Hydro­gen bonding and C—H⃛O interactions in 2‐[1‐(1‐naphthyl)ethyl]benzoic acid at 150 K

The title acid, C₁₉H₁₆O₂, crystallized in the centrosymmetric space group Pnna with three mol­ecules in the asymmetric unit (apparently the first reported instance of Z′ = 3 in this space group). Four intermolecular hydrogen bonds have O_D?O_A distances of 2.660 (2), 2.594 (2), 2.633 (2) and 2.646 (2) Å, and angles of 177 (2), 179 (2), 175 (2) and 175 (2)°. The four hydrogen bonds form two R(8) cyclic dimers, one about a twofold axis. Five leading intermolecular C—H?O interactions are present. Although first‐ and second‐level graph sets involving these nine interactions are dominated by finite patterns, a three‐dimensional network becomes evident upon analysis of higher‐level graphs. A number of intramolecular C—H?O interactions are also present.     

Hydro­gen bonding and C—H⋯O interactions in 3‐(3‐amino­phthal­imido)phthalic acid dihydrate

The title compound, C₁₆H₁₀N₂O₆·2H₂O, crystallized in the centrosymmetric triclinic space group P with one organic mol­ecule and two water mol­ecules as the asymmetric unit. Eight intermolecular hydrogen bonds have donor?acceptor distances in the range 2.602 (2)–3.289 (2) Å, with angles in the range 137 (2)–177 (2)°. These generate a three‐dimensional hydrogen‐bond network. There is a single intramolecular hydrogen bond. There are six significant intermolecular C—H?O interactions with H?O distances in the range 2.39–2.74 Å, and C—H?O angles in the range 131–157°.     

Hydro­gen bonds and C—H⋯O interactions in 2‐(2‐methyl­benzyl)­malonic acid at 150 K

The title compound, C₁₁H₁₂O₄, crystallized in the centrosymmetric space group Pbca with one mol­ecule as the asymmetric unit. The two hydrogen bonds have O_D?O_A distances of 2.667 (2) and 2.628 (2) Å, and O—H?O angles of 179 (2) and 177 (2)°. Each hydrogen bond forms an R(8) cyclic dimer about a center of symmetry. The leading intermolecular C—­H?O interaction has an H?O distance of 2.66 Å and a C—H?O angle of 160°. Taken together with the hydrogen bonds, it results in a three‐dimensional network of inter­actions. The structure is compared with that of a close analog, benzyl­malonic acid.     

Hydro­gen bonds and C—H⋯O ­interactions in the enol tautomer of 4‐­(phenylsulfonyl)spiro­[cyclo­pentane‐1,9′‐[9H]­fluorene]‐2,3‐dione

The title compound, 2‐hydroxy‐1‐(phenyl­sulfonyl)­spiro­[cyclo­pentene‐4,9′‐[9H]­fluoren]‐3‐one, C₂₃H₁₆O₄S, crystallized in the centrosymmetric space group P2₁/n with one mol­ecule as the asymmetric unit. The hydroxyl‐H atom is ordered and participates in a single intramolecular hydrogen bond and in a single intermolecular hydrogen bond, in which the O_D—H distance is 0.90 (2), H?O_A is 2.34 (3), O_D?O_A is 2.987 (2) Å and O_D—H?O_A is 129 (2)°. The intermolecular hydrogen bond forms an R(12) cyclic dimer about a center of symmetry. There are six leading C—H?O interactions. Taken together, these interactions form a three‐dimensional network. Structural comparisons are made with tetrabenzodi­spiro­[4.0.4.3]­tridecatetraene.     

C—H⋯N and C—H⋯π interactions in 2‐ethoxy‐4,6‐diphenylpyridine‐3‐carbonitrile

The title compound, C₂₀H₁₆N₂O, has two mol­ecules in the asymmetric unit and the crystal structure shows that the central pyridine ring of each mol­ecule has a flat boat conformation. The terminal C atom in one of the mol­ecules is disordered over two positions, with relative occupancies of 0.594 (14) and 0.398 (14). Intermolecular C—H?N and C—H?π interactions and π–π stacking, along with intramolecular C—H?N and C—H?π interactions, help to stabilize the structure.     

