5,5′-Di-tert-butyl-2,2′-dihydroxy-3,3′- methanediyldibenzaldehyde and its allyl-protected dialcohol and dialdehyde precursors

Article abstract of DOI:10.1107/S010827010402089X

5,5′-Di-tert-butyl-2,2′-dihydroxy-3,3′- methanediyldibenzaldehyde, C₂₃H₂₈O₄, (IV), has been structurally characterized in two polymorphic forms. The tetragonal form, (in I4₁/a) has been reported previously but i

Full text of DOI:10.1107/S010827010402089X

organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
patterns, which have OÐHÁ Á ÁO directions running either
anticlockwise (as in Fig. 2) or clockwise around the same ring.
Ê
The highest residual electron-density peak is 1.26 A from
Ê
atom C28 and 1.39 A from atom C27, and may indicate a
minor disorder of that allyl group.
ISSN 0108-2701
5,50-Di-tert-butyl-2,20-dihydroxy-
3,30-methanediyldibenzaldehyde
and its allyl-protected dialcohol
and dialdehyde precursors
Sandrine Goetz, Julia Barreira Fontecha and Vickie
McKee*
Chemistry Department, Loughborough University, Leicestershire LE11 3TU, England
Correspondence e-mail: v.mckee@lboro.ac.uk
Received 9 August 2004
Accepted 24 August 2004
Online 9 October 2004
5,50-Di-tert-butyl-2,20-dihydroxy-3,30-methanediyldibenzalde-
hyde, C23H28O4, (IV), has been structurally characterized in
two polymorphic forms. The tetragonal form, (in I41/a) has
been reported previously but is redetermined and reinter-
preted here, while the monoclinic form, (in C2/c) is reported
for the ®rst time. In both polymorphs, the molecule lies on
a crystallographic twofold axis. Two precursors in the
synthesis of (IV), namely 2,20-bis(allyloxy)-5,50-di-tert-butyl-
3,30-methanediyldibenzenemethanol (C29H40O4) and 2,20-bis-
(allyloxy)-5,50-di-tert-butyl-3,30-methanediyldibenzaldehyde
(C29H36O4) have also been characterized.
The dialcohol was oxidized using MnO2 to form the
analogous dialdehyde, 2,20-bis(allyloxy)-5,50-di-tert-butyl-3,30-
methanediyldibenzaldehyde, (III). As Fig. 3 shows, the phenyl
planes are inclined at 74.17 (5)ꢀ and the tert-butyl groups are
on the same side of the molecule. One of the allyl groups is
disordered, and this disorder was modelled as a 70:30 occu-
pancy of two conformations. Again, the molecules are linked
by hydrogen bonding into a double chain, in this case running
Comment
The diphenolic dialdehyde 5,50-di-tert-butyl-2,20-dihydroxy-
3,30-methanediyldibenzaldehyde, (IV), has been used to
synthesize new polynucleating macrocycles by Schiff base
condensation with diamines (Barreira Fontecha et al., 2002).
Compound (IV) was prepared in three steps from the known
dialcohol analogue 5,50-di-tert-butyl-2,20-dihydroxy-3,30-me-
thanediyldibenzenemethanol, (I) (Dhawan & Gutsche, 1983).
The structure of 2,20-bis(allyloxy)-5,50-di-tert-butyl-3,30-
methanediyldibenzenemethanol, (II), is shown in Fig. 1. The
molecule is non-planar, with the two aryl rings inclined at
78.84 (9)ꢀ with respect to one another and the tert-butyl
groups lying on opposite sides of the molecule. The apparent
folding of the molecule is actually due to rotation about the
C12ÐC4 and C12ÐC13 bonds, and the conformation adopted
is probably a consequence of the hydrogen-bonding network
throughout the lattice. Hydrogen bonding between alcohol
groups generates eight-membered rings [graph-set notation
R44(8)] and links the molecules into a double chain running
parallel to the a axis (Fig. 2 and Table 1). The H atoms on the
hydroxy groups are disordered, and these atoms were
modelled with 50% occupancy of two equivalent positions. As
a result there are two self-consistent hydrogen-bonding
Figure 1
A view of the structure of (II). The H atoms on the two alcohol functions
are disordered and only one position is shown for each. Displacement
ellipsoids are drawn at the 50% probability level.
