organic compounds
Data collection
Re®nement
Siemens CCD three-circle diffract-
ometer
! scans
Absorption correction: empirical
(SADABS; Sheldrick, 1996)
Tmin = 0.583, Tmax = 0.643
61 228 measured re¯ections
7069 independent re¯ections
6477 re¯ections with I > 2ꢃ(I)
Rint = 0.022
max = 28.28ꢁ
Re®nement on F2
R[F2 > 2ꢃ(F2)] = 0.056
wR(F2) = 0.136
S = 1.003
2886 re¯ections
211 parameters
H atoms treated by a mixture of
independent and constrained
re®nement
ꢁ
h = 11 ! 11
k = 33 ! 33
w = 1/[ꢃ2(Fo2) + (0.0636P)2]
where P = (Fo2 + 2Fc2)/3
(Á/ꢃ)max = 0.003
l = 18 ! 18
943 standard re¯ections
frequency: 1000 min
intensity decay: none
3
Ê
Áꢄmax = 0.47 e A
3
Ê
0.45 e A
Áꢄmin
=
Table 5
Torsion angles (ꢁ).
Re®nement
Re®nement on F2
R[F2 > 2ꢃ(F2)] = 0.026
wR(F2) = 0.061
S = 1.142
7069 re¯ections
359 parameters
H atoms treated by a mixture of
independent and constrained
re®nement
w = 1/[ꢃ2(Fo2) + (0.0212P)2
+ 2.1579P]
(III)
(IVa)
(IVb) (IVb)
Molecule 1 Molecule 2
(V)
where P = (Fo2 + 2Fc2)/3
(Á/ꢃ)max = 0.002
3
C2ÐC1ÐC11ÐO11 124.7 (3) 105.94 (17) 114.75 (17) 128.70 (17) 119.7 (6)
C2ÐC1ÐC11ÐO12 61.3 (3) 73.11 (16) 65.44 (17) 54.89 (18) 61.3 (5)
C1ÐC2ÐC21ÐO21 29.4 (4) 41.7 (2)
C1ÐC2ÐC21ÐO22 154.0 (3) 138.93 (14) 109.20 (16) 134.35 (14) 127.9 (5)
Ê
Áꢄmax = 0.35 e A
3
Ê
0.27 e A
Áꢄmin
=
69.4 (2)
44.7 (2)
50.9 (7)
Table 3
Hydrogen-bonding geometry (A, ) for (IVb).
The C and O atoms of the disordered solvent in (II) were re®ned
isotropically. All H atoms on C atoms, except those of the disordered
solvent in (II), were located by difference Fourier synthesis and were
re®ned with ®xed individual displacement parameters [U(H) =
1.5Ueq(Cmethyl) or U(H) = 1.2Ueq(C)] using a riding model with
ꢁ
Ê
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
O12ÐH12Á Á ÁO11Ai
O22ÐH22Á Á ÁO21Aii
O12AÐH12AÁ Á ÁO11i
O22AÐH22AÁ Á ÁO21ii
0.79 (3)
0.76 (3)
0.83 (3)
0.90 (4)
1.88 (3)
1.86 (3)
1.80 (3)
1.84 (4)
2.6627 (17)
2.6186 (17)
2.6320 (17)
2.7347 (17)
174 (3)
175 (3)
178 (3)
171 (3)
Ê
aromatic CÐH = 0.95 A, methyl CÐH = 0.98 A, secondary CÐH =
Ê
Ê
Ê
0.99 A and tertiary CÐH = 1.00 A. The hydroxyl H atoms of (IVa),
(IVb) and (V) were re®ned isotropically, whereas the hydroxyl H
atoms in (III) were re®ned with ®xed individual displacement
parameters [U(H) = 1.2Ueq(O)] using a riding model with OÐH =
Symmetry codes: (i) 1 x; 1 y; 1 z; (ii) 2 x; 1 y; 1 z.
Ê
0.84 A and allowing the OH groups to rotate about the CÐO axis.
The absolute structure of (I) could not be determined reliably [Flack
(1983) parameter 0.3 (13)].
Compound (V)
For all compounds, data collection: SMART (Siemens, 1995); cell
re®nement: SMART; data reduction: SAINT (Siemens, 1995);
program(s) used to solve structure: SHELXS97 (Sheldrick, 1990);
program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997);
molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991).
Crystal data
C11H8Cl6O4ÁH2O
Z = 2
Dx = 1.770 Mg m
Mo Kꢀ radiation
3
Mr = 434.89
Triclinic, P1
a = 8.616 (3) A
Ê
Cell parameters from 2320
re¯ections
Ê
b = 9.281 (2) A
ꢁ = 1±20ꢁ
ꢂ = 1.069 mm
T = 173 (2) K
Ê
c = 10.460 (4) A
1
ꢀ = 100.53 (2)ꢁ
ꢅ = 94.00 (2)ꢁ
ꢆ = 95.06 (2)ꢁ
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: SK1412). Services for accessing these data are
described at the back of the journal.
Plate, colourless
0.25 Â 0.20 Â 0.10 mm
3
Ê
V = 816.0 (5) A
Data collection
Siemens CCD three-circle diffract-
ometer
! scans
Absorption correction: empirical
(SADABS; Sheldrick, 1996)
Tmin = 0.776, Tmax = 0.901
11 168 measured re¯ections
2886 independent re¯ections
1709 re¯ections with I > 2ꢃ(I)
Rint = 0.086
max = 25.03ꢁ
ꢁ
References
h = 10 ! 10
Avitabile, G., Ganis, P. & Nemiroff, M. (1973). Cryst. Struct. Commun. 2, 455±
457.
Cser, F. & Sasvari, K. (1976). J. Chem. Soc. Perkin Trans. 2, pp. 478±480.
Destro, R., Filippini, G., Gramaccioli, C. M. & Simonetta, M. (1969). Acta
Cryst. B25, 2465±2472.
k = 11 ! 11
l = 12 ! 12
69 standard re¯ections
frequency: 900 min
intensity decay: none
Diels, O. & Alder, K. (1928). Ann. Chem. 460, 98±122.
Flack, H. D. (1983). Acta Cryst. A39, 876±881.
È
È
Hunig, S., Markl, G. & Sauer, J. (1979). Integriertes Organisches Praktikum,
pp. 83±88. Weinheim: VCH.
Table 4
Hydrogen-bonding geometry (A, ) for (V).
ꢁ
Ê
P¯uger, C. E., Harlow, R. L. & Simonsen, S. H. (1973). J. Cryst. Mol. Struct. 3,
277±283.
Sheldrick, G. M. (1990). Acta Cryst. A46, 467±473.
Sheldrick, G. M. (1991). SHELXTL-Plus. Release 4.1. Siemens Analytical
X-ray Instruments Inc., Madison, Wisconsin, USA.
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
O22ÐH22Á Á ÁO1W i
O1WÐH1WÁ Á ÁO11
O1WÐH2WÁ Á ÁO21ii
0.96 (7)
0.94 (7)
0.74 (6)
1.60 (7)
2.01 (7)
2.12 (6)
2.564 (6)
2.852 (6)
2.835 (6)
176 (6)
148 (6)
165 (7)
È
Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany.
Sheldrick, G. M. (1997). SHELXL97. University of Gottingen, Germany.
È
Siemens (1995). SMART and SAINT. Siemens Analytical X-ray Instruments
Inc., Madison, Wisconsin, USA.
Symmetry codes: (i) x 1; y; z; (ii) 2 x; 2 y; 1 z.
ꢀ
1342 Bolte, Degen and Egert Five Diels±Alder adducts
Acta Cryst. (2000). C56, 1338±1342