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Crystal structures of three indole derivatives: 3-ethnyl-2-methyl-1-phenyl-sulfonyl-1H-indole, 4-phenyl-sulfonyl-3H,4H-cyclo-penta-[b]indol-1(2H)-one and 1-{2-[(E)-2-(5-chloro-2-nitro-phen-yl)ethen-yl]-1-phenyl-sulfonyl-1H-indol-3-yl}ethan-1-one chloro-form monosolvate.

Gopinath S, Sethusankar K, Ramalingam BM, Mohanakrishnan AK - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: Compounds (I) and (II) crystalize with two independent mol-ecules in the asymmetric unit.The indole ring systems in all three structures deviate only slightly from planarity, with dihedral angles between the planes of the pyrrole and benzene rings spanning the tight range 0.20 (9)-1.65 (9)°.These indole ring systems, in turn, are almost orthogonal to the phenyl-sulfonyl rings [range of dihedral angles between mean planes = 77.21 (8)-89.26 (8)°].

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Affiliation: Department of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India.

ABSTRACT
The title compounds, C17H13NO2S, (I), C17H13NO3S, (II), and C24H17ClN2O5S·CHCl3, (III), are indole derivatives. Compounds (I) and (II) crystalize with two independent mol-ecules in the asymmetric unit. The indole ring systems in all three structures deviate only slightly from planarity, with dihedral angles between the planes of the pyrrole and benzene rings spanning the tight range 0.20 (9)-1.65 (9)°. These indole ring systems, in turn, are almost orthogonal to the phenyl-sulfonyl rings [range of dihedral angles between mean planes = 77.21 (8)-89.26 (8)°]. In the three compounds, the mol-ecular structure is stabilized by intra-molecular C-H⋯O hydrogen bonds, generating S(6) ring motifs with the sulfone O atom. In compounds (I) and (II), the two independent mol-ecules are linked by C-H⋯O hydrogen bonds and C-H⋯π inter-actions, while in compound (III), the mol-ecules are linked by C-H⋯O hydrogen bonds, generating R 2 (2)(22) inversion dimers.

No MeSH data available.


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The crystal packing of compound (I), viewed down the b axis, showing C12B—H12B⋯O2Ai inter­molecular hydrogen bond link the independent mol­ecules running parallel to the [101] direction and further inter­connected by C10A—H10A⋯Cg1ii, C11A—H11A⋯Cg2ii and C16A—H16A⋯Cg3iii inter­actions. Cg2 is the centre of the gravity of the pyrrole ring (atoms N1B/C1B/C6B/C7B/C8B), and Cg1 and Cg3 are the centres of the gravity of benzene rings C1B–C6B and C1A–C6A, respectively. [Symmetry codes: (i) −x + 1, y + , −z + 1; (ii) −x + 2, y − , −z + 1; (iii) −x + 1, y + , −z.]
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fig6: The crystal packing of compound (I), viewed down the b axis, showing C12B—H12B⋯O2Ai inter­molecular hydrogen bond link the independent mol­ecules running parallel to the [101] direction and further inter­connected by C10A—H10A⋯Cg1ii, C11A—H11A⋯Cg2ii and C16A—H16A⋯Cg3iii inter­actions. Cg2 is the centre of the gravity of the pyrrole ring (atoms N1B/C1B/C6B/C7B/C8B), and Cg1 and Cg3 are the centres of the gravity of benzene rings C1B–C6B and C1A–C6A, respectively. [Symmetry codes: (i) −x + 1, y + , −z + 1; (ii) −x + 2, y − , −z + 1; (iii) −x + 1, y + , −z.]

Mentions: In the crystal packing of compound (I), the mol­ecules are linked via inter­molecular C16B—H16B⋯O2A(−x + 1, y + , −z + 1) hydrogen bonds running parallel to the [101] direction. The crystal packing is further stabilized by inter­molecular C10A—H10A⋯Cg1, C11A—H11A⋯Cg2 and C16A—H16A⋯Cg3 inter­actions, with separations of 3.727 (2), 3.546 (2) and 3.699 (3) Å at (−x + 2, y − , −z + 1) and (−x + 1, y + , −z), respectively. Cg2 is the centre of gravity of pyrrole ring N1B/C1B/C6B/C7B/C8B, and Cg1 and Cg3 are the centres of gravity of benzene rings C1B–C6B and C1A–C6A, respectively. C—H⋯π inter­actions run parallel to the [210] direction (Table 1 ▸ and Fig. 6 ▸).