o776 # 2004 International Union of Crystallography
DOI: 10.1107/S010827010402089X
Acta Cryst. (2004). C60, o776±o780

organic compounds
parallel to c (Fig. 4); however, the interactions are all of the
type CÐHÁ Á ÁO C (Table 2). There is also some ꢀ±ꢀ stacking
across the hydrogen-bonded chain involving the benzaldehyde
groups. The section incorporating atoms O1/C1/C2/C3/C7
In the tetragonal form, (IVa), the asymmetric unit contains
half of the molecule, with a twofold axis passing through atom
C12 (Fig. 5), while in the monoclinic form, (IVb), the asym-
metric unit contains two independent half molecules, each
having twofold symmetry (Fig. 6). The molecular conforma-
tion and bond lengths are similar in the two polymorphs; the
tert-butyl groups are on opposite sides of the linked aryl rings
and the phenol H atoms are involved in intramolecular
hydrogen bonds with the adjacent carbonyl groups (Tables 3
and 4). In (IVb), there is additional intermolecular hydrogen
bonding involving one of the carbonyl groups (C13 O3).
Atom C13 forms a CÐHÁ Á ÁO C hydrogen bond to atom O3
of a neighbouring molecule at ( x, 2 y, 1 z), resulting in
zigzag chains parallel to c. The second molecule does not show
a corresponding interaction. As in the precursors, the phenyl
rings are inclined with respect to one another: in the tetra-
gonal form, the phenyl rings are inclined at 61.48 (5)ꢀ, whereas
in the monoclinic polymorph, the values are 73.58 (5) and
75.04 (5)ꢀ.
overlaps the O4/C23/C16±C18 section of a neighbouring
1
molecule at (x,
y, 12 + z). The planes of the interacting
2
benzaldehyde rings are inclined at 12.33 (7)ꢀ, while atoms O1
Ê
and C1 are 3.274 (2) and 3.357 (2) A, respectively, from the
mean plane of the interacting phenyl ring (Fig. 4).
Compound (IV) has been characterized in two polymorphic
forms. We obtained the tetragonal form, (IVa) (space group
I41/a), by recrystallization of the crude material from diethyl
ether, while Masci et al. (2004) obtained the same polymorph
by recrystallization from methanol. A second polymorph was
formed as a side product in the synthesis of a macrocyclic
complex; crystals of (IVb) in the monoclinic space group C2/c
were obtained from a methanol solution containing 1,5-di-
aminopentan-3-ol and nickel(II) nitrate.
Figure 4
The CÐHÁ Á ÁO C hydrogen-bonded chain parallel to b in (III).
1
2
1
2
[Symmetry codes: (vi) x,
y, 12 + z; (vii) x,
y, 12 + z.]
Figure 2
The hydrogen bonding in (II), producing a double chain parallel to a.
Only one of the two orientations of the hydrogen bonding within the
R44(8) ring is shown. [Symmetry codes: (i) 1 + x, y, z; (ii) x, 2 y, z;
(iii) 1 x, 2 y, z.]
Figure 5
A view of the structure of polymorph (IVa); intramolecular hydrogen-
bonding interactions between the phenol and aldehyde functions are
shown as dashed lines. Dotted lines show interatomic distances in the
Ê
Figure 3
A view of the structure of (III), showing the disorder in one allyl group.
Displacement ellipsoids are drawn at the 50% probability level.
range 3.42±3.47 A in the ꢀ±ꢀ overlap region. Displacement ellipsoids are
drawn at the 50% probability level. [Symmetry codes: (viii) 2 x, 32 y,
z; (ix) 2 x, 1 y, z.]
ꢁ
Acta Cryst. (2004). C60, o776±o780
Sandrine Goetz et al. C29H40O4, C29H36O4 and C23H28O4 o777

organic compounds
In form (IVa), the molecules are packed as shown in Figs. 5
and 7. In contrast to the previous report of this structure
(Masci et al., 2004), we have identi®ed ꢀ±ꢀ interactions (the
most direct overlap being between the sections containing
atoms O1/C1/C2/C7/C6; see Fig. 5) linking the molecules into
sets of zigzag ribbons running parallel to either the a or the b
axis. As can be seen in Fig. 5, ꢀ-stacked pairs of rings are
parallel and related by inversion; the distance between the
mean plane of the benzaldehyde ring containing atoms O1 and
C7 and the centroid of the neighbouring phenyl ring at (2 x,
1
In polymorph (IVb), the two independent molecules form
Ê
y, z) is 3.361 (4) A.
