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 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 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 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)°.     

4‐Iodo‐N‐(2‐nitro­phenyl­sulfanyl)­aniline: π‐stacked sheets generated by a combination of N—H⃛O and C—H⃛O hydrogen bonds

Molecules of the title compound, C₁₂H₉IN₂O₂S, are linked by one N—H⃛O hydrogen bond [H⃛O = 2.16 Å, N⃛O = 2.935 (4) Å and N—H⃛O 147°] and two C—H⃛O hydrogen bonds [H⃛O both 2.49 Å, C⃛O = 3.231 (5) and 3.220 (5) Å, and C—H⃛O = 135 and 134°] into sheets which themselves are weakly linked by an aromatic π–π‐stacking interaction between iodinated rings in centrosymmetrically related mole­cules. There are no iodo–nitro interactions.     

Two isomorphous benzene­sulfon­amide crystal structures determined by intermolecular C—H⃛O,C—H⃛π and C—H⃛Cl interactions

The title compounds, N‐[5‐(4‐chloro­phenyl)­furan‐2‐yl­methyl]‐4‐methyl‐N‐(prop‐2‐ynyl)­benzene­sulfon­amide, (Ia), and N‐[5‐(2‐chloro­phenyl)­furan‐2‐yl­methyl]‐4‐methyl‐N‐(prop‐2‐ynyl)­benzene­sulfon­amide, (Ib), both C₂₁H₁₈ClNO₃S, have isomorphous crystal structures. The crystal packing is mainly determined by intermolecular C—H?O and C—H?π interactions. These interactions are very similar in (Ia) and (Ib). Additional intermolecular C—H?Cl interactions appear less important and are different in (Ia) and (Ib). The different positions of the Cl atoms result in small variations of the crystal packing of the two compounds.     

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°.     

Tris(2‐pyridyl)­phosphine oxide: how C—H⃛O and C—H⃛N interactions can affect crystal packing efficiency

Tris(2‐pyridyl)­phosphine oxide, (I), C₁₅H₁₂N₃OP, is isomorphous with tris(2‐pyridyl)­phosphine. Because of a combination of C—H⋯O and C—H⋯N interactions, the crystal packing is denser in the title compound than in the related compounds tri­phenyl­phosphine oxide and tris(2‐pyridyl)­phosphine.     

Hydro­gen bonding and C—H⋯X interactions in 3‐fluoro‐2‐[1‐(1‐naph­thyl)ethyl]benzoic acid

The title acid, C₁₉H₁₅FO₂, crystallized in the centrosymmetric space group P with one mol­ecule as the asymmetric unit. There is a single hydrogen bond, with an O_D?O_A distance of 2.632 (2) Å and an O_D—H?O_A angle of 177 (3)°, which forms an R(8) cyclic dimer about a center of symmetry. There is a single leading intermolecular C—H?X interaction, with an H?F distance of 2.49 Å and a C—H?F angle of 147°. Three leading intramolecular C—H?X interactions appear to play a significant role in determining the orientation of the methyl and carboxyl groups.     

4,4′‐Tri­methyl­enedipyridinium bis­[carboxy­methyl­phos­pho­nate(1–)]: a three‐dimensional framework structure built from O—H⃛O,N—H⃛O and C—H⃛O hydrogen bonds

In the title compound, C₁₃H₁₆N₂²⁺·2C₂H₄O₅P⁻, the cation lies across a twofold rotation axis in space group Fdd2. The anions are linked into molecular ladders by two O—H⃛O hydrogen bonds [H⃛O = 1.73 and 1.77 Å, O⃛O = 2.538 (2) and 2.598 (3) Å, and O—H⃛O = 160 and 170°], these ladders are linked into sheets by a single type of N—H⃛O hydrogen bond [H⃛O = 1.75 Å, N⃛O = 2.624 (3) Å and N—H⃛O = 171°] and the sheets are linked into a three‐dimensional framework by a single type of C—H⃛O hydrogen bond [H⃛O = 2.48 Å, C⃛O = 3.419 (4) Å and C—H⃛O = 167°].     

N‐(6‐Amino‐3,4‐di­hydro‐3‐methyl‐5‐nitro­so‐4‐oxopyrimidin‐2‐yl)‐(S)‐glutamic acid: a three‐dimensional framework structure built from O—H⃛O,N—H⃛O and O—H⃛N hydrogen bonds

The title compound, C₁₀H₁₃N₅O₆, exhibits a highly polarized molecular–electronic structure and the conformation is influenced by two intramolecular N—H⃛O hydrogen bonds. The mol­ecules are linked into a single framework by hydrogen bonds of types O—H⃛O [O—H = 1.22, H⃛O = 1.38, O⃛O = 2.558 (6) Å and O—H⃛O = 160°], N—H⃛O [H⃛O = 2.26, N⃛O = 2.866 (6) Å and N—H⃛O = 126°] and O—H⃛N [O—H = 1.26, H⃛N = 1.56, O⃛N = 2.811 (6) Å and O—H⃛N = 170°]. The substructure generated by the O—H⃛O and N—H⃛O hydrogen bonds takes the form of a double helix.     

