The nitrate dihydrate of an aqua­dicopper(II) complex cation with guanidino­acetic acid and a novel trianionic disubstituted guanidine as ligands at 120 K

The structure of the title compound, aqua­[[mu]-(N¹-carboxylato­methyl­guanidino)­oxidoacetato]([mu]-guanidino­acetic acid)­di­copper(II) nitrate dihydrate, [Cu₂(C₅H₆N₃O₅)(C₃H₇N₃O₂)(H₂O)]NO₃·2H₂O, contains two enantiomers of the di­copper(II) complex cation that comprise water, neutral zwitterionic guanidino­acetic acid and the trianion of (N¹-carboxy­methyl­guanidino)­hydroxy­acetic acid as ligands. Extensive hydrogen bonding creates three-dimensional connectivity but is largely confined to layers that each contain both cation enantiomers. These layers are related to one another by crystallographic symmetry and are therefore identical in composition and connectivity.

S1. Comment

As part of a continuing study of Cu^II complexes with aminoacids (Felcman & de Miranda, 1997; de Miranda & Felcman, 2001) we previously reported the structure of [Cu₂(NO₃)₂(gaa)₄], (I), [gaa = guanidinoacetic acid, H₂NC(═NH₂)NHCH₂CO₂; de Miranda et al., 2002]. Green crystalline (I) had been isolated from a reaction mixture containing Cu^II(NO₃)₂, guanidinoacetic acid and aspartic acid. Obtained along with (I) from this reaction mixture were blue crystals of the title compound, (II), whose structure we now report. The sample crystal used for the analysis presented here came, in fact, from a subsequent preparation of (II), again accompanied by (I), but in the absence of aspartic acid, which must therefore, when present, be merely a spectator species.

For convenience, the asymmetric unit in the structure of (II) is described in terms of two subunits, labelled identically and distinguished by suffixes A and B, of formula C₈H₁₉Cu₂N₇O₁₀, where this formula corresponds to an aquadicopper complex cation of formula (C₈H₁₅Cu₂N₆O₈)⁺, a nitrate, NO₃⁻, counter anion and two hydrate water molecules (see Scheme and Fig. 1). Only the cation merits further detailed discussion.

Three ligand species contribute to the variously distorted approximately square-planar cooordinaton of Cu (Table 1) in the complex cation of (II). The first and simplest of these is the water molecule, O8. The second is the bismonodentate bridging (µ²) guanidinoacetic acid species, gaa, with formula C₃H₇N₃O₂, comprising O1, O2, C1–C3 and N1–N3, in its zwitterionic and therefore neutral form. Previous examples of complexes containing zwitterionic gaa are (I) (de Miranda et al., 2002) and [CuCl₂(gaa)₂] (Silva et al., 2001). The third and most interesting is the tetradentate bischelate species, oag³⁻, formulated (C₅H₆N₃O₅)³⁻, comprising C4–C8, N4–N6 and O3–O7 and corresponding to the trianion of the previously unkown (N¹-carboxymethylguanidino)hydroxyacetic acid. In this last case, O3 and N4 form bonds with Cu2, thus creating a five-membered chelate ring, and O5 and O6 form bonds with Cu1 in a similar manner. However O5 forms a further bond with Cu2 and therefore has an additional bridging function, thus creating a further six-membered ring.

The chemical identity of the individual atoms within the oag³⁻ species was determined initially by consideration of the atomic displacement parameters but is supported by comparison of these with those found for atoms of corresponding type in gaa. Further support for the correctness of the atom designations comes from the positions of H atoms determined by difference synthesis and their satisfactory contribution to the hydrogen-bonding scheme discussed later.

The structural subunits A and B and the complex cations within them are identical in their connectivity and therefore, as noted above, have been labelled in an identical manner and distinguished by suffix. It is clear from Table 1 that with few exceptions, e.g. the angles at N6, the bond distances and angles of the two complex cations within the asymmetric unit are very similar. However the cations differ in their configuration at the asymmetric centre C7, which is R at C7A (subunit A) and S at C7B (subunit B). The differing R and S configurations at C7A and C7B are, however, compatible with the formation of oag³⁻ from non-chiral components in the manner suggested below (see supplementary Scheme).

Extensive hydrogen-bonding (Table 2 and Fig. 2) creates layers parallel to (010). Most of the values given in Table 2 correspond to hydrogen-bonds within the layer and once again demonstrate the similarity of the structural subunits. The most obvious and inevitable exceptions are when interlayer hydrogen bonds are considered (e.g. the marked differences for pairs of donor atoms such as N6A/N6B and O9A/O9B), because the layers occur centred on y = 1/8 and at intervals of 1/4 thereafter. Thus any one layer is related to any other layer with a different y coordinate by only one of the crystallographic symmetry elements of the space group P2₁/c. Further, for any one layer, while it is related to its immediate neighbour on one side by a crystallographic centre of symmetry, the relationship to the layer on the other side must be that of the c-glide plane, and the interlayer hydrogen-bonds must reflect this.

The new ligand, oag³⁻, is considered to be derived from two gaa molecules. Nakai et al. (1979) have reported that gaa in the presence of Ag₂CO₃ supported on Celite generates guanidine by the loss of a two-C-atom moiety, either hydroxyacetic acid, HOCH₂CO₂H, (III), or the oxidized species HC(O)CO₂H, (IV). If (IV) is not directly formed it will be readily generated by oxidation of (III) by the Ag salt in air. In our reaction media, Cu^II is available to bring about the oxidation of (III) to (IV), which then permits the reaction with another molecule of gaa to provide the new ligand (see supplementary Scheme). There is partial and somewhat circumstantial evidence for this as follows. Consideration of the stoichiometry and charge balance of the formula, [Cu₂(NO₃)₂(gaa)₄] (de Miranda et al., 2002), of the overall neutral complex in green (I) now suggests that Cu is present there in the +1 oxidation state, because the gaa in this complex is once again present in its uncharged zwitterionic form and NO₃⁻ is the only anion present. This assumption would be consistant with both the involvement of Cu(II) ?in? the genesis of oag³⁻ and the recovery of crystals of blue (II) in admixture with green (I) from our reaction mixtures.

