Oxonium (dihydrogen 1-amino-ethane-1,1-diyldiphospho-nato-κN,O)[hydrogen (1-amino-1-phosphono-ethyl)phospho-nato-κN,O]palladium(II) trihydrate.

The title compound, (H(3)O)[Pd(C(2)H(7)NO(6)P(2))(C(2)H(8)NO(6)P(2))]·3H(2)O, was synthesized by the reaction of [Pd(H(2)O)(4)](NO(3))(2) with 1-amino-ethane-1,1-diyldiphospho-nic acid in aqueous solution. The asymmetric unit contains one mol-ecule of the complex existing as an anion, an oxonium counter-ion and three solvent water mol-ecules. The Pd(II) ion occupies a position on a pseudo-twofold axis, which is not realized crystallographically. The slightly distorted square-planar coordination environment of the Pd(II) ion consists of the O atoms from two phospho-nic acid groups and two N atoms of the amino groups in cis positions. The crystal structure displays N-H⋯O and O-H⋯O hydrogen bonding, which creates a wide three-dimensional network.

Related literature

For general background and the medical use of organic diphospho­nic acids, see: Matczak-Jon & Videnova-Adrabinska (2005 ▶); Curic et al. (1996 ▶); Szabo et al. (2002 ▶). For related structures, see: Shkol’nikova et al. (1991 ▶).

Experimental

Crystal data

(H3O)[Pd(C2H7NO6P2)(C2H8NO6P2)]·3H2O

M = 586.53

Orthorhombic,

a = 9.9412 (2) Å

b = 9.0941 (2) Å

c = 19.9004 (3) Å

V = 1799.12 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.47 mm−1

T = 100 K

0.48 × 0.29 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.536, T max = 0.823

53680 measured reflections

5568 independent reflections

5545 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.015

wR(F 2) = 0.041

S = 1.09

5568 reflections

301 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.80 e Å−3

Δρmin = −0.61 e Å−3

Absolute structure: racemic twin (Flack, 1983 ▶), 2697 Friedel pairs

Flack parameter: 0.362 (11)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810000930/hg2625sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000930/hg2625Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(H3O)[Pd(C2H7NO6P2)(C2H8NO6P2)]·3H2O	Dx = 2.165 Mg m−3
Mr = 586.53	Melting point: 542 K
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 9199 reflections
a = 9.9412 (2) Å	θ = 3.0–30.7°
b = 9.0941 (2) Å	µ = 1.47 mm−1
c = 19.9004 (3) Å	T = 100 K
V = 1799.12 (6) Å3	Prism, yellow
Z = 4	0.48 × 0.29 × 0.14 mm
F(000) = 1184

Bruker APEXII CCD diffractometer	5568 independent reflections
Radiation source: fine-focus sealed tube	5545 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 8.26 pixels mm-1	θmax = 30.7°, θmin = 2.1°
φ and ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
Tmin = 0.536, Tmax = 0.823	l = −28→28
53680 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.015	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.041	w = 1/[σ2(Fo2) + (0.0254P)2 + 0.6821P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
5568 reflections	Δρmax = 0.80 e Å−3
301 parameters	Δρmin = −0.61 e Å−3
6 restraints	Absolute structure: racemic twin (Flack, 1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.362 (11)

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.

