(1R,2S,3R,6S,7R,8S)-Tricyclo­[6.2.1.02,7]undeca-4,9-diene-3,6-diol

Banister, S.D.; Clegg, J.K.; Coster, M.J.; Jolliffe, K.A.; Kassiou, M.

doi:10.1107/S1600536806051002

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(1R,2S,3R,6S,7R,8S)-Tricyclo[6.2.1.0^2,7]undeca-4,9-diene-3,6-diol

S. D. Banister, J. K. Clegg, M. J. Coster, K. A. Jolliffe and M. Kassiou

The asymmetric unit of the title compound, C₁₁H₁₄O₂, contains two molecules. The alcohol groups have cis stereochemistry and are involved in hydrogen bonding (acting as both donors and acceptors), resulting in the formation of an infinite three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051002/er2024sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051002/er2024Isup2.hkl Contains datablock I

CCDC reference: 633685

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.003 Å
R factor = 0.052
wR factor = 0.118
Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.766     0.990
            Tmin(prime) and Tmax expected:      0.974     0.990
            RR(prime) =      0.786
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.79

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           32.65
           From the CIF: _reflns_number_total               3539
           Count of symmetry unique reflns         3551
           Completeness (_total/calc)             99.66%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT792_ALERT_1_G Check the Absolute Configuration of C5     = ...          R
PLAT792_ALERT_1_G Check the Absolute Configuration of C6     = ...          S
PLAT792_ALERT_1_G Check the Absolute Configuration of C7     = ...          S
PLAT792_ALERT_1_G Check the Absolute Configuration of C9     = ...          R
PLAT792_ALERT_1_G Check the Absolute Configuration of C16    = ...          R
PLAT792_ALERT_1_G Check the Absolute Configuration of C17    = ...          S
PLAT792_ALERT_1_G Check the Absolute Configuration of C18    = ...          S
PLAT792_ALERT_1_G Check the Absolute Configuration of C20    = ...          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   9 ALERT level G = General alerts; check

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX (Bruker–Nonius, 2003); cell refinement: SAINT (Bruker–Nonius, 2003); data reduction: SAINT and XPREP (Bruker–Nonius, 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997), WinGX32 (Farrugia, 1999), POV-RAY 3.5 (Cason, 2002) and WebLab ViewerPro 3.7 (Molecular Simulations, 2000); software used to prepare material for publication: enCIFer (Version 1.1; Allen et al., 2004).

(1R,2S,3R,6S,7R,8S)-Tricyclo[6.2.1.0^2,7]undeca-4,9-diene-3,6-diol top

Crystal data top

C₁₁H₁₄O₂	F(000) = 768
M_r = 178.22	D_x = 1.267 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 782 reflections
a = 12.5265 (15) Å	θ = 3.8–30.9°
b = 10.7003 (13) Å	µ = 0.09 mm⁻¹
c = 13.9454 (13) Å	T = 150 K
V = 1869.2 (4) Å³	Prism, colourless
Z = 8	0.30 × 0.28 × 0.12 mm

Data collection top

Bruker–Nonius APEXII-FR591 diffractometer	3539 independent reflections
Radiation source: rotating anode	2747 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω and φ scans	θ_max = 32.7°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −19→15
T_min = 0.766, T_max = 0.990	k = −13→16
21673 measured reflections	l = −21→21

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0599P)² + 0.0703P] where P = (F_o² + 2F_c²)/3
3539 reflections	(Δ/σ)_max < 0.001
247 parameters	Δρ_max = 0.31 e Å⁻³
1 restraint	Δρ_min = −0.28 e Å⁻³

