The title compound (systematic name: benzene-4,4′,4′′,4′′′,-4′′′′,4′′′′′-hexaylhexabenzonitrile dichloromethane disolvate), C48H24N6•2CH2Cl2, crystallizes as an inclusion compound during the slow diffusion of methanol into a solution of hexakis(4-cyanophenyl)benzene in CH2Cl2. The hexakis(4- cyanophenyl)benzene molecule lies on an axis of twofold rotation in the space group Pbcn. Weak C—H•••N interactions between hexakis(4-cyanophenyl)benzene molecules define an open network with space for including guests. The resulting structure is a new pseudopolymorph of hexakis-(4-cyanophenyl)benzene. The eight known pseudopolymorphs have few shared architectural features, in part because none of the intermolecular interactions that are present plays a dominant role or forces neighboring molecules to assume particular relative orientations

Gagnon, Eric

Maly, Kenneth E.

Maris, Thierry

Wuest, James D.

English

Scholars Commons

Wilfrid Laurier University 
Scholars Commons @ Laurier 
Chemistry Faculty Publications Chemistry 
2006 
A New Pseudopolymorph of Hexakis-(4-cynaophenyl)benzene 
Eric Gagnon 
Université de Montréal 
Kenneth E. Maly 
Wilfrid Laurier University, kmaly@wlu.ca 
Thierry Maris 
Université de Montréal 
James D. Wuest 
Université de Montréal 
Follow this and additional works at: https://scholars.wlu.ca/chem_faculty 
Recommended Citation 
Gagnon, Eric; Maly, Kenneth E.; Maris, Thierry; and Wuest, James D., "A New Pseudopolymorph of Hexakis-
(4-cynaophenyl)benzene" (2006). Chemistry Faculty Publications. 8. 
https://scholars.wlu.ca/chem_faculty/8 
This Article is brought to you for free and open access by the Chemistry at Scholars Commons @ Laurier. It has 
been accepted for inclusion in Chemistry Faculty Publications by an authorized administrator of Scholars 
Commons @ Laurier. For more information, please contact scholarscommons@wlu.ca. 
A new pseudopolymorph of hexakis-
(4-cyanophenyl)benzene
Eric Gagnon, Kenneth E. Maly, Thierry Maris* and
James D. Wuest
DeÂpartement de Chimie, UniversiteÂ de MontreÂal, MontreÂal, QueÂbec, Canada H3C 3J7
Correspondence e-mail: thierry.maris@umontreal.ca
Received 19 July 2006
Accepted 3 November 2006
Online 12 December 2006
The title compound (systematic name: benzene-4,40,400,4000,-
40000,4000 00-hexaylhexabenzonitrile dichloromethane disolvate),
C48H24N62CH2Cl2, crystallizes as an inclusion compound
during the slow diffusion of methanol into a solution of
hexakis(4-cyanophenyl)benzene in CH2Cl2. The hexakis(4-
cyanophenyl)benzene molecule lies on an axis of twofold
rotation in the space group Pbcn. Weak C H  N inter-
actions between hexakis(4-cyanophenyl)benzene molecules
de®ne an open network with space for including guests. The
resulting structure is a new pseudopolymorph of hexakis-
(4-cyanophenyl)benzene. The eight known pseudopoly-
morphs have few shared architectural features, in part because
none of the intermolecular interactions that are present plays
a dominant role or forces neighboring molecules to assume
particular relative orientations.
Comment
Networks of hydrogen bonds continue to be used extensively
