{"id":17063,"date":"2016-11-01T10:55:08","date_gmt":"2016-11-01T10:55:08","guid":{"rendered":"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=17063"},"modified":"2016-12-03T10:19:20","modified_gmt":"2016-12-03T10:19:20","slug":"the-largest-c-c-c-angle","status":"publish","type":"post","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17063","title":{"rendered":"The largest  C-C-C angle?"},"content":{"rendered":"<div class=\"kcite-section\" kcite-section-id=\"17063\">\n<p>I am now inverting the <a href=\"http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=17041\">previous question<\/a> by asking <em>what is the largest angle subtended at a chain of three connected 4-coordinate carbon atoms<\/em>? Let&#8217;s see if further interesting chemistry can be unearthed.<\/p>\n<p>Specifying only angles &gt; 130\u00b0, the following distribution is obtained.<\/p>\n<p><img decoding=\"async\" class=\"aligncenter size-full wp-image-17064\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/10\/CCC-large.jpg\" alt=\"ccc-large\" width=\"450\" srcset=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/10\/CCC-large.jpg 920w, https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/10\/CCC-large-300x232.jpg 300w, https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/10\/CCC-large-768x593.jpg 768w\" sizes=\"(max-width: 920px) 100vw, 920px\" \/><\/p>\n<ul>\n<li>Note the maximum at ~138\u00b0. This is typical of that found in spiro-cyclopropanes, although I have not checked if other kinds of compound can also sustain this angle.<\/li>\n<li>There appear to be a few examples at 180\u00b0 but these appear to be simple errors in the crystal coordinates.<\/li>\n<li>The first real example occurs at 166\u00b0<span id=\"cite_ITEM-17063-0\" name=\"citation\"><a href=\"#ITEM-17063-0\">[1]<\/a><\/span> and contains an almost hemispherical carbon atom, doi: <a href=\"http:\/\/doi.org\/10.5517\/CCZBB2P\">10.5517\/CCZBB2P<\/a> <span id=\"cite_ITEM-17063-1\" name=\"citation\"><a href=\"#ITEM-17063-1\">[2]<\/a><\/span><img decoding=\"async\" class=\"aligncenter size-full wp-image-17069\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/10\/FETBUD.jpg\" alt=\"fetbud\" width=\"450\" srcset=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/10\/FETBUD.jpg 463w, https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/10\/FETBUD-300x272.jpg 300w\" sizes=\"(max-width: 463px) 100vw, 463px\" \/><\/li>\n<li>A second example is a sprung spiro-cyclopropane <span id=\"cite_ITEM-17063-2\" name=\"citation\"><a href=\"#ITEM-17063-2\">[3]<\/a><\/span> in which the large angle is maintained without the help of a metal.<br \/>\n <img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-17067\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/10\/VAJHAP.jpg\" alt=\"vajhap\" width=\"391\" height=\"272\" srcset=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/10\/VAJHAP.jpg 391w, https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/10\/VAJHAP-300x209.jpg 300w\" sizes=\"auto, (max-width: 391px) 100vw, 391px\" \/><\/li>\n<li>This latter example suggests that a structural modification as shown below might take the angle to almost 180\u00b0 (calc. \u03c9B97XD\/Def2-TZVPP = 177.2\u00b0<span id=\"cite_ITEM-17063-3\" name=\"citation\"><a href=\"#ITEM-17063-3\">[4]<\/a><\/span>). <img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-17081\" src=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/11\/VAJHAP.jpg\" alt=\"vajhap\" width=\"431\" height=\"376\" srcset=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/11\/VAJHAP.jpg 431w, https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/11\/VAJHAP-300x262.jpg 300w\" sizes=\"auto, (max-width: 431px) 100vw, 431px\" \/><\/li>\n<\/ul>\n<p>It is remarkable how much the standard angle subtended at four-coordinate carbon (109.47\u00b0) can be opened. It makes one wonder whether something approaching 180\u00b0 is achievable, and what the properties of such a molecule might be.