Structure of 1-(4-Nitrophenyl)pyrrole,-imidazole,-pyrazole and -1,2,4-triazole derivatives

Makoto Ishihara, Masahiko Tonogaki, Shigeru Ohba, Yoshihiko Saito, Masaki Okazaki, Takayuki Katoh, Koji Kamiyama

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Abstract

Structures of seven related compounds were determined to assess the nonlinear optical properties of the crystals. Mo Kα, ,λ = 0.71073 Å. 2-Methyl-l-(4-nitrophenyl)imidazole (I), C10H 9N3O2, Mr=203.2, monoclinic, P2 1/c, a= 17.513 (3), b = 7.405 (1), c= 16.819 (3)Å, β = 118.25 (1) °, V = 1921.4 (6) Å 3, Z = 8, Dx = 1.40 Mg m -3, Mo Kα, μ = 0.095 mm-1, F(000) = 848, T = 300 (1) K, R = 0.049 for 2172 reflections. 2,4-Dimethyl-l-(4- nitrophenyl) imidazole (II), C11H11N3O 2, Mr = 217.2, orthorhombic, P21ab, a = 11.808 (3), b = 22.132 (7), c=3.999(1) Å, V =1045.1(5) Å3, Z=4, Dx= 1.38 Mg m -3, Mo Kα, μ = 0.092 mm -1, F(000) = 456, T = 297 (1) K, R = 0.064 for 723 reflections. 2-Ethyl-l-(4-nitrophenyl)imidazole (III), C11H11N 3-O2, Mr = 217.2, orthorhombic, Pca2 1, a = 24.159 (5), b = 4.033 (1), c = 10.658 (2) Å, V= 1038.4 (4) Å3, Z = 4, Dm = 1.38 (1), Dx = 1.39 Mg m -3, μ, = 0.093 mm-1, F(000) = 456, T = 300 (1) K, R = 0.043 for 926 reflections. 1-(4-Nitrophenyl)-2-phenylimidazole (IV), C 15H11N3O2, Mr = 265.3, triclinic, P1, a = 9.350 (2), b = 11.893 (3), c = 12.658 (3) Å, α = 103.73 (2), β= 103.68(2), γ,= 97.05 (2) ° , V = 1304.6 (6) Å3, Z = 4, Dx = 1.35 Mg m-3, Mo Kα, μ, = 0.087 mm-1, F(000) = 552, T = 297 (1) K, R = 0.043 for 1804 reflections. 1-(4-Nitrophenyl)pyrazole (W), C9H7N 3O2, Mr-189.2, monoclinic, P21/n, a = 11.519(2), b= 10.342(2), c=7.077(1)Å, β= 93.68 (1) °, V = 841.3 (2) Å3, Z = 4, Om = 1.49 (1), Dx = 1.49 Mg m-3, Mo Kα, μ = 0.103 mm-1, F(000) = 392, T = 299 (1) K, R = 0.045 for 1188 reflections. 3,5-Dichloro-l-(4-nitrophenyl)-l,2,4- triazole (VI), C8H4N4O2Cl 2, Mr=259.1, monoclinic, P21, a = 11.282(4), b= 11.902(5), c =3.753 (1)Å, β= 92.81 (3) °, V= 503.3 (3) Å3, z= 2, Dx = 1.71 Mg m -3, Mo Kα, μ, = 0.632 mm-1, F(000) = 260, T= 297 (1) K, R = 0.023 for 639 reflections. 1-(4-Nitrophenyl)pyrrole (VII), C10H8N 2O2, Mr = 188.2, orthorhombic, Fdd2, a = 13.651 (2), b = 10.930 (2), c = 11.721 (2) Å, V= 1748.8 (5) Å3, Z = 8, Dm = 1.42(1), Dx = 1.43 Mgm -3, Mo Kα, μ = 0.096 mm-l, F(000) = 784, T = 301 (1) K, R = 0.044 for 342 reflections. The nitro groups are almost in the plane of the benzene rings with dihedral angles of less than 14 °. On the other hand, the five-membered hetero rings make angles of more than 36 ° to the benzene rings [except for (V): 2.5 (3)° and (VII): 15.1 (4) °] reflecting the steric repulsion between the hetero ring substituent proximal to the junction and the phenyl group. The molecular arrangements of (1I) and (III) are essentially identical and are in a zigzag mode. When there is no substituent on the five-membered hetero ring, the molecules are packed with the long axes parallel (VII) or anti-parallel (V) to each other. Crystals of (VII) are expected to exhibit good nonlinear optical properties.