S2. Experimental

To a solution of gaa (1.171 g, 10 mmol) in 50% aqueous ethanol (50 ml) were successively added, with stirring, nitric acid (0.1 mol L⁻¹, until pH < 7), aspartic acid (1.331 g, 10 mmol) and copper nitrate trihydrate (2.462 g, 10 mmol). After stirring the solution for 1 h at 303 K, KOH solution (0.1 M) was slowly added until precipitation occurred. The mixture was filtered, and ethanol (25 ml) was added to the filtrate. On standing at room temperature, green crystals of (I) and blue crystals of (II) were slowly deposited from the solution. The two types of crystal were separated manually. The crystal used in the structure analysis reported here was obtained in essentially this manner, except that aspartic acid was absent from the reaction mixture.

S3. Refinement

Intensity data were taken over the full Ewald sphere. Only the monoclinic crystal system permitted solution and refinement of the structure, and this system was confirmed as appropriate by checkCIF. The maximum residual electron density was 0.85 Å from Cu2B. Anisotropic displacement parameters were refined for all non-H atoms. H atoms attached to C atoms were placed by geometric means with N—H distances of 0.99 and 1.00 Å for methylene (C2 and C5) and tertiary (C7) H atoms, respectively. H atoms attached to N and water O atoms were initially found in sensible, if approximate, positions by difference synthesis and thereafter idealized as follows. SHELXL97 AFIX 93 with N—H distances of 0.88 Å was used for H atoms of terminal NH₂ groups (N2, N3 and N5). For the remaining H atoms, the coordinates were allowed to refine but with DFIX used to constrain the N—H distance in the case of secondary amine atoms N1 and N6 and SADI used to restrain the O—H distances for water O8, O9 and O10 atoms. For all H atoms, U_eq was set to 1.2U_iso of the non-H atom to which they are attached.

Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 1990).

Figures

	Fig. 1. Subunit A of (II), showing the labelling scheme (the suffix A has been deliberately suppressed), which applies equally to subunit B. Non-H atoms are shown as 50% probability ellipsoids and H atoms as spheres of arbitrary radii. Dashed lines represent hydrogen-bonds.
	Fig. 2. A portion of the layer at y = 1/8 in the structure of (II), viewed along b. Non-H atoms are shown as 50% probability ellipsoids and H atoms as spheres of arbitrary radii. H atoms other than those involved in hydrogen-bond (dashed lines) formation have been omitted for clarity, and only selected atoms are labelled.

aqua[µ-(N¹-carboxatomethylguanidino)oxidoacetato](µ-guanidinoacetic acid)dicopper(II) nitrate dihydrate

Crystal data

[Cu2(C5H6N3O5)(C3H7N3O2)(H2O)]NO3·2H2O	F(000) = 2224
Mr = 548.38	Dx = 2.060 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 17990 reflections
a = 15.2979 (2) Å	θ = 2.9–27.5°
b = 13.0020 (2) Å	µ = 2.49 mm^−1
c = 17.7821 (2) Å	T = 120 K
β = 90.0302 (7)°	Block, blue
V = 3536.92 (8) Å^3	0.20 × 0.15 × 0.15 mm
Z = 8

Data collection

Enraf–Nonius KappaCCD area detector diffractometer	7933 independent reflections
Radiation source: Enraf–Nonius FR591 rotating anode	7112 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ϕ and ω scans	h = −19→19
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	k = −16→16
Tmin = 0.890, Tmax = 0.923	l = −23→22
33782 measured reflections

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)] = 0.035	Hydrogen site location: geom and difmap
wR(F^2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ^2(Fo^2) + (0.0253P)^2 + 6.7574P] where P = (Fo^2 + 2Fc^2)/3
7933 reflections	(Δ/σ)max = 0.001
589 parameters	Δρmax = 0.93 e Å^−3
70 restraints	Δρmin = −1.03 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.

'Linear' torsion angles excluded as per PLATON alerts O6A Cu1A O1A C1A −160.4 (11).. . . ? O5A Cu2A O3A C4A 11 (2).. . . ? O3A Cu2A O5A C7A −33 (2).. . . ? O3A Cu2A O5A Cu1A −174 (2).. . . ? O1A Cu1A O6A C8A 152.9 (12).. . . ? O6B Cu1B O1B C1B 143.0 (8).. . . ? N4B Cu2B O2B C1B 177.4 (5).. . . ? O5B Cu2B O3B C4B 67.9 (6).. . . ? O2B Cu2B N4B C6B −137.7 (5).. . . ? O2B Cu2B N4B C5B 33.2 (7).. . . ? O3B Cu2B O5B C7B −57.3 (6).. . . ? O3B Cu2B O5B Cu1B 102.4 (5).. . . ? O1B Cu1B O6B C8B −141.7 (8).. . . ?

