{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-09443c57f0df4fc2858fb24c20b40acf","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"5ef03a0aba387f9706c65e02d896fefbba4acdfe8b4d9848739571012e11060b","doi":"10.1039/C3CC46663A","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-ceba9f9f21b90cd2","route_slugs":["ord-09443c57f0df4fc2858fb24c20b40acf-0917137799ae","ord-09443c57f0df4fc2858fb24c20b40acf-ee33078af1b4"],"reactant_slugs":["ord-compound-a0b7b5b2ba43327b0cb6","ord-compound-283307760fa5e198593a"],"product_slugs":["ord-compound-a0ed1b219cb63af3e20e"],"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":"846"}],"inputs":{"CCCCN5CN(c3cccc(N2CN(CCCC)c1ccccc12)n3)c4ccccc45":{"components":[{"identifiers":[{"type":"NAME","value":"CCCCN5CN(c3cccc(N2CN(CCCC)c1ccccc12)n3)c4ccccc45"}],"amount":{"moles":{"value":0.0025,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"B(c1ccccc1)(O)O":{"components":[{"identifiers":[{"type":"SMILES","value":"B(c1ccccc1)(O)O"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"CC(C)(C)C(=O)Oc2c1ccccc1cc3ccccc23":{"components":[{"identifiers":[{"type":"SMILES","value":"CC(C)(C)C(=O)Oc2c1ccccc1cc3ccccc23"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.5,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":100,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":6,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"c4ccc(c2c1ccccc1cc3ccccc23)cc4"},{"type":"SMILES","value":"c4ccc(c2c1ccccc1cc3ccccc23)cc4"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":4}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1039/C3CC46663A"}}},"entities":[{"slug":"ord-compound-a0b7b5b2ba43327b0cb6","name":"C6H7BO2 · ORD HXITXNWTGFUOAU-UHFFFAOYSA-N","smiles":"OB(O)c1ccccc1","inchi":"InChI=1S/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9H","formula":"C6H7BO2"},{"slug":"ord-compound-283307760fa5e198593a","name":"C19H18O2 · ORD NNLUDDFJYFYFSY-UHFFFAOYSA-N","smiles":"CC(C)(C)C(=O)Oc1c2ccccc2cc2ccccc12","inchi":"InChI=1S/C19H18O2/c1-19(2,3)18(20)21-17-15-10-6-4-8-13(15)12-14-9-5-7-11-16(14)17/h4-12H,1-3H3","formula":"C19H18O2"},{"slug":"ord-compound-a0ed1b219cb63af3e20e","name":"C20H14 · ORD LUBXLGUQZVKOFP-UHFFFAOYSA-N","smiles":"c1ccc(-c2c3ccccc3cc3ccccc23)cc1","inchi":"InChI=1S/C20H14/c1-2-8-15(9-3-1)20-18-12-6-4-10-16(18)14-17-11-5-7-13-19(17)20/h1-14H","formula":"C20H14"}],"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-ceba9f9f21b90cd2","title":"Literature experiment — 10.1039/C3CC46663A","source_type":"paper","doi":"10.1039/C3CC46663A","url":"https://doi.org/10.1039/C3CC46663A","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"]}