7,9-Bis(hy­droxy­meth­yl)-7H-purine-2,6,8(1H,3H,9H)trione

Daudon, M.; Bazin, D.; Adil, K.; Bail, A.L.

doi:10.1107/S1600536811018186

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1458

doi:10.1107/S1600536811018186

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7,9-Bis(hydroxymethyl)-7H-purine-2,6,8(1H,3H,9H)trione

M. Daudon,^a D. Bazin,^b K. Adil ^c and A. Le Bail ^c ^*

^aLaboratoire de Biochimie A, AP-HP, Hopital Necker, 149 rue de Sèvres, 75743 Paris Cedex 15, France, ^bLaboratoire de Physique des Solides, Bat. 510, Université Paris XI, 91045 Orsay, France, and ^cLaboratoire des Oxydes et Fluorures, UMR 6010 CNRS, Université du Maine, Avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France
^*Correspondence e-mail: armel.le_bail@univ-lemans.fr

(Received 9 May 2011; accepted 13 May 2011; online 20 May 2011)

The structure of the title uric acid derivative, C₇H₈N₄O₅, from human kidney stones, is characterized by the C and O atoms of one of the two hydroxymethyl groups being disordered nearly equally over three different sites. In the crystal, molecules are connected by a three-dimensional hydrogen-bonding scheme though they look stacked in planes nearly parallel to ( $[\overline{1}]$ 04).

Related literature

For related structures, see: Ringertz (1966 ) for uric acid and Parkin & Hope (1998 ) for the dihydrate. For urolithiasis, see: Tanagho & McAninch (2000 ); Jungers et al. (2005 ); Moe (2006 ); Knoll (2007 ). For recent characterization of new urinary stones, see: Le Bail et al. (2009 ); For purine biosynthesis, see: Ashihara et al. (2008 ). For hydroxymethylation of uric acid, see: Lubczak et al. (2002 ).

Experimental

Crystal data

C₇H₈N₄O₅
M_r = 228.17
Monoclinic, P 2₁ /c
a = 5.3226 (6) Å
b = 11.5541 (13) Å
c = 14.5931 (18) Å
β = 97.340 (7)°
V = 890.09 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 150 K
0.22 × 0.12 × 0.06 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.677, T_max = 0.746
33302 measured reflections
3075 independent reflections
2127 reflections with I > 2σ(I)
R_int = 0.064

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.166
S = 1.03
3075 reflections
169 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9⋯O2ⁱ	1.04	1.70	2.7270 (18)	169
N1—H1⋯O6ⁱⁱ	0.86	1.98	2.8388 (18)	179
N3—H3⋯O8ⁱⁱⁱ	0.84	1.88	2.7104 (19)	167
O71—H71⋯O2^iv	0.84	2.04	2.873 (4)	172
O72—H72⋯O9ⁱ	0.84	2.01	2.834 (5)	169
O73—H73⋯O8^v	0.84	2.17	2.892 (6)	144
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+3, -y, -z+1; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x+2, -y, -z+1; (v) x+1, y, z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008) and McMaille (Le Bail, 2004 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ) and ESPOIR (Le Bail, 2001 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001 ) and ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018186/zl2370sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018186/zl2370Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811018186/zl2370Isup3.mol

Supporting information file. DOI: 10.1107/S1600536811018186/zl2370Isup4.cml

checkCIF report

Comment top

Urolithiasis, which is as old as mankind is now the third most common urinary disease (Jungers et al., 2005; Moe, 2006; Knoll, 2007). This disease constitutes a major health problem and there is evidence to show that its incidence has increased continually in past decades (Tanagho & McAninch, 2000). Among the different chemical phases found in kidney stones, let's quote calcium oxalate, calcium phosphate, uric acid, ammonium hydrogen urate and magnesium ammonium phosphate which are the main components of stones, with differences in their distribution being found in different population groups.

Recently, at the surface of uric acid kidney stones, a green deposit has been observed for different patients. Since classical FTIR measurements were not able to characterize such deposit, X-ray diffraction experiments have been performed.

