Pseudopolymorphism and polymorphic transition behavior of N-(4′-methoxyphenyl)-2-naphthalenesulfonamide

Article abstract of DOI:10.1021/cg301457v

The title compound afforded four different types of crystals as pseudopolymorphs upon crystallization from a variety of different solvents. Single-crystal X-ray analysis revealed that the nonsolvated crystals exclusively formed a zigzag chain motif throug

Full text of DOI:10.1021/cg301457v

Article
pubs.acs.org/crystal
Pseudopolymorphism and Polymorphic Transition Behavior
of N‑(4′-Methoxyphenyl)-2-naphthalenesulfonamide
†
†
†
‡
†
Takahiro Sakai, Kosuke Katagiri, Yuki Uemura, Hyuma Masu, Masahide Tominaga,
,†
and Isao Azumaya*
†Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan
‡Chemical Analysis Center, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba-city, Chiba 263-8522, Japan
*
S Supporting Information
ABSTRACT: The title compound afforded four different types of crystals
as pseudopolymorphs upon crystallization from a variety of different
solvents. Single-crystal X-ray analysis revealed that the nonsolvated crystals
exclusively formed a zigzag chain motif through hydrogen-bonding
interactions (H-bonds). In contrast, the solvent-containing crystals formed
a helical chain motif through H-bonds to give rise to channel-shaped
network structures. The inner spaces of the channels were occupied by
solvent molecules from the crystallization solvent. These solvent-containing
crystals could be converted to the nonsolvated crystals by removal of the
solvent molecules by drying under reduced pressure at 45 °C. They also
showed mutual polymorphic transitions via a solvent-exchange process.
8
INTRODUCTION
state resulted from their twisted synclinal conformation and
■
were also reported.
The regulation of the crystal polymorphism and pseudopoly-
morphism of organic compounds has recently been the subject
of considerable interest from several different scientific areas,
including medicinal chemistry and materials science, because
crystal polymorphs and pseudopolymorphs exhibit different
In this paper, four types of crystals have been reported from
the pseudopolymorphism of N-(4-methoxyphenyl)-2-naphtha-
lenesulfonamide (1), which was designed to investigate the
effect of weak noncovalent interactions on the solvent inclusion
properties built in addition to the robust infinite hydrogen-
bonding network. We also report the polymorphic transitions
between the pseudopolymorphs, which were observed during
the solvent removal and solvent-exchange processes.
physical and chemical properties as a consequence of thei1r
different molecular arrangements or conformations in the crystal.
Differences in crystal structure may occur as a consequence of
differences in the molecular conformation and noncovalent inter-
2
actions of a material, such as the hydrogen-bonding (H-bond),
3
4
aromatic−aromatic, and other interactions, that can result in an
alternative packing arrangement. In addition, polymorphic
transitions between different crystalline forms in response to
EXPERIMENTAL SECTION
■
Synthesis of N-(4-Methoxyphenyl)-2-naphthalenesulfonamide
(1). 2-Naphthalenesulfonyl chloride (10 mmol) was added dropwise
to a stirred solution of 4-methoxyaniline (11 mmol) in a mixture of
CH Cl (200 mL) and pyridine (30 mmol, 2.4 mL) under an Ar
atmosphere. The resulting mixture was stirred at room temperature for
h and then poured into ice and extracted with chloroform. The
organic layer was washed sequentially with 2 M HCl (200 mL),
saturated aqueous NaHCO (200 mL), and brine (200 mL) and dried
over Na SO . The solvent was evaporated, and the crude product was
recrystallized from a mixture of chloroform and hexane (1:1) to give
the pure desired product (2.56 g, 82%). mp 89−90 °C. H NMR (400
MHz, CDCl , 25 °C) δ: 8.68 (d, J = 8.8 Hz, 1H), 8.07 (d, J = 7.2 Hz,
1H), 8.03 (d, J = 8.4 Hz, 1H), 7.95 (d, J = 8.0 Hz, 1H), 7.68 (t, J = 8.0 Hz,
1H), 7.61 (t, J = 7.6 Hz, 1H), 7.42 (t, J = 8.0 Hz, 1H), 6.76 (d, J =
2.0 Hz, 1H), 6.62 (d, J = 12.0 Hz, 1H), 3.69 (s, 3H) ppm. C NMR
100 MHz, CDCl ) δ: 158.10, 135.93, 134.86, 132.02, 129.30, 129.24,
28.84, 128.62, 127.87, 127.47, 125.73, 122.43, 114.46, 55.39 ppm.
