Bis[triaqua-(1H-1,2,4-triazole-3,5-dicarboxyl-ato-κO,N)copper(II)] di-μ-aqua-bis-[diaqua-(1H-1,2,4-triazole-3,5-dicarboxyl-ato-κO,N)copper(II)].

In the title compound, [Cu(C(4)HN(3)O(4))(H(2)O)(3)](2)[Cu(2)(C(4)HN(3)O(4))(2)(H(2)O)(6)], both monomeric and dimeric mol-ecules are present in the solid state. In the monomeric compound, the Cu(II) atom is five-coordinated in a square-pyramidal configuration by one O atom and one N atom from one 1H-1,2,4-triazole-3,5-dicarboxyl-ate (TZDCA(2-)) ligand and three O atoms from water mol-ecules. In the centrosymmetric binuclear complex, each Cu(II) atom is six-coordinated in an octa-hedral geometry by one O atom and one N atom from one TZDCA(2-) ligand and four O atoms from water mol-ecules, two of which bridge the Cu(II) atoms. In the structure, there are intra-molecular O-H⋯O and N-H⋯O hydrogen bonds, and in the crystal, inter-molecular O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds link symmetry-related mol-ecules, forming a three-dimensional supra-molecular structure.

Related literature

For related structures, see: Billing et al. (1970 ▶); Ouellette et al. (2006a ▶,b ▶, 2007 ▶); Zhai et al. (2007 ▶). For the preparation of 1,2,4,-triazole-3,5-dicarboxylic acid, see: Baitalik et al. (2004 ▶).

Experimental

Crystal data

[Cu(C4HN3O4)(H2O)3]2[n class="Chemical">Cu2(C4HN3O4)2(H2O)6]

M = 1090.70

Monoclinic,

a = 12.056 (2) Å

b = 11.432 (2) Å

c = 14.958 (3) Å

β = 123.65 (3)°

V = 1716.1 (5) Å3

Z = 2

Mo Kα radiation

μ = 2.57 mm−1

T = 293 K

0.10 × 0.10 × 0.08 mm

Data collection

Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2000 ▶) T min = 0.783, T max = 0.821

16043 measured reflections

3020 independent reflections

2866 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.115

S = 1.17

3020 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.54 e Å−3

Data collection: CrystalClear (Rigaku, 2000 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026993/su2127sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026993/su2127Isup2.hkl

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

[Cu(C4HN3O4)(H2O)3]2[Cu2(C4HN3O4)2(H2O)6]	F(000) = 1096
Mr = 1090.70	Dx = 2.111 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3290 reflections
a = 12.056 (2) Å	θ = 2.0–31.0°
b = 11.432 (2) Å	µ = 2.57 mm−1
c = 14.958 (3) Å	T = 293 K
β = 123.65 (3)°	Prism, blue
V = 1716.1 (5) Å3	0.10 × 0.10 × 0.08 mm
Z = 2

Mercury CCD diffractometer	3020 independent reflections
Radiation source: fine-focus sealed tube	2866 reflections with I > 2σ(I)
graphite	Rint = 0.051
ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	h = −14→14
Tmin = 0.783, Tmax = 0.821	k = −13→13
16043 measured reflections	l = −17→17

