Evaluating the secondary bioactive metabolites in Geodia corticostylifera.

Ophiactis savignyi could be discovered all over the world in tropical marine environments. People could have aided in the spread of O. savignyi, particularly in the western and eastern populations of Panama's Isthmus. The brittle star Ophiactis savignyi, often known as savigny's brittle star, coexists alongside the sponge Geodia corticostylifera. The focus of this research has been to assess the functional relevance of G. corticostylifera secondary metabolites as antifoulant against mussels, protection against generalist fish, and chemical cues to affiliated brittle stars. Both in flow-through and static seawater laboratory studies, O. savignyi which has previously been connected with sponges, was given both treated and control mimics at the same time. The sponge extract was also tested for its ability to protect fish against predators and fouling. Deterrence test using chemicals indicated that the normal level of the sponge extract may also suppress generalist fish predation in the field as well as the mussel Perna perna's normal attachment in clinical contexts. According to the findings, G. corticostylifera crude extract has many roles in the aquatic environments, apparently being accountable for this sponge's tighter relationship with O. savignyi, which protects the ophiuroid and inhibits epibionts on itself.

Crystal structure and Hirshfeld surface analysis of two imidazo[1,2-a]pyridine derivatives: N-tert-butyl-2-(4-meth-oxy-phen-yl)-5-methyl-imidazo[1,2-a]pyridin-3-amine and N-tert-butyl-2-[4-(di-methyl-amino)-phen-yl]imidazo[1,2-a]pyridin-3-amine.

In the title imidazo[1,2-a]pyridine derivatives, N-tert-butyl-2-(4-meth-oxy-phen-yl)-5-methyl-imidazo[1,2-a]pyridin-3-amine, C19H23N3O, (I), and N-tert-butyl-2-[4-(di-methyl-amino)-phen-yl]imidazo[1,2-a]pyridin-3-amine, C19H24N4, (II), the 4-meth-oxy-phenyl ring in (I) and the 4-(di-methyl-amino)-phenyl ring in (II) are inclined to the respective imidazole rings by 26.69 (9) and 31.35 (10)°. In the crystal of (I), mol-ecules are linked by N-H⋯N hydrogen bonds, forming chains propagating along the [001] direction. The chains are linked by C-H⋯π inter-actions, forming layers parallel to the (010) plane. In (II), the crystal packing also features N-H⋯N hydrogen bonds, which together with C-H⋯N hydrogen bonds link mol-ecules to form chains propagating along the c-axis direction. The chains are linked by C-H⋯π inter-actions to form layers parallel to the (100) plane. Inversion-related layers are linked by offset π-π inter-actions [inter-centroid distance = 3.577 (1) Å]. The inter-molecular inter-actions of both compounds were analyzed using Hirshfeld surface analysis and two-dimensional fingerprint plots.

Crystal structures of 1-benzene-sulfon-yl-2-methyl-3-(4-nitro-benzoyl)-2,3-di-hydro-1H-indole and 1-benzene-sulfon-yl-2-methyl-3-[(thio-phen-2-yl)carbon-yl]-2,3-di-hydro-1H-indole.

In the title indole derivatives, C22H16N2O5S, (I) and C20H15NO3S2, (II), the sulfonyl-bound phenyl rings are almost orthogonal to the indole ring system, subtending dihedral angles of 88.33 (10) and 87.58 (16)°, respectively. In both compounds, the sulfonyl S atom has a distorted tetra-hedral geometry [O-S-O = 119.98 (9) and N-S-C = 104.01 (8)° for compound (I) and O-S-O = 120.08 (18) and N-S-C = 104.91 (14)° for compound (II)] and the sum of the bond angles at N indicates sp2 hybridization. The mol-ecules of both (I) and (II) feature intra-molecular C-H⋯O hydrogen bonds that generate S(6) ring motifs with the sulfone O atom. In the crystals, mol-ecules of (I) are linked by C-H-O hydrogen bonds, forming R44(18) ring motifs while mol-ecules of (II) are linked by C-H-O and C-H-S hydrogen bonds, forming R22(12) ring motifs. Compound (II) was refined as an inversion twin.