Original languageEnglish
Pages (from-to)184-188
Number of pages5
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume48
Issue number1
DOIs
Publication statusPublished - 1992

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Pyrroles
Derivatives
Benzene
Optical properties
Crystals
Triazoles
Dihedral angle
1,2,4-triazole
imidazole
4-nitrophenyl
pyrazole
Molecules

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

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Structure of 1-(4-Nitrophenyl)pyrrole,-imidazole,-pyrazole and -1,2,4-triazole derivatives. / Ishihara, Makoto; Tonogaki, Masahiko; Ohba, Shigeru; Saito, Yoshihiko; Okazaki, Masaki; Katoh, Takayuki; Kamiyama, Koji.

In: Acta Crystallographica Section C: Crystal Structure Communications, Vol. 48, No. 1, 1992, p. 184-188.

Research output: Contribution to journalArticle

Ishihara, Makoto ; Tonogaki, Masahiko ; Ohba, Shigeru ; Saito, Yoshihiko ; Okazaki, Masaki ; Katoh, Takayuki ; Kamiyama, Koji. / Structure of 1-(4-Nitrophenyl)pyrrole,-imidazole,-pyrazole and -1,2,4-triazole derivatives. In: Acta Crystallographica Section C: Crystal Structure Communications. 1992 ; Vol. 48, No. 1. pp. 184-188.
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title = "Structure of 1-(4-Nitrophenyl)pyrrole,-imidazole,-pyrazole and -1,2,4-triazole derivatives",
abstract = "Structures of seven related compounds were determined to assess the nonlinear optical properties of the crystals. Mo Kα, ,λ = 0.71073 {\AA}. 2-Methyl-l-(4-nitrophenyl)imidazole (I), C10H 9N3O2, Mr=203.2, monoclinic, P2 1/c, a= 17.513 (3), b = 7.405 (1), c= 16.819 (3){\AA}, β = 118.25 (1) °, V = 1921.4 (6) {\AA} 3, Z = 8, Dx = 1.40 Mg m -3, Mo Kα, μ = 0.095 mm-1, F(000) = 848, T = 300 (1) K, R = 0.049 for 2172 reflections. 2,4-Dimethyl-l-(4- nitrophenyl) imidazole (II), C11H11N3O 2, Mr = 217.2, orthorhombic, P21ab, a = 11.808 (3), b = 22.132 (7), c=3.999(1) {\AA}, V =1045.1(5) {\AA}3, Z=4, Dx= 1.38 Mg m -3, Mo Kα, μ = 0.092 mm -1, F(000) = 456, T = 297 (1) K, R = 0.064 for 723 reflections. 2-Ethyl-l-(4-nitrophenyl)imidazole (III), C11H11N 3-O2, Mr = 217.2, orthorhombic, Pca2 1, a = 24.159 (5), b = 4.033 (1), c = 10.658 (2) {\AA}, V= 1038.4 (4) {\AA}3, Z = 4, Dm = 1.38 (1), Dx = 1.39 Mg m -3, μ, = 0.093 mm-1, F(000) = 456, T = 300 (1) K, R = 0.043 for 926 reflections. 