Powder diffraction revealed a mixture of uric acid (Ringertz, 1966) together with traces of its dihydrate (Parkin & Hope, 1998) and an unknown phase which could be indexed by using the McMaille software (Le Bail, 2004). An hypothesis for an uric acid derivative was suggested by the direct space software ESPOIR (Le Bail, 2001), however the structure could not be completed till a tiny single-crystal was selected in the powder. From the structure solution, a hydroxymethyl group was found attached to N9. High thermal parameters at room temperature obscured the nature of some disorder occurring around of the C7 atom: three peaks on the Fourier difference map, all looking lighter than a C atom, but heavier than a H one, two of them at 0.9 Å from each other were observed. At 150 K, the thermal motions were considerably smaller, allowing to propose an interpretation: a second hydroxymethyl group, CH₂OH attached to N7, nearly equally disordered over three different O atom sites. The largest difference densities (0.78, 0.54) in the final structural model are close to C9 of the not disordered hydroxymethyl group (exactly between H9A and H9B) and O8. If O8 may be slightly splitted, given its large U₃₃, the most intense residue close to C9 is unclear, possibly due to some disorder also for this hydroxymethyl group. Positional disorder was observed in uric acid dihydrate with superimposition of the six- and five-membered rings (Parkin and Hope, 1998). Such a disorder is unlikely to occur in the title compound. Different parts of the samples examined by powder diffraction may show variations in cell parameters as well as strong peak asymetries suggesting inhomogeneities, possibly corresponding to more or less disorder.

The ORTEP diagram of the title compound is shown in Fig. 1. Atoms numbering adopts the purine system. Molecules are connected by a three-dimensional hydrogen bonding scheme (Fig. 2 and Table 2), though they are stacked in planes nearly parallel to (104) (Fig. 3), corresponding by far to the most intense reflection.

In humans, uric acid is the main urinary metabolite of purines, therefore, its alteration is a mark of disorders associated with purine metabolism. A review on the biosynthesis of caffeine and related purine alkaloids was published recently (Ashihara et al., 2008). But how the title compound is biosynthesized in humans is not yet fully understood. Hydroxymethylation of uric acid is known to occur with formaldehyde (Lubczak et al., 2002).

Related literature top

For related structures, see: Ringertz (1966) for uric acid and Parkin & Hope (1998) for the dihydrate. For urolithiasis, see: Tanagho & McAninch (2000); Jungers et al. (2005); Moe (2006); Knoll (2007). For recent characterization of new urinary stones, see: Le Bail et al. (2009); For purine biosynthesis, see: Ashihara et al. (2008). For hydroxymethylation of uric acid, see: Lubczak et al. (2002).

Experimental top

Samples are coming from human kidney stones, always identified as a green part at the surface of uric acid calculi. Either they could originate from a natural cause or from the consequence of a chemical treatment of the patients (about ten cases). Since the patients took various medications for different unsimilar pathologies or had no treatment at all, the cause looks more probably natural.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008) and McMaille (Le Bail, 2004); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and ESPOIR (Le Bail, 2001); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. ORTEP view (Farrugia, 1997) of the title molecule; displacement ellipsoids are drawn at the 50% probability level. The nine hydrogen atoms bonded to C7, O71, O72 and O73, with ~1/3 occupancies are omitted for the sake of clarity.
	Fig. 2. DIAMOND (Brandenburg, 2001) projection of the structure along the a axis. The N1—H1···O6, N3—H3···O8 and O9—H9···O2 hydrogen bonds ensuring the formation of layers are represented by dashed lines. H atoms with ~1/3 occupancy are not represented.
	Fig. 3. DIAMOND (Brandenburg, 2001) projection of the structure along the b axis showing the layers stacked parallel to (104). H atoms with ~1/3 occupancy are not represented. The disordered OH group (O71, O72, O73) is mainly involved in inter-layers hydrogen bonding.

