{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-1f80fc91351044169de00370335b01e3","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"ebde7f4b645e8837ac7266f04e16254a316c3ecaba2f715dbfa63d13a7afbfbc","doi":"10.1021/ja903091g","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-d6a3d93306e01742","route_slugs":["ord-1f80fc91351044169de00370335b01e3-0b4f83da527a","ord-1f80fc91351044169de00370335b01e3-f5b90870ccae"],"reactant_slugs":["ord-compound-cd2578454c27f2bc0a19","ord-compound-f498d392cfea0448a175"],"product_slugs":["ord-compound-79e8f97e6761a597257e"],"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":"1910"}],"inputs":{"CCN(CC)C(=O)Oc1cccc(OC(=O)N(CC)CC)c1":{"components":[{"identifiers":[{"type":"SMILES","value":"CCN(CC)C(=O)Oc1cccc(OC(=O)N(CC)CC)c1"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.51,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"Br[Mg]c1ccccc1":{"components":[{"identifiers":[{"type":"SMILES","value":"Br[Mg]c1ccccc1"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"CC(O)c1ccccc1P(c2ccccc2)c3ccccc3":{"components":[{"identifiers":[{"type":"NAME","value":"CC(O)c1ccccc1P(c2ccccc2)c3ccccc3"}],"amount":{"moles":{"value":0.0255,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]}},"conditions":{"temperature":{"setpoint":{"value":25,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":7,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"CCN(CC)C(=O)Oc2cccc(c1ccccc1)c2"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":76}}],"reaction_role":"PRODUCT"}],"analyses":{"analytical_yield":{"type":"CUSTOM","details":"isolated analytical_yield"}}}],"provenance":{"doi":"10.1021/ja903091g"}}},"entities":[{"slug":"ord-compound-cd2578454c27f2bc0a19","name":"C6H5BrMg · ORD ANRQGKOBLBYXFM-UHFFFAOYSA-M","smiles":"[Br][Mg][c]1ccccc1","inchi":"InChI=1S/C6H5.BrH.Mg/c1-2-4-6-5-3-1;;/h1-5H;1H;/q;;+1/p-1","formula":"C6H5BrMg"},{"slug":"ord-compound-f498d392cfea0448a175","name":"C16H24N2O4 · ORD ABCUTBFYSXRGFI-UHFFFAOYSA-N","smiles":"CCN(CC)C(=O)Oc1cccc(OC(=O)N(CC)CC)c1","inchi":"InChI=1S/C16H24N2O4/c1-5-17(6-2)15(19)21-13-10-9-11-14(12-13)22-16(20)18(7-3)8-4/h9-12H,5-8H2,1-4H3","formula":"C16H24N2O4"},{"slug":"ord-compound-79e8f97e6761a597257e","name":"C17H19NO2 · ORD ZTMCLHQCGHSJBU-UHFFFAOYSA-N","smiles":"CCN(CC)C(=O)Oc1cccc(-c2ccccc2)c1","inchi":"InChI=1S/C17H19NO2/c1-3-18(4-2)17(19)20-16-12-8-11-15(13-16)14-9-6-5-7-10-14/h5-13H,3-4H2,1-2H3","formula":"C17H19NO2"}],"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-d6a3d93306e01742","title":"Literature experiment — 10.1021/ja903091g","source_type":"paper","doi":"10.1021/ja903091g","url":"https://doi.org/10.1021/ja903091g","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"]}