{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-057d0433bd0c45f5a220ba504f388a03","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"f3ab1d115e4b8027d0fcbea4c480222658d3e0280d4fdc8babf6a2dd959f901a","doi":"10.1021/ja210249h","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-eb0600fcd356f3c6","route_slugs":["ord-057d0433bd0c45f5a220ba504f388a03-b5c9488f5a04","ord-057d0433bd0c45f5a220ba504f388a03-26cd5f8dc799"],"reactant_slugs":["ord-compound-67d97c22440781269217","ord-compound-16fd1fc064e7a281a7e8"],"product_slugs":["ord-compound-6c431779018261dba045"],"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":"739"}],"inputs":{"dcype":{"components":[{"identifiers":[{"type":"NAME","value":"dcype"}],"amount":{"moles":{"value":0.080000006,"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":0.6,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"c2ccc1ocnc1c2":{"components":[{"identifiers":[{"type":"SMILES","value":"c2ccc1ocnc1c2"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":120,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":12,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"c4ccc3cc(c2nc1ccccc1o2)ccc3c4"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":9}}],"reaction_role":"PRODUCT"}],"analyses":{"analytical_yield":{"type":"CUSTOM","details":"isolated analytical_yield"}}}],"provenance":{"doi":"10.1021/ja210249h"}}},"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":"ord-compound-16fd1fc064e7a281a7e8","name":"C7H5NO · ORD BCMCBBGGLRIHSE-UHFFFAOYSA-N","smiles":"c1ccc2ocnc2c1","inchi":"InChI=1S/C7H5NO/c1-2-4-7-6(3-1)8-5-9-7/h1-5H","formula":"C7H5NO"},{"slug":"ord-compound-6c431779018261dba045","name":"C17H11NO · ORD XTFVRSDPQJOAQJ-UHFFFAOYSA-N","smiles":"c1ccc2cc(-c3nc4ccccc4o3)ccc2c1","inchi":"InChI=1S/C17H11NO/c1-2-6-13-11-14(10-9-12(13)5-1)17-18-15-7-3-4-8-16(15)19-17/h1-11H","formula":"C17H11NO"}],"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-eb0600fcd356f3c6","title":"Literature experiment — 10.1021/ja210249h","source_type":"paper","doi":"10.1021/ja210249h","url":"https://doi.org/10.1021/ja210249h","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"]}