{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-39ba5825f8c9418ca6544ed804cf9675","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"355c092ab21ce6dd57f3202cb79c174babe717676c1615ca2aa3251d6af2361e","doi":"10.1039/C5SC02942B","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-cbcaa2fcf3fd2746","route_slugs":["ord-39ba5825f8c9418ca6544ed804cf9675-2dcf13e039a8","ord-39ba5825f8c9418ca6544ed804cf9675-8692b2b00fc4"],"reactant_slugs":["ord-compound-e8facb323e0392aa90c1","oxazole"],"product_slugs":["ord-compound-9614754118928c8e9205"],"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":"1578"}],"inputs":{"dcypt":{"components":[{"identifiers":[{"type":"NAME","value":"dcypt"}],"amount":{"moles":{"value":0.048000004,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"c1cocn1":{"components":[{"identifiers":[{"type":"SMILES","value":"c1cocn1"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"CN(C)C(=O)Oc1ccccc1":{"components":[{"identifiers":[{"type":"SMILES","value":"CN(C)C(=O)Oc1ccccc1"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.6,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":110,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":36,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"c2ccc(c1ncco1)cc2"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":56}}],"reaction_role":"PRODUCT"}],"analyses":{"analytical_yield":{"type":"CUSTOM","details":"isolated analytical_yield"}}}],"provenance":{"doi":"10.1039/C5SC02942B"}}},"entities":[{"slug":"ord-compound-e8facb323e0392aa90c1","name":"C9H11NO2 · ORD MYOHNZJKOAODMX-UHFFFAOYSA-N","smiles":"CN(C)C(=O)Oc1ccccc1","inchi":"InChI=1S/C9H11NO2/c1-10(2)9(11)12-8-6-4-3-5-7-8/h3-7H,1-2H3","formula":"C9H11NO2"},{"slug":"oxazole","name":"Oxazole","smiles":"C1=COC=N1","inchi":"InChI=1S/C3H3NO/c1-2-5-3-4-1/h1-3H","formula":"C3H3NO"},{"slug":"ord-compound-9614754118928c8e9205","name":"C9H7NO · ORD RQCBPOPQTLHDFC-UHFFFAOYSA-N","smiles":"c1ccc(-c2ncco2)cc1","inchi":"InChI=1S/C9H7NO/c1-2-4-8(5-3-1)9-10-6-7-11-9/h1-7H","formula":"C9H7NO"}],"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-cbcaa2fcf3fd2746","title":"Literature experiment — 10.1039/C5SC02942B","source_type":"paper","doi":"10.1039/C5SC02942B","url":"https://doi.org/10.1039/C5SC02942B","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"]}