ABAB ꢀ-stacked columns parallel to the b axis (Fig. 8). The
relative rotation between adjacent layers prevents steric
Figure 8
A unit-cell plot for polymorph (IVb), projected down b, showing ꢀ-
stacked columns parallel to b and inter- and intramolecular hydrogen
bonding (dashed lines). O atoms are shown as shaded circles.
interference between successive tert-butyl groups (Fig. 6). The
benzaldehyde rings are almost parallel [interplanar angle =
6.34 (10)ꢀ], with average interplanar separations of 3.48 and
Ê
3.32 A between the ring containing atoms O1 and C7 and that
containing O3 and C19 at ( x, y, 12 z) and ( x, 1 + y, 21 z),
respectively. Again, the shortest ꢀ±ꢀ interactions are between
the carbonyl groups and the phenyl rings of neighbouring
molecules in the stack.
Experimental
Compound (I) was synthesized according to the procedure of
Dhawan & Gutsche (1983). For the synthesis of (II), compound (I)
(10 g, 27 mmol), allyl bromide (7 g, 58 mmol), anhydrous K2CO3
(7.42 g) and acetone (100 ml) were placed in a 250 ml three-necked
round-bottomed ¯ask ®tted with a re¯ux condenser and a sealed
stirrer unit, and were re¯uxed for 20 h with stirring. The reaction
mixture was then poured into water (200 ml) and the aqueous layer
was extracted three times with diethyl ether. The organic layer was
washed with a 2 M sodium hydroxide solution and dried over an-
hydrous K2CO3. The solvent was removed under vacuum, leaving a
white solid, which was recrystallized from dichloromethane/
n-hexane; the yield was 9.0 g (74%). Colourless crystals suitable for
X-ray studies were obtained by slow evaporation of a solution of
dichloromethane/pentane (1:5). Thin-layer chromatography (TLC)
on silica gel (diethyl ether/petroleum ether 40/60, 45:55): RF = 0.68.
Analysis calculated for (II)Á0.5H2O: C 75.45, H 8.95%; found: C 75.64,
Figure 6
A view of the two independent molecules in polymorph (IVb). A twofold
axis passes through atoms C12 and C24. Displacement ellipsoids are
1
drawn at the 30% probability level. [Symmetry code: (x) x, y,
z.]
2
1
H 9.06%. H NMR (CDCl3, p.p.m.): 7.24 (d, 2H, ArH), 7.01 (d, 2H,
ArH), 6.07 (m, 2H, allyl CH), 5.34 (dd, 2H, allyl CH2), 5.30 (dd,
2H, allyl CH2), 4.73 (d, 4H, CH2OH), 4.34 (d, 4H, allyl CH2), 4.70
(s, 4H, CH2OH), 4.07 (s, 2H, ArCH2Ar), 1.26 [s, 18H, C(CH3)3]. IR
(KBr, cm 1): 3272 [s, ꢁ(OH)], 3081 [w, ꢁ(allyl CH2)], 883 (m, 1,2,3,5
tetrasubstitution of Ar).
Compound (III) was synthesized by a method similar to that
reported by Taniguchi (1984). Activated MnO2 (50 g) was added to a
solution of (II) (9 g, 20 mmol) in chloroform (200 ml). The reaction
mixture was re¯uxed for 19±20 h, after which time MnO2 was ®ltered
off and the organic layer dried over anhydrous MgSO4. The solvent
was removed under vacuum, leaving a pale-yellow oil that crystallized
under vacuum over a period of one week. The solid was then washed
with cold methanol to remove the yellow impurities. Colourless
Figure 7
Aunit-cell plot for polymorph (IVa), viewed down the a axis, showing the
ꢀ±ꢀ-stacked ribbons running parallel to a and parallel to b. O atoms are
shown as shaded circles. Dashed lines indicate the ꢀ±ꢀ overlapped
sections.
ꢁ
o778 Sandrine Goetz et al.
C29H40O4, C29H36O4 and C23H28O4
Acta Cryst. (2004). C60, o776±o780

organic compounds
crystals suitable for X-ray studies were obtained by slow evaporation
of a diethyl ether solution of the product. The yield was 7.0 g (78%).
