Bis­(ethyl­enedi­amine-N,N')(pyrimidine-2-carboxyl­ato-N¹,O)­cobalt(III) bis­(tri­fluoro­methane­sulfonate) dihydrate

In the title compound, the coordination geometry of the Co^III atom is only slightly distorted from regular octahedral, and the racemic nature of the material was confirmed by X-ray structure analysis.

S1. Comment

Studies of electron-transfer reactions between two metal centres, where 2,2'-bipyrimidine (bpm) or its ring-substituted analogues would serve as a chelating bridging ligand, included a preparation of [Co(en)₂(bpm)](CF₃SO₃)₃ complex (en = ethylenediamine) (Dixon et al., 1981) and its chloride analogue. Hovewer, under unpredictable circumstances we ended up with the title compound. Most likely, the relatively high impurity of the bpm batch (Lancaster Syntheses Ltd) used for the preparation without purification is responsible for such a result. In order to understand unusual `reaction path', the products obtained were characterized by X-ray structure analysis. The analysis revealed bis(ethylenediamine)(pyrimidin-2-ylcarboxylato)cobalt(III) bis(trifluoromethanesulfonate) dihydrate, (I), and its chloride analogue. As 2,2'-bipyrimidine was not coordinated to the metal atom, the analysis of the commercial chemical was undertaken. It revealed the presence of pyrimidine-2-carboxylic acid which has been of higher preference to be coordinated via mixed O,N-donated ligands than N,N of bpm. Due to the low quality of the data collected for bis(ethylenediamine)(pyrimidine-2-carboxylato)cobalt(III) chloride 1.5-hydrate, (II), the detailed description of crystal and molecular structure will be given only for bis(ethylenediamine)(pyrimidin-2-ylcarboxylato)cobalt(III) bis(trifluoromethanesulfonate) dihydrate, (I).

The solved structures revealed the same cation structure with ethylenediamine as a bidentate ligands. Cobalt is in a 3+ oxidation state and two ethylenediamine ligands and pyrimidinyl-2-carboxylato ligand (which was supposed to be bpm) built an octahedral environment. Tris-bidentate ligands in the complexes might introduce certain degree of octahedral distortion. However, the title complex reveals minor octahedral distortion. In the structures with different ligands electron-donating ability of nitrogen varies, thus Co—N bond lengths might be different. Here, five Co—N bonds with mean value 1.952 (2) Å are all nearly equal. The bite angle values range from 83.84 (7) to 86.60 (8)°. Other bonding angles do not deviate significantly from 90° (<2°). In the synthesis of (II), optically pure, Δ absolute configuration was obtained whereas in (I), the racemate appeared. Chirality of these complexes can be deduced from the space-group symmetry. Three-dimensional hydrogen-bond network involves: (a) N—H···O between ethylenediamine ligands and trifluoromethanesulfonates in the [111] direction; (b) N—H···N between ethylenediamine ligands and N atoms of pyrimidine-2-carboxylato ligand; (c) O—H···O between crystalline water molecules and crystalline water molecules towards trifluoromethanesulfonate anions.

S2. Experimental

Crystals of both compounds were grown by slow evaporation from ethanol and acetone mixtures affording acceptable crystallographic samples. The crystals obtained were used for intensity data collection. In order to minimize crystal decay, the data for (I) were collected at low temperature (100 K), while the data for (II) were collected at room temperature.

S3. Refinement

H atoms were located from a different synthesis and refined isotropically.

