N. V. Tsaryk, A. V. Dudko, A. N. Kozachkova and V. I. Pekhnyo
The asymmetric unit of title compound, [Co(C3H10NO7P2)2(H2O)2], contains one half-molecule of the complex. The CoII atom is located on an inversion centre and displays a distorted octahedral coordination geometry defined by four O atoms of two 3-azaniumyl-1-hydroxypropylidene-1,1-bisphosphonato ligands in the equatorial plane and two water molecules located in axial positions. The ligand molecules, which exist in a zwitterionic state, form two six-membered chelate rings with chair conformations. In the crystal, molecules are interlinked by O—H
O and N—HO hydrogen bonds, forming a three-dimensional supramolecular structure.
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Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811045120/ez2263sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536811045120/ez2263Isup2.hkl |
CCDC reference: 858136
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.003 Å - R factor = 0.029
- wR factor = 0.080
- Data-to-parameter ratio = 16.6
(C-C) = 0.003 ÅcheckCIF/PLATON results
No syntax errors found
Comment top
In recent years the design and synthesis of novel metal-organic coordinationcompounds based on gem-diphosphonic acids has attracted much interest due totheirstructural diversity and possible applications in many areas (Matczak-Jon &Videnova-Adrabinska, 2005). Particular attention has been paid to3-amino-1-hydroxypropane-1,1-diyl)bis(phosphonic acid) (pamidronic acid)due to its biological activity and as a result of its usage as a drug toprevent calcification and inhibit bone resorption, etc.(Matkovskaya et al., 2001).
The molecular structure of title complex is shown in Fig. 1; as illustrated themolecule of the complex forms discrete monomeric units. The asymmetric unitcontains one-half of the formula unit [Co(C3H10NO7P2)2(H2O)2],with the Co atom lying on an inversion center.
The CoII ion is coordinated in a slightly distorted octahedral geometrywhich consists of six oxygen atoms, two fromwater molecules located in the axial positions and four from thetwo phosphonate groups of two different ligands, which exist inzwitterionic form, creating two six-membered [O, O] chelate rings.The Co—O bond lengths andthe O—Co—O angles have expected values (Allen et al., 2004)andconform well to the previously reported related structure (Bon etal., 2010). In the packing, O—H···O and N—H···O hydrogen-bondsexist between the water molecules, phosphonate, hydroxyl O atoms and nitrogenatoms of the amino group (Fig. 2, Table 1). Thus, the molecules are interlinkedby these hydrogen bonds to create a three-dimensional structure which partiallyinfluences and stabilizes the configuration of the molecule.
Related literature top
For general background to organic diphosphonic acids and their applications,see: Matczak-Jon & Videnova-Adrabinska (2005). For applications ofbisphosphonate metal complexes in medicine, see: Matkovskaya et al.(2001). For a related structure, see: Bon et al. (2010).Forbond-length data, see: Allen et al. (2004).
Experimental top
Light pink crystals of the title compound were obtained from a mixture ofCo(NO3)2.6H2O (0,25 mmol; 0,0728 g) and3-aminohydroxypropilidene-1,1-diphosphonic acid (0,5 mmol; 0,1175 g) in 20 ml H2O. The combined solution was allowed to slowly evaporate. After 30 days,suitable crystals for X-ray data collection were obtained.
Refinement top
All non-H atoms were refined with anisotropic displacement parameters. H atomsbonded to O and N atoms were located in a difference Fourier map. Theirpositions were refined freely whereas displacement parameters were fixed toUiso(H) = 1.5Ueq(N,O).The H1n atom of the amino groupwas refined with a distance restraint (N—H= 0.91 Å). Other H atomsbonded to C were positioned geometrically and refined using a riding modelwith C—H = 0.99 Å for CH2 with Uiso(H) = 1.2Ueq(C).