N‐Benzylformamide at 150 K

The title compound, C₈H₉NO, crystallizes with Z′ = 2. Each type of independent molecule links into a separate N—H...O hydrogen‐bonded chain in the a‐axis direction. There are also three weak C—H...O hydrogen bonds, which join the molecules into a two‐dimensional sheet parallel to (001). The molecules exhibit the trans conformation of the –NHCHO group and an anti conformation around the (Ph)C—NH(CHO) bond. The formamide group in each of the symmetry‐independent molecules is twisted out of the benzyl group plane, forming angles of 75.96 (10) and 65.23 (11)° with this plane. The significance of this study lies in the comparison drawn between the experimental and calculated data of the crystal structure of the title compound and the data of several other derivatives possessing the –CH₂—NH—CO– group. The correlation between the IR spectrum of this compound and the hydrogen‐bond energy is also discussed. This molecular system is of particular interest to biochemists because of its preventative function against toxic products of alcohols in human metabolism.     

Bis(3‐nitro­phenyl) di­sulfide forms no C—H⃛O hydrogen bonds

In the title compound, C₁₂H₈N₂O₄S₂, the mol­ecules lie across twofold rotation axes in the space group C2/c. There are no intermolecular C—H?O hydrogen bonds, but the mol­ecules are linked into chains along [001] by aromatic π?π stacking interactions.     

C—H⃛π interactions in 9‐(n‐do­decylamino­methyl)­anthracene

The title compound, C₂₇H₃₇N, which is intended to be included in the structure of a sulfon­amide porphyrin for the preparation of Langmuir–Blodgett films, consists of a do­decyl chain linked to an anthracene mol­ecule through an amino­methyl group. The angle between the least‐squares plane of the anthracene and the do­decyl chain is 11.44 (8)°. The mol­ecules are arranged in zigzag layers head‐to‐head, with the hydro­carbon chains side‐by‐side. The structure is stabilized by C—H?π interactions, the strongest having an H?centroid distance of 2.63 Å.     

C—H⃛O and C—H⃛π interactions in 1‐acetyl‐4‐(p‐chloro­benzyl­idene­amino)‐3‐ethyl‐4,5‐di­hydro‐1H‐1,2,4‐triazol‐5‐one

The title compound, C₁₃H₁₃ClN₄O₂, contains both a phenyl and a triazole ring, both of which are approximately coplanar with the entire mol­ecule. The triazole ring has substituents at the 1‐, 2‐ and 4‐positions. Intramolecular C—H⃛O and C—H⃛N interactions, together with intermolecular C—H⃛O and C—H⃛π interactions, help to stabilize the structure.     

2‐Cyano‐N‐(4,6‐dimethoxypyrimidin‐2‐yl)acetamide: complex sheets built from N—H...O and C—H...O hydrogen bonds

Molecules of the title compound, C₉H₁₀N₄O₃, (I), are linked into complex sheets by a combination of one N—H...O hydrogen bond and two C—H...O hydrogen bonds. Comparisons are drawn between (I) and some related compounds in respect of both their molecular conformations and their hydrogen‐bonding arrangements.     

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.     

4‐(Allyl­amino)‐2‐amino‐6‐benzyl­oxy‐5‐nitro­so­pyrimidine from synchrotron data at 150 K: double chains built from N—H⋯N,N—H⋯O,N—H⋯π(arene) and aromatic π–π‐stacking interactions

In the title compound, C₁₄H₁₅N₅O₂, the intramolecular dimensions are consistent with a highly polarized electronic structure. The mol­ecules are linked into chains by a combination of N—H?N, N—H?O and N—H?π(arene) hydrogen bonds, and the chains are linked in pairs by aromatic π–π‐stacking interactions     

4,4′‐Bis(4‐iodo­phenyl­amino­methyl)­azoxy­benzene: hydrogen‐bonded sheets built from C—H⃛O and C—H⃛π(arene) hydrogen bonds

Borohydride reduction of N‐(4‐nitro­benzyl­idene)‐4‐iodo­aniline has yielded the title compound, 1,2‐bis­[4‐(4‐iodo­phenyl­amino­methyl)­phenyl]­diazene 1‐oxide, C₂₆H₂₂I₂N₄O. The mol­ecules lie across centres of inversion in P2₁/c, with the azoxy O atom disordered over two sites, each having an occupancy of 0.5. The mol­ecules are linked into sheets by a combination of C—H⃛O and C—H⃛π(arene) hydrogen bonds.     

2‐Amino­benzimidazolium O‐ethyl malonate: eight independent N—H⋯O hydrogen bonds generate sheets

The title compound, C₇H₈N₃⁺·C₅H₇O₄⁻, crystallizes with Z′ = 2 in space group P2₁/c; eight independent N—H⋯O hydrogen bonds [H⋯O = 1.75–1.88 Å, N⋯O = 2.699 (2)–2.829 (2) Å and N—H⋯O = 147–179°] link the four inde­pendent ions into sheets.