	x	y	z	Uiso*/Ueq
Pd1	0.277544 (8)	0.490311 (10)	0.552262 (8)	0.00533 (3)
P1	0.18198 (3)	0.27187 (4)	0.450244 (18)	0.00635 (6)
P2	0.45406 (3)	0.13836 (4)	0.414989 (18)	0.00657 (6)
P3	0.18727 (3)	0.72538 (4)	0.648914 (17)	0.00648 (6)
P4	0.46193 (3)	0.80633 (4)	0.704329 (19)	0.00694 (6)
C1	0.36318 (13)	0.30710 (15)	0.43864 (7)	0.0064 (2)
C2	0.37971 (15)	0.42927 (16)	0.38612 (7)	0.0101 (2)
H2A	0.3247	0.5142	0.3990	0.015*
H2B	0.3506	0.3930	0.3421	0.015*
H2C	0.4744	0.4587	0.3838	0.015*
C3	0.35636 (14)	0.65907 (15)	0.67191 (7)	0.0068 (2)
C4	0.34278 (15)	0.53574 (17)	0.72415 (7)	0.0107 (2)
H4A	0.2757	0.4642	0.7088	0.016*
H4B	0.3142	0.5777	0.7672	0.016*
H4C	0.4298	0.4866	0.7298	0.016*
N1	0.41461 (12)	0.36316 (14)	0.50470 (6)	0.0071 (2)
H11N	0.488 (2)	0.403 (3)	0.4966 (12)	0.009*
H12N	0.429 (2)	0.295 (3)	0.5263 (11)	0.009*
N2	0.41624 (12)	0.59683 (14)	0.60867 (6)	0.0071 (2)
H21N	0.487 (2)	0.545 (3)	0.6173 (12)	0.009*
H22N	0.447 (2)	0.661 (3)	0.5861 (11)	0.009*
O1	0.13407 (10)	0.40368 (12)	0.49205 (5)	0.00857 (18)
O2	0.17592 (11)	0.13034 (12)	0.49408 (6)	0.0109 (2)
H2O	0.121 (2)	0.072 (2)	0.4877 (12)	0.016*
O3	0.11271 (12)	0.25861 (13)	0.38397 (6)	0.0100 (2)
O4	0.59246 (11)	0.19312 (13)	0.38559 (6)	0.0108 (2)
H4O	0.595 (2)	0.180 (3)	0.3495 (13)	0.016*
O5	0.37046 (11)	0.06419 (12)	0.36199 (5)	0.01071 (19)
H133	0.379 (2)	−0.084 (3)	0.3421 (12)	0.016*
O6	0.48312 (10)	0.05260 (13)	0.47795 (6)	0.00955 (19)
O7	0.13394 (10)	0.60237 (12)	0.60317 (5)	0.00854 (19)
O8	0.20867 (11)	0.86805 (13)	0.60679 (6)	0.0109 (2)
H8O	0.238 (2)	0.846 (3)	0.5705 (9)	0.016*
O9	0.10146 (11)	0.75447 (13)	0.70822 (6)	0.0119 (2)
O10	0.50545 (12)	0.90097 (12)	0.64312 (6)	0.01182 (19)
H10O	0.470 (3)	0.982 (3)	0.6345 (16)	0.018*
O11	0.38539 (11)	0.88643 (13)	0.75747 (5)	0.01041 (19)
O12	0.58885 (11)	0.72475 (14)	0.72731 (6)	0.0118 (2)
H12O	0.649 (2)	0.778 (3)	0.7377 (12)	0.018*
O13	0.38258 (11)	−0.19735 (12)	0.33187 (5)	0.00984 (19)
H131	0.447 (3)	−0.227 (3)	0.3520 (13)	0.015*
H132	0.382 (2)	−0.212 (3)	0.2878 (12)	0.015*
O14	0.80746 (11)	0.83022 (13)	0.75959 (5)	0.01002 (18)
H141	0.813 (2)	0.801 (2)	0.7968 (9)	0.015*
H142	0.822 (3)	0.917 (3)	0.7586 (12)	0.015*
O15	0.30815 (12)	0.81984 (13)	0.49016 (6)	0.0136 (2)
H151	0.257 (3)	0.820 (3)	0.4577 (13)	0.020*
H152	0.356 (2)	0.888 (2)	0.4850 (13)	0.020*
O16	0.37176 (13)	0.14546 (13)	0.62029 (6)	0.0138 (2)
H161	0.376 (3)	0.179 (3)	0.6551 (13)	0.021*
H162	0.287 (3)	0.126 (3)	0.6135 (13)	0.021*

