{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-1de389a422104d5e855c71f5a6c3628e","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"c5c43fec1a7f1bb584c82763191d4c10eb2a045f787ef66e8a10c03ade0b5287","doi":"10.1021/ja903091g","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-d6a3d93306e01742","route_slugs":["ord-1de389a422104d5e855c71f5a6c3628e-3fbb9c983371","ord-1de389a422104d5e855c71f5a6c3628e-318bb5ef085b"],"reactant_slugs":["ord-compound-cd2578454c27f2bc0a19","ord-compound-d834841dea03a98a8380"],"product_slugs":["ord-compound-759959592f9e530384ed"],"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":"1897"}],"inputs":{"CCN(CC)C(=O)Oc1ccc(C)cc1":{"components":[{"identifiers":[{"type":"SMILES","value":"CCN(CC)C(=O)Oc1ccc(C)cc1"},{"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"}]},"dppp":{"components":[{"identifiers":[{"type":"NAME","value":"dppp"}],"amount":{"moles":{"value":0.0255,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]}},"conditions":{"temperature":{"setpoint":{"value":25,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":1,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"Cc2ccc(c1ccccc1)cc2"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":10}}],"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-d834841dea03a98a8380","name":"C12H17NO2 · ORD HEAYNANJBNIHRA-UHFFFAOYSA-N","smiles":"CCN(CC)C(=O)Oc1ccc(C)cc1","inchi":"InChI=1S/C12H17NO2/c1-4-13(5-2)12(14)15-11-8-6-10(3)7-9-11/h6-9H,4-5H2,1-3H3","formula":"C12H17NO2"},{"slug":"ord-compound-759959592f9e530384ed","name":"C13H12 · ORD ZZLCFHIKESPLTH-UHFFFAOYSA-N","smiles":"Cc1ccc(-c2ccccc2)cc1","inchi":"InChI=1S/C13H12/c1-11-7-9-13(10-8-11)12-5-3-2-4-6-12/h2-10H,1H3","formula":"C13H12"}],"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"]}