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: HELENA (Spek, 1997b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997b).

bis(ethylenediamine)pyrimidinyl-2-carboxylato Co(3+) trifluoromethanesulfonate dihydrate

Crystal data

[Co(C5H3N2O2)(C2H8N2)2](CF3O3S)2·2H2O	Z = 2
Mr = 636.42	F(000) = 648
Triclinic, P1	Dx = 1.881 Mg m^−3
a = 6.4976 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.729 (1) Å	Cell parameters from 25 reflections
c = 14.741 (1) Å	θ = 20–24°
α = 73.40 (1)°	µ = 1.06 mm^−1
β = 81.98 (1)°	T = 100 K
γ = 74.61 (1)°	Prismatic, orange
V = 1123.8 (2) Å^3	0.28 × 0.28 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	4867 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 30.4°, θmin = 2.5°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (PLATON97; Spek, 1997a)	k = −17→18
Tmin = 0.817, Tmax = 0.899	l = −20→20
7328 measured reflections	3 standard reflections every 87 reflections
6780 independent reflections	intensity decay: 0.7%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	All H-atom parameters refined
S = 0.95	Calculated w = 1/[σ^2(Fo^2) + (0.045P)^2 + 1.1493P] where P = (Fo^2 + 2Fc^2)/3
6780 reflections	(Δ/σ)max = 0.014
417 parameters	Δρmax = 0.63 e Å^−3
0 restraints	Δρmin = −0.48 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Co1	0.27444 (5)	0.03937 (3)	0.77233 (2)	0.00817 (8)
N1	0.1381 (3)	0.15845 (18)	0.66682 (14)	0.0127 (4)
H11N	0.022 (5)	0.194 (3)	0.689 (2)	0.017 (8)*
H12N	0.115 (5)	0.129 (3)	0.625 (2)	0.014 (7)*
C1	0.2849 (4)	0.2345 (2)	0.62385 (17)	0.0134 (4)
H11	0.247 (4)	0.277 (2)	0.563 (2)	0.009 (7)*
H12	0.278 (4)	0.282 (2)	0.6652 (19)	0.009 (7)*
C2	0.5065 (4)	0.1593 (2)	0.61894 (16)	0.0137 (4)
H21	0.618 (4)	0.206 (2)	0.5974 (19)	0.008 (6)*
H22	0.512 (5)	0.114 (2)	0.574 (2)	0.015 (7)*
N2	0.5417 (3)	0.08153 (17)	0.71597 (14)	0.0110 (4)
H21N	0.589 (4)	0.117 (2)	0.7491 (19)	0.007 (6)*
H22N	0.650 (5)	0.018 (3)	0.711 (2)	0.023 (8)*
N3	0.4234 (3)	−0.07992 (17)	0.87463 (14)	0.0107 (4)
H31N	0.328 (5)	−0.099 (3)	0.921 (2)	0.022 (8)*
H32N	0.507 (5)	−0.052 (2)	0.894 (2)	0.014 (7)*
C3	0.5282 (4)	−0.1810 (2)	0.83923 (18)	0.0145 (4)
H31	0.663 (4)	−0.168 (2)	0.8079 (18)	0.004 (6)*
H32	0.552 (5)	−0.247 (3)	0.890 (2)	0.021 (8)*
C4	0.3802 (4)	−0.1881 (2)	0.77187 (18)	0.0148 (4)
H41	0.452 (5)	−0.244 (2)	0.739 (2)	0.013 (7)*