7,9-Bis(hydroxymethyl)-7H-purine- 2,6,8(1H,3H,9H)trione top

Crystal data top

C₇H₈N₄O₅	F(000) = 472.0
M_r = 228.17	D_x = 1.703 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 241 reflections
a = 5.3226 (6) Å	θ = 4–15°
b = 11.5541 (13) Å	µ = 0.15 mm⁻¹
c = 14.5931 (18) Å	T = 150 K
β = 97.340 (7)°	Fragment, pale-green
V = 890.09 (18) Å³	0.22 × 0.12 × 0.06 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3075 independent reflections
Radiation source: fine-focus sealed tube	2127 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
ω scans; 30 settings	θ_max = 32.3°, θ_min = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −7→7
T_min = 0.677, T_max = 0.746	k = −17→17
33302 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.166	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0816P)² + 0.5575P] where P = (F_o² + 2F_c²)/3
3075 reflections	(Δ/σ)_max < 0.001
169 parameters	Δρ_max = 0.78 e Å⁻³
1 restraint	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₇H₈N₄O₅	V = 890.09 (18) Å³
M_r = 228.17	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.3226 (6) Å	µ = 0.15 mm⁻¹
b = 11.5541 (13) Å	T = 150 K
c = 14.5931 (18) Å	0.22 × 0.12 × 0.06 mm
β = 97.340 (7)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3075 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2127 reflections with I > 2σ(I)
T_min = 0.677, T_max = 0.746	R_int = 0.064
33302 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	1 restraint
wR(F²) = 0.166	H-atom parameters constrained
S = 1.03	Δρ_max = 0.78 e Å⁻³
3075 reflections	Δρ_min = −0.37 e Å⁻³
169 parameters

