{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-0fdb504bed264b54a8549cb1ca7e4ee0","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"a2d1baad3c3705df23ce7020d2d862599177d3b5b3febf655c4c7a15839d6e17","doi":"10.1021/ja410883p","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-2f09760077504b47","route_slugs":["ord-0fdb504bed264b54a8549cb1ca7e4ee0-4d7fa633157f","ord-0fdb504bed264b54a8549cb1ca7e4ee0-0afbdd23808d"],"reactant_slugs":["ord-compound-67d97c22440781269217","carbon-dioxide"],"product_slugs":["ord-compound-a366100a0b9e00d3fefa"],"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":"654"}],"inputs":{"dppf":{"components":[{"identifiers":[{"type":"NAME","value":"dppf"}],"amount":{"moles":{"value":0.085,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"CC(C)(C)C(=O)Oc2ccc1ccccc1c2":{"components":[{"identifiers":[{"type":"SMILES","value":"CC(C)(C)C(=O)Oc2ccc1ccccc1c2"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.5,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"O=C=O":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C=O"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":48,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(O)c2ccc1ccccc1c2"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":30}}],"reaction_role":"PRODUCT"}],"analyses":{"analytical_yield":{"type":"CUSTOM","details":"isolated analytical_yield"}}}],"provenance":{"doi":"10.1021/ja410883p"}}},"entities":[{"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":"carbon-dioxide","name":"Carbon dioxide","smiles":"O=C=O","inchi":"InChI=1S/CO2/c2-1-3","formula":"CO2"},{"slug":"ord-compound-a366100a0b9e00d3fefa","name":"C11H8O2 · ORD UOBYKYZJUGYBDK-UHFFFAOYSA-N","smiles":"O=C(O)c1ccc2ccccc2c1","inchi":"InChI=1S/C11H8O2/c12-11(13)10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,(H,12,13)","formula":"C11H8O2"}],"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-2f09760077504b47","title":"Literature experiment — 10.1021/ja410883p","source_type":"paper","doi":"10.1021/ja410883p","url":"https://doi.org/10.1021/ja410883p","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"]}