{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-044aae029a9b4c889908f8f3b5c4ff9c","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"cc008c7ba749d7e1a11353b92459bec0f60cf6e1c31d6646576bc0eda748dc3c","doi":"10.1021/acs.orglett.6b02656","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-515625e66ce7c072","route_slugs":["ord-044aae029a9b4c889908f8f3b5c4ff9c-f7f0fae45684","ord-044aae029a9b4c889908f8f3b5c4ff9c-d037714f46a8"],"reactant_slugs":["ord-compound-810cb9aa2d4bbae7695d","ord-compound-b712286fa3b7ea53e5f6"],"product_slugs":["ord-compound-4981228acdaa84b76941"],"selection_notes":["Only explicitly marked REACTANT inputs become graph starting points.","Only products with a positive reported numeric YIELD become graph destinations; all reported outcomes remain in raw.","One representative record per exact reactant/product structure set; other conditions are not additional transformations.","Some source yields use float_value rather than a typed percentage; the original value is retained without asserting units.","At least one source reactant quantity is zero; no stoichiometric amount is inferred from this placeholder."],"raw":{"identifiers":[{"type":"REACTION_TYPE","value":"100"}],"inputs":{"Cc1ccc([Mg]Br)cc1":{"components":[{"identifiers":[{"type":"SMILES","value":"Cc1ccc([Mg]Br)cc1"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"c2(OC)ccc1cc(N3CCCC3)ccc1c2":{"components":[{"identifiers":[{"type":"SMILES","value":"c2(OC)ccc1cc(N3CCCC3)ccc1c2"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.2,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"ItBu":{"components":[{"identifiers":[{"type":"NAME","value":"ItBu"}],"amount":{"moles":{"value":0.040000003,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]}},"conditions":{"temperature":{"setpoint":{"value":60,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":24,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"Cc3ccc(c2ccc1cc(N4CCCC4)ccc1c2)cc3"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":79}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1021/acs.orglett.6b02656"}}},"entities":[{"slug":"ord-compound-810cb9aa2d4bbae7695d","name":"C7H7BrMg · ORD ZRJNGFJIBZKXTP-UHFFFAOYSA-M","smiles":"Cc1cc[c]([Mg][Br])cc1","inchi":"InChI=1S/C7H7.BrH.Mg/c1-7-5-3-2-4-6-7;;/h3-6H,1H3;1H;/q;;+1/p-1","formula":"C7H7BrMg"},{"slug":"ord-compound-b712286fa3b7ea53e5f6","name":"C15H17NO · ORD CDUPUVUDMVIGAC-UHFFFAOYSA-N","smiles":"COc1ccc2cc(N3CCCC3)ccc2c1","inchi":"InChI=1S/C15H17NO/c1-17-15-7-5-12-10-14(6-4-13(12)11-15)16-8-2-3-9-16/h4-7,10-11H,2-3,8-9H2,1H3","formula":"C15H17NO"},{"slug":"ord-compound-4981228acdaa84b76941","name":"C21H21N · ORD SMWWZNRJCXJPNB-UHFFFAOYSA-N","smiles":"Cc1ccc(-c2ccc3cc(N4CCCC4)ccc3c2)cc1","inchi":"InChI=1S/C21H21N/c1-16-4-6-17(7-5-16)18-8-9-20-15-21(11-10-19(20)14-18)22-12-2-3-13-22/h4-11,14-15H,2-3,12-13H2,1H3","formula":"C21H21N"}],"dataset":{"dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","name":"NiCOlit","description":"Nickel-catalyzed cross-couplings extracted from organic reaction publications","records_in_source":1762,"path":"data/9b/ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545.parquet","sha256":"195765643b4aaad79d9ed82de6737a4855b9f2716e0bc0aa10cff950b7604d39","bytes":126909,"repository_url":"https://github.com/open-reaction-database/ord-data/blob/83f971f586f6ad18f358ae4ae99d045e94ed2066/data/9b/ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545.parquet","download_url":"https://huggingface.co/datasets/open-reaction-database/ord-data/resolve/93475c46949f9218e1dfb6624096025135db2add/data/9b/ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545.parquet"},"publication":{"slug":"ord-publication-515625e66ce7c072","title":"Literature experiment — 10.1021/acs.orglett.6b02656","source_type":"paper","doi":"10.1021/acs.orglett.6b02656","url":"https://doi.org/10.1021/acs.orglett.6b02656","note":"Publication DOI reported by the Open Reaction Database. Experimental record data adapted under CC BY-SA 4.0; https://creativecommons.org/licenses/by-sa/4.0/"},"license":"CC-BY-SA-4.0","license_url":"https://creativecommons.org/licenses/by-sa/4.0/","attribution":"Open Reaction Database contributors and the cited original publications","changes":["Bounded selection across datasets and publications","Deduplicated exact transformations across conditions","Canonicalized molecular structures using RDKit; calculated identifiers, formulae and molecular weights","Explicitly incomplete directed branches for all recorded reactants and positively measured products","Removed submitter account and contact fields from provenance; retained scientific input and outcome fields"]}