Special details top

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	Occ. (<1)
O2	1.0659 (2)	−0.20036 (10)	0.35524 (10)	0.0250 (3)
O6	1.3617 (2)	0.14185 (10)	0.48924 (9)	0.0241 (3)
O8	0.5565 (3)	0.35248 (12)	0.28547 (13)	0.0430 (4)
O9	0.2229 (2)	0.11073 (11)	0.19866 (10)	0.0278 (3)
H9	0.1080	0.1830	0.1860	0.042*
N1	1.2092 (3)	−0.02650 (11)	0.41726 (10)	0.0174 (3)
H1	1.3389	−0.0620	0.4458	0.021*
N3	0.8444 (3)	−0.03560 (11)	0.30815 (10)	0.0175 (3)
H3	0.7360	−0.0740	0.2739	0.021*
N7	0.8876 (3)	0.26000 (12)	0.37849 (11)	0.0247 (3)
N9	0.6403 (3)	0.15297 (12)	0.27429 (11)	0.0224 (3)
C2	1.0404 (3)	−0.09345 (13)	0.35937 (11)	0.0167 (3)
C4	0.8172 (3)	0.08053 (13)	0.32201 (11)	0.0162 (3)
C5	0.9722 (3)	0.14401 (13)	0.38595 (11)	0.0165 (3)
C6	1.1933 (3)	0.09272 (13)	0.43511 (11)	0.0161 (3)
C8	0.6827 (4)	0.26569 (15)	0.31068 (14)	0.0273 (4)
C9	0.4761 (3)	0.12956 (15)	0.18565 (13)	0.0236 (4)
H9A	0.4850	0.1962	0.1435	0.028*
H9B	0.5407	0.0606	0.1559	0.028*
C7A	0.9677 (4)	0.35741 (15)	0.44018 (14)	0.0268 (4)	0.339 (3)
H7A1	1.1376	0.3428	0.4744	0.032*	0.339 (3)
H7A2	0.9734	0.4301	0.4045	0.032*	0.339 (3)
O71	0.7889 (9)	0.3644 (4)	0.4997 (3)	0.0325 (11)	0.339 (3)
H71	0.8173	0.3134	0.5407	0.049*	0.339 (3)
C7B	0.9677 (4)	0.35741 (15)	0.44018 (14)	0.0268 (4)	0.340 (6)
H7B1	0.8166	0.3902	0.4638	0.032*	0.340 (6)
H7B2	1.0823	0.3278	0.4938	0.032*	0.340 (6)
O72	1.0842 (9)	0.4407 (3)	0.4008 (3)	0.0244 (13)	0.340 (6)
H72	0.9764	0.4847	0.3717	0.037*	0.340 (6)
C7C	0.9677 (4)	0.35741 (15)	0.44018 (14)	0.0268 (4)	0.321 (6)
H7C1	0.9760	0.3322	0.5053	0.032*	0.321 (6)
H7C2	0.8424	0.4209	0.4298	0.032*	0.321 (6)
O73	1.2214 (10)	0.3999 (4)	0.4221 (4)	0.0344 (15)	0.321 (6)
H73	1.2569	0.3717	0.3723	0.052*	0.321 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0232 (6)	0.0108 (5)	0.0381 (7)	0.0017 (4)	−0.0069 (5)	−0.0015 (5)
O6	0.0215 (6)	0.0168 (5)	0.0301 (7)	0.0027 (4)	−0.0114 (5)	−0.0047 (5)
O8	0.0344 (8)	0.0159 (6)	0.0700 (11)	0.0077 (5)	−0.0270 (8)	−0.0004 (6)
O9	0.0188 (6)	0.0212 (6)	0.0422 (8)	−0.0021 (5)	−0.0010 (5)	0.0016 (5)
N1	0.0157 (6)	0.0121 (6)	0.0224 (7)	0.0027 (5)	−0.0051 (5)	0.0001 (5)
N3	0.0161 (6)	0.0106 (6)	0.0237 (7)	−0.0005 (5)	−0.0057 (5)	−0.0006 (5)
N7	0.0221 (7)	0.0125 (6)	0.0355 (8)	0.0039 (5)	−0.0117 (6)	−0.0033 (5)
N9	0.0200 (7)	0.0122 (6)	0.0313 (8)	0.0000 (5)	−0.0113 (6)	0.0023 (5)
C2	0.0152 (7)	0.0126 (6)	0.0211 (7)	0.0003 (5)	−0.0019 (6)	0.0008 (5)
C4	0.0135 (7)	0.0127 (6)	0.0209 (7)	−0.0001 (5)	−0.0030 (5)	0.0020 (5)
C5	0.0158 (7)	0.0113 (6)	0.0211 (7)	0.0019 (5)	−0.0027 (6)	0.0001 (5)
C6	0.0159 (7)	0.0134 (6)	0.0179 (7)	0.0010 (5)	−0.0016 (5)	−0.0001 (5)
C8	0.0231 (9)	0.0147 (7)	0.0397 (10)	0.0022 (6)	−0.0129 (8)	−0.0005 (7)
C9	0.0204 (8)	0.0193 (8)	0.0282 (9)	−0.0016 (6)	−0.0078 (7)	0.0027 (6)
C7A	0.0307 (10)	0.0149 (7)	0.0329 (9)	0.0015 (6)	−0.0031 (7)	−0.0041 (6)
O71	0.049 (3)	0.024 (2)	0.025 (2)	0.0127 (18)	0.0052 (18)	0.0001 (15)
C7B	0.0307 (10)	0.0149 (7)	0.0329 (9)	0.0015 (6)	−0.0031 (7)	−0.0041 (6)
O72	0.022 (2)	0.0179 (19)	0.032 (2)	−0.0022 (16)	0.0001 (16)	0.0008 (15)
C7C	0.0307 (10)	0.0149 (7)	0.0329 (9)	0.0015 (6)	−0.0031 (7)	−0.0041 (6)
O73	0.028 (3)	0.027 (2)	0.048 (3)	−0.003 (2)	0.002 (2)	0.005 (2)