H42	0.247 (5)	−0.205 (2)	0.805 (2)	0.017 (7)*
N4	0.3223 (3)	−0.07507 (17)	0.70356 (14)	0.0119 (4)
H41N	0.425 (5)	−0.068 (3)	0.657 (2)	0.024 (8)*
H42N	0.193 (6)	−0.066 (3)	0.684 (3)	0.036 (10)*
N5	0.1903 (3)	0.13991 (16)	0.85708 (13)	0.0091 (3)
C5	0.2895 (4)	0.2116 (2)	0.87482 (16)	0.0119 (4)
H5	0.417 (5)	0.223 (2)	0.841 (2)	0.018 (8)*
C6	0.2029 (4)	0.2689 (2)	0.94357 (17)	0.0133 (4)
H6	0.276 (5)	0.321 (2)	0.954 (2)	0.013 (7)*
C7	0.0151 (4)	0.2490 (2)	0.99339 (17)	0.0140 (4)
H7	−0.055 (5)	0.288 (2)	1.041 (2)	0.012 (7)*
N6	−0.0873 (3)	0.17898 (16)	0.97499 (13)	0.0113 (4)
C8	0.0042 (3)	0.12876 (18)	0.90764 (15)	0.0092 (4)
C9	−0.1016 (3)	0.04899 (18)	0.88281 (15)	0.0092 (4)
O7	0.0062 (2)	0.00158 (14)	0.81920 (11)	0.0110 (3)
O8	−0.2755 (3)	0.03443 (14)	0.92236 (11)	0.0123 (3)
S1	0.10777 (9)	0.14576 (5)	0.41580 (4)	0.01303 (12)
O1	0.0886 (3)	0.09320 (15)	0.34281 (12)	0.0165 (4)
O2	0.3267 (3)	0.13434 (16)	0.43357 (12)	0.0175 (4)
O3	−0.0354 (3)	0.12652 (17)	0.49948 (13)	0.0221 (4)
C10	0.0103 (4)	0.2962 (2)	0.35977 (18)	0.0169 (5)
F1	0.0049 (3)	0.35803 (13)	0.41964 (11)	0.0229 (3)
F2	0.1345 (3)	0.33033 (13)	0.28278 (11)	0.0245 (3)
F3	−0.1878 (3)	0.31634 (15)	0.33318 (13)	0.0298 (4)
S2	0.28482 (9)	0.61881 (5)	0.24925 (4)	0.01280 (12)
O4	0.0746 (3)	0.60365 (16)	0.24621 (15)	0.0248 (4)
O5	0.4458 (3)	0.57489 (17)	0.18328 (14)	0.0267 (4)
O6	0.2864 (3)	0.73205 (14)	0.25284 (12)	0.0151 (3)
C11	0.3704 (4)	0.5329 (2)	0.36573 (19)	0.0209 (5)
F4	0.3916 (3)	0.42384 (13)	0.37522 (13)	0.0277 (4)
F5	0.5591 (3)	0.54570 (16)	0.37952 (15)	0.0398 (5)
F6	0.2283 (4)	0.56298 (18)	0.43291 (13)	0.0500 (6)
O9	0.2497 (4)	0.45926 (18)	0.07490 (15)	0.0279 (5)
H91	0.304 (7)	0.498 (4)	0.105 (3)	0.060 (13)*
H92	0.119 (7)	0.457 (3)	0.094 (3)	0.049 (13)*
O10	0.8285 (4)	0.43453 (18)	0.11212 (16)	0.0265 (4)
H101	0.740 (7)	0.461 (4)	0.153 (3)	0.056 (13)*
H102	0.779 (8)	0.461 (4)	0.061 (4)	0.062 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0054 (1)	0.0120 (2)	0.0081 (1)	−0.0016 (1)	0.0011 (1)	−0.0053 (1)
N1	0.0081 (9)	0.0184 (10)	0.0118 (9)	−0.0023 (8)	0.0025 (7)	−0.0066 (8)
C1	0.0121 (11)	0.0160 (11)	0.0111 (10)	−0.0033 (9)	0.0007 (8)	−0.0025 (9)
C2	0.0121 (10)	0.0186 (11)	0.0098 (10)	−0.0039 (9)	0.0017 (8)	−0.0036 (9)
N2	0.0093 (9)	0.0134 (9)	0.0120 (9)	−0.0036 (7)	0.0007 (7)	−0.0058 (7)
