In the 2:3 adduct of 3,5-dihydroxybenzoic acid and 4,4'-bipyridine, 2C(7)H(6)O(4). 3C(10)H(8)N(2), the two components are linked by six independent O-H ... N hydrogen bonds [O ... N 2.685 (3)-2.814 (3) Angstrom and O-H ... N 170-178 degrees] into a C-4(4)(32)[R-4(4)(30)] chain of rings. Each chain is linked to two neighbouring chains by means of aromatic pi...pi stacking interactions.

The title compound is a salt, bis(4,4'-bipyridyl-4,4'-diium) bis[3,4-dihydroxy-3-cyclobutene-1,2-dionate(1 -)] 3,4-dihydroxy-3-cyclobutene-1,2-dionate( 2C(10)H(10)-N-2(2+) . 2C(4)HO(4)(-). C4O42-. The cations and the (C4O4)(2-) anions are linked by two types of short N-H ... O hydrogen bond [N ... O 2.595(2) and 2.622(2) Angstrom; N-H ... O 167 and 170 degrees] to form a planar rectangular net built from a single type of centrosymmetric R-8(6)(56) ring. The (C4HO4)(-) anions are linked by paired short O-H ... O hydrogen bonds [O ... O 2.471(2)Angstrom and O-H ... O 152 degrees] into centrosymmetric dimers containing an R-2(2)(10) motif. A [(C4HO4)(-)](2) dimer lies at the centre of each R-8(6)(56) ring, and is linked to it by two C-H ... O hydrogen bonds [C ... O 3.318(3) and 3.165 (3) Angstrom; C-H ... O 155 and 151 degrees].

The 1:1 adduct of 5-hydroxyisophthalic acid and 4,4'-trimethylenedipyridine is a salt, [HNC 5 H 4 (CH 2 ) 3 C 5 H 4 N] + .[HOC 6 H 3 (COOH)COO] - (C 13 H 15 N 2 + .C 8 H 5 O 5 - ). The anions are linked into C(7) chains by means of O-H...O hydrogen bonds [O...O 2.734 (2) A and O-H...O 176°], and these chains are linked by the cations via O-H...N and N-H...O hydrogen bonds [O...N 2.620 (2) A, O-H...N 175°, N...O 2.748 (2) A and N-H...O 176°] into four identical but independent interpenetrating three-dimensional frameworks.

The title compound, piperazine-1,4-diium 3,4-dihydroxy-3-cyclobutene-1,2-dionate(2-) dihydrate, is a hydrated salt, C 4 H 12 N 2 2+ .C 4 O 4 2- .2H 2 O. The water molecules and the centrosymmetric anions are linked by O-H...O hydrogen bonds into two-dimensional nets built from a single type of R 8 6 (24) ring. Adjacent nets are linked by the centrosymmetric cations, each of which forms four N-H...O hydrogen bonds, with four different anions as acceptors.

Tn the 1:2 adduct formed between 1,3,5-trihydroxybenzene (phloroglucinol) and 2,2'-bipyridyl, C6H6O3.2C(10)H(8)N(2), the triol molecules and half of the bipyridyl molecules are linked into chains by means of O-H ... N hydrogen bonds, forming a stem, while the other half of the bipyridyl molecules are pendent from this stem, via O-H ... N hydrogen bonds.

In the hydrogen-bonded structure of the title complex, O2S(C6H4OH)(2).C10H8N2 or C12H10O4S.C10OH8N2, the bis-phenol molecules are linked into C(8) chains by means of O-H ... O=S hydrogen bonds, and the 2,2'- bipyridyl units, which act as single accepters only, are pendent from these chains by means of O-H ... N hydrogen bonds. Pairs of these chains, related by centres of inversion, are mutually interlocked via their pendent arms.