Crystal structures of (E)-(3-ethyl-1-methyl-2,6-di-phenyl-piperidin-4-yl-idene)amino phenyl carbonate and (E)-(3-isopropyl-1-methyl-2,6-di-phenyl-piperidin-4-yl-idene)amino phenyl carbonate.

In the title compounds, C27H28N2O3, (I), and C28H30N2O3, (II), the conformation about the C=N bond is E. The piperidine rings adopt chair conformations with the attached phenyl rings almost normal to their mean planes, the dihedral angles being 85.82 (8) and 85.84 (7)° in (I), and 87.98 (12) and 86.42 (13)° in (II). The phenyl rings are inclined to one another by 52.87 (8)° in (I) and by 60.51 (14)° in (II). The main difference in the conformation of the two compounds is the angle of inclination of the phen-oxy-carbonyl ring to the piperidine ring mean plane. In (I), these two planes are almost coplanar, with a dihedral angle of 2.05 (8)°, while in (II), this angle is 45.24 (13)°. In the crystal of (I), mol-ecules are linked by C-H⋯O hydrogen bonds, forming inversion dimers with R 2 (2)(14) loops. The dimers are linked via C-H⋯π inter-actions forming a three-dimensional network. In the crystal of (II), there are no significant inter-molecular inter-actions present.

Purification, crystallization, preliminary X-ray diffraction and molecular-replacement studies of great cormorant (Phalacrocorax carbo) haemoglobin.

Haemoglobin is the iron-containing oxygen-transport metalloprotein that is present in the red blood cells of all vertebrates. In recent decades, there has been substantial interest in attempting to understand the structural basis and functional diversity of avian haemoglobins. Towards this end, purification, crystallization, preliminary X-ray diffraction and molecular-replacement studies have been carried out on cormorant (Phalacrocorax carbo) haemoglobin. Crystals were grown by the hanging-drop vapour-diffusion method using PEG 3350, NaCl and glycerol as precipitants. The crystals belonged to the trigonal system P3121, with unit-cell parameters a=b=55.64, c=153.38 Å, ß=120.00°; a complete data set was collected to a resolution of 3.5 Å. Matthews coefficient analysis indicated that the crystals contained a half-tetramer in the asymmetric unit.

(E)-1,3-Dimethyl-2,6-di-phenyl-piperidin-4-one O-(phen-oxy-carbon-yl)oxime.

The title piperidine derivative, C26H26N2O3, has an E conformation about the N=C bond. The piperidine ring has a chair conformation and its mean plane is almost perpendicular to the attached phenyl rings, making dihedral angles of 87.47 (9) and 87.34 (8)°. The planes of these two phenyl rings are inclined to one another by 60.38 (9)°. The plane of the terminal phenyl ring is tilted at an angle of 32.79 (9)° to the mean plane of the piperidine ring. The mol-ecular conformation is stabilized by two intra-molecular C-H⋯O contacts. There are no significant inter-molecular inter-actions in the crystal.

Methyl 1-phenyl-3-p-tolyl-1,9b-di-hydro-3H-chromeno[4,3-c]isoxazole-3a(4H)-carboxyl-ate.

In the title compound, C25H23NO4, the pyran ring of the chroman moiety has an envelope conformation with the methyl-ene C atom as the flap. The isoxazole ring has a twist conformation on the O-C bond. The dihedral angle between their mean planes is 57.87 (9)°. The attached phenyl and benzene rings are twisted away from its mean plane by 56.19 (10) and 50.57 (10)°, respectively. These two rings are normal to each other, subtending a dihedral angle of 89.2 (1)°. In the crystal, there are no classical hydrogen bonds; the mol-ecules are linked via C-H⋯π inter-actions, forming a two-dimensional network lying parallel to (10-1).

Methyl 9-hy-droxy-15-methyl-2-oxo-11-(pyren-1-yl)-10-oxa-15-aza-tetra-cyclo-[7.6.0.0(1,12).0(3,8)]penta-deca-3(8),4,6-triene-12-carboxyl-ate.

In the title compound, C32H25NO5, the furan and pyrrole rings each adopt an envelope conformation, the respective flap atoms being the C atom bearing the pyrene substituent and the CH2 atom adjacent to the N atom. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond. In the crystal, C-H⋯O contacts link the mol-ecules, forming a two-dimensional network parallel to (001).

