{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-0021943c24784c9298710a97140aec6d","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"b3129456ddfbe046c9567f4c7daaaf8929bb04de0a7a70879867bea292d49c80","doi":"10.1002/anie.200453765","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-db517057e96cd604","route_slugs":["ord-0021943c24784c9298710a97140aec6d-e44c497c87b1","ord-0021943c24784c9298710a97140aec6d-77ad283c1f9e"],"reactant_slugs":["ord-compound-68f0d7e5ac851580942f","ord-compound-810cb9aa2d4bbae7695d"],"product_slugs":["ord-compound-a0dfc94aaedc80e3af22"],"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":"1331"}],"inputs":{"PCy3":{"components":[{"identifiers":[{"type":"NAME","value":"PCy3"}],"amount":{"moles":{"value":0.3734,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"Cc1ccc([Mg]Br)cc1":{"components":[{"identifiers":[{"type":"SMILES","value":"Cc1ccc([Mg]Br)cc1"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"COCOc2ccc1CCCCc1c2":{"components":[{"identifiers":[{"type":"SMILES","value":"COCOc2ccc1CCCCc1c2"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":1.867,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":15,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"Cc3ccc(c2ccc1CCCCc1c2)cc3"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":92}}],"reaction_role":"PRODUCT"}],"analyses":{"analytical_yield":{"type":"CUSTOM","details":"isolated analytical_yield"}}}],"provenance":{"doi":"10.1002/anie.200453765"}}},"entities":[{"slug":"ord-compound-68f0d7e5ac851580942f","name":"C12H16O2 · ORD LYHJECZUEZOABA-UHFFFAOYSA-N","smiles":"COCOc1ccc2c(c1)CCCC2","inchi":"InChI=1S/C12H16O2/c1-13-9-14-12-7-6-10-4-2-3-5-11(10)8-12/h6-8H,2-5,9H2,1H3","formula":"C12H16O2"},{"slug":"ord-compound-810cb9aa2d4bbae7695d","name":"C7H7BrMg · ORD ZRJNGFJIBZKXTP-UHFFFAOYSA-M","smiles":"Cc1cc[c]([Mg][Br])cc1","inchi":"InChI=1S/C7H7.BrH.Mg/c1-7-5-3-2-4-6-7;;/h3-6H,1H3;1H;/q;;+1/p-1","formula":"C7H7BrMg"},{"slug":"ord-compound-a0dfc94aaedc80e3af22","name":"C17H18 · ORD QEZMSFVMIVYNEK-UHFFFAOYSA-N","smiles":"Cc1ccc(-c2ccc3c(c2)CCCC3)cc1","inchi":"InChI=1S/C17H18/c1-13-6-8-15(9-7-13)17-11-10-14-4-2-3-5-16(14)12-17/h6-12H,2-5H2,1H3","formula":"C17H18"}],"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-db517057e96cd604","title":"Literature experiment — 10.1002/anie.200453765","source_type":"paper","doi":"10.1002/anie.200453765","url":"https://doi.org/10.1002/anie.200453765","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"]}