The 4,4′-bisphenols (1), X (C 6 H 4 OH) 2 [ a , X = nil; b , X = O; c , X = S; d , X = 502; e , X = CO; f , X = CH 2 ; g , X = CMe 2 ; h , X = C(CF 3 ) 2 ], when co-crystallized from alcoholic solutions with hexamethylenetetramine, (CH 2 ) 6 N 4 (HMTA), form 1:1 adducts (4 a )–( h ). 4,4′-Thiodiphenol–hexamethylenetetramine (1/1), (4 c ), C 12 H 10 O 2 S.C 6 H 12 N 4 , and 4,4′- sulfonyldiphenol–hexamethylenetetramine (1/1), (4 d ), C 12 H 10 O 4 S.C 6 H 12 N 4 , are orthorhombic, Pmn 2 1 , (4 c ) a = 15.029 (2), b = 9.7954 (8), c = 5.9817 (11) Å and (4 d ) a = 14.779 (2), b = 10.2558 (15), c = 5.9817 (8) Å, with Z = 2, and the structures consist of zigzag chains comprising strings of alternating bisphenol and HMTA units, each lying across mirror planes and linked by O—H...N hydrogen bonds. In addition, both (4 c ) and (4 d ) exhibit C—H...\pi(arene) hydrogen bonds with one CH 2 group of the HMTA unit acting as a donor to two different arene rings; (4 d ) also exhibits multiple C—H...O=S hydrogen bonds with three C—H bonds in each HMTA unit acting as donors towards a single sulfone O atom. 4,4′-Isopropylidenediphenol–hexamethylenetetramine (1/1), (4 g ), C 15 H 16 O 2 .C 6 H 12 N 4 , is monoclinic, C 2/ c , a = 25.093 (6), b = 7.1742 (13), c = 23.612 (7) Å, \beta = 110.42 (2)°, with Z = 8, and again the structure is built from chains of alternating bisphenol and HMTA units linked by O—H...N hydrogen bonds, but these now form double helices around twofold rotation axes; the double helices are themselves linked into sheets by C—H...O hydrogen bonds. The trisphenol (2), CH 3 C(C 6 H 4 OH) 3 , forms three adducts (5 a )–( c ) with HMTA, having trisphenol:HMTA ratios of 1:2 (5 a ), 2:3 (5 b ) and 1:1 (5 c ). 1,1,1-Tris(4-hydroxyphenyl)ethane–hexamethylenetetramine (1/2), (5 a ), C 20 H 18 O 3 .(C 6 H 12 N 4 ) 2 , is orthorhombic, P 2 1 2 1 2 1 , a = 6.9928 (10), b = 14.0949 (15), c = 30.999 (4) Å, with Z = 4, and the trisphenol units and half the HMTA units form a triple helix around a 2 1 axis, in which each strand consists of alternating phenol and HMTA units, linked as usual by O—H...N hydrogen bonds. The remaining HMTA units, which are external to the triple helix, are connected to it by O—H...N hydrogen bonds and are formed into externally buttressing stacks. The triol (3), 1,3,5-C 6 H 3 (OH) 3 , forms a 2:3 adduct (6) with HMTA. 1,3,5-Trihydroxybenzene–hexamethylenetetramine (2/3), (6), C 6 H 6 O 3 .(C 6 H 12 N 4 ) 1.5 , is monoclinic, C 2/ c , a = 23.598 (2), b = 7.136 (2), c = 19.445 (3) Å, \beta = 96.822 (11)°, with Z = 8, and the dominant structural motif consists of centrosymmetric rings containing two molecules each of (3) and HMTA, connected by O—H...N hydrogen bonds; these rings are themselves linked into a chain-of-rings by further HMTA units lying on twofold rotation axes. The hydrogen-bonding patterns are codified using the graph-set approach.

The 1:1 adduct formed between 1,4-diazabicyclo[2.2.2]octane and 1,3,5-benzenetricarboxylic acid is a salt, C6H13N2+.C9H5O6-. The components both lie on a mirror plane and are linked by O-H ... O, O-H ... N and N-H ... O hydrogen bonds into planar two-dimensional sheets; these sheets are formed by repetition of a single R-6(6)(38) ring which thus generates a tiling pattern with plane group pg.

In (1'-benzoylferrocenyl)diphenylmethanol, [(PhCO-C5H4)Fe(C5H4)]CPh2OH (C30H24FeO2), there is an intramolecularO-H ... O hydrogen bond with O ... O 2.891 (2) Angstrom; the ferrocenyl unit adopts an eclipsed conformation and the molecules are linked into centrosymmetric dimers by C-H ... O hydrogen bonds with C ... O3.357 (3) Angstrom, to generate a cyclic R-4(4)(16) motif.

In the 1:1 adduct formed by hexamethylenetetramine (HMTA) and 1,1,1-tris(3-hydroxyphenyl)ethane, C6H12N4.C20H18O3, the tris-phenol acts as a triple donor of hydrogen bonds of type O-H ... N and the HMTA as a triple acceptor of such hydrogen bonds, with O ... N distances of 2.777(4), 2.781(4) and 7.795(3)Angstrom. The components are assembled into infinite nets comprising hexagonal rings, and pairs of such nets an interwoven; the pairs of interwoven nets are, in addition, connected by C-H ... O hydrogen bonds with a C ... O distance of 3.339(5)Angstrom.

