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Crystal structure and Hirshfeld analysis of 2-[bis-(1-methyl-1H-indol-3-yl)meth-yl]benzoic acid.

ABSTRACT: In the title compound, C₂₆H₂₂N₂O₂, the dihedral angles between the 1-methyl-indole units (A and B) and the benzoic acid moiety (C) are A/B = 64.87 (7), A/C = 80.92 (8) and B/C = 75.05 (8)°. An intra-molecular C-H⋯O inter-action arising from the methyne group helps to establish the conformation. In the crystal, R ₂ ²(8) carb-oxy-lic acid inversion dimers linked by pairs of O-H⋯O hydrogen bonds are observed. A Hirshfeld surface analysis shows that the greatest contributions are from H⋯H, C⋯H/H⋯C and O⋯H/H⋯O contacts (percentage values = 54.6%, 29.6% and 10.1%, respectively).

SUBMITTER: Sapari S

PROVIDER: S-EPMC6218917 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structure and Hirshfeld surface analysis of 4-{[(anthracen-9-yl)meth-yl]amino}-benzoic acid di-methyl-formamide monosolvate.

Project description:The title compound, C22H17NO2·C3H7NO, was synthesized by condensation of an aromatic aldehyde with a secondary amine and subsequent reduction. It was crystallized from a di-methyl-formamide solution as a monosolvate, C22H17NO2·C3H7NO. The aromatic mol-ecule is non-planar with a dihedral angle between the mean planes of the aniline moiety and the methyl anthracene moiety of 81.36?(8)°. The torsion angle of the Car-yl-CH2-NH-Car-yl backbone is 175.9?(2)°. The crystal structure exhibits a three-dimensional supra-molecular network, resulting from hydrogen-bonding inter-actions between the carb-oxy-lic OH group and the solvent O atom as well as between the amine functionality and the O atom of the carb-oxy-lic group and additional C-H?? inter-actions. Hirshfeld surface analysis was performed to qu-antify the inter-molecular inter-actions.

| S-EPMC7199275 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of 4-{[(anthracen-9-yl)meth-yl]amino}-benzoic acid.

Project description:In the mol-ecule of the title anthracene derivative, C22H17NO2, the benzene ring is inclined to the mean plane of the anthracene ring system (r.m.s. deviation = 0.024 Å) by 75.21 (9)°. In the crystal, mol-ecules are linked by pairs of O-H⋯O hydrogen bonds, forming classical carb-oxy-lic acid inversion dimers with an R 2 2(8) ring motif. The dimers are linked by C-H⋯π inter-actions, forming a supra-molecular framework.

| S-EPMC6944086 | biostudies-literature

2,6-Bis(trifluoro-meth-yl)benzoic acid.

Project description:The title compound, C(9)H(4)F(6)O(2), contains two mol-ecules in the asymmetric unit, one of which exhibits disorder in both of its trifluoro-methyl groups. The dihedral angles between the benzene ring and the carboxyl group are 71.5?(2) and 99.3?(2)° in the two independent mol-ecules. The compound exhibits a catemeric structure resulting from inter-molecular O-H?O hydrogen bonding between the carboxyl groups.

| S-EPMC2969748 | biostudies-literature

Crystal structure of 4-(tri-methyl-germ-yl)benzoic acid.

Project description:The title compound, [Ge(CH3)3(C7H5O2)], was obtained as a by-product in the synthesis of the corresponding aldehyde. Two slightly different mol-ecules are present in the asymmetric unit. In both mol-ecules, the geometry of the aromatic ring plane is distorted by varying intensities. Additionally, the Ge atoms deviate from the mean aromatic ring planes. Whereas the distance of the Ge atom to the ring plane is only 0.101?(4)?Å in the first mol-ecule, this distance is increased to 0.210?(4)?Å in the second. In the crystal structure, centrosymmetric O-H?O hydrogen-bonded dimers are formed. The title compound is isostructural with the Si analogue [Haberecht et al. (2004 ?). Acta Cryst. E60, o329-0330].

| S-EPMC4459299 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and computational study of the 1:2 co-crystal formed between N,N'-bis-[(pyridin-4-yl)meth-yl]ethanedi-amide and 3-chloro-benzoic acid.

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| S-EPMC7274012 | biostudies-literature

2,2'-(Disulfanedi-yl)di-benzoic acid N,N-di-methyl-formamide monosolvate: crystal structure, Hirshfeld surface analysis and computational study.

