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Crystal structure and Hirshfeld surface analysis of new polymorph of racemic 2-phenyl-butyramide.

ABSTRACT: A new polymorph of the title compound, C₁₀H₁₃NO, was obtained by recrystallization of the commercial product from a water/ethanol mixture (1:1 v/v). Crystals of the previously reported racemic and homochiral forms of 2-phenyl-butyramide were grown from water-aceto-nitrile solution in 1:1 volume ratio [Khrustalev et al. (2014 ▸). Cryst. Growth Des. 14, 3360-3369]. While the previously reported racemic and enanti-opure forms of the title compound adopt very similar supra-molecular structures (hydrogen-bonded ribbons), the new racemic polymorph is stabilized by a single N-H⋯O hydrogen bond that links mol-ecules into chains along the c-axis direction with an anti-parallel (centrosymmetric) packing in the crystal. Hirshfeld mol-ecular surface analysis was employed to compare the inter-molecular inter-actions in the polymorphs of the title compound.

SUBMITTER: Rigin S

PROVIDER: S-EPMC6658964 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Racemic mefloquinium chloro-difluoro-acetate: crystal structure and Hirshfeld surface analysis.

Project description:In the racemic title mol-ecular salt, C17H17F6N2O+·C2ClF2O3- (systematic name: 2-{[2,8-bis-(tri-fluoro-meth-yl)quinolin-4-yl](hy-droxy)meth-yl}piperidin-1-ium chloro-difluoro-acetate), the cation, which is protonated at the piperidine N atom, has the shape of the letter, L, with the piperidin-1-ium group being approximately orthogonal to the quinolinyl residue [the Cq-Cm-Cm-Na (q = quinolinyl; m = methine; a = ammonium) torsion angle is 177.79?(18)°]. An intra-molecular, charge-assisted ammonium-N-H?O(hydrox-yl) hydrogen bond ensures the hy-droxy-O and ammonium-N atoms lie to the same side of the mol-ecule [Oh-Cm-Cm-Na (h = hydrox-yl) = -59.7?(2)°]. In the crystal, charge-assisted hydroxyl-O-H?O-(carboxyl-ate) and ammonium-N+-H?O-(carboxyl-ate) hydrogen bonds generate a supra-molecular chain along [010]; the chain is consolidated by C-H?O inter-actions. Links between chains to form supra-molecular layers are of the type C-Cl??(quinolinyl-C6) and the layers thus formed stack along the a-axis direction without directional inter-actions between them. The analysis of the calculated Hirshfeld surface points to the dominance of F?H contacts to the surface (40.8%) with significant contributions from F?F (10.5%) and C?F (7.0%) contacts.

| S-EPMC6038619 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of 3-cyano-phenyl-boronic acid.

Project description:In the title compound, C7H6BNO2, the mean plane of the -B(OH)2 group is twisted by 21.28?(6)° relative to the cyano-phenyl ring mean plane. In the crystal, mol-ecules are linked by O-H?O and O-H?N hydrogen bonds, forming chains propagating along the [101] direction. Offset ?-? and B?? stacking inter-actions link the chains, forming a three-dimensional network. Hirshfeld surface analysis shows that van der Waals inter-actions constitute a further major contribution to the inter-molecular inter-actions, with H?H contacts accounting for 25.8% of the surface.

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A triclinic polymorph of tri-cyclo-hexyl-phosphane sulfide: crystal structure and Hirshfeld surface analysis.

Project description:The title compound, (C6H11)3PS (systematic name: tri-cyclo-hexyl-?5-phosphane-thione), is a triclinic (P-1, Z' = 1) polymorph of the previously reported ortho-rhom-bic form (Pnma, Z' = 1/2) [Kerr et al. (1977 ?). Can. J. Chem. 55, 3081-3085; Reibenspies et al. (1996 ?). Z. Kristallogr. 211, 400]. While conformational differences exist between the non-symmetric mol-ecule in the triclinic polymorph, cf. the mirror-symmetric mol-ecule in the ortho-rhom-bic form, these differences are not chemically significant. The major feature of the mol-ecular packing in the triclinic polymorph is the formation of linear chains along the a axis sustained by methine-C-H?S(thione) inter-actions. The chains pack with no directional inter-actions between them. The analysis of the Hirshfeld surface for both polymorphs indicates a high degree of similarity, being dominated by H?H (ca 90%) and S?H/H?S contacts.

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Crystal structure and Hirshfeld surface analysis of ethyl 5-phenyl-isoxazole-3-carboxyl-ate.

Project description:The title compound, C12H11NO3, is an inter-mediate used in the synthesis of many drug-like mol-ecules. The mol-ecule is almost planar, with the phenyl ring inclined to the isoxazole ring by 0.5 (1)°. The ester moiety has an extended conformation and is almost in the same plane with respect to the isoxazole ring, as indicated by the O-C-C-N torsion angle of -172.86 (18)°. In the crystal, mol-ecules are linked via pairs of C-H⋯O hydrogen bonds with the same acceptor atom, forming inversion dimers with two R21(7) ring motifs. The mol-ecules stack in layers lying parallel to (10-3). Analysis using Hirshfeld surface generation and two-dimensional fingerprint plots explores the distribution of weak inter-molecular inter-actions in the crystal structure.

| S-EPMC5382615 | 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

A new monoclinic polymorph of N-(3-methyl-phen-yl)eth-oxy-carbo-thio-amide: crystal structure and Hirshfeld surface analysis.