TLC on silica gel (diethyl ether/petroleum ether 40/60, 30:70): RF =
0.50. Analysis calculated for (III)Á0.5H2O: C 76.11, H 8.15%; found: C
76.08, H 8.15%. 1H NMR (CDCl3, p.p.m.): 10.4 (s, 2H, CHO), 7.75 (d,
2H, ArH), 7.30 (d, 2H, ArH), 6.06 (m, 2H, allyl CH), 4.40 (dd, 2H,
allyl CH2), 4.44 (dd, 2H, allyl CH2), 4.13 (s, 2H, ArCH2Ar),
1.26 [s, 18H, C(CH3)3]. IR (KBr, cm 1): 1660 [ꢁ(C O)], 3081
[w, ꢁ(allyl CH2)], 885 (m, 1,2,3,5 tetrasubstitution of Ar).
Table 2
Hydrogen-bonding geometry (A, ) for (III).
ꢀ
Ê
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
C5ÐH5Á Á ÁO1vii
0.95
0.95
2.46
2.62
3.406 (2)
3.560 (2)
171
170
C14ÐH14Á Á ÁO4vi
1
Symmetry codes: (vi) x; 12 y; 21 ‡ z; (vii) x; 21 y; ‡ z.
2
Compound (III)
Compound (IV) was obtained using the method described by Boss
& Scheffold (1976). To a solution of (III) (7 g, 15.6 mmol) in ethanol
(150 ml) were added 10% Pd on activated charcoal (1.5 g) and
p-toluenesulfonic acid (0.7 g) in water (5 ml). The stirred suspension
was re¯uxed for 2 d, after which time the reaction mixture was
®ltered hot. On cooling, the product precipitated out as a pale-yellow
powder, which was ®ltered off (yield 1 g). An additional portion of
(IV) (3 g) was obtained on concentration of the resulting ®ltrate.
Pale-yellow crystals of (IVa) suitable for X-ray studies were obtained
by slow evaporation from a solution of the product in diethyl ether.
The yield was 4 g (70%). TLC on silica gel (diethyl ether/petroleum
ether 40/60, 30:70): RF = 0.64. Analysis calculated: C 74.97, H 7.66%;
found: C 74.51, H 7.86%. 1H NMR (CDCl3, p.p.m.): 11.19 (s, 2H, ArÐ
OH), 9.86 (s, 2H, CHO), 7.64 (d, 2H, ArH), 7.37 (d, 2H, ArH), 4.03
(s, 2H, ArCH2Ar), 1.26 [s, 18H, C(CH3)3]. IR (KBr, cm 1): 1658
[ꢁ(C O)], 1270 [s, ꢁ(ArOH)], 1216 (s).
Crystal data
3
C29H36O4
Mr = 448.58
Dx = 1.150 Mg m
Mo Kꢂ radiation
Monoclinic, P21=c
Cell parameters from 7890
re¯ections
Ê
a = 16.2931 (10) A
ꢅ = 2.4±23.3ꢀ
ꢆ = 0.08 mm
T = 150 (2) K
Ê
b = 10.1951 (6) A
1
Ê
c = 16.4318 (10) A
ꢃ = 108.367 (1)ꢀ
Ê
V = 2590.4 (3) A
Z = 4
3
Block, colourless
0.26 Â 0.16 Â 0.14 mm
Data collection
Bruker SMART 1000 CCD area-
detector diffractometer
! scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
Tmin = 0.900, Tmax = 1.000
17 928 measured re¯ections
4559 independent re¯ections
3620 re¯ections with I > 2ꢇ(I)
Rint = 0.020
ꢅmax = 25.0ꢀ
h = 19 ! 19
k = 12 ! 12
l = 19 ! 19
Compound (II)
Crystal data
Re®nement
C29H40O4
Z = 2
Dx = 1.159 Mg m
Mo Kꢂ radiation
Re®nement on F2
R[F2 > 2ꢇ(F2)] = 0.043
wR(F2) = 0.123
S = 1.02
4559 re¯ections
w = 1/[ꢇ2(F2o) + (0.058P)2
+ 1.0861P]
3
Mr = 452.61
Triclinic, P1
a = 10.6025 (11) A
where P = (F2o + 2Fc2)/3
(Á/ꢇ)max = 0.001
Ê
Ê
Ê
Cell parameters from 2476
re¯ections
b = 11.9199 (12) A
3
ꢅ = 2.3±27.2ꢀ
ꢆ = 0.08 mm
T = 150 (2) K
Ê
Áꢈmax = 0.29 e A
c = 12.4180 (13) A