by crystal engineers to help maintain the integrity of crystals
and to position their constituent molecules predictably
(Wuest, 2005). Hydrogen bonds offer the advantages of
strength and directionality, leading to the formation of robust
networks that frequently de®ne cavities or channels for the
inclusion of guests. Crystal engineers have also explored the
potential of weaker intermolecular interactions, which can
exhibit some of the geometric, structural and spectroscopic
characteristics of hydrogen bonds (Desiraju, 2002). For
example, we recently reported a study of structures main-
tained in part by weak C H  N interactions involving the
nitrile groups of hexakis(4-cyanophenyl)benzene, (I) (Maly et
al., 2006). Despite having a well de®ned molecular geometry
imposed by the hexaphenylbenzene core, compound (I)
crystallized under seven different sets of conditions to give
inclusion compounds with widely different structures.
Although networks maintained by C H  N interactions
were observed in all of these pseudopolymorphs, the parti-
cular geometries of the interactions varied widely and the
overall structures proved to depend critically on the choice of
solvent. These observations underscore the dif®culty of using
C H  N interactions to engineer crystals with predictable
structural features.
This conclusion has now been reinforced by the analysis of
the structure of a new pseudopolymorph obtained by crys-
tallizing compound (I) from CH3OH CH2Cl2 as the
dichloromethane disolvate, (II). In this structure, the molecule
of (I) lies on an axis of twofold rotation directed through
atoms C1 and C4 in the plane of the inner benzene ring
composed of atoms C1 C4/C3i/C2i [symmetry code: (i) ÿx, y,
organic compounds
o4 # 2007 International Union of Crystallography DOI: 10.1107/S0108270106046452 Acta Cryst. (2007). C63, o4 o6
Acta Crystallographica Section C
Crystal Structure
Communications
ISSN 0108-2701
Figure 1
A view of the structure of (II), showing the atom numbering scheme of
the asymmetric unit. Displacement ellipsoids are drawn at the 50%
probability level. Only one part of the disordered solvent molecules is
shown. The unlabeled parts of the molecules are related by the symmetry
operation ( x, y, z + 12).
ÿz + 12]. The hexaphenylbenzene core of compound (II) has a
chiral propeller conformation, with torsion angles in the range
61.97 (4) 73.37 (4) (Fig. 1). Similar conformations have been
noted in other pseudopolymorphs of compound (I) (Maly et
al., 2006).
The observed structure contains equal numbers of each
enantiomer. The disc-like shape of hexaphenylbenzene and its
derivatives normally favors structures in which the molecules
lie parallel and de®ne distinct layers. For example, hexa-
phenylbenzene itself (Bart, 1968), its inclusion compound with
anisole (Larson et al., 1990), and its derivatives substituted in
the para position by 4-(carboxyphenyl)ethynyl (Kobayashi et
al., 2005), iodo (Kobayashi et al., 2005), carboxy (Kobayashi et
al., 2000), tri¯uorovinyloxy (Spraul et al., 2004), hydroxy
(Kobayashi et al., 1999), ethynyl (Constable et al., 2000),
CONH2 (Kobayashi et al., 2003) and CN (Maly et al., 2006)
