Crystal structures of 6-chloro-indan-1-one and 6-bromo-indan-1-one exhibit different inter-molecular packing inter-actions.
ABSTRACT: The two title compounds are analogs of 1-indanone that are substituted at the 6-position with chlorine and bromine. Although very similar in mol-ecular structure, the crystal structures are not isomorphous and reveal that 6-chloro-indan-1-one, C9H7ClO (I), and 6-bromo-indan-1-one, C9H7BrO (II), exhibit unique inter-molecular packing motifs. The mol-ecules of the chloro analog (I) pack with a herringbone packing motif of C-H?O inter-actions, whereas the bromo derivative (II) packs with offset face-to-face ?-stacking, C-H?O, C-H?Br and Br?O inter-actions. Compound (II) was refined as a two-component non-merohedral twin, BASF 0.0762?(5).
Project description:The main purpose of this publication was to obtain the S-enantiomer of indan-1-ol with high enantiomeric excess and satisfactory yield. In our research, we used carrot callus cultures (Daucus carota L.), whereby the enzymatic system reduced indan-1-one and oxidized indan-1-ol. During the reaction of reduction, after five days, we received over 50% conversion, with the enantiomeric excess of the formed S-alcohol above 99%. In turn, during the oxidation of racemic indan-1-ol after 15 days, 36.7% of alcohol with an enantiomeric excess 57.4% S(+) remained in the reaction mixture. In addition, our research confirmed that the reactions of reduction and oxidation are competing reactions during the transformation of indan-1-ol and indan-1-one in carrot callus cultures.
Project description:The mol-ecular structure of (2E)-1,4-bis-(4-chloro-phen-yl)but-2-ene-1,4-dione [C16H10Cl2O2, (1)] is composed of two p-chlorophenyl rings, each bonded on opposite ends to a near planar 1,4-trans enedione moiety [-C(=O)-CH=CH-(C=O)-] [r.m.s. deviation = 0.003?(1)?Å]. (2E)-1,4-Bis(4-bromo-phen-yl)but-2-ene-1,4-dione [C16H10Br2O2, (2)] has a similar structure to (1), but with two p-bromophenyl rings and a less planar enedione group [r.m.s. deviation = 0.011?(1)?Å]. Both mol-ecules sit on a center of inversion, thus Z' = 0.5. The dihedral angles between the ring and the enedione group are 16.61?(8) and 15.58?(11)° for (1) and (2), respectively. In the crystal, mol-ecules of (1) exhibit C-Cl?Cl type I inter-actions, whereas mol-ecules of (2) present C-Br?Br type II inter-actions. van der Waals-type inter-actions contribute to the packing of both mol-ecules, and the packing reveals face-to-face ring stacking with similar inter-planar distances of approximately 3.53?Å.
Project description:The title compound, C(15)H(10)Br(2)O, is a chalcone with 2-bromo-phenyl and 4-bromo-phenyl rings bonded to opposite sides of a propenone group. The dihedral angle between mean planes of the benzene rings is 71.3?(1)°. The angle between the mean plane of the prop-2-ene-1-one group and the mean planes of the 2-bromo-phenyl and 4-bromo-phenyl rings are 64.2?(9) and 71.3?(1)°, respectively. A weak inter-molecular C-H?O inter-action and two weak C-Br?? inter-actions are observed, which contribute to the stability of the crystal packing.
Project description:The reaction of 1,5-di-bromo-pentane with urotropine results in crystals of the title mol-ecular salt, 5-bromo-urotropinium bromide [systematic name: 1-(5-bro-mo-pent-yl)-3,5,7-tri-aza-1-azoniatri-cyclo-[220.127.116.11<sup>3,7</sup>]decane bromide], C<sub>11</sub>H<sub>22</sub>BrN<sub>4</sub> <sup>+</sup>·Br<sup>-</sup> (<b>1</b>), crystallizing in space group <i>P</i>2<sub>1</sub>/<i>n</i>. The packing in compound <b>1</b> is directed mainly by H?H van der Waals inter-actions and C-H?Br hydrogen bonds, as revealed by Hirshfeld surface analysis. Comparison with literature examples of alkyl-urotropinium halides shows that the inter-actions in <b>1</b> are consistent with those in other bromides and simple chloride and iodide species.
Project description:In the title 1,3,2-dioxaphospho-rinane derivative, C(10)H(11)Br(2)O(4)P, the 1,3,2-dioxaphospho-rinane ring adopts a chair conformation, having the P=O bond equatorially oriented and the phen-oxy group axially oriented. The bromo substituent is in an axial position opposite to the phen-oxy group and the bromo-methyl group is in an equatorial position opposite to the P=O bond. In the crystal packing, mol-ecules are linked through weak C-H?O and C-H?Br inter-actions to form chains along the b axis. The chains are arranged into sheets parallel to the ab plane. In adjacent sheets, mol-ecules are arranged in an anti-parallel fashion. Inter-molecular C-H?? inter-actions are also observed.