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
Cu1A	−0.05930 (2)	0.11693 (3)	0.752151 (17)	0.01536 (9)
Cu2A	−0.281021 (19)	0.13660 (3)	0.725787 (17)	0.01147 (8)
O1A	−0.07892 (12)	0.11793 (16)	0.64516 (10)	0.0165 (4)
O2A	−0.22518 (12)	0.12728 (15)	0.62867 (10)	0.0160 (4)
C1A	−0.14767 (17)	0.1216 (2)	0.60633 (14)	0.0123 (5)
C2A	−0.13754 (17)	0.1180 (2)	0.52184 (14)	0.0139 (5)
H2A	−0.1674	0.0560	0.5022	0.017*
H2B	−0.1661	0.1791	0.4995	0.017*
N1A	−0.04651 (15)	0.11578 (19)	0.49930 (12)	0.0145 (5)
H1A	−0.0056 (17)	0.116 (2)	0.5335 (15)	0.017*
C3A	−0.02173 (17)	0.1212 (2)	0.42708 (15)	0.0131 (5)
N2A	−0.08097 (15)	0.12034 (18)	0.37314 (12)	0.0165 (5)
H2C	−0.0646	0.1240	0.3258	0.020*
H2D	−0.1368	0.1161	0.3845	0.020*
N3A	0.06317 (15)	0.12761 (19)	0.41003 (13)	0.0178 (5)
H3A	0.0797	0.1313	0.3627	0.021*
H3B	0.1025	0.1282	0.4461	0.021*
O3A	−0.38949 (12)	0.16013 (15)	0.66714 (10)	0.0150 (4)
O4A	−0.53034 (12)	0.20154 (15)	0.68045 (10)	0.0162 (4)
C4A	−0.45764 (16)	0.1792 (2)	0.70745 (14)	0.0125 (5)
C5A	−0.44780 (16)	0.1731 (2)	0.79175 (14)	0.0120 (5)
H5A	−0.4678	0.2383	0.8148	0.014*
H5B	−0.4845	0.1166	0.8116	0.014*
N4A	−0.35666 (13)	0.15478 (17)	0.81136 (12)	0.0119 (4)
C6A	−0.33859 (17)	0.1341 (2)	0.88208 (14)	0.0131 (5)
N5A	−0.39872 (15)	0.1224 (2)	0.93565 (13)	0.0195 (5)
H5C	−0.4546	0.1285	0.9246	0.023*
H5D	−0.3826	0.1086	0.9821	0.023*
N6A	−0.25412 (15)	0.1204 (2)	0.90266 (13)	0.0169 (5)
H6A	−0.243 (2)	0.093 (2)	0.9448 (13)	0.020*
C7A	−0.18332 (17)	0.1567 (2)	0.85878 (14)	0.0153 (5)
H7A	−0.1897	0.2329	0.8534	0.018*
O5A	−0.17853 (12)	0.11357 (16)	0.78587 (10)	0.0183 (4)
C8A	−0.09691 (17)	0.1352 (2)	0.90000 (14)	0.0131 (5)
O6A	−0.03145 (12)	0.11898 (16)	0.85721 (10)	0.0166 (4)
O7A	−0.09329 (12)	0.13644 (16)	0.96943 (10)	0.0171 (4)
O8A	0.06155 (14)	0.0942 (2)	0.73082 (12)	0.0323 (6)
H8A	0.101 (2)	0.097 (3)	0.7617 (18)	0.039*
H8B	0.080 (3)	0.100 (3)	0.6889 (13)	0.039*
O9A	0.19234 (14)	0.07847 (18)	0.82914 (12)	0.0216 (4)
H9A	0.2351 (17)	0.110 (2)	0.815 (2)	0.026*
H9B	0.196 (2)	0.0164 (13)	0.828 (2)	0.026*
O10A	0.33526 (13)	0.18678 (18)	0.79699 (12)	0.0224 (4)
H10A	0.366 (2)	0.173 (3)	0.8322 (14)	0.027*
H10B	0.365 (2)	0.179 (3)	0.7602 (14)	0.027*
N7A	0.19460 (15)	0.12538 (18)	0.58010 (13)	0.0151 (5)
O11A	0.11330 (13)	0.11475 (18)	0.58923 (12)	0.0237 (5)
O12A	0.22390 (13)	0.12553 (17)	0.51362 (11)	0.0212 (4)
O13A	0.24369 (13)	0.13639 (17)	0.63444 (11)	0.0233 (5)
Cu1B	0.44259 (2)	0.10281 (3)	0.158105 (17)	0.01188 (8)
Cu2B	0.21784 (2)	0.10287 (3)	0.185284 (17)	0.01411 (8)
O1B	0.42322 (12)	0.08951 (15)	0.26515 (10)	0.0146 (4)
O2B	0.27720 (12)	0.07245 (16)	0.27968 (10)	0.0161 (4)
C1B	0.35418 (17)	0.0851 (2)	0.30315 (14)	0.0123 (5)
C2B	0.36256 (17)	0.0919 (2)	0.38792 (14)	0.0133 (5)
H2E	0.3307	0.1532	0.4061	0.016*
H2F	0.3354	0.0304	0.4110	0.016*
N1B	0.45365 (14)	0.09845 (18)	0.41137 (12)	0.0127 (4)
H1E	0.4948 (17)	0.089 (2)	0.3803 (15)	0.015*
C3B	0.47645 (17)	0.11719 (19)	0.48256 (14)	0.0122 (5)
N2B	0.41698 (15)	0.12578 (18)	0.53605 (12)	0.0151 (5)
H2H	0.3612	0.1191	0.5251	0.018*
H2G	0.4332	0.1381	0.5827	0.018*
N3B	0.56136 (14)	0.12706 (18)	0.49978 (13)	0.0152 (5)
