitle>Acta crystallographica. Section C, Crystal structure communications</jtitle><addtitle>Acta Cryst. C</addtitle><date>1991-02-15</date><risdate>1991</risdate><volume>47</volume><issue>2</issue><spage>468</spage><epage>470</epage><pages>468-470</pages><issn>0108-2701</issn><eissn>1600-5759</eissn><coden>ACSCEE</coden><abstract>C27H32O2S, Mr = 420.61, monoclinic, P2(1)/c, a = 8.4756(13), b = 14.710(2), c = 18.425(3) A, beta = 99.575(13) degrees, V = 2265.2(6) A3, Z = 4, Dx = 1.23 g cm-3, mu = 1.5567 cm-1, Mo K alpha, lambda = 0.7107 A, F(000) = 904, T = 298 K, R = 0.0630 for 2942 reflections [Fo greater than or equal to 6 sigma (Fo)]. The cyclooctane portion of the [5.3.1] ring system assumes the boat-chair conformation while the cyclohexene portion has the boat conformation. As has been observed in other [5.3.1]undecene systems, ring strain appears to cause a distortion of the geometry of the bridgehead alkene. The bond length C7--C8 [1.343(5) A] is long for an isolated C--C double bond. The Csp2--Csp3 bond lengths at C7 are asymmetric with C7--C6 being 1.498(5) A while C7--C11 is 1.535(5) A. The maximum deviation from ideality for the torsion angles around the double bond is 16.2(4) degrees (absolute value). This twist in the alkene group is reflected in the non-planarity of the group [max. deviation 0.193(6) A for C9] and in the dihedral angle between the nearly planar portions (C6, C7, C8, C11 and C7, C8, C9, C15), which is 9.4(2) degrees.</abstract><cop>5 Abbey Square, Chester, Cheshire CH1 2HU, England</cop><pub>International Union of Crystallography</pub><pmid>2025408</pmid><doi>10.1107/S0108270190008320</doi><tpages>3</tpages></addata></record> |
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| identifier | ISSN: 0108-2701 |
| ispartof | Acta crystallographica. Section C, Crystal structure communications, 1991-02, Vol.47 (2), p.468-470 |
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| subjects | Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds Bridged Bicyclo Compounds - chemistry Condensed matter: structure, mechanical and thermal properties Exact sciences and technology Molecular Structure Organic compounds Physics Stereoisomerism Structure of solids and liquids crystallography Structure of specific crystalline solids X-Ray Diffraction |
| title | Structure of (±)-(1R,6S)-1-benzyloxy-8,11,11-trimethyl-6-phenylthiobicyclo[5.3.1]undec-7-en-3-one |
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