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.17	w = 1/[σ2(Fo2) + (0.0397P)2 + 6.4925P] where P = (Fo2 + 2Fc2)/3
3020 reflections	(Δ/σ)max < 0.001
272 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −0.54 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
Cu2	−0.00361 (5)	0.00777 (4)	0.38176 (4)	0.0204 (2)
O5	−0.0608 (3)	0.1733 (3)	0.3706 (3)	0.0251 (10)
O6	0.0026 (3)	0.3562 (3)	0.3659 (3)	0.0273 (10)
O7	0.2747 (4)	−0.1431 (3)	0.3948 (3)	0.0386 (13)
O8	0.4173 (3)	−0.0451 (3)	0.3711 (3)	0.0322 (11)
O12	−0.1496 (3)	−0.0099 (3)	0.1914 (3)	0.0299 (10)
O13	0.0607 (3)	−0.1507 (3)	0.4033 (3)	0.0401 (13)
O14	−0.1385 (3)	−0.0368 (3)	0.4098 (2)	0.0229 (9)
N4	0.2191 (4)	0.2525 (3)	0.3602 (3)	0.0239 (11)
N5	0.2979 (4)	0.1643 (3)	0.3662 (3)	0.0224 (11)
N6	0.1440 (3)	0.0784 (3)	0.3743 (3)	0.0179 (10)
C5	0.1271 (4)	0.1964 (4)	0.3656 (3)	0.0194 (12)
C6	0.0143 (4)	0.2496 (4)	0.3669 (3)	0.0195 (12)
C7	0.2535 (4)	0.0614 (4)	0.3741 (3)	0.0190 (12)
C8	0.3216 (4)	−0.0531 (4)	0.3805 (4)	0.0234 (12)
Cu1	0.51531 (5)	0.10043 (5)	0.13087 (5)	0.0233 (2)
O1	0.5666 (3)	−0.0657 (3)	0.1367 (3)	0.0280 (10)
O2	0.4995 (3)	−0.2483 (3)	0.1359 (3)	0.0271 (10)
O3	0.2329 (3)	0.2532 (3)	0.1120 (3)	0.0302 (10)
O4	0.0728 (3)	0.1515 (3)	0.1110 (3)	0.0310 (10)
O9	0.6516 (3)	0.1440 (3)	0.1069 (3)	0.0302 (10)
O10	0.6585 (3)	0.1163 (3)	0.3205 (3)	0.0316 (10)
O11	0.4531 (3)	0.2599 (3)	0.1113 (3)	0.0351 (10)
N1	0.2712 (4)	−0.1437 (3)	0.1204 (3)	0.0253 (11)
N2	0.1924 (3)	−0.0561 (3)	0.1154 (3)	0.0229 (11)
N3	0.3567 (3)	0.0310 (3)	0.1222 (3)	0.0210 (11)
C1	0.3685 (4)	−0.0882 (4)	0.1249 (4)	0.0217 (12)
C2	0.4882 (4)	−0.1371 (4)	0.1318 (3)	0.0215 (11)
C3	0.2427 (4)	0.0478 (4)	0.1159 (3)	0.0199 (12)
C4	0.1757 (4)	0.1610 (4)	0.1129 (4)	0.0212 (12)
H5	0.36710	0.16420	0.36410	0.0270*
H12A	−0.09350	−0.01230	0.17580	0.0450*
H12B	−0.19850	−0.06340	0.18780	0.0450*
H13A	0.01660	−0.21390	0.38700	0.0600*
H13B	0.12470	−0.14650	0.39470	0.0600*
H14A	−0.21270	−0.00110	0.37720	0.0340*
H14B	−0.16800	−0.10650	0.39590	0.0340*
H2	0.12460	−0.08260	0.11240	0.0280*
H9A	0.61880	0.14370	0.03990	0.0460*
H9B	0.68010	0.21210	0.13200	0.0460*
H10A	0.60750	0.13340	0.34120	0.0480*
H10B	0.70320	0.17910	0.33550	0.0480*
H11A	0.50060	0.32140	0.13270	0.0530*
H11B	0.38230	0.26930	0.11000	0.0530*

