{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-01620ebcad10497f8627a651a8b81ac7","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"cd7d1c9e9f25fdd04221f4717bd9778fb87e2e9eb1fdc4178862a4561c93e64d","doi":"10.1002/chem.201003731","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-c59b507bb09f3295","route_slugs":["ord-01620ebcad10497f8627a651a8b81ac7-3980beedf90a","ord-01620ebcad10497f8627a651a8b81ac7-117a58945840"],"reactant_slugs":["ord-compound-ab6534b54a4f47bb56f7","ord-compound-810cb9aa2d4bbae7695d"],"product_slugs":["ord-compound-a150c46901b358c4d421"],"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":"1604"}],"inputs":{"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"}]},"CC(C)P(C(C)C)C(Nc1ccccc1n3nc(c2ccccc2)cc3c4ccccc4)c5ccccc5":{"components":[{"identifiers":[{"type":"NAME","value":"CC(C)P(C(C)C)C(Nc1ccccc1n3nc(c2ccccc2)cc3c4ccccc4)c5ccccc5"}],"amount":{"moles":{"value":0.1,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"COCOc2ccc1ccccc1c2c3c(OCOC)ccc4ccccc34":{"components":[{"identifiers":[{"type":"SMILES","value":"COCOc2ccc1ccccc1c2c3c(OCOC)ccc4ccccc34"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.5,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":66,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":24,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"COCOc2ccc1ccccc1c2c4c(c3ccc(C)cc3)ccc5ccccc45"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":82}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1002/chem.201003731"}}},"entities":[{"slug":"ord-compound-ab6534b54a4f47bb56f7","name":"C24H22O4 · ORD YIAQRNNJNMLGTP-UHFFFAOYSA-N","smiles":"COCOc1ccc2ccccc2c1-c1c(OCOC)ccc2ccccc12","inchi":"InChI=1S/C24H22O4/c1-25-15-27-21-13-11-17-7-3-5-9-19(17)23(21)24-20-10-6-4-8-18(20)12-14-22(24)28-16-26-2/h3-14H,15-16H2,1-2H3","formula":"C24H22O4"},{"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-a150c46901b358c4d421","name":"C29H24O2 · ORD DWNFDQJQYNIEGK-UHFFFAOYSA-N","smiles":"COCOc1ccc2ccccc2c1-c1c(-c2ccc(C)cc2)ccc2ccccc12","inchi":"InChI=1S/C29H24O2/c1-20-11-13-23(14-12-20)26-17-15-21-7-3-5-9-24(21)28(26)29-25-10-6-4-8-22(25)16-18-27(29)31-19-30-2/h3-18H,19H2,1-2H3","formula":"C29H24O2"}],"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-c59b507bb09f3295","title":"Literature experiment — 10.1002/chem.201003731","source_type":"paper","doi":"10.1002/chem.201003731","url":"https://doi.org/10.1002/chem.201003731","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"]}