{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-48c5360b326744d3b8bb865956232f05","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"4cc3b7c4264abd3cee8d92f6046e2f9edd3328ba17b46c9b8fc54fa2043969d8","doi":"10.1021/ol9029534","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-c3306294ca24169c","route_slugs":["ord-48c5360b326744d3b8bb865956232f05-47c91b58b4e7","ord-48c5360b326744d3b8bb865956232f05-d6ee3b1291ce"],"reactant_slugs":["ord-compound-d3096a91dfe13b9df26c","ord-compound-6b341acbbfcc5fb19609"],"product_slugs":["ord-compound-daa934cdb9368dc81862"],"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":"893"}],"inputs":{"PCy3":{"components":[{"identifiers":[{"type":"NAME","value":"PCy3"}],"amount":{"moles":{"value":0.05,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"c4ccc(B3OB(c1ccccc1)OB(c2ccccc2)O3)cc4":{"components":[{"identifiers":[{"type":"SMILES","value":"c4ccc(B3OB(c1ccccc1)OB(c2ccccc2)O3)cc4"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"CN(C)C(=O)Oc1cccc2ncccc12":{"components":[{"identifiers":[{"type":"SMILES","value":"CN(C)C(=O)Oc1cccc2ncccc12"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.25,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":110,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":16,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"c3ccc(c1cccc2ncccc12)cc3"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":80}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1021/ol9029534"}}},"entities":[{"slug":"ord-compound-d3096a91dfe13b9df26c","name":"C12H12N2O2 · ORD HGFFUYIDPDPZEP-UHFFFAOYSA-N","smiles":"CN(C)C(=O)Oc1cccc2ncccc12","inchi":"InChI=1S/C12H12N2O2/c1-14(2)12(15)16-11-7-3-6-10-9(11)5-4-8-13-10/h3-8H,1-2H3","formula":"C12H12N2O2"},{"slug":"ord-compound-6b341acbbfcc5fb19609","name":"C18H15B3O3 · ORD VOXXGUAZBWSUSS-UHFFFAOYSA-N","smiles":"c1ccc(B2OB(c3ccccc3)OB(c3ccccc3)O2)cc1","inchi":"InChI=1S/C18H15B3O3/c1-4-10-16(11-5-1)19-22-20(17-12-6-2-7-13-17)24-21(23-19)18-14-8-3-9-15-18/h1-15H","formula":"C18H15B3O3"},{"slug":"ord-compound-daa934cdb9368dc81862","name":"C15H11N · ORD QAQUJJBBUGVGMO-UHFFFAOYSA-N","smiles":"c1ccc(-c2cccc3ncccc23)cc1","inchi":"InChI=1S/C15H11N/c1-2-6-12(7-3-1)13-8-4-10-15-14(13)9-5-11-16-15/h1-11H","formula":"C15H11N"}],"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-c3306294ca24169c","title":"Literature experiment — 10.1021/ol9029534","source_type":"paper","doi":"10.1021/ol9029534","url":"https://doi.org/10.1021/ol9029534","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"]}