{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-0c7e154815894fe0af42053252f23b35","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"94309d4457613810fb83580cb6c22fbfb3bc9f1539e7282742a0182f975088d4","doi":"10.1021/acscatal.8b03436","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-3e7695dc58476fe6","route_slugs":["ord-0c7e154815894fe0af42053252f23b35-cb0024975211","ord-0c7e154815894fe0af42053252f23b35-dd559d6b2e59"],"reactant_slugs":["ord-compound-4cfbbafa2aaecd4966e8","anisole"],"product_slugs":["ord-compound-6f4b2d613065cbbb0edd"],"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":"253"}],"inputs":{"CCn2cnc1ccccc12":{"components":[{"identifiers":[{"type":"SMILES","value":"CCn2cnc1ccccc12"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"CDC":{"components":[{"identifiers":[{"type":"NAME","value":"CDC"}],"amount":{"moles":{"value":0.075,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"COc1ccccc1":{"components":[{"identifiers":[{"type":"SMILES","value":"COc1ccccc1"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.75,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":90,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":16,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"CCn3c(c1ccccc1)nc2ccccc23"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":72}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1021/acscatal.8b03436"}}},"entities":[{"slug":"ord-compound-4cfbbafa2aaecd4966e8","name":"C9H10N2 · ORD WVNMLOGVAVGQIT-UHFFFAOYSA-N","smiles":"CCn1cnc2ccccc21","inchi":"InChI=1S/C9H10N2/c1-2-11-7-10-8-5-3-4-6-9(8)11/h3-7H,2H2,1H3","formula":"C9H10N2"},{"slug":"anisole","name":"Anisole","smiles":"COC1=CC=CC=C1","inchi":"InChI=1S/C7H8O/c1-8-7-5-3-2-4-6-7/h2-6H,1H3","formula":"C7H8O"},{"slug":"ord-compound-6f4b2d613065cbbb0edd","name":"C15H14N2 · ORD NWMBNEWCGZPOIT-UHFFFAOYSA-N","smiles":"CCn1c(-c2ccccc2)nc2ccccc21","inchi":"InChI=1S/C15H14N2/c1-2-17-14-11-7-6-10-13(14)16-15(17)12-8-4-3-5-9-12/h3-11H,2H2,1H3","formula":"C15H14N2"}],"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-3e7695dc58476fe6","title":"Literature experiment — 10.1021/acscatal.8b03436","source_type":"paper","doi":"10.1021/acscatal.8b03436","url":"https://doi.org/10.1021/acscatal.8b03436","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"]}