Synthesis and crystal structure of a second polymorph of N,N′-bis(salicylidene)-3,5,3′,5′-tetramethyl-biphenyl-4, 4′-diamine

L. Xu; X. Qi; S. J. Kim

doi:10.1007/s10947-006-0417-2

Synthesis and crystal structure of a second polymorph of N,N′-bis(salicylidene)-3,5,3′,5′-tetramethyl-biphenyl-4, 4′-diamine

L. Xu, X. Qi, S. J. Kim

Department of Chemistry & Nanoscience

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

Abstract

The Schiff base compound N,N′-bis(salicylidene)-3,5,3′, 5′-tetramethyl-biphenyl-4,4′-diamine was synthesized and crystal structure was determined by single-crystal X-ray diffractometry. The result shows that there is another polymorphic form (B) in structure besides published one (A) [1]. In structure B, there are four aromatic rings. The dihedral angles between the phenol rings and the adjacent dimethylbenzene rings are distinctly larger than that formed by the dimethylbenzene rings, possibly as a result of the steric hindrance of the methyl groups and the presence of intramolecular O-H...N hydrogen bonds. The remarkable defference between A and B lies in the angles of C1-C6 ring and C25-C30 ring, which are 51.64(13)° and 7.40(7)° in B and A, respectively. Crystal data for the title compolex C ₃₀H₂₇N₂O₂: Monoclinic, P2(1)/c, a = 14.346(3) Å, b = 12.258(2) Å, c = 14.265(3) Å; β = 99.515(4)°, V = 2474.1(7) Å³, Z = 4.

Original language	English
Pages (from-to)	994-997
Number of pages	4
Journal	Journal of Structural Chemistry
Volume	47
Issue number	5
DOIs	https://doi.org/10.1007/s10947-006-0417-2
State	Published - Sep 2006

Bibliographical note

Funding Information:
There are neither S–S stacking nor weak intermolecular hydrogen interactions, and the crystal packing (Fig. 3) is controlled by van der Waals forces. This work was supported by the Korea Research Foundation Grant (KRF-2004-005-C00093) and Research Innovation Program of Nanjing Forestry University (CX03-070-1). Supplementary material. CCDC 287023 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/ retrieving.html [or from the Cambridge Crystallographic Data Center (CCDC), 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)1223-336033; e-mail: [email protected]].

Keywords

Crystal structure
N,N′-bis(salicylidene)-3,5,3′,5′-tetramethyl- biphenyl-4,4′-diamine
Schiff base

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10.1007/s10947-006-0417-2

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@article{dd5df6e54d76418ab164b0eb44a854a6,

title = "Synthesis and crystal structure of a second polymorph of N,N′-bis(salicylidene)-3,5,3′,5′-tetramethyl-biphenyl-4, 4′-diamine",

abstract = "The Schiff base compound N,N′-bis(salicylidene)-3,5,3′, 5′-tetramethyl-biphenyl-4,4′-diamine was synthesized and crystal structure was determined by single-crystal X-ray diffractometry. The result shows that there is another polymorphic form (B) in structure besides published one (A) [1]. In structure B, there are four aromatic rings. The dihedral angles between the phenol rings and the adjacent dimethylbenzene rings are distinctly larger than that formed by the dimethylbenzene rings, possibly as a result of the steric hindrance of the methyl groups and the presence of intramolecular O-H...N hydrogen bonds. The remarkable defference between A and B lies in the angles of C1-C6 ring and C25-C30 ring, which are 51.64(13)° and 7.40(7)° in B and A, respectively. Crystal data for the title compolex C 30H27N2O2: Monoclinic, P2(1)/c, a = 14.346(3) {\AA}, b = 12.258(2) {\AA}, c = 14.265(3) {\AA}; β = 99.515(4)°, V = 2474.1(7) {\AA}3, Z = 4.",

keywords = "Crystal structure, N,N′-bis(salicylidene)-3,5,3′,5′-tetramethyl- biphenyl-4,4′-diamine, Schiff base",