Structure description top
In recent years the design and synthesis of novel metal-organic coordinationcompounds based on gem-diphosphonic acids has attracted much interest due totheirstructural diversity and possible applications in many areas (Matczak-Jon &Videnova-Adrabinska, 2005). Particular attention has been paid to3-amino-1-hydroxypropane-1,1-diyl)bis(phosphonic acid) (pamidronic acid)due to its biological activity and as a result of its usage as a drug toprevent calcification and inhibit bone resorption, etc.(Matkovskaya et al., 2001).
The molecular structure of title complex is shown in Fig. 1; as illustrated themolecule of the complex forms discrete monomeric units. The asymmetric unitcontains one-half of the formula unit [Co(C3H10NO7P2)2(H2O)2],with the Co atom lying on an inversion center.
The CoII ion is coordinated in a slightly distorted octahedral geometrywhich consists of six oxygen atoms, two fromwater molecules located in the axial positions and four from thetwo phosphonate groups of two different ligands, which exist inzwitterionic form, creating two six-membered [O, O] chelate rings.The Co—O bond lengths andthe O—Co—O angles have expected values (Allen et al., 2004)andconform well to the previously reported related structure (Bon etal., 2010). In the packing, O—H···O and N—H···O hydrogen-bondsexist between the water molecules, phosphonate, hydroxyl O atoms and nitrogenatoms of the amino group (Fig. 2, Table 1). Thus, the molecules are interlinkedby these hydrogen bonds to create a three-dimensional structure which partiallyinfluences and stabilizes the configuration of the molecule.
For general background to organic diphosphonic acids and their applications,see: Matczak-Jon & Videnova-Adrabinska (2005). For applications ofbisphosphonate metal complexes in medicine, see: Matkovskaya et al.(2001). For a related structure, see: Bon et al. (2010).Forbond-length data, see: Allen et al. (2004).
Computing details top
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2010); software used to prepare material for publication: publCIF (Westrip, 2010).
Figures top
| Fig. 1. The molecular structure of the title compound. Displacement ellipsoidsare drawn at the 50% probability level. | |
| Fig. 2. Crystal packing of the title compound viewed down the a axis,showing the three-dimensional chain structure. Hydrogen bonds are shown asdashed lines. |
Crystal data
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| [Co(C3H10NO7P2)2(H2O)2] | F(000) = 578 |
| Mr = 563.08 | Dx = 2.172 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 3543 reflections |
| a = 7.3292 (2) Å | θ = 2.7–30.6° |
| b = 10.8172 (3) Å | µ = 1.46 mm−1 |
| c = 12.6403 (3) Å | T = 100 K |
| β = 120.801 (1)° | Block, pink |
| V = 860.79 (4) Å3 | 0.50 × 0.25 × 0.15 mm |