Special details top

Experimental. The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.72941 (15)	0.54259 (18)	0.30629 (13)	0.0170 (4)
H1	0.7804	0.4818	0.2768	0.020*
C2	0.62560 (16)	0.5337 (2)	0.25284 (13)	0.0214 (4)
H2	0.6132	0.5884	0.2003	0.026*
C3	0.55117 (17)	0.4523 (2)	0.27667 (14)	0.0234 (4)
H3	0.4867	0.4501	0.2409	0.028*
C4	0.56511 (15)	0.36320 (19)	0.35829 (13)	0.0165 (4)
H4	0.6046	0.2887	0.3336	0.020*
C5	0.62953 (16)	0.41745 (19)	0.44161 (13)	0.0179 (4)
H5	0.6640	0.3457	0.4756	0.021*
C6	0.72023 (15)	0.51143 (18)	0.41380 (13)	0.0160 (4)
H6	0.7897	0.4740	0.4345	0.019*
C7	0.56524 (19)	0.4935 (2)	0.51834 (17)	0.0302 (5)
H7	0.5162	0.4434	0.5599	0.036*
C8	0.6598 (2)	0.5561 (2)	0.57037 (14)	0.0313 (5)
H8A	0.6371	0.6127	0.6227	0.038*
H8B	0.7131	0.4953	0.5942	0.038*
C9	0.69722 (16)	0.62626 (19)	0.48060 (13)	0.0187 (4)
H9	0.7582	0.6853	0.4902	0.022*
C10	0.59376 (18)	0.6849 (2)	0.44797 (17)	0.0261 (5)
H10	0.5856	0.7633	0.4169	0.031*
C11	0.51623 (19)	0.6056 (2)	0.4710 (2)	0.0349 (6)
H11	0.4422	0.6178	0.4595	0.042*
C12	0.68280 (15)	−0.10642 (19)	0.63270 (14)	0.0181 (4)
H12	0.6343	−0.1769	0.6149	0.022*
C13	0.69617 (17)	−0.02617 (19)	0.54562 (13)	0.0209 (4)
H13	0.7590	−0.0330	0.5079	0.025*
C14	0.62081 (17)	0.0543 (2)	0.52095 (14)	0.0217 (4)
H14	0.6290	0.1038	0.4649	0.026*
C15	0.52274 (16)	0.0673 (2)	0.58135 (14)	0.0200 (4)
H15	0.4741	−0.0035	0.5647	0.024*
C16	0.54486 (17)	0.0598 (2)	0.68989 (14)	0.0222 (4)
H16	0.4768	0.0351	0.7222	0.027*
C17	0.63195 (16)	−0.0383 (2)	0.71807 (14)	0.0209 (4)
H17	0.5974	−0.1026	0.7599	0.025*
C18	0.5865 (2)	0.1822 (2)	0.73985 (16)	0.0336 (6)
H18	0.5329	0.2506	0.7476	0.040*
C19	0.6290 (2)	0.1239 (3)	0.83401 (17)	0.0425 (7)
H19A	0.6631	0.1859	0.8769	0.051*
H19B	0.5740	0.0758	0.8692	0.051*
C20	0.71012 (19)	0.0400 (2)	0.78214 (15)	0.0310 (5)
H20	0.7586	−0.0095	0.8245	0.037*
C21	0.7641 (2)	0.1359 (2)	0.71871 (19)	0.0352 (6)
H21	0.8370	0.1361	0.7000	0.042*
C22	0.6910 (2)	0.2195 (2)	0.69408 (19)	0.0377 (6)
H22	0.7023	0.2905	0.6545	0.045*
O1	0.77176 (12)	0.66658 (13)	0.29236 (10)	0.0213 (3)
O2	0.46118 (11)	0.32170 (15)	0.38876 (11)	0.0240 (3)
O3	0.78382 (11)	−0.15982 (14)	0.65897 (11)	0.0219 (3)
O4	0.46856 (12)	0.18158 (15)	0.55625 (11)	0.0253 (3)
H1O	0.830 (2)	0.671 (2)	0.326 (2)	0.038*
H2O	0.468 (2)	0.281 (3)	0.437 (2)	0.038*
H3O	0.773 (2)	−0.219 (2)	0.704 (2)	0.038*
H4O	0.412 (2)	0.176 (3)	0.584 (2)	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0185 (9)	0.0183 (9)	0.0144 (7)	−0.0026 (8)	0.0008 (6)	0.0003 (7)
C2	0.0223 (10)	0.0293 (11)	0.0124 (7)	−0.0043 (9)	−0.0051 (7)	0.0044 (8)
C3	0.0227 (10)	0.0321 (12)	0.0152 (8)	−0.0056 (9)	−0.0066 (7)	0.0030 (8)
C4	0.0145 (8)	0.0189 (10)	0.0161 (7)	−0.0029 (7)	−0.0015 (6)	0.0014 (7)
C5	0.0222 (10)	0.0164 (9)	0.0151 (7)	−0.0041 (8)	−0.0014 (7)	0.0023 (7)
C6	0.0161 (9)	0.0176 (10)	0.0143 (7)	0.0001 (7)	−0.0036 (6)	0.0024 (7)
C7	0.0376 (12)	0.0276 (12)	0.0255 (9)	−0.0177 (10)	0.0145 (9)	−0.0090 (9)
C8	0.0520 (15)	0.0265 (12)	0.0155 (9)	−0.0150 (11)	0.0017 (9)	−0.0016 (8)
C9	0.0213 (9)	0.0205 (10)	0.0142 (7)	−0.0043 (8)	−0.0006 (7)	−0.0008 (7)
C10	0.0260 (11)	0.0222 (11)	0.0301 (10)	0.0024 (9)	0.0006 (8)	−0.0085 (9)
C11	0.0213 (11)	0.0325 (14)	0.0508 (15)	−0.0006 (10)	0.0088 (10)	−0.0184 (12)
C12	0.0194 (10)	0.0160 (10)	0.0189 (8)	0.0024 (8)	0.0011 (7)	−0.0002 (7)
C13	0.0243 (10)	0.0217 (10)	0.0167 (8)	0.0012 (9)	0.0044 (7)	−0.0009 (8)
C14	0.0266 (10)	0.0245 (11)	0.0140 (8)	−0.0005 (9)	0.0017 (7)	0.0017 (8)
C15	0.0214 (10)	0.0188 (10)	0.0199 (8)	−0.0009 (8)	−0.0008 (7)	0.0036 (7)
C16	0.0203 (10)	0.0275 (11)	0.0188 (9)	0.0091 (8)	0.0037 (7)	0.0056 (8)
C17	0.0239 (10)	0.0225 (10)	0.0163 (8)	0.0049 (8)	0.0031 (7)	0.0056 (8)
C18	0.0444 (14)	0.0327 (13)	0.0237 (10)	0.0191 (11)	−0.0070 (10)	−0.0073 (9)
C19	0.0592 (17)	0.0476 (16)	0.0208 (10)	0.0267 (14)	−0.0081 (11)	−0.0112 (11)
C20	0.0381 (13)	0.0349 (13)	0.0201 (9)	0.0161 (10)	−0.0072 (9)	−0.0087 (9)
C21	0.0363 (14)	0.0316 (13)	0.0378 (12)	−0.0056 (11)	−0.0116 (11)	−0.0109 (11)
C22	0.0549 (17)	0.0222 (12)	0.0360 (12)	−0.0039 (11)	−0.0130 (12)	−0.0079 (10)
O1	0.0196 (7)	0.0239 (8)	0.0204 (7)	−0.0068 (6)	−0.0030 (5)	0.0056 (6)
O2	0.0170 (7)	0.0284 (9)	0.0266 (7)	−0.0057 (6)	−0.0041 (6)	0.0107 (7)
O3	0.0199 (7)	0.0206 (8)	0.0252 (7)	0.0050 (6)	0.0043 (6)	0.0056 (6)
O4	0.0204 (7)	0.0285 (8)	0.0270 (7)	0.0052 (7)	0.0025 (6)	0.0113 (7)