	U11	U22	U33	U12	U13	U23
Cu2	0.0215 (3)	0.0096 (3)	0.0376 (3)	0.0003 (2)	0.0211 (3)	0.0019 (2)
O5	0.0252 (16)	0.0143 (15)	0.047 (2)	−0.0007 (12)	0.0270 (15)	0.0022 (13)
O6	0.0313 (17)	0.0137 (16)	0.049 (2)	0.0024 (13)	0.0298 (17)	0.0010 (14)
O7	0.040 (2)	0.0133 (16)	0.082 (3)	0.0048 (15)	0.046 (2)	0.0052 (17)
O8	0.0322 (18)	0.0224 (17)	0.059 (2)	0.0065 (14)	0.0359 (18)	0.0019 (16)
O12	0.0283 (17)	0.0197 (16)	0.046 (2)	−0.0011 (13)	0.0232 (16)	−0.0058 (14)
O13	0.038 (2)	0.0178 (17)	0.084 (3)	0.0009 (15)	0.046 (2)	0.0049 (17)
O14	0.0207 (15)	0.0112 (14)	0.0397 (18)	−0.0004 (12)	0.0185 (14)	0.0021 (13)
N4	0.0247 (19)	0.0134 (18)	0.042 (2)	0.0041 (15)	0.0237 (18)	0.0021 (16)
N5	0.0193 (17)	0.0155 (18)	0.041 (2)	0.0007 (14)	0.0221 (17)	−0.0007 (16)
N6	0.0217 (18)	0.0070 (16)	0.0291 (19)	0.0020 (13)	0.0166 (16)	0.0015 (14)
C5	0.021 (2)	0.013 (2)	0.030 (2)	−0.0005 (16)	0.0177 (19)	−0.0002 (17)
C6	0.022 (2)	0.012 (2)	0.028 (2)	−0.0005 (17)	0.0161 (19)	−0.0009 (17)
C7	0.021 (2)	0.013 (2)	0.025 (2)	0.0027 (17)	0.0140 (18)	0.0022 (16)
C8	0.026 (2)	0.015 (2)	0.031 (2)	0.0035 (18)	0.017 (2)	−0.0009 (18)
Cu1	0.0210 (3)	0.0137 (3)	0.0399 (4)	−0.0015 (2)	0.0198 (3)	0.0011 (2)
O1	0.0277 (17)	0.0152 (16)	0.052 (2)	0.0029 (13)	0.0290 (16)	−0.0010 (14)
O2	0.0264 (16)	0.0140 (16)	0.052 (2)	0.0028 (13)	0.0287 (16)	0.0021 (14)
O3	0.0283 (17)	0.0115 (15)	0.056 (2)	0.0022 (13)	0.0267 (17)	0.0002 (14)
O4	0.0278 (17)	0.0203 (17)	0.052 (2)	0.0039 (13)	0.0266 (17)	0.0024 (15)
O9	0.0302 (17)	0.0166 (16)	0.053 (2)	−0.0025 (13)	0.0289 (17)	0.0021 (15)
O10	0.0275 (17)	0.0252 (17)	0.045 (2)	0.0013 (14)	0.0219 (16)	−0.0071 (15)
O11	0.0296 (17)	0.0144 (16)	0.069 (2)	−0.0006 (13)	0.0321 (18)	0.0027 (16)
N1	0.0240 (19)	0.0114 (18)	0.047 (2)	−0.0011 (14)	0.0237 (19)	−0.0015 (16)
N2	0.0178 (18)	0.0157 (19)	0.039 (2)	0.0003 (14)	0.0182 (17)	0.0012 (16)
N3	0.0189 (17)	0.0170 (18)	0.032 (2)	0.0016 (14)	0.0172 (16)	0.0017 (15)
C1	0.023 (2)	0.013 (2)	0.032 (2)	0.0018 (17)	0.017 (2)	0.0003 (17)
C2	0.0107 (19)	0.026 (2)	0.024 (2)	0.0070 (17)	0.0072 (18)	−0.0032 (18)
C3	0.022 (2)	0.013 (2)	0.026 (2)	−0.0004 (17)	0.0142 (19)	0.0021 (17)
C4	0.017 (2)	0.018 (2)	0.030 (2)	0.0040 (17)	0.0139 (19)	0.0020 (18)