all have crystal structures in which the molecules are roughly
coplanar. In contrast, the new polymorph of (I) reported here
crystallizes to form a structure in which the molecules occupy
two sets of planes, which intersect along the b axis at an angle
of 68.29 (3). The only previously reported non-coplanar
architecture was obtained when hexakis(4-carbamoyl-
phenyl)benzene was crystallized under hydrothermal condi-
tions (Kobayashi et al., 2003).
In the structure of (II), each molecule of (I) is surrounded
by 14 neighbors, with ten neighbors linked to the central
molecule by a total of 12 C H  N interactions involving
H  N distances less than 2.80 AÊ and C H  N angles greater
than 90 (Fig. 2 and Table 1). Four additional neighbors have
C H  N interactions that are only slightly longer [H  N
distances of 2.85 (1) AÊ ] (Fig. 2). The resulting network de®nes
spaces for including partially disordered dichloromethane
molecules, which engage in van der Waals interactions and
C H  N interactions with nearby molecules of (I). Speci®-
cally, atom Cl1 is in close contact [3.324 (8) AÊ ] with the
centroid (Cg1) of the inner benzene ring of the molecule at
(x + 1, y, z), with a C29 Cl1  Cg1 angle of 163.6 (3).
Approximately 21% of the volume of the crystal is accessible
to guests, as measured by standard methods (Spek, 2003). This
value falls within the wide range of percentages (15 58%)
found in the other seven known pseudopolymorphs of (I). It is
interesting to note that compound (I) crystallizes from pure
methanol as an inclusion compound of composition
(I)2CH3OH (Maly et al., 2006), whereas crystallization from
CH3OH CH2Cl2 produces an inclusion compound containing
only CH2Cl2, which is presumably a preferred guest.
Together, these observations con®rm that nitrile groups
tend to engage in C H  N interactions and can help direct
the construction of open molecular networks. However, the
use of these interactions in crystal engineering is limited by
their weakness and lack of clear directional preferences, which
lead, in the case of (I), to crystallization as multiple pseudo-
polymorphs with very diverse structures.
Experimental
Hexakis(4 cyanophenyl)benzene, (I), was synthesized according to
the reported method of Maly et al. (2006). Crystals were grown by
placing a solution of compound (I) in CH2Cl2 (0.1 M, 2 ml) at the
bottom of a test tube, then carefully covering it with successive layers
composed of pure CH2Cl2 (1 ml), a 1:1 mixture of CH2Cl2 and
CH3OH (1 ml), and ®nally pure CH3OH (2 ml). The test tube was
sealed tightly and left undisturbed. Crystals of (II) appeared after
several days.
Crystal data
C48H24N62CH2Cl2
Mr = 854.58
Orthorhombic, Pbcn
a = 11.0921 (3) AÊ
b = 19.3442 (3) AÊ
c = 20.1742 (4) AÊ
V = 4328.73 (16) AÊ 3
Z = 4
Dx = 1.311 Mg m
3
Cu K radiation
 = 2.82 mm 1
T = 150 (2) K
Block, colorless
0.15  0.08  0.07 mm
Data collection
Bruker SMART 6000
diffractometer
! scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
Tmin = 0.700, Tmax = 0.850
57445 measured re¯ections
3865 independent re¯ections
3494 re¯ections with I > 2(I)
Rint = 0.051
max = 68.2

