{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-0aa88fcd592b4f94bcb9f0b2df7f42ef","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"ef7718b5ea0a3fe12f813925c17d964e602868f815630adbf4a2b479d6eb91fa","doi":"10.1246/cl.2011.913","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-4ea4f58397b7742b","route_slugs":["ord-0aa88fcd592b4f94bcb9f0b2df7f42ef-802f2e11ea98","ord-0aa88fcd592b4f94bcb9f0b2df7f42ef-851016bf40e1"],"reactant_slugs":["ord-compound-e6a8ac22511b58297184","ord-compound-b63e8ae82a1e097c7b67"],"product_slugs":["ord-compound-bfd65a16f10b9e80bcc6"],"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":"962"}],"inputs":{"dcypf":{"components":[{"identifiers":[{"type":"NAME","value":"dcypf"}],"amount":{"moles":{"value":0.05,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"OB(O)c1ccc(C(F)(F)F)cc1":{"components":[{"identifiers":[{"type":"SMILES","value":"OB(O)c1ccc(C(F)(F)F)cc1"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"COC(=O)Oc2ccc1ccccc1c2":{"components":[{"identifiers":[{"type":"SMILES","value":"COC(=O)Oc2ccc1ccccc1c2"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.5,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":60,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":48,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"FC(F)(F)c3ccc(c2ccc1ccccc1c2)cc3"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":64}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1246/cl.2011.913"}}},"entities":[{"slug":"ord-compound-e6a8ac22511b58297184","name":"C12H10O3 · ORD LUSSNKSMQDHEQS-UHFFFAOYSA-N","smiles":"COC(=O)Oc1ccc2ccccc2c1","inchi":"InChI=1S/C12H10O3/c1-14-12(13)15-11-7-6-9-4-2-3-5-10(9)8-11/h2-8H,1H3","formula":"C12H10O3"},{"slug":"ord-compound-b63e8ae82a1e097c7b67","name":"C7H6BF3O2 · ORD ALMFIOZYDASRRC-UHFFFAOYSA-N","smiles":"OB(O)c1ccc(C(F)(F)F)cc1","inchi":"InChI=1S/C7H6BF3O2/c9-7(10,11)5-1-3-6(4-2-5)8(12)13/h1-4,12-13H","formula":"C7H6BF3O2"},{"slug":"ord-compound-bfd65a16f10b9e80bcc6","name":"C17H11F3 · ORD WAMZBPUDXGSDGC-UHFFFAOYSA-N","smiles":"FC(F)(F)c1ccc(-c2ccc3ccccc3c2)cc1","inchi":"InChI=1S/C17H11F3/c18-17(19,20)16-9-7-13(8-10-16)15-6-5-12-3-1-2-4-14(12)11-15/h1-11H","formula":"C17H11F3"}],"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-4ea4f58397b7742b","title":"Literature experiment — 10.1246/cl.2011.913","source_type":"paper","doi":"10.1246/cl.2011.913","url":"https://doi.org/10.1246/cl.2011.913","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"]}