<\/p>\n<p>&nbsp;<\/p>\n<h2>References<\/h2>\n    <ol class=\"kcite-bibliography csl-bib-body\"><li id=\"ITEM-17063-0\">V. Gonz\u00e1lez-L\u00f3pez, M.A. Leyva, and M.J. Rosales-Hoz, \"Coupling of acetylene molecules on ruthenium clusters, involving cleavage of C\u2013Si bonds in the alkyne and coordination of a phenyl ring of a SiPh3 group\", <i>Dalton Transactions<\/i>, vol. 42, pp. 5401, 2013. <a href=\"https:\/\/doi.org\/10.1039\/c3dt32335h\">https:\/\/doi.org\/10.1039\/c3dt32335h<\/a>\n\n<\/li>\n<li id=\"ITEM-17063-1\">Gonzalez-Lopez, V.., Leyva, M.A.., and Rosales-Hoz, M.J.., \"CCDC 903652: Experimental Crystal Structure Determination\", 2013. <a href=\"https:\/\/doi.org\/10.5517\/cczbb2p\">https:\/\/doi.org\/10.5517\/cczbb2p<\/a>\n\n<\/li>\n<li id=\"ITEM-17063-2\">R. Boese, D. Blaeser, K. Gomann, and U.H. Brinker, \"Spiropentane as a tensile spring\", <i>Journal of the American Chemical Society<\/i>, vol. 111, pp. 1501-1503, 1989. <a href=\"https:\/\/doi.org\/10.1021\/ja00186a058\">https:\/\/doi.org\/10.1021\/ja00186a058<\/a>\n\n<\/li>\n<li id=\"ITEM-17063-3\">H. Rzepa, \"VAJHAP\", 2016. <a href=\"https:\/\/doi.org\/10.14469\/hpc\/1861\">https:\/\/doi.org\/10.14469\/hpc\/1861<\/a>\n\n<\/li>\n<\/ol>\n\n<\/div> <!-- kcite-section 17063 -->","protected":false},"excerpt":{"rendered":"<p>I am now inverting the previous question by asking what is the largest angle subtended at a chain of three connected 4-coordinate carbon atoms? Let&#8217;s see if further interesting chemistry can be unearthed. Specifying only angles &gt; 130\u00b0, the following distribution is obtained. Note the maximum at ~138\u00b0. This is typical of that found in [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"jetpack_post_was_ever_published":false,"_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":true,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_memberships_contains_paid_content":false,"activitypub_content_warning":"","activitypub_content_visibility":"","activitypub_max_image_attachments":5,"activitypub_interaction_policy_quote":"anyone","activitypub_status":"","footnotes":"","jetpack_publicize_message":"","jetpack_publicize_feature_enabled":true,"jetpack_social_post_already_shared":true,"jetpack_social_options":{"image_generator_settings":{"template":"highway","default_image_id":0,"font":"","enabled":false},"version":2}},"categories":[1745,4],"tags":[1553,157,1918],"ppma_author":[2661],"class_list":["post-17063","post","type-post","status-publish","format-standard","hentry","category-crystal_structure_mining","category-interesting-chemistry","tag-angle","tag-metal","tag-subtended-angle"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.5 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>The largest C-C-C angle? - Henry Rzepa&#039;s Blog<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17063\" \/>\n<meta property=\"og:locale\" content=\"en_GB\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"The largest C-C-C angle? - Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"og:description\" content=\"I am now inverting the previous question by asking what is the largest angle subtended at a chain of three connected 4-coordinate carbon atoms? Let&#8217;s see if further interesting chemistry can be unearthed. Specifying only angles &gt; 130\u00b0, the following distribution is obtained. Note the maximum at ~138\u00b0. This is typical of that found in [&hellip;]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17063\" \/>\n<meta property=\"og:site_name\" content=\"Henry Rzepa&#039;s Blog\" \/>\n<meta property=\"article:published_time\" content=\"2016-11-01T10:55:08+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2016-12-03T10:19:20+00:00\" \/>\n<meta property=\"og:image\" content=\"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/10\/CCC-large.jpg\" \/>\n<meta name=\"author\" content=\"Henry Rzepa\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"Henry Rzepa\" \/>\n\t<meta name=\"twitter:label2\" content=\"Estimated reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"1 minute\" \/>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"The largest C-C-C angle? - Henry Rzepa&#039;s