In situ crystallization and crystal structure determination of chlorobenzene

Nath, N.; Naumov, Panče

doi:10.20450/mjcce.2015.682

Cited by 6 publications

(6 citation statements)

References 23 publications

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“…2) confirms its identity as chloroalbofungin and that the site of chlorination is as predicted. The C-Cl bond length of 1.741 (2) Å is consistent with other C-Cl single bonds from aromatic systems, for example, chlorobenzene, which was cryocrystallized and found to have a C-Cl bond length of 1.736 (2) Å (Nath & Naumov, 2015). The molecular geometry of 2 is not greatly perturbed from 1 and, as shown in Table 2, the corresponding bond lengths are in good agreement, albeit the standard uncertainties for 2 are larger due to the poorer data quality.…”

Section: Figuresupporting

confidence: 76%

Albofungin and chloroalbofungin: antibiotic crystals with 2D but not 3D isostructurality

She

Sung

et al. 2020

Acta Crystallogr C

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The potent antibiotics albofungin [systematic name: (1S,4R,8aR)-13-amino-1,15,16-trihydroxy-4-methoxy-12-methyl-3,4,8a,13-tetrahydro-1H-xantheno[4′,3′,2′:4,5][1,3]benzodioxino[7,6-g]isoquinoline-14,17(2H,9H)-dione, C27H24N2O9, 1] and its chlorinated analogue chloroalbofungin (the 11-chloro analogue, C27H23ClN2O9, 2) have been crystallized following their isolation from the bacterial strain Streptomyces chrestomyceticus and their structures determined by single-crystal X-ray diffraction. The novel N-aminoquinolone molecular arrangement shows N—N bond lengths of 1.4202 (16) and 1.424 (2) Å in 1 and 2, respectively. The regiochemistry of chloro substitution in the A-ring is para to the quinolone O atom, with a C—Cl bond length of 1.741 (2) Å. The absolute stereochemistry at three chiral centres of the xanthone rings (i.e. 10S, 13R and 19R) is confirmed. Both compounds crystallize in chiral Sohncke space groups consistent with enantiopurity, but are not fully isostructural. A preserved supramolecular construct (SC) confers two-dimensional (2D) isostructurality, but the SC self-associates via either a twofold screw operation in 1, giving a monoclinic P21 structure, or a twofold rotation in 2, affording a monoclinic C2 structure with a doubled unit-cell axis.

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Section: Figuresupporting

confidence: 76%

Albofungin and chloroalbofungin: antibiotic crystals with 2D but not 3D isostructurality

She

Sung

et al. 2020

Acta Crystallogr C

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“…The rhombic motif of C-HÁ Á Á interactions generated over 2800 hits in the CSD search, of which the most interesting are the closely related mono-substituted benzenes: chlorobenzene (MCBENZ; Biswas, 1958;André et al, 1971;Nath & Naumov, 2015), bromobenzene (ZZZSPA; Biswas, 1958) and iodobenzene (REKYAI; Merz, 2006). Each of these crystallizes in space-group type Pbcn and adopts a near identical molecular packing of the phenyl rings to that observed in phenol hemihydrate.…”

Section: Database Surveymentioning

confidence: 99%

Phenol hemihydrate: redetermination of the crystal structure by neutron powder diffraction, Hirshfeld surface analysis and characterization of the thermal expansion

Fortes

2020

Acta Cryst E

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Phenol hemihydrate, C5H5OH·0.5H2O, crystallizes in the space group Pbcn, Z = 8. The previously published crystal structure [CSD refcode PHOLHH; Meuthen & von Stackelberg (1960). Z. Elektrochem. 64, 387–390] is shown to be incorrect. Pairs of phenol molecules, related by an inversion centre, are bridged by one water molecule via O—H...O hydrogen bonds; an extended R 4 4(8) hydrogen-bonded motif links these inversion dimers into chains parallel to the c axis. Packing of the chains is achieved by weaker T-shaped C—H...π interactions between nearest neighbour phenol molecules in the bc plane. Analysis of the thermal expansion and parameterization with a Debye model in terms of the linear elastic moduli shows that the c axis is ∼3 times stiffer than the two orthogonal directions.

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“…In 2015, Nath and Naumov published the structure of a crystal of chlorobenzene 51 [62]. To analyze the intermolecular interactions, the analysis of Hirschfeld partitioning was carried out for chlorobenzene.…”

Section: Organohalogen Compoundsmentioning

confidence: 99%

Organoelement Compounds Crystallized In Situ: Weak Intermolecular Interactions and Lattice Energies

2019

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The in situ crystallization is the most suitable way to obtain a crystal of a low-melting-point compound to determine its structure via X-Ray diffraction. Herein, the intermolecular interactions and some crystal properties of low-melting-point organoelement compounds (lattice energies, melting points, etc.) are discussed. The discussed structures were divided into two groups: organoelement compounds of groups 13–16 and organofluorine compounds with other halogen atoms (Cl, Br, I). The most of intermolecular interactions in the first group are represented by weak hydrogen bonds and H···H interactions. The crystal packing of the second group of compounds is stabilized by various interactions between halogen atoms in conjunction with hydrogen bonding and stacking interactions. The data on intermolecular interactions from the analysis of crystal packing allowed us to obtain correlations between lattice energies and Hirshfeld molecular surface areas, molecular volumes, and melting points.

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In situ crystallization and crystal structure determination of chlorobenzene

Cited by 6 publications

References 23 publications

Albofungin and chloroalbofungin: antibiotic crystals with 2D but not 3D isostructurality

Albofungin and chloroalbofungin: antibiotic crystals with 2D but not 3D isostructurality

Phenol hemihydrate: redetermination of the crystal structure by neutron powder diffraction, Hirshfeld surface analysis and characterization of the thermal expansion

Organoelement Compounds Crystallized In Situ: Weak Intermolecular Interactions and Lattice Energies

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