| Z = 2 |
Data collection
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| Bruker APEXII CCD diffractometer | 2613 independent reflections |
| Radiation source: fine-focus sealed tube | 2273 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.020 |
| φ and ω scans | θmax = 30.6°, θmin = 2.7° |
| Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −10→9 |
| Tmin = 0.528, Tmax = 0.811 | k = −12→15 |
| 6688 measured reflections | l = −18→12 |
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| 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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.080 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.04 | w = 1/[σ2(Fo2) + (0.0452P)2 + 0.4224P] where P = (Fo2 + 2Fc2)/3 |
| 2613 reflections | (Δ/σ)max = 0.003 |
| 157 parameters | Δρmax = 0.70 e Å−3 |
| 1 restraint | Δρmin = −0.41 e Å−3 |
Crystal data
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| [Co(C3H10NO7P2)2(H2O)2] | V = 860.79 (4) Å3 |
| Mr = 563.08 | Z = 2 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 7.3292 (2) Å | µ = 1.46 mm−1 |
| b = 10.8172 (3) Å | T = 100 K |
| c = 12.6403 (3) Å | 0.50 × 0.25 × 0.15 mm |
| β = 120.801 (1)° |
Data collection
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| Bruker APEXII CCD diffractometer | 2613 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2007) | 2273 reflections with I > 2σ(I) |
| Tmin = 0.528, Tmax = 0.811 | Rint = 0.020 |
| 6688 measured reflections |
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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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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-factorwR and goodness of fit S are based on F2, conventionalR-factors R are based on F, with F set to zero fornegative 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 largeas those based on F, and R- factors based on ALL data will beeven larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
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| x | y | z | Uiso*/Ueq | ||
| Co1 | 0.0000 | 0.5000 | 0.0000 | 0.01045 (9) | |
| P1 | 0.25936 (6) | 0.70145 (4) | −0.05843 (4) | 0.00902 (10) | |
| P2 | −0.12574 (6) | 0.58120 (4) | −0.28208 (4) | 0.00964 (10) | |
| O1 | 0.1630 (2) | 0.72770 (13) | −0.29229 (12) | 0.0156 (3) | |
| H1O | 0.127 (4) | 0.802 (3) | −0.289 (2) | 0.023* | |
| O2 | 0.25165 (18) | 0.60515 (12) | 0.02492 (11) | 0.0124 (2) | |
| O3 | 0.1139 (2) | 0.81197 (12) | −0.07370 (12) | 0.0145 (3) | |
| H3O | 0.154 (4) | 0.874 (3) | −0.079 (2) | 0.022* | |
| O4 | 0.48210 (18) | 0.74524 (13) | −0.01964 (11) | 0.0137 (3) | |
| O5 | −0.1323 (2) | 0.49001 (12) | −0.19349 (11) | 0.0143 (3) | |
| O6 | −0.2632 (2) | 0.69798 (12) | −0.29892 (12) | 0.0151 (3) | |
| H6O | −0.334 (4) | 0.712 (2) | −0.365 (2) | 0.023* | |
