{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-034b877749b343f996c0536d9d0c2b05","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"bf44b52d6e6687c4489ec883ac6df18eeb307af3ffa703569f0e08f31acd4876","doi":"10.1002/chem.201103784","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-7ede0b389b2328fc","route_slugs":["ord-034b877749b343f996c0536d9d0c2b05-db95f3cf17fe","ord-034b877749b343f996c0536d9d0c2b05-07d31bc2bcac"],"reactant_slugs":["ord-compound-8bcf10c923cd157ddd08","ord-compound-178efa12452177b2348a"],"product_slugs":["ord-compound-4bd8b4f79c4b3a043a28"],"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":"1199"}],"inputs":{"C[Zn](C)(C)([Li])([Li])c1cccc2ccccc12":{"components":[{"identifiers":[{"type":"SMILES","value":"C[Zn](C)(C)([Li])([Li])c1cccc2ccccc12"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"PCy3":{"components":[{"identifiers":[{"type":"NAME","value":"PCy3"}],"amount":{"moles":{"value":0.04,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"CC(C)N(C(=O)c1ccc(OC)cc1)C(C)C":{"components":[{"identifiers":[{"type":"SMILES","value":"CC(C)N(C(=O)c1ccc(OC)cc1)C(C)C"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.5,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":50,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":9,"precision":3,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"CC(C)N(CC(=O)c3ccc(c1cccc2ccccc12)cc3)C(C)C"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":45}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1002/chem.201103784"}}},"entities":[{"slug":"ord-compound-8bcf10c923cd157ddd08","name":"C14H21NO2 · ORD IZNMHGFRJFLYSK-UHFFFAOYSA-N","smiles":"COc1ccc(C(=O)N(C(C)C)C(C)C)cc1","inchi":"InChI=1S/C14H21NO2/c1-10(2)15(11(3)4)14(16)12-6-8-13(17-5)9-7-12/h6-11H,1-5H3","formula":"C14H21NO2"},{"slug":"ord-compound-178efa12452177b2348a","name":"C13H16Li2Zn · ORD RQQALDKYRKUJIO-UHFFFAOYSA-N","smiles":"[Li][Zn]([Li])([CH3])([CH3])([CH3])[c]1cccc2ccccc12","inchi":"InChI=1S/C10H7.3CH3.2Li.Zn/c1-2-6-10-8-4-3-7-9(10)5-1;;;;;;/h1-7H;3*1H3;;;","formula":"C13H16Li2Zn"},{"slug":"ord-compound-4bd8b4f79c4b3a043a28","name":"C24H27NO · ORD FJWUYWJUJWSDQT-UHFFFAOYSA-N","smiles":"CC(C)N(CC(=O)c1ccc(-c2cccc3ccccc23)cc1)C(C)C","inchi":"InChI=1S/C24H27NO/c1-17(2)25(18(3)4)16-24(26)21-14-12-20(13-15-21)23-11-7-9-19-8-5-6-10-22(19)23/h5-15,17-18H,16H2,1-4H3","formula":"C24H27NO"}],"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-7ede0b389b2328fc","title":"Literature experiment — 10.1002/chem.201103784","source_type":"paper","doi":"10.1002/chem.201103784","url":"https://doi.org/10.1002/chem.201103784","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"]}