N3	0.0085 (9)	0.0143 (9)	0.0110 (9)	−0.0031 (7)	0.0002 (7)	−0.0058 (7)
C3	0.0138 (11)	0.0119 (11)	0.0172 (11)	0.0005 (9)	−0.0006 (9)	−0.0063 (9)
C4	0.0153 (11)	0.0128 (11)	0.0177 (11)	−0.0037 (9)	0.0015 (9)	−0.0070 (9)
N4	0.0076 (9)	0.0167 (10)	0.0137 (9)	−0.0036 (7)	0.0013 (7)	−0.0078 (8)
N5	0.0061 (8)	0.0117 (9)	0.0097 (8)	−0.0015 (7)	0.0001 (6)	−0.0042 (7)
C5	0.0102 (10)	0.0137 (10)	0.0125 (10)	−0.0041 (8)	−0.0006 (8)	−0.0035 (8)
C6	0.0149 (11)	0.0117 (10)	0.0142 (10)	−0.0028 (9)	−0.0003 (8)	−0.0053 (8)
C7	0.0161 (11)	0.0131 (11)	0.0132 (10)	−0.0011 (9)	0.0001 (9)	−0.0069 (8)
N6	0.0106 (9)	0.0124 (9)	0.0104 (9)	−0.0009 (7)	0.0019 (7)	−0.0052 (7)
C8	0.0067 (9)	0.0096 (9)	0.0102 (9)	0.0004 (7)	−0.0006 (7)	−0.0031 (8)
C9	0.0080 (9)	0.0093 (9)	0.0094 (9)	−0.0004 (8)	−0.0016 (7)	−0.0021 (8)
O7	0.0075 (7)	0.0156 (8)	0.0120 (7)	−0.0035 (6)	0.0012 (6)	−0.0072 (6)
O8	0.0070 (7)	0.0161 (8)	0.0137 (8)	−0.0025 (6)	0.0024 (6)	−0.0056 (6)
S1	0.0098 (2)	0.0187 (3)	0.0128 (3)	−0.0030 (2)	0.0023 (2)	−0.0093 (2)
O1	0.0140 (8)	0.0219 (9)	0.0173 (8)	−0.0023 (7)	0.0000 (7)	−0.0132 (7)
O2	0.0102 (8)	0.0262 (10)	0.0174 (8)	−0.0008 (7)	−0.0028 (6)	−0.0103 (7)
O3	0.0214 (10)	0.0296 (10)	0.0187 (9)	−0.0110 (8)	0.0110 (7)	−0.0129 (8)
C10	0.0126 (11)	0.0210 (12)	0.0194 (12)	−0.0003 (9)	−0.0018 (9)	−0.0119 (10)
F1	0.0240 (8)	0.0240 (8)	0.0255 (8)	−0.0039 (7)	0.0009 (6)	−0.0166 (7)
F2	0.0300 (9)	0.0220 (8)	0.0178 (7)	−0.0032 (7)	0.0034 (6)	−0.0044 (6)
F3	0.0163 (8)	0.0333 (9)	0.0431 (10)	0.0046 (7)	−0.0124 (7)	−0.0196 (8)
S2	0.0121 (3)	0.0131 (3)	0.0129 (3)	−0.0014 (2)	0.0004 (2)	−0.0049 (2)
O4	0.0169 (9)	0.0224 (10)	0.0366 (11)	−0.0053 (8)	−0.0092 (8)	−0.0060 (8)
O5	0.0282 (11)	0.0274 (10)	0.0221 (10)	−0.0007 (8)	0.0090 (8)	−0.0130 (8)
O6	0.0144 (8)	0.0136 (8)	0.0165 (8)	−0.0019 (6)	0.0019 (6)	−0.0052 (6)
C11	0.0206 (13)	0.0195 (12)	0.0202 (12)	−0.0019 (10)	−0.0026 (10)	−0.0032 (10)
F4	0.0228 (8)	0.0154 (8)	0.0391 (10)	−0.0035 (6)	−0.0059 (7)	0.0029 (7)
F5	0.0391 (11)	0.0298 (10)	0.0528 (12)	−0.0135 (8)	−0.0319 (10)	0.0044 (9)
F6	0.0664 (15)	0.0469 (12)	0.0158 (8)	0.0123 (11)	0.0095 (9)	−0.0049 (8)
O9	0.0352 (13)	0.0251 (11)	0.0250 (11)	−0.0044 (9)	−0.0046 (9)	−0.0103 (8)
O10	0.0327 (12)	0.0240 (10)	0.0199 (10)	0.0020 (9)	0.0010 (9)	−0.0104 (8)

