{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-a484fec79b294998b62270bf4067c250","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"1ccf3ad113c914a066fdd3f4e1a0d22e17acf3dfa00ff038b241cacd32af0324","doi":"10.1021/acs.organomet.5b00874","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-ebd1c98e92762187","route_slugs":["ord-a484fec79b294998b62270bf4067c250-71441919782c","ord-a484fec79b294998b62270bf4067c250-c766e36bd640"],"reactant_slugs":["ord-compound-d2375780582b558517f7","ord-compound-3685c37d99c086fc08bb"],"product_slugs":["ord-compound-dce923ee7c5c5a526cf2"],"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":"1381"}],"inputs":{"COc1ccc(C)cc1":{"components":[{"identifiers":[{"type":"SMILES","value":"COc1ccc(C)cc1"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":1,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"PCy3+ItBu":{"components":[{"identifiers":[{"type":"NAME","value":"PCy3+ItBu"}],"amount":{"moles":{"value":0.1,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"Cc1ccccc1[Mg]Br":{"components":[{"identifiers":[{"type":"SMILES","value":"Cc1ccccc1[Mg]Br"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":110,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":10,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"Cc2ccc(c1ccccc1C)cc2"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":91}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1021/acs.organomet.5b00874"}}},"entities":[{"slug":"ord-compound-d2375780582b558517f7","name":"C8H10O · ORD CHLICZRVGGXEOD-UHFFFAOYSA-N","smiles":"COc1ccc(C)cc1","inchi":"InChI=1S/C8H10O/c1-7-3-5-8(9-2)6-4-7/h3-6H,1-2H3","formula":"C8H10O"},{"slug":"ord-compound-3685c37d99c086fc08bb","name":"C7H7BrMg · ORD DVXDIGKNJYSMFM-UHFFFAOYSA-M","smiles":"Cc1cccc[c]1[Mg][Br]","inchi":"InChI=1S/C7H7.BrH.Mg/c1-7-5-3-2-4-6-7;;/h2-5H,1H3;1H;/q;;+1/p-1","formula":"C7H7BrMg"},{"slug":"ord-compound-dce923ee7c5c5a526cf2","name":"C14H14 · ORD SHMKKPZGLDISGT-UHFFFAOYSA-N","smiles":"Cc1ccc(-c2ccccc2C)cc1","inchi":"InChI=1S/C14H14/c1-11-7-9-13(10-8-11)14-6-4-3-5-12(14)2/h3-10H,1-2H3","formula":"C14H14"}],"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-ebd1c98e92762187","title":"Literature experiment — 10.1021/acs.organomet.5b00874","source_type":"paper","doi":"10.1021/acs.organomet.5b00874","url":"https://doi.org/10.1021/acs.organomet.5b00874","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"]}