Project description:Each of the title dis-symmetric di-Schiff base compounds, C15H12Cl2N2O2 (I) and C14H9BrCl2N2O (II), features a central azo-N-N bond connecting two imine groups, each with an E-configuration. One imine bond in each mol-ecule connects to a 2,6-di-chloro-benzene substituent while the other links a 2-hydroxyl-3-meth-oxy-substituted benzene ring in (I) or a 2-hydroxyl-4-bromo benzene ring in (II). Each mol-ecule features an intra-molecular hydroxyl-O-H?N(imine) hydrogen bond. The C-N-N-C torsion angles of -151.0?(3)° for (I) and 177.8?(6)° (II) indicates a significant twist in the former. The common feature of the mol-ecular packing is the formation of supra-molecular chains. In (I), the linear chains are aligned along the a-axis direction and the mol-ecules are linked by meth-oxy-C-H?O(meth-oxy) and chloro-benzene-C-Cl??(chlorobenzene) inter-actions. The chain in (II) is also aligned along the a axis but, has a zigzag topology and is sustained by Br?O [3.132?(4)?Å] secondary bonding inter-actions. In each crystal, the chains pack without directional inter-actions between them. The non-covalent inter-actions are delineated in the study of the calculated Hirshfeld surfaces. Dispersion forces make the most significant contributions to the identified inter-molecular inter-actions in each of (I) and (II).
Project description:The title compound, [Mg(C44H24Br4N4)(H2O)2] or [Mg(TBrPP)(H2O)2], where TBrPP is the 5,10,15,20-tetra-kis-(4-bromo-phen-yl)porphyrinato ligand, was obtained unintentionally as a by-product of the reaction of the [Mg(TBrPP)] complex with an excess of di-methyl-glyoxime in di-chloro-methane. The entire mol-ecule exhibits point group symmetry 4/m. In the asymmetric unit, except for two C atoms of the phenyl ring, all other atoms lie on special positions. The Mg(II) atom is situated at a site with symmetry 4/m, while the N and the C atoms of the porphyrin macrocycle, as well as two C atoms of the phenyl ring and the Br atom lie in the mirror plane containing the porphyrin core. The H atoms of the axially bonded water mol-ecule are incompatible with the fourfold rotation axis and are disordered over two sites. In the crystal, mol-ecules are packed in rows along . Weak inter-molecular C-H?? and C-H?Br inter-actions, as well as O-H?Br hydrogen bonds, stabilize the crystal packing.
Project description:The crystal structures of three isomeric (E)-N'-(chloro-phenyl-methyl-idene)-N-methyl-2-(thio-phen-2-yl)acetohydrazides (C14H13ClN2OS) are described, with the Cl atom in ortho (I), meta (III) and para (IV) positions in the benzene ring. The ortho-bromo derivative (II) (C14H13BrN2OS), which is isostructural with its chloro congener (I), is also reported. Mol-ecules (I)-(III) have similar conformations, which approximate to l-shapes, as indicated by their N-C-C-Ct (t = thio-phene) torsion angles of -90.1?(3), -91.44?(18) and -90.7?(9)°, respectively. The conformation of (IV) is different, with an equivalent torsion angle of -170.75?(11)° corresponding to a more extended shape for the mol-ecule. The thio-phene ring in each structure features 'flip' rotational disorder. The packing for (I) and (II) features inversion dimers, linked by pairs of C-H?O inter-actions, which generate R22(14) loops. In the crystal of (III),  C(8) chains arise, with adjacent mol-ecules linked by pairs of C-H?O hydrogen bonds. The packing for (IV) features unusually short C-H?O inter-actions arising from an H atom attached to the benzene ring (H?O = 2.18?Å), which lead to C(9)  chains. Hirshfeld fingerprint percentage contact contributions are similar for the four title compounds.
Project description:In the title compound, C(16)H(11)BrO(2), the isocoumarin ring system is planar (r.m.s. deviation = 0.015?Å) and subtends a dihedral angle of 88.90?(2)° with the bromo-benzene ring. In the crystal, mol-ecules are linked, forming a three-dimensional packing pattern involving C-H?O inter-actions, Br?O contacts [3.4734?(10)?Å] and ?-? stacking inter-actions with centroid-centroid distances ranging from 3.667?(2) to 3.765?(2)?Å.
Project description:In the title compound, C15H10BrFO, the mol-ecular structure consists of a 3-bromo-phenyl ring and a 4-fluoro-phenyl ring linked via a prop-2-en-1-one spacer. The 3-bromophenyl and 4-fluorophenyl rings make a dihedral angle of 48.90 (15)°. The mol-ecule has an E configuration about the C=C bond and the carbonyl group is syn with respect to the C=C bond. In the crystal, mol-ecules are linked by C-H⋯π inter-actions between the bromo-phenyl and fluoro-phenyl rings of mol-ecules, resulting in a two-dimensional layered structure parallel to the ab plane. The mol-ecular packing is stabilized by weak Br⋯H and F⋯H contacts, one of which is on the one side of each layer, and the second is on the other. The inter-molecular inter-actions in the crystal packing were further analysed using Hirshfeld surface analysis, which indicates that the most significant contacts are Cl⋯H/H⋯Cl (20.8%), followed by C⋯H/H⋯C (31.1%), H⋯H (21.7%), Br⋯H/H⋯Br (14.2%), F⋯H/H⋯F (9.8%), O⋯H/H⋯O (9.7%).