{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-19b4b91f970c4c6f804e7f7922b0dc85","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"69c62b466f84f083f4b7f322bccc0b457f009d8f51f57c1d773aa2e05625c8e5","doi":"10.1021/ol502583h","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-248ae97eab198793","route_slugs":["ord-19b4b91f970c4c6f804e7f7922b0dc85-7938fd42519f","ord-19b4b91f970c4c6f804e7f7922b0dc85-49913babf39d"],"reactant_slugs":["ord-compound-562366bda5adaac8f422","ord-compound-23bcaf9dc713576bac2c"],"product_slugs":["ord-compound-3d98b08a5efcb4d217d5"],"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":"1662"}],"inputs":{"Cc2ccc(B1OCC(C)(C)CO1)cc2":{"components":[{"identifiers":[{"type":"SMILES","value":"Cc2ccc(B1OCC(C)(C)CO1)cc2"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"COc2ccc(c1ccccc1)cc2":{"components":[{"identifiers":[{"type":"SMILES","value":"COc2ccc(c1ccccc1)cc2"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.3,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"ICy":{"components":[{"identifiers":[{"type":"NAME","value":"ICy"}],"amount":{"moles":{"value":0.060000002,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]}},"conditions":{"temperature":{"setpoint":{"value":120,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":12,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"Cc3ccc(c2ccc(c1ccccc1)cc2)cc3"},{"type":"SMILES","value":"Cc3ccc(c2ccc(c1ccccc1)cc2)cc3"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":76}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1021/ol502583h"}}},"entities":[{"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"},{"slug":"ord-compound-23bcaf9dc713576bac2c","name":"C12H17BO2 · ORD ZSPBWRPQSPRISS-UHFFFAOYSA-N","smiles":"Cc1ccc(B2OCC(C)(C)CO2)cc1","inchi":"InChI=1S/C12H17BO2/c1-10-4-6-11(7-5-10)13-14-8-12(2,3)9-15-13/h4-7H,8-9H2,1-3H3","formula":"C12H17BO2"},{"slug":"ord-compound-3d98b08a5efcb4d217d5","name":"C19H16 · ORD XNYPQVNKEFUPST-UHFFFAOYSA-N","smiles":"Cc1ccc(-c2ccc(-c3ccccc3)cc2)cc1","inchi":"InChI=1S/C19H16/c1-15-7-9-17(10-8-15)19-13-11-18(12-14-19)16-5-3-2-4-6-16/h2-14H,1H3","formula":"C19H16"}],"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-248ae97eab198793","title":"Literature experiment — 10.1021/ol502583h","source_type":"paper","doi":"10.1021/ol502583h","url":"https://doi.org/10.1021/ol502583h","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"]}
