{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-024c78fdebc9462fb4cb46a732263034","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"61ac80bf1e02eef70e3d5ca7bb4e952455dbf7dcc8ae9d8fcf4fc4a92e5ca6da","doi":"10.1021/ja200398c","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-eb9e45f2bd5aabe4","route_slugs":["ord-024c78fdebc9462fb4cb46a732263034-4d595bb1ca15","ord-024c78fdebc9462fb4cb46a732263034-8d522ef0669d"],"reactant_slugs":["ord-compound-5e0f938accfb9d3a03da","ord-compound-23643e3a2d50b57f6d3a"],"product_slugs":["ord-compound-562366bda5adaac8f422"],"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":"922"}],"inputs":{"PCy3":{"components":[{"identifiers":[{"type":"NAME","value":"PCy3"}],"amount":{"moles":{"value":0.0878,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"COc1ccc(B(O)O)cc1":{"components":[{"identifiers":[{"type":"SMILES","value":"COc1ccc(B(O)O)cc1"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"CCN(CC)C(=O)Oc1ccccc1":{"components":[{"identifiers":[{"type":"SMILES","value":"CCN(CC)C(=O)Oc1ccccc1"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.439,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":130,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":24,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"COc2ccc(c1ccccc1)cc2"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":52}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1021/ja200398c"}}},"entities":[{"slug":"ord-compound-5e0f938accfb9d3a03da","name":"C11H15NO2 · ORD XOIJDIYJCTXRQR-UHFFFAOYSA-N","smiles":"CCN(CC)C(=O)Oc1ccccc1","inchi":"InChI=1S/C11H15NO2/c1-3-12(4-2)11(13)14-10-8-6-5-7-9-10/h5-9H,3-4H2,1-2H3","formula":"C11H15NO2"},{"slug":"ord-compound-23643e3a2d50b57f6d3a","name":"C7H9BO3 · ORD VOAAEKKFGLPLLU-UHFFFAOYSA-N","smiles":"COc1ccc(B(O)O)cc1","inchi":"InChI=1S/C7H9BO3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5,9-10H,1H3","formula":"C7H9BO3"},{"slug":"ord-compound-562366bda5adaac8f422","name":"C13H12O · ORD RHDYQUZYHZWTCI-UHFFFAOYSA-N","smiles":"COc1ccc(-c2ccccc2)cc1","inchi":"InChI=1S/C13H12O/c1-14-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-10H,1H3","formula":"C13H12O"}],"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-eb9e45f2bd5aabe4","title":"Literature experiment — 10.1021/ja200398c","source_type":"paper","doi":"10.1021/ja200398c","url":"https://doi.org/10.1021/ja200398c","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"]}