1-(4-Nitrophenyl)-2-phenylimidazole (IV), C 15H11N3O2, Mr = 265.3, triclinic, P1, a = 9.350 (2), b = 11.893 (3), c = 12.658 (3) {\AA}, α = 103.73 (2), β= 103.68(2), γ,= 97.05 (2) ° , V = 1304.6 (6) {\AA}3, Z = 4, Dx = 1.35 Mg m-3, Mo Kα, μ, = 0.087 mm-1, F(000) = 552, T = 297 (1) K, R = 0.043 for 1804 reflections. 1-(4-Nitrophenyl)pyrazole (W), C9H7N 3O2, Mr-189.2, monoclinic, P21/n, a = 11.519(2), b= 10.342(2), c=7.077(1){\AA}, β= 93.68 (1) °, V = 841.3 (2) {\AA}3, Z = 4, Om = 1.49 (1), Dx = 1.49 Mg m-3, Mo Kα, μ = 0.103 mm-1, F(000) = 392, T = 299 (1) K, R = 0.045 for 1188 reflections. 3,5-Dichloro-l-(4-nitrophenyl)-l,2,4- triazole (VI), C8H4N4O2Cl 2, Mr=259.1, monoclinic, P21, a = 11.282(4), b= 11.902(5), c =3.753 (1){\AA}, β= 92.81 (3) °, V= 503.3 (3) {\AA}3, z= 2, Dx = 1.71 Mg m -3, Mo Kα, μ, = 0.632 mm-1, F(000) = 260, T= 297 (1) K, R = 0.023 for 639 reflections. 1-(4-Nitrophenyl)pyrrole (VII), C10H8N 2O2, Mr = 188.2, orthorhombic, Fdd2, a = 13.651 (2), b = 10.930 (2), c = 11.721 (2) {\AA}, V= 1748.8 (5) {\AA}3, Z = 8, Dm = 1.42(1), Dx = 1.43 Mgm -3, Mo Kα, μ = 0.096 mm-l, F(000) = 784, T = 301 (1) K, R = 0.044 for 342 reflections. The nitro groups are almost in the plane of the benzene rings with dihedral angles of less than 14 °. On the other hand, the five-membered hetero rings make angles of more than 36 ° to the benzene rings [except for (V): 2.5 (3)° and (VII): 15.1 (4) °] reflecting the steric repulsion between the hetero ring substituent proximal to the junction and the phenyl group. The molecular arrangements of (1I) and (III) are essentially identical and are in a zigzag mode. When there is no substituent on the five-membered hetero ring, the molecules are packed with the long axes parallel (VII) or anti-parallel (V) to each other. Crystals of (VII) are expected to exhibit good nonlinear optical properties.",
author = "Makoto Ishihara and Masahiko Tonogaki and Shigeru Ohba and Yoshihiko Saito and Masaki Okazaki and Takayuki Katoh and Koji Kamiyama",
year = "1992",
doi = "10.1107/S0108270191004109",
language = "English",
volume = "48",
pages = "184--188",
journal = "Acta Crystallographica Section C: Crystal Structure Communications",
issn = "0108-2701",
publisher = "International Union of Crystallography",
number = "1",

}

TY - JOUR

T1 - Structure of 1-(4-Nitrophenyl)pyrrole,-imidazole,-pyrazole and -1,2,4-triazole derivatives