5
environmental changes have also notably attracted attention in
the development of functional solid materials. Compared to a
prevailing reversible change of the structures and properties
between two crystalline forms, the mutual crystal-to-crystal
transformations bearing the reversibility between three or four
crystal structures were rarely exemplified.
We have previously reported that some compounds, such as
aromatic amides and aromatic sulfonamides, exhibited poly-
morphism and pseudopolymorphism depending on the
crystallization conditions used. For example, 1,2-bis(N-p-
fluorobenzoyl-N-methylamino)benzene showed 13 types of
polymorphs and pseudopolymorphs, and the crystal-to-crystal
phase transitions between these crystals, as well as the aromatic
sulfonamides containing fluorine groups on the benzenesulfonyl
moieties, showed polymorphs and pseudopolymorphs following
2
2
2
3
2
4
1
3
6
1
3
1
6a
(
3
1
6e
crystallization from a variety of standard solvents. In addition,
the details on the sulfonamides that underwent spontaneous
Received: October 6, 2012
Revised: November 29, 2012
Published: December 5, 2012
7
resolution or helical network structure constructed in the solid
©
2012 American Chemical Society
308
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Crystal Growth & Design
Article
Figure 1. Reaction scheme for the preparation of the sulfonamide 1, and crystallization conditions and pseudopolymorphic forms.
Table 1. Crystallographic Data for Sulfonamides 1
1
a
1b
1c
formula
C H NO S
C H NO S·0.5C H
C H NO S·0.5C H
9
1
7
15
3
17 15
3
6
6
17 15
3
7
cryst syst
monoclinic
Pbca
monoclinic
monoclinic
space group
a (Å), α (deg)
b (Å), β (deg)
c (Å), γ (deg)
V (Å3)
P2 /n
1
P2 /n
1
11.372(1), 90
9.4405(8), 90
28.453(2), 90
3054.6(5)
1.363
10.865(2), 90
10.856(1), 90
6.335(1), 100.004(3)
26.008(5), 90
1762.8(6)
1.328
6.3533(6), 98.229(1)
26.403(3), 90
1802.3(30
1.310
Dcalc (Mg m−3)
Z
8
4
4
T (K)
150
150
120
R , wR (all data)
0.0760, 0.1606
0.0822, 0.1320
benzene
0.0705, 0.1513
toluene
1
2
recryst from
CHCl /cycloexane
3
H-bond motif
CCDC number
zigzag (type A)
900772
helical (type B)
900773
helical (type B)
900774
1
d
1e
1f
formula
C H NO S·0.5C H
C H NO S·C H
C H NO S·C H
10
1
7
15
3
6
12
17 15
3
8
10
17 15
3
8
cryst syst
monoclinic
monoclinic
monoclinic
space group
a (Å), α (deg)
b (Å), β (deg)
c (Å), γ (deg)
V (Å3)
P2 /c
P2 /c
P2 /c
1
1
1
12.744(5), 90
10.917(3), 90
11.193(1), 90
6.242(2), 93.911(5)
6.175(2), 96.594(4)
32.434(9), 90
2172(1)
6.0493(7), 98.736(1)
32.694(4), 90
2188.1(4)
1.274
22.864(9), 90
1815(2)
1.301
Dcalc (Mg m−3)
1.283
Z
4
4
4
T (K)
150
120
120
R , wR (all data)
0.0525, 0.1133
0.0850, 0.1523
o-xylene
0.0483, 0.0962
p-xylene
1
2
recryst from
CHCl /cyclohexane
3
H-bond motif
CCDC number
helical (type C)
900775
helical (type D)
901300
helical (type D)
901301
+
MS (FAB): m/z = 314.1 [M + H] . Elemental Anal. Calcd for
Measurement. X-ray data for the crystals were collected on a
charge-coupled device diffractometer using graphite monochromated
C H O NS: C, 65.16; H, 4.82; N, 4.47. Found: C, 65.05; H, 4.84; N, 4.44.
1
8
15
3
3
09
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Figure 3. Crystal structure of the sulfonamide 1b depicted as a ball-
and-stick model. (a) Helical chain units via H-bonds. (b) Arrangement
of helical chain units through CH/π interactions (top view). (c)
Arrangement of helical chain units through CH/π interactions (side
view). Black- and red-dotted lines show H-bonds and CH/π
interactions, respectively. Magenta- and cyan-colored molecules are
the enantiomeric conformers of each other.