| O7 | −0.1968 (2) | 0.52889 (12) | −0.40857 (11) | 0.0137 (3) | |
| O8 | 0.1663 (2) | 0.33228 (13) | 0.02254 (13) | 0.0158 (3) | |
| H81 | 0.270 (4) | 0.320 (2) | 0.007 (2) | 0.024* | |
| H82 | 0.082 (4) | 0.283 (2) | −0.014 (2) | 0.024* | |
| N1 | 0.4212 (3) | 0.38826 (17) | −0.30480 (17) | 0.0192 (3) | |
| H2N | 0.356 (4) | 0.323 (3) | −0.297 (2) | 0.029* | |
| H3N | 0.553 (5) | 0.394 (2) | −0.237 (3) | 0.029* | |
| H1N | 0.439 (4) | 0.383 (3) | −0.3675 (19) | 0.029* | |
| C1 | 0.1504 (2) | 0.63551 (16) | −0.21320 (15) | 0.0108 (3) | |
| C2 | 0.2914 (3) | 0.52507 (17) | −0.20331 (16) | 0.0140 (3) | |
| H2A | 0.4370 | 0.5391 | −0.1330 | 0.017* | |
| H2B | 0.2357 | 0.4493 | −0.1858 | 0.017* | |
| C3 | 0.3018 (3) | 0.50443 (17) | −0.31959 (18) | 0.0164 (4) | |
| H3A | 0.1565 | 0.4980 | −0.3922 | 0.020* | |
| H3B | 0.3743 | 0.5750 | −0.3325 | 0.020* |
Atomic displacement parameters (Å2)
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| U11 | U22 | U33 | U12 | U13 | U23 | |
| Co1 | 0.01100 (15) | 0.00938 (17) | 0.00988 (16) | −0.00047 (11) | 0.00457 (12) | 0.00097 (12) |
| P1 | 0.00920 (18) | 0.0085 (2) | 0.00885 (19) | −0.00167 (14) | 0.00423 (15) | −0.00129 (15) |
| P2 | 0.01040 (19) | 0.0090 (2) | 0.00774 (18) | −0.00077 (14) | 0.00333 (15) | −0.00018 (15) |
| O1 | 0.0225 (6) | 0.0115 (6) | 0.0157 (6) | 0.0003 (5) | 0.0118 (5) | 0.0027 (5) |
| O2 | 0.0120 (5) | 0.0124 (6) | 0.0107 (5) | −0.0017 (4) | 0.0042 (4) | 0.0020 (5) |
| O3 | 0.0171 (6) | 0.0076 (6) | 0.0190 (6) | −0.0005 (5) | 0.0094 (5) | −0.0013 (5) |
| O4 | 0.0110 (5) | 0.0168 (7) | 0.0133 (6) | −0.0049 (4) | 0.0063 (5) | −0.0040 (5) |
| O5 | 0.0163 (6) | 0.0141 (6) | 0.0103 (6) | −0.0043 (5) | 0.0052 (5) | 0.0014 (5) |
| O6 | 0.0148 (6) | 0.0147 (6) | 0.0109 (6) | 0.0051 (5) | 0.0031 (5) | 0.0004 (5) |
| O7 | 0.0162 (6) | 0.0125 (6) | 0.0092 (5) | −0.0015 (5) | 0.0041 (5) | −0.0030 (5) |
| O8 | 0.0139 (6) | 0.0134 (6) | 0.0210 (6) | −0.0007 (5) | 0.0096 (5) | −0.0009 (5) |
| N1 | 0.0186 (7) | 0.0182 (8) | 0.0237 (8) | −0.0020 (6) | 0.0129 (7) | −0.0071 (7) |
| C1 | 0.0114 (7) | 0.0099 (8) | 0.0103 (7) | −0.0005 (6) | 0.0050 (6) | 0.0001 (6) |
| C2 | 0.0155 (7) | 0.0125 (8) | 0.0125 (7) | 0.0038 (6) | 0.0061 (6) | −0.0007 (7) |
| C3 | 0.0181 (8) | 0.0156 (9) | 0.0180 (9) | 0.0017 (6) | 0.0111 (7) | −0.0008 (7) |
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| Co1—O2i | 2.0494 (12) | O1—H1O | 0.85 (3) |
| Co1—O2 | 2.0494 (12) | O3—H3O | 0.76 (3) |
| Co1—O8i | 2.1221 (14) | O6—H6O | 0.74 (3) |
| Co1—O8 | 2.1221 (14) | O8—H81 | 0.89 (3) |
| Co1—O5i | 2.1225 (13) | O8—H82 | 0.77 (3) |
| Co1—O5 | 2.1225 (13) | N1—C3 | 1.487 (3) |
| P1—O2 | 1.5031 (13) | N1—H2N | 0.88 (3) |
| P1—O4 | 1.5199 (12) | N1—H3N | 0.91 (3) |
| P1—O3 | 1.5469 (14) | N1—H1N | 0.870 (17) |