H3E	0.5772	0.1392	0.5465	0.018*
H3F	0.6012	0.1214	0.4644	0.018*
O3B	0.10794 (13)	0.12387 (17)	0.24228 (11)	0.0204 (4)
O4B	−0.03081 (12)	0.17404 (17)	0.22669 (11)	0.0202 (4)
C4B	0.04217 (17)	0.1475 (2)	0.20136 (15)	0.0158 (5)
C5B	0.05229 (16)	0.1411 (2)	0.11728 (14)	0.0144 (5)
H5E	0.0160	0.0843	0.0973	0.017*
H5F	0.0322	0.2061	0.0939	0.017*
N4B	0.14390 (14)	0.12330 (18)	0.09873 (12)	0.0143 (5)
C6B	0.16342 (17)	0.1106 (2)	0.02732 (15)	0.0150 (5)
N5B	0.10531 (15)	0.1121 (2)	−0.02805 (13)	0.0212 (5)
H5G	0.0496	0.1220	−0.0180	0.025*
H5H	0.1224	0.1031	−0.0748	0.025*
N6B	0.24958 (15)	0.0907 (2)	0.00950 (13)	0.0176 (5)
H6E	0.259 (2)	0.093 (3)	−0.0388 (11)	0.021*
C7B	0.31600 (17)	0.1431 (2)	0.05323 (15)	0.0160 (5)
H7E	0.3001	0.2176	0.0560	0.019*
O5B	0.32330 (12)	0.10532 (15)	0.12704 (10)	0.0140 (4)
C8B	0.40400 (17)	0.1338 (2)	0.01189 (15)	0.0133 (5)
O6B	0.47061 (12)	0.12367 (15)	0.05441 (10)	0.0157 (4)
O7B	0.40668 (12)	0.14207 (16)	−0.05733 (10)	0.0179 (4)
O8B	0.56199 (12)	0.05998 (17)	0.17714 (11)	0.0183 (4)
H8E	0.5981 (18)	0.084 (3)	0.1489 (16)	0.022*
H8F	0.582 (2)	0.068 (3)	0.2189 (11)	0.022*
O9B	0.67393 (13)	0.15798 (17)	0.08668 (11)	0.0198 (4)
H9E	0.7241 (13)	0.144 (3)	0.096 (2)	0.024*
H9F	0.659 (2)	0.2163 (16)	0.096 (2)	0.024*
O10B	0.84133 (13)	0.12883 (19)	0.11875 (12)	0.0236 (5)
H10E	0.866 (2)	0.127 (3)	0.0788 (13)	0.028*
H10F	0.874 (2)	0.151 (3)	0.1509 (16)	0.028*
N7B	0.69272 (15)	0.09694 (18)	0.33043 (13)	0.0170 (5)
O11B	0.61249 (12)	0.07797 (18)	0.32025 (11)	0.0227 (5)
O12B	0.72013 (14)	0.10693 (17)	0.39659 (11)	0.0224 (4)
O13B	0.74235 (13)	0.10689 (18)	0.27619 (12)	0.0254 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1A	0.00671 (15)	0.0320 (2)	0.00733 (15)	0.00272 (13)	0.00061 (12)	−0.00102 (12)
Cu2A	0.00653 (15)	0.02092 (17)	0.00696 (15)	0.00039 (12)	0.00065 (11)	−0.00006 (12)
O1A	0.0105 (9)	0.0294 (11)	0.0096 (9)	0.0005 (8)	−0.0002 (7)	−0.0020 (8)
O2A	0.0084 (9)	0.0287 (11)	0.0109 (9)	0.0004 (8)	0.0011 (7)	0.0008 (8)
C1A	0.0122 (12)	0.0152 (13)	0.0096 (12)	0.0010 (10)	0.0014 (10)	−0.0001 (9)
C2A	0.0094 (12)	0.0224 (14)	0.0101 (12)	0.0000 (10)	0.0004 (10)	0.0003 (10)
N1A	0.0080 (10)	0.0276 (13)	0.0080 (10)	−0.0002 (9)	0.0005 (8)	−0.0007 (9)
C3A	0.0132 (12)	0.0126 (12)	0.0134 (12)	−0.0001 (10)	0.0017 (10)	−0.0003 (9)
N2A	0.0154 (11)	0.0264 (13)	0.0076 (10)	0.0000 (9)	0.0028 (9)	0.0006 (9)
N3A	0.0121 (11)	0.0315 (14)	0.0099 (11)	0.0007 (10)	0.0042 (9)	0.0009 (9)
O3A	0.0094 (9)	0.0257 (10)	0.0098 (8)	0.0020 (8)	0.0012 (7)	−0.0007 (7)
O4A	0.0095 (8)	0.0261 (11)	0.0129 (9)	0.0039 (8)	−0.0018 (7)	−0.0016 (8)
C4A	0.0112 (12)	0.0138 (12)	0.0123 (12)	−0.0003 (10)	0.0016 (10)	−0.0004 (9)
C5A	0.0076 (11)	0.0179 (13)	0.0103 (12)	0.0027 (10)	−0.0004 (9)	−0.0002 (10)
N4A	0.0058 (10)	0.0193 (11)	0.0105 (10)	0.0000 (8)	0.0004 (8)	−0.0008 (8)
C6A	0.0097 (12)	0.0196 (13)	0.0100 (12)	0.0015 (10)	0.0014 (10)	−0.0023 (10)
N5A	0.0099 (11)	0.0397 (15)	0.0090 (11)	0.0017 (10)	0.0020 (9)	0.0018 (10)
N6A	0.0092 (10)	0.0322 (14)	0.0093 (11)	0.0014 (9)	−0.0010 (9)	0.0044 (9)
C7A	0.0100 (12)	0.0259 (15)	0.0101 (12)	−0.0003 (10)	0.0017 (10)	−0.0022 (10)