Blog","robots":{"index":"index","follow":"follow","max-snippet":"max-snippet:-1","max-image-preview":"max-image-preview:large","max-video-preview":"max-video-preview:-1"},"canonical":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17063","og_locale":"en_GB","og_type":"article","og_title":"The largest C-C-C angle? - Henry Rzepa&#039;s Blog","og_description":"I am now inverting the previous question by asking what is the largest angle subtended at a chain of three connected 4-coordinate carbon atoms? Let&#8217;s see if further interesting chemistry can be unearthed. Specifying only angles &gt; 130\u00b0, the following distribution is obtained. Note the maximum at ~138\u00b0. This is typical of that found in [&hellip;]","og_url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17063","og_site_name":"Henry Rzepa&#039;s Blog","article_published_time":"2016-11-01T10:55:08+00:00","article_modified_time":"2016-12-03T10:19:20+00:00","og_image":[{"url":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/10\/CCC-large.jpg","type":"","width":"","height":""}],"author":"Henry Rzepa","twitter_card":"summary_large_image","twitter_misc":{"Written by":"Henry Rzepa","Estimated reading time":"1 minute"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"Article","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17063#article","isPartOf":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17063"},"author":{"name":"Henry Rzepa","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/#\/schema\/person\/2b40f7b9c872a4dc1547e040a11b6281"},"headline":"The largest C-C-C angle?","datePublished":"2016-11-01T10:55:08+00:00","dateModified":"2016-12-03T10:19:20+00:00","mainEntityOfPage":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17063"},"wordCount":202,"commentCount":1,"image":{"@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17063#primaryimage"},"thumbnailUrl":"http:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/10\/CCC-large.jpg","keywords":["Angle","metal","Subtended angle"],"articleSection":["crystal_structure_mining","Interesting chemistry"],"inLanguage":"en-GB","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17063#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17063","url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=17063","name":"The largest C-C-C angle? 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Here thought I might take a look at how it might act as such. There are up to\u00a0five binding modes with one metal that one might envisage:\u2026","rel":"","context":"In &quot;crystal_structure_mining&quot;","block_context":{"text":"crystal_structure_mining","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1745"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/05\/078.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":18399,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=18399","url_meta":{"origin":17063,"position":1},"title":"CH\u22c5\u22c5\u22c5\u03c0 Interactions between methyl and carbonyl groups in proteins: a small molecule check.","author":"Henry Rzepa","date":"May 29, 2017","format":false,"excerpt":"Derek Lowe highlights a recent article postulating\u00a0CH\u22c5\u22c5\u22c5\u03c0 interactions in proteins. Here I report a quick check using the small molecule crystal structure database (CSD). The search query (DOI:\u00a010.14469\/hpc\/2594)\u00a0is shown below. The distance refers to that between the (normalised) position of a hydrogen on a 4-coordinated carbon atom and the centroid\u2026","rel":"","context":"In &quot;crystal_structure_mining&quot;","block_context":{"text":"crystal_structure_mining","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1745"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/05\/152-1024x637.