{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-0109b10a4ed940e291bd07f7daaf5d24","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"66392482d3cf826c9ceb2e00b6d9227985594957c540639d7f36a4d02aba2d6e","doi":"10.1021/jo00041a004","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-b9ec16b78ffd439a","route_slugs":["ord-0109b10a4ed940e291bd07f7daaf5d24-ebf99bc8312c","ord-0109b10a4ed940e291bd07f7daaf5d24-341225a9216e"],"reactant_slugs":["ord-compound-0547b6e043cae9d71d7d","ord-compound-91ec2fedf5c06ff1d438"],"product_slugs":["ord-compound-6930de8b039f066bd6cc"],"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":"1646"}],"inputs":{"Cl[Mg]c1ccccc1":{"components":[{"identifiers":[{"type":"SMILES","value":"Cl[Mg]c1ccccc1"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"CCN(CC)C(=O)Oc1cccc(OCOC)c1":{"components":[{"identifiers":[{"type":"SMILES","value":"CCN(CC)C(=O)Oc1cccc(OCOC)c1"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":1.6,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":25,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":16,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"COCOc2cccc(c1ccccc1)c2"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":80}}],"reaction_role":"PRODUCT"}],"analyses":{"analytical_yield":{"type":"CUSTOM","details":"isolated analytical_yield"}}}],"provenance":{"doi":"10.1021/jo00041a004"}}},"entities":[{"slug":"ord-compound-0547b6e043cae9d71d7d","name":"C13H19NO4 · ORD DXTZKQVUXKNHJA-UHFFFAOYSA-N","smiles":"CCN(CC)C(=O)Oc1cccc(OCOC)c1","inchi":"InChI=1S/C13H19NO4/c1-4-14(5-2)13(15)18-12-8-6-7-11(9-12)17-10-16-3/h6-9H,4-5,10H2,1-3H3","formula":"C13H19NO4"},{"slug":"ord-compound-91ec2fedf5c06ff1d438","name":"C6H5ClMg · ORD GQONLASZRVFGHI-UHFFFAOYSA-M","smiles":"[Cl][Mg][c]1ccccc1","inchi":"InChI=1S/C6H5.ClH.Mg/c1-2-4-6-5-3-1;;/h1-5H;1H;/q;;+1/p-1","formula":"C6H5ClMg"},{"slug":"ord-compound-6930de8b039f066bd6cc","name":"C14H14O2 · ORD JRRIIYFCKLVGAP-UHFFFAOYSA-N","smiles":"COCOc1cccc(-c2ccccc2)c1","inchi":"InChI=1S/C14H14O2/c1-15-11-16-14-9-5-8-13(10-14)12-6-3-2-4-7-12/h2-10H,11H2,1H3","formula":"C14H14O2"}],"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-b9ec16b78ffd439a","title":"Literature experiment — 10.1021/jo00041a004","source_type":"paper","doi":"10.1021/jo00041a004","url":"https://doi.org/10.1021/jo00041a004","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"]}