Figure 2. Crystal structure of the sulfonamide 1a depicted as a ball-
and-stick model. (a) Zigzag chain units via H-bonds. (b) Arrangement
of zigzag chain units through CH/π interactions (top view). (c)
Arrangement of zigzag chain units through CH/π interactions (side
view). Black- and red-dotted lines show H-bonds and CH/π
interactions, respectively. Magenta- and cyan-colored molecules are
the enantiomeric conformers of each other.
RESULTS AND DISCUSSION
■
A variety of different crystallization conditions were investigated
for the aromatic sulfonamide 1 and ultimately led to the isola-
tion of four different types of pseudopolymorphs (Figure 1),
including (i) crystal 1a (type A), which was obtained from the
vapor diffusion of cyclohexane into a chloroform solution; (ii)
1
b and 1c (type B), which were obtained following the slow
Mo Kα (λ = 0.71073 Å) radiation. Data collections for all crystals were
carried out at low temperature (100−150 K) using liquid nitrogen. The
crystal structures were solved by direct methods (SHELXS-97) and
evaporation of a benzene or a toluene solution; (iii) 1d (type
C), which was obtained from the vapor diffusion of cyclohexane
into a solution of 1 in chloroform and cyclohexane; and (iv) 1e
and 1f (type D), which were formed following the slow evapora-
tion of an o-xylene or p-xylene solution. X-ray crystallographic
analyses were performed on single crystals of 1a−1f. Crystal
data and intermolecular interaction geometries of all the
pseudopolymorphs are shown in Table 1, and Tables S1 and
S2 of the Supporting Information.
9
refined by full-matrix least-squares (SHELXL-97). All non-hydrogen
atoms were refined anisotropically, and hydrogen atoms were included
as their calculated positions. Powder X-ray diffraction (PXRD) data
were recorded on a RIGAKU RINT 2000/PC diffractometer using
Cu Kα (λ = 1.5418 Å) radiation with the curved Ni monochromator
transmission mode. Data collections for all compounds were carried out
at room temperature.
3
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Figure 5. Crystal structure of the sulfonamide 1e depicted as a ball-
and-stick model. (a) Helical chain units via H-bonds. (b) Arrangement
of helical chain units through CH/π interactions (top view). (c)
Arrangement of helical chain units through CH/π interactions (side
view). Black- and red-dotted lines show H-bonds and CH/π
interactions, respectively. Magenta- and cyan-colored molecules are
the enantiomeric conformers of each other.
Figure 4. Crystal structure of the sulfonamide 1d depicted as a ball-
and-stick model. (a) Helical chain units via H-bonds. (b) Arrangement
of helical chain units through CH/π interactions (top view). (c)
Arrangement of helical chain units through CH/π interactions (side
view). Black- and red-dotted lines show H-bonds and CH/π
interactions, respectively. Magenta- and cyan-colored molecules are
the enantiomeric conformers of each other.
1b and were connected to 1 though CH/π interactions
(
Table S2, Supporting Information). The molecular packing
Type A crystal 1a had an orthorhombic system, space group
Pbca, and included eight molecules in the unit cell. In the
nonsolvated crystal of 1a, both enantiomeric conformers of the
sulfonamide 1 were alternately connected to form the zigzag
chain motif though H-bonds between the oxygen atoms of the
sulfonyl group and the nitrogen atoms of the sulfonamide
group (N1−O2: 3.074(3) Å, Figure 2a). The zigzag chain units
extend along the c axis through CH/π interactions. The void
space of the unit cell was fairly closed and not capable of
including any solvent molecules (Figure 2b,c).
of the toluene-containing crystal 1c was similar to that of 1b
(Figures S9−S11, Supporting Information).
The cyclohexane-containing type C crystal 1d had a
monoclinic system with space group P2 /c and included four
1
molecules of 1 and two molecules of cyclohexane in the unit cell.
The sulfonamide 1 associated along the b axis through H-bonds
to effectively construct a homochiral helical chain motif (N1−O2:
2.850(2) Å, Figure 4a). The helical chain units consisted of
homochiral networks and were adjacent to an enantiomeric
chain connected by CH/π interactions to form a channel-shaped
network structure (Figure 4b,c). The walls of the channels, which
contained cyclohexane molecules, were formed by two
naphthalene and two benzene groups. The molar ratio of 1 to
the cyclohexane molecules was 2:1 (from crystal analysis).