O5A	0.0102 (9)	0.0361 (12)	0.0085 (9)	0.0013 (8)	0.0003 (7)	−0.0043 (8)
C8A	0.0088 (12)	0.0189 (13)	0.0116 (12)	−0.0016 (10)	0.0003 (10)	−0.0004 (10)
O6A	0.0075 (9)	0.0310 (11)	0.0113 (9)	0.0027 (8)	0.0002 (7)	−0.0017 (8)
O7A	0.0119 (9)	0.0315 (11)	0.0081 (9)	0.0004 (8)	0.0007 (7)	−0.0006 (8)
O8A	0.0097 (10)	0.0771 (19)	0.0102 (10)	0.0078 (11)	0.0012 (8)	−0.0011 (11)
O9A	0.0165 (10)	0.0282 (11)	0.0202 (10)	−0.0036 (9)	0.0002 (8)	0.0017 (9)
O10A	0.0141 (10)	0.0365 (13)	0.0166 (10)	0.0008 (9)	0.0014 (8)	0.0038 (9)
N7A	0.0125 (11)	0.0185 (12)	0.0142 (11)	−0.0016 (9)	0.0020 (9)	0.0013 (9)
O11A	0.0094 (9)	0.0446 (13)	0.0170 (10)	−0.0046 (9)	0.0019 (8)	0.0027 (9)
O12A	0.0164 (10)	0.0353 (12)	0.0120 (9)	−0.0041 (9)	0.0047 (8)	−0.0013 (8)
O13A	0.0166 (10)	0.0376 (13)	0.0157 (10)	−0.0029 (9)	−0.0047 (8)	0.0019 (9)
Cu1B	0.00708 (15)	0.02091 (18)	0.00765 (15)	−0.00005 (12)	0.00000 (12)	0.00013 (12)
Cu2B	0.00705 (15)	0.02764 (19)	0.00762 (15)	0.00080 (13)	0.00041 (12)	0.00048 (12)
O1B	0.0091 (8)	0.0247 (10)	0.0100 (9)	−0.0007 (7)	0.0007 (7)	0.0006 (7)
O2B	0.0097 (9)	0.0270 (11)	0.0115 (9)	−0.0034 (8)	−0.0018 (7)	0.0020 (8)
C1B	0.0146 (12)	0.0126 (12)	0.0096 (12)	−0.0019 (10)	0.0000 (10)	0.0013 (9)
C2B	0.0091 (12)	0.0214 (14)	0.0093 (12)	−0.0024 (10)	−0.0014 (10)	0.0009 (10)
N1B	0.0067 (10)	0.0232 (12)	0.0083 (10)	−0.0003 (9)	0.0003 (8)	−0.0002 (8)
C3B	0.0151 (13)	0.0107 (12)	0.0109 (12)	−0.0001 (10)	−0.0002 (10)	0.0006 (9)
N2B	0.0134 (11)	0.0237 (12)	0.0081 (10)	0.0000 (9)	−0.0005 (9)	−0.0030 (9)
N3B	0.0105 (10)	0.0247 (12)	0.0104 (10)	−0.0015 (9)	−0.0008 (9)	−0.0021 (9)
O3B	0.0118 (9)	0.0377 (12)	0.0116 (9)	0.0044 (8)	0.0010 (8)	0.0015 (8)
O4B	0.0105 (9)	0.0369 (12)	0.0132 (9)	0.0044 (8)	0.0045 (7)	0.0035 (8)
C4B	0.0112 (12)	0.0235 (14)	0.0126 (12)	−0.0018 (11)	−0.0013 (10)	0.0024 (10)
C5B	0.0065 (11)	0.0254 (14)	0.0114 (12)	0.0025 (10)	0.0014 (10)	0.0030 (10)
N4B	0.0065 (10)	0.0254 (12)	0.0110 (10)	0.0025 (9)	0.0019 (8)	−0.0014 (9)
C6B	0.0109 (12)	0.0229 (14)	0.0111 (12)	0.0012 (10)	−0.0009 (10)	0.0020 (10)
N5B	0.0102 (11)	0.0432 (16)	0.0101 (11)	0.0018 (10)	−0.0013 (9)	0.0011 (10)
N6B	0.0094 (11)	0.0324 (14)	0.0111 (11)	0.0015 (9)	0.0009 (9)	−0.0010 (10)
C7B	0.0113 (12)	0.0258 (15)	0.0109 (12)	−0.0001 (11)	0.0005 (10)	0.0021 (10)
O5B	0.0093 (9)	0.0247 (10)	0.0079 (8)	0.0000 (7)	0.0007 (7)	0.0001 (7)
C8B	0.0096 (12)	0.0178 (13)	0.0126 (12)	0.0005 (10)	−0.0006 (10)	−0.0008 (10)
O6B	0.0092 (9)	0.0273 (11)	0.0105 (9)	0.0003 (7)	0.0008 (7)	0.0007 (7)
O7B	0.0135 (9)	0.0310 (11)	0.0091 (9)	0.0000 (8)	0.0015 (7)	0.0010 (8)
O8B	0.0112 (9)	0.0330 (12)	0.0107 (9)	0.0013 (8)	0.0001 (7)	0.0007 (8)
O9B	0.0147 (10)	0.0265 (11)	0.0182 (10)	0.0031 (9)	−0.0021 (8)	−0.0016 (8)
O10B	0.0130 (10)	0.0426 (14)	0.0153 (10)	−0.0018 (9)	0.0001 (8)	−0.0032 (9)
N7B	0.0133 (11)	0.0231 (13)	0.0148 (11)	0.0014 (9)	−0.0011 (9)	−0.0009 (9)
O11B	0.0090 (9)	0.0438 (13)	0.0154 (10)	−0.0014 (9)	−0.0019 (8)	−0.0017 (9)
O12B	0.0180 (10)	0.0364 (12)	0.0127 (10)	−0.0017 (9)	−0.0040 (8)	−0.0023 (8)
O13B	0.0161 (10)	0.0424 (14)	0.0178 (10)	−0.0039 (9)	0.0059 (8)	−0.0047 (9)