Geometric parameters (Å, º)

Co1—O7	1.915 (2)	C8—C9	1.514 (3)
Co1—N4	1.940 (2)	C9—O8	1.232 (3)
Co1—N1	1.956 (2)	C9—O7	1.284 (3)
Co1—N2	1.957 (2)	S1—O3	1.441 (2)
Co1—N3	1.959 (2)	S1—O2	1.444 (2)
Co1—N5	1.962 (2)	S1—O1	1.454 (2)
N1—C1	1.490 (3)	S1—C10	1.830 (3)
C1—C2	1.508 (3)	C10—F1	1.332 (3)
C2—N2	1.497 (3)	C10—F2	1.333 (3)
N3—C3	1.487 (3)	C10—F3	1.336 (3)
C3—C4	1.511 (3)	S2—O5	1.439 (2)
C4—N4	1.489 (3)	S2—O4	1.438 (2)
N5—C8	1.348 (3)	S2—O6	1.460 (2)
N5—C5	1.346 (3)	S2—C11	1.823 (3)
C5—C6	1.386 (3)	C11—F6	1.324 (3)
C6—C7	1.379 (3)	C11—F5	1.329 (3)
C7—N6	1.346 (3)	C11—F4	1.326 (3)
N6—C8	1.321 (3)
O7—Co1—N4	86.59 (8)	N6—C8—C9	119.36 (19)
O7—Co1—N1	90.64 (8)	N5—C8—C9	114.41 (18)
N4—Co1—N1	92.61 (9)	O8—C9—O7	125.8 (2)
O7—Co1—N2	176.19 (8)	O8—C9—C8	120.35 (19)
N4—Co1—N2	91.78 (9)	O7—C9—C8	113.84 (19)
N1—Co1—N2	85.99 (8)	C9—O7—Co1	116.12 (14)
O7—Co1—N3	91.79 (8)	O3—S1—O2	115.01 (11)
N4—Co1—N3	86.60 (8)	O3—S1—O1	115.96 (11)
N1—Co1—N3	177.40 (9)	O2—S1—O1	113.37 (10)
N2—Co1—N3	91.55 (9)	O3—S1—C10	103.14 (12)
O7—Co1—N5	83.84 (7)	O2—S1—C10	104.42 (11)
N4—Co1—N5	169.61 (8)	O1—S1—C10	102.72 (11)
N1—Co1—N5	91.54 (8)	F1—C10—F2	108.5 (2)
N2—Co1—N5	98.01 (8)	F1—C10—F3	108.04 (19)
N3—Co1—N5	89.65 (8)	F2—C10—F3	107.9 (2)
C1—N1—Co1	108.62 (15)	F1—C10—S1	111.00 (17)
N1—C1—C2	106.43 (19)	F2—C10—S1	111.12 (16)
N2—C2—C1	106.77 (18)	F3—C10—S1	110.11 (18)
C2—N2—Co1	109.38 (14)	O5—S2—O4	115.46 (13)
C3—N3—Co1	109.36 (14)	O5—S2—O6	113.88 (11)
N3—C3—C4	106.73 (19)	O4—S2—O6	113.86 (11)
N4—C4—C3	107.56 (19)	O5—S2—C11	104.53 (12)
C4—N4—Co1	108.50 (15)	O4—S2—C11	104.78 (13)
C8—N5—C5	117.03 (19)	O6—S2—C11	102.44 (11)
C8—N5—Co1	111.64 (15)	F6—C11—F5	109.0 (3)
C5—N5—Co1	131.26 (16)	F6—C11—F4	108.0 (2)
N5—C5—C6	120.4 (2)	F5—C11—F4	107.2 (2)
C7—C6—C5	118.0 (2)	F6—C11—S2	110.02 (18)
N6—C7—C6	122.0 (2)	F5—C11—S2	110.44 (19)
C8—N6—C7	116.3 (2)	F4—C11—S2	112.11 (19)
N6—C8—N5	126.2 (2)
N1—Co1—O7—C9	−94.09	O3—S1—C10—F3	−64.09
N3—Co1—O7—C9	86.85	O3—S1—C10—F2	176.38
N4—Co1—O7—C9	173.33	O4—S2—C11—F6	−55.70
N5—Co1—O7—C9	−2.61	O5—S2—C11—F6	−177.55
O7—Co1—N1—C1	164.22	O6—S2—C11—F6	63.42
N2—Co1—N1—C1	−17.56	O5—S2—C11—F4	−57.32
N4—Co1—N1—C1	−109.16	O6—S2—C11—F4	−176.36
N5—Co1—N1—C1	80.36	O4—S2—C11—F4	64.52
N1—Co1—N2—C2	−11.24	O5—S2—C11—F5	62.14
N3—Co1—N2—C2	167.91	O6—S2—C11—F5	−56.90
N4—Co1—N2—C2	81.26	O4—S2—C11—F5	−176.01
N5—Co1—N2—C2	−102.23	Co1—O7—C9—O8	−178.99
O7—Co1—N3—C3	98.13	Co1—O7—C9—C8	1.10
N2—Co1—N3—C3	−80.04	Co1—N1—C1—C2	42.20
N4—Co1—N3—C3	11.65	Co1—N2—C2—C1	37.17
N5—Co1—N3—C3	−178.04	Co1—N3—C3—C4	−36.32
O7—Co1—N4—C4	−75.75	Co1—N4—C4—C3	−40.43
N1—Co1—N4—C4	−166.23	Co1—N5—C5—C6	−175.62
N2—Co1—N4—C4	107.70	Co1—N5—C8—N6	175.24
N3—Co1—N4—C4	16.25	C5—N5—C8—N6	−2.09
O7—Co1—N5—C5	−179.56	Co1—N5—C8—C9	−3.94
N1—Co1—N5—C5	−89.09	C5—N5—C8—C9	178.73
N2—Co1—N5—C5	−2.91	C8—N5—C5—C6	1.08
N3—Co1—N5—C5	88.60	C7—N6—C8—C9	−179.90
O7—Co1—N5—C8	3.60	C8—N6—C7—C6	1.19
N1—Co1—N5—C8	94.07	C7—N6—C8—N5	0.95
N2—Co1—N5—C8	−179.75	N1—C1—C2—N2	−51.48
N3—Co1—N5—C8	−88.23	N3—C3—C4—N4	50.02
O1—S1—C10—F2	−62.72	N5—C5—C6—C7	0.83
O1—S1—C10—F3	56.81	C5—C6—C7—N6	−2.04
O2—S1—C10—F3	175.36	N6—C8—C9—O8	2.85
O1—S1—C10—F1	176.40	N5—C8—C9—O8	−177.91
O2—S1—C10—F1	−65.05	N6—C8—C9—O7	−177.24
O3—S1—C10—F1	55.50	N5—C8—C9—O7	2.01
O2—S1—C10—F2	55.82

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11N···O6^i	0.85	2.15	2.991 (3)	174 (3)
N1—H12N···O3	0.86	2.22	3.019 (2)	155 (3)
N2—H21N···O6^ii	0.88	2.27	3.044 (3)	147 (2)
N2—H22N···O1^iii	0.94	2.12	3.025 (3)	162 (3)
N3—H31N···N6^iv	0.88	2.26	3.129 (3)	167 (3)
N3—H32N···O8^v	0.84	2.15	2.987 (3)	172 (3)
N4—H41N···O2^iii	0.89	2.10	2.921 (3)	152 (3)
N4—H42N···O1^vi	0.89	2.06	2.928 (3)	164 (4)
O9—H91···O5	0.91	2.13	3.042 (3)	175 (4)
O9—H92···O10^vii	0.86	1.96	2.798 (4)	166 (4)
O10—H101···O5	0.85	2.15	2.908 (3)	149 (4)
O10—H102···O9^viii	0.81	1.98	2.754 (2)	161 (5)

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