Project description:The title compound, C10H13NOS, is a second monoclinic polymorph (space group P21/c, Z' = 2) of the previously reported C2/c (Z = 1) polymorph [Tadbuppa & Tiekink (2005 ?). Z. Kristallogr. New Cryst. Struct. 220, 395-396]. Two independent mol-ecules comprise the asymmetric unit of the new polymorph and each of these exists as a thioamide-thione tautomer. In each molecule, the central CNOS chromophore is strictly planar [r.m.s. deviations = 0.0003 and 0.0015?Å] and forms dihedral angles of 6.17?(5) and 20.78?(5)° with the N-bound 3-tolyl rings, thereby representing the major difference between the mol-ecules. The thione-S and thio-amide-N-H atoms are syn in each mol-ecule and this facilitates the formation of an eight-membered thio-amide {?SCNH}2 synthon between them; the dimeric aggregates are consolidated by pairwise 3-tolyl-C-H?S inter-actions. In the extended structure, supra-molecular layers parallel to (102) are formed via a combination of 3-tolyl-C-H??(3-tol-yl) and weak ?-? inter-actions [inter-centroid distance between 3-tolyl rings = 3.8535?(12)?Å]. An analysis of the Hirshfeld surfaces calculated for both polymorphs reveals the near equivalence of one of the independent mol-ecules of the P21/c form to that in the C2/c form.

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Crystal structure and Hirshfeld surface analysis of 3-amino-5-phenyl-thia-zolidin-2-iminium bromide.

Project description:In the cation of the title salt, C9H12N3S+·Br-, the thia-zolidine ring adopts an envelope conformation with the C atom adjacent to the phenyl ring as the flap. In the crystal, N-H?Br hydrogen bonds link the components into a three-dimensional network. Weak ?-? stacking inter-actions between the phenyl rings of adjacent cations also contribute to the mol-ecular packing. A Hirshfeld surface analysis was conducted to qu-antify the contributions of the different inter-molecular inter-actions and contacts.

| S-EPMC6775745 | biostudies-literature

m-Xylylenediaminium sulfate: crystal structure and Hirshfeld surface analysis.

Project description:The crystal structure of the title salt {systematic name: [1,3-phenyl-enebis(methyl-ene)]bis-(aza-nium) sulfate}, C8H14N2 (2+)·SO4 (2-), consists of infinite (100) sheets of alternating organic and inorganic entities The m-xylylenediaminium cations are linked to the sulfate anions by N-H?O and asymmetric bifurcated N-H?(O,O) hydrogen bonds, generating a three-dimensional network. A weak C-H?O inter-action also occurs. The Hirshfeld surface analysis and the two-dimensional fingerprint maps indicate that the packing is dominated by H?O/O?H and H?H contacts.

| S-EPMC4908557 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of 1,3-diethynyladamantane.

Project description:The title compound, C14H16, exhibits exceptionally weak inter-molecular C-H⋯π hydrogen bonding of the ethynyl groups, with the corresponding H⋯π separations [2.91 (2) and 3.12 (2) Å] exceeding normal vdW distances. This bonding complements distal contacts of the CH (aliphatic)⋯π type [H⋯π = 3.12 (2)-3.14 (2) Å] to sustain supra-molecular layers. Hirshfeld surface analysis of the title compound suggests a relatively limited significance of the C⋯H/H⋯C contacts to the crystal packing (24.6%) and a major contribution from H⋯H contacts accounting 74.9% to the entire surface.

| S-EPMC7273986 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of pulcherrin J.

Project description:The title compound, C29H36O4 [systematic name (4aR,5R,6aS,7R,11aS,11bR)-4a-hydroxy-4,4,7,11b-tetramethyl-1,2,3,4,4a,5,6,6a,7,11,11a,11b-dodecahydrophen-anthro[3,2-b]furan-5-yl cinnamate], a natural diterpene known as pulcherrin J, was isolated from stem barks of medicinally important Caesalpinia pulcherrima (L.). The crystal structure of pulcherrin J shows it to be composed of a central core of three trans-fused cyclo-hexane rings and a near planar five-membered furan ring, along with an axially oriented cinnamate moiety and an -hydroxy substituent attached at positions 4a and 5 of the steroid ring system, respectively. The absolute structure was established with the use of Cu Kα radiation. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds to generate [100] C(8) chains. Hirshfeld surface analysis indicates that the most significant contacts in packing are H⋯H (67.5%), followed by C⋯H (19.6%) and H⋯O (12.9%).

| S-EPMC5730321 | biostudies-literature

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