Geometric parameters (Å, º)

Cu1A—O8A	1.911 (2)	Cu1B—O5B	1.9066 (18)
Cu1A—O6A	1.9161 (19)	Cu1B—O6B	1.9126 (18)
Cu1A—O5A	1.9207 (19)	Cu1B—O1B	1.9344 (18)
Cu1A—O1A	1.9259 (19)	Cu1B—O8B	1.939 (2)
Cu2A—O5A	1.920 (2)	Cu2B—O5B	1.9179 (18)
Cu2A—N4A	1.927 (2)	Cu2B—N4B	1.928 (2)
Cu2A—O2A	1.9308 (18)	Cu2B—O2B	1.9486 (18)
Cu2A—O3A	1.9832 (19)	Cu2B—O3B	1.9825 (19)
O1A—C1A	1.259 (3)	O1B—C1B	1.255 (3)
O2A—C1A	1.253 (3)	O2B—C1B	1.260 (3)
C1A—C2A	1.511 (3)	C1B—C2B	1.515 (3)
C2A—N1A	1.450 (3)	C2B—N1B	1.457 (3)
C2A—H2A	0.9900	C2B—H2E	0.9900
C2A—H2B	0.9900	C2B—H2F	0.9900
N1A—C3A	1.341 (3)	N1B—C3B	1.335 (3)
N1A—H1A	0.872 (18)	N1B—H1E	0.847 (18)
C3A—N2A	1.319 (4)	C3B—N2B	1.321 (3)
C3A—N3A	1.337 (3)	C3B—N3B	1.341 (3)
N2A—H2C	0.8800	N2B—H2H	0.8800
N2A—H2D	0.8800	N2B—H2G	0.8800
N3A—H3A	0.8800	N3B—H3E	0.8800
N3A—H3B	0.8800	N3B—H3F	0.8800
O3A—C4A	1.290 (3)	O3B—C4B	1.279 (3)
O4A—C4A	1.245 (3)	O4B—C4B	1.253 (3)
C4A—C5A	1.509 (3)	C4B—C5B	1.505 (4)
C5A—N4A	1.457 (3)	C5B—N4B	1.458 (3)
C5A—H5A	0.9900	C5B—H5E	0.9900
C5A—H5B	0.9900	C5B—H5F	0.9900
N4A—C6A	1.315 (3)	N4B—C6B	1.315 (3)
C6A—N5A	1.333 (3)	C6B—N5B	1.326 (4)
C6A—N6A	1.355 (3)	C6B—N6B	1.380 (3)
N5A—H5C	0.8800	N5B—H5G	0.8800
N5A—H5D	0.8800	N5B—H5H	0.8800
N6A—C7A	1.416 (3)	N6B—C7B	1.449 (4)
N6A—H6A	0.849 (18)	N6B—H6E	0.872 (18)
C7A—O5A	1.414 (3)	C7B—O5B	1.406 (3)
C7A—C8A	1.537 (4)	C7B—C8B	1.539 (3)
C7A—H7A	1.0000	C7B—H7E	1.0000
C8A—O7A	1.236 (3)	C8B—O7B	1.236 (3)
C8A—O6A	1.276 (3)	C8B—O6B	1.275 (3)
O8A—H8A	0.812 (17)	O8B—H8E	0.809 (17)
O8A—H8B	0.800 (17)	O8B—H8F	0.809 (17)
O9A—H9A	0.815 (17)	O9B—H9E	0.807 (17)
O9A—H9B	0.810 (17)	O9B—H9F	0.808 (17)
O10A—H10A	0.801 (17)	O10B—H10E	0.804 (17)
O10A—H10B	0.801 (17)	O10B—H10F	0.808 (17)
N7A—O13A	1.232 (3)	N7B—O13B	1.235 (3)
N7A—O11A	1.262 (3)	N7B—O12B	1.255 (3)
N7A—O12A	1.264 (3)	N7B—O11B	1.265 (3)
O8A—Cu1A—O6A	88.91 (9)	O5B—Cu1B—O6B	86.17 (8)
O8A—Cu1A—O5A	167.85 (11)	O5B—Cu1B—O1B	98.03 (8)
O6A—Cu1A—O5A	84.65 (8)	O6B—Cu1B—O1B	174.81 (8)
O8A—Cu1A—O1A	87.43 (9)	O5B—Cu1B—O8B	163.10 (9)
O6A—Cu1A—O1A	175.94 (8)	O6B—Cu1B—O8B	89.85 (8)
O5A—Cu1A—O1A	99.27 (8)	O1B—Cu1B—O8B	86.98 (8)
O5A—Cu2A—N4A	94.03 (8)	O5B—Cu2B—N4B	93.44 (8)
O5A—Cu2A—O2A	97.26 (8)	O5B—Cu2B—O2B	94.40 (8)
N4A—Cu2A—O2A	168.59 (9)	N4B—Cu2B—O2B	171.34 (8)
O5A—Cu2A—O3A	177.90 (7)	O5B—Cu2B—O3B	170.99 (9)
N4A—Cu2A—O3A	83.90 (8)	N4B—Cu2B—O3B	83.79 (9)
O2A—Cu2A—O3A	84.83 (8)	O2B—Cu2B—O3B	89.00 (8)
C1A—O1A—Cu1A	132.21 (17)	C1B—O1B—Cu1B	131.53 (17)
C1A—O2A—Cu2A	134.95 (18)	C1B—O2B—Cu2B	133.93 (17)
O2A—C1A—O1A	128.2 (2)	O1B—C1B—O2B	127.9 (2)
O2A—C1A—C2A	114.5 (2)	O1B—C1B—C2B	117.5 (2)
O1A—C1A—C2A	117.3 (2)	O2B—C1B—C2B	114.6 (2)
N1A—C2A—C1A	112.0 (2)	N1B—C2B—C1B	111.6 (2)
N1A—C2A—H2A	109.2	N1B—C2B—H2E	109.3
C1A—C2A—H2A	109.2	C1B—C2B—H2E	109.3
N1A—C2A—H2B	109.2	N1B—C2B—H2F	109.3
C1A—C2A—H2B	109.2	C1B—C2B—H2F	109.3
H2A—C2A—H2B	107.9	H2E—C2B—H2F	108.0
C3A—N1A—C2A	122.4 (2)	C3B—N1B—C2B	122.1 (2)
C3A—N1A—H1A	118 (2)	C3B—N1B—H1E	117 (2)
C2A—N1A—H1A	120 (2)	C2B—N1B—H1E	121 (2)
N2A—C3A—N3A	120.2 (2)	N2B—C3B—N1B	121.2 (2)
N2A—C3A—N1A	120.1 (2)	N2B—C3B—N3B	119.7 (2)
N3A—C3A—N1A	119.7 (3)	N1B—C3B—N3B	119.1 (2)
C3A—N2A—H2C	120.0	C3B—N2B—H2H	120.0
C3A—N2A—H2D	120.0	C3B—N2B—H2G	120.0
H2C—N2A—H2D	120.0	H2H—N2B—H2G	120.0
C3A—N3A—H3A	120.0	C3B—N3B—H3E	120.0