3
1
ꢂ = 64.611 (2)ꢀ
ꢃ = 82.672 (2)ꢀ
ꢄ = 66.330 (2)ꢀ
Ê
0.18 e A
317 parameters
H-atom parameters constrained
Áꢈmin
=
Block, colourless
0.29 Â 0.17 Â 0.12 mm
3
Ê
V = 1296.7 (2) A
Polymorph (IVa)
Data collection
Bruker SMART 1000 CCD area-
detector diffractometer
' and ! scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
Tmin = 0.938, Tmax = 1.000
9408 measured re¯ections
4565 independent re¯ections
3085 re¯ections with I > 2ꢇ(I)
Rint = 0.025
Crystal data
C23H28O4
Mr = 368.45
Tetragonal, I41=a
Ê
a = 12.7930 (7) A
c = 24.158 (2) A
Ê
V = 3953.7 (4) A
Mo Kꢂ radiation
Cell parameters from 3205
re¯ections
ꢅmax = 25.0ꢀ
h = 12 ! 12
ꢅ = 2.8±22.8ꢀ
ꢆ = 0.08 mm
T = 150 (2) K
k = 14 ! 14
1
Ê
l = 14 ! 14
3
Re®nement
Z = 8
Dx = 1.238 Mg m
Tablet, yellow
0.28 Â 0.20 Â 0.05 mm
3
Re®nement on F2
R[F2 > 2ꢇ(F2)] = 0.057
wR(F2) = 0.173
S = 1.04
4565 re¯ections
w = 1/[ꢇ2(F2o) + (0.0843P)2
+ 0.7234P]
Data collection
where P = (F2o + 2Fc2)/3
(Á/ꢇ)max < 0.001
Bruker SMART 1000 CCD area-
detector diffractometer
' and ! scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
Tmin = 0.931, Tmax = 1.000
19 093 measured re¯ections
1736 independent re¯ections
1203 re¯ections with I > 2ꢇ(I)
Rint = 0.056
ꢅmax = 25.0ꢀ
3
Ê
Áꢈmax = 0.69 e A
3
Ê
0.22 e A
310 parameters
H-atom parameters constrained
Áꢈmin
=
h = 15 ! 15
k = 15 ! 15
Table 1
Hydrogen-bonding geometry (A, ) for (II).
l = 28 ! 28
ꢀ
Ê
Re®nement
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
Re®nement on F2
R[F2 > 2ꢇ(F2)] = 0.043
wR(F2) = 0.120
S = 1.04
1736 re¯ections
w = 1/[ꢇ2(F2o) + (0.0446P)2
+ 4.6694P]
O1ÐH1OAÁ Á ÁO4i
O1ÐH1OBÁ Á ÁO4iv
O4ÐH4OAÁ Á ÁO1iv
O4ÐH4OBÁ Á ÁO1v
0.83
0.82
0.91
0.84
1.93
1.99
1.85
1.90
2.744 (3)
2.749 (2)
2.749 (2)
2.744 (3)
166
155
167
177
where P = (F2o + 2Fc2)/3
(Á/ꢇ)max < 0.001
3
Ê
Áꢈmax = 0.19 e A
3
Ê
0.21 e A
125 parameters
H-atom parameters constrained
Áꢈmin
=
Symmetry codes: (i) 1 ‡ x; y; z; (iv) x; 1 y; z; (v) x 1; y; z.
Acta Cryst. (2004). C60, o776±o780
ꢁ
Sandrine Goetz et al. C29H40O4, C29H36O4 and C23H28O4 o779

organic compounds
Polymorph (IVb)
Except as described below, H atoms bonded to C atoms were
placed at calculated positions and re®ned using a riding model. The
Ê
constrained CÐH distances were 0.95, 0.98, 0.99 and 0.99 A for aryl,
Crystal data
3
C23H28O4
Mr = 368.45
Dx = 1.174 Mg m
Mo Kꢂ radiation
methyl, methylene and ethylene H atoms, respectively. The Uiso(H)
values were set at 1.2Ueq(C) for methylene and aryl H atoms, and at
1.5Ueq(C) for tert-butyl H atoms. For (II), the disordered H atoms
bonded to atoms O1 and O4 were located from difference maps and
Monoclinic, C2=c
Cell parameters from 3051
re¯ections
Ê
a = 26.809 (2) A
ꢅ = 2.6±25.6ꢀ
Ê
b = 8.4543 (7) A
1
2
Ê
c = 21.3720 (18) A
Ê
ꢆ = 0.08 mm
T = 153 (2) K
were not further re®ned; their Uiso(H) values were ®xed at 0.04 A .
