Hydrogen bonding assemblies in host–guest complexes with 18-crown-6

Hydrogen bonding assemblies in host–guest complexes

with 18-crown-6

M.S. Fonaria,*, Yu.A. Simonova, V.Ch. Kravtsova, J. Lipkowskib,E.V. Ganinc, A.A. Yavolovskiid

aInstitute of Applied Physics, Academy of Sciences of Moldova, Academy str 5, MD 2028 Chisinau, MoldovabInstitute of Physical Chemistry, Polish Academy of Sciences Warsaw, Poland

cPhysico-Chemical Institute of Environment and Human Protection National Academy of Sciences of Ukraine, Odessa, UkrainedBogatsky Physico-Chemical Institute of the National Academy of Science of Ukraine Odessa, Ukraine

Received 14 December 2001; revised 13 May 2002; accepted 13 May 2002

Abstract

Recent X-ray crystal structural data for two novel 1:2 host-guest complexes of 18-crown-6 with neutral organic molecules,

thiaamide hydrazide of 2-aminobenzoic acid and thiaamide hydrazide of 4-amino-1,2,5-thiadiazole-3-carbonic acid are

reported. The supramolecular structures of these two and five relative complexes are discussed from the point of view of

participation of donor groups in coordination with the crown ether, and donor and acceptor groups in the self-assembly of the

guest molecules. Guest molecules have incorporated amine and hydrazine moieties as proton donors and carbonyl oxygen and

sulfur (in thiadiazole and in thiaamine moieties) as proton acceptors. The guest–guest interactions appeared to be crucial in the

final architecture.

q 2003 Elsevier Science B.V. All rights reserved.

Keywords: Crown ether; Host–guest complex; H-bonding; X-ray crystallography

1. Introduction

The macrocycles that Pedersen named crown

ethers [1] have now been known for more than

three decades and their structures, free and bound

with metallic and organic cations as well as with

neutral species, have been reported [2,3]. Despite

extensive study and application of crowns, novel

properties continue to emerge. The relative simpli-

city of an appropriate model system based on the

crown ether allows specific interactions to be

isolated and studied in the absence of many other

interactions that are present in natural biological

systems.

We are interested in the 18-crown-6 chemistry

using this suitable module in complexes with neutral

organic molecules to obtain extended supramolecular

networks. Some previous examples [4,5] seemed

interesting and encouraged us to study novel supra-

molecular complexes.

0022-2860/03/$ - see front matter q 2003 Elsevier Science B.V. All rights reserved.

PII: S0 02 2 -2 86 0 (0 2) 00 5 13 -6

Journal of Molecular Structure 647 (2003) 129–140

www.elsevier.com/locate/molstruc

* Corresponding author. Tel.: þ373-2-738154; fax: þ373-2-

738149.

E-mail address: [email protected] (M.S. Fonari).

http://www.elsevier.com/locate/molstruc

Crystal structures of the 18-crown-6 complexes

with the ethyl ester of 4-amine-1,2,5-oxadiazole-3-

carbonic acid (EE), (complex I, composition 1:1),

hydrazide of 4-(2-chloroethylamino)-1,2,5-oxadia-

zole-3-carbonic acid (HC), (II, 1:2), amide of 4-

amine-1,2,5-oxadiazole-3-carbonic acid monohydrate

(AA), (III, 1:1:1) [6], hydrazide of 2-aminobenzoic

acid monohydrate (HA), (IV, 1:2:2), hydrazide of 5-

amine-1-benzyl-1,2,3-triazole-4-carbonic acid (HB),

(V, 1:2) [7], thiaamide hydrazide of 2-aminobenzoic

acid (TB), (VI, 1:2), and thiaamide hydrazide of 4-

amino-1,2,5-thiadiazole-3-carbonic acid (HT), (VII,

1:2) are discussed. The neutral organic molecules

have an amine or hydrazine group as a suitable H-

donor for complex formation and different acceptor

centers in the neighboring position of five-membered

(diazole, triazole, thiadiazole) or aromatic rings to

provide an opportunity for self-assembly (Scheme 1).