AU - Ishihara, Makoto

AU - Tonogaki, Masahiko

AU - Ohba, Shigeru

AU - Saito, Yoshihiko

AU - Okazaki, Masaki

AU - Katoh, Takayuki

AU - Kamiyama, Koji

PY - 1992

Y1 - 1992

N2 - Structures of seven related compounds were determined to assess the nonlinear optical properties of the crystals. Mo Kα, ,λ = 0.71073 Å. 2-Methyl-l-(4-nitrophenyl)imidazole (I), C10H 9N3O2, Mr=203.2, monoclinic, P2 1/c, a= 17.513 (3), b = 7.405 (1), c= 16.819 (3)Å, β = 118.25 (1) °, V = 1921.4 (6) Å 3, Z = 8, Dx = 1.40 Mg m -3, Mo Kα, μ = 0.095 mm-1, F(000) = 848, T = 300 (1) K, R = 0.049 for 2172 reflections. 2,4-Dimethyl-l-(4- nitrophenyl) imidazole (II), C11H11N3O 2, Mr = 217.2, orthorhombic, P21ab, a = 11.808 (3), b = 22.132 (7), c=3.999(1) Å, V =1045.1(5) Å3, Z=4, Dx= 1.38 Mg m -3, Mo Kα, μ = 0.092 mm -1, F(000) = 456, T = 297 (1) K, R = 0.064 for 723 reflections. 2-Ethyl-l-(4-nitrophenyl)imidazole (III), C11H11N 3-O2, Mr = 217.2, orthorhombic, Pca2 1, a = 24.159 (5), b = 4.033 (1), c = 10.658 (2) Å, V= 1038.4 (4) Å3, Z = 4, Dm = 1.38 (1), Dx = 1.39 Mg m -3, μ, = 0.093 mm-1, F(000) = 456, T = 300 (1) K, R = 0.043 for 926 reflections. 1-(4-Nitrophenyl)-2-phenylimidazole (IV), C 15H11N3O2, Mr = 265.3, triclinic, P1, a = 9.350 (2), b = 11.893 (3), c = 12.658 (3) Å, α = 103.73 (2), β= 103.68(2), γ,= 97.05 (2) ° , V = 1304.6 (6) Å3, Z = 4, Dx = 1.35 Mg m-3, Mo Kα, μ, = 0.087 mm-1, F(000) = 552, T = 297 (1) K, R = 0.043 for 1804 reflections. 1-(4-Nitrophenyl)pyrazole (W), C9H7N 3O2, Mr-189.2, monoclinic, P21/n, a = 11.519(2), b= 10.342(2), c=7.077(1)Å, β= 93.68 (1) °, V = 841.3 (2) Å3, Z = 4, Om = 1.49 (1), Dx = 1.49 Mg m-3, Mo Kα, μ = 0.103 mm-1, F(000) = 392, T = 299 (1) K, R = 0.045 for 1188 reflections. 3,5-Dichloro-l-(4-nitrophenyl)-l,2,4- triazole (VI), C8H4N4O2Cl 2, Mr=259.1, monoclinic, P21, a = 11.282(4), b= 11.902(5), c =3.753 (1)Å, β= 92.81 (3) °, V= 503.3 (3) Å3, z= 2, Dx = 1.71 Mg m -3, Mo Kα, μ, = 0.632 mm-1, F(000) = 260, T= 297 (1) K, R = 0.023 for 639 reflections. 1-(4-Nitrophenyl)pyrrole (VII), C10H8N 2O2, Mr = 188.2, orthorhombic, Fdd2, a = 13.651 (2), b = 10.930 (2), c = 11.721 (2) Å, V= 1748.8 (5) Å3, Z = 8, Dm = 1.42(1), Dx = 1.43 Mgm -3, Mo Kα, μ = 0.096 mm-l, F(000) = 784, T = 301 (1) K, R = 0.044 for 342 reflections. The nitro groups are almost in the plane of the benzene rings with dihedral angles of less than 14 °. On the other hand, the five-membered hetero rings make angles of more than 36 ° to the benzene rings [except for (V): 2.5 (3)° and (VII): 15.1 (4) °] reflecting the steric repulsion between the hetero ring substituent proximal to the junction and the phenyl group. The molecular arrangements of (1I) and (III) are essentially identical and are in a zigzag mode. When there is no substituent on the five-membered hetero ring, the molecules are packed with the long axes parallel (VII) or anti-parallel (V) to each other. Crystals of (VII) are expected to exhibit good nonlinear optical properties.