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":18205,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=18205","url_meta":{"origin":17063,"position":2},"title":"\u03c0-Facial hydrogen bonds to alkynes (revisited): how close can an acidic hydrogen approach?","author":"Henry Rzepa","date":"April 17, 2017","format":false,"excerpt":"Following on from my re-investigation of close hydrogen bonding contacts to the \u03c0-face of alkenes, here now is an updated scan for H-bonds to alkynes. The search query (dataDOI: 10.14469\/hpc\/2478) is similar to the previous one: QA is any of N,O,F,Cl. X is any atom, including metals and non-metals. The\u2026","rel":"","context":"In &quot;crystal_structure_mining&quot;","block_context":{"text":"crystal_structure_mining","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=1745"},"img":{"alt_text":"","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2017\/04\/triple-inter-1024x672.jpg?resize=350%2C200","width":350,"height":200},"classes":[]},{"id":30548,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=30548","url_meta":{"origin":17063,"position":3},"title":"Molecules of the year 2025: Benzene-busting inverted sandwich.","author":"Henry Rzepa","date":"January 1, 2026","format":false,"excerpt":"Sandwich compounds are the colloquial term used for molecules where a metal atom such as an iron dication is \"sandwiched\" between two carbon-based rings as ligands, most commonly cyclopentadienyl anion (the \"bread\") as in e.g. Ferrocene - a molecule first discovered in 1951. An \"inverted\" sandwich is where the carbon\u2026","rel":"","context":"In &quot;Interesting chemistry&quot;","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":29799,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=29799","url_meta":{"origin":17063,"position":4},"title":"Short B-H&#8230;H-O Interactions in crystal structures &#8211; a short DFT Exploration using B3LYP+D4 and r2scan-3c","author":"Henry Rzepa","date":"October 27, 2025","format":false,"excerpt":"In the previous post, I was commenting that the transition state for borohydride reduction of a ketone contained some close contacts between the hydrogen of the borohydride and the hydrogen of water. A systematic search of the CSD reveals a modest number of such contacts have been observed in crystal\u2026","rel":"","context":"In &quot;Interesting chemistry&quot;","block_context":{"text":"Interesting chemistry","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=4"},"img":{"alt_text":"","src":"","width":0,"height":0},"classes":[]},{"id":16573,"url":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?p=16573","url_meta":{"origin":17063,"position":5},"title":"How does an OH or NH group approach an aromatic ring to hydrogen bond with its \u03c0-face?","author":"Henry Rzepa","date":"June 22, 2016","format":false,"excerpt":"I previously used data mining of crystal structures to explore the directing influence of substituents on aromatic and heteroaromatic rings. Here\u00a0I explore, quite literally, a different angle to the hydrogen bonding interactions between a benzene ring and\u00a0OH or NH groups. I start by defining a benzene ring with a centroid.\u2026","rel":"","context":"In &quot;Chemical IT&quot;","block_context":{"text":"Chemical IT","link":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/?cat=2"},"img":{"alt_text":"aromatic-pi-query","src":"https:\/\/i0.wp.com\/www.ch.ic.ac.uk\/rzepa\/blog\/wp-content\/uploads\/2016\/06\/aromatic-pi-query-1-e1466580253270.jpg?resize=350%2C200","width":350,"height":200},"classes":[]}],"jetpack_likes_enabled":false,"authors":[{"term_id":2661,"user_id":1,"is_guest":0,"slug":"admin","display_name":"Henry Rzepa","avatar_url":"https:\/\/secure.gravatar.com\/avatar\/897b6740f7f599bca7942cdf7d7914af5988937ae0e3869ab09aebb87f26a731?s=96&d=blank&r=g","0":null,"1":"","2":"","3":"","4":"","5":"","6":"","7":"","8":""}],"_links":{"self":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/17063","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=17063"}],"version-history":[{"count":16,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/17063\/revisions"}],"predecessor-version":[{"id":17138,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=\/wp\/v2\/posts\/17063\/revisions\/17138"}],"wp:attachment":[{"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=17063"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=17063"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=17063"},{"taxonomy":"author","embeddable":true,"href":"https:\/\/www.ch.ic.ac.uk\/rzepa\/blog\/index.php?rest_route=%2Fwp%2Fv2%2Fppma_author&post=17063"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}