Methyl 8-bromo-3-[1-(4-meth-oxy-phen-yl)-4-oxo-3-phenyl-azetidin-2-yl]-1-methyl-1,2,3,3a,4,9b-hexa-hydro-chromeno[4,3-b]pyrrole-3a-carboxyl-ate.

In the title compound, C30H29BrN2O5, the ß-lactam ring is essentially planar, with the O atom displaced from this plane by 0.856 (9) Å, and forming dihedral angles of 24.35 (13) and 89.42 (14)° with the planes of the benzene substituent groups on this ring. The tetra-hydro-pyran ring adopts an envelope conformation with the C atom bearing the ß-lactam ring as the flap. In the crystal, weak C-H⋯O hydrogen bonds with carboxyl and tetra-hydro-pyran O-atom acceptors give rise to a chain structure extending along the b-axis direction.

14-Meth-oxy-4,6-dimethyl-9-phenyl-8,12-dioxa-4,6-di-aza-tetra-cyclo-[8.8.0.0(2,7).0(13,18)]octa-deca-2(7),13,15,17-tetra-ene-3,5,11-trione.

The title compound, C23H20N2O6, crystallizes with two mol-ecules in the asymmetric unit in which the dihedral angles between the mean planes of the pyran and phenyl rings are 66.6 (1) and 61.9 (1) °. The fused pyrone and pyran rings each adopts a sofa conformation. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules, forming a two-dimensional network parallel to [001].

(1'S,12'R,13'S,17'S)-15',15'-Dimethyl-1,2-dihydro-11',14',16',18'-tetra-oxa-7'-aza-spiro-[indole-3,8'-penta-cyclo-[10.6.0.0(2,9).0(3,7).0(13,17)]octa-deca-ne]-2,10'-dione.

In the title compound, C22H24N2O6, the indole ring has a twist conformation and the tetra-hydro-2H-pyran-2-one ring a half-chair conformation. One of the pyrrolidine rings adopts an envelope conformation on the N atom, while the other has a twist conformation; the 'butterfly' angle between their mean planes is 62.98 (11)°. The dioxolane ring adopts a twist conformation and the tetra-hydro-furan ring has an envelope conformation on the C atom in the fused tetra-hydro-2H-pyran-2-one ring adjacent to the O atom of the tetra-hydro-furan ring. The 'butterfly' angle between the mean planes of these two five-membered rings is 69.14 (10)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming chains along the a axis.

Ethyl (2E,4E)-5-(3-bromo-phenyl-sulfon-yl)penta-2,4-dienoate.

In the title compound, C13H13BrO4S, both C=C double bonds adopt an E conformation. The S atom has a distorted tetra-hedral geometry with bond angles ranging from 102.17 (13) to 119.77 (14)°. The ethyl acrylate substituent adopts an extented conformation with all torsion angles close to 180°. In the crystal, mol-ecules are linked into centrosymmetric R 2 (2)(14) dimers via pairs of C-H⋯O hydrogen bonds.

4-Bromo-2-(dieth-oxy-meth-yl)phenyl benzoate.

In the title compound, C18H19BrO4, the aromatic rings enclose a dihedral angle of 81.9 (7)°. There are no short directional contacts in the crystal structure.

14-Eth-oxy-4,6-dimethyl-9-phenyl-8,12-dioxa-4,6-diaza-tetra-cyclo-[8.8.0.0(2,7).0(13,18)]octa-deca-2(7),13,15,17-tetra-ene-3,5,11-trione.

In the title compound, C23H20N2O6, the fused pyrone and pyran rings each adopt a sofa conformation. The dihedral angle between the mean planes of the pyran and phenyl rings is 61.9 (1)°. In the crystal, mol-ecules are linked by two pairs of C-H⋯O hydrogen bonds, forming dimers. These dimers are linked via a third C-H⋯O hydrogen bond, forming a two-dimensional network parallel to (10-2).

Diethyl 2,6-dimethyl-4-[4-(3-phenyl-acrylo-yloxy)phen-yl]-1,4-dihydro-pyridine-3,5-dicarboxyl-ate hemihydrate.

