Crystal structure of 3-({[(morpholin-4-yl)carbono-thio-yl]sulfan-yl}acet-yl)phenyl benzoate.

In the title compound, C20H19NO4S2, the morpholine ring adopts the expected chair conformation. The central phenyl ring makes dihedral angles of 67.97 (4) and 7.74 (3)°, respectively, with the benzoate phenyl ring and the morpholine mean plane. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming zigzag chains along the b-axis direction. C-H⋯π inter-actions link centrosymmetrically related mol-ecules, reinforcing the three-dimensional structure.

N-(6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)benzene-sulfonamide.

The asymmetric unit of the title compound, C13H11ClN4O2S, contains two mol-ecules (A and B), in which the dihedral angles between the 1H-imidazo[4,5-c]pyridine system and terminal phenyl ring are 80.83 (10) and 62.34 (1)°. In the crystal, A-B dimers are linked by pairs of N-H⋯N hydrogen bonds, which generate R (2) 2(10) loops. The dimers are linked by C-H⋯O and C-H⋯Cl inter-actions, generating a three-dimensional network. Aromatic π-π stacking inter-actions [shortest centroid-centroid distance = 3.5211 (12) Å] are also observed.

1,1',1'',1'''-(Oxydi-methane-tri-yl)tetra-kis-(4-fluoro-benzene).

In the title compound, C26H18F4O2, the dihedral angles between pairs of benzene rings linked to the same C atom are 80.55 (8) and 79.11 (7)°. The crystal packing features C-H⋯π inter-actions and shows stacking when viewed along the c axis.

(6-Meth-oxy-2-oxo-2H-chromen-4-yl)methyl morpholine-4-carbodithio-ate.

In the title compound, C(16)H(17)NO(4)S(2), the 2H-chromene ring system is nearly planar, with a maximum deviation of 0.070 (1) Å, and the morpholine ring adopts a chair conformation; the bond-angle sum for its N atom is 357.9°. The dihedral angle between the the 2H-chromene ring and the best plane through the morpholine ring is 89.09 (6)°. An intra-molecular C-H⋯S hydrogen bond occurs. In the crystal, C-H⋯O hydrogen bonds generate R(2) (2)(8) rings and π-π inter-actions occur between fused benzene rings of the chromene system [shortest centroid-centroid distance = 3.5487 (8) Å].

3-(2-Bromo-acet-yl)phenyl benzoate.

In the title compound, C15H11BrO3, the dihedral angle between the benzene rings is 72.59 (6)°. In the crystal, pairs of C-H⋯π contacts form inversion dimers. Additional C-H⋯O hydrogen bonds generate R2(1)(6) ring motifs and stack these dimers along the b axis. Short inter-molecular Br⋯O contacts of 3.254 (3) Šare also observed and link the stacks into a three-dimensional network.

2-Oxo-2-(2-oxo-2H-chromen-3-yl)ethyl pyrrolidine-1-carbodi-thio-ate.

There are two independent mol-ecules in the asymmetric unit of the title compound, C16H15NO3S2, in which the pyrrolidine rings adopt envelope conformations, with a methyl-ene C atom as the flap. The dihedral angles betweeen the near-planar 2H-chromene ring systems [maximum deviations = 0.0167 (20) and 0.0136 (19) Å] and the pyrrolidine rings (all atoms) are 83.83 (11) and 82.43 (11)°. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds occur for one of the mol-ecules. Further C-H⋯O links involving both mol-ecules generate a three-dimensional network.

(7-Chloro-2-oxo-2H-chromen-4-yl)methyl di-ethyl-carbamodi-thio-ate.

In the title compound, C15H16ClNO2S2, the 2H-chromene ring system is nearly planar, with a maximum deviation of 0.023 (2) Å. In the crystal, C-H⋯O hydrogen bonds give R 2 (1)(7) motifs, which generate [100] chains. C-H⋯π and π-π inter-actions between chromene moieties [shortest ring centroid-centroid distance = 3.6199 (13) Å] consolidate the packing.

2-Oxo-2-(2-oxo-2H-chromen-3-yl)ethyl di-ethyl-dithio-carbamate.

