{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-0643c36a41c64e7297bc47e5d6391d12","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"7e068803a2493f4eba7d02f42e40a412d05307ac86d9cffc96c79f30f5ecde3e","doi":"10.1021/acs.orglett.6b03861","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-e427391a30acc456","route_slugs":["ord-0643c36a41c64e7297bc47e5d6391d12-a9289b09cd94","ord-0643c36a41c64e7297bc47e5d6391d12-6003416bd8b8"],"reactant_slugs":["ord-compound-cd2578454c27f2bc0a19","ord-compound-7d359c99132ab4058ad1"],"product_slugs":["ord-compound-d50cb8e14243f34ef8e8"],"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":"1251"}],"inputs":{"Br[Mg]c1ccccc1":{"components":[{"identifiers":[{"type":"SMILES","value":"Br[Mg]c1ccccc1"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"c1ccc3c(c1)oc2ccccc23":{"components":[{"identifiers":[{"type":"SMILES","value":"c1ccc3c(c1)oc2ccccc23"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.5,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":2,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"c3ccc(c1c(O)cccc1c2ccccc2)cc3"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":74}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1021/acs.orglett.6b03861"}}},"entities":[{"slug":"ord-compound-cd2578454c27f2bc0a19","name":"C6H5BrMg · ORD ANRQGKOBLBYXFM-UHFFFAOYSA-M","smiles":"[Br][Mg][c]1ccccc1","inchi":"InChI=1S/C6H5.BrH.Mg/c1-2-4-6-5-3-1;;/h1-5H;1H;/q;;+1/p-1","formula":"C6H5BrMg"},{"slug":"ord-compound-7d359c99132ab4058ad1","name":"C12H8O · ORD TXCDCPKCNAJMEE-UHFFFAOYSA-N","smiles":"c1ccc2c(c1)oc1ccccc12","inchi":"InChI=1S/C12H8O/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H","formula":"C12H8O"},{"slug":"ord-compound-d50cb8e14243f34ef8e8","name":"C18H14O · ORD XXKHDSGLCLCFSC-UHFFFAOYSA-N","smiles":"Oc1cccc(-c2ccccc2)c1-c1ccccc1","inchi":"InChI=1S/C18H14O/c19-17-13-7-12-16(14-8-3-1-4-9-14)18(17)15-10-5-2-6-11-15/h1-13,19H","formula":"C18H14O"}],"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-e427391a30acc456","title":"Literature experiment — 10.1021/acs.orglett.6b03861","source_type":"paper","doi":"10.1021/acs.orglett.6b03861","url":"https://doi.org/10.1021/acs.orglett.6b03861","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"]}