AB - Structures of seven related compounds were determined to assess the nonlinear optical properties of the crystals. Mo Kα, ,λ = 0.71073 Å. 2-Methyl-l-(4-nitrophenyl)imidazole (I), C10H 9N3O2, Mr=203.2, monoclinic, P2 1/c, a= 17.513 (3), b = 7.405 (1), c= 16.819 (3)Å, β = 118.25 (1) °, V = 1921.4 (6) Å 3, Z = 8, Dx = 1.40 Mg m -3, Mo Kα, μ = 0.095 mm-1, F(000) = 848, T = 300 (1) K, R = 0.049 for 2172 reflections. 2,4-Dimethyl-l-(4- nitrophenyl) imidazole (II), C11H11N3O 2, Mr = 217.2, orthorhombic, P21ab, a = 11.808 (3), b = 22.132 (7), c=3.999(1) Å, V =1045.1(5) Å3, Z=4, Dx= 1.38 Mg m -3, Mo Kα, μ = 0.092 mm -1, F(000) = 456, T = 297 (1) K, R = 0.064 for 723 reflections. 2-Ethyl-l-(4-nitrophenyl)imidazole (III), C11H11N 3-O2, Mr = 217.2, orthorhombic, Pca2 1, a = 24.159 (5), b = 4.033 (1), c = 10.658 (2) Å, V= 1038.4 (4) Å3, Z = 4, Dm = 1.38 (1), Dx = 1.39 Mg m -3, μ, = 0.093 mm-1, F(000) = 456, T = 300 (1) K, R = 0.043 for 926 reflections. 1-(4-Nitrophenyl)-2-phenylimidazole (IV), C 15H11N3O2, Mr = 265.3, triclinic, P1, a = 9.350 (2), b = 11.893 (3), c = 12.658 (3) Å, α = 103.73 (2), β= 103.68(2), γ,= 97.05 (2) ° , V = 1304.6 (6) Å3, Z = 4, Dx = 1.35 Mg m-3, Mo Kα, μ, = 0.087 mm-1, F(000) = 552, T = 297 (1) K, R = 0.043 for 1804 reflections. 1-(4-Nitrophenyl)pyrazole (W), C9H7N 3O2, Mr-189.2, monoclinic, P21/n, a = 11.519(2), b= 10.342(2), c=7.077(1)Å, β= 93.68 (1) °, V = 841.3 (2) Å3, Z = 4, Om = 1.49 (1), Dx = 1.49 Mg m-3, Mo Kα, μ = 0.103 mm-1, F(000) = 392, T = 299 (1) K, R = 0.045 for 1188 reflections. 3,5-Dichloro-l-(4-nitrophenyl)-l,2,4- triazole (VI), C8H4N4O2Cl 2, Mr=259.1, monoclinic, P21, a = 11.282(4), b= 11.902(5), c =3.753 (1)Å, β= 92.81 (3) °, V= 503.3 (3) Å3, z= 2, Dx = 1.71 Mg m -3, Mo Kα, μ, = 0.632 mm-1, F(000) = 260, T= 297 (1) K, R = 0.023 for 639 reflections. 1-(4-Nitrophenyl)pyrrole (VII), C10H8N 2O2, Mr = 188.2, orthorhombic, Fdd2, a = 13.651 (2), b = 10.930 (2), c = 11.721 (2) Å, V= 1748.8 (5) Å3, Z = 8, Dm = 1.42(1), Dx = 1.43 Mgm -3, Mo Kα, μ = 0.096 mm-l, F(000) = 784, T = 301 (1) K, R = 0.044 for 342 reflections. The nitro groups are almost in the plane of the benzene rings with dihedral angles of less than 14 °. On the other hand, the five-membered hetero rings make angles of more than 36 ° to the benzene rings [except for (V): 2.5 (3)° and (VII): 15.1 (4) °] reflecting the steric repulsion between the hetero ring substituent proximal to the junction and the phenyl group. The molecular arrangements of (1I) and (III) are essentially identical and are in a zigzag mode. When there is no substituent on the five-membered hetero ring, the molecules are packed with the long axes parallel (VII) or anti-parallel (V) to each other. Crystals of (VII) are expected to exhibit good nonlinear optical properties.

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SN - 0108-2701

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