Cu2—O5	1.989 (4)	O4—C4	1.230 (7)
Cu2—O12	2.386 (4)	O9—H9A	0.8500
Cu2—O13	1.926 (4)	O9—H9B	0.8500
Cu2—O14	1.959 (4)	O10—H10B	0.8500
Cu2—N6	2.013 (4)	O10—H10A	0.8500
Cu2—O14i	2.617 (3)	O11—H11A	0.8500
Cu1—N3	2.007 (4)	O11—H11B	0.8500
Cu1—O9	1.931 (4)	N4—N5	1.354 (6)
Cu1—O10	2.373 (4)	N4—C5	1.322 (7)
Cu1—O1	1.984 (4)	N5—C7	1.325 (6)
Cu1—O11	1.931 (4)	N6—C7	1.336 (7)
O5—C6	1.280 (6)	N6—C5	1.360 (6)
O6—C6	1.226 (6)	N5—H5	0.8500
O7—C8	1.248 (6)	N1—N2	1.354 (6)
O8—C8	1.241 (7)	N1—C1	1.302 (8)
O12—H12B	0.8300	N2—C3	1.332 (6)
O12—H12A	0.8300	N3—C1	1.368 (6)
O13—H13A	0.8500	N3—C3	1.338 (7)
O13—H13B	0.8500	N2—H2	0.8500
O14—H14A	0.8500	C5—C6	1.500 (7)
O14—H14B	0.8500	C7—C8	1.520 (7)
O1—C2	1.220 (6)	C1—C2	1.497 (8)
O2—C2	1.276 (6)	C3—C4	1.513 (7)
O3—C4	1.264 (6)
O5—Cu2—O12	89.33 (14)	Cu1—O10—H10B	108.00
O5—Cu2—O13	175.94 (16)	Cu1—O10—H10A	105.00
O5—Cu2—O14	88.58 (17)	Cu1—O11—H11B	115.00
O5—Cu2—N6	83.67 (16)	H11A—O11—H11B	111.00
O5—Cu2—O14i	86.96 (14)	Cu1—O11—H11A	127.00
O12—Cu2—O13	94.73 (14)	N5—N4—C5	102.5 (4)
O12—Cu2—O14	94.74 (13)	N4—N5—C7	111.3 (5)
O12—Cu2—N6	93.33 (15)	Cu2—N6—C7	147.9 (3)
O12—Cu2—O14i	174.72 (14)	Cu2—N6—C5	108.3 (3)
O13—Cu2—O14	91.41 (17)	C5—N6—C7	103.9 (4)
O13—Cu2—N6	95.76 (17)	N4—N5—H5	132.00
O13—Cu2—O14i	89.02 (14)	C7—N5—H5	117.00
O14—Cu2—N6	168.74 (14)	N2—N1—C1	103.1 (4)
O14—Cu2—O14i	81.43 (12)	N1—N2—C3	110.9 (4)
O14i—Cu2—N6	90.00 (14)	Cu1—N3—C1	108.2 (3)
O9—Cu1—N3	165.50 (16)	Cu1—N3—C3	148.5 (3)
O1—Cu1—O9	88.77 (17)	C1—N3—C3	103.4 (4)
O1—Cu1—O10	91.04 (14)	C3—N2—H2	138.00
O1—Cu1—O11	174.72 (16)	N1—N2—H2	111.00
O1—Cu1—N3	83.50 (17)	N4—C5—N6	113.6 (5)
O9—Cu1—O10	94.13 (16)	N6—C5—C6	119.3 (4)
O9—Cu1—O11	91.57 (17)	N4—C5—C6	127.0 (4)
O11—Cu1—N3	95.02 (17)	O5—C6—O6	126.8 (5)
O10—Cu1—O11	94.20 (14)	O5—C6—C5	113.1 (4)
O10—Cu1—N3	98.25 (15)	O6—C6—C5	120.1 (5)
Cu2—O5—C6	115.6 (4)	N5—C7—N6	108.6 (4)
Cu2—O14—Cu2i	98.57 (13)	N6—C7—C8	128.7 (4)
Cu2—O12—H12A	99.00	N5—C7—C8	122.7 (5)
