{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-01f8176700a74753bb53316d1105a3fc","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"1e7af7a20dda96afe5b1e360fc9c847500f0bf0df4c1a4e73207e5efb5ace433","doi":"10.1021/ja8056503","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-97e05f98cef066b7","route_slugs":["ord-01f8176700a74753bb53316d1105a3fc-53c6bc99bd95","ord-01f8176700a74753bb53316d1105a3fc-27332f55ba4a"],"reactant_slugs":["ord-compound-4e79f3b25e74453c3d15","ord-compound-6b341acbbfcc5fb19609"],"product_slugs":["ord-compound-f4598c222be25ab0e36e"],"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":"362"}],"inputs":{"CC(=O)Oc2ccc1cc(O)ccc1c2":{"components":[{"identifiers":[{"type":"SMILES","value":"CC(=O)Oc2ccc1cc(O)ccc1c2"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.25,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"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"}]}},"conditions":{"temperature":{"setpoint":{"value":110,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":12,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"Oc3ccc2cc(c1ccccc1)ccc2c3"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":42}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1021/ja8056503"}}},"entities":[{"slug":"ord-compound-4e79f3b25e74453c3d15","name":"C12H10O3 · ORD KOSWEOFSNRRAQH-UHFFFAOYSA-N","smiles":"CC(=O)Oc1ccc2cc(O)ccc2c1","inchi":"InChI=1S/C12H10O3/c1-8(13)15-12-5-3-9-6-11(14)4-2-10(9)7-12/h2-7,14H,1H3","formula":"C12H10O3"},{"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-f4598c222be25ab0e36e","name":"C16H12O · ORD PZOXFBPKKGTQDZ-UHFFFAOYSA-N","smiles":"Oc1ccc2cc(-c3ccccc3)ccc2c1","inchi":"InChI=1S/C16H12O/c17-16-9-8-14-10-13(6-7-15(14)11-16)12-4-2-1-3-5-12/h1-11,17H","formula":"C16H12O"}],"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-97e05f98cef066b7","title":"Literature experiment — 10.1021/ja8056503","source_type":"paper","doi":"10.1021/ja8056503","url":"https://doi.org/10.1021/ja8056503","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"]}