5‐[N‐(1H‐Benzotriazol‐1‐yl­methyl)­amino]‐3‐tert‐butyl‐1‐phenyl­pyrazole: sheets built from N—H⋯N,C—H⋯N and C—H⋯π(pyrazole) interactions

In the title compound, C₂₀H₂₂N₆, the mol­ecules are linked into a chain of rings by N—H?N [H?N 2.16 Å, N?N 2.950 (3) Å and N—H?N 149°] and C—H?N [H?N 2.55 Å, C?N 3.481 (3) Å and C—H?N 165°] hydrogen bonds, and these chains are linked into sheets by means of C—­H?π(pyrazole) interactions.     

Crystal engineering via C—H⋯F and C—H⋯π interactions in two substituted indoles

The crystal structures of 1‐(4‐fluoro­phenyl)‐2‐phenyl‐4,5,6,7‐tetra­hydro‐1H‐indole, C₂₀H₁₈FN, and 1‐(4‐fluoro­phenyl)‐6,6‐di­methyl‐2‐phenyl‐4,5,6,7‐tetra­hydro‐1H‐indole, C₂₂H₂₂FN, have been determined in order to study the role of `organic fluorine' in crystal engineering. These mol­ecules pack in the crystal structure via different types of molecular motifs utilizing weak C—H⋯F and C—H⋯π interactions.     

Hydro­gen bonding and C—H⃛O interactions in 4‐phenanthrenemethanol at 150 K

The title compound, C₁₅H₁₂O, crystallizes in the centrosymmetric space group I4₁/a with one mol­ecule in the asymmetric unit. In the single hydrogen bond, the H atom is ordered, the O_D?O_A distance is 2.788 (1) Å and the O—H?O angle is 176 (1)°. Each hydroxyl group forms hydrogen bonds with two other hydroxyl groups and the resulting chains of interactions, in four non‐linked subsets of mol­ecules, propagate along [001]. The single leading intermolecular C—H?O interaction has an H?O distance of 2.81 Å and a C—H?O angle of 140°; the single leading intramolecular C—H?O interaction has an H?O distance of 2.24 Å and a C—H?O angle of 152°. The phenanthrene core is less nearly planar in this structure than in the room temperature structure of phenanthrene‐4‐carboxylic acid.     

Hydro­gen bonds and C—H⃛O interactions in N‐(2‐hydroxy‐1,1‐dimethyl­ethyl)benzamide at 150 K

The title compound, C₁₁H₁₅NO₂, crystallized in the centrosymmetric space group P2₁/n with one mol­ecule in the asymmetric unit. There is a single intermolecular hydrogen bond, in which the N_donor?O_acceptor distance is 3.0374 (11) Å and the N—H?O angle is 171.0 (12)°. The single intramol­ecular hydrogen bond has an O_donor?O_acceptor distance of 2.6279 (11) Å and an O—H?O angle of 161.8 (14)°. The four leading intermolecular C—H?O interactions have H?O distances ranging from 2.52 to 2.65 (2) Å and C—H?O angles ranging from 125.2 (9) to 143°. Chains of interactions form two‐dimensional networks.     

An analysis of C—H⋯O and C—H⋯π interactions in three substituted 4‐ketotetra­hydro­indoles

The crystal and molecular structures of the three 4‐ketotetrahydro­indoles 2‐(4‐chloro­phenyl)‐1‐(4‐fluoro­phenyl)‐6,6‐dimethyl‐4,5,6,7‐tetra­hydro‐1H‐indol‐4‐one (C₂₂H₁₉ClFNO), (I), 1‐(4‐fluoro­phenyl)‐2‐(4‐methoxy­phenyl)‐6,6‐di­methyl‐4,5,6,7‐tetra­hydro‐1H‐indol‐4‐one (C₂₃H₂₂FNO₂), (II), and 6,6‐dimethyl‐1,2‐di­phenyl‐4,5,6,7‐tetra­hydro‐1H‐indol‐4‐one (C₂₂H₂₁NO), (III), have been determined via single‐crystal X‐ray diffraction in order to study the intermolecular interactions therein. All three structures are stabilized via intermolecular C—H⋯O and C—H⋯π interactions, generating different molecular motifs.     