ꢃ = 120.618 (1)ꢀ
Ê
V = 4168.7 (6) A
Z = 8
2
The Uiso(H) values of the tert-butyl H atoms were ®xed at 0.05 A ,
Ê
3
Tablet, light brown
0.48 Â 0.38 Â 0.16 mm
2
and those of the H atoms on atoms C27 and C24 at 0.04 A . For (IVa),
Ê
H atoms bonded to O atoms were placed at calculated positions, with
Data collection
Ê
a constrained OÐH distance of 0.84 A and with Uiso(H) set at 1.5Ueq
of the carrier O atom. In (IVb), the Uiso values for the tert-butyl H
Bruker SMART 1000 CCD area-
detector diffractometer
' and ! scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
Tmin = 0.919, Tmax = 1.000
14 739 measured re¯ections
3668 independent re¯ections
2235 re¯ections with I > 2ꢇ(I)
Rint = 0.049
2
atoms were ®xed at 0.05 A , while the phenol H atoms were located
Ê
from difference maps and their positions re®ned, with Uiso(H) values
2
®xed at 0.05 A .
ꢅmax = 25.0ꢀ
Ê
h = 31 ! 31
k = 10 ! 10
For all determinations, data collection: SMART (Bruker, 1998);
cell re®nement: SMART; data reduction: SAINT (Bruker, 1998);
program(s) used to solve structure: SHELXTL (Sheldrick, 2001);
program(s) used to re®ne structure: SHELXTL; molecular graphics:
SHELXTL; software used to prepare material for publication:
SHELXTL.
l = 25 ! 25
Re®nement
Re®nement on F2
R[F2 > 2ꢇ(F2)] = 0.047
wR(F2) = 0.132
S = 1.01
3668 re¯ections
251 parameters
H atoms treated by a mixture of
independent and constrained
re®nement
w = 1/[ꢇ2(F2o) + (0.0393P)2
+ 4.8718P]
where P = (F2o + 2Fc2)/3
(Á/ꢇ)max < 0.001
3
Ê
Áꢈmax = 0.20 e A
The authors thank Professor M. A. McKervey and Dr
H. Q. N. Gunaratne, CSS Limited, for helpful discussions.
3
Ê
0.18 e A
Áꢈmin
=
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: BM1580). Services for accessing these data are
described at the back of the journal.
Table 3
Hydrogen-bonding geometry (A, ) for (IVa).
ꢀ
Ê
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
O2ÐH2Á Á ÁO1
0.92 (2)
1.80 (2)
2.645 (2)
151 (2)
References
Barreira Fontecha, J., Goetz, S. & McKee, V. (2002). Angew. Chem. Int. Ed. 41,
4554±4556.
Boss, R. & Scheffold, R. (1976). Angew. Chem. 88, 578±579.
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin,
USA.
Dhawan, B. & Gutsche, C. D. (1983). J. Org. Chem. 48, 1536±1539.
Masci, B., Levi Mortera, S., Seralessandri, L. & Thuery, P. (2004) Acta Cryst.
C60, o107±o109.
Sheldrick, G. M. (2001). SHELXTL (Version 6.12) and SADABS (Version
6.12). Bruker AXS Inc., Madison, Wisconsin, USA.
Taniguchi, S. (1984). Bull. Chem. Soc. Jpn, 57, 2683±2684.
Table 4
Hydrogen-bonding geometry (A, ) for (IVb).
ꢀ
Ê
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
O2ÐH2Á Á ÁO1
O4ÐH4Á Á ÁO3
C13ÐH13Á Á ÁO3ii
0.94 (2)
0.88 (2)
0.95
1.81 (2)
1.85 (2)
2.57
2.625 (3)
2.631 (2)
3.454 (3)
144 (2)
147 (2)
156
Symmetry code: (ii) x; 2 y; 1 z.
ꢁ
o780 Sandrine Goetz et al.
C29H40O4, C29H36O4 and C23H28O4
Acta Cryst. (2004). C60, o776±o780