For the formulation of a linear (1D), sheet (2D) or

carcass (3D) structure in complexes with 18-crown-6,

not only the mutual complementarity of the guest

donor and crown acceptor binding sites is important,

but also the capability of guest molecule for the self-

assembly.

2. Discussion

2.1. Chain structures

In the structure of I the components are assembled

into alternating chains running along the b direction in

the unit cell (Fig. 1). The crown ether exhibits unusual

‘different-faced’ geometry due to asymmetric binding

with amine and ethyl groups of EE coordinated to

macrocyclic rings in a face-to-tail manner. The amine

group forms two NH· · ·O hydrogen bonds,

N(3)· · ·O(4) 3.087(2) and N(3)· · ·O(16) 3.202(2) A,

while the ethyl group donates two hydrogens, one

from the methyl and one from the methylene group for

CH· · ·O interactions, both being approximately linear,

C(4)· · ·O(1) 3.311(3), C(4)–H· · ·O(1) 2.43 A, angle

C(4)–H· · ·O(1) 1508, and C(5)· · ·O(7) 3.537(3),

C(5)–H· · ·O(7) 2.58 A, angle C(5)–H· · ·O(7) 1758.

Apart from geometric details, the range of C–H· · ·O

interactions is very similar to that observed in the

binary complexes of 18-crown-6, with, for example,

dimethylsulfoxide (C· · ·O 3.287(3)–3.598(3) A) [8]

or with methyl 10-camphor sulfonate (C· · ·O dis-

tances from 3.264(7) to 3.801(7) A) [9]. The weak

Scheme 1. Guest molecules incorporated into molecular complexes I–VII.

M.S. Fonari et al. / Journal of Molecular Structure 647 (2003) 129–140130

CH· · ·OyC and CH· · ·N hydrogen bonds, C· · ·O

3.311(3) and C· · ·N 3.417(3) A between the hydrogen

atoms of the crown-ether methylene groups and

carbonyl oxygen and diazole nitrogen atoms as

acceptor binding sites of the EE molecule also

contribute to the overall system of interaction. The

mutual arrangement of the components is character-

ized by a dihedral angle of 57.4(1)8 between the mean

plane of the oxadiazole moiety and the mean plane of

six oxygen atoms of the crown ring.

The distinctive feature of I is the participation of

ethyl moiety in coordination to the crown ether. The

numerous previously described examples for 18-

crown-6 complexes [10] show the involvement of

guest methyl [11–26] or methylene group [27–30] in

the center-of-symmetry related C–H· · ·O hydrogen

bonds. The different-faced coordination for the 18-

crown-6 molecule often provides the host-guest

alternate chain structure and was found previously

in its 1:1 complex with 6-chloro-7-sulphamido-3,

4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide [31],

and in the ternary 18-crown-6 complexes with the

hydrates of acetic [32], maleic [33], succinic [34]

acids, and isonitrosocyanoacetamide [35].

The chain motif for complex II is depicted in Fig. 2

It is developed along the [110] direction in the

unit cell. Two HC molecules approach in a similar

face-to-face manner to the crown ring, and each

affords three NH· · ·O(crown) hydrogen bonds with

the participation of all hydrazine hydrogen atoms and

all crown ether oxygen atoms in coordination, N· · ·O

distances N(1)· · ·O(4) 2.905(4), N(2)· · ·O(1) 3.110(4),

N(2)· · · O(7) 3.092(4) A. The hydrogen atoms of the

hydrazine group are in a cis-position to the N(1)–N(2)

covalent bond in HC, that ensures their complete

involvement in the coordination to the same crown

molecule, unlike the trans-orientation of these hydro-

gen atoms in phenylhydrazide monohydrate [36], that

provides hydrogen bonds with the different molecules.