Geometric parameters (Å, º) top

C1—O1	1.442 (2)	C12—C17	1.534 (3)
C1—C2	1.502 (3)	C12—H12	1.0000
C1—C6	1.540 (3)	C13—C14	1.323 (3)
C1—H1	1.0000	C13—H13	0.9500
C2—C3	1.319 (3)	C14—C15	1.496 (3)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.495 (3)	C15—O4	1.441 (2)
C3—H3	0.9500	C15—C16	1.541 (3)
C4—O2	1.440 (2)	C15—H15	1.0000
C4—C5	1.529 (3)	C16—C17	1.564 (3)
C4—H4	1.0000	C16—C18	1.572 (3)
C5—C6	1.566 (3)	C16—H16	1.0000
C5—C7	1.567 (3)	C17—C20	1.569 (3)
C5—H5	1.0000	C17—H17	1.0000
C6—C9	1.569 (3)	C18—C22	1.509 (4)
C6—H6	1.0000	C18—C19	1.548 (3)
C7—C11	1.500 (4)	C18—H18	1.0000
C7—C8	1.542 (3)	C19—C20	1.536 (3)
C7—H7	1.0000	C19—H19A	0.9900
C8—C9	1.533 (3)	C19—H19B	0.9900
C8—H8A	0.9900	C20—C21	1.514 (4)
C8—H8B	0.9900	C20—H20	1.0000
C9—C10	1.510 (3)	C21—C22	1.326 (4)
C9—H9	1.0000	C21—H21	0.9500
C10—C11	1.329 (3)	C22—H22	0.9500
C10—H10	0.9500	O1—H1O	0.87 (3)
C11—H11	0.9500	O2—H2O	0.81 (3)
C12—O3	1.436 (2)	O3—H3O	0.90 (3)
C12—C13	1.497 (3)	O4—H4O	0.80 (3)

