{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-1e998cbfb7ea4c9dbcf670fc03e7f8ed","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"ff24f257b370388cc3304f8fbcf2842962261c4efda444f90516bacd4d145c7d","doi":"10.1021/acs.orglett.6b03861","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-e427391a30acc456","route_slugs":["ord-1e998cbfb7ea4c9dbcf670fc03e7f8ed-9d99a47803e9","ord-1e998cbfb7ea4c9dbcf670fc03e7f8ed-712f0497561c"],"reactant_slugs":["ord-compound-810cb9aa2d4bbae7695d","ord-compound-7d359c99132ab4058ad1"],"product_slugs":["ord-compound-bc7e1487a59a74819e35"],"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":"1249"}],"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"}]},"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"}]},"I(2-Ad)":{"components":[{"identifiers":[{"type":"NAME","value":"I(2-Ad)"}],"amount":{"moles":{"value":0.05,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":2,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"Cc3ccc(c1ccccc1c2ccccc2O)cc3"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":91}}],"reaction_role":"PRODUCT"}],"analyses":{"analytical_yield":{"type":"CUSTOM","details":"isolated analytical_yield"}}}],"provenance":{"doi":"10.1021/acs.orglett.6b03861"}}},"entities":[{"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-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-bc7e1487a59a74819e35","name":"C19H16O · ORD IJLOFQAUVYZHDI-UHFFFAOYSA-N","smiles":"Cc1ccc(-c2ccccc2-c2ccccc2O)cc1","inchi":"InChI=1S/C19H16O/c1-14-10-12-15(13-11-14)16-6-2-3-7-17(16)18-8-4-5-9-19(18)20/h2-13,20H,1H3","formula":"C19H16O"}],"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"]}