Two center-of-symmetry-related HC molecules in II

via NH· · ·OyC hydrogen bonding mode form a planar

centrosymmetric dimer, N(3)· · ·O(2)(2x þ 1; 2y;

2z) 2.873(4) A, graph set R22(12) [37]. Crown

molecules and HC dimers alternate in the chain. The

mutual arrangement of the components is character-

ized by a dihedral angle of 47.0(1)8 between the mean

plane of oxadiazole moiety and the mean plane of six

oxygen atoms of the crown ring. Chlorine atoms do

not contribute to the overall system of H-bonded

interactions.

Both in I and II the interactions shorter than the

sum of van der Waals radii are absent between the

neighboring chains.

2.2. Ribbon structure

In III co-crystallisation leads to a ternary

complex with stoichiometry 1:1:1. The polar water

solvent is inserted as an ambifunctional complemen-

tary mediator between AA and the macrocyclic

Fig. 1. Chains in I.

M.S. Fonari et al. / Journal of Molecular Structure 647 (2003) 129–140 131

heterocycle (Fig. 3). It provides two OH· · ·O

hydrogen bonds, O(1w)· · ·O(10) 2.842(4) and

O(1w)· · ·O(16) 2.959(5) A with two crown oxygen

atoms. As H-acceptor, water molecule is involved in

NH· · ·O hydrogen bond with the amine group of the

AA molecule, N(4)· · ·O(1w) 2.783(4) A. The dihe-

dral angle between the mean plane of the oxadiazole

moiety and the mean plane of the six oxygen atoms

of the crown ring is 70.0(1)8. The organization of the

18-crown-6-water-AA associate in III resembles the

arrangement of the ternary complex of 18-crown-6

with water and 3,4-diamino-1,2,5-oxadiazole [38],

where the water molecule provides two OH· · ·O

hydrogen bonds with the macrocycle, and donates a

lone pair for the interaction with the 3,4-diamino-

1,2,5-oxadiazole molecule. In III the AA molecules

related by the glide plane are organised into a planar

herringbone chain through the NH· · ·N,

N(3)· · ·N(2)(x, 2y þ 2; z þ 1=2) 3.077(5) A and

NH· · ·OyC, N(3)· · ·O(2)(x, 2y þ 2; z 2 1=2)

2.854(5) A hydrogen bonds, R22(10). The chain is

imprisoned between two successive rows of crown

molecules, thus constituting the ribbon propagated in

the bc plane. The ribbons are mutually oriented by

the crown-ethers’ hydrophobic parts in the direction

of each other and the contacts shorter than the sum of

van der Waals radii were not found betweenFig. 3. Ribbons in III. H-atoms of crown molecules are omitted for

the sake of clarity.

Fig. 2. Chains in II. All H-atoms except those of hydrazine groups are omitted for the sake of clarity.


the neighboring ribbons (Fig. 3). In III the 18-crown-

6 molecule exhibits a rare, single-faced coordination

mode. A search of CSD [10] gave only a few

examples of single-faced coordination of neutral

molecules such as amminetrihydroboron [39], mono-

aqua-trifluoroborone [40], benzenesulfonamide [41],

and nitrosoaniline [42] in their 1:1 complexes with

18-crown-6. Commonly, water molecules as

mediators between crown ring and neutral molecules

interact in the same way on the both sides of the

centrosymmetric cavity and donate two hydrogen

atoms for H-bonds with 18-crown-6 and a lone pair

for an H-bond with the guest molecule. As examples

one should mention of the hydrates of 18-crown-6

complexes with the derivatives of phenol [43–47],

acids [48–51], sulfonyl derivatives [52–54], and

hydrates of 18-crown-6 itself [55,56].

2.3. Layer structures

We succeeded in setting up 2D structures when

the water molecule served as a pyramidal connector

between HA and 18-crown-6 in the ternary

complex IV, when the methylene group was

introduced as an angular fragment into the HB

molecule between phenyl and triazole rings in V,

and when sulfur atoms of the thiadiasole ring and

terminal SyC group of the TB molecule contrib-

uted to the overall system of interactions in VI.

These neutral molecules afford an opportunity for

the structures to develop in two directions, and

facilitate the formation of 2D networks.

In IV the centrosymmetric complex HA-18-

crown-6-HA is stabilized by six center-of-sym-

metry-related NH· · ·O hydrogen bonds between

three hydrogen atoms of the hydrazine fragment

of the HA molecule and all oxygen atoms of the

macrocycle; N· · ·O N(1)· · ·O(4)(2x þ 2; 2y;

2z þ 1) 2.961(1), N(2)· · ·O(1) 2.995(1), N(2)

· · ·O(7) 3.141(1) A (Fig. 4). As in HC, the

hydrogen atoms of the hydrazine group are located

in cis-positions with respect to the N(1)–N(2)

bond. The HA and 18-crown-6 molecules in IV are

arranged in such a way that the dihedral angle

between the mean plane of the phenyl ring of HA

and the mean plane of six oxygen atoms of the

crown ether is 23.5(4)8. The water molecule behaves

as a bridge between two, glide-plane-related, HA

molecules. It affords two hydrogen bonds: with a

lone pair of the nitrogen atom of the amine-group,

and the carbonyl oxygen atom of the HA molecule,

O(1w)· · ·N(2) 2.925(1), and O(1w)· · ·O(2)

2.913(1) A. The lone pair of the water molecule

accepts the H-atom of the amine-group of the HA

molecule, N(3)· · ·O(1w) 3.102(1) A. Thus, via

NH· · ·O hydrogen bonds, HA and the water

molecules alternate in the chains. Due to the

pyramidal geometry of water, these chains are

developed in a staircase mode, and the centrosym-

metric crown molecules attached to them form

closed centrosymmetric cages that combine four

crown molecules, six HA, and four water mol-

ecules. Each associate is stabilized by 32 NH· · ·O

hydrogen bonds, which are NH· · ·O(crown) and

NH· · ·O(water) interactions. The assembly of these

cages forms the layer. The layers are propagated

parallel to the bc plane in the unit cell.

The host–guest interaction mode between HB

and the crown ether in V closely resembles IV

(Fig. 5). The hydrazine group donates all hydrogens

for NH· · ·O hydrogen bonds: N(1)· · ·O(4)(2x;

2y þ 1; 2z) 2.897(3), N(2)· · ·O(1) 3.223(4), and

N(2)· · ·O(7) 3.082(4) A. The HB molecules related

by a twofold screw axis form corrugated chains via

NH· · ·O and NH· · ·N hydrogen bonds,

N(3)· · ·O(2)(2x; y 2 1=2; 2z þ 1=2) 3.075(3), and

N(3)· · ·N(2)(2x; y 2 1=2; 2z þ 1=2) 3.116(4) A. In

the complex the dihedral angle between the mean

plane of six oxygen atoms of the macrocycle and

the triazole ring of HB is equal to 76.8(1)8. This T-

shaped arrangement is rather typical for the

complexes of eighteen-membered crown ethers

(for example, 18-crown-6 and the A and B isomers

of dicyclohexyl-18-crown-6) with amino derivatives

of benzene and five-membered heterocycles [57,

58]. The HB chains associated with the crown

molecules provide a pleated layer structure. In the

layer six HB and two 18-crown-6 molecules are

joined to form a centrosymmetric cage which is

stabilized by 16 intermolecular hydrogen bonds of

the NH· · ·O(crown) and NH· · ·OyC types.

The centrosymmetric formula unit of the 1:2

molecular complex VI is shown in Fig. 6. The

amine group of each TB molecule defined by N(3)

atom, provides two N–H· · ·O hydrogen bonds with

crown oxygen atoms, N(3)· · ·O(14) 2.960(2) A,


N(3)· · ·O(17)(2x þ 1; 2y þ 2; 2z) 3.175(2) A

(details of hydrogen bonding for VI and VII are

given in Table 1). Besides, in host–guest inter-

actions the closest to the thiaamide fragment amine

group of hydrazine moiety defined by the N(2)

atom, takes part, N(2)· · ·O(11)(x, y 2 2; z )

3.173(2) A. Its hydrogen atom is directed in the

opposite side with respect to the hydrogen atoms of

N(3) amine group and provides the assembly of the

TB-18-crown-6-TB complexes into the chains,

running along b direction in the unit cell.

The dihedral angle between the mean plane of

phenyl ring in TB and the mean plane of the six

oxygen atoms of the macrocycle is equal 39.62(3)8.

The intramolecular NH· · ·O hydrogen bond

closes the 6-membered ring, N(4) · · ·O(1)

2.762(2) A, and affords a system of two conjugated

rings with a dihedral angle between the mean

planes of phenyl ring and H-cycle equal 9.6(2)8.

The center-of-symmetry-related TB molecules are

self-assembled into the chains via three different

hydrogen bonding patterns (Fig. 7). In two of them

the amine group attached to the phenyl ring takes

part, N(4)· · ·O(1)(2x þ 2; 2y þ 1; 2z) 2.951(2) A,

R22(12); N(4)· · ·S(1)(2x þ 2; 2y þ 1; 2z)

3.636(2) A, R22(18). The third supramolecular syn-

thon combines nitrogen and sulfur atoms of two

center-of-symmetry-related thiosemicarbazide moi-

eties, N(1)· · ·S(1)(2x þ 1; 2y þ 1; 2z) 3.316(2) A,

R22(10). In VI the chains of TB molecules running

along a direction in the unit cell and the rows of

18-crown-6 molecules attached to them alternate in

the layers developed in the ab plane (Fig. 8).

2.4. 3D network

The centrosymmetric formula unit of the 1:2

molecular complex VII is shown in Fig. 9.

Fig. 4. Layer in IV. Non-functional H-atoms are omitted for the sake of clarity.


The amine group of each HT molecule is bonded

to the crown ether through a set of N–H· · ·O

interactions, N· · ·O 2.970(2) 23.170(2) A (details

in Table 1); each hydrogen atom of the amine

group is involved in bifurcated NH· · ·O hydrogen

bonds. The C(8)–N(3) bond deviates at an angle of

68 from the normal to the mean plane of the six

oxygen atoms of the macrocycle. The thiadiazole

Fig. 5. Layer in V. H-atoms of crown molecules are omitted for the sake of clarity.

Fig. 6. Side view of VI. Intra- and intermolecular hydrogen bonds are shown as dashed lines.


ring forms a dihedral angle of 21.28 with the same

plane. In HT, as in all the guest molecules

described above, the intramolecular NH· · ·O hydro-

gen bond closes the 6-membered ring, N(4)· · ·O(1)

2.819(2) A, and provides an almost planar system

of two conjugated rings, with a dihedral angle of

2.82(2)8.

The HT-18-crown-6-HT complexes are com-

bined into chains via a centrosymmetric module of

two NH· · ·S hydrogen bonds, N(2)· · ·S(1)(2x þ 1;

2y þ 1; 2z þ 1) 3.344(1) A, R22(8). The chains run

along c direction in the unit cell (Fig. 10).

