Crystal structure and Hirshfeld surface analysis of 1-(2,4-di-chloro-benz-yl)-5-methyl-N-(thio-phene-2-sulfon-yl)-1H-pyrazole-3-carboxamide.
ABSTRACT: In the title compound, C16H13Cl2N3O3S2, the thio-phene ring is disordered in a 0.762?(3):0.238?(3) ratio by an approximate 180° rotation of the ring around the S-C bond linking the ring to the sulfonyl unit. The di-chloro-benzene group is also disordered over two sets of sites with the same occupancy ratio. The mol-ecular conformation is stabilized by intra-molecular C-H?Cl and C-H?N hydrogen bonds, forming rings with graph-set notation S(5). In the crystal, pairs of mol-ecules are linked by N-H?O and C-H?O hydrogen bonds, forming inversion dimers with graph-set notation R22(8) and R12(11), which are connected by C-H?O hydrogen-bonding inter-actions into ribbons parallel to (100). The ribbons are further connected into a three-dimensional network by C-H?? inter-actions and ?-? stacking inter-actions between benzene and thio-phene rings, with centroid-to-centroid distances of 3.865?(2), 3.867?(7) and 3.853?(2)?Å. Hirshfeld surface analysis has been used to confirm and qu-antify the supra-molecular inter-actions.
Project description:In the title compound, C13H11N3S2, the phenyl ring is twisted from the 1,2,4-triazole plane by 63.35?(9)° and by 47.35?(9)° from the thio-phene plane. In the crystal, chains of mol-ecules running along the c-axis direction are formed by N-H?S inter-actions [graph-set motif C(4)]. The 1,2,4-triazole and phenyl rings are involved in ?-? stacking inter-actions [centroid-centroid distance = 3.4553?(10)?Å]. The thio-phene ring is involved in C-H?S and C-H?? inter-actions. The inter-molecular inter-actions in the crystal packing were further analysed using Hirshfield surface analysis, which indicates that the most significant contacts are H?H (35.8%), followed by S?H/H?S (26.7%) and C?H/H?C (18.2%).
Project description:The title compound, C(15)H(14)O(3)S, has two symmetry-independent mol-ecules in the asymmetric unit with almost identical geometry. The dihedral angle between the benzene and thio-phene rings is 1.61?(11)° in one mol-ecule and 7.21?(11)° in the other. In both mol-ecules, C-H?O hydrogen bonds generate rings of graph-set motif S(5). The crystal structure is stabilized by C-H?O hydrogen bonds, C-H?? inter-actions and ?-? inter-actions involving the benzene and thio-phene rings, with centroid-centroid distances of 3.5249?(13) and 3.6057?(13)?Å.
Project description:In the title compound, C17H18N2O3S2, the pyrimidine ring adopts a shallow sofa conformation, with the C atom bearing the axially-oriented thio-phene ring as the flap [deviation = 0.439?(3)?Å]. The plane of the thio-phene ring lies almost normal to the pyrimidine ring, making a dihedral angle of 79.36?(19)°. In the crystal, pairs of very weak C-H?O hydrogen bonds link the mol-ecules related by twofold rotation axes, forming R 2 (2)(18) rings, which are in turn linked by another C-H?O inter-action, forming chains of rings along . In addition, weak C-H??(thio-phene) inter-actions link the chains into layers parallel to  and ?-? inter-actions with a centroid-centroid distance of 3.772?(10)?Å connect these layers into a three-dimensional network.
Project description:The title compound, C11H8N2O3S, is roughly planar; the di-hedral angle between the planes of the thio-phene and benzene rings is 8.38?(10)°. An intra-molecular O-H?N hydrogen bond generates an S(5) ring motif. In the crystal, mol-ecules are linked into centrosymmetric dimers by pairs of O-H?O hydrogen bonds with an R 2 (2)(22) graph-set motif. Aromatic ?-? stacking inter-actions [centroid-centroid sep-ar-ations = 3.653?(3) and 3.852?(3)?Å] link the dimers into a three-dimensional network.