	U11	U22	U33	U12	U13	U23
Pd1	0.00476 (4)	0.00531 (4)	0.00592 (4)	0.00017 (3)	−0.00038 (4)	−0.00138 (4)
P1	0.00546 (15)	0.00627 (15)	0.00734 (15)	0.00002 (11)	−0.00077 (11)	−0.00155 (12)
P2	0.00633 (13)	0.00681 (15)	0.00657 (14)	0.00094 (11)	−0.00007 (11)	−0.00088 (12)
P3	0.00557 (14)	0.00721 (15)	0.00667 (15)	0.00051 (11)	0.00001 (11)	−0.00196 (12)
P4	0.00715 (14)	0.00637 (15)	0.00732 (14)	−0.00025 (11)	−0.00118 (11)	−0.00102 (12)
C1	0.0067 (5)	0.0059 (5)	0.0066 (5)	−0.0002 (4)	−0.0007 (4)	−0.0005 (4)
C2	0.0112 (6)	0.0077 (6)	0.0114 (6)	0.0000 (5)	0.0000 (5)	0.0017 (5)
C3	0.0083 (5)	0.0057 (5)	0.0064 (5)	0.0000 (4)	−0.0004 (4)	−0.0008 (4)
C4	0.0113 (6)	0.0111 (6)	0.0098 (6)	−0.0008 (5)	−0.0014 (5)	0.0030 (5)
N1	0.0056 (5)	0.0080 (5)	0.0078 (5)	0.0005 (4)	−0.0012 (4)	−0.0016 (4)
N2	0.0063 (5)	0.0073 (5)	0.0077 (5)	−0.0007 (4)	0.0001 (4)	−0.0017 (4)
O1	0.0051 (4)	0.0104 (5)	0.0102 (4)	0.0008 (3)	−0.0014 (3)	−0.0049 (4)
O2	0.0090 (4)	0.0095 (5)	0.0141 (5)	−0.0031 (4)	−0.0020 (4)	0.0026 (4)
O3	0.0075 (4)	0.0135 (5)	0.0092 (5)	0.0005 (4)	−0.0027 (3)	−0.0034 (4)
O4	0.0082 (4)	0.0152 (5)	0.0089 (5)	−0.0004 (4)	0.0031 (3)	−0.0006 (4)
O5	0.0125 (5)	0.0090 (5)	0.0106 (5)	0.0019 (4)	−0.0032 (4)	−0.0029 (4)
O6	0.0101 (5)	0.0085 (5)	0.0101 (5)	0.0021 (4)	−0.0002 (3)	0.0009 (4)
O7	0.0063 (4)	0.0100 (5)	0.0093 (5)	0.0008 (3)	−0.0003 (3)	−0.0042 (4)
O8	0.0127 (5)	0.0082 (5)	0.0119 (5)	0.0009 (3)	−0.0006 (4)	0.0011 (4)
O9	0.0088 (4)	0.0175 (5)	0.0094 (5)	0.0016 (4)	0.0021 (4)	−0.0047 (4)
O10	0.0136 (5)	0.0086 (5)	0.0133 (5)	−0.0024 (4)	0.0032 (4)	0.0017 (4)
O11	0.0127 (5)	0.0089 (5)	0.0096 (4)	0.0021 (4)	−0.0006 (4)	−0.0024 (4)
O12	0.0089 (5)	0.0097 (5)	0.0167 (5)	0.0004 (4)	−0.0051 (4)	−0.0018 (4)
O13	0.0093 (4)	0.0108 (5)	0.0094 (5)	0.0009 (4)	−0.0020 (4)	−0.0014 (4)
O14	0.0100 (4)	0.0101 (5)	0.0099 (5)	−0.0014 (4)	−0.0005 (4)	0.0007 (4)
O15	0.0148 (5)	0.0129 (5)	0.0131 (5)	−0.0017 (4)	0.0014 (4)	0.0033 (4)
O16	0.0180 (5)	0.0133 (5)	0.0101 (5)	−0.0017 (4)	−0.0008 (4)	−0.0002 (4)

