organic compounds
Table 2
Hydrogen-bonding geometry (A, ).
The entire molecule of (I), including the methoxy group, is
Ê
planar (mean deviation 0.006 A from the plane of the ring;
ꢀ
Ê
Ê
maximum deviation 0.201 A for C14). This is ascribable to the
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
formation of a bifurcated intermolecular hydrogen bond from
H4 of a neighbouring molecule to O11 and O13 (Fig. 1). The
interaction shown in Fig. 1 extends to form corrugated sheets
of molecules which are hydrogen bonded together by mol-
ecules of water of crystallization (see Table 2).
O2ÐH2Á Á ÁO1Wi
O4ÐH4Á Á ÁO11ii
O4ÐH4Á Á ÁO13ii
O6ÐH6Á Á ÁO11
0.85 (2)
0.86 (3)
0.86 (3)
0.90 (2)
0.86 (2)
0.92 (2)
1.85 (2)
1.98 (2)
2.32 (3)
1.66 (2)
2.00 (2)
2.02 (2)
2.7017 (16)
2.6727 (15)
3.0881 (17)
2.4860 (14)
2.8514 (16)
2.9345 (14)
171 (2)
137 (2)
149 (2)
150 (2)
172 (2)
175 (2)
O1WÐH1WÁ Á ÁO6iii
O1WÐH2WÁ Á ÁO4iv
Symmetry codes: (i) 12 x; 21 y; z; (ii) x; y; z 21; (iii) x; y; z; (iv) x; y; 12 z.
Experimental
Re®nement
Compound (I) was prepared by the Houben±Hoesch reaction of
phloroglucinol with methoxyacetonitrile in the presence of an-
hydrous HCl and ZnCl2 (Deng et al., 1997). Crystals were obtained by
recrystallization from water.
Re®nement on F2
R[F2 > 2ꢄ(F2)] = 0.041
wR(F2) = 0.109
S = 1.050
2180 re¯ections
w = 1/[ꢄ2(Fo2) + (0.0647P)2
+ 0.0798P]
where P = (Fo2 + 2Fc2)/3
(Á/ꢄ)max = 0.003
3
Ê
Áꢅmax = 0.25 e A
3
Ê
0.30 e A
185 parameters
All H-atom parameters re®ned
Áꢅmin
=
Crystal data
Extinction correction: SHELXL97
(Sheldrick, 1997)
Extinction coef®cient: 0.0031 (7)
3
C9H10O5ÁH2O
Dx = 1.518 Mg m
Mo Kꢁ radiation
Cell parameters from 24172
re¯ections
Mr = 216.19
Monoclinic, C2/c
Ê
a = 17.3138 (5) A
Ê
b = 7.33300 (10) A
Ê
ꢂ = 2.66±27.56ꢀ
ꢃ = 0.129 mm
T = 150 (2) K
The re®ned CÐH distances are in the range 0.94 (2)±1.03 (2) A.
Data collection and re®nement: COLLECT (Hooft, 1998); data
reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to
solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to
re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
SHELXTL (Sheldrick, 1995).
1
Ê
c = 16.8507 (5) A
ꢀ = 117.8380 (10)ꢀ
3
Ê
V = 1891.81 (8) A
Z = 8
Block, colourless
0.35 Â 0.10 Â 0.10 mm
Data collection
Nonius KappaCCD diffractometer
!±' scans
1594 re¯ections with I > 2ꢄ(I)
Rint = 0.076
We thank the EPSRC X-ray crystallography data collection
Absorption correction: multi-scan
(SORTAV; Blessing, 1995, 1997)
Tmin = 0.811, Tmax = 1.000
24172 measured re¯ections
2180 independent re¯ections
ꢂ
max = 27.56ꢀ
Â
Ã
service for diffraction data, and Ministerio para a Ciencia e
Tecnologia, Portugal, for the award of a studentship (PRAXIS
XXI BD 13451/97) to ESBF.
h = 22 ! 22
k = 9 ! 9
l = 21 ! 21
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: BJ1012). Services for accessing these data are
described at the back of the journal.
Table 1
Selected geometric parameters (A, ).
ꢀ
Ê
References
C1ÐC2
C1ÐC6
1.4190 (18)
1.4265 (18)
1.4499 (17)
1.2466 (15)
1.5096 (18)
1.4084 (16)
1.4246 (17)
C2ÐO2
C2ÐC3
C3ÐC4
C4ÐO4
C4ÐC5
C5ÐC6
C6ÐO6
1.3495 (15)
1.3831 (18)
1.3872 (19)
1.3537 (16)
1.3849 (19)
1.3808 (18)
1.3527 (16)
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Blessing, R. H. (1997). J. Appl. Cryst. 30, 421±426.
C1ÐC11
C11ÐO11
C11ÐC12
C12ÐO13
O13ÐC14
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C2ÐC1ÐC6
116.34 (11)
124.61 (11)
119.06 (11)
120.54 (12)
116.80 (11)
122.66 (11)
108.82 (10)
111.25 (10)
120.47 (12)
118.08 (11)
C3ÐC2ÐC1
C2ÐC3ÐC4
O4ÐC4ÐC5
O4ÐC4ÐC3
C5ÐC4ÐC3
C6ÐC5ÐC4
O6ÐC6ÐC5
O6ÐC6ÐC1
C5ÐC6ÐC1
121.45 (12)
119.69 (12)
117.42 (12)
121.18 (12)
121.39 (12)
118.91 (12)
117.23 (12)
120.57 (11)
122.20 (12)
C2ÐC1ÐC11
C6ÐC1ÐC11
O11ÐC11ÐC1
O11ÐC11ÐC12
C1ÐC11ÐC12
O13ÐC12ÐC11
C12ÐO13ÐC14
O2ÐC2ÐC3
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Inc., Madison, Wisconsin, USA.
È
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È
Heitsch, H., Rathmann, R., Hauen, B. M. & Schulz, K.-H. (1990). Acta
Cryst. C46, 1715±1718.
O2ÐC2ÐC1
ꢁ
212 Ester S. B. Ferreira et al.
C9H10O5ÁH2O
Acta Cryst. (2001). C57, 211±212