{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-5289a19bd47e46c488a82e8cb9e65ea1","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"23f251fe7948a4b8f9744ca5922d5f052ba6b13a3b3f864c198a5306072c76a6","doi":"10.1002/anie.201403823","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-6fb181c9cd5463a2","route_slugs":["ord-5289a19bd47e46c488a82e8cb9e65ea1-78e55eb1ddf7","ord-5289a19bd47e46c488a82e8cb9e65ea1-044cd387480f"],"reactant_slugs":["acetophenone","ord-compound-67d97c22440781269217"],"product_slugs":["ord-compound-53d0a92fb3aa9e1f6996"],"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":"540"}],"inputs":{"CC(C)(C)C(=O)Oc2ccc1ccccc1c2":{"components":[{"identifiers":[{"type":"SMILES","value":"CC(C)(C)C(=O)Oc2ccc1ccccc1c2"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.3,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"L2":{"components":[{"identifiers":[{"type":"NAME","value":"L2"}],"amount":{"moles":{"value":0.060000002,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"CC(=O)c1ccccc1":{"components":[{"identifiers":[{"type":"SMILES","value":"CC(=O)c1ccccc1"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":150,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":24,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(c1ccccc1)Cc3ccc2ccccc2c3.O=C(c1ccccc1)C(c3ccc2ccccc2c3)c5ccc4ccccc4c5"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":35}}],"reaction_role":"PRODUCT"}],"analyses":{"analytical_yield":{"type":"CUSTOM","details":"isolated analytical_yield"}}}],"provenance":{"doi":"10.1002/anie.201403823"}}},"entities":[{"slug":"acetophenone","name":"Acetophenone","smiles":"CC(=O)C1=CC=CC=C1","inchi":"InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3","formula":"C8H8O"},{"slug":"ord-compound-67d97c22440781269217","name":"C15H16O2 · ORD SUGMMMOSTHSMJT-UHFFFAOYSA-N","smiles":"CC(C)(C)C(=O)Oc1ccc2ccccc2c1","inchi":"InChI=1S/C15H16O2/c1-15(2,3)14(16)17-13-9-8-11-6-4-5-7-12(11)10-13/h4-10H,1-3H3","formula":"C15H16O2"},{"slug":"ord-compound-53d0a92fb3aa9e1f6996","name":"C46H34O2 · ORD IJBRHQFOMHRPKL-UHFFFAOYSA-N","smiles":"O=C(Cc1ccc2ccccc2c1)c1ccccc1.O=C(c1ccccc1)C(c1ccc2ccccc2c1)c1ccc2ccccc2c1","inchi":"InChI=1S/C28H20O.C18H14O/c29-28(22-10-2-1-3-11-22)27(25-16-14-20-8-4-6-12-23(20)18-25)26-17-15-21-9-5-7-13-24(21)19-26;19-18(16-7-2-1-3-8-16)13-14-10-11-15-6-4-5-9-17(15)12-14/h1-19,27H;1-12H,13H2","formula":"C46H34O2"}],"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-6fb181c9cd5463a2","title":"Literature experiment — 10.1002/anie.201403823","source_type":"paper","doi":"10.1002/anie.201403823","url":"https://doi.org/10.1002/anie.201403823","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"]}