In the title ester derivative, C28H29NO6·0.5H2O, the 1,4-dihydro-pyridine ring has a flattened boat conformation. The mean plane is almost perpendicular to the attached benzene ring, making a dihedral angle of 86.87 (9)°. The terminal phenyl ring is inclined to the central benzene ring by 67.56 (12)°. In the crystal, mol-ecules are bridged via O-H⋯O hydrogen bonds involving the partially occupied water mol-ecule, and this arrangement is strengthened by a pair of N-H⋯O hydrogen bonds and C-H⋯O inter-actions. The ethyl atoms of one of the ethyl ester groups are disordered over two sites with an occupancy ratio of 0.716 (5):0.284 (5).

Methyl 6-eth-oxy-3-phenyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-car-boxylate.

In the title compound, C(20)H(19)NO(5), the dihedral angle between the mean plane of the pyran ring (which has a half-chair conformation) and the benzene ring of the chromeno ring system is 7.21 (7)°. The dihedral angle between the mean plane of the chromeno ring system and the isoxazole ring is 21.78 (6)°, while the isoxazole ring forms a dihedral angle of 72.60 (8)° with the attached phenyl ring. In the crystal, mol-ecules are linked via pairs of C-H⋯O hydrogen bonds, forming inversion dimers with an R(2) (2)(10) ring motif. These dimers are linked via C-H⋯N hydrogen bonds, forming chains along [001].

3-(2-Methyl-phen-yl)-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-carbo-nitrile.

In the title compound, C(18)H(14)N(2)O(2), the pyran ring of the chromeno ring system has a half-chair conformation, and the dihedral angle between its mean plane and the benzene ring is 5.3 (2)°. The isoxazole ring forms a dihedral angle of 74.6 (2)° with the attached benzene ring and is inclined to the mean plane of the chromeno ring system by 15.06 (19)°. In the crystal, there are no significant inter-molecular inter-actions.

Diethyl [(2-chloro-anilino)(1,3-diphenyl-1H-pyrazol-4-yl)meth-yl]phospho-nate.

In the title compound, C(26)H(27)ClN(3)O(3)P, the mean plane of the central pyrazole ring forms a dihedral angle of 71.37 (14)° with the chloro-phenyl ring. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers with R(2) (2)(10) ring motifs. The 3-phenyl ring is disordered with four C atoms occupying two sets of sites with an occupancy ratio of 0.748 (4):0.252 (4).

(6bS*,14R*,14aR*)-Methyl 14-(4-methyl-phen-yl)-7-oxo-6b,6c,7,12b,14,14a-hexa-hydro-1H-pyrano[3,2-c:5,4-c']dichromene-14a-carboxyl-ate.

In the title compound, C(28)H(22)O(6), the chromeno ring system is almost planar, with a dihedral angle between the mean planes of the pyran and benzene rings of 1.87 (8)°. The pyran ring bearing the methyl-phenyl substituent has a half-chair conformation while the other pyran ring has an envelope conformation with the tetra-substituted C atom as the flap. The benzene ring of the chromeno ring system is inclined to the benzene ring fused to the latter pyran ring by 74.66 (9)°. These aromatic rings are inclined to the 4-methyl-phenyl ring by 52.67 (9) and 66.63 (10)°, respectively. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming a two-dimensional network parallel to the bc plane.

14-Eth-oxy-4,6,9-trimethyl-8,12-dioxa-4,6-diaza-tetra-cyclo-[8.8.0.0(2,7).0(13,18)]octa-deca-2(7),13,15,17-tetra-ene-3,5,11-trione.

In the title compound, C(19)H(20)N(2)O(6), the pyrone and pyran rings adopt envelope conformations with the same common C atom as the flap, the dihedral angle between the planes of the remaining ring atoms being 68.27 (4)°. The planar atoms of the pyran ring and the diaza-cyclic ring are almost coplanar, the dihedral angle between their mean planes being 3.29 (7)°. Moreover, the planar atoms of the pyrone ring and benzene ring of the coumarin unit are also close to coplanar, the dihedral angle between their mean planes being 8.03 (9)°. The meth-oxy group lies in the plane of the benzene ring, with a dihedral angle between their mean planes of 9.4 (2)°. In the crystal, the molecules are linked by C-H⋯O hydrogen bonds resulting in sheets of mol-ecules in the ac plane.