Re®nement
Re®nement on F 2
R[F 2 > 2(F 2)] = 0.058
wR(F 2) = 0.138
S = 1.02
3865 re¯ections
286 parameters
H-atom parameters constrained
w = 1/[2(Fo
2) + (0.119P)2]
where P = (Fo
2 + 2Fc
2)/3
(/)max < 0.001
max = 0.27 e AÊ
3
min = 0.28 e AÊ
3
H atoms were placed in idealized positions, with C H distances
in the range 0.95 0.99 AÊ , and re®ned using a riding model, with
Uiso(H) 1.2Ueq(C).
The dichloromethane solvent molecule was found to be disordered
over two sites. The ®rst molecule (C29, Cl1 and Cl2) was re®ned with
restraints on the C Cl distances and atomic displacement para
meters by the use of SADI and DELU instructions in SHELXL97
organic compounds
Acta Cryst. (2007). C63, o4 o6 Gagnon et al.  C48H24N62CH2Cl2 o5
Figure 2
View of a molecule of (I) (black) in compound (II), showing the
neighboring molecules that are linked to it by C H  N interactions
(broken lines), with H  N distances of less than 2.80 AÊ (dark gray) and
H  N distances of 2.85 (1) AÊ (light gray). H atoms not involved in
hydrogen bonding have been omitted for clarity.
(Sheldrick, 1997). The second part of the disordered dichloro
methane molecule (C30, Cl3 and Cl4) was re®ned to be similar to the
®rst part by the use of SAME and EADP instructions in SHELXL97.
With these restraints, the occupancy factors converged to 0.5312 (11)
and 0.4688 (11).
Data collection: SMART (Bruker, 2001); cell re®nement: SMART;
data reduction: SAINT (Bruker, 2003); program(s) used to solve
structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne
structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
SHELXTL (Bruker, 2000); software used to prepare material for
publication: enCIFer (Allen et al., 2004) and publCIF (Westrip,
2006).
The authors are grateful to the Natural Sciences and
Engineering Research Council of Canada (NSERC), the
MinisteÁre de l'EÂ ducation du QueÂbec, the Canada Foundation
for Innovation, the UniversiteÂ de MontreÂal and the Canada
Research Chairs Program for ®nancial support. In addition,
we thank Professor Jurgen Sygusch for providing access to a
Bruker SMART 6000 CCD diffractometer equipped with a
rotating anode.
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: GZ3032). Services for accessing these data are
described at the back of the journal.
References
Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J.
Appl. Cryst. 37, 335 338.
Bart, J. C. J. (1968). Acta Cryst. B24, 1277 1287.
Bruker (2000). SHELXTL. Version 6.10. Bruker AXS Inc., Madison,
Wisconsin, USA.
Bruker (2001). SMART. Version 5.624. Bruker AXS Inc., Madison, Wisconsin,
USA.
Bruker (2003). SAINT. Version 6.45. Bruker AXS Inc., Madison, Wisconsin,
USA.
Constable, E. C., Eich, O., Fenske, D., Housecroft, C. E. & Johnston, L. A.
(2000). Chem. Eur. J. 6, 4364 4370.
Desiraju, G. R. (2002). Acc. Chem. Res. 35, 565 573.
Kobayashi, K., Kobayashi, N., Ikuta, M., Therrien, B., Sakamoto, S. &
Yamaguchi, K. (2005). J. Org. Chem. 70, 749 752.
Kobayashi, K., Sato, A., Sakamoto, S. & Yamaguchi, K. (2003). J. Am. Chem.
Soc. 125, 3035 3045.
Kobayashi, K., Shirasaka, T., Horn, E. & Furukawa, N. (2000). Tetrahedron
Lett. 41, 89 93.
Kobayashi, K., Shirasaka, T., Sato, A., Horn, E. & Furukawa, N. (1999).
Angew. Chem. Int. Ed. 38, 3483 3486.
Larson, E. M., Von Dreele, R. B., Hanson, P. & Gust, J. D. (1990). Acta Cryst.
C46, 784 788.
Maly, K. E., Maris, T., Gagnon, E. & Wuest, J. D. (2006). Cryst. Growth Des. 6,
461 466.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
GoÈ ttingen, Germany.
Sheldrick, G. M. (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin,
USA.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7 13.
Spraul, B. K., Suresh, S., Glaser, S., Perahia, D., Ballato, J. & Smith, D. W. Jr
(2004). J. Am. Chem. Soc. 126, 12772 12773.
Westrip, S. P. (2006). PublCIF. In preparation.
Wuest, J. D. (2005). Chem. Commun. pp. 5830 5837.
organic compounds
o6 Gagnon et al.  C48H24N62CH2Cl2 Acta Cryst. (2007). C63, o4 o6
Table 1
Hydrogen bond geometry (AÊ , ).
DÐH  A DÐH H  A D  A DÐH  A
C19ÐH19  N2i 0.95 2.65 3.5076 (17) 151
C7ÐH7  N2ii 0.95 2.61 3.5355 (16) 165
C21ÐH21  N3iii 0.95 2.69 3.320 (2) 124
C29ÐH29B  N4iv 0.99 2.59 3.288 (9) 127
Symmetry codes: (i) x 1; y 1; z; (ii) x 12; y 32; z; (iii) x 12; y 12; z;
(iv) x 12; y 12; z 12.