C3A—N3A—H3B	120.0	C3B—N3B—H3F	120.0
H3A—N3A—H3B	120.0	H3E—N3B—H3F	120.0
C4A—O3A—Cu2A	114.45 (16)	C4B—O3B—Cu2B	114.16 (17)
O4A—C4A—O3A	123.5 (2)	O4B—C4B—O3B	124.2 (2)
O4A—C4A—C5A	118.9 (2)	O4B—C4B—C5B	117.7 (2)
O3A—C4A—C5A	117.5 (2)	O3B—C4B—C5B	118.1 (2)
N4A—C5A—C4A	110.0 (2)	N4B—C5B—C4B	109.4 (2)
N4A—C5A—H5A	109.7	N4B—C5B—H5E	109.8
C4A—C5A—H5A	109.7	C4B—C5B—H5E	109.8
N4A—C5A—H5B	109.7	N4B—C5B—H5F	109.8
C4A—C5A—H5B	109.7	C4B—C5B—H5F	109.8
H5A—C5A—H5B	108.2	H5E—C5B—H5F	108.2
C6A—N4A—C5A	117.6 (2)	C6B—N4B—C5B	117.2 (2)
C6A—N4A—Cu2A	127.16 (18)	C6B—N4B—Cu2B	128.33 (19)
C5A—N4A—Cu2A	113.96 (16)	C5B—N4B—Cu2B	113.88 (16)
N4A—C6A—N5A	124.2 (2)	N4B—C6B—N5B	124.2 (2)
N4A—C6A—N6A	119.0 (2)	N4B—C6B—N6B	117.6 (2)
N5A—C6A—N6A	116.8 (2)	N5B—C6B—N6B	118.2 (2)
C6A—N5A—H5C	120.0	C6B—N5B—H5G	120.0
C6A—N5A—H5D	120.0	C6B—N5B—H5H	120.0
H5C—N5A—H5D	120.0	H5G—N5B—H5H	120.0
C6A—N6A—C7A	122.5 (2)	C6B—N6B—C7B	117.2 (2)
C6A—N6A—H6A	120 (2)	C6B—N6B—H6E	112 (2)
C7A—N6A—H6A	118 (2)	C7B—N6B—H6E	113 (2)
O5A—C7A—N6A	114.4 (2)	O5B—C7B—N6B	113.1 (2)
O5A—C7A—C8A	108.7 (2)	O5B—C7B—C8B	110.5 (2)
N6A—C7A—C8A	109.6 (2)	N6B—C7B—C8B	108.7 (2)
O5A—C7A—H7A	108.0	O5B—C7B—H7E	108.2
N6A—C7A—H7A	108.0	N6B—C7B—H7E	108.2
C8A—C7A—H7A	108.0	C8B—C7B—H7E	108.2
C7A—O5A—Cu2A	113.92 (15)	C7B—O5B—Cu1B	110.62 (15)
C7A—O5A—Cu1A	109.08 (15)	C7B—O5B—Cu2B	116.33 (15)
Cu2A—O5A—Cu1A	126.72 (10)	Cu1B—O5B—Cu2B	130.43 (10)
O7A—C8A—O6A	124.3 (2)	O7B—C8B—O6B	124.9 (2)
O7A—C8A—C7A	120.8 (2)	O7B—C8B—C7B	119.9 (2)
O6A—C8A—C7A	114.9 (2)	O6B—C8B—C7B	115.1 (2)
C8A—O6A—Cu1A	114.18 (17)	C8B—O6B—Cu1B	114.00 (16)
Cu1A—O8A—H8A	125 (3)	Cu1B—O8B—H8E	115 (2)
Cu1A—O8A—H8B	121 (3)	Cu1B—O8B—H8F	118 (2)
H8A—O8A—H8B	112 (4)	H8E—O8B—H8F	105 (3)
H9A—O9A—H9B	117 (4)	H9E—O9B—H9F	116 (4)
H10A—O10A—H10B	106 (4)	H10E—O10B—H10F	111 (4)
O13A—N7A—O11A	120.8 (2)	O13B—N7B—O12B	121.1 (2)
O13A—N7A—O12A	121.1 (2)	O13B—N7B—O11B	120.4 (2)
O11A—N7A—O12A	118.1 (2)	O12B—N7B—O11B	118.6 (2)
O8A—Cu1A—O1A—C1A	173.7 (3)	O5A—Cu1A—O6A—C8A	−11.48 (19)
O5A—Cu1A—O1A—C1A	3.8 (3)	O5B—Cu1B—O1B—C1B	−0.8 (2)
O5A—Cu2A—O2A—C1A	−8.3 (3)	O8B—Cu1B—O1B—C1B	−164.6 (2)
N4A—Cu2A—O2A—C1A	163.1 (4)	O5B—Cu2B—O2B—C1B	22.6 (3)
O3A—Cu2A—O2A—C1A	171.9 (3)	O3B—Cu2B—O2B—C1B	−149.0 (3)
Cu2A—O2A—C1A—O1A	1.8 (5)	Cu1B—O1B—C1B—O2B	12.1 (4)
Cu2A—O2A—C1A—C2A	−178.70 (18)	Cu1B—O1B—C1B—C2B	−170.36 (18)
Cu1A—O1A—C1A—O2A	1.1 (4)	Cu2B—O2B—C1B—O1B	−26.9 (4)
Cu1A—O1A—C1A—C2A	−178.33 (18)	Cu2B—O2B—C1B—C2B	155.50 (19)
O2A—C1A—C2A—N1A	177.6 (2)	O1B—C1B—C2B—N1B	−2.3 (3)
O1A—C1A—C2A—N1A	−2.8 (3)	O2B—C1B—C2B—N1B	175.6 (2)
C1A—C2A—N1A—C3A	−174.3 (2)	C1B—C2B—N1B—C3B	171.9 (2)
C2A—N1A—C3A—N2A	−5.6 (4)	C2B—N1B—C3B—N2B	3.3 (4)
C2A—N1A—C3A—N3A	174.3 (2)	C2B—N1B—C3B—N3B	−176.9 (2)
N4A—Cu2A—O3A—C4A	2.02 (18)	N4B—Cu2B—O3B—C4B	−4.6 (2)
O2A—Cu2A—O3A—C4A	−176.24 (19)	O2B—Cu2B—O3B—C4B	−179.8 (2)
Cu2A—O3A—C4A—O4A	175.9 (2)	Cu2B—O3B—C4B—O4B	−172.4 (2)
Cu2A—O3A—C4A—C5A	−4.6 (3)	Cu2B—O3B—C4B—C5B	8.7 (3)
O4A—C4A—C5A—N4A	−175.2 (2)	O4B—C4B—C5B—N4B	172.2 (2)
O3A—C4A—C5A—N4A	5.2 (3)	O3B—C4B—C5B—N4B	−8.9 (4)
C4A—C5A—N4A—C6A	−171.3 (2)	C4B—C5B—N4B—C6B	176.7 (2)
C4A—C5A—N4A—Cu2A	−3.4 (3)	C4B—C5B—N4B—Cu2B	4.8 (3)
O5A—Cu2A—N4A—C6A	−12.1 (2)	O5B—Cu2B—N4B—C6B	17.2 (3)
O2A—Cu2A—N4A—C6A	176.4 (4)	O3B—Cu2B—N4B—C6B	−171.4 (3)
O3A—Cu2A—N4A—C6A	167.6 (2)	O5B—Cu2B—N4B—C5B	−172.01 (19)