O1—C1—C2	108.05 (16)	C13—C12—C17	113.81 (16)
O1—C1—C6	110.96 (15)	O3—C12—H12	107.4
C2—C1—C6	113.88 (16)	C13—C12—H12	107.4
O1—C1—H1	107.9	C17—C12—H12	107.4
C2—C1—H1	107.9	C14—C13—C12	120.29 (18)
C6—C1—H1	107.9	C14—C13—H13	119.9
C3—C2—C1	121.92 (18)	C12—C13—H13	119.9
C3—C2—H2	119.0	C13—C14—C15	120.01 (18)
C1—C2—H2	119.0	C13—C14—H14	120.0
C2—C3—C4	122.05 (18)	C15—C14—H14	120.0
C2—C3—H3	119.0	O4—C15—C14	109.21 (16)
C4—C3—H3	119.0	O4—C15—C16	111.55 (17)
O2—C4—C3	108.41 (16)	C14—C15—C16	113.61 (17)
O2—C4—C5	111.72 (16)	O4—C15—H15	107.4
C3—C4—C5	113.47 (16)	C14—C15—H15	107.4
O2—C4—H4	107.7	C16—C15—H15	107.4
C3—C4—H4	107.7	C15—C16—C17	114.03 (17)
C5—C4—H4	107.7	C15—C16—C18	116.85 (18)
C4—C5—C6	116.01 (15)	C17—C16—C18	102.49 (17)
C4—C5—C7	116.41 (17)	C15—C16—H16	107.7
C6—C5—C7	102.03 (16)	C17—C16—H16	107.7
C4—C5—H5	107.3	C18—C16—H16	107.7
C6—C5—H5	107.3	C12—C17—C16	114.42 (16)
C7—C5—H5	107.3	C12—C17—C20	115.89 (17)
C1—C6—C5	115.73 (15)	C16—C17—C20	102.69 (17)
C1—C6—C9	114.98 (16)	C12—C17—H17	107.8
C5—C6—C9	102.86 (15)	C16—C17—H17	107.8
C1—C6—H6	107.6	C20—C17—H17	107.8
C5—C6—H6	107.6	C22—C18—C19	99.6 (2)
C9—C6—H6	107.6	C22—C18—C16	108.69 (18)
C11—C7—C8	100.03 (18)	C19—C18—C16	98.88 (19)
C11—C7—C5	108.99 (19)	C22—C18—H18	115.8
C8—C7—C5	98.74 (18)	C19—C18—H18	115.8
C11—C7—H7	115.6	C16—C18—H18	115.8
C8—C7—H7	115.6	C20—C19—C18	93.63 (18)
C5—C7—H7	115.6	C20—C19—H19A	113.0
C9—C8—C7	93.62 (16)	C18—C19—H19A	113.0
C9—C8—H8A	113.0	C20—C19—H19B	113.0
C7—C8—H8A	113.0	C18—C19—H19B	113.0
C9—C8—H8B	113.0	H19A—C19—H19B	110.4
C7—C8—H8B	113.0	C21—C20—C19	100.1 (2)
H8A—C8—H8B	110.4	C21—C20—C17	107.95 (17)
C10—C9—C8	100.80 (18)	C19—C20—C17	99.64 (19)
C10—C9—C6	107.70 (16)	C21—C20—H20	115.7
C8—C9—C6	99.06 (16)	C19—C20—H20	115.7
C10—C9—H9	115.7	C17—C20—H20	115.7
C8—C9—H9	115.7	C22—C21—C20	107.4 (2)
C6—C9—H9	115.7	C22—C21—H21	126.3
C11—C10—C9	106.8 (2)	C20—C21—H21	126.3
C11—C10—H10	126.6	C21—C22—C18	108.1 (2)
C9—C10—H10	126.6	C21—C22—H22	125.9
C10—C11—C7	108.5 (2)	C18—C22—H22	125.9
C10—C11—H11	125.7	C1—O1—H1O	106.7 (18)
C7—C11—H11	125.7	C4—O2—H2O	108.2 (19)
O3—C12—C13	109.68 (16)	C12—O3—H3O	108.9 (17)
O3—C12—C17	110.91 (16)	C15—O4—H4O	104 (2)