4,4′-Isopropylidenediphenol-1,4-diazabicyclo[2.2.2]octane (1/1), (1), C15H16O2.C6H12N2, monoclinic, P2/a, a = 11.385 (2), b = 6.5565 (12), c = 13.076 (2) Å, \beta = 96.240 (11)°, with Z = 2; the two components of the adduct, which each lie across twofold axes, are joined into simple chains via O—H...N hydrogen bonds in a motif with graph set C_{2}^2(17). 4,4′-Oxodiphenol-1,4-diazabicyclo[2.2.2]octane (1/1), (2), C12H10O3.C6H12N2, orthorhombic, P212121, a = 9.4222 (11), b = 11.1886 (15), c = 15.694 (2), with Z = 4; the diamine component is disordered by rotation about the N...N vector, having two orientations [populations 0.76 (1) and 0.24 (1)] rotated by 48 (3)° from coincidence: the components are joined into chains via O—H...N hydrogen bonds in a motif with graph set C_{2}^2(17); pairs of these chains are joined into ladders by C—H...O hydrogen bonds in a motif of graph set R_{2}^2(22). 4,4′-Thiodiphenol-l,4-diazabicyclo[2.2.2]octane (1/1), (3), C12H10O2S.C6H12N2, isomorphous, a = 9.5785 (11), b = 11.4525 (13), c = 15.759 (2) Å (and ipso facto isostructural), with (2); the diamine disorder is characterized by two equally populated orientations related by a rotation about the N...N vector of 37.1 (2)° and pairs of chains are now joined into ladders by C—H...S hydrogen bonds. 4,4′-Thiodiphenol-1,4-diazabicyclo[2.2.2]octane (2/1), (5), (C12H10O2S)2.C6H12N2, monoclinic, P21/n, a = 8.3198 (9), b = 11.4006 (13), c = 15.056 (2) Å, \beta = 104.955 (8)°, with Z = 2; the diamine component of the adduct is disordered across a centre of inversion, and the bisphenol components are linked into chains by O—H...O hydrogen bonds in a motif with graph set C(12). These chains form cross-links via the diamine component by means of O—H...N hydrogen bonds in a C_{3}^3(19) motif to yield sheets within which are large hydrogen-bonded rings described by the unusual graph set R_{8}^8(62).

In 1,1,1-tris(4-hydroxyphenyl)ethane, C20H18O3 (1), monoclinic la, a = 7.9781 (10), b = 18.558 (3), c = 11.1995 (13) Å, \beta–101.668 (9)°, with Z = 4, each of the hydroxyl groups acts as both a donor and an acceptor of hydrogen bonds of the type O—H...O. The molecules are thus connected into square nets, graph set R^4_4(38), pairs of which are then interwoven; the nets are themselves interconnected by further hydrogen bonds to give a continuous three-dimensional network. In 1,1,1-tris(4-hydroxyphenyl)ethane-l,4-diazabicyclo[2.2.2]octane–water (1/1/1), C20H18O3.C6H12N2.H2O (2), triclinic P\overline 1, a = 10.421 (2), b = 10.734 (2), c = 10.9756 (13) Å, \alpha = 76.645 (12), \beta 74.513 (11), \gamma = 89.305 (13)°, with Z = 2, the water molecules are linked to the trisphenol and the diamine units by O—H...O and O—H...N hydrogen bonds, respectively, to form a linear aggregate. These aggregates are linked into chains by the formation of O—H...N hydrogen bonds between the trisphenol and the neighbouring diamine; however, alongside hydrogen-bond formation between the trisphenol and the diamine, there is also partial transfer of a proton, so that the intra-chain links between trisphenol and diamine units are in fact a mixture of O—H...N and N—H...O hydrogen bonds. These chains in the [101] direction are cross-linked by further O—H...O hydrogen bonds, involving only trisphenol O atoms, which form chains in both the [010] and [001] directions, thus generating a continuous three-dimensional network. Adduct (3), 1,1,1-tris(4-hydroxyphenyl)ethane–piperazine (4/3), (C20H18O3)4.(C4H10N2)3, triclinic P\overline 1, a = 12.5049 (11), b = 12.7046 (10), c = 14.6226 (9) Å, \alpha = 113.738 (6), \beta = 100.839 (6), \gamma = 102.438 (7)°, with Z = 1, has two independent trisphenol molecules in general positions and three independent piperazine molecules lying about centres of inversion. The five independent components of the asymmetric unit are linked together by means of three O—H...N and one O—H...O hydrogen bonds to form an open aggregate containing no hydrogen-bonded rings. These aggregates are connected into three sets of interlinked chains in the [010], [001] and [\overline 110] directions: the [010] and [\overline 110] chains employ only O—H...O hydrogen bonds, while the [001] chains employ both O—H...N and N—H...O hydrogen bonds. Additionally, the inversion symmetry at each piperazine unit gives rise to further interlinks.

