{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-1091a8dda4354acea3af21347b87e078","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"6c804abb06655ff7d36602fbdcc92cc179b0deeb3ff3930a3b1f134249380c52","doi":"10.1002/chem.201603436","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-3b2a2dd77984a610","route_slugs":["ord-1091a8dda4354acea3af21347b87e078-7ff9468e5520","ord-1091a8dda4354acea3af21347b87e078-839244363139"],"reactant_slugs":["ord-compound-d4b337ca4c7df7573492","ord-compound-00a13c40e73737285c13"],"product_slugs":["ord-compound-0dddd923311996bfa74d"],"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":"35"}],"inputs":{"COc1ccc2ccccc2c1":{"components":[{"identifiers":[{"type":"SMILES","value":"COc1ccc2ccccc2c1"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.3,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"SIMes":{"components":[{"identifiers":[{"type":"NAME","value":"SIMes"}],"amount":{"moles":{"value":0.030000001,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"[Li]C":{"components":[{"identifiers":[{"type":"SMILES","value":"[Li]C"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":25,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":12,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"Cc2ccc1ccccc1c2"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":88}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1002/chem.201603436"}}},"entities":[{"slug":"ord-compound-d4b337ca4c7df7573492","name":"C11H10O · ORD LUZDYPLAQQGJEA-UHFFFAOYSA-N","smiles":"COc1ccc2ccccc2c1","inchi":"InChI=1S/C11H10O/c1-12-11-7-6-9-4-2-3-5-10(9)8-11/h2-8H,1H3","formula":"C11H10O"},{"slug":"ord-compound-00a13c40e73737285c13","name":"CH3Li · ORD DVSDBMFJEQPWNO-UHFFFAOYSA-N","smiles":"[Li][CH3]","inchi":"InChI=1S/CH3.Li/h1H3;","formula":"CH3Li"},{"slug":"ord-compound-0dddd923311996bfa74d","name":"C11H10 · ORD QIMMUPPBPVKWKM-UHFFFAOYSA-N","smiles":"Cc1ccc2ccccc2c1","inchi":"InChI=1S/C11H10/c1-9-6-7-10-4-2-3-5-11(10)8-9/h2-8H,1H3","formula":"C11H10"}],"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-3b2a2dd77984a610","title":"Literature experiment — 10.1002/chem.201603436","source_type":"paper","doi":"10.1002/chem.201603436","url":"https://doi.org/10.1002/chem.201603436","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"]}