In the title compound, C16H17NO3S2, the dihedral angles between the O/C/C/S group and the 2H-chromene ring system and the thio-carbamate group are 14.46 (9) and 83.30 (9)°, respectively. The bond-angle sum at the N atom is 360.0°. One of the methyl C atoms lies above the thio-carbamate plane and one lies below it [deviations = 1.264 (3) and -1.147 (3) Å, respectively]. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds generate R 2 (2)(10) loops. Weak aromatic π-π stacking inter-actions [shortest centroid-centroid distance = 3.8138 (11) Å] are also observed.

(6-Meth-oxy-2-oxo-2H-chromen-4-yl)methyl piperidine-1-carbodi-thio-ate.

In the title compound, C17H19NO3S2, the maximum deviation of atoms in the 2H-chromene ring system is 0.0097 (14) Šand the piperidine ring adopts a chair conformation. The dihedral angle between the 2H-chromene ring and the piperidine ring (all atoms) is 87.59 (8)°. In the crystal, inversion dimers linked by pairs of C-H⋯O inter-actions generate R 2 (2)(22) loops. Further C-H⋯O hydrogen bonds link the dimers into [110] chains and weak aromatic π-π stacking [shortest centroid-centroid distance = 3.824 (8) Å] is also observed.

(7-Chloro-2-oxo-2H-chromen-4-yl)methyl pyrrolidine-1-carbodi-thio-ate.

In the title compound, C15H14ClNO2S2, the 2H-chromene ring system is essentially planar, with a maximum deviation of 0.0133 (10) Å. Three C atoms and their attached H atoms of the pyrrolidine ring are disordered [occupany ratio 0.874 (7):0.126 (7)] with both disorder components adopting a twisted conformation. The dihedral angle between the 2H-chromene ring system and the major occupancy component of the pyrrolidine ring is 89.45 (7)°. In the crystal, inversion dimers linked by pairs of C-H⋯S and C-H⋯O inter-actions generate R (2) 2(24) and R (2) 2(10) loops, respectively. Further C-H⋯O hydrogen bonds link the dimers into [100] chains. C-H⋯π inter-actions also occur and there is very weak π-π stacking [inter-planar spacing = 3.650 (5) Å; centroid-centroid distance = 4.095 (7) Å] between inversion-related chloro-benzene rings.

(6-Meth-oxy-2-oxo-2H-chromen-4-yl)methyl pyrrolidine-1-carbodithio-ate.

In the title compound, C(16)H(17)NO(3)S(2), the 2H-chromene ring is close to being planar [maximum deviation = 0.034 (2) Å] and the pyrrolidine ring is twisted about the C-C bond opposite the N atom. The dihedral angle between the ring-system planes is 75.24 (16)° and an intra-molecular C-H⋯S inter-action occurs. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds and the packing also exhibits π-π inter-actions, with a distance of 3.6106 (13) Šbetween the centroids of the benzene rings of neighbouring mol-ecules.

(5,7-Dimethyl-2-oxo-2H-chromen-4-yl)methyl pyrrolidine-1-carbodithio-ate.

In the title compound, C(17)H(19)NO(2)S(2), the 2H-chromene ring system is almost planar, with a maximum deviation of 0.044 (2) Å, and the pyrrolidine ring adopts an envelope conformation. The dihedral angle between the 2H-chromene system and the planar part of the pyrrolidine ring is 83.65 (8)°. A weak intra-molecular C-H⋯S hydrogen bond occurs. The crystal structure features C-H⋯O hydrogen bonds and π-π inter-actions, with a centroid-centroid distance of 3.5728 (16) Å.

(5,7-Dimethyl-2-oxo-2H-chromen-4-yl)methyl diethyl-dithio-carbamate.

In the title compound, C(17)H(21)NO(2)S(2), the coumarin ring system is nearly planar, with a maximum deviation of 0.080 (2) Šfrom the mean plane. An intra-molecular C-H⋯S hydrogen bond occurs. The crystal structure features C-H⋯S hydrogen bonds and weak π-π inter-actions with a centroid-centroid distance of 3.679 (1) Å.

Methyl N-{4-[(4-meth-oxy-phen-oxy)meth-yl]-2-oxo-2H-chromen-7-yl}carbamate.