Pd1—N1	2.0223 (12)	C3—N2	1.5028 (18)
Pd1—O1	2.0226 (10)	C3—C4	1.535 (2)
Pd1—N2	2.0247 (12)	C4—H4A	0.9800
Pd1—O7	2.0256 (10)	C4—H4B	0.9800
P1—O3	1.4926 (12)	C4—H4C	0.9800
P1—O1	1.5349 (11)	N1—H11N	0.83 (2)
P1—O2	1.5560 (12)	N1—H12N	0.77 (2)
P1—C1	1.8442 (14)	N2—H21N	0.86 (2)
P2—O5	1.5027 (11)	N2—H22N	0.80 (2)
P2—O6	1.5039 (12)	O2—H2O	0.774 (16)
P2—O4	1.5759 (11)	O4—H4O	0.73 (3)
P2—C1	1.8418 (14)	O5—H133	1.40 (3)
P3—O9	1.4801 (12)	O8—H8O	0.805 (16)
P3—O7	1.5366 (11)	O10—H10O	0.83 (3)
P3—O8	1.5593 (12)	O12—H12O	0.791 (17)
P3—C3	1.8435 (14)	O13—H133	1.06 (2)
P4—O11	1.4926 (11)	O13—H131	0.80 (3)
P4—O12	1.5335 (12)	O13—H132	0.89 (2)
P4—O10	1.5530 (12)	O14—H141	0.788 (16)
P4—C3	1.8196 (14)	O14—H142	0.80 (3)
C1—N1	1.4998 (18)	O15—H151	0.82 (3)
C1—C2	1.5342 (19)	O15—H152	0.785 (16)
C2—H2A	0.9800	O16—H161	0.76 (3)
C2—H2B	0.9800	O16—H162	0.87 (3)
C2—H2C	0.9800
N1—Pd1—O1	88.58 (5)	H2A—C2—H2C	109.5
N1—Pd1—N2	94.26 (5)	H2B—C2—H2C	109.5
O1—Pd1—N2	174.28 (5)	N2—C3—C4	109.07 (11)
N1—Pd1—O7	175.31 (5)	N2—C3—P4	110.22 (9)
O1—Pd1—O7	89.73 (4)	C4—C3—P4	110.38 (9)
N2—Pd1—O7	87.82 (5)	N2—C3—P3	106.05 (9)
O3—P1—O1	113.50 (6)	C4—C3—P3	109.08 (10)
O3—P1—O2	114.25 (7)	P4—C3—P3	111.91 (7)
O1—P1—O2	109.28 (6)	C3—C4—H4A	109.5
O3—P1—C1	110.74 (6)	C3—C4—H4B	109.5
O1—P1—C1	103.61 (6)	H4A—C4—H4B	109.5
O2—P1—C1	104.58 (6)	C3—C4—H4C	109.5
O5—P2—O6	117.27 (7)	H4A—C4—H4C	109.5
O5—P2—O4	111.35 (7)	H4B—C4—H4C	109.5
O6—P2—O4	107.79 (6)	C1—N1—Pd1	112.02 (8)
O5—P2—C1	106.38 (6)	C1—N1—H11N	106.1 (16)
O6—P2—C1	108.26 (6)	Pd1—N1—H11N	115.9 (16)
O4—P2—C1	105.06 (6)	C1—N1—H12N	106.4 (17)
O9—P3—O7	113.81 (6)	Pd1—N1—H12N	108.9 (17)
O9—P3—O8	111.01 (7)	H11N—N1—H12N	107 (2)
O7—P3—O8	109.53 (6)	C3—N2—Pd1	112.01 (8)
O9—P3—C3	112.71 (6)	C3—N2—H21N	111.1 (16)
O7—P3—C3	102.92 (6)	Pd1—N2—H21N	113.9 (16)
O8—P3—C3	106.34 (6)	C3—N2—H22N	110.5 (16)
O11—P4—O12	116.37 (6)	Pd1—N2—H22N	107.3 (16)
O11—P4—O10	115.30 (7)	H21N—N2—H22N	101 (2)
O12—P4—O10	105.83 (7)	P1—O1—Pd1	113.98 (6)
O11—P4—C3	108.45 (7)	P1—O2—H2O	120.4 (18)
