{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-0613dec247ec478fb6967c3abee06913","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"126c75cdd6fded51af1ba3ba49e6dcc127f234a23efc17d6594cb8236360f39c","doi":"10.1021/ol101592r","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-4eef893d310e6136","route_slugs":["ord-0613dec247ec478fb6967c3abee06913-2d1ca7392e3d","ord-0613dec247ec478fb6967c3abee06913-02ff8b6895fd"],"reactant_slugs":["ord-compound-595a3180e8eff86e0eb6","ord-compound-f4836aa2c9a4b5cce0c1"],"product_slugs":["ord-compound-70a7ec193f15b5e3e130"],"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":"767"}],"inputs":{"PCy3":{"components":[{"identifiers":[{"type":"NAME","value":"PCy3"}],"amount":{"moles":{"value":0.05,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"CC(C)(C)C(=O)Oc1cccc2ccccc12":{"components":[{"identifiers":[{"type":"SMILES","value":"CC(C)(C)C(=O)Oc1cccc2ccccc12"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.25,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"F[B-](F)(F)c1ccncc1.[K+]":{"components":[{"identifiers":[{"type":"SMILES","value":"F[B-](F)(F)c1ccncc1.[K+]"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":110,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":4,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"c3ccc2c(c1ccncc1)cccc2c3"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":32}}],"reaction_role":"PRODUCT"}],"analyses":{"analytical_yield":{"type":"CUSTOM","details":"isolated analytical_yield"}}}],"provenance":{"doi":"10.1021/ol101592r"}}},"entities":[{"slug":"ord-compound-595a3180e8eff86e0eb6","name":"C15H16O2 · ORD LQSGTVGOLFWRJY-UHFFFAOYSA-N","smiles":"CC(C)(C)C(=O)Oc1cccc2ccccc12","inchi":"InChI=1S/C15H16O2/c1-15(2,3)14(16)17-13-10-6-8-11-7-4-5-9-12(11)13/h4-10H,1-3H3","formula":"C15H16O2"},{"slug":"ord-compound-f4836aa2c9a4b5cce0c1","name":"C5H4BF3KN · ORD SLPOSOZRTRIRQS-UHFFFAOYSA-N","smiles":"F[B-](F)(F)c1ccncc1.[K+]","inchi":"InChI=1S/C5H4BF3N.K/c7-6(8,9)5-1-3-10-4-2-5;/h1-4H;/q-1;+1","formula":"C5H4BF3KN"},{"slug":"ord-compound-70a7ec193f15b5e3e130","name":"C15H11N · ORD HBUWLNOJQAZUQZ-UHFFFAOYSA-N","smiles":"c1ccc2c(-c3ccncc3)cccc2c1","inchi":"InChI=1S/C15H11N/c1-2-6-14-12(4-1)5-3-7-15(14)13-8-10-16-11-9-13/h1-11H","formula":"C15H11N"}],"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-4eef893d310e6136","title":"Literature experiment — 10.1021/ol101592r","source_type":"paper","doi":"10.1021/ol101592r","url":"https://doi.org/10.1021/ol101592r","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"]}