Crystal structures of three indole derivatives: 3-ethnyl-2-methyl-1-phenyl-sulfonyl-1H-indole, 4-phenyl-sulfonyl-3H,4H-cyclo-penta-[b]indol-1(2H)-one and 1-{2-[(E)-2-(5-chloro-2-nitro-phen-yl)ethen-yl]-1-phenyl-sulfonyl-1H-indol-3-yl}ethan-1-one chloro-form monosolvate.

Gopinath S, Sethusankar K, Ramalingam BM, Mohanakrishnan AK - Acta Crystallogr E Crystallogr Commun (2015)

The crystal packing of compound (I), viewed down the b axis, showing C12B—H12B⋯O2Ai inter­molecular hydrogen bond link the independent mol­ecules running parallel to the [101] direction and further inter­connected by C10A—H10A⋯Cg1ii, C11A—H11A⋯Cg2ii and C16A—H16A⋯Cg3iii inter­actions. Cg2 is the centre of the gravity of the pyrrole ring (atoms N1B/C1B/C6B/C7B/C8B), and Cg1 and Cg3 are the centres of the gravity of benzene rings C1B–C6B and C1A–C6A, respectively. [Symmetry codes: (i) −x + 1, y + , −z + 1; (ii) −x + 2, y − , −z + 1; (iii) −x + 1, y + , −z.]
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fig6: The crystal packing of compound (I), viewed down the b axis, showing C12B—H12B⋯O2Ai inter­molecular hydrogen bond link the independent mol­ecules running parallel to the [101] direction and further inter­connected by C10A—H10A⋯Cg1ii, C11A—H11A⋯Cg2ii and C16A—H16A⋯Cg3iii inter­actions. Cg2 is the centre of the gravity of the pyrrole ring (atoms N1B/C1B/C6B/C7B/C8B), and Cg1 and Cg3 are the centres of the gravity of benzene rings C1B–C6B and C1A–C6A, respectively. [Symmetry codes: (i) −x + 1, y + , −z + 1; (ii) −x + 2, y − , −z + 1; (iii) −x + 1, y + , −z.]
Mentions: In the crystal packing of compound (I), the mol­ecules are linked via inter­molecular C16B—H16B⋯O2A(−x + 1, y + , −z + 1) hydrogen bonds running parallel to the [101] direction. The crystal packing is further stabilized by inter­molecular C10A—H10A⋯Cg1, C11A—H11A⋯Cg2 and C16A—H16A⋯Cg3 inter­actions, with separations of 3.727 (2), 3.546 (2) and 3.699 (3) Å at (−x + 2, y − , −z + 1) and (−x + 1, y + , −z), respectively. Cg2 is the centre of gravity of pyrrole ring N1B/C1B/C6B/C7B/C8B, and Cg1 and Cg3 are the centres of gravity of benzene rings C1B–C6B and C1A–C6A, respectively. C—H⋯π inter­actions run parallel to the [210] direction (Table 1 ▸ and Fig. 6 ▸).

Bottom Line: Compounds (I) and (II) crystalize with two independent mol-ecules in the asymmetric unit.The indole ring systems in all three structures deviate only slightly from planarity, with dihedral angles between the planes of the pyrrole and benzene rings spanning the tight range 0.20 (9)-1.65 (9)°.These indole ring systems, in turn, are almost orthogonal to the phenyl-sulfonyl rings [range of dihedral angles between mean planes = 77.21 (8)-89.26 (8)°].

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India.

ABSTRACT
The title compounds, C17H13NO2S, (I), C17H13NO3S, (II), and C24H17ClN2O5S·CHCl3, (III), are indole derivatives. Compounds (I) and (II) crystalize with two independent mol-ecules in the asymmetric unit. The indole ring systems in all three structures deviate only slightly from planarity, with dihedral angles between the planes of the pyrrole and benzene rings spanning the tight range 0.20 (9)-1.65 (9)°. These indole ring systems, in turn, are almost orthogonal to the phenyl-sulfonyl rings [range of dihedral angles between mean planes = 77.21 (8)-89.26 (8)°]. In the three compounds, the mol-ecular structure is stabilized by intra-molecular C-H⋯O hydrogen bonds, generating S(6) ring motifs with the sulfone O atom. In compounds (I) and (II), the two independent mol-ecules are linked by C-H⋯O hydrogen bonds and C-H⋯π inter-actions, while in compound (III), the mol-ecules are linked by C-H⋯O hydrogen bonds, generating R 2 (2)(22) inversion dimers.

No MeSH data available.


Related in: MedlinePlus