The type D crystal 1e crystallized in a monoclinic system
In contrast, type B crystal 1b, which crystallized in a mono-
clinic system with space group P2 /n, and included four
1
molecules of 1 and two molecules of benzene in the unit cell. As
shown in Figure 3a, the one-handed enantiomers of 1 associated
along the b axis through H-bonds, effectively constructing a
homochiral helical chain motif (N1−O2: 2.887(2) Å). Each of
the enantiomeric helical chain units faced each other to form
the channel-shaped network structure along the c axis through
van der Waals interactions. The same enantiomeric helical
chain units associate along the a axis though CH/π interactions
with space group P2 /c and included four molecules of 1 and
1
four molecules of o-xylene in the unit cell. The sulfonamide 1
associated along the b axis through H-bonds to effectively
construct a homochiral helical chain motif (N1−O2: 2.893(9) Å,
Figure 5a). The helical chain units were adjacent to an enantio-
meric chain connected by van der Waals and CH/π interactions
(
Figure 3b,c). Benzene molecules filled up the channel space of
3
11
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Figure 6. Experimental (black) and simulated (red) PXRD patterns for (a) 1a (type A), (b) 1b (type B), (c) 1d (type C), and (d) 1e (type D).
to form a channel-shaped network structure, which was
constructed from two molecules of 1 facing each other and
the outer side of two other molecules of 1 (Figure 5b,c). The
channels of 1e contained two molecules of o-xylene. The molar
ratio of 1 to the o-xylene molecules was 1:1 (from crystal
analysis). The molecular packing of 1f is similar to that of 1e
In contrast, exposure of the crystals of 1a to benzene vapor for
72 h or o-xylene vapor for 7 days led to absorption of benzene or
o-xylene to afford 1b or 1e, respectively. Complete conversion
from 1a to 1d was also observed following the soaking of
powdered crystals of 1a in cyclohexane for 72 h.
The mechanism for the transformation of the nonsolvated
crystal (1a) to the solvent-containing crystals (1b, 1d, and 1e)
would involve the sulfonamide molecules of a racemic zigzag
H-bonding chain in 1a alternately changing the sign of
their synclinal conformations to form a homochiral helical
H-bonding chain. At the same time, the oxygen atom involved
in the H-bonding network switched from O2 to O1, effectively
reducing the length of the b axis and resulting in the formation
of void spaces for the solvent molecules (Figure 8). In contrast,
when the solvent molecules were removed by heating under
reduced pressure, the sulfonamide molecules of the homochiral
helical H-bonding chains in 1b, 1d, and 1e alternately changed
the sign of their synclinal conformations to form a racemic
zigzag H-bonding chain. The oxygen atom involved in the
H-bonding network then simultaneously switched from O1 to
O2 to extend the length of the b axis, resulting in the filling of
the void spaces (Figure 8).
(
Figures S18−S20, Supporting Information). Although the
homochiral H-bonding motifs of 1b−1f were similar to each
other, they differed from each other in terms of their molecular
packing.
The PXRD patterns of crystals 1a, 1b, 1d, and 1e are shown
in Figure 6, and they were all in good agreement with the
PXRD patterns simulated from the single-crystal data. The
products of the solid-state transformations were, therefore,
identified by comparison between the PXRD patterns measured
on the solid material.
As shown in Figure 7, the solid-state transformations
between the solvent-containing crystals (1b, 1d, and 1e) and
the nonsolvated crystal (1a) were mutually reversible. The
nonsolvated crystal (1a) was obtained by removal of the
solvent molecules of from the solvent-containing crystals (1b,
1d, and 1e) by drying under reduced pressure at 45 °C for 72 h.
3
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Furthermore, reversible polymorphic transitions occurring as
a consequence of solvent-exchange processes between the
solvated crystals (1b, 1d, and 1e) were observed. When crystals
of 1d or 1e were exposed to benzene vapor for 72 h, the
benzene was absorbed into the channels. The displacement of
the cyclohexane or o-xylene solvent molecules by benzene then
occurred to generate crystals 1b. Similarly, 1b and 1d could be
converted to 1e by the vapor diffusion of o-xylene over a 7 day
period. In addition, 1b and 1e could be converted to 1d following
a 72 h soaking period in cyclohexane. During the interconversion
processes of 1b, 1d, and 1e, the helical H-bond networks of
1
were preserved and the channels could accommodate the
corresponding solvent molecules. This means that the homochiral
H-bonding chains in the crystals 1b, 1d, and 1e were robust and
the polymorphic transitions were in accord with considerations
on the shape and size of solvent molecules. In addition, the
reversible polymorphic transitions are considered to be assisted
by CH/π interactions between sulfonamide 1 and solvent
molecules in the case that benzene, toluene, or xylene was used
(
Table S2, Supporting Information).