The HT molecule is rich in donor and acceptor

binding sites, namely two primary and two

secondary amine groups as H-donors, and two

sulfur atoms, one carbonyl oxygen and two nitrogen

atoms of thiadiazole ring as acceptors. It facilitates

the self-assembly of HT molecules via a plethora

Table 1

Hydrogen bonds in complexes VI and VII

D–H· · ·A d(D–H), A d(H· · ·A), A d(D· · ·A), A /(DHA),8 Symmetry operation for the H-acceptor

Complex VI

N(1)–H(1N1)· · ·S(1) 0.81(2) 2.60(2) 3.316(2) 147(2) 2x þ 1; 2y þ 1; 2z

N(2)–H(1N2)· · ·O(11) 0.82(2) 2.41(2) 3.173(2) 154(2) x, y2y þ 1; z

N(3)–H(1N3)· · ·O(17) 0.88(2) 2.34(2) 3.175(2) 158(2) 2x þ 1; 2y þ 2; 2z

N(3)–H(2N3)· · ·O(14) 0.83(2) 2.20(2) 2.960(2) 152(2) X, y, z

N(4)–H(1N4)· · ·S(1) 0.81(2) 2.87(2) 3.636(2) 158(2) 2x þ 2; 2y þ 1; 2z

N(4)–H(2N4)· · ·O(1) 0.87(2) 2.15(2) 2.951(2) 153(2) 2x þ 2; 2y þ 1; 2z

N(4)–H(2N4)· · ·O(1) 0.87(2) 2.18(2) 2.762(2) 124(2) x, y, z

Complex VII

N(2)–H(2N)· · ·S(1) 0.86(2) 2.53(2) 3.344(1) 158(2) 2x þ 1; 2y þ 1; 2z þ 1

N(3)–H(1N3)· · ·O(14) 0.84(2) 2.38(2) 3.038(2) 136(2) x, y, z

N(3)–H(1N3)· · ·O(17) 0.84(2) 2.49(2) 3.170(2) 139(2) x, y, z

N(3)–H(2N3)· · ·O(17) 0.86(2) 2.21(2) 3.033(2) 160(2) 2x þ 1; 2y; 2z;

N(3)–H(2N3)· · ·O(11) 0.86(2) 2.42(2) 2.970(2) 122(2) x, y, z;

N(4)–H(1N4)· · ·S(1) 0.86(2) 2.53(2) 3.374(1) 167(2) x 2 1; y 2 1; z

N(4)–H(2N4)· · ·O(1) 0.89(2) 2.17(2) 2.819(2) 129(2) x, y, z;

Fig. 7. Chain constituted of TB molecules in VI. H-bonds are shown as dashed lines.


of diverse hydrogen bonds and non-hydrogen

interactions. Two center-of-symmetry-related HT

molecules are linked in the dimer through four

short interactions arranged in zipper-like mode, two

NH· · ·N hydrogen bonds, N(1)· · ·N(5)(2x þ 1; 2y;

2z þ 1) 3.013(2) A, R22(10) and two

N(2)· · ·S(2)(2x þ 1; 2y; 2z þ 1) contacts of

3.259(2) A which close the 12-membered ring.

The pair of N· · ·S centrosymmetric interactions,

N(6) · · ·(2)(2x; 21 2 y; 1 2 z) 3.236(2) A com-

bines these dimers in the ribbon (Fig. 11). The

ribbons are also sustained by two NH· · ·S hydrogen

bonds between the hydrogen atom of the primary

amine group defined by N(4) and the terminal

sulfur atom S(1), N(4)· · ·S(1)(x 2 1; y 2 1; z )

3.374(1) A. The guest ribbons run in the [110]

direction, and along c axis direction they are linked

into the 3D network via a centrosymmetric module

of two above mentioned NH· · ·S hydrogen bonds,

N(2)· · ·S(1)(2x þ 1; 2y þ 1; 2z þ 1) (Fig. 10).

Thus, self-assembly of HT molecules in VII

provides a 3D network unlike IV, V, and VI, where

the 2D structures are built of the combination of the

guest chains and 18-crown-6 molecules.

In all the complexes I–VII the conformation of 18-

crown-6 molecule corresponds to the ideal D3d

geometry.

