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4,4'-Bis(prop-2-yn-yloxy)biphen-yl.

ABSTRACT: The title compound, C(18)H(14)O(2), crystallizes with one half-mol-ecule in the asymmetric unit. The mol-ecule lies on an inversion center, located at the mid-point of the central C-C bond. As a result, the benzene rings are coplanar. No classical hydrogen bonds or stacking inter-actions are observed in the crystal structure.

SUBMITTER: Zhang W

PROVIDER: S-EPMC2915354 | biostudies-other | 2007

REPOSITORIES: biostudies-other

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4,4'-Bis(prop-2-yn-yloxy)biphen-yl.

Zhang Wu W Yao Li L Tao Ruo-Jie RJ

Acta crystallographica. Section E, Structure reports online 20071218 Pt 1

The title compound, C(18)H(14)O(2), crystallizes with one half-mol-ecule in the asymmetric unit. The mol-ecule lies on an inversion center, located at the mid-point of the central C-C bond. As a result, the benzene rings are coplanar. No classical hydrogen bonds or stacking inter-actions are observed in the crystal structure. ...[more]

PMID: 21200870

Similar Datasets

Comparison of the crystal structures of 4,4'-bis-[3-(4-methyl-piperidin-1-yl)prop-1-yn-1-yl]-1,1'-biphenyl and 4,4'-bis-[3-(2,2,6,6-tetra-methyl-piperidin-1-yl)prop-1-yn-1-yl]-1,1'-biphen-yl.

Project description:As part of a comprehensive program to discover α9α10 nicotinic acetyl-choline receptor antagonists, the title compounds C30H36N2, (I), and C36H48N2, (II), were synthesized by coupling 4,4'-bis-(3-bromo-prop-1-yn-1-yl)-1,1'-biphenyl with 4-methyl-piperidine and 2,2,6,6-tetra-methyl-piperidine, respectively, in aceto-nitrile at room temperature. In compound (I), the biphenyl system has a twisted conformation with a dihedral angle of 26.57 (6)° between the two phenyl rings of the biphenyl moiety, while in compound (II), the biphenyl moiety sits on a crystallographic inversion centre so the two phenyl rings are exactly coplanar. The terminal piperidine rings in both compound (I) and compound (II) are in the chair conformation. In compound (I), the dihedral angles about the ethynyl groups between the planes of the phenyl rings and the piperidine ring N atoms are 37.16 (16) and 14.20 (17)°. In compound (II), the corresponding dihedral angles are both 61.48 (17)°. There are no noteworthy inter-molecular inter-actions in (I), but in (II) there is a small π-overlap between inversion-related mol-ecules (1 - x, 1 - y, 1 - z), with an inter-planar spacing of 3.553 (3) Å and centroid-to-centroid separation of 3.859 (4) Å.

| S-EPMC4647388 | biostudies-literature

Comparison crystal structure conformations of two structurally related biphenyl analogues: 4,4'-bis-[3-(pyrrolidin-1-yl)prop-1-yn-1-yl]-1,1'-biphenyl and 4,4'-bis-{3-[(S)-2-methyl-pyrrolidin-1-yl]prop-1-yn-1-yl}-1,1'-biphen-yl.

Project description:The title compounds, C26H28N2, (I), and C28H32N2, (II), were designed based on the structure of the potent α9α10 nicotinic acetyl-choline receptor antagonist ZZ161C {1,1'-[[1,1'-biphen-yl]-4,4'-diylbis(prop-2-yne-3,1-di-yl)]bis-(3,4-di-methyl-pyridin-1-ium) bromide}. In order to improve the druglikeness properties of ZZ161C for potential oral administration, the title compounds (I) and (II) were prepared by coupling 4,4'-bis-(3-bromo-prop-1-yn-1-yl)-1,1'-biphenyl with pyrrol-idine, (I), and (S)-2-methyl-pyrrolidine, (II), respectively, in aceto-nitrile at room temperature. The asymmetric unit of (I) contains two half mol-ecules that each sit on sites of crystallographic inversion. As a result, the biphenyl ring systems in compound (I) are coplanar. The biphenyl ring system in compound (II), however, has a dihedral angle of 28.76 (11)°. In (I), the two independent mol-ecules differ in the orientation of the pyrrolidine ring (the nitro-gen lone pair points towards the biphenyl rings in one mol-ecule, but away from the rings in the other). The torsion angles about the ethynyl groups between the planes of the phenyl rings and the pyrrolidine ring N atoms are 84.15 (10) and -152.89 (10)°. In compound (II), the corresponding torsion angles are 122.0 (3) and 167.0 (3)°, with the nitro-gen lone pairs at both ends of the mol-ecule directed away from the central biphenyl rings.

| S-EPMC4647364 | biostudies-literature

Crystal structure of 4,4'-bis-[3-(piperidin-1-yl)prop-1-yn-1-yl]-1,1'-biphen-yl.