C—H⋯π, π–π and C—H⋯Cl interactions in chloro‐substituted Schiff bases and 4‐chloro‐N‐[4‐(di­methyl­amino)­benzyl­idene]­aniline

Molecular packing analyses were carried out on 15 crystal data sets of chloro‐substituted Schiff bases, including that of the title compound, C₁₅H₁₅ClN₂. C—H⋯π and π–π interactions play a major role in the molecular self‐assembly in the crystal. The former interactions favor mol­ecules assembling into a screw, with a non‐centrosymmetric crystal structure. When the molecular dipole is small, π–π interactions favor a parallel, but not usually antiparallel, mode of packing. Weak C—H⋯X hydrogen bonds (X = Cl or Br) and X⋯X interactions seem to be a secondary driving force in packing. The title mol­ecule takes the trans form and the two benzene rings are twisted around the central linkage in opposite directions. In the crystal structure, mol­ecules interact through C—H⋯π and π–π interactions, forming a `dimer' and further forming double chains along [001]. The double chains are extended along [10] through C—H⋯Cl hydrogen bonds, forming double layers in (010). In the third direction, there are only ordinary, weaker, van der Waals interactions, which explains the crystal habit (i.e. thin plate).     

Hydro­gen bonds and C—H⋯O interactions in 2,2′‐dimethoxybiphenyl‐5,5′‐dimethanol at 150 K

The title compound, C₁₆H₁₈O₄, crystallized in the centrosymmetric space group P2₁/c with one mol­ecule in the asymmetric unit. The two hydroxyl‐H atoms are ordered, and are involved in intermolecular hydrogen bonds with O_donor?O_acceptor distances of 2.761 (1) and 2.699 (1) Å, and O—H?O angles of 157 (2) and 168 (2)°. Seven leading intermolecular C—H?O interactions have H?O distances ranging from 2.41 to 2.76 Å and C—H?O angles ranging from 125 to 170°. The hydrogen bonds and C—H?O interactions form chain and ring patterns, resulting in a richly three‐dimensional network. The bi­phenyl twist angle is 67.2 (1)°.     

Hydrogen‐bonding and C—H⋯π interactions in ethyl 4‐acetyl‐5‐methyl‐3‐phenyl‐1H‐pyrrole‐2‐carboxylate monohydrate

In the title compound, C₁₆H₁₇NO₃·H₂O, the pyrrole ring is distorted slightly from ideal C_2v symmetry. Three strong hydrogen bonds link the substituted pyrrole and water mol­ecules to form infinite chains, in which the hydrogen bonds form rings and chain patterns. Two intermolecular C—H?π interactions maintain the internal cohesion between these chains. The molecular structure differs slightly from that of the isolated mol­ecule calculated by ab initio quantum‐mechanical calculations. In the latter model, the non‐H substituent atoms share the plane of the pyrrole ring, except for the phenyl group, which lies almost perpendicular to this plane.     

C[triple‐bond]C—H⋯N hydrogen bonding in 3‐methylthio‐4‐propargylthioquinoline

The title compound, C₁₃H₁₁NS₂, contains a C[triple‐bond]C—H?N hydrogen bond to a pyridine‐type N atom, with a C?N distance of 3.305 (4) Å and an H?N distance of 2.28 Å. This is one of the shortest C—H?N hydrogen bonds known.     

O—H⋯O‐bridged dimers linked via C—H⋯O and C—H⋯π inter­actions in 4,6‐di‐O‐benzyl‐myo‐inositol 1,3,5‐orthoformate

The centrosymmetric O—H⋯O‐bonded head‐to‐head dimers of the title compound, C₂₁H₂₂O₆, are linked together via bifurcated C—H⋯O inter­actions along the a axis and via favourable C—H⋯π inter­actions along the b axis in the crystal structure.     

Syntheses of N‐[3‐(1‐methyl‐1H‐2‐imidazolyl)propyl]benzamides and N‐[3‐(1‐methyl‐1H‐2‐imidazolyl)propyl]benzenesulfonamides

A series of substituted N‐(4‐substituted‐benzoyl)‐N‐[3‐(1‐methyl‐1H‐imidazol‐2‐yl)propyl]amines ( 13 ) and N‐arylsulfonyl‐N‐[3‐(1‐methyl‐1H‐imidazol‐2‐yl)propyl]amines ( 14 ) were prepared from the reaction of 3‐(1‐methyl‐1H‐imidazol‐2‐yl)propan‐1‐amine ( 7 ) with substituted benzoyl chloride or substituted‐benzene sulfonyl chloride respectively. Compound 7 was prepared by two independent methods.