Cu2—O12—H12B	100.00	O8—C8—C7	115.7 (4)
H12A—O12—H12B	128.00	O7—C8—O8	128.2 (5)
Cu2—O13—H13A	129.00	O7—C8—C7	116.1 (5)
Cu2—O13—H13B	104.00	N1—C1—N3	114.1 (5)
H13A—O13—H13B	119.00	N1—C1—C2	128.9 (4)
Cu2—O14—H14B	118.00	N3—C1—C2	117.0 (5)
H14A—O14—H14B	98.00	O1—C2—O2	127.2 (5)
Cu2i—O14—H14A	114.00	O1—C2—C1	116.1 (4)
Cu2—O14—H14A	119.00	O2—C2—C1	116.6 (5)
Cu2i—O14—H14B	109.00	N3—C3—C4	129.5 (4)
Cu1—O1—C2	115.2 (4)	N2—C3—N3	108.6 (4)
Cu1—O9—H9B	109.00	N2—C3—C4	121.9 (5)
H9A—O9—H9B	110.00	O3—C4—C3	115.4 (5)
Cu1—O9—H9A	109.00	O4—C4—C3	116.1 (4)
H10A—O10—H10B	101.00	O3—C4—O4	128.5 (5)
O12—Cu2—O5—C6	−95.3 (3)	C5—N6—C7—C8	−179.2 (4)
O14—Cu2—O5—C6	170.0 (3)	Cu2—N6—C5—N4	179.9 (3)
N6—Cu2—O5—C6	−1.9 (3)	C7—N6—C5—N4	−0.1 (5)
O14i—Cu2—O5—C6	88.5 (3)	C5—N6—C7—N5	0.3 (4)
O5—Cu2—O14—Cu2i	−87.14 (15)	Cu2—N6—C5—C6	2.0 (4)
O12—Cu2—O14—Cu2i	−176.35 (12)	Cu2—N6—C7—C8	0.9 (8)
O13—Cu2—O14—Cu2i	88.80 (15)	Cu2—N6—C7—N5	−179.7 (4)
O14i—Cu2—O14—Cu2i	−0.02 (13)	C7—N6—C5—C6	−178.0 (3)
O5—Cu2—N6—C5	−0.2 (3)	C1—N1—N2—C3	0.6 (5)
O5—Cu2—N6—C7	179.7 (6)	N2—N1—C1—N3	−0.5 (5)
O12—Cu2—N6—C5	88.8 (3)	N2—N1—C1—C2	179.9 (5)
O12—Cu2—N6—C7	−91.3 (6)	N1—N2—C3—N3	−0.5 (5)
O13—Cu2—N6—C5	−176.2 (3)	N1—N2—C3—C4	−178.9 (4)
O13—Cu2—N6—C7	3.8 (6)	C3—N3—C1—C2	179.9 (4)
O14i—Cu2—N6—C5	−87.1 (3)	C3—N3—C1—N1	0.2 (5)
O14i—Cu2—N6—C7	92.8 (6)	Cu1—N3—C1—N1	179.6 (3)
O5—Cu2—O14i—Cu2i	89.02 (17)	C1—N3—C3—C4	178.4 (4)
O13—Cu2—O14i—Cu2i	−91.57 (18)	Cu1—N3—C3—C4	−0.5 (9)
O14—Cu2—O14i—Cu2i	0.02 (16)	Cu1—N3—C1—C2	−0.7 (5)
N6—Cu2—O14i—Cu2i	172.68 (16)	Cu1—N3—C3—N2	−178.7 (4)
O11—Cu1—N3—C3	−6.2 (6)	C1—N3—C3—N2	0.2 (4)
O9—Cu1—O1—C2	−166.9 (3)	N6—C5—C6—O6	175.4 (4)
O10—Cu1—O1—C2	99.0 (3)	N4—C5—C6—O6	−2.2 (6)
N3—Cu1—O1—C2	0.8 (3)	N6—C5—C6—O5	−3.6 (5)
O1—Cu1—N3—C1	0.0 (3)	N4—C5—C6—O5	178.8 (4)
O1—Cu1—N3—C3	178.9 (6)	N6—C7—C8—O7	−5.1 (7)
O10—Cu1—N3—C1	−90.1 (3)	N6—C7—C8—O8	175.1 (4)
O10—Cu1—N3—C3	88.8 (6)	N5—C7—C8—O8	−4.3 (6)