A New Pseudopolymorph of Hexakis-(4-cynaophenyl)benzene

Wilfrid Laurier University

Wilfrid Laurier University Scholars Commons @ Laurier Chemistry Faculty Publications Chemistry 2006 A New Pseudopolymorph of Hexakis-(4-cynaophenyl)benzene Eric Gagnon Université de Montréal Kenneth E. Maly Wilfrid Laurier University, kmaly@wlu.ca Thierry Maris Université de Montréal James D. Wuest Université de Montréal Follow this and additional works at: https://scholars.wlu.ca/chem_faculty Recommended Citation Gagnon, Eric; Maly, Kenneth E.; Maris, Thierry; and Wuest, James D., "A New Pseudopolymorph of Hexakis-(4-cynaophenyl)benzene" (2006). Chemistry Faculty Publications. 8. https://scholars.wlu.ca/chem_faculty/8 This Article is brought to you for free and open access by the Chemistry at Scholars Commons @ Laurier. It has been accepted for inclusion in Chemistry Faculty Publications by an authorized administrator of Scholars Commons @ Laurier. For more information, please contact scholarscommons@wlu.ca. A new pseudopolymorph of hexakis-(4-cyanophenyl)benzeneEric Gagnon, Kenneth E. Maly, Thierry Maris* andJames D. WuestDeÂpartement de Chimie, UniversiteÂ de MontreÂal, MontreÂal, QueÂbec, Canada H3C 3J7Correspondence e-mail: thierry.maris@umontreal.caReceived 19 July 2006Accepted 3 November 2006Online 12 December 2006The title compound (systematic name: benzene-4,40,400,4000,-40000,4000 00-hexaylhexabenzonitrile dichloromethane disolvate),C48H24N62CH2Cl2, crystallizes as an inclusion compoundduring the slow diffusion of methanol into a solution ofhexakis(4-cyanophenyl)benzene in CH2Cl2. The hexakis(4-cyanophenyl)benzene molecule lies on an axis of twofoldrotation in the space group Pbcn. Weak C H  N inter-actions between hexakis(4-cyanophenyl)benzene moleculesde®ne an open network with space for including guests. Theresulting structure is a new pseudopolymorph of hexakis-(4-cyanophenyl)benzene. The eight known pseudopoly-morphs have few shared architectural features, in part becausenone of the intermolecular interactions that are present playsa dominant role or forces neighboring molecules to assumeparticular relative orientations.CommentNetworks of hydrogen bonds continue to be used extensivelyby crystal engineers to help maintain the integrity of crystalsand to position their constituent molecules predictably(Wuest, 2005). Hydrogen bonds offer the advantages ofstrength and directionality, leading to the formation of robustnetworks that frequently de®ne cavities or channels for theinclusion of guests. Crystal engineers have also explored thepotential of weaker intermolecular interactions, which canexhibit some of the geometric, structural and spectroscopiccharacteristics of hydrogen bonds (Desiraju, 2002). Forexample, we recently reported a study of structures main-tained in part by weak C H  N interactions involving thenitrile groups of hexakis(4-cyanophenyl)benzene, (I) (Maly etal., 2006). Despite having a well de®ned molecular geometryimposed by the hexaphenylbenzene core, compound (I)crystallized under seven different sets of conditions to giveinclusion compounds with widely different structures.Although networks maintained by C H  N interactionswere observed in all of these pseudopolymorphs, the parti-cular geometries of the interactions varied widely and theoverall structures proved to depend critically on the choice ofsolvent. These observations underscore the dif®culty of usingC H  N interactions to engineer crystals with predictablestructural features.This conclusion has now been reinforced by the analysis ofthe structure of a new pseudopolymorph obtained by crys-tallizing compound (I) from CH3OH CH2Cl2 as thedichloromethane disolvate, (II). In this structure, the moleculeof (I) lies on an axis of twofold rotation directed throughatoms C1 and C4 in the plane of the inner benzene ringcomposed of atoms C1 C4/C3i/C2i [symmetry code: (i) ÿx, y,organic compoundso4 # 2007 International Union of Crystallography DOI: 10.1107/S0108270106046452 Acta Cryst. (2007). C63, o4 o6Acta Crystallographica Section CCrystal StructureCommunicationsISSN 0108-2701Figure 1A view of the structure of (II), showing the atom numbering scheme ofthe asymmetric unit. Displacement ellipsoids are drawn at the 50%probability level. Only one part of the disordered solvent molecules isshown. The unlabeled parts of the molecules are related by the symmetryoperation ( x, y, z + 12).