Project description:The title 1:1 solvate, C14H10O4S2·C3H7NO, features a twisted mol-ecule of 2,2'-di-thiodi-benzoic acid (DTBA), with the central C-S-S-C torsion angle being -88.57?(6)°, and a mol-ecule of di-methyl-formamide (DMF). The carb-oxy-lic acid groups are, respectively, close to co-planar and twisted with respect to the benzene rings to which they are connected as seen in the CO2/C6 torsion angles of 1.03?(19) and 7.4?(2)°. Intra-molecular, hypervalent S?O inter-actions are noted [S?O = 2.6140?(9) and 2.6827?(9)?Å]. In the crystal, four-mol-ecule aggregates are formed via DTBA-O-H?O(DMF) and DTBA-O-H?O(DTBA) hydrogen bonding, the latter via an eight-membered {?OHCO}2 homosynthon. These are linked into supra-molecular layers parallel to (011) via benzene-C-H?O(DTBA) and DTBA-C=O??(benzene) inter-actions, with the connections between these, giving rise to a three-dimensional architecture, being of the type benzene-C-H??(benzene). An analysis of the calculated Hirshfeld surfaces indicates, in addition to the aforementioned inter-molecular contacts, the presence of stabilizing inter-actions between a benzene ring and a quasi-?-system defined by O-H?O hydrogen bonds between a DTBA dimer, i.e. the eight-membered {?OCOH}2 ring system, and between a benzene ring and a quasi-?(OCOH?OCH) system arising from the DTBA-O-H?O(DMF) hydrogen bond. The inter-centroid separations are 3.65 and 3.49?Å, respectively.

| S-EPMC7336788 | biostudies-literature

3,5-Bis[(pyridin-4-yl)meth-oxy]benzoic acid.

Project description:Single crystals of the title compound, C19H16N2O4, were obtained under hydro-thermal conditions by an unintended recrystallization of the employed microcrystalline starting material. The [(pyridin-4-yl)meth-oxy]benzoic acid unit is nearly planar, with a maximum deviation from the least-squares plane of 0.194?(2)?Å. This plane is inclined by 35.82?(6)° to that defined by the second (pyridin-4-yl)meth-oxy group [in which the largest deviation from the least-squares plane is 0.013?(2)?Å]. In the crystal, mol-ecules are linked by O-H?N hydrogen bonds involving the acid hy-droxy group and a pyridine N atom into chains parallel to [-201].

| S-EPMC3588300 | biostudies-literature

The crystal structure, Hirshfeld surface analysis and energy frameworks of 2-[2-(meth-oxy-carbon-yl)-3,6-bis-(meth-oxy-meth-oxy)phen-yl]acetic acid.

Project description:In the title compound, C14H18O8, (I), the meth-oxy-carbonyl [-C(=O)OCH3] and the acetic acid [-CH2C(=O)OH] groups are inclined to the benzene ring by 79.24?(11) and 76.71?(13)°, respectively, and are normal to each other with a dihedral angle of 90.00?(13)°. In the crystal, mol-ecules are linked by a pair of O-H?O hydrogen bonds forming the familiar acetic acid inversion dimer. The dimers are linked by two C-H?O hydrogen bonds and an offset ?-? inter-action [inter-centroid distance = 3.6405?(14)?Å], forming layers lying parallel to the (10) plane. The layers are linked by a third C-H?O hydrogen bond and a C-H?? inter-action to form a supra-molecular framework.

| S-EPMC7336770 | biostudies-literature

2-Methyl-sulfonyl-4-(trifluoro-meth-yl)benzoic acid.

Project description:In the title mol-ecule, C(9)H(7)F(3)O(4)S, the S and the methyl C atoms of the methyl-sulfonyl group deviate from the benzene ring plane by 0.185?(2) and -1.394?(3)?Å, respectively. In the crystal, O-H?O hydrogen bonds link the mol-ecules into chains along [201]. Weak C-H?O inter-actions further link these chains into layers parallel to the ac plane.

| S-EPMC3379423 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of a third polymorph of 2,6-di-meth-oxy-benzoic acid.

Project description:A third crystalline form of the title compound, C9H10O4, crystallizing in the centrosymmetric monoclinic space group P21/c, has been identified during screening for co-crystals. The asymmetric unit comprises a non-planar independent mol-ecule with a synplanar conformation of the OH group. The sterically bulky o-meth-oxy substituents force the carb-oxy group to be twisted away from the plane of the benzene ring by 74.10 (6)°. The carb-oxy group exhibits the acidic H atom disordered over two sites between two O atoms. A similar situation has been found for the second tetra-gonal polymorph reported [Portalone (2011 ▸). Acta Cryst. E67, o3394-o3395], in which mol-ecules with the OH group in a synplanar conformation form dimeric units via strong O-H⋯O hydrogen bonds. In contrast, in the first ortho-rhom-bic form reported [Swaminathan et al. (1976 ▸). Acta Cryst. B32, 1897-1900; Bryan & White (1982 ▸). Acta Cryst. B38, 1014-1016; Portalone (2009 ▸). Acta Cryst. E65, o327-o328], the mol-ecular components do not form conventional dimeric units, as an anti-planar conformation adopted by the OH group favors the association of mol-ecules in chains stabilized by linear O-H⋯O hydrogen bonds.

| S-EPMC7784654 | biostudies-literature

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