CONCLUSION
■
In conclusion, we have demonstrated that N-(4′-methoxy-
phenyl)-2-naphthalenesulfonamide showed pseudopoly-
morphs by crystallization from a variety of different solvents.
Single-crystal X-ray analysis revealed that the nonsolvated
crystals 1a exhibited racemic zigzag H-bonding networks with
closed channels, whereas the solvent-containing crystals
(
1b−1f) exhibited helical H-bonding networks with channels.
In the type B crystals (1b and 1c), each of the enantiomeric
helical chain units faced each other to form the channels,
which contained benzene or toluene molecules with a 2:1
sulfonamide/solvent ratio. In the type C crystals (1d), the
channels were formed by the outer sides of four molecules of
1
and contained cyclohexane with a 2:1 sulfonamide/solvent
ratio. The channels of the type D crystals (1e and 1f) were
constructed from two molecules of 1 facing each other and the
outer sides of two molecules of 1 and contained cyclohexane
with a 1:1 sulfonamide/solvent ratio. The solvent-containing
Figure 7. Summary of transformations.
Figure 8. Plausible mechanism of the solid-state transformations.
3
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crystals (1b, 1d, and 1e) were converted to nonsolvated crystal
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1
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We believe that the results obtained from this investigation will
lead to the development of a methodology for controlling the
polymorphism of pharmaceutical compounds.
(
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ASSOCIATED CONTENT
■
(5) (a) Hori, K.; Koma, Y.; Kurosaki, M.; Itoh, K.; Uekusa, H.;
*
S
Supporting Information
1
H and 13C NMR spectroscopic data and all crystallographic
Takenaka, Y.; Ohashi, Y. Bull. Chem. Soc. Jpn. 1996, 69, 891−897.
(b) Thaimattam, R.; Xue, F.; Sarma, J. A. R. P.; Mak, T. C. W.;
data and crystallographic information files (CIF). This material
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Plass, K. E.; Matzger, A. J. Langmur 2003, 19, 7149−7152. (d) Croker,
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AUTHOR INFORMATION
Corresponding Author
Tel: +81-87-894-5111, ext. 6308. Fax: +81-87-894-0181. E-mail:
azumayai@kph.bunri-u.ac.jp.
■
*
(
g) Drebushchak, T. N.; Ogienko, A. A.; Boldyreva, E. V.
CrystEngComm 2011, 13, 4405−4410. (h) Minkov, V. S.;
Drebushchak, V. A.; Ogienko, A. G.; Boldyreva, E. V. CrystEngComm
Notes
The authors declare no competing financial interest.
2
011, 13, 4417−4426. (i) Tamura, R.; Iwama, S.; Gonnade, R. G.
CrystEngComm 2011, 13, 5269−5280. (j) Braga, D.; D’Agostino, S.;
Grepioni, F.; Gandolfi, M.; Rubini, K. Dalton Trans. 2011, 40, 4765−
4777.
ACKNOWLEDGMENTS
■
This work was supported by the Science Research Promotion
Fund through the Promotion and Mutual Aid Corporation for
Private Schools of Japan.
(6) (a) Kato, T.; Okamoto, I.; Masu, H.; Katagiri, K.; Tominaga, M.;
Yamaguchi, K.; Kagechika, H.; Azumaya, I. Cryst. Growth Des. 2008, 8,
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871−3877. (b) Katagiri, K.; Kato, T.; Masu, H.; Tominaga, M.;
Azumaya, I. Cryst. Growth Des. 2009, 9, 1519−1524. (c) Tohaya, T.;
Katagiri, K.; Katoh, J.; Masu, H.; Tominaga, M.; Azumaya, I.
CrystEngComm 2010, 12, 3493−3495. (d) Masu, H.; Sagara, Y.;
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M.; Kagechika, H.; Yamaguchi, K.; Azumaya, I. CrystEngComm 2011,
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