Polymorphism, polar morphology and absolute structure determination of 4-iodo-4′-nitrobiphenyl (INBP)

Gaël Labat; Norwid Rasmus Behrnd; Gaëtan Couderc; Michel Bonin; Julius Tsuwi; Athanasios Batagiannis; Ricarda Berger; Mariana Bertoni; Anna Prodi-Schwab; Jürg Hulliger

doi:10.1039/b915469h

Polymorphism, polar morphology and absolute structure determination of 4-iodo-4′-nitrobiphenyl (INBP)

Gaël Labat, Norwid Rasmus Behrnd, Gaëtan Couderc, Michel Bonin, Julius Tsuwi, Athanasios Batagiannis, Ricarda Berger, Mariana Bertoni, Anna Prodi-Schwab, Jürg Hulliger

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

4-Iodo-4′-nitrobiphenyl (INBP), a typical nonlinear optical molecule, features three polymorphs: Fdd2 as known before and two new forms, P2/c and P2. Monopolar crystals of the Fdd2 structure express a polar morphology and allowed an absolute structure determination. Iodo substituents cover the (001) and related faces. A negative pyroelectric coefficient was observed. The P2/c form was obtained from sublimation. Heating INBP (Fdd2) in the range of 150 to 180 °C ended in a second polar form (P2). DSC and dielectric measurements allowed us to assume a diffuse type of phase change from Fdd2 into P2. Lattice energy calculations for Fdd2 and P2/c yielded very similar energies. The twinning state observed for crystals not expressing polar symmetry is explained as a 50: 50 % intergrowth of Fdd2 and P2/c. Periodic fragments allowed the close packing mode of all three polymorphs to be understood. A Hirshfeld surface analysis makes evident that apart from a strong linear synthon (I⋯NO ₂) other interactions in all three forms are very similar.

Original language	English (US)
Pages (from-to)	1252-1262
Number of pages	11
Journal	CrystEngComm
Volume	12
Issue number	4
DOIs	https://doi.org/10.1039/b915469h
State	Published - 2010
Externally published	Yes

ASJC Scopus subject areas

General Chemistry
General Materials Science
Condensed Matter Physics

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title = "Polymorphism, polar morphology and absolute structure determination of 4-iodo-4′-nitrobiphenyl (INBP)",

abstract = "4-Iodo-4′-nitrobiphenyl (INBP), a typical nonlinear optical molecule, features three polymorphs: Fdd2 as known before and two new forms, P2/c and P2. Monopolar crystals of the Fdd2 structure express a polar morphology and allowed an absolute structure determination. Iodo substituents cover the (001) and related faces. A negative pyroelectric coefficient was observed. The P2/c form was obtained from sublimation. Heating INBP (Fdd2) in the range of 150 to 180 °C ended in a second polar form (P2). DSC and dielectric measurements allowed us to assume a diffuse type of phase change from Fdd2 into P2. Lattice energy calculations for Fdd2 and P2/c yielded very similar energies. The twinning state observed for crystals not expressing polar symmetry is explained as a 50: 50 % intergrowth of Fdd2 and P2/c. Periodic fragments allowed the close packing mode of all three polymorphs to be understood. A Hirshfeld surface analysis makes evident that apart from a strong linear synthon (I⋯NO 2) other interactions in all three forms are very similar.",

author = "Ga{\"e}l Labat and Behrnd, {Norwid Rasmus} and Ga{\"e}tan Couderc and Michel Bonin and Julius Tsuwi and Athanasios Batagiannis and Ricarda Berger and Mariana Bertoni and Anna Prodi-Schwab and J{\"u}rg Hulliger",

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T1 - Polymorphism, polar morphology and absolute structure determination of 4-iodo-4′-nitrobiphenyl (INBP)

AU - Labat, Gaël

AU - Behrnd, Norwid Rasmus

AU - Couderc, Gaëtan

AU - Bonin, Michel

AU - Tsuwi, Julius

AU - Batagiannis, Athanasios

AU - Berger, Ricarda

AU - Bertoni, Mariana

AU - Prodi-Schwab, Anna

AU - Hulliger, Jürg

PY - 2010

Y1 - 2010

N2 - 4-Iodo-4′-nitrobiphenyl (INBP), a typical nonlinear optical molecule, features three polymorphs: Fdd2 as known before and two new forms, P2/c and P2. Monopolar crystals of the Fdd2 structure express a polar morphology and allowed an absolute structure determination. Iodo substituents cover the (001) and related faces. A negative pyroelectric coefficient was observed. The P2/c form was obtained from sublimation. Heating INBP (Fdd2) in the range of 150 to 180 °C ended in a second polar form (P2). DSC and dielectric measurements allowed us to assume a diffuse type of phase change from Fdd2 into P2. Lattice energy calculations for Fdd2 and P2/c yielded very similar energies. The twinning state observed for crystals not expressing polar symmetry is explained as a 50: 50 % intergrowth of Fdd2 and P2/c. Periodic fragments allowed the close packing mode of all three polymorphs to be understood. A Hirshfeld surface analysis makes evident that apart from a strong linear synthon (I⋯NO 2) other interactions in all three forms are very similar.

AB - 4-Iodo-4′-nitrobiphenyl (INBP), a typical nonlinear optical molecule, features three polymorphs: Fdd2 as known before and two new forms, P2/c and P2. Monopolar crystals of the Fdd2 structure express a polar morphology and allowed an absolute structure determination. Iodo substituents cover the (001) and related faces. A negative pyroelectric coefficient was observed. The P2/c form was obtained from sublimation. Heating INBP (Fdd2) in the range of 150 to 180 °C ended in a second polar form (P2). DSC and dielectric measurements allowed us to assume a diffuse type of phase change from Fdd2 into P2. Lattice energy calculations for Fdd2 and P2/c yielded very similar energies. The twinning state observed for crystals not expressing polar symmetry is explained as a 50: 50 % intergrowth of Fdd2 and P2/c. Periodic fragments allowed the close packing mode of all three polymorphs to be understood. A Hirshfeld surface analysis makes evident that apart from a strong linear synthon (I⋯NO 2) other interactions in all three forms are very similar.

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Polymorphism, polar morphology and absolute structure determination of 4-iodo-4′-nitrobiphenyl (INBP)

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