Project description:In the title mol-ecule, C(16)H(16)O(4)S, the enone fragment, thio-phene ring and benzene ring are individually essentially planar. The thio-phene ring is disordered over two sites, corresponding to a rotation of approximately 180° about the single C-C bond to which it is attached. The approximate ratio of occupancies for the major and minor components is 0.872?(2):0.128?(2). The major component of the thio-phene ring and the benzene ring are twisted from each other by 13.92?(19)°. An intra-molecular C-H?O hydrogen bond generates an S(5)S(5) ring motif. The crystal structure is stabilized by inter-molecular C-H?O hydrogen-bonding inter-actions. In addition, a ?-? stacking inter-action, with a centroid-centroid distance of 3.852?(2)?Å, and short S?O [2.9378?(12)?Å] and O?O [2.5811?(16)?Å] contacts are observed.
Project description:In the title compound, C(22)H(19)NOS(2), the thio-phene rings form angles of 69.74?(18) and 65.56?(16)° with the benzene ring. The piperidone ring adopts a half-chair conformation due to the presence of the conjugated ketone systems. Both thio-phene rings are disordered over two orientations [occupancies of 0.758?(2)/0.242?(2) and 0.588?(2)/0.412?(2)] at 180° from one another. In the crystal, weak inter-molecular C-H?O hydrogen bonds, C-H?? and aromatic ?-? stacking inter-actions [shortest centroid-centroid separation = 3.865?(3)?Å] help to stabilize the packing.
Project description:In the title compound, C(14)H(13)N(3)OS(2), the thio-phene ring is disordered over two orientations by ca 180° about the C-C bond axis linking the ring to the rest of the mol-ecule, with a site-occupancy ratio of 0.651?(5):0.349?(5). The central 1,3,4-oxadiazole-2(3H)-thione ring forms dihedral angles of 9.2?(5), 4.6?(11) and 47.70?(7)° with the major and minor parts of the disordered thio-phene ring and the terminal phenyl ring, respectively. In the crystal, no significant inter-molecular hydrogen bonds are observed. The crystal packing is stabilized by ?-? inter-actions [centroid-centroid distance = 3.589?(2)?Å].
Project description:In the title compound, C(16)H(10)Cl(2)F(3)N(3)S, the dihedral angle between the quinoline and thio-phene ring systems is 4.94?(10)°. The NH group of the hydrazone moiety does not form a hydrogen bond, due to a steric crowding. In the crystal, the thio-phene ring takes part in weak ?-? stacking inter-actions with the pyridine ring [centroid-to-centroid separation = 3.7553?(19)?Å and inter-planar angle = 5.48?(12)°] and the benzene ring [3.7927?(19)?Å and 4.58?(12)°]. Together, these lead to  stacks of mol-ecules in an alternating head-to-tail arrangement, with two ?-? stacking contacts between each adjacent pair.
Project description:The title compound, C18H20N4O2S2, is a new 1,3,4-oxa-diazole and a key pharmacophore of several biologically active agents. It is composed of a meth-yl(thio-phen-2-yl)-1,3,4-oxa-diazole-2(3H)-thione moiety linked to a 2-meth-oxy-phenyl unit via a piperazine ring that has a chair conformation. The thio-phene ring mean plane lies almost in the plane of the oxa-diazole ring, with a dihedral angle of 4.35?(9)°. The 2-meth-oxy-phenyl ring is almost normal to the oxa-diazole ring, with a dihedral angle of 84.17?(10)°. In the crystal, mol-ecules are linked by weak C-H?S hydrogen bonds and C-H?? inter-actions, forming layers parallel to the bc plane. The layers are linked via weak C-H?O hydrogen bonds and slipped parallel ?-? inter-actions [inter-centroid distance = 3.6729?(10)?Å], forming a three-dimensional structure. The thio-phene ring has an approximate 180° rotational disorder about the bridging C-C bond.
Project description:In the title thio-phene-derived Schiff base compound, C(12)H(8)N(2)S(2), the thio-phene ring is slighty rotated from the benzothia-zole group mean plane, giving a dihedral angle of 12.87?(6)°. The largest displacement of an atom in the mol-ecule from the nine-atom mean plane defined by the non-H atoms of the benzothia-zole ring system is 0.572?(1)?Å, exhibited by the C atom at the 3-position of the thio-phene ring. In the crystal, weak C-H?S hydrogen bonds involving the thio-phene group S atom and the 4-position thio-phene C-H group of a symmetry-related mol-ecule lead to an infinite one-dimensional chain colinear with the c axis. The structure is further stabilized by ?-? inter-actions; the distance between the thia-zole ring centroid and the centroid of an adjacent benzene ring is 3.686?(1)?Å. The crystal studied was an inversion twin with the ratio of components 0.73?(3):0.27?(3).