{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-0a40b71b52044d37810c759df392c98f","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"51d1e3cacd38477edba403aaa1e85e0cd1567899cebe6c279edbcb6ba98098ca","doi":"10.1021/acs.organomet.9b00543","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-c63153632e828a22","route_slugs":["ord-0a40b71b52044d37810c759df392c98f-6440304fd705","ord-0a40b71b52044d37810c759df392c98f-61f75b328532"],"reactant_slugs":["ord-compound-c4224958bee37ded911e","ord-compound-c72e6b0a716b787d8e29"],"product_slugs":["ord-compound-371971301096a5490e7b"],"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":"1031"}],"inputs":{"Cc1cccc(C)c1B(O)O":{"components":[{"identifiers":[{"type":"SMILES","value":"Cc1cccc(C)c1B(O)O"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"dcypf":{"components":[{"identifiers":[{"type":"NAME","value":"dcypf"}],"amount":{"moles":{"value":0.0033250002,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"CC(C)(C)OC(=O)Oc2ccc1ccccc1c2":{"components":[{"identifiers":[{"type":"SMILES","value":"CC(C)(C)OC(=O)Oc2ccc1ccccc1c2"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.133,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":60,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":4,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"Cc1cccc(C)c1c3ccc2ccccc2c3"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":70}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1021/acs.organomet.9b00543"}}},"entities":[{"slug":"ord-compound-c4224958bee37ded911e","name":"C15H16O3 · ORD CUFPXYFHDGLCPI-UHFFFAOYSA-N","smiles":"CC(C)(C)OC(=O)Oc1ccc2ccccc2c1","inchi":"InChI=1S/C15H16O3/c1-15(2,3)18-14(16)17-13-9-8-11-6-4-5-7-12(11)10-13/h4-10H,1-3H3","formula":"C15H16O3"},{"slug":"ord-compound-c72e6b0a716b787d8e29","name":"C8H11BO2 · ORD ZXDTWWZIHJEZOG-UHFFFAOYSA-N","smiles":"Cc1cccc(C)c1B(O)O","inchi":"InChI=1S/C8H11BO2/c1-6-4-3-5-7(2)8(6)9(10)11/h3-5,10-11H,1-2H3","formula":"C8H11BO2"},{"slug":"ord-compound-371971301096a5490e7b","name":"C18H16 · ORD DYJVADCPNYBVBL-UHFFFAOYSA-N","smiles":"Cc1cccc(C)c1-c1ccc2ccccc2c1","inchi":"InChI=1S/C18H16/c1-13-6-5-7-14(2)18(13)17-11-10-15-8-3-4-9-16(15)12-17/h3-12H,1-2H3","formula":"C18H16"}],"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-c63153632e828a22","title":"Literature experiment — 10.1021/acs.organomet.9b00543","source_type":"paper","doi":"10.1021/acs.organomet.9b00543","url":"https://doi.org/10.1021/acs.organomet.9b00543","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"]}