Project description:The title compound, C28H32N2, (I), is one of a second generation of compounds designed and synthesized based on a very potent and selective ?9?10 nicotinic acetyl-choline receptor antagonist ZZ161C {1,1'-[[1,1'-biphen-yl]-4,4'-diylbis(prop-2-yne-3,1-di-yl)]bis-(3,4-di-methyl-pyridin-1-ium) bromide}, which has shown analgesic effects in a chemotherapy-induced neuropathy animal model. Compound (I) was synthesized by the reaction of 4,4'-bis-(3-bromo-prop-1-yn-1-yl)-1,1'-biphenyl with piperidine at room temperature in aceto-nitrile. The single-crystal used for X-ray analysis was obtained by dissolving (I) in a mixture of di-chloro-methane and methanol, followed by slow evaporation of the solvent. In the crystal of (I), the biphenyl moiety has a twisted conformation, with a dihedral angle of 25.93?(4)° between the benzene rings. Both piperidine head groups in (I) are in the chair conformation and are oriented so that the N-atom lone pairs of each piperidine group point away from the central biphenyl moiety.

| S-EPMC5458311 | biostudies-other

4,4'-Bis[(E)-(2,3-diiodo-prop-2-en-1-yl)-oxy]biphen-yl.

Project description:Iodine adds across both triple bonds of 4,4'-bis-(prop-2-yn--yl-oxy)biphenyl, yielding the 4,4'-bis-(2,3-diiodo-all-yloxy)biphenyl title compound, C(18)H(14)I(4)O(2); the 2,3-diiodo-ally-oxy substituents have the I atoms in an E configuration. In the biphenyl portion of the mol-ecule, the aromatic rings are inclined by 37.8?(2)°.

| S-EPMC3052146 | biostudies-literature

2,6-Bis(prop-2-yn-yloxy)naphthalene.

Project description:The title compound, C(16)H(12)O(2), crystallizes with one half-mol-ecule in the asymmetric unit. The mol-ecule lies on an inversion centre, located at the mid-point of the naphthyl group. All non-H atoms are almost coplanar, with a mean deviation from the least-squares plane of 0.0536?(11)?Å. Mol-ecules are linked into a three-dimensional framework by a combination of C-H?O and C-H??(arene) hydrogen bonds.

| S-EPMC2959568 | biostudies-literature

2,3-Bis(prop-2-yn-yloxy)naphthalene.

Project description:In the crystal structure of the title compound, C(16)H(12)O(2), no classical hydrogen bonds or aromatic π-π stacking inter-actions were observed. The mol-ecules are linked into a three-dimensional framework by a combination of C-H⋯O and C-H⋯π(arene) hydrogen bonds.

| S-EPMC2960027 | biostudies-literature

4,4'-Bis(benzimidazol-1-yl)biphen-yl.

Project description:The mol-ecule of the title compound, C(26)H(18)N(4), resides on a crystallographic inversion centre with a dihedral angle of 44.94?(5)° between the benzimidazole ring system and the benzene ring. The primary hydrogen bond is C-H?N and inversion-related pairs of these generate a chain of rings along the c-axis direction; ??? stacking involving the benzimidazole groups with inter-planar separations of ca 3.4?Å complete the inter-actions.

| S-EPMC2915210 | biostudies-literature

2,2'-Bis(prop-2-yn-yloxy)-1,1'-binaphth-yl.

Project description:In the title compound, C(26)H(18)O(2), the mol-ecule is located on a twofold rotation axis. The two naphthyl ring planes in the mol-ecule are nearly perpendicular to each other [dihedral angle = 82.42?(1)°. No classical hydrogen bonds or aromatic ?-? stacking inter-actions were observed.

| S-EPMC2915361 | biostudies-other

4,4'-Bis(2-methoxy-lstyr-yl)biphen-yl.

Project description:The title compound, C(30)H(26)O(2), was prepared by the reaction of a Wittig reagent and 2-methoxy-benzaldehyde. The mol-ecule lies about an inversion centre located at the midpoint of the C-C bond between the inner benzene rings. The crystal structure is stabilized by C-H?? inter-actions.

| S-EPMC2977130 | biostudies-literature

N-[4-(Prop-2-yn-yloxy)phen-yl]maleimide.

Project description:In the title compound, C(13)H(9)NO(3), the dihedral angle between the benzene and maleimide rings is 64.1 (2)°. In the crystal structure, mol-ecules interact via C-H⋯O inter-actions.

| S-EPMC2967977 | biostudies-literature

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