{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-2ecd8e0afe144385989bb49f57d53867","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"4df20ca8089a3542bb5b3906585f59244a970729012482ce8f0ef4b229f67edf","doi":"10.1002/anie.200907287","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-5afe27f73272e28c","route_slugs":["ord-2ecd8e0afe144385989bb49f57d53867-5ebe4d210f12","ord-2ecd8e0afe144385989bb49f57d53867-93845ba8f0c9"],"reactant_slugs":["morpholine","ord-compound-83d0babbb9afbc7ee574"],"product_slugs":["ord-compound-dfea70ca1bf587b31eb9"],"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":"708"}],"inputs":{"C1COCCN1":{"components":[{"identifiers":[{"type":"SMILES","value":"C1COCCN1"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"IPr":{"components":[{"identifiers":[{"type":"NAME","value":"IPr"}],"amount":{"moles":{"value":0.05,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"Cn3c1ccccc1c2ccc(OC(=O)C(C)(C)C)cc23":{"components":[{"identifiers":[{"type":"SMILES","value":"Cn3c1ccccc1c2ccc(OC(=O)C(C)(C)C)cc23"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.5,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":3,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"Cn4c1ccccc1c3ccc(N2CCOCC2)cc34"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":66}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1002/anie.200907287"}}},"entities":[{"slug":"morpholine","name":"Morpholine","smiles":"C1COCCN1","inchi":"InChI=1S/C4H9NO/c1-3-6-4-2-5-1/h5H,1-4H2","formula":"C4H9NO"},{"slug":"ord-compound-83d0babbb9afbc7ee574","name":"C18H19NO2 · ORD UEMZMPSQXAPWJF-UHFFFAOYSA-N","smiles":"Cn1c2ccccc2c2ccc(OC(=O)C(C)(C)C)cc21","inchi":"InChI=1S/C18H19NO2/c1-18(2,3)17(20)21-12-9-10-14-13-7-5-6-8-15(13)19(4)16(14)11-12/h5-11H,1-4H3","formula":"C18H19NO2"},{"slug":"ord-compound-dfea70ca1bf587b31eb9","name":"C17H18N2O · ORD CJVDUSGCZFBVOY-UHFFFAOYSA-N","smiles":"Cn1c2ccccc2c2ccc(N3CCOCC3)cc21","inchi":"InChI=1S/C17H18N2O/c1-18-16-5-3-2-4-14(16)15-7-6-13(12-17(15)18)19-8-10-20-11-9-19/h2-7,12H,8-11H2,1H3","formula":"C17H18N2O"}],"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-5afe27f73272e28c","title":"Literature experiment — 10.1002/anie.200907287","source_type":"paper","doi":"10.1002/anie.200907287","url":"https://doi.org/10.1002/anie.200907287","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"]}