| P1—C1 | 1.8367 (17) | C1—C2 | 1.542 (2) |
| P2—O5 | 1.5115 (13) | C2—C3 | 1.527 (3) |
| P2—O7 | 1.5149 (13) | C2—H2A | 0.9900 |
| P2—O6 | 1.5609 (14) | C2—H2B | 0.9900 |
| P2—C1 | 1.8422 (16) | C3—H3A | 0.9900 |
| O1—C1 | 1.448 (2) | C3—H3B | 0.9900 |
| O2i—Co1—O2 | 180.0 | P2—O5—Co1 | 130.65 (7) |
| O2i—Co1—O8i | 92.52 (5) | P2—O6—H6O | 111 (2) |
| O2—Co1—O8i | 87.48 (5) | Co1—O8—H81 | 126.4 (17) |
| O2i—Co1—O8 | 87.48 (5) | Co1—O8—H82 | 107 (2) |
| O2—Co1—O8 | 92.52 (5) | H81—O8—H82 | 107 (2) |
| O8i—Co1—O8 | 180.0 | C3—N1—H2N | 111.7 (18) |
| O2i—Co1—O5i | 92.85 (5) | C3—N1—H3N | 109.5 (17) |
| O2—Co1—O5i | 87.15 (5) | H2N—N1—H3N | 109 (2) |
| O8i—Co1—O5i | 90.19 (5) | C3—N1—H1N | 107.2 (19) |
| O8—Co1—O5i | 89.81 (5) | H2N—N1—H1N | 113 (2) |
| O2i—Co1—O5 | 87.15 (5) | H3N—N1—H1N | 106 (2) |
| O2—Co1—O5 | 92.85 (5) | O1—C1—C2 | 108.19 (14) |
| O8i—Co1—O5 | 89.81 (5) | O1—C1—P1 | 108.73 (11) |
| O8—Co1—O5 | 90.19 (5) | C2—C1—P1 | 107.85 (11) |
| O5i—Co1—O5 | 180.00 (7) | O1—C1—P2 | 109.67 (11) |
| O2—P1—O4 | 114.17 (7) | C2—C1—P2 | 108.63 (12) |
| O2—P1—O3 | 110.62 (8) | P1—C1—P2 | 113.62 (9) |
| O4—P1—O3 | 110.93 (8) | C3—C2—C1 | 113.39 (14) |
| O2—P1—C1 | 109.00 (8) | C3—C2—H2A | 108.9 |
| O4—P1—C1 | 105.91 (8) | C1—C2—H2A | 108.9 |
| O3—P1—C1 | 105.73 (8) | C3—C2—H2B | 108.9 |
| O5—P2—O7 | 114.46 (8) | C1—C2—H2B | 108.9 |
| O5—P2—O6 | 111.46 (8) | H2A—C2—H2B | 107.7 |
| O7—P2—O6 | 108.02 (7) | N1—C3—C2 | 108.60 (15) |
| O5—P2—C1 | 107.58 (7) | N1—C3—H3A | 110.0 |
| O7—P2—C1 | 108.58 (8) | C2—C3—H3A | 110.0 |
| O6—P2—C1 | 106.40 (8) | N1—C3—H3B | 110.0 |
| C1—O1—H1O | 119.0 (17) | C2—C3—H3B | 110.0 |
| P1—O2—Co1 | 129.11 (7) | H3A—C3—H3B | 108.4 |
| P1—O3—H3O | 115 (2) | ||
| O4—P1—O2—Co1 | −170.27 (9) | O4—P1—C1—C2 | 61.76 (13) |
| O3—P1—O2—Co1 | 63.77 (11) | O3—P1—C1—C2 | 179.55 (12) |
| C1—P1—O2—Co1 | −52.07 (12) | O2—P1—C1—P2 | 58.97 (11) |
| O8i—Co1—O2—P1 | −55.98 (10) | O4—P1—C1—P2 | −177.76 (9) |
| O8—Co1—O2—P1 | 124.02 (10) | O3—P1—C1—P2 | −59.97 (11) |
| O5i—Co1—O2—P1 | −146.30 (11) | O5—P2—C1—O1 | −177.36 (11) |
| O5—Co1—O2—P1 | 33.70 (11) | O7—P2—C1—O1 | 58.25 (13) |
| O7—P2—O5—Co1 | 166.92 (9) | O6—P2—C1—O1 | −57.80 (13) |
| O6—P2—O5—Co1 | −70.11 (12) | O5—P2—C1—C2 | 64.58 (13) |
| C1—P2—O5—Co1 | 46.17 (13) | O7—P2—C1—C2 | −59.81 (13) |
| O2i—Co1—O5—P2 | 148.83 (11) | O6—P2—C1—C2 | −175.86 (11) |
| O2—Co1—O5—P2 | −31.17 (11) | O5—P2—C1—P1 | −55.46 (11) |
| O8i—Co1—O5—P2 | 56.30 (11) | O7—P2—C1—P1 | −179.85 (8) |
| O8—Co1—O5—P2 | −123.70 (11) | O6—P2—C1—P1 | 64.10 (11) |
| O2—P1—C1—O1 | −178.61 (10) | O1—C1—C2—C3 | −31.88 (19) |
| O4—P1—C1—O1 | −55.34 (13) | P1—C1—C2—C3 | −149.34 (13) |
| O3—P1—C1—O1 | 62.45 (12) | P2—C1—C2—C3 | 87.10 (16) |
| O2—P1—C1—C2 | −61.51 (13) | C1—C2—C3—N1 | −173.76 (14) |
Symmetry code: (i) −x, −y+1, −z.
