{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-02afb49d4df44df49cf67a3f3e752e4c","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"14f51d2b529344a721236ab6f40fed1b00473c20ca26313a5a931af329e67b1e","doi":"10.1002/adsc.201600590","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-577bbf568f51a218","route_slugs":["ord-02afb49d4df44df49cf67a3f3e752e4c-5dd35a8df02f","ord-02afb49d4df44df49cf67a3f3e752e4c-643dc00c73f8"],"reactant_slugs":["ord-compound-e412cbd0f85fa6339bca","ord-compound-acd3673bded4cb200fa9"],"product_slugs":["ord-compound-f5c8e6806219a09f0995"],"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":"1077"}],"inputs":{"dcype":{"components":[{"identifiers":[{"type":"NAME","value":"dcype"}],"amount":{"moles":{"value":0.020000001,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"CCO[Si](OCC)(OCC)c1cccc(C)c1":{"components":[{"identifiers":[{"type":"SMILES","value":"CCO[Si](OCC)(OCC)c1cccc(C)c1"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"CN(C)C(=O)Oc2ccc1ccc(N(C)C)cc1c2":{"components":[{"identifiers":[{"type":"SMILES","value":"CN(C)C(=O)Oc2ccc1ccc(N(C)C)cc1c2"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.2,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":120,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":12,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"Cc3cccc(c2ccc1ccc(N(C)C)cc1c2)c3"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":43}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1002/adsc.201600590"}}},"entities":[{"slug":"ord-compound-e412cbd0f85fa6339bca","name":"C13H22O3Si · ORD FGLFSDHJENOLAP-UHFFFAOYSA-N","smiles":"CCO[Si](OCC)(OCC)c1cccc(C)c1","inchi":"InChI=1S/C13H22O3Si/c1-5-14-17(15-6-2,16-7-3)13-10-8-9-12(4)11-13/h8-11H,5-7H2,1-4H3","formula":"C13H22O3Si"},{"slug":"ord-compound-acd3673bded4cb200fa9","name":"C15H18N2O2 · ORD NKZBKHMNDKJNFZ-UHFFFAOYSA-N","smiles":"CN(C)C(=O)Oc1ccc2ccc(N(C)C)cc2c1","inchi":"InChI=1S/C15H18N2O2/c1-16(2)13-7-5-11-6-8-14(10-12(11)9-13)19-15(18)17(3)4/h5-10H,1-4H3","formula":"C15H18N2O2"},{"slug":"ord-compound-f5c8e6806219a09f0995","name":"C19H19N · ORD FAYPFKWLDJARFS-UHFFFAOYSA-N","smiles":"Cc1cccc(-c2ccc3ccc(N(C)C)cc3c2)c1","inchi":"InChI=1S/C19H19N/c1-14-5-4-6-16(11-14)17-8-7-15-9-10-19(20(2)3)13-18(15)12-17/h4-13H,1-3H3","formula":"C19H19N"}],"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-577bbf568f51a218","title":"Literature experiment — 10.1002/adsc.201600590","source_type":"paper","doi":"10.1002/adsc.201600590","url":"https://doi.org/10.1002/adsc.201600590","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"]}