O1—C1—C2—C3	−156.2 (2)	O3—C12—C13—C14	−164.68 (19)
C6—C1—C2—C3	−32.4 (3)	C17—C12—C13—C14	−39.8 (3)
C1—C2—C3—C4	−0.1 (3)	C12—C13—C14—C15	1.3 (3)
C2—C3—C4—O2	158.8 (2)	C13—C14—C15—O4	164.07 (19)
C2—C3—C4—C5	34.1 (3)	C13—C14—C15—C16	38.8 (3)
O2—C4—C5—C6	−156.38 (17)	O4—C15—C16—C17	−162.26 (16)
C3—C4—C5—C6	−33.5 (3)	C14—C15—C16—C17	−38.3 (3)
O2—C4—C5—C7	−36.3 (2)	O4—C15—C16—C18	−42.9 (2)
C3—C4—C5—C7	86.6 (2)	C14—C15—C16—C18	81.1 (2)
O1—C1—C6—C5	151.00 (16)	O3—C12—C17—C16	159.78 (17)
C2—C1—C6—C5	28.8 (3)	C13—C12—C17—C16	35.5 (3)
O1—C1—C6—C9	31.2 (2)	O3—C12—C17—C20	40.5 (2)
C2—C1—C6—C9	−91.0 (2)	C13—C12—C17—C20	−83.7 (2)
C4—C5—C6—C1	3.0 (3)	C15—C16—C17—C12	2.1 (3)
C7—C5—C6—C1	−124.59 (19)	C18—C16—C17—C12	−125.17 (19)
C4—C5—C6—C9	129.22 (17)	C15—C16—C17—C20	128.49 (19)
C7—C5—C6—C9	1.63 (19)	C18—C16—C17—C20	1.2 (2)
C4—C5—C7—C11	−62.5 (2)	C15—C16—C18—C22	−60.4 (2)
C6—C5—C7—C11	64.9 (2)	C17—C16—C18—C22	65.1 (2)
C4—C5—C7—C8	−166.32 (17)	C15—C16—C18—C19	−163.75 (19)
C6—C5—C7—C8	−39.0 (2)	C17—C16—C18—C19	−38.3 (2)
C11—C7—C8—C9	−49.6 (2)	C22—C18—C19—C20	−50.3 (2)
C5—C7—C8—C9	61.56 (19)	C16—C18—C19—C20	60.5 (2)
C7—C8—C9—C10	49.8 (2)	C18—C19—C20—C21	50.4 (2)
C7—C8—C9—C6	−60.31 (18)	C18—C19—C20—C17	−59.9 (2)
C1—C6—C9—C10	58.8 (2)	C12—C17—C20—C21	58.1 (2)
C5—C6—C9—C10	−67.92 (19)	C16—C17—C20—C21	−67.3 (2)
C1—C6—C9—C8	163.26 (17)	C12—C17—C20—C19	162.12 (18)
C5—C6—C9—C8	36.56 (19)	C16—C17—C20—C19	36.7 (2)
C8—C9—C10—C11	−33.1 (2)	C19—C20—C21—C22	−33.7 (2)
C6—C9—C10—C11	70.1 (2)	C17—C20—C21—C22	70.0 (2)
C9—C10—C11—C7	−0.3 (3)	C20—C21—C22—C18	−0.1 (3)
C8—C7—C11—C10	33.3 (2)	C19—C18—C22—C21	33.5 (2)
C5—C7—C11—C10	−69.6 (2)	C16—C18—C22—C21	−69.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2ⁱ	0.87 (3)	1.86 (3)	2.730 (2)	175 (3)
O3—H3O···O1ⁱⁱ	0.90 (3)	1.82 (3)	2.720 (2)	171 (3)
O4—H4O···O3ⁱⁱⁱ	0.80 (3)	1.93 (3)	2.731 (2)	175 (3)
O2—H2O···O4	0.81 (3)	1.97 (3)	2.777 (2)	174 (3)

Symmetry codes: (i) x+1/2, −y+1, z; (ii) −x+3/2, y−1, z+1/2; (iii) x−1/2, −y, z.

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