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| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1O···O5ii | 0.85 (3) | 2.05 (3) | 2.845 (2) | 155 (2) |
| O3—H3O···O7ii | 0.76 (3) | 1.72 (3) | 2.4627 (19) | 167 (3) |
| O6—H6O···O4iii | 0.74 (3) | 1.78 (3) | 2.5124 (18) | 175 (3) |
| O8—H81···O4iv | 0.89 (3) | 1.88 (3) | 2.7277 (18) | 160 (2) |
| O8—H82···O1v | 0.77 (3) | 2.25 (3) | 2.8953 (19) | 142 (3) |
| N1—H2N···O6v | 0.88 (3) | 2.15 (3) | 2.975 (2) | 156 (2) |
| N1—H3N···O2iv | 0.91 (3) | 2.30 (3) | 3.096 (2) | 146 (2) |
| N1—H3N···O5vi | 0.91 (3) | 2.32 (3) | 3.030 (2) | 134 (2) |
| N1—H1N···O4vii | 0.87 (2) | 2.33 (2) | 3.071 (2) | 143 (2) |
Symmetry codes: (ii) −x, y+1/2, −z−1/2; (iii) x−1, −y+3/2, z−1/2; (iv) −x+1, −y+1, −z; (v) −x, y−1/2, −z−1/2; (vi) x+1, y, z; (vii) −x+1, y−1/2, −z−1/2.
Experimental details
| Crystal data | |
| Chemical formula | [Co(C3H10NO7P2)2(H2O)2] |
| Mr | 563.08 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 100 |
| a, b, c (Å) | 7.3292 (2), 10.8172 (3), 12.6403 (3) |
| β (°) | 120.801 (1) |
| V (Å3) | 860.79 (4) |
| Z | 2 |
| Radiation type | Mo Kα |
| µ (mm−1) | 1.46 |
| Crystal size (mm) | 0.50 × 0.25 × 0.15 |
| Data collection | |
| Diffractometer | Bruker APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
| Tmin, Tmax | 0.528, 0.811 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 6688, 2613, 2273 |
| Rint | 0.020 |
| (sin θ/λ)max (Å−1) | 0.715 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.080, 1.04 |
| No. of reflections | 2613 |
| No. of parameters | 157 |
| No. of restraints | 1 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.70, −0.41 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2010), publCIF (Westrip, 2010).
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| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1O···O5i | 0.85(3) | 2.05(3) | 2.845(2) | 155(2) |
| O3—H3O···O7i | 0.76(3) | 1.72(3) | 2.4627(19) | 167(3) |
| O6—H6O···O4ii | 0.74(3) | 1.78(3) | 2.5124(18) | 175(3) |
| O8—H81···O4iii | 0.89(3) | 1.88(3) | 2.7277(18) | 160(2) |
| O8—H82···O1iv | 0.77(3) | 2.25(3) | 2.8953(19) | 142(3) |
| N1—H2N···O6iv | 0.88(3) | 2.15(3) | 2.975(2) | 156(2) |
| N1—H3N···O2iii | 0.91(3) | 2.30(3) | 3.096(2) | 146(2) |
| N1—H3N···O5v | 0.91(3) | 2.32(3) | 3.030(2) | 134(2) |
| N1—H1N···O4vi | 0.870(17) | 2.33(2) | 3.071(2) | 143(2) |
Symmetry codes: (i) −x, y+1/2, −z−1/2; (ii) x−1, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z; (iv) −x, y−1/2, −z−1/2; (v) x+1, y, z; (vi) −x+1, y−1/2, −z−1/2.