O11—Cu1—N3—C1	174.9 (3)	N5—C7—C8—O7	175.5 (4)
Cu2—O5—C6—O6	−175.7 (4)	N1—C1—C2—O1	−178.9 (5)
Cu2—O5—C6—C5	3.3 (4)	N3—C1—C2—O1	1.5 (6)
Cu1—O1—C2—C1	−1.4 (5)	N3—C1—C2—O2	179.0 (4)
Cu1—O1—C2—O2	−178.6 (3)	N1—C1—C2—O2	−1.4 (7)
C5—N4—N5—C7	0.4 (4)	N2—C3—C4—O3	−178.9 (4)
N5—N4—C5—C6	177.5 (4)	N2—C3—C4—O4	0.7 (6)
N5—N4—C5—N6	−0.2 (5)	N3—C3—C4—O3	3.1 (7)
N4—N5—C7—N6	−0.4 (5)	N3—C3—C4—O4	−177.4 (4)
N4—N5—C7—C8	179.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O6ii	0.85	1.87	2.709 (6)	169
N5—H5···O8	0.85	2.46	2.773 (5)	103
N5—H5···O2iii	0.85	1.89	2.655 (7)	148
O9—H9A···O1iv	0.85	2.50	3.221 (5)	144
O9—H9A···O2iv	0.85	2.49	3.256 (5)	150
O9—H9B···O7iii	0.85	1.85	2.596 (5)	145
O10—H10A···O2iii	0.85	2.02	2.798 (6)	151
O10—H10B···O5v	0.85	2.59	3.103 (6)	120
O10—H10B···N1iii	0.85	2.10	2.863 (5)	149
O11—H11A···O8iii	0.85	1.84	2.650 (5)	160
O11—H11B···O3	0.85	1.83	2.662 (6)	167
O12—H12A···O6ii	0.83	2.15	2.811 (6)	137
O12—H12B···O1vi	0.83	2.49	3.111 (6)	132
O12—H12B···N4ii	0.83	2.19	2.821 (5)	133
O13—H13A···O4ii	0.85	1.89	2.714 (5)	164
O13—H13B···O7	0.85	1.81	2.654 (7)	172
O14—H14A···O10vi	0.85	1.86	2.686 (5)	163
O14—H14B···O3ii	0.85	1.76	2.599 (5)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O6i	0.85	1.87	2.709 (6)	169
N5—H5⋯O8	0.85	2.46	2.773 (5)	103
N5—H5⋯O2ii	0.85	1.89	2.655 (7)	148
O9—H9A⋯O1iii	0.85	2.50	3.221 (5)	144
O9—H9A⋯O2iii	0.85	2.49	3.256 (5)	150
O9—H9B⋯O7ii	0.85	1.85	2.596 (5)	145
O10—H10A⋯O2ii	0.85	2.02	2.798 (6)	151
O10—H10B⋯O5iv	0.85	2.59	3.103 (6)	120
O10—H10B⋯N1ii	0.85	2.10	2.863 (5)	149
O11—H11A⋯O8ii	0.85	1.84	2.650 (5)	160
O11—H11B⋯O3	0.85	1.83	2.662 (6)	167
O12—H12A⋯O6i	0.83	2.15	2.811 (6)	137
O12—H12B⋯O1v	0.83	2.49	3.111 (6)	132
O12—H12B⋯N4i	0.83	2.19	2.821 (5)	133
O13—H13A⋯O4i	0.85	1.89	2.714 (5)	164
O13—H13B⋯O7	0.85	1.81	2.654 (7)	172
O14—H14A⋯O10v	0.85	1.86	2.686 (5)	163
O14—H14B⋯O3i	0.85	1.76	2.599 (5)	169

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .