Maximum Atomic Deviation Research Articles

Aqua(5,10,15,20-tetraphenylporphyrinato-κ4N)cadmium(II)–18-crown-6 (1/1)

The title compound, [Cd(C44H28N4)(H2O)]·(C12H24O6), was made by the reaction of the [Cd(TPP)] with an excess of 18-crown-6 in chloro­benzene (where TPP is tetra­phenyl­porphyrinate). The CdII cation is chelated by a TPP anion and coordinated by a water mol­ecule in a distorted N4O square-pyramidal geometry, the CdII cation being displaced by 0.7533 (9) Å from the mean plane of four N atoms of TPP anion. The porphyrin core presents a significant distortion, the maximum atomic deviation from the 24-atom mean plane is 0.1517 (2) Å. The 18-crown-6 mol­ecule is linked with the CdII complex via classical O—H⋯O hydrogen bonds. In the crystal, weak C—H⋯π inter­actions link the complex and 18-crown-6 mol­ecules into a three-dimensional supra­molecular architecture.

1-Ethyl-2-phenyl-3-[2-(trimethylsilyl)ethynyl]-1H-indole

The title compound, C21H23NSi, was synthesized by Sonogashira-type reaction of 1-ethyl-3-iodo-2-phenyl-1H-indole with tri­methyl­silyl­acetyl­ene. The indole ring system is nearly planar [maximum atomic deviation = 0.0244 (15) Å] and is oriented at a dihedral angle of 51.48 (4)° with respect to the phenyl ring. The supramolecular aggregation is completed by weak C—H⋯π inter­actions of the methylene and phenyl groups with the benzene and pyrrole rings of the indole ring system. The methyl groups of the tri­methyl­silyl unit are equally disordered over two sets of sites.

1-Methoxy-11H-benzo[b]fluoren-11-one

In the title compound, C18H12O2, the non-H atoms are nearly coplanar, the maximum atomic deviation being 0.113 (2) Å. π–π stacking is observed in the crystal structure, the shortest centroid–centroid distance being 3.5983 (19) Å. The mol­ecular packing is further stabilized by weak C—H⋯O hydrogen bonds, forming an infinite chain along [100] and generating a C(6) motif.

1-Hydroxy-11H-benzo[b]fluoren-11-one

The title compound, C17H10O2, is nearly planar, the maximum atomic deviation being 0.053 (2) Å. In the mol­ecule, an intra­molecular O—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, inversion-related mol­ecules are linked by pairs of weak C—H⋯O hydrogen bonds, forming dimers. π–π stacking is observed in the crystal structure, the closest centroid–centroid distance being 3.7846 (16) Å.

(E)-3-(1-Phenylethylidene)indolin-2-one

In the title mol­ecule, C16H13NO, the indoline-2-one ring system is nearly planar [maximum atomic deviation = 0.082 (2) Å] and is oriented at a dihedral angle of 66.60 (12)° with respect to the phenyl ring. In the crystal, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into supra­molecular dimers.

2-(2-Hydroxyphenyl)-1,3-benzothiazole-6-carbaldehyde

The mol­ecule of the title compound, C14H9NO2S, is nearly planar, the maximum atomic deviation being 0.081 (2) Å. An intra­molecular O—H⋯N bond generates an S(6) ring motif. In the crystal, inversion-related mol­ecules linked by a pair of weak C—H⋯O hydrogen bonds form a supra­molecular dimer. π–π stacking is observed between the thia­zole and benzene rings of adjacent mol­ecules, the centroid–centroid distance being 3.7679 (9) Å.

(E)-2-[1-(4-Fluorophenyl)pent-1-en-3-ylidene]malononitrile

The title mol­ecule, C14H11FN2, is approximately planar except the ethyl group, the maximum atomic deviation being 0.105 (5) Å. The fluoro­phenyl ring and 2-propyl­idene­malononitrile unit are located on the opposite sides of the C=C double bond, showing an E configuration.

3-(2-Bromophenyl)thiazolo[3,2-a]benzimidazole

The title compound, C15H9BrN2S, was prepared by the reaction of 1-bromo-2-(2,2-dibromo­vin­yl)benzene with 1H-benzo[d]imidazole-2(3H)-thione. The thia­zolo[3,2-a]benz­imidazole fused-ring system is nearly planar, the maximum atomic deviation being 0.049 (4) Å. This mean plane is oriented at a dihedral angle of 71.55 (17)° with respect ot the bromo­phenyl ring. π–π stacking is observed in the crystal structure, the centroid–centroid distance between the thia­zole and imidazole rings of adjacent mol­ecules being 3.582 (2) Å.

(5S)-3-Chloro-4-diallylamino-5-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]furan-2(5H)-one

The title compound, C20H30ClNO3, was obtained via a tandem asymmetric Michael addition–elimination reaction of (5S)-3,4-dichloro-5-(l-menth­yloxy)-2(5H)-furan­one and diallyl­amine in the presence of potassium fluoride. The mol­ecular structure contains an approximately planar five-membered furan­one ring [maximum atomic deviation = 0.0221 (3) Å] and a six-membered ring adopting a chair conformation.

(1E,4Z,6E)-5-Hydroxy-1,7-bis(2-methoxyphenyl)-1,4,6-heptatrien-3-one

In the title compound, C21H20O4, the central hepta­trienone unit is approximately planar, with a maximum atomic deviation of 0.1121 (11) Å; the two benzene rings are twisted with respect to the hepta­trienone mean plane by 2.73 (5) and 29.31 (4)°. The mol­ecule exists in the enol form and the hy­droxy group forms an intra­molecular hydrogen bond with the neighboring carbonyl group. Weak inter­molecular C—H⋯O hydrogen bonding is present in the crystal structure.

4,5,6,7-Tetrachloro-N-(2,3,4-trifluorophenyl)phthalimide

The asymmetric unit of the title compound, C14H2Cl4F3NO2, contains two independent mol­ecules. In each mol­ecule, the phthalimide ring system is nearly planar [maximum atomic deviation = 0.031 (2) or 0.038 (2) Å] and oriented with respect to the benzene ring at 65.04 (7) or 71.76 (10)°. Weak inter­molecular C—H⋯O and C—H⋯F hydrogen bonding is present in the crystal structure.

5-(Hydroxymethyl)furan-2-carboxylic acid

In the title compound, C6H6O4, the furan ring is nearly coplanar with the carboxyl group, the maximum atomic deviation being 0.0248 (9) Å. The crystal packing is stabilized by classical O—H⋯O and weak C—H⋯O hydrogen bonding.

Whole-molecule disordered (E)-2-(1-hydroxy-3-phenylprop-2-en-1-ylidene)-4,5-dimethoxycyclopent-4-ene-1,3-dione isolated fromLindera oxyphylla(Lauraceae)

In the mol­ecule of the title compound, C16H14O5, all non-H atoms are approximately co-planar [maximum atomic deviation = 0.064 (5) Å]. The hy­droxy group is a hydrogen-bond donor to a carbonyl O atom. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure. The crystal structure is ’whole-mol­ecule disordered’ about an axis that runs approximately along the length of the mol­ecule; the occupancy of the two disorder components was set as exactly 0.5. An intra­molecular O—-H⋯O hydrogen bond exists in each component.

Rauniticine-allo-oxindole B methanol monosolvate.

The title penta­cyclic oxindole alkadoid, isolated from Uncaria longiflora, crystallizes as a methanol solvate, C20H22N2O4·CH4O. The five-membered ring comprising the indole fused ring is nearly planar [maximum atomic deviation = 0.031 (2) Å], whereas the five-membered ring having alphatic C atoms adopts an envelope shape (with the tertiary N atom representing the flap). The six-membered ring that shares an N atom with the envelope-shaped ring adopts a chair shape; the six-membered ring having an O atom is sofa-shaped. The carb­oxy­lic acid group acts as a hydrogen-bond donor to a methanol mol­ecule; this, in turn, acts as a hydrogen-bond donor to the double-bond carboxyl O atom of an adjacent mol­ecule, generating a chain. Adjacent chains are linked by N—H⋯O hydrogen bonds, forming a layer motif.

3-(Pyridin-4-yl-thio)-pentane-2,4-dione.

In the title compound, C10H11NO2S, the acetyl­acetone group crystallizes in the keto form with all the non-hydrogen atoms in the acetyl­acetone group approximately co-planar with a maximum atomic deviation 0.055 (2) Å; the dihedral angle between the acetyl­acetone group and the pyridine ring is 85.90 (6)°. An intra­molecular O—H⋯O hydrogen bond involving the acetyl­acetone group forms a six-membered ring.

10-Hydroxy-2-azapentacyclo[10.8.0.02,10.04,9.015,20]icosa-1(12),4(9),5,7,13,15(20),16,18-octaene-3,11-dione

In the title compound, C19H11NO3, the isoindolinone ring system is approximately planar with a maximum atomic deviation of 0.071 (1) Å and the five-membered ring of the dihydro­benzo[g]indol-3-one unit assumes an envelope conformation. The naphthalene ring system makes a dihedral angle of 39.47 (4)° with the mean plane of the isoindolinone system. Inter­molecular O—H⋯O and C—H⋯O hydrogen bonding helps to stabilize the crystal structure.

Ethyl 5-bromo-1-benzofuran-2-carboxyl-ate.

In the title compound, C11H9BrO3, the benzofuran fused-ring system is almost planar, with a maximum atomic deviation of 0.024 (5) Å; the carboxyl –CO2 fragment is aligned at 4.8 (7)° with respect to the fused-ring plane. Weak inter­molecular C—H⋯O hydrogen bonding is present in the crystal structure. π–π stacking is also observed between parallel mol­ecules, the centroid–centroid distance between benzene and furan rings of adjacent mol­ecules being 3.662 (3) Å.

(5S)-3-Chloro-5-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]-4-(4-methylpiperidin-1-yl)furan-2(5H)-one

The title compound, C20H32ClNO3, was obtained via a tandem asymmetric Michael addition–elimination reaction of (5S)-3,4-dichloro-5-(l-menth­yloxy)furan-2(5H)-one and 4-methyl­piperidine in the presence of potassium fluoride. The furan­one ring is approximately planar [maximum atomic deviation = 0.022 (2) Å] while the cyclo­hexane ring adopts a chair conformation. Weak inter­molecular C—H⋯O hydrogen bonding is present in the crystal structure.

4-Amino-3-methylbenzoic acid–1,2-bis(4-pyridyl)ethane (1/1)

In the crystal structure of the title 1:1 adduct, C12H12N2·C8H9NO2, the 4-amino-3-methyl­benzoic acid mol­ecules and 1,2-bis­(4-pyrid­yl)ethane mol­ecules are linked by inter­molecular O—H⋯N, N—H⋯O and N—H⋯N hydrogen bonds, forming a two-dimensional supra­molecular network parallel to (001). In the 1,2-bis­(4-pyrid­yl)ethane mol­ecule, the two pyridine rings are twisted to each other by a dihedral angle of 12.12 (8)°. The non-H atoms of the 4-amino-3-methyl­benzoic acid mol­ecule are almost coplanar, the maximum atomic deviation being 0.029 (1) Å. Weak C—H⋯π inter­actions are present in the crystal structure.

N-{2-[(4S)-4-tert-Butyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl}-5,6-diphenyl-1,2,4-triazin-3-amine

The title compound, C28H27N5O, was synthesized using palladium cross-coupling amination of 3-bromo-5,6-diphenyl-1,2,4-triazine with 2-[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]aniline. The oxazoline ring is almost planar, with a maximum atomic deviation of 0.023 (5) Å. The phenyl rings make dihedral angles of 29.0 (1) and 54.6 (1)° with the triazine ring while the benzene ring makes a dihedral angle of 0.6 (1)° with the oxazoline ring. The conformation of the mol­ecule is influenced by strong intra­molecular N—H⋯N and weak C—H⋯N hydrogen bonds. In the crystal, screw-axis related mol­ecules are linked into supra­molecular chains by inter­molecular C—H⋯O hydrogen bonds. π–π stacking is observed between the oxazoline and triazine rings of adjacent mol­ecules, with a centroid–centroid distance of 3.749 (2) Å.