author = "L. Xu and X. Qi and Kim, {S. J.}",

note = "Funding Information: There are neither S–S stacking nor weak intermolecular hydrogen interactions, and the crystal packing (Fig. 3) is controlled by van der Waals forces. This work was supported by the Korea Research Foundation Grant (KRF-2004-005-C00093) and Research Innovation Program of Nanjing Forestry University (CX03-070-1). Supplementary material. CCDC 287023 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/ retrieving.html [or from the Cambridge Crystallographic Data Center (CCDC), 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)1223-336033; e-mail: [email protected]].",

year = "2006",

month = sep,

doi = "10.1007/s10947-006-0417-2",

language = "English",

volume = "47",

pages = "994--997",

journal = "Journal of Structural Chemistry",

issn = "0022-4766",

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TY - JOUR

T1 - Synthesis and crystal structure of a second polymorph of N,N′-bis(salicylidene)-3,5,3′,5′-tetramethyl-biphenyl-4, 4′-diamine

AU - Xu, L.

AU - Qi, X.

AU - Kim, S. J.

N1 - Funding Information: There are neither S–S stacking nor weak intermolecular hydrogen interactions, and the crystal packing (Fig. 3) is controlled by van der Waals forces. This work was supported by the Korea Research Foundation Grant (KRF-2004-005-C00093) and Research Innovation Program of Nanjing Forestry University (CX03-070-1). Supplementary material. CCDC 287023 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/ retrieving.html [or from the Cambridge Crystallographic Data Center (CCDC), 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)1223-336033; e-mail: [email protected]].

PY - 2006/9

Y1 - 2006/9

N2 - The Schiff base compound N,N′-bis(salicylidene)-3,5,3′, 5′-tetramethyl-biphenyl-4,4′-diamine was synthesized and crystal structure was determined by single-crystal X-ray diffractometry. The result shows that there is another polymorphic form (B) in structure besides published one (A) [1]. In structure B, there are four aromatic rings. The dihedral angles between the phenol rings and the adjacent dimethylbenzene rings are distinctly larger than that formed by the dimethylbenzene rings, possibly as a result of the steric hindrance of the methyl groups and the presence of intramolecular O-H...N hydrogen bonds. The remarkable defference between A and B lies in the angles of C1-C6 ring and C25-C30 ring, which are 51.64(13)° and 7.40(7)° in B and A, respectively. Crystal data for the title compolex C 30H27N2O2: Monoclinic, P2(1)/c, a = 14.346(3) Å, b = 12.258(2) Å, c = 14.265(3) Å; β = 99.515(4)°, V = 2474.1(7) Å3, Z = 4.

AB - The Schiff base compound N,N′-bis(salicylidene)-3,5,3′, 5′-tetramethyl-biphenyl-4,4′-diamine was synthesized and crystal structure was determined by single-crystal X-ray diffractometry. The result shows that there is another polymorphic form (B) in structure besides published one (A) [1]. In structure B, there are four aromatic rings. The dihedral angles between the phenol rings and the adjacent dimethylbenzene rings are distinctly larger than that formed by the dimethylbenzene rings, possibly as a result of the steric hindrance of the methyl groups and the presence of intramolecular O-H...N hydrogen bonds. The remarkable defference between A and B lies in the angles of C1-C6 ring and C25-C30 ring, which are 51.64(13)° and 7.40(7)° in B and A, respectively. Crystal data for the title compolex C 30H27N2O2: Monoclinic, P2(1)/c, a = 14.346(3) Å, b = 12.258(2) Å, c = 14.265(3) Å; β = 99.515(4)°, V = 2474.1(7) Å3, Z = 4.

KW - Crystal structure

KW - N,N′-bis(salicylidene)-3,5,3′,5′-tetramethyl- biphenyl-4,4′-diamine

KW - Schiff base

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DO - 10.1007/s10947-006-0417-2

M3 - Article

AN - SCOPUS:33847276173

SN - 0022-4766

VL - 47

SP - 994

EP - 997

JO - Journal of Structural Chemistry

JF - Journal of Structural Chemistry

IS - 5

ER -

Synthesis and crystal structure of a second polymorph of N,N′-bis(salicylidene)-3,5,3′,5′-tetramethyl-biphenyl-4, 4′-diamine

Abstract

Bibliographical note

Keywords

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