Whole Molecule Disorder in a Solid Solution of Two Indoloacridines

Sridharan, Makuteswaran; Prasad, K. J. Rajendra; Kotheimer, Amanda E.; Wagner, Timothy R.; Zeller, Mat­thias

doi:10.1007/s10870-009-9562-8

Cited by 8 publications

(6 citation statements)

References 21 publications

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“…The N-H group does not form a classical hydrogen bond in the solid state and no strong π-π stacking interactions are observed. Other than van der Waals dispersive forces the packing of the compound in the solid state is dominated by C- In a recent publication (Sridharan et al, 2009b) we reported the structure of the dehydrogenated derivative of the title compound. It crystallizes in a primitive inversion symmetric setting with a similar volume as for the structure of the title compound.…”

Section: S1 Commentmentioning

confidence: 99%

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9-Chloro-1-methyl-7-phenyl-5,6-dihydro-13H-indolo[3,2-c]acridine

Sridharan¹,

Prasad²,

Zeller³

2009

Acta Cryst E

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The title compound, C26H19ClN2, is a 5,6-dihydro-13H-indolo[3,2-c]acridine prepared by condensation of a 2,3,4,9-tetrahydro-1H-carbazol-1-one with 2-aminobenzophenone. The crystals undergo a destructive phase change upon cooling at varying temperatures between 270 and 200 K, depending on cooling rate and disturbance by vibration, thus indicating supercooling of the metastable room-temperature structure at lower temperature. The overall planarity of the indolo[3,2-c]acridine part of the molecule is interrupted by the saturated ethylene group, and the planes of the two halves exhibit a dihedral angle of 22.05 (6)° with each other while themselves being essentially planar. Packing is dominated by C—H⋯π interactions. No classical hydrogen bonds or stacking interactions are observed.

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Section: S1 Commentmentioning

confidence: 99%

“…They were refined with isotropic displacement parameters U iso of 1.5 (methyl) or 1.2 times U eq (all others) of the adjacent C or N atom. Overlay of the title compound with its hydrogenated counterpart (Sridharan et al, 2009b). The chlorobenzene part of the top molecule was used to define the overlay of the two compounds.…”

Section: S3 Refinementmentioning

confidence: 99%

9-Chloro-1-methyl-7-phenyl-5,6-dihydro-13H-indolo[3,2-c]acridine

Sridharan¹,

Prasad²,

Zeller³

2009

Acta Cryst E

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“…For our synthetic strategy, 2,3,4,9-tetrahydro-1H-carbazol-1-ones prepared in our laboratory were used as precursors, opening new avenues for the synthesis of highly functionalized carbazole derivatives such as 1-hydroxyimino-2,3,4,9-tetrahydro-1H-carbazoles, 1-hydroxycarbazoles, and 1-hydroxy-2-formylcarbazoles. The functionalized carbazoles thus prepared lead to mukonine isomers, oxazolocarbazoles, girinimbine isomers, pyranocarbazoles, indoloisoflavones, indolocoumarins, indoloxanthones, benzocarbazoles, carbazolyloxypropanolamines and pyrazolo-, isoxazolo-, furo-, oxazino-, pyrimido-, pyridazino-, ISSN 2056-9890 pyrido-, pyrazino-and indolo-carbazoles in excellent yields (Shanmugasundaram & Rajendra Prasad, 1999;Sridharan & Rajendra Prasad, 2011;Sridharan, Beagle et al, 2008 and references cited therein). Herein, we report the synthesis and crystal structure of 1-hydroxy-8-methyl-9H-carbazole-2carbaldehyde (Fig.…”

Section: Chemical Contextmentioning

confidence: 99%

Synthesis and crystal structure of 1-hydroxy-8-methyl-9H-carbazole-2-carbaldehyde

Thiruvalluvar¹,

Sridharan²,

Prasad

et al. 2021

Acta Cryst E

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Two crystallographically independent molecules are present in the asymmetric unit of the title compound, C14H11NO2, with virtually identical geometries. The carbazole units are planar. The hydroxy group at position 1, carbaldehyde group at position 2, and methyl group at position 8 (with the exception of two H atoms) are coplanar with the attached benzene rings. The dihedral angle between the two benzene rings is 2.20 (9)° in molecule A and 2.01 (9)° in molecule B. The pyrrole ring makes dihedral angles of 0.82 (10) and 1.40 (10)° [0.84 (10) and 1.18 (10)° in molecule B] with the (–CH3)-substituted and (–OH and –CHO) substituted benzene rings, respectively. The molecular structure is stabilized by the intramolecular O—H...O hydrogen bonds, while the crystal structure features N—H...O and C—H...O hydrogen bonds. A range of π–π contacts further stabilizes the crystal structure.

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“…14 Solid solutions using whole organic molecules have been lightly investigated as highlighted by Cherukuvada and Nangia in their review of eutectic systems. 15 Examples of molecular solid solutions include benzoic acid/4-fluorobenzoic acid, 16 oxa-androgens, 17 indoloacridines, 18 and tritylnitrile/tritylisonitrile 19 systems although very few have investigated the change in physical properties beyond a change in melting point. This technique is readily used in the inorganic solid state literature in order to alter the properties of materials such as superconductors.…”

Section: Introductionmentioning

confidence: 99%