The crystal structure of 5-acetoxy-6-methoxy-8-nitroquinoline

Sax, M.; Desiderato, R.

doi:10.1107/s0365110x67002658

Cited by 15 publications

(5 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The bond distances and angles are displayed in Fig. 2 and are found to be in reasonable agreement with reported values [for the cyanomethyl sulfone moiety, see the three references listed above; for aromatic sulfone parameters, see Sime & Woodhouse (1974) and Harlow, Simonsen, Pfluger & Sammes (1974); for the quinolyl moiety, see Sax & Desiderato (1967) and Castellano & Prout (1971)]. Fig.…”

supporting

confidence: 84%

“…The deviations from the plane arise from a folding about the C(11)-C(16) bond axis and a twisting about the C(8)... C(13) axis. (3) A conformation in which the methylene group, rather than the sulfonyl O atoms, most closely approaches the ring N atom is not surprising since a strong repulsion between a N lone-pair and an electronegative O atom has been clearly demonstrated in a derivative of 8-nitroquinoline where the nitro group was rotated 59.2 ° out of the quinolyl plane (Sax & Desiderato, 1967). The fact that the S atom deviates markedly (-0.260 A) from the quinolyl plane might also be attributed to the repulsion between 0(2) and N(15).…”

mentioning

confidence: 99%

See 1 more Smart Citation

8-Quinolyl cyanomethyl sulfone

Harlow¹,

Simonsen²,

Sammes³

1976

Acta Crystallogr Sect B

View full text Add to dashboard Cite

supporting

confidence: 84%

mentioning

confidence: 99%

8-Quinolyl cyanomethyl sulfone

Harlow¹,

Simonsen²,

Sammes³

1976

Acta Crystallogr Sect B

View full text Add to dashboard Cite

“…The reasons for the non-planarity of the molecule are not obvious since in other isoquinoline derivatives and quinoline derivatives [such as those reported by Merritt & Duffin (1970)], the deviations from planarity appear to be much smaller. However, Sax & Desiderato (1967) reported that 5-acetoxy-6-methoxy-8-nitroquinoline was folded by 1.9 ° in an almost identical manner to that found in our study. Unfortunately, the studies by Genet (1965) on isoquinoline hydrochloride are not sufficiently precise to resolve this problem.…”

supporting

confidence: 53%

1-Phenyl-3-methylisoquinoline hydrobromide

Rychłewska¹,

Palenik²,

Kosturkiewicz³

1975

Acta Crystallogr Sect B

View full text Add to dashboard Cite

Abstract. C:6H~4NBr, M= 300.20, orthorhombic, Pbca, a=14.207(3), b=16.107(6), c=11.560(4) A, V= 2645 (1) Aa, Z=8, Dx= 1"508, D,,= 1"52 g cm -3. The conventional R was 0.032 for the 1368 reflections [I> 2o'(1)] measured with a Syntex PI diffractometer.The X-ray analysis confirms that the title compound is the product of the cyclization of 3,4-diphenylbut-3-en-2-one oxime benzoate in nitrobenzene solution.Introduction. X-ray diffraction data were measured with graphite-monochromated Mo Kc~ radiation. A crystal 0.34 x 0.39 x 0.44 mm was used. The unit-cell dimensions were obtained from a least-squares fit of the 20, 09, 2' and ~0 values for 15 reflections. A variable speed (1 to 24 ° min -1) 0-20 scan technique was used in measuring all the independent reflections to a maximum 20 of 45 °. The scan range was 1 ° on either side of the e:-e2 peaks. The 1368 reflections with I>2.0a(I) were used in the analysis. The intensities were reduced to a set of structure amplitudes on an

show abstract

“…No anomalous or unusual thermal i motions are exhibited by the heavy (non-hydrogen) atoms. The following abbreviations are used: 8HQNO for 8-hydroxyquinoline-N-oxide (this study); Cu-8HQN for copper-8-hydroxyquinolinate (Palenik, 1964a); Zn-8HQN for zinc-8-hydroxyquinolinate dihydrate (Palenik, 1964b); AMNQN for 5-acetoxy-6-methoxy-8-nitroquinoline (Sax & Desiderato, 1967); and MNQ for 6-methoxy-8-nitro-5(1H)-quinolone (Sax, Desiderato, & Dakin, 1969 Table 6 gives the equation for the least-squares best plane (Schomaker, Waser, Marsh & Bergman, 1959) for the quinoline moiety and the deviations of the atoms from this plane. The ring is quite planar, the largest deviation, 0.014 A, being due to C(4).…”

Section: +Klb*c*u23)]mentioning

confidence: 99%

The molecular and crystal structure of 8-hydroxyquinoline N-oxide

Desiderato¹,

Terry²,

Freemann³

et al. 1971

Acta Crystallogr Sect B

Self Cite

View full text Add to dashboard Cite

The structure of 8-hydroxyquinoline-N-oxide was determined from diffractometer data by a direct method. The compound crystallizes in the monoclinic system with space group P21/c. The cell data are: a= 12.1364 (4), b=4.9211 (2), c= 13"1384 (4) /~, fl= I09"26 (1) °, Dealt= 1-449 g.cm -a, De,,p= 1.46 g.cm -3, Z= 4. The structure was solved by a direct method. A total of 1528 reflections were used in a full-matrix least-squares refinement. R was reduced to a final value of 0.053. Bond lengths between non-hydrogen atoms have e.s.d.'s between 0.002 and 0.003 A. The e.s.d.'s of the various bond angles (non-hydrogen atoms) range from 0"01 to 0"02 °. Distances and angles involving the hydrogen atoms have e.s.d.'s of 0.02/~ and 1 °, respectively. The two C-N distances of the quinoline ring are unusually long and the quinoline moiety is surprisingly similar to naphthalene in terms of bond distances and angles. It is believed that the inductive effect of the N-O group may in part be responsible for the C-N lengthenings. The hydroxyl hydrogen atom is bonded to the dative oxygen atom via a short intramolecular hydrogen bond. The direct relationship between the N-O dative bond distance and the strength of a hydrogen bond to the dative oxygen atom appears to be substantiated in this study.

show abstract

The crystal structure of 5-acetoxy-6-methoxy-8-nitroquinoline

Cited by 15 publications

References 1 publication

8-Quinolyl cyanomethyl sulfone

8-Quinolyl cyanomethyl sulfone

1-Phenyl-3-methylisoquinoline hydrobromide

The molecular and crystal structure of 8-hydroxyquinoline N-oxide

Contact Info

Product

Resources

About