ÿz + 12]. The hexaphenylbenzene core of compound (II) has achiral propeller conformation, with torsion angles in the range61.97 (4) 73.37 (4) (Fig. 1). Similar conformations have beennoted in other pseudopolymorphs of compound (I) (Maly etal., 2006).The observed structure contains equal numbers of eachenantiomer. The disc-like shape of hexaphenylbenzene and itsderivatives normally favors structures in which the moleculeslie parallel and de®ne distinct layers. For example, hexa-phenylbenzene itself (Bart, 1968), its inclusion compound withanisole (Larson et al., 1990), and its derivatives substituted inthe para position by 4-(carboxyphenyl)ethynyl (Kobayashi etal., 2005), iodo (Kobayashi et al., 2005), carboxy (Kobayashi etal., 2000), tri¯uorovinyloxy (Spraul et al., 2004), hydroxy(Kobayashi et al., 1999), ethynyl (Constable et al., 2000),CONH2 (Kobayashi et al., 2003) and CN (Maly et al., 2006)all have crystal structures in which the molecules are roughlycoplanar. In contrast, the new polymorph of (I) reported herecrystallizes to form a structure in which the molecules occupytwo sets of planes, which intersect along the b axis at an angleof 68.29 (3). The only previously reported non-coplanararchitecture was obtained when hexakis(4-carbamoyl-phenyl)benzene was crystallized under hydrothermal condi-tions (Kobayashi et al., 2003).In the structure of (II), each molecule of (I) is surroundedby 14 neighbors, with ten neighbors linked to the centralmolecule by a total of 12 C H  N interactions involvingH  N distances less than 2.80 AÊ and C H  N angles greaterthan 90 (Fig. 2 and Table 1). Four additional neighbors haveC H  N interactions that are only slightly longer [H  Ndistances of 2.85 (1) AÊ ] (Fig. 2). The resulting network de®nesspaces for including partially disordered dichloromethanemolecules, which engage in van der Waals interactions andC H  N interactions with nearby molecules of (I). Speci®-cally, atom Cl1 is in close contact [3.324 (8) AÊ ] with thecentroid (Cg1) of the inner benzene ring of the molecule at(x + 1, y, z), with a C29 Cl1  Cg1 angle of 163.6 (3).Approximately 21% of the volume of the crystal is accessibleto guests, as measured by standard methods (Spek, 2003). Thisvalue falls within the wide range of percentages (15 58%)found in the other seven known pseudopolymorphs of (I). It isinteresting to note that compound (I) crystallizes from puremethanol as an inclusion compound of composition(I)2CH3OH (Maly et al., 2006), whereas crystallization fromCH3OH CH2Cl2 produces an inclusion compound containingonly CH2Cl2, which is presumably a preferred guest.Together, these observations con®rm that nitrile groupstend to engage in C H  N interactions and can help directthe construction of open molecular networks. However, theuse of these interactions in crystal engineering is limited bytheir weakness and lack of clear directional preferences, whichlead, in the case of (I), to crystallization as multiple pseudo-polymorphs with very diverse structures.ExperimentalHexakis(4 cyanophenyl)benzene, (I), was synthesized according tothe reported method of Maly et al. (2006). Crystals were grown byplacing a solution of compound (I) in CH2Cl2 (0.1 M, 2 ml) at thebottom of a test tube, then carefully covering it with successive layerscomposed of pure CH2Cl2 (1 ml), a 1:1 mixture of CH2Cl2 andCH3OH (1 ml), and ®nally pure CH3OH (2 ml). The test tube wassealed tightly and left undisturbed. Crystals of (II) appeared afterseveral days.Crystal dataC48H24N62CH2Cl2Mr = 854.58Orthorhombic, Pbcna = 11.0921 (3) AÊb = 19.3442 (3) AÊc = 20.1742 (4) AÊV = 4328.73 (16) AÊ 3Z = 4Dx = 1.311 Mg m3Cu K radiation = 2.82 mm 1T = 150 (2) KBlock, colorless0.15  0.08  0.07 mmData collectionBruker SMART 6000diffractometer! scansAbsorption correction: multi-scan(SADABS; Sheldrick, 2001)Tmin = 0.700, Tmax = 0.85057445 measured re¯ections3865 independent re¯ections3494 re¯ections with I > 2(I)Rint = 0.051max = 68.2Re®nementRe®nement on F 2R[F 2 > 2(F 2)] = 0.058wR(F 2) = 0.138S = 1.023865 re¯ections286 parametersH-atom parameters constrainedw = 1/[2(Fo2) + (0.119P)2]where P = (Fo2 + 2Fc2)/3(/)max < 0.001max = 0.27 e AÊ3min = 0.28 e AÊ3H atoms were placed in idealized positions, with C H distancesin the range 0.95 0.99 AÊ , and re®ned using a riding model, withUiso(H) 1.2Ueq(C).The dichloromethane solvent molecule was found to be disorderedover two sites. The ®rst molecule (C29, Cl1 and Cl2) was re®ned withrestraints on the C Cl distances and atomic displacement parameters by the use of SADI and DELU instructions in SHELXL97organic compoundsActa Cryst. (2007). C63, o4 o6 Gagnon et al.  C48H24N62CH2Cl2 o5Figure 2View of a molecule of (I) (black) in compound (II), showing theneighboring molecules that are linked to it by C H  N interactions(broken lines), with H  N distances of less than 2.80 AÊ (dark gray) andH  N distances of 2.85 (1) AÊ (light gray). H atoms not involved inhydrogen bonding have been omitted for clarity.(Sheldrick, 1997). The second part of the disordered dichloromethane molecule (C30, Cl3 and Cl4) was re®ned to be similar to the®rst part by the use of SAME and EADP instructions in SHELXL97.With these restraints, the occupancy factors converged to 0.5312 (11)and 0.4688 (11).Data collection: SMART (Bruker, 2001); cell re®nement: SMART;data reduction: SAINT (Bruker, 2003); program(s) used to solvestructure: SHELXS97 (Sheldrick, 1997); program(s) used to re®nestructure: SHELXL97 (Sheldrick, 1997); molecular graphics:SHELXTL (Bruker, 2000); software used to prepare material forpublication: enCIFer (Allen et al., 2004) and publCIF (Westrip,2006).The authors are grateful to the Natural Sciences andEngineering Research Council of Canada (NSERC), theMinisteÁre de l'EÂ ducation du QueÂbec, the Canada Foundationfor Innovation, the UniversiteÂ de MontreÂal and the CanadaResearch Chairs Program for ®nancial support. In addition,we thank Professor Jurgen Sygusch for providing access to aBruker SMART 6000 CCD diffractometer equipped with arotating anode.Supplementary data for this paper are available from the IUCr electronicarchives (Reference: GZ3032). Services for accessing these data aredescribed at the back of the journal.ReferencesAllen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J.Appl. Cryst. 37, 335 338.Bart, J. C. J. (1968). Acta Cryst. B24, 1277 1287.Bruker (2000). SHELXTL. Version 6.10. Bruker AXS Inc., Madison,Wisconsin, USA.Bruker (2001). SMART. Version 5.624. Bruker AXS Inc., Madison, Wisconsin,USA.Bruker (2003). SAINT. Version 6.45. Bruker AXS Inc., Madison, Wisconsin,USA.Constable, E. C., Eich, O., Fenske, D., Housecroft, C. E. & Johnston, L. A.(2000). Chem. Eur. J. 6, 4364 4370.Desiraju, G. R. (2002). Acc. Chem. Res. 35, 565 573.Kobayashi, K., Kobayashi, N., Ikuta, M., Therrien, B., Sakamoto, S. &Yamaguchi, K. (2005). J. Org. 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C63, o4 o6Table 1Hydrogen bond geometry (AÊ , ).DÐH  A DÐH H  A D  A DÐH  AC19ÐH19  N2i 0.95 2.65 3.5076 (17) 151C7ÐH7  N2ii 0.95 2.61 3.5355 (16) 165C21ÐH21  N3iii 0.95 2.69 3.320 (2) 124C29ÐH29B  N4iv 0.99 2.59 3.288 (9) 127Symmetry codes: (i) x 1; y 1; z; (ii) x 12; y 32; z; (iii) x 12; y 12; z;(iv) x 12; y 12; z 12.

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A New Pseudopolymorph of Hexakis-(4-cynaophenyl)benzene

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