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Record W2987418708 · doi:10.1107/s2056989019013896

Crystal structures of the two isomeric hydrogen-bonded cocrystals 2-chloro-4-nitrobenzoic acid–5-nitroquinoline (1/1) and 5-chloro-2-nitrobenzoic acid–5-nitroquinoline (1/1)

2019· article· en· W2987418708 on OpenAlex
Kazuma Gotoh, Hiroyuki Ishida

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.

Bibliographic record

VenueActa Crystallographica Section E Crystallographic Communications · 2019
Typearticle
Languageen
FieldChemistry
TopicCrystal structures of chemical compounds
Canadian institutionsUniversity of Toronto
Fundersnot available
KeywordsQuinolineHydrogen bondChemistryNitroBenzoic acidRing (chemistry)CrystallographyCrystal structureMoleculeCrystal (programming language)StereochemistryMedicinal chemistryOrganic chemistry

Abstract

fetched live from OpenAlex

The structures of two isomeric compounds of 5-nitroquinoline with chloro- and nitro-substituted benzoic acid, namely, 2-chloro-4-nitrobenzoic acid–5-nitroquinoline (1/1), (I), and 5-chloro-2-nitrobenzoic acid–5-nitroquinoline (1/1), (II), both C 7 H 4 ClNO 4 ·C 9 H 6 N 2 O 2 , have been determined at 190 K. In each compound, the acid and base molecules are held together by an O—H...N hydrogen bond. In the crystal of (I), the hydrogen-bonded acid–base units are linked by a C—H...O hydrogen bond, forming a tape structure along [1\overline{2}0]. The tapes are stacked into a layer parallel to the ab plane via N—O...π interactions between the nitro group of the base molecule and the quinoline ring system. The layers are further linked by other C—H...O hydrogen bonds, forming a three-dimensional network. In the crystal of (II), the hydrogen-bonded acid–base units are linked into a wide ribbon structure running along [1\overline{1}0] via C—H...O hydrogen bonds. The ribbons are further linked via another C—H...O hydrogen bond, forming a layer parallel to (110). Weak π–π interactions [centroid–centroid distances of 3.7080 (10) and 3.7543 (9) Å] are observed between the quinoline ring systems of adjacent layers. Hirshfeld surfaces for the 5-nitroquinoline molecules of the two compounds mapped over shape index and d norm were generated to visualize the weak intermolecular interactions.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.001
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Science and technology studies, Open science, Research integrity, Insufficient payload (model declined to judge)
Consensus categoriesMeta-epidemiology (narrow), Science and technology studies
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: none
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.776
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.000
Meta-epidemiology (narrow)0.0020.002
Meta-epidemiology (broad)0.0020.002
Bibliometrics0.0020.005
Science and technology studies0.0020.004
Scholarly communication0.0000.001
Open science0.0050.003
Research integrity0.0010.003
Insufficient payload (model declined to judge)0.0020.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.011
GPT teacher head0.240
Teacher spread0.229 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it