Geometric parameters (Å, º) top

O2—C2	1.2450 (19)	N9—C4	1.380 (2)
O6—C6	1.2524 (19)	N9—C8	1.414 (2)
O8—C8	1.236 (2)	N9—C9	1.491 (2)
O9—C9	1.401 (2)	C4—C5	1.376 (2)
O9—H9	1.0371	C5—C6	1.426 (2)
N1—C2	1.387 (2)	C9—H9A	0.9900
N1—C6	1.406 (2)	C9—H9B	0.9900
N1—H1	0.8627	C7A—O71	1.371 (5)
N3—C4	1.3673 (19)	C7A—H7A1	0.9900
N3—C2	1.377 (2)	C7A—H7A2	0.9900
N3—H3	0.8402	O71—H71	0.8400
N7—C8	1.377 (2)	O72—H72	0.8400
N7—C5	1.414 (2)	O73—H73	0.8400
N7—C7A	1.470 (2)

C9—O9—H9	114.0	C4—C5—C6	120.28 (14)
C2—N1—C6	127.52 (13)	N7—C5—C6	131.83 (14)
C2—N1—H1	116.4	O6—C6—N1	120.36 (14)
C6—N1—H1	116.1	O6—C6—C5	127.36 (14)
C4—N3—C2	118.90 (13)	N1—C6—C5	112.28 (13)
C4—N3—H3	121.9	O8—C8—N7	127.05 (17)
C2—N3—H3	118.8	O8—C8—N9	125.52 (16)
C8—N7—C5	108.41 (13)	N7—C8—N9	107.43 (14)
C8—N7—C7A	123.00 (14)	O9—C9—N9	112.21 (16)
C5—N7—C7A	127.88 (14)	O9—C9—H9A	109.2
C4—N9—C8	107.66 (13)	N9—C9—H9A	109.2
C4—N9—C9	127.92 (14)	O9—C9—H9B	109.2
C8—N9—C9	122.74 (14)	N9—C9—H9B	109.2
O2—C2—N3	122.35 (14)	H9A—C9—H9B	107.9
O2—C2—N1	121.10 (14)	O71—C7A—N7	105.2 (2)
N3—C2—N1	116.54 (13)	O71—C7A—H7A1	110.7
N3—C4—C5	123.92 (14)	N7—C7A—H7A1	110.7
N3—C4—N9	126.78 (14)	O71—C7A—H7A2	110.7
C5—C4—N9	109.29 (13)	N7—C7A—H7A2	110.7
C4—C5—N7	107.20 (13)	H7A1—C7A—H7A2	108.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9···O2ⁱ	1.04	1.70	2.7270 (18)	169
N1—H1···O6ⁱⁱ	0.86	1.98	2.8388 (18)	179
N3—H3···O8ⁱⁱⁱ	0.84	1.88	2.7104 (19)	167
O71—H71···O2^iv	0.84	2.04	2.873 (4)	172
O72—H72···O9ⁱ	0.84	2.01	2.834 (5)	169
O73—H73···O8^v	0.84	2.17	2.892 (6)	144

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

Experimental details

Crystal data
Chemical formula	C₇H₈N₄O₅
M_r	228.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	5.3226 (6), 11.5541 (13), 14.5931 (18)
β (°)	97.340 (7)
V (Å³)	890.09 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.22 × 0.12 × 0.06

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.677, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	33302, 3075, 2127
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.752

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.166, 1.03
No. of reflections	3075
No. of parameters	169
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.78, −0.37

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008) and McMaille (Le Bail, 2004), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008) and ESPOIR (Le Bail, 2001), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2001) and ORTEP-3 (Farrugia, 1997), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9···O2ⁱ	1.04	1.70	2.7270 (18)	169
N1—H1···O6ⁱⁱ	0.86	1.98	2.8388 (18)	179
N3—H3···O8ⁱⁱⁱ	0.84	1.88	2.7104 (19)	167
O71—H71···O2^iv	0.84	2.04	2.873 (4)	172
O72—H72···O9ⁱ	0.84	2.01	2.834 (5)	169
O73—H73···O8^v	0.84	2.17	2.892 (6)	144

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

Acknowledgements

The authors thank the reviewer for strong improvements of the description of the disordered part of the structure.

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