In the title compound, C15H16O6S2, each molecule utilizes CH2, CH3 and aromatic C-H bonds to form C-H ... O hydrogen bonds to four other molecules, with C ... O distances of 3.256(4), 3.336(4), 3.425(3) and 3.431(3)Angstrom: the molecules are thereby linked into a continuous three-dimensional network.

In the 1:1 adduct formed by 1,1,3-tris(2-methyl-4-hydroxy-5-tert-butylphenyl)butane and hexamethylenetetramine (HMTA; alternative name: 1,3,5,7-tetraazatricyclo[3.3.1.1(3,7)]decane), C37H52O3 . C6H12N4, the trisphenol [alternative name: 4,4',4 ''-(butane-1,1,3-triyl)tris(2-tert-butyl-5-methylphenol)] acts as a triple donor and a single acceptor of hydrogen bonds, while the HMTA acts as a double acceptor, The tris-phenol and HMTA units are linked into C-2(2)(16) chains along [101] by means of O-H ... N hydrogen bonds, with O ... N distances of 2.759(4) and 2.828(4)Angstrom; the tris-phenol units are themselves linked into C(14) chains along [010] by O-H ... O hydrogen bonds, each having an O ... O distance of 2.828 (4) Angstrom. These two types of chain intersect to generate two-dimensional nets built from alternating R-6(6)(40) and R-6(6)(60) rings; despite the size of these rings, interweaving of the nets is prevented by the presence of the tert-butyl groups in the tris-phenol.

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In the isomorphous 2:1 adducts of furan-2,5-diylbis-(diphenylmethanol) with dimethylformamide, (DMF), [2(C30H24O3):1(C3H7NO)] (II), and with dimethyl sulfoxide (DMSO), [2(C30H24O3):1(C2H6OS)] (III), the centrosymmetric molecular aggregate consists of two molecules of the diol, linked via O-H...O hydrogen bonds involving only the hydroxyl O atoms, and one molecule of either DMF or DMSO disordered across other centres of inversion and linked to the diol dimer by O-H...O hydrogen bonds. In the 2:1 adduct with pyridine, [2(C30H24O3):1(C5H5N)] (IV), the molecular aggregate is similar in structure to those in (II) and (III), but with detailed differences in the hydrogen-bonding scheme within the diol dimer.

Tris(4-methoxyphenyl)methanol, C22H22O4, crystallizes in space group P2(1) with two molecules in the asymmetric unit. The molecules are linked into dimers by a weak O-H ... O hydrogen bond [O ... O 3.035 (3) Angstrom].

The title compound, [Ti(C11H19O2)(2)Cl-2], has a cis configuration. The racemic compound crystallizes in space group P2(1)/c with two molecules in the asymmetric unit: the mean Ti-Cl distance is 2.266(5) Angstrom and the mean Ti-O distances are (trans to O) 1.919(7) and (trans to Cl) 1.999(9) Angstrom.

Molecules of ferrocene-1,1'-diylbis(2-phenylethanedione), [Fe(C13H9O2)(2)], lie across twofold rotation axes. One of the O atoms in each diketone unit acts as an acceptor of two intermolecular C-H ... O hydrogen bonds. Hydrogen bonds employing cyclopentadienyl C-H bonds as donors generate spirals of molecules around the 3(1) axes, while those employing phenyl C-H bonds as donors generate two-dimensional sheets.

The title compound, [Fe-2(C5H5)(2)(C16H20O)], formed by reduction of propionoylferrocene and subsequent dehydration, crystallizes as a racemic mixture of RR and SS forms. In the central C-O-C fragment, the angle at the O atom is 115.7(2)degrees.