{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-082252729bf6471d99cda2e19eb547d5","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"b9eb41c33a248f83edce9cb6bb1603cc96a0fcb9d9cc4d21bc940208edb46bdb","doi":"10.1021/ja5029793","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-6b2477c410b6b304","route_slugs":["ord-082252729bf6471d99cda2e19eb547d5-ae7e950e8e63","ord-082252729bf6471d99cda2e19eb547d5-b127b2cc18ec"],"reactant_slugs":["ord-compound-3551653ac45ba21f6447","ord-compound-17b15bf8068c2ca41023"],"product_slugs":["ord-compound-e2c521fdf1d9ecd01de6"],"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":"460"}],"inputs":{"dppf":{"components":[{"identifiers":[{"type":"NAME","value":"dppf"}],"amount":{"moles":{"value":0.1,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"CC(C)c3cc(C(C)C)c(C(=O)Oc2ccc1ccccc1c2)c(C(C)C)c3":{"components":[{"identifiers":[{"type":"SMILES","value":"CC(C)c3cc(C(C)C)c(C(=O)Oc2ccc1ccccc1c2)c(C(C)C)c3"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.5,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"CCCCN=C=O":{"components":[{"identifiers":[{"type":"SMILES","value":"CCCCN=C=O"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":24,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"CCCCNC(=O)c2ccc1ccccc1c2"}],"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":"10.1021/ja5029793"}}},"entities":[{"slug":"ord-compound-3551653ac45ba21f6447","name":"C26H30O2 · ORD LGAUQWNLQJNCTM-UHFFFAOYSA-N","smiles":"CC(C)c1cc(C(C)C)c(C(=O)Oc2ccc3ccccc3c2)c(C(C)C)c1","inchi":"InChI=1S/C26H30O2/c1-16(2)21-14-23(17(3)4)25(24(15-21)18(5)6)26(27)28-22-12-11-19-9-7-8-10-20(19)13-22/h7-18H,1-6H3","formula":"C26H30O2"},{"slug":"ord-compound-17b15bf8068c2ca41023","name":"C5H9NO · ORD HNHVTXYLRVGMHD-UHFFFAOYSA-N","smiles":"CCCCN=C=O","inchi":"InChI=1S/C5H9NO/c1-2-3-4-6-5-7/h2-4H2,1H3","formula":"C5H9NO"},{"slug":"ord-compound-e2c521fdf1d9ecd01de6","name":"C15H17NO · ORD IKCJNZVSLPKXLB-UHFFFAOYSA-N","smiles":"CCCCNC(=O)c1ccc2ccccc2c1","inchi":"InChI=1S/C15H17NO/c1-2-3-10-16-15(17)14-9-8-12-6-4-5-7-13(12)11-14/h4-9,11H,2-3,10H2,1H3,(H,16,17)","formula":"C15H17NO"}],"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-6b2477c410b6b304","title":"Literature experiment — 10.1021/ja5029793","source_type":"paper","doi":"10.1021/ja5029793","url":"https://doi.org/10.1021/ja5029793","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"]}