O12—P4—C3	102.96 (7)	P2—O4—H4O	110.0 (19)
O10—P4—C3	106.88 (6)	P2—O5—H133	126.4 (10)
N1—C1—C2	108.33 (11)	P3—O7—Pd1	114.80 (6)
N1—C1—P2	109.88 (9)	P3—O8—H8O	108.8 (17)
C2—C1—P2	112.13 (9)	P4—O10—H10O	122 (2)
N1—C1—P1	106.40 (9)	P4—O12—H12O	113.7 (19)
C2—C1—P1	108.40 (9)	H133—O13—H131	105 (2)
P2—C1—P1	111.49 (7)	H133—O13—H132	110 (2)
C1—C2—H2A	109.5	H131—O13—H132	116 (2)
C1—C2—H2B	109.5	H141—O14—H142	110 (2)
H2A—C2—H2B	109.5	H151—O15—H152	106 (3)
C1—C2—H2C	109.5	H161—O16—H162	106 (3)
O5—P2—C1—N1	162.48 (9)	O7—P3—C3—N2	42.06 (10)
O6—P2—C1—N1	35.62 (11)	O8—P3—C3—N2	−73.07 (10)
O4—P2—C1—N1	−79.34 (10)	O9—P3—C3—C4	47.74 (11)
O5—P2—C1—C2	−76.99 (11)	O7—P3—C3—C4	−75.28 (10)
O6—P2—C1—C2	156.15 (10)	O8—P3—C3—C4	169.59 (9)
O4—P2—C1—C2	41.19 (11)	O9—P3—C3—P4	−74.69 (9)
O5—P2—C1—P1	44.78 (9)	O7—P3—C3—P4	162.28 (7)
O6—P2—C1—P1	−82.09 (8)	O8—P3—C3—P4	47.16 (9)
O4—P2—C1—P1	162.95 (7)	C2—C1—N1—Pd1	80.78 (11)
O3—P1—C1—N1	163.27 (9)	P2—C1—N1—Pd1	−156.42 (6)
O1—P1—C1—N1	41.23 (10)	P1—C1—N1—Pd1	−35.59 (11)
O2—P1—C1—N1	−73.22 (10)	O1—Pd1—N1—C1	17.73 (10)
O3—P1—C1—C2	46.95 (11)	N2—Pd1—N1—C1	−157.30 (10)
O1—P1—C1—C2	−75.08 (10)	C4—C3—N2—Pd1	79.72 (12)
O2—P1—C1—C2	170.47 (9)	P4—C3—N2—Pd1	−158.94 (6)
O3—P1—C1—P2	−76.95 (9)	P3—C3—N2—Pd1	−37.63 (10)
O1—P1—C1—P2	161.02 (7)	N1—Pd1—N2—C3	−156.26 (9)
O2—P1—C1—P2	46.57 (8)	O7—Pd1—N2—C3	19.52 (9)
O11—P4—C3—N2	167.68 (9)	O3—P1—O1—Pd1	−148.99 (7)
O12—P4—C3—N2	−68.45 (10)	O2—P1—O1—Pd1	82.21 (7)
O10—P4—C3—N2	42.79 (11)	C1—P1—O1—Pd1	−28.83 (8)
O11—P4—C3—C4	−71.76 (11)	N1—Pd1—O1—P1	10.10 (7)
O12—P4—C3—C4	52.11 (11)	O7—Pd1—O1—P1	−165.52 (7)
O10—P4—C3—C4	163.35 (10)	O9—P3—O7—Pd1	−150.89 (7)
O11—P4—C3—P3	49.93 (9)	O8—P3—O7—Pd1	84.19 (7)
O12—P4—C3—P3	173.79 (7)	C3—P3—O7—Pd1	−28.61 (8)
O10—P4—C3—P3	−74.96 (9)	O1—Pd1—O7—P3	−165.75 (7)
O9—P3—C3—N2	165.08 (9)	N2—Pd1—O7—P3	9.09 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11N···O1i	0.83 (2)	2.28 (2)	3.0527 (16)	154 (2)
N1—H12N···O16	0.77 (2)	2.38 (2)	3.0647 (18)	149 (2)
