### 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), C_{10}H _{9}N_{3}O_{2}, M_{r}=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, D_{x} = 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), C_{11}H_{11}N_{3}O _{2}, M_{r} = 217.2, orthorhombic, P2_{1}ab, a = 11.808 (3), b = 22.132 (7), c=3.999(1) Å, V =1045.1(5) Å^{3}, Z=4, D_{x}= 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), C_{11}H_{11}N _{3}-O_{2}, M_{r} = 217.2, orthorhombic, Pca2 _{1}, a = 24.159 (5), b = 4.033 (1), c = 10.658 (2) Å, V= 1038.4 (4) Å^{3}, Z = 4, D_{m} = 1.38 (1), D_{x} = 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 _{15}H_{11}N_{3}O_{2}, M_{r} = 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) Å^{3}, Z = 4, D_{x} = 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), C_{9}H_{7}N _{3}O_{2}, M_{r}-189.2, monoclinic, P2_{1}/n, a = 11.519(2), b= 10.342(2), c=7.077(1)Å, β= 93.68 (1) °, V = 841.3 (2) Å^{3}, Z = 4, O_{m} = 1.49 (1), D_{x} = 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), C_{8}H_{4}N_{4}O_{2}Cl _{2}, M_{r}=259.1, monoclinic, P2_{1}, a = 11.282(4), b= 11.902(5), c =3.753 (1)Å, β= 92.81 (3) °, V= 503.3 (3) Å^{3}, z= 2, D_{x} = 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), C_{10}H_{8}N _{2}O_{2}, M_{r} = 188.2, orthorhombic, Fdd2, a = 13.651 (2), b = 10.930 (2), c = 11.721 (2) Å, V= 1748.8 (5) Å^{3}, Z = 8, D_{m} = 1.42(1), D_{x} = 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 language | English |
---|---|

Pages (from-to) | 184-188 |

Number of pages | 5 |

Journal | Acta Crystallographica Section C: Crystal Structure Communications |

Volume | 48 |

Issue number | 1 |

DOIs | |

Publication status | Published - 1992 |

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### Cite this

*Acta Crystallographica Section C: Crystal Structure Communications*,

*48*(1), 184-188. https://doi.org/10.1107/S0108270191004109

**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.

Research output: Contribution to journal › Article

*Acta Crystallographica Section C: Crystal Structure Communications*, vol. 48, no. 1, pp. 184-188. https://doi.org/10.1107/S0108270191004109

}

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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U2 - 10.1107/S0108270191004109

DO - 10.1107/S0108270191004109

M3 - Article

AN - SCOPUS:0000311912

VL - 48

SP - 184

EP - 188

JO - Acta Crystallographica Section C: Crystal Structure Communications

JF - Acta Crystallographica Section C: Crystal Structure Communications

SN - 0108-2701

IS - 1

ER -