O5A—Cu2A—N4A—C5A	−178.67 (18)	O3B—Cu2B—N4B—C5B	−0.61 (19)
O2A—Cu2A—N4A—C5A	9.8 (6)	C5B—N4B—C6B—N5B	−0.7 (4)
O3A—Cu2A—N4A—C5A	1.00 (18)	Cu2B—N4B—C6B—N5B	169.8 (2)
C5A—N4A—C6A—N5A	4.5 (4)	C5B—N4B—C6B—N6B	−178.1 (2)
Cu2A—N4A—C6A—N5A	−161.7 (2)	Cu2B—N4B—C6B—N6B	−7.6 (4)
C5A—N4A—C6A—N6A	−177.6 (2)	N4B—C6B—N6B—C7B	−37.0 (4)
Cu2A—N4A—C6A—N6A	16.2 (4)	N5B—C6B—N6B—C7B	145.4 (3)
N4A—C6A—N6A—C7A	19.5 (4)	C6B—N6B—C7B—O5B	72.0 (3)
N5A—C6A—N6A—C7A	−162.4 (3)	C6B—N6B—C7B—C8B	−165.0 (2)
C6A—N6A—C7A—O5A	−61.4 (4)	N6B—C7B—O5B—Cu1B	142.17 (18)
C6A—N6A—C7A—C8A	176.3 (2)	C8B—C7B—O5B—Cu1B	20.1 (3)
N6A—C7A—O5A—Cu2A	58.6 (3)	N6B—C7B—O5B—Cu2B	−54.3 (3)
C8A—C7A—O5A—Cu2A	−178.60 (16)	C8B—C7B—O5B—Cu2B	−176.30 (16)
N6A—C7A—O5A—Cu1A	−153.65 (19)	O6B—Cu1B—O5B—C7B	−13.41 (18)
C8A—C7A—O5A—Cu1A	−30.9 (2)	O1B—Cu1B—O5B—C7B	163.52 (17)
N4A—Cu2A—O5A—C7A	−24.08 (19)	O8B—Cu1B—O5B—C7B	−90.2 (3)
O2A—Cu2A—O5A—C7A	154.24 (18)	O6B—Cu1B—O5B—Cu2B	−173.98 (14)
N4A—Cu2A—O5A—Cu1A	−165.07 (14)	O1B—Cu1B—O5B—Cu2B	2.96 (15)
O2A—Cu2A—O5A—Cu1A	13.25 (15)	O8B—Cu1B—O5B—Cu2B	109.3 (3)
O8A—Cu1A—O5A—C7A	82.6 (5)	N4B—Cu2B—O5B—C7B	14.44 (19)
O6A—Cu1A—O5A—C7A	24.36 (18)	O2B—Cu2B—O5B—C7B	−169.24 (19)
O1A—Cu1A—O5A—C7A	−154.53 (17)	N4B—Cu2B—O5B—Cu1B	174.11 (14)
O8A—Cu1A—O5A—Cu2A	−134.9 (4)	O2B—Cu2B—O5B—Cu1B	−9.58 (14)
O6A—Cu1A—O5A—Cu2A	166.86 (14)	O5B—C7B—C8B—O7B	164.6 (2)
O1A—Cu1A—O5A—Cu2A	−12.03 (15)	N6B—C7B—C8B—O7B	40.0 (3)
O5A—C7A—C8A—O7A	−158.0 (2)	O5B—C7B—C8B—O6B	−19.3 (3)
N6A—C7A—C8A—O7A	−32.3 (4)	N6B—C7B—C8B—O6B	−143.9 (2)
O5A—C7A—C8A—O6A	23.4 (3)	O7B—C8B—O6B—Cu1B	−175.6 (2)
N6A—C7A—C8A—O6A	149.1 (2)	C7B—C8B—O6B—Cu1B	8.5 (3)
O7A—C8A—O6A—Cu1A	177.8 (2)	O5B—Cu1B—O6B—C8B	2.47 (19)
C7A—C8A—O6A—Cu1A	−3.7 (3)	O8B—Cu1B—O6B—C8B	166.03 (19)
O8A—Cu1A—O6A—C8A	178.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O11A	0.87 (2)	2.07 (2)	2.921 (3)	164 (3)
N1B—H1E···O11B	0.85 (2)	2.10 (2)	2.933 (3)	169 (3)
N2A—H2C···O4B	0.88	1.95	2.804 (3)	164
N2A—H2D···O12B^i	0.88	2.20	3.076 (3)	172
N2B—H2G···O4A^ii	0.88	2.00	2.866 (3)	166
N2B—H2H···O12A	0.88	2.11	2.980 (3)	169
N3A—H3A···O3B	0.88	2.19	3.061 (3)	172
N3A—H3B···O12A	0.88	2.21	3.072 (3)	166
N3B—H3E···O3A^ii	0.88	2.22	3.099 (3)	176
N3B—H3F···O12B	0.88	2.19	3.056 (3)	168
N5A—H5C···O7B^iii	0.88	2.15	2.991 (3)	159
N5A—H5D···O9B^iii	0.88	2.15	2.942 (3)	150
N5B—H5G···O7A^iv	0.88	2.21	3.055 (3)	162
N5B—H5H···O9A^iv	0.88	2.04	2.901 (3)	166
N6A—H6A···N6B^v	0.85 (2)	2.52 (3)	3.158 (4)	132 (3)
N6B—H6E···O9A^iv	0.87 (2)	2.57 (2)	3.328 (3)	146 (3)
O8A—H8A···O9A	0.81 (2)	1.86 (2)	2.664 (3)	170 (4)
O8A—H8B···O11A	0.80 (2)	1.86 (2)	2.653 (3)	175 (4)
O8B—H8E···O9B	0.81 (2)	1.87 (2)	2.673 (3)	172 (4)
O8B—H8F···O11B	0.81 (2)	1.87 (2)	2.669 (3)	172 (3)
O9A—H9A···O10A	0.82 (2)	1.85 (2)	2.663 (3)	172 (4)
O9A—H9B···O10B^vi	0.81 (2)	2.19 (2)	2.896 (3)	146 (3)
O9A—H9B···O13B^vi	0.81 (2)	2.63 (3)	3.212 (3)	131 (3)
O9B—H9E···O10B	0.81 (2)	1.85 (2)	2.651 (3)	173 (4)
O9B—H9F···O3A^vii	0.81 (2)	2.18 (2)	2.930 (3)	155 (3)
O10A—H10A···O7B^viii	0.80 (2)	2.10 (2)	2.870 (3)	161 (4)
O10A—H10B···O4A^ii	0.80 (2)	2.16 (2)	2.926 (3)	160 (4)
O10B—H10E···O7A^ix	0.80 (2)	2.05 (2)	2.840 (3)	169 (4)
O10B—H10F···O4B^ii	0.81 (2)	2.01 (2)	2.802 (3)	166 (4)

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