2.5. X-ray crystallography

Crystals of compounds VI and VII were obtained

in nearly quantitative yield from slow evaporation of

the reactants at room temperature. Intensity data for

both complexes were collected at 150 K on a Nonius

Kappa CCD diffractometer equipped with graphite

monochromated Mo Ka radiation using v rotation

with sample-to-detector distance of 40 mm. Prelimi-

nary orientation matrix and unit cell parameters were

obtained from the peaks of the first 10 frames,

respectively, and refined using the whole data set.

Frames were integrated and corrected for Lorentz and

Fig. 8. Layer in VI. Non-functional H-atoms are omitted for the sake of clarity.

Fig. 9. Side view of VII. Intra- and intermolecular hydrogen bonds

are shown as dashed lines.


polarization effects using DENZO [59]. The scaling

and global refinement of crystal parameters were

performed by SCALEPACK [59]. Reflections, which

were partly measured on previous and following

frames, are used to scale these frames. The structures

were solved by direct methods using SHELXS [60] and

refined by full-matrix least-squares based on F 2 using

SHELXL-97 [61]. Hydrogen atoms of methylene

groups were included in calculated positions and

refined with isotropic displacement parameters

according to the riding model, while the N-bound

H-atoms were found from Fourier maps and refined

without any constraints.

2.6. Crystal data

The structures of I–V were taken from published

reports [6,7].

Crystal data for VI: M ¼ 684.83, pale yellow,

prismatic, 0.25 £ 0.25 £ 15 mm, monoclinic, sp.gr.

P21=c; a ¼ 10.437(1) A, b ¼ 7.942(1) A, c ¼

19.958(1) A, b ¼ 90.89(2)8, Z ¼ 2, V ¼ 1654.13(9)

A3 Dc ¼ 1.375 g/mm3; final GoF ¼ 1.180, R1 ¼

0.0537, wR2 ¼ 0.0957 based on 3740 reflections

with I . 2sðIÞ: Crystallographic data for VI have

been deposited with the Cambridge Crystallographic

Data Center as Supplementary Publication No.

CCDC-182691.

Crystal data for VII: M ¼ 700.85, pale yellow,

prismatic, 0.15 £ 0.15 £ 25 mm, triclinic, sp.gr. P 2

1; a ¼ 9.112(3) A, b ¼ 9.637(2) A, c ¼ 10.479(3) A,

a ¼ 111.89(1)8, b ¼ 90.69(1)8, g ¼ 113.62(1)8,

Z ¼ 1, V ¼ 768.06(4) A3 Dc ¼ 1.515 g/mm3; final

GoF ¼ 1.077, R1 ¼ 0.0466, wR2 ¼ 0.0868 based on

5296 reflections with I . 2sðIÞ: Crystallographic data

for VII have been deposited with the Cambridge

Fig. 10. Layer in VII. Non-functional H-atoms are omitted for the sake of clarity.

Fig. 11. Ribbon constituted of HT molecules in VII. H-bonds are shown by dashed lines.


Crystallographic Data Center as Supplementary

Publication No. CCDC-175853.

3. Conclusions

The crucial factor that determines the structural

type and architecture (one-, two- or three dimension-

ality) of 18-crown-6 complexes with neutral organic

molecules is the mutual complementarity of donor

and acceptor groups in the guest and complex

stoichiometry.

4. Supplementary data

(cif files) for the complexes discussed in this

article, have been deposited at the Cambridge

Crystallographic Data Center under the deposition

numbers 143357 (I), 143358 (II), 143359 (III),

160249 (IV), 160250 (V), 182691 (VI), 175853

(VII). The lists of Fo2 and Fcalc

2 for all the structures

are available from the authors upon request.

Acknowledgements

The authors thank Ms I.G. Filippova for assistance

in the publication preparation. The authors from

Chisinau are indebted to CRDF-MRDA (Project No.

MP2-3021) for financial support.

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Hydrogen bonding assemblies in host–guest complexes with 18-crown-6

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Transcript of Hydrogen bonding assemblies in host–guest complexes with 18-crown-6