In the title compound, C(19)H(17)NO(6), the dihedral angle between the 2H-chromene ring system and benzene ring is 5.34 (6)°. A short intra-molecular C-H⋯O contact occurs. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, generating C(8) chains propagating in [010]. The chains are linked by C-H⋯O inter-actions and the packing also exhibits π-π stacking inter-actions between benzene and pyran rings, with a centroid-centroid distance of 3.676 (9) Å.

(3-Oxo-3H-benzo[f]chromen-1-yl)methyl piperidine-1-carbodithio-ate.

In the title compound, C(20)H(19)N O(2)S(2),the 3Hbenzo-chromene ring system is nearly planar, with a maximum deviation of 0.036 (2) Å, and the piperidine ring adopts a chair conformation: the bond-angle sum for its N atom is 358.7°. The dihedral angle between the 3H-benzo[f]chromene ring and the piperidine ring is 89.07 (8)°. In the crystal, C-H⋯O hydrogen bonds lead to [010] C(6) chains and weak aromatic π-π inter-actions between the fused pyran ring and fused benzene ring of benzochromene [centroid-centroid distance = 3.652 (1) Å] are also observed.

(3-Oxo-3H-benzo[f]chromen-1-yl)methyl N,N-dimethyl-carbamodithio-ate.

In the title compound, C(17)H(15)NO(2)S(2), the 3H-benzo[f]chromene ring system is distinctly twisted; the dihedral angle between the pyran ring and its opposite benzene ring is 9.11 (8)°. The N,N-dimethyl-carbamodithio-ate residue lies almost perpendicular to the pyran ring [dihedral angle = 85.15 (7)°]. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into C(10) chains propagating in [001].

(2-Oxo-2H-benzo[h]chromen-4-yl)methyl morpholine-4-carbodithio-ate.

In the title compound, C(19)H(17)NO(3)S(2), the morpholine ring is in a chair conformation. In the coumarin ring system, the dihedral angle between the benzene and pyran rings is 3.9 (1)°. In the crystal, weak C-H⋯O inter-actions link the mol-ecules into corrugated layers parallel to (102). The crystal packing also exhibits π-π inter-actions, with distances of 3.644 (1) and 3.677 (1) Šbetween the centroids of the benzene rings of neighbouring mol-ecules.

(7-Chloro-2-oxo-2H-chromen-4-yl)methyl piperidine-1-carbodithio-ate.

In the title compound, C(16)H(16)ClNO(2)S(2), the piperidine ring is in a chair conformation. In the coumarin ring system, the dihedral angle between the benzene and pyran rings is 3.5 (1)°. In the crystal, a weak C-H⋯O hydrogen bond links mol-ecules into chains along [001]. In addition, π-π stacking inter-actions are present involving the benzene and pyran rings, with a centroid-to-centroid distance of 3.712 (2) Å. The crystal studied is a nonmerohedral twin with refined components 0.221 (1) and 0.779 (1).

Crystal structure of (7-methyl-2-oxo-2H-chromen-4-yl)methyl piperidine-1-carbo-di-thio-ate.

In the title compound, C17H19NO2S2, the 2H-chromene ring system is nearly planar, with a maximum deviation of 0.0383 (28) Å, and the piperidine ring adopts a chair conformation. The 2H-chromene ring makes dihedral angles of 32.89 (16) and 67.33 (8)°, respectively, with the mean planes of the piperidine ring and the carbodi-thio-ate group. In the crystal, C-H⋯O and weak C-H⋯S hydrogen bonds link the mol-ecules into chains along [001]. The crystal structure also features C-H⋯π and π-π inter-actions, with a centroid-centroid distance of 3.7097 (17) Å.

Crystal structure of (7-chloro-2-oxo-2H-chromen-4-yl)methyl N,N-di-methyl-carbamodi-thio-ate.

In the title compound, C13H12Cl N O2S2, the 2H-chromene ring system is almost planar, with a maximum deviation of 0.005 (2) Å. The packing features C-H⋯S hydrogen bonds and π-π inter-actions between fused benzene rings of chromene [shortest centroid-centroid distances = 3.6553 (13) and 3.5551 (13) Å].