{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-2e733412453844acb39bfbc6d500a2e2","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"d8dd8d2ba3c4a0d89e8ddaf169ef389e8cab12ce8cdeeb280b59969e27d9130e","doi":"10.1002/anie.200907287","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-5afe27f73272e28c","route_slugs":["ord-2e733412453844acb39bfbc6d500a2e2-fadd9677c1f5","ord-2e733412453844acb39bfbc6d500a2e2-ae42dc8976ea"],"reactant_slugs":["morpholine","ord-compound-415cc70d7a5484846814"],"product_slugs":["ord-compound-fa1d947e90253f99735b"],"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":"688"}],"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"}]},"c2ccc(OCOc1ccccc1)cc2":{"components":[{"identifiers":[{"type":"SMILES","value":"c2ccc(OCOc1ccccc1)cc2"},{"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":"c2ccc(N1CCOCC1)cc2"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":26}}],"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-415cc70d7a5484846814","name":"C13H12O2 · ORD VTXLTXPNXYLCQD-UHFFFAOYSA-N","smiles":"c1ccc(OCOc2ccccc2)cc1","inchi":"InChI=1S/C13H12O2/c1-3-7-12(8-4-1)14-11-15-13-9-5-2-6-10-13/h1-10H,11H2","formula":"C13H12O2"},{"slug":"ord-compound-fa1d947e90253f99735b","name":"C10H13NO · ORD FHQRDEDZJIFJAL-UHFFFAOYSA-N","smiles":"c1ccc(N2CCOCC2)cc1","inchi":"InChI=1S/C10H13NO/c1-2-4-10(5-3-1)11-6-8-12-9-7-11/h1-5H,6-9H2","formula":"C10H13NO"}],"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"]}