N2—H21N···O7i	0.86 (2)	2.01 (2)	2.8245 (17)	159 (2)
N2—H22N···O10	0.80 (2)	2.53 (2)	2.9844 (17)	117.7 (19)
O2—H2O···O6ii	0.77 (2)	1.79 (2)	2.5582 (15)	174 (3)
O4—H4O···O11iii	0.73 (3)	1.94 (3)	2.6593 (16)	170 (3)
O13—H133···O5	1.06 (2)	1.40 (3)	2.4558 (16)	174 (2)
O8—H8O···O15	0.81 (2)	1.76 (2)	2.5607 (17)	173 (3)
O10—H10O···O16iv	0.83 (3)	1.80 (3)	2.6298 (17)	172 (3)
O12—H12O···O14	0.79 (2)	1.71 (2)	2.4608 (16)	159 (3)
O13—H131···O3v	0.80 (3)	1.79 (3)	2.5728 (16)	165 (2)
O13—H132···O9vi	0.89 (2)	1.62 (2)	2.5044 (16)	174 (2)
O14—H141···O3vii	0.79 (2)	1.96 (2)	2.7220 (16)	162 (2)
O14—H142···O11viii	0.80 (3)	1.90 (3)	2.6911 (17)	171 (3)
O15—H151···O4ix	0.82 (3)	2.18 (3)	2.9904 (18)	169 (3)
O15—H152···O6iv	0.79 (2)	1.97 (2)	2.7504 (17)	176 (3)
O16—H161···O14ix	0.76 (3)	2.19 (3)	2.8534 (16)	147 (3)
O16—H162···O8x	0.87 (3)	2.48 (3)	3.0109 (17)	120 (2)
O16—H162···O2	0.87 (3)	2.62 (3)	3.1809 (16)	123 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11N⋯O1i	0.83 (2)	2.28 (2)	3.0527 (16)	154 (2)
N1—H12N⋯O16	0.77 (2)	2.38 (2)	3.0647 (18)	149 (2)
N2—H21N⋯O7i	0.86 (2)	2.01 (2)	2.8245 (17)	159 (2)
N2—H22N⋯O10	0.80 (2)	2.53 (2)	2.9844 (17)	117.7 (19)
O2—H2O⋯O6ii	0.77 (2)	1.79 (2)	2.5582 (15)	174 (3)
O4—H4O⋯O11iii	0.73 (3)	1.94 (3)	2.6593 (16)	170 (3)
O13—H133⋯O5	1.06 (2)	1.40 (3)	2.4558 (16)	174 (2)
O8—H8O⋯O15	0.81 (2)	1.76 (2)	2.5607 (17)	173 (3)
O10—H10O⋯O16iv	0.83 (3)	1.80 (3)	2.6298 (17)	172 (3)
O12—H12O⋯O14	0.79 (2)	1.71 (2)	2.4608 (16)	159 (3)
O13—H131⋯O3v	0.80 (3)	1.79 (3)	2.5728 (16)	165 (2)
O13—H132⋯O9vi	0.89 (2)	1.62 (2)	2.5044 (16)	174 (2)
O14—H141⋯O3vii	0.79 (2)	1.96 (2)	2.7220 (16)	162 (2)
O14—H142⋯O11viii	0.80 (3)	1.90 (3)	2.6911 (17)	171 (3)
O15—H151⋯O4ix	0.82 (3)	2.18 (3)	2.9904 (18)	169 (3)
O15—H152⋯O6iv	0.79 (2)	1.97 (2)	2.7504 (17)	176 (3)
O16—H161⋯O14ix	0.76 (3)	2.19 (3)	2.8534 (16)	147 (3)
O16—H162⋯O8x	0.87 (3)	2.48 (3)	3.0109 (17)	120 (2)
O16—H162